Hot "Chick"

Ben and Carl weren't very popular at school. They were sometimes picked on but for the most part they were just invisible. They were grateful that they found each other since otherwise each would have been a complete loner, both at school and also away from school.

Every weekend Ben would come over to Carl's place to play video games. That, in addition to reading comic books and computer and gaming magazines, was all they pretty much did.

Ben often talked about how great it would be if they found some "hot chicks". Ben longed for that kind of intimacy with a woman and wondered, as a virgin (which Carl was, too), what it would be like to kiss the head cheerleader, say, or just to be with a girl in an intimate way. Carl longed for intimacy too but it was a little more complex for him. See, Carl had a secret - a secret going by the name of "Karly". Karly loved to dress in his older sister's pretty things. Carl couldn't get the girls but he, too, wanted to be with a girl just as much as Ben. However, Carl found a way to remedy the feminine lacuna in his life: he could dress up and be the girl to whom he could do whatever his lusting heart desired! But, because Karly looked so hot and sexy, which was completely contrary to the skinny, dorky, long-haired gamer Carl, the whole sex thing became entwined with Karly: it was Karly who wanted to experience what it was like to have sex...as Karly!

One Friday night, when Carl's family were up at the Lake House, Ben came over to stay the night. He was going off again about how he just wanted to meet a "hot chick" and to make love to her all night while they were both surfing on the internet on their laptops. Carl could see from the bedroom mirror that Ben was looking at porn on his laptop, and that Ben was noticeably hard under his pants.

Carl told Ben that he could dress up as a girl just for fun. Ben laughed and said "whatever, you're weird". Carl went into his sister's bedroom and came back out as Karly an hour later, wearing thigh-his, high heels, a frilly skirt, tube top, and some make-up. Ben looked up and his jaw dropped!

Karly brought Ben over to the bed and said "Just pretend that I'm a girl, then you can live out you fantasy". Ben was hesitant but intrigued. He couldn't believe how hot Karly (Carl!) looked all gussied up as a girl! He checked out Karly became really hard. He finally gave in. "Okay, we're just experimenting - doing this since this is the next best thing, er, well, you know what I mean". "Yes, of course!" Karly responded.

Karly was sitting at the edge of the bed and Ben was still standing. She hopped on the bed on all fours and turned around to see Ben. "What do you think of this?" Ben was slightly trembling, and his pants had a incredible bulge. "Uh, yeah, that's hot". "How about this?" Karly laid on her back and spread her legs, holding her thighs to help lift up her ass a little and bring her ankles by her ears. Karly's panties shifted a little and showed her tight butthole. "Yeah, that's nice" Ben said, with a quiver in his voice.

Karly got up. "You want me to suck your cock?" Ben hesitated and then replied "Um, sure". Karly came back to the edge of the bed where Ben was standing, unzipped his pants, and pulled out his cock. She couldn't believe how big it was. He had never seen his friend's cock, and and she couldn't believe that she was looking at it, holding it, about to suck it! While on all fours on the bed, engulfed his cock. She had never done this before so she took it in too quickly, gagging a little. Ben couldn't believe it. The feeling of the cool air caressing his exposed, rock hard cock, and then being sucked by a hot, wet mouth, was enough to make him cum, so he immediately said "Wait...you're gonna make me...". Karly just sucked really hard, thinking that that's what you're supposed to do. She sucked on Ben's cock like it was a large straw. Ben said "Wait, stop...just keep your lips wrapped around it and hold still". She complied, and Ben just slowly moved his cock in and out of Karly's mouth. "Oh my god, that feels so good", Ben said. He was slowly fucking Karly's mouth.

Karly was really hard now and was able to loosen up her throat. She loved the way it felt on her tongue and her throat as Ben slid his shaft in and out, gently holding the back of her head, knees bent, moaning, "Oh my god, I can't believe it...Ooooh". But Karly wanted more. She at that point really wanted a pussy so that Ben could really fuck her. That's when Karly thought that maybe she could use the only hole she has down there as a sort of 'make-shift' pussy.

