how was your first time getting fucked by a guy?

[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!

[juicyphallus]

I was a victim of abuse since I was 12 years old and by the time I was 14-15, I was quite regularly being sucked by 2 older men ( separately) who were well known to my family. I was quite well endowed even during my teen days and had a habit of exposing myself and masturbating right from school days without fully understanding the consequences, I was simply aroused almost all the time, my friends banished me from groups, was ostracised and was labelled as abnormal ( for both my habit and my size). But few men took advantage of my loneliness and started sexually abusing me. Anyways, I?ve always been a bit on the submissive side and my first time sucking was rather a forced one while I was 15,and the guy was 31 and married. I still remember it so vividly!! He always sucked me behind our garage and took my cum in his mouth while masturbating himself, talk real dirty during the act, he was driven by crazy sexual hunger and would say things like he would make me his wife and that my cock was abnormally big for my age. But that one day, he forced me to suck him and came all over my face.. although I don?t want to remember that incident but the truth is that was my first time sucking a cock

[MatthewX]

I recently added a blog post on this site with that story. Check it out.

[jjourneyman]

We all remember our firsts... right? I was 14 + 2 days. It was totally consensual, and opened my eyes to a different and exciting sexual avenue. To make a long story short, I had sucked his cock the day earlier. It was the first of firsts for me. That afternoon and well into the night, I masturbated to the thought of having swallowed another man's cum. I went through the whole range of emotions from disgust to elation.

The next day I was back for more. This time, he wanted to take me fully... and when I mean fully... he was between 7 and 8 inches. He asked me to wear a pair of high heels that were his wife's. It was easy for me to slip into them, plus it gave us extra height. He generously lubed me and his cock before the main event. The first time he took me, I was bent over the kitchen island. One second I felt the head of his cock at my ass, the next he was inside me.

I felt somewhat of a pop when he entered me fully. Only later would I know that he had passed through my rectum and was now inside my intestine. It didn't hurt, it was just a funny feeling inside my stomach.

He came in a matter of a few minutes. I was exhausted, as was he. Even though the house was cool, I could feel his sweat dripping on my lower back.

After a short break, he pulled out of me, and after wiping down, we went into the living room and watched some porn. It wasn't long before each of us were hard again. This time he fucked me doggy with me kneeling against the couch.

We carried on quite some time after that, but in the meantime, it never affected my affinity or desire for girls.

[Spininmywheels]

I?m not going to go into detail but it was absolutely amazing and I loved it.

[dbaker]

I was about 45 when I lost my cherry to a guy whom I had been sucking for several months, he was a really nice guy and I liked him a lot and decided I wanted to give myself to him. One day after we had sucked each other off and were laying in bed talking I told him that I wanted him to take my virginity the next time we met. It was a few days later we were at his house, showered together and I made sure I was clean inside then injected some lube up inside me, we layed down in bed and started in a 69 position and he worked my hole with his fingers while we sucked each other, after several minutes I was pretty worked up and ready for him to get his cock inside, his was only about 5” or so and not very thick but he had a quite large mushroom head.
I turned over on my back and pulled my legs up so he could could get it in, he pushed it in a little and then all the way in, it didn’t hurt at all because of his size and he had me stretched out with his fingers, when he began fucking me and kissing my neck I was breathless at how good it felt to be fucked like that.
we were both very excited and it only lasted about 15 minutes until he came inside me and collapsed on top of me, we layed there for several minutes with my arms around him until he went soft and slipped out of me, then he kissed his way down to my cock and gave me one of the most sensual blowjobs I’ve ever had.
He fucked me again a week later and that time I dressed up real sexy for him, I was getting very emotional attached to him after he cherried me and after the 4th time he fucked me I told him that I was falling in love with him, somehow I thought he felt the same way about me but I was wrong, the next day he wrote me a dear John letter and dumped my like a hot rock ��

[Tarz1986]

I was about 45. I had sucked him off a couple of times before. He did me bare back. I was face down and ass up. He lubed me up then loosened me up with a couple of fingers. I had been practicing with dildos before this so I was used to having objects up my ass. He started slow but soon got up to speed. He did slow down a couple of times so as not to cum to soon. I enjoyed the prostate massage but did not cum. Eventually he did cum. And over all I enjoyed the experience as much as he did.

