What made you try anal the first time?

[darkknight01]

Same here except hub's finger

Would you like to try it? Or are you fine without it.

 

[FGB]

I was home from work about an hour when the doorbell rang. I answered the door to found a slightly drunk and very horny Lisa, a nineteen year old vixen all over me. When I finally got my tongue back I said "Well Hello!"
"I want you to tie me up and fuck my ass!" she breathed into my ear.

I told her that I didn't know what the hell she had been doing that day, but whatever it was I approved! I stripped her clothes off first, then grabbed some 1/8" nylon 100% braided rope and applied some slip knots with knotted stays.

Basically adjustable nylon rope handcuffs. (Boy scout training paid off once again!). We smoked a joint as I informed her that if I put the ropes on her I was going to do everything that I wanted to do and she was going to get ate and fucked in every fuckable hole she had. Yeah, that didn't exactly turn her off!

So we retired into my water bed and I tied her left wrist to her left ankle and did the same to her right. I blindfolded her and placed a small "G" spot Vibe and some lube on a pillow close by. I raised her ass up a little and place another pillow under her so that I would have access to her pussy and asshole without any difficulty. I told her what I was going to do to her as I moved the the foot of the bed and pressed the head of my dick to her lips. She greedily sucked it in and I slowly with short strokes followed up with the rest. I'm only slightly above average in length and girth which makes me ( I've been told) the right size for around the world fucking. I quickly changed positions into a me on top 69 position for a few minutes before rolling over placing her on top... water beds are great for this kind of stuff! She came with a shuttering, squealing orgasm before I rolled her over and proceeded to fuck her into two more varying speed and intensity.

I let here catch her breath a minute or two before I turned on the vibrator as I slowly ate her out again occasionally dipping my tongue lower, lightly flicking it against her virgin rosebud while drifting the tip of the vibe the length of her letting it rest a couple of seconds on her clit before moving on.

Deciding that I had better get down to it. ( To say I was rock hard at this point I hope is unnecessary!) I lubed up my middle finger and slowly started teasing her asshole by slowly sliding just the tip in before withdrawing and then adding a slight amount more each time. After this stopped causing her to jerk and moan I started in with the "G" spot Vibe. Now I instinctively knew that this was good for only so far so I brought out the mate to it, Straight but with many little bumps molded into it. Well, using that on her ass and going down on her caused her to damn near pass out!

I decided it was time, so I lubed up and slowly inserted the head of my dick into one of the tightest and hottest holes I have yet to run across! Hearing her moan and softly oh, oh... I asked her if I was hurting her and if should stop?

She said, shaking like a leaf, that if I did she would probably kill me!

Taking that as an order to stop screwing around and fuck her, I slowly started going deeper and faster until I spanking her with my thighs.

Damn. I held on as long as I could at that pace; meanwhile she was cumming in the longest orgasm I have yet to experience in a woman. Meanwhile I was pumping away like a runaway locomotive...Eyes crossed, breathing hard...It felt like my soul flowed out my dick into her I came so hard. Everything turned red and when I was aware once again, I was still buried in her my arms wrapped around her and faces were cheek to cheek.

She asked me if I was OK, I said yes, how about you? She said great but she needed to go to the bathroom and clean up. I laughed and said that I would go with her too after a few minutes.

So that was my and her first time to have anal sex. Later she told me that she had been watching Porno's all afternoon and that the anal sex scenes made her want to try it and that I was the only man she trusted that much. She thought that since I had taught her everything else about sex that I was the man for the job!

Damn! I loved that woman. (RIP)

 

[PantyPlay]

And did you enjoy it the first time?

Also if you're fingering someone anally-or yourself-do you ever feel stuff up there you shouldn't? Is that common? Sorry to ask!

After several years of exploring panties and lingerie for powerful masturbation, my fantasies evolved to being a panty slut and doing slutty things... with a cock. Not attracted to men per se, but cocks are amazingly erotic and powerful. I finally bought myself a big (groan) realistic-shaped (to feed my fantasy) dildo.

