Your first anal experience?

[priapusone]

I want to taste it so bad!

 

[burnie4434]

My first experience was the day after I sucked my first cock and with the same guy. I found the night before that I loved sucking a cock. The next night I was sucking his cock when he told me he wanted to fuck me. He assured me he would be gentle and stop if I asked him to so I aggreed. He first lucked my ass the I felt him put lube on my ass. He the started to finger me with one and soon three fingers. That felt good. I then felt the head of his cock pushing At my hole. I relaxed and felt the head entwr me. There was a little pain and then it felt good. He slowly kept getting more if his cick into me until I felt his balls on my ass. He then started to fuck me. I quickly got used to it and squezzed my ass muscles and told him to fuck me hard which he did. After he fucjed me for about 10 minutes he came in my ass. He left his cick in my ass until it git aoft and fell out. He asked if I liked it and I told him I loved it but now my ass felt empty. He laughed and he told me that he knew I would like it.

 

[fde2blk]

Great story, love to fill your void

 

[woman_inside]

I'd finally decided to take the plunge and have sex with another man, I put up an ad explaining more or less what I was looking for and discussed it a bit more with the first guy that replied - even though it was my first time I was too horny to wait for more replies and was determined to get fucked before I changed my mind; if I'd been braver, I would have gone to a gay bar to get picked up instead of putting up an ad. Anyway, I went to his place, as agreed I pretended to be unconscious while he stripped me and dressed me as his maid. Then I started 'cleaning' while he fondled my butt and when he caressed my legs he asked me if my boyfriend liked me hairy, I answered I was a virgin. He took me to the bathroom and made me shave my legs and armpits. He then took me to his bed, we French kissed, he caressed my chest and nipples, telling me how much he loved my big breasts, he put on a condom telling me he didn't want to make me pregnant, told me to lie on my back and put my legs on his shoulders, and fucked me. It didn't really hurt, but I was so tight he had trouble getting his cock inside me.

 

[phfantsy78]

I'm hoping mine happens real soon, I found several itimes on line at adammale(.) com that I wanted to try, 1) being a 3 piece anal traier set (trainer, middle, Large), 2)vibrating cock, 3) anal plug 4) twist 'n shout dildo, plus 2 bottles lube. Now I know I'm not going to take them all at once, My goal would be to use the trainer first, and the middle from the kit and then the vivbrator last, plus I got to pick a free gift and chose the DVD of hardcore gay sex. My idea would be is when the package arrives, go to a near hotel with an over night bag, for at least 2 nights, stop at the store on the way there and pick a few pairs of pantyhose. Hopefully the TV at the hotel could be hooked up with a small DVD player. Take a nice shower dry off off and get a pair of the panyhose on, turn on the DVD and whip out the trainer and go from there...I'm hoping that my very long time desire will be met and more things will or pop-up...I think this will be the correct step for me to enter into the world of anal sex and I hope it will my put on the path to trying a real cock.

 

[Curioustallis]

neeed it

This needs a bump. I'm laying here with a dildo in my ass and wishing to get a chance to post my first to this thread.

 

[TomBoner]

After an hour chatting at the bar together we were both so horny that we were ready to explode. When we finally made it to my hotel room, we both just stripped naked and started 69'ing until we each unleashed a massive load of hot creamy sperm and semen into each others mouths.

We recovered for the better part of an hour before we both started getting hard again. I somewhat hesitantly asked him if he wanted to be the first person to take me anally. He anxiously responded yes and admitted it would be his first time giving anal. For a couple of 30 year old guys we figured we had waited long enough.

I went to the bathroom and got the bottle of lotion and returned to the bed, giving him the bottle. I laid down flat on my back and pulled my legs up to my chest. He smiled as he saw my exposed twitching anal entrance and poured a large amount of lotion onto his fingers. The feel of his cool, lubricated fingers spreading lotion on my virgin hole made my own cock pulsate harder and my heart raced in sexual overload.

His fingers slowly started probing my hole and opening the entrance. I could see his own cock getting even harder and knew that I was moments away from a sexual act I'd fantasized about for so long. Finally after he had gotten 3 fingers into me and made my own anal lubrication start to flow he got up on his knee's with his cock aligned with my crack.

