Cross Dresser at Convention Pt. 01


Part I: The dare

Dennis an IT professional met his friend Tim at the hotel where the convention was to take place. “Hey Tim how are you?”

“Pretty good. How was your trip?”

Dennis replied, “It was interesting, I took a train just for the experience. I saw a lot of countryside and was able to prepare more for the convention. The trip was affordable. Hey why don’t we share a room and cut expenses?”

They registered and got a top level room with a view of the skyline across from another high rise hotel building. When they got to the room they started to settle in. Tim ordered some cokes and a large bottle of Jim Beam whiskey to smooth out the pre-convention nervousness. After a couple drinks Tim said, “Hey look at what I got for my wife at the gift shop.” He held up a bottle of his wife’s favorite perfume. “She says no man can resist it. I have to admit it includes me.” He opened it and let Dennis have a whiff.

Dennis said, “man that does smell good.” Then Dennis bragged, “I got these from a lingerie store across the street for my wife. The bikini panties won’t cover the top of her ass crack.” He held up a set of sheer white cotton bikini panties with a pink bow and frills with a matching bra with clasp in the front hidden by a pink bow. “And look at this,” holding up a sheer slinky reddish orange stretchy cotton dress with a velvety touch. Dennis couldn’t help himself and rubbed the fabric to show Tim how smooth and sexy it felt. He let Tim feel of it. “When I was in the store with a lady clerk helping me choose the fabrics and style I started getting a hard on. She held the panties to my nose and giggled, but they do smell good. Here.” He handed them to Tim to get a smell of them. Here they were grown professionals smelling panties in a hotel room together, but Tim acknowledged to himself the smell was the reward in itself. Somehow the panties smelled titillating and sexy although no woman had probably worn them before. Dennis was obviously proud of his purchases. “Look at these also, the saleswoman got me a pair of matching sexy evening shoes to go with it, but now that I look, she gave me the wrong size. Shoot those are about big enough for my feet.”

Tim noted that nipples and pussy hair would show through the underwear.

“Hey let’s go down to the introductory session,” said Dennis.

“Ok, let’s go.” Tim responded. They went down the elevator chatting about technical things, the convention organization, and the hotel set up. “After hours there is a bar and dance floor on the first sub floor. It is supposed to be pretty good.”

After the brief session they decided to check out the bar. They went down to it and it was a cozy dimly lit bar with sexy lighting, low music, with a good dance floor. The waitresses wore mini bikinis that showed camel toe, and even in the low light you could see their nipples through the thin material of their tops. Tim could swear he could see pubic hair from the sides of one of the waitresses outfit. He was getting turned on. It looked like Dennis was feeling the same way.

They had a few drinks each and a very light lunch. Both were getting a little buzzed and decided to go back to their room and get out of the suits and wear something more comfortable and they would come back to the bar. It was already getting late evening and other patrons were beginning to show up to the bar, including some nice looking women, some of whom were business professionals also attending the convention which would start the first full day in the morning.

They had a few more drinks in the room. Dennis kept touching and holding up the panties and dress. He showed Tim, “The back slit goes all the way down to the ass crack. The dress is just long enough to cover the butt cheeks while standing or walking.”

Tim said, “Are you sure she will wear those?”

Dennis replied, “You are right she might not. Actually I probably need to take them back. It is nice to imagine her wearing those though. I can just imagine how it would feel to hug her and rub her body wearing those.”

They continued to talk and cut cracks and jokes about the clothes and good looking women, the bar and the waitresses. They were getting drunk and horny. Getting ready to go down to the club, Tim said jokingly, “Hey why don’t you try those on before we go, then you will have a better feel for them.”

Discreetly Tim set his smart phone on record mode. It captured the following events with movie, and snap shots also.

After some more joking and kidding around Dennis decided to slip them on, just to imagine how his wife would feel wearing them. Tim kept spurring him on. First he got naked in front of Tim but Tim encouraged him saying they were close friends and it did not matter. He slid the panties on, and Tim gave him a small pat on the ass saying how soft and sexy they were, and gave a little squeeze as a joke.

“Come on put on the bra.” Dennis had never put on a bra and so the two of them figured it Bayan Escort out together. Tim said, “You bought her a padded bra?”

