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Old 05-22-2008, 09:54 PM   #1
Mr. Briggs
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What was your best Anal Experience?

I know a lot of us here enjoy Anal Stimulation. So let's hear it what was your best Anal Experience?
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Old 05-22-2008, 10:58 PM   #2
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Quote:
Originally Posted by Mr. Briggs View Post
I know a lot of us here enjoy Anal Stimulation. So let's hear it what was your best Anal Experience?
My best time was alone with a toy. I had a nice Jelly dong that was 5 to 6 inches long and about 1.25 to 1.5 inches in diameter. Probably closer to 1.25. I had a tube with a flat surface and was able to straddle it, with one leg in and one leg out. I set the dong, which had fake balls allowing it to balance on the tub edge. Using plenty of lube, I road that thing for all I was worth. Uhmm. I was really able to get a good rythme going and it got to really feeling good. That just egged me on to ride it faster and harder. My cock, which had softened a little after the initial penetration, grew back to rock hardness and that tickle inside just kept building until a cam. It wasn't like and orgasm I would get from stroking off or using a vibrator on my glanse. The cum just fountained out of me. My legs were weak for an hour afterward, that might have been from all the effort, but that orgasm was just wonderful. Hugs, Jenna
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Old 05-22-2008, 11:05 PM   #3
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my ex was against anal for a while, but loved when i would rim her and when i would slide a finger in her when i'd eat her pussy. so, one night, we were out kinda late and i had her bent over, fingering her pussy and giving her one helluva rimjob, when i started eatting her pussy and slid a few fingers in her ass she handed me a condom and told me she wanted me in her ass. it was incredible because she got really into it and then got her vibrator out and she found out she cums really fast with DP action.
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Old 05-22-2008, 11:12 PM   #4
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Yumm!

My girl put on the strap on.... She gave it to me slow in the missionary position.. This is one of my fantasies, to be the girl and get fucked! Wrapping my legs around her back and pulling her into me was hot!!!

Then I got on top and rode that thing, She stroked me while I bounced on the cock. It didn't take long before I was spurting cum all over her, which I doused my face in.
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Old 05-22-2008, 11:29 PM   #5
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Originally Posted by nbghyt56 View Post
my ex was against anal for a while, but loved when i would rim her and when i would slide a finger in her when i'd eat her pussy. so, one night, we were out kinda late and i had her bent over, fingering her pussy and giving her one helluva rimjob, when i started eatting her pussy and slid a few fingers in her ass she handed me a condom and told me she wanted me in her ass. it was incredible because she got really into it and then got her vibrator out and she found out she cums really fast with DP action.
For that kind of anal experience, it would have to be my wife's tight ass. It is even tighter than her pussy. Gets me off even quicker than her pussy. But I always worry I am going to hurt her. Many times, when I am in her pussy and I have gotten into a good rythm and it is really feeling good for her, she go on about how it feels like I am in her ass. One time, I was in her ass, and just holding still because I knew any movement would set me off. She put her vibrator on her clit and I felt it through her body. We both came in seconds! Hugs, Jenna
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Old 05-24-2008, 08:22 PM   #6
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Since anal sex is about the only sex I really engage in, it is hard to say what the best time was. It would be like saying which breath was your favorite. I will say that on the flip side, I hate it if anything isn't quite right. Yesterday, my partner said I could fuck him last night if I would buy him a cup of coffee. (I hate doing that as I hate the smell let alone the love-affair addition people have to that substance.) Nevertheless, I did.) Unfortunately, when we started playing around anally, he discovered that he was bleeding a bit. Thus we had to stop the activity. He was very generous in that he let me place a thumb up there while we both masturbated. It isn't as good, but I'd never want to injure anybody while fucking.

If I could have just one sexual wish it would be that I could fuck up until the day I die, and that my partner could take it without ever causing any damage. I have this fear that one day we'll get old, and I cannot get it up, he cannot take it in his ass, or age just makes it where it is too difficult to get into a position where we can fuck.
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Old 05-25-2008, 03:33 PM   #7
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It was early in my sexul life, I had been with women and I had sucked quie a few cocks, but I had only been fucked a couple of times, then I met the guy in Manhattan. He was about average in every respect....looks, hight, weight, etc. Then we undressed. His cock wasn't a bit average! It was huge! So fucking big I had no thought about taking it in my ass, and at first, I didn't think he was going to try.