He lowered his hands down and raised my buttocks up until my anal entrance came in contact with his throbbing, purple, swollen mushroom shaped head. I felt him start to push it into my tightness and my own cock got even more engorged in response. Finally, with little resistance from my now more than ready ass-hole, he slid his long hard smooth penis fully into my anxiously accepting hole.

With my rear end pulled up slightly in that position his cock head lined up perfectly with my prostate gland and as it started pressing against it I moaned out loudly in total overwhelming pleasure. While starting to fuck me with deep, slow, steady thrusts he took his hand, still with some residual lotion on it, and started to stroke my excited penis. I was in absolute heaven feeling a real live throbbing hard cock fucking me for the first time while my own hardness was being stroked into what I knew would be a mind blowing orgasm.

I watched intently as I started to see his face giving the expressions I knew only too well was indicating his own impending orgasm. His eyes started to close and his head tilted back slightly. I reached down between my legs and allowed my index finger to wrap around his hard thick shaft. The feeling of my finger touching his penis seemed to send him over the edge. I spread my legs wide, allowing him to sink himself fully into my body and enjoyed feeling the underside of his cock spasming as he started to unload his ejaculation into me.

I don't know why it seemed so sexually satisfying to allow him to cum inside my body, but I felt a sense of overwhelming enjoyment with feeling his hot thick cream being shot deep into my anal cavity. His cock exploded again and again and again as he experienced what he would later say was one of his most powerful orgasms. I knew just how powerful his ejaculation had been when his juicy sperm and semen leaked from my body an hour or so later. As for then he just buried his hardness fully within me and started stroking my own cock even harder.

With the prostate stimulation it didn't take long. It was also a very unique orgasm due to that fact. Rather than long hard streams of cum my penis just spasmed wildly and shot small spurts of cum all over my stomach and chest. It wasn't that it was any less cum, it just was a totally different sort of ejaculation. Finally when it was done we both stayed perfectly still and content for the better part of a couple of minutes before he finally slowly withdrew his cock from me and left me to enjoy the deposit he had made within me.

 

[jackstud]

Very exciting Tom

 

[TomBoner]

^^^ Glad you enjoyed it jack.

 

[simpleman911]

i was younug

He didn't enter me he just licked may ass and jacked me off. What a camping trip that was. It felt so good. He asked me to stroke him and I did gladly. I was scared, he was older but watching him edge then cum was amazing. Later I started fingering myself and then using small dildos. No man has ever been in my ass. Im not attracted to men but do love hard straight cocks. Weird I guess.

 

[mwmdallas]

My first anal was also the first time I ever had sex with another man. I was recently divorced and thought I would try tasting a cock for my first time. I posted an ad in an online personals page and an experienced guy responded. We traded some emails, phone calls, and chat sessions before he invited me to his place. He knew it was my first time ever with another man, I was never more nervous then when I knocked on the door to his place. He was very kind and considerate, we talked for over an hour before any dicks came out. I still remember the first time I knelt in front of him and took his cock into my mouth. I thought for my first time we would just trade hand jobs and/or blowjobs. Little did I know what he had in store for me.

After playing with each other and taking turns sucking each others cock on the sofa he suggested heading to his bedroom. As we lay together on his bed he started playing with my ass. It didn't take a rocket scientist to figure out what he wanted to do, especially after a finger or two was slid into my ass. I didn't need much convincing. He stood me on the floor leaning over his bed and lubed me up real good. I remember feeling his condom clad cock pushing against my ass and wondering just exactly what I had got myself into. He stopped just as soon as the head of his cock slid in and waited for me to get used to the feeling of his cock in me. Soon he slowly slid the rest of his cock in. I felt a little discomfort initially, but that soon passed. He "flexed" his cock in my ass then slowly started fucking me. It didn't take him long to fill his condom with cum. It was amazing I could feel his cock pulse as he shot his load.

I went back one more time several weeks later and discovered about all he wanted to do was slide his cock into my ass. It was a remarkable first time to have sex with a man and get my ass filled.

 

[bps]

That's a thrilling tale. You had the courage to go for it and it sounds as though you both got what you wanted.

