I absolutely love it I was about 38 my first time
I absolutely love it I was about 38 my first time
I don’t remember the exact first time but I’ve always loved playing with my ass. My buddy and I would jack and suck each other since we were kids. I loved having him fuck me but he said it hurt him for me to do it. He was much bigger than me, a solid 9” and thick(awesome cock). We figured out if he rode me he could take it as slow as he wanted and that let me stroke him while he did. Loved catching his load on my face and chest. Damn I miss that!
My first time getting fucked was amazing. There were about 15 people in the room watching us. I was fucking a chick missionary while her husband plunged his thick 8” cock in my ass. Our audience was impressed.
"Not doing the anal thing" - is that because you never had the chance, or is it because you don't prefer that?Originally Posted by Ebonybifemme7
First time was a bit awkward but really liked it.
My first time wasn’t terribly pleasant. We were both anal nubies, and really didn’t know what we were doing. I allowed my buddy, Dave, to enter me from the rear— doggie style. Despite copious amounts of Astroglide slathered on his amply sized cock, and an equally generous amount in and around my opening, he was able to penetrate only two or three inches — and it hurt like heck!
I wanted him to stop, but I was eager to fulfill Dave’s fantasy. After maybe 10 minutes of trying, he put me on my back, and I draped my knees over Dave’s shoulders. In that position, he was able to work his cock past my sphincter and eventually, a quarter-inch at a time, all the way inside me!
As he began sawing his cock in and out, his blissful expression and gentle, contented moans left little doubt he was thoroughly enjoying his first anal sex. Down below, my only sensation was a slightly uncomfortable feeling of pressure and fullness. Perhaps for Dave’s benefit, I pretended to enjoy being fucked. I wriggled my hips, urged him to “fuck me harder” and begged him to “fill me with your cum!” I even tugged sensuously at my own cock as by middle aged fuck buddy pounded away, but truthfully, I wasn’t really all that aroused, and never got more than semi-erect.
Okay, there was some satisfaction in knowing I could cross bottoming for another guy off my sexual bucket list, and I truly did enjoy feeling Dave’s cock spasming and throbbing as he orgasmed inside me. I’ll concede I was also strangely aroused by the feeling of Dave’s semen trickling out of me after he withdrew. But being fucked for the first time wasn’t quite the the fulfilling, erotic experience I’d imagined it might be. If there was any payoff, it was the unusually intense orgasm I had when Dave finally brought me off by hand.
I bottomed for Dave five or six more times that summer in a variety of different positions and I’m pleased to say our subsequent experiences were significantly more enjoyable, and that I occasionally long to explore that again.
My first time wasn’t terribly pleasant. We were both anal nubies, and really didn’t know what we were doing. I allowed my buddy, Dave, to enter me from the rear— doggie style. Despite copious amounts of Astroglide slathered on his amply sized cock, and an equally generous amount in and around my opening, he was able to penetrate only two or three inches — and it hurt like heck!
I wanted him to stop, but I was eager to fulfill Dave’s fantasy. After maybe 10 minutes of trying, he put me on my back, and I draped my knees over Dave’s shoulders. In that position, he was able to work his cock past my sphincter and eventually, a quarter-inch at a time, all the way inside me!
As he began sawing his cock in and out, his blissful expression and gentle, contented moans left little doubt he was thoroughly enjoying his first anal sex. Down below, my only sensation was a slightly uncomfortable feeling of pressure and fullness. Perhaps for Dave’s benefit, I pretended to enjoy being fucked. I wriggled my hips, urged him to “fuck me harder” and begged him to “fill me with your cum!” I even tugged sensuously at my own cock as by middle aged fuck buddy pounded away, but truthfully, I wasn’t really all that aroused, and never got more than semi-erect.
Okay, there was some satisfaction in knowing I could cross bottoming for another guy off my sexual bucket list, and I truly did enjoy feeling Dave’s cock spasming and throbbing as he orgasmed inside me. I’ll concede I was also strangely aroused by the feeling of Dave’s semen trickling out of me after he withdrew. But being fucked for the first time wasn’t quite the the fulfilling, erotic experience I’d imagined it might be. If there was any payoff, it was the unusually intense orgasm I had when Dave finally brought me off by hand.
