first time anal sex

[effingbored]

What Is everyone's first Anal Experience (Or If You Want To, Youd First Few Experiences) For Both receiving And Giving. What Happened, Who Was It, What Did It Feel Like, etc.

[doughejk]

I've only ever received. It was with this dude who played saxaphone in the band. He had a huge cock(like 9ish ") and was really rough. he through me down on the bed and spread my legs. he also fucked me doggy and then on my belly with his weight pressing down on me. needless to say their was so much cum on those sheets

[GoogleMaster]

The first time I received any anal play I was making out with a girlfriend. We were getting hot and heavy on her bed and I was naked, or basically naked. I wasn't expecting it, she didn't ask and we had never discussed it. She just softly put pressure on, then in, my ass. She didn't do much except use her tiny finger to fill my asshole. Later, when we had finished and were getting dressed she just said "I hope you liked that. I thought you would so I did it." She was right I liked it.

The first time I gave anal we had been drinking tequila shots for most of the night. Although it was something I had discussed with my girlfriend, it was also something she wasn't really interested in. However, that night she offered and I accepted! We used lots of lube and a condom and went slowly. In the end she loved the feeling and asked for it more.

[generalhammond]

My GF and myself were both 16. Wednesday night was sex night as her mum and sister were at girl guides. We had been having sex for about a year and \I had played with her ass many times and fingered her there. She seemed to like it!!

We were in her favorite position. Her bent over her bed and me fucking her from behind. I was fingering her ass and thought id give it a go. I went in nice and slowly. I was about 3/4 of the way in before i started thrusting. After a few she started moaning. I asked her if if was ok and she said yes. I carried on for about a minute and a half befoe the combination of me being really turned on and the tightness of her ass around me made me cum.
She turned round and said 'is it ok to do that there???'
I think I said something like 'Yeah gotta be!'

[serendipitous]

Never given it.

First time was on my own with fingers, pens etc. working up to vibrators, dildos and buttplugs up to the point where I can take a 2.5" diameter plug inside my sissy pussy.

[smalldickbound]

It's been a while but if I remember right, it was after seeing a porn that had anal fucking in it... and I decided I wanted to try it... at the time, the only thing available was a plunger handle. I used vaseline and slid it in... it was uncomfortable but interesting. Ever since, I've tried a number of different things and someday might actually try the real thing.

First time I tried with a girl, it didn't go as I thought... I am short, she had a big butt and well, I got in barely but couldn't stay in because I am short

[Ezreal]

my first anal with my GF was a disaster when i put it in she shouted and said it hurt so much. i want to try anal sex but wtf she dont want it anymore.

[HolyAnarchy]

It happened about 3 years ago with my ex boyfriend. I was quite prepared for it since I already fucked myself a couple of times with improvised toys. Didnt hurt THAT bad.

[isi10]

My first anal experience date of our wedding night when my Wife forced me permanent chastity and she told me that I would not have any sexual relations with her.
My Wife told me that I have the right only to anal sex on me.
Since my woman takes me several times a week with a dildo while I still have my chastity.

[butterflyslave]

Originally Posted by Ezreal

my first anal with my GF was a disaster when i put it in she shouted and said it hurt so much. i want to try anal sex but wtf she dont want it anymore.

Unfortunately, if a person's first time is a bad experience then it is hard to convince them to try it again. If you can convince her to try again, I would suggest going really slow. My first time, we never even worked up to having him inside me. He started with his finger inside while he fucked me normally, and then he worked up to a plug, and then a dildo. And then I was too overwhelmed to continue and I begged him to just let me cum.

The next time, I was less nervous and knew what to expect. He was able to work up into going inside me, but I wouldn't let him move while he was inside me. It took a lot of restraint on his part, but it has worked out for the best since now I am willing to keep trying it.

Good luck convincing her to try again. Again i would suggest getting a small toy and only propose that to her rather than you inside her.

[Bi_joey]

First time i used vasaline and a finger in the bath, that moved onto pens etc.

Now I like finding new things to shove up there and a few sexual parters have joined in

[leashbottom]

my first time was when i was 12... two weeks shy of 13... a neighbor who was 64... He was really big and it was painful at first... then He grabbed my nipples and twisted them.. i was on all four... i reacted and ended up taking every inch... after that i loved it

[Schwink]

My first time when I was about 13. I found a vibrator in my mom's drawer and wanted to try it after watching it in porn. It HURT really bad. I have no idea why I ever tried it a second time. Now I love it though. I always end up size queening, even though my slimmest vibrator feels the best. I took Deep Dickin' Derek and I keep trying to get the Hitachi head in there.

[lolo15]

Originally Posted by effingbored

What Is everyone's first Anal Experience (Or If You Want To, Youd First Few Experiences) For Both receiving And Giving. What Happened, Who Was It, What Did It Feel Like, etc.

My mistresses forbade me all penetrations.
It is only from behind.
I am penetrated with a dildo regularly.
At first, it was a funny feeling.
I take a lot of pleasure from anal sex.
The only orgasms that are allowed me her anal

[leashbottom]

i have never Topped.... strictly a bottom...
i was 12 and He was 64... and really hung... 10 1/2 inches
He took a belt to my bare ass then made me suck his cock for a while before making me lube His cock and my ass with KY... then he put me on all four and began forcing that huge cock up my virgin ass... it hurt and He managed to get the head and an inch or two into my ass. i tried to pull away several times but he was twice my size and manhandled me easily. Then he reached around and really quickly grabbed my nipples in His big fingers, pinching and twisting them hard. That sudden pain made me react without thinking, made me instinctively jerk away... which was back, making me impale myself on His rock hard prick. i took every inch up my ass, i could feel His cockring against my stretched asshole... He began grinding His hips against my bare butt cheeks and then started pounding me hard... He dragged me around the bed... flipping me around into different positions, never letting His cock fall out and gave my asshole one hell of a reaming... i don't know when it stopped hurting but i was loving it pretty quick after it started... It was a long time before He pulled out and shoved His cock into my mouth and flooded it with His hot cum...
I went back every day to get butt-fucked for four years