What was your best Anal Experience?

[klippert]

The best is fucking my wife's ass... with that said. 25 yr back, when I thought I was gay....and living the lifestyle.. I hooked up with a good looking fella...mix'd race, White-Hispanic...(get it)
anyhoo...when he dropped his pants... big dick. fortunately for me, he was a bottom... he began a long fetish for me...HUNG Bottoms. luv'd watching his big cock bouncing around...and easy for to reach....or pull back and suck while doing 'doggie' rim job

 

[t1m1d1]

Two stories, one was being spit-roasted by two beautiful Thai tgirls. My only threesome and caused a shattering anal orgasm! The other was being fucked by a beautiful African tgirl, large cock and amazing sex, the best I've ever had with anyone. We maybe met 7-8 times, wish I could meet her again. Both great personal memories!

 

[Mr. Briggs]

Two stories, one was being spit-roasted by two beautiful Thai tgirls. My only threesome and caused a shattering anal orgasm! The other was being fucked by a beautiful African tgirl, large cock and amazing sex, the best I've ever had with anyone. We maybe met 7-8 times, wish I could meet her again. Both great personal memories!

Wow!!! Nice

 

[Mr. Briggs]

The best is fucking my wife's ass... with that said. 25 yr back, when I thought I was gay....and living the lifestyle.. I hooked up with a good looking fella...mix'd race, White-Hispanic...(get it)
anyhoo...when he dropped his pants... big dick. fortunately for me, he was a bottom... he began a long fetish for me...HUNG Bottoms. luv'd watching his big cock bouncing around...and easy for to reach....or pull back and suck while doing 'doggie' rim job

Hmm hung bottoms! Sexy idea.

 

[BiiCuz]

Being trans formed into a fem and have a Daddy dom take my cherry with 5'' then a couple weeks later he invites a cross dresser with 7+" and they take turns at both ends but alway filling up the backend

 

[Mr. Briggs]

Being trans formed into a fem and have a Daddy dom take my cherry with 5'' then a couple weeks later he invites a cross dresser with 7+" and they take turns at both ends but alway filling up the backend

WOW!!!!

 

[CottonForMe]

Love reading everyone's experiences and hope to have similar experiences some time.
Mine is a simple one. My partner had just cum in me and went to the bathroom. I was on the bed stretching (unwittingly in a provocative position). He came out and entered me like he owned me. He gave me a hard pounding and another load. So far that is my favorite anal experience.

Mmmmmm...............

 

[alerner0070]

My best anal experience was with my ex wife. She started with just fingers, then moved to dildos. Eventually, she bought a strap on and that was so exquisite. She would look into my eyes as my legs wrapped around here pulling her in. Eventually we had enough anal play that she was able to fist me. OMG, the feeling of being FULL. Never came so hard in my life.

 

[pussycatmeowth]

With an older guy who really knew what he was doing. He'd slowly enter me from underneath, until it was all the way in, then gently rock us together. He'd hold my cock firmly and stroke it up and down, pulling my foreskin back and forward.

From the first time it felt amazing, like the end of his cock in my ass, somehow was connected up through to mine as he pushed it deep into me. I tried to hold back but it was too intense and I shot a huge amount of spunk all over him, I was so naive, I thought he'd be mad but he was delighted of course and responded, pouring his semen into me.

I had wonderful sex too years later, with a girlfriend who was totally into anal. She liked to be held tightly, my shoulders forcing her legs right back as she'd reach down with her right hand, covering the entrance to her vagina, so my heavily lubed cock would slide into her ass.

Using the technique of my male partner I would take my time, allowing her ass to get used to my cock and only after at least 5 minutes would I begin to fuck her a little faster. By now she'd be rubbing her clitoris, pulling the hood back with her index and third finger and using her middle finger to caress the little button as fast as she could.

We got so good at it we'd often come together, usually my cock stiffening to it's hardest as my orgasm approached, was enough to get her there too and we be locked together, her ass muscles contracted tightly against my bloated penis as it pulsed out streams of come into her as she masturbated her clit furiously as her climax ripped through her.

Afterwards it was always difficult to withdraw, my cock would still be so stiff, I had to pull it out really carefully. Sometimes we'd go again when I got my breath back in a few minutes (I was in my 20's still) and she'd be more relaxed, my cock would just slide all the way straight in this time, in one thrust and of course it would take longer. Her orgasm this time around, if she had one, would be so intense she'd almost pass out.

 

[pussycatmeowth]

Double post sorry

 

[Hitchiker69]

My best anal ever, receiving, was clearly my first, when I lost my anal cherry. I was with an older guy who seduced me...I was 100% willing and playing along...with drinks and a massage. Once we got started sucking and otherwise fooling around, naked in bed, I found he was on top of me and fully hard. His cock was probing my hole, and I was ready and willing to take him up my ass.

I'd already fucked several guys, and I was curious why they liked it so much.

So I spread my legs and thrust my hips towards him, letting him know clearly that I wanted him in me. He responded by grabbing my ass and pulling it to his cock, again with my full cooperation, we worked together. As he entered me I felt filled up in a deeply satisfying way. There was no pain, but I did feel stretched and full. He was a perfect considerate lover, driving deeper only enough to meet my pelvic thrusts until he was as deep as he could get. I was loving having him in me, and I met his thrusts as I locked my legs around him. We moved together , humping deeper and faster and harder. I was swooning, and fucking with complete abandon like a complete cock slut, which I was. I loved not only the feel of his cock plowing deep in my ass, but also the idea that my ass could excite a man so much, and arouse him to new heights of wild passion, which I felt too. I loved giving myself to him
We fucked like wild animals, deep, fast, hard and raw. He was sweating on me as we fucked, and I kissed him on the cheek, to let him know I was all his to take my ass, mouth, french kisses and all. ( He'd wanted to kiss me earlier, but I wasn't willing then)
I don't know how long we fucked, but it was totally satisfying and I'm glad I let him fuck me.
Ever since that night I've offered my ass to every guy I get in bed with. Some want it, some don't. Some anal sex is good, some isn't. Some guys are too domineering, very greedy, almost raping me.
I've never had another anal experience as good as that one.

