Search Results for: first time anal

Stag Do With Dad's Best Man

Posted by: Teddybayr Age: 18 Posted on: 10 Oct 2024 4 comments
1 likes 22 views Category: First Time Tags: Advice, Confession, Secret, Bear, Daddy, Dad, Older, Married, Husband, Straight, Younger, Twink, Naive, Old and Young, Sex, First time anal, Virgin, Gay, Rough, Party, Stag do sexzesty

My parents said I was too young to go to my Dad's stag do last year. So my Dad's best man brought me. When we showed up my Dad was a bit pissed at first but Hunter (the best man) calmed him down and told him we'd share a hotel room. The lads all pulled, including my Dad (gross). Except Hunter, he's d...
The night went by in a blur. I remember Hunter stood behind me, bending me over, me reaching out trying to hold onto the hotel bathroom's doorframe, but my hands kept slipping with the force of him behind me, jackhammering away. And then him refusing to pull out when he'd finished. He said it was my fault I fel... » Read more
The Quest Continues ( Am I Gay?)

Posted by: ShyGuy01997 Age: 18+ Posted on: 29 Sep 2024 6 comments
4 likes 24 views Category: Masturbation Male-Male Tags: Arab, big dick, first time anal, am I gay, oral sex, zesty , anal

This is another story on my quest to see whether I was gay or not.( Back in those days I didn't know about bisexuality, just gay and straight, I was pretty dumb about that sorta thing now that I think about it, lol.)

For those of you who read my previous story I know I said I was going to give a follow up a... » Read more
First Time Anal

Posted by: strokershot Age: 18+ Posted on: 16 Sep 2024 8 comments
9 likes 45 views Category: Sex Stories Anal Tags: anal, cum, buddy, cock, ass

First time doing anal with a buddy.

My buddy and I had planned a night to hang out at his apartment. He had moved to a new place and we had hung out a few times. We would watch t.v and eventually get naked and start sucking each others cocks. This night was no different. The expectation was we would chill, get ... » Read more
First Anal Sex

Posted by: StrokerAce Age: 26 then Posted on: 24 Aug 2024 6 comments
10 likes 38 views Category: Sex Stories Anal Tags: first time anal sex, rough sex, makeup sex

The first asshole I stuck my cock in

Since I first learned about sex I knew I would turn out to be a kinky sumbitch. Like most horny young lads I craved the day when life would present me with pussy. But my first kink was anal sex. I became obsessed with anal sex. The thought of sliding my cock into a woman&rsq... » Read more
How I Came To Love Anal Sex As A Bottom

Posted by: Ricksvca Posted on: 04 Aug 2024 4 comments
8 likes 49 views Category: Sex Stories Male Gay Tags: Gay, Anal sex as a bottom, first time anal

This is the true story of how I came to love being fucked in the ass by a man.

I am bisexual and this is the true story of how I came to love being fucked in the ass by a man. When I first started having sex with men (age 22) I had no desire to have any kind of anal sex... » Read more
Big Lake Stories Part 4

Posted by: robbicu Age: 20-24 Posted on: 29 Apr 2024 4 comments
3 likes 37 views Category: Sex Stories Male Gay Tags: hand job, blowjob, anal, first time anal sex, first time gay sex

A continuation of stories from Big Lake partially based on fact, from around 1975. For context, see parts 1 - 3.

Pierce woke up to a banging on the front door. He sat up, blinking in the dark and looked at the clock next to his bed. 1:47. The cottage was freezing and he could hear s... » Read more
Showing My Boner for the First Time

Posted by: SoloTouchArchive Author: Bobby Posted on: 10 Oct 2020 16 comments
21 likes 2034 views Category: Masturbation Male-Male Tags: First time anal, male male

Still can't believe this happened
I used to love calling over to my friend Steve's house growing up. If it was early in the morning during school holidays he was likely to be still in his pjs and I would regularly get to see him getting dressed. This involved him removing his pjs and me seeing his willy, bum, chest, eve... » Read more
What a sensational feeling.

Posted by: HappilyMarried Age: 60 Posted on: 08 Jan 2019 11 comments
13 likes 169 views Category: Sex Stories Anal Tags: anal, dildo, male

First time anal.

