First anal

My first time getting fucked in the ass was relatively young age 12. I had a lot of experience playing with my ass by myself with cucumber’s and tool handles etc but never a real cock. Same age buddy and I were doing a sleep over at his house and we decided to get naked and Jack off together. I remember the excitement of seeing his beautiful cock and I asked if he wanted to try fucking me. He said yes and we got some hand lotion and in he went. For me it was wonderful and he went until he had an orgasm in my ass. I was instantly addicted and we ended up doing it on a regular basis until he went away to another high school. I remember walking home on many occasions with cum dripping down my legs. I was extremely lucky that my first was with such a nice friend. Getting fucked for an anal bottom is a wonderful experience but the first time is a great memory.

My first experience was with a small pen and some Vaseline as I was pretending I was having my temp taken. A few months later, I bought a blue vibrating dildo. The girth was much bigger than the pen and a little bigger than my own cock. I would strip naked with a tube of warming KY and lay on a towel. It took some practice, but I finally worked the massive dildo inside of me. I’d fuck myself with it and everytime I came HARD. That’s when I knew i was anal erotic.

I had been dating a slightly older woman while in college and she was very adventuresome. She was very buxom and enjoyed having sex without invitation. She lived out of state so I didn't see her often but if she visited, I knew that there would be ample sex and lots of nude exploration. She was the first to introduce me to receiving a prostate massage while giving me head. It was then a totally unique experience and led to incredible pleasure.

My first experience was gloved fingers from my female partner. She only used one finger, but eventually moved onto a second. The second was uncomfortable, which made sense due to the lack of activity down there. I would eventually like to try plugs, dildos and the real thing.

i have also given anal, which was uncomfortable for her. The next time we just played with ice cubes. I would like to try it again with others Using plugs dildos and my penis. Maybe even tryout a fucking machine.

I have had a rectal thermometer/toy/anal fetish since I was 3. My very first orgasm was a prostate orgasm at 14. I was playing back there with my fingers and kept rapidly pressing on the sweet spot before I even knew what a prostate was. I almost blacked out and ejaculated a huge puddle. After that. I was locked in the public bathrooms hone bathrooms or my bedroom 8 to 10 times a day…lol. I've slowed it down to 3 or 4 times a week these days. Sometimes more sometimes less.

I only had one partner (female) that had a finger in my ass while sucking my cock.Unbelievable feeling!

First anal was at a company prescribed physical exam performed by a very large male physician.

After the genital /penis portion I was instructed to turn around and place my elbows down upon the table end and spread my feet.

I next felt my butt cheeks spreading apart followed by a slick greasy touch to my virgin cherry rectum and suddenly a rapid thrust forward which caused my knees to lockup and a excruciating jolt internally simultaneously.

A bit of ejaculate was present at the end of my penis.

My first anal as a result of my first prostate exam. Fretter

My first experience was gloved fingers from my female partner. She only used one finger, but eventually moved onto a second.

The first time wifey used a gloved finger on me was amazing

The first time wifey used a gloved finger on me was amazing. She started with one finger which was not too difficult as i enjoy butt plugs. then she put in a second finger and that drove me wild the thrusting and the feel of the latex was so lovely. three fingers was too much but mainly because she lost the aility to move them about and curl them up to my prostate.