Been a while since our last post mainly due to having other priorities in life pop up. I’m sure like for many other people the last two years have been crazy. We’ve dealt with both being out of work for a good chunk of time, finding new jobs, and in general just finding ways to stay positive and keeping our heads above water.

During that time we’ve always kept ourselves open sexually for new opportunities. There were a few one offs (once on vacation in Mexico) and even another who was on and off for a couple of months (see last few posts), but at the end of the day none of them really fit for what we were looking for.

Well that may be coming to a change as Jenna has recently met someone new and to put it simply, he checks all the boxes. He is 39 years old which is probably the sweet spot as we were looking for someone older and mature without being too old and there being too much of an age gap. He is single and is looking for something ongoing and long term. He is also very open to the idea of being a third in a relationship. He is 6’3, which is another ideal as we were hoping to find someone physically bigger than me (6’1) if possible. Jenna has also mentioned he is very handsome with piercing blue eyes, and shaggy brown hair. Through texting with him and her one meetup she's had so far she has also mentioned that he has an amazing personality. He is very open and great at communicating, funny and very easy going.

Sexually, he is very controlling and dominant which is exactly what we are looking for. He likes to take charge, set rules and get his way while also making sure that Jenna is completely satisfied. I will refer to him as James moving forward.

With that background out of the way I can get into the details of the past two weeks and how everything came together. About two weeks ago now Jenna received a message on her snapchat, a simple “Happy New Year”. To preface, I will mention that the only people Jenna has on this snapchat are people that I have usually vetted and potential candidates for a bull/bf. She didn’t recognize his name when the chat initially came through and wasn’t sure who it was, but because she knew it was someone who had potential, she replied and their conversation started.

I don't have too many details on the specifics of their conversations, but I do know they got intense fairly quickly. She mentioned to me a few days after the first chat that she’s been talking to a guy and that she’s really enjoying it. Mentioning that they have a really good connection and that he’s very good at dirty talk. Not only that but he was also very open about what he was looking for and about himself/his life in general, which Jenna really appreciated. She asked me if I knew where this guy was from originally (Reddit, Online sites, Personals), I looked but couldn’t find any convo with him anywhere. We found out later that he had replied over a year ago to one of our postings on a personal site. At the time he was really intrigued by both her picture and our posting, however he was in a relationship back then so it didn’t go much further than him adding her on Snapchat and a few messages.

One important thing to note is that he lives a decent distance away, nothing too far but also far enough that seeing each other isn’t a simple task. It so happened that he was planning on being in town on Friday the 14th, so as the two of them chatted and they made plans that they would meet up for a date that night. That week could not go fat enough for Jenna. All week she was on her phone as they texted back and forth, mentioning how she couldn’t wait for Friday and that she had a really good feeling about him. I would fall asleep around 11pm most nights but she would continue texting till 1am most nights, building up the anticipation. He really understood her sexual needs and knew just what to say to get her going.

Fast forward to Friday afternoon, his plan was to get in around 8pm and the two of them would meet downtown for dinner. Of course the sexual tension was through the roof so they both decided that if things went well at dinner, they could grab a hotel room for the night. My role would be to drop her off at 8pm for her date and then either stick around and pick her up after or go home and pick her up in the morning if things went well (which all signs were pointing to).

She got a text from James at 5pm saying that the friend he was supposed to visit just tested positive for Covid. He had already left and was on his way to our city so he was going to come regardless now. This meant two things, that he would need to get a hotel regardless since he couldn’t stay with his friend and also that he would have a lot more spare time on Saturday since he wouldn’t be seeing his friend. He went ahead and booked a hotel. In the meantime Jenna was finishing off getting ready, doing her hair/makeup while she had me painting her toenails. She took several pictures in different lingerie that she sent to him to have him choose what she would wear that night. He chose her all white lingerie set (pic posted separately)

During our drive downtown she kept saying how nervous/excited she was. She felt something different with James than with any other guy she had talked to in the past and was on edge to finally meet him. She wore a pair of sexy tight fitting black pants that hugged her ass and a floral top that showed quite a bit of cleavage along with a glimpse of her sexy white bra she had on underneath. All complemented by a coat of bright red lipstick.

We parked our car down the street from the restaurant, which was also a block away from the hotel. I kissed her goodbye as she walked towards the restaurant. I walked the other way to grab myself a dinner nearby as well. She met James out front but realized the wait was over an hour for a table so they would have to switch plans. He mentioned the hotel had a nice restaurant in it and it seemed like there were open tables when he was leaving, so they decided to head back there. Jenna texted me the update and also asked if I could grab some drinks for them cause they will likely just head up to the room after dinner, oh and also to grab a pack of condoms (somehow we had both forgotten to grab these). Within those 10 mins of being with him she already knew she would be spending the night, so I walked over to the liquor store and grabbed a bottle of Rose and then to the 7-11 to grab some condoms. I went back to the car and placed both things in her overnight bag and then went to grab food. We decided we’d both meet after dinner for me to pass her overnight bag to her before I left to go home.

We met outside the hotel at 9:30 and she told me how amazing of a time she was having and was so happy/excited that she met him. We shared one final kiss as I passed her the bag and she turned and walked towards the elevator to meet back up with James.

I just realized how long this has already gotten, so I will stop here for now and make another separate post with the details of the night/next day shortly.