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 18 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 18 views Category: Masturbation Male-Male Tags: Arab, big dick, first time anal, am I gay, oral sex, zesty , anal review review review review

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 29 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
Big Lake Stories Part 4

Posted by: robbicu Age: 20-24 Posted on: 29 Apr 2024 4 comments
3 likes 32 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
What a sensational feeling.

Posted by: HappilyMarried Age: 60 Posted on: 08 Jan 2019 11 comments
13 likes 166 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 229 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 616 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
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