John knocked on the door to his friend’s house and it swung gently open. The latest chart music boomed from inside. 

He called out, “Hi its John?”

No answer; so he went further in the house the music was coming from upstairs so John went to investigate. He needed to find someone so he could pick up the money. The music was louder upstairs and though he called out again no one answered.

Then he saw his friend’s thirty year old son Tim. He was dancing around in a red lace thong to the music. Tim saw John and froze; the look of fear on Tim’s face evident to see, Tim grabbed for a towel on the bed as John stepped into the room.

Tim stammered something but John wasn’t really listening. He liked how Tim looked. Then he focused on the words. Tim was trying to make excuses for wearing a girl’s thong. John held up a hand to stop Tim talking.

John asked, “Do you enjoy wearing the panties?”

Tim looked at the floor and whispered, “Yes!”

“Then don’t be embarrassed Tim.”

“Take the towel off.”

Tim dropped the towel to the floor.

“Do you have any other lingerie Tim?”

Tim did not answer he just shook his head. John said, “Follow me?”

Tim followed John in to the main bedroom. John was looking through the make up on the table and picked out a lipstick. John moved and applied the scarlet lipstick to Tim’s lips. Then John rummaged through the draws until he found a red bra and black lace top hold up stockings; he handed them to Tim and said, “Put them on.”

Tim complied and was soon sliding the stockings up his legs, the tingle of the sheer material against Tim’s legs made his cock twitch. John noticed the reaction putting the lingerie on had on Tim.

John checked in the closet and found a pair of black four inch high heels and a wrap dress. Again he handed them to Tim but before he could say a word Tim was moving to put them on. Good girl John thought to himself.

Tim stood in front of John dressed as a girl, embarrassment flooding his body mixed with tingles of pleasure as the various materials caressed his body.

John walked back to Tim’s room and Tim followed without a word. John turned to Tim and said, “I will call you Tammy, now dance sexy for me baby.”

And pressed play on Tammy’s stereo.

Tammy swayed her hips; caressing her body with her hands as she danced to the music. Soon Tammy’s eyes were closed and she was lost in her own world as she danced; an inner sexiness she hadn’t been aware of coming to the surface. Her hands all over her body caressing her small breasts and pulling her dress up to expose her stocking tops and thong.

John sat on the bed watching Tammy come to life in front of him. His cock throbbed and pushed against his trousers; he undid his trousers and pulled his cock out and gently stroked as he watched this vixen in front of him.

Tammy opened her eyes and realised John had his cock out and in that moment Tammy was thrilled at the reaction she had on him. She slipped her dress off as she danced.

John watched as Tammy slipped her dress of her shoulders and slide it down her body exposing first her bra and then her thong and stockings. He stroked his cock and felt the wetness as juices flowed.

Tammy saw John masturbating his cock and she was in awe and without hesitation she dropped to her knees and crawled across the floor and between his legs. Until her face was just a couple of inches from his cock.

John watched Tammy drop to her knees and crawl on all fours across the floor to him like a hungry animal. Her eyes solely focused on his cock. When she was close to his cock John reached out and with a hand on the back of her head pulled her in and pushed his cock between her lips; the warmth of her mouth around his cock intoxicating.

All of a sudden John grabbed the back of Tammy’s head and his cock pushed through her lips. She expected to vomit but was surprised at the sweet taste of his cock and the way it felt nice filling her mouth. Her tongue licked the cock in her mouth feeling the texture of the flesh and contours of the muscles. Tammy realised she liked this and soon she started gently sucking on John’s cock. Vaguely in the height of her own pleasure and submission she heard John moaning in pleasure.

John watched as Tammy bobbed her head up and down on his cock the gentle suction of her mouth sending waves of pleasure through his body. His arousal built and he started thrusting up. The head of his cock hitting the back of Tammy’s mouth; she didn’t resist and seemed to try and get more of his cock in her mouth.

