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Describe your first time anal

Hell, I'll give this a go, even if I'd never really talk about it elsewhere >.<

Well, my partner had already tried it before and spoken of it in pretty negative terms, but as people who like to experiment, I remember after being together for a long time she suggested it, to my shock as you can imagine. It's a little more difficult to really get in in my experience, always, ALWAYS use lots of lubricant, and I use a condom for sanitary reasons but that's just me. Warm up to it. It felt good in a mental sense as I couldn't believe what was happening :') But it was slow going, I wanted her to be comfortable, and it's not exactly something you can rush. She didn't particularly enjoy it, and after a while we gave up because she clearly wasn't enjoying it, and I don't see the point if it isn't good for both parties. But we both wanted to try it again, and she started using toys and a plug to get used to it.

I remember the first "proper" anal sex as I count it as incredible, I'd taken her from behind while we watched a movie, and all of the slipping and sliding had me poking her. She whispered the suggestion that I try again, and with a lot of lube, I sank right in. I prefer vaginal sex personally, there's this warmth and wetness, and if your partner can flex her pelvic floor it's just insane. But anal is distinctly tighter than the vagina, and I think it has this mental appeal as you know it's unconventional, you know not every woman will let you do it, it's the hot rush of being trusted and being able to really push what can be done sexually. I find anal gets you to climax faster, as the tightness doesn't let up, and when you're that comfortable and really thrusting it's this kind of lock in that doesn't let up, like the rush of someone riding you without an inch of letup.

I was lucky, found it pretty great personally, and to my amusement, found out that more women are open to it than I previously thought. So that's my take, had no idea this would be the first thread I reply to :')
 
I'm a 31 year old gay guy, the first time I received anal sex & subsequently lost my virginity hurt like hell, so it was disappointing & not a day I look back on fondly haha, I was hoping it was going to feel amazing. The pain put me off receiving for a long while but over time as I talked to other gay guys about it and gained sexual experience with them they showed me it's the type of lubrication that is the key to minimising the pain to nothing.

When I was younger I used crap lubes - that went sticky too quickly & so there was too much friction in my butt causing a lot of pain. What I have been using for a long while now for anal sex is cooking oil. Yes seriously cooking oil - olive, canola etc......any of those works just fine but first rub plenty on and in your hole & then make him apply it on his dick............. It doesn't have to be extra virgin oil either! I don't have any pain now & really look forward to getting fucked, his cock slides in and out a lot more easily. There's nothing quite like a dick rubbing on my prostate as I am about to cum. And the orgasm is just insanely good. ;):)

Also it's good to know he isn't worrying about putting me in any pain so he can just focus & enjoy fucking me while I lay there.
 
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I was about 17 and I had no idea what I was doing.


It's old hat now. Some foreplay and then just enough crisco to coat the head and most of the shaft is plenty to get things done right.
 
CoastTwoCoast said:
Cooking oil, eh? I learned a new tip for future anal adventures. Cheers!
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No problem. Cooking oil has worked a lot better for me than any water based lube I have used. And I have tried many! Not sure whether you are a man or woman but the giver needs to make sure he doesn't just quickly thrust his dick into him/her. He needs to slowly put it in so it gives the oil the chance to get spread out inside the receiver and then he can build up to a faster speed. It's worked so well for me! :)
 
Jason1985 said:
No problem. Cooking oil has worked a lot better for me than any water based lube I have used. And I have tried many! Not sure whether you are a man or woman but the giver needs to make sure he doesn't just quickly thrust his dick into him/her. He needs to slowly put it in so it gives the oil the chance to get spread out inside the receiver and then he can build up to a faster speed. It's worked so well for me! :)
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Cool! I'm a woman. Haha I had a painful experience with someone rushing like that in the past, but an experience from the beginning of the year went smoothly. The guy definitely needs to take his time.
 
no condom was my first time
with a random chick, being drunk

Just Being Young : )

No consequences like HIV taken, btw
 
I'm a man, 34 years old. First time I had anal sex was when I was about 18, g/f was 17. I really fucking wanted to do it and definitely pressured her by mentioning it over and over. I did a bit of finger play during sex and she seemed to enjoy it, so I pushed for it even more. I do feel a bit bad that I pressured her but we were so young, I didn't really think about her. :\ I never tried entering her without her asking though.

Anyway, one day she came over after school, house was empty, we were making out and she shyly asked me to grab some baby oil and fuck her ass. For fucks sake, I was so eager, it was ridiculous! So, she stripped out of her school uniform (!), bent over and I lubed her up (this has haunted my dreams). I did a bit of finger probing but didn't really want to wait so I poked it in and it really fucking her hurt. I could only penetrate a few inches before she would stiffen and show signs of pain, so I pulled out. She wanted to continue but just instructed me to only enter very slowly and shallowly, which I did and it worked. We both enjoyed it (well, I fucking did, and she claimed too) and I loved being able to come inside her with no fear ofanything living coming back out :)

We had more anal over the next few years and eventually I could pound her as hard as I wanted. Usually, after I came in her and pulled out, her breasts and neck would get all flushed and her pelvis would start to shudder. I could basically brush her clit and she would cum insanely. I guess she could have been faking it all as she was a chronic liar and would say/do anything to please me. She was a beautiful and sweetly compliant young girl. I was a prick to her to be honest, just used her in many ways. I am sorry for that :(

We had a few rather messy anal sessions which certainly lessened both our appetites for anal but figured out when the best times to do i were.
 
