My Second one night stand, with a guy I met on Craigslist [f/m] (series) | 2016

The next time I tried craigslist, I posted my own add :

"WHAT I'M ALL ABOUT: I'm looking for friends, and/or more.

My bottom line: I'm not looking for a long-term, emotional (or necessarily physical) relationship. I Love Sexting. I want to meet men who will exchange naughty messages with me, so that I may enjoy them when alone. I want to read personal stories, fantasies, and outrageous accounts of sexual decadence ...

I need a smart man. One who has a way with words. I want my brain to get as wet as my panties.

*The ultimate physical specimen: dark hair, dark eyes, tall and fit. (imagine Keanu Reeves, circa The Matrix trilogy) But I have been known to stray from type. You don't have to LOOK a certain way; if you make Me FEEL a certain way ...

If it did go beyond texting, I would enjoy seeing how a man reacts to spending the evening at a sex club. I have always wanted to give a hand-job, while on the dance floor. I know of just such a place ...

My STATS: * · 5'9" * · White * · Curvy * · Brunette * · Blue-green eyes * · Never Married * · No children * · Don't smoke * · Don't drink

MOST IMPORTANTLY: YOU MUST BE OVER 18, AND SINGLE. I DON'T WANT ANY CRAZY-GIRLFRIEND DRAMA !! "

I was quickly inundated with so many replies to my ad, that I had to shut it down after 8 hours. I sifted through several emails, and after a few days, I finally whittled the list down to a guy name Sean.

He was Way nastier than Eli. He wanted to talk on the phone right away; and though I was nervous to do phone time ( it had been more than 20 years since my pre-teen phone-sexaholic days) I figured I would avoid another Eli, if I Knew that this guy could Actually talk to a woman.

It was HOT! and DIRTY! This guy was down with all the weird stuff I talked about. He egged me on to some places where I felt sexual shame (and I was both freaked out, and incredible turned on by it). We spoke a few more time, and texted every day over the course of 2 weeks, until we managed to set up a date that worked for both of us. My parents were leaving town for a week, so I'd have the house to myself...

I drove an hour to the town where he lives (which, I will say, was not as long, nor nerve-racking, as I had thought that it would be) His directions were perfect. I had to drive down a narrow, one-way back alley, and then he came into view.

*Now, I had received 2 face pictures, and was told he was 6'4", 225 pounds. WELL, I've got a buddy that's 6'4", and Sean was 6'2" Tops. And I KNOW what 225 pounds looks like, and this guy was HUGE!! I'll offer the following visual to illustrate the point: later, when he bent over to get out of my car; his incredibly loose track pants, flashed More than a bit of crack - I got a facefull of gigantic pimply lard-ass. [Note: this guy had requested anal rape from me; which I was interested in, because all the other boys I've been with rejected ass play; and I just wanna see if I can locate a prostate, and make a man cum like he Never has before. So when I saw that pasty-white, cellulite laden back-side, I almost shed a tear. Butt he was already at my place, so I persevered, and made the best of it.]

He was a smoker, so we went out back for him to light up. I had him hold my dog's leash, while I zipped inside to get myself set up for Go Time. He had mentioned that he had a fantasy involving walking up behind a woman in a office; bent over her desk, wearing a white shirt, short skirt, no panties, no bra. So, being the awesomeness that I am; I went out, the very next day after work, and bought a white shirt, to complete the scene I would set up in my bedroom [Note : I had always lamented the fact that when you entered my bedroom; you didn't look upon the bed first; but instead the desk. And here was an opportunity to enjoy witnessing someone seeing my room for the first time (* I enjoy judging people on how they react to it; the decor is rather... different ; ) and this guy should love what he sees!! I went so far as to record a soundbite of background office noise, printed out one of the face photos he'd sent me to frame for my desk, and I set up my iPad with an image of a pie chart on the screen; to complete the look. I maaaaay have also brought in a coffee cup (empty of course; as I don't drink coffee, but the illusion doesn't have to go into That much detail: this guy is only gonna See ME standing there!! The Show is more for my enjoyment!]

I Did get a good reaction; he liked it and said that it was exactly what he was looking for. We undressed me, but I kept on the black fishnet stockings, and he laid me down on the end of the bed. He complimented me on my tits, and said I was gorgeous. I had my hand between my legs, and he was standing in front of me, rubbing up against me, pulling on his dick, while we dirty talked. I was getting So Excited to be proper fucked by the promised 8" cock. I was wet beyond belief, and tingling with excitement...

