Once I met a trans man off of craigslist personals, back when that website was still up. “t4m - looking for bare sex” was the title. Now, I’m not a discriminating man - I’ll fuck anyone with a pussy, as long as they’re willing to fuck raw and let me shoot my seed inside them. I met him, we had a couple drinks, and when we got to my bedroom, he said he didn’t want bare sex after all, that he was ovulating and it was too risky.
I said fine, and we made out and fucked a bit with a condom on. Then, I ate him out for a while, and I asked him to suck me bare with no condom, since that feels really good. He complied, and as he was sucking me, I said we should do some external rubbing, teasing my cock against his pussy. This is usually a good strategy for sluts who really want your bare cock inside but are feeling hesitant. I’ve found it works on women, on trans men, anyone with a pussy.
He looked nervous, but he was so eager and horny his lust overtook his common sense. He told me to go ahead, and he lay back, angling his cunt up for me, his face flushed with anticipation. As I rubbed the head of my cock along his vulva and clit, I lightly pushed the tip of my cock against the entrance to his vagina each time I passed the tip of my cock over it. I teased him, over and over again, and every time his hips buckled up toward me, I let him push against me for just a moment before pulling back.
His breathing got heavier and heavier, until he started saying “more! more! go deeper!”
That’s when I knew I had him. I slipped the tip of my cock into his vagina, and out again, not going very deep at all. His eyes were alive with lust, and he kept begging me to go harder begging for more. Every few strokes I would go deeper and deeper until I was bottoming out in his cunt with each stroke, and we were both moaning with pleasure. At last, I was fucking him bare, going all the way in, feeling my cock push deep inside his pussy.
God, it felt so good, and his eyes widened with excitement and pleasure as he gave in to his primal feelings and let me enter him all the way over and over again. “Yes!” he moaned as he felt me slide into him, his wet hot pussy clenched around my throbbing cock.
As I got closer and closer to cumming, I warned him, but he was too lost in pleasure to do anything but beg for him to cum inside him. I happily obliged.
After that, he knew he was too far gone to make any pretense of protected sex with me. We fucked twice again that night before I drove him home in the morning, and both times I came inside him as he greedily wrapped his legs around me, begging for my seed.
s-u-f-j-a-n-s-t-e-v-e-n-s
theartofmadeline
