New! Aunt Hilda’s Girl

A businesswoman’s nephew drops out of college to take a “Gap” year. She isn’t thrilled that he decides to move in with her. She puts him to work at her office, and also keeps him busy with her housekeeping. Her Gay, male boss, takes a fancy to the boy. Auntie sees a way to be rid of the wastrel and also get some workplace benefits.... 

Chapter I: The Dilemma

    Hilda Pendergast wasn’t thrilled that her nephew Giles, was on his way from college to her home. His father, her brother, was in Europe with his newest girlfriend. The boy’s mother had just moved to California with her latest “Boy Toy.” Neither parent had time for their own, 19 year old, college drop-out son.

    So, Giles Pendergast was coming to love with Auntie Hilda. Not only for the summer, but for the following “Gap” year, that he was taking. Hilda had done well for herself and was now an executive with the largest bank in Massachusetts. She worked out of their main, Boston office. She was a very busy lady. 

    She had her own social life that she didn’t care for her family to know about. The boy was going to be a problem. Well, if their was one way to get rid of a spoiled, lazy teenager it was to put him to work. Giles arrived with hair down to his shoulders, wearing tight jeans and sandals. That wouldn’t do either, with her social set or her business associates.

    She was going to have to stand her ground. She knew just what to do. It was Saturday. She made lunch for the both of them and served some wine. Then after lunch she began to work on Giles.

    “So, you studied business administration, in college? Because you’re going to work you know. And I have just the job for you. I need an admin at my new position and I’ll be able to hire my own. So, you will be interviewing for the job. In fact, tomorrow some of my co-workers and the Executive VP of our Boston branches will be dining here at the house,” Hilda said.

    “It would be a good time for you to meet them. But from the looks of your clothes in your suitcases and your hair, you’ll need to have your tresses done over and some business casual clothes,” Hilda said.

    “Have my hair done? Isn’t that a sort of sissyish, feminine term? And do we have time to shop for clothing prior to then?” Giles asked.

    “Feminine? What’s masculine and what’s feminine these days? The lines are pretty blurred if you ask me? Especially here in Boston. My hairdresser, Dora will be here Sunday morning. She’s doing my hair and staying for lunch. You just need a trim, a shaping and styling,” Aunt Hilda said.

    “As for the clothes? I wear very feminine attire away from the office. But at the office, I prefer mannishly styled, female suits, slacks and blazers. We’re very close to the same size. You’re slender. We’re close to the same height. You might be a little taller? My business casual wear will fit you,” Hilda stated.

    Hilda was correct. Her clothing did fit Giles. Though Giles protested mildly about having his hair styled and wearing his Aunt’s “Mannishly Cut” attire, he was secretly turned on. Giles was a closet crossdresser. Since going off to college he’d been unable to dress in his mother’s clothing.

    But when he’d had some extra money, at Columbia University, where he’d went to school, he’d frequented a Transvestite Dressing Service in New York. There the “Mistress” would put makeup on him, along with a wig. Then she’d dress him as a female and allow him to masturbate as she spanked him for being a “Bad” girl. 

    Having his hair done by his Aunt’s hairdresser and having Auntie dress him in her slacks, a tops and blazer, was a turn on for him. He even agreed with her to wear pantyhose and ballet flats, when she said that would feel better with her satin slacks.

    Dora had styled Giles’s hair beautifully. The women from Hilda’s office adored the way that Giles looked. But it was Jacque Lapointe, the Executive VP that really took an interest in Giles. Prior to dinner, Jacques Lapointe, Aunt Hilda Pendergast’s, Homosexual boss, was just enchanted with her nephew, young nineteen-year-old, Giles Pendergast.

    Jacques really enjoying talking with Giles, prior to and during the dinner. Hilda noted it. When she approached her boss Jaques, after the dinner, she was still wondering if she should bring up anything about hiring her nephew, though? 

    “Mr. Lapointe, I wondered if I couldn’t bring up something privately about work?” Hilda asked.

    “Hilda, please? I’m at your home and just enjoyed a beautiful dinner with you. Just call me Jacques. Of course Hilda. What is it you’d like to speak with me about?” Jacques asked.

    “Well it’s my nephew. He just completed two years at Columbia University in New York. He’s enrolled in Business Studies. He’s taking a gap year now. With my new promotion I understand I’m entitled to hire my own Admin. With your approval of course, sir. Is there any company rules that would prevent me from hiring my nephew?” Hilda asked.

    Jacques couldn’t believe his good fortune. Hilda wanted to hire that beautiful, pretty young boy? Jacques knew he would love to have that cute looking, piece of Boy Toy Eye Candy, at the office.

    “No Hilda. There isn’t any such company rule. And if there is, then we’ll circumvent it. Have him come in tomorrow for an interview. I’ll interview him myself with you,” Jacques said.

    “Well there is his hair and his wardrobe. I’d like to shop with him for some things for the office. In fact he’s wearing some of my things, right now,” Hilda blushed.

    “Well they certainly fit him very well. And his hair looks to be nicely styled,” Jacques added.

    “Yes, my hairdresser just did do his hair,” Hilda explained.

    “Well his hair looks great to me, then. Hilda do you have a corporate credit card?” Jacques asked. 

    “Why yes. But I only use it for business travel,” Hilda said.

    “Well let’s make an exception in this case. My admin, Ms. Kravitz, approves all expenses. I’ll explain things to her. This coming week, why not take your nephew to Granby Street Boutique? Here take my business card. Ask for Francois. In fact I’ll contact him this evening. I have his personal number. Tell Francois I want your nephew properly fitted for clothing for the office, as well as some personal attire,” Jacques said.

    Hilda knew her boss was Gay. He’d frequently bring his latest, effeminate Boy Toy, to office parties. It was known throughout the executive offices of Rockland Financial Services. Just as it was well known, that there were two LGBT males and one LGBT female on the board of directors of Rockland. Hilda also knew that Granby Street Boutique was where all the well-taken-care-of young Homosexuals in Boston shopped for their clothing.

    Did she care that her boss already had a crush on her nephew Giles? Of course not. By moving in with Hilda, instead of one of his divorced parents, Giles was infringing on his Aunt Hilda’s social life. Hilda was a dominant Lesbian that played the field. One of her lovers was Dora, her hairdresser.

    Hilda also liked to go to the LGBT clubs around Boston to find submissive young Femmes to take home. How was she going to do all of that without Giles finding out? She certainly didn’t want her Brother, Giles’ father, knowing. Nor did she want her brother’s gossipy ex-wife, Giles’ mothering informed, either.

    If her boss could keep Giles occupied socially, that would be a plus. Maybe Giles was gay? “Well, we’re going to find out soon, won’t we?” Hilda asked herself.

    Monday, when Hilda took Giles to the Granby Street boutique to be fitted for Office wear, Giles looked a little uncomfortable, when Francois, felt around Giles upper thighs and his crotch region as Giles tried on clothing. Giles was surprised by how much his Aunt spent on him.

    “Don’t worry dear. This is all being paid for by my company. My boss, Mr. Lapointe told me to put it on the corporate card,” Hilda said.

    Of course Giles got the job and began working for his aunt in her new, private office. Jacques Lapointe dropped by from time to time just to get a look at his new piece of Boy Toy  Eye-Candy. Giles settled in at both work and his Aunt Hilda’s home. Hilda had to adjust her schedule and her personal life.

    Weekends she’d say she was doing “Some things with the girls,” in order to spend an evening having sex with Dora or whatever submissive femme she might pick up at an LGBT nightclubs. Giles didn’t seem to mind. Then Hilda began to notice something about her clothing. Hilda had a portable rack in her dressing room where she hung up clothing she’d worn and was planning on taking to be dry cleaned.

    Hilda was very fastidious about how she hung things up or even how she placed her panties in her clothes hamper. Her clothing, especially what she’d hung up to take to the cleaners was being disturbed and moved around. She wasn’t imagining things. Could it possibly be her nephew Giles? Was he wearing her things? Could Giles be a closet crossdresser?

    Hilda would find out sooner than she had thought she would. Jacques wanted her to go out of town on business to see a very important client. While she was out of town, of course, Jacques would have Giles report directly to him. Hilda had already instituted a list of household chores that Giles had to do around the house to keep himself useful.

    A landscaping service took care of the outside. And even though a housecleaning service came in once a month, she expected Giles to perform routine cleaning and to assist with meal preparations to remain useful around her large, opulent home.

    Since she’d been in secondary school, Hilda had worked at one sort of job or the other to make her own spending money. She’d also began saving money at a young age. By the time she was in college, studying finance, she’d started investing. Once she’d begun to climb the corporate ladder, she’d started to accumulate some wealth.

    She’d also kept astute contacts with friends in other business occupations, such as real estate. One of her Lesbian friends had told her of a hot listing on a home that she’d soon be putting up.

    “It’s lovely Hilda. Located in a private community. It’s an estate type sale. The children are selling off their late parents’ home, furnishings and possessions. The market for sellers is soft right now. And these kids just want to unload everything and split the proceeds,” her Lesbian, Realtor friend had said.

    Hilda gave a somewhat reasonable, but now, very solid offer and the Heirs took it immediately. As the realtor had described the home was in a very private, secure, gated community and quite large and elegant. One feature was an alarmed security system with motion activated cameras. Hilda used the alarm system whenever she left the home, as well as at night.

    She’d also used the cameras to keep tabs on her housekeeping service, as well as the monthly landscape company. She now planned to use the motion cameras to ascertain whether or not her nephew Giles was a Sissy Crossdresser. 

