First time anal

[live4thebj]

First time taking it in the ass and/or first time fucking an ass. Tell us about it. Man or woman.

 

[Leaderoft5b]

I was 50 at the time and she was 29 - a woman from my running club who I was having an affair with. She wasn't married but living with someone. I was single at the time.
One weekend she attended a running seminar at a fairly local hotel and had a double room to herself over the Friday and Saturday nights. We'd been having regular (vaginal) sex at my house for a few weeks so she invited me to join her at the hotel over both nights.
On the first night we just fucked as we had been used to doing. She was slim, athletic with a great body and it was honestly the best sex I'd ever had.
On the second night I'd been eating her pussy for close to half an hour and as I prepared to put my cock inside her she surprised me by asking me to fuck her up the arse - (I'm British!)
It was clearly something that she enjoyed and wanted but to be honest it was a first for me. However of course I went along with it and with some help from baby oil it was a great experience, almost certainly to never be repeated.

 

[live4thebj]

I was 50 at the time and she was 29 - a woman from my running club who I was having an affair with. She wasn't married but living with someone. I was single at the time.
One weekend she attended a running seminar at a fairly local hotel and had a double room to herself over the Friday and Saturday nights. We'd been having regular (vaginal) sex at my house for a few weeks so she invited me to join her at the hotel over both nights.
On the first night we just fucked as we had been used to doing. She was slim, athletic with a great body and it was honestly the best sex I'd ever had.
On the second night I'd been eating her pussy for close to half an hour and as I prepared to put my cock inside her she surprised me by asking me to fuck her up the arse - (I'm British!)
It was clearly something that she enjoyed and wanted but to be honest it was a first for me. However of course I went along with it and with some help from baby oil it was a great experience, almost certainly to never be repeated.

Why not repeat it?

 

[Leaderoft5b]

Why not repeat it?

It was 15 years ago, don't see the woman any more, I'm now with someone else, can't maintain a hard-on any more.

 

[pumper71]

I had started seeing a girl I had known for many years, we finally hooked up and the sex was great. She was a little naive towards the kinkier side of sex and was quite embarrassed when she asked what other things we could do in bed. When I mentioned anal she was a bit shy in admitted she hadn’t done it before so I brushed it off and said let’s see how it goes. The next day she came around she walked in and said, you can fuck me in bum if you want.
So I did, and an half an hour later she’d lost her anal cherry.

 

[live4thebj]

It was 15 years ago, don't see the woman any more, I'm now with someone else, can't maintain a hard-on any more.

I can relate. I need direct constant stimulation to remain hard.

 

[StrongMaster7]

I waited a long time and then the opportunity was there. I’ll just say that may be where my sadistic streak first showed up. After some play, my lady friend got on all fours and presented her ass to me to fuck. I was hard and ready, but her anus was tight, very tight. I worked a finger in, then two. I was lubing her up and got three fingers in. I loved the sounds she made as I shoved my fingers in her ass and rubbed her clit. Then I positioned myself behind her, put the tip of my stiff cock against her lubed hole and pushed. Like a brick wall. Asshole tighter than ever.

Then she changed her tone. In a low growl she told me to fuck her ass. Shove it in. Push harder. If it hurts, make it hurt. And something in me changed too. I leaned over her and told her this was going to hurt but I wasn’t going to stop. And I grabbed her hips and began to force my cock into her anus. The sounds she made were too fucking hot. Animal sounds. And she kept repeating for me not to stop, to push harder, and to make it hurt. And that is what I did. After what seemed like a long time, the resistance suddenly relaxed and the full length of my cock pushed into her ass. She screamed into the pillow and then began moaning as I pumped my cock in her shithole. If felt amazing. So warm, very warm. And that tight ring of her sphincter muscles slid up and down my cock as I fucked her ass. That would drive me over the edge. I began to slow down and control myself and she said for me to fuck her harder and faster and to come deep in her ass. And I did.

Haven’t had many chances since then...

 

[live4thebj]

I waited a long time and then the opportunity was there. I’ll just say that may be where my sadistic streak first showed up. After some play, my lady friend got on all fours and presented her ass to me to fuck. I was hard and ready, but her anus was tight, very tight. I worked a finger in, then two. I was lubing her up and got three fingers in. I loved the sounds she made as I shoved my fingers in her ass and rubbed her clit. Then I positioned myself behind her, put the tip of my stiff cock against her lubed hole and pushed. Like a brick wall. Asshole tighter than ever.