 

[witchydiana85]

Some guys are too domineering, very greedy, almost raping me.

I've noticed this tendency, too; I ask them to go slowly, and they do for a bit, but then instinct/arousal takes over and they plough into me with abandon. With a bit more lube it's usually fine, but so many complain that it, "Ruins the sensation." Wish I hadn't put up with that shit when I was younger so much.

Best anal experience I've ever had was with a sweet woman I met when I went back to uni a decade ago; she was strong yet gentle, would listen, and knew how to move with me instead of making it all about her.

 

[bedroomexplorer]

My best anal is one where I never actually got penetrated. One night after a really rough day, I told my wife I wanted to get fucked in the ass. She simply said she would do that. I confirmed what I had heard and before too long we were laying in bed and she was giving me a hand job while telling me how she would push a dildo deep into my ass and how much I would enjoy it. My body was so turned on that her touch was electric and I was quivering with the thought of what she would do to my ass. I was telling her how I would let her fuck me however she wanted. We had agreed that she would wear a strap on and we would soon go and buy a dildo for her to use. I have never had a sexual experience like that before I was quivering with pleasure with just the anticipation of being penetrated. I still think about that time to this day. Last Friday she made me scream as she fucked my ass with a tantus dildo with a handle. We never did find the cum I shot that night.

 

[Julie_in_the_north]

With my ex, on our honeymoon. She entered me so slowly, gently and tenderly, but at the same time stretched and filled me so perfectly. I had the most delicious orgasm. In fact I think I came twice. But as we’ve since separated, the memory is now tinged with sadness too..

 

[load69]

Here's mine

https://imgur.com/Ok06bPP

 

[oneblueye]

hey...

I know a lot of us here enjoy Anal Stimulation. So let's hear it what was your best Anal Experience?

A couple years ago, I was here and getting bored. So I click over to CL when it was still up. I was going thru the ads and I saw one that was in my area for an erotic massage. So I contacted the guy and we set it up for the next day.
So the next day I dropped my kid off at school, found the guys address. Knocked on the door the nice looking guy answered and let me in we sat at the kitchen table talking for a couple minutes. Then he suggested that we get started.
I got undressed and up on the table, then he got undressed as well, this was unusual to me as I was used to women giving me massages and they never got naked. I didn't care, as he got up by my head and was working my neck and shoulders, I felt him adjust himself so his cock would drop in the palm of my hand. So I gave him a squeeze and started slowly jerking him, about two minutes into it I asked him if he was alright with what I was doing, he just smiled and continued.
Then getting toward the end of the massage he told me to flip over on my back once more.
Then he started jacking me off real slow and squeezing my cock as he got toward the end of the stroke. Of course, I had to ask him if this was extra, he laughed agai and said no, then he asked if I ever had a prostate orgasm. I said "what?" that was when he slipped his well oiled middle finger into my ass and took my power of speech away. I just felt these freaking warm waves just gushing over me after a while it felt like my cock was on fire and he stopped jacking my dick. He just kept working his middle finger on my prostate. All of a sudden I saw a flash like the noon day sun exploding in the middle of my forehead and I caught sight of a huge blob of cum shooting over my body and at his head.

 

[spawnofdavey]

Best anal experience I've ever had was with a sweet woman I met when I went back to uni a decade ago; she was strong yet gentle, would listen, and knew how to move with me instead of making it all about her.

Now this sounds like the kind of experience I'm looking for.

 

[bobb64]

my best was my first time. I spent the night with him and he took me three times that night.

 

[BlueEyes1969]

In a threesome. Lots of rimming and fingering before each of the trio had the opportunity to be penetrated by another. The playing and foreplay was so hot transforming the anal experience into spectacular feelings!

 

[Trimjob69]

Having my ex fuck me with a strapon

 

[SmoothAndSweet]

all were good except with a few who I let go bareback inside of me

 

[Escierto]

all were good except with a few who I let go bareback inside of me

Why was that a problem?

 

[RobLivesInTexas]

The best anal experience I've ever had was bottoming (I usually top) for a married buddy. His cock has a nice upward curve, so when he was in me while I was on my back, his cock hit my prostate over and over. The last time was just the two of us, and I came big time. The first time he fucked me, it was in an all-male threeway, all of us married, in a hotel room. His cock was hitting my prostate, and the other man was sucking my cock as I sucked his cock. It think it was one of the most powerful orgasms of my life. An ass ful of cum, a mouth full of cum, and my load in another man's mouth, almost simultaneously.

 

[Biguy77578]

I posted this before but not on this thread.
I met a guy coming out of an ABD on a slow night. He asked me to to his house. He ha 2 male roommates that were not at home. We showered together cleaning our asses real well then rimmed each other. That by itself as amazing. He the positioned me on all 4's greased up mz ass and proceeded to fuck me so good in every position.

 

[Travisspank]

Met my regular FB a couple weeks ago. We usually only have quickies, but had some extra time for long cock and ball worship session that he took a few clips of, followed by a long hard punishing fuck and creampie. As he fucked me from behind he grabbed both my arms behind my back and pounded me until he bred me. When he finished he pulled out and gave me his cock to suck. We did 69 for a bit and when I got him hard again he fucked me for another 30 min and put second load in my hole then collapsed on top of me until it finally slipped out and I could feel his cum leaking all over my open hole. After he recovered he sucked me off and I came in his mouth and he swallowed. It was fucking amazing.