Guys: Your first anal experience as a bottom

How turned on were you by your first experience as an anal bottom? (receiving from a guy or a strapon?)

Did you try out "dry runs" with a dildo?

Did you find it too painful, and did not try it again afterwards?

Or, did you feel that, after the initial pain subsided, that you found yourself in another dimension of sexual pleasure?

After your first time, was your reaction:

"No more, man! Hurts too fucking much!"

"Maybe I should try it again and see how it goes this time."

"Oh, shit, man, that was fucking AWESOME!"

Also, what made you want to submit your ass to penetration in the first place?

If your first experience was getting pegged, what made you finally decide to go "the whole 9 yards" and look to get fucked by a REAL cock?

Your thoughts/experiences?

 

Also:

If you guys also like to "top", do you find the experience as hot and as stimulating as when you're the one getting his butt fucked?

 

Further..........

Do you find your orgasm is more intense when you're the guy getting fucked, or when you are on top?

Or, do you find your orgasms just intense no matter if you are bottoming or topping.........

 

If you are a "barebacking" bottom, do you find that when you feel the guy's hard shaft spitting out multiple jets of hot sperm deep inside your ass, that it further heightens your own orgasm?

 

My wife and I had been playing and I was using a dildo on her. After a few orgasms she was very wound up and I was going to town on her missionary while she had the dildo in her hand and was teasing my hole with it. The vibrations were driving me crazy, so I reached back and guided it into my ass. It was a pretty big one and I was surprised I took it. Once it was inside me the vibrations felt so good, it didn’t take long with it against my prostate to send me over the edge.
I think the whole thing really surprised my wife, she thought it was just a tease and had no idea I liked it so much. That started a desire in me I didn’t know I had. I had always been curious about sucking a guy but now I wanted to be fucked. Fast forward many years I found a guy online while on a business trip to do just that. I had no idea a real cock would be even better than the dildos I had been using. Boy did that open a new chapter in my life.

 

I take it that you're assuming that guys were grown ass men when they choose to check out anal sex... when not all of us were grown ass men when we first got fucked in the ass or it was attempted. Like, none of the stuff you put here applies to me and more so when I'm not a bottom and even being rather versatile in this, eh, I can take or leave fucking a guy - because I grew up doing it. My first experience with it... was messier than anything else since the man didn't try to penetrate me but creamed the shit out of my butt crack. A friend was the first to get it in me; it hurt a little, then it felt kinda nice but would feel better once all of my male friends were able to bust a nut - and I had adult dicks in my ass, stretching my hole just to get the head in so their cum could go in me and it hurt but it felt good and I didn't complain because I wasn't a crybaby and innately understanding that if I whined and complained about it, no one would want to fuck me.

In my beginning, I had no idea that men have a prostate gland or that it could be stimulated to induce orgasms and, almost to my "shame" I didn't learn about our prostate until I was an adult but, okay, that would explain a few things I'd felt when being fucked. But on the whole of it, my liking to be fucked seemed to be different from the way other guys wanted to be - and especially the more effeminate gay dudes who were total bottoms and totally dedicated to always being the girl when it came to having sex and they were not of a mind to fuck me in return so there were adjustments that had to be made.

And becoming aware of the whole top/bottom dynamic that, as someone who came up being versatile, didn't make a lot of sense to me to give up my ass to someone who wasn't of a mind to give up theirs. And while some guys were playing with dildoes and sticking other inanimate objects in their ass, I was being fucked with the real thing and this was not something that was a "game" or "fantasy" for me as far as being fucked went - still very much a part of the whole of things but I couldn't deal with guys who expected me to just give up my ass and wanting to treat me like I was a woman - or an effeminate gay man.

I can take or leave bottoming. I have never been a bottom; cannot adopt that mindset and I'm too literal-minded to think of my ass as being a pussy; I accept that, in some ways, I get into the "being the girl" part of things because I suck cock and if a guy's my idea of the right guy, sure - he can get this ass but with the understanding that I have a dick and I like using it; otherwise, what's the point in being versatile?

