how was your first time getting fucked by a guy?

[Gregshaw]

My very first time getting my ass fucked was by a contractor who was doing a job where I worked. I was 19 & he was probably 30. I accidentally heard him fucking one of the company reps in a locked storeroom late one night when everyone else had gone home. It was electrifying to see him banging away at another guy who was bare ass & bent over. I couldn't get out outta my head but eventually I knew that I had to get the same.

I managed to get to work with him, he was kinda blue collar scruffy & loud but he was alright to work with & I suggested going out for a few drinks on his last day once he'd finished his instalation. Since he liked me he agreed & yeah I lied about my age but back then some bars weren't as thoro in checking IDs.

I was terrified but managed to mention what I'd seen & he was silent at first but I gained his trust because he realized that I'd not said anything. Anyways he took me back to his hotel & eventually I plucked up enough courage to actually touch him coz he wouldn't do anything until I'd shown him I was serious. My hands shook like crazy but eventually I was able to run my hands down to his crotch & touch my first cock. I though i was making a mess of it but I was amazed when he started to get hard & make little groans of pleasure. Eventually we got down to it in bed.

He was VERY careful & took his time loosening me up & backing off when it was too much but eventually I was face down on the bed, legs spread my bare ass feeling his groin bump against me & it felt AMAZING to have his hard cock moving in & out of my ass. It didn't hurt at all. When he came inside me he thrust harder & harder making my cock rub on the towel we'd out on the bed & I ended up shooting my own load in a way i'd never known was possible.

I stayed the night & he had my ass again in the morning with me on the bed my back & ankles on his shoulders & him kneeling by the edge. If last night felt amazing this time felt even better & it has stayed as my favorite position but after that he moved outta state to another job & I never saw him again

[ImBiVersatile]

One of the hottest threads ever!

[bnicks122016]

My first time I was 21 and in college. To that point I had only been with women. I had been doing a bit of nude modeling that turned into some gay modeling. This was back in the 80s, so pretty taboo at the time. It had been mostly been me and mother nude guy that had progressed int o some oral. Which to my surprise I enjoyed.
I have never been sure of the entire situation. The man who hired me was also the photographer, and I had suspected he was just a guy with money who liked guys. And what proceeded to happen pretty much convinced me.
I had just done a solo shoot for him and when it was finished I was extremely horny. It had lasted a couple of hours and for most of it he had me fondling myself etc. So I was ready to get home no jerk off.
The guy was in his 40s, good looking and in good shape, but had never made a pass of any kind at me before this. As we were finishing up and getting ready to go he made a comment about how much I seemed to enjoy the session. I was still nude and pretty hard. I kind of laughed and said that I had and would need to take care of things later.
He said he understood, and at that point asked if I would like some help. I was a little stunned to be honest. The only gay I had done to that point was for pay and never to organize. He walked over to me and put my hand on his crotch. He was very hard and said he would like to help with my problem.
The next thing I know we were in a deep kiss and he had his hand on my very hard cock. We laid on the bed I had been modeling on and nature took over. I unzipped his pants and released a very hard 7? cock. We were making out and stroking each other when he whispered to me to suck his cock like I knew I wanted to. He pushed my head down with very little resistance and I was soon bobbing up and down on his hard cock. He started taking dirty calling me a slut, his good little cocksucker etc. That turned me on even more nd he knew it. I was so hard!
He had maneuvered me into a 69 position and started fingering and licking my ass. That was a first for me and I was ready to explode. When he stopped I literally groaned in agony. He laughed and said he had something I would really enjoy.
I knew what he wanted and he knew what I wanted. He put me on my back and told me to tell him what I wanted. I was so worked up, I told him I wanted him to fuck me. He smiled and lubed up. He was very patient and over the next 10 minutes he was fully inside me. He knew how to fuck a man and over the next 20 minutes made me feel things I never thought I?d feel. After the initial pain I couldn?t get enough. When I came it was the most intense orgasm I had ever had. Shortly father he came inside me and whispered I was his now.
over the next 18 months I had the most amazing sex with him I have had with anyone

[park ave]

I can sum up my first time getting fucked by a guy in two words: it hurt. And the second time it hurt too. A lot. It wasn't until the third third time when I finally got a handle on things that I understood it for the first time.