My first anal was also the first time I ever had sex with another man. I was recently divorced and thought I would try tasting a cock for my first time. I posted an ad in an online personals page and an experienced guy responded. We traded some emails, phone calls, and chat sessions before he invited me to his place. He knew it was my first time ever with another man, I was never more nervous then when I knocked on the door to his place. He was very kind and considerate, we talked for over an hour before any dicks came out. I still remember the first time I knelt in front of him and took his cock into my mouth. I thought for my first time we would just trade hand jobs and/or blowjobs. Little did I know what he had in store for me.

After playing with each other and taking turns sucking each others cock on the sofa he suggested heading to his bedroom. As we lay together on his bed he started playing with my ass. It didn't take a rocket scientist to figure out what he wanted to do, especially after a finger or two was slid into my ass. I didn't need much convincing. He stood me on the floor leaning over his bed and lubed me up real good. I remember feeling his condom clad cock pushing against my ass and wondering just exactly what I had got myself into. He stopped just as soon as the head of his cock slid in and waited for me to get used to the feeling of his cock in me. Soon he slowly slid the rest of his cock in. I felt a little discomfort initially, but that soon passed. He "flexed" his cock in my ass then slowly started fucking me. It didn't take him long to fill his condom with cum. It was amazing I could feel his cock pulse as he shot his load.

I went back one more time several weeks later and discovered about all he wanted to do was slide his cock into my ass. It was a remarkable first time to have sex with a man and get my ass filled.

 

[oral_tendency]

After an hour chatting at the bar together we were both so horny that we were ready to explode. When we finally made it to my hotel room, we both just stripped naked and started 69'ing until we each unleashed a massive load of hot creamy sperm and semen into each others mouths.

We recovered for the better part of an hour before we both started getting hard again. I somewhat hesitantly asked him if he wanted to be the first person to take me anally. He anxiously responded yes and admitted it would be his first time giving anal. For a couple of 30 year old guys we figured we had waited long enough.

I went to the bathroom and got the bottle of lotion and returned to the bed, giving him the bottle. I laid down flat on my back and pulled my legs up to my chest. He smiled as he saw my exposed twitching anal entrance and poured a large amount of lotion onto his fingers. The feel of his cool, lubricated fingers spreading lotion on my virgin hole made my own cock pulsate harder and my heart raced in sexual overload.

His fingers slowly started probing my hole and opening the entrance. I could see his own cock getting even harder and knew that I was moments away from a sexual act I'd fantasized about for so long. Finally after he had gotten 3 fingers into me and made my own anal lubrication start to flow he got up on his knee's with his cock aligned with my crack.

He lowered his hands down and raised my buttocks up until my anal entrance came in contact with his throbbing, purple, swollen mushroom shaped head. I felt him start to push it into my tightness and my own cock got even more engorged in response. Finally, with little resistance from my now more than ready ass-hole, he slid his long hard smooth penis fully into my anxiously accepting hole.

With my rear end pulled up slightly in that position his cock head lined up perfectly with my prostate gland and as it started pressing against it I moaned out loudly in total overwhelming pleasure. While starting to fuck me with deep, slow, steady thrusts he took his hand, still with some residual lotion on it, and started to stroke my excited penis. I was in absolute heaven feeling a real live throbbing hard cock fucking me for the first time while my own hardness was being stroked into what I knew would be a mind blowing orgasm.

I watched intently as I started to see his face giving the expressions I knew only too well was indicating his own impending orgasm. His eyes started to close and his head tilted back slightly. I reached down between my legs and allowed my index finger to wrap around his hard thick shaft. The feeling of my finger touching his penis seemed to send him over the edge. I spread my legs wide, allowing him to sink himself fully into my body and enjoyed feeling the underside of his cock spasming as he started to unload his ejaculation into me.

I don't know why it seemed so sexually satisfying to allow him to cum inside my body, but I felt a sense of overwhelming enjoyment with feeling his hot thick cream being shot deep into my anal cavity. His cock exploded again and again and again as he experienced what he would later say was one of his most powerful orgasms. I knew just how powerful his ejaculation had been when his juicy sperm and semen leaked from my body an hour or so later. As for then he just buried his hardness fully within me and started stroking my own cock even harder.

