Failed Play Date Redemption

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.

For New Years we attended a hotel takeover. In the middle of the day, Roxy decides she wants to give me a show. Dressed in her typical sexy elegant way, she doesn't even bother removing anything. She grinds herself to a rather intense orgasm.

"You'd better stop teasing me, little girl, or I'm gonna fuck you in those shorts and make you wear them." I may or may not have been discouraged by his statement. Well, mostly not. At all. So, as all decent husbands do, he made good on his promise. Threat? Either way, I enjoyed every minute of it.

The "Reno" was a house we renovated earlier this year. While under construction we used it a few times for photo shoots. This particular day we had just had 6 inches of snow and the back yard was pristine. This is how it started. How it finished was in the front room on a Turkish rug in front of the window. The folding table was an unfortunate casualty.

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...

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.

You know how it is. Perfectly fine holiday weekend. Then Bang! She's stuck waist deep on top of a filing cabinet in a bikini. In the Garage no less. One thing leads to another, and before you know it we are naked on the weight bench. The kid interrupts us. The Neighbors listened in. But, by golly, we made it!

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

So, we accidentally made a sex tape (more dets in the Intro Vid). Now, now, we had planned to take a few pictures for a theme day. And maybe short clip. We did not intend for that to escalate into the fifth time having sex in the last 24 hours. Turns out we nearly broke him...

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.