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Describe your first time anal

First time anal M/F - was ok, was not planned but seemed to move into that direction - she wasn't that into it and felt she was doing it simply to please me which sort of turned me off (I could sense she was uncomfortable) so we stopped Anal and continued having fun.

First time anal M/M on the receiving end - amazing experience, was planned. Guy was a really sweet older bi (married) hairy chubby guy (bear) - he was really gentle, knew what he was doing and took enough time making sure I was ready. It was mega intense, a bit robotic but didn't OMFG that hurts / stop now etc - he came really quickly and left (as expected) I did not come but felt really satisfied.

First time anal M/M on the giving end - amazing experience, not planned. Was with my regular FWB, was giving him a massage and started kissing his neck, his back, sort of moved down a bit further and he seemed to be really enjoying it. Slipped a finger in and he again gave all the signals that he was having fun, moved on a bit further and - phew, grunting hairy beary sex followed. We both came, I came deep inside him (safe) he came shortly afterwards.

Not in the first question but - First time cumming from Anal (and repeated so many times), cowboy style - looking into his dark brown eyes, kissing him, feeling him etc then I had 'that' feeling inside of me - then out of nowhere busted all over his chest :D.
 
Pagey said:
It genuinely makes a very very big difference. Too big just doesn't work for anal, or at least takes more getting used to. But as I said, don't give up on it!
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<3 thanks!!! bf is comin end of the month so I guess this is somethin to consider lols
 
My first time was in a shower with my girlfriend's (now wife) vibrator. She had gotten a new one and I was bored and horny and decided to try it on me. What I didn't expect was how difficult it was to bend and push. It didn't hurt much but I gave up after a couple of mins because it was too much work.
 
She was drunk. Felt good for me as a giver. I was pleasantly surprised. Miss slow cummer was cumming unusually fast this way which excited me even more.

In college, a girl stuck a finger in my ass during a blowjob. Stopped her after about 30 seconds or so. I was too freaked and too immature to be able to enjoy it.

Still not my thing. Had a girl who knew what she was doing give me a rim job and some TUMA (tongue up my ass) after I had gotten a Brazilian wax. When she is confident in what she is doing, it feels good.

Still don't want anything else up my ass. Don't like it when the doctor has to do it to check my prostate.

It's a spontaneous thing as a giver, but the first time you bump into a turd, it scars you mentally.
 
Giving, at university to an elderly OU student. Receiving, in a park in Southall, receiving was just a little large for comfort. Regularly do it both ways. Giving with out a condom too often results in pipe infection
 
I was fucking this goth chick I met at a bar and she had mentioned earlier she was into anal, so I just stuck it in her ass. She was ok with it and her pussy was really wet so it went in easy. I fucking loved it. It felt so good. I did her in the ass the next day with no condom and hit up the shower immediatly afterwards. I wanted to hit her ass raw cuz it felt so good with a condom on. Looking back it was probly not exactly safe to ass fuck some random slut but Im ok so far. Ive since then fucked every girl I could up her poop shoot. Sometimes I just like to finger a woman's asshole a bit when shes sucking me off. But yeah I dont think I would like it in my ass. But yeah I love to give it to a woman up her ass. I can understand however how they may not like it and being the gentleman I always ask first and if the answer is no, I wont stick it up her arsehole.
 
OMG this is so sad I can barely remember my first time receiving anal. I had just came out at age 22 and I had to get drunk off my ass to even go into a gay bar... 4 hours later I was black out drunk but I do remember how bad it hurt and how hot this guy was so I just gritted my teeth and took it. Since then I have mostly been a top!
 
Cadamec said:
She was drunk. Felt good for me as a giver. I was pleasantly surprised. Miss slow cummer was cumming unusually fast this way which excited me even more.

In college, a girl stuck a finger in my ass during a blowjob. Stopped her after about 30 seconds or so. I was too freaked and too immature to be able to enjoy it.

Still not my thing. Had a girl who knew what she was doing give me a rim job and some TUMA (tongue up my ass) after I had gotten a Brazilian wax. When she is confident in what she is doing, it feels good.

Still don't want anything else up my ass. Don't like it when the doctor has to do it to check my prostate.

It's a spontaneous thing as a giver, but the first time you bump into a turd, it scars you mentally.
Click to expand...

I got remarkably turned on when I hit the shit. It really turned me on. It added some friction. I probly shouldnt have came in her pussy after sticking it up her ass. She ended up going to the hospital with a nasty infection. Still didnt break up with me or stop giving me her asshole.
 
I kinda wanna try this so a few questions.

Best way to prepare so I'm not in horrible pain, or worse yet rip! I've had my ass rip (not from sex) n had to have surgery. Worst pain ever!!

So, lots of lube right? Start with finger(s), toys, then his dick?

I kno being relaxed will help a lot!

N, a rumor I heard in my teens, is it safe for a man to cum in ur ass? This would b with my fiancee of 5 yrs so we don't use condoms.

I really wanna try but after havin ass surgery I'm nervous as fuck!

Please, any tips or advice I'll take!!
 
Err, do you have scarring from your ass surgery? Scar tissue doesn't stretch very well....
 
Ah ok. It might make things a little more uncomfortable, and he'll have to be gentle, I'd say.

For sure lots of lube, and try to be very relaxed! A lot of people hate the feelings of fingers up their butt, myself included. You could try it and see how it goes. A toy is a good way to get started. Then when it's time for the main event, make sure you are very, very relaxed and very lubed up. He should go in gently and slowly, and sometimes it helps if you bear down, can make it more comfortable.

If you guys aren't using condoms anyway, I don't see what harm it could do for him to jizz in your ass.

My ex was really large, and I used to prep by doing shots of rum and taking muscle relaxers and stuff. LOL didn't really help much, tho.

Good luck, and have fun! <3
 
For your first time I would not suggest any pain killers etc - Pain can be a sign of something is wrong and if that natural defense is blocked then you could end up hurting yourself.

Lube, finger, fingers after the initial play you will feel your ass muscle relax a little bit, then move onto something else. Being in control of the situation may make you feel a bit more comfortable and relaxed so you sit on top, go slowly give your body time to get used to the feeling before going lower/deeper. Pushing out (like your going to the toilet) as you sit on him can make you open up a bit easier - once in you may get the feeling that you need to go to the loo, its normal so don't worry. Depending on how big he is, you actually have another muscle deeper in your ass that needs to be nudged a few times before allowing entry. Just go slowly :)
 
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