Bottoms. Just how painful was penetration for you when you first first bottomed for a guy?

[PozConverted]

I was 18, he was 24. We were boyfriends. I had sucked his cock several times and he made me understand I loved cock. He was also the first one to make me taste cum in my mouth. Wanting to make love came naturaly, and the first time was unexpected actually. He was very kind and gentle, rimmed my hole and prepared me to be open. He entered in me raw, I felt so happy and so hot, I really felt his cock penetrating me, he was cautious to make it sweet. It was not painful at all, he dumped his load in me (my very first one). I suppose this was the important and sweet situation that made me aware I was a bottom.

[tighthole64]

VERY painful here.  Met a partbered guy on a boat.  As was my first time, he took it somewhat gentle with his 7, but it didn't last long as I didn't know the fine art of cleaning out very well.  Took me back to his partner who had a good and was a rough fuck. Had my first kesson with a shower shot. My ass was bleeding and sore for a few days.  Although sore I spent the night and got seededed multiple times by both

[leatherpunk16]

It HURT. A lot. I bled all over a random guy's new perfectly white Martha Stewart bedsheets. And when morning came, I found that my dick was quite bruised as well. Not related to the bottoming, but was definitely part of the overall experience. 

[PissPigBrooklyn]

I was just 18 and he was a year or two older. He had picked me up the night before and given me a blowjob in an alley. (My first where I had cum in somebody's mouth. I went down on him but couldn't take his cum in my mouth. Skip (that was his name)  jerked off and asked if I wanted to come over to his house the following day and get fucked. I said yes. Next day I showed up. I was scared but as rock hard as I had ever been. He took his time and used a lot  of lube. There was no pain as I remember but a lot of pressure. He just kept telling me to breathe in through my mouth. I did and all of a sudden the pressure went away and I was filled with intense pleasure as he kept pumping away. I felt his dick swell inside me and his breathing increased. I figured he was cumming and I was right. As soon as it was over and he withdrew his dick, I wanted more but instead I got a blowjob from him. It was wonderful! I got hooked on getting fucked until I had an experience with a guy in a situation where I did not want to get fucked or at least wasn't ready for it. That hurt like hell even as I tried to relax (and if I remember correctly he wasn't super hung or anything) For a long time after that, I wasn't into getting fucked and most of my encounters were oral. If I got fucked at all it was by smaller guys with plenty of KY (lube of choice back then.) I was starting to learn how to enjoy it again when someone else just fucked me too damn hard and without lubricant (to be fair, this time I had wanted to get fucked but I had wanted a little more ass foreplay and more lube. I think he used only spit) Again it hurt like hell and I got fissures. I had a bad experience with an M.D. in a city hospital. (This was 1974 or 75) and it wasn't until I got a gay doctor a few months later that I began to relax again. Which was good because at this time, I became a part time hustler for a while (I was terrible at it) and though my experiences were mostly oral or even just hand jobs, a couple guys did want to fuck me. Fortunately they were not rough. Soon i met my second boyfriend. (My first boyfriend and I had, despite his protestations a strictly oral relationship. I think that is why we broke up) I knew he was going to fuck me and I wanted him to. We did on the first date. He was patient and kind and used a lot of lube and foreplay but very determined. He entered me and I breathe d deeply to relax. I relaxed immediately and was transported to bottomboy heaven. We fucked nearly every night for six months. We were together three years. Since him, getting fucked has been mostly a pleasurable experience and the times when it is not are due to me not being prepared or not being in the mood. A couple times, I tried to do it when I just wasn't feeling up to par physically. But for the most part, it's incredible and I thinank Skip for the fantastic introduction he gave me.

[Willing]

I don't know,  waiting for the pain 😵

[satyricon1]

My first time was about 5 years ago.  I had been chatting with a fellow who is several years older than I, and we agreed to get together.  When  arrived, he introduced me to his partner who was recovering from prostate surgery, and then we moved to the front room where we started kissing and feeling each other up.  After about 10 minutes, we moved up to the game room upstairs, complete with sling.  After more naked play, sucking, massaging, and exploring, he asked me if I was ready to be fucked and if I wanted him to use a condom; he had his testing results from earlier in the week, but since it was my first time, I preferred that he use a condom.  He put it on, lubed it up, and slipped into my ass without too much difficulty (I have been playing with it since I was quite young, and routinely use good sized toys on it, so the size was no difficulty for me).   Interesting feelings as he gently moved within me at first and I liked it very much.   I hadn't been expecting to get fucked, and had not cleaned out other than taking a dump before hand.   We took a break and cleaned up and out in the shower, then went back upstairs.  

    We went back upstairs to the play room, and  he asked me to fuck him -- without condom, so I did, which was also a first for me.  After about a half hour of play, he put me in the sling; he asked if I still wanted the condom, but since I wanted to feel the difference and  his testing was clear, I told him he didn't need to use the condom the 2nd time.   Quite frankly, I couldn't really tell much of a difference.  