When I was a teen, I was seeing an older married man, who was, as they say, on the 'down low.' Our usual activity was me blowing him. Weather permitting we would go somewhere deserted (a nearby beach was a favorite destination), although on occasion he'd spring for an inexpensive motel room, and I'd suck him off.

Even when we were outdoors he liked both of us to be naked when I blew him, as he liked me to kiss and lick my way down his body to his cock, and also so that while I was sucking him he could stroke my cock (he had told me more than once that I sucked better when I was horny). At some point, in addition to stroking my cock he started playing with my balls and then lightly fingering my asshole, and that became part of our usual routine while I blew him.

Well one night we're at the beach and I'm sucking him, and, as I realized later, he had squirted a bit of lube onto his finger, which he started to gently work into my asshole. I was slightly startled, but he had me keep doing what I was doing (sucking his cock, that is), and, I have to say that after the initial surprise wore off, his finger moving in and out of my ass actually felt good. Plus it felt sexy to have his finger moving in my ass, with me lying naked across him and sucking his adult cock.

But I was unacquainted with anal sex at the time, so I did not expect what came next. He said something like, 'Here, stay like this,' meaning on all fours, and he moved around behind me, put some more lube directly on my ass, and, taking me by my hips, began to work his (rather large) cockhead into my asshole.

Well. I was, as you may imagine, very familiar with that cock. It was maybe 6 or 6.5 inches, but it was quite thick. It was tough enough getting my mouth around it, and the thought of it in my ass was scary. I tried to relax and follow his instructions, but he wasn't particularly patient and continued to push his cock in. Additionally, our sessions together had always been more about his pleasure than mine. So I gritted my teeth and tried to get past the pain. It felt as if he got most if not all of his cock in my ass. He pumped quickly until he had a moaning orgasm and came inside me. But it had really hurt.

The second time was no better. We followed the same plan, a deserted beach, at night, both of us getting naked, and me thinking I'd just be giving him a blowjob. But he maneuvers around behind me, and despite my misgivings and him urging me to relax, plus him assuring me that it will get better, it didn't. He fucked my ass with that thick cock of his again. Mercifully, he came relatively quickly, but frankly I wasn't loving it.

The third time was actually different. He had gotten us a room, which he didn't often do, perhaps because I had been visibly unhappy the last two times out. This time, however, rather than waiting for him to direct me into doggie position (as I later learned it was called), I decided to take the initiative and, while I was blowing him, suggest fucking while he lay flat on the bed. He lubed my ass and I lubed his hard cock (which was actually fun to do), and, straddling him, I was able to ease myself down onto his cock at my own pace. The pain was still there but considerably lessened, and I was much more aware this time of the fullness of his cock inside me and my ass moving against it.

He was a big man and I was a slim teen, so this position was easy for us to maintain. He held my upper arms and my hands were on his chest so I was able to ease my ass up and down against his thrusts. As my ass moved on his cock, things got heated, and for the first time I was able to feel what it was like to have a man's cock swell inside me and pump cum in my ass as he came. Notwithstanding the first two sessions, it was, I felt, the first time I had really been fucked.

After he had cum and while I was still straddling him and his cock was still in my ass, I could imagine how my girlfriends had felt when we fucked and I had cum in them and my cock still pulsed inside them. It was terribly intimate and sexy. I would have lain down on his sweaty chest and kissed him long and deep, but he never liked to kiss, so I think I just rolled off him. Sex with him was always primarily about him getting his rocks off.

Just as an afterword, I didn't entirely 'get' anal sex until my second lover, who was much more patient. Plus our relationship was reciprocal, whereas with the first I was more of a boytoy. And additionally his cock was less thick (and actually quite gorgeous). Even though our sex was primarily oral, anal sex was with us an act of incredible sexiness and physical intimacy. I'm just glad I had the opportunity to explore unprotected anal sex with him back in the 70s before it became a worry.

