What Was Your Experience Like When You Bottomed For A Guy For The First Time?

[ilovejstrokesdonk]

In A Brief Summary Describe Your Experience The First Time You Bottomed For A Guy

[loveguys72]

Briefly, it was wonderful!

[G-Lexington]

My first boyfriend. I had topped him several times, and he had never asked to top me, so I figured those were our "roles". But one night, we were making out naked in bed, with me on top. And I decided to ask. "Can I bottom this time?" He said "sure", so we started working me open. Having done it with him, I managed to loosen up quicker than I thought. We wrapped him, lubed him, and I slowly slid back onto him, finally sitting up on him as I took it all in.

It was...strange. I expected to feel absolutely mind-blowingly incredible, or for it to hurt like hell. It was neither. It was pleasant, erotic, unusual, fun. I enjoyed feeling it move in and out. I got my prostate working, and that felt even better...but still not earth-shattering. We both reached orgasm in short order, although for me, it was more novelty than sheer experience. I've bottomed a few times since then, and always enjoy it. But I definitely prefer topping.

Lex

[Rolyo85]

It was my third time ever having sex. I was at a party, a guy started gravitating around me, we got drunk, he got friendly. At some point he told me he was straight but didn't really pull entirely away. However, the party currents split us apart for a while, and I met this singer - tall, big, hairy guy (a bass). Within three sentences, we knew that we'd be leaving together, but then the "straight" guy reappeared (I didn't know either of them btw, and they didn't know each other). So the singer told the guy he should make out with me in front of him, and I made it happen.

In the end, we left all three of us together, and spent the night at the "straight" guy's bathtub and then bedroom, doing second and third base stuff. At some point sex got into it, and the singer was willing to let me top him, but I had had too much to drink and wasn't sure it was happening, so I figured, what the hell, and let him go at it instead.

It felt weird and awkward, but not painful. I didn't really enjoy it, but I was satisfied to have done it.


As a side note, the "straight" guy freaked out afterwards and never talked to either of us again, but me and the singer are still good friends, even though we don't live in the same place anymore.

[G-Lexington]

As masturbatory fuel, this thread isn't doing well at all, is it?

Lex

[Hard-up1]

It was poignant. For me, it was later in life, but my partner, early. He was experienced, but I was not. The role reversal sounds strange, but we didn't feel so.

I found it moving. I'm an emotional sort at core, but calm in other circumstances.

[G-Lexington]

Poignant. That's a good word for it.

Lex

[cgymike]

As masturbatory fuel, this thread isn't doing well at all, is it?

Lex

Um...this IS HT after all...not all threads are jack off material...LOL

But yeah ...first time was painful - I think he used very little lube. I felt like peeing right away and in fact I think I did before even reaching the bathroom. Also, as an inexperienced top he didn't do it in the best position and also didn't ask if I had cleaned out beforehand so not sure I was crap free up there so that may have made it more uncomfortable.

Not memorable for pleasure.

Sorry lex...

[G-Lexington]

Oh, no, I'm not complaining. I think it's interesting and instructive. But I'm guessing that the OP was hoping for something a bit more...salacious.

Lex

[doctorsun]

Poignant is a good word for it. It was a milestone in a way. That said, it wasn't really much to speak of. It went pretty well for a few minutes but then he happened to slip out and I don't know if he just never managed to get it back in right or what, but it wasn't very pleasant. It never hurt or anything, it just didn't do anything for me. Plus, he didn't have much stamina and had to quit pretty quickly because he was tired. So, it ended up being kind of a bust. But still, it was an important moment.

[Anders123]

Most of my sexual experiences have been with a woman, so the act of topping is what feels the safest and most comfortable for me. That said, I would be eager to bottom for somebody I felt I could really trust. As an act, I admit I find it a little intimidating, but I think my anxiety would be minimal with a caring partner.

Sorry, nothing salacious here either.

[M10000]

He fucked me 4 times in 6 hours. It wasnt fun. Thats what you get when your friend is telling you to go out and get poked

[looseliam]

I was ecstatic! I kept thinking "finally ffs!"

