Date with an Angle/Sex with a Devil

I met a man on Match this past week. We exchanged a few, somewhat dull emails. Stable job, loft downtown, funny, excruciatingly nice. Clearly I will eat him alive. He is 44 yet looks like he is 20. A cubby, Michelangelo figure last seen wearing wings and painted on the ceiling of the Sistine Chapel. Wait, is that mean? No. I agreed to a date mostly because I miss having someone in DTown that will go to shit-hole clubs to see live music with me as does Chicago.

*side note – Chicago is a regular you have yet to hear about*

There was also the promise of sushi; frankly I had no choice but to say yes.

Simultaneously, I met a man on OKCupid. Also stable job, house in my same neighborhood, funny. We exchanged several long and detailed emails discussing our various sexual conquests. Witty repartee, and biting sarcasm abounded. As did the increasing hardening of my nipples with each email. This man made no secret that he had a girlfriend and a 100% open relationship, the inner workings of which fascinates me endlessly. I bombarded him with questions and was having a most excellent dialog when at one point he writes to me “My girlfriend and I read your last email and were laughing our asses off. Her exact words were – Oh my god, you HAVE to fuck her!”

Umm what? How does that work. Turns out that he shares with her his ‘hunt’ and she was particularly intrigued by my notes. Have I mentioned that this man is a Dom that is also interviewing full-time Subs for playtime *gasp*

Need I mention how ridiculously turned on I was by the thought of him discussing me with her. What is wrong with me…And what bizarre universe have I landed in.

At one point he mentioned her name to me and it did not take me long to locate her profile. Yes, I was curious…so sue me. Little did I know she would check who was “stalking” her and send me a note less then an hour later. She was so flattering and funny and well, down right gracious that I immediately was taken with her, as well. Best line out of an email “we decided that no matter what happens sexually with you and X, we want you in our lives as our friend. You and I can drink wine together; you can fuck X and if he treats you well in bed, he can drink wine with us too”. Wow. In the words of BB – I have landed in my perfect situation. A power top that that can NSA fuck me and a super cool chick that I might actually be able to get along with. I happen to mention my date and what club I will be at with the Cherub and the unmistakable pink coat I would be wearing. Just sayin.

Cherub and I meet at the sushi restaurant. Despite it being less then two blocks from my house, I felt like I needed an out. We had nice, very benign, very ‘first-date-ish’ conversation. He paid for dinner – love that. We head to the club and upon my entry, my senses are on high alert and my heart is pounding as I survey the area trying to catch the eye of any man that resembled my OKCupid Dom. Nothing. Given this, I send Cherub off for cocktails and sit back and enjoy the eye candy.
*who knew there was this many hipster/rockabilly boys in DTown and why the fuck am I not hanging out with them*

During one of the many trips Cherub made to the bar, I feel someone standing behind me. So close that I can feel breath on my neck. A hand moves my hair away from my ear and says “Your date is boring”. I smile. Predictably my nipples instantly become rock hard. “How long have you been standing there?” “Long enough for me to know your date is boring.” I whimper. Now given how many stranger danger situations I get myself into, I am only 75% sure this is OKC. As Cherub approaches with a drink for me, the strangers says “I like your coat”. And I know it’s him.

While I enjoyed the drinking and the bands, he seemed to delight in ensuring I knew of his presence. A brush of a hand across my arm. Fingers pressed into the small of my back as he walked behind me. A breath on my neck. Anything he could get away with. Needless to say, I was dripping wet. The show goes on and towards the end, I lose track of him. Cherub and I walk out and I start to think that I cannot get home to masturbate fast enough. Cherub returns me to my car, a few hugs, a kiss on the cheek and an invitation to a movie and I was speeding the blocks to my home.

I crashed through the front door, shedding clothes as I leaped into my bed and grabbed my trusty vibrator. I just get comfortable when I hear the telltale jingle of a text message. “What is your address, I want to fuck you”. Ahhhh….the evening has just begun.

Without saying a word, he enters my home, takes hold of me and proceeds to kiss me. He tosses me on my sofa and attacks my neck, my nipples, my lips. He pinches at me, prods his fingers into me, all the while the only words are “do you like it”. Finally he asks “do you want me to fuck you?” I am not sure how audible my agreement was, but he must have gotten the point. “Then strip and get on your knees!” Uhhhh… Imagine if you will, a cross between a kitten sighing and a moan and the sound a starving man makes when presented with a juicy, medium rare fillet. I waste no time getting out of my clothes and he wastes none pushing me down on the hardwood floor and shoving his cock in me. Oh my… “Do you like that you little whore?” “For such a slut you sure are tight.” Slap on the back of my ass. Hair pulled. Teeth bearing into my back and ass. “I am going to fuck your tight hole.” Slap, pull, bite.

*wait, am I having sex with BB…no no*

Two and a half hours and several orgasms later, he announces he must go home. When questioned about what I am doing the next day, I say that I am spending it with my nephew and he suddenly morphs into the Avon Lady. “Oh that is great! He is nine, right? Oh they are so fun at that age. Wow, I really like your place. Thanks for having me over. Call me next week when you are in town. Bye”

Okay…what just happened. And how to I ensure it happens again.

Sushi dinner, zero dollars. Tickets to a great band, zero dollars. Cocktails at a hip club, zero dollars. Getting fucked by a guy you picked up while on a date with someone else, POINTS!