[heisaflirt]

I was around 50 yrs old, wife knew I was bisexual and we had met a couple who the male wanted to experiment, they were into the Hotwife cuck scene like ourselves, both of them were really hot and after our first meet we decided to all meet again. He and I texted a bit and talked about each of us being virgins, and we both wanted to experiment farther than just sucking which we had both had experience doing at that point. We decided to meet, him come to our house, and my wife suggested that she leave, I kind of wanted her to stay to watch them a bit, but I really thought it was hot just the two of us so I would not have any inhibitions. I thought that whole week it wouldn't really happen but each day came and then it was "tomorrow" and I knew I had better eat right, douche,,,, research it. My wife had her thoughts as well and she shaved me completely the night before. the day of I was pretty nervous but also excited, when I got home from work my wife was getting dressed to got out to a restaurant by herself that had a busy bar as well. She teased me a bit and then... I was on my own and it was really happening,, He had texted saying he was on his way. I showered, douched again, got out a medium sized dildo and tried to get myself ready. I was very nervous but also feeling pretty dirty as well. we had texted about kissing and we were both turned on by it. when he pulled up I opened the door and just grabbed him on the front porch and made out with him. I thought that was pretty hot that the neighbors may see. We didn't spend a lot of time talking, I had thought we might get in the hot tub, but we decided to go right to the bedroom. The best part of the story is when he layed down and I started making out with him and grabbing his dick,, then I worked my way down and pulled his pants off and... by god after swinging 25 years and seeing a few big dicks and maybe 3 really really big dicks he had one of those 3 holy cow big dicks for real. I had seen a picture next to a beer can but didn't really realize it was literally that big..... I sucked him for a while and then I straddled him and worked his dick in my ass it really went in pretty easy,, I guess I am a dildo slut. I remember thinking I am really getting fucked for real now. He bent me over the bed and started fuckiing me, I remember him saying his wife couldn't take his whole dick in her ass. He fucked me hard and rough until I had to stop. we tried a few other positions I didn't cum while he fucked me but I did leak on the bed. It was maybe the best sex ever in some ways.. a great first time for sure...

[joseluis]

excellent story

[joseluis]

excellent story

[mrheem]

My first time was in college. A friend was over drinking and smoking pot. He should not have been driving so I told him he could crash at my place. He was sleeping on the floor in a sleeping bag. It was cold in the apartment so I told him he could sleep in my bed with me. He got in bed with me and pretty soon I could feel his hard cock on my back. I rolled over and we started kissing and then 69-ing. Eventually I told him I wanted him to fuck me. It took some time to take him, but after that initial "uncomfortable" stage it felt amazing. I came without touching my cock and came right after I did. It was so nice.

[ilovetowatchcs]

My first time was with a married neighbor. I had blown him a few times, and one day I asked him to fuck me. Because I had done it wih dildos and liked the feeling. And he did it slow, then a little faster - then came in my ass. And unless you have been fucked in the ass, but by the right guy and cock, you will never know how sexually exciting it is.

[Sundazzled]

I'll concede that I don't have much experience in this department, but four years ago did find myself playing with, Dave, a 63 year old retired dentist who was separated from his wife and very eager to explore his bisexual side.

Because Dave lived on a secluded 20 acre property in rural Delafield, much of our sex play took place outdoors in Dave's hot tub or on the big redwood deck surrounding it. For the first few months, our encounters typically revolved around mutual masturbation, cock-to-cock play and giving Dave oral. I really had no ambition to explore other activities, but one July evening we were lounging around nude on the deck drinking tequila shots and cooling down between dips in the hot tub when Dave turned to me and out of the blue asked "Would you ever consider letting me fuck you?"

I don't know; maybe it was the tequila talking. Maybe it was a suppressed fantasy to try something new and decidedly taboo. Maybe I just wanted to help a friend fulfill one of the fantasies on his rather large bucket list. Whatever the reason, I found myself saying yes, and the next thing I knew the two of us were boundingbbare-assed up to Dave's bedroom!

