A Perfect date!
We met online with him pretending to be a pretty girl while I was trolling for younger sissy types. He was 27 and pretty. I'm much older, and very handsome. He said he couldn't come out when he was in high school but had always wanted to go to prom in a pretty dress. It sounded like a fun and easy role play. it'd just wear my usual slacks and jacket, and he could dress anyway he liked.
There is an airport bar on the outskirts of town with a old style dark bar with a dance floor and some retro disco ball sort of decor. Perfect!
We met a few days earlier at the bar for drinks and he loved the place. I told him, sternly:
"I'll have a room here and I expect us to use it. Use it a lot."
He looked back at me with his sweet, pretty eyes, slowly nodding his head in agreement. I could tell he was nervous. Perfect!
I booked the room and made my plans to bring some wine and whiskey to the room. I also figured I would bring some fun toys to use on him when things got down and dirty. I do love the sounds a submissive fuck toy makes when I'm ramming his ass while he has a gag of some sort stuffed in his mouth. It's the best. Of course, you can't leave their hands free, or they will pull the gag right out. So, some sort of kinky restraints are always in order as well. I decided on cute pink and white leather cuffs, a dog collar and ankle cuffs as well. Perfect!
He sent me a picture of the pink prom dress and some matching pink high heels he planned to wear, for my approval. I got hard right away. I told him they would do.
The plan was for me to pick him up at his apartment, so he could run out, all dressed up, and leap quickly into my car and leave for the hotel. He was nervous one of his neighbors might recognize him in the pink dress and heels. I agreed, but I certainly had other plans.
He told me he would be alone in his apartment dressing, with his roommate not being home until much later. He wanted a private time to dress in all the pretty lingerie and prom dress for me, with no one else around. He said this would give him plenty of private time with a lot of room to spare. His roommate doesn't know he secretly wants to be just like a girl sometimes.
I told him I would be a gentleman and bring him a flower at the front door. He thought that would be 'Fabulous!' Perfect!
I packed the pink leather cuffs and the dog collar in my jacket pockets. I brought a panel gag, one of my favorites, in my slacks pocket. It's the kind that is fashioned like a fat rubber cock, with the head being big and round like a ball. It should barely fit in his mouth with the panel strapped over it, and around his head, holding everything in place. He will be gagged with a fat cock shaped and sized dildo in his mouth, with no way to push it out.
I expected that when I see him, I'll be impressed and excited with him in his pretty pink dress and high heels. So, I'll be ready for round one right away. That was my plan. I was hard, all the way to his apartment. Perfect!
I realized I'd forgotten a flower, but it didn't matter. When I arrived at his door, he slowly opened it, just a bit, looking out at me, shyly and very nervous. I stood there calmly. Waiting. My hands were behind me, hoping he might think I had the flower there as a surprise. After a moment, he opened the door and invited me in. I stepped in and closed the door behind me. he seemed confused that we were not leaving right away. I stood by the closed front door admiring him in his pretty outfit. I was getting even harder now. I asked him to pose. I wanted photos.
'Oh my gosh!" He exclaimed. "I'm not all that pretty!"
Well, he was. He has skillfully combed his hair in a cute little flip up over his head and added a pink ribbon to hold it in place. He had carefully applied some basic make up. A little eye liner, some soft pink highlights on his cheekbones, and some pink, peach flavored lipstick. Very soft, very understated. I liked that.
The dress was pink with white ruffles and an open front showing some clever cleavage he has somehow made up with the use of a tight push up bra and some enhancement fillers. The brief outline of a red lace bra was peeking out just slightly behind the ruffles of the dress. His waist was tight and slim. The dress fell over his hips very nicely. He was wearing white hose and the pink heels he had showed me before.
He was shy at first, posing for my phone's camera. But as I complimented him and told him how much I was looking forward to tonight, he loosened up and took my suggestions. Sitting, standing, turning, etc. He gently lifted the dress up his smooth shaved legs, at my request. At the top of the stockings were lace surrounds. Holding the stockings up were pretty red lace garters coming down from under the dress. He was wearing a red girdle or a garter belt of some kind. "Very sexy", I noted.
Lastly, I asked him to turn away from me. I wanted a nice back shot to complete my small collection of pictures. He turned, but was nervous again. I could tell. He should be.
I took a few pictures as I moved closer to him. He jumped in surprise when my hand touched his shoulder.
"You look amazing. I don't think I can wait for later. I'm sorry, but you will need to make yourself up all over again when I'm done."
He was surprised I was so close when he turned his head back to respond. I took his head in my hand and held it so I could kiss him, turning him toward me. He tried to resist for just a moment but quickly understood and gave in to my advance.
"It's Okay. I'll have time to redo whatever we ruin."
We kissed for a long time. Our hand wandering over each other's bodies. The dress was satin and very slippery. My hands were all over it, and him.
Him? Well, at that moment, I realized he had become that pretty girl he always dreamed of being. He kissed me like a girl would. He wrapped one arm around my shoulders like a girl would. He slipped his hand into my crotch, grabbing my cock like any horny girl would. My hands ran up and down his long sexy back, over his bottom, and up onto his breasts.
I was already far beyond the foreplay, though. I wanted him. I wanted to blow a big wet load inside him. I was ready to go to home base right now. I didn't think about him. Or her. I just made an excuse, dropping her over the back of the couch, pulling her dress up over her back, and going for it.
"I'll do my best to not ruin your make up, sweetie."
I agreement, she begged me: "There's lube in my purse. Please use some, I wasn't ready for this so soon!"
Perfect!
With that, I pulled the sexy thong back panty down to her knees, spread her sweet round cheeks, sprayed a nice stream of lube in her hole, and pushed my jizz leaking cock right in.
"OH, my fucking God!" She shrieked like a little girl. It was great!
I mounted her with my hand holding her head face down in the pillows on the couch. She was struggling with her hands and arms waving up and down trying to get hold of something. Her legs spread, one heel off her foot, the other still on. I held her down as I got into a nice fucking rhythm and didn't stop.
"You're going to love this, you little bitch!"
When I felt myself getting very close, I grabbed her tit and squeezed hard. The perky tit, soft silky dress and lace bra felt really sexy in my hand. I pushed her face deeper into the soft couch pillows. I pushed harder, stopped, then jammed in hard again. A squeal came out of her sweet little mouth. I pumped until I released my nasty full load in her tight, slippery little butt cunt.
I held her there for a few minutes. Catching our breath.
Finally, I lifted myself off of her. I stood up, looking down at the ravaged little slut in the pretty pink dress. Well, the dress was half off of her. The sexy red garter and panties were not where they should be. Her carefully combed hair was a mess. One stocking was pulled down to her knee, the other still barely hanging on by one red garter up by her ass. I was a bit wrinkled as well. I pressed my shirt down and adjusted my slacks. I think I'll e fine. But she is going to need a bit of a makeover.
I gently spoke, trying to not break the quiet moment. "That was fun. I am looking forward to some dinner and that dance. But I can't wait for another round. How about you?"
She glanced back over her shoulder at me. Then back down at her wrinkled outfit. Then back, looking into my eyes. She smiled.
Perfect!
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