Where it happened: Woman's apartment
Langauge: Eng
Sex: Male
Rating: 5
Category: Straight
Speaking about first times! Mine was quite unusual. I was in high school in my jr year and I walked home from school every day. On the way, I had to pass a housing project. That year, I very often saw this woman who’d set in a chair just outside her front door. She was probably in her mid to late 20s and me being the young horny teen that I was, I’d look at her on my way by peering up her skirt. She was around 5’6″ tall and probably around 110 to 115 pounds. In other words; she was BUILT! I’d then get home thinking about what I’d just seen and would jerk off thinking about how I’d love to get my hand up that skirt for a good feel of what I had just seen.
Then, this one afternoon as I walked by, she spoke. She said “Hey” and I ask “Who, me”? She said “Yes. Do you have a minute”? I said “Yes” and walked over to her. She then ask if I had any money on me. I told her that I had a few dollars. She said “Would you like to have sex with me”? I was caught off guard for a minute and didn’t answer. She said “If you’re interested, come on in” and she got up and headed into her apartment. I had already got an instant hard on and this was all it took. I followed her into her apartment. I couldn’t believe my luck. I was dying to get a feel of those inner thighs that always turned me on so much. After going to school day after day and seeing the girls at school in there short skirts and shorts I just instinctively knew just how good and soft they’d be.
She took me back to her bedroom and ask for the money first. I gave it to her and she started taking off her clothes. I then told her “Really, all I want is to feel your legs and have you play with me a little” showing her my fisted hand as if jerking off. I knew she’d know what I meant. She said “Sure; drop your pants and come on over here” I did showing my cock to my first woman. I sat besides her on her bed and reached over placing my hand on one of her wonderful thighs. She then reached over taking my cock in her hand and started stroking it. I ran my hand down between her legs feeling some of the softest flesh on a woman’s body. I just knew it would feel like this and if anything, it was even better feeling! I quickly went off shooting cum on both of us.
This was my first experience with sex other than jsrking myself off. In later weeks, I’d drop by and see her on my way home as often as I could afford it for a feel of her wonderful feeling thighs and her expert hand jobs. We ended up laying down on the bed where she’d lube her hand and rub my cock against her inner thigh until I’d cum on it. This sure felt good.
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