Jenny and I left the reception dinner and headed home to her house. On the way out, the same good-looking young valet helped me into Jenny’s car. As he was closing the door, he smiled, said his name was Travis, and handed me his business card. He once again told me how beautiful I was and asked for me to give him a call sometime. I felt so pretty and sexy that a total stranger would see me as a beautiful woman and, more importantly, would want to pursue me. The night had proven to be the first of many for me. Not only had I pulled off the masquerading as a drop-dead gorgeous woman and pleasuring another man’s cock, but I was also being hit on by the valet.
I shared with Jenny what had happened between Brad and me in the lady’s room after she left. I very much wanted Jenny’s opinion on the matter and what she felt about the way I was now thinking about the whole “becoming Rachel” thing. I had never dreamed of dressing up en femme, kissing, and going down on another man, but here I found myself. I felt somewhat guilty for sharing a very intimate moment with Sarah’s fiancé, but I really couldn’t control myself. I loved the way I looked dressed as Rachael and the freedom to openly express my long-time hidden and suppressed feminine emotions. It hit me that at twenty-two years of age, I had missed out on exploring my true sexuality my whole life. Yes, I had just pulled off the night as being beautiful Rachael, but where did this leave me now? I was both conflicted and excited at the same time.
Jenny said, “Wow, you did what with Brad? Holy smokes, Sarah would be upset if she found out you and Brad hooked up. She’s been hurt before as it is no little secret that Brad is a player and tends to cheat on her. After the last time, he swore he’d never do that again”
I responded “Well, he sure as heck didn’t think twice about taking me into his arms. He’s got a lot of charm; I just couldn’t resist. He is so gook looking, and his strong muscular body melted any thoughts of me saying no to him.”
Jenny laughed and said she did notice Brad was looking at me all night. She also thought that Sarah had noticed, but she didn’t say anything to her about it. I told Jenny that I now had thoughts of Brad taking me sexually as a real woman and I couldn’t stop thinking about his large firm cock; what was happening to me?”
Jenny said I wasn’t wrong for thinking this way as I had completely dived into the en femme experience. For all intent and purposes, I was no longer the weak and pathetic Mark, I was now truly the young, vibrant, and sexy Rachael that I so much wanted to be all my life.
Once at Jenny’s apartment, we changed out of our formal dresses and slipped into matching pink and white-laced negligees. At Jenny’s insistence, she had me remain all dolled up as part of my continued feminization training. I certainly had no problem with that as I so much enjoyed my new persona. We retired to her living room couch and talked as sisters often do. We chatted about tomorrow’s wedding and what I was going to do regarding Brad. Jenny was torn between telling me not to act on my feelings for Sarah’s benefit, but her knowing that I very much wanted to be a woman, she also wanted me to further explore being a woman with Brad.
As I lay in bed, I relived the evening’s events. Being all dolled up, having Brad’s body pressed up against mine, our tongues probing each other’s mouths, and taking his massive cock deep into my throat was intoxicating. Jenny entered my room to say goodnight, and as she was walking out of the bedroom, she placed a small box on the dresser. She smiled and said, “Enjoy, my little sister. I got this little gift for you and saved giving it to you for tonight.”
Once she left, I opened the box to find a dildo and a bottle of strawberry-scented lubricant. Gosh, Jenny sure thought of everything. The fake cock was just over eight inches in length, had a good size girth, and had life-sized testicles. I lay back in bed, and once again thinking of pleasuring Brad’s beautiful cock and swallowing his cum drove me wild. I removed my satin panties and applied lubricant to my index finger. I gently inserted it into my rectum. It felt odd to have a foreign object in my bottom, but I imagined it was Brad’s finger working my hole. I then took the dildo and started sucking on it as I placed two fingers into my hole. The lubricant was heat-stimulating and it felt wonderful. I took the cock into my mouth and began practicing as if I was sucking a real cock. I slowly worked it past my gag reflex to replicate deep throating a real cock. The dildo and Brad’s cock were similar, but the feeling was not the same. A real cock had a heartbeat, smelled musky, tasted so good, and climaxed. But this was the next best thing, and I had Jenny to thank for it.
I removed the cock from my mouth as I was confident I could easily deep throat another cock with little difficulty. The motivation to learn this would have surprised me earlier in the month, but after three weeks of intense feminization training, I was showing a lot of progress. I was very eager to quickly master the art of sucking and taking a man’s cock. With that thought, I lubed up the dildo and placed the head at my bottom’s entrance. I pushed the cock ever so slowly into my rectum. I felt a little resistance and some discomfort, but steady pressure and my willingness to learn this drove the head past my sphincter muscle. I held my breath as the feeling of discomfort slowly subsided. I proceeded to push the cock into my ass.
I was surprised at how easy it now went all the way in as if my ass was sucking it in. The whole cock was now deeply inserted with the testicles firmly pressing up against my ass cheeks. I massaged the balls as if they were Brad’s. Oh, how I would love to have my ass filled with a real man’s cock. I then began working my ass with the fake cock. In and out I penetrated myself for about five minutes, repeatedly hitting my prostate gland. I was surprised when my totally limp little cock started to spurt cum as I climaxed into a wonderfully pleasing orgasm. I reached down and cupped my penis to collect all my hot cum. Holding the cock steady in my ass, I fed all the cum into my mouth. Thinking the whole time it was Brad pleasing me, I swirled the cum with my tongue for a while. I so much enjoyed the taste and consistency of my seed. I imagined Brad ordering me to swallow his come and, in a few gulps, I swallowed every drop. I quickly fell asleep with the cock still in me and the happy thoughts only a true woman could have.