    For her own informational purposes she had done quite a bit of recent research on crossdressing. And in the event that she discovered that Giles was an effeminate, limp-wrist faggot, she intended to use his weakness for women’s attire, to her own advantage. The cameras in her boudoir, as well as Giles’ room were set to activate.

    She’d also set up the cameras in her bath as well as Giles’ bath, along with the living room and kitchen viewers. She felt that those should be enough to observe what she wanted to see.

    She left an entire rack of clothing in her boudoir that was eventually destined for the dry cleaners. Her clothes hamper was also filled with lingerie and panties she had recently worn. If indeed her nephew was the sissified femme she believed him to be, he was going to be like a child in a candy factory during the week of her absence.

    When Hilda was done with her business and ready to fly home, she decided to assert herself even more firmly with her nephew. She called him and said, “I’m taking a Friday, mid-afternoon flight from New York. I should be walking thru the front door by 6 PM. I’ll expect dinner on the table and a fresh drink when I arrive, Giles.”

    “The house had better be spotless, also. And don’t make plans for Saturday either, dear. I’ll have numerous errands for you to run for me throughout the morning. However you can plan on viewing a movie with Auntie after a late lunch,” Hilda decreed. 

    “Oh yes, Auntie. I understand. I really missed you Aunt Hilda,” Giles answered sweetly.

    Giles had Hilda’s favorite dish and drink, prepared for dinner. After dinner, Hilda announced, “Before you begin the after dinner cleanup Giles, I want you to run my bath. Please put two scoops of salts and two caps full of oil in the bath. Tap on my boudoir door when my bath is ready. I’ll let you know when I’m ready for you to comb some warm-oil conditioner thru my hair in the entertainment room, Giles.” 

    “Yes ma’am Aunt Hilda,” Giles said, surprised at Hilda’s recent overt assertiveness. 

    Yet, after Giles cleaned the dining room and kitchen, he found himself, seated obediently beside his Aunt Hilda, combing hot-oil conditioner thru her hair, after she had taken her bath. When he was done with the combing, Hilda said, “Why don’t you get some sleep now precious? I have a long day planned for you tomorrow dearest.”

    In fact, Hilda did have Giles up very early. She gave him three errand lists, saying, “First, take my clothing cart out to your car. Unload the attire and take it to the dry cleaners. Get a ticketed receipt for each and every item. Next, here is a list of things I need at the drugstore. Among them is scented Massengill Douche, Tampons and Sanitary Napkins. Then stop at Merle Norman’s. There is an entire list of cosmetics and hair coloring I want you to pick up for me, Giles.”

    While Giles was occupied being Aunt Hilda’s Errand Boy, Hilda was in her private office reviewing the videos from the security cameras. She began with the camera in Giles’ bedroom. There, after a number of fast forwards, she watched Giles stand on a chair, and take a Cosmetic kit as well as a set of hot rollers from the top of his closet.

    Now Hilda knew he’d purchased his own makeup and means to do his own hair. He also had his own bottle of depilatory to remove body hair. It was becoming obvious that Giles was a crossdresser. Hilda also noted Giles was wearing a lounging robe she’d hung on the cart with the clothing for the dry cleaners. 

    Going thru the videos taken in Giles bathroom Hilda could see he’d used her bath salts and oils. He’d also shaven his legs, besides using depilatory. The videos taken in Hilda’s boudoir showed Giles picking out clothing from what was on the dry cleaning trolley, as well as taking shoes from some boxes in Hilda’s closet. 

    The boxes had been marked for various charities. Hilda simply  hadn’t made the time just yet to deliver the shoes. Hilda was surprised at how well her high heels fit Giles. One of the videos taken in Hilda’s bath, with Giles at her clothes hamper; as well as one taken in her boudoir, might have been considered disturbing for some Maiden Aunt’s. But not for Hilda Pendergast. 

    While Giles was going thru the hamper picking out panties and lingerie, he began to sniff a pair of Hilda’s nicest satin panties. While he sniffed one pair of his Aunt’s panties, Giles wrapped another pair around his stiffened erection. As he sniffed away enjoying the scent of his Aunt’s fragrant pussy that was left on the panties, Giles masturbated himself to an orgasm. 

    Hilda actually laughed out loud, saying to herself, “I can’t wait for that pathetic pansy to watch this replay with me. I cannot imagine how the little sissy faggot will react when he watches himself jacking off into my panties? Well at least he hand washed the ejaculate out of my underwear.” 

    Hilda watched plenty of footage of Giles cleaning house in full makeup with styled hair. Then she again laughed hysterically as Giles pranced around her bedroom and once again masturbated as he danced seductively in front of the full-length viewing mirror in her boudoir. 

    She shook her head as he licked his own sperm off of the mirror prior to cleaning it. She edited the video down to the highlights, prior to transferring it onto a DVD for later viewing. Giles returned later with the dry cleaning tickets, Hilda’s cosmetics, douche, tampons, sanitary napkins and hair color. 

    Hilda had Giles fix lunch and clean up the kitchen, prior to sitting down in the entertainment room. Then she said, “I’ve already seen parts of this video. I think you’re going to enjoy it. It’s sort of a surprise for you.”

    Giles was puzzled. As the DVD began to play, and Giles watched himself sashay into his Aunt Hilda’s boudoir, in full femme attire, vivid makeup and an updo hairstyle, he embarrassingly stood up to leave the room.

    “Sit your little pansy ass back down you sissy. Isn’t that what they call people like you honey? From my most recent research, the popular name for girls like you is Sissy. Isn’t it?” Hilda asked, putting her arm around her nephew’s shoulder and hugging him tightly against her bosom.

    By the time the DVD was only half way thru, Giles was sobbing and begging Hilda to turn it off.

    “No way, you little faggot. I’m not turning anything off. I watched every bit of this and then some. These are just the highlights. Oh look Giles, you’re sniffing my panties while you jack-off into another pair,” laughed Hilda. 

    “Did you enjoy the scent of Auntie’s pussy Giles? Would you like to sniff Auntie’s pussy in real time honey?” Hilda asked as Giles sniffled like a baby. 

    Once the video was over, Giles had his head in his Aunt Hilda’s lap and was crying his eyes out. Hilda rubbed his back gently and whispered softly, “Don’t worry sweetie. You can make it all up to me but it will take a lot of effort and hard work on your part. Auntie Hilda will take care of this though, sweetie” Hilda promised.

    “But first you need to take off those slacks and underwear so that Aunt Hilda can use this hairbrush to beat your ass red-raw. So do that. Now Giles,” Hilda said.

    As Giles took off his slacks, he paused and asked, “My underwear also Aunt Hilda?” 

    “Yes. Your underwear. Do you think that I really care if I see that tiny, little dick you have? I just watched you shoot ejaculate all over my mirror. Plus I observed you beating-off into my panties. Do you think I’ll be shocked when I see that little clit that you call a penis, you sissy?” Hilda asked.

    Hilda rubbed Giles’ ass and said, “While I’m spanking you with this lovely, hardback, antique hairbrush, I want you to repeat the same thing over and over. I want you to say, I am a sissy-faggot-crossdresser. I want to become a girl. Repeat that over and over as I beat your ass. Do you hear me, girly?”

    “Yes Auntie. I’m a sissy-faggot-crossdresser. I want to become a girl,” Giles blubbered.

    “Here we go, bitch,” Hilda said as she began to paddle Giles’ ass.

    Giles kicked, screamed, wiggled his legs like a girl, and sobbed hysterically as Hilda smacked his ass until it was bright red. The entire time Giles blubbered out his “Sissy” mantra. When Hilda was done she pushed him off of her lap to the carpeted floor. Giles laid there on the floor whimpering until Hilda told him to kneel in front of her.

    Giles looked up at his Aunt like some sort of whipped puppy-dog. That was just what Hilda wanted to see.

    “You listen to me Sissy, and you listen well. If you know what is good for you, you will obey everything I say from here on. If you resist me even a little, a copy of this DVD will be sent to your father. If you still continue to piss me off after that, a copy will be sent to Mummy. Then I’ll send a copy to the Columbia University Registrars office,” Hilda threatened.

    “I can always show a copy to your co-workers and maybe put some of it up on Facebook. Do you understand me Sissy?” Hilda asked.

    “Yes ma’am Aunt Hilda. I’ll behave. Please don’t sent it to anyone, please?” Giles trembled.

    “Excellent. From here on, you are now enrolled in Aunt Hilda’s Girl’s Finishing School for Debutantes. Your training begins today. I am the Headmistress as well as your instructor. I intend to make your wildest dreams into your very own reality, Sissy. Whenever you are in this house, you may consider yourself as my niece,” Hilda said.

    “You will be called by the name of Gillian. Gillian Anne Pendergast. You may dress as a male, albeit an effeminate one, at the office and for a time, when we leave the home to shop or socialize. But here at my home, you are a girl. My girl. And you will learn everything there is to know about being a girl. You will look like a girl, you will smell like a girl, talk like a girl, move like a girl, walk like a girl and think like a girl,” Hilda promised. 

    “To stay in practice, even at work, I expect your entire body to be smooth, hairless and scented. You’ll wear panties and pantyhose underneath your office attire. Your toes will always be painted. Whether you like it or not, you will become increasingly feminine in public as well as at the office. Don’t fret. Rockland Financial is a very forward thinking corporation,” Hilda asserted.

    “Three of the members of our Board or Directors are Transgender. Two are gay men. One is a Lesbian. And Boston is a very forward thinking city. And guess what? I looked into it. At Columbia University, the college you just withdrew from? Well, it has a sorority for transgender girls. You have no fears for your future Gillian Anne,” Hilda smiled.

    “No matter how far we ever take this, Auntie will see to it that you are covered honey. Any questions, Princess?” Hilda asked.