Dennis said, “I was not sure what to buy so I got that so she could enhance her form more if she wants to, but really she doesn’t need it.”

Tim helped him slide on the dress. It was fairly easy because of the slit in the back, and it was short and a little slippery. Tim noticed indeed the slit was open all the way to the ass crack showing down the ass crack with about ¾ inch of the panties showing.

Facing his buddy Tim rubbed the sides of the dress and said, “sexy, it even makes my dick hard.” Without knowing why he took Dennis’s hand and put on his cock to show him. “See?”

Drunk, and unwittingly Dennis rubbed Tim’s cock to feel its hardness, but lingered longer at it than he meant.

The smart phone captured Dennis feeling and cock rubbing.

Tim got his wife’s perfume out and put some on Dennis rubbing it on the sides of his face, down his back and to the ass crack. Fortunately Dennis did not have much of a hairy back or ass. He said, “You look great, here try these on,” and got the shoes out. He sort of pushed Dennis onto the bedside. As he slipped on the shoes he could not help but look up the skirt of the dress to the panties, out of habit. Dennis had long hair and Tim combed it for him it to look more feminine. “You look sexy.”

Dennis gave a hearty laugh.

“No, you are supposed to giggle, not laugh,” Tim said.

“Hey just for kicks let’s go to the club like this and see if you can get some dances and free drinks. Come on, I dare you.”

So off they went.

When they walked into the dimly lit club in front of some other men, Tim purposely lightly smacked Dennis on the ass and rubbed his hand on his butt feeling the panty lines through the fabric, squeezed the butt cheek and pinched his ass which brought a giggle from Dennis playing the role, but was also drunk.

Tim walked away to get a drink and find a place to sit or stand and watch.

Dennis was looking around a little, almost shyly trying to figure out what to do next. Then a man came up putting his arm around Dennis and gave him a small but strong drink. It was good and Dennis gulped it down not realizing how strong it was. The man still had his arm around him with his hand on Dennis’s bare back through the slit in the dress. He guided Dennis to the dance floor asking him to dance. Reaching the dance floor the man’s hand slid over the top of his panties. Dennis did not resist, playing the role and not knowing what else to do. As they started to dance the man’s hand occasionally would venture down his ass crack a little. Bumping around a little Dennis realized the man was getting a hard on, and suddenly realized he would have to somehow hide his bulge, so when things got too close he put his head on the man’s shoulder while dancing to get some space between them.

The man excused himself and said he had to get another drink and would be back.

Dennis was exhilarated. It was fun pretending to be a lady and find out what it was like to get dances and free drinks so easily.

Another man came up in the mean time and also brought a drink. It was a different drink and it tasted good. Dennis was enjoying trying different drinks. His new partner also took him onto the dance floor, and as they danced Dennis could feel the man’s hands exploring his body. This one snuck a hand up the back of his dress and he could feel the hand slip under his panties and feel of his ass, one hand grazing across his asshole. This was a new experience. Suddenly he realized the man’s hand might be getting too close to his balls so he brought the man’s hand up to the small of his back, where the hand explored his ass crack. As they moved around the man brought Dennis’s hand over his cock and rubbed Dennis’s hand up and down the cock all the way to the balls. Obviously he wanted Dennis to know what good equipment he had. Besides the brief encounter feeling Tim’s hardness, this was the only other time he felt another man’s cock. Dennis had to think in his drunken mind whether he was doing it because he liked it or as part of his cover.

Having a few more dances and getting groped, Dennis realized he might be getting a thrill of feeling these cocks, balls, and asses. Some of them drew his arms around to the backsides and ass cheeks. He had to hug them close, fondle them, and arch his back so they wouldn’t feel his cock, especially because he was getting a hard-on.

Dennis guided the dances more toward the darker corners of the room, near the bathroom hallways. The more drunk he got, the more dances he got, and the more he fondled.