He knelt between my legs and started sucking my cock, then he was licking my balls, and after a while he started to tongue and finger my asshole. God! it felt good. I was nearly coming and didn't realize what was happening until my legs were over his shoulders and my knees were pushed down on either side of my head. I was staring at my cock, catching the pre-cum dripping into my mouth and unaware of his cock nudging into my ass until the cockhead was inside. I felt the breath gasping from me as my spincter was stretched further then I could imagine. The rest of the fuck was relitively easy. He fucked with long, slow strokes, pushing deep into me again and again. I came! I shot a huge load of cum into my mouth and over my face. He licked the cum from my face as I swallowed the globs that found the way into my mouth, then I felt his cock jerk my asshole wider as he came and came and came.

When it was over, after his cock softened and slipped from inside my ass, he lay beside me, his cock limp but still huge lying across his thigh. I did something then I never thought I do. I knelt up beside him, leaned forward, and took his cock into my mouth. I sucked him clean. I sucked him until he was hard again and ready for another great fuck.
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Old 05-27-2008, 11:09 AM   #8
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Red face

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Old 09-10-2008, 02:00 AM   #9
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wife's strap on

When my wife first fuck me with her cock. 10 inch long and 2 inch thick. And buried deep inside my ass.
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Old 09-10-2008, 02:08 AM   #10
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wife's strap on

Edited out.

Last edited by Vacheron58 : 09-14-2008 at 08:48 AM. Reason: Edited out. Erroneous repeat.
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Old 09-10-2008, 07:49 PM   #11
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My best I would have to say was the first time my ex cross dressed me and fucked the hell out of me with a strap on. She had fingered me before during bj's but this night she wanted complete role reversal. I don't remember screaming when I came (she said I did) but I remember I couldn't stop shaking afterwards. We did it several more times after that but the first was best. One of the most intense orgasms I have ever had.
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Old 09-10-2008, 08:17 PM   #12
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Quote:
Originally Posted by Mr. Briggs View Post
I know a lot of us here enjoy Anal Stimulation. So let's hear it what was your best Anal Experience?
I'm hoping I haven't had my "best" anal experience yet, since I have never had a real cock inside me;YET. The 2nd best time though was first strap-on experience with my wife. But for now: best anal memory was first time I felt my cock in my wifes ass.
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Old 09-14-2008, 06:31 AM   #13
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Pitching or catching?

I got snowed in at my step son's apt. There was only one bed. I sleep in the nude as did he. He is a really big guy so the bed was crowded. I snuggled up close to him and fell asleep. During the night he wakes me up "Hey hey wake up!" I was trying to fuck him in my sleep. "I'm sorry, horny dream" He surprised me by saying"We can use lube" So I sucked his cock and laid him on his back, he threw his legs back and apart like a pro. I slid into his wonderful tight ass and slowly fucked him. It was pure heaven. I fucked him til the sun came up. Gave him a nice hot shower and cooked him breakfast. Sent him off with a big smile on his face. We fuck still to this day. I'm 58 and he is 26. I love him and am always ready for him if he ever needs anything.
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Old 09-14-2008, 12:56 PM   #14
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My most recent best anal experience occurred recently when LadyC brought home a very young guy named Jake. First, she had him fuck my mouth with brutal thrusts deep into my throat, then half an hour after I drank his delicious cum, LadyC ordered me down on all fours, then using saliva provided by her female sub Kay as lube, she guided Jake's cock into my asshole. He fucked me slowly, very gently, the sort of as fucking that you want to go on and on, and while he was fucking me, LadyC wiggled herself under me and took the end of my cock in her mouth. I came almost instantly. She swallowed my cum and continued to suck my cock, just the knob, using her teeth on the tender flesh just below the cockhead. Then Jake was fucking faster, faster and harder. He was coming. He came, the spasms of his cock jerk my asshole wider as his cum spurted into me. He kept his cock in my ass until I had come. This time instead of swallowing she kissed it into my mouth, then LadyC had Jake pull his cock from my ass and push it into my mouth to be bathed.