I bottomed for Dave five or six more times that summer in a variety of different positions and I’m pleased to say our subsequent experiences were significantly more enjoyable, and that I occasionally long to explore that again.
The first time I received anal was absolutely fantastic. It felt so good. My wife had used a dildo on my ass a few times and also the guy's cock was well lubed as was myasshole.
I was 48 when i had the courage to reply to a CL ad, and went to his house and right away he could tell i was nervous. so we had a couple of shots and he helped undress me while he kept his T-shirt and sweatpants on, and me in my birthday suit. He only had intentions of giving me oral as we planned. He sat me on his couch while he knelt and i was like this is it!! he would suck me for 10 minutes at a time then would slap his forehead with my dick and it made me laugh! he knew how to calm me down! Felt sooo good!!
Can't really remember HOW it was, but I do remember the first guy that fucked me. Being my first time, I'm pretty sure that it didn't feel too good, BUT . . . . the idea that some guy was actually fucking me was a rush in itself. Up until then my mind-set was, "fucking was what a man did to a woman". but here I was on all fours with some guy kneeling behind me fucking away like there was no tomorrow. So, mentally ans emotionally, it was the greatest feeling in the world, physically, it must have been good cause here I am today still doing it. BTW, I still to this day have a pic, that my wife took. This is it, a 30 something year old pic that my wife took of me getting fucked for the very first time.........(by a guy)
Last edited by imariver; Jan 18, 2020 at 4:50 PM.
actually my first time was pretty good. years ago , before aids, i went to an abs to get a blowjob, maybe even give one. a guy came in my booth, and we sucked each others cock. then he wanted to fuck my ass . i never did this before , but i said what the hell , i wanted to try everything. so he lubed up my ass and his cock , and preceded to fuck me. as i recall , i didn't feel much pain ,and i liked the idea of being somebody's bitch. being bent over and being fucked like a cheap whore, by a stranger felt so dirty and erotic at the same time. he didn't fuck long before he said , '' your ass is so hot'' , and then came in my pussy. i felt like a sexy whore with a strangers cum in me. on the way home i felt his cum leaking out of me , and i thought , this must be what other whores feel like after they fuck. it was a sensual experience to feel like a female slut !
Nice!! Wish i was there
My first time was in a hotel in NYC. If felt so good, but the guy came after about 4 strokes. Disappointing. I’ve bottomed somewhat regularly and really enjoy it. Last guy I bottomed for is really, really thick. I absolutely loved it, once it opened up. A little pain @ the beginning, but he was gentle and patient. Unfortunately I up getting hemorrhoids and have had some bleeding too. Sucks as I REALLY, REALLY like this guy. But not sure I can do it again. No bottoming for 2 months now & I definitely miss it!
When I was 24, I visited my cousin in NYC while I was driving to Chicago. She told me I could stay at her place for a while if I wanted, since she was leaving for a few days for work. We ate dinner at a restaurant, and she gave me the keys to her apartment. What I didn't know, was that she had a gay roommate. They were around 27 or 28 years old at the time. He was at the restaurant with us, and was hitting on me all night, saying how pretty my lips were going to look around his cock, and how much he was going to ravage my ass so much that I wouldn't be able to walk. I was blushing, but laughed it off. My cousin said he was harmless.
My cousin left to go to the airport, and I went to the apartment to get some sleep. I found her room, and crashed on her bed. Her roommate came home maybe an hour or two later, and knocked on the bedroom door. I answered it, and he apologized about his behavior earlier, and asked if I wanted to drink with him while watching a movie. I said sure. He made us a cocktail, and we sat on the sofa while the TV was on. He asked what movie I wanted to watch, and he started to list some out. They were all gay porn movies. I told him I wasn't interested, but he picked one out, anyways. He asked if I ever watched gay porn, and I said, no. He said to at least give it a try. I laughed, so I said sure, whatever.
