After having the best sex of my life but having my ex leave because of it, I went back on Ashley Madison immediately, of course. My thought process was very much “Fuck you, I know someone wants me.” Since I was 100% sure I couldn’t maintain a real relationship & pretty sure no single guy would want me, it was an obvious choice. Needless to say someone did want me, a gorgeous bald, buff Italian guy in his early 40’s who had been married for 10 years, was not 5’10” (men are liars, he was 5’7″), was slightly stocky & hairy.
He was not as captivating as The Tourist but he filled a need. Mine to feel desired at a time when I was still wearing shape wear on a daily basis because my body was so sad and his need to feel loved and wanted. We met at Starbucks and I determined he wasn’t a serial killer. He eye fucked me for a bit and then asked me if I’d go out to his car. We started making out and he told me to get in his backseat, To which I responded “I wasn’t expecting to go that far today because I’m on my period” but he said that he just wanted to watch. That was his kink and actually a scene we played out a few times. I would masturbate and he would watch but I wasn’t supposed to make eye contact with him or acknowledge his presence. More often than not he would film it or take pics. I never watched the films or looked at the pics because I didn’t want my disgust to overshadow the joy he took in them.
That first day though in the back of his truck, at 10am, in a corner of the parking lot, I shyly rubbed my pussy for him while he watched wolfish and hungry. The exchange ended with me sucking his cock till he came, notable because I still wasn’t very good at that and because he’s only the second guy I’d ever made cum. I played at sucking cock as a teenager but I wasn’t very good at it to say the least and teen boys know how to jack off extremely well which gave me an out. So they would just finish and I would watch pretending to be sexy and frankly glad my “job” was over. Then I got married and he didn’t lick pussy so I rarely sucked cock. Of course when I did there was no motivation to finish because then I would lose any chance of cumming. If he wasn’t able to fuck me because he’d already came then I would lie there alone and frustrated wishing I could bring out my vibrator and not feel awkward about it. I once waited until my ex was snoring, then snuck to the living room, my vibrator and I so I could cum. I did and it was wonderful but sad and shameful at the same time.
The Detective was different though and for a month we existed in our own little bubble. Sex of all kinds in hotel room after hotel room. Naked cuddling and being so horny that he wouldn’t be able to wait for room service to arrive before he thrust his hard dick into my pussy, that being interrupted of course by the room service guy. Who of course knew what he interrupted and was wearing the smirk to show it. In between he would send hot and heavy texts sometimes while his wife was in the next room. I tried not to think of her and rarely asked about their relationship. All I knew was that they had never had any kids, they focused on their careers instead, that she knew he cheated but just wanted him to be discreet and that he would never divorce her because she was his best friend.
So we went, I wore lingerie for the first time in a very long time for him while we played out his fantasies. He always had his Go Pro camera with him and I just ignored it. I could pretend everything was good with him but my hunger wasn’t satisfied so I continued to sleep with other men. I didn’t want to get attached to him or so I said. He knew though of course and would interrogate me while he fucked me. He wanted to know how many, details about the sex, them and whether their cocks were bigger then his which most of the time they were. The interrogation turned him on and gave him license to punish me, which turned me on. That was the first time I ever gushed with manual stimulation. He rubbed my pussy hard and kept repeating that this was his pussy and told me to repeat that, which I did. I came and came and then of course we fucked again.
I did fall for him though, he was wonderful and intoxicating and liked me. One night we made the mistake of falling asleep together and as I stroked his arm, “I love you” tumbled out of my mouth. I was shocked at myself and how terribly cliché it all was. I promised to myself though, no extra dick from that night forward. Then he disappeared.
Not from the world, just my world due to a credit card statement that had eight hotel charges on it. A bit excessive to say the least and his wife was furious. He chose her like I always knew he would but tried to tell me it would only be a little while. I said no and tearfully let him go via email of course since he was on house arrest, gone forever.
He wasn’t really though because six months later I went back on AM disgusted by terrible dates and terrible sex and guess who found me? The Detective of course. I still wanted him and I looked better so he really wanted me. This time the staleness of the sex and desperation of him turned me off. We slept together twice and the second time was just as bad as the first. So when he “Poof” disappeared this time, I almost felt a sense of relief. So now I have a strict scorched earth policy unless of course their FWB’s which is a whole different kind of fucked up.
Confessions of a Terrible Dater 