   We finished up the session, sucking each other off.

    A year later, I was chatting with another guy one evening, and he wanted to come up and meet me -- it was already 9 pm, but I was intrigued and said sure.  When he arrived, we talked for a bit, and then moved to the bedroom where we went through the preliminaries -- kissing, massage, licking, sucking, rimming; while he was rimming me he asked if he could fuck me (I had seen his testing, too), and I agreed.  He slipped in and went to work on me, and after about 15 minutes, he asked if he could cum in me.  I was curious to see if I could feel his cock pulsing, and the cum shooting.  I could feel the pulsing but not the actual ejaculation of cum -- just a pleasant warm feeling spreading through my innards.  

     Then covid hit, and I didn't do anything more for a couple of years.  Looking to do some more now!

 

[Guest]

Yes, it hurt quite a bit and although he used lube he just pushed. I had used a dildo on myself on previous occasions - but very slowly - so knew at least that I enjoyed taking it. But he didn't finger me to loosen me up and I didn't have the benefit of poppers. I was at least on a sort of on a mental high though so was able to take it (just). At least no blood as anal tears are not good. Once he got past my ring it was ok and he did fuck me slowly, He was a reasonable size and I simply couldn't have taken a hard fuck though, nor a fat cock. Really, in hindsight, preparation is everything to a pleasurable first - and subsequent - experience. I still dildo myself regularly to keep my hole relatively open but not loose. For quite some time after my first experience I used the one finger, two fingers then three fingers on guys if I was topping them and them on me.

[Bttm2go]

No pain at all. I played with a lot of toys, so I was pretty open already.

[gangbangsuperstar]

wasn’t too painful for me at all. my older brother has a pretty big dick and it had just gotten to its full size but he and his 2 buddies he shared me with had been working my pussy open with a 6 inch jelly dildo for a few weeks while I sucked their cocks pretty much every day. plus they had already figured out how to douche my boyhood clean so there was no messy first time. I managed to take all 3 of their loads 3 times each. my brother made sure to go first even though he had the biggest cock, so that he could always say he took my viginity. lol but technically since I was the first person he ever fucked, he lost his virginity to me also, as did my younger brother, 2 of 3 cousins that fucked me, several boys from my school, one of my fuckbuddies younger brothers, another fuckbuddies younger sister, and a few other randoms, including a horny young guy who just fucked me this winter. so while ive only lost my virginity 3 times (top/bottom/and topping a girl) I have actually had over a dozen people lose their virginity to me. the key is, my brother had me ready to get fucked so I loved it from the first time and was willing to get fucked by anyone, anytime, anywhere right away. like all guys had to say is “wanna get fucked?” and I would be ready to take it. plus getting fucked by my brothers big meaty cock regularly made it easy for me to start getting fucked by large men when I did, including big dicked black men. pretty sure I was the only boy in class getting DPed as a freshman. lol

[Guest]

It hurt a lot.

It felt like I was being ripped in half.

He used lots of lube and was real gentle.He would push in an inch.Wait.Another inch.Wait.After he was balls deep in me he started fucking me real slow.It still hurt but I bit the pillow and took it like a good bottom.

[mixnzz]

at 16 my boy hole was tight.....i said it will never fit.....but with lube and time he got it in....and the truth, i was hooked

[LetsPOZBreed]

There was definitely a level of pain, but the guy was gentle about it.  So, it was more just the sensation of being penetrated for the first time.  I got accustomed to it as it went on (and he never really fucked me that hard in the end).  

There were times later on that were definitely PAINFUL, but that was in very different circumstances...

[downtownswallow]

First time hurt.  The Top was older and experienced, so he worked my hole for a while but his cockhead was very pronounced and stung when he eased in.  I was so excited I begged him to keep his cockhead in me while my hole relaxed.  He eventually ended up giving me a wonderful "took my cherry" session.  About 7 years later I took another, older Top's cock raw and was properly bred.

[Liverpool]

First time I bottomed I was 16. Was speaking to a guy about 4 miles from me on a chatroom. Went to his place without even seeing him first (risky ik but a big turn on). His dick was really small so I hardly felt anything. The anal wasn't great but he was extremely kinky and I loved everything else. The second time was when I knew how painful taking dick could be. To this day it's one of the biggest dicks I've taken and he was so hot. He entered me slowly a few times but it was always so painful that I quickly pulled away - obviously a fatal mistake. I should have listened to him when he told me to take it slow. In the end I gave up and wanked him until he came in my mouth. Third time was the first time dick sent me to heaven. 

[StlBottom]

No pain, discomfort, just went in smooth and deep.  Had been getting penetrated for several years, fingers, dildos, if it had the right shape, we tried it.  Did get sore after a few of the gangbangs encounters I had, but in a good and memorable way.