I let a man take my virginity.
A few years back I wrote a true story about my first sissygasm. Since that time I’ve grown a lot as a sissy and not too long ago I lost my virginity to a man. This is what happened.
I had been posting hookup ads on craigslist, reddit, and various other sites trying to find some sex with a hot guy. Typically these posts and email chains went no where due to circumstances I’m sure a lot of you sissies out there are familiar with. Until I landed a pretty good match.
So I went all out slutty girl. I shaved my entire body, flushed out my ass till it was sparkly clean, and did my hair and makeup. I dressed up in my skimpy little school girl outfit complete with lace bralette, white stockings with a garter belt, pink micro skirt, white tie-up top, and a pair of crotchless panties. As well as my pink chastity device, locked and with the key left at home.
He offered to pick me up in his car so i threw on a pair of PJs and a big hoodie to hide under while i walked down the street where I agreed to wait on the street corner for him. I had my glass buttplug in while I sat on the curb waiting for what seemed like forever. I had loaded up some sissy hypno audio to listen to while i waited so it wasn’t so bad.
Needless to say when I saw him driving up my heart was racing. This was one of the best feelings ever. The rush of adrenaline of knowing I was finally going to get fucked like a hot little slut in heat was thrilling and wonderful.
Anyway, he pulled up in a pretty cool toyota MR2 and i hopped in.
He was pretty decent looking guy and nice too. We talked a bit in the car on the drive over to his place which was out the middle of fucking nowhere. About half way there i took off my hoodie and PJ bottoms to show off for him a bit and jokingly told him not crash the car while he was staring at me.
We eventually made it to his place and I followed him inside. It was kind of a shitty apartment but whatever I wanted cock.
So there I was. Dressed up, locked up, and looking hot.
He left the back window shades open and we sat on the couch. I kind of liked that the window was open and was secretly hoping a neighbor or two could see what was about to go down.
He asked for a lap dance which I happily jumped at the opportunity to perform. I started grinding my ass into his crotch and felt his dick get hard under his jeans and felt it slide between my ass cheeks. Fuck it was so hot to know that I was turning him on. I had made this guy horny and made his cock swell with my sexy grinding and breathless whispering.
After a little bit of sexy teasing and touching, I dropped to my knees and started undoing his pants. Then out flopped his cock. I’m not gonna lie, it looked a bit smaller than it did in the pics we swapped earlier but it was still a pretty nice cock.
I looked up at him with my cute little cock sucker eyes and started worshiping his cock. Kissing the tip, licking the shaft, sucking his balls into my mouth. I stroked his dick while I sucked the tip. I made it nice and sloppy for him before i started to take him into my throat. I must have looked like a porn star when I swallowed his penis balls deep and looked up at him with my eyes watering.
It was one of my better blowjobs to be honest.
That must have riled him up a bit because he lifted my head off his dick to tell me he was ready to fuck. The look and feeling elation on my face must have been perfect. I stood up and hopped onto the couch. I was bending over the back of the couch on my knees with my ass sticking out. I was facing the open window.
He slid on a condom and pulled out my glass plug.
Here’s where things got kinda crazy. He was rough with me. Something I was not prepared for. He didn’t really warm me up or anything so i was grateful to have been plugged for a few hours prior.
He started fucking me right away, hard and deep. He would thrust into me balls deep and then slowly pull out then plow into me again and again. It hurt. Fuck it hurt in a good way. I could feel him inside me bottoming out my ass. I was whimpering like a little bitch and with each thrust i kind of moved away a bit. He totally noticed he was hurting me a little and grabbed my hips to make sure i couldn’t get away. He leaned over and started tell me to “just take it, cmon. Just take it” Fuuuuuck. It was so hot, it hurt really deep. It was crazy. To love the feeling of being abused and used like a fleshlight for a man’s pleasure was fucking up my mind and my ass. My moaning got loud enough for his neighbors to hear through the shitty thin walls of the cheap apartment.
This went on and on for like an hour until i thought i was gonna lose my mind lost in fuck puppet bliss. Then with a final deep thrust he came inside me. I had finally done it and I loved it. I knew right then and there I would never be the same.
I fell into the couch while we went to go wash his dick, and when he returned we watched some TV for a bit.
We moved to his bedroom and things got wild.
We started fucking like animals. He pouned me harder and faster than before making me moan really loudly and even scream a bit. Shit was falling off the side table and we rocked the bed frame against the wall. Everyone in that shitty apartment building must have heard him fucking me like a whore. At that point we were still doggystyle fucking, but things changed a bit when he flipped me over onto my side.
I didn’t know until then how amazingly good it would feel to get fucked on from behind on my side. I found myself fucking my ass backwards onto his dick because it felt so good. I was panting and moaning, desperately trying to fuck him back. I could feel how hard i was trying to get him deeper inside me. Fuck it was so so so fucking hot to feel so submissive and horny for this guy.
He must have noticed how badly i needed his cock so he flipped me over onto my back and lifted my legs over my head to fuck me.
He was pounding me and pressing his body into mine. His abs were rubbing into my pink chastity cage and he was hitting my prostate for sure. I was gone. I had never felt this way. It was sissy heaven. I was legs spread with a guy between them. Fucking me like a filthy little slut.
I wasn’t ready for how that felt. To be held down and fucked like a submissive girl AND to be kissed was…I don’t even know how i felt about it. It blew my mind.
I lost track of time I don’t even know where my brain went. All I understood was raw hot sex.
He busted his second nut and left me sweaty and panting in his bed while we went to go wash up again.
I layed there on my back and felt my lossened wet, stretched out asshole with my fingers and. It was perfect.
Anyway after that he drove me back home and that was that.
It was a pretty great experience overall. 9/10 wish we didn’t have to use condoms.
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