Yes, I understand that this is just me and the way I am and it's the way I grew up with all of this... but I couldn't help but to laugh for a moment at the presumption that anal bottoms don't get to be anal bottoms until they're adults and they're all into being a bottom, which isn't quite the same as being willing to bottom if/when you're not a bottom.

This should be fun...

PS: This is a conversation I've had with my protege, who for some reason seems to think that I'm a bottom and he often talks to me like I'm "his bitch" and how good he's going to fuck me - but then gets all weird when I tell him that, sure, he can get this ass... but I won't be the only one getting fucked. He bought into the whole top/bottom thing and in his mind, he's a top... and all other men are bottoms and I do find it offensive to be seen like I'm a "sub bottom" whose willing to do whatever to please a guy when... I'm not like that, never been like that, have no reason to be like that..

 

It was a bit awkward as he wasn't experienced topping. He had good size cock with some girth and we had a tough time getting it in me. But, once it started to push inward, it hurt but only until he slid it all the way in. I might have gasped because it felt so good and couldn't believe it was actually happening. He gradually built up speed until he was banging me hard. When he pulled it out I felt kind of disappointed because I was enjoying it more than I ever thought. From then on, I decided I was a total bottom when with guys.

 

How turned on were you by your first experience as an anal bottom? Wasn't a "guy" was a transexual prostitute and I wasn't expecting it, it turned me on

Did you try out "dry runs" with a dildo? Yeah I've had a dildo up my ass before

Did you find it too painful, and did not try it again afterwards? Wsn't too painful as "she" was very small, stang a bit and I've not done it since.

Or, did you feel that, after the initial pain subsided, that you found yourself in another dimension of sexual pleasure? Well I came pretty darn quick so must have enjoyed it!

After your first time, was your reaction:

"Oh, shit, man, that was fucking AWESOME!"

Also, what made you want to submit your ass to penetration in the first place? It wasn't meant to happen, thought she was a she, was astride me and slipped my cock into her knickers where it touched her cock... That was a surprise but after she made me suck it she lifted my legs up and fucked me

 

I'm similar in that the first time a guy's cock penetrated my ass and fuck me was in my childhood. My best friend across the street and I started experimenting even before our cocks could get hard, let alone semen come out of them, evolving gradually from stroking to cocksucking to ass rimming to pushing our soft cockheads into our assholes. Eventually in puberty we were full on fucking, and all of it was so much fun. Given that our sexual relationship was from 8-13 years of age, it was way past childhood experimentation: looking back I now know that it was a full on gay relationship.

But then I stupidly, crazily repressed all those gay feelings until my first girlfriend of 3 years broke my heart at 30, breaking up with me for the third time. That's when all those gay desires came flooding back, and all I had sex with from then on were guys--until girlfriend#2 from 54-57 years of age. She knew all the details of my past gay sex life (we were monogamous while we were together), and knew that I still hadn't had a man fuck my ass, despite my fantasizing about it since I was 35. I was just the top with guys. So she pegged me with a dildo strap-on one night, and grew to enjoy it a lot because of the power feeling it gave her. But I never actually liked it, always wishing it was a real guy fucking my ass.

It's weird, even now at 61, and living exclusively as a gay man, I still consider myself a bottom virgin, almost like I'm still repressing my boyfriend's cock in my ass when I was a kid. I'm crazy about rimming and fucking guys' asses more than I can say, but I am so ready to get my ass fucked again, and really feel what I imagine is that wonderful masculine power making me his. But I can't really say what the experience will be like for me. But right now, my biggest wish is to have a regular versatile fuck buddy (if gay love were to come, that would be fine too).

 

Only one way to find out: Drop that repression stuff, gird your loins, get boned in the butt. Easier said than done? It's pretty easy once you convince yourself that you have no reason to repress anything and especially something that happened so damned long ago. I get that messing with girls demands that you set other kinds of sex aside for the sake of them but, maybe it was just me, but I wasn't giving up dick just for pussy and no more than I'd give up pussy just to get some dick; no, thi bes going both way thing was way too much fun, way too exciting, and got me laid.

