It Happened on a Dare

This story is about 3 friends Jay (19), John (21) & Steve (22), one day while walking down the street they saw what they thought was the most beautiful woman stroll by, it wasn't until they heard her talk that they knew it wasn't a girl but a man dressed as one.

Jay said "God I can't believe it she was so beautiful."

"Shit but is was a fucking dude," John said.

"Yeah what a shame, such a waste no pussy to fuck," Steve fired back.

As the continued to walk Steve said, "hey Jay with that ass you'd make a cute girly-boy."

"Fuck you Steve," Jay yelled back.

"Shit man I think you might be right Steve," John said.

A few days passed and there was no more talk about it, until on night the three were together again in Steve's house. There was a major snow storm that evening and power had gone out leaving them with no tv, internet or phone as it seems a cell tower must have gone off line in the area. Steve was lucky in that his home had a working fireplaces in the living room, bedroom and dining room.

Steve loaded them with wood and they huddled around the fire in the living room talking about mostly nonsense until Steve brought up the subject of that guy dressed as a woman they passed on the street.

"Hey you know that dude from the other day, I saw her again when I was out shopping she does have one fine ass even if it does have a cock connected on the opposite side," Steve said.

"Fuck dude you a fucking homo or something?" John said.

"No man I mean such a waste, could you imagine being with her and then finding out she had a cock?" Steve asked.

Jay sat quietly and listened to his friends as they talked taking in their words.

"Dude you could still fuck her ass you fucking homo," John replied.

"So wait, if you fucked her ass would that be gay, I mean look at her she was a beauty?" Jay finally spoke out.

"Well I think it would be, I mean how could an ass on a girl like her satisfy you like a girls pussy?" Steve asked.

Steve got up and brought the other guys a shot of JD and a beer and they all downed the shot and sipped on their beers.

"So you mean to tell me if that hot thing dropped her pants and you saw a wanker hanging down between her legs you wouldn't fuck that ass if she bent over for you?" John asked.

"Well, I mean if nobody was around I might," Steve answered.

Steve took the shot glasses filling them again and giving the others another beer. The men quickly downed the shot and he filled the glasses again as they downed 3 more shots each.

Jay not being used to drinking passed out as the other 2 men continued their conversation.

"So you mean to tell me if she was here like that, pointing at the passed out Jay, you wouldn't pull her dress up and fuck her ass?" John asked.

"Well I don't know, I mean if she had an ass like Jay's, I don't know." John answered.

The two men had a few more shots and another couple of beers as Jay lay there. You could see they had some very horny ideas floating around in their minds.

"Shit man don't you think Jay would make a pretty hot chick? I mean he got that ass, that tiny frame of a body (5'4" 115lbs), those deep blue eyes and long blonde hair. And that almost hairless body, Jay had no chest or back hair, almost invisible pure blonde hair on his legs and a face that is devoid of anything resembling even peach fuzz on his face," Steve said.

"Crap man now that you say that he would make one beauty of a girl," John said as he eyed his passed out friend up & down.

Steve disappears before coming back with a pretty outfit left behind after his sister left from a previous visit thinking if she kept enough clothes here she could fly in with no luggage next time and have a nice wardrobe to wear.

"I think this looks like it should fit him," Steve said as he held a pretty blue sundress, a set of shear blue panties and a matching bra up in the air showing his friend.

John grabbed the dress & draped it over Jays clothes, with shorts and sandals on the dress covers him well and you the two could see all the pretty feminine parts of his body accentuated under those girls clothes.

The two men stared at the dress before Steve said, "Fuck he would make one hot girl."

Jay woke up looking at the dress lying atop him, still in a drunken state he said, "what the fuck are you doing?"

"I mean we thought you'd make a cute girl and I dare you to put that shit on & prance around for us," Steve said.

Steve knew Jay never turned down a dare and you could see the look in Jay's eyes knowing he wouldn't back away.

"Fuck you two ok here goes," Jay said as he took the clothes into the spare bedroom that Steve's sister kept her clothes in.

After what seemed like quite a while Jay comes out, not only is he dressed in the dress but he put on the bra, panties and even went into Steve's sisters dresser and put on matching nylons and a pair of blue 4" heels. Everything he found fit him like it was bought just for himself he marveled at how the material of the panties felt on his small 4 1/2" cock thinking to himself how girly he actually felt in them. The other men could see he had even pulled his long blonde hair into a very girlish looking ponytail and upon further exam found he had done a complete makeup job on his face.

Both men stood with mouths ajar just staring at what was standing in front of them.

"So I guess you like what you see?" Jay asked.

The two men just stood there for what seemed like minutes before Steve said, "crap you the best looking girl I have ever seen!"

"I fucking totally agree, man I would take you out in a heartbeat," John said his mouth agape as he started at his friend.

Jay stood there not knowing if it was the booze or the soft lacey material rubbing all over his hard cock. He felt a tingle run through him, not around his cock this time but actually inside his own ass almost as if his body was telling him something, but what?

"So you think I'm pretty?" Jay asked, noticing for some reason his voice sounded softer, sweeter almost girlish.

"Wow say something again that sounded awesome," Steve said.

"What should I say?" Jay asked, again his voice sounding even higher pitched but also softer, a sweet angelic sound.

"Amazing fucking amazing," was all John could say.

Suddenly the lights came back on Jay could see now in the bright light that both men standing in front of him had so very hard cock bulging against their shorts.

"Wow I guess I had an effect on you two!" Jay said laughingly.

"I have another dare for you, I bet you wouldn't go out like that with the two of us, bet you'd be too chicken for that!" Steve said.

"Yeah I like that, so you got the balls to do it?" John asked.

"Fuck you too, let's go it stopped raining," Jay said going into the bedroom taking Steve's sisters pretty little blue purse with him.

They went out and Jay noticed how many guys turned their heads as he walked by, it took a bit but he was swaying his hips like all the runway models he's seen on tv had.

"Crap that's hot," Steve said as he cupped Jays tight swaying ass.

Jay pulled his hand away and said, "this girl isn't free, at least wine and dine me."

Jay was taken by how good he felt wearing these clothes made him feel much more free than he has ever felt. The material of the panties combined with how smooth his legs felt in the nylons, his hair swinging freely in the girlish ponytail, his waist feeling cradled in that dress, the only thing he wished is that he filled out that lacey bra he was wearing. Finally they found a restaurant that was still open several blocks away as it seems the power outage was contained to a small area.

They showed them to their table and the waiter pulled out the seat for Jay who smiled and gave him a girlish sounding, "Thank you."

They ate all the time talking and laughing at how many men were staring at Jay's new feminine persona. Finally they left and went back to Steve's house had a few more drinks and passed out, Jay made his way to the spare bedroom and lay on the bed fully clothed in his pretty blue outfit just loving the way he felt.

About and hour later John lay on the bed spooning Jay in a drunken stupor, Jay just lay there in wonderment as he felt his friends hard swollen manhood pressing through his shorts against the dress and panty material he was wearing. Jay could feel a tingle inside him his cock no longer hard but feeling something different, still he thought seeming like sexual desire but so much different like it wasn't an external desire like when his cock grows hard but something below his manhood impaled deeper as if something inside him was trying to find a way out...........