    Giles was still kneeling at his Aunt Hilda’s feet, naked except for a shirt. His ass was on fire from his paddling and it was beat red. His head was spinning with everything that just transpired, including his Aunt’s recent lengthy pronouncement.

    “Well, Aunt Hilda. I don’t know. It all has happened so fast. It all sounds so well thought out from your perspective. I’m certain I’ll have numerous questions later, but none at the moment,” Giles stated.

    “Just remember Gillian. I have numerous copies of that DVD. By Monday there will be duplicates in my safety deposit boxes. My attorney will have several. If I am a victim of any sort of perceived foul play? Well, Mummy and Daddy will be the very first to get copies. So consider your hands being tied at this juncture, Angel. Understood?” 

    “Yes, of course, Auntie Hilda,” Giles whispered with his head hung, looking at the floor.

    “Okay Doll. Let’s get Miss Gillian Anne, all dolled up,” said Hilda, snapping her fingers and heading towards her boudoir. 

Chapter II: Princess Gillian Anne

    Hilda did not waste a moment’s time. By Monday, when her Sissy nephew Giles walked into the offices of Rockland Financial, “Gillian” had spent the entire remainder of the past weekend as Auntie Hilda’s pretty niece. Giles entire body, other than his eyebrows and the thick tresses upon his head,  was hair-free, smooth and scented. Even his eyebrows had been thinned and arched.

    Hilda had more plans to further sissify and feminize her nephew’s appearance, however she was saving it for the weekend. Giles wore pantyhose underneath his grey, slim-fit, ladies’ slacks. His matching, grey blazer was draped over a white, wide-necked blouse with pearl buttons. On his feet, Giles wore ballet flats. 

   Giles’ skin had been scented so heavily after his Sunday evening bath, that if anyone got close to him, they would think he smelled very pretty. On Saturday evening, for the very first time, Hilda had made her new “Niece” sleep with curlers in her hair and wear a nightgown Gillian was also made to paint her toenails a ravishing Coral Pink.

    “Gillian” had also worn the curlers until after breakfast Saturday morning when Hilda had finally shown her how to comb out her hair and spray it for “an Extra-hold set” throughout the day, Saturday. Because the  curlers had been left in for so long, and “Gillian” had worn a hair-net to bed Sunday night, Giles still had quite a bit of curl and wave in his Bobbed hair, 

at the office Monday. Giles was very self conscious about the curls and waviness, and kept fingering and patting his hair which was just off the top of his shoulders. A few of the office girls were whispering about Giles’ hair and one girl that had to stop into Hilda’s office that day, actually mentioned how “Pretty” Giles smelled.

    However, it was the following week at the office when Giles’ appearance did really cause quite a stir. Hilda had decided that something needed to be done with Giles’ hair. However, she insisted that he be attired as “Gillian” to make the trip to “Femme Fatale” the salon owned by Hilda’s lover, Dora.

    Dora had once mentioned to Hilda that she had a few, “Sissies” that frequented her salon on occasion. Dora had said, “I’ve always attempted to make certain my salon was very Transgender friendly. I have three males that come in on their own, as girls, for beauty services. I also have two women that bring their very pretty spouses in to me. There is one mother that brings in her twenty-two year-old son, who still serves as his mother's Lady’s maid.”

    Hilda had spoken to Dora about her plans for Giles, saying, “I eventually want “Gillian” as I now refer to her, to one day, at the very least, date my boss Jacques. However, I want to go slowly for the time being. This Saturday, I was wondering if we could do something in the way of coloring her hair and piercing her ears?”

    “Of course we can do that. It would be better though, if I can have a look at Giles, when dressed as Gillian. It would be easier for us to decide on the color and style, as well as, if we want to put in highlights,” Dora said.

    “Oh by all means. I want her to get comfortable going out in public as a girl, anyway. This will be her first time out of the house as a female, but she’s been dressing at home now in the evenings and on weekends for the past week at this point,” Hilda said.

    “Bring her in early. I’ll let my girls who are working this coming Saturday know. Most all of my regular clients are aware of my very open Transgender policies. She’ll be just fine. Trust me. I’ll perform all of her beauty services. Just stay close by her, comfort her, and keep her relaxed. Maybe you could give her a valium on the drive to the salon, Hilda?” Dora suggested.

    Hilda did insist that “Gillian” dress properly and also ingest a Valium on the drive to the hairdresser’s. She put Gillian in pink, kitten heels, a floral print, pink and white, sundress, with a wide-brimmed, straw sunhat, and sunglasses. Gillian carried a pink, leather, over-the-shoulder bag. By the time they arrived at the salon, Hilda had also decided that her niece needed a manicure. 

    After a shampoo and condition, Dora looked things over, and said, “We need to give her a blunt cut, just a bit shorter. For a base color, I’d go from her light-brown hair to a darker, medium brown, with some caramel highlights. I’d also start with two ear-piercings and coral pink polish with slight nail-extenders.”

    When Giles mildly protested the nail extenders and the double-piercing, (As opposed to just one set of earrings) Hilda calmly whispered to Giles, “If I were you girly, I’d sit here quietly and really enjoy your first salon experience, honey. You’ll be coming here quite a bit, you know? Besides. You wouldn’t want me to send Daddy some photos of you from last Saturday night at bedtime would you? You looked so cute in those hair-curlers, wearing that powder-blue nightie, with shiny face cream on, and your lips coated with that fresh, hot-pink lipstick. I’ll bet Daddy would just love to see that, wouldn’t he? What do you think, Baby?” 

    Gillian/Giles nodded and smiled, saying, “I think nail extenders and double pierced ears are just what I need, Auntie Hilda.”

    Never having had “her” hair ever colored and never seeing a woman having it done, “Gillian/Giles” was curious about the process. “She” watched intently as Dora applied her color, with an applicator bottle, to darken her hair. More fascinating for the Sissy-Boy, was the highlighting process. 

    It was strangely erotic, as well as shaming, for the emasculated male to have his hair foil-wrapped and watch as the caramel highlights were brushed into his medium brown hair. Then Giles watched mesmerized, as Dora glued on the acrylic nail extenders and painted his nails coral pink. Once the hair color set, and while Giles’ hair was still wet, Dora began to roll the Sissy’s hair up on curlers.

    For the second time in a week, Giles was having his hair set on rollers, on a Saturday. As Dora set Giles’ hair, she asked Hilda, “Do you recall that I told you that I have a Mother, who brings in her twenty-two year-old-son for regular beauty treatments? He lives 24/7 as a girl, and serves as her Sissy-Maid? Do you recall that Hilda? Well, they have their hair, nails and everything else, done together about twice a month.”

    “When she has me set his hair, she brings in the rollers from home, along with a hair-net and scarf. Once his hair is set, I spray it heavily, put the hair-net over it, and wrap the set hair up, tightly, in the scarf. He goes home with his hair up in rollers, just like some sort of Curler Queen. Sometime after they get home, Mummy gives her Sissy-Boy his comb out,” Dora smiled. 

    Both Giles as well as his Aunt Hilda thought about how very shaming that must be? Giles was then made to sit and read a fashion and hair magazine while his wet-set, dried naturally. While Giles read the Mag, he looked at his pink, painted nail extenders. He hoped his aunt didn’t leave the polish on for work at the office Monday.

    He more or less knew he’d be wearing the extenders at the very least, until his nails grew to that length. Dora came over to the now, very prissy Giles, and double pierced both of his earlobes. In two of the holes, she put a pink pearl stud. A baby-blue stud went into the other set of piercings. 

    After Dora set each piercing stud in place, she felt Giles’ damp, colored tresses. She removed a roller or two, to check the degree of curling. Dora did not like to use very much heat with a color-treatment or a perm. She used a slightly warm hand held hair dryer, some gooey styling pomade, a can of spray lacquer, a rattail comb and her fingers, to style Giles’ hairdo into numerous, dangling, girlishly elegant, long, barrel curls.

    “If we put your hair up, these style curls will form into a gorgeous Updo, Gillian,” Dora said.

    Once Dora was done with the stylization, she used the vast array of cosmetics at her disposal, to enliven Giles’ makeup, into a vivid, glowing, beautifying, masterpiece. Giles was overwhelmed with his very sumptuous, obviously feminine, appearance. After several years, of closeted crossdressing, Giles’ Aunt Hilda, was making Giles’ fantasies into a significant reality.

    Giles wondered if this was too much, too soon? However, his Aunt was very assertive and determined. And although Giles wondered if he shouldn’t offer some resistance, he realized that every time his Aunt Hilda saw to it that he was fully dressed, coiffed and made-up, as “Gillian Anne,” he felt so very alive, fulfilled and tantalizingly sensual. 

    Giles wished so very much that he could find a girlfriend to share his feminine side with. Dora removed Giles’ salon-style makeup smock, and stood Giles up and turned him from the mirror towards his smiling Aunt Hilda.

    “You look so very lovely today, my pretty niece, Gillian Anne. Smile for me dear. Ah yes. That’s a good girl. Dora, you did such a fantastic job with her. Now remember Gillian, you can’t shampoo until, at the very soonest, Tuesday afternoon. Of course we’ll wait until Tuesday evening and maybe give you a nice, roller set at bedtime?” Aunt Hilda proposed. 

    “Gillian” hoped that her Aunt didn’t want to do lunch. She’d been out in public long enough today and she wanted to go home and enjoy dressing in private. She felt quite “Heady” after being at the Salon. She had to admit that having her feminization furthered in a Beauty Salon was very exciting.

    As she was leaving the salon, she loved the way her barrel curls tickled the side of her face, and she adored the way the miasma of perfumed and chemical scents enveloped her. So much was happening in her life in a very, girlish way. She was however, apprehensive when her Aunt Hilda brought up “Transitioning.” 