[nettlekiss]

My first experience with another guy I was 19 and craigslist personals was a thing. I was really nervous at first but so fucking horny. It had been so long since I had anything in me and was usually only a finger . I was watching "sketchy sex" porn and really turned me on fantasizing about having someone's big cock filling my ass with cum, by that point I was desperate to have a cock in me. I made a post on craigslist hoping to find someone, which didn't take too long at all.
We decided to meet at the 4-H center not too far away from where I lived. When I got there I was really nervous thinking "I'm really about to do this? Am I really going to let another guy fuck me?" After he pulled up and parked I got out of the car. We walked to the back of his truck. It was really dark where we parked at the 4-H center, which made me feel a lot better about the situation. He unbuttoned his jeans and pulled out his cock and told me to take my pants off and bend over the tailgate of his truck. I couldn't see exactly how big his cock was but I found out as soon as he put the head of his cock on my ass. He was gentle knowing that it was my first time with another guy. As I felt this cock start to enter me I tensed up and held my breath. He slowly pushed his large cock into my ass until he was fully inside of me. After a little bit I started to relax, when he felt me relax he started thrusting in and out of me. It hurt a little bit but it hurt really fucking good. It wasn't too long before he said he was going to cum. After a few thrusts I could feel his warm cum filling me up. Never in a million years would I have thought I would let another man do that to me, but after that I was hooked, he made me his little cum slut and I wanted more. That first experience of another guy breeding me has to be my favorite sexual experience.
Being impregnated by a stranger has to be my favorite way to have sex.

[cw1860]

My first time getting fucked by a guy was last night at 62. Been fantasizing about it for a long time. Finally got the opportunity last night. Went to a men's club and while sitting in the steam room another guy came in. We exchanged some small talkand before I knew what was happening I was on my knees sucking his cock. After a few minutes he asked me if I wanted to go to his room. After some more sucking he asked me if I was ready I could get on my knees and get ready. FINALLY a dream was about to cum true. As I waited o. My knees waiting for him to begin. I felt the lube dribble onto my back door. He slowly inserted one finger and then two. He asked you ready I said yes and I felt his fingers leave and was replaced by the head of his cock. Slowly he inserted his cock into my ass it felt better than I could ever imagine! Dildos and vibrators can't compare to the pleasure of having a real cock sliding into you! As I relaxed he started thrusting harder and harder soon the rhythmic slapping of flesh on flesh feeling his hips slamming into my ass cheeks. Out of nowhere I hear myself begging him to fuck me. I think the entire place knew I was getting fucked and enjoying it! Just before he came he pulled out and shot his cum on my ass! As fantastic as that was I wanted more! And before I left last night I was fucked two more times before I headed back home. Needless to say I was pretty stretched out by the time I left. Loved every thrust! Can't wait to do it again! I'm hooked on anal! Also tried my first BBC! Loved it!

[by~his~side]

I?m not going to go into detail but it was absolutely amazing and I loved it.

Spinin, the fun is in the details! You really should share.

[DLazguy]

My first time was while I was working overseas. There was a guy that I would talk to and hang out with from time to time. He was openly bi and a cool person to talk with.

One day we were hanging out in his room, I was sitting in a chair by his bed and he was sitting in a chair about 7 feet away. I don't remember what he said exactly, but my reply was "suck my dick". I didn't mean literally, it was just my reply. He stood up and walked over to me, knelt down, and grabbed my zipper. He looked up at me as if to ask for permission. I said something along the lines of "you won't". He thought I was calling his bluff. What he didn't know was that I've had men suck my dick before.

