CL Hookup

I'm straight (bi?), but have been experimenting with a lot of different fantasies recently. Just kind of having fun and trying stuff out. Being with a TS woman I've always found hot, as well as strap-on stuff with hetero women. This is a story about my first time with a TS. Names and facts changed but of course sex stuff is true.

I put an ad up online with some pictures that said:

Straight masc looking for TS top

- straight masculine handsome, looking for a top TS to teach me. Never been with a TS before but I love giving oral, getting rimmed, getting fucked.

Got some responses from rather unattractive cross dressers wanting me to top them, couple of normal looking guys wanting to hook up or rim me. Wasn't much interested in them. Got a couple attractive t-girls though, only one of them seemed to match up with my interests. Her name was Tina.

We started messaging on kik, sent each other a couple nudes and decided to meet up at her place that weekend. We texted a little bit after that, just talking about our sexual interests and what we were each into. On Saturday night, when we were supposed to meet, she texted me.

Tina: hey :) so my friends actually are dragging me out to the club tonight. Can u come over earlier? Then we have more time to relax together b4 I leave??

Me: we can reschedule if you want I don't mind lol

Tina: no just come over at 8 o clock??

Tina: I'm not leaving until 11 ha

Me: okay that's fine too. See you then :)

I had that familiar nervous feeling as I walked up to her door. I knocked, fiddling with my fingers while I waited for her answer. Right as it opened, I remember thinking, "really hope I don't get mugged in there."

But, Tina was standing there in front of me. Tina was probably an inch shorter than me at 5'9", slim, big boobs and a tight ass. She had long black hair and thick lips and look Asian, maybe Filipino with her dark skin and cute nose. She was wearing a black skirt and white top, she looked like she was already ready to go out. She was super feminine and I never would have guessed she was a TS just from looking at her.

"Hi," she said, "Come in here."

She took my hands and guided me to the couch, locking the door behind us. I felt kind of nervous being in this random persons apartment, but she quickly put an end to that feeling by getting close and giving me a peck on the lips. I kissed her back and she pulled my hands to her butt, which I started massaging gently. Her ass was surprisingly soft and my cock started to get hard as I kissed her soft mouth. She stuck his tongue in my mouth as I kissed her, responding to my aggression.

"Sit down," she giggled, pulling back from me. "Drop your pants."

I dropped them, and she pulled my shirt over my head as well, leaving my naked except for my socks and shoes. That felt kind of weird but she quickly made me lay down on the couch and started kissing her way from my ankles to my thighs, all the way until her tongue licking all over my dick. She grabbed my hands and put them at my side while she started throating my cock all the way, sliding her tongue up and down my dick making loud sucking noises.

She had me hard almost right away, groaning as she fucked her mouth with my cock. After I was hard, she put my hand back on my dick for me and I started stroking it. Her mouth ran down my cock, licking my balls, and ending up in my ass, sticking her tongue up my ass. Her soft little hands pushed my legs up to give her better access to my hole as I jerked myself off, writhing on his tongue. After a couple minutes of this, she came back up and started sucking my dick again, her hands on my butt, squeezing my ass and thumbing my hole.

I started breathing hard, thrusting my cock in her mouth as I got closer to cumming. She stopped right before I came and pulled me up, planting a tongue kiss on my mouth. I kissed her back and she growled a little, smiling. I felt her hard cock pressing up against me through her skirt. I rubbed it through her clothes and she pressed harder, purring in my mouth.

She pulled off and took my hand, leading me to her bedroom. Once we were there, she laid down on the bed and lifted up her skirt, revealing her cock in a pair of blue lacy panties.

I got on my knees right away and leaned in to kiss her balls, sliding her panties to her ankles. She moaned a little and I stuck out my tongue to lick from the base to the tip of her cock, sucking on the head and then taking her until I gagged. Her dick wasn't that big, maybe 6", with a slight curve to the left. I started sucking her cock and licking it while I bobbed my head up and down. With my other hand I coated her dick in saliva and started stroking it. I listened to her little moans as I blew her cock, massaging her balls and using my tongue to circle her cock head as I tried to get her deeper in my throat.

I did this for maybe a minute before she pushed me off and grunted.

"Oh, shit. I almost came baby."

I smiled and licked the tip of her dick. "You must be pent up. Do you want to cum?"

She bit her lip and pushed her dick forward to my tongue, jerking it a little. "Yes, but I feel bad," she said sheepishly, "Kind of quick, no?"

I laughed and just started bobbing my head on her dick again before taking it out and saying, "Do you want to cum in my mouth?"

"Mhmmm" she purred, jerking the base of her dick while I bobbed my head back and forth.

"Do you want to cum on my face?"

Her eyes lit up and she pulled her cock out. "Oh my god baby! Yes I do!" She started jerking it slowly, staring down at me while I looked up, tongue out of my wide open mouth, licking her cock head.

"Cum on my face baby, give me your cum."

She started jerking harder, looking down at me. "Close your eyes," she said breathlessly, smiling a little as her orgasm approached, "I'm about to cum baby, close your eyes."

I closed my eyes, feeling her cock at the tip of my tongue. She let out a cute little high pitched moan as she came. I felt her warm cum shoot on my face and cheeks, a little bit getting in my hair and dripping back to my tongue.

"Oooh yesss baby, that's so good. Yess baby."

She kept shooting her cum on my face, finally finishing and sitting back on the bed. I kept my eyes closed to avoid getting semen in my eyes and started licking it off her dick, trying to swallow it. She gently pushed me back and left, coming back with a wet rag, and cleaned my face off.

"Oh my god baby I came in your hair," she laughed.

I smiled and shrugged, kissing her lips as she finished cleaning me up.

"I think it's your turn."

She stood me up and started sucking my dick again, thrusting my cock all the way down her throat over and over again, getting my cock to full mast in under a minute. I let her tight mouth suck and slide on my cock while the urge to cum built back up in me. Her hands ran over my ball sack, massaging my nuts and two of her wet fingers went to my ass, rubbing my hole while she sucked.

"Can I cum in your mouth?" I grunted, trying to talk while she face fucked herself.

She moaned "mhmmmmmm" which sent me over the edge, and I came deep in her throat while she kept sucking. I shoved my balls to her chin as she milked my cock, her hands on my ass cheeks, pulling me hard inside her.

"Sssshiittt... fuck!" I came really hard in her throat. She didn't gag or make any noises at all. She just swallowed it and when I was done she pulled off and licked the tip of my dick, squeezing out the last bit of cum with her little hand.

The orgasm took everything out of me and I sat naked on her bed, catching my breath. She stayed on her knees sucking my cock until it got sensitive. Then she got up and she French kissed me again, spanking my butt, and leaving to the bathroom to fix her hair.

I laid there for a few minutes before getting dressed and leaving, kissing her soft lips again before I left. I got home and laid down in my bed and fell right asleep.

Next time we met up she fucked me on the couch.