    However, her increasing girlish countenance at the office had to lead somewhere? She hoped her Aunt Hilda would settle on some “Girl Lessons” today. More and more, Gillian was adjusting and cooperating increasingly. 

    Continued “Charm Instruction” would sharpen Gillian’s feminine skills so that she could be more at ease as a girl out shopping, at the salon, when dining or at a nightclub. The eventuality of presenting as Gillian in the workplace had yet to become any sort of reality for her. She was comfortable as Giles in the office, albeit, a more effeminate Giles of late.

    When Monday came around, Giles nervously prepared for his workday. His Aunt Hilda had flatly refused to allow Giles to shampoo the curls out of his hair over the weekend. 

    “We already went over that at the salon Saturday, with Dora, Giles. If you shampoo sooner than Tuesday afternoon you’ll hasten the dissolution and fading of the hair color and highlighting,” Aunt Hilda huffed.

    “Yes, I know Auntie, but these barrel curls are impossible to brush out and they’re so very girly,” Giles whined.

    “But the curls and waves do go wonderfully with the color and highlighting Giles. After all sweetie, it’s only another couple of days. You can shampoo when you take a bath Tuesday night,” Aunt Hilda promised.

    “Could I remove the piercing studs, just at the office?” Giles practically begged.

    “No Giles. You need the studs to stay in to widen the holes properly, so you can wear other earrings at a later date. What are you concerned about Giles? Are you worried about looking too femme? You weren’t concerned about anything like that when you were sneaking around dressing in my nicest clothing, or sniffing and masturbating into my panties were you?” Aunt Hilda asked.

    “No, I guess I wasn’t?” Giles sniffled, shamefully. 

    “Giles, I am really trying to help you. Now listen to me as I explain things. You’ve lived a life of shame, hiding your feminine side from everyone. You should be very proud of your inner, innate, femininity. By having some curl in your hair, and by wearing pretty earrings, you show pride in the girl that lives within you, Giles,” Aunt Hilda exhorted. 

    “Your new, pretty hair color and highlights say a lot about who you are Giles. The people where we work really like you and will be very supportive of you Giles. Just wait and see. Allow them to complement you and thank them. Things are going to be wonderful, sweetie,” his Aunt Hilda promised.

    Giles entered the office wearing a pair of one-inch kitten heels. His spirally barrel curls swirled and framed his smooth, pretty face. Hilda was determined to soon have him wearing light makeup into the workplace. Both of the pink and baby blue studs shimmered in the bright office lighting. Hilda had fitted her prim nephew with a beige, camisole top.

    Over the cami-top he wore a Burgundy blazer and matching, flared Burgundy slacks. Hilda couldn’t wait to get Giles on hormones so that his hips would soon flare. Just the other day, Hilda had also been looking at Purses at the Granby Street Boutique that quite a few male secretaries around Boston had been purchasing. Quite a few Gay young males would give anything to have a handsome, sexy boss like Jacques Lapointe interested in them.

    Giles’ curled, colored and highlighted hair caught the eye of several of the women that had already clocked-in at Rockland Financial that morning. One girl, Tessa, that had a report for Hilda, stopped at Giles desk to check that Hilda was in. 

    “Yes, Tessa let me contact her for you,” said Giles, reaching for his cell phone.

    “Wait Giles. I just wanted to tell you. A few of the girls, including me, just love what you did with your hair, honey. We just love the way you darkened it and those Caramel Highlights are to die for sweetie. Where did you have it done and who did it? You look simply amazing you know, darling?” Tessa cooed, as if Giles were one of the girls.

    “Aunt Hilda took me to Femme Fatale. Her friend, the owner, Dora, did everything. Even my ears,” Giles said, loosening up, a little.

    “Well she did a fantastic job. And yes, I just love the pink and blue pearl studs. They look so cool. Do you mind me asking if the barrel curls are from a perm or a roller set? Tessa asked.

    “A roller set. Aunt Hilda didn’t want me shampooing until the color really took, after about three days. So, you know? I’m really not supposed to be referring to her as Aunt Hilda around the office. It’s Ms. Pendergast,” Giles said, fluttering his fingers in a girlish manner.

    “Let me call her for you. Ms. Pendergast? Yes, Tessa Mannheim is here and would like to go over a report with you? I’ll send her right in. She’s all yours Tessa,” said Giles with a sweeping motion of his hand towards the door to Hilda’s inner office.

    Jacque Lapointe had gotten a very good look at Giles and wanted an even better one. In fact he wanted to compliment Giles face to face. The young admin was looking increasingly effeminate and Jacques simply wanted to get his foot in the doorway if the young male was “Coming Out.” He really needed to find out just what was going on.

    As the top exec in the office, Jacque could have easily had Hilda come to his office about a new account he wanted her to take over. Instead he called her. They scheduled a meeting right after lunch, in her office. Hilda told Giles to just let Mr. Lapointe right thru. 

    Jacque made certain he stopped at Giles desk to complement him.

    “Just go right in Mr. Lapointe. She’s waiting for you sir,” Giles said.

    “Thank you Giles. Giles, I just wanted to say that I think you really look fabulous these days. I mean today you look really, very nice,” Jacque smiled.

    “Well thank you sir, that’s very nice of you to say,” Giles remarked.

    Jacque went into Hilda’s office and they talked at length about the new account. Jacque trusted Hilda thoroughly. Once they had completed their discussion, Jacque brought up Giles’ appearance to see Hilda’s reaction. 

    “I told Giles I really love the way he looks of late. He really is such a good looking young boy, Hilda,” Jacque said.

    “Well thank you Mr. Lapointe. I’ve really been striving to see to it that he takes more care with his appearance. So the earrings are no problem as far as the office dress code, sir?” Hilda asked.

    “Hilda. We’ve known one another for so long. When we’re talking personally in the office like this. I’m Jacque and you’re Hilda. If you’re comfortable with that, of course?” Jacque asked.

    “Yes I am Jacque. So, as I asked, the earrings are okay with you?” Hilda repeated.

   “Yes, they are. In fact I love them. What I mean is. Well, if ladies can wear them, why not males? You know Hilda, we humans often go against nature and shortchange ourselves. Think about it. The male Peacock, is far more flamboyant than the female of that species. And what about the male Lion and that large, beautiful mane compared to the female?” Jacque replied.

    “Yes that is true. Well then, what I wanted to ask is this. I’ve been thinking of having Giles get yet another ear piercing. Much higher up on the ear lobe. That wouldn’t be a dress code issue would it then?” Hilda asked.

    “No. Not at all Hilda. I think it would likely look really great. Hilda. You seem to have a lot of say so and quite a bit of control over the way Giles looks and dresses? Am I correct? If I’m not being too nosy of course?” Jacque asked.

    “Oh no. Don’t worry one bit about that Jacque. No, you are welcome to ask that. Yes, in fact I have a lot of control over the way that Giles both looks and dresses. I have a great amount of control over any decision as to Giles’ everyday appearance,” Hilda said, with close set eyes.

    “I’m the one that took him to the salon and insisted he have his ears pierced and his hair colored as well as curled. I’ve been encouraging him to dress up a bit more elegantly, especially for the office,” Hilda added with a pursed lip smile.

    “That’s interesting, Hilda. Most interesting. Well then let me congratulate you on your progress. I for one, really do like everything I am seeing, concerning Giles, these days,” said Jacques emphatically. 

    “That’s wonderful to hear, Jacque. I intend to continue on my quest to refine Giles’s tastes in clothing, jewelry, as well as hairstyling,” Hilda promised.

    “Well, I’ll be keeping my eyes on Giles then,” Jacques said, shaking Hilda’s hand.

    On the following Saturday, Hilda saw her primary care physician, Edna Redmond. Edna was a Sorority Sister from College. She and Hilda had stayed in touch when Hilda had went off to Grad School and Edna had attended medical school. They were both, exemplary professionals. 

    Though, in college, they had had an on and off, purely, sexual  relationship. They both realized if romance entered into their liaison, they might curtail either one or both of their careers. Still, they remained close friends and were always there to help one another. 

    During the visit at Edna’s office, Hilda shared some of her plans, though not all, concerning her effeminate nephew Giles. Edna listened carefully. Then she commented, saying, “You just might be helping, Giles/Gillian in the long run, Hilda. Gender confusion and Gender dysphoria, can be quite debilitating. Might you be sharing this information with me as you are seeking some assistance from me?” 

    “Now that you mention it, Edna. If you could provide some medical assistance in this matter, it might take things easier for everyone and help expedite the process,” Hilda agreed.

    “As you well know, I’ve experienced a few cases of patients that transitioned from male to female. I might be able to assist with Giles? Then why don’t we make an appointment for him? He probably hasn’t had a physical in some time? Who knows? I’ll discuss gender dysphoria with him and delve into his feelings on possible transitioning?” Edna replied. 

    Edna had Saturday appointments every other week. Hilda waited two weeks and made an appointment for Giles on a day when she was also taking him to the hair salon. Giles spent the early morning having his roots touched up, his brows and lashes tinted, and his third set of ear-piercings done. That morning Hilda had put Giles in a pair of dark panty-hose and matching Capri slacks. 

    Then Hilda had Giles step into a pair of three-inch, black, closed-toe pumps. Giles didn’t mind going to the salon as a sexy version of Gillian. But he was a little troubled about having a physical at a doctor’s office, even if the Physician was a close friend of his Aunt Hilda’s.

