Mrs. Iglesias: Chapter II: Bobby or Babette?

Priscilla Gay Bouffant

Chapter II: Bobby or Babette?

      As I have already said, I played sports in high school. Baseball, mostly, and I was pretty good. However, deep inside, I’d started to develop an interest in female clothing, makeup and hairstyles. My dad had taken off with his secretary and left mom, my older sister and me, on our own.
    We had moved in with mom’s older sister and our female cousin, who was older than both sis and me. No. Not one of them ever tried dressing me up, doing my hair or putting makeup on me.
    They didn’t have to. I’d get turned on watching them do each other’s hair, makeup, and getting ready for dates. They were not modest. One of the four would always seem to wander into a hallway, in a bra and panty set, or with a towel wrapped around their head and another around their boobs, coming out of the shower. It was a female dominated household.
    I had a part time job and began dating at sixteen. I began to realize that I really enjoyed it when one of my dates got into the car looking like she’d just stepped out of a beauty parlor. I’d always compliment them on their hair. They loved it. They told me how “sweet” I was to notice.
    In actuality I wanted to know if they’d went to a beauty parlor to have it done? I wanted to know if they had set it with curlers, or had a recent perm? I’d never ask though. Guys never ask questions like that. At long last, I decided to start dressing in women’s attire, privately.
   Living with my mom, sister, aunt and female cousin, meant there was plenty of ladies’ clothing, makeup and shoes, around to wear. I just had to find the time, when none of the four females were in the house. Plus, they’d have to be gone long enough for me to dress up, put on makeup and fix my long hair in a girly style.
    My big chance came, when the four ladies of the house took a week-long trip to a beach resort and I couldn’t get time off from my summer job. I actually lied about that. I could have gotten time off and went with them. I just wanted a week alone to find out what it would be like, dressing-up, putting on makeup and fixing my long hair up in a girlish style.
    My sister was the closest to my size, so I decided to use her clothing. I breathed a sigh of relief when I saw she had some stuff in one of the laundry hampers. It would be better than messing up her clean stuff. Then I’d have to launder it.
    I dressed the entire week in the same skirt and blouse and one of her rompers. I wore the same pantyhose with both outfits. I used some makeup my cousin had left behind, that she’d already been using. I had to wear my aunt’s high-heels, in order to find a pair that fit the best. The paramount event occurred when I washed my hair and set it on hot rollers.
    I’d already put lipstick, mascara and blush on. I had on a really, sexy bathrobe, belonging to my mom. It was hot pink, with ruffles at the opening. My auntie’s prettiest pair of marabou high-heeled slippers were on my feet. Looking in the mirror at myself with my dark blond hair in rollers and makeup on my face, I felt like a girl getting ready to go out on a date.
    I stood up and walked several steps to a full-length mirror. The heels on the marabous caused me to mince daintily and swing my hips. I preened and pranced effeminately in front of the mirror. The robe fell open to reveal my engorged penis. I looked sweet enough to eat!
    I reached to my penis and wrapped my fingers around it. I stopped, went back to the vanity and returned with some hand lotion. Pouring the hand lotion into my right hand I began to masturbate. I purred like a kitten.
    The feelings I got were better than any I’d ever experienced when being sexually intimate with a female. I just wanted, so much to be a girl at that moment. I started to fantasize about being dressed up and in some sort of bondage at a beauty salon.
    The women in the salon were forcing me to get a permanent wave. Then they were going to dress me as a maid and make me wait on all the rich, lady customers. I couldn’t control myself any longer. My sperm spurted wildly from my cock. It was the most awesome orgasm I’d ever experienced.
    My crossdressing “parties” continued for nearly a year. I experienced many, peaceful and erotic moments. But along with those moments came confusion and sometimes embarrassment. I became very talented with my hair and makeup. I’d purchased some books on those subjects.
    I also purchased books and had viewed on-line material on crossdressing. A lot of it made me feel better about my sexuality. Some of the material about submissive t-girls or “sissies” turned out to be pretty erotic.
    I kept my literature well hidden in my bedroom closet, along with the cosmetics and haircare products I’d procured at a beauty supply shop which was a good distance from our home. The following summer, my mother, my sister Anna, Auntie Delia, and our cousin Laura where all heading to Knotts Berry Farm for a week-long vacation.