Tammy’s tongue could taste the juice that leaked more and more from the head of John’s cock and each drop just made Tammy hungry for more.

John was in heaven with this delicious whore’s mouth on his cock but he wanted more. He grabbed Tammy by the shoulders and throw her face down on the bed. He dropped on top of her and heard her gasp as she was pinned down.

In her ear he whispered, “Suck my fingers wet!”

He thrust two fingers in her mouth. Once he felt that his fingers were nice and wet, he took them from Tammy’s mouth and pulled her thong aside. His fingers thrust them deep in her ass stretching her. Tammy squealed in shock.

Tammy felt John’s weight on her pinning her down. She sucked on his fingers as he instructed and felt his cock pressing against her ass. She knew what was coming and instead of resisting she accepted her position. Tammy gasped as he pushed his two fingers deep into her ass and felt the friction as John fingered her ass hard. The pain to start; then turning to pleasure; she moved her hips and ass to make the finger thrusts go in her at a better angle.

John felt Tammy shift position make her ass better able to accept his fingers and at that moment he knew she was ready. He pulled his fingers out of her ass and masturbated his cock up and down the cleft of her ass, his juices lubricating her. He placed the wet head of his cock at the entrance to Tammy’s ass and was rewarded with the sight of her asshole twitch. He pushed in and soon his cock was buried deep in her.

Tammy winced as John’s cock entered her and her hands clenched the bed. But she knew this is what she needed. She was positive she could feel every inch and vein of his cock as it slide deep in her. Her mind raced with pleasure of submitting to a man. Then she felt the first deep thrust and the sudden emptiness as he pulled back and then the pleasure as she was filled again. Over and over the sensation of pleasure from the thrusts and the sadness of emptiness.

John was soon pumping Tammy’s ass like a jack hammer the tightness of her ass on his cock sending thrills through his body. The arousal was amazing and he knew he was soon going to cum. He reached under Tammy and rubbed her lace covered cock. He was rewarded with Tammy raising her ass to accept each thrust and was breathing hard, her body trembling.

Tammy was in heaven each time Johns cock buried deep in her ass then he reached and started rubbing her lace covered cock. The multiple sensations drove her crazy and then she orgasmed her cum filling her panties. She wanted Johns cum after that, she wiggled her ass and pushed back onto his cock.

“Fuck me John!” she said.

John was in heaven; he had this sissy ass and he was pounding away like crazy, the tightness on his cock pushing him closer and closer to orgasm. He felt Tammy cum as he rubbed her cock and her ass push onto him. He was so close to cumming. Then Tammy begged for him to fuck her. So he did thrusting harder and harder until his body could take no more. John’s orgasm washed over him and he pumped cum deep in Tammy’s ass. Two, three spurts of cum emptied from his cock filling Tammy’s ass.

Tammy felt Johns cock throb and he pushed deep in her ass. She heard his grunts and realised he was Cumming in her. At that moment she was pleased that she could make a guy cum and was shocked by that revelation. She relished the spasms Johns cock did inside her as he filled her with cum. All too soon he stopped and she realised it was over for her. Tammy felt John moving and withdrawing his cock from her insides and the emptiness was horrible, the feeling of his cum leaking from her did not satisfy her the way his cock did.

John moved and pulled his cock from Tammy’s wonderful ass he could easily be on love with this sissy as she fucked like a pro and clearly wanted it. He pulled his trousers up and smoothed himself down watching Tammy just lay there on the bed his cum leaking from her.

He moved Tammy to a seated position and leaned in to her and kissed her full on the lips. When he broke the kiss he told her.

“Tell your dad to give you the money he owes you and that you will bring it over to me. But spend the money getting yourself something pretty things!”

“Yes John,” she responded.

Tammy watched John leave and resolved to be sexier the next time she see him. Tammy picked up her phone and texted her dad the message about the money hoping he gave her the money that day.