Priscilla Gay Bouffant
As I came to Alicia’s bed, I was tense and apprehensive. Alicia “shushed” me and put her arms around me. We merged our wet lips together. Our hands rubbed all over each other’s bodies. We squeezed one another’s breasts. Our hands went to our partner’s penis.
Then Alicia took hold of the vitamin E oil. She lubed our penises and turned me around. She put two very oily fingers in my rectum. I hissed slightly, and she slapped my butt and called me a “sissy.” Once my penis was fully erect, she told me I was ready.
Alicia’s penis was certainly hard enough to enter me. I knelt on all fours as she mounted me. She pushed her penis slowly into my anus. She played with my cock by reaching underneath my butt. Once her penis was all the way inside me, she started moving it in and out very slowly.
The feeling was incredible. Especially when the very head of her penis would press against my prostate. How I grew to love that wonderful feeling. I had initially said to her as she entered me, “Please, be gentle with me, Alicia my darling?”
“Of course, my, pet. After all, you’re a virgin in this way, aren’t you, love? I feel so honored to be taking your virginity, my Babette. Trust me, my love. Once you have had sex like this, you’ll want it in no other fashion,” Alicia promised.
I got into a rhythm with her. Pushing back, squeezing her penis with my butt cheeks, and pulling away and releasing her cock. Each time she contacted my prostate, a quiver would run thru my body. I moved closer and closer to that sissy nirvana where I didn’t need my penis to be touched in order to climax.
When I did start to spurt, I whimpered and then cried out blissfully and adoringly, “Oh my darling Alicia, I love you so very much!”
I screamed ecstatically. I couldn’t help myself. But the feeling of ultimate surrender was still yet to come. As Alicia finally pumped her warm ejaculate into my anus, the sensations were emotionally captivating. I’d never felt so rewarded as to take the seed of my lover into my inner being.
It was as if the warming from her semen went throughout my entire spirit and filled me through and through. At that moment, I was beyond being girlish. My essence was womanly, within every fiber of my being.
I slept the bottomless, satiated slumber of the pleasure ridden trollop. I only stirred when touched or fondled by my gorgeous lover. I had reached the shores of Lesbos. For now, I was uncertain I ever wanted to return. However, in the days, weeks and even months to follow, I would find a new direction and a new emphasis, through Alicia.
Even prior to my enrollment at Winthrop, I knew that many of the Winthrop Girls were already committed to a relationship with a wealthy, dominant, Cassandra Sister. Others were hoping to acquire a similar station, prior to or upon graduation.
I’d spoken to mother about it, and we were both of the same opinion. That, for the time being, if the opportunity arose, the ideal situation would be with a mature female living within a fifty-mile radius of the San Francisco Bay region. Just as my roommate Alicia once did, I’d never, ever considered, any sort of relationship with any member of the male sex.
That was out of the question, back then. But after many evenings of anal sex, when I looked at pictures of handsome male actors, athletes, or models, I would get a stirring in my loins, butterflies in my stomach, and a faint sort of lightheadedness.
When Alicia spoke of romantic, sexy evenings with her William, I would feel so excited listening to her. Mentally, I would imagine myself in such a sexual situation with one of the fantasy men from a magazine photo.
As my dress, speech and manner had become more and more feminine, so had my thought process. I was really becoming more and more like a girl, and more interested in men, every day.
As a marketing tool, all students at Winthrop had to do a publicity video for the school, as a promotion. Everything was carefully scripted and rehearsed. We were coiffed, dressed and made up perfectly. We talked about ourselves and the school. We spoke of our goals, our dreams and our aspirations.
In mine, I came off as a real girly-girl. I talked about how I liked being pretty, having my hair done, and wearing makeup and stylish clothes. I let the viewers know I loved cooking, doing housework and looking my best. The lady directing the video even had a couple of shots of me in class and walking around the campus.
The better and more interesting videos were usually shared with Cassandra Sisters on the Winthrop website, where only authorized members could log in. Apparently, that is where Diego viewed my video, thru Phyllis Demarche, a Cassandra Sister, whom he knew intimately and gave tennis lessons to.
Winthrop had no problem connecting a student with a carefully screened male, if the student was willing to meet him. Ms. Demarche contacted Winthrop on Diego’s behalf and Diego Iglesias went thru the very vigilant scrutiny of a Winthrop screening and background check.
