Got Flipped!
Since 2014 I have had multiple experiences with TS girls (+25), solely as a top. In both 2016 & 2022 I had the opportunity to try being bottom when I was with two versatile girls but passed as I did not like the idea at the time.
After the 2022 experience was passed up, I have probably thought about it every week and have grown to love TS porn (thanks Reddit!). Unfortunately in the experiences I have had since then, all the women have been complete bottoms or have not been able to maintain an erection.
Until last week.
I matched with a Cuban lady on a swingers site, who was Trans and through the communication I believed she was only a bottom. Needing some action badly due to multiple days of hangover horn, we agreed to meet and within 90 minutes of matching I was at her door.
After a glass of wine and some hand action in which she placed a cock ring on both of us, she ushered me to the bedroom before saying in broken English “Me first. Stamina. Si?” Shocked as I was expecting only to top I stammered and agreed to “try” as it was my first time outside of pegging and asked her to please be gentle.
With some slow very lubricated fingering and passionate kissing I was in ecstasy as I could feel her rock hard cock digging into my balls. She repositioned and started to enter me once she decided I was open enough, and slowly inch by inch she slid in. Taking what felt like an eternity I was in a trance and breathing deep, only to snap out of both when I finally felt her balls pressing against my own.
No thrusting to begin with only grinding and more passionate kissing, I felt incredible inside but noticed I had gone totally soft even though I was incredibly aroused and even with the cock ring. When she noticed this she changed position lifting my legs and began to thrust, slowly and only half way in and out. After about 5x mins I began to get an erection again and she stood me up off the bed, standing side on against her dresser so we could both watch in the mirror.
My erection was now fully throbbing as she spread my cheeks and slid back into me. I was so horny at this moment I could feel an orgasm building even though she hadn’t touched my cock since the foreplay before sex. She stood there speaking in Spanish in my ear as she thrust into me, getting harder with each one. Pulling out almost all the way slowly, then thrusting her full length hard then holding it for 3-5 seconds. On the hold I could feel her pulsing against my prostate and started to leak a little pre-cum.
A couple of minutes of this and I knew I was about to burst, and having had hands free orgasms during pegging I knew the sensation. I asked her to stop as I was about to cum… which had the opposite effect. She made a guttural noise as she started to fuck me harder and faster… I don’t even think I lasted 90 seconds.
I could see in the mirror my rock hard cock spurting like a burst fire hose, cum spraying everywhere as she had an almost evil grin whilst still pumping away. When I started to recover from the brain melting orgasm I pulled away and told her I needed a break then would fuck her as soon as I was ready.
“No. No finish. Stamina, si?” And pushed me face first onto the bed. Quick as a flash she mounted me and I can’t describe fully how hard she fucked me on all fours. She fucked me like how I like to fuck… so that was an eye opener.
10 minutes of doggy style and 5 minutes of ploughing me into the mattress lying prone, I was just enduring it and mentally realising she’s was treating me like how I’ve treated some people during sex, just something to cum in.
This realisation weirdly got me hornier again and my half flaccid cock began to rise again. As her breathing began to labour, she pulled out and lay on her back, quickly pulling my into position to straddle her.
“You work. Sit”
I was so embarrassed as I had never imagined being on top, but found myself squatting on her dick and attempting to ride (very poorly). Thinking this may also be a good time to recover as I could be in control was absolutely not the case. From this position, she grabbed my hips and thrust up into me with great vigour hitting what felt like even deeper than before.
I seen the clock and realised she had been fucking me relentlessly for 40 minutes at this point which again strangely got me even more aroused as I was trying to bounce on her her dick and watching my own erection get back to full mast.
When she seen I was fully erect again, with sweat pouring from her brow and body, she flipped me over without even removing herself an inch from my ass. With one swift motion she held one leg over her shoulder and finally grabbed my dick, starting to stroke furiously as she pumped into me.
Looking me in the eye she said “Si, Si, now!”
Knowing exactly what was happening as her thrusts became harder and more erratic, her jerking sent me over the edge into a 2nd orgasm as she started buck and push even deeper into me, unloading her cum all the way inside as she let out a squeal/scream of passionate delight.
I could not believe it at the time and also retelling it now, still cannot believe it. Lying there giggling together, she got back up and brought through the wine. We waited about 30 mins and she began to finger and stroke herself, showing me everything along the way.
As I regained an erection she bent over in front of me and spread her ass exposing her open hole, glistening with lube from her fingering. I took this as the invitation to enter and knowing fine well that after 2x orgasms I would need to really work hard to get over the line. Plus, I wanted to give some payback for the drilling she gave me and didn’t want to be outdone!
I really went to town on her, pumping fully stroke basically right from the beginning, hammering her soaking hole which felt amazingly both a snug fit but loose enough to really get into. She leaned back on her knees and turned her head to kiss me as we watched in the mirror. I started to jerk her and she asked me to slower… I remembered she did not offer me the same kindness so timed my thrusting in with the down stroke of the jerk and kept up a fast pace. Within about a minute she started to buck again and pushing back onto me she started to cum.
As I was thrusting into her I could feel her cum start to leak from my ass down the back of my balls and this sent my caveman horn brain into overdrive, releasing her cock and grabbing both hips really driving my length into her balls deep. Pushing her down in the mattress I held her firmly in position and told her I would not stop until I cum. Pounding and pounding, hearing her whimper i eventually felt the sweet release of orgasm and emptied myself into her ass.
This was 11x days ago… and I haven’t stopped masturbating or thinking about it since.