My first anal experience I was 18. It was with my boss. He asked me to stay the night with him and I accepted. I knew it was to have sex even though he didn't flat out say it. We went to his place. He sucked my dick till I came. Then he got me on my hands and knees and fucked me good. That was when I knew I could never be just straight. Loved it.
Your first anal experience?
- Thread starter mrbimystery
- Start date
tristantrotsky
Literotica Guru
- Joined
- Jun 25, 2012
- Posts
- 9,927
This is an amazing story. When this kind of sex is consensual and without coercion it can be a wonderful thing. I was older than you, twenty-five I guess. I always preferred giving head, and still do. But if my Boyfriend wants anal I'm always anxious to please him.
Funnbrandy
Literotica Guru
- Joined
- Jun 29, 2014
- Posts
- 833
My first anal....
So this seems to be mostly gay experiences but since I'm bi I feel I'm entitled to ad my story, by the way it's a straight anal experience so if that makes you squeamish please click back arrow now, lol.
I was younger, still lived at home, me and my boyfriend were watching movies on the couch on a lazy Sunday, parents were upstairs. We were spooning on the couch and as usual his hand went up my shirt and began groping my breasts, I pushed my ass up against his cock and slow, rhythmic dry humping began. Soon he was kissing my neck and we were hot and heavy, I slide down my shorts and let him finger me from behind, he pulled his pants down just far enough to pull out his cock, which was rock hard at this point.
He began to guide it into my pussy which was soaked by this time, halfway in I stopped him and told him to grab a condom, "I don't have one", he said, "I don't either!", I said. Frustrated I laid back down, but again he slide his cock in and thruster a few times, again I pulled away and he pulled out, this went on over and over, he would slide it in and pump a few times in a moment of my weakness, before having a moment of responsibility and making him pull out, I was so horny I couldn't help myself.
Then in the heat of things between pull outs and kissing my neck and went to put it in again, except this time he pushed up against my butt and the head of his wet cock slide in my ass, I jumped a little as he realized his mistake, "sorry", he said with a slight giggle. At that time I had never tried anal, I had been rimmed and a little finger play but never cock even though I thought about it.
I reached back with one hand and purposely guided is cock up against my ass again, this time he slide it in just past the head, again I jumped a little at the discomfort but he kept it in, again I reached back and grabbed his cock by the shaft, but this time I left it in place as he slowly began to stroke it in and out, my hand only allowing him to go an inch nor two into my ass.
Slowly over the next 15 or twenty minutes my hand slide back a little at a time, allowing more and more of his cock to enter as I relaxed more and more and was able to handle more and more, eventually my hand pushed back as far as it would go, allowing 3 or so inches into me until finally I stopped gripping his shaft and simply kept a flat hand pushed against the base of his cock to keep him from getting over zealous with the thrusting.
He was really good and slowly and gently fucked my ass, I don't think he ever got balls deep but most of his thick 6" cock was buried in my ass, we would slow and stop at time to avoid cumming as this was his first anal experience as well and was clearly loving it.
Soon I felt the tell take sign of heavy breathing on the back of my neck and he thrusted harder and deeper, I quickly grabbed his shaft again before he began slamming my ass in ecstasy, Just as I did I could feel his cock start to pulse, I quickly tried to pull it out but he had already began cumming, as I did pull it out I could feel cum squirt between my ass cheeks and run down on the couch, he moaned and squeezed me tightly as he shot all over my ass.
Soon he finished and the plan to clean up the mess was surmised, lol, it was a good first experience and definitely not my last
So this seems to be mostly gay experiences but since I'm bi I feel I'm entitled to ad my story, by the way it's a straight anal experience so if that makes you squeamish please click back arrow now, lol.
I was younger, still lived at home, me and my boyfriend were watching movies on the couch on a lazy Sunday, parents were upstairs. We were spooning on the couch and as usual his hand went up my shirt and began groping my breasts, I pushed my ass up against his cock and slow, rhythmic dry humping began. Soon he was kissing my neck and we were hot and heavy, I slide down my shorts and let him finger me from behind, he pulled his pants down just far enough to pull out his cock, which was rock hard at this point.
