This is an event that happened to me when I was about 19, but still living at home. My step-mom and my father had gone on a hunting trip together, and left my step-mom's best bud, Terry-Ann to, well, not *baby-sit* exactly, but to help me take care of the household stuff, feed the dogs, clean, etc...we had a big house in Palo Alto, Ca.
Terry was fairly hefty, with long, mousy-blonde/brown hair. Long hair on even a heavy woman makes her look pretty hot to me. At some point in the evening, we ended up talking about relationships, while watching tv, and sitting on my parent's bed. The conversation started to turn suspiciously erotic when she started to ask me about what I liked to do with my girlfriends sexually...and being a horny 19-year-old, I told her. It was nice to have an older adult woman to talk about such things with.
After a bit, she got pretty bold, and started to caress my thighs through my jeans as she talked. Eventually, she ended up rubbing my bulge, and asking me, "Do you like that?" I admitted I did. I started to feel weird about it, and said, "Um, I've got to go to bed now!"
(I did have classes in the morning, at the local Junior College)
She got *very* disappointed, as I left my parent's bedroom...and was just laying there in my own bed, thinking about how weird it felt to have my step-mom's friend come onto me like that, and how I'd just escaped letting it go further. But as the minutes ticked on, I got more and more horny, until I couldn't stand it any longer. This was about 15 minutes of deliberation later...
I stripped off completely, and went back into Mum and Dad's bedroom, and told her I'd changed my mind...She left her nightgown on, but started to jack me in a very masterful fashion. I tried to kiss her, but she said, "Sorry, I'm not in love with you...this is just for fun." I said OK and began to play and suckle upon her ample breasts which she offered me as an alternative...shouldering off the top part of her nightgown for me. It was so electric and *forbidden* and *nice* to be the sex object of this older woman, who clearly knew what she was doing to me.
The thing the lent an extra bizarre kink to it all, was that during this little erotic drama, Terry-Ann's 7-year-old daughter was slumbering in darkness right on Terry's other side of the bed.
I knew that Terry-Ann was kind of "white-trashy", and I guess the allure of her invitation to be jacked off and such her breasts while her own offspring was in the bed was too much to resist as a kink factor. She'd told me that her boyfriends have done her while her daughter watched before...and that she was used to it. I'm not saying I'd do that again today...but it just goes to show you how the hormones of a 19-year-old lad can make them do the most bizarre things.