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Gay Stories
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Bi-Sexual Male / 23
Helped Him Transition
At 17 I had an older woman that I fucked. She was my first and it was heaven. She was nicely put together at 62 but not a spec of gray hair, very nice body, tits sagged but still were nice. I would fuck her, eat her, fuck her ass, she blew me, licked my ass, we did everything include go to the nude beach by her house and rub each other with lotion and let people watch and wonder. I even helped out a few of her friends, most chubby, some really fat, others not very attractive but it was pussy, mouth and ass and I loved it all.
One day she told me about her nephew. He was going to be spending the weekends with her. She said it wouldn't stop us at all. When I met him he was embarrassed. She and I were nude, he was in a see through nightie with stockings on. She didn't tell me he was gay. That night while in bed with her she explained that he can only be his femme self with her. He was a virgin in all aspects of sex, but felt very feminine. She helped blow out his hair, do makeup and buy him girls clothes. He was only 15, small framed, had an indented waist and looked like a very pretty girl. sometimes she's use suction on his boobs to make them stand out a bit, sometimes more on his nipples which were pretty puffy anyway. One night we were all watching some movie and she moves on the floor and starts blowing me in front of him or her. She tells him to come and watch, to get close so "she" can learn how to do it. I ended up blowing my load into his mouth. It was kinda hot actually knowing that was the first cock to be in his mouth.
After I recouped, she told him to suck me hard again. When hard, she rubbed some vaseline on his ass and told us to go into the spare bedroom. He was almost crying, saying he wasn't ready, but she made him go in anyway. I wasn't sure what to do but she told me to fuck him and be very gentle. She said to "make love" to him-her and to treat him like a girl. In the room he was offering to suck me to completion again, instead I did treat him like a girl. I kissed, sucked his puffy nipples till he was moaning like a girl, then with her on her back I got into missionary with her and slowly eased into a virgin asshole. It was heaven, he was in a bit of pain, I gave her time to get used to it then fucked. I shot deep inside her new found pussy. When we went out she asked if she was a "real" woman now. the answer was yes, and with that she inspected his butthole and found my cum.
She wanted me to take "her" out on dates dressed as a woman, and I did. My friend paid for everything, and the gurl and I were dating, and sleeping together every weekend. We would even go on the nude beach, where her pumped tits looked like budding teen girls tits. She kept a bikini bottom on, and trimmed the bush to fit into the skimpiest one that my friend bought. I even buttfucked her under a blanket on the beach with a few older couples and male pervs watching.
For over a year, I had a 60+ woman who would do anything imaginable with me, plus a teen gurlfriend. Kissing, making out, feeling up, blowjobs in the car, fucks at the beach. One time after heshe gained more confidence as a woman, not just a teen gurl, I took her out and she tucked herself in (it was tiny anyway) and with public hair she looked on the beach like any 15 or 16 year old girl with a pussy.
It was fun, it was also something I never speak about to anyone, taking the gurls virginity, dating a TS is my dirty little secret. I know that she is gay and lives as a femme, I still occasionally see my old friend, but we don't fuck. I made a promise when I got married and I meant it. My wife is pregnant with a big belly, a full bush below and I love fucking preggo pussy.
One day she told me about her nephew. He was going to be spending the weekends with her. She said it wouldn't stop us at all. When I met him he was embarrassed. She and I were nude, he was in a see through nightie with stockings on. She didn't tell me he was gay. That night while in bed with her she explained that he can only be his femme self with her. He was a virgin in all aspects of sex, but felt very feminine. She helped blow out his hair, do makeup and buy him girls clothes. He was only 15, small framed, had an indented waist and looked like a very pretty girl. sometimes she's use suction on his boobs to make them stand out a bit, sometimes more on his nipples which were pretty puffy anyway. One night we were all watching some movie and she moves on the floor and starts blowing me in front of him or her. She tells him to come and watch, to get close so "she" can learn how to do it. I ended up blowing my load into his mouth. It was kinda hot actually knowing that was the first cock to be in his mouth.
After I recouped, she told him to suck me hard again. When hard, she rubbed some vaseline on his ass and told us to go into the spare bedroom. He was almost crying, saying he wasn't ready, but she made him go in anyway. I wasn't sure what to do but she told me to fuck him and be very gentle. She said to "make love" to him-her and to treat him like a girl. In the room he was offering to suck me to completion again, instead I did treat him like a girl. I kissed, sucked his puffy nipples till he was moaning like a girl, then with her on her back I got into missionary with her and slowly eased into a virgin asshole. It was heaven, he was in a bit of pain, I gave her time to get used to it then fucked. I shot deep inside her new found pussy. When we went out she asked if she was a "real" woman now. the answer was yes, and with that she inspected his butthole and found my cum.
She wanted me to take "her" out on dates dressed as a woman, and I did. My friend paid for everything, and the gurl and I were dating, and sleeping together every weekend. We would even go on the nude beach, where her pumped tits looked like budding teen girls tits. She kept a bikini bottom on, and trimmed the bush to fit into the skimpiest one that my friend bought. I even buttfucked her under a blanket on the beach with a few older couples and male pervs watching.
For over a year, I had a 60+ woman who would do anything imaginable with me, plus a teen gurlfriend. Kissing, making out, feeling up, blowjobs in the car, fucks at the beach. One time after heshe gained more confidence as a woman, not just a teen gurl, I took her out and she tucked herself in (it was tiny anyway) and with public hair she looked on the beach like any 15 or 16 year old girl with a pussy.
It was fun, it was also something I never speak about to anyone, taking the gurls virginity, dating a TS is my dirty little secret. I know that she is gay and lives as a femme, I still occasionally see my old friend, but we don't fuck. I made a promise when I got married and I meant it. My wife is pregnant with a big belly, a full bush below and I love fucking preggo pussy.
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