This happened back in the summer of 2017, when I was a grad student. I’d met a slightly older girl, we’ll call her B. on OK cupid, and we went and got coffee and wandered around the neighborhood. She was a BBW, with an expressive smile, beautiful eyes framed with librarian glasses, and bobbed haircut. And magnificent boobs.
As we wandered and chatted I became deeply aware of how much I wanted her. Hesitantly I asked to kiss her, and our lips met with warm passion under the flowering dogwood tree. We meandered back, and ended up in my bedroom.
We kissed, first gently and then intently. I slipped off her shirt and cupped her breast through her bra. She slipped her hands down to the hem of my shirt and lifted it off, her arms holding me close. Between kisses, little gasps and moans we ended up naked, her pink folds ready for my now swollen cock. And then we had to slip it in.
Alas missionary didn’t really work. She leaned back on the bed, as I sicssored into her. But when I went to reach for the condom to roll it on, my cock lost just enough hardness to make it not slip in. She looked at me and said “Just stick it in”.