With the prostate stimulation it didn't take long. It was also a very unique orgasm due to that fact. Rather than long hard streams of cum my penis just spasmed wildly and shot small spurts of cum all over my stomach and chest. It wasn't that it was any less cum, it just was a totally different sort of ejaculation. Finally when it was done we both stayed perfectly still and content for the better part of a couple of minutes before he finally slowly withdrew his cock from me and left me to enjoy the deposit he had made within me.

Damn, I'm a virgin who's been thinking about what it would be liked to get fucked and that's very hot.

 

[Jerseyshore]

My first time was when I was a very young man. He was much older and had recently brought me out. I was ready to please him and he was very gentle and patient. It was quite wonderful as I came and felt him cum inside of me. There was a deep feeling of oneness that I never forgot.

 

[Jerseyshore]

Lovely story Tom

 

[bdave2]

From anal phobic to loving it

My first wasn't very nice at all. I was on leave from the army and I was very drunk at a gay party. I was pushed down and raped in a hallway. 'Came to with a bloody ass and a few weeks of discomfort. I was anal-phobic for several years. This changed when I went into a sauna about 3 in the morning to sober up in my late 20s. Everyone had left and the young attendant chatted me up in the steam room and offered me a massage. He was a student at a local college, but he had been a massage therapist. He gave me a wonderful massage and I was becoming just a mass of relaxed jelly. When he approached my ass and grazed my rosebud I panicked and tensed up. He was very patient and kept sliding his thumbs up my thighs and into my ass crack. After many minutes I began to moan as his thumbs pushed along the insides of my ass cheeks. He then began to gently massage the edges of my asshole. He teased me like this for ages and ages and just the very tips of his thumbs began to slip in and out just a little bit. I started repeatedly saying, "Please, please. Oh, god that's good." He continued to tease me even though I was still begging him, "Please, please." Finally after I was becoming quite loose he plunged one thumb into me as he continued to massage my asshole and slide up inside me. After both thumbs were inside he began to stroke and stretch me and I was beside myself. I finally cried out, "Fuck me, fuck me. For god's sake, please fuck me. Please." I didn't even believe it was me saying this. I was face down. He reached over to pick up a different kind of massage oil and pulled me back along the massage table until my feet were on a ledge near the floor. He dribbled the oil down my crack and slid into me so gently my asshole was like a slippery glove caressing his cock. He was hard as a rock and my ass vibrated when I clamped down on him as he was sliding in and out. He kept fucking me for a very long time. I was practically delirious and babbling incoherently. He eventually reached under me and jacked me off as he started to ram into me very hard. I think we came at the same time. I remember the feeling of his warm cum dribbling down my legs when he went to get a towel to clean me up. I wanted to tell him to leave it as I loved the feel of it draining out of me, but I was too exhausted to move. I curled up on the massage table. He covered me with a towel and I went to sleep. I sure as hell wasn't ass phobic any more. Being fucked is great when you have a skilled lover. Sigh.

 

[jackstud]

Very beautiful Dave. So glad your feeling good about anal now. Your story excited me. PM me

 

[Tmmldr]

My first wasn't very nice at all. I was on leave from the army and I was very drunk at a gay party. I was pushed down and raped in a hallway. 'Came to with a bloody ass and a few weeks of discomfort. I was anal-phobic for several years. This changed when I went into a sauna about 3 in the morning to sober up in my late 20s. Everyone had left and the young attendant chatted me up in the steam room and offered me a massage. He was a student at a local college, but he had been a massage therapist. He gave me a wonderful massage and I was becoming just a mass of relaxed jelly. When he approached my ass and grazed my rosebud I panicked and tensed up. He was very patient and kept sliding his thumbs up my thighs and into my ass crack. After many minutes I began to moan as his thumbs pushed along the insides of my ass cheeks. He then began to gently massage the edges of my asshole. He teased me like this for ages and ages and just the very tips of his thumbs began to slip in and out just a little bit. I started repeatedly saying, "Please, please. Oh, god that's good." He continued to tease me even though I was still begging him, "Please, please." Finally after I was becoming quite loose he plunged one thumb into me as he continued to massage my asshole and slide up inside me. After both thumbs were inside he began to stroke and stretch me and I was beside myself. I finally cried out, "Fuck me, fuck me. For god's sake, please fuck me. Please." I didn't even believe it was me saying this. I was face down. He reached over to pick up a different kind of massage oil and pulled me back along the massage table until my feet were on a ledge near the floor. He dribbled the oil down my crack and slid into me so gently my asshole was like a slippery glove caressing his cock. He was hard as a rock and my ass vibrated when I clamped down on him as he was sliding in and out. He kept fucking me for a very long time. I was practically delirious and babbling incoherently. He eventually reached under me and jacked me off as he started to ram into me very hard. I think we came at the same time. I remember the feeling of his warm cum dribbling down my legs when he went to get a towel to clean me up. I wanted to tell him to leave it as I loved the feel of it draining out of me, but I was too exhausted to move. I curled up on the massage table. He covered me with a towel and I went to sleep. I sure as hell wasn't ass phobic any more. Being fucked is great when you have a skilled lover. Sigh.