    “Don’t concern yourself about Edna, dear. We’re very close and I informed her of the little experiment we’re conducting concerning your sexuality. She’s not only impressed, she agreed to cooperate and allow you to visit her office as Gillian to help us out. Just be on your very best feminine behavior Princess,” Hilda smiled as she handed Giles a sequined, pullover top in a Burgundy shade.

    Giles’ lipstick was a wet-look, deep crimson gloss. The rest of his makeup was strikingly vivid. His longer fingernails were painted to match his lips. He’d begun to think his nails were far too long for a male, even for one who worked as his aunt’s admin. 

    The Sissy-Boy’s blunt-cut bobbed tresses had been blown out into a sleek, shiny, styling. Even as much as he was into his Gillian persona, Giles felt far too sexy looking for a doctor’s visit. His aunt ignored his concerns.

    “Doll-Face. Just let me worry about how you look. You look just fine to be going to the salon. And can a girl help it if she made her doctor’s appointment for right after her salon trip? Get into the car Sugar, and just relax. Auntie Hilda has this as usual,” Hilda added. 

    During the drive from the salon to the doctor’s, Hilda thought ahead. By the next beauty parlor appointment, she wanted her sissy nephew to be on a sufficient amount of female hormones, and a large enough dose of anti-depressants that she’d have no trouble getting him to sit still to have his lips plumped with some collagen injections. 

    When Hilda turned to look at him as they arrived at the parking garage nearest to Edna’s, she noted how devastatingly beautiful her nephew had become after a salon makeover. She’d taken quite a few photos of “Gillian” since the transformation began. And of course she’d done plenty of video’s under the guise of “reviewing” the DVD’s to track Gillian’s progress.

    All of the photos as well as the video’s would be used as leverage should Giles ever want to back out of what Hilda had planned for him. Hilda also hoped that Edna could persuade Giles to attempt transitioning, so that Hilda did not have to resort to trickery to get Giles pumped full of Estrogen. 

    Edna conducted a very thorough physical. She also did a lengthy interview, carefully probing Giles’ emotional state concerning his transformation. Giles warmed to Edna, unusually enough. Midway thru the physical, Giles felt very comfortable even when Edna began to refer to him as “Gillian.”

    During the consultation Edna finally asked, “How comfortable do you think you would be, with Hormone Replacement Therapy, or what we refer to as, HRT? It is reversible, though it is a big step. I’d also recommend some mood altering medication. I believe you still consider crossdressing as something to be ashamed of,” Edna probed.

    “It isn’t, you know. Especially if it might just be who you are Gillian? The medication, in small dosages, just might assist you in being comfortable with being Gillian. I can put you on mild dosages of Estrogen and an anti-depressant and we’ll monitor you closely,” Edna suggested. 

    Hilda was thrilled as she and Giles/Gillian left Edna’s office with the proper prescriptions. She wondered if she could possibly procure bootleg versions of either or both drugs? Gillian had received her first estrogen injection. She had prescriptions for both Estradiol tablets and breast cream. 

    The anti-depressant was in a very mild, starter dose. Hilda planned on making certain that both she and Gillian, had a really “girly” weekend ahead of them. She’d see to it that as frequently as possible, her pretty niece was to be totally immersed in all things girlish and excessively feminine. 

Chapter III: Jacque’s Young Lady Friend

    Jacque Lapointe could see that physically, Giles Pendergast had certainly been further feminized. His eyebrows and lashes had obviously been tinted. His ears had been further pierced, just as his Aunt Hilda had mentioned she’d planned on doing. His attire had an even more feminine cut to it. Somehow though, his features were changing?

    Jacque decided he needed to make a further move if he ever planned on a romantic encounter with this beautiful young boy. Jacque also realized any move he was about to plan on making, had to begin with an approach thru Hilda Pendergast. Under the guise of a discussion of a recent new client contact, he asked Hilda to come to his office.

    They discussed the new account at length, made some suggestions, and then Jacque paused. He’d already thought over what he wanted to say, and he decided to jump in with both feet.

    “Hilda, I wanted to comment on how much I like the changes to Giles’s brows and lashes. The tint really goes well with his hair color. I’ve got to hand it to you Hilda, you really have your nephew looking almost pretty. And the third ear piercing does add something to his improving appearance,” Jacque said.

    “Thank you Jacque. You know though, I do think that Giles is very, very pretty. He’s even become pretty in a very feminine way. Don’t you think, Jacque? Pretty, in that very same way, that those nice cute boys, that you’ve brought to the company parties, are so very pretty?” Hilda replied.

    “Yes Hilda. You are quite correct, there. Yes, I thought the very same thing. Giles is actually prettier than any of my past boyfriends have been. In fact, Giles is a living doll, Hilda,” Jacque said with purpose.

    “I’m so very glad you’ve finally noticed Jacque. I’ve been trying to get you to take notice of my Giles for quite some time,” Hilda admitted.

    “Then Hilda. Would you mind at all if I purchased a gift for your nephew? Maybe some jewelry? I see that he now has a set of small hoops in one set of his piercings. And a set of little, silver stars in another piercing. Why don’t I get him a really nice set of dangling, jeweled, pendants, for the third piercing? Along with a matching bracelet and necklace?”  Jacque proposed. 

    “I think that’s just a lovely idea Jacque. Yes, some very pretty, girlish pendants. With a lovely bracelet and necklace that any girl would simply adore and cherish? Yes, please. Please do that Jacque? Jacque? I wonder if you and I might discuss something privately over a Sunday Brunch at Brennan’s? This coming Sunday, if you will?” Hilda asked.

    “Why of course Hilda,” Jacque agreed.

    “Wonderful then. Yes, I think you and I just might have similar interests and goals Jacque? Where my nephew is concerned, that is? And if you like Jacques, you may give those earrings along with the bracelet and necklace to Giles right here in the office. I would see to it that he wore them, also,” Hilda promised. 

    That conversation had taken place on a Monday of the work week. By that Thursday, of the same week, Jacque had purchased the beautiful jewelry and informed Hilda he would present it to her nephew upon the following day after lunch. Hilda thanked Jacque and let him know she would look forward to it.

    By this juncture, the Estrogen and Estradiol had not only softened Giles physically, but along with the mood-elevators, the effeminate Giles was now extra compliant in an emotional sense. Upon one recent Saturday afternoon, where he’d had a mild hissy fit resisting his Aunt, Hilda had punished Giles by making the pretty “Gillian” stand in a corner as if she were a pre-teen.

    Then, “Gillian” had sobbed out her frustrations with her pretty, pug nose, stuck in a corner of her boudoir. Hilda had approached her and asked, “Well Gillian. Are you ready to let Aunt Hilda give you an enema and a rectal douche? Then will you lay down on your bed and Auntie will insert your new butt plug? Auntie only wants you to wear it so that you can walk prettier for Auntie?”

    Gillian had complied and she now even wore the plug in her rectum when she went to the office. On the Friday that Jacque was to give Giles his new Jewels, Hilda had seen to it that her nephew wore something extra pretty to the office. Hilda had made certain that along with a nice pair of grey, stretch slacks, Giles wore an effeminate, pink, snug fitting Angora top.

    Fitting nicely over the Angora top was a cute, white, pearl button, crop-cardigan. Giles now frequently filed his elongated, clear-lacquered fingernails while at his desk. He was doing so, upon that particular Friday when Jacque Lapointe confidently strode into the outer office where Giles answered the phone and performed his other clerical, secretarial duties.

    “Good afternoon Mr. Lapointe. Ms. Pendergast didn’t mention she was expecting you. Should I call her for you sir?” Giles asked.

    “No Giles. I’m here to see you. Giles, you wear such pretty earrings now, and you always look so nice that I decided to get you some jewelry. I do hope you’ll wear it?” Jacques said, holding the box containing the earrings out to Giles.

    At the same time Hilda came out from her office behind Giles and greeted Jacques with a smile. Giles was overwhelmed. He looked back at his aunt, then at Jacques. Giles extended his hand and reached out almost instinctively for the gift-wrapped box containing the earrings. 

    He opened the box and gasped at the sheer beauty of the opal, dangling, pendant, jewel encrusted earrings. His aunt said, “Oh those are beautiful Giles. That was so very darling of Mr. Lapointe to get you those sweetie. You must try them on this instant and show your appreciation to Mr. Lapointe with a little hug and a kiss of thanks. Here, let Auntie Hilda assist you dear.”

    “Jacque he’s just overwhelmed. Let me help you Giles?” Hilda said.

    Giles stood up awkwardly, blushing. Hilda removed the set of silver stars in one set of piercing holes in the lower lobe. She hung the gorgeous opal pendants front and center for everyone to see.

    “Now thank Mr. Lapointe Giles. A big hug and a little kiss on the cheek. Tell him how lovely they are. Then go look at yourself in the mirror, honey?” Hilda encouraged.

    Giles obeyed, though reluctantly and slightly awkwardly. He put his arms around Jacques broad back and hugged him. Then he gave Jacques a soft, warm, affectionate, moist kiss on the cheek, saying, “Thank you so very much Mr. Lapointe they are so very pretty. Did you want me to look at myself in the mirror Aunt Hilda?” Giles asked. 

    Giles was close to crying with shame, as he wiggled his way to the mirror on the far wall. His aunt followed him. As Giles looked into the mirror, Hilda tapped the earrings so they would tinkle. Giles got a chill down his back and as he touched the earrings he shivered down his spine.

    He turned back around to Jacque, misty-eyed, but smiling softly. Jacques then said, “There’s more. Here’s a necklace and bracelet that match.”

    “Oh that’s so nice. Giles you must put those on also,” Hilda said.