He began to guide it into my pussy which was soaked by this time, halfway in I stopped him and told him to grab a condom, "I don't have one", he said, "I don't either!", I said. Frustrated I laid back down, but again he slide his cock in and thruster a few times, again I pulled away and he pulled out, this went on over and over, he would slide it in and pump a few times in a moment of my weakness, before having a moment of responsibility and making him pull out, I was so horny I couldn't help myself.
Then in the heat of things between pull outs and kissing my neck and went to put it in again, except this time he pushed up against my butt and the head of his wet cock slide in my ass, I jumped a little as he realized his mistake, "sorry", he said with a slight giggle. At that time I had never tried anal, I had been rimmed and a little finger play but never cock even though I thought about it.
I reached back with one hand and purposely guided is cock up against my ass again, this time he slide it in just past the head, again I jumped a little at the discomfort but he kept it in, again I reached back and grabbed his cock by the shaft, but this time I left it in place as he slowly began to stroke it in and out, my hand only allowing him to go an inch nor two into my ass.
Slowly over the next 15 or twenty minutes my hand slide back a little at a time, allowing more and more of his cock to enter as I relaxed more and more and was able to handle more and more, eventually my hand pushed back as far as it would go, allowing 3 or so inches into me until finally I stopped gripping his shaft and simply kept a flat hand pushed against the base of his cock to keep him from getting over zealous with the thrusting.
He was really good and slowly and gently fucked my ass, I don't think he ever got balls deep but most of his thick 6" cock was buried in my ass, we would slow and stop at time to avoid cumming as this was his first anal experience as well and was clearly loving it.
Soon I felt the tell take sign of heavy breathing on the back of my neck and he thrusted harder and deeper, I quickly grabbed his shaft again before he began slamming my ass in ecstasy, Just as I did I could feel his cock start to pulse, I quickly tried to pull it out but he had already began cumming, as I did pull it out I could feel cum squirt between my ass cheeks and run down on the couch, he moaned and squeezed me tightly as he shot all over my ass.
Soon he finished and the plan to clean up the mess was surmised, lol, it was a good first experience and definitely not my last
So this seems to be mostly gay experiences but since I'm bi I feel I'm entitled to ad my story, by the way it's a straight anal experience so if that makes you squeamish please click back arrow now, lol.
I was younger, still lived at home, me and my boyfriend were watching movies on the couch on a lazy Sunday, parents were upstairs. We were spooning on the couch and as usual his hand went up my shirt and began groping my breasts, I pushed my ass up against his cock and slow, rhythmic dry humping began. Soon he was kissing my neck and we were hot and heavy, I slide down my shorts and let him finger me from behind, he pulled his pants down just far enough to pull out his cock, which was rock hard at this point.
He began to guide it into my pussy which was soaked by this time, halfway in I stopped him and told him to grab a condom, "I don't have one", he said, "I don't either!", I said. Frustrated I laid back down, but again he slide his cock in and thruster a few times, again I pulled away and he pulled out, this went on over and over, he would slide it in and pump a few times in a moment of my weakness, before having a moment of responsibility and making him pull out, I was so horny I couldn't help myself.
Then in the heat of things between pull outs and kissing my neck and went to put it in again, except this time he pushed up against my butt and the head of his wet cock slide in my ass, I jumped a little as he realized his mistake, "sorry", he said with a slight giggle. At that time I had never tried anal, I had been rimmed and a little finger play but never cock even though I thought about it.
I reached back with one hand and purposely guided is cock up against my ass again, this time he slide it in just past the head, again I jumped a little at the discomfort but he kept it in, again I reached back and grabbed his cock by the shaft, but this time I left it in place as he slowly began to stroke it in and out, my hand only allowing him to go an inch nor two into my ass.
Slowly over the next 15 or twenty minutes my hand slide back a little at a time, allowing more and more of his cock to enter as I relaxed more and more and was able to handle more and more, eventually my hand pushed back as far as it would go, allowing 3 or so inches into me until finally I stopped gripping his shaft and simply kept a flat hand pushed against the base of his cock to keep him from getting over zealous with the thrusting.
