Tom Boy Tom Girl

Carl came by to see his 23 year old girlfriend, Tammy. She grew up as a tom boy, but turned out to be a beautiful woman. Carl was clean and well groomed.

"Come in," Tammy said at the door. She had a nice figure with a perfect butt. When they made love, Carl loved to hold her butt cheeks while they fucked. They were hard when she flexed, and she had a strong muscular vagina that seemed to pull his cock in. He could not talk her into trying anal though.

"You are looking nice today." Carl said noticing she had a new hairdo, and was wearing some new ear rings.

Tammy replied, "Thank you. I have to go out of town for a day or two for my job. Are you going to help me with setting up the new TV system?"

"Yes of course. I brought all the tools I will need."

"Timmy will be here if you need anything. He may want to watch you."

Carl replied, "Okay, good. He can keep me company."

With a kiss and a hug, Tammy grabbed her travel bag and left.

Carl had met Timmy before. Timmy had a slight build, and was younger than Tammy. Timmy just turned 18. Tammy had told Carl that Timmy was effeminate and had grown up as a sissy boy. While she had played with toy cars and toy guns, he had grown up playing dolls and dressing them.

Soon Carl had to dispose of some empty boxes, and needed a towel to wipe things off. He knocked on Timmy's bedroom door. "Sorry to bother you but could I get a towel, and where should I put these empty boxes?"

Timmy said, "Come in. I will see if I have one in here." Timmy was wearing some tight cotton shorts with small flowers printed on them. They were too small and exposed his genital package and ass cheeks.

Stepping through the door, Carl could see the bedroom was well kept, the bed was made up, the pillow cases had lacey edges and so did the bed spread. "Nice room," he said.

While Carl was still putting the system together and setting it up, Timmy had changed clothes and was wearing a skin tight pair of silk shorts that sank into his ass crack and exposed even more of his bottom, and were so small they showed part of his ass crack. He also wore a silk tank top that had the bottom half cut off just barely covering the top half of his chest.

To celebrate finishing the job, Carl lit up a joint and shared it with Timmy. Soon he was giving power hits to Timmy. Timmy loved being face to face like that. Carl turned on the system and asked Timmy, "do you want to select a channel?"

"Yes," Timmy was getting a little high and enjoying himself.

Timmy asked as he selected channels, "How do you think I look?"

"Fine," Carl replied.

Carl reached into his bag and brought out a gift he had chosen for Timmy. He said, "Here this is for you. Do you like it?" It was a small glass molding like a vase with a set of roses in full color about three inches high, and it was scented so you could smell roses.

Timmy said, "For me?" He reached for the small vase and smelled it. "Oh that is awesome. Thank you."

Carl always brought some strong wine with him to share with Tammy. She was out of town so he offered some to Timmy. Taking two glasses with ice from the kitchen Carl poured the strong wine and handed a glass to Timmy.

"Thank you." Timmy was very happy.

Timmy found a channel he wanted to look at. It was of two young men exchanging pleasantries, and then hugging letting their hands drift. One of them reached a hand under the band of the others shorts and was fondling his ass.

Carl just let him enjoy himself, and gave him another power hit, and refilled his glass.

Timmy was getting stoned and drunk. He wanted to give Carl a thank you hug but didn't get up. Carl walked over in front of him like he was going to give another power hit. Timmy had his arms out to give a hug. Closing his eyes Timmy wrapped his arms around Carl and leaned in. Carl was still standing so Timmy's arms went around his ass and with his eyes closed his face was right at Carl's crotch.

Moving his hands and face, Timmy hugged vigorously. His mouth ended up over the tip of Carl's cock which was already getting hard. Carl was fascinated and watched as hugging his crotch turned into kissing his cock through his clothes.

