sinfulallure
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I had my first anal penetration in a group scene about a year back. Wifey went bananas with exitement, We would love to hear how you lost your anal virginity.
T&M
T&M
First time anal , male or female
- Thread starter sinfulallure
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deluxe3000
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Sounds like a sexy time for both of you.
I lost my anal virginity with a masseuse who catered to bi curious men. I saw him about three times for massage and hand jobs only until the fourth time I went over to see him with some condoms and some lube and asked if he would fuck me. He did and it was very, very erotic. Didn't feel particularly good but was such a turn on to have a man above me, my legs over his shoulder, and him slowly pushing his cock into me until we were fucking in earnest. Would love to repeat it again one day.
I lost my anal virginity with a masseuse who catered to bi curious men. I saw him about three times for massage and hand jobs only until the fourth time I went over to see him with some condoms and some lube and asked if he would fuck me. He did and it was very, very erotic. Didn't feel particularly good but was such a turn on to have a man above me, my legs over his shoulder, and him slowly pushing his cock into me until we were fucking in earnest. Would love to repeat it again one day.
bi_asian_guy
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*****
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PredatorSmile
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Lost mine some time ago. BF came home, angry after his B-ball team lost to rivals. That was around the same time I was dealing with the fact that he was bisexual. He didn't feel like talking, and I wanted to comfort him. He went to the bathroom, and i was banging on the door, asking to be let in to talk to him. He grabbed me and pulled me inside, clothes and all. Just turned me around, dropped my shorts and took me.
Just me, him, soap and water. No questions. No words. I'd never seen him so angry or so passionate before. I've loved that kind of sex ever since.
No, I don't pick fights with him just to get some !
Just me, him, soap and water. No questions. No words. I'd never seen him so angry or so passionate before. I've loved that kind of sex ever since.
No, I don't pick fights with him just to get some !
BedtimeStories77
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I was 21 (and pregnant) the first time I had anal sex successfully with a man. Before that, two other men tried, but I pulled away (and didn't let them continue) due to their eagerness.
Before I had my first "successful" anal experience I did engage in anal play a lot. I loved (and still do) it.
So, I was 21 and pregnant when I engaged in anal sex with the man I was seeing at the time. It was either late night or early morning, and we had been sleeping in spoons position. I was horny, and loved the feeling of his cock pressing against my asshole. (I'm guessing he had morning wood.) Using my own spit, I "lubed" my asshole...slid a finger in and so on. I then "lubed" his cock as best I could while reaching behind me.
Holding his cock in place, I slowly began pushing back against him. Even that alone felt really good.
I pumped my hips as if I was dry fucking,and slowly the head of his cock did go in. Once I had that much in I brought my hand forward and got myself a little more comfortable.
I continued to "pump" back against him. At some point, he woke up. He placed a hand on my hip and thrusted forward. Luckily, I shot myself forward at the same time, so his stab didn't hurt much. lol I told him "he was in the other hole" and to let me take control of things.
Even with that one kinda uncomfortable stabbing, I was soooooo wet (without my pussy being touched at all by that point)! I've always had stronger, more intense orgasms through anal. And my pussy always drips a lot too.
Before I had my first "successful" anal experience I did engage in anal play a lot. I loved (and still do) it.
So, I was 21 and pregnant when I engaged in anal sex with the man I was seeing at the time. It was either late night or early morning, and we had been sleeping in spoons position. I was horny, and loved the feeling of his cock pressing against my asshole. (I'm guessing he had morning wood.) Using my own spit, I "lubed" my asshole...slid a finger in and so on. I then "lubed" his cock as best I could while reaching behind me.
Holding his cock in place, I slowly began pushing back against him. Even that alone felt really good.
I pumped my hips as if I was dry fucking,and slowly the head of his cock did go in. Once I had that much in I brought my hand forward and got myself a little more comfortable.I continued to "pump" back against him. At some point, he woke up. He placed a hand on my hip and thrusted forward. Luckily, I shot myself forward at the same time, so his stab didn't hurt much. lol I told him "he was in the other hole" and to let me take control of things.
Even with that one kinda uncomfortable stabbing, I was soooooo wet (without my pussy being touched at all by that point)! I've always had stronger, more intense orgasms through anal. And my pussy always drips a lot too.
sereneone4u
quod nutrit me destruit
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Still a virgin in that aspect...but there are some Lit men in the running....
buttpluglover
Virgin
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- Oct 15, 2005
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As addicted as I am to anal stimulation, I, too, am an anal virgin. Really gotta change that someday.
angelkitty7888
Really Really Experienced
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- Oct 12, 2006
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i'm an anal virgin too but i do like playing there... my girlfriend isn't overly into sharing her kinks yet... (she's found out some of mine by raiding my porn collection lol) maybe when she gets more comfortable with the idea we'll get there (and when we get a strap-on...)
sinfulallure
Experienced
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- Nov 25, 2006
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- 52
I can still feel the feeling as it happened , a piccie of that night
lost it and loved it
Back a few years ago, had a buddy who would come over about once a week. We were into a lot of passionate kissing, mutual j/o and sucking one another. After a few weeks of this, he brought up fucking me. As I had no experience with either anal sex or ass play, I declined.
