Sam's Night Out

Sam hoped out of the car and headed for the hotel door. The third hotel in two weeks he thought to himself. He glanced around as he walked to the reception desk. There was a couple at the small bar which caught his eye. Sam's thought about how long it had been since he has had a chance to hang out with a pretty girl like that.

The check in process was frustrating as always. He always got frustrated when they would seem to start the paperwork once he is standing there, even though all his information was sent along with his booking. Before long he was handed his room key and directed to the elevator.

Sam walked in and hits the number 17. Before the door closed, a couple more people step in, it was the couple from the bar. They were a fit and attractive couple, about 30 years old. The guy reached to press the button and saw it was already lit.

"Looks like we're on the same floor", he smiled. He introduced himself as Dan, and his friend Kim.

Sam introduced himself and some idle elevator chat began about the weather. Kim interrupted and whispered something into Dan's ear. He smiled and said "Say... are you interested in heading out on the town with us tonight?"

Sam instinctively began to decline, but he saw the look of disappointment in Kim's eyes and decided "screw it, I deserve this" and agreed.

Kim jumped a little bit with excitement. "Yay, this is going to be SO fun. It's a dress-up party! Don't worry about a thing, we have just the right thing for you to wear" They agreed to meet in Kim & Dan's room in 45mins to get ready.

Sam had been to dress up parties before, but only on Halloween, and it was January. As he put this things in place in his room, and started up his laptop to check email he grabbed a beer from the mini-bar.

He finished his email check, and his second beer and noticed the time had flown by. He got up and headed to Kim and Dan's room.

When he knocked on the door, it was only a couple seconds before Kim opened the door. She was standing in front of him wearing short shorts and a tank top. Her breasts weren't large, but Sam had trouble looking away from her hard nipples. Kim jumped up and down again, beaming, "We're so happy you came".

Dan came over, and handed them each a shot of a bright blue liquor. It smelled sweet, and they all slammed the shots. Sam felt the warmth as it slid down his throat. There was a terrible aftertaste.

Kim reached behind her and handed Sam another glass. "Here's a chaser for you".

They sat down on the couch in their large suite and started chatting. Before long, Sam could feel the effect of the beers and shot. He definitely wasn't drunk, but he felt really good.

Kim seemed to read this thoughts, and told him that Dan was going to go start getting ready, and she would help him get dressed. They still hadn't told him what his costume would be.

Dan disappeared into the bedroom and Kim brought Sam into the bathroom. Every time she reached over to get something he couldn't help but look at her perfect ass in those skimpy little shorts. She smiled as she took out a razor and shaving cream "First... all your body hair has to go".

She still wouldn't tell him what the costume was... but the idea of Kim shaving him sounded pretty good. So Sam removed his shirt. Kim knelt down in front of him, her face right at his crotch as she looked up. "These too" as she unbuttoned his pants and slid them down. She smiled as Sam's firm cock outlined his boxer briefs.

Kim began rubbing the shaving cream onto his legs in a very seductive way and Sam couldn't help from getting harder and harder in front of her. Before long she had shaved his chest, arms and legs, then smiled again as she looked up at him, hooked her fingers into the waistband of his boxers and slid them down.

To Sam's surprise, she gave his cock a quick lick, then sucked the head briefly before rubbing in the shaving cream and finishing shaving him smooth.

Just as they were finishing up the door opened and another girl stepped in. It wasn't until Kim called Dan over that Sam realized that Dan was dressed as a girl, a very sexy girl.

Dan handed Sam a pair of red panties and as he slipped them on they all smiled. Kim let him know that she had to get ready too, but "Danielle" would help him finish up.

Sam was shocked as he realized what he was about to do, but extremely aroused. He had to keep reminding himself that Danielle was actually Dan, as his eyes kept going to check out her ass every time she turned around. Danielle had much larger breasts than Kim, and beautiful long hair.

He was so busy checking out Danielle while trying not to, that he barely realized he had put on his own fake breasts, top and skirt. Danielle then had him sit down so she could do his makeup and hair.

As Danielle was finishing up his makeup, Kim returned, dressed as a guy. A cute guy, but definitely a guy, even a little bit of a 5 O'clock shadow.

Kim couldn't stop complimenting Sam on how good "she" looked. Both Kim and Danielle seemed to be flirting with him as they finished the makeup, and he was having trouble remembering which was okay to look at, and which was really a guy.