The first time I was smart enough to use a lot of lube and after about an hour, it sank in completely and I exploded. That sensation of being penetrated and filled drove me wild. While the dildo I'd bought was way too big for an amateur I was persistent and patient and had many hard pounding sessions with myself.

Regarding the second, with the wife, I did encounter... "foreign objects" but that's the chance you take.

 

[klippert]

before losing my virr'ginity. My G'rrrl friend and I were into oral sex.. since it felt so good rimming her and being rimmed.. well, Why not try fucking her ass...

 

[bluesky496]

And did you enjoy it the first time?

Also if you're fingering someone anally-or yourself-do you ever feel stuff up there you shouldn't? Is that common? Sorry to ask!

it was simple ,my lover wanted to use me for anal sex so we did it and yes i enjoyed it .

 

[sguy1234]

My first time was caused by a slip of the tongue......er........cock It was totally accidental, but bloody hell I've loved it ever since.

That is hot.

 

[thebeesknees]

it was simple ,my lover wanted to use me for anal sex so we did it and yes i enjoyed it .

yes ....what she said about sums it up!!!

 

[Kittycansquirt]

I tried it because.....

I'll try about anything once. The first time was horrible, he didn't know what he was doing and there was not enough lube at all...I bled for days before going to the doctor to find I had an internal tear. I was scared to try again...but I'm very glad I did. I became more comfortable and bought some beads and desensitizing lube to prepare me better. Now I beg for it....especially in love with my beads, I even put them in sometimes before going out to run errands.

 

[Mbiguy77]

I was 18 first time I had anal. I worked in retail. My boss hit on me constantly and I turned him down out of fear that word would spread that I liked cock. Well one night the only road that I can take to get home was closed and he offered to let me stay with him.

We went to his place. We got there and just sat and watched a movie. He said he only had one bed and said he wouldn't mind if I joined him. I asked what I should wear to sleep in. He told me he would be naked. He also said he has been dieing to see me naked and would love for me to come to bed naked too. So I went to bed with him. I couldn't help but marvel at his glorious huge cock. We 69'd each other. He gave fantastic head. He said before he made me cum he wanted to fuck me. I told him I hadn't done it yet so he would have to be easy.

He indeed was easy. He eased it in with lube. After several minutes I asked how much was in. He pushed and by then it didn't hurt anymore. He said, "All of it." He was slow at first. He asked if it hurt. I told him it didn't anymore. I told him it actually felt kinda good. He started going faster. He said he loved how my tight pussy felt. He grabbed my ass and started fucking me good. It didn't take him long to cum. Probably 15 minutes. I loved the fact that he didn't tell me he was going to cum until he was already cumming. That way I couldn't chicken out. After he was done he got between my legs and sucked me off.

We fell asleep together. Next morning I woke up horny for more. He was still asleep but had morning wood. We were spooning. I got up next to him and pushed his cock back in me. That woke him up. He kissed the back of my neck which drives me wild. I ended up getting on top of him and riding his cock.

I would work for that same company for another year. We had sex countless times during that period. Word eventually got out but by then I didn't care.

 

[tristantrotsky]