As we kept meeting, I grew to really like him, and loved pleasing him and since he would mention fucking me from time to time, I decided to give him what he wanted. I bought a few butt toys of varying sizes and some lube made for anal (it was a little thicker than most lubes). A few days before he was to visit again, I began using the butt toys to strech my hole a little, working up to a butt plug with a 1 3/8" diameter.
After we had settled into bed and things got really passionate, I told him that I was ready to try getting fucked. His eyes lit up and he was more than receptive to the idea. Luckily, he was experienced. He first put lube on his finger and gentle worked it into me, then after I was comfortable, added a 2nd finger. The time had come, he rolled on a condom, lubed it well, added more lube to my hole. He placed my legs on his shoulders and guided the head of his cock (which was 8" long and about 6" in circumference) to my asshole and began pushing gently. There was a little pain, but not bad and my hole started to open as he slowly pushed forward. When he was in a little, my sphincter muscle stretched around the head of his cock, then snapped shut around the shaft....what a feeling that was. He gently moved in and out, going a little deeper each time. Finally, after about 10 minutes, he was all the way in me and started fucking me a little faster. It didn't take long and he was cumming while inside me.
I loved the feeling of getting fucked the very first time, and we had many meetings that ended up with him fucking me, always with me on my back, so it took a while before I had a chance to experience other positions.
Back a few years ago, had a buddy who would come over about once a week. We were into a lot of passionate kissing, mutual j/o and sucking one another. After a few weeks of this, he brought up fucking me. As I had no experience with either anal sex or ass play, I declined.
As we kept meeting, I grew to really like him, and loved pleasing him and since he would mention fucking me from time to time, I decided to give him what he wanted. I bought a few butt toys of varying sizes and some lube made for anal (it was a little thicker than most lubes). A few days before he was to visit again, I began using the butt toys to strech my hole a little, working up to a butt plug with a 1 3/8" diameter.
After we had settled into bed and things got really passionate, I told him that I was ready to try getting fucked. His eyes lit up and he was more than receptive to the idea. Luckily, he was experienced. He first put lube on his finger and gentle worked it into me, then after I was comfortable, added a 2nd finger. The time had come, he rolled on a condom, lubed it well, added more lube to my hole. He placed my legs on his shoulders and guided the head of his cock (which was 8" long and about 6" in circumference) to my asshole and began pushing gently. There was a little pain, but not bad and my hole started to open as he slowly pushed forward. When he was in a little, my sphincter muscle stretched around the head of his cock, then snapped shut around the shaft....what a feeling that was. He gently moved in and out, going a little deeper each time. Finally, after about 10 minutes, he was all the way in me and started fucking me a little faster. It didn't take long and he was cumming while inside me.
I loved the feeling of getting fucked the very first time, and we had many meetings that ended up with him fucking me, always with me on my back, so it took a while before I had a chance to experience other positions.
A few years ago, I had just started working at a mall job while I was in grad school. On my first day of work, in the middle of training, my female boss told me not to take it the wrong way but she really wanted to fuck me. It was the most forward thing a woman had ever said to me, and I have to say, it turned me on.
For the rest of the day, all we could do was talk about different things that turned us on. She was a pretty kinky girl. She said that she had a strap-on, but she had never had the chance to use it. I wanted to fuck her in the ass, and suggested that I would be ok with her using her strap-on on me if I could fuck her in the ass also.
That night she came over to my place and went straight to it. Later I learned that she was not much for small talk. I remember I was on my back and she was sucking my cock. After a while, she went lower and started rimming me. That was a first for me, but I really loved it. After that, I told her to put her cock on because I wanted it inside me. I bent over because I always wanted to try getting it doggy style. After a time, she lubed me up with lots of gel and proceeded to place her cock at my ass. She was so gentle, there was hardly any pain. Once she was in, it just felt so good. We used to take turns fucking each other in the ass.
We hooked up a lot. We had a 3-way with another girl. One time, she asked me to take part in a 3-way with one of her other bimale friends but I was young and chickened out. It is something I have thought about a lot over the years. I wished I had given it a try.