We were both anal newbies at this point, and really didn't know what we were doing. I'd been pegged a few times with a dildo during threesome play, but had never experienced the real deal. I got down the the doggie position as Dave applied Astrolube to my backside and to his penis. Since Dave had never been with another man, I agreed to let him fuck me bareback. He was strangely insistent about that. He placed his cockhead against my hole, pushed forward, and went in no more than an inch or two before I began to experience a lot of pain, pressure and an uncomfortable sense of fullness. Dave paused for a few moments, grabbed my hips, and pushed forward again eliciting a yelp of pain.

It was apparent Dave wasn't going to penetrate me in this position, so we tried again with me on my back, Dave kneeling between my legs and my knees draped over his shoulders. He applied more lube, and resumed his assault on my anal virginity. Again, he got only his cock head inside me before I begged him to stop again.

We tried for the next 40 minutes in probably six different positions to get Dave's cock fully inside me, and I dare say he was determined to make it happen. We tried with me bent over, resting my torso on the bed and Dave standing behind me. We tried lying on our sides, we tried with Dave lon his back and me straddling his cock. Ad soon as he attempted to drive his cock home, I felt bright pain and an uncomfortable sense of fullness and pressure. Ultimately, we abandoned the effort.

Over the next week, I had lunch with a gay friend, TJ, who I figured would have some expertise in matters of anal sex. After he got over the shock of learning that I was actively bisexual, I told him about my disappointing first try at bottoming for Dave. TJ explained that successful anal penetration can't be rushed and requires several steps. First he recommended an enema with warm, soapy water to clean the anal cavity. Then he recommended having Dave insert one or two fingers to stretch my opening. Then TJ recommended having David work a dildo or butt plug into my anus before attempting penetration with his own cock. He cautioned that anal sex requires oceans of lubricant, and recommended buying a syringe for putting lube inside my anal cavity. Last, my gay friend advised that first timers generally find it easier to be on top "cowboy style" and lower themselves onto the penetrating partner. This, he said, puts everything at the correct anatomical angle and gives the partner bring penetrated control over the speed and depth of penetration.

Following a shopping trip to Walgreen's and the the local sex shop, I phoned Dave and offered him another go at my virgin ass, and he invited me to come out to his place the following weekend.

Long story made short, we followed TJ's instructions to the letter. I actually sort of enjoyed having Dave administer the warm water enema, and the feeling as he inserted one, then two lubed fingers into my opening. After about 15 minutes of fingering, I asked Dave to lube up my pretty, pink dildo.nI tried to relax as he worked it inside me with minimal resistance. There was lots of pressure and an odd sense of needing to poop. But there was no pain this time -- just mild discomfort when he pushed the thing past my sphincter. Dave worked the dildo rhythmically in and out of my backdoor for probably 10 minutes. Then he applied a virtual flood of Astrolabe and told me I was about to receive a good fucking.


Now lying on his back, I straddled Dave, reached behind, positioned his cockhead against my opening and bore down firmly. As before, he went in maybe two inches. I breathed deeply, then bore down again, and to my astonishment, Dave's cock went right in -- right to the hilt!

I began bouncing up and down on Dave's penis, occasionally reaching back to fondle his balls. Beong fucked wasn't particularly pleasant for me, but looking into Dave's eyes, I could see he was in ecstacy. After about five or six minutes, I could tell Dave was getting close. His breathing became ragged, his ball sac was drawn up tight, his nipples were erect. All the signs were there... and then I felt this cock go absolutely rigid inside me. It twitched and throbbed, and Dave groaned loudly, "Oh, fuck,yeah!" I knew I was receiving a load of his cum deep inside me ... and the thought of it strangely thrilled me.

We lay together in a post-orgasmic heap until Dave's erection subsided and his spent pecker fell out, causing a trickle of fresh semen to flow out of me and down onto my balls ... proof positive that I had actually been fucked by another man.

[Sundazzled]

I'll concede that I don't have much experience in this department, but four years ago did find myself playing with, Dave, a 63 year old retired guy who was separated from his wife and very eager to explore his bisexual side. Because Dave lived on a secluded 20 acre property, much of our sex play took place outdoors in Dave's big hot tub or on his big redwood deck. For the first few months, our encounters typically revolved around mutual masturbation, cock-to-cock play and my giving Dave oral. I really had no ambition to explore other activities, but one July evening we were lounging around nude on the deck drinking tequila shots and cooling down between dips in the hot tub when Dave turns to me and out of the blue asks "Would you ever consider letting me fuck you?"

