I’m not going to try and tell you that all my experiences with online dating was like the first one.  I’ve had lots of great sex with women from this website and a few others.  However, every once and awhile you run into a slight disaster.  My second encounter was all based on a set of tits.  That set of tits you see in this post.  Great looking aren’t they?  A nice busty babe that posted her profile here.As quick I was to judge my first conquest by the nice ass she had, I judged this one purely on those lovely massive mellons.  Again, I contacted her, but this time I decided to use a different approach.  I was going to be assertive this time, after all, she was posting on a swinger style online dating service.

By the second email I was telling her that I want to titty fuck those massive mellons of hers and that we should meet up on the weekend.  She wasn’t sure if she should, she hardly knew me, and when she finally did decide to meet up with me it was only a half-hearted acceptance.  Still, I was coming off my first success and I thought this would be my second success in as many weeks.

I met her at a small motel, one of those little dives that you could pay by the hour if you weren’t going to be there for long.  She was pretty, plump, and shy.  She didn’t say much and soon I found out that she wouldn’t do much either.  We went into the room, we talked a little, I kissed her on the lips.  It was working out at first, I lead her to the bed, started fondling her breasts through this loose knit sweater she was wearing.  She was a perfect busty and fondling her got me sporting wood pretty quickly.

I got her down to just her bra, released the hooks, and out popped wonderland of tits.  I start sucking on her nipples when she says, “I can’t go through with this, it’s too soon, I don’t know you well enough”  My Blue-Balls alert went off instantly.  I said something to the effect that she should relax and enjoy it.  She followed with a definitive “No!”

Well, no means no, I wasn’t about to keep beating a dead horse no matter how badly I wanted to fuck her.  She put her clothing back on, but it was friendly still.  We talked, chatted, she apologized and said she was just a little nervous and that this was her first time doing something like this (you’ll be surprised how often you hear that line).  I was cool though, even though this meeting didn’t go as well as I thought it would, I still held out hope for a future fucking with her (this did happen, but I’ll tell that tale at another time).

Moral of the story?  Not all first encounters go as well as can be expected, but you should always keep your options open.  The busty babe eventually did put out and it was well worth the wait.  If I had acted like a prick that night I would have never titty fucked her like I did a few weeks later.  She’s another babe in my stable of fuck mates.  We don’t meet as frequently as I would like (I love her big tits), but we do get together regularly when we both have free time.  So, just keep this in mind when you first start searching for casual sex partners online.

I decided that my first post about online dating and casual sex should begin with the woman that started it all. Her screen name was Thornbird, yes a little bit romantic and a whole lot silly, but also wildly passionate and looking for something that wasn’t being fulfilled in her life.

She posted her profile at this website. She didn’t want to post a picture of her face on the website, she wanted to remain somewhat anonymous, but also wanted to make it clear what she was looking for and also that she had the body that would please in so many ways. Thornbird was a 23 year old teacher, she was recently married, but also desperately bored. Married life wasn’t working out quite the way she expected it to. That’s where I make my entrance into this little story.

I won’t lie to you, her tight ass is what sold me on her, I couldn’t care what her profile said. That ass is what I wanted and I was going to make my first online dating experience with someone that would be a memorable fuck. Since this was my first attempt at online dating and seeking out a casual sex partner I wasn’t exactly sure how I should proceed. I’ve never had trouble approaching women in person, but my first online attempt made me feel a bit nervous, a bit tentative, and wondering how to approach her became a challenge to me.

I decided that her choice in screenname, the occupation she had listed, and the way in which she wrote, marked the signs of an intelligent woman that wouldn’t be won over with, “Wanna fuck?” as an opening to an email. What to do? I decided to play it shy, but playful and in my first email I came off gentle yet mischievous at the same time. I paid great detail to her profile, asked questions, and just merely hinted at the topic of sex. We wrote back and forth for a week, she was more in a rush than I thought. Apparently her husband was going away on a weekend trip, all the other prospects that contacted her weren’t up to snuff in her books, but she decided that I was the one for her.

It was three years ago on a cold snowy day in New York. I was to meet her at her house in a quaint suburban neighborhood, far away from the sounds of the city, and where the upper middle-class went to isolate themselves from commoners. Her house had high hedges, the neighbors would be hard pressed to be nosy, and once I drove up the driveway and the gates shut behind me there was a feeling of isolation. As I learned later, normally people don’t meet at their house, but for her this was a turn-on, that she would be sleeping with another man in the bed she normally would share with her husband.

I walked up the snowy front walkway, the door opened. First time I saw her face, beautiful blue eyes, but I hardly noticed that as she answered the door in just that little black thong. Her breasts exposed, perky tits pointing upwards, a b-cup but just barely, the cold wind making her shiver a bit or was it the excitement of this first sexual advance, I’m not sure, but it thrilled me. She didn’t invite me in at first, but turned, she struck that pose. Her tight ass in the black thong and a picture perfect duplication of what she posted online.

My dick immediately responded. I moved inside the doorway, she wasn’t moving yet, then she felt me pressing up against her, she felt my hands reach around and cup her breasts, and she moved forward, “Come In” She didn’t turn again, started walking up the staircase, and didn’t give me instructions to follow, but that’s exactly what I did.

I’ve masturbated many times looking at her in the thong, she kept that image going in my mind, as I didn’t see her face again until we reached the master bedroom. No unnecessary words were used by her, she turned with her best stern school teacher voice and said, “Fuck Me” It was too good to be true, but too real to be a dream. I was already removing my clothing as we walked up the steps, the coat, the sweater, and she moved forward and unzipped my jeans and helped to release my erect dick from confinement. Thornbird wanted it rough, she helped me off with my clothing in a feverish manner. She lead me to the bed, she got on first, she got on her knees and wanted it from behind. Peeling off the g-string she slapped her ass once, “Fuck Me”, I got behind her, guided my dick into her pussy, and from the first thrust she was extremely wet and my dick glided into her velvet love box. I moved inside her like beast, she yelped a little, a slapped her ass pretty hard just to watch it giggle a little, just to hear her whine a bit. I would lean forward to pinch her hard nipples. It was a mad thunderous insanity that left my body quaking with the joys of a rough wild uncontrolled orgasm.

We fucked repeatedly over the next two days, none was as wildly passionate as the first, but all were memorable to say the least. That was my first experience with online dating and this website. It wasn’t my last, won’t be my last, but it will always be my first online date that ended so wonderfully exciting. Thornbird and I still regularly meet, fuck, have a good time together. We officially are fuck buddies and it’s a fucking good time.