My First Time

Story Info
First Time: Jim was 33 years old and I was 18.
770 words
4.27
65.7k
16
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

Jim was 33 years old and his family was friends with mine. I always had looked up to some of the guys older than me and he was no different and very popular. I had been working at a grocery store and he came through the line and i bagged the items he had purchased. He asked could I help him put his things in his vehicle I said sure. So after loading his car he gave me a tip, He started some small talk and said, Come over to his house and we have some fun some time.

A couple of weeks later, I went to his house. It was summer time so I had on a T-shirt and some cut off jeans. I rang the doorbell, he came to door said look what someone brought him. We both smiled. He said well get comfortable sit on the couch and tell me about your day. We chatted. He asked if I cared for something to drink? I said sure. I was thinking soda. Well it wasn't, It was soda with Bourbon with cola. He asked if I had ever tried it before? Yes and it burned a little was my response. You will get used to it was his response. After a few minutes i was feeling the effects of the alcohol and I was giggling and getting numb. Since I had not built up a tolerance It got in my system fast. He asked did I want to watch some movies? I said Sure!

He put in straight porn girls sucking guys sucking and having sex. To an 18 year old boy this was awesome and the bulge in my shorts was getting hard. I had never seen porn before now.

As we drank more he put in gay porn guys sucking and having sex. He asked had I ever thought of that and i said sure just curious. He told me to stand up he pulled off my T-shirt and pulled off my shorts and underwear. Giggling all the time. I was naked and I sat back on the couch. I was drinking watching and listening to the movie I was getting horny. Jim sat beside me. He kissed my lips and had his hand in my lap. He was lightly jerking and playing with my cock. He licked and kissed my neck working his way to my nipples. He licked and bit them. I moaned. He said good you are nipple sensitive.

He then worked his way down to the rim of my cock. He pulled out some lubricant and put it on his middle finger. He then was applying it to my butt hole while sucking my cock after a few minutes I felt like my cum was going to explode. I told him I was going to cum. He motioned to go ahead. Wow! when I had my orgasm my butt was pulsating on his finger. It was euphoric. I thought that was the best orgasm ever. Was I wrong.

He said we are going to bedroom. I could still hear the movie. He had me lay down on my stomach. He had the lubricant and placed it on one finger and inserted it in my butt hole. Then he was trying to stretch my hole. Jim applied two fingers in my hole and he stretched again and said relax and breathe. He put three lubed fingers in my hole, it was a little uncomfortable He told me to relax and breathe and it will get to where it feels good. He got nude and he applied the lubricant on his 7 inch cock. He gently inserted his cock in my hole. He was right initially it hurt as he kept working patiently he said relax and exhale when he is pushing his cock in. It was exactly as he said. He started pinching and playing with my nipples which sent me into another realm of euphoria.

He was really grinding away. it felt so good. We were both sweating. After a few minutes he was going to cum. When he started to cum I started to cum as well, my butt hole was pulsating on his cock while he was shooting his warm load inside me. It was the best orgasm ever. I told him I felt guilty. He said don't it was me not you. I saw him a few times after that and the sex got even better. He said you will always remember the first time. He was correct and ever so often I crave cock it's like a drug.

Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
11 Comments
jrt20jrt20almost 2 years ago

I had a similar experience around that age but in addition to him sucking me he wanted me to fuck him which I did many times over a several month period until I got a girlfriend

AnonymousAnonymousabout 2 years ago

A good appetizer.

DustyDevilDustyDevilabout 4 years ago
needs a little more polish

Good start but needs to be expanded some. Hotter sex act would help.

HuckPilgrimHuckPilgrimover 4 years ago
Good work

Great story! thanks for sharing.

Riki1942Riki1942over 4 years ago
Orgasmic Contractions

I know exactly what you mean about those orgasmic contractions your sphincter ring make on your partners cock while you cum. It feels so fantastic as your hole clamps down over and over while you are stretched around a hard cock. It's one of those pleasures that a guy isn't aware of if he has never been fucked. I always try to cum before my buddy does so he will still be fully hard and inside me so I can feel that when I start to shoot my load. I like to have him on his back with me on top and riding him. I can sit down with him in me all the way to the base of his cock and grind my hole in little circles on him. That sideways pressure of his cock in my hole feels so good, a little like it does when my ring is clamping down on him when I cum.

Show More
Share this Story

Similar Stories

Becoming His Girl An older man teaches a boy to forget his girlfriend.in Gay Male
Backseat Introduction Girlfriend's dad and boyfriend share the back seat.in Gay Male
Friend's Father During a long weekend at a friend's, his father takes me.in Gay Male
It's Not Gay, It's Just Sex My brother-in-law and I learn to satisfy each other.in Gay Male
Straight Construction Dad Explores Married coworker and I have first male sex experience.in Gay Male
More Stories