A lot. A whole lot. I submit to you that if you and that friend were happily having sex and he was boning you, you're not a virgin so the first thing is to stop believing that you are. If you're ready, then go find a guy and start making up for all that lost time. If you sit around waiting for a fuck buddy, well, let's just say that if I were you, I wouldn't be waiting because the odds of you finding one are slim to next to none and considering how many guys have a great sense of stranger danger and are afraid to have casual sex with a guy so they can see if he can be regular.

Otherwise, you will not know what the experience will be like for at this point in your life.

 

Not how that should have started out but fuck it would be hot if that's what you were looking for. And I would if she looked like a she.b

My wife has used small dildos on me, I would like her to actually use something around the size of an average cock and take time to relax me and fuck me but she isn't really into it.

I asked a hooker to peg me with a strap on She asked if I was getting off on it. I guess she wanted me to moan, I guess I just wanted to relax and see how it felt till I did get to being comfortable and excited by it. No regrets, I wanted it and want cock.

I've not been fucked by a guy, I've not been with a guy but I would take it up the ass. If it was a regular hook up I would want to fuck him for the experience or I would be happy to return the favour if that was a mutual feeling.

I don't have any desire for a gay relationship or emotional connection just sex for fun. Mutual oral and giving each other pleasure for fun.

Fucking a guy is not high priority, I want to be fucked but will return the favour. I don't want to be a total bottom as I have a cock and like using it.

I guess I would be vers if hooking up with a guy.

At this point I would jump in boots and all for any experience to test my fantasy so that would be fuck a guy, get or give oral and even take it up the ass depends on the opportunity that presents. If I do one or any of those things I would soon know if I'm going to try more.

Yes, I think it would hurt a little but then it would start to feel good. It's partly mindset to get off on it because you know you want it but there may be reasons people get off like. It could be any I list below or it may be a romantic emotional connection.

It's taboo
It's submissive
It's fun
It's a fantasy unfolding
"I like Ass play"
I want to know how it feels
It's experimenting
It's sex
Something new to try
Might be curious
Might simply be gay or Bi and male sexual orientation comes naturally.

 

The first time I experience anal penetration using a toy was not a painful because we found a nice size one. Not too big in diameter. The experience was great. I wanted to do it mainly out of curiosity. To see how it would be to be to have something up there. I slowly increase the size (mainly out of greed ) and found that it did hurt. I was slightly rushing due to being horny, but once it was in...heaven. However, I was still repressing those feelings of pleasure so it took me a while to get used to it. This went away over time after accepting...I like what i like and how it makes me feel. Now tho...I can't get enough. My heart races in anticipation of stuffing my ass with my toy or machine. What made me want a real dick? The feeling of something warm and pulsating inside you. The thought of looking at your own dick and wondering what it would be like to take one in your ass.

 

[QUOTE="GrayGuy57, post: 9447717, member: 322681"]How turned on were you by your first experience as an anal bottom? (receiving from a guy or a strapon?)

Did you try out "dry runs" with a dildo?

Did you find it too painful, and did not try it again afterwards?

Or, did you feel that, after the initial pain subsided, that you found yourself in another dimension of sexual pleasure?

After your first time, was your reaction:

"No more, man! Hurts too fucking much!"

"Maybe I should try it again and see how it goes this time."

"Oh, shit, man, that was fucking AWESOME!"

Also, what made you want to submit your ass to penetration in the first place?

If your first experience was getting pegged, what made you finally decide to go "the whole 9 yards" and look to get fucked by a REAL cock?

