When I was in college circa 2009, I lived with 2 friends and their gfs. One night, everyone was gone except for one of the gfs and she had a friend over hanging out in our living room. I’d just gotten home from work and changed into some comfy clothes including some thin athletic shorts. I would consider myself generally playful and an inadvertent flirt. The gf was sitting in our living room chair and in order to get to the couch so that I could sit, I stepped over her in the chair and playfully straddled her for a moment. She could feel my cock dangling in my thin shorts and reached out and grasped my shaft, resulting in me swelling in her hand instantly. We locked eyes for a second and I continued stepping over her to the couch.

After her friend left she talked about not feeling like sleeping alone and asked if she could sleep with me. I was so worked up at this point so I happily obliged. Once we were in bed I couldn’t help it. My cock was throbbing while she let me spoon her, poking her plump little ass. She was reaching back and playfully touching me, at which point her conscience kicked in and she admitted we shouldn’t do more. I told her if I didn’t cum I was going to lose my mind, and told her I was going to get out of bed to get off. I sat in my desk chair and pulled up some porn on my computer. She stood over my shoulder and watched while I stroked my cock to videos until I exploded in front of her.

Wishing I had the kinks then that I do now and would’ve found some more fun ways to play for her.