[T] My First Sissygasm

I just had the most amazing experience with my first ever hands-free, pure-anal orgasm yesterday and I had to share it somewhere.

The inspiration for this breakthrough was a clip of another t-girl riding a suction cup dildo on her bed by mounting it on a textbook. My absolute favorite toy is this jelly purple 8″ with a suction cup base so I had to give it a try, and yesterday morning I was working from home before a big interview and had the apartment to myself. So why not? Sure, I may have been pushing the timing on the interview but I was cock-thirsty and didn’t want to be distracted either.

So I stripped down and mounted my rubber lover on a differential equations textbook I hadn’t used since college. At the head of the bed I put a looping porn clip that had been sent to me by a penpal. Alternating rough anal and a big facial. It got me nice and excited as I lovingly stroked lube up and down the purple cock’s shaft. Finally I readied myself by spreading my legs to the floor at the edge of my bed as I buried my facing in the mattress, then worked 2 heavily lubed fingers into myself. It was tight even though the excitement, a third finger wouldn’t fit all the way in yet. I could tell just from that how sensitive I would be this anal session.

Finally, I was ready to mount. I splayed my legs nice and wide and started by grinding my round ass so the tip rubbed against my hole. After a few minutes of teasing I needed more. My hand went between my legs to grip the shaft while I struggled to work the head into me. It took a few minutes of slipping and writhing the slickness into my still tight hole.

As I felt myself wrap around the bulging tip I took a minute to breathe and pinch my now puffed up nipples. Then I relaxed and sunk down, feeling my tightness slide against every inch as it pressured deeper and deeper parts of me until I felt it bottom out. I pushed myself back up a little on my knees, then started arching and relaxing my lower back to let my ass pop up and down on the shaft.

I developed a rhythmic rocking that started building a gasping pleasure, leaving me doubled over. I got overexcited, slamming hard up and down, trying to give myself more but ruining the rhythm. I grabbed and pulled at a handful of my shiny auburn hair in a frustrated bid for further stimulation. I could tell I got close but missed the mark. I slowed down, sinking all the way back on and collapsing face down in the mattress. Then the pleasure hit me again. I needed to keep pushing myself deep. My hips bucked perpendicular to the direction of penetration and I felt the stimulation of deep rocking pleasure fill me. I felt the little squeaking “oh” of pleasure in the back of my throat that only comes from anal stimulation. It built, and built, and built until it came out in spurt after spurt after spurt. And I collapsed forward, spent and unable to move for minutes afterward.

After a wobbly kneed shower I got dressed with only 10 minutes to spare for the interview. Which I crushed, by the way! The relaxation definitely boosted my confidence. :)

Source: reddit.com/r/gonewildstories/comments/tpdqi9/t_my_first_sissygasm