It was quite lengthy. Extensive enough that my first year at Winthrop was nearly over when my counselor, Amber spoke to me about Diego’s apparent interest in meeting me.
“So, Babette. My first question would be, have you ever considered any sort of a liaison with a man? And by the way, Babette. Diego Iglesias is a very worldly cultivated man. He’s thirty-five. He’s a world class tennis star and professional athlete. And he’s been socially interconnected with any number of actresses, models and females of wealth, beauty and fame,” Amber winked.
“He’s not the boy next door. Now, personally, if it were me, that he was interested in, I’d be flattered to no end. He’s as handsome and manly as the day is long. So, I believe you need to talk this all over with your mother, Diedre. If indeed, you both are comfortable with it, you could contact me or Headmistress Lydia Faberge during the summer break,” Amber added.
“With our sanction, you could arrange a few casual dates, dinners, or coffee klatches, for you and your family to get to know Diego over the summer. That way you will know what direction you want to take during your second and last year at the Academy,” Amber said wisely.
I agreed with Amber, though I was still obligated to discuss it the following day with Lydia Faberge. It was agreed that I would contact Lydia, by cell phone initially, if mother and I approved of a meeting with Diego.
“So, tell me Babette. Which way are you leaning on this? I think that we wouldn’t even be talking about this if you were not interested in meeting him? Remember dear. You aren’t even twenty-one. He’s thirty-five and far more sophisticated than you. You know something Babette? I think you find all this terribly exciting, don’t you?” Lydia smiled.
“Yes ma’am, Ms. Lydia, I do. It’s all very exciting. And yes, I’d like to meet him. According to Ms. Amber he’s an absolute hunk,” I said, as Lydia Faberge, uncharacteristically burst out laughing.
“You mean you haven’t even seen a photo of him? Well goodness. Let me enlighten you. Here is one of him at Wimbledon two years ago. He’s with that American actress that recently married the Arab Sheik,” Lydia said, handing me a People magazine where they had a photo spread of him, and the actress together.
He was absolutely gorgeous! Very swarthy in a Mediterranean sort of way. Tall and trim, with rippling muscles. My penis was juicing, and my anus was twitching. I was determined to convince mother to allow me at least a couple of dates. I imagined she would at least want to meet him.
And the gorgeous actress? Looking at her, I wondered who did her hair, what sort of makeup she wore, and who designed her clothes? Sexually and romantically my attention was riveted on Diego Iglesias.
“You may keep the magazine, Babette. And you can be assured that Diego is well aware of your sexual nuances. You have a wonderful summer. Call me if indeed you want to meet him, and Deidre approves. I will arrange for Diego to contact you. Only phone Ms. Amber if I am unavailable,” Lydia added, before standing to hold and kiss me.
I could not wait to tell Alicia! When I did, she predictably freaked.
“Oh, my goodness! This is fantastic. With his winnings and his endorsements, he’s got to be fabulously wealthy. A multi-millionaire and set for life no doubt. And he’s a real playboy. He’s Spanish and raised by a really old school, very traditional Castilian family. That’s part of his interest in you,” Alicia said.
“So, you know of him also? I was just never into tennis. Baseball was my sport,” I chimed in and then paused. Wow. Playing baseball seemed like eons ago.
“I’d like to see you play baseball now. You’d be afraid to break one of your nail extenders. Yes, I know of him. He was ranked number one in the world on a few different occasions. Besides your great looks, I’ll bet he must have really been smitten with that girly-girl, style queen, trophy-girlfriend thing you’ve got going on. That’s what lured William,” Alicia added.
“Understand that William can have any female he wants. And he still does. He’s a handsome, wealthy surgeon. Nurses at the hospital fall all over themselves trying to get him into bed. He has come home on occasion smelling of another female’s perfume. But he came home. Plus, he got into my bed,” she said, wisely.
“It’s my job to keep him interested and I do. He doesn’t want a career girl. And he doesn’t want someone who wants a maid and who is going to sit around the house all day and watch TV and get fat. Sure, he has someone come in once a month to do the heavy cleaning,” Alicia added.
“But when he comes home at a normal hour, he wants me there, with a clean house, and a hot, freshly cooked meal. And he wants me there looking great, with a drink in my hand for him, ready to massage his feet and give him a blow job,” Alicia smiled.
