First sexual encounter

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39m

When I was a kid I had a neighbor that was a family friend and someone I did household chores for. Mow the lawn, rake leaves, shovel snow and the like.
She was a gorgeous full figured Mombod in her 40s with two older boys. She had a major impact on what I discover attractive to this day. I remember this women alway coming over the house from a very young age and being a friend of my mothers. I’m not sure what happened to her husband but for some reason he just disappeared one day and no one talked about it. So I’m not sure what to say about that. Anyway. I spent a lot of time with this woman growing up. She would watch me when my mom was out of town. I’d spend the night at her house. Her boys were older than me, and not very nice to me they would at all times pick on me. I remember sleeping in the same bed as her, when I was really young. She was like a second mom.

one summer, let’s call her miss Johnson. Miss Johnson’s youngest son moved out of the house and went away to school. (Miss Johnson’s other son moved out a year earlier) So I became the primary person for household chores, I was 16.

Well, this summer miss Johnson’s house was being renovated and she was staying at my house. this is when I became obsessed with finding and sniffing her panties. Every chance I got.
One morning I was being a little perv and snooping in her room and masturbating to a pair of her panties when she walked in on me. I had no idea she was even in the house and wondered I was alone. I panicked and tried to cover myself. Ms Johnson just laughed at me and called me out. Saying I was a perv and was bad and shouldnt be going through other people’s belongings, let alone underwear. I ran out of the room and she followed me and cornered me in my room. She told me that she knew this is what I have been doing. She had been finding her underwear wet. Miss Johnson told me that later we would have a talk about this and unless I wanted her to tell my mother, we would talk.

Well later that night, filled with anxiety and my mind running through scenarios of disaster. I went to my room after chores and what did I discover? Miss Johnson sitting in my chair and a pair of panties on my pillow! My mind was blown. I didn’t have a clue what was going on. I just stood there ready to piss myself. I knew she wanted to talk to me, but this is not what I expected.
After an incredibly long awkward silence. She spoke, “you didn’t finish this time” (or something like that?) anyway. My brain froze, I could breathe. Miss Johnson stood, walk over to me and whispered in my ear. “I want to see what you’ve been doing” “how long have you been doing this?” “Have you always looked at me this way?” “Am I the only one?” “Did you do this at my home as well?” “Should I talk to your mother?” “ why did you think I wouldn’t find out when you cum in my panties and leave them wet in my room?”

I was scared, confused, ashamed and… aroused? wondered I’d die. My dick was rock hard and why wouldn’t it. She was in lingerie? I’d never seen any before. I didn’t know clothes like this existed.
Miss Johnson walked over to my bed, picked up the panties, (this was when I noticed them) walked back over to me and held them out to me. “You like to smell them?” “To touch yourself with them?” “Do it for me!” After a long pause. I wondered fuck it. I took them and sucked in a deep sniff.

She just watched me from the chair. Never touched me or herself. Never made a sound. Miss Johnson just watched me smell her panties and pleasure myself. As I was getting ready to finish she said “cum in them” no idea how she knew I was ready but I did as I was told. Miss Johnson stood, Walked over to my bed and took them and smelled them. Right there she smelled them. I watched her one leg at a time put them on. my brain froze again. I didn’t know what to do. Miss Johnson said “this stays between us ok?” I shook my head said something intelligent (yea right) she said “when you were little and you’d spend the night at my house and sleep in my bed you would always dry hump me in your sleep” “such a perverted little boy” she left the room.

I went to her door a few minutes later and it was locked. I listened and could hear breathing and moaning and the buzz of what I later understood was a vibrator. I jerked off right there outside her door.

The next day she went to stay with another friend while her house was being finished and after her house was done I did a few household things outside but she wouldn’t invited me in. Miss johnson acted like it never happened. After about four months out of the blue she invited me in. Miss Johnson told me there would be some ground rules that we could not under any circumstances touch one another. she then gave me a pair of her panties and she watched me masturbate into them.

Then, she took them from me put them on and for the first and last time, sat me down on the couch laid on the floor in front of me and masturbated with a dildo. This was my first time seeing a woman do this and this was the last time we did anything together. She sat me down a few days later and told me that what we did was wrong, and it can’t happen again. A few years later, she sold the house and moved away, and I never saw her again.

NSFW: yes

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