He was really good and slowly and gently fucked my ass, I don't think he ever got balls deep but most of his thick 6" cock was buried in my ass, we would slow and stop at time to avoid cumming as this was his first anal experience as well and was clearly loving it.
Soon I felt the tell take sign of heavy breathing on the back of my neck and he thrusted harder and deeper, I quickly grabbed his shaft again before he began slamming my ass in ecstasy, Just as I did I could feel his cock start to pulse, I quickly tried to pull it out but he had already began cumming, as I did pull it out I could feel cum squirt between my ass cheeks and run down on the couch, he moaned and squeezed me tightly as he shot all over my ass.
Soon he finished and the plan to clean up the mess was surmised, lol, it was a good first experience and definitely not my last
That could have been me. Almost the same story.
tristantrotsky
Literotica Guru
- Joined
- Jun 25, 2012
- Posts
- 9,927
So this seems to be mostly gay experiences but since I'm bi I feel I'm entitled to ad my story, by the way it's a straight anal experience so if that makes you squeamish please click back arrow now, lol.
I was younger, still lived at home, me and my boyfriend were watching movies on the couch on a lazy Sunday, parents were upstairs. We were spooning on the couch and as usual his hand went up my shirt and began groping my breasts, I pushed my ass up against his cock and slow, rhythmic dry humping began. Soon he was kissing my neck and we were hot and heavy, I slide down my shorts and let him finger me from behind, he pulled his pants down just far enough to pull out his cock, which was rock hard at this point.
He began to guide it into my pussy which was soaked by this time, halfway in I stopped him and told him to grab a condom, "I don't have one", he said, "I don't either!", I said. Frustrated I laid back down, but again he slide his cock in and thruster a few times, again I pulled away and he pulled out, this went on over and over, he would slide it in and pump a few times in a moment of my weakness, before having a moment of responsibility and making him pull out, I was so horny I couldn't help myself.
Then in the heat of things between pull outs and kissing my neck and went to put it in again, except this time he pushed up against my butt and the head of his wet cock slide in my ass, I jumped a little as he realized his mistake, "sorry", he said with a slight giggle. At that time I had never tried anal, I had been rimmed and a little finger play but never cock even though I thought about it.
I reached back with one hand and purposely guided is cock up against my ass again, this time he slide it in just past the head, again I jumped a little at the discomfort but he kept it in, again I reached back and grabbed his cock by the shaft, but this time I left it in place as he slowly began to stroke it in and out, my hand only allowing him to go an inch nor two into my ass.
Slowly over the next 15 or twenty minutes my hand slide back a little at a time, allowing more and more of his cock to enter as I relaxed more and more and was able to handle more and more, eventually my hand pushed back as far as it would go, allowing 3 or so inches into me until finally I stopped gripping his shaft and simply kept a flat hand pushed against the base of his cock to keep him from getting over zealous with the thrusting.
He was really good and slowly and gently fucked my ass, I don't think he ever got balls deep but most of his thick 6" cock was buried in my ass, we would slow and stop at time to avoid cumming as this was his first anal experience as well and was clearly loving it.
Soon I felt the tell take sign of heavy breathing on the back of my neck and he thrusted harder and deeper, I quickly grabbed his shaft again before he began slamming my ass in ecstasy, Just as I did I could feel his cock start to pulse, I quickly tried to pull it out but he had already began cumming, as I did pull it out I could feel cum squirt between my ass cheeks and run down on the couch, he moaned and squeezed me tightly as he shot all over my ass.
Soon he finished and the plan to clean up the mess was surmised, lol, it was a good first experience and definitely not my last
Thanks for sharing. Much appreciate your refreshing honesty and openness.
Funnbrandy
Literotica Guru
- Joined
- Jun 29, 2014
- Posts
- 833
Thanks!