great story.

 

[darkheels]

A toy I made myself when I was younger.

 

[nudeguy76]

sort of...willing?

I had met a guy online. We talked and he gave me his address. Not living far, i was there quickly. I climbed the stairs after he buzzed me into the building. When i reached his doorway, it was opened a bit. Closing it behind me, i said hello. From the other room i saw the flickering of a tv and heard, "come on in". I quickly took off my clothes. Walking nude into this strangers living room felt naughty! Was he alone? He looked up, shocked, but soon smiling. He stood up and approached me, still clothed. Telling me how hot it was to have a nude man show up at his place, he slid his shorts down. Reaching out to grab his shaft, i dropped to my knees......mmmmmmmmmm! (Want to hear more?.....)

 

[FistedSister]

A crayon.

That's right! Someone dared me.

 

[Marcus63]

Back when I was married, we picked up a vibe for the wife at the local toy & gift. The next day, while fooling around, she said it was pretty small and would probably go in my butt pretty easily. A little lube later, I was hooked, as she worked it in and out while stroking me to a finish all over myself. Soon I was playing with her vibe more often than she was...

We have a slim vibe about 6 or 7 inches long. I have used it on my wife more than a few times. I love when it's in her ass and I'm in her pussy, or the other way around.
Anyway, one night we came home and started fooling around, I got the vibe out and started playing with her when she said she wanted to used it one me. I said ok and she rubbed it on my cock and balls and slowly slid it past my balls and touched my asshole with it.
it felt really good and I said put it in a little, she did, then I said you can put it in a little more and she did. she was slowly sliding it in and out of my ass and I said, put it all the way in, and she said, it already is.
She wrapped her lips around my cock and within a few minutes I blew a huge load in her mouth. I want her to buy a strap on and use it on me and I'd like to try a real cock, I know how one feels in my mouth, now I want to know how one feels in my ass.

 

[sxcjockbi69]

mmm all these stories are a real turn on,i am actually seeking a guy 47+ for my 1st time,i love my beads and vibe but yearn for the real thing someday! x x

 

[Emmcee20]

Lots of great stories here. My first time was with a dildo my ex-wife bought for me as a birthday present. I had taken her anal cherry some while before which surprised me as she was a very sexual woman and 13 years older than me but had never had any anal attention until I (lucky for me!!) came along when we met at college.

She had fingered my hole during sex and saw how I reacted and she loved to do that while she blew me. She presented me with this parcel on my birthday which contained a couple of anal magazines, some lube and a 7" dildo. It was a soft latex and realistic looking outer coating that was thick and veiny but it had a 'ball sac' that you could fill with (ideally) warm water and, at the right moment, squeeze it to create the feel of cumming.

Naturally we had an early night after a birthday dinner and a few drinks. She had obviously planned everything and when we went to bed she had me browsing the mags while she got things sorted and then she massaged me all over until she got to my butt where she paid plenty of attention, grazing a nail around the perineum and my ring. Then came the lubed finger/s. I was on my back and legs spread she could sit beside me and control the whole situation. It was a long and titillating experience where she knew how to draw out all the wonderful sensations.

My own hard 6" was bobbing around in the air begging for her attention when she introduced the bulbous head of the dildo to my now open back door. It slid in a way and she paused. I felt it stretch me but it was never too painful and she took her time. She had me tighten my ring on it which pushed it out a little and when I released she slid it deeper and twisted it slightly. After several repeats of this I had all 7" inside me and I felt wonderfully full.

