I was groomed by a much older woman who took my virginity and used me as her personal sex toy for over a year. 10/10, would recommend. [FM]

I turned 18 right before my senior year of high school (I’m 27 now). My folks are divorced and I lived with my mom in those years. She was/is a corporate attorney and travels a lot for work, so she was often away during the week and some weekends. I was pretty independent and she’d leave me money for groceries, food and stuff. (This makes it sound like she was an awful mom but she totally is not, by the way.) She also had a friend of hers who lived nearby come and “check on” me a lot – “Lisa.”

Lisa was about 49 at that time. She was very “suburban mom attractive” – about 5’6, dark brown hair, liked her makeup. Pretty well-endowed (she’d had two daughters). She and my mom had been friends since college and had both been through divorces. Lisa knew me since I was a baby. She always talked about how handsome I was when I was a teenager, giving me shoulder rubs and playing with my hair – that sort of stuff.

So one Monday evening in my senior year, Lisa comes over to “check in” on me while mom was away. She cooked me some mac & cheese and asked if I wanted to watch a movie. I didn’t really, but said okay, and she turned it on. I forget what movie it was now, but there was a lot of sex. A bunch of good scenes, and they went on for quite a while. About halfway through, I was pretty hard, and had sorta angled my leg to hide my boner.

After a while, Lisa moved her hand and rested it on my knee. She started making little circles on my inner leg with her fingertips. I had no idea how to respond, and was obviously surprised, but it did not exactly make me less hard. I remember the scene on TV – there was a couple going at it doggy style, and the woman’s breasts were bouncing back and forth as she was being taken. Lisa moved her hand slowly up my thigh until her fingers were on my cock, over my shorts. I think I gasped, because it felt really good (a girl had never felt my cock before).

She sorta “shhhh”‘ed me and started squeezing my cock through my shorts. Then, she undid my zipper and eased it out. Without saying anything, she stroked my dick as we watched this sex scene. I probably came in less than a minute, and it went all over my shirt.

“Was that good, honey?” She said. I nodded or something. Then she sent me to go change. We watched the rest of the movie and didn’t say anything about it.

The next night – Tuesday – Lisa came over in the evening again, again to “check on” me. It was late. She asked if I liked what she had done the night before. I sorta stammered “yeah,” and my cock instantly got hard again. She asked if I wanted her to do something like that again, and again, I said… “uh, yeah.”

But instead, she took my hand and led me up to my bedroom. She told me to get undressed and that she’d be right back. She went to the bathroom, and I stripped down. I honestly had no idea what was going to happen. My heart was pounding and my cock felt like it was gonna explode.

When she came back, she was in just a towel. She dropped it in my room and let me look her over. Her tits were full and beautiful, hips were curvy and womanly, and her pussy was closely trimmed. She asked if I had wondered what she looked like naked before (I had) and if I’d ever been with a girl before (I hadn’t). She said she hadn’t thought so, and she made me lie down on my back on my bed. She straddled me and squeezed my cock with one hand while running the other over my chest. She told me that I had to swear not to tell my mother about any of this. I swore, because I began to realize what was about to happen.

Then, Lisa eased herself on top of me and sank down on my cock. She probably didn’t ride me for more than a minute or two before I came. She let me blow my load inside her (“that’s it, baby – let me have all of it…”), and she kept riding for another few minutes – I stayed hard – until she came, too.

She stayed over and slept in the guest room. Early the next morning, I woke up when Lisa came in again. She was wearing just a big t-shirt and panties, which she stripped off in my room again. I was obviously surprised, but almost instantly hard again. She mounted me again and rode me, longer this time, until she came, and then she reached around and played with my balls until I came too – inside her again.

This is getting kinda long, so I guess I’ll summarize other stuff:

* our relationship was definitely not equal – she used my dick as her personal dildo. She usually rode me, but occasionally had me go on top and fuck her missionary
* She taught me to eat her pussy. During the school week, she would tell me to come by her house really early on my way to school so I could go down on her and make her cum. If I was lucky (not always), she would lie back on her couch and let me slip my cock inside and fuck her until I came, too.
* She would only suck my cock when she needed me to get hard, fast. She never let me cum in her mouth.
* She would usually only suck my cock if she had just fucked me, I had cum, and she wanted to keep going. To get me hard again, she’d suck on me, and I would usually come back in a few minutes. (Ah, to be 18 again.) She would tease me and play with my soft cock until it was hard again so she could fuck it.
* Not infrequently, she would use these play cuffs to restrain me to the bed at her place, with my wrists above my head. That way, she would get me hard, fuck my cock for a while, and then sit on my face and make me eat her pussy. She would cum over and over and over like this, usually while she played with my cock but didn’t let me cum. She would end those sessions by finally letting me cum inside her, and she made me ask for it.

My mom never found out about anything. I finally went off to college and that put an end to it all.

So, I know some folks would call her a predator, and I guess she sort of was. She definitely took advantage of me. For a few years after that, I was really confused when girls I was with didn’t take the initiative and just tell (order?) me what to do. I had no idea how to take the “lead” role. But eventually, I figured it out. In retrospect, getting “initiated” like that was… actually amazing, especially for such a young guy. I got a lot of great experience and some mind-blowing sex. I miss it!

Source: reddit.com/r/gonewildstories/comments/hem1ma/i_was_groomed_by_a_much_older_woman_who_took_my

13 comments

  1. You should definitely share some more stories about her, sounds like a dream come true.

  2. This was my dream 2 years ago. I’m glad you got to experience it. If you were to compare her to any celebrity, public figure, redditor,etc. Who does she most closely resemble?

  3. If you were legal, all fair, I guess. I don’t think I’d have minded.

  4. I had something similar except I was more dominant and it didn’t last as long, but yeah 10/10. I never posted about it but everybody downvotes me when I comment about it because I was underage and I guess that’s my fault in their minds.

  5. You are one lucky person, to have had such a great experience with a great woman, believe me this type of adventure will live forever with you, so use it wisely!
    Oscar

  6. I had my share of older women when I was younger but not this much of a age difference. Enjoyed the story.
    I guess I was just a Male slut at age 13 I use to sneak the neighbors daughter out at night, after my first I went on a fuck-a-thon until age 25 I settled down got married, Aids was on the rise during late 80s so something has to change but this brings back some good memories. Thank you for sharing.

  7. I had something silar happen but it was a friends babysitter. She was 19 I was like 14. I had lots of fun lol.

  8. Aye there is a Jim Jefferies skit on that. The words go something like: “Boys and girls are simply not the same….if a girl sleeps with her teacher…she ends up in therapy for years and eventually becomes a stripper – whereas boys just go hi-five their mates”.

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