I don't know, maybe it was the tequila. Maybe it was a suppressed fantasy, or may I just wanted to please my friend help fulfill one of the fantasies on his rather large sexual bucket list. Whatever the reason, I found myself saying yes, and the next thing I knew the two of us were boundingbbare-assed up to Dave's bedroom!

We were both anal newbies at this point, and really didn't know what we were doing. I'd been pegged a few times with a dildo during threesome play, but had never experienced the real thing. I got down the the doggie position as Dave applied Astrolube to my opening and to his penis. Since Dave had never been with another man, I agreed to let him fuck me bareback. He placed his cockhead against my hole, pushed forward, and went in no more than an inch or two before I began to experience a lot of pain, pressure and an uncomfortable sense of fullness. Dave paused for a few moments, grabbed my hips, and pushed bforears again causing me to yelp on pain.

It was apparent Dave wasn't going to penetrate me in this position, so we tried again with me on my back, Dave kneeling between my legs and my knees draped over his shoulders. He applied more lube, and resumed his assault on my anal virginity. Again, he got only his cock head inside me before I begged him to stop again.

We tried for the next 40 minutes in probably six different positions to get Dave's cock fully inside me, and I dare say he was determined to make it happen. We tried with me bent over, resting my torso on the bed and Dave standing behind me. Wevtriedlying on our sides, we tried with Dave lying on his back and me straddling his cock. Ad soon as he attempted to drive his cock home, I felt bright pain and an uncomfortable sense of fullness and pressure. Ultimately, we abandoned the effort, and I allowed Dave to cum by rubbing his cock externally against my butt hole.

Over the next week, I had lunch with a gay friend, TJ, who I figured would have some expertise in matters of anal sex. After he got over the shock of learning that I was actively bisexual, I told him about my disappointing first try at bottoming for Dave. TJ explained that successful anal penetration can't be rushed and requires several steps. First he recommended an enema with warm, soapy water to clean the anal cavity. Then he recommended having Dave insert one or two fingers to stretch my opening. Then TJ recommended having David work a dildo or butt plug into my anus before attempting penetration with his own cock. He cautioned that anal sex required oceans of lubricant, and that I should obtain a syringe for putting lube inside my anal cavity. Last, my gay friend advised that first timers generally find it easier to be on top and lover themselves onto the penetrating partner's peris. This, he said puts everything at the correct anatomical angle and would give me complete control over the speed and depth of penetration.

Following a shopping trip to Walgreen's and the the local sex shop, I phoned Dave and offered him another go at my virgin ass, and he invited me to come out to his place the following weekend.

Long story made short, we followed TJ's instructions to the letter. I actually sort of enjoyed having Dave administer the warm water enema, and his inserting one, then two lubed fingers into my opening. After about 15 minutes, Dave lubed up my pretty, pink dildo and worked it inside me with minimal resistance. There was pressure and fullness, but no pain this time, and only mild discomfort when he pushed the thing past my sphincter muscle. He worked the dildo in and out of my backdoor for probably 10 minutes, then applied a virtual flood of Astrolube.

Now lying on his back, I straddled Dave, reached behind, positioned his cockhead against my opening and bore down firmly. As before, he went in maybe two inches. I breathed deeply, then bore down again, and to my astonishment, Dave's cock went right in to the hilt!

I began bouncing up and down on Dave's penis, occasionally reaching back to fondle his ballsac. Bring fucked wasn't particularly pleasant for me, but looking into Dave's eyes, I could see he was in ecstacy. After about five or six minutes, I could tell Dave was getting close to orgasm. Hi breathing was ragged, his ball sac was drawn up tight, his nipples were erect. All the signs were there... and then I felt this cock go absolutely rigid inside me. It began to twitch and throb, and Dave groaned "Oh, fuck,yeah!" I knew that I was receiving a load of his cum deep inside me ... and the thought of it strangely thrilled me.

