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A First for Me.

Posted by a gay man:

August 28, 2026

By KestrelElbow9092

He was a Crossdresser, (Pete)smooth petite hung. His " Wife"(Pat) was a chubby attractive woman who accepted his life style, but she ran the show about who fucks her man and she gets some too. Meaning, as a 3some with him or she can go get it without him. That was the terms of the deal, no negotiations. " I can get any cock for me or you." She knew how slutty men could get, she knew about glory holes and cruising, but caught him coming out of a cheap motel with his bag of clothes. Also blackmail evidence if he strays.
I started to tire of the interview process emailing her, but then it turned quickly. " Willing to meet you, but not to play.." The 3 of us had normal lunch, picturing him dressed up and could see it..She was built, nice tits and cleavage, pretty face..oh I wanted a taste of her,but played it cool. We agreed to meet at a motel for first time fun. Pics finally exchanged hours before we meet. She liked what I was packing and his semi bulge in his panties turned me on, smooth ass in thong. Her? A tit Pic with cum on them.
I was nervous as she opened the door, she was wearing a summer type dress and no bra. She kissed me grabbed my crotch hard..looked me dead in the eye, " This is mine from this moment or you can leave now." waiting for my reaction..meekly " yes ma'am." She smiled. His name.." Patti" come out and meet our guest." He was a woman through and through. Teddy with panties, heels, long blond wig, make up done perfectly..she obviously does his make up. She sat back and watched our first kiss, groping her fake tits, feeling his cock as he released mine. Me naked, him staying in his outfit the whole time, me and him 69 on our sides and finally getting my cock to his shaved hole. My thick cock slid in easily and I paralyzed him as his head went down..two slow thrusts letting him adjust..he got into it. She was now naked rubbing, on her phone, a doughy girl, but very erotic. She abruptly had me stop, pull out.." Go wash your cock.." stood in tub soaking cock..wondering what the fuck was up. When I came out he was jerking and cumming on her tits. Then went in bathroom and closed door. She lay back, arms open, I was on her and put my cock in her, very nimble, legs way back, sucking tits sliding cum to her mouth, I began to really fuck her and we almost came together. As we lay there, Patti still in bathroom. I guess she saw his emails wanting to play without her..he didnt know she knew until I was washing my cock. She whistled he came out and hungrily cleaned her, ass up, plug in place. I left, that was fun!
Email from her.." I meant it, that cock is mine and it better always be loaded, I'll know." I laughed it off.
Then she sent me my address, where I worked and very graphic pictures of me with Patti. With " So?" I sent ," Yes Ma'am."
" Good, see you in 45 minutes...I know exactly where to go."

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