Some years later, after talking about that fantasy with another girlfriend, I decided to give sex with a guy a try. I placed an add in adult friend finder and met a cool guy. He was also a straight acting bisexual guy. He put me at ease with his personality. a few days later he came over to get to know one another. After chatting for a while, we eventually got to touching one another. I was fascinated with his cock, since this was my first time with another guy. After we sucked each other, I told him I wanted him to fuck me. I got up on the couch and bent over doggy style, of course. He rimmed me and lubed me up really good because he was a bit thicker than I am. When I felt his cock at my ass, I was thinking it was amazing that I was finally doing it. After he was in and started fucking me, I was thinking it was fucking amazing. It felt so good, I remember wondering why I had not done it before. It was so good, I was leaking precum all over my couch.
The one thing I really want to do is meet a down to earth male/female couple to play with. Still looking for that one....
For the rest of the day, all we could do was talk about different things that turned us on. She was a pretty kinky girl. She said that she had a strap-on, but she had never had the chance to use it. I wanted to fuck her in the ass, and suggested that I would be ok with her using her strap-on on me if I could fuck her in the ass also.
That night she came over to my place and went straight to it. Later I learned that she was not much for small talk. I remember I was on my back and she was sucking my cock. After a while, she went lower and started rimming me. That was a first for me, but I really loved it. After that, I told her to put her cock on because I wanted it inside me. I bent over because I always wanted to try getting it doggy style. After a time, she lubed me up with lots of gel and proceeded to place her cock at my ass. She was so gentle, there was hardly any pain. Once she was in, it just felt so good. We used to take turns fucking each other in the ass.
We hooked up a lot. We had a 3-way with another girl. One time, she asked me to take part in a 3-way with one of her other bimale friends but I was young and chickened out. It is something I have thought about a lot over the years. I wished I had given it a try.
Some years later, after talking about that fantasy with another girlfriend, I decided to give sex with a guy a try. I placed an add in adult friend finder and met a cool guy. He was also a straight acting bisexual guy. He put me at ease with his personality. a few days later he came over to get to know one another. After chatting for a while, we eventually got to touching one another. I was fascinated with his cock, since this was my first time with another guy. After we sucked each other, I told him I wanted him to fuck me. I got up on the couch and bent over doggy style, of course. He rimmed me and lubed me up really good because he was a bit thicker than I am. When I felt his cock at my ass, I was thinking it was amazing that I was finally doing it. After he was in and started fucking me, I was thinking it was fucking amazing. It felt so good, I remember wondering why I had not done it before. It was so good, I was leaking precum all over my couch.
The one thing I really want to do is meet a down to earth male/female couple to play with. Still looking for that one....
Hyperion717
Experienced
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- Jun 7, 2002
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Delete
Last edited:
Programmer Cat
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I can't tell about the first time I received anal; I was underage and it involved a female teacher.
AussieAngel
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damn...Programmer Cat said:
i bet its a great story too
Programmer Cat
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AussieAngel said:damn...
i bet its a great story too
Yeah, my violin instructor was hot, and I was hot for teacher.
AussieAngel
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tease!!Programmer Cat said:
aconsenter
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male to male, plus one
They had arrived before me. I walked by his car and saw the room # in the car window. His friend opened the door and as I went in I watched his naked ass go into the bathroom. There laid my master/man, cock sticking up into the air and his arms folded behind his head on the pillow. I smiled and walked over and planted a big wet kiss onto his big cock. I stripped down and climbed between his legs. As I stroked his cock, my tongue went to work on his sack and balls, licking all the way down to his asshole. He was moaning and pumping his cock into the air waiting for my mouth which he knew would find him. I sucked his cock in and started bobbing up and down, wishing he would just give me his cum quickly. But he never does. His friend slid onto the bed and cupped my balls while he kissed my back. I took master/mans cock all the way, deep throating til his pubes were ticking my nose. He told his friend to "watch this" and pushed my head down until my face was jammed into his stomach. I had emailed him and told him I wanted fucked and that was what i was there for. He pushed me off and told me to bend over at the end of the bed. I did as i was told and felt a cold slickness being placed on and in my asshole. My body was shaking with anticipation, desire and a little fear for what was about to happen. There was no turning back now. I felt a slight pressure and kabam, he pushed hard into me. I let out a loud, painful yell and it made him freeze for a moment. He asked if I was okay and I couldn't answer for a couple moments. I finally said yes, but slow down. He laughed and started moving in and out real slowly, but ignoring my moans as he pumped hard on the in strokes. Well, his friend slipped up and stuck his cock in my face and i sucked him while I was being fucked by master/man. We went through all the positions and ended with both of them cumming on me. After we were done and cleaning up, I told him it was my first time for anal. He said "damn if I'd have known that I would have been more gentle". His friend said "that's bullshit, you are never gentle". Very fun and pleasurable. Haven't had anyone since, almost three years ago.