As were we watching, he asked what I thought. I said it wasn't really my thing, I preferred women. He then asked if I wanted to watch straight or lesbian porn. He was so straightforward about his sexual advances and watching porn, at that point I was like, well, I watched gay porn with this guy, might as well watch porn I liked. I said straight porn was fine. While we were watching, he sat closer to me, asking me if I liked anal. I said I did. He asked me if I ever played with my ass. I told him, yeah. He asked me if I ever wanted to suck cock, and I told him, yeah. He put his hand on my hand, and put it on his cock, which was getting hard. He said that if I wanted to suck cock, tonight was my chance.
He unbuttoned and unzipped his jeans, and pulled his pants and underwear down. His cock was pretty huge, but at that moment, it was still not fully erect, just semi-hard and flaccid. I was just staring at it. When I looked at him, he said to just start kissing it, so I did. Then I started licking it, and then putting it in my mouth. I was thinking how wonderful it was, having another man's cock in my mouth. His cock started to get bigger and harder, and I'd say it was close to 8 inches, and it had some girth. I was only able to put half of it in my mouth. He told me to open my mouth as wide as I could, and to relax my neck. Slowly, he pushed my head down. I gagged a few times, and tears were coming out of my eyes. I was getting closer to putting all of his cock in my mouth and throat. He asked me if I wanted to keep sucking on his cock, or if I wanted to get fucked in my ass. I told him that I wanted to get fucked in my ass.
He started to take my clothes off, and then his clothes. He told me to turn around. I asked if if he could put on a condom, but he said that he didn't have one, but he was safe. I was naive and dumb at the time, so I said that it was okay. Luckily, it was true (I got tested a couple of times afterward). He rimmed my ass for a while, and then put his cock inside me. It was nice and slow. When he felt my legs and butt tightening up, he'd slap my ass and told me to relax. He got deeper and deeper inside me until he had his entire cock up my ass. He reached around and stroked my cock while he fucked me from behind. I was moaning with every stroke of his cock. Unfortunately, he didn't last long, he came inside my ass, and I immediately came as I felt his cock throbbing in my ass.
That was just the beginning. We showered together, and slept in his bed. He woke me up later that night and we had sex again, then we slept some more. In the morning, we ate some bagels and fruit, and then fucked some more. He had some weed that we smoked, and although I don't remember much, I remember that we fucked a lot, and he had recorded some of it. There's a sextape of me somewhere, sucking on his cock while he was cumming. Of me getting fucked from behind, and then turning around to suck on his cock after. For some reason, I didn't seem to care. I was turned on by how uninhibited I was. I have an inkling that he showed my cousin the sextape, but she hasn't said anything about it to this day.
As first experiences go that one strikes me as pretty good. It is good you were able to be so uninhibited and enjoy yourself!
My first time was when we were almost that same age (actually, I did not have pubic hair yet). We had been playing various games that included sucking and fingering and even some spanking, and then one afternoon, in our secret "hideout: in the woods, he asked me if he could fuck me. We had found an old automobile bench seat that had somehow been discarded and hid it in our hideout, so I took off my blue jeans and pulled down my briefs and laid on it on my stomach. I think he must have used spit to lube my little hole, but I remember it wasn't uncomfortable at all when he started entering me. To tell the truth, our penises were still pretty small at that point, even when they were erect, so that probably accounts for his ease in entering and my immediate feeling of enjoyment. We were both really aroused, so it didn't take long before he climaxed inside me. Even after he came, his penis stayed hard and he continued to fuck me for several minutes. It really felt wonderful. He was sort of hugging me, and it just felt great being that close. I was very relaxed in one way, but my own little penis was rigid! He had only recently been producing semen, so after he finally pulled his penis out, I could feel the cum running down my balls.
The first time I had sex with a man. I met him in an adult theatre and never got his name. I told him I'd never been with a man and he told me he understood. We went back to his place and got naked. He was a very good teacher. It helped that he had a 7 inch cock. He would do something like rim my ass to me then let me do the same thing to him. When he stuck his dick up my ass I almost came. When he did shoot his load into me I all but started purring. I have loved anal ever since.
I was 45 years old. He was the first dick I had in my mouth. After our 3rd time together.l asked him to fuck me. I had been using a dildo between the sessions to loosen up. He fucked me bare back. I felt great and no pain.
I was 45 years old. He was the first dick I had in my mouth. After our 3rd time together.l asked him to fuck me. I had been using a dildo between the sessions to loosen up. He fucked me bare back. I felt great and no pain.
