Blackmailed by an older woman [m/f] | 2016

I struggled where to post this - you see, it has it's sexy parts, but it also has some very not fun parts. However, since the story really revolves around sex, I ultimately decided to post it here. I will take care to try to indulge the sexy parts of the story for the sake of this subreddit.

This occurred in 2007. I (male) was an early 20's college grad, recently out of a relationship and going through a bit of a dry spell. I had just moved in with some buddies and it was very much of a frathouse/bro kind of lifestyle, which was a lot of fun, but it also meant all my friends knew exactly who I was hooking up with and when.

Being the sexual deviant I always have been, I sought out to satisfy my urges online - specifically the seedy underbelly of the internet we all know as craigslist. I responded to a few ads for a couple of days without a lot of success, when I finally stumbled upon one that really caught my attention: (note: this is paraphrased from my memory, not verbatim copy)

Subject: Boytoy companionship wanted - 38 - w4m

Seeking younger guy for regular weekend meetings. Boyfriend lives out of town and may be involved from time to time, but mostly it will just be you and I. I want a younger male I can teach and do things with out of the bedroom with as well.

Attached was a picture of her chest and body. She was a gorgeous woman - a few extra pounds - but very nicely proportioned where it mattered. Awesome. A sexy older female looking for a no-strings attached relationship with a younger guy. What more could I want?

I spent some time writing my email to her, describing who I was, what I wanted, what I looked like. I wanted to make a good impression and stand out from the heap of e-mails she was surely receiving, and luckily it seemed to work. She responded back quickly, we engaged in conversation over a few days, and then made plans to meet that weekend.

The first time we met I was nervous. We popped open a bottle of wine and drank while hanging out on her bed. After thirty minutes or so of conversation, and the tone getting more and more flirty, she got up and said she'd be right back. Shortly after, she re-entered the room with nothing but a bath robe on. She approached me, sat on my lap, and we began making out.

I was kissing all over her body - her neck, her shoulders, down to her gorgeous size D breasts, down her stomach, past her pelvis, trailing down her thighs, then finally back up to the prize my lips sought: her beautiful shaved pussy. I took my time alternating between licking, sucking, and fingering, changing my technique in response to the moans and movements of her body. I was determined to put her pleasure above my own, and I succeeded. The first wave of orgasm her body and immediately I could feel her clench around my fingers. Her wetness grew on my tongue and all over my hand.

After that, we spent many hours fucking. She was no stranger to rough sex and demanded I pull her hair, spank her, basically anything I wanted. We both came many times that night. It was a great time and we both fell asleep exhausted. I spent the night and when we woke up we went to breakfast together.

I started visited regularly. The sex was great, we'd hang out and watch a movie, go for walks, go out to dinner together. Then things started getting kinda weird.

You see, she had this boyfriend out in Washington. She used to stream us having sex over webcam to him. The whole thing - me eating her out, me fucking her in ass, or us just lying there cuddling, whatever we were doing. Occasionally she'd turn to the camera and say things like, "You see how hard he's fucking me, babe?". I mean, I didn't really care, but it was just kinda weird. She'd always tell me her boyfriend was going to fly both of us to an extravagant vacation and pay for everything.

Visits became more infrequent for me after a while as I started prioritizing other things in my weekends over making the drive to her house (it was a good 40 minutes from me). She started complaining that I wasn't spending enough time with her, that I no longer slept over or did other things with her. Truthfully, for me it was always about the sex and I knew it was time to cut off .. whatever this was .. and that conversation did not go well. She was upset, claiming I was just using her and I was just like the last guy she dated (?). Nonetheless I made my intentions clear and left intending to never talk to her again.

And then shit got really weird... (prepare to lose your boner)

She called me up a few days later after work and repeated back to me my current residing address, work office address, job title, and e-mail address of both my parents. No idea how she got the information, considering we didn't really talk about these things too much. She told me that she showed up at the work of the last guy who did this to her and told her employer all about their illicit relationship and all the (supposed) terrible things he was doing to her. She told me that I better shape up and start spending time with her again or she'd do the exact same thing to me.

I was freaked out. I didn't want to have anything to do with this person. She was obviously the kind of crazy you hope to never run into in your life, but I most definitely had. I was just out of college and starting to get my career off the ground. I couldn't risk being humiliated by my family/friends/roommates/coworkers and potentially fired. I lost a lot of sleep over that phone call and knew I had to get myself out of this mess.

Instead of doing anything impulsive, I hatched a plan: I would become the most uninteresting man in the world. I visited her the following weekend. I was extremely mechanical during sex. I did the job and made sure she got off, but nothing more. During conversation I intentionally gave shallow, unintelligent sounding responses. I created awkward silence, and pretended to miss social cues. I lost my manners at restaurants. In short, I became the uncoolest person to hang out with.

And within three visits it worked. She didn't invite me back. Bullet dodged.

In hindsight, it was an interesting experience, but I'm not sure if I learned a lesson. Perhaps it's if you treat sex like a buffet platter sometimes you're bound to pay for it one way or another. Can't say that ever stopped me from having more crazy sexual experiences afterwards though. Just thought I'd share this very odd time in my life.