He unzipped my pant and looked up at me for permission again. "You won't", I said. He reached in my boxers and pulled my cock out and began sucking me. He sucked me nice and slow for about 5 minutes. He got up and we both stripped down completely. I'm about 7 inches, cut and thick, but he had a nice 8+ inch, thick, cut cock. We stroked each other's cock as we got into bed. I laid back and let him suck me again. This time gave my balls some attention. after a few minutes, I sat up and pushed him back to lay down. I moved up and grabbed both our cocks with my hand and started stroking us. It was suck a turn on for my cock to touch his, to stroke both at the same time and to see that much hard cock together. After stroking our cocks for a bit, I got into position to wrap my mouth around his big, hard cock. That much meat in my mouth felt amazing. I licked the shaft, sucked his balls, played with the head, and took as much of his cock into my mouth as I could.

After about 5 minutes of me sucking him, he lifted me up and pushed me to lay back. He got in between my legs and stroked my cock. He then started rubbing the tip of his cock against my hole, as if to ask for permission. I didn't say a word, I just nodded. He pushed the tip in, stopped, pushed another inch or so in, stopped and proceed to put every inch into me, stopping after every inch or so. He now had ALL 8+, thick inches buried all the way into my tight hole. The rush was amazing. There was another man's cock in me. He slowly started stroking his cock with my ass and it felt great. The only downside was that we had to be quiet because others were in rooms nearby with thin walls. He fuck me for a good 10 minutes before he came. He pumped every drop of his load deep into me. I took every inch of his cock and there was no pain at all.

We said our goodnights as I left and I walked back to my room with his cum running down my leg. I wasn't in pain the next day, but I could still feel that his big cock fucked me the night before. This was the first and only time that I've been fucked. I think that this experience is the reason that I like bigger cocks. I like the full and stretched feeling and I like feeling multiple inches going in and out of me. I've used a 10 inch dildo and hope to find a fwb with 10 inches to fuck me on a regular basis. Now I just need to experience a man fucking me like there's no tomorrow before he fills me with cum. Then I can go home and fuck my wife with my ass full.

[jimkimball]

The guy only had a 7" cock and it wasn't thick at all ,so it wasn't that great,he was a younger guy and we did it half a dozen times,it was ok but if I ever do it again I want some bigger and thicker .

[Secretcumlover]

I played around with a friend when I was around 12. I remember spreading my ass cheeks while he pressed the head against my asshole..but we never got it inside. We knew nothing about lube at that age..decades before the internet was born.
In my 40s I met u with a guy on CL and we hooked up a couple times . It was mainly oral but on the second trip he straddled my cock and rode it. You could see the pain and pleasure in his face and moans. Without much lube I was getting sore so had him stop. I asked if he had any lube and had him lube up my ass while I laid on my back, legs in the air and stroking my cock. He got me lubed up and soon felt the head of his small cock pushing inside me. He was only around 3" and pretty thin so it wasn't too bad and felt fucking amazing. I lifted my hips towards him to help him fuck me.. I remember moaning in pleasure amd telling him to fuck me harder. I think he got about 3 pumps in before he shot his load and stopped. I was so bummed it ended so quickly. I still hope to find a guy with a decent sized cock to fuck me someday.

[Neonaught]

My first attempt at bottoming didn't go well. He didn't know what he was doing and just shoved his cock in me and it hurt like hell. To add insult to the injury, he came in about 6 strokes and it was over before the pain passed. After that, I'm all top.