[bankside]

Neither of us had a world of experience, very little. I have been versatile in my inclinations since before I was aware it was even possible for a guy to not be versatile, so I was looking forward everything we could do together. He was worried about hurting me due to his size, and assumed topping would not be feasible. I assumed that I would not get hurt because that's why god created lube and patience. And practice makes perfect. I was right.

Turns out we can hurt each other in the wrong position or at the wrong angle or at the wrong time, me due to length and depth, him due to girth. But that's why we don't fuck each other in the wrong position or at the wrong angle or at the wrong time.

It is equal parts art, skill, and instinct. And it is really fucking good, still, 14 years later.

[eastofeden]

It sucked....The first time I bottomed I didn't consent...I got raped when I was a teenager by two older gay men. Thankfully I left my body and went somewhere else so I only remember the struggle beforehand and what I felt like afterward...

[vacancy3]

^omg dude i am so sorry for your trauma....1st time for me was painful

[MisterMajestic]

Of course there was pain at first, then discomfort second and fianally Mental & physical acceptance at what was happening...That's how I sum it up...

At first my Bud kept saying "Relax, relax, relax."....Then I Mentally & physically let go and he could feel and sense that and then he kept saying "This is intense, intence.."...He Fucked me Missionary style the entire time, pausing at times, but he knew better than to SUGGEST we do any other position because once he pulled out I wasnt going to let him back in...

The aftermath of that? During that time I was co-managing a Hotel and it was painful walking up & down 3 levels of stairs (No elevator) and sitting down on even the softest anything was a task in itself. I think I went through the After Fuck pain for 2 to 3 days...

It didnt scare me away though...We remained Fuck Buddies for about 6-months...

[rareboy]

I was ecstatic! I kept thinking "finally ffs!"

This was me. It was earth shattering and life changing.

And my God, he was good.

[hylas]

penetration hurt, but once he was in, it was really amazing. i was outrageously loud ^^

after, i started crying... because i was so overwhelmed by the experience (in a good way).

my partner, not knowing why i was suddenly sobbing uncontrollably, almost shit his pants, fearing he did something terribly wrong...

(btw, he was an exploitative, predatory bastard... but i have to admit, sex was good.)

[AshyPhoenix]

It was probably the best sexual encounter I've ever had, even though I was still mostly a virgin (I'd fooled around with a couple other guys, but it never got to penetration). The guy was hung like a horse, but he made me feel so comfortable that it didn't hurt one bit. I sure miss him.

[Wvnudist]

The first time was wonderful best sex I ever had makes wonder why I waited so long gay sex is the best

[Saybrooke]

Pain :'( it was awful...

[ronboy]

It hurt a little. But you get past that when you realize that the pain eventually disappears, and the man you love is physically inside of you while you are being affectionate.

I loved him so much, and he loved me too.....

[umjreon88]

Well, this song sums it up in a few lines except for the blood part:



I've been fingered before my first time with my first boyfriend so I thought it wouldn't, but it freaking did! But slowly the pain went away and he gave me a good pounding. Briefly, inspiring yet strange.

[Harke the Boeotarch]

It hurt. There was blood. No lube.

[blublud]

I was 25. He was a few years younger. We had had oral many times before but never fucked. One night, he stayed over at my house and he wanted to fuck. "Let's do each other", he said. So, side by side, I gradually entered him until I was all the way in. The sensation of gripping warmth on my dick was amazing. Before too long I came. Then we parted for a cig and recovery.

After a bit, he said it was my turn to get fucked. I was leery of the expected pain but, since he didn't show much at all when I did him, and he's at least an inch shorter and lots thinner than me, I thought it wouldn't/shouldn't hurt much.

As he entered me, I grimaced a bit, but not in pain. More like discomfort. Once he was all the way in, he waited a bit then began thrusting. OMG! It felt way better than I ever expected. What surprised me the most was that, when he came, I could actually feel him spurt inside me.

[EuroSoccer]

It sucked....The first time I bottomed I didn't consent...I got raped when I was a teenager by two older gay men. Thankfully I left my body and went somewhere else so I only remember the struggle beforehand and what I felt like afterward...

[ParisZ]

Honestly... I felt like it was my duty, and that I didn't really have a choice (not in a negative way, of course haha)

[LatimerRd]

A great experience. Pain and pleasure and better than I ever imagined it would be. An much anticipated and desired adventure that led to others.