Best time you had anal? (I don't care who answers: male, female, etc.)

Bet after writing this you had a big wet spot .

 

Best time I had anal, was in threesomes mmf and mmm

 

Several years ago i got involved with a friends GF, they'd been together for many years and had very little experience prior to each other, they were in a slump and decided to expand their sexual horizons, our first time together was in a threesome, i had a great sexual connection with her and things just flowed. Afterwards they decided they'd give an open relationship a try, me and her started hooking up more regularly. We were hooking up one night, we'd already fucked once and were working up to a second time when she asked if i had lube for anal, i knew for a fact she'd never done anal and asked if she was sure, she told me she was sure and she'd always wanted to try but after one failed attempt years before where he couldn't get it in he'd never shown any interest after that. I'd talked about anal before and she said seeing as i had experience she wanted me to be her first, cause if she could handle me she knew she could handle him, i was more than happy to be the one so i lubed up and started her out with a finger and she confirmed she still wanted to take me, now at 7 long and roughly 7 around i'm anything but small so i didn't expect to get much more than the tip in before she tapped out, with her face in a pillow and her ass up i pushed myself in, i gave her a minute once the tip was in and waited for her to give me the green light, i eased in as she moaned into the pillow and white knuckle clenched the sheets, once i was all the way in i stopped, she asked me to keep going, i told her i was all the way, she looked back with a grin and asked for a minute, she gave me the go ahead and i began thrusting slowly, as she began playing with herself, i let her call the shots and paced myself accordingly, once i started to fuck her at a decent pace i knew i wasn't going to last cause she was incredibly tight, fortunately i didn't have to hold off long, her orgasm hit and sent me over the edge at the same time.

few weeks later buddy mentioned he'd popped her anal cherry finally, i guess she hadn't told him and well i didn't have the heart to tell him i'd actually already broken her in

 

OMG! The intensity, thoughts of being caught, and adrenaline had to be through the roof!! Sex in public is nothing compared to that lol.

 

Was that the one and only time, with the wifey not ever finding out?
You would have thought that she would have taken the middle, for playing it safe.
Unless of course, this was all pre-planned...

 

Well, I previously posted my "best" anal experience, now I'll post my most infamous.

It was when I was dating my husband. We both awoke on a Sunday morning, somewhat hungover from the previous night. We started to fool around a bit and fondle each other.

Next, he climbed on top of me, and started fucking me in the missionary position while fingering my asshole. Then, without any warning, he pulled out of my ****, and went up my ass. I was surprised, may have whimpered in pain, but didn't stop him. He continued until he climaxed in my ass. We engaged in anal sex quite a bit back then.

So, after that, for years, he "slut shamed" me about the time he fucked me in the ass, with only my on juices as lubricant.

 

Sounds like some of you ladies need to be carrying around your own lube and for having it in easy reach, for these back door surprises ....

 

Faaa that’s hot

 

LOL.....and look where that got her......or got you, actually!
So, she never found out?

 

Damn that's hot for sure and the only thing for more, would have been with you crying out and for waking her up, to catch you both in the act...

 

Slow fucking can be the best at times and especially if it's for fucking her mouth.
Slow and gentle like, until the cum begins to spurt and flow...

 

Damn girl, you're about to have some cumming going on without even seeing your ass.
Ummmmmmm, seeing your ass. Now there's a thought.
Speaking of your ass, you actually orgasm-ed from it, or was it for having your clitty rubbed, during it all.

 

Which begs the question of how many women can actually do that.
How about it ladies, anyone?

 

Well, you must have been very "accommodating" there.

The artist formerly known as Mistress Margaret.

 

My favorite time was at a swing club outside of Chicago many years ago. My wife and I had been there many times and I was feeling more aroused than usual.

Instead of being partially dressed I went completely naked, nothing but a red face. Most people were fully clothed maybe twenty percent topless or bottomless. A lot curious people.

My wife wore genie pants and nothing else, she found a guy who wanted to fuck anyone in anyway in front of everyone. I gave into the situation, I had been walking around naked in front of everyone for an hour by that time, I had let a few people fondle me while we chatted.

Standing one foot on the floor the other on a sofa I let him lube me in front of at least two dozen people. That was extremely exhilarating and for a moment I began to feel like that was enough and I didn't think I wanted to continue.

At that point I was aroused and embarrassed in equal measure, so I didn't walk away and gave in to the situation and let him fuck me with an audience watching. They cheered when he reached around and jerked me off.

That was the best.

 

To cum in a married woman's ass while her husband watched, and especially when she demanded it is truly a great experience

 

My favorite was the first time my fiancé and I had anal. She’d said she’d done it before with her ex husband but she didn’t like it…..he was clumsy and didn’t do anything for her. Our first time involved a lot of anal foreplay and she really got into it. Her anal only orgasm was incredible. Only woman I’d had anal with that came that way……no additional stimulation needed.

 

The first time..
the sight of her empty pussy, as I was fully inside her anus was too much for me

 

Of my four women experience with anal although the first three were better than the fourth, I still am partial to my first time with my first wife when she was 19 and she wanted to try it her first time too, having heard stories about it. There wasn't a lot of choices for lube then and all I could find in the house was vegatable oil so we went with that. She held her nice asscheeks apart poised on her knees with me behind her. Vegatable oil was dripping down over her pussy as I put my head to her tiny puckerhole and after a few attempts pushed with more pressure and I heard a little snapping noise and my head was in her ass. She clutched and screamed into her pillow as I eased in a little at a time until about halfway in she stopped me and I fucked her that way till I throbbed it full. She collapsed face down and layed there sobbing into her pillow with her legs quivering.

 

it was new years and i was in a nightclub. i was at the bar ordering drinks but the barman said someone had paid for them and pointed to a guy. the guy came over to me i thanked him. next thing he took me into an office. whipped out his cock next thing i know im sucking him off, then i fucked him in the ass. as soon as i came in him, he said right my turn. had me over the desk. shoved his cock up my ass and fucked me until he came inside me.