Then she changed her tone. In a low growl she told me to fuck her ass. Shove it in. Push harder. If it hurts, make it hurt. And something in me changed too. I leaned over her and told her this was going to hurt but I wasn’t going to stop. And I grabbed her hips and began to force my cock into her anus. The sounds she made were too fucking hot. Animal sounds. And she kept repeating for me not to stop, to push harder, and to make it hurt. And that is what I did. After what seemed like a long time, the resistance suddenly relaxed and the full length of my cock pushed into her ass. She screamed into the pillow and then began moaning as I pumped my cock in her shithole. If felt amazing. So warm, very warm. And that tight ring of her sphincter muscles slid up and down my cock as I fucked her ass. That would drive me over the edge. I began to slow down and control myself and she said for me to fuck her harder and faster and to come deep in her ass. And I did.

Haven’t had many chances since then...

I was hooking up with this mom that I was doing doggy style then she screamed shove it up my ass. So I did just that. She didn’t even flinch! One single hard push and I was in all the way then just started pounding. She was fun and weird. Made a strange offer to me.

 

[soflabbwlvr]

I really have two stories here. The first time I tried and the first time I succeeded.
My college girlfriend and I had been together for about three years, and eventually got to discussing anal sex. I wanted to try it. She wasn't so sure. After a few months she agreed to try it. I can't remember what we used for lube, but it was probably baby oil. Anyway, I got behind her and tried to push it in, and got nowhere. Backed up and tried again - still nothing. Then again. And again. Eventually she had enough and honestly, so had I. We tried again a few days later, and same result. For the next year or so we tried, but made zero progress. Eventually we just quit trying. We broke up, but it had nothing to do with that.

About 6 mos. later my roommates and I were hosting a house party. A girl I knew brought a friend with her, and as soon as our eyes locked I was interested. She was a little thick, with big eyes and huge breasts. I didn't know where to look. My friend introduced us, but I had to go attend to some hosting duties. Later in the evening we met near the beer keg and I asked her if she wanted to go to my room to do some coke. Of course she said yes. We slipped away, did some lines, and started kissing between lines. I reached under her sweater and found those huge tits. She unzipped my pants, pulled out my cock and sucked it. I tugged off her jeans, crawled between her thighs and dove into her hairy muff. When she was wet enough I entered her and fucked until we both came. I pulled out, and we paused to do some more lines. She sucked me to hardness again, and then laid back on the bed. I entered her pussy that was already full of my cum. Suddenly I had an idea. I pulled out, placed the head of my cock against her asshole, and kissed her. She kissed me back, and then I pushed into her. I entered her with one push. She grunted, her big eyes opened even wider. I pulled back, pushed again, and was buried in her ass. I couldn't believe it. She didn't object, so I pumped in and out until I was ready to come again. I shot my second load, this time filling her ass. I pulled out, got dressed, and did some more lines with her before walking her back downstairs. The last thing she said to me was, "Don't tell anyone, I don't want my boyfriend to find out."

 

[PegMahone]

I was young, in my early 20s. I was always curious about anal sex but all the girls I was with over time said the same thing. No! It hurts, it does not feel good and girls only do it in porn.

I’m into enthusiasm, if a girl is not into it things are hard to enjoy so I don’t push it.

But I was curious if they were telling the truth. Being an adventurous person i decided to see what it felt like. So I got a small candle and lay on the couch, then I used the same lube I was stroking with to ease the candle in my virgin ass.

It felt exotic and amazing. It did not hurt, it did not take long before I had an explosive orgasm that was easily double the power of the average orgasm. I was mind blown.

I couldn’t believe it, so I waited and tried again later using only the candle. That’s when I became addicted, the candle alone made me cum. Hard.

Now my girl at the time would have reacted poorly to my discovery so I kept it to myself for a long time. Keeping it hidden is how it became a full blown fetish. I can’t get enough.

I have come a long way from a candle since the early nineties. Now my all time favorite toy is a 17” tentacle that I can take to the base. It is an otherworldly pleasure that only experience can describe. The best part is, my wife is totally cool with it.

My most favorite toy ever! 17” long with a base that is 3.75” wide.

 

[AnnaUK1968]

My first anal was on my wedding night, I was 22.
My (now ex-) husband was a big guy, and we had regular anal throughout our marriage.
I've enjoyed it with other partners and with toys ever since.

 

[Luvloosepussy]

My first anal was on my wedding night, I was 22.
My (now ex-) husband was a big guy, and we had regular anal throughout our marriage.
I've enjoyed it with other partners and with toys ever since.

Big guy as in size or big as in cock size??

 

[AnnaUK1968]

Big guy as in size or big as in cock size??

Both!

 

[Luvloosepussy]

did you enjoy it??

 

[AKcouple907]

First time I ever peformed anal was on our wedding night. We were really drunk and my wife TOLD me to put it in her ass. Every since then I have been hooked. I never ask for it but when she tells me to, I do not hesitate. Its soooo hot.

 

[Wonderer67]

This was 1995 and i was recently divorced and making up for lost time. I always wanted to have anal sex with my first wife, but she was not interested in anal at all.

