My Wedding Datebycubsrule1972©
It all started as a bet. A high dollar bet. I worked in the advertising business in graphic art. I'd always been a creative type. I was single and living the high life in the big city. The business I worked for was making great income so I was paid well and my bosses were always throwing money around. I was going to clubs about 5 nights a week, meeting plenty of girls and getting laid a lot. LIFE WAS GOOD.
One day in the break room at work a co-worker named Darren was talking about a wedding he had to attend the following month in Seattle where he wasn't going to know anyone but the groom. He was worried about being bored silly but he was single and didn't want the baggage of taking a date.
I listened and said, "just take a friend...I'd love to see Seattle." He laughed and said taking a guy wasn't exactly the right message he wanted to send to people he didn't know. I shrugged it off and went back to work.
Later that afternoon, my boss Jen called me into her office. Darren was in there too.
Jen smiled at me and said "I have a proposition to get you to Seattle with Darren." My eyes widened, and I asked her to explain.
She paused and then began. "You know how Darren's boss and I are always making a little friendly competition. I heard your conversation about going to Seattle and had a crazy idea. I think I could teach you to dress and act like a girl and make you passable enough to be Darren's date. Darren's agreed to the idea."
My immediate response was "You've got to be kidding Jen. I don't want to see Seattle that badly and if you haven't noticed...I'm a man."
Jen then shocked me by saying "I have twenty thousand dollars riding on your ability to pass. I'll cut you and Darren each five thousand of that if you pull it off."
Bewildered, I just stared a minute. I'd never thought about dressing like a girl. I certainly wasn't gay and knew Darren wasn't. Then my creative juices started to flow. I DID want to see Seattle and would do it nearly cost free this way PLUS an extra $5k cash if I pulled that off. How bad could it be? I looked at Darren and he nodded approval.
I looked back at Jen and slowly said "Ok Jen. Let's make some cash"
Over the next month, Jen came over to my apartment several times. Initially she brought shoes, dresses, and makeup. We went over a more feminine walk, getting comfortable in a dress, talking like a girl, and how to apply makeup. I struggled with the shoes most of all. Heels are hard to walk in but I knew I had to pick it up if I was going to pass. She also gave me the female name of "Amanda" and began to use that solely during our sessions.
As the wedding weekend grew closer, Jen started to work with my hair. Fortunately, I have blond hair that I wore in a tail at the time. She helped style it with more body and a more feminine look. The rest of my body was thin of build but with about 10 extra pounds that situated near my hips and butt. I didn't have hair on my chest or back but did of course on my legs which she had me start shaving regularly.
The Thursday before the wedding Jen came over for her last session.
Arriving, she said "Ok Amanda. We've covered walking, talking, your hair, your makeup, your dress, and your name. But we haven't covered what's going to be under that dress." She reached into her handbag and pulled out a set of false breasts. I looked at her skeptically but she said without any breasts at all, my dress wouldn't lay right and I'd fail for sure. She explained the cocktail dress she'd chosen went high enough toward my neck and had enough on each sleeve that these forms wouldn't show at all. I realized she was right so I took them and the bra she handed me.
I removed my shirt and fumbled with the bra.
"Here, let me help" Jen said. She showed me to place the bra to my chest and reach back to fasten it. Then insert the forms. I looked down at my new rack.
"B-Cup?" I asked.
"No, C, nice ones I might add" she replied, which made me giggle. Then she went to her bag again and to my surprise pulled out a garter thong and stockings.
"What? Why do I need hose of any kind?" Jen asked me to trust her and explained I needed the hose to keep my legs feminine, the thong to help feminize my butt and that true pantyhose would distract from the thong's effect. Hence, the garter and stockings. Grudgingly, I put it all on and came back to the living room feeling very immodest.
Jen looked at me and said "wow, you just might get lucky Amanda."
"SHUT UP!" I told her laughingly. "This is for $5k and a trip to Seattle". She just shrugged and laughed.
After that I tried on the cocktail dress, slipped into my heels, and did my makeup and hair. Looking at myself in the mirror I really was impressed and for the first time began to believe we might win the bet. While looking at myself, I heard Jen open my front door and say "Hello Darren."
For a moment I panicked before it hit me that he would be my "date" to a wedding while I was dressed just like this. Nervously, I walked back to the living room.
Jen looked at me and said "Darren, I'd like you to meet your date Amanda." Darren was clearly taken aback. I think he expected to see me as I look at work with maybe a touch of makeup and a skirt. It took him a minute to even say hello. In his eyes I thought I saw a bit of attraction even. Strangely, it didn't creep me out. I kind of liked the control I had.
Jen said "ok lovebirds, the last part of my planning is making sure you guys can walk and dance together." She worked on walking with me on Darren's arm and then some slow dancing. I was uncomfortable as the woman in a dance, but found it easy to follow his lead and we kept it all pretty basic.
Finally Jen looked at us both and said "my work here is done. Good luck and bring home the prize."