    Obediently, Giles walked over to where Jacque was standing and accepted the other two, gift-wrapped boxes. He set both boxes on his desk. He was shaking slightly. He untied the ribbon of one box. He took deep breath and tried relaxing. He opened the box. It was the charm bracelet. He sighed and fastened the bracelet on his left wrist.

    Giles daintily held his slender wrist in the air and giggled. The girlish giggle helped him to relax. He said, “Oh it’s so very pretty.”

    He did the same with the box that held the Opal necklace. His Aunt Hilda came behind him and fastened the necklace in place saying, “It’s so lovely Giles. Go look at how pretty everything looks against your top and sweater. Then I think you owe Jacque another hug, a kiss on the cheek and a word of thanks?”

    This time, Giles practically sashayed over to the viewing mirror, almost bouncing upon his Kitten heels. His hips swayed prettily to Jacque’s prurient delight. Giles played delicately with all of the jewelry. He was in full, “Gillian” mode at the moment. Impulsively he spun on his pretty heels. Giles swayed almost confidently towards Jacque, smiling almost seductively.

    He honestly didn’t know what had gotten into him? Even Hilda was surprised. Was it possibly the fact that he’d just received his first pieces of jewelry from a potential suitor? Certainly the female hormones and the mood-elevators had to be at work as well?

    Whatever combination it was, this time when Giles hugged Jacque and thanked him, he gave him a soft, moist kiss upon his lips. Jacque loved it. Hilda was thoroughly pleased and beyond surprised. It wasn’t until a very pleased Jacque had left the office that it became apparent to Giles that he’d just kissed his homosexual boss on the lips.

    Self-consciously Giles began to remove the jewelry. His aunt spoke out saying, “Don’t you dare take off any of those gifts. You’ll wear everything proudly for the remainder of the day. And if anyone asks where you got those beautiful gifts you will tell them Mr. Lapointe gave them to you.” 

    Giles took a deep breath and said, “Yes Aunt Hilda.”

    Giles was in no mood to stand in the corner of the office. He wore the jewelry and did not remove it until he undressed at home before helping his aunt prepare a light dinner. Hilda looked forward to what would be her conspiratorial brunch with Jacques that coming Sunday. 

   Once she and Jacques were seated and imbibing, Hilda took a folder from the briefcase she’d brought to the brunch. Smiling, she said to Jacques, “Let’s both agree that we both know that each other are Gay? Shall we? I knew you’d understand, Jacque.”

    “You’re always so up front Hilda. I like that. What’s in the packet?” Jacque asked, modulating his tone of voice just as Hilda had done. Accounting for the brunch crowd in the restaurant.

    “First. Let me also say that I noticed from the very beginning, when you met Giles, that you had an attraction for him. I want you to know I fully approve. Giles needs a strong man in his life, just like you Jacque. His parents were terrible role models. I’ve taken up the slack of course. Until you see fit to take over,” Hilda announced.

    “Now. I realize you’ve noted Giles’ increasing effeminate, if not feminine appearance at the office? Well, not all that long after you met Giles, I discovered that my sweet nephew is a Crossdresser. Yes, that’s correct. With some assertiveness, a little coaxing, and occasional ultimatums, I have cultivated that feature of my nephew’s personality,” Hilda stated. 

   “At this stage, Giles’ life as a female named Gillian, is flourishing both at home and frequently in public. I’ve even started my new niece, Gillian on female hormones. You can view everything from the photos and DVD in that File Folder. Those are your’s to take home and keep if you’d like. Feel free to peek at the photos now Jacque,” Hilda said.

    “I will, Hilda. Oh my goodness. You’ve got to be kidding? She is simply stunning Hilda. Gillian, as you call her, looks fantastic,” Jacques said, excitedly.

    “Well thank you, Jacque. I thought you’d may approve? And when you watch the DVD, you’ll be able to ascertain how I have trained Gillian to move, speak, walk and act just like an elegant twenty-year old debutante,” bragged Hilda.

    “Jacque, I wanted to tell you my further plans for Gillian. I hope, if you are attracted to her, that the two of you could begin dating soon? Then we could see how that goes? What do you think, Jacque?” Hilda asked.

    Jacque was excited by just the thought of having this pretty, feminine, boy in his arms. But of course he had questions. He said to Hilda, “I’d love that Hilda. But what about Gillian? Is she going to be on board with something like that?”

    “Hmm? Well. Gillian just might need a little push in that direction? Or maybe it would be more like a little shove, if you know what I mean? However, between the two of us, I think that together, we could provide such an impetus for her,” Hilda replied.

    “All right. But how so Hilda? What would you suggest we do?” Jacque asked.

    “Well, here’s a little plan I have. It begins with a little bit of a Girly-Girl weekend, that I have planned for Gillian and I. It will take place during the long, four-day weekend that occurs just prior to the end of Summer and the start of Autumn,” Hilda stated.

    “That Friday night, Gillian and I will have a little private party with just the two of us. We’ll do each others nails and give each other green-clay facials, and watch a movie. Then Saturday morning, we’ll go to the Femme Fatale Salon and Spa for complete makeovers. As you can see, immersing my niece Gillian into all things feminine is a big part of what I’ve been doing Jacque,” Hilda added.

    “Now. I’ve told Gillian, that after our makeovers, we’ll take beauty naps back at the estate. Then we’ll get ready and dine that evening at the country club. But that’s when I plan for you to step in, Jacque, and sweep Gillian off of her feet. You’ll show, right after we get back from the salon, and we undress, and put on our robes to take our beauty naps,” Hilda said.

    Jacque was puzzled and asked, “That all sounds well and good Hilda, but just how do I do that? Sweep her off her feet that is?”

    “Well let me finish. I’ll outline the entire plan,” Hilda explained.

    Jacque listened intently as Hilda described her carefully thought out proposition, for getting Jacque and Gillian together, romantically. Jacques was more than surprised at what Hilda was proposing. He liked the idea, but it seemed to have some risk concerned with it? When Hilda completed her proposal, Jacque expressed his misgivings.

    “Hilda I am thrilled you would want me to court your niece Gillian. It’s just that, what you have just outlined sounds like forcible abduction and rape, at one point,” Jacque opined.

    “Jacque. I did say that Gillian will likely need a bit of a shove in the right direction, didn’t I? I really believe that with both of us doing everything we can to persuade her, she’ll get right in line. Besides Jacque. What is she going to do? Is she going to run to the police and tell them she’s a Sissy Crossdresser? Then is she going to tell them, that her aunt’s sexy homosexual boss, whom she once kissed on the lips, when he gave her some jewelry, just had anal sex with her?” Hilda asked.

    “Jacque, she melted when you gave her those earrings along with the bracelet and necklace. She wears them constantly at home. She’s also worn them shopping, to the hair salon and to the doctor’s office. She giggled and kissed you on the lips Jacque, and she was dressed as a boy that day. Let’s give this a try Jacques?” Hilda requested.

    “You are correct Hilda. I think it’s worth it for me. Having a girlfriend like Gillian would be a dream come true for me. I adore effeminate young boys. But a gorgeous, twenty-year-old, feminized Sissy-Boy is all too much to pass up. It’s a deal. Hilda I know what’s in this for me. But tell me Hilda. What’s your angle?” Jacque asked.

    “Well ever since Giles moved in, I’ve had to sacrifice my privacy. I did not want his parents gossiping about my being a Lesbian, so I basically went back into the closet and stopped bringing my girlfriends home,” Hilda said.

    “I’m actually still spending my evenings out at their residences. So if I can find Gillian a regular boyfriend, I can have my personal life back. Truthfully Jacque, you are the perfect man for her. She’s always needed someone in her life who is strong, commanding and assertive. She needs someone to tell her exactly what to do every minute of the day,” Hilda sighed.

    “Well I can assure you I’ll be glad to do that. Is there anything I can do for you at work, Hilda?” Jacque asked.

    “Yes. As a matter of fact. I’d like to be the person that you recommend to the Board, as your second-in-command when that position opens up,” Hilda added.

    “I was already going to see to it that you got that job Hilda,” Jacque smiled.

    “Well that’s nice. Well then, with Ms. Prudence ready to retire, why not take Gillian as your new Admin, and let me hire a cute, little piece of Lesbian fluff for my office?” Hilda asked.

    “Done, Hilda. So we have a deal then?” Jacque asked.

    “I’d like to think of it more as a pact or an alliance, Jacque,” Hilda stated.

    “Agreed. I’ll shake on that. So you want me there at your home, at noon on Saturday, September 4th? And I’ll be dressed in a lounging robe, hiding out in the room next to Gillian’s boudoir ready to go?” Jacques smiled, feeling better about things.

    “Yes, I’ll text you,” Hilda added.

     Hilda Pendergast looked forward to the long Holiday weekend. It was upon her before she knew it. Everything was set. She and Gillian spent Friday having a quiet dinner prior to taking their baths and watching a movie. They did each other’s nails and then shared green-clay facials. Gillian was already showing some very nice growth in her breasts.

    “You are going to need to come out, very soon at work honey, and begin wearing a bra there also. I told you that the firm where we work is very Transgender friendly. It’s not good to spend five days a week, eight hours a day, without a bra on. Especially with your new, sprouting breasts, dear,” Hilda chided her niece.

    Saturday they drove together to the salon. Hilda let Jacque know they were in route. As Gillian was getting her first perm, a body-wave actually, they’d be there at the salon for a few hours. Gillian sat nearly frozen and totally mesmerized as she watched Dora tighten the waving rods in her hair. This was even more intricate than having her hair colored.

    It was a long process that included the application of the perm solution as well as the processing time. Then after the intensity of the curl was checked, a rinse and the adding of the neutralizer, came next. Dora decided to give Gillian a tight, roller, wet-set after the perm was complete. 