I was 21 and had been thinking about it and fantasizing about it for so long. There was an old vibrator of my sister's that I had swiped and was increasingly using for practice. I had a van (it was the '70s after all) where I had had a bunch of sexual adventures with both sexes. One night in a parking lot near a favorite cruising park I was starting to suck and older man (30s, I think) off when he stuck his hands down my jeans and began playing with my ass. When his fingers made it through to my hole and he began pushing them in I sort of involuntarily pushed back to take them. He then commented that I seemed hungry for penetration and did I want him to fuck me? Well, I didn't have to be asked twice, and quickly down came the pants. I had some vaseline in the van and he began to work it into me (again, it was the '70s) which felt great. Taking his cock though was strange and a bit awkward and it took me a few minutes to get used to his hardness pressing inside me and relax.
But soon enough he had me on my stomach and was fucking me hard like a man who hadn't had any hole in a while. He was grunting hard against my neck and into my ear with every stroke, which I found very hot. Then he thrusted and bit harder and a bit faster and grunted a bit louder and I could feel liquid spurting into my ass. When he pulled out he unexpectedly pulled my head towards his and kissed me hard (I had never been kissed by a man before, it was strange but fitting). He then asked me if I was OK, I said yes, and if I came too, and I said no. But later when I got up there was a big glob of semen on the floor and my cock was dripping, so I guess maybe I did. Even so, after he left and I drove a bit I could feel his cum leaking out into my underwear which made me so horny that I had to stop somewhere dark and use some of it to jerk off my now hard cock, and I came very hard. I also instantly knew that I wanted to be fucked again asap.
As I have related here before,, I was 12-13 he was 19 just out of high school.. my cousin.. I was sent to spend the summer on their farm.. I shared his bed.. first we slept naked then started hj.. then he sucked me and fingered me.. then was fingering me a lot.. I liked it.. then about a week later started humping my ass crack.. a couple nights later I was on my stomach and he had been fingering me for a good while and had three fingers in me.. he climbed on top of me holding me in place.. I felt him pour a lot of oil in my ass and then felt his cock in my crack.. nothing new he had done it a few times before.. but this time his cock found my pussy hole and I felt pressure agents it.. he said he was going to open my pussy with his cock and to relax like I did when he fingered me.. so I did.. little by little he opened my pussy.. then pushed the head of his cock in me.. he was big and thick.. it never really hurt all that much.. do to all the fingering.. I felt my pussy stretch to fit his cock.. then he slowly lowered himself down on to me driving his cock into me.. once balls deep inside me hi posed for a couple minutes to slow me to get relaxed with him inside me.. then he started fucking me.. slow at first.. the more relaxed I got the harder he fucked me.. soon I was moaning getting louder and louder.. the harder and faster he fucked me., soon he was pounding away at me.. then he stoped and rolled me over.. put my legs in his elbows and climbed on and in me again.. he went in me way deeper this way.. it felt so good I was moaning loudly.. he fucked me pretty hard and blew his cum deep inside of my pussy.. he woke me early the next morning and fucked me again.. I was his and his three friends cum dump that summer.. I grew to need it want it go looking for it..
After being stalked and beaten to a pulp on a regular basis by the school bullies, there was no way I was not going to experiment when I got on my own. They (the school bullies) might think I was gay, but I had to know. So, after having sex with several women and throughly enjoying myself, I went to the gay section of a local movie palace turned porn theater, and let myself get picked up. I told the man I had never been with another man and he said he understood. He was an excellent teacher. He would do something to me then have me do it to him, like rim. I had never thought of that before. Ass fingered and toys yes, but tongue? But Oh it felt so good. When it came to anal sex, he was very gentle and fucked me till he came, then he let me fuck him. I was quite pleased with myself. It's still true that whenever somebody fucks me and cums. I want to purr.
The first time I had anal sex with a guy was in my mid-30s during a brief period between relationships with women. I'd long been curious what sex was like from the woman's perspective, had lovers who really seemed to enjoy sucking my cock and anal sex. So I decided that given I was at that moment without a female to concern myself with and wasn't having sex it would be a good time to find out if ever I were going to. I answered an ad in 'Pennysaver' (no internet back then) from a married bi-guy who was 46, eleven years older. We talked a bit on the phone about my thoughts on it all and a few days later he came over to my house for some fun.
