[MF] An Old Friend (39F) Of The Family Shows Me (18M) A Side Of Her I Never Knew About Before

Thought I would share an unusual yet memorable experience that left me quite puzzled yet gratified about what transpired. Growing up, my mom’s old school friend named Jessica became well known with the family since before I was born. She apparently used to babysit me when I was little but all I can remember about that was her house. She worked in the public schools and she was my teacher for a couple of classes, Comprehensive and Foods class. She attended church twice a week and did a lot of stuff for the Church. I’m now 18 and a couple of years ago she took another job and moved to NY. In May of this year she got divorced and moved back though never heard why.

Not long after she came back my mom and sister were gossiping about her and said she moved into a small apartment and got a “temporary job” as my mom put it, as a stripper. It surprised all of us which is why they were gossiping about her because the Jessica we always knew was very religious, reserved and carefully spoken. She would never even show any skin beyond her arms below the neckline, that’s how reserved she always was. The new Jessica is more spontaneous, very open with talking about herself and now suddenly working as a stripper? None of us could believe it yet Jessica apparently was quite open about it. I would have never saw this kind of behavior coming from her but whatever she did in NY certainly seemed had an effect on her or maybe we were just getting to know the real Jessica? I dunno but what transpired still shocks me to this day.

Fast forward to October, she went back to taking community college courses, for what I don’t know but seemed odd to me that she didn’t go back to teaching. I had recently broken up with my g/f. Now I don’t know the details but my sister apparently told Jessica about my breakup and I get a text from her saying she was with my sister and was told about what happened and wanted to know if I was ok and if I needed some company. I had assumed she meant company as her and my sister coming over and as I was wanting an excuse to go out drinking anyway, I said sure. I figured we’d all could go out to the bars as I don’t like going alone.

I’m staying in a fully furnished apt above a garage and I’m only like 5 min away from my sisters house where they were at and quite a few hours had passed so wasn’t sure what was holding them up, it was now 10 pm and I figured that they weren’t coming. I was pretty bummed as it was and now more bummed that I wouldn’t have anyone on hand to go drinking with because my best friend never did text me back that night on if he wanted to go with me or not. I finally get a knock at the door and it’s just Jessica by herself wearing a tight skirt, form fitting shirt and tall high heel leather boots and I’ve never seen her wear any type of clothing like that before. I let her in, offer her something to drink and we sit on the couch. She’s asking how I’m feeling, etc and I’m like “well nothing some booze can’t numb” and I asked if she wanted to go out with me to the bars so I can drink my sorrows away but she insists on just hanging out saying “we can have as much fun here” and at the moment I wasn’t catching on to what she meant as I insisted it was boring here, I wanted to get all liquored up but I later realized that must have been her first hint she was trying to drop to me.

Further in a conversation about what I don’t recall, she drops another hint by casually mentioning “the fastest way to get over someone is to have a one night fling with another girl” Again I didn’t think much of it and took it as a suggestion for me to find someone willing for a one night stand as I respond that I’m not much of a pickup artist and I was naive enough that I didn’t realize she was setting out bait for me. I mean why would I? She was twice my age and if she’s the same age as my mom then she is around39 yrs old but looks a little older than that to me. Someone I picture baking me cookies, not seducing me. I just figured she was trying to help by saying whatever she could come up with but I didn’t think anything other than booze was going to make me feel better that night.

So she takes another approach and asks me to take her picture. She makes a pose and so I oblige and then she starts doing various other poses to get me to take more and more pics. Then she gets more into it and her poses get more suggestive and it seemed a little awkward. The way she posed, for the first time, did get me to notice her physically like that and I suppose that was her intent, she has a decent body for her age if nothing else. She stands up and asks “want to make some pics for your friends?” I didn’t really follow what she meant at all, seemed like a strange question doesn’t it? Well I just nervously said “sure”. She tells me to come over there and reaches her hand up through the leg of my shorts and starts playing with my cock. I kind of freaked out a little and just froze. I didn’t understand and I was so nervous and this seemed so out of place so all I could think of to do was hide behind my cell phone taking her picture. Lol I felt kinda retarded at that moment but I was definitely getting turned on now as it finally sinks in that she has been gradually seducing me and purposefully so with the intent on sex before she even arrived. I was just too naive to realize her intent but I was just so taken back by it all because either I was just seeing a side of her I never have all those years growing up or she just changed somehow.

She worked her hand and it felt surprisingly good, by that I mean better than my own and her hand was so smooth. But coming from a woman her age seemed quite awkward to me yet at the same time seemed pretty hot. I don’t know why, maybe because it seemed like a taboo thing? Then she says another strange thing I didn’t get. She’s looking up at me and says “so how long did you think you were going to keep this from me?” as she pulls down my shorts and i’m like “uhm, I dunno” She opens the fly of my boxers and pulls my cock out to start sucking on it. Her tongue felt amazing, she was very good at giving head and now I’m remembering funny enough that this woman used to teach sex ed in school but I’m just in disbelief and confused as to why she wanted to do this. None of her behavior makes any sense to me. It’s like she is an evil twin sister or something. She stands up and motions for me to lay on the couch and she continues giving me oral then she pulls off her panties and asks if I’m ok with this. I said “well it’s kind of awkward. We probably shouldn’t be doing this” she interrupts me before I can finish my sentence saying “you’ll be ok, I’m going to finish what I started” basically dismissing me. She straddles me holding my cock into position to put me inside her and I interrupt coming up with an excuse saying “uhm, I don’t have, you know, any condoms with me or anything like that” She just smiled and squatted down forcing me in her before I could react saying “you’re fine, just do as I say and don’t cum in me. Going in it felt so good so I said “well can I at least take my boxers off?” So she pulled off of me raising up. I’m a little embarrassed as I took them off because I haven’t trimmed up down there in a while, been too lazy.

