Guy #3 (This is Where Things Start to Get Hot)

My first date with Guy #3 almost never happened…but I’m glad it did. Our correspondence was drawn-out, and intermittent. Work, life and personal obligations kept us both busy and distracted, and threatened to kill whatever momentum we might have had on email. Our start-and-stop emails continued for a few weeks until we finally made a date.

And then I almost didn’t go through with it.

We only talked on the phone briefly before meeting, and I got a bad vibe. It gave me cold feet, and I came thisclose to canceling—about a dozen times. But against my better judgment, I went through with the date. And he instantly put me at ease. My doubts and fears were set aside. (I later even admitted to almost canceling. And he understood exactly why I came close to doing so.)

We had a long, lingering dinner, with much flirting, sexy conversation and lusty looks. When we finally got up to leave, we kissed for the first time, and it was a great kiss. He suggested we head to a nearby bar, where we got carried away. Fortunately it was a quiet night at the bar, and we were in an out-of-the-way corner where we couldn’t be observed. There was a lot of making out…and more. Without actually removing any clothes, he saw all of my body parts. My breasts. My pussy. My ass. (I, of course, had worn my oldest, ugliest panties because I thought there was no chance this lousy date could end with anything more than a kiss. That will teach me.) I saw his cock. It was very indecent, and I loved every moment of it.

Our second date was at his house, over dinner, cooked by him. Even if we’d never gotten naked, it would have been one of the more sensual dates I’ve ever been on. He sat me on a stool, wouldn’t let me lift a finger to help, and hand-fed me morsels as he prepared dinner. Once food and drink was consumed, he led me into his bedroom and brought out his box of toys. Before he even got me naked, he took things out and explained how they worked. (Definitely a boy who liked his toys!) Even that was a sensual experience as he was sliding different ropes over the insides of my wrists, for example, so I could understand what they felt like. The last thing he pulled out was his assortment of cuffs. He explained what he liked and disliked about each type, and ended by wrapping his favorites around my wrists. Then he stood me up (I’d been lying on his bed during this), undressed me and attached ankle cuffs, too.

From that point on, things become a bit of a blur. At one point I was cuffed to the wall, arms and legs spread. (Yes, he’s definitely kinky. He has eye bolts strategically placed in his bedroom wall.) There were clothespins on nipples and he was flogging my breasts and pussy. Later I was on my hands and knees, and he was flogging my ass, then spanking me with his bare hand. (But no over the knee!) Finally there was a vibrator on my clit and his cock was being rubbed across my face. When we eventually went to sleep I was still wearing the cuffs (though they weren’t attached to anything) and every time I woke up they were a constant reminder.

In the morning there was more play, including some cock worship that ended with him cumming on my face, neck and chest, and leaving it there to dry. We finally emerged from the bedroom, he cooked me breakfast and we napped on the couch for a lot of the day. I went home with aching nipples, smelling of dried cum and big smile on my face.

Our next date was much more vanilla because we ended up at my house (not so many toys), though he did leave me with a hand-shaped bruise on my thigh that I enjoyed for a week or two. Unfortunately, things didn’t work out with G#3. He said he didn’t have enough time for a relationship. Who knows if he was telling the truth. I would have loved to have seen where things would have gone had we had a few more dates. But he definitely got my juices flowing!

I did learn some things about myself from him:

1. When playing with someone new and experiencing new things, I can get sensation overload. For example, the cuffs, clothespins and flogger was just a bit too much, too soon. I need to try one new thing at a time.

2. I’ve always known I was a cock slut, but I’ve never been forced to beg for it before. And I loved it. (What vanilla guy in his right mind is going to refuse a blow job?) G#3 teased me with his cock nonstop, but he never let me suck it. And it torments me to this day.

3. I can be a bit of a martyr when things get painful or intense, and rather than using my safe word, I just grit my teeth and hope that it’ll slow down or the top will notice. I know some doms want to push subs to use their safe word, just to make sure they’ll use it. Since I don’t have a lot of experience with safe words, if I’m with someone new, I probably need to tell them…check in with me and ask me how I’m doing. With G#3, there were a few uncomfortable times where I just hoped he’d slow things down, but I didn’t ask him to. At other times, he noticed.

4. Since I haven’t yet made a strong connection between pain and pleasure, I don’t enjoy mind fucks that have to do with pain…they just serve to terrify me. Mind fucks that have to do with bringing out my slutty side…those are a huge turn on.