Glad you enjoyed
Glad you enjoyed
Pittdude1972
Literotica Guru
- Joined
- May 14, 2009
- Posts
- 811
Glad you enjoyed
Great story.
first time
I have already told this story to some people on here but here goes.
i had only slept with women at this point some were relationships some where just casual some were relationship but at this point i started to become curios about trying a cock. at this point a friend who i knew who was bi and i knew a turn on for him was to give guys their first gay experience. for about a year he had been trying to convince into letting him have my way with me however 3 months into that year i had become really curios i starting getting of to gay porn. however i did not do anything about it for a year until a group of my friends were at his house once they all left he said something like now they have all gone wanna have sex i though to my self i have to do this or i will regret this when i said lets do it i think he was quite taken back but he told me follow him to his bedroom when we were in his bedroom he told me to get naked once we were both naked i was told to get on my knees when i opened my mouth i really did not know what i would be the top or the bottom but when i started to bob up and down on his cock and when started lick and suck i was really liking it and i realised i was as hard as steel i was really enjoying sucking his cock for about 45 mins i was sucking and he was moaning when he came in my mouth i swallowed all his cum it had quite nice taste he then got me on my back he then started to lick my ass it felt really good i neally came he used it to get him hard again he then stopped licking i then felt a cold sensation on my ass then i found out his lubbed cock head was on the entrance of my ass he inserted the head in my ass i felt a sharp pain he said he will go slow and after that it will feel great. I felt inch by inch of his cock go inside once he was fully in me he started to fuck me the pain quickly became absolute pleasure after him fucking me doggy stlye he got me on my back put my legs in the air and he inserted himself in me again there was still a bit of pain but it went quickly after half an hour i came soo hard he came deep inside me after that i knew i was bi and after that where ever i was with a guy i was the bottom
I have already told this story to some people on here but here goes.
i had only slept with women at this point some were relationships some where just casual some were relationship but at this point i started to become curios about trying a cock. at this point a friend who i knew who was bi and i knew a turn on for him was to give guys their first gay experience. for about a year he had been trying to convince into letting him have my way with me however 3 months into that year i had become really curios i starting getting of to gay porn. however i did not do anything about it for a year until a group of my friends were at his house once they all left he said something like now they have all gone wanna have sex i though to my self i have to do this or i will regret this when i said lets do it i think he was quite taken back but he told me follow him to his bedroom when we were in his bedroom he told me to get naked once we were both naked i was told to get on my knees when i opened my mouth i really did not know what i would be the top or the bottom but when i started to bob up and down on his cock and when started lick and suck i was really liking it and i realised i was as hard as steel i was really enjoying sucking his cock for about 45 mins i was sucking and he was moaning when he came in my mouth i swallowed all his cum it had quite nice taste he then got me on my back he then started to lick my ass it felt really good i neally came he used it to get him hard again he then stopped licking i then felt a cold sensation on my ass then i found out his lubbed cock head was on the entrance of my ass he inserted the head in my ass i felt a sharp pain he said he will go slow and after that it will feel great. I felt inch by inch of his cock go inside once he was fully in me he started to fuck me the pain quickly became absolute pleasure after him fucking me doggy stlye he got me on my back put my legs in the air and he inserted himself in me again there was still a bit of pain but it went quickly after half an hour i came soo hard he came deep inside me after that i knew i was bi and after that where ever i was with a guy i was the bottom
Last edited:
I was younger still living at home. I had found my moms toys and lube. The first one I tried was her vibe then I tried to move up but they were to big so I went back to the vibe. I used it until the batteries were dead. Washed everything then put it all back.
My first anal exp, was with an older guy. We had been hooking up for mutual oral for a bit and one day he started rimming me and inserting his fingers, i enjoyed the sensation enough to let him enter me. At first there was some pain that faded to pleasure, i remember him bring me to me first anal orgasam. It was great havent gone that far with another since. always willing if it feels right though.
always willing if it feels right though.