They had arrived before me. I walked by his car and saw the room # in the car window. His friend opened the door and as I went in I watched his naked ass go into the bathroom. There laid my master/man, cock sticking up into the air and his arms folded behind his head on the pillow. I smiled and walked over and planted a big wet kiss onto his big cock. I stripped down and climbed between his legs. As I stroked his cock, my tongue went to work on his sack and balls, licking all the way down to his asshole. He was moaning and pumping his cock into the air waiting for my mouth which he knew would find him. I sucked his cock in and started bobbing up and down, wishing he would just give me his cum quickly. But he never does. His friend slid onto the bed and cupped my balls while he kissed my back. I took master/mans cock all the way, deep throating til his pubes were ticking my nose. He told his friend to "watch this" and pushed my head down until my face was jammed into his stomach. I had emailed him and told him I wanted fucked and that was what i was there for. He pushed me off and told me to bend over at the end of the bed. I did as i was told and felt a cold slickness being placed on and in my asshole. My body was shaking with anticipation, desire and a little fear for what was about to happen. There was no turning back now. I felt a slight pressure and kabam, he pushed hard into me. I let out a loud, painful yell and it made him freeze for a moment. He asked if I was okay and I couldn't answer for a couple moments. I finally said yes, but slow down. He laughed and started moving in and out real slowly, but ignoring my moans as he pumped hard on the in strokes. Well, his friend slipped up and stuck his cock in my face and i sucked him while I was being fucked by master/man. We went through all the positions and ended with both of them cumming on me. After we were done and cleaning up, I told him it was my first time for anal. He said "damn if I'd have known that I would have been more gentle". His friend said "that's bullshit, you are never gentle". Very fun and pleasurable. Haven't had anyone since, almost three years ago.
DontThankJustSpank
Experienced
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- Nov 27, 2006
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both from a man and a woman - on different occasions
Both times were when I was in college-truly first time was with a man I was dating, we had "played around" back there a lot but I was pretty scared of how much it would hurt. Ok, it turns out that if you get about 30 minutes of oral sex, rimming, and lots of lube--it doesn't hurt. Loved it x10!
Very heavily in the rotation in the marriage bed. Husband loves doing it himself as well as seeing another man do it to me. Gets hard when I talk about him doing it that way...
Both times were when I was in college-truly first time was with a man I was dating, we had "played around" back there a lot but I was pretty scared of how much it would hurt. Ok, it turns out that if you get about 30 minutes of oral sex, rimming, and lots of lube--it doesn't hurt.
Loved it x10!Very heavily in the rotation in the marriage bed. Husband loves doing it himself as well as seeing another man do it to me. Gets hard when I talk about him doing it that way...
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Programmer Cat
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AussieAngel said:tease!!
Sorry. I could tell you about the first time I took it up the ass from somebody I loved, though. Not to mention the first time I took the active role in anal sex.
PredatorSmile
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Programmer Cat said:
Do tell. It' s always better with someone who cares about you.
Cenobite
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- Mar 13, 2004
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Hmm, well my first time was with a guy I'd hooked up with on IRC to figure out if I was bi or not.
Turned out I was.
He tried to climb onto me but found some difficulty involved (being thick does kinda make things awkward) so I offered to try him instead... was quite painful and all that, but eventually ended up feeling good, and rather vacant afterwards.
Turned out I was.
He tried to climb onto me but found some difficulty involved (being thick does kinda make things awkward) so I offered to try him instead... was quite painful and all that, but eventually ended up feeling good, and rather vacant afterwards.
tango48
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- May 19, 2006
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when i was 12 (1960), i joined an all boys school, my previous schooling was in co-ed schools. i did not know what bi or homo was, the one big difference being boys here were very open in exposing themselves contraray to girls in my previous school who expeosed themselves only to a few of us. then one day a boy dared me to show, and took me in his hand, next time he knelt and took me in his mouth but i pulled away still limp. one day a boy showed me his backside and asked to do the same, and before i knew i experienced my first (of three) anal penetrations, two then and one much later. but since then i have been a topper.
without realizing i became bi, i have had many nice relationships with males, both younger and older than i am since, and it is my secret. experiences include, beeing rimmed, sucked, showering, the whole mile!
the first male i had was at 16, a friend broght his boy to my place, and we had a go together, it took a bit of pushing but finally i was in, and it was not bad, as were the many other times that followed! that was also my first male sucking me experinence. i enjoy male company equally as of females, and over the years its been an overall nice experience being bi.
this is the first time i have come out of the closet (so to say), thanks to literotica and all of you nice people here!
without realizing i became bi, i have had many nice relationships with males, both younger and older than i am since, and it is my secret. experiences include, beeing rimmed, sucked, showering, the whole mile!
the first male i had was at 16, a friend broght his boy to my place, and we had a go together, it took a bit of pushing but finally i was in, and it was not bad, as were the many other times that followed! that was also my first male sucking me experinence. i enjoy male company equally as of females, and over the years its been an overall nice experience being bi.
this is the first time i have come out of the closet (so to say), thanks to literotica and all of you nice people here!
