What was your best Anal Experience?

Oohh… ok… so i guess she must have a great endowment lol…. Though i bet all her body is gorgeous.. im vers so i love the giving and receiving. I mostly topped with my trans lover.. her ass was just too good not to fuck it..
Interesting that you said she must be endowed. How did you guess? As she says, that entitles her to be the top. Her ass is very nice but I only get to lick her hole.
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She really looks lovely. You lucky man. No chance you can get back together?
 
My girl's cock is slightly over seven inches. It takes my breath away whenever I see it. Which is every day. Five years and I still love to look at it.
 
My girl's cock is slightly over seven inches. It takes my breath away whenever I see it. Which is every day. Five years and I still love to look at it.
Oh wow big.. nice… bet it feels amazing when she penetrates you… yeah my lovers cock is gorgeous too… perfect size for me
 
Oh wow big.. nice… bet it feels amazing when she penetrates you… yeah my lovers cock is gorgeous too… perfect size for me
She is not gentle, I will say that but I like it. It's strange that she is super feminine but she fucks like a man. She takes my ass and uses it hard. Once I asked her, do you think of my ass as a pussy for your cock? She said, no, I think of it as an ass for my cock.
 
Giving or Receiving?
It's really impossible to pick just one but if I have to choose one it was when I fucked my wife in the ass while she was riding a Houston fireman. Feeling his cock through the thin wall between pussy and ass was absolutely incredible.
I have a few more incredible times.
 
The best time was when I was pegged and fisted two days in a row in a hotel room. I was just a bit sensative the second day. Being pegged and fisted that second day was unbelievable. I couldn't get enough. And gratefully, she was more than willing to make me yell in ecstacy and pain over and over.
 
Buddy and I were drinking heavily, watching one of the Lord of the Rings movies, and most unexpectedly he told me to take off my pants. I gave him a "what", shook my head and went back to my drink and movie. He said he was serious. I didn't respond. If his voice wasn't serious enough, he took off his belt, unbuttoned, and unzipped his pants before I could respond. Dropping his pants and underwear, I was shocked and not sure what was going on. He told me again, "take off your pants". I was too stuck in the uncertainty of the moment to do much more than mutter. He splash grabbed my drink away, turned me over and ripped my pants and underwear off. I was barely making out his verbal rattle of "you better listen to me when I speak. I expect you to follow directions. My directions". He held me pinned down in shock, and whipped my bare butt with his belt about twenty times. Freaked and in tears, he continued to spank my bare bottom with his hand. His spanking me lasted about three to five minutes. I laid there in tears and shock for about a minute, until he came back, and pinned me again. He took lube and spread it all up inside me. There really wasn't much time between the few moments he spent lubing my hole, squeezing my butt cheeks, and spanking me a few more times. He pulled himself by my hips to get between my legs, then used his thumbs to push my butthole appart and thrust his long hard dick inside me. "Take my cock and tell me you like it". He wasn't much for words, but clear on commands. I was spanked until I responded exactly how he told me. His fucking me was not as painful as I imagined it to be, but it was forceful and rough. It was at least a thirty minute labor chore. I wasn't going