All this occurred while Kay and Teri were watching....adding to my humiliation and pleasure.
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Old 09-17-2008, 10:14 AM   #15
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There was a memorable time for me in the shower with a mini cucumber. On my knees, legs spread wide. One arm propping me up, the other banging the cucumber in and out with wild abandon.

I don't know why it felt so good that one time, but I'm sure the whole house must have heard me even over the noise of the shower.
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Old 09-17-2008, 12:00 PM   #16
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There was a memorable time for me in the shower with a mini cucumber. On my knees, legs spread wide. One arm propping me up, the other banging the cucumber in and out with wild abandon.

I don't know why it felt so good that one time, but I'm sure the whole house must have heard me even over the noise of the shower.
I thought that in Kiwi land you used sheep for relief.!!
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Old 09-17-2008, 06:54 PM   #17
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I thought that in Kiwi land you used sheep for relief.!!
Who told you that?! That's a blatant, slanderous lie!

Except on Saturdays.
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Old 09-20-2008, 03:54 PM   #18
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I was atop Billy-boy ala 69 with pillow over his groin on which I could rest my head while ignoring his cock. I had come once and he was licking me toward a second orgasm when I felt Teri's fingers widening the furrow of my behind, then her tongue was wetting my anus. A moment or two later, he tongue was replaced by one finger, then two which had been lubed in my pussy. When my hole was widened, the fingers abandoned it and Teri's tongue wiggled inside. My orgasm exploded! I don't squirt very often, but that time I did! I soaked Billy-boy's face and filled his mouth. Before I rolled off him, I removed the pillow, put his cock in my mouth and instantly siphoned an enormous flood of semen from him. I rewarded Teri by doing for her what she had done for me as soon as she had mounted Billy-boy.
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Old 09-20-2008, 03:55 PM   #19
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Quote:
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I was atop Billy-boy ala 69 with pillow over his groin on which I could rest my head while ignoring his cock. I had come once and he was licking me toward a second orgasm when I felt Teri's fingers widening the furrow of my behind, then her tongue was wetting my anus. A moment or two later, he tongue was replaced by one finger, then two which had been lubed in my pussy. When my hole was widened, the fingers abandoned it and Teri's tongue wiggled inside. My orgasm exploded! I don't squirt very often, but that time I did! I soaked Billy-boy's face and filled his mouth. Before I rolled off him, I removed the pillow, put his cock in my mouth and instantly siphoned an enormous flood of semen from him. I rewarded Teri by doing for her what she had done for me as soon as she had mounted Billy-boy.
That's hot.
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Old 01-18-2011, 05:07 PM   #20
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I have two favourites.

Th first is when my wife used a strapon on me. I loved the feeling of her body and breasts on my back when laying on our sides while being penetrated. Then on my hands and knees feeling her grab my waist and pound me. A hugely intimate experience!

The second is a little 'out there'. I can put my own dick in my bum. T ne of the first times I did this I had the camera set up through the tv to watch and it didn't take long for me to cum in my own ass. I then watched as the cum dribbled out.
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Old 01-18-2011, 10:06 PM   #21
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My best time was the first real cock I had inside me. I am a bi total bottom. I have a friend with benefits that I visit once a week and he is a very dominate top. one day when I showed up he told me that I would be taking care of his cock along with a friend of his. (My first threesome) . Up till that day I had only sucked his cock. After I had sucked them both to full hardness, my friend took my anal cherry while i continued to suck the other guy. Man it was soooo wonderful to feel him inside me with a cock in my mouth. Anyway, after my friend came. they spent the next three hours taking turns in my ass and in every position you could ever imagine until they could not fuck anymore.

does it get any better then that
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Old 01-19-2011, 05:48 PM   #22
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Quote:
Originally Posted by chrstn View Post
I have two favourites.

Th first is when my wife used a strapon on me. I loved the feeling of her body and breasts on my back when laying on our sides while being penetrated. Then on my hands and knees feeling her grab my waist and pound me. A hugely intimate experience!