I have a friend that has always wanted to be the first to perform anal sex on me and cum inside me for some reason, but I've never been to fond, or even had a desire of having my ass played with. He brings it up every time we see each other and whenever we talk on the phone, whic... » Read more
First Time Anal With My Best Friend

Posted by: Vixen Age: 22 Posted on: 29 Mar 2018 7 comments
12 likes 230 views Category: Masturbation Female-Female Tags: Female-Female, Masturbation Female-Female, sex stories anal, anal sex, best friend, anal play, sex stories cum lovers, rabbit

First Time Anal With My Best Friend. Wine and tequila involved!

My best friend Andrea and I were always very close to each other. We always tell each other about all of our relationships. We give each other relationship advice, we tell each other about every guy we fuck and we actually go into exquisite d... » Read more
First Time Anal Play With My Ex

Posted by: SoloTouchArchive Author: Dole_666 Age: 24 Posted on: 04 Feb 2018 7 comments
5 likes 1225 views Category: Masturbation Male-Female Tags:

I was the first guy to play with my ex-girl friend's asshole.
This story happened a couple years ago. I was dating a girl who was four years younger then me (I was 24, she was 20.) I was finished with school, but she was still attending university. Sadly, it was also a long distance relationship, so the times I got to s... » Read more
Anal For The First Time

Posted by: S3xAddict Age: 20s Posted on: 05 Mar 2017 3 comments
3 likes 619 views Category: Sex Stories Couples Tags: First time, anal, sleeping, family

First time fucking girlfriend in her ass.

This happened while still in high school around second semester senior year. My girlfriend and I were hanging out one Friday night when she was suppose to go to a friend's house for the night. Walking her there we were surprised to find her friend was not home, she tota... » Read more
Lessons From Cousin Larry

Posted by: SoloTouchArchive Author: Rick Age: 46 Posted on: 25 Oct 2016 1 comments
4 likes 1277 views Category: Sex Stories Male Gay Tags: first time, anal, cousins

This was my first time with another male, I still remember it so well.
This took place twenty-six years ago when I was 15 but I remember it very well. I had been playing around with my cock for years but never long enough to orgasm or ejaculate. I used to get horny though. Sitting in class and watching the girls used to... » Read more
First Time Anal Play...

Posted by: Sparkypaul Age: 17 then Posted on: 08 May 2016 6 comments
10 likes 1436 views Category: Masturbation Male-Female Tags: Anal Play, Mutual Masturbation, Orgasm, Teen, First Time

First time anal play with my girlfriend on a camping trip.
My girlfriend Debbie went with my parents and I on a camping trip in the southern California desert many years ago. We were both 17 at the time and although sexually active she didn't want to "go all the way" yet. However, we always looked for a opportunity to p... » Read more
First Time Anal Play

Posted by: nyjerker Age: 32 then Posted on: 05 Oct 2014 0 comments
1 likes 3388 views Category: Masturbation Male-Female Tags: toys, anal, phone sex

phone sex leads to new inspiration
Her name on was candy girl. We found each other in some chat room. We went private and had some cyber sex. Eventually it lead to phone sex, her real name was Lisa, she was very sexy on the phone and about 10 years younger than me. We always got off a couple of times, usually she could ... » Read more
First Time Stings!

Posted by: SoloTouchArchive Author: Tiffany Age: 18 Posted on: 24 Feb 2005 1 comments
5 likes 689 views Category: Masturbation Female Solo Tags:

So curious, I decided to try out anal.

First I got everything I needed to start. Vaseline as lube, and a metal Cigar holder *very big*. The only clothes I left on were my socks and t-shirt. The t-shirt, I like to roll up over my boobs. Then I went to my computer desk and slid my bum on the edge of my cha...
first time anal, anal practice, anal masturbation » Read more
First time anal experience.

Posted by: SoloTouchArchive Author: pan-t-snfr69 Posted on: 30 Dec 2004 3 comments
3 likes views Category: Sex Stories First Time Tags:

Well I discovered I am bisexual, and here is the story of my first serious experience with another man.I've been with a few men who have shown me how much fun a blow job can be done by another man. I love pussy, but this has been a whole new world for me. Anyway, this past summer, I had a day off from work and was alon... » Read more