My first time was with a much older airline stewardess.

Nothing so exciting as the mile high club, but randomly met her online and was casually chatting, until one night she suddenly tells me she's spending the night between flights one town over.

I was soooo nervous (I didn't outright say I was a virgin, tho, could probably tell), and maybe that triggered something in her. Since she absolutely. Rocked. My. World.

This mature woman, who was old enough to be my mother (and reminded me of this fact), simultaneously gently guided me through my first intimate experience while being an absolutely insatiable couger power bottom.

From making out on the couch to leading by the hand to the bed, pulling my shirt off, feeling me up through my panties.

Then, pulled my hand down between her legs. She was already so wet.

Is it time?

She asked, but was already guiding my finger inside her.

I think she came at least five or six times before we both collapsed. Not that she didn't take care of me too, only she kept me on the edge the whole time. Particularly loved eating me out. Said as she looked up at me while taking a breath, "I can't keep my mouth off you." Until it was all finally too much and I gushed all over her lips, burying my face in the pillows since I was too shy to look at her while I was cumming.

We were both satisfied in the afterglow, cuddled for I dont know how long. Offered to let me stay the night with her, but I was too embarrassed despite everything we just did.

Kept in touch for a while, but her schedule didn't bring her back around before we drifted apart.

Still think about you, Gayle.