The second is a little 'out there'. I can put my own dick in my bum. T ne of the first times I did this I had the camera set up through the tv to watch and it didn't take long for me to cum in my own ass. I then watched as the cum dribbled out.
HOT HOT HOT
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Old 02-01-2011, 12:54 AM   #23
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I've had plenty of great anal experiences with women, but a thread like this one makes me think of my own ass , and for that reason I'll say this -- I truly believe my best anal experience still lies ahead, and I imagine it may well involve another guy.

I'd have to say that the most memorable toy experience -- though not necessarily the best -- was the first time I got off with nary a touch to my cock. I'd always felt this was possible, had actively sought it, and in the process had had plenty of very satisfying solo sessions centered around ass play.

but somehow, in spite of all the thrills and chills there had never been any spills. to climax I'd always resorted to a wank. how and why that changed is hard to explain. putting it simply, I can say a big part of it was that I found a super relaxed position and motion that really turned the trick.

it was a pretty long, slim dildo that time, maybe 6.5 - 7 inches, and I'd suctioned it to the closed toilet seat and was working back and down onto it in what I suppose you might call reverse cowboy.

I'd been going a while, had tried some other placements, positions and angles, when I suddenly realized I was feeling something completely new. the stimulation was intense, the kind of thing that might cause you to bail. but I didn't. I just kept moving, letting my body feel the flow and move in ways to wring more pleasure from the moment. very soon I knew something amazing was about to happen. then it did. I'd never felt anything like it; it was a full body event, for sure, but also quite nearly an out-of-body thing. once you know something like that, you don't forget it

you cannot unlearn an anal orgasm.
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Old 02-01-2011, 01:44 AM   #24
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I know a lot of us here enjoy Anal Stimulation. So let's hear it what was your best Anal Experience?
The day I got my bad boy prostate massager.

Holy moly. What an extraordinary feeling.

Think i might have a play again later
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Old 02-02-2011, 01:03 AM   #25
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During my misadventurous years as a bi married guy, I was in New Jersey on business and connected with a tall, good-looking younger guy via good old Craigslist. We got happily naked in my hotel room and he got between my legs on the bed and started sucking my cock and balls and occasionally licking my ass (which I adore). I'm sort of a versatile top so I figured I was going to get a lovely blowjob and that would be that.

He got me hot and hard for a while with his mouth. Then he slid up on his knees and pushed my legs up in the air. He took his hard cock in his hand and started rubbing the head against my cock, taint and balls and really talking dirty about the first time he was fucked and how great it felt. He just kept talking in this rumbly, sexy voice and barely tickling around my anus with the tip of his cock. It kind of took my breath away...it was a very hot moment.

Then he started to just poke my taint and my ass over and over again with the head of his cock and bump my prostate a little every time. Poke, poke, poke. I started leaking precum like crazy. This went on for probably 10 minutes and he talked quietly to me the whole time about how nice my ass was and such. It was exquisite torture.

He kept saying "I want to fuck you" and "I want you to feel my cock inside you." I remember just kind of feeling delirious (prostate stimulation will do that to you) and finally saying, "Then fuck me."

And he did...bareback (which was stupid) and slow. I honestly don't remember if we had lube or not but he took his time and it felt amazing. He kept talking to me the whole time: "I knew you'd like this the moment I saw you" and "Your ass is so fucking hot" and such. Not only was I being fucked for the first time but he was making love to me.

It didn't hurt (and it never has caused pain even with bigger guys who fucked me later) but it was a mind-blowing feeling. I was on my back, legs in the air, hard cock filling me totally and then being completely out of me for a long, long second, hitting my prostate with the ridge on the head of his cock every time and the whole time listening to him tell me how much he loved fucking me. I was being royally fucked the way I'd royally fucked so many women and I really got off on it.

He finally got close and pulled out and came -- hard -- all over my stomach and chest. I remember him rubbing his cum into the hair on my chest and laughing about the look on my face. It's funny that I can remember that but I honestly don't even recall if I came myself during or after. I do remember my ass buzzed pleasantly through an entire meeting in Philly the next day and on the plane ride home that night.

What made it special wasn't just that it was my first time to be fucked. What made it special was that it may have been the first and only time in my life I was well and truly seduced.
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