Prom Dress Contest for The Boys

1. the ad

I watch all the sissy porn I can find. Finally I placed an ad in a local gay dating site looking for any guys who wanted to compete in a little dress up contest. I'd provide a safe place for a photo shoot, a little fashion show, and a chance to meet up for drinks. First, second and third place would win 20 dollars and a date with me. I posted a picture of my cock. 

I didn't expect too many responses. But to my surprise, I did. I scheduled a party that weekend at my house. I had 10 or so RSVP. I used the upstairs for a place to dress and do their make up and hair. I have a friend who is a hairdresser who volunteered to help out. On the main floor was the party. Snacks, drinks and some naughty porn on the Tv to get everyone in the mood. I set up a wedding and a prom photo booth out on the back patio. Everyone enjoyed having their pictures taken with each other, and with me. It was a nice way to meet all the prospects. 

For some of the fun pictures the guys in drag would kiss me on the cheek. I'd have my arm around them. I was wearing a nice suit. I looked good for an old fart of 55. Everyone would Oooh and Ahhh when a kiss or a feel up would happen. It was fun.

One by one I took the pretty crossdressers downstairs. The fashion show was going to be in the den upstairs, but I wanted a little alone time first. I have a dark bedroom down there with a big king bed. I installed some large wood beams along the walls and a few up on the ceiling. There are metal rings and some chains hanging down here and there. Not too many, but just enough to give the room a creepy dungeon feeling. I've got some naughty pictures on the walls. Mostly of ladies bound and gagged or kneeling with a cock in their mouth.  It's a sex room. You don't have to wonder about it. It's right there in your face. 

The first 2 guys freaked out and went home. I apologized and gave them Uber fair. But the third one wrapped his lace covered arms around my neck and asked, with his smooth, red lips, what he needed to do to win first place. I told him to kiss me real nice, and that would be a good start. I encouraged the sissy boys in their pretty outfits. I told them how cute and sexy they are. I tried not to get too excited. And not all of them were into having me touch and kiss them. But some of them were. 

2. the show

After I made out with the sissy's in the basement, I tried not to mess up their outfits or make up, we started the fashion show.  Six decided to say and give winning a try. 

Joanne, we named her, was probably the best of show. Tall, young, pretty and she had her own hair. Long flowing blonde hair she must have spent hours on beforehand. She was the one who kissed me first. She was in her moms wedding dress. White satin and lace. It was short. Very short. Mom must be a small lady. Joanne stayed true to fashion by wearing a full white satin garter with 4 straps on each thigh, and sexy white lace top nylon stockings. She was walking in a pair of shiny white 4 inch heels. The top of the dress was all lace. From the middle of her waist all the way up around her neck. Her arms were also lace covered to the wrist. Very pretty. Very classy. The sheer lace was see-through for the most part. Leaving the clear outlines of the cute little strapless push up bra she had on under it. The bra cups were full from what must be silicone breast forms. Solid C cups for sure. Very sexy! She posed for everyone, especially for me. We all took lots of photos until it got a little nasty. She was bent over in my face, only a satin panty between her hairless hole and my nose, spreading her butt cheeks out for me. I called it 'cause it was time for number two. 

Jenny was who she called herself. This slightly chubby slut was in an all black prom or bridesmaid's dress. It was very short too. Her legs were covered in black nylon, back seamed stockings, that went up just under her ass cheeks. She was expertly walking in her slutty black high heels with red trim. They were held tightly in each foot with wide straps around her ankles with a little brass paddle lock on each one. Bondage style. 'Fuck me' heels for sure. The front of the dress plunged deeply, falling off her shoulders, exposing her smooth chest completely. She was wearing a leather harness style bra with many straps wrapping tightly around her perky boy tits. A long Elvira type deep black wig and a black BDSM collar completed her outfit. The collar had the word 'Slut" on it. She had dark eyeliner and bright red lipstick. Very naughty. I liked her a lot. When I kissed her earlier, she sucked my tongue so hard into her mouth I thought she might tear it out. She said in a deep, sultry voice, "You might think you are going to fuck me, but don't be so sure. I'll be the one doing the fucking. I'll most surely fuck you like a bitch, good sir." She fit right in down in the basement dungeon. 

