I Remember My First M2M
I was in mid teens and started having sex with this much older woman. Tess was an OK looking, 62 year old with an incredible body, hairy pussy and DD titties that she loved sucked on and rubbed. She taught me everything about sex, and more than I bargained for. She brought over a few friends, one at a time to spend "naked time" with the two of us. I ended up fucking other women. She would usually send us into the guest room as her bedroom was reserved for she and I. I fucked 5 of her friends, one really fat woman who was only about 33 and one woman at 38 who was incredible in her body however; she was a butterface. The other three were older than Tess. Then she brought over a short rather chubby girl. She was only 20 i was in my mid teens, and she and I were kissing, I was feeling her tiny little boobs, and sucking on her puffy yet erect nipples. Tess left us and I was horny as hell. The girl sucked my cock and I asked to fuck. We went to the spare bedroom and the girl got dressed and under the covers right away, leaving her perky little boobs exposed. When I went down on her, there was no pussy instead a cock. she called it a clit but it was a cock. However; no balls. She'd had the surgery to help with her hormones so very little testosterone I guess.
She told me to kiss it, since she'd sucked mine, and I didn't want to but I asked if I could fuck her after I did it. She said yes, so horny teen me, kissed the shemales cock, licked it as per her instructions, and it got pretty hard which surprised me with no balls. She pulled me up and face to face, she was already lubed and held my cock at her asshole. I pushed in and fucked her. After i was lying next to her on the bed, thinking about having just fucked a guy, and she got on top of me. Her lubed cock was hard and again no balls . . . but she pushed into me despite my trying to get her off me. She pumped me for a few minutes then grew soft and pulled out. "It's only right, after all you did it to me" she said.
Tess came back, we were dressed in the living room and watching a movie on TV. Tess immediately asked me if I like her, i mumbled I didnt know and she asked if I fucked her. I didn't answer, the gurl piped up "My ass is sure sore from something". Tess kissed me and congratulated me then asked me if I got it in return. The gurl said I did. Tess asked if my ass hurt and I said no. The gurl left and with that tess talked about the pleasure a mans ass can give him.
She started taking me over her knee to play and open up my asshole. She played on my prostate, and finger fucked me then would fuck me with a vibrator. As I got used to it, she'd use strapons to fuck me, then strapons that vibrated. It became part of our regular sex, and the gurl came over a few more time. Each time I fucked her and she stuck her not totally functioning cock in me and played around. Then one night alone Tess while I was bent over her knee her playing with my asshole, asked me to tell her intimately and in detail of what the gurl and I did. By this time Tess convinced me it didn't make me less manly, in fact it made me more of a man as I opened myself up to all types of pleasure. She had another friend who wanted to have sex with me. This time it was another man, a man in his 50s, married to a woman but he wanted me. She didn't tell him about the girl, only her fingers, vibes and dildoes. He wanted to take my virginity. I guess in a way it would be, first cum in my mouth and first one to cum in my butt.
I just came back from the night with him. I got fucked by him 3 times, and sucked him off once. At the end he gave me $1000 in cash. Tess and the gurl were waiting for me. I had to tell them all the sordid details. That was a eight years ago now and I've definitely realized what pleasure a woman and a man can bring. Or anyone in between!
