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Describe your first time anal

1st time giving was with my ex, she had done it loads of times before & was used to it, started by giving her oral sex then working down & rimmed her for a while, after a bit used myfingers with loads of lube to get her ready then when I had worked up to 3 fingers she went into doggy style & we had bum sex.
I wil admit this here as I don't really care, i've had buttplugs used before quite a few times & it makes me cum very hard. The 1st time she tried to stick a dildo in my arse which I wasn't pleased with at all but over time I began to trust her again & she used a vibrating buttplug while giving me a blow job which worked very well.
 
I was drunk with my girlfriend at the time. After about 30 - 45 min of fucking her from behind, I tried putting it in her ass. It hurt like hell regardless of the buzz, and I could only get part of my head in. Not fun. Titfucking on the other hand is amazing.
 
I know legit 1 guy who does deserve a 6 inch dick up his ass with no lube roughly, but jesus man thats crazy, this bloke slept with my mrs, idk what she did to you but damn man that is brutal!
 
she stole from me and talked shit about me constantly you'd have to know here to realize it was not a bad thing i did all my friends also hated that bitch
 
Tried anal once, we were drunk, she grabbed my cock and said something like, "eeyar, try it in me ass." Then she was like "arghh, dafooq". Then we just carried on with vaginal sex. We never even talked about it again, just never did it. I'm not that bothered because, when I was 15, my school mate shagged is girlfriend up the arse and said he got shit all over his cock and on his mum's couch. That put me off a bit.
 
something I HATE but my husband loves. So he gets it twice a year, on his birthday and one other day of his choice.

Unless I want something really bad. Its a great bargaining tool....
 
I know I'm a little late to the party, but here's my story.

I've been with my bf for 14 years. He's always wanted anal and I always said no. He hadn't/hasn't been paying me much attention, so I started fooling around (mostly just mutual masturbation in a feeble attempt to avoid "technically" cheating on our respective partners) with a guy on the side.

One thing lead to another and he started playing around back there. It felt unbelievably good and it made me cum really hard. When my bf plays back there, he usually plays for 30 seconds and then immediately wants to shove something in there (which I hate). Fast forward a little and now my second guy is using a vibrator or dildo in my ass and he even stuck his cock in there a few times. Since my second guy is smaller than my bf, I figured that I would get used to him fucking me in the ass (which does make me cum if I play with my clit at the same time) before I spring that pleasant surprise for my bf on his birthday or something.
 
My first time taking it was when I was 19. I was seeing a guy for whom it was a big deal so I "Did it for love". My arse was tight, I was uptight and truthfully I never really enjoyed it. A few years later though I picked up an Indian guy who also wanted to fuck me and that was a different story. Had my legs up on his shoulders and fucked me face to face and it didn't hurt at all. I had the most amazing orgasm and remember hitting the headboard with my cum I was so turned on. Don't know what he did differently but it definitely worked.;)

Might not have been the first time I was top but I remember fucking one guy, lying on my back with him sat on me and feeling his pulse through the head of my cock....That was quite intimate but unfortunately he turned out to be a bit of a dickhead which soured the memory. Another time I fucked a guy in a sauna in New Zealand and he wanted it really forceful. Took me a little while to get into my stride but that was pretty intense as well.

These days I don't do anal either way unless I feel a connection with someone. If I do it though, everything has to be clean. If I'm expecting to be fucked, I'll douche first and if I'm going to top someone, they need to do the same....The smell of poop is a real turn off. But equally, a guy who takes the time to be clean is a real turn on.:)
 
I was pretty wasted (as usual) at some club I got into with a fake ID....the guy was all tatted up, and about 10 years older than me. We went to Denny's, then to his place. I thought we were just gonna fuck "normally", but he turned me over and told me to relax...then he put his dick in my ass. It wasn't bad...probably because I was wasted and he was really hot.
 
I just had anal for the very first time!
Neither my husband or I had ever tried it before, but I wanted to try something new and had been reading up on it. We used plenty of lube. In his inexperience, he pushed really hard trying to get it in the hole, so when he rammed it home, it did hurt at first (kind of like someone pinched my asshole), but once he was in, it was smooth sailing. It wasn't bad at all! I was expecting it to feel much more intense and stingy than it actually does. At one point I even asked him to go faster. All in all, I'd say it was a good experience, and I'll definitely want to try it again. I spent so much time being nervous about trying it just to find out it's no big deal.8)
 
i have had anal sex well over 100 times (or more) and it still fucking hurts. i always use LOTS of lube and the guys are usually not too big..normal sized thickness. can someone answer why does it still hurt if i have done it soooo many times?
 
skittlesxo said:
i have had anal sex well over 100 times (or more) and it still fucking hurts. i always use LOTS of lube and the guys are usually not too big..normal sized thickness. can someone answer why does it still hurt if i have done it soooo many times?
Click to expand...

You may have an anal fissure ? Maybe your just not that 'into it' and do not like the feelings it brings? It should not 'hurt' - it can give you pain but not in a way that you want it to stop, your obviously experienced or I would have said maybe your going to quickly at the start (which can hurt) / try changing positions etc.
 
I was 12 when I had anal sex the first time. Although I had masturbated to orgasm experiencing orgasm through anal sex was different for me then. My virginity was taken my an older 16 year old. I remember the sex and the orgasm I reached very well. I had expected pain but there no pain when he entered me. I just remember pain when he thrust deep. It was years later when I had anal sex again. I was 24 then. I noticed a man looking at me several times one night at a bar and he eventually came to speak to me. We talked about one thing and another and we ended up going to his apartment. I was and wasn't expecting sex but one thing led to another and I was in a bed nude with a man for sex for the first time in my life and 12 years since I had had sex with another male. I was expecting and wanted to receive him anally. There was foreplay, touching, tasting, and probing. He wanted to take me but I think he wasn't sure if I wanted to be taken. I remember he timidly started by touching my anus with his finger but not actually penetrating. I had some lubricant and once I gave it to him there was no doubt. It was different and exciting to have another probing me back there after so long but it felt good. He went from finger to penis after what appeared a long time. I can remember vividly when he entered me. Filling and exciting is all I can say. No pain just pleasure. He thrust slowly at first but but soon got the rhythm right. It lasted a half hour. I was reaching for every inch and he was giving me every inch. I reached orgasm as I hadn't ever before. I exploded and he exploded seconds after. That's my second time but really the first because it was sex as an adult, pleasurable, and memorable.
 
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