[smallandbi]

I was 21 and a guy in his late 50s was hitting onto me in a bar. He knew I was a virgin and boasted that he had a big fat cock, and he could break in me. I was excited and went back to his flat. I was drunkenly trying to fondle him through his pants. I could not really feel anything though. He pulled his pants down and freed his cock. It was no more than 2 inches at best and totally soft and very slender. I thought my cock was small, but this thing was miniature. He made me get undressed and down on all fours and smeared loads of KY jelly into and around my hole. He was franticly rubbing his cock trying to get it hard. He was struggling to get even semi hard, and could not penetrate me at all. His cock just kept bending with every attempt to fuck me. Then without any warning he came all over my bottom. Not shooting but it just oozed out and kept oozing. He apologized and said he suffered from ED and not had sex for nearly 25 years and simply got over excited. We had some more beer. We watched some gay porn, and we tried again after an hour. I sucked his old and now very shrivelled cock like a limpet. It stayed completely soft, but oddly he groaned a lot. When I flicked my tongue under the tip of his helmet, he kept saying he was about to cum again. He never did and his cock seemed to get smaller. I finally deemed it a lost cause and gave up. I made my excuses, cleaned myself up, dressed and left. I was thoroughly disappointed.

[Spininmywheels]

Spinin, the fun is in the details! You really should share.

OK by~his~side if you must.
I met a couple a while back on line and after several weeks of messaging each other we all decided to meet.
They invited me over to their home and they were the sweetest down to earth people you?d ever want to meet. When I got there we sat around taking and the wife (Jane) offered me some snacks and a beverage. During our conversations we discussed what we liked and disliked, Jane said that she doesn?t usually join in but love to watch and assist if necessary. Not long afterwards the husband (Joe) were in the living room playing with each others cocks and then proceeded to suck each other. At one point I was sitting on the edge of the couch while Joe was sucking me very nicely, I was enjoying it immensely and I leaned back on the couch with my eyes closed and enjoying the bj. As I was blissfully relaxing Jane leaned over me and placed her nipple against my lips, I opened my mouth and proceeded to suck on her tits.
Not long after that Jane suggested we move into the bedroom where we would be more comfortable. One there Joe and I continued enjoying each other as Jane watched. After a little more time Jane asked if I?ve ever been fucked by a guy? I replied no. She the asked would you like to? I without hesitation replied Yes I would.
They were both happy to here that.
I proceed to get on all fours and Joe started lubing my as up and playing with it for a while loosening it up for his entry. In the meantime Jane is talking to me and encouraging me and coaching me as things developed.
Then the time came. Joe asked if I was ready and I replied yes. He then slowly, carefully and patiently worked his hard cock into my awaiting ass. After a few minutes he was deep inside of me and now fucking in a nice rhythm. I was enjoying the hell out of it. And then when I didn?t think things could get any better the unthinkable happened. Jane knelt alongside me and started to stroke my cock.
Now I?m being fucked by a guy for the first time and being milked by his wonderful wife.
Joe continued fucking me an then blew his hot load into my Virgin ass. After Joe shot his load Jane continued milking me until I blew my load and then collapsed on the bed.
Afterwards we all laid there with great big smiles on our faces.
It was a great time. We did get together several times after that. We are still in touch but has been years since we got together. I miss them and the times we had together.

So bi~his~side, is that detailed enough? I enjoyed telling it and sort of reliving it.

[friesbaconnekkid]

OK by~his~side if you must.
I met a couple a while back on line and after several weeks of messaging each other we all decided to meet.
They invited me over to their home and they were the sweetest down to earth people you?d ever want to meet. When I got there we sat around taking and the wife (Jane) offered me some snacks and a beverage. During our conversations we discussed what we liked and disliked, Jane said that she doesn?t usually join in but love to watch and assist if necessary. Not long afterwards the husband (Joe) were in the living room playing with each others cocks and then proceeded to suck each other. At one point I was sitting on the edge of the couch while Joe was sucking me very nicely, I was enjoying it immensely and I leaned back on the couch with my eyes closed and enjoying the bj. As I was blissfully relaxing Jane leaned over me and placed her nipple against my lips, I opened my mouth and proceeded to suck on her tits.
Not long after that Jane suggested we move into the bedroom where we would be more comfortable. One there Joe and I continued enjoying each other as Jane watched. After a little more time Jane asked if I?ve ever been fucked by a guy? I replied no. She the asked would you like to? I without hesitation replied Yes I would.
They were both happy to here that.
I proceed to get on all fours and Joe started lubing my as up and playing with it for a while loosening it up for his entry. In the meantime Jane is talking to me and encouraging me and coaching me as things developed.
Then the time came. Joe asked if I was ready and I replied yes. He then slowly, carefully and patiently worked his hard cock into my awaiting ass. After a few minutes he was deep inside of me and now fucking in a nice rhythm. I was enjoying the hell out of it. And then when I didn?t think things could get any better the unthinkable happened. Jane knelt alongside me and started to stroke my cock.
Now I?m being fucked by a guy for the first time and being milked by his wonderful wife.
Joe continued fucking me an then blew his hot load into my Virgin ass. After Joe shot his load Jane continued milking me until I blew my load and then collapsed on the bed.
Afterwards we all laid there with great big smiles on our faces.
It was a great time. We did get together several times after that. We are still in touch but has been years since we got together. I miss them and the times we had together.