I leaned forward to reach and unravel my boxers over my foot as she is still hovering over me and she must have thought I was trying to get up because she pushed my shoulder back forcing me down shaking her head “Oh no you don’t, lay back. You’ll enjoy it, trust me” even though I wasn’t intending on stopping but whatever so I just let her do what she wanted for a few. She starts off riding me pretty hard and she’s really into it and at some point I started to say “hold on” as I wasn’t too comfortable yet with any of this even though it felt really good but I’m thinking it’s only because this is rebound sex but she shushed me “shh, you’ll be fine” and pulled my head shoving my mouth over on her boob. A few moments later I’m getting into it much more now and when I start groaning and breathing hard she tells me to “rear end her” which she meant doggy style position I take it. So I give her what she wants and pound her from behind as she is leaned over on the couch and after she gets off she starts to take off her clothing and lays down. I get on top and fuck her for a while longer as I decided to record a close up video of me pounding her pussy. After a while she says “let me suck you off before you get carried away.” I lay back on the couch and she tells me to take her picture and she puts my cock in her mouth making like a pose of sorts as she does it.

It didn’t take me long with that tongue of hers that I told her I was about to cum and she kept going as I unloaded into her mouth. She swallows and opens wide for the camera, I guess to show me that she swallowed all of it and says with a laugh “bet you’re not thinking about your ex now are ya?” I certainly wasn’t. “there now you got some pics to show your guy friends” I’m taking that to mean she enjoys the thought of others getting off on her. Honestly this isn’t the first time I’ve been with a girl that likes to take naughty pics, maybe it’s a narcissism thing. In case anyone here cares to see a few of them I put them in order of occurrence so it’s in timeline with the story. You can see how she goes from fairly innocent to showing her true intent. Kind of funny I thought

1. [Imgur]([https://i.imgur.com/RASw6KA.jpg](https://i.imgur.com/RASw6KA.jpg))
2. [Imgur]([https://i.imgur.com/JEs2l69.jpg](https://i.imgur.com/JEs2l69.jpg))
3. [Imgur]([https://i.imgur.com/5fr3j3O.jpg](https://i.imgur.com/5fr3j3O.jpg))
4. [Imgur]([https://i.imgur.com/ZuOrWOq.jpg](https://i.imgur.com/ZuOrWOq.jpg))
5. [Imgur]([https://i.imgur.com/1UYZKEr.jpg](https://i.imgur.com/1UYZKEr.jpg))
6. [Imgur]([https://i.imgur.com/9XUlTCJ.jpg](https://i.imgur.com/9XUlTCJ.jpg))
7. [Imgur]([https://i.imgur.com/VWmqKuA.jpg](https://i.imgur.com/VWmqKuA.jpg))
8. [Imgur]([https://i.imgur.com/vJMShgz.jpg](https://i.imgur.com/vJMShgz.jpg))
9. [Imgur]([https://i.imgur.com/bzY1qUs.jpg](https://i.imgur.com/bzY1qUs.jpg))
10. [Imgur]([https://i.imgur.com/WRM3k0e.jpg](https://i.imgur.com/WRM3k0e.jpg))
11. [Imgur]([https://i.imgur.com/ol7s52J.jpg](https://i.imgur.com/ol7s52J.jpg))
12. [Imgur]([https://i.imgur.com/HGwz0ib.jpg](https://i.imgur.com/HGwz0ib.jpg))
13. [Imgur]([https://i.imgur.com/VsUMTpL.jpg](https://i.imgur.com/VsUMTpL.jpg))
14. [Imgur]([https://i.imgur.com/dbC8Ejj.jpg](https://i.imgur.com/dbC8Ejj.jpg))

Despite some initial awkwardness, she did at least take my mind off the ex and made me feel better. I told her she was really good at that and she said she had a lot of practice with her ex husband because oral was his favorite. We got dressed and talked for a bit longer. I decided to ask what made her decide to do this. She just smiled and cryptically said “I just wanted to bond with you so figured now was a good time get it done but I wasn’t leaving until you gave it up whether you liked it or not anyway” then she laughed

What exactly does that mean? I still don’t really get it but was a better experience than I would have ever suspected and certainly never saw something like this ever happening. Since then usually when I see her it’s when I’m over at mom’s house. She would always look at me in a way she never did before and smirk quite often but we haven’t spoken of that incident since. I have another similar story to this too where I have some pics of an older woman though I’ll have to fudge my age. I’ll get around to sharing it soon.

Source: reddit.com/r/gonewildstories/comments/a4dpn7/mf_an_old_friend_39f_of_the_family_shows_me_18m_a