Your thoughts/experiences?
[/QUOTE]

I was incredibly turned on - I was 31 and had only started playing with guys (just oral and mutual wanking) a year earlier. The guy was a very gentle but masculine middle aged guy who took it slow. Unfortunately he was well endowed and I had no idea of how to receive anal, so it hurt a lot at first. After a while, the pain subsided though not completely but it was offset by the excitement. I hadn't tried dildos or anything really other than my fingers and assumed it would be easy. As it turned out, I got crabs from him and I was so mortified by the experience that I didn't want to meet guys for a while at all, nevertheless a couple of months later we met up again and then met on and off for a couple of years, usually late at night as I was coming home I would call him and go to his apartment for a quick session. He always fucked me missionary, we tried other positions but they were more painful for me. It got easier over time but it wasn't until several years later I realised how to relax my anus to make anal sex with a well endowed guy pleasurable. All in all though it was good and introduced me to the joys of being a bottom. What led me to it - well, it just felt natural. I realized immediately when I started seeing guys that I wanted to be fucked and that I was a pure bottom - topping others never did much for me. There's the physical sensation of being penetrated which no dildo can reproduce and the mental feeling of being the passive, receptive partner is very exciting to me.

 

My first anal experience wasn't the best by a long shot.
Pre-teen friend with a tiny dick fucked me without lube until he came in me. We started out me trying to fuck him. It was his idea. My dick was way too big for his unlubed butthole so he suggested we try the other way. He liked it enough to cum in me but for me it was like a finger in my ass. I enjoyed sucking him much more than being fucked by him. We were young and inexperienced so if I was being fucked by a small dick today I know I would do it very differently, on my back instead of bent over.

 

I have a prostate! Stimulating it totally rocks! Butt plugs, dildos, fingers, cocks? In my ass if you would.

I discovered how great penetration felt by experimenting on myself.

Also, being penetrated is, in my worldview, an essential piece of guy-on-guy sex. Every bi guy should be both penetrator and penetratee. (That doesn't seem to be a word. Prolly oughta be.)

I don't find being the penetratee to be a matter of "bottoming". It's too integral to the overall act. You're both fucker and fuckee (look at that, another new word!) though likely not at the same time.

(A brief--yeah, right--aside here. When I met my second wife, she was having an ongoing affair with her boss. Cool with me. In fact we quickly got to the point where we had him over for threesomes. And he was bi! We agreed that if we couldn't all be together, that any pair of us could fuck. So her boss and I also ended up in an affair. Anyway, here's where I'm going with this..one of our favorite things entailed her lying on her stomach and one of us guys mounting her and penetrating her ass, and the other guy penetrating his ass. Yay! The middle guy was penetrator AND penetratee. Also, FYI, the filling in that sandwich drove that bus!)

It didn't usually hurt much. Relax, relax, relax and lube, lube, lube.

The one time that it was too painful for me to continue (remember, I hate being a sub) was when I tried being double-anally penetrated. Christ on a pogo stick, that hurt! Felt like a blind surgeon was performing a hemorrhoidectomy with a rusty butter knife. Still, I gotta try!

Overall, I love being fucked.

 

I picked a guy that was a perfect size for me... nothing too big.. and he understood it was my 1st..very slow and easy .

 

I have enjoyed dildo play in my ass, my wifes strapon and other dildos. I have only done it with our old gay friend and my best friend . They were both smaller then the dildos that I had used in the past, so I was plesantly surprised when I was penetrated at how nice and easy it slid in my ass. I had prostate orgasms with both and it was a pleasurable experienced. My wife isn't as timid as they were. When she fucks my ass, its like Payback She is anything but timid and has taken me to new levels of pleasure.. I actually like her intensity more.

 

I probably would have never gone bi if it hadn't been for my wife. When she would give me a blow job she would sometimes rub my asshole. Then one time she slid a finger inside and tickled my prostate. It really turned me on. We progressed to using a dildo. I thought I was in heaven. She told me though that a real dick feels even better and suggested that I try a real one. After much discussion about it and realizing that she was okay with it, I decided to give it a try. She was right and I was hooked. We still have sex as much as before, but now I just have to have a dick now and then. The feeling of a dick sliding in and out and hitting the prostate is awesome. I have enjoyed it every time. She asked if I had sucked him too and when I said I hadn't, she said "try it, you'll like it". She was wrong about it. I love it. I'm so glad my wife suggested me having sex with another guy.

 

You don't know know lucky you are @GregS.

 

Very lucky, dude. Keep her.