...Then, he apologized...

He said that his dick was not co-operation, and he was having trouble getting hard. He explained that he was very nervous, and hadn't been out of town in a while, and was freaked out by my house.

His list of grievances about my home: -my house makes noises; His house doesn't make any noises. -my dog had stared at him weird, when we came in. -it was too hot : Big Boy was getting sweaty while he pounded me with his semi [it Never got better - sorry to ruin the ending, but it had to be admitted. We Did manage a few different positions; even his half-cocked stiffy was pretty impressive, I gotta say, - I felt it in there] -my Christmas lights wear freaking him out, because they flashed, and change colour -the oddly placed ceiling-height windows in my room, make it felt like a dungeon, and he was freaked-out, to be in there (THAT one was my favourite, considering he didn't even mention the flames on the walls!)

So he zipped up and we just kissed (it was good. At first he used a bit too much tongue, but was easily corrected). We tried a blow job - That was GREAT!! He Likes teeth!! You have no idea (unless you do) the pleasure of giving head, when you don't have to master the mechanics of sucking cock; so that you manage just the right amount of pressure to Not scarp it with a tooth!! He Wanted bite marks! And I happily chewed on that that flaccid dick like a mouth full of toffee. I was able to get him semi hard with the blow job, so then he flipped me over, and attempted to stuff it up my ass (without lube! *He thought my Ample wetness would do the trick) I was so glad in that moment, that he wasn't rock hard and thick!! I explained to him that anal sex doesn't work that way, that he'd have to 'warm me up' first, and you need a rock hard cock. I guess it was his first time and he'd only seen it in porn (where the girls are pre-stretched out and lubed before the cameras role) After profuse apology, we eventually headed to the office, for a smoke break.

He started with the "I might not be able to stay here tonight," After I had Just burned a joint. He explained that he hasn't been out of town in a long time, and because I picked him up, and he didn't have a clean exit strategy, he was uncomfortable. I told him, in no uncertain terms; that I was NOT doing the 2 hour run, to take him home. He back-and-forth-ed for an hour, debating whether or not to leave, until I finally made the decision for him, and told him to call a cab for himself. When he inquired about the cost of a ride, he was told $70: the Exact amount he had taken with him (Fate?) I prompted him to book the taxi, and told him that we'd try again another day.

We spent the 45 minute wait talking, and a couple of times we tried again, but his dick was not feeling it. He told me that this Particular cock has a mind of it's own :"When I'M in the mood, HE doesn't get hard. When I'm not in the mood, HE's hard," [and get this: his cock's name is "George". My father's name. I shit you not!]

I did manage to get off twice that night - once when he was using a vibrator inside me while I rubbed my clit, and then later in the office; while he has having a smoke, I sat right in front of him, spread my legs open wide, and started playing with myself while he watched. Then I grabbed his hand, and directed it to my pussy. He slipped in his middle finger and slowly, then at my instruction, more quickly, jabbed in and out of me, while I pinched and rubbed my clit. I told him to "put more fingers in there," and he obediently inserted another. I wriggled in delight as I asked for more, and he said he wanted to get his whole fist in my pussy (*he managed to get just past the last knuckle - good effort - the angle was off, as I was scooched down in a fold-up canvas camping chair, legs dangling off the sides.)

We dressed after that, and walked to a donut shop across the road, so he could get a coffee (did I mention he was tired, and yawned All Night!) He kept going on about how he felt like an asshole, and I kept trying to talk him down. It wasn't weird for me (I suppose being in MY element was helping) but he just couldn't get comfortable. We talked and joked while we waited. The cab picked him up, to go back home at 1:00 in the morning. He told me "it's Not you, you're great " we kissed good bye, and he drove away. We texted a few times during his ride home: him apologizing, me telling him not to feel bad. I eventually went to bed around two.

He texted me the next morning at 7:00, to say that he hadn't slept all night; because he was ashamed. We chatted for a bit, and then I went back to sleep. I sent him a few messages that afternoon but he didn't respond. The next day, after another attempt to contact him, he finally said he was sick, that I shouldn't worry: "we're still friends". One more "I feel like shit" text from him the next day, and then I didn't hear from him for months, until I finally messaged him to ask what's what? He explained that he was embarrassed by his performance, and assumed that I didn't want to see him again. True. But I wanted confirmation that it Wasn't Me! Which I got, and felt much better. He suggested we could try again, but I just couldn't be bothered. I ended up signing up for the free online dating site, Zoosks, to try my luck there ...