. I was straight my whole life and then into college I met a friend you could say was a femboy that was a gay virgin and convinced me 1 time to try it out. I was reluctant but he persuaded me. I have slept with only women my whole life being on top felt amazing and I couldn’t image it ever feeling as good on bottom from a guy but said it would be kept secret and if I didn’t like it he would never ask again. So I read lots of articles and educational videos on how to have safe anal sex preparing for my first time as I didn’t want it to hurt and even just trying to finger myself was uncomfortable to say the least. But after learning about anal sex, its both physical but also mental. Learned you need to clean yourself out, go on a diet, you need to push out/never suck in or there will be pain, lots of lube, and mentally preparing I decided I was ready. So we met back at his place, i had replace thoughts of him with thoughts of women to be more comfortable and mentally relax myself as I had to begin getting physically intimate and started touching, kissing, cuddling. Had my eyes closed but had to open and just accept what was happening as things got more intense and started to french kiss and taking off clothes. He was 9 inches, which i was reconsidering as i didn’t think even a gay virgin guy could even handle something that big on day one. But I couldn’t think as I had become too sexually aroused. It was a long process so skipping throw a bunch of stuff that happened like getting second thoughts but him helping me get the confidence back, so he was able to get me to eventually blow him to get him aroused and also lubricated a bit, totally wasn’t expecting it to taste so clean, guess he prepared as well. He had me bend over his couch arm and, with a lot of KY jelly, i mean it was like half the bottle, he began to press into me and even when i was thinking maybe I can’t do that he is just to big to get in… well…. i guess KY can get a thick stick through any hole because after another assertive pressure he finally penetrated into me… all 9 inches. Slept with about 5 other women in my life, being a top and the feeling of being inside pussy was an amazing experience but now here i was with a guy and me being the bottom and it was an experience all it’s own. it wasn’t better than being with a women and on top but was not worse than being with a women and on top. it was a different category of pleasure all together. I did struggle a lot to try and not suck in that sometimes did hurt but i did adapt rather easily and it was feeling amazing.

Skipping details to not make it to raunchy, after about 5 min i got this feeling that didn’t make sense, i was turned on but i didn’t have that big of an erection but i could tell i was having the same feeling like i got when i’m about to cum inside a woman and it happened. I came from anal sex on the first try. it’s the weirdest feeling to happened but it did… and i was rather fond of the feeling. LSS to wrap this up, i ended up in his bed, we took turns on each other, idk what got into me but i woke up hold him like the girls i slept with would wake up to me, head on his chest sleeping. i dont know why but i made him breakfast and we still remained friends just with benefits before he found a bf and i found a gf and our lives moved on from there. But cumming hands free from anal sex, its possible and it actually feels really good