Where it happened: walking home
Langauge: English
Sex: Male
Rating: 2
Category: Straight
My first time was with our 42 y/o neighbor lady. I wish I could tell you she was a real “hottie”, but in truth she was very plain looking and the whole thing was very embarrassing.
One day I was walking home from school, and I saw “Mrs. M” walking down her driveway in her robe and slippers dragging her trash can to the street. So I offered to help her, and she asked me if she could borrow my muscles for a few minutes to move some things out of her basement. (To describe her – Mrs. M had dark brown hair and was very full figured, but had a very plain face as she rarely wore makeup.)
Anyway, when we were down in the basement I caught a glimpse of her tits when she bent over once, so when we were through moving stuff upstairs I asked if I could use her bathroom before I left. So I promptly started jerking off, and without realizing that her bathroom door did not lock properly she walked in on me – I had my pants around my ankles, and I was sitting on the toilet with my dick in my hands. I was completely humiliated and embarrassed.
I guess I could make up some lies at this point and say that she stripped off her robe and jumped me, but in reality she looked appalled and told me to get dressed and that she was going to call my mother. All the while she called me “pervert” and “sick little boy” and things like that. So I started begging and pleading with her not to tell, and after about 15 minutes of that she agreed not to say anything.
Before I left she asked why I did it, and I told her it was because I caught a glimpse of her tits. . .and that I had never seen a woman’s breasts before. Mrs. M immediately changed her tone and actually seemed flattered by this, so I went on and on telling her how beautiful I thought she was (I was lying through my teeth) and that I had always wanted her (yeah, right). So while she was sitting on the couch she laid back and told me to sit by her. . .when I did she pulled her robe back exposing her big brown pussy, and told me that it was my lucky day.
“Okay, go ahead and put it in me,” she said. “I’ll give you 5 minutes, and then you have to go. You better hurry up before I change my mind.” So I awkwardly pulled down my pants and underwear, and because I was so nervous I had a hard time getting an erection. So Mrs. M started stroking me off (she looked bored the whole time), and finally told me it was probably hard enough to insert. So I took the head of my dick and rubbed it up and down over her slit, and she got frustrated with this and reached down and inserted it herself.
We humped for a few minutes before I shot my load in her, and then she told me to go home. I remember that it felt really good, and that she was real loose. She told me to promise not to tell anyone. . .Over the next few years she would frequently fuck me whenever she needed it, although
neither one of us was real attracted to the other one.
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