Joe was a novice for sure. He was in his sister's purple prom dress. It was a bit tight. He had shaved everywhere, and done a good job, but he was not the most feminine of the group. He was trying, trying very hard. He had on tan pantyhose and flats. The white bra straps under the dress kept showing and he kept trying to tuck them back. He has slicked his hair back then fluffed it up a little bit. it looked pretty good actually. I liked it the best of his efforts. He looked like the awkward girl who didn't have a date to the prom. He didn't pose much. He just stood there waiting for the moment to be done. 

He was the most nervous of all the guests. Even of the ones who left. He didn't really want to go downstairs with me. Somehow he forced himself to make it down the stairs. We didn't make in into the bedroom. He held my hand and closed his eyes, waiting for a kiss right there on the landing. When I slipped my tongue in his mouth and pressed my lips to his, he let out a huge sigh and got into the kiss really hard. Every squeeze and hug I gave him released another sigh or moan of pleasure. "I want this really bad. I hope you choose me for that date."

Paige was a drag queen fag. I didn't like her. Most of what is worst, in my opinion, for the gay community. Much too much make up, a very flashy outfit, too long fingernails, big hair, not hers, and a attitude that just says I'm the devil's gift to fagdom. Her silly attempts to make a feminine sounding voice, trying to walk like a runway model, and just her overall bad attitude toward everyone else, made me want to take her downstairs and leave her there. Bound and gagged. I did my best to calm her down when we were in the basement. "Look, I'm really just looking for a sweet little sissy boy to make me feel good. I don't want, or need the whole floor show. Can you just do that?" She kissed me on the cheek and went back upstairs. I thought she would leave. But she settled right in and made friends with all the other girl-guys. 

Jerry was pretty cute. He was older. probably in his 40's. But he was sweet and told me he was looking for a relationship. He was divorced several times over and finally came out and quickly lost what few friends he had left. He had been dressing for years and none of his wives accepted it. He was tall, fit and charming. He chose a classy red dinner outfit. Black nylons and heels shown through the slit in the long, flowing dress. Just a bit of make up and a nice, neat short hair doo. He was pretty. I told him so. He liked my dungeon, even though he said he had never been a bondage fan. But he was willing to try, for me. We had a short, sweet kiss, then he told me why he was there. "I don't know if this would ever work out with us, but I'm willing, and obedient."

His photo shoot went very well. He knew some classic poses and he looked nice doing them. Everyone was impressed. 

Finally we have Dory. Yes, like the fish. A bubbly chubby baby girl with rosey red cheeks, curley blonde hair. A pink and red dress with petticoats and frills everywhere. White cotton tights, white cotton sleeves and matching gloves,  Accessories included a pink choker neck collar, matching pink wrist and ankle cuffs, and pink tennis shoes. Hanging from a strap around her neck was a oversized, adult baby pacifier. The yellowish rubber ball of the pacifier was as big as a plumb. It looked like it was there waiting to be used to silence the little bitch when she was crying. The top of the dress was form fitted around two huge tits. Big rubber falsies I assumed. Triple D cups at least. They bounced and bobbed all around when she laughed. And she laughed a lot. I liked her right away.  I mentioned that this was a prom or a wedding sort of affair. But she said "Oh, I wore this to my prom a couple of years ago, and everyone was just fine with it then." She bounced all around the room the whole time she was there. Everyone loved her. She was the definition of FUN. 

Down in the basement, she told me she would be the first to volunteer to be the BDSM slut for the party. We could pull a train on her if we wanted. She showed me her wrist cuffs and smiled. She said she was addicted to sex. She wants it all the time. "I work from home. I make a lot of money. I do whatever I like. I don't get to hook up for real very often. I have a lot of dildo toys and bondage stuff. I love your dungeon! Can I move in here? You need to fuck me. I'll let you do whatever. I like you, Daddy. " She had opened the top of her dress and her boobs fell out. Yes, they were huge. She had a white lace corset holding it all together. The fake nipples were as big around as tennis balls. They were  dark pink and very erect . She was rubbing them all over me when we talked and kissed. She was trying to get me to suck the nipples through the lace bar cups. She was trying to get my pants off. She told me I could tit fuck her right now. She wouldn't let anyone know. "Maybe you'd like to strap me down to that bed and tit fuck me? You can fuck my tits and I'll I'll suck you off. I'd like you to blow a load all over my face. I'll lick it all up and swallow it all too." It took me a little off guard. Such a sweet girl. I almost gave in. Her boobs were really fun. She smelled really nice. Peaches. But someone knocked on the door upstairs. I guess we'd been down there a while. We went back upstairs.

More coming soon