We lay together in a post -orgasmic heap until his erection subsided and his spent pecker fell out, causing a small trickle of fresh semen flow out of me and down onto my balls ... proof positive that I had actually been fucked by another man.





I'll concede that I don't have much experience in this department, but four years ago did find myself playing with, Dave, a 63 year old retired guy who was separated from his wife and very eager to explore his bisexual side. Because Dave lived on a secluded 20 acre property, much of our sex play took place outdoors in Dave's big hot tub or on his big redwood deck. For the first few months, our encounters typically revolved around mutual masturbation, cock-to-cock play and my giving Dave oral. I really had no ambition to explore other activities, but one July evening we were lounging around nude on the deck drinking tequila shots and cooling down between dips in the hot tub when Dave turns to me and out of the blue asks "Would you ever consider letting me fuck you?"

I don't know, maybe it was the tequila. Maybe it was a suppressed fantasy, or may I just wanted to please my friend help fulfill one of the fantasies on his rather large sexual bucket list. Whatever the reason, I found myself saying yes, and the next thing I knew the two of us were boundingbbare-assed up to Dave's bedroom!

We were both anal newbies at this point, and really didn't know what we were doing. I'd been pegged a few times with a dildo during threesome play, but had never experienced the real thing. I got down the the doggie position as Dave applied Astrolube to my opening and to his penis. Since Dave had never been with another man, I agreed to let him fuck me bareback. He placed his cockhead against my hole, pushed forward, and went in no more than an inch or two before I began to experience a lot of pain, pressure and an uncomfortable sense of fullness. Dave paused for a few moments, grabbed my hips, and pushed bforears again causing me to yelp on pain.

It was apparent Dave wasn't going to penetrate me in this position, so we tried again with me on my back, Dave kneeling between my legs and my knees draped over his shoulders. He applied more lube, and resumed his assault on my anal virginity. Again, he got only his cock head inside me before I begged him to stop again.

We tried for the next 40 minutes in probably six different positions to get Dave's cock fully inside me, and I dare say he was determined to make it happen. We tried with me bent over, resting my torso on the bed and Dave standing behind me. Wevtriedlying on our sides, we tried with Dave lying on his back and me straddling his cock. Ad soon as he attempted to drive his cock home, I felt bright pain and an uncomfortable sense of fullness and pressure. Ultimately, we abandoned the effort, and I allowed Dave to cum by rubbing his cock externally against my butt hole.

Over the next week, I had lunch with a gay friend, TJ, who I figured would have some expertise in matters of anal sex. After he got over the shock of learning that I was actively bisexual, I told him about my disappointing first try at bottoming for Dave. TJ explained that successful anal penetration can't be rushed and requires several steps. First he recommended an enema with warm, soapy water to clean the anal cavity. Then he recommended having Dave insert one or two fingers to stretch my opening. Then TJ recommended having David work a dildo or butt plug into my anus before attempting penetration with his own cock. He cautioned that anal sex required oceans of lubricant, and that I should obtain a syringe for putting lube inside my anal cavity. Last, my gay friend advised that first timers generally find it easier to be on top and lover themselves onto the penetrating partner's peris. This, he said puts everything at the correct anatomical angle and would give me complete control over the speed and depth of penetration.

Following a shopping trip to Walgreen's and the the local sex shop, I phoned Dave and offered him another go at my virgin ass, and he invited me to come out to his place the following weekend.

Long story made short, we followed TJ's instructions to the letter. I actually sort of enjoyed having Dave administer the warm water enema, and his inserting one, then two lubed fingers into my opening. After about 15 minutes, Dave lubed up my pretty, pink dildo and worked it inside me with minimal resistance. There was pressure and fullness, but no pain this time, and only mild discomfort when he pushed the thing past my sphincter muscle. He worked the dildo in and out of my backdoor for probably 10 minutes, then applied a virtual flood of Astrolube.

Now lying on his back, I straddled Dave, reached behind, positioned his cockhead against my opening and bore down firmly. As before, he went in maybe two inches. I breathed deeply, then bore down again, and to my astonishment, Dave's cock went right in to the hilt!

