Some of my little short stories seem to have some success, so I’m going to write a couple more of these. They’ll both involve an ex gf who we’ll call Jane. She hasn’t featured in any of my stories thus far, but if any of you read my first and second M/M experiences, this is the gf mentioned in those. This first story involves her first handjob and how she unknowingly made me cum in my pants.

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For some background, Jane had a massive crush on me all through high school. It never amounted to much because I had a gf at the time even though it didn’t stop her from being flirty and making very obvious hints about her crush. Even to the point of having friends call me to see if I liked her. I did, of course, but didn’t want to come right out and admit it to her friend since I was with someone else at the time. She moved to a different school during our last years of high school, primarily because she felt embarrassed by her crush and had to see me regularly knowing that we could never be together. There’s a bit more to it than that, she had friends in the new school already and it was technically closer, but her crush was the primary reason.

Eventually I broke up with my high school gf and it was more than a little messy. Jane immediately came to mind and I reached out about a week later. I know it was a little rushed, especially being fresh out of a relationship that lasted a few years. I explained what had happened and let her know I was single now and found out she was still available too. We decided to take things slowly and just hang out as friends at first. I already knew her friends that had gone to my school, but none of the ones that had been at her new school.

This was a few years after high school and I had a night shift job. At the time she wasn’t working, but this left us plenty of free time over the weekends. We mostly hung out in groups, meeting up for bowling or going to a local bar. We never really went on a proper date. I was still healing, but we still wanted to keep each other reserved. It took me forever to ask her out. Her friends would pester me, asking when I was going to do it but my nerves kept getting the better of me.

Eventually it happened and we got together. We started doing a bit more one on one dates but still regularly hung out with the friend group. Her and her friends really made this relationship the highlight of my 20s. I learned she was a virgin, had only had a couple of boyfriends, and that she’d never gone further than making out. I’ve never been one to pressure any of the women I’ve been with. We talked about sex, obviously, and I encouraged her to let me know when she was ready and we’d move at whatever speed she was comfortable with. We spent a lot of time making out in the car after our dates or group hangouts. Some nights we just spent hours in her driveway chatting until the wee hours of the morning.

Jane had a cute face with exceptionally big blue eyes, a weakness of mine. She had the largest tits out of anyone I’ve ever been with, before or since, with a nice pair of DDs. They were like these perfectly shaped orbs dangling from her chest with light brown nipples and an oval areola. I spent plenty of time playing with those girls and she loved showing them off. Constantly wearing push up bras and low cut tops. Even after being together for a few years she would have to (jokingly) remind me where her eyes were. She had a naturally flat stomach, soft but still flat. Her hips were incredibly wide and she had the massive plump ass to go along with them. Her body was absolute perfection.

I’ve mentioned my basement set up in a previous story. It was mostly unfinished with a TV and some furniture on a chunk of carpet. We ended up here pretty often, watching TV and with lots of making out, dry humping, and breast play. She had rubbed my cock through my jeans a few times, but only ever briefly as she worked up the courage to do more. This short story is about the first time she look things a little further.

We had already been making out for some time. Her top was off and I was loving my time with her tits. I was on top of her, grinding my hard cock against her pussy. I could tell how turned on she was. She had a strong, noticeable aroma whenever she was horny and it was something I loved. She had an amazing scent and an equally great taste.

I felt her hand moving down between us. I lifted myself to give her access to whatever she was trying to reach. My jeans were a loose fit and my body trembled with anticipation as I felt her hand venture beneath them. I lifted off more to give her as much access as possible. Her hand explored my cock, only the thing fabric of my underwear preventing direct skin on skin contact. It wasn’t long before I felt her fingers squirming beneath the waistband and that incredible moment of her bare hand finding my cock for the first time as she let out a soft little moan into my mouth.

She had no idea what she was doing down there. Everything was loose enough that she had plenty of room to move her hand around and she used that to touch my cock all over. Feeling every inch of it. Tracing her finger around the ridge where the head meets the shaft. Gripping and fondling my full balls with her inexperienced hand. While she never got to the point where she was giving me a proper handjob, I consider this among the best I’ve ever had. The way her virgin hand explored me was one of the most exhilarating things I’ve ever experienced.

A combination of things came together in this moment. I knew this was her first experience. I could feel her eagerly exploring me. I hadn’t cum in a few days. Her tits always got me more horny than I could ever have imagined. I could feel an orgasm slowly approaching. I would have come much sooner if she was jerking me off properly, but what she was doing managed to get me to the edge and keep me hovering there for much longer than I was used to. I didn’t want to freak her out and cover her hand in a hot sticky mess the first time, but I felt like I was about to cum any second.

I put my hand around her wrist and told her “if you keep going there’s going to be a pretty big mess.” I wanted to let her make that decision and she decided it was best to stop before I could cum. She wasn’t quite ready for that yet, which I understood and let her take her hand out.

That’s when I realized it was too late. Somehow I kept a straight face as I felt the muscles in my groin tense and relax. Tense and relax. Tense and relax. My body decided I was going to cum whether I wanted to or not. All the muscles around my cock tensed up and I felt myself pulsating in my pants without anymore stimulation. I couldn’t help it. I was cumming for her.

I must have kept a straight enough face somehow because when it came up a few years she told me she had no idea she made me cum that night. She thought I had stopped her just before it happened. I immediately left for the washroom and she had assumed I went to quickly finish myself off, knowing how close she had me. Really I was off cleaning up the incredibly massive amount of cum in my pants. It was my place, so I had fresh clothes to change in to and she must not have noticed that either. Sometimes it can be hard to tell one pair of jeans from another.

Things progressed and I eventually tighter her how to give a proper handjob and she loved how easily I made her cum with my fingers and tongue. The actual sex was pretty straight forward and never anything out of the ordinary, but her pussy was incredible. That perfect feeling where she’s not so tight it hurts and no so loose that I couldn’t feel anything. She had a pussy that fit me perfectly and a body that I was obsessed over. I only add this because I can’t think of any sex that we had that was particularly noteworthy or story-worthy. However there’s one series of events I’m going to write about next. A little bit about how often we made enough other cum with plenty of oblivious friends mere feet away. But that’s a story for another day.