“And at night if he wants sex, I’m ready for that. No matter what he wants to do. Career girls don’t do that. Sissies do that. So, if you plan on getting involved with a real playboy, know that you’ll have to do what I do. Tigers don’t change their stripes. I have the feeling Diego Iglesias is a real tiger,” Alicia warned.
“But, with what I’ve taught you, with what you’ll learn here next year, and your own natural instincts, you’ll know what to do to keep him interested. We need to stay in touch after I graduate this year. Come here. I want a big hug and kiss from my bitch,” Alicia ordered.
When the term ended for me, Alicia had already graduated. The goodbye was almost tearful for me, but Alicia told me that she didn’t want her bitch crying in front of William. So, I waited until I got back to my room.
After I arrived home, I waited for a few days to talk to my mother about meeting Diego. She looked at me, both interested and puzzled. She stared at me and remained silent. Then she spoke.
“Well, I am not completely surprised by this. At the holidays it was apparent you were becoming increasingly giddy and girlish. If you have now developed an interest in men, I see that as a natural progression. I have to add that I am quite impressed that a man so handsome, worldly and famous as Diego Iglesias has an interest in my daughter,” mother said.
“You do know who he is, don’t you? A world class tennis player and international playboy? He’s also fifteen-years your senior? I know your aunt, Laura and Anna will be very excited to find out about this. I would expect all of us to be very enthusiastic about meeting him,” Mother added.
“So, all of you have heard of him and I didn’t?” I inquired.
“Possibly because while you were busy playing and watching baseball, all of the rest of us in the household were doing the same with tennis?” Mother shrugged.
“Yes, it’s all okay with me as long as you are keen on this. I’ll break the exciting news to the rest of the household. Feel free to contact Lydia and tell her I send all my best,” mother closed.
The very next time everyone was together at a Sunday brunch, which we all attended at a local restaurant, mother made the announcement. My aunt, cousin and sister were all very pleased and surprised. Early that evening, as fate would have it, Diego called me on my cell phone around 6 PM.
I was in my room, going thru my wardrobe to see what to wear to mother’s business office Monday morning. I decided to lay on my bed to take the call.
“Well, hello Diego I’m very excited you’d call. Yes, of course I’m excited. Oh, you’re so cute. Dinner, well I’d love that. When? My entire family? There are five of us, you know? Oh, so Lydia did tell you? Yes, I’ll have to ask. Do you have a moment?” I said, walking from my room.
I found mother and aunt Delia in the living room and had to get Laura and Anna from their bedrooms. Then I made the announcement.
“Diego has asked if we could all have dinner at his home, next Saturday evening at 6PM? Or if another date would be better could we all pick one?” I asked.
It didn’t take long for everyone to agree on the date Diego had proposed. All I had to ask was what to wear.
“Well, please dress casually. We’ll eat in the dining room. I’ll hire a chef and his assistant for the evening, to cook and serve. We’ll have drinks. Just a nice evening where I can meet you and your family, and everyone can meet me. In the meantime, can I call and talk with you during the upcoming week?” Diego asked.
“Of yes, please. Of course, you can. And I’m very thrilled about dinner, Diego. I hope you don’t mind if any of us overdress. Ladies tend to do that when they dine with famous tennis stars. Don’t be modest. Of course, you’re famous. Yes, have a good evening. It was wonderful talking with you, Diego,” I closed.
We had some nice, insightful phone conversations during the week. I made certain to make a Saturday appointment with Gladys at “Delightfully Ambrosia.” I didn’t know about any of the other ladies in our household. But, if I was going to Diego’s for dinner, I would definitely be overdressed, elegantly coiffed and vividly made up.
If this man wanted a Barbie doll, girly girl, I was going to convince him that I was that girl. Alicia had already told me what it was like to be the pampered trophy girl of a rich man. All Alicia needed to do was keep herself beautiful for William, prepare delicious, wholesome meals for him, keep the home spotless and remain modestly silent unless spoken to.
If William had male friends over, Alicia would serve them and then leave the room, to allow them to discuss “Man things” in private. If there were other females present, Alicia was given permission to go into another room and discuss “girl things” with them. Never was she ever to discuss politics, sports, current events or finances. In fact, if the subjects weren’t beauty, fashion, housekeeping or recipes, Alicia was absolutely clueless and disinterested.