    Dora was using a warm blow dry on Gillian’s roller set, when Jacque texted Hilda to let her know that he was ready, and in place. He was having a tall glass of Kentucky Bourbon. Hilda smiled. A little alcohol would loosen him up for the event. 

    On the drive back to Hilda’s estate, Hilda really fussed over her niece’s pretty perm. Hilda had Gillian patting her puffy waves that the roller set had produced. Her hair was in a lovely, teased, evening bouffant. 

    “That ‘Do’ is perfect for an evening dinner at the country club. Remember to wear a hair net when you take your nap. Are you hungry? That lunch at the salon was filling. Let’s just do our naps when we get home. Don’t forget that you can’t shampoo until Tuesday evening,” Hilda said.

    “But what about work Tuesday? I can’t traipse into the office with a teased bouffant, can I?” Gillian asked.

    “Oh we’ll do something with it,” Hilda shrugged.

    Hilda escorted Gillian into Gillian’s boudoir and helped her undress. She already had everything ready. She had just put Gillian’s robe on her and put a lady’s hairdo bonnet over her tresses to protect her bouffant. Then Jacques walked in. He was also wearing a robe, along with slippers. He held a half empty glass of bourbon in one hand.

    Jacque already had a partial erection. Gillian was startled and didn’t know what to say. She stammered, “Mr. Lapointe, what are you doing here?”

    “Relax Gillian. He’s here to make love to you dear. It’s about time, don’t you think?” Hilda asked.

    “What? No, I don’t want to do that. I’m not gay. I’m straight. I want to find a girlfriend,” Gillian insisted emotionally. 

    “Now, now dear. It’s a little bit late for a girlfriend, don’t you think, Princess? Please don’t be difficult Gillian?” Hilda requested.

    “But you can’t do this to me. I won’t stand for it. Now get him out of my room. Both of you need to get out of my room. Now!” Gillian said, raising her voice, yet blubbering.

    “You leave us no choice than, darling. Jacque? Shall we?” Hilda said.

    Jacque immediately placed Gillian in a sort of bear hug, as he kissed her neck. Gillian tried vainly to pull away from him. In the meantime Hilda took some handcuffs and bound Gillian’s hands in front of her. Together, Hilda and Jacques carried a wiggling, wriggling and screaming, Gillian to her bed and laid her down on her back. 

    As Gillian tried to struggle, Jacque got onto the bed. He knelt between Gillian’s thighs and lifted Gillian’s legs and rested them on his shoulders. Gillian kicked and screamed, yelling, “I hate you both. Let me go, now!”

    Jacque now pushed Gillian’s legs towards her. In the meantime Hilda took Gillian’s cuffed hands and arms and pulled them over her head. Pushing Gillian’s cuffed wrists to the mattress Hilda immobilized Gillian’s arms by snugging the sissy’s arms between her own legs. Then Hilda reached up and grabbed Gillian’s legs and held them high in the air. Hilda gripped her niece’s legs tightly.

    Hilda now had Gillian’s arms, held snugly between her own legs. She was also holding Gillian’s legs steadily in the air. Gillian was now immobilized and her ass was a very easy target for Jacque to begin  lubricating. Jacque squirted a desensitizing lubricant into Gillian’s rectum. Them he smeared plenty of lube onto his own hardened cock. Gillian screamed, “Don’t do this. Please don’t do this? I don’t want to be fucked by a man. I’m not gay I tell you.”

    Jacque had never had such a reluctant lover, as Gillian. All the effeminate boys he had dated, were very willing to take Jacque’s penis into their rectum. It was a new, as well as a very exciting experience for Jacque. Jacques was actually becoming very aroused by the struggling, sobbing Gillian. His cock was as hard as a rock. 

    “Gillian, please relax and try to enjoy this for yourself, girl? Jacque will be very, very gentle. He is known as an extremely caring lover,” Hilda whispered. 

    “I’m not a girl. And I don’t want to dress as a girl any longer. Do you hear me Aunt Hilda? Now take those handcuffs off of me and let me go, now!” Gillian whined and began to cry, totally exasperated by her helpless plight. 

    “And how would you know what sort of lover Jacques is anyway, Aunt Hilda? He’s gay and I’ve never seen you with a man, ever,” Gillian sighed and closed her eyes, sobbing.

    “I will be gentle with you, Gillian my love. I’ll make this feel as wonderful as possible,” Jacques said.

    “Oh no. You’re going to screw me anyway aren’t you?” Gillian said, sounding as if she’d given up completely.

    Jacque had a perfect target in Gillian’s rectum as her supple legs were held high above her head. Jacque began to slowly enter Gillian. Hilda watched, smiling. Soon her sissy nephew would at last know what is was like to be a real woman. Jacque entered Gillian’s ass, further, and he listened carefully as Gillian grunted. 

    Gillian was now moaning. She’d stopped protesting. She was breathing in and out, hoping that she would experience the least bit of discomfort as possible, from being butt-fucked. The desensitizing lube was working well, to lessen any irritation. The butt plugs Gillian had used to allegedly “Assist her to walk more girlishly” had done the job of widening her rectal canal. 

    As Jacques finally worked the last inch of his long, fat penis inside of Gillian, Gillian let out a long moan and said, “Oh my gracious. Oh, is it all the way in finally? Oh thank goodness. Oh? Oh my. Oh, now you’re really fucking me aren’t you? I can’t believe this? Oh, Aunt Hilda you’re going to allow him to fuck my ass aren’t you?”

    Now that Jacque’s cock was snugly within Gillian’s anus, he took Gillian’s legs away from Hilda and held onto them himself. In that way, he could carefully manipulate each stroke of his cock, as it went in and out of Gilian’s tight ass. Hilda now held Gillian’s handcuffed wrists within her own hands. 

    Jacque liked the looks of Gillian’s growing tits. He’d need to grab a hold of those on the next occasion when he planned to fuck the sissy from behind. 

    “Enjoy what he’s doing Gillian. Enjoy it my girl. You’re being treated just as if you were a real female young lady. Push back against him and feel, as well as enjoy, what he’s doing,” exhorted Hilda. 

    Gillian had her eyes closed now, and was moaning and sighing as Jacque thrust against her. Hilda laughed and said, “Someone likes being screwed doesn’t she, now, Princess? Your little cock is getting stiff, Gillian honey. Admit it. You love being fucked by your man, don’t you girl?”

    “I do not. I don’t like being fucked like this. I’m not a girl. I’ll never be a girl. Oh my gosh. Oh my goodness,” Gillian said as she began to thrust and push back against Jacques as he screwed her. 

    Hilda smiled as she watched her sissy niece get into the same rhythm that her lover was into. Hilda even released Gillian’s arms from between her legs, though she didn’t yet, take the handcuffs off of her. From the looks of Gillian’s erection, the way her eyes were closed tightly, and the way she puckered her lips, Hilda could see that her niece was finally getting into being screwed like a female.

    Jacque was very excited. Gillian grunted and pushed off with her arched back. Hilda’s puss was getting wet. She felt as if should be masturbating but she held off until later. Jacques was certainly beyond aroused. He seemed as if he would be going off very shortly. Gillian’s breathing began to pick up also.

    It looked to Hilda as if there was going to be some fireworks very, very soon. Gillian began to push harder and harder against Jacque’s very manly thrusts. Gillian’s gasps and her prissy, little squeals became louder and more pronounced. And then, as Gillian felt Jacque’s penis pulse inside of her rectum, she finally let out a pronounced, piercing  shriek. 

    As the shriek resonated, Gillian’s back arched and she howled. Sperm began to squirt from her small, but exposed penis. It shot into the air randomly with some landing on her flat tummy. A small amount of ejaculate squirted wildly and splattered upon her tits. Jacque began to pump his cum into Gillian’s ass.

    As the couple orgasmed nearly simultaneously, Hilda unlocked the handcuffs on her niece’s wrists. Then she massaged the girl’s hands and wrists before Hilda moved away and out of the boudoir. With her hands free, the climaxing Gillian reached towards her lover as if to embrace him. 

    As Jacque and Gillian completed their orgasms, Jacque lowered Gillian’s legs and rolled onto the bed next to her. He suckled her tits and kissed her eyes and face. Gillian moaned, crazily. Tears dripped from the effeminate Girly-Boy’s eyes. Gillian went in and out of giggling and then sobbing.

    She was borderline hysterical as her emotions were completely askew. She knew that she was not supposed to have enjoyed being buggered by a male, but indeed she had. She’d enjoyed it all well enough to have had a shuddering orgasm. At long last she embraced Jacque and kissed him forcefully.

    She bit his lip and his cheek. She growled gutturally and pulled him down on top of her. Finally she said, “I really don’t know what is going on, because I’m so confused right now. But I want to hold you and I want you to hold me. I need to know that everything is okay. Just love me and hold me,” Gillian begged as she smilingly, closed her eyes.

    While the couple embraced, Hilda took care of business. She canceled the reservations at the Country Club and made new dining reservations for Gillian and Jacques at Brennan’s in Boston. She would be having Dora over in her bed this evening. Hilda then put several suitcases of Gillian’s clothing, cosmetic and hair care products into Jacque’s vehicle. 

    As far as Hilda was concerned, Gillian could spend the entire weekend and beyond at Jacque’s residence. Jacque had brought his dining clothes to Hilda’s estate. As he and Gillian dressed for dinner, Hilda informed them of the change in dining plans. She also let Jacque in on the fact that Gillian now belonged to him.

    “Keep her as long as you wish. In fact, as far as I’m concerned, the sooner you can get her to move in with you, the better. I’ll be packing up all of her things for a permanent move to your residence as soon as next week,” Hilda added.