I woke the next morning and took a long hot shower. Afterward, Jenny came in and asked if I experimented with her gift. I smiled and said it was truly amazing and I loved every minute of it. She then went over to her vanity and came back with a douche kit. She had me get on all fours in the tub and asked me to trust her. She said all good girls need to clean themselves properly after a good ass fucking.
I said, “Jenny, I have always trusted you, so... What do you have in mind?” With that, Jenny took the bottle and attached a long hose, and told me to slightly spread my legs. She lubed up the applicator end and inserted it into my bottom. The thin lubricated hose easily penetrated my rectum and made its way deep into my bowels. Then, Jenny told me to relax as she released the liquid from the bottle. She instructed me to hold all the liquid until she gave me permission to release it back out. Once the bottle was empty, my ass was filled and the urge to release became tremendous. I held it for a little while longer and then Jenny gave me the go to dump the liquid.
The feeling of release was nothing like I had ever felt before. The warm liquid shot out of me and left me with a totally clean rectum. Jenny said if I wanted to take Brad’s cock tonight, I’d be all ready to enjoy the experience. Jenny was such a gem and I thanked her for her instruction.
I shaved my body again and prepped it with a good dose of floral scented beauty cream. Jenny instructed me to come into her room where she had laid out all my foundation lingerie. There were nude stockings, satin waist cincher with garters, gaff, and a matching strapless satin and lace bra. I put everything on and then Jenny inserted my 32B silicone breast forms. Having the fake breasts gently tug on the strapless bra felt wonderful. Their position and size were very proportionate to my slim frame and once again, with the stain cincher fully tightened, gave me that very desired hourglass figure.
Jenny had me put on one of her long baby blue silk robes to cover up while she got ready. I fixed a few mid-morning mimosas as we chatted about the day’s upcoming events. Once Jenny was dressed in her undergarments, we helped each other into our maid of honor and bridesmaid dresses. I loved the long flowing satin sleeveless dress with a thigh-high slit and one shoulder strap. I felt like a Greek goddess and couldn’t help but stare in the mirror at how the dress accentuated my long thin legs and slim waistline.
I then sat down at the vanity, slipped on, and laced up my silver high-heel sandals. The five-inch heels were now a breeze to walk in and I loved how they lifted my firm little ass and rotated my hips forward as I walked. When Jenny was done, we applied our perfume and headed toward Sharon’s boutique for our hair and makeup sessions.
Sharon met us with a warm smile and immediately had Jenny and me sit down at her dual-station makeup station. Sharon said she would do my hair and makeup and Victoria, a new girl, would do Jenny’s. Sharon was an expert and began working foundation and concealers onto my face. She prepped my face for what would be another hour of total beatification. She tweezed my eyebrows further and showed me how she was able to arch them without losing volume. She filed them in with an eyebrow pencil to set the nice feminine arched look. She worked dark and light green eye shadow and finished my eyes off with silver and gold glitter to both highlight and match my dress. She then deftly highlighted my eyes with a heavy coat of eyeliner, and mascara, and then attached thick false eyelashes, followed by more mascara.
Next, Sharon, using a dark red lip liner, exaggerated my lips contours to give me thicker and fuller lips. I loved the feeling of being made up. Sharon then carefully applied a matching lipstick. She finished them with a clear gloss coat and told me to press down on a napkin to set everything into place. She then applied some blush to further define my already angular cheekbones. Sharon then attached her signature gold-hooped earrings to complete the look. I wasn’t permitted to look into the mirror yet, but I knew the finished work would be truly remarkable. My heart raced with anticipation to see beautiful Rachael emerge once again.
Sharon then began to truly work her magic by attaching real hair extensions to my existing hair. She started with the top and back of my head and weaved in about twenty-one inches of beautiful long auburn hair. Then came the front and side sections and when she was done, she said no one would know that all the hair wasn’t really mine. She then began styling my hair as the bridesmaids had all agreed to have a French style half up and half down updo. Sharon spent considerable time braiding, curling, and setting my super long and flowing hair atop my head. She left several curly tendrils gently tangling on each side of my face. They served as a reminder of just how ultra-feminine I looked. She weaved in a thin strand of silver and gold beads that matched the earrings and soon-to-be-worn necklace.
After Sharon set my hair, she finally allowed me to look in the mirror. I was truly stunned. Yesterday, I looked like beautiful Rachael; today, I looked like a goddess who had been blessed with spectacular beauty. I really was speechless. The thought that immediately entered my mind was I never wanted to go back to being Mark. I decided then that I’d have to do whatever it took for me to live like and be Rachael. Jenny just stared at me with an open mouth and exclaimed “Oh my God, Rachael, you are the most beautiful woman I have ever seen; I am just simply jealous.” We both giggled sillily as Sharon had us move on to having our nails repainted to match our darker lipstick shades.
I stood in front of the full-length mirror and took in every aspect of my appearance. Totally unbelievable! There are woman impersonators who don’t look as real or convincing as me. I was very happy that Jenny had asked me to do this for Sarah. If it weren’t for Jenny’s insistence, I would have never realized just how powerful my suppressed feminine desires were. Now, I was letting my true self rise to the top and honestly, I didn’t care what anyone would think if they knew I was a man. Today, I would go to Sarah’s wedding and play out my fantasy of being a beautiful bridesmaid. I did have a thought of what it would be like to be a bride someday, but perhaps, that would be for another day. I first would have to find a boyfriend and experiment with dating and learning how to pleasure a man in every way a woman would. I had so much to now look forward to and I loved every bit of being Rachael.