    My sister and our cousin Laura were both finishing up their 2nd and 3rd years at separate colleges. Laura would be meeting mother and Aunt Delia at the hotel suite they’d rented. My sister Anna would be coming by the house first, before heading south. I had a crazy plan I’d hatched.
    I really wanted to get “caught” while dressed in female attire. I wanted some kind of closure and possibly support with my crossdressing fantasies. Recently, mother and Aunt Delia had boxed some women’s clothing to give to charity. I’d offered to drop the stuff off. From those boxes I’d procured a substantial wardrobe that I’d hidden in our attic.
    Then I’d taken the remainder of the attire to Goodwill. My plan was to be fully dressed, made up and coiffed when my sister Anna dropped by the house, before she continued on to Buena Park. To say my sister Anna was surprised when she saw me would be an understatement.
    I’d went all out that Saturday morning. “Babette”, which was the name I’d begun calling myself, looked smashing. I’d actually shaved my legs and used depilatory on the remainder of my body hair. I’d purchased some “falsies” to put in my brassiere. I had on a tight panty-girdle. I wore an A-line skirt, satin blouse, pantyhose, and two-inch heels.
    I’d taken such great care to get my hair and makeup perfect. My mascara was heavy, but just right. I used a soft foundation and rose blush. I painted on a creamy nude lipstick and pink eyeshadow. Because mother and auntie Delia had left the night prior, I’d set my hair and slept in rollers with setting gel, and a hairnet.
    I had bouncy curls all the way to my shoulders. I’d been growing my hair long and keeping it neatly trimmed at a hairstyling shop. When my sister Anna entered the house I casually walked from the kitchen to the living room, holding a glass of iced tea out for her. Smiling I set the tea down on the coffee table and did a twirl, showing off my clothing and my swaying curls.
    “Hello Anna. That’s freshly made iced tea if you’d enjoy some. How was the drive down? Do you like the way I look? Here give me a hug,” I said.
    She did give me a hug, just as I hugged her. Then she covered her mouth and looked at me questioningly. Shaking her head, she sat down and stared at me.
     “Bobby. Why are you dressed like a female? And how long have you been doing it? Because, honey, your makeup and hair look fabulous. I recognize some of the clothes also. Those are things we had packed up to go to charity. What’s going on Bobby? You can talk to me you know? Anna said.
    I sat down across from her and said, “Yes, I know I can talk to you Anna. Which is why I picked you to come out to, before I informed the rest of our family’s household. I’m dressed like this because I enjoy it, Anna,” I said.
    I’ve been doing it for nearly a year now. I just don’t know how to tell mother, Aunt Delia or Laura. I don’t want to hide it any longer Anna and I need to find out if this is who I want to be. Because I don’t know,” I sighed and whimpered.
    “Bobby, I understand. Mom and the rest of the family will also empathize. We’ll all help you to come to grips with this. Why don’t you give me a couple of days after we return from Buena Park? Then I’ll talk to mother. I’ll let her decide how, when and what to tell Aunt Delia and Laura,” Anna said as she walked over and embraced me, compassionately.
    When Anna did finally inform mother, it took mom a few days to discuss it between the three of us. At that moment in time Laura and Auntie Delia were out grocery shopping.
     “Bobby, the first thing I want you to realize is that there is nothing improper about wanting to dress as you do. In today’s society, this is much more normal and not so unusual as you might think it is. I’d also like you to hear that from a licensed, therapy professional,” she said.
    “I had a GYN appointment yesterday and I spoke of you to my Doctor, Eva San Moritz. She told me of a woman who specializes in counseling males who find comfort when wearing women’s clothing. I’d like you to see her. Her name is Gayle Broderick. Why don’t you let me set up an appointment?” Mother asked.
    I agreed with her. By the end of both my 1st and 2nd visits with Gayle Broderick I felt so much better. She wanted me to really get in touch with what she called my “inner girl”. She also wanted to do a session with mother and Anna, without me. I agreed.
    After that session she wanted to do another conference with the three of us, with me as “Babette”. I said I could go along with that. We picked an evening where Aunt Delia and Laura were going to a client’s home to take measurements and discuss a design and remodeling job.