After they both went home, I packed up everything she'd given me and went to bed, excited for the trip but terrified for being a woman in public.
Darren and I flew out the next day. I was travelling as a regular man so it looked like two co-workers travelling together. We got in late and night and checked in. I thought about going out for the night but decided to get rested. The wedding was at 2pm the next day. We weren't sharing rooms so I had a peaceful slumber. The next morning, I started to get ready.
Unpacking my wedding attire, I noticed a plastic bag I hadn't packed. Pulling it out and opening it, I saw it contained a red silk babydoll and a note from Jen. "Amanda, one last tip. Shave everywhere and here's a little gift just in case you feel extra feminine at night."
"Good God," I thought in frustration.
After unpacking everything, I showered and did shave everywhere. I normally shaved my pubic hair so that part was easy. I also shaved behind my balls and up my ass and gave my legs a fresh shave to silk them up. I pulled on my garter thong and bra and then sat in front of the mirror to do my makeup and hair. The makeup was fairly basic to avoid complications but I had a nice eye shadow, eyeliner, foundation, blush and of course red lipstick. Happy with the results I watched myself in the mirror as I fastened on a necklace, bracelet and earrings (both ears were already pierced, making that part easy) and then pulled up my stockings. I have to admit, I did look sexy. Finally, I stepped into the light green dress and my heels. Looking for flaws in the mirror I began to really feel feminine. I reached up to touch my breast and gave a pouting look to myself. I was ready to tackle the challenge and called Darren to tell him.
He knocked on my door and when I opened it he again had a look of shock.
"You look great Amanda." I smiled and told him he did as well.
Darren is a good looking man at 6'2" with short brown hair, deep blue eyes, and an athletic body. He was in an olive suit that fit him well and it made me feel good to know he found me attractive as a woman. Taking his arm, we walked to the elevator and into my first public outing.
We took a cab to the wedding and I swear the cabbie was giving me eyes. Stepping out walking into the church, Darren kept me close by. We were seated by the usher and so far so good. As we sat and chatted, Darren took my hand and held it. We'd discussed wanting to look like we were together and this was part of that role. The wedding itself was nice and very romantic. Most of the lady guests were sitting close to their dates and though it sounds cliched, love was in the air. I even felt a bit like a date in love myself.
After the wedding we had a drink in the hotel bar before the reception started. We both agreed everything was working well and that we just had to keep it up. Gathering courage once again, we headed to the reception. The first real test for me was meeting Darren's friend the groom. He of course wanted to know all about Darren's date, how we met, how long we'd been together, why Darren hadn't told him about me, etc. Between laughing and teasing, I think we passed it all.
Early on then, the reception was a bit dull. We were seated with some older couples and other than one of the men staring at my chest, it was pretty uneventful.
At one point Darren whispered in my ear, "after a couple dances, you can go upstairs if you want. I think we've won the bet." Feeling released and excited, I found myself loosening up a lot.
I excused myself to go get a drink and while ordering, felt a hand on my back. I turned and it was Darren.
"Hey, I had to get out of there for now too. Our table sucks."
I laughed in agreement and then handed him his drink. I realized then he hadn't moved his hand from my back. He sat on the stool next to me and kept it there while he took a drink. I figured we'd stick with appearances as well and placed my hand on his leg giving him a wink.
"We pulled it off didn't we."
"Better than I ever dreamed" he replied as he smiled and stared into my eyes.
For just a moment I really felt like he wanted to make a move on me, but snapping into reality I moved my hand and said "the music is starting, we should go back in and dance."
They started with a cheesy slow song and Darren and I danced on the floor with all the other couples. He held me close to him and we just moved together not talking. I began to realize that his move in the bar had been true attraction, even if it was subconscious. Now his hands strayed lower on my back. I was so torn between melting at his attraction but knowing and feeling like the man I was.
When another slow song came on and we maintained our positions, I whispered in his ear, "are you trying to get lucky here?" and smiled at him.
His slow reply was "I've just never had such a sexy date to dance with."
With that, I did melt and leaned in to give him a quick peck on his cheek. He smiled back at me and then gently lifted my chin and slowly kissed me on the lips. Though nervous, and confused, I found myself liking it. A lot. His lips were coarser than girls I've kissed and had a salty taste to them. His hand then completely crossed the curvature of my butt and I began to realize I was his date, his girl and that I wanted him sexually, as a girl.
As the song ended, I pulled away from him and said "I'm going to take you up on that offer and head upstairs." He looked crestfallen as I turned and took a couple steps.
Turning back I said "aren't you coming?"
He gave the biggest smile I'd ever seen from him and walked to me. With his arm around me we entered the elevator and as soon as the door closed he kissed me again. I kissed back with more passion this time, amazed at how badly I wanted to keep kissing him and more.
We got to my room and I pinned him against the wall in a deep passionate kiss. Our tongues intertwined and my body was rubbing against his.
