Exploration

First of all, I need to apologize for the lack of post for almost a month. This is because I have been taking some time exploring my bottom side. I had been almost pure top so far, probably about 95% top and 5% bottom. But recently that shifted a bit, as you noticed from my recent posts. Even then, I still viewed bottoming as an extra, not a priority. I'm really envious of those flex who really enjoy being fucked as much as fucking itself. So I thought of letting myself loose and just explore how much bottoming I can really get and enjoy. I decided to allow for several fucks and make a conclusion.

1. Katong Guy
Hooked up with him from a sex app and went to his place. He is in his late 30s, has ah beng look with lean fit bod. Not very toned but lean abs and defined pecs and dark nipples. He spotted a 7 inch thick straight cock. He is really "wet", likes to give wet kisses and tongue bath on my whole body. He entered me in missionary at first but he wasn't slow enough and his cock is quite large so it was a little painful. He started slow but he was too horny to hold back and gave me a rough pounding after a while. He flipped me to doggy but it got too painful for me so I lied down and he continued pounding me from behind. About several minutes later, he slammed me harder, cummed, and collapsed on top of me. How did I fell ? His cock is thick enough to stretch my hole and give me the filled feeling. But the pleasure eluded me most of the time because his fucking was so straightforward. I got hard because of the rubbing against the bed, not because of the fuck.
Overall - 2/10

2. TJ
29 years old lean toned guy I met several months ago for blowjob. He's a pure top who loves to suck, such a rare species, so last time he just sucked me til I cummed. He has a, in my opinion, a beautiful 6.5 inch uncut straight cock with medium thickness. It's beautiful because his foreskin is neither tight nor loose so it slightly covered the head when getting harder, until it's fully hard and exposed the red juicy head. He sucked me well and made me very horny that I actually moaned when his finger went into my arse. He entered me in missionary, slowly while kissing me and playing with my nipples throughout the entry. I was hard during the entry but then there was a slight pain when his cock got past my anal muscle but it soon went off as he pumped me. He gave me a slow and steady pumping. He wanted to jerk my cock but I pushed his hand away as I didn't want to be distracted by that. My stayed soft because it wasn't pleasurable enough although not painful as well. Very slowly, it became semihard. When he tilted my up such that he entered me straight from the top, my cock instantly got hard. He gave me a hard pounding which surprisingly was not painful, maybe because of the angle. Another fifteen minutes of the fuck and he came inside me. Then he sucked me til I came too.
Overall - 6/10

3. Mark
35 years old caucasian who has been living in Sg for a few years. Nice lean fit body with beautiful pecs and abs. He has a very long cock, about 8 inch but less than average thickness, making it looks like a thin prick. Lots of foreplay and he prepared me well. But as soon as the cock went in, I could feel it poking against my arse wall and it was darn painful. Less than two minutes fucking, I couldn't take it anymore and I had to stop him. In the end I fucked him instead. He has a cum fetish so he made me cum into his mouth and swallowed all my cum. He even ate his own cum after he shot.
Overall - 1/10

4. Lee
He's the guy who introduced me to the pleasure of being fucked in this post. The routine is similar, lots of foreplay and he prepared my arse well. His thick cock really stretched and filled my hole passage. Strange at first, but the moment the fucking began, the pleasure built up. Both because of my hole fully filled and because his cock always rubbed against my prostate. He flipped me to doggy which got me worried but he learnt his lesson and gave me a shallow rapid thrusts instead of deep ones. Another ten minutes we're both on our sides and he fucked me from behind. When he said he's cumming, my hand instinctively touched my cock briefly and my cock sprayed few shots of cum. He came about the same time.
Overall - 9/10

5. AT
Part-time model in Sg in his 20s, quite famous in this circle. He has been trying to hook up with me but always backed out everytime because I told him I would rather fuck him instead of getting fucked. So when I'm looking for a top this time round, he was more than obliged to help. His 7 inch cock with average thickness was a pure bliss during the entry, no pain and he kept me slightly away from full entry that it didn't poke the arse wall. Then he flipped me so that I lied on the bed faced down. Then he rammed into me hard and fast, which was okay because the penetration was less deep in that position. Although his cock rubbed onto my prostate every now and then, the pleasure was not strong enough like in the case of Lee. Maybe because it's not thick enough. My cock was semihard throughout. After he came, he volunteered to let me fuck him. He claimed that he's a flex top but don't enjoy being fucked. Yet when I pounded him silly, he was moaning like a bitch in heat and his cock was rock hard.
Overall - 4/10

6. JR
30 years old fit guy who claimed to be a flex. He's a big fan of SM but I'm not into it so we agreed to meet for normal hook up. His nipples are like the button to his cock hardon. By pinching and squeezing hard (bet it's so painful), his cock will get rock hard. His cock is average in all sense, 5.5 inch and normal thickness. The entry was smooth but that's about it. Every thrust he made didn't really make me feel anything, slight discomfort, no pain, and that's all. It might even get soft during the fuck so I had to pinch his nipples hard again. He couldn't cum while fucking and begged me to fuck him instead. I couldn't say no to those puppy eyes so I gave him the pounding of his life.
Overall - 1/10

7. AK
A Taiwanese visting Sg for holiday. He's a cute guy in his 30s, fit body with nice pecs although no visible abs, and nice large dark nipples. He's a flex so we agreed on a flip fuck. When his brief was off, an insanely hard and thick cock but a little less than average length came out. It was so thick that my whole hand could barely hold it in full and that made me scared a little. But he was so sweet and the intense foreplay relaxed me. He entered me first after applying lots and lots of lube. And it really helped because I felt little pain, mostly uncomfortable because of his very thick cock. He was like an energizer bunny so he fucked me with quick rapid thrusts in various positions. Because his cock was not so long, even a deep thrust wasn't quite painful. The fullness feeling in fact was more pleasurable. After about 20 minutes of intense fucking, he came inside me (in a condom). I asked him if he needed to rest because he just came but he wanted me to fuck him right away. A sweet guy during foreplay changed into an energizer bunny as a top then changed into a total slut as a bottom. He mumbled lots of dirty talk (in mandarin) and asked me to keep fucking him harder. His cock grew rock hard again after about a minute of pounding. Half of the time, however, he pounded himself in that I would stay still and he moved his ass back and forth. As I pounded him very hard in doggy, he sprayed his cum hands-free onto the bedsheet.
Overall - 7/10 (if I were to rate the topping experience alone, it would be 10/10).

General conclusion : I actually felt good more than I had expected. Two fucks were darn good (by Lee and AK), and one was pretty good (by TJ). This is almost half in proportion so I guess I should really explore this side of mine more. What do you think ?

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.