He needed to pee so Dennis snuck away and went down the hall to a small bathroom he found in the darkness at the end of a hall. As Dennis entered, he was shoved, and the main light was turned off. A hand went over his mouth and he heard a shhhh! The silhouette of a man pushed him backward and he stumbled back to sitting on a toilette facing the crotch of a man. “Shhhh!” He watched in the dim light as the man unzipped and pulled out a cock beginning to drip precum. Dennis tried to think of something to say. “Shhh!” He couldn’t make a disturbance at the club or his wife might find out. The cock with precum is wiped across his lips. Reflexively he licks his lips and his tongue scrapes the cockhead. Suddenly the man grabbed the hair on the back of his head and rubbed his face against his crotch feeling the pubic hairs on his face, lips, and nose. It smelled of pubic manhood. His face is rubbed all around the balls, until his lips are underneath the ball sack, and the man said, “kiss and lick.” He forcefully said, “lick further back.” He does and he feels his tongue scrape across the anus, feeling ass cheeks on both sides of his tongue. His head is held there for a few minutes, and is told to taste and kiss. He kissed and tasted the asshole and cheeks, the perenium, and is told, “kiss and lick up between the balls, then taste, suck and tongue massage my balls.”

The man took his cock and placed the head between Dennis’s lips and said, “lick the top, stick your tongue in the hole.” He thought as long as he had the cock in his mouth the man was distracted and this might give him some time to think of a way out of this. “Now lick around the flange of the crown. Lick up and down the shaft.” The man began pumping the cock in and out, some strokes half way and some all the way. Then he pulled out so only the head was in his mouth and came in spurts, and a flow. He was told to slowly roll the cum all around his mouth, and in his cheeks, taste it good then swallow. This is the first time Dennis had tasted cum. It was good he thought. The balls tasted good, and besides being humiliated, he enjoyed sucking them. The taste of cum remained in his mouth, but he could also taste a little of the asshole on his lips. At least the man was clean he thought.

For the first time Dennis he had just sucked and swallowed, rimmed an asshole and sucked balls, kissed ass, kissing and licking everything.

The man left leaving the room dark, and the door partially ajar. He sat there and pulled down his panties to pee sitting down while trying to regain composure. He peed long and hard. He had not noticed a hole in the wall before, but when a light went on he could see through it and that there was a utility closet on the other side and a figure was moving around. The figure approached the hole covering almost all the light. The hole was large and oval. The figure unzipped and soon he was presented with a cock and balls through the hole.

Undecidedly he leaned forward toward the cock, maybe to get a look in the utility room. There must have been another hole in the wall as a hand grabbed the hair at the back of his head and pulled it strongly forward and rubbed his face against the crotch. The cock and balls were completely through the hole. He kissed and licked the balls hoping that is all the guy wanted. A hand pushed one of the balls against his lips and a voice said suck it. Hoping to delay the guy he sucked the ball. The other ball was pushed into his mouth. Then his head was forced below the ball sack and somehow the man hunched up so his asshole was at the hole in the wall and for a second time Dennis was made to lick and rim an asshole. The taste of the last one had worn away when his mouth was drenched with cum. He was made to lick fervently all over the anus and kiss and lick the ass cheeks and perenium below the balls. Now he feared getting used to licking assholes. He thought about how did he get into this. As his face was pulled up the cock shaft licking and kissing he was now presented with a throbbing cock pushing into his mouth for a second time.

He licked the piss slit, and ran his tongue all around the cock head. The voice said tease it, and lick it. Suck it hard, I want to see your lips pull out. He pulled the cock head out of the mouth and said lick it I want to see your tongue all around it. Suddenly the cock was pushed into his mouth and gushed spurts of cum hard against the back of his mouth. Swish it around and taste it good, the man said.

Just as he swallowed and sucked it clean the door pushed open. A figure came in and he noticed the light in the hole had gone dark and that person was gone. The new one was desperate to piss, but also desperate to cum. He had a hard on and could not piss until he took care of it. Unexpectedly he saw Dennis sitting there with a dress and panties pulled back up, with heels square on the floor. Without a moment hesitation he thrust the cock in Dennis’s mouth. He tasted several drops of pee and then the sweet taste of precum practically flowing out the piss hole. The cock swelled and burst with spurts of cum in his mouth and throat. Cum flowed out his nostrils, coated inside his cheeks, and at the same time oozed down his throat. It was a big forceful load, and the man squeezed the remaining drops out leaving his deflating cock in his mouth until he started to relax. His head was held firm and as the cock deflated his head was pulled all the way to the pubic hairs. With a few drops at first then a couple small squirts the man started pissing in his mouth holding his head. He couldn’t help but swallow but some of it spilled out over the man’s balls and down onto Dennis’s dress. When the pissing stopped the man said to suck the piss off his balls. Some of the piss had dripped down to his asshole, and he was made to lick piss off the asshole, licking asshole for the third time that evening. The smell of cum remained in his nostrils, and the smell of his own breath had cum, piss, and the smell of asshole.