He reached behind me and started to part my dress over my shoulders. It fell to the floor and I felt exposed but sexy to him. He kissed me again as his hand moved to caress my breasts. Suddenly, I remembered the babydoll Jen had packed for me and wanted it.
"Darren, let me change into something for you. 10 seconds." I quickly slipped into the babydoll, taking my breast forms and placing them in as well. I left my corset and stockings on. I walked back and as I approached him, his desire was apparent.
"Do you like it?" I asked.
"I want you" was his simple reply.
I kissed him again and began undoing the buttons on his shirt. He was not wearing an undershirt and I rubbed his firm chest with my hands. He leaned his head back and inhaled deeply. That gave me an opening to lean in and lick his chest. God it was sexy. Light brown hair that wasn't thick. He rubbed the back of my hair and moaned my name.
I realized what came next and I was ready. I slowly pushed him to seating in the hotel room chair and then followed him down ending on my knees. Kissing and licking his stomach I reached for his zipper. Like Julia Roberts in Pretty Woman, I unfastened his pants and gave his legs a tug to get his crotch in a better position. Then I reached in and grabbed his cock. Darren gasped at my touch. I pulled his cock out to view and figured it must have been 7" long. Much bigger than mine. As I lowered my head to it, I thought "you go girl" and with excitement, I led the head into my waiting lips for my first taste of cock. Like the rest of him, it had a more salty taste than girls. His smell was masculine but pleasant.
His breathing accelerated quickly as I started to slowly slide up and down like girls have done to me. My left hand moved to caress his balls. I was only able to take about 4" before I was afraid of gagging. He didn't seem to mind as his breathing and moaning continued. He also began to rub my hair with both hands. God I was 100% girl. I wanted to satisfy him. I picked up my pace and could tell he was getting into a rhythm with me. I wasn't sure if he was going to cum in my mouth but as his breathing got shallow and his hips started to buck, I had my answer. I braced myself, and he exploded into my mouth. The taste was as I'd heard, subtly sweet, and oyster salty. I swallowed all of it and then kissed his cock as he slowly got his breath back.
I lean up and rested my head on his belly. After a moment or two, he pulled my head up and kissed me deeply which made me happy since I'd just swallowed his semen. He pulled me to my feet and led me to the bed and laid me down. He then laid on top of me and told me how fantastic that was. As we started to make out his hands reached down to unclasp my stockings and pull down my thong. He slid down, pausing to kiss my breasts. I wanted so badly for them to be real. Getting lower he parted my legs. My dick was so hard and he commented about what a nice clit I had. He kissed and licked it a few times, then worked to my balls and finally lifted my legs. I was not expecting this at all!
I gasped as he began to work his tongue around my asshole. God it felt good and he seemed to be liking it. As I writhed in pleasure, I felt some pressure against it and realized he was inserting a finger. I did my best to relax and let him in. Slowly it worked and he began to wriggle it gently around in me. It felt very nice to me and I encouraged him with my moans.
"God Darren that feels wonderful" I whispered.
"Are you my girl Amanda?" he asked.
I moaned an "mmm hmm" to him and then, when I was at the peak of pleasure I shouted "make love to me Darren. Make me your girl."
With that, he slid back up me, hiked my legs in the air over his shoulder and positioned himself to enter me.
"Are you ready for this Amanda?"
Again, an "mmm hmm" and smile from me. As he slowly pushed inside, the size overwhelmed me. I'm sure I had a look of pain on my face.
He slowed down and said "I'm hurting you."
I whispered "go slowly but please don't stop".
Between his licking of me and my saliva on him, we were well enough lubricated and after a few shorter slow thrusts, he gently entered me entirely. The pressure in my ass was intense but so was the pleasure of taking him. He held it in me for a long moment while I leaned up to kiss him. Then, he started fucking me.
My ass relaxed and I was into it. He wasn't thrusting hard but had a rhythm going. He also began to stroke me which felt wonderful. I told him I loved having him inside me and that seemed to really turn him on. I could feel his cockhead raking across my prostate and began to head toward an orgasm. My hands reached around his back to brace myself to him.
"Keep fucking me Darren....keep fucking me" escaped my lips. He picked up his rhythm getting me so close....so close..until I cried out and felt a wetness growing on my stomach. Now it was my turn to breathe heavy.
After my orgasm, Darren rolled my legs together and me onto my side with him behind me. His cock never left me completely during the move. I knew he was ready to cum himself and he wanted this position. Now his pace really picked up. I was truly getting fucked. I moaned hard with each thrust, always having loved girls who did that with me. He was like a piston driving in and out. I was so ready to take his load. Finally he paused for a second, held his breath, and nailed into me holding the position. I felt his cock convulse and knew I was taking his semen. When he finally stopped thrusting we just lay there. Him slowly softening inside me, his girl.
Eventually we separated. He rolled to his back and I nestled my head in between his chest and shoulder, kissing his chest periodically. His arm was caressing my hair and shoulders and I drifted to sleep to dream about my own wedding....to my own man Darren.