Soon she was playing with my nipples and stroking my new friend in and out of me smoothly and increasing the pace. I started leaking all over my stomach as the intensity grew and as she started stroking my cock in rhythm to the dildo she asked me if I was ready. I was deliriously in pleasure and didn't quite know what she meant but said yes. With four or five hard shaftings of the dildo and my cock, she then squeezed its ball sac and the jet of fluid flooded my insides and I exploded in my orgasm. Best birthday present ever! She timed it beautifully. Sadly the rubber latex of the ball sac didn't last as long as the dildo but it became a pretty regular part of our play.

 

[fasolati23]

Intro to ass fucking

I have told this story before and the reaction from one or two people was that they were sorry that I experienced the "violation."
I don't feel that way at all. I remember it as just as an experience. Not one I would want anyone to go thru because they might not handle it well.
I was 21 and new to drinking. With the exception of a couple of experimental bi-sexual events spread out from age ... I was straight. I was dating and considering marriage.
I went to a bar, got totally drunk and was offered a ride home by a guy who was probably a couple of years older than me.
I woke up in a bed, face down, totally naked. As I slowly came out of my drunken stupor I realized that there was someone on top of me. I was laying there with my legs spread eagled and he had his penis in my ass.
I think my first reaction was one of total embarrassment. Macho guys were not supposed to be laying there getting their ass fucked. Actually I was not all that macho. Anyway I lay there pretending to be still asleep. I concentrated on the sensation of his dick going in and out of my ass. I felt him sliding around on my body from the lubricant. I realized that it felt good. I was enjoying the sensation of his cock filling my ass and sliding in and out.
I knew when he was going to ejaculate and felt it when he did. It actually felt cold.
I felt his body shifting around as he got off of me. It was then that I realized that there was someone else in the room. He and the other person were whispering. I was mortified to realize that someone had been watching me get my ass fucked. I wondered if it was a female or not. I am not sure why that made a difference.
I was thinking about pretending to be waking up but I remained very still, pretending to be asleep. I just didn't know how to handle looking someone in the eye who had just fucked my ass.
Then it happened. He got up and the other person took his place. I felt the new warm body settling down between my legs. I felt his penis brushing across m ass cheeks and knew it was another man. I felt him fitting his cock head into my opening. I was worried that I was going to experience pain. I knew I must have missed what I was sure was inevitable pain of a dick in my virgin ass for the first time because I was passed out. Now this guy felt bigger and I felt pressure. He slid into me and the pleasant feeling of the fat cock sliding in and out of me returned.
I lay there, breathing deep and trying not to react to the sensations of the penis in my ass. Again I felt the coolness of his cum squirting up my ass and he too got up from the bed.
I could tell that one of them had left the room from the sound of the door opening and closing. The one who stayed was getting back on the bed, I was sure he was going to fuck my ass for the third time.
It was then that I realized that my pretending to be asleep was not working. He knew I was awake. He pushed at my hips and whispered for me to roll over. I did. I did so keeping my arm over my eyes , still not wanting to have eye to eye contact with anyone.
I realized that my own penis was semi erect. I had felt the sensation of pre-cum leaking out while my ass was being fucked. It would actually feel like it was squirting each time he pushed into me. I felt him take it in his hand and massage it for a few seconds before I experienced the fantastic sensation of his mouth closing down over it. I had had oral sex performed on me before but never was the feeling as intense as it was then. I gave up all pretext of being asleep and let my self go, enjoying the fantastic sensations of having my dick sucked after having my ass fucked.
He kept me in his mouth until I had emptied a load that seemed bigger than any before. He sucked me dry. He kissed my belly and got up. I stayed in my same position with my arm still across my eyes. I heard him go into the bathroom and then out the bedroom door. It was at that point that I got up the courage to sit up. I got my self together and gathered the courage to go out the bedroom door.
I was in his mother's house. He and she were sitting in the den. He introduced me as his friend who had spent the night. I was able to actually pretend that everything was as normal as could be. Made my excuses and left. I never looked back.
I have gone all these years wondering about it all and wanting to try it all again. Someday, maybe.