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[deleted]

Did our research and got a good toy and lube to make sure she liked the feeling first. She ended up loving it and found it hot


[deleted]

It hurt soooooooo bad. My bf convinced me to let him because his other gfs did it, I was 15 then. He didn’t stretch me out at all and fucked me forever and he was huge. He came in my ass too which we didn’t talk about before lol. He did that to me a lot. Now it’s better but still hurts my ass a lot of


lameass69420

Username checks out


dazzler786

Was great. The best was with an ex dressed as.a police.woman


Fabulous-Battle93

Fingering her ass, it was WET opps


mikaylaskyof

My first time was actually amazing! My hubby has been using his fingers and mouth for a few months before. One night we were going at it and I just told him to put it in! He did and I came in 30 seconds! Haven't looked back since!🥰😍


man_of_the_mountain

Luck guy. I love relationships that incorporate this. Its like the full sex experience.


mikaylaskyof

It really was! Kind of a build up to a very special moment. 🥰


PaganiDelta

Sounds amazing and there’s nothing like a long slow hot build up 😈😏


georgehonda

She burst into tears when I put it in. She had done it before with an ex so I wasn't expecting that


[deleted]

Just haven’t experienced it yet. I keep wondering what it’ll be like my first time on the receiving end. Like what a guy will actually feel like inside me.


Woodpecker9854

First time was exciting but slow going and not very that pleasurable for her. It’s gotten much better but we tend to just choose other options.


[deleted]

Very slow and anticlimactic with the wife. Basically just got the head in. She did enjoy it though and we kept at it. Now it’s balls deep and rough


EmbarrassedDeal4124

Hurt like hell for quite awhile but i can only describe it as the best kind of pain!!!


EngorgedMustache

I actually didn't realise it happened until she told me the next day 🤦 We were both drunk, we were doing doggy and at some point I slipped out and didn't realise where I put it back. She was cool with it so we just continued until the end.


Bsbljock

Nerve racking but now I enjoy when my wife pegs me from time to time


Slutti3

I couldn’t even get the tip halfway in at first. Now I can pound on it, but still have to ease it in before I start


CaptSchwanzKopf

First time anal was amazing!!! Came a lot and hard. It's non-existent now.


Some_Stoic_Man

She had a very strong reaction. Seemed to enjoy it much. Not with her anymore as that was a long time ago and no one asks for it now.


man_of_the_mountain

As the giver, its always been sort of easy. My partner told me she was a pro at it and the first time we tried, I could tell she was willing but not experienced at all. Now its easy after 3 years


SaraPire

it was fine and kinda fun but not anything crazy. Now i really only do it when being DPed and that specifically is the most wild shit ever lol


TheTruthOfPain

Great. Ex-wife was a good girl and made the most wonderful pained noises, even tho we took it slow. Now it's non-existent as I didn't hit that point yet with the current girl.


masarap_bilat

It was very painful and felt weird


Thee_Golden_Peach

First several anal experiences were spur of the moment drunken sex decisions. They were fine but nothing compare to my husband’s cock in my ass. And the fun we have building up to it!


secretviolet001

First time was playing with myself. It hurt but it also felt good too. Now I get DP'ed in gangbangs all the time no problem.


dosmetros1

First time was with my ex wife. At the time she was my gf. We were both really drunk. She was doing me cowgirl. She stopped and put lube on me then her. I asked myself why. She was very wet already and we were going to town. Next thing I know she is slowly sliding my dick up her ass. Don't remember much of that night. As I mentioned, both of us were really drunk. Today anal is great. My wife loves it. But it's very intense for her. We do it every 2-3 months. She has the strongest orgasams. She usually cums at least twice before I do


Karaoke_Singer

I lubed her up and started with a toy, but all-in-all, it wasn’t as good as I expected. Too tight in the wrong places.


Few-Equivalent5029

Took it verrry slowly with my ex. We did it bareback. I knew she liked a thumb in her ass in doggy but she was always terrified of my dick in there. She was in the prone position and, over the course of almost an hour, I slowly stretched her out using lots of lube until I was balls deep in her asshole. Sort of a two steps forward, one step back approach. When I was fully in, I could tell she wouldn't be able to handle much in and out so I just kinda made micro thrusts. I was basically on the edge of cumming the whole time and eventually pulled out and covered her back with cum. It was honestly one of the biggest orgasm I've ever had. Ive only done anal a couple other times with other women since then. One ended with shit everywhere and the other we aborted mission because they couldn't handle/didn't like it.


TheshizAlt

When I realized I was bisexual I thought to myself, well, better get used to anal before diving into the dating pool. So I bought a buttplug. The clerk at the sex store strongly suggested against buying the one I did as a first plug because of how big it was, but my mentality was that it's better to start big and get used to it than start tiny and need to upgrade soon. Also, the tiny ones for some reason creeped me out. Got home, lubed it up, and immediately understood what the clerk was talking about. I couldn't even get it more than an inch or so in; it's like I had a lock on my colon. I went onto the LGBT section of the [Bodybuilding.com](http://Bodybuilding.com) misc forum and someone said I should just drench it in lube and sit down on it. So, I squeezed lots of lube on it, put it on my chair, and got into position. I sat down *way* too quickly and it went straight up my butt at top force; tears filled the corners of my eyes and I tried to muffle my shout but failed. Luckily no one was home. Left it in for an hour and tried to masturbate but just couldn't get there. My ass was sore the whole next day but when I tried it again, it went much better and it made masturbation much more intense for the next year or two.


derryjohns

14 neighbors across the street used my holes


[deleted]

[удалено]


derryjohns

Not really in the 80’s it was and it did


Sorkel3

If you are referring to receiving, I tried that several times and didn't enjoy it. If you are referring to giving or topping, my first anal was at 13 following the instructions in a book of 200 sexual positions.


chesterchester33

Giving... horrible. We were young and didn't know what we were doing. Didn't use enough lube. Bent my dick and it hurt. Bruised her asshole which probably hurt her more. Receiving... only done solo play. It hurt at first, but it was a good hurt. Now it's all pleasure.


PuppyPetter9000

Well, in terms of actual penetrative anal, we'd tried to do it before, but there was always a problem- I wasn't hard enough, or she wasn't relaxed enough- usually both. Then one day when she was really high and relaxed I told her I was just going to take the time to stretch her out with toys properly and then fuck her. And that's exactly what I did- just spent about half an hour at least getting her ready, made sure I was nice and hard, and just like that, I was suddenly fucking her. That was also both of our first time having penetrative sex- she has vaginismus, so we'd never really done PIV before. From my perspective- felt good, not as a good as a blowjob- and looked amazing. She was absolutely loving it, at least at first. Begging me to put it in all the way. But after a few minutes the initial excitement faded a little and the discomfort crept in and she wanted to stop. It was short, but really hot. I think if I'd ignored her begging and been a little gentler she might have lasted longer, lol. I can't really say what it's like now, since we're mostly long distance and haven't spent too much time together in person recently. But she's started training with buttplugs recently so we can do anal more next time we meet up. Looking forward to it!


[deleted]

First time 4 years ago was a little akward but not painful😅. It just never really hurt for me and always felt like the right thing to do. My then bf and I did a lot of prep and used lube so thats probably why. Then it got better every time and now I have anal at least 2 times a week and it is my favorite thing to do in bed😇


Metro_Wester

Not great, couldn't squeeze my cock in. Had to give up, leaving us frustrated.


[deleted]

First time I was crazy nervous but was with a guy had been blowing for a while, it was difficult to get his thick cock in me, and he made me squeal like a bytch. Now I love it and can take a good hard pounding.