I began bouncing up and down on Dave's penis, occasionally reaching back to fondle his ballsac. Bring fucked wasn't particularly pleasant for me, but looking into Dave's eyes, I could see he was in ecstacy. After about five or six minutes, I could tell Dave was getting close to orgasm. Hi breathing was ragged, his ball sac was drawn up tight, his nipples were erect. All the signs were there... and then I felt this cock go absolutely rigid inside me. It began to twitch and throb, and Dave groaned "Oh, fuck,yeah!" I knew that I was receiving a load of his cum deep inside me ... and the thought of it strangely thrilled me.

We lay together in a post -orgasmic heap until his erection subsided and his spent pecker fell out, causing a small trickle of fresh semen flow out of me and down onto my balls ... proof positive that I had actually been fucked by another man.

[Neonaught]

Congratulations on pushing past your initial difficulties. I have always said that all you need for the first fuck is lube, courage and patience!

[Sundazzled]

Congratulations on pushing past your initial difficulties. I have always said that all you need for the first fuck is lube, courage and patience!

Thanks. I'm hardly an experienced bottom. Dave fucked me twice that first night, and two other times. I never really found it that enjoyable, although I did derive some satisfaction from helping my friend fulfill his anal sex fantasies and seeing the obvious pleasure it brought him. I also enjoyed the intense and prolonged orgasms I experienced after, presumably the result of prostate stimulation.

I haven't bottomed since September 2018, but I'm not discounting the possibility of doing it again, given the right partner and the proper motivation.

[Neonaught]

Thanks. I'm hardly an experienced bottom. Dave fucked me twice that first night, and two other times. I never really found it that enjoyable, although I did derive some satisfaction from helping my friend fulfill his anal sex fantasies and seeing the obvious pleasure it brought him. I also enjoyed the intense and prolonged orgasms I experienced after, presumably the result of prostate stimulation.

I haven't bottomed since September 2018, but I'm not discounting the possibility of doing it again, given the right partner and the proper motivation.

I get you about anal sex doing little for you but for seeing the obvious pleasure you are giving him. I had the same experience with a buddy. For years I always topped him and he loved it. A couple of years ago he mentioned he missed fucking so I started bottoming for him. I enjoyed it but that was mostly because I really feel affectionate for this guy and love making him feel good.

I have had a few bottoms that had powerful and continuous prostate orgams when I fuck them and I'd sure like to have that happen to me!!!

[Small one]

Had a friend both around 35 we had a few 3 sums with my girl at the time. He was fucking her as I was getting blown he saw I had a butt plug in and asked about it.I told him I enjoyed anal play. We had some toys and asked if he wanted to see more which he agreed. I started pulling out different size dildos and riding them as he watched. We finished up and they went home.
He called me about an hour later and said he had a question said sure but he said it needed to be in person. He came back and had all kinds of questions about our toys we talked I told him I also liked to suck cock and she knew and also watched. I got him started on smaller ones we played thru the night into the morning. He then asked if I would fuck him Hell yea I did and he loved my small cock using his hole. At that point I blew my load in him and pulled out. I had never been fucked by a real cock and asked for him to fuck me he agreed. I blew him until he was hard and guided his cock in my ass wow this was so much better than dildos. He fucked me hard until he shot his load in my already worked hole I was leaking precum big time when he pulled out I put a butt plug in to save my first load and sucked him clean also a first.
After that night we fucked and sucked each other for almost 2 years at least 3 times a week until he moved damn hot times Saved a pic. of his soft cock need to find another. Have one guy that only lets me suck his cock sometimes.

