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What was your best Anal Experience?

I would have to say one of my all time best anal experiences was with my wife involved. Now keep in mind I have had several really good ones but this one was very good. Me and my wife had met with another bi couple. We were all playing, me sucking the guys cock him sucking me. His wife sucking me my wife sucking him. Then the women both sucking cocks with us at the same time. It went on for a few hours both us guys had fucked and cum in the others wives. But the last session I was on my back the husband had his cock in my ass. His wife was fingering his ass as he pumped mine. And my wife with cum still in her pussy was straddling over my face as I licked her clit and pussy and ass. My wife squirted all over me the guys wife stroking my cock fingering his ass as he fucked my ass. I lost it and shot my load all over the wife's hand and my belly. My ass tightened and he came in my ass. It was truly the most erotic and best experience I ever had. Mainly because it was shared with my wife. And when we got home the next day and took a shower together and laud in bed and talked about it, it's an amazing thing to share that with the woman you love.
 
Probably a tie between the first time my wife used a huge double ended dildo on me and my first double penetration from my boyfriend and his friend. Although getting fisted by my wife was also incredibly pleasurable
 
Not that there was a cock in my ass, i'm not into that but i've had a gf, who fingered my asshole and gave me a nice and horny prostate massage, while jerking me off in her face. I came so intensive legshaking...Loved it.🥰
 
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One particular experience comes to mind. I had contacted a well-reviewed erotic massage provider that offered happy endings, I asked if she offered prostate massages. She responded that prostate massages were her specialty. We ended up having a one-hour session where she concentrated solely on my cock and my prostate, both externally and internally. It was an amazing session! I came in buckets!
 
Probably the first time because I just asked and didn't realize it was as simple as that. A close second would be getting pegged and having my first anal orgasm.
 
I was getting fingered and teased right in my arsehole by my hookup partner.

He finally started to fuck me and got his cock in my arsehole without too much force. It took some thrusts, but I shuddered and shook as I had a dry orgasm for several minutes. I was moaning like a girl and squealing as he fucked me.

Even after he finished fucking me and came all over my arse, I was shaking and moaning for over half an hour. I must've dry orgasmed for over an hour.

Yes, I was dressed in sexy lingerie. I think it was blue.
 
To this day I went to a guy's all dressed up skirt tights heels will thong make up and all he had a nice 6.5 to 7 inch cock little thicker but not so huge it hurt, just nice stretch and long enough to hit my button he started slow and steady but after a while I was pushing back on him like I had lost my mind and maybe I did it felt so flipping amazing and I came hard and he fucked me right through my orgasim and felt like I was building to another but did not before he came but omg was 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.
 
Masturbating with a vibrating butt plug in my ass and a heap of lube on my cock. Must have been rumbling my prostate, because I came like a fountain in a surprisingly short time.
 
My apartments living room window faces onto the walkway between apartments. The drapes were closed, and I can hear people talking as they walk by.

My FB came over, I answered the door completely naked and very ready.

i was leaning forward, hands on the windowsill as he lubed then entered me and fucked me.

My neighbor was hanging out with a friend, sipping wine and chatting, I could hear every word. That was hot as hell, especially when my buddy reached around and jerked me off.
 
JulesLA said:
With a trans lover. Early morning of her bday.. i was 85% still asleep while being the little spoon.. by the time i fully woke up it was with her cock deep inside me. She fucked me spooning, doggy, cow girl and reverse cowgirl.
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That has happened to me but I was 100% asleep when my girlfriend pulled my underwear off so she could get her cock in my ass. It's crazy to wake up with someone thrusting their cock up your ass about to cum! Did you enjoy your experience as much as I did?
 
Escierto said:
That has happened to me but I was 100% asleep when my girlfriend pulled my underwear off so she could get her cock in my ass. It's crazy to wake up with someone thrusting their cock up your ass about to cum! Did you enjoy your experience as much as I did?
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Oh it was amazing. I was pretty much asleep as i started to feel her cock get hard in her panties and she started to hump my ass… she then took her panties off and started semi penetrating me with my my boxers still on… until she couldnt help herself anymore and pulled my boxers off as quickly as she could, put spit on her hand, rubbed it on my asshole and shoved her raging hard cock in. I guess i was so horny from the whole thing because she went in pretty easily.
 
JulesLA said:
Oh it was amazing. I was pretty much asleep as i started to feel her cock get hard in her panties and she started to hump my ass… she then took her panties off and started semi penetrating me with my my boxers still on… until she couldnt help herself anymore and pulled my boxers off as quickly as she could, put spit on her hand, rubbed it on my asshole and shoved her raging hard cock in. I guess i was so horny from the whole thing because she went in pretty easily.
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We belong to a unique club! Are you still with her?
 
my best experience was my first time riding a homemade dildo, this one I formed from white air dry clay, letting it dry a few days prior and then I put 2 thick condoms over and then taped the base to a stack of old pillows and started bouncing on it and I started secreting a white dripping like a Combination mix of pre cum and cum, it wasnt clearlike precum but not really fully white cum either, but it had a creamy juicy texture, and while not really cumming at first, the thrusts would push against me on the inside and I would just ooze it out from my cock head, where I gathered it onto my fingers rather than let it land on the bed or pillows and I lapped it up like some sort of sissy slut as I bounced up and down over and over and then I had the most mind blowing cum explosion as it shot across the bed and I hadn't even stroked my cock at all yet, it was all anal internal and it shot through my entire pelvis all throughout my dick, and it had been spectacular but my legs wers shaky and wobbly all throughout, even into the next day. Never been able to repeat it.
 
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JulesLA said:
Damn she is gorgeous… i bet sex with her must be out of this world… got to love sex when you can both top and bottom.. z
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Thank you. It is out of this world but it's a one way street. She is a pure top.
 
Escierto said:
Thank you. It is out of this world but it's a one way street. She is a pure top.
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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..
 
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