This is a work of fiction. Any character portrayed living or dead is purely coincidental.
Jessica was sitting in the bar. She was 26 and dressed in her favorite football cheerleader outfit with tan nylons and white sneaks. Some guys soon walked into the bar. They ordered beers and a few other drinks. One guy walked up to Jessica. "Hi I'm Kevin, 45 and 8.5in." Jessica looked him up and down. She smiled as she ordered her beer. "Have you ever been with a man before?" He asked. Jessica laughed. "Of course." She said. Kevin kept making small talk.
After a few minutes he excused himself. He went back over to his buddies. Jessica enjoyed her beer then got up and headed for the bathroom. The bar only had one bathroom and it was unisex. Kevin got up a minute later and tried the door. It was locked. He knocked lightly. Jessica opened the door. Kevin took her in with his eyes. She was a good 5ft 6in. And he was good foot taller than her. He pushed her sternly. He looked at her. "I want you to blow me."
He looked at her as he closed the bathroom door. Jessica looked up at him with pleading eyes. In her trembling voice she had him bend down. She whispered something in his ear. Kevin didn't say anything for a minute. Jessica took unzipped his pants and his cock flung out. Jessica took her red lips licked them good. "I like a guy who goes commando." Kevin smiled. He placed his hands on top of her head. Jessica swallowed all she could. She got him to almost cum but stopped. Kevin looked at her angry. Jessica got up slipped a piece of paper in his pants pocket. She walked out of the bathroom and ordered another beer. She then left.
Kevin was watching her leave. He told his friends to hang on as he ran out the bar. Once outside he looked for Jessica. He shrugged his shoulders thinking all was lost. He walked back into the bar and put his hands in his pocket. He pulled out some money and the note. He read the note. Meet me at the cheap motel on third, third door. Kevin wasted no time.
The motel was a good three miles from the bar. He said his goodbyes to his friends then left. He got to the motel knocked on the third door. Jessica opened it up. Kevin excused himself in then shut the door. Jessica had a wicked smile. "Have you been with another man before?" Kevin didn't answer. "Have you been with a cross dresser before?" Kevin again didn't answer.
Jessica looked at him to say something. After a brief moment Kevin spoke. "I never fucked a cheerleader before." Jessica smiled. "Finish what you started bitch." Jessica walked over to Kevin and dropped his pants. Jessica took her tongue and licked his shaft. She licked from the base to the tip of the head. She spat on it then swallowed. Kevin kept his hands firmly on her head as she continued to suck. "Oh God." Kevin said. Jessica could feel Kevin's head swell. She tasted the pre cum. "Oh fuck yeah." He said. Jessica really worked her mouth.
Finally Kevin shot his thick load in Jessica's mouth. Some of the cum dribbled out of Jessica's mouth and onto her shirt. "That's great honey." As Kevin then shot another load down her throat. Jessica got up and Kevin slapped Jessica's ass in a playful way. He then lifted her skirt. Jessica smirked to herself as Kevin saw she wasn't wearing panties. He saw her little cock. "That's so cute." Jessica felt Kevin's hand push her back down like he was going to fold her in half. With her ass up in the air. Kevin then went and began to insert his cock into Jessica screamed as he inserted it in. He pushed it all the way in. Kevin pushed it all the way in. His ball sack slapped Jessica's ass. He then slowly started to pull out then push it in. He gained a rhythm as both began to moan. "Don't stop." Jessica said. Kevin kept fucking her ass hard.
After a few minutes Kevin shot his load into Jessica's ass. When he removed his cock he shot another load that hit the back of Jessica's left leg. Kevin walked to the front of Jessica and began to stroke her cock. They kissed as he kept stroking her cock. Just before she shot her load Kevin pushed her cock down to her right leg. Jessica shot her own load on herself. Jessica took her top off. Kevin bent down and began to suck on her nipples. "Suck these nipples." Jessica screamed. Kevin pushed Jessica down onto the bed he stood above her.
Jessica watched as Kevin jerked his cock off. He went and shot his cum all over Jessica's face and chest. They then went into the shower. Kevin inserted his cock into Jessica's nylons they rubbed cocks while kissing. Then Kevin went and urinated in Jessica's nylons. "I'm sorry." Jessica smiled. "No big deal." As Kevin smiled they kissed some more.
He bent her over a second time and began to fuck her ass again. Both moaned. "Fuck me, Oh Shit." Jessica screamed. Kevin shot his load one more time for the night. "My turn." Kevin smiled as Jessica walked behind Kevin and began to give him a rim job. Kevin moaned. Jessica smirked to herself seeing Kevin get excited again. "Looks like it's going to be fuck session all night." Jessica said to herself. She stopped the rim job as she looked at Kevin.
"How was that?" Kevin smiled. "You are the best gay crossdressing lover." Jessica blushed. Knowing how happy he made his boyfriend. He then gave her boyfriend a small chuckle. "2-4-6-8 you may watch as I masturbate."