Of course, she was required to provide William with whatever type of sex he was fascinated in having, at any given time. She was never to question any of his liaisons with other females. I loved thinking about having this sort of one-sided relationship with a man, and I hoped that Diego would provide me with this sort of bond.
The best part was, as long as Alicia did what William required of her she was showered with expensive clothing, perfumes, jewels and any number of lovely automobiles. She had the carte blanche use of any number of credit cards to shop, go to the salon, or indulge in any sort of expense for herself that improved her appearance.
I giddily minced into “Delightfully Ambrosia” on the Saturday morning of our dinner date with Diego. I had booked my appointment with Gladys Millstone who was absolutely overjoyed to see me. She called me her “Little Babette Cheree” and welcomed me with a loving embrace and a kiss on the lips.
Her increasingly feminized step-son, Nikki, washed my hair. By now, darling “Nikki” was wearing high heels, heavier makeup and a flowered romper. I had to wonder what Nikki’s father thought of his progressively sissified son. Of course, at that time I didn’t know that Nikki’s “father” was Gladys’s feminized spouse, Candace, who doubled as her assistant manager at the salon.
Oh well. So much for that. Once Gladys got me into a cape and her styling chair she asked me, “So darling, what are we doing today? And by the by, dearie. I was speaking to my fellow Cassandra Grand High Matriarch, Lydia Faberge just yesterday. She tells me my little Babette is being sought out very aggressively by none other, then the former Wimbledon Champion, Diego Iglesias.”
“Bravo for you, young lady. I almost envy you. Though my tastes in males run to those who are very effeminate. Even as such, I must wonder if a roll in the hay with a manly stud-muffin like Mr. Iglesias, wouldn’t bring out the best in me on any given day? They seem to be taking very nice care of your tresses at Winthrop. The coloring looks recent,” she implied.
“Why not simply a light trim, and a nice, tight roller set, with setting lotion? If your date is tonight, a girly-girl, very curly style might appear very striking. What are you wearing my pet?” Gladys asked.
“I planned on four-inch, ankle strap heels, a camisole top and the briefest, tightest mini-skirt I can find. Of course, I’ll add in an uplift brassiere. Of course, very, very vivid evening makeup,” I smiled.
“Gracious me, you are going for the kill, aren’t you? Though, if Lydia was correct, all the ladies in your family will be present so I doubt you’ll see Diego’s bedroom, will you?” Gladys smiled.
Gladys took her time with my trim, as well as my very tight roller set. She loved chatting with her customers and friends. Once my hair was properly set on mid-sized plastic curlers, Gladys had me sit under a hot dryer. I sat and read the latest Marie Claire, as the pleasing scent of the setting lotion wafted around me.
During my comb-out, I asked Gladys some questions about a few procedures I was thinking about. “You do permanent makeup here, as well as collagen lip injections?” I asked.
“Yes. I would do the lip-plumping first. Then I’d try permanent lip color. You’d be surprised how much that would change things. Why don’t I put you down for the entire series of plumping and tattooing for your lips? I’m planning on doing my step-sissy Nikki and I could do both of you at the same time,” Gladys offered.
“Okay. Then who would you recommend for implants and possibly getting my nuts clipped,” I asked.
“Why don’t you talk to your mother’s GYN Eva San-Moritz? I’m sure her nurse-practitioner would counsel you on both procedures. Eva is currently giving my new sissy-wife Candace, massive injections of estrogen and testosterone blockers. If that doesn’t chill Candace out, then she will be getting castrated, herself. Candace gets a little snippy with me, now and then. I won’t tolerate it,” Gladys demurred.
“I didn’t realize that you were married to Candace, your assistant manager. Then she is Nikki’s father?” I asked, incredulously.
“She was Nikki’s father. I won’t permit Nikki to call her daddy any longer. She is now Auntie Candace and Nikki must call me mommy. Here at the salon, Candace calls me, Ms. Millstone. At home I insist she call me Master Gladys, or if I’m in the mood it is Grand High Matriarch Gladys,” Gladys laughed.
“There you are darling. A perfectly lovely, curly roller set. You’ll be the belle of the ball. Go home and take a nap. Wear a hair-net. You know how to fluff and spray it, before you go out. Have a lovely evening with Diego and your family,” Gladys said.
On the drive home, all I could think of was being in bed with Diego and I hadn’t even seen him in person yet.
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