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.

Sharon finished off the makeover by having me put on a long, beautiful necklace to match the hair jewelry. It gently lay on my open chest just above the alluring cleavage created by my breast forms. Sharon had shaded a little bit of rouge to the inner edges of my breasts to enhance the appearance of cleavage. Sharon then had me put on some dangly bracelets on both wrists and a few delicate rings on each hand to complete my jewelry.

Jenny and I both thanked Sharon and as it was now 2 pm, we headed over to the wedding venue, which was at the new town hotel and convention center. We valeted Jenny’s car and made our way to the receiving area where all the other wedding party members would be gathering. The hotel staff had drinks and light snacks for us and immediately Jenny and I had some champagne to loosen up a bit. After four hours of getting dressed and made up as gorgeous women, we were glad to relax and have a light conversation. Jenny and I were by far the most beautiful of all the women present. We both received plenty of comments on how we looked and how everyone felt our beauty would overshadow that of the bride.

Sarah was still in the hotel’s salon getting ready and her mother said she would be done in about an hour. Jenny and I continued to mingle and had a few more drinks. The groomsmen arrived and I caught a glimpse of Brad walking in and making his way over to the bar area. He turned and looked in my direction and I caught him doing a double take. He couldn’t hide his excitement at seeing me. His reaction gave me a warm feeling deep inside and it served as affirmation that he was very much still attracted to me. It didn’t take long for him to work his way over to me.

“Hi Rachael, I’ve got to say, you’re a major distraction for me today. I will also admit, that I had a hard time falling asleep last night as you were in my thoughts. Yeah, Sarah and I left the reception together, but as she felt it wasn’t right to see each other this morning, she ended up sleeping alone at her house. Is it wrong for me to admit I fell asleep to thoughts of kissing you and holding you in my arms?”    

I smiled and responded, “Well, based on what we did last night in the lady’s room, is that all you thought about?”

Brad blushed and said, “Well, I’d be lying if I told you no because I thought about doing a lot more with you, but I’m trying my best to be gentlemanly.”

I giggled and said he should only be thinking about his soon-to-be wife, especially on his wedding day. Brad blushed again and said a man isn’t tied to one woman until the rings on his finger. Well, that may be technically true, but it was morally questionable.

“So,” Brad said, “Did you think about me?”

“Yes, I did, and it wasn’t just about us kissing. I couldn’t help thinking about anything else other than your hard cock.”

Brad laughed and said he thought so as he felt I enjoyed our brief, but very intimate time together. How right he was.

“You know Brad, I was thinking if you weren’t going to get married, how nice it would be for us to date because you are so much my type. It’s a shame you are someone else’s man.”

I could see Brad quickly thinking. He leaned in closely and whispered in my ear, “Well, the wedding isn’t for another two hours, how about you meet me in ten minutes upstairs in room 505. I’ll be waiting for you and if you’re up for it, we can be alone for a while.”

I looked over at Jenny and she just smiled and gave me an almost imperceptible head nod of approval.

Brad disappeared into the crowd, and I quickly finished my drink. What would be the harm I thought? He was right, or at least my selfish sex-craved womanly mind was telling me it was right. I decided I would go for it, I would let Brad have his way with me, one last time before he was no longer available.

I made my way with clicking heels to the rear lobby elevators, stepped inside, and with my heart beginning to race, pressed the button for floor five. My heart increased the closer I got to room 505. I lightly tapped on the door, and I heard Brad instruct me to enter. I pushed open the door and stepped into his room. He had pulled the shades shut and with just a few tall skinny candles flickering, I could see him standing by the bed. He walked over and without any hesitation, wrapped both arms around my waist and pulled me into him. Our mouths met and we began kissing intensely. His tongue worked its way around mine and for a moment, I felt as if I was floating.

I interlaced my hands around Brad’s neck and leaned into his strong and firm body. I immediately felt his huge cock straining against his trousers. I was so into the moment, alone with Brad, in a dark room, and having him get ready to have his way with me. Our kissing became more intense as I reached down and started massaging his cock through the material of his pants. He moaned deeply as I squeezed his throbbing member, and I knew it was time for me to release his sweet cock. I so much wanted to taste him and take him deep into my mouth. I pushed Brad onto the bed, and he willingly complied by unbuckling his trousers. I lowered the zipper and pulled his trousers and boxers down and off his muscular legs. 

Brad’s cock was standing fully erect and just waiting for me to pounce. I snuggled up onto the bed and began softly kissing Brad’s mouth and neck. The whole time we kissed, I gently caressed his cock and balls. He was completely shaven, and I loved the smoothness of his skin. I switched to Brad’s shirt and unbuttoned it, now exposing his massive chest and well-defined abdomen. He was a hunk that could easily have been a male model if he had chosen that profession. I rolled on top of him and commenced kissing and nibbling on his body. I slowly worked my way down to his lower abdomen and I could tell Brad was fully enjoying my touch.

He said, “Rachael, you are so hot, I can’t believe we are actually doing this, please don’t stop, I want so much to have you suck my cock.”

I continued my nibbling and kissing, getting lower until my mouth was on his pubic bone. I stroked his cock with my hand and Brad’s penis started producing precum. I pinched the head of his cock with two fingers, grabbed a glob of precum, and placed it on my lips. I liked my lips and said, “Are you ready Brad to feel my hot mouth on your cock?”

“Yes, Rachael, please don’t make me wait, I want you to suck me.”

Using my tongue, I slowly licked his entire shaft from base to head, stopping every few inches to kiss the edges. Brad loved this as he moaned even deeper, and his breathing became quicker.