So bi~his~side, is that detailed enough? I enjoyed telling it and sort of reliving it.


That sounds a lot like my first time, with my friends Tim and Arlene. Having her there made it especially memorable.

[Tinycockkev]

Ive been married for a long time. I have a really small dick and love small penis humiliation. I love being a sub and started sucking guys cocks when my wife is away. I really love being a tiny dick cock sucker for dom guys it?s such a turn on. The last time I was sucking this guys cock he flipped me over and fucked me hard. I had never been fucked before and I fucking loved it. I felt so submissive stroking my tiny dicklet while he fucked my ass, then pulled out and shot a huge load in my mouth, so fucking hot. I think about it all the time

[joseluis]

WOW!!! What a great story!!!

[Unholybi]

Happened just once, right after coming back from honeymoon lol I was 31 he was gorgeous young ladyboy with modest cock. He didn?t last long but we have both cum at the same time to our surprise. Never seen her after, wish we continued for longer. Since that only being pegged by my female lover. Love anal unfortunately couldn?t meet proper guy since my first and only cock so far.

i remember to this day looking back over my shoulder to find a beautiful creature happily smiling holding my hips pounding my ass, and that gorgeous yet fake breasts. Night of a long time dream come true ☺️ it’s been 8 years now and I miss you Caz

[licyou69]

It was good, but not great. The only negative aspect was he's an older guy like me and was having trouble keeping it hard. After several failed attempts at him getting in me and staying hard, he took off the condom. With a promise he wouldn't cum in me, I let him back in me bare. It felt amazing when he was finally able to work up a good stroke inside me. Unfortunately, he still wasn't able to keep it hard for long, so he pulled out and I got him to cum with a combination blowjob/handjob. At least I was able to swallow his cum instead of him dumping it into a condom. A couple of weeks later I let another man fuck me and it was amazing. He was strong, energetic, and pounded my submissive ass like I needed.

[JerzeeGawker]

Getting my ass cherry popped


I am a male at the time in my 30's. I was separated from wife living with an older female with benefits. GAWD could the woman moan and quick to orgasm as well as often !
I am no stranger to sucking a little, and I do me little under 6 inches in length and about 1 3/4 diameter. About like my own junk is.
So I get this hankering for a little on the side male to male. Now I am a good size city in Upstate NY off 90.
I locate a site I can try to find same sex partner willing. I get a reply as availability. NOW !
We agree to met at a flower shop where he works. Now this is before everyone started taking selfies and sex vids on their phones. I drive to the shop walk in, introduce myself and he goes and puts the closed sign up out to lunch. We go behind this curtain. Wasting no time we both drop our pants past our knees. He drops down and takes my cock into his mouth and lets it GROW ! After a minute or two he stands up. Asks me "You ever took it in the ass before ?" I told him . . " Nope Care to pop that cherry !?" His reply . . . " Love to !" With a shit eating grin on his face ( no pun intended ) I spin around and bend the knees to widen my little ass cheeks. He dropped to his knees and rimmed me a new. Jammed his tongue up my ass a good inch or so. Was amazing !!!! He applies some time of lotion and "slides" right in All the way to his ball sac ! Balls deep on the first cherry busting stiff cock ever ! After a minute or two of "getting use to it " he starts slowly pulling out. When just his head is in my tight freshly broke cherry asshole he stops, holds for a few seconds and Slides it nice and steady back in. After he bottoms is when our balls meet. The longer he fucked me the harder my dick got ! I was just about to the blowing my load point when his lets loose a stream of hot fluids filling my ass ! OMG AMAZING ! ! ! After 3 solid hot streams deep in my ass he slides our drops to his knees and cleans up the outside of my asshole and blows me till I pull out and shoot my load on his face. We cleaned up said our goodbyes and I have not had another experience like that since.

