Today I got a Friend Request on Facebook from a woman named Jessica. I looked at her pictures, and she only had two posted. Neither looked familiar. I thought it was probably spam and that if I looked around long enough I would find her seductive request for me to check out her naughty photos on another website. But just before I clicked away, I saw that she went to the same high school I did in El Cajon, a suburb of San Diego, and graduated the same year. I looked at the pictures again. Nope, I still didn't recognize her.
I sent her a message saying:
Your face definitely looks familiar, but it has been a long time. I'm going to have to pull out my yearbooks. Hope you're well in Kansas! Tony
And here was her reply:
you were my bestest bud like 10 grade...had honors english together...um used to hang out, my mom was crazy and felt you up once.. lol
Ooooohhhhhh, this is Jessica whose Mom felt me up! That's right. I went to go visit her down the street from where I lived in her trailer park. I can't remember what we were doing that day, but I remember her Mom flirting with me. Then as I was leaving her Mom followed me outside into the driveway that ran through the park. She gave me a hug goodbye, and then put her hand on my crotch and said something like, "You sure are a cutie. Why don't you let Momma check out the goods." Even at 15 I thought it was hysterical. Crazy woman! However, I do also recall that I wanted to visit Jessica at home more often...
Oddly, that was not the first time a mother felt me up. The year before that when I was 14, we lived in an apartment complex, and our apartment faced the pool. Across the pool was another apartment inhabited by a woman with two kids named Elizabeth who couldn't have been older than 19. Liz was a pretty woman with curly dark hair, and she lived with her very tall husband named Darren. In the summer between my freshman and sophomore year I was home all the time, and I started hanging out with Liz to pass the time.
She could tell when my mom was home because she could see Mom's parking space from her living room window. One day when the parking space was empty Liz came over to my house and opened the door without knocking. I was laying on the couch in the living room talking on the phone. Liz closed the door and came in. I gave her a funny look, but kept talking. Liz walked over to me and straddled me on the couch, and I quickly became very aware that her genitals were closer to mine than anyone's had ever been before. She reached back and put her hand down the leg of my shorts, and within seconds was rubbing my crotch. She used her other hand to grab one of my hands in the front and push it up her shirt. I was so nervous that I kept my conversation going on the phone out of complete fear of what would happen should it end. Liz got annoyed that I wasn't getting off the phone though, and before long she got up and did a little tantrum walk as she left the house and slammed the door.
On a warm night soon after that Liz and I met in the pool. Darren wasn't home, and Liz decided to try again. As we talked and swam around in the pool, she started getting very flirty. Soon her top came off, and she backed me up to the edge of the pool, conveniently covering the only light in the area. She wrapped her legs around me and pulled my face to her as I started licking her breasts. I can't remember what stopped it, but I think it might have been Mom calling me from the living room.
Liz's last attempt was made in her house one night when Darren was out. We were hanging out watching movies in her house, and I remember her laying on the floor next to me. I can't remember how it started but I do remember some connection between her breasts and my boner. But as I laid there on the floor, Darren walked in. I rolled onto my stomach in about a half second, and then laid there greeting Darren and asking about his day while I waited for my pants to loosen up. As soon as I felt I could stand without my tent pole giving me away, I said goodbye and practically ran out the door.
Darren was no fool though, and after that Liz said she wasn't allowed to hang out with me anymore. I didn't care though. At the end of that summer I got my first bj from a girl in the grade below me, and Liz with her lactating breasts became old news.
I slept with very few women in the next few years because by 17 I realized that my time was much better spent with men, but interestingly, the last woman I slept with in December 2003 in Sydney was a mother. She may very well be the last woman I have sex with. Wouldn't it be interesting if I started and ended my female sexual experiences with mothers? I guess that brings a new definition to the term "Momma's Boy"...
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