In those days, the handjob came after I had her naked and had been fingering her a while. I had lots of precum by that time.
Sounds like a really good experience, she obviously grips mine in the boxers but she does rub it on the surface first
Something similar many years ago at the stripper bar. She was rubbing her ass on my penis with a specific goal I dared ask if she would also touch with her hand. I kept in in my pants but out of my underwear, condom on, wearing loose sweat pants. She touched nicely a few times, and stroked me after she triggered my ejaculation with her ass. That felt quite good.
I posted about meeting with an attached woman discreetly in another post. I have received a couple of handjobs with her hand wrapped around my cock and I fondled her breasts. I actually really would like to try her rubbing my cock over my underwear until she makes me orgasm. It’s been a fantasy since a lovely young lady brought me close but I ended up having her pleasure me orally to the finish about three years ago. More to follow.
I posted about things in the thread Getting masturbated. So far only straight handjobs, full hand on, with a condom on because it’s in my car - no mess that way.
I got to try the underwear thing today Same woman who gives me edging hj When we met unplanned we briefly talked about a probable time to play. I said I had a bit of time but she didn’t have a lot, but fine to meet if we kept it short today, no edging. I was fine with it especially that she gave me a reduced price. She was a little surprised I asked her to rub and touch me over my underwear but she went along. It felt like the time I had it before except that she went all the way. I was pretty excited and turned on, soon I was leaking through my underwear. She said “I guess you will just cum that way.” I almost came and she stopped because it didn’t take long, commenting on feeling the orgasm through the shaft. She ended up edging me twice more before making me cum. After that she wiped her hand, used sanitizer and asked to see how much I came. I always fondled her breasts the other times except that time, she mentioned it and that I must have been into it for not touching her breasts. I said I would have liked it and looked at them, she gave me a bit of time to play with them before she had to go. All that to say I got a variation of a hj in underwear and I like telling the details.