Well I was really horny and was fucking my ass with a dildo I found in my moms drawer in the shower. I used lube and cleaned myself and enjoyed it and felt ready to finally be fucked in the ass. I texted my Bisexual friend who is dying to fuck me but I haven't been ready. He came ASAP. I was naked and wet from the shower and I had the door open for him already. He came in to seeing me on all fours with my ass up waiting to be fucked. He came to me and whipped his cock out and shoved it down my throat. He was making me tear up and gag but he needed to get super hard. He then just put on lube and didn't use the condom I left for him. He lubed my ass up and then slowly started to insert his cock in me. He slapped my ass and demanded I call him papi. He kept going in slowly but gradually going in deeper and faster. I started to moan uncontrollably as it was so painful but so amazing. He kept fucking me until he was almost about to cum. I told him to let me know so I can turn around and swallow him but he said "Shut up! I'm breeding you my son." He came all inside my ass as he shoved his cock deeper in me and pushed me down so I couldn't stop him. He then pulled out and made me clean his top off from the cum and his dick tasted like my ass juice. I then farted out the cum onto his hand as he made me slurp up the cum that was inside my ass and made me swallow it. He then made me lay down as he made me clean off his balls, taint and for his own fun, his ass as he took a nice shit before coming in. He sat on my face as he was trying to get hard again. I wanted to get up but as soon as he got hard again, he held me down so he can fuck me in my face. I started to really get upset and say no but he said I would love it and he shut me up with his cock. He fucked my face with no care for me tearing up and gagging and throwing up a bit. He then turned me over as he was about to cum again and shoved it inside my ass and came inside again. At that point I was so used I couldn't get up. He just zipped up his pants, and left. He then later sent me a video from his phone that he took during the whole thing. I loved it.
 
Don't mean to sound like a creep but I've been jacking off for over an hour reading all this.... It's hot as fuck!!!
 
My first time was one of the worst experiences of my life. I was a teenager and it took me years to recuperate from the shame. I was 16 and didnt have much knowledge on the subject. I went on a weekend camping trip with my boyfriend. Started drinking prior to leaving. Cheap vodka mixed with sugary bug juice. We stopped at burger king on the way. I am not and never have been a fan of greasy fast food. I had been working all day and didnt eat. I inhaled a whopper and ate fries washing it down with vodka and bug juice. I hope you can see where this story is going. Lots of friends were with us for privacy got in the back of his car. Small enclosed are summer hot and humid. I am not going to write out the rest. If I knew then, what I know now lol.
I did learn the dos and donts of preparation for that. I was 30 when i finally tried again. Much better this time around.
 
First time? Damn. I can't remember that far back.

While I'd like to say it was unforgettable, I guess I'd have to say it was actually forgettable. :\
 
my first anal

The first time I had anal sex was with my current wife. She has always had a very wet pussy, sometimes so wet her juices drip down her crack. On that night we had both been drinking and alcohol magnifies how wet she gets and how horny she gets. We were fucking missionary when she swiveled her hips and my dick slid out. I didn't think anything about it so I went back inside her and it wasn't long before it happened again but this time she raised her hips. I had never done anal before so I didn't think anything about it but was confused by her teasing. I went back inside her a third time and almost immediately she popped me out again only this time she moved so the head of my dick was lined up perfectly with her asshole. The closest I was to buttfucking before this was an ex who dared me to put it in her butt but started screaming for me to take it out before I could get the head in so I thought the same would happen here and I would have called her bluff. I started pushing my dick in her ass and when the head popped in I stopped waiting for her to tell me to take it out but she didn't. I thought to myself "ok it's just the head but she won't take the rest." A few pumps later and half of my dick was in her ass and I stopped again. I thought "don't fuck this up by hurting her; there's only pussy juice as lube and she probably wants to adjust." About that time she started doing little fuck motions getting impatient with me stopping and starting. I got the hint and took over fucking her ass with small strokes getting more and more of my dick up her ass until her magic asshole opens up and I'm fucking with long strokes. She's moaning and I can't believe she can take this kind of pounding in her ass when her anal orgasm hits. Me being new to anal with her I continue fucking her like I was before. That's when she starts moaning "cum" over and over and it makes me hot hearing that so I start fucking her as hard as I can taking my dick out until just the head is in and slamming back into her. Her moans of "cum" getting more distressed when I slam my dick all the way into her and start cumming harder than I have ever cum in my life. I cum so hard I arch my back and close my eyes while I'm shooting inside her. When I'm finally done shooting my load inside her I start to wonder about the protocol for exiting the exit hole. She wanted me inside her ass as fast as possible, does that mean I should get out as fast too? I decided to let her take the lead. My dick stayed super hard for longer than normal inside her ass so I started clenching and unclenching making it spasm and she responded by clenching her asshole. I started to back out of her but she stopped me which was fine because I was staring at the sight of my thick dick stretching her asshole with her pussy dripping right above. After what seemed like an eternity my dick started to soften and as it did naturally started backing out. When only the head was left I pulled out of her with a gasp from her. I didn't know what to expect after I pulled out but was pleasantly surprised to see I was only slimed and not stained. In the 20 years since this first assfucking I've only gotten dirty a few times and she never prepares for anal. To this day we don't use any lube other than her pussy juice and I've only fucked her to more than 2 anal orgasm once. When I still had not cum after the second one she made me was her dick and fuck her pussy.
 
Received, spontaneous, hated, agreed because I was stoned, and couldn't wait for it to be over. I did not have an orgasm, he made such a mess I couldn't take laying there and had to shower.
 
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