She pulled back and Ben looked at her. "Why'd you stop? That was feeling so good. What's wrong?" Karly looked at him, "Do you want to try fucking me?" Ben looked at her, puzzled. "How? you mean like pretend fucking like rubbing against you?" Karly felt too embarrassed to ask him to put his cock into her hole, so she just said "yeah". Ben said, "Okay, but, shouldn't we get a condom or something?" Luckily, she had brought one from her sister's room, expecting something like this to happen. She slid it onto his cock, and he moaned and trembled and she slid it on. Then she turned around and bent over in front of Ben. He stared at her ass and hosed legs in heels, her slender body, and her ass just propped up waiting to receive him. "Oh my god, I can't believe I'm doing this..." Ben said under his quivering breath.

He came up behind her and started to rub his shaft against her panties as she was bent over. Upon first contact he was shaking with ecstasy. They looked at each other through the bedroom window, which was reflecting their taboo sex on the bed. He started to rub his cock against the crack of her panty-covered ass. He grabbed her by the waist and ass as he dry-humped her.  Karly then pulled down her panties. Ben asked "Wait, what are you doing?" "It'll feel better if you don't rub on the panties".

He started up again and she was right, to feel his cock, still wet from Karly's mouth, was gliding nicely along the top of her ass crack. Karly gently pushed back with each thrust made by Ben. "Do you have any lotion?" Ben asked "This feels awesome but I want it to glide more". Karly told Ben that the lotion was next to the bed. He reached over, pumped a bunch lotion onto his cock and then started rubbing it on top of Karly's ass crack. He couldn't believe that he was finally experiencing what it was like (perhaps) to have sex with a hot chick. He couldn't believe the moment he was in.

Karly then asked for more lotion, and when he started to apply it, she reached back, grabbed Ben's hand with lotion in it, and directed him to rub it all over her crack, even over her hole. The feeling of his hand gliding over her tight hole made Karly tremble with sexual excitement.

Ben started to rub his hard cock again, but Karly was getting impatient. She wanted his cock inside her tight butthole, but didn't know how to tell Ben. So she hatched a plan. She moved forward a little more than usual so that Ben's cock would fall away from her ass crack, and then moved back, so that the head of his cock came flush against her pussy hole. "Whoa, hold on, that was close...", said Ben, not even thinking that that was an intentional maneuver by Karly. He didn't even think about penetrating her - it didn't even cross his mind. He just thought that this was as good as it gets with a "hot chick" without a pussy.

Before he could move it up and place it on the crack of her ass, Karly pushed back so that her hole stretched to engulf the head of Ben's cock, wrapping tightly around it, popping in and sliding in with a majestic glide. "Aaaaaahhh!" she cried out, and her knees trembled, feeling him fill her tight hole. "Ooooh noooo.....my gaaaaa" Ben said.

"Fuck me, Ben. Fuck me like I'm a girl", she said. He couldn't believe how amazing it felt: tight, hot, wet, and oh the sensation! She couldn't believe the sensation. He couldn't help himself now. He was looking down at his cock sliding in and out of her hole. It was so tight that each slide out of her hole, he could see it pulling back the sides of her pussy because it was so tightly wrapped around his hard shaft. He looked at her, his cock pumping her butthole, and the reflection in the mirror of them fucking. He saw himself fucking an incredibly hot chick. He could smell the floral scent of the lotion mixed with the scent of her ass pussy. He was completely possessed with sexual desire.

It had only been 4 minutes since they began, and 1 minute since they started fucking. But he felt like he was going to cum - big time. He slowed down to slow, long strides in and out. He then realized he was without a doubt going to cum. So, he continued with his long strides in and out, drilling her and ramming her ass to make sure he was deep in her. She screamed in ecstasy each time he pounded her like that. Her cock would bounce up and down each time, and first she came. Her cum went squirting everywhere, on the bed, on her stomach, and on her chin even! "Aaah, Ahh, I'm cumming..." Then, Ben came. He couldn't believe it. "Oh my god, I'm cumming! Ohhhh". He came so much that it started to leak at the edges of his condom. They both collapsed trembling.

Karly stayed Karly the rest of the night. They continued to 'explore' their fantasies the entire weekend. But after that, things were awkward between Ben and Carl. But they found  solution: whenever Karly came out, the awkwardness went away and Ben and Karly had nothing but a lot of fun!