Danielle announced that she was all done, and had Sam stand up to look in the mirror. Sam couldn't believe his eyes, he looked amazing!

His excitement and all the flirting was obvious though, as his skirt was tenting a little in the front. Kim got down in front of him once again and began adjusting things, before long, his cock was out and she took it in her mouth again. When he looked in the mirror it looked like a guy was sucking his cock, but he knew Kim was a girl, it was so confusing.

Danielle had her back turned to them, as Kim sucked his cock. It was nice that she wasn't watching, but Sam couldn't keep himself from looking at her great ass as Kim sucked him. He was staring directly at Danielle ass when he felt his balls tighten and he exploded into Kim's mouth. Looking down he saw Kim taking the load in her mouth.

After cleaning him up, Kim tucked Sam back into his panties and fixed his skirt. "There we go, all better", she chuckled.

As they walked out of the bathroom, Kim asked Sam how he liked her costume, and even showed him her full costume as she called it. She unzipped her pants and took his hand. He reached in and felt a firm cock. "It's a strap-on" she boasted. Sam gave it a squeeze, the rubbery member felt quite realistic. He pulled back though as he looked at his hand in a guy's pants holding his cock... this was sure playing games with his mind. They each had one more drink before heading out to the bar.

When they arrived at the club, Sam couldn't believe how many people were there. The girls were all dressed so sexy, and the guys were all so cute. He remembered that the guys were girls and those girls were actually guys, like he and Dan.

As they walked over to the bar, Sam kept catching himself looking at the girls, even though he knew they were guys.

He kept reminding himself to look at the guys, because they were the real girls. It took a while, but he started getting used to checking them out, as many had great firm bums.

After finishing their drinks they headed out to the dance floor and the three of them were dancing together until a cute girl, wearing a hat, golf shirt and pants, caught Sam checking out her ass. She walked over and begins dancing with Sam.

The four of them now looked like two couples. The new guy introduces herself as Sean, and grabs Sam's butt and smiles.

Sam and Sean danced closer and flirted heavier as they groped each other. At one point, Sam was rubbing his ass into Sean's crotch and he thought he felt something. After turning back around, Sean took Sam's hand and slid it to his crotch. It turned out Sean was wearing a strap on too. Sam reached inside and gave it a squeeze, it felt very realistic, like Kim's.

As they danced, Sean kept leading them towards the dark corner of the dance floor. They were flirting and teasing and Sean convinced him to give her cock a little lick. Sam dropped to his knees and unzipped Sean's pants. The strap on popped out and he gave it a little lick, then took the head in his mouth and sucked it briefly before rising back to his feet. Sean gave him a big, deep kiss in appreciation.

Somehow Dan and Kim had seen what Sam did and cheered a little as they came back over. They told Sam and Sean that the bar was closing, and suggested they all go back to their room for drinks.

Sam was so excited when Sean agreed, and their hands were all over each other on the cab ride back. When they got up to the room Kim handed everyone a drink and they sat down on the couches. She then turned to Dan and began making out with him right in front of Sam and Sean.

Sean looked at Sam, and he looked back, and they too began making out.

Sean's hands went down Sam's panties and pulled his cock free and began stroking it. They looked over and Dan and Kim were gone, but they heard moans of pleasure coming from the bedroom.

Sean dropped to her knees and began sucking Sam's cock. Sam was so hot, ready to explode, then Sean would stop touching his cock and kiss other areas until he cooled down, then tease him again. Sam was getting so close each time, then Sean's hand began rubbing his ass, and Sean inserted a finger as she sucked.

Sam began begging Sean to let him finish, and Sean told him that since he was dressed as a girl tonight, he'd have to finish using his pussy. Sean then slid another finger into Sam's ass and started working it. Sean unzipped her pants and let her strap on out. She pushed it up against Sam's slick ass and pressed it in.

Sam was lost in pleasure as Sean fucked his ass. It felt so good, and he needed to cum so badly now. He begged for more and Sean picked up the pace.

Finally, he heard Sam start to moan and felt the strap on get even bigger in his ass, that put him over the edge and he began to cum. At that same point he felt and explosion in his ass as Sean blew his load deep into Sam.

Only then did Sam realize that not everyone was dressed up at the party they were at.