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#Cuckold #Mature #Trans #Virgin
By August Moon
A young man sees a handsome man sitting on a bench and they begin a relationship that turns out to be love.
I would see him sitting on a bench every day with a sketch pad. And I became intrigued by him. So I began to sit on the next bench close to him. One day I got up the nerve to go talk with him.
“Hello, my name is Bart. I am so intrigued by you for some reason. I mean it’s not like I’m into men, but we’ll there’s just something about you that I want to know. Something intimate and so exciting. I hope I’m making some sort of sense. Oh my here I am just rambling on and haven’t even given you a chance to speak.” He said to the older handsome man.
“Oooh that’s okay, I found you very amusing, not that I would make fun of you. My name is Jerry, and I have noticed you sitting there watching me. Perhaps there is some hidden interest between us that needs exploring.” He said as he looked the young man over. “I sit here sketching boys, young men and men. Then when I get home, I add the final touch.”
“Something personal for yourself? Can I buy you a cup of coffee and a piece of pie so we can talk more ?” Bart said to the man
They rose and headed off to a nearby Deli and placed their order. They sat well out of the ear shot of others. They talked about themselves and their interests. Bart told him that he worked as an investment manager and that he was single and exploring different options. The older man said he was a retired college professor, who taught sociology. He told Bart that he became bored just sitting at home and took a walk in the park and decided he would sketch people waiting on the bus. Since then he has come to know some peace. They sat and talked for nearly three hours. After that they would meet at the park and then go to the Deli or a nearby restaurant to eat. Their friendship grew.
One night as Bart lay in his bed, he began to think about Jerry and fell asleep. He had arrived at Jerry’s home and they began to drink. Jerry asked him if he wanted to watch some porn. The booze was affecting him and he said yes. They sat together on the sofa. The movie was a cross dressing movie. His cock hardened and Jerry took note of it. Jerry slipped an arm around him and he scooted up to Jerry, their bodies touching one another. Jerry turned his head and placed his lips on Bart’s. Jerry whispered into his ear, “I want to make you my gurl.” Bart heard the alarm go off and realized he had been dreaming. The next day he met Jerry at the same place and Jerry asked him if he would be his date to a party on Friday. They both laughed and Bart agreed to go with him. Friday came and Bart got ready and waited for Jerry to come and pick him up for the party. A limousine pulled up and Jery opened the door and Bart stepped in. After the party they went to Jerry’s home. Bart was feeling the effects of the partying as he sat on the sofa. Jerry fixed them a drink and asked Bart if he’d like to watch a movie. He said sure and the movie started and Jerry sat down on the sofa with Bart. Bart started to think, Deja vu. The movie started and it was a cross dressing one. Bart’s heart skipped a beat and his cock started to harden. This wasn’t a dream, it was for real. He watched the movie and Jerry also.
“From the looks of your trousers, it seems as though you enjoy this sort of action. Mmmmm, yesss for sure.” He said to Bart softly. And moving closer.
Bart’s heart was beating much faster and his cock stayed hard. Bart felt Jerry’s arm slip around his back and then as if in a Trance he moved closer to Jerry and their bodies touched, just like in the dream. What now he thought, would he be kissed by Jerry and would he let him? The suspense was exciting. And he wondered was he deep down gay? He had never been with a man yet in secret he envied what women wore. Then he felt Jerry’s hand on his face and he let him turn his face. Just like in the dream, Jerry moved his face onto Bart’s and he kissed him on the lips. Bart found himself responding to Jerry’s kiss. Then he heard Jerry whisper, “I’m going to make you into my gurl.” He felt so giddy and he moaned as he put his arms around Jerry’s neck. He felt a change coming over him as though he was becoming a new person. Jerry stood up and took him by the hand to a large room. Jerry instructed him to undress completely. He took measurements of his body and then told him to put on the items he laid on the bed. Still feeling the effects of the earlier drinks and sipping on a new one brought by Jerry, he didn’t hesitate to don the items on the bed. The first ones were a lace yellow matching bra and panty set. They were a snug fit. Next came a garter and stockings. His cock was straining against the material of the panties. Next he put on a lace yellow silk slip. Followed by two lace yellow petticoats. By this time he was burning with sexual desires. Lastly was a pretty yellow A-Frame dress and a long hair wig.
Jerry had disappeared and Bart picked up his drink and made his way to the living room, passing the Den, he saw Jerry sitting on a couch. He went in and Jerry patted a place close to him.
“Mmmm you look gorgeous my love. Sooo sexy and sooo innocent.” Jerry said softly to him.
He took Bart into his arms and kissed him. Bart now felt so feminine. He wasn’t male any longer and he, she now felt so free. She noticed his robe open and could see his cock. She had never sucked a cock but was drawn to it. She reached down to grasp it. It felt so hard but yet so soft. She slid down on her knees and spread his legs. The robe opened wider revealing a handsome looking cock. She held it and coming closer she kissed the head tasting his precum. It was sweet tasting and she ran her tongue along its crack lapping up more. She slipped her mouth over its head and swallowed as much as she could without gagging. She began to move her head up and down on his hard cock. As she sucked, she became so turned on by it. She rubbed it against her cheek and planted kisses along its length. She teased the head with her tongue. He began to push into her, grabbing her by the head and holding her head in place. He shot his first load into her virgin mouth. She swallowed fast, losing some out of the side of her mouth. His next three shots came in fast session’s. She swallowed all of them and then with her tongue she cleaned him up. She moved back up to sit next to him. He put his arm around her and turned her head and kissed her deeply.
“Honey, I hope you can spend the night. I want to finish making you my gurl.”
“Mmmm yeeesss, daddy I’d like that. Thank you for helping me to find myself. I hope I can be all that you want.”
They stayed up a little longer talking and then they went to bed. She cuddled into him and held his warm cock. They woke up with Jerry having his cock next to her pussy’s entrance. She turned her head and kissed him.
“Fuck me! I want your cock in my pussy,” she moaned.
He grabbed the gel and began to apply it to her pussy. She shuddered as he did this. He then put more on his cock. He placed his cock at the entrance and started to push it in. She bit on some sheet as the cock met the sphincter. He shoved it into her pussy and began to fuck her. It was a while before she caught on to his rhythm and started to push up to meet him.
“Ooooh honey, honey it feels sooo good. Mmmm yeeesss, I love it! Oooh god, yeeesss fuck my pussy, please fuck me hard. I want you, I love you so much oh honey fuck me. Make yours! Aaaah yeeesss, yeeesss! Mmmmmm.”
Jerry began to use long strokes on her pussy. She was pushing up hard. She wanted all the cock she could get. His rhythm increased as he neared his orgasm. She was panting hard and felt him shoot his first load into her. She pushed up hard as he filled her up with his seed. They laid together kissing.
“I’m going to call you Marty from now on and you are now my gurl. Okay?”
“Yes daddy yes. I want to just make you happy in any way I can. I love you! I really do!”
They showered together and spent they day loving on each other.
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By August Moon
#Cuckold #Mature #Trans #Virgin