jerkme2005
Really Experienced
- Joined
- Oct 30, 2011
- Posts
- 542
first anal
Had a neighborhood friend in my teens that we used to play down my basement together experimenting with sex. We started off with jerking each other then giving each other blow jobs. I remember him coming over one night and told me he had something he wanted to try. He was spending the night and went over to his overnight bag and took out a jar of vaseline. I asked him what was that for and told me to take off my pjs and he would show me. I took off my pjs and he applied some vaseline to his finger and then started to massage my anus while jerking me off, it really felt good that i started to moan, with that he applied some pressure and slid his finger in me. Ooh! he look at me and said you like that. I said yes and he slid another finger in, he worked his two digits in and out of my ass while greasing up his slim cock, he was about 5", mine was much bigger. He told me to turn over and lie on my stomach, I knew what he was going to do and he said he would go slow to tell him if he was hurting me. I thought he must be learning all this from his gay uncle who lived with his family. He slid his slim cock slowly into me, it took a little while to adjust but when it felt okay he started to really fuck me. It did not take him long to cum. When he was finished, I said my turn, he said he couldn't wait to take my big cock he has been dreaming about it. Another story!
Had a neighborhood friend in my teens that we used to play down my basement together experimenting with sex. We started off with jerking each other then giving each other blow jobs. I remember him coming over one night and told me he had something he wanted to try. He was spending the night and went over to his overnight bag and took out a jar of vaseline. I asked him what was that for and told me to take off my pjs and he would show me. I took off my pjs and he applied some vaseline to his finger and then started to massage my anus while jerking me off, it really felt good that i started to moan, with that he applied some pressure and slid his finger in me. Ooh! he look at me and said you like that. I said yes and he slid another finger in, he worked his two digits in and out of my ass while greasing up his slim cock, he was about 5", mine was much bigger. He told me to turn over and lie on my stomach, I knew what he was going to do and he said he would go slow to tell him if he was hurting me. I thought he must be learning all this from his gay uncle who lived with his family. He slid his slim cock slowly into me, it took a little while to adjust but when it felt okay he started to really fuck me. It did not take him long to cum. When he was finished, I said my turn, he said he couldn't wait to take my big cock he has been dreaming about it. Another story!
rainbowdash30
Literotica Guru
- Joined
- Nov 11, 2015
- Posts
- 1,621
Receiving: as is the way with these things, we started slowly; for a couple of weeks during our intimate fun, he would tease around my hole with his finger - and sometimes his tongue - while going down on me. This progressed to him sticking the tip of his well-moistened finger inside me, shallowly at first, before going a bit deeper. I started to love the feeling and I wanted more, so ... I finally felt ready for him to stick his cock in me.
We used a lot of lubricant, both before and during, and I think it might've killed the feeling a bit (even now, I hate too much lube because the lack of friction makes it feel like you're getting a medical exam); anyway, he went slowly until I got used to the thickness inside me.
Once I got over my worries about it hurting, I really enjoyed it; there's something so wonderful about that sensation of fullness, of those veins tickling your most intimate core, and ye Goddesses, the feeling of that warm, wet stickiness coating the very fibres of your being! Wonderful, nothing like it.
Giving: a friend of mine who was curious about anal asked me to peg him; I agreed, so long as he was sure he really wanted it. He told me that he enjoyed prostate stimulation, almost more than masturbation, and that he wanted to take that to the next level. Once I was sure he was serious, I picked up a beginner's strap-on (six inches long, not too thick, pretty much smooth) and went 'round to his place.
We fooled around a little first to get us both in the mood (he really enjoyed me fingering his hole and doubtless was glad that I'd trimmed my nails beforehand) and he ended up face down on the bed; I lubed up my cock and his hole, then inserted it in him slowly, with him moaning all the while (I never really think of guys moaning, weirdly; grunts, sure, but moaning was a new thing to me at the time and I liked the sound). Once he was comfortable, I went faster and faster until he came unaided (i.e. without either of us touching his cock).
Proud of that one.
I've done both girls and guys since, but those are stories for another day.
We used a lot of lubricant, both before and during, and I think it might've killed the feeling a bit (even now, I hate too much lube because the lack of friction makes it feel like you're getting a medical exam); anyway, he went slowly until I got used to the thickness inside me.
Once I got over my worries about it hurting, I really enjoyed it; there's something so wonderful about that sensation of fullness, of those veins tickling your most intimate core, and ye Goddesses, the feeling of that warm, wet stickiness coating the very fibres of your being! Wonderful, nothing like it.
