Yes. I met him on Craigslist and messaged back and forth for a few days and then met up at his place.
Unplanned but I’d hoped it would happen. At a school sports swimming lesson. I had to share a changing cubicle with another boy. When we both were naked we were both hard up erect. We had a feel of each other’s cocks. Then at the end of the lesson when we had some time we hand jobbed each other to cum. It was my first time doing it for another boy but he’d done it before. He had some lube for solo masturbation which he used on my cock and he gave me a good one. The next times were planned!
Not really. It was with my freshman college roommate. It was late, we'd both gone to bed, I was quietly (I thought) masturbating. It turned out she was also. She heard me and came over to my bed where she whispered, "Need a hand?" It startled me and then I laughed as she slid in next to me. One thing led to another. It was the first time but not the last time.
My Festive Flash competition story was I recently published-- https://www.lushstories.com/stories/incest-fantasy/driving-home-for-christmas Hope you read and enjoy it! Don't forget to comment. ☺️
Recently published https://www.lushstories.com/stories/lesbian/women-desire It's part two of my Women series where Kate and Maura continue their journey of fem desire. The first part is https://www.lushstories.com/stories/lesbian/women-murder
Quote by garterbelt
First time I had same sex, was not planned, it just happened. He and I were looking through his dad's playboys and he asked if I wanted to wear his sister's bra and panties. Well of course I wanted too!! He then told me since I dressed like a girl I should suck him like one. I got to wear his sister's lingerie every time I would suck him, I wore her lingerie a lot!!
Same
First time I had sex with a guy it wasn't really planned it just happened.Spent the night at a classmates house.We were looking at a Penthouse magazine and I couldn't get over how the women in lingerie looked so sexy.In my minds eye I imagined that I was a girl and I just had to give my friend a handjob.We were already masturbating at that stage anyway.I just took over for him and next thing I knew he ejaculated all over my hand
First time for me was at a sleepover with a friend.We were in his room looking at one of his Moms Victoria Secret catalogs.He was saying how sexy the women looked whereas I was totally wishing I was one of those women. We both started to jerk off .I took it it a bit further tho and gave him a blowjob ,he exploded in my mouth and I swallowed all of his jizz
My really first time was unplanned. I was at my all boys school. We were sitting in a darkened lecture theater watching a historical movie. The boy sitting next to me put his hand on my thigh. I knew instantly what he wanted. I spread my legs to show I was willing and his hand moved to the ridge of my erection. I let him get my erect cock out and have a good feel. Then he wanked me off to cum. That was before the swimming lesson event I described above.
Never planned but I think I was subconsciously ready as I jumped at the chance, I was really horny about the idea of jerking off together and we repeated many times after that. We jerked each other off for almost two years before he moved on to dating women. He was a year older than me and I always liked our time together and missed it and was from then on very open to the idea of getting with hopefully another friend. I certainly jerked off thinking about many of my friends after first getting together with my neighbor friend.
I think 90% of sex between new partners (possible exception being Bill’s “accident,” which is hot AF by the way) is planned by one or the other. In most cases, if you think it was unplanned, that just means it was unplanned by you.
My newest story: Midlife Resurgence: Piñas Coladas
Not in the contest but Festively Flashing: Disrobed
Festive Flash competition entry: Amy's Mom
I get dicked by a federal agent in Recommended Read Dick Job
I pork everyone in my other Recommended Read, Pork by Northwest
Card catalog? Hard catalog! My library
Quote by dpw
Not on my part but maybe on his.
Went hiking with an older neighbor when I was in my teens.We went skinny dipping in a cool mountain pond on a hot day.He came up behind me and pressed his erection against my butt cheeks, pulled me around to face him and kissed me on the mouth with tongue.I got a major boner and ended up giving him a blow job.I must have done it right as he rewarded me with his creamy load
Mine was not planned at all. Had known him since high school.. We were in our 30s. Went over for the weekend to party with him and some girls we had coming over. Sometime around 3am, I felt myself going out. I don't remember getting to the back bedroom or anyone leaving. Came to with him inside me on top. I remember him seeing my eyes come open. I was so drugged, I just kept staring at my own cock wondering why was it erect during this...then I passed back out. Didn't remember that event for year but heard 2 years ago that karma had taken him to the other side and 6ft under. That brought back all these memories of it...and for some reason I started to fetishize it.