I'd decided going in that I wasn't going to hold back in any aspect - not just dabble with sucking or something, but kissing, nipple play, mutual sucking, anal; the whole range. So that gent arrives and the first thing I notice is that at 6'4" he's way taller than my 5'7". He asked if that was going to be a problem for me and of course I said "no". I've dated women as tall as 6'1" so height is of no great importance to me.
We touched and hugged a bit and then I just leaned over and kissed him full-mouth. He was a bit surprised as he expected me to be a bit hesitant, it being my first time. Then he just went with it. Clothes vanished, we were stroking each other, frotted a bit and then I took his cock into my mouth, licked it up and down, around the head, licked and sucked his balls, all the best things I'd liked that women had done for me as best I could (he still says I suck cock better than anyone he's met). Having a hard cock in my mouth turned out to be even more enjoyable then I'd imagined! Then he had a turn and we ended up in 69 for a long time, both leaking plenty of pre-cum in the process.
Finally I told him I really wanted to feel his cock in my ass and to get fucked. So I kneeled down with my butt in the air, he lubed my hole and his cock and gradually worked his way in. I was (and still always am) a bit tight but there was only a bit of mild discomfort before things got accommodating and he fucked me pretty thoroughly, with me moving and pushing back against his movement. I loved the feeling of fullness, his cock hitting my prostrate and the feeling of my cock and balls hanging down and swinging around (I've always found that to be sexy, both from my own standpoint and the feeling of the guy I'm fucking). After a while he asked if I'd like to return the favour because he couldn't hold off cumming much longer and of course I took him up on the offer. After some time I felt the need to have his cock in me again and we got into missionary with my legs up and his arms holding them, bending over and kissing deeply from time to time. Whoohoo, that was great as well! Eventually he pulled out, removed his condom and shot a load on my chest. We switched positions and I fucked him until I pulled out and did the same - we kinda rubbed the cum between our chests for a time while kissing and then went for a shower. And that was my first time...
In the three decades since we've had sex many times and in many places. My friend isn't "exclusive" to me and plays with other guys, but only bottoms with me (and I with him). I haven't had sex with other guys solo much, but we've had many threesomes, always with a bottom where we take turns at either end. Somehow it always seems to be my job to get the "third" off, but I love making people cum so...
The sad thing with ageing is that we're generally no longer "all we once were" and while my friend still gets hard enough for a most enjoyable suck the last couple of times he hasn't been able to get hard enough to get into my ass. I guess we just have to take things as they come and enjoy what we have while we have it.
More than you wanted to know perhaps, but there it is.
Last edited by Fiddlestyx; Sep 28, 2022 at 2:34 PM.
It was a great experience. He used a well lubed condom and my wife had previously used a dildo on me some. It was so great. I yelled for him to pump harder and harder. Unfortunately it was several years ago and I haven't repeated lf. I sure hope I can soon' I want it so much.
Wow, such a hot pic !!!!...made me hard...Can't really remember HOW it was, but I do remember the first guy that fucked me. Being my first time, I'm pretty sure that it didn't feel too good, BUT . . . . the idea that some guy was actually fucking me was a rush in itself. Up until then my mind-set was, "fucking was what a man did to a woman". but here I was on all fours with some guy kneeling behind me fucking away like there was no tomorrow. So, mentally ans emotionally, it was the greatest feeling in the world, physically, it must have been good cause here I am today still doing it. BTW, I still to this day have a pic, that my wife took. This is it, a 30 something year old pic that my wife took of me getting fucked for the very first time.........(by a guy)
Wish I was the bottom.....
Mmmm sounds fantastic, I think I'd be the same way.....
My first time I was a little drunk but it was awesome he was a tall muscular black guy he pounded the hell out of me my shoulder was bruised from hitting the wall he came twice it was great ! He was at least 8-9 inches i walked funny for two days
Lucky guy that your wife is into it my ex would never but at least she fucked the hell,out me with her strap ons
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