From all of what Tammy had told him, Timmy was still a virgin, and had never dated. Now he could see that Timmy was sexually pent up, and eagerly absorbed attention. Carl held the back of Timmy's head and guided it up and down his shaft slowly letting Timmy kiss it all the way down and between the balls, smelling of his crotch all the way back up. While he held Timmy's lips against his cockhead, he started unzipping his pants letting Timmy feel the vibration with his lips and letting him know what was about to happen. He unbuckled his belt and let Timmy kiss the leather of his belt and smell it. He rubbed the leather belt against Timmy's lips, nose, and face. He inserted the tip of it in Timmy's mouth and let him kiss and suck it for a minute.

While doing that he started to pull his pants down a little letting the band of his underwear free the top of his cock. Now he brought Timmy's mouth back to it with his eyes still shut in bliss. Carl watched as Timmy started naturally kissing, licking, sucking, and smelling his cock.

Now, Carl started giving him encouragement, "Go ahead and lick around the flare."

Like a new idea had struck him, Timmy licked all around the flare, the crown and the piss slot. Licking the piss slot seemed to invigorate him, as he had a taste of precum for the first time. He wanted to taste more so he sank his mouth further down the cock, sucking hard enough that it pulled his lips out fully stretched when he drew back up.

Carl said, "You have perfect lips."

He licked the shaft all the way down between the balls. The pubic hairs tickled his nose. With his mouth over the cock he gently blew air down the shaft and through the pubic hairs of Carl's balls. He could feel the heat off the cock rise into his mouth and on his face.

Carl said, "Kiss and suck the balls for me."

Timmy was engulfed in new experiences and tenderly kissed and then sucked each one of the balls, letting his tongue travel to the skin behind the balls. He let his lips form a perfect circle just the right size for the balls to squeeze in. Tasting balls for the first time was a wonderful experience he never anticipated.

Carl asked, "Is it good."

"Uh huh," Timmy replied.

"Lick between the balls again and go all the way back until you are licking the ass cheeks." Carl hunched his crotch up and spread his legs some to allow for Timmy's head.

Eagerly Timmy licked all the way back vigorously tasting the wrinkly scrotum skin, and then the perineum, and then the brown wrinkles, not realizing at first he was licking Carl's asshole for the first time. He licked the ass crack around the asshole, and the butt cheeks. He licked the asshole again marveling that it didn't taste bad and how it felt against his tongue. He licked all the way back to the top noticing how puffy the cum vein was and how nice the velvety skin tasted. When he got to he top, Carl pushed Timmy's mouth over his cock.

"Suck it."

When Timmy pulled out to the cock head he licked the cockhead getting a little more precum with a heavier taste to it. Carl was pumping his cock in and out but suddenly pushed hard and held Timmy's head on it.

"Close your lips around it tight and don't loosen up."

Holding Timmy's head tightly, Carl started bucking and Timmy could feel the cock expand. Then he felt the cum vein pulsing on his tight lips, and a volley of cum splashed into the back of his mouth and throat. Carl shot several good streams of cum into Timmy's mouth, and held Timmy in place for a few minutes. "Suck it clean Timmy."

Timmy could taste a glob of the cum on his tongue. He sample tasted it and lavished on the opportunity to have his first taste of cum.

All of the new tastes and smells were even more enhanced by the pot smoking.

Timmy had to be pushed off his cock. Carl asked, "Where is your restroom?" He had to pee.

Timmy pointed to his bedroom and followed Carl in there to show where it was.

After he peed, Carl started to zip up, but then he saw Timmy had come up beside him. Thinking Timmy had to pee also Carl turned toward him a little to trade places, but unexpectedly, Timmy dropped to his knees and happily sucked the pee drops from the end of Carl's cock. It seemed he couldn't get enough of cock.

Carl saw the clothes hamper had panties in it. They weren't Tammy's.

They went back to the living room and got another glass of wine and as Timmy selected another of his favorite genre movie, Carl lit up another joint.

Timmy seemed more open and uninhibited.

Carl asked, "Are you wearing panties?"

"Yes." Timmy had taken his top off and was wearing those very small silk shorts.

