Failed Play Date Redemption

Until more recently, I've never been a fan of anal play. I would have to be in just the right mood, and then it wouldn't last long. However, I had recently decided to make a more concerted effort to see if I could make it more comfortable and enjoyable on a regular basis. That's when we broke out the butt plugs. You remember? The ones from the first set of intro videos? Yeah, those were NOT working. So... we ordered a new set. Rainbow stainless steel, with a cute gem on the end! Perfect! One afternoon, we decided to give them a try. The little one was easy, and we played because, well, we had to give it a full test run, right? The plan was to wear it or a bit in preparation for later that evening. However, it did not pass the test and quickly fell out.... while I was walking down the stairs. So, we upgraded to the medium later that evening. That one, to, was fairly easy, so we played some more. Gave it the full test run. We never did make it to full anal. He did, however, fuck me good and proper with my new butt plug in place. Now... now he likes to call me his little ass slut. What can I say? I know what I like.

While we have very regular sex, I, (James of SexyJammies) need assistance. See, I broke my back. Some what significantly enough and stubbornly enough to have lasting neurological effects. Some days end in complete satisfaction while others, an equal number I might add, end in frustration. Better living through Chemistry to the rescue. Trimix is serious ED medication. This video is all about the first time it was given to me. Don't worry its still hot, just with underpinnings. Watch the intro first for the entire backstory...

So shes a bit spoiled. She isn't "make slow sweet love me" kinda gal. Hasn't really ever been. She likes horsepower! From time to time she wants a bit more. So, he sometimes oblige her. This was one of those times. What started as a post shower romp, evolved into one of the rougher sessions we've have in a bit.

What can I say? I was in a take charge kind of mood. It doesn't happen often, but it does happen. A few other things that don't happen often... I came so hard riding him that my legs were shaking, and I squirted all over his lap. Usually I need tools to assist with both of those things, especially when on top. I guess I was just in the right kind of mood that day.

We had spent the day on the run from one errand to the next. On the drive home I encouraged her to give me a little show. It didn't take long of that before I need to pull of the road and document the experience. I'm sure you can see where this is going

We had a rare opportunity, with a three plus hour drive ahead of us, to make some stops and take some pictures. So we stumble on this Industrial Park with lots of cool goodies to shoot near and on. She had packed for the potential occasion so of course she HAD to get naked outside more than once. I may have encouraged some of that. That may have been a bit to much encouragement ;-) At our final stop of the day we decide we'd had enough. The rest you can see for yourself. And do listen for the Bothersome Cessna, who attended all our shoots that day.

So the week the planet shut down last year we had plans. Sexytime with sexy friends plans. Obviously, we had to reevaluate those. Instead we had some Whiskey, took some pictures, and viola! Desktop Anal sorta just happened!

She has, until just recently, always harbored a bit of hesitation around butt play. So we do much of our anal play either in or just after a shower. So after a few weeks of teasing I catch her in just the right mindset right after a nice evening shower. So we give you Roxy's First anilingus! The rest, as they say, is history.

I don't typically give road head. It makes me nervous. I'm terribly afraid he's going to wreck the car and I'm going to die in a fiery car crash with a cock in my mouth. It's not that I have it planned to go out in a less glamourous fashion. Quite the contrary. I would just prefer to be a lot older when it happens. Anyway, there was this house party. I'm not going to spoil it for you. You can listen if you so choose. Here's what I will say. It was HOT. I was horny. And I decided that I needed a cock in my mouth, ASAP! I'm fairly certain it went on for a bit before he turned the camera on. What made him turn the camera on? It may have been because I give amazing blow jobs. But what's more likely is that he did it after I asked him to finger fuck me and make me squirt. And he did just that.

This Video turned out very differently than planned. We had be talking to a third for some time, feeling out if he wanted to be apart of our fun. We met for a date to get to the face to face out of the way. I'm not saying he cat-fished us, but he certainly did not put his best foot forward. The date was a bust. So we left. We took some flasher pics and video, as you will see in the intro. This always paves the way for more fun at home. As we say the worst case scenario on a SexyDate is that we end up having sex with each other. Enjoy... SJ