anywhere except forwards and backwards on a couch while he controlled my hips, shoulders, and ass. My butt was hard spanked and fucked with him telling me to control my tears and please him by telling him how much I loved having his dick inside me and being his bitch. I fully complied with everything he told me to do. It wasn't out of pleasure or sexual satisfaction, as much as it was wanting to calm his spanking me and give him the satisfaction of clearly dominating me. He gave me a two week mental health reprise. All felt forgotten. Then he took me up to his parent's summer cottage, and no sooner than we entered the front door it was clear by his voice that I was getting my ass thrashed and fucked again. No belt, but my bare cheeks were turned bright red from a hairbrush he brought. The second time was more painful than the first. He used lube again, but getting pounded hard by his 8" cock and balls for forty-five minutes left my ass soar for two days. I was bent over a second time and given a short fifteen minute "you like being my bitch" fuck the next morning before we left. Another reprise of two or three weeks was good. I figured out that when I drove us places, my ass wouldn't belong to him for the rest of the night. So, that helped. Then after a Tears For Fears concert we attended at a winery, he drove me to our old high school football field. I followed him, and only got the classic "I'll show you". As cliche as you can imagine, there was a bench behind the far end bleachers where you could look out to a lake and see up to the stars. If I didn't already kind of know what was coming, he dropped his pants and underwear and made it clear. "No spanking tonight, if, if you tell me how much you want my cock inside you, and do exactly what I say when I fuck you". Please don't call me your bitch, I said. "Deal. But only if you do everything else I want?". I answered, yes. Then I looked at his naked body and long hard erection, and stripped naked for him to do with me as he pleased. I won't deny I was more than a little freaked as well as simultaneously being highly aroused. He put both his hands on my hips and turned my butt around. This time without being forceful, he pushed my shoulders lightly and bent me over the bench. I like that he consistently cares about not leaving me as analy roughed up as he could. He proceeded as a good gentlemen by lubing up my butthole. He pushed his erect hard cock all the way inside my ass pretty fast. It hurt to tears worse than I ever remembered. Then he didn't do a thing. I stopped crying and stayed bent over with his eight inches all the way up inside my butthole for what must have been three, maybe five minutes. I felt him slowly moving a few inches back and forth. He found a good rhythm doing me like this. I couldn't believe my almost womanly moan that arose from my groin and came out of my mouth. I realized right then he wasn't doing much of the moving forward and back on his big hard penis. It was me. I couldn't believe how amazing it felt moving my asshole back and forth over his rock hard cock. Fuckng his big penis felt so good. Even more, was how incredible it felt as my bare ass pushed and slapped against his strong stomach and hips. The sound of spanking his pumping and fucking hips made my bare ass so turned on that I was naturally reminded how much more I appreciated his cock inside my butt more than his belt, brush, or hand slapping and spanking my butt red, making me cry in submission to him. He dropped down by my ear and said "you won't be my bitch anymore if you tell me you're my summer lover". I answered without hesitation that I was indeed his submissive summer lover.
 
