From Top to Bottom

I'm mostly a top as I have said before. In fact, I had been an exclusive top since my younger days until about a couple of years ago. My virgin bottom experience was with my ex. He was a flex who couldn't get enough being shagged but sometimes he hungered for shagging an arse too. Although I was very reluctant, I gave in to him, being a good bf, hah... I must say that the experience was really unimpressive. It wasn't painful at all because his gun was not big at all (it was about 5 inch long and below average thickness). But it wasn't enjoyable either. I didn't really feel any pleasure, more like discomfort most of the time. The shitty feeling, if you get what I mean. Anyway I couldn't complain because throughout our two years of relationship, he fucked me probably about several times only. Ever since then, I occasionally become bottom for another flex top who is hot enough and so that I can fuck him in return. It wasn't because I enjoy being fucked at all. And I thought I would never understand the pleasure of being a bottom.

That was until some time last year when I finally found the elusive pleasure. This matured guy messaged me in one of the dating site. He's in his late 30s, fit muscular bod, claimed to be flex top with L uncut cock.
Him : I'm really horny now. Wanna fuck me ?
Me : U sure ? U're a flex top right ? Do u really enjoy being fucked ?
Him : Yeah, I really could use a hard cock inside my ass now
We exchanged a few more messages and after I got his address, I went to clean up and prepare. On the way there, I kept wondering if he really enjoy being fucked and if this is not his trick to get my arse instead. But I was fully prepared anyway, I cleaned up my down there, lol...

When he opened the door, I saw a very good looking and sexy guy in front of me. His t-shirt couldn't conceal his defined pecs and nipples. He invited me in and we sat in the living room, chit chatting for a bit with a glass of wine and jazz music at the background. A short while later, he couldn't resist and moved next to me, caressing my pecs. The came the lips and we made out fiercely on the sofa, all clothes off. The kissing went down to my pecs, nipples, abs and cock. He wasn't a good sucker but he tried his best. "Let's go to your bed", I told him.

He nodded and brought me in to neat and cosy bedroom. He really set the ambience right, with scented tea candles and a pack of condom, a bottle of lube and lots of tissue paper. I pushed him down to the bed and began servicing his body. His nipples were really hard and he moaned a lot when I sucked on his nipples. His cock was rock hard at that point, and it was quite large. Average length, around 6 inch but it was thick. Thick enough for my palm to hold in full. I'm not much of a cock sucker myself so I tried my best swallowing that huge tool but I gagged a few times. Then I spread open his legs and a smooth arse came to view. He shaved it, not bad... I took the lube, squeezed a generous amount and smear it on his arse. Then one finger went in and he let out a moan. I fingered him while playing with his nipples and it sent him moaning like mad. Then I added one more finger. And his legs got tensed up a bit. Bad news, I thought. He was still moaning so I continued with one more finger which followed by his plea "I want your cock". So came the condom and more lube, and I positioned myself to enter him missionary. He was tense in anticipation so it was hard entering him ! I sucked his nipples to relax him a bit and he did. He let out a soft moan when my cock made entry slowly. But when it was fully inside, he was a little grimacing. "Are you ok ?", I asked him. He nodded and replied "Fuck me please". Since he gave green light, I started plowing his ass slowly. After several minutes of slow fucking (which got me bored), then I realized that everytime my cock was at the deepest, he would tense his body. And his cock was totally soft. So I pulled out my cock completely and just sat looking at him. He asked what was wrong and I told him that I couldn't bear fucking him when he was in pain and discomfort. And he apologized very sincerely. It was very nice hearing him trying to explain and kept apologizing. Then he finally asked the question "Can I fuck you instead ?". If any random guy asked, I would say no. But he was sweet as fuck, so I thought I'll give it a try. His thick cock made me very nervous though. I told him that and he assured me that he would treat me well.

And he did just that. He serviced my body and my cock and prepared my arse with lots of fingering to make sure I'm fully relaxed. He even rimmed me, something very few tops do. And he was darn good with his tongue, as opposed to his sucking skill. After like almost half an hour of rimming and fingering, he readied himself to enter me. Lots of lube was used and he constantly played with my nipples or my cock while slowly entering. He was painstakingly patient and despite his thick cock, the entry was very smooth without any pain at all. He asked me if I was feeling ok because he noticed that my cock got soft. I told him I'm fine and I don't normally get hard being fucked. Then he asked if he could start the fuck. That was very sweet of him, wasn't it ? After my nod of agreement, then he started with a slow long fuck. At that time, I felt something strange. It wasn't the shitty feeling anymore. But an odd feeling of having my ass stretched and fully filled with a cock, that was somewhat good. Then suddenly he did something different. He was gyrating his hips such that his cock somewhat rubbed around my ass and it sent me jolt of pleasures which made my cock semihard ! I couldn't hold back from moaning everytime he did that. After about fifteen minutes, he pulled out his cock and kissed me. "Fuck, what did you do ? I've never felt anything like that before", I told him in between my breath. He laughed a bit and said that he probably hit my prostate. Darn, now I know what I did to those guys who succumbed to my fucking, lol... He signalled me to flip and go for doggy. Which I did. When he started fucking again, it was ok at first. And when he gyrated his hips again, the pleasures sent me to heaven. Until he started ramming deep into me, which turn the pleasure to pain and I had to stop him. He apologized again (sweet guy) and suggested missionary again. And then we continued with slow long fucking in missionary position again. As the pleasure getting more intense, he jerked my cock while I played with his nipples. Then he asked me if I wanted to cum together. And I told him to fuck me faster. He did that and he jerked me faster too. As we both moaned louder, he finished off with long strong thrust and each thrust made my cock shot a spray of cum onto my pecs and abs. Then he collapsed on top of me, both of us were wet of sweat. He gave me a kiss before pulling out his cock from my ass and laughed saying that my ass looks so nice after being fucked. We chatted a bit afterwards while resting about being a bottom. At the end of it, I concluded that I need cock of the right size in order to get the pleasure. Just right thickness so that it fills my ass and stretches it comfortably. Just right length as longer cock will probably just hit my prostate wall instead of rubbing, making it painful instead of pleasure. And so I need to be very selective when finding a top.