Giving: a friend of mine who was curious about anal asked me to peg him; I agreed, so long as he was sure he really wanted it. He told me that he enjoyed prostate stimulation, almost more than masturbation, and that he wanted to take that to the next level. Once I was sure he was serious, I picked up a beginner's strap-on (six inches long, not too thick, pretty much smooth) and went 'round to his place.
We fooled around a little first to get us both in the mood (he really enjoyed me fingering his hole and doubtless was glad that I'd trimmed my nails beforehand) and he ended up face down on the bed; I lubed up my cock and his hole, then inserted it in him slowly, with him moaning all the while (I never really think of guys moaning, weirdly; grunts, sure, but moaning was a new thing to me at the time and I liked the sound). Once he was comfortable, I went faster and faster until he came unaided (i.e. without either of us touching his cock).
Proud of that one.
I've done both girls and guys since, but those are stories for another day.
onemadvagabond
Literotica Guru
- Joined
- Jan 3, 2011
- Posts
- 847
My first time was a little uncomfortable at first. The night started out with myself and my best friend at the time just hanging out. We were young and had little experience in things sexual. We started off playing truth or dare and after a bit it was all dares. Strip to your underwear. Run outside naked and it escalated from there. We kept up the pretense of the game all the way through.
That night was my first everything. First kiss. First blowjob, receiving and giving. First time entwined with someone else naked. First sex, both giving and receiving as well. Although it started out uncomfortable, it got better because we were smart enough to use lube. I had experimented with anal play on myself before then so I wasn't completely new to it, but that was my first time getting fucked. I have since come to REALLY enjoy a nice cock sliding in and out of me. Preferably on my back with the heels of my feet on his ass helping to pull the man into me. I also learned that night that I LOVE giving head.
Not everyone enjoys receiving, but I guess I was just made for it.
That night was my first everything. First kiss. First blowjob, receiving and giving. First time entwined with someone else naked. First sex, both giving and receiving as well. Although it started out uncomfortable, it got better because we were smart enough to use lube. I had experimented with anal play on myself before then so I wasn't completely new to it, but that was my first time getting fucked. I have since come to REALLY enjoy a nice cock sliding in and out of me. Preferably on my back with the heels of my feet on his ass helping to pull the man into me. I also learned that night that I LOVE giving head.
Not everyone enjoys receiving, but I guess I was just made for it.
amylin456
Literotica Guru
- Joined
- Feb 1, 2010
- Posts
- 14,066
Receiving: as is the way with these things, we started slowly; for a couple of weeks during our intimate fun, he would tease around my hole with his finger - and sometimes his tongue - while going down on me. This progressed to him sticking the tip of his well-moistened finger inside me, shallowly at first, before going a bit deeper. I started to love the feeling and I wanted more, so ... I finally felt ready for him to stick his cock in me.
We used a lot of lubricant, both before and during, and I think it might've killed the feeling a bit (even now, I hate too much lube because the lack of friction makes it feel like you're getting a medical exam); anyway, he went slowly until I got used to the thickness inside me.
Once I got over my worries about it hurting, I really enjoyed it; there's something so wonderful about that sensation of fullness, of those veins tickling your most intimate core, and ye Goddesses, the feeling of that warm, wet stickiness coating the very fibres of your being! Wonderful, nothing like it.
Giving: a friend of mine who was curious about anal asked me to peg him; I agreed, so long as he was sure he really wanted it. He told me that he enjoyed prostate stimulation, almost more than masturbation, and that he wanted to take that to the next level. Once I was sure he was serious, I picked up a beginner's strap-on (six inches long, not too thick, pretty much smooth) and went 'round to his place.
We fooled around a little first to get us both in the mood (he really enjoyed me fingering his hole and doubtless was glad that I'd trimmed my nails beforehand) and he ended up face down on the bed; I lubed up my cock and his hole, then inserted it in him slowly, with him moaning all the while (I never really think of guys moaning, weirdly; grunts, sure, but moaning was a new thing to me at the time and I liked the sound). Once he was comfortable, I went faster and faster until he came unaided (i.e. without either of us touching his cock).