Buddy and I were drinking heavily, watching one of the Lord of the Rings movies, and most unexpectedly he told me to take off my pants. I gave him a "what", shook my head and went back to my drink and movie. He said he was serious. I didn't respond. If his voice wasn't serious enough, he took off his belt, unbuttoned, and unzipped his pants before I could respond. Dropping his pants and underwear, I was shocked and not sure what was going on. He told me again, "take off your pants". I was too stuck in the uncertainty of the moment to do much more than mutter. He splash grabbed my drink away, turned me over and ripped my pants and underwear off. I was barely making out his verbal rattle of "you better listen to me when I speak. I expect you to follow directions. My directions". He held me pinned down in shock, and whipped my bare butt with his belt about twenty times. Freaked and in tears, he continued to spank my bare bottom with his hand. His spanking me lasted about three to five minutes. I laid there in tears and shock for about a minute, until he came back, and pinned me again. He took lube and spread it all up inside me. There really wasn't much time between the few moments he spent lubing my hole, squeezing my butt cheeks, and spanking me a few more times. He pulled himself by my hips to get between my legs, then used his thumbs to push my butthole appart and thrust his long hard dick inside me. "Take my cock and tell me you like it". He wasn't much for words, but clear on commands. I was spanked until I responded exactly how he told me. His fucking me was not as painful as I imagined it to be, but it was forceful and rough. It was at least a thirty minute labor chore. I wasn't going anywhere except forwards and backwards on a couch while he controlled my hips, shoulders, and ass. My butt was hard spanked and fucked with him telling me to control my tears and please him by telling him how much I loved having his dick inside me and being his bitch. I fully complied with everything he told me to do. It wasn't out of pleasure or sexual satisfaction, as much as it was wanting to calm his spanking me and give him the satisfaction of clearly dominating me. He gave me a two week mental health reprise. All felt forgotten. Then he took me up to his parent's summer cottage, and no sooner than we entered the front door it was clear by his voice that I was getting my ass thrashed and fucked again. No belt, but my bare cheeks were turned bright red from a hairbrush he brought. The second time was more painful than the first. He used lube again, but getting pounded hard by his 8" cock and balls for forty-five minutes left my ass soar for two days. I was bent over a second time and given a short fifteen minute "you like being my bitch" fuck the next morning before we left. Another reprise of two or three weeks was good. I figured out that when I drove us places, my ass wouldn't belong to him for the rest of the night. So, that helped. Then after a Tears For Fears concert we attended at a winery, he drove me to our old high school football field. I followed him, and only got the classic "I'll show you". As cliche as you can imagine, there was a bench behind the far end bleachers where you could look out to a lake and see up to the stars. If I didn't already kind of know what was coming, he dropped his pants and underwear and made it clear. "No spanking tonight, if, if you tell me how much you want my cock inside you, and do exactly what I say when I fuck you". Please don't call me your bitch, I said. "Deal. But only if you do everything else I want?". I answered, yes. Then I looked at his naked body and long hard erection, and stripped naked for him to do with me as he pleased. I won't deny I was more than a little freaked as well as simultaneously being highly aroused. He put both his hands on my hips and turned my butt around. This time without being forceful, he pushed my shoulders lightly and bent me over the bench. I like that he consistently cares about not leaving me as analy roughed up as he could. He proceeded as a good gentlemen by lubing up my butthole. He pushed his erect hard cock all the way inside my ass pretty fast. It hurt to tears worse than I ever remembered. Then he didn't do a thing. I stopped crying and stayed bent over with his eight inches all the way up inside my butthole for what must have been three, maybe five minutes. I felt him slowly moving a few inches back and forth. He found a good rhythm doing me like this. I couldn't believe my almost womanly moan that arose from my groin and came out of my mouth. I realized right then he wasn't doing much of the moving forward and back on his big hard penis. It was me. I couldn't believe how amazing it felt moving my asshole back and forth over his rock hard cock. Fuckng his big penis felt so good. Even more, was how incredible it felt as my bare ass pushed and slapped against his strong stomach and hips. The sound of spanking his pumping and fucking hips made my bare ass so turned on that I was naturally reminded how much more I appreciated his cock inside my butt more than his belt, brush, or hand slapping and spanking my butt red, making me cry in submission to him. He dropped down by my ear and said "you won't be my bitch anymore if you tell me you're my summer lover". I answered without hesitation that I was indeed his submissive summer lover.
What a great story. Thank you for sharing it.
 