I was seeing this very hot, redheaded Italian woman from South Philly. A real Philly gal with all the attitude and everything. She was a firecracker!

She had a boyfriend and I was seeing someone else too but we were introduced and connected right away. There was instant attraction and desire.

I don’t remember if we talked about anal, or if it just happened… We’d been seeing each other for a few weeks and slept with each other maybe 5-6 times. We were going at it doggy style and she told me to get some more lube and put it in her ass.

I did not have to be told twice.

Took a bit to get it in. It was tougher than I would have thought, but finally she just opened up and I was in her ass almost balls deep. She had me go slow for a bit, then I sped up.

This was not her first rodeo, taking it in the ass, and she was good at communicating with me, telling me to push, keep up the pressure, stop, slow down. Etc.

It was like a dream come true and how I envisioned it: tight, naughty, sensual, intimate…

She was pretty into anal and we fucked that way a few times that summer before we both sort of went our separate ways.

Summer of 95 was one I will never forget.

 

[Pabiporffor]

I was in my teen years, he in his mid-20s with that quiet, experienced confidence that puts a girl at ease. The foreplay and preparation were unhurried, and any fears I had melted away with my relaxing sphincter.

I admit when penetration time came, a lot of that fear came back. The first inch made me wince a little
but he talked me through it and filled me slow and steady.

Sex itself felt a confusing mix of mild ache and deep wobblyness, scary yet oddly intriguing. His pace was restrained, not ultra slow, but at that point that says I'm going to take my pleasure and try not to hurt you. I guess you could call it the polite pace. Admittedly, it wasn't always comfortable, and I squirmed a lot, but I clung on and took it.

Thing is when you're a teen, you might be technically an adult, but you don't always feel you're treated like one. So, to have this older guy on top making love to me really made me feel like a woman.

 

[Zosofan1000]

It was 15 years ago, don't see the woman any more, I'm now with someone else, can't maintain a hard-on any more.

I hear ya brother. Even with the blue pills, I have to fuck at a snails pace. Any serious exertion and all of the blood drains from my dick.

 

[gtnlynn]

My wife's first and only anal experience was in college. She was having consensual sex with her fwb. With no warning, he pulled out of her pussy and rammed his hard cock into her ass. No lube. It hurt like hell! She screamed and kicked him away. She hasn't let any other cocks get near her ass since then.

 

[KyleR215]

Never performed to me, unless you include doing it myself with toys.

I have only done it to a woman twice.

The first time I was in my twenties and dating a woman in her late 30’s. We were at a party down the shore and we both got fucked up on Goldschläger.

We were on the floor, I was behind her spooning her but thrusting into her hard. Long quick thrusts. I came out and went back into her but into her ass. I kept thrusting and she let out a yelp and told me to stop and that I was in her ass. I went to pull out and she stopped me and told me to let her get used to it. I got to finish in her ass and we returned to the party.

Then many years later, an ex was interested in exploring. I kept bringing up the topic of anal to her. We had never done it together. We were both sober. She was on al fours, I took my time with prep, fingers and lube. Finally, when she was ready, I got into position behind her and watched as the tip of my cock slipped into that tight little hole and then clasp around my cock.

It was amazing, awesome to watch and put me over the edge quickly. She said she liked it. Enjoyed how it felt and how it felt when I cam in her ass.

Those were the only two times

 

[Zosofan1000]

When I was in college, I dated a girl who was sexually adventurous. She surprised me by taking me to an adult video store (this was the '90), pulled me into a booth and fucked me in the booth. Then I surprised her by making her strip naked in my bedroom. I bound her to the headboard with ropes I had pre-tied and sodomized her (consenually of course). She later said she loved it but wished I had lasted longer.

 

[UtilityCurve]

Admittedly, it wasn't always comfortable, and I squirmed a lot, but I clung on and took it.

Have you ever done it again? Any less uncomfortable?

 

[Pabiporffor]

Have you ever done it again? Any less uncomfortable?

Tonnes of times

 

[kccasey]

I masturbated with anal sex for many years. Using household items and later dildos. First time anal was with a TS prostitute I met at a bar, I was 21 years old. When I sucked her cock and took her up my ass it was life changing. Except I was scared. Homosexuality was very frowned on then. As a result I went for years without sex other than masturbation, most often with dildos.
I married and sex with my wife was ok, but not that exciting for me. I did get her to fuck me with strap Ons but she tired of that.
Now she has given me permission to seek sex outside of marriage. Even suggested that I look for another man, which I have.
Have made two connections through silver daddies. OMG, I am such a cock slut. I love sucking cock and getting my ass fucked. Both are strictly tops and I am fine with that. Anal sex is just the best thing ever. It is a pain to prepare for, with enemas though. I probably would have been happier as a gay man, but maybe not.

 

[UtilityCurve]

Tonnes of times

That answers both questions! Glad for you (and for the guy or guys).