Back on the dance floor, Dennis had not thought of bringing mouth wash or breath freshener, so he accepted a couple more drinks to hide the smell of sex and cum on his breath. He started looking for a back way out, and then someone came up behind Dennis and held him around the waist

Hugging Dennis from behind he put a finger in his mouth and it felt like he deposited a pill in his mouth. He brought Dennis’s hand with drink to his mouth and fed the rest of it until he swallowed it all, washing down what ever pill he slipped in his mouth. He fed his fingers in Dennis’s mouth in and out saying don’t let your teeth scrape it. Dancing to a dark corner of the room behind some equipment, he started to kiss and hug Dennis. Dennis tried putting his head on the man’s shoulder but this man reached down into Dennis panties searching for the pussy he thought was there. Quickly Dennis slid his face down the man’s chest and stretched his ass out so the man could not reach his crotch. But the man was able to find the asshole. First he felt the asshole with a finger. Before Dennis could react the finger was in his asshole to the second knuckle, and soon a second finger and then a third. The man was pulling up on the asshole stretching it and nearly pulling Dennis’s feet off the floor. In an effort to get the man’s fingers out of his ass, Dennis let his face drift further down the man’s chest. “Oh I see what you want,” and he pushed Dennis head toward the belt buckle opening the fly with one hand and pulling out his cock. He presented the cock to Dennis’s mouth and said, “open.” When Dennis did not open his mouth the man with a by now desperate hard on slapped Dennis extremely hard on the face bringing tears to his eyes enough to blind his vision. Dennis complied and opened his mouth, feeling the cock saw into his mouth and ram his throat. Draining his cum into Dennis’s mouth the man commanded Dennis to suck his balls, lick and kiss his ass all over and up and down the ass crack, and finally kissing licking the asshole, sucking on the anal rim. Dennis had never known other men like their assholes licked and rimmed so much. His wife never did it.

A couple hours before daybreak Dennis sauntered back into their room. Tim who had continued to drink all night and took a Viagra instead of a meth pill by mistake said, “you look a mess, let me help you with that. Tell me what happened.” Tim started helping undress Dennis taking note on how good the dress felt. He removed the dress feeling it all the way down the sides, back and ass crack letting his hand drift inbetween the cheeks. He slid the panties down copping a feel of the butt cheeks and crotch, just touching the asshole with his finger out of curiosity. Dennis was so out of it he would never know.

Dennis began, “I went to the bathroom and a man pushed me in and turned out the lights before I knew it he had jammed his cock in my mouth.”

Tim asked, “What did you do?”

“I didn’t see a way out of it because if I cause a commotion I might lose my reputation and my wife might find out, so I did what he told me.”

Tim asked, “What did he tell you to do?”

Dennis continued, “He made me stick my tongue in the pee hole, and lick all around the head, and up and down the shaft. He made me taste it.”

Tim was getting a raging hard on. “Then what?”

“He made me suck his balls and below the sack all the way to the asshole. He made me kiss and lick his asshole. Tim I didn’t want to do it but he made me. Then he made me kiss and lick his entire ass, I can still taste it. When he stuck his cock in my mouth again he came and made me taste it and swirl it all around before swallowing it.”

“Did it taste bad?” Dennis was sitting on the edge of the bed and Tim hugged his head close to his crotch. Dennis didn’t flinch, and then Tim held his face against his cock. Still no flinch.

“No, it was ok, and he was clean. His asshole wasn’t all that bad, but his cum tasted good.”

Tim said, “here lay down on the bed on your back.” Tim had just been in his underwear but now took them off.

Dennis closed his eyes and felt the world kind of swirling, as he was really drunk and had taken some kind of pill.

Tim said, “Stay there I have to go pee real quick before I get too hard to pee.” Dennis thought in a stupor, “Why should I care if he has to pee?”