Proud of that one.
I've done both girls and guys since, but those are stories for another day.
Can totally agree with first part 'receiving' from my experience(s).. Using a small plug or dildo just before for a while also helps a lot... But always use a good lube..
luckyseven
Really Experienced
- Joined
- Feb 23, 2005
- Posts
- 1,163
What a Night!!!
My first anal experience happened when I was a teenager was with one of my friends. We'd been larking around for a few years, rubbing our cocks together when we got together. We sometimes used to suck each other off. That summer we were staying at his grandparents. They had a large house in the country and we could more or less do as we pleased. They had a large secluded pool and we used to skinny-dip and often stayed nude for much of the day. His grandparents were active nudist so no eyebrows were raised. I remember I enjoyed being nude and often got an erection and got quite randy and we would often masturbate together. He wasn’t that big. Maybe a little over 6” and not particularly thick. He was cut not like me so which at the time I thought was fascinating. We shared a bedroom and most nights we would rub our cocks together and I enjoyed sucking his circumcised cock. Then as a complete surprise he asked if I wanted to try some arse play and actually started fingering my arse. I wasn't sure because I'd never done that before but after the initial shock the sensation was unbelievable. Then he asked if I wanted the real thing so I got on my hands and knees and he fucked me from behind. He started slowly and after five minutes he barely got the head in but as I relaxed he got his full 6” in and started to pick up the pace and I naturally started push back against him as he thrusted and I managed to get a full erection and began to ooze copious amounts of pre-cum. It felt so good I clenched up hard as he shot his load in me. His erection soon softened and he eventually popped out leaving his cum leaking down my balls. What a night to remember!
My first anal experience happened when I was a teenager was with one of my friends. We'd been larking around for a few years, rubbing our cocks together when we got together. We sometimes used to suck each other off. That summer we were staying at his grandparents. They had a large house in the country and we could more or less do as we pleased. They had a large secluded pool and we used to skinny-dip and often stayed nude for much of the day. His grandparents were active nudist so no eyebrows were raised. I remember I enjoyed being nude and often got an erection and got quite randy and we would often masturbate together. He wasn’t that big. Maybe a little over 6” and not particularly thick. He was cut not like me so which at the time I thought was fascinating. We shared a bedroom and most nights we would rub our cocks together and I enjoyed sucking his circumcised cock. Then as a complete surprise he asked if I wanted to try some arse play and actually started fingering my arse. I wasn't sure because I'd never done that before but after the initial shock the sensation was unbelievable. Then he asked if I wanted the real thing so I got on my hands and knees and he fucked me from behind. He started slowly and after five minutes he barely got the head in but as I relaxed he got his full 6” in and started to pick up the pace and I naturally started push back against him as he thrusted and I managed to get a full erection and began to ooze copious amounts of pre-cum. It felt so good I clenched up hard as he shot his load in me. His erection soon softened and he eventually popped out leaving his cum leaking down my balls. What a night to remember!
JaneRose65
Literotica Guru
- Joined
- May 1, 2016
- Posts
- 1,119
Sounds like a perfect first encounter
amylin456
Literotica Guru
- Joined
- Feb 1, 2010
- Posts
- 14,066
it does sound interesting..
luckyseven
Really Experienced
- Joined
- Feb 23, 2005
- Posts
- 1,163
Up until about 2 years ago I had never entertained the thought of being with another man again. After my wife and I considered a swingers expeience it was only a matter of time before we invited another man or woman (or both) into our bed. Soon after we had a few experiences with other couples I found myself watching her sucking on and riding another guy's cock and wishing I could do the same.
One night when we were lying in the afterglow of our lovemaking, my wife turned to me and asked if being close to another guy made me horny?' 'It's OK.' she said. 'I don't mind. If you want to be with a guy, that's cool. All I ask is that you let me watch."
How she knew was beyond me but since then we regularly hook up with another couple where we enjoy exploring our bi-sexuality.
