tagTranssexuals & CrossdressersCollege Shemale babysitter

College Shemale babysitter

bytomf15©

Disclaimer: All characters are 18 and over.



Jessica pulled up in front of a large house at the end of the street. She looked down at the text; 1278 Backstreet.

"This is the right place," she thought. Jessica was a fairly normal, attractive college girl. She studied hard, partied on weekends, and liked to work out. There was one thing that separated her from her classmates. She was a shemale. It was a secret she had never told anyone, for fear of them rejecting her. As such, she was still a virgin, being to afraid to let a guy in her pants. She was at the house to babysit, to help pay for her tuition. The couple who hired Jessica said they had two kids, a young baby girl, and a eighteen year old son they didn't trust to not invite friends over and trash the house. So they hired Jessica to watch the kid and make sure their older son didn't get into trouble.

Jessica walked up to the door and knocked softly. After a short while, it was opened by a tall, brown haired young man. He was broad shouldered and rippling with muscle. He had a face that was both aggressive and friendly at the same time.

"Is this 1278 Backstreet?" Jessica asked.

"Sure is. I'm Tom," the hot boy replied with a smile. "And you are?"

"I'm Jessica, the babysitter." she said, taken aback by this hunk. She was not expecting him to be so, well, hot.

"Come on in. My parents just left. They'll pay you tonight." Tom stepped back and allowed her to enter. "My sister's in the room upstairs. I'm just about done my workout, then ill probably take a shower. The baby food is in the kitchen. He walked into the basement and Jessica heard the sound of a barbell being lifted.

As Tom finished his last set of bench presses, he thought about the blonde college babysitter. She was pretty short, about 5'5'', and had huge, firm breasts that must be at least a D-cup, packed into a low cut top that showed ample cleavage. They jiggled a bit whenever she moved. Jessica had a beautiful face with striking blue eyes. As Tom imagined getting intimate with her, he felt his pants start to get tight.

"Shit," he said under his breath as he went up stairs to shower. Going to the bathroom, he saw Jessica bending over to pick up his sister and put her to bed. Her tight black leggings hugged her bubble butt just made Tom harder.

He quickly closed the door and pulled off his clothes. He got into the glass walled shower and turned on the water. As he washed, he pictured Jessica and his cock grew to full length. He slowly started stroking it, thinking about the sexy blonde's big tits and firm ass. He imagined himself fucking her tight pussy, and seeing her gorgeous face in ecstasy as he pounded her.

After having put the baby to bed, Jessica decided to go to the bathroom to freshen up a bit. She slowly opened the door and upon seeing Tom jerking off naked in the shower, stifled a gasp and almost closed the door to leave, but the sight of the hot muscular boy in there almost hypnotized her.

As she watched him stroking his huge cock, she felt her leggings get tight as her shemale dick hardened. So entranced by Tom, she started to rub her crotch with one hand and her breasts with another. Jessica got so horny that she pulled out her stiff cock and started to masturbate as well.

Tom was interrupted by a moan from across the room. He whirled around and saw Jessica rubbing her ... dick! Jessica gasped and tried to cover it."I'm so sorry!" She was afraid this would happen. He would freak out at her being a shemale and walking in on him masturbating.

"It's okay," Tom whispered. Recently, he had started watching a bit of Shemale porn, and had been desperate to fuck. And now, he has his chance! He took in the lust in her eyes, the bouncing tits, and the hard shemale cock."I've been wanting a girl like you." He stepped up to her, closed the door, and grabbed her big ass. Jessica looked up at the attractive man in front of her and lost control.

She grabbed his head and kissed him passionately. They started to feel each other, her hands going over his well muscled body, and his caressing her tits. He tore her top and bra off, and started to suck on her erect nipples. Jessica moaned with pleasure. This was the most intimate she had ever gotten with a boy. She rubbed her little four inch dick against his giant nine inch cock. Jessica almost came on the spot.

"Mmmm, feels nice, doesn't it?" he asked. "Now I want you to get on your knees and suck my cock, slut." Being dominated turned Jessica on even more. She got down, a started to stroke his big hard rod while jerking herself off furiously. She took his fat head in her mouth and started to suck with her soft lips. She started off slow, swirling her tongue around the head.

"Go deeper," Tom ordered. She sucked harder, trying to fit as much cock as possible in her tight throat. He grabs her head and starts to facefuck her.She gags as his huge cock is thrust in and out of her mouth. "Take it like a good slut!" He pulls his cock out and slaps Jessica's tits. "Turn around!" She presents to him her big firm ass. Tom spanks her, "You want this in your ass, whore?" He growls.

"Yes! Yes! Fuck me please!" she begs. He places the cock head on Jessica's virgin asshole and slowly pushes it in, inch by inch. Once he's halfway in, he pulls out almost all the way, then plunges deep and starts to fuck Jessica's tight ass like an animal.

"You like having this big cock fuck your ass?" Tom panted.

"Yes, oh God yes! Fuck me harder!" She screamed. He flips her on her back, and rams her asshole while squeezing her big tits and pinching her nipples. Jessica shrieks in pleasure. She jerks her little cock as fast as possible.

"I'm gonna cum!" She moans, and her shemale dick squirts out her seed all over her stomach. Her ass tightens even more, and Tom can barely stand it. He pulls out and puts his cock in Jessica's face.

"I'm gonna cum too. Jerk my big dick into your slutty mouth and tits." She grabs his huge cock with both hands and strokes furiously.

"I need it! I neeed your cum!" Tom explodes, shooting the first string of cum directly into her open mouth. He keeps gushing cum, covering her face and covers her tits with his jizz. Jessica swallows and looks up at him. "Maybe I should babysit your sister more often.

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