I grabbed his cock to better control it and opening wide, lowered my head onto his shaft. I sucked on the head of his cock for a few minutes and extracted all the precum; he tasted wonderful.

Having recently practiced on the dildo Jenny gave me the night before, I wasted no time in lowering my head onto his entire shaft. I relaxed my throat muscles and took Brad’s full eight inches of firm cock deep into my throat. I held him there for a few seconds before releasing his cock and then taking him back into my mouth. I slowly picked up the pace and with my other hand, began massaging his balls.

“God, Rachel, you’re killing me, at this pace, I’m going to come quickly.”

I eased up on my sucking and deep throating.

I released Brad’s cock from my mouth and said “Brad, would you like to fuck my ass?”

“Oh, baby doll, yes, please, let me fuck your ass, I want you so bad.”

I got off the bed, reached down, and pulled off my gaff. I told Brad I would keep my dress on as I didn’t want to mess with undressing and redressing. Brad went over to the nightstand and produced a bottle of lubrication. Did Brad plan that for use on Sarah or did he anticipate using that on me? Either way, I didn’t care, now was the time for Brad to fully fuck me like I had been thinking and dreaming of since yesterday.

Brad instructed me to get on all fours on the bed. I willingly complied. I reached under my dress hem and grabbed my small penis and balls and moved them forward. I lowered my chest and shoulders onto the bed and lay my head sideways on the pillow.

Brad nestled up behind me and draped my dress hem across and to one side of my back. My heart was pounding with anticipation and excitement. My only concern was if Brad’s massive cock could fit into my small little ass. Brad used the lubricant to grease up his head and shaft. He squeezed a good amount onto my hole and using one finger, worked it deep into my rectum. He probed my ass with his greased finger like he was a professional. Since I had stretched out my bottom last night pretty well with the dildo, I was confident I could at least get his head past my sphincter.

“Are you ready, Rachael?”

“Yes, I am, please fuck me, Brad, I can’t wait any longer.”

With that, I felt Brad’s head of his cock pressing past my sphincter and entering my rectum. I was surprised at experiencing only slight discomfort, but now Brad was easily in and pushing deeper into me. His cock felt so much nicer than the lifeless dildo. I felt his soft, smooth firmness, and warmth as he penetrated me deeper. Oh, God, I was in heaven.

Brad said, “Okay, my baby doll Rachael, just relax, I’m going to pick up the pace and as you’re feeling so damn good, I hope I can last more than a few minutes.”

Brad wasn’t lying, he picked up the pace considerably. I was amazed at how deeply he was fucking my pretty little ass. I was taking every inch of his throbbing cock and I couldn’t have felt more feminine. Girls have it so good. They can suck cock and receive cock anytime they wanted. Brad reached up and placed both his hands on my hips. He was no longer being gentle with me; he was hammering away at full speed. Brad’s breathing intensified and I felt him quickly approaching orgasm.

“Hey baby doll, how about I come in your mouth, so I don’t leak all out of you during the wedding.” Wow, Brad was being so considerate, and as I truly wanted to taste and swallow his seed, it would work out perfectly having him shoot his load into my mouth.

“Okay, Brad, I would love that, let me finish you off with my mouth.”

I rotated around on all fours and took Brad’s cock back into my mouth. This time, Brad took full control and holding my head on both sides with his hands, he began fucking my face. I breathed steadily and easily allowed him to deep throat me again. After a few minutes, Brad pulled out, grabbed his cock, and began jerking himself to orgasm. He told me to open my mouth and seconds later, he shot four large size spurts of hot cum expertly into my waiting mouth.

Before I could swallow Sarah’s man’s seed, Brad reached down and lifted me up. Our mouths met and we shared a very intimate French kiss. Our tongues swirled Brad’s cum around before both of us swallowed every drop down.

“God, Rachael, you are totally amazing, I can’t believe I came so fucking hard. I think I can’t live without this kind of sex.”

What did I just hear, Brad was loving me sexually, but he was about to tie the knot with Sarah. This would have to end for sure, even though I certainly wanted to explore and experience much more with him.  

We pulled ourselves together and we both freshened up before heading back to the wedding party. Before leaving the room, Brad asked if I could be his mistress. Deep down, I was conflicted because Brad still thought I was Rachael, not Mark pretending to be Rachael. How would that work, if we continued, eventually he would discover I was a man. But I had done some soul searching and decided I wanted to start my full-time transition to becoming Rachael. With Jenny’s help, she could help me navigate the complexities of becoming a real woman.

“Brad, I would very much like to be your mistress, but there is something I have to share with you, I am not who you think I am.”

Before I could speak another word, Brad placed a finger on my mouth and told me he already knew that I wasn’t a real woman. He said he figured it out when he saw that Jenny and I looked a lot like each other. He knew she had a twin brother and suspected I had filled in to be one of Sarah’s bridesmaids. He said he was turned on by the fact that I looked like a woman but was a man. He said he would continue to see me if I wanted. I shared with him my desire to become a real woman and he said he would support me in any way he could. I was so relieved and happy at the same time. Now, I could have Brad’s cock, or any other man’s cock, anytime I wanted.

So, in the end, Brad wasn’t so bad after all. He had some things to work out with Sarah, but until then, I would be at his beck and call, and I looked forward to servicing him sexually in whatever way he wanted. I would work on my transition as planned and hopefully, with Brad’s continued sexual encounters, and Jenny’s sisterly advice and help, I’d truly become Rachael.