She’s Got Something Extra: His First Trans Hookup

I was at the bar, and her smile was what caught me. It was so warm, and bright, and I felt like she wanted me just seeing it. I had always been really attracted to Indian women, since college, and had dated two of them. She had something extra, even beyond her heritage. She was a vision, silky wheat colored skin and dark hair, I wanted to touch her, and I had to talk to her.

Did I know she was trans when I started talking to her? Yes. I can’t say that I didn’t. There was something about her jaw line, when she turned her face, and when she smiled. It was like there was a second face, an echo, or a shadow. She had this foxy, otherworldly look to her.

And then we were talking, and she was laughing, and I felt like things were going really well. I had to ask her, and I could have blown it. “Anushka, can I ask, you’re trans, right?”

She nodded, and sipped her drink, not breaking eye contact.

I continued, kicking myself for even talking about this. “If we were to … be together, that would be something I’ve never done before. Is that OK? I’m not gay.”

She laughed, like she was relieved I asked. “Listen, Robert, I’m not gay either. I’m a woman, and I date men. Gay men don’t like me, because I have a woman’s body.” Then she leaned forward and put her hand on my shoulder, and whispered, “but if I decide to fuck you, I’m going to blow your fucking mind. I know my way around a cock.” She kissed me on the cheek. “I understand you in ways that you don’t even know. I can open you up to parts of yourself you didn’t know existed.”

Then I went for it, kissing her full on the mouth and putting my hand on her neck. She put her hand on my inner thigh, and nuzzled her face into my chest; she smelled of jasmine and coconut. “Let’s get out of here,” she whispered.

I got the check and the Uber instantly, and we were home on my couch making out before I knew it. Anushka was in her bra and panties, between my knees, sucking my cock, and I was naked. She slurped her wide mouth off my erection, and asked, “hey, can I stick a finger in your ass?”
“No one’s ever done anything with my ass before, but…”

“How about this, I’ll try it, and if you don’t like it, we’ll stop?” I nodded; her mouth on my cock was like oxygen to me, and I needed it more than anything. She drooled onto her hand while she was pumping, and reached under my taint to finger my asshole. My anus released gratefully with her slow, gentle pressure, and she pressed in, slowly hooking her finger into my prostate.

I moaned, and it felt like my cock was swelling in size even more. Anushka alternated pressure back and forth on my prostate and my cock, so that they were in opposite directions, and I felt like I was going to shoot out a geyser of cum. It was amazing, it was like I was the girl and the guy at the same time.

Usually I have to negotiate so much with women to get them to let me give them pleasure, and she was the one working on me this time. I felt like I was going to cum at any second, and she knew it. She slowed me down, took her mouth off my cock and hand out of my ass. She put her hand on my dick and squeezed. “You about ready to fuck me, big boy?”

“Yeah, let’s do it.”

“I’m going to show you my cock now, is that OK?” I nodded again, and she brought down her panties. Her prick was small and thin, and curved up when she had it off.

“Can I touch it?”

She laughed. “You better!”

I felt her penis, throbbing, like a huge clit. It was a real turn-on. She put her hand on my thigh. “You can jack me off while you fuck me, if you want.”

Anushka climbed up on the couch, and turned around, her ass facing me. She slowly lowered herself onto me, and I tried not to hyperventilate. Her ass felt so tight, so warm, and good, it got me going all over again. As she started working her way up and down on my cock, I ran my
along her thighs, and fisted her cock. Pre-cum coated my thumb as I rubbed the head. She was panting; I was grunting. I grasped her tit with my other hand, and pulled her close to me, keeping up the rhythm. We came together, me in her ass, and her in my hand. Deep pleasure washed over me in waves, and I felt better than I had in a long time. I released her cock as she softened and wiped my hand on my boxers. She was smiling at me.

“What do you think?”

“You’re fucking amazing, Anushka,” I said, and we kissed as we laughed together.

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