    A few years after dad had left us, mother and Auntie Delia had begun a home interior and decorating business. They had become pretty successful with it. Since then they had hired another decorator, two sales people and three remodeling sub-contractors. During the summers, both my cousin Laura and my sister Anna worked with them.
    Mom took off from work early that afternoon. My sister Anna had come home at lunch to help me get ready as “Babette”. I had taken an indefinite leave of absence from the after school and summer job I had, to tend to “family matters”.
    The people I worked for had told me to contact them whenever I wanted to return to work for them. My sister Anna said she wanted me to look cute and sexy at the therapist office, but not too “overdone.” I began my preparations with a hot bubble bath. I shaved extra close in all the areas where I’d been using depilatory.
   After putting on body lotion and powder, I got ready to transform into Babette. Anna put me into a very tight waist cincher she would sometimes wear when she wanted to really define her figure. It was my first real experience with having to feel any discomfort to look really beautiful.
    For me, wearing that waist cincher, was one of the most femininely defining moments in my journey to emasculation. As Anna tightened and snugged the laces, I felt as if I’d been captured in this effeminizing web. A web, that was never going to release me, until I fully capitulated to it.
    Anna produced a more expensive set of life-like falsies and a new bra. The falsies had the added advantage of a mild adhesive to hold them in place. I didn’t ask any questions, but along with the very pretty, flowered brassiere she handed me, I suspected she and mother had been shopping.
    Anna then attired me in a panty girdle with garter straps. Shortly after, I slipped into real stockings for the first time, instead of pantyhose. The feeling of those silken stockings on my smooth, hairless legs, enlivened me from deep within my psyche.
    Anna held up and showed me, the loveliest skirt and blouse set. The blouse was white, with billowing sleeves and very snug, starched cuffs. It had a lace appliqued button front. At the front of the collar was a pert, black bow. The red skirt fit me as would a second skin. It snugged around my now slimmer waistline.
    It had a faux, waist-defining, black cummerbund surrounded by a red belt that tied with a cute bow. Both new pieces of apparel fit me perfectly, as did the new, three-inch heeled pumps I slipped onto my feet. I looked at Anna and asked, “Anna, where did all of this come from?”
    “Mother, auntie, Laura and I all pitched in to get you new stuff. All of what you have recently been wearing is going to charity, where it belongs. Mother is great with sizing. We weren’t certain about the shoes, but you don’t have a huge foot at all. In fact, for a boy of your height your feet are quite dainty,” she smiled.
    “Wait. Auntie and Laura know about this? Since when?” I asked, practicing my walk in the new pumps. The highest heels I’d worn until now were two-inch. These three-inch heels would take a little time to adjust to.
    “Since whenever mother had a talk with them. Relax, Babette. They’re very cool with everything. In fact, you might call them very excited. They can’t wait until the five of us go shopping together at Elaine’s Boutique,” Anna smiled.
    “Auntie Delia and Laura will be here to meet you as Babette when we get back from Doctor Gayle Broderick’s. We all want to dine together soon. We just have to come up with a restaurant where the possibility of someone knowing us is slim,” Anna said.
    “In any event, should we see someone that knows us, you’re Babette, my cousin visiting from San Diego. Everything is going to work out well Babette. You’re in our very strong, capable, female hands now. We’re going to take excellent care of our new girl, honey,” she smiled, giving me a hug.
    Anna continued with my makeup and hair. My hair was up in a wet set, with brush rollers. It still needed to dry a little longer. She had a lot of fun painting my face. With my dark blond hair, she wanted to use some warm, “autumn” tones of cosmetics.
    She began with a balmy apricot foundation. Then she blended in a deep peach blusher along with a tawny brown eye shadow. She used a rich rust mascara, before she blended my lipsticks. She went with a copper tinted lip-liner, and filled in between the outline, with a shimmery, terracotta tube of wet-look lipstick.
    I begged her to let me see myself in the mirror. I gasped. I looked like one, very sexy chick, getting ready to glam up for her boyfriend on a hot, steamy date. To me, up to this very day, there is nothing more arousing, then seeing myself in a mirror, fully made up, sporting a French manicure, along with my hair tightly put up in curlers.