[trs50ms]

I'll start be saying my asshole has always been my erogenous zone. I tried getting fucked when I was younger, but at age 12, the young guy just weren't long enough to penetrate me and ended up just poking at it, which felt good, but just didn't get the job done. Later in life at the age of 57, I met a guy in his early 30's on Silverdaddies and we hooked up. The first few times we sucked each other off and it was good. He had a 7" uncut cock with an average cum load. On one of our meetings he asked me if I done anything else because he said he wanted to fuck. I told him the it was something I had always fantasized, so we set up a time a few weeks later to meet. We drove out to the secluded beach and parked my SUV, got out and he got into the back of it laying on his back. I got in and closed the hatch. He had alreadu pulled down his pants exposing his already hard cock. I got even more excited as I slipped my shorts off and started sucking on his thick cock. I stopped and asked if he was ready to fuck, he said yes. I rolled a condom over his throbbing cock an lubed it up as well as my ass. I knelt on one knee over him and reached down to position his cock for entry. The feeling of the head of his cock against my asshole was amazing!! I pressed against it to push it in. I kept pressing as it began to go in, the pain and discomfort of it was actually euphoric. At this point, I start jamming it in as I wanted him inside me bad. I felt it pop in and I sat down ball deep on him. That feeling was indescribable, having a real cock deep inside me was fucking mind blowing. I began to slowly ride up and down on his cock and he was loving it. I eventually picked up the pace fucking like the pure whore I had become!! He had to stop me several times, he wasn't ready to cum. The more he fucked me the more it became emotional for me as well as the pleasure of the big cock inside me. After about 20 minutes, he couldn't hold it back, so I sat down on his cock and he started pumping is cum inside. I could have gone longer, but I knew he had held back as long as he could. We laid there for about 15 minutes, with his semi hard cock still in me, and talked about doing it again in the future. We would eventually meet several time over 3 years, eventually fucking bareback and getting his cum inside my ass. Each time got better and better. He was a hell of a lover. I eventually moved and we were not able to hook up as much as then.

[Modude]

Had a friend both around 35 we had a few 3 sums with my girl at the time. He was fucking her as I was getting blown he saw I had a butt plug in and asked about it.I told him I enjoyed anal play. We had some toys and asked if he wanted to see more which he agreed. I started pulling out different size dildos and riding them as he watched. We finished up and they went home.
He called me about an hour later and said he had a question said sure but he said it needed to be in person. He came back and had all kinds of questions about our toys we talked I told him I also liked to suck cock and she knew and also watched. I got him started on smaller ones we played thru the night into the morning. He then asked if I would fuck him Hell yea I did and he loved my small cock using his hole. At that point I blew my load in him and pulled out. I had never been fucked by a real cock and asked for him to fuck me he agreed. I blew him until he was hard and guided his cock in my ass wow this was so much better than dildos. He fucked me hard until he shot his load in my already worked hole I was leaking precum big time when he pulled out I put a butt plug in to save my first load and sucked him clean also a first.
After that night we fucked and sucked each other for almost 2 years at least 3 times a week until he moved damn hot times Saved a pic. of his soft cock need to find another. Have one guy that only lets me suck his cock sometimes.

Mmmmm that's a nice cock...

[Robin Black]

Similar ages, maybe a bit younger because I don't think either of us had pubic hair yet. I was on an old couch we had dragged out to our "hideout" in the woods, and was on my stomach. Don't know what we used for lube, but it did not hurt when he penetrated me. He only fucked me for a few minutes before he climaxed. No semen yet, so nothing to clean up!

[DMercator]

Had a friend both around 35 we had a few 3 sums with my girl at the time. He was fucking her as I was getting blown he saw I had a butt plug in and asked about it.I told him I enjoyed anal play. We had some toys and asked if he wanted to see more which he agreed. I started pulling out different size dildos and riding them as he watched. We finished up and they went home.
He called me about an hour later and said he had a question said sure but he said it needed to be in person. He came back and had all kinds of questions about our toys we talked I told him I also liked to suck cock and she knew and also watched. I got him started on smaller ones we played thru the night into the morning. He then asked if I would fuck him Hell yea I did and he loved my small cock using his hole. At that point I blew my load in him and pulled out. I had never been fucked by a real cock and asked for him to fuck me he agreed. I blew him until he was hard and guided his cock in my ass wow this was so much better than dildos. He fucked me hard until he shot his load in my already worked hole I was leaking precum big time when he pulled out I put a butt plug in to save my first load and sucked him clean also a first.
After that night we fucked and sucked each other for almost 2 years at least 3 times a week until he moved damn hot times Saved a pic. of his soft cock need to find another. Have one guy that only lets me suck his cock sometimes..

OK... that was pretty hot!