    Gillian was oblivious. As she and Jacque dined at Brennan’s she felt relaxed. For whatever reason, her usual angst, over whether or not the people around her realized she was some sort of Trans-Female, wasn’t present? She felt perfectly comfortable being perceived as a pretty girl out with her boyfriend.

    She was very surprised, but not miffed, when Jacque took several of her suitcases into his house. Jacques showed her around, saying, “You may use this boudoir next to mine, for privacy. However, this evening, I expect you to be in my bed.”

    Gillian smiled and shrugged, answering, “Of course. I didn’t expect it to be any other way.” 

    As Jacque dimmed the lights in his bedroom, Gillian knelt in front of him. She looked radiant in a silver peignoir. Jacque was seated on the edge of the bed. As if she’d been doing it all her life, the kneeling Gillian took Jacque’s penis in her dainty, beautifully French-Manicured fingers. 

    She hadn’t cleaned off even a speck of her vivid masque of makeup. She looked and felt so glam with her elaborate evening hairdo. She knew that by the morning her hair and face would be a complete mess. 

    But she also realized, that was simply what girls did. They made themselves beautiful so that their men could cover them in sperm. And then their only choice was to play with makeup and hair spray and make themselves pretty once again. As Gillian’s lips surrounded Jacque’s expanding cock she looked up pleadingly into his eyes.

    “Do you plan to fill my mouth with your cream, my Master? Or would you like to impale my rectum once again?” Gillian asked.

    Gillian knew that her days as Auntie Hilda’s ward were either numbered or over with. She had a brand new Superior to supplicate herself to. As Jacque’s cock went in and out of her mouth, she looked up at him, wide-eyed and smiling.

    “When I decide I’m hard enough you may climb onto the bed and kneel on all fours. I’ll be taking you doggie style, my little sissy French Poodle. I have the lube right here. You may stop sucking me sissy-girl. Kneel on the bed and make yourself more useful,” Jacque demanded.

    “Yes sir, my master,” Gillian answered.

    As Jacque entered her rectum with his massive cock, Gillian knew she had better learn to enjoy this. She really didn’t have a choice. If he wanted her to bark and yip like a little sissy poodle she would gladly do that for him. His cock slid in beautifully. Gillian began to thrust. She knew who was in charge now.

    She idly hoped that Jacque would have her boudoir redecorated in pinks and white, with pretty lace curtains? She wondered if he would buy her a pretty Barbie car?

Chapter IV: Ms. Gillian Anne Lapointe 

    Gillian minced down the sidewalk, patting her scarf covered curls with her delicate fingers. She loved a late morning touch up at the salon. They always served her a light lunch during her beautification. She was returning to the office. As she walked into the lobby, the security guard stood up and retrieved the elevator for her.

    “Good afternoon Ms. Lapointe. You look just lovely today ma’am,” the guard said.

    “Thank you Charles,” Gillian sang, smiling. 

    Gillian wouldn’t dare think of removing the scarf from her sprayed curls until she was seated in her outer office just outside of Jacque’s main suite. She looked at her calendar. She’d be doing brunch with Auntie and Dora, Sunday at 10. She then pulled her compact from her purse and checked her hair, face and mouth.

    Never satisfied, Gillian touched up her lipstick. Gillian and Jacque had been married for three years. There was still an amazing sexual spark between them. She barely ever saw Jacque peeking over the top of a menu, to leer at some sweet, effeminate looking, gay, sissy faggot, in any restaurant any longer. 

    She glanced thru a small glass opening between her outer office and Jacque’s. Yes. Jacque was back from lunch and on the phone. He saw Gillian and motioned for her to enter his office. 

    Gillian still had her testicles and her tiny penis. Jacque frequently  liked to play with them, and give them sucks, licks, and kisses when they made love. Gillian strolled into the office. As he was still speaking on the phone, Jacque motioned for her to close and lock the inner door. Gillian did so. 

    Gillian stood by his desk with her hand on her hip. Jacques completed his call and set the phone up for auto-message answering. Then he electronically locked the outer door that led to Gillian’s office. Turning to his recently beautified wife he said, “You look sensational, Kitten. Come here to me Precious.”

    Gillian strode to him apprehensively and he grabbed her, pulling her to him roughly. Gillian actually disliked being manhandled like this when she first stepped from the salon. She was very fussy about her appearance. Jacque really didn’t care. When he wanted some of her sissy-ass-pussy, he took it. Regardless.

    Jacque kissed her very mannishly and ran his fingers thru her tight curls and prissy ringlets. He inhaled her rich perfume deeply. Gillian couldn’t move a muscle when he took her into his strong arms, and she just melted. It was as if she could actually faint right now. Jacque was such a strong and overpowering man. 

    “Oh Jacque. You are so excessively masculine. I don’t even know what to do with you? You’ll have me all mussed, before we even get home,” Gillian said, ever so prissily.

    “And then you can have even more fun, primping and preening to put yourself back together Angel. You knew you were marrying a sexual brute when you minced down the aisle in that Mermaid gown and those six-inch heels. I practically raped you in the Limo on the way to the Jet-Port,” Jacque growled. 

    “I know, you animal. You made me suck your balls dry while the limo driver watched in the rearview mirror,” Gillian gasped.

    “Yes. And I fucked your ass silly in the bedroom of Emilio’s private jet before we even landed at Malaga,” Jacques laughed.

    “I’m getting fucking hot, just talking about it. Take your blazer off and unbutton your blouse girl. Then let me unhook your bra. I want to feel those tits I paid so much for, your sexy bitch,” Jacque laughed.

    “Oh they do look great. Geez. Bend over the desk. Bend over now, you hot, little slut,” said Jacque as he took hold of the slightly built, very slender Gillian, and propelled  her across his office.

    “Oh please Jacque? Can’t you wait until we get home?” Gillian simpered.

    “We’ll have fun on the way home. Don’t fret. We didn’t take two cars today. Remember? I drove. You left your car home. You can suck my cock on the interstate. Right now I want to feel and squeeze those boobs ,and fuck your ass pussy,” Jacque demanded.

    “Hold onto the desk Babe. This is going to be a wild ride. Get the lubricant out of your Louis Vuitton bag, you sexy rich-bitch,” Jacque teased. 

    Gillian felt as if she were being treated like a complete street-walking whore. She had once thought, that being the wife of the company president was going to change things, as far as sex went. But, she had miscalculated Jacque Lapointe. Jacque took what he wanted, when he wanted it.

    Gillian was still his admin. And girly admins always got bent over the desk when the boss wanted to get laid. Gillian held tightly to the desktop as Jacque greased up her asshole and his own hard cock. Her miniskirt was pushed up. Her panties were down around her knees. Her legs were spread.

    She had taken her blazer off, and unbuttoned her blouse. Her unsnapped brassiere was still tangled around her wrists. Jacque had not even allowed her the time to completely remove her bra. As Jacque squeezed her tits and pinched her nipples, his slick, hard cock went in and out of her ass. 

    Gillian’s body shook from Jacque pounding away at her rectum. His balls slapped against her ass. But then, Jacque reached around her waist. And then his gooey, lubricated fingers began to manipulate the tiny nub that was Gillian’s useless penis. Those very same fingers massaged her little balls. 

    “Oh how good that feels!” Gillian thought to herself.

    Yes. Her cock was useless as far as ever being used again to screw a female. And it really never got very hard any longer. Far too much Estrogen flowed thru her ultra-feminine body. And of course, her balls could never manufacture and eject very much sperm any longer. 

    But none of that mattered to Gillian. Because when Jacque banged her ass as he was doing at that moment, and he played with what remained of her shrunken genitals, Gillian could make, “A Very Nice Little Sissy Cum.” A Sissy Cum, was a more introspective sort of climax. However, a sort of very weak, milky discharge would dribble from Gillian’s tiny penis. And it would feel ever so good for her.

    And it was worth it. It was worth leaving work looking like a cheap,  disheveled motel prostitute, that had just jumped down from the cab of a tractor trailer. It was worth going 75 Miles Per Hour on the interstate with her wet, crimson lips wrapped around the same cock that had just been in her rectum. 

    It was even worth, opening the card that would come with the One Dozen, Long Stemmed Roses that she would receive Monday morning at the office, after the weekend. She’d smile and blush, when the card would read, “You’re still the hottest babe I’ve ever bent over my desk.”

    It was worth all of that and more, just to be known as Ms. Gillian Anne Lapointe. As Jacques pumped out his first ejaculation of the weekend, Gillian’s minuscule penis dribbled a milky-white seminal fluid. Gillian thought back to those days when she had often sniffed a pair of Auntie Hilda’s panties and jacked off into another pair. 

    She thought about how lucky she was that Auntie was so very understanding. Auntie Hilda knew exactly what her Sissy Nephew needed. And she gave it to him. 

    Jacque zipped up his pants after Gillian had licked his cock clean. Gillian did her best to make herself look presentable. Then Jacque stated, “It’s 2 PM on a Friday afternoon Gillian. Hilda will take care of things for the rest of the day. That’s why I promoted her. Let’s leave early.”

    As they left the office, Gillian remarked to Jacque, “That’s so true honey. Auntie Hilda always takes care of everything. Doesn’t she?”

    As the married couple passed by Hilda’s office they heard Auntie Hilda say, “You two lovebirds have a wonderful weekend.”

    It was then that Hilda made the note to herself to order Gillian’s one dozen roses to be delivered to the office on Monday. 

    As Gillian slid into the passenger seat of Jacque’s Jaguar, she fixed her lipstick for the 80 Mile Per Hour blow job she as about to give to her husband. Gillian loved having her lipstick look just perfect. 

The End