Losing My Anal Cherry

I was with my first Boyfriend for six months, and I sucked him off every time we were together - I mean, why else would he choose to be with me? my sparkling conversation, my sophisticated wit? I think not. But, although he complimented me on my bare bum, calling it nicely rounded and girlish, he never showed any interest in sticking anything up it. When it came to anal, I was a late starter. Messing around as a kid a schoolfriend once suggested he wanted to put his cock up my bum, I wasn't shocked or outraged, I just looked at his cock and it simply seemed impossible to me for something as big as that cock to fit into such a small tight orifice. He didn't argue and we did other stuff instead, tossing each other off. Much later, I was twenty-five, and sex with my first adult Boyfriend was strictly oral, I sucked him off a lot, much to our mutual satisfaction. My second Boyfriend was a little more experimental, and took pleasure in pushing my limits. Naturally by then I'd seen lots of Gay Anal Porn and was mildly curious - but a little scared to know what it was like. When he said he expected anal during his next visit I was obedient to his wishes. I don't know whether he knew he'd be taking my anal cherry, or if he even cared. I didn't want to appear unworldly by admitting it. He's seriously hung, and my doubts about 'something as big as his cock fitting into such a small tight orifice' as my poor defenseless little bum-hole began resurfacing. I watched some online Porn studying their facial expressions and positions, and prepared and lubricated accordingly. I was jittery as a virgin bride (if such a thing exists anymore) when he arrived. Maybe he'd have forgotten? I got down naked to suck his cock as usual, but after a few moments of this he shoved my head away irritably and said 'no, I want your arse'. So I got on all-fours on the bed, bum raised and legs parted, and he took me doggy-style. After a little initial awkward resistance and squirming around, once his glans had forced it's way in, the rest slid in surprisingly easily. It took my breath away, felt oddly strange. I made all the whimpering grunts and moans I'd heard on the Porn clips, and they weren't all entirely for effect. I enjoyed the way my own cock & balls dangled, then flipped and jerked as he began to fuck me. Some time later, after we'd both cum and he'd pulled out I asked 'was that alright, did I do it OK?' And he said 'you'll get better', which I took as approval. I preferred sucking cock, and still do, but I'm happy to take anal too if that's what my Boyfriend wants. He comes to me to do all the dirty grubby little things his wife won't do, so if I want him to come back for more - which I do, I can refuse him nothing! We did it that way a number of times subsequently. He once texted me to say that he only had time for a brief visit, no conversation, so I had to be ready. So I was there when he arrived for me, naked, lubricated, bottom raised for him, he didn't even undress, just lowered his pants and fucked me straight away without a single word, like I was a cheap whore, he shot his load in my bum, then went back to his office. I felt deliciously sundered and delightfully used…

 

[Massacre]

My first time we were in 69 and looking up at her asshole it was so cute and it started there.

 

[Twalter22]

A bottle of Bourbon. A very horny young lady her vibrator and me hoping I would be able to get it up later that night.

 

[itsstillme]

The first time was all his idea. He was slow and gentle, but it didn't do much for me.

 

[MrSneakyinPA]

school days.scared of preg.did anal mostly. sometimes felatio, od helping hand to cls mate guys in toilet during class time.

My g/f had us try it for that reason. She didn't like it. Couldn't get it in.

But my first time, receiving was a neighbor told me I'd like it. He was right. We only did it twice, I've wanted to do it again ever since.

 

[klippert]

rimming giving and receiving made me want to try it...and noticing the only girl in a group of us watching porn one night that didn't make the EEE'UUU comment when the Porn'let was taking a cock up her ass...

 

[LegsOpenedWide]

...Still not been brave enough to try anything up there yet ... though have discovered when playing with myself that it feels nice to just feel around the area.

 

[Hard_Rom]

A slutty friend with benefits pissed me off. I knew she did anal but did not like it. Plus I wear a large size in condom. But she insulted and humiliated me behind my back. I found out. Next time she called looking to get away from her hubby and his drinking buddy I told her anal, bondage and humiliation was the price. She was such a slut she agreed not thinking I was that serious. She complained and even refused a couple of times. I just told her she could leave at any time and go back to her husband. She really hated his drinking buddy, so she stayed. Real porn star experience that night. She had her barslutting outfit in the car and put it on before she came in. Ended up three holing, tying up, whipping and throwing her out naked. Then I told her why I was so pissed off. Told her if she wanted her barslut outfit back she had to do another session. Three days later she came back, after she said her ass didn't feel funny anymore. She begged forgiveness, I used her like a pornstar again. Then forgave her. Only ass fucked her on special occasions after that.

 

[theslutbunny]

Was drunk, and the guy was very persuasive. It hurt like fuck, but yeah, I enjoyed it.

 

[Fill_de_Puta]

Giving - I was asked to do it because she loved it.
Receiving - It was just something that I needed to try.