My first probally the best.
A girl I knew I met at a bar. Went home with her.
I was in my early 20’s and she was a good 10 years older
In bed I was toying with her rosebud… some women I had been with before were
Not comfortable with me touching.
This girl was ok… even pushed into my finger..
she whispers want to try? I said yes and she reached for a jar of Vaseline.
Handed it to me.. i remember the excitement of it all.
Being allowed to toy with her. Pushing a finger into her rectum.
I greased my self up and slowly pushed my cock into her.
The feeling was indescribable.. I had been in many pussys before.
But the feeling as I entered her ass was nothing I ever felt before.
It was tight. Tighter than I ever felt. And the heat. Was it like over a hundred degrees in her butt.
I slid in her and almost immediately came.. was just awesome..
After we showered and fucked the Traditional way.. was the only time I was with her.
But through time I experienced both sexed with anal sex.. still feels amazing
 
With the only regular male lover I've had, one occasion that began, as our sessions usually did, with me sucking him on my knees. Then we went to bed, and he started fucking me reverse cowgirl style - me sitting on his cock, facing him. He ordered me to play with my nipples, and then to stroke my cock. Being ordered like that, and me doing all the work of squatting on his cock, felt incredibly submissive, and the position allowed both his cock to go in all the way in (it was extremely erotic to feel his pubic hair against my ass) and to stimulate my prostate, although I didn't orgasm from the stimulus.
OMG that is the type of sex I consider volcanic! So dirty (I am submissive also) and I need to experience exactly what you did. I love cock too honey, please PM me as I've read some of your posts, and man they make me horny and hard. I have 24 gay males stories on LIT, username is PG564E. Latest title is "AFTERNOON DELIGHT". If you read my works, your cock is going to feel like a piece of iron. Gay sex is primal, and the best of all in my opinion. Hope to hear from you soon, I don't think we have talked in the past.
 
I have bottomed for many men and I have many great experiences. A half a dozen times I have cum hands free and the feeling was incredible but very messy. ;)
 
A long time ago I took strapon. I rode it cowgirl, which was nice, but she clearly did not want me to think of myself as a female taking cock, which to me was the whole point.
I like a dildo that's as cocklike as possible. My Lovense Hush is only a dual-motor vibrator, but feeling it controlled by someone is very nice, and it's possible to do that over the Web.
I use my imagination, and I have had amazing experiences in cyber chat with a like-minded mature trans girl or a man.
I can cum handsfree if I take it to the edge first, and I can multiple orgasm.
 
With the only regular male lover I've had, one occasion that began, as our sessions usually did, with me sucking him on my knees. Then we went to bed, and he started fucking me reverse cowgirl style - me sitting on his cock, facing him. He ordered me to play with my nipples, and then to stroke my cock. Being ordered like that, and me doing all the work of squatting on his cock, felt incredibly submissive, and the position allowed both his cock to go in all the way in (it was extremely erotic to feel his pubic hair against my ass) and to stimulate my prostate, although I didn't orgasm from the stimulus.
OMG, YES! As a submissive myself, I love that kind of experience.
 
OMG, YES! As a submissive myself, I love that kind of experience.

With the only regular male lover I've had, one occasion that began, as our sessions usually did, with me sucking him on my knees. Then we went to bed, and he started fucking me reverse cowgirl style - me sitting on his cock, facing him. He ordered me to play with my nipples, and then to stroke my cock. Being ordered like that, and me doing all the work of squatting on his cock, felt incredibly submissive, and the position allowed both his cock to go in all the way in (it was extremely erotic to feel his pubic hair against my ass) and to stimulate my prostate, although I didn't orgasm from the stimulus.
Im looking forward to something exactly like that in about 34 minutes :)
 
Every time with my girl is the best. Like tonight.

I was tired and I went to bed early so I was asleep when she came to bed. She embraced me, waking me up and as she lay there, she put my hand on the male organ in her panties. After she took her panties off, I sucked on her cock so she would be stiff and ready to fuck me. I took my t-shirt and underwear off so I was completely nude and then I got some lubricant and put it in my hole and the residue on my hand on her cock.

I lay on my side away from her and I could feel her position her cock at my anus and then push the head in. It slide in easily and she put one of her hands on my shoulder for leverage as she likes to do. A few thrusts of her groin and she had completely penetrated me. I love that moment when she has mounted me and we are tied together with her cock like a man and woman.

Now she began to fuck me in earnest and I moaned almost continuously panting "Oh baby" from time to time. She fucked me hard for only a couple of minutes before she let out a sharp "Ohhhh!" and I knew that she was going to have her orgasm.

With each spurt of cum from her cock, she thrust her cock up into me hard even though she couldn't get any deeper. She ejaculated four or five times grunting "Ugh" each time until she was finished breeding me. Then she pulled out and rolled over on her back spent from her fucking.

I immediately rolled over towards her and embraced her telling her "Thank you for fucking me. I think you definitely made me pregnant this time." We both laughed but I could sense her load of sperm inside me being absorbed into my body. I told her "You're my fucker, my lover, and I belong to you." I did feel that she had marked and possessed me with her sperm inside me. I was seeded and bred by her and I wondered, is this how it is for a woman with her man?
 
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