the night a sissy flipped me [M20] over and took my virginity
i've never told anyone this because it was too embarrassing. it was back in college, a late night on a weekday, and honestly being a horny 20-something, freshly out of a relationship had a lot to do with it. i was browsing online dating ads when i found the profile of a leggy asian girl, she had her face blurred out and had short tagline: looking for fun.
i had to take my chances and shot her a message hoping she was still online. she was and was quick to respond. i sent her shirtless pictures and she sent me booty shots. when i asked to meet she told me she was transitioning and asked if I was sure. I didn't flinch. She sent me her address and asked me to send her a text when I was close.
I parked and rang the door for her apartment. It was a small studio and completely dark except for the corner where her bed was. When she answered the door I remember having to stretch my neck up to see her face. I was expecting a petite thing I'd be able to throw around, use and leave. No, if I leaned in my head would be resting against her chest and despite the black cocktail dress she looked strong. she invited me in and took my jacket from me as I sat on her bed.
"do you want something to drink?"
"I'm fine... actually, maybe some water?"
i watched her walk over to her kitchen, the dress barely covering her ass as she reached into her cupboard for a glass. she came back, handed me the water and said "take them off." she didn't wait for me to respond or put down the glass, she grabbed my jeans and started yanking them down. it's almost like she didn't want to give either of us time to think. she started licking and sucking and i was in heaven. i grabbed her head and pushed her down but there was no resistance, she just swallowed me whole and didn't stop until i was shaking, shooting my load down her throat. she looked up at me after swallowing and asked "can you go again?" while stroking my dick. out of the corner of my eye i saw her touching herself too and I think I was too shocked to say anything. the orgasm and regret -- both made it hard to say anything. that's when she flipped me over. I had been laying down at the edge of the bed until now and she reached under my hips and turned me around like I was a blanket. I didn't have time to react. I think I asked if she had a condom. She mumbled something back and I didn't get a chance to say anything again because she was inside me. i almost threw up from the pain. she wasn't just taller than me, she was bigger than me everywhere and i was a virgin at that point. i don't know if she even used lube or if it was just spit. she bent me over and held me down, putting the head in, then sliding the shaft in until i was spasming in pain or pleasure i don't know. it hurt, it definitely hurt, but i didn't stop her. she kept pumping her cock into my virgin hole until i felt her suddenly pushing harder, faster, and seize up, collapsing on top of me. i felt something leak out.
my mind was a blur and my face was still pressed into her bed when she got up off me.
"oh shit it's bleeding" she said.
i couldn't look at her. i grabbed the wet napkin she was holding out for me and wiped myself. i threw on my jeans and shoes and left as fast as I could. in my car I could feel where she had marked me, raw and aching. where she had turned me into her toy for the night, taking my anal cherry and masculinity with each thrust. part of me thinks i've never really recovered from being fucked by a girl