    That day, just before my visit to Doctor Gayle, I still had my penis intact. I was never so glad to be wearing a highly restrictive panty girdle. It would have been embarrassing for Anna to see the boner that was trying to force its way thru my new skirt.
    My hair was still just slightly damp, and scented with setting gel, which was perfect for a blow dry styling, Anna had told me. She took the rollers out. While she blew my hair dry, she back-combed and fluffed it with a brush, for more volume. My tresses were now below my shoulders, although I was keeping them evenly trimmed at a hair-styling shop.
    Anna told me to close my eyes, so she could spray the cascade of curls that had developed from my tight, wet, roller set. When she stopped to pat everything in place, she had brushed all my hair around the back of my pate and over to the right side, touching my shoulder. She then pinned up everything on the left side with a large butterfly barrette.
    Anna stood behind me, her hands on my shoulders. I peered at my feminized self, as I looked into a full-length mirror. I was captivated and aroused by the reflection of the girl I viewed. I inhaled, “Oh, Anna. How did you ever manage to make me so very lovely and girlish? I could almost cry,” I simpered in my overwhelmed effeminacy.
    “Oh no, please don’t cry Babette? Never cry wearing full makeup. Here comes mother. Wait until she sees you, darling,” Anna smiled.
     My mother was overwhelmed by my appearance. I really think that was the day when we all three decided that we wanted to see more of Babette. Much more. As I sat in the empty waiting room, of Gayle Broderick’s office, I felt relaxed and composed.
     Gayle’s receptionist announced, “Ms. Chambers. You, Anna and Babette can see Doctor Gayle now.”
     Chambers was mother’s maiden name. She filed divorce papers for desertion when dad took off with his tramp of a secretary. After three years, dad was gone without a trace and mother reclaimed her maiden name. Under California law, she was entitled to give Anna and I the same name, and she did.
    Doctor Gayle was very impressed with how I looked, acted and spoke. Anna had been working with me on my speaking voice and using telltale feminine mannerisms. Doctor Gayle commented on my improved appearance and comportment and then asked some questions.
    “Well, Ms. Chambers, or Deidre. I know you said you preferred me to use your first name. How do you like your new daughter? And are the three of you and the rest of the family making any plans to see a lot more of Babette?” Gayle asked.
    “I know my sister Delia and my niece Laura cannot wait to meet Babette this evening. Yes. Babette has been a truly lovely, breathtaking, gush of fresh air for all of us. I hope she continues to polish and improve her appearance and her feminine comportment,” Mother replied.
    “Babette, I want to hear from you. How do you feel right now, and what sort of plans are you thinking of for your near future and beyond, darling?” Doctor Gayle asked.
    “Right now, I feel very safe, really loved and supported, as well as hopeful of exploring more of my feminine side. I’d love to remain as Babette for the entire summer. I know this coming school year, my last in high school, I’ll likely need to attend classes as Bobby. But after graduation I really intend to explore a life as Babette on a long-term basis. If I have the support of my family in that, of course,” I said.
    “Very good, Babette. What I see in your family, is a very nurturing, quite strong, all-female support system rallying around you. This is what you really need during this especially critical transitional stage which you are in. Before we hear from Anna, I’d like to hear from your mother Diedre, once again,” the doctor added.
    We all took turns speaking and the love and compassion I heard from mother and sister was just so encouraging. We put together some plans for the rest of the summer, my last year of high school, and the summer beyond. I would continue my sessions with doctor Gayle twice a month for the entirety of summer.
    Then, once a month during my senior year of high school. Arriving home, I was greeted lovingly by my Aunt Delia and her daughter Laura. I did a sassy, sexy twirl for them. I stood a little nervously as Laura circled around me.
    “Anna, what did you do to Babette? I know one thing. You’re giving me my next makeover. Babette, all the rest of the ladies in this household are keeping our boyfriends away from you, girl. You are going to be a heartbreaker,” Laura laughed.
    Getting into bed that night, with a green clay facial masque on, I felt the cool satin sheets and my silky peignoir against my smooth, hairless skin. I fell off to sleep and slept like a baby, waking up really refreshed. I listened to the chirping birds that morning and it was as if they were singing to me about the promise of tomorrow.