[Secretcumlover]

I played around with a friend when I was around 12. I remember spreading my ass cheeks while he pressed the head against my asshole..but we never got it inside. We knew nothing about lube at that age..decades before the internet was born.
In my 40s I met u with a guy on CL and we hooked up a couple times . It was mainly oral but on the second trip he straddled my cock and rode it. You could see the pain and pleasure in his face and moans. Without much lube I was getting sore so had him stop. I asked if he had any lube and had him lube up my ass while I laid on my back, legs in the air and stroking my cock. He got me lubed up and soon felt the head of his small cock pushing inside me. He was only around 3" and pretty thin so it wasn't too bad and felt fucking amazing. I lifted my hips towards him to help him fuck me.. I remember moaning in pleasure amd telling him to fuck me harder. I think he got about 3 pumps in before he shot his load and stopped. I was so bummed it ended so quickly. I still hope to find a guy with a decent sized cock to fuck me someday.
Well years later , I finally got my ass fucked good and hard. I started using grinder and AFF. The first guy lived about an hour away and I drove to his house and we played in his camp trailer. I sucked him off until I swallowed his load. He stayed hard and tried to fuck me. He started to cum as soon as the thick head popped in. Luckily he jumped off me and I was able to catch his second load in my mouth! A few months later I met up with a guy with a fat 6.5" cock nicknamed "the hole puncher" . We tried for about an
hour and he couldnt get the head to slide in so we gave up. Months later we gave it another shot. Thos time I fucked myself in the shower with a decent size dildo after going through my internal cleaning routine. When I got to his house i sucked hos cock for about 20 minutes because that gets me horny af! He then placed 3 pillows under my belly to lift my ass in the air. He lingered and tongued my assfrom behind while rubbing my cock. After lubing up my ass he easily slid a average size dildo right into my ass. With the dildo inside me he laid on my back and went through the humping motions. After a few minutes of this he brought the fat head of his dick to my ass and slid up and down my lubed cheeks with his cock gliding over my puckering asshole. He removed the dildo and placed his cock against my ass and pushed right in. I jumped and whimpered in pain for jist a moment but was soon lifting my ass towards him to get all of his cock inside me. Fucking him back and grinding my ass onto his cock felt fucking amazing! Soon I'm telling him , begging him to fuck me faster . A few minutes of hard fucking he told me he's going to cum . Instinctively im yelling " fuck my ass, shoot that hot cum deep inside me " . He stayed hard inside me and continued to fuck me while reaching down and rubbing my rock hard cock. I'm now laying more on my side with one leg up exposing my cum filled asshole to him. Over and over he'd pull his cock out, rub it against my asshole then slam his entire cock back inside me. The pleasure was insane!
Afterwards he had me lay on my back and slide towards the bottom of the bed where he had kneeled down to blow me. That man knows how to suck cock..WOW. within minutes I had the biggest orgasm I've had in years filling his mouth with cum. I could hear him slurping and swallowing ot down over his moans . He only lives a few blocks away and plan to make this a frequent thing. He has a buddy from out of town that stays occasionally. Supposedly he has a thick 9" cock and we are planning and all day or all night playdate soon.
I can knock a few things off my bucket list. Sucking one while the other fucks me.. a glory hole to feed me. Both of them taking turns fucking me.