Carl said, "Let me see."

Timmy stood up, "Okay."

As he pulled them down he turned. Carl felt of his ass cheeks. "You don't mind me touching do you?"

Timmy was so glad he asked. "Go ahead."

Carl slid his hands to the bottom cheeks hanging out and up to the sides and small of his back and over the exposed ass crack. Sticking a finger in the crack, he pulled the shorts down and saw Timmy was wearing bright thong panties.

Carl knew that Timmy loved skin lotion but could never get it rubbed on his back. Carl turned Timmy around to see the panties from the front, not covering everything. Now all that Timmy was wearing was the panties. "Nice butt," said Carl.

"Thank you."

As he pulled the panties all the way to Timmy's ankles, Carl tapped his leg to lift and he pulled the panties all the way off. Timmy was completely naked.

Timmy had a hard on from all the events and the movies playing again. The air on his skin from being naked made his cock harder, and with another man seeing him naked was a turn on.

They had some more strong wine, and Carl gave more power hits to Timmy.

Carl said, "I brought something for you."

Timmy said in surprise, "For me?"

"Yes, smell this. I brought you some skin lotion."

Timmy smelled the lotion and it had sort of a tropical smell.

"It is edible, here," Carl put a little of it on his finger and pushed it into Timmy's mouth. Timmy sucked the finger clean twirling his tongue all over it and sucking it dry.

"Lay over the side of your bed and I'll put some on your back."

Carl couldn't help but admire the soft and shapely ass cheeks as he watched Timmy go back into his room and submissively layed over the bed. Now his fine ass was in complete view and he was reminded of the one thing that Tammy would not let him do.

Carl started rubbing the lotion into Timmy's skin in small circles all the way up to his neck. He rubbed the small hairs of his neck, behind the ears, and let his finger play into Timmy's ears. This sensation turned Timmy on so much, his whole body seemed to get hot. Carl rubbed the lotion all the way to the small of the back and then he started working around the sides of Timmy's bottom. Carl's cock was hard again.

Carl felt the softness of the ass cheeks, and massaged the ass crack. He rubbed the lotion firmly all the way down the ass crack, and firmly massaged the cheeks. Pulling one cheek aside he put lotion on the anus and rubbed it in.

Timmy was in heaven with all the personal attention. He felt a coolness on his asshole, and then Carl's finger seeming to massage his asshole. He felt his asshole move to one side then another as the finger kept working around. It felt like the finger was going in. Then it felt like the finger had stopped, but was pushing in, but very slowly.

Soon the finger was pushed all the way in, and then slowly pulled out. Another finger was added and he felt his butthole being moved all around. He felt a coolness.

He giggled when he felt Carl's cock sliding between his ass cheeks. Then he felt it rub all the way down his crack and back up. More lotion was applied to his butthole which felt funny. He had never thought about what that might feel like.

The head of Carl's cock was pressing on his asshole. Timmy could not predict what might happen. He just took everything much as a new adventure.

Curiously he felt the head of Carl's cock get warmer as it felt like it was squeezing into his asshole. He felt it move around a little and press in more. It felt like it was getting deeper but the hole was too small. Then he started to get a fullness as it felt like the shaft of the cock was going in.

Timmy did not want it to end. He felt close to Carl and loved the feel of Carl's cock sliding in and out of his asshole. When Carl grunted and clinched in an explosive orgasm tightly hugging Timmy, he felt fulfilled and loved. It was satisfying to know the cum from the balls he sucked had pumped into his mouth and his asshole.

Discreetly Carl had videoed every thing from the time he placed his cell phone and his camera in ideal positions in the living room, bathroom, and bedroom. He had some nice shots of the tight shorts, the panties, and the naked shapely ass, and of the ass up position on the bed exposing his anus and ass crack.

These pictures and videos would go well with the collection he had taken of his girl friend.

Carl was enjoying life. He was getting good pussy, and some tight ass.