Umm, yeah, that happened…

On Sunday, I went and dropped my boyfriend off at an airport for his business trip. There was a lot of driving involved, on top of being tired from not getting enough sleep the night before. And then, once I dropped him off I was having a hard time keeping myself from blubbering, but I made it home safely. Then, once I got home… things got crazy…

(Since my boyfriend and I have been attending the club, we have become friends with some very different people. One of these friends is a bisexual man who likes to dress up in ladies clothing.)… just a little background info.

Okay, so on Sunday once I got home, I fed our kids, showered, packed lingerie and sexy outfits, packed makeup, packed some wine and beer, and then hit the road for some “girly” fun.

I was going to hang out with this guy who enjoys wearing ladies clothing. My boyfriend encouraged me to go, and I wanted to get my mind off of being alone while he is gone. Had I stayed home I would have went to bed and probably cried myself to sleep. Going to hangout seemed a better option.

I did not know what to expect. All he had said was that he wanted to take some new pictures, that I should bring some makeup, and I need to bring sexy clothes. I packed almost all of my lingerie and sexy outfits, as well as all of my makeup. Once I arrived…. the night began!

I pulled up and guy him came out to greet me and help carry in what I brought. Once inside, we showed our outfits and talked makeup. He also informed me that we were going to make boobs for him… we were to make them out of old panty hose and rice! But, first I was to do his makeup.

This was the first time that I put makeup on anyone other than myself, our kids, or my younger brother when we were little. My friend wanted a smoky eye, foundation covering his whole face, and basically whatever else I wanted to do…. So, I mixed some foundation to get the correct color and started to apply it. Then, I powdered his face. I applied some of my favorite eye liners and eye shadows to his eyelids, but I let him put on his mascara. After his eyes were done, I applied a little shimmering blush, and then some lipstick. He looked good.

Once his face and the rice boobs were finished, it was time for him to get into some outfits and take some new pictures.

I, also, did not know what expect from this part of the night. I picked out an outfit and he put it on. He even put on my underwear that I brought. (When I agreed to go and hang with him, I just thought what I was bringing was for me to put on and that we would take pictures, and he would wear his own outfits and I would take pictures of just him too….. I assumed too much!)

Once he got dressed and put a wig on, he put some tranny porn on the tv, and then pulled his dick out of the side of the underwear and played with it. I started snapping photo after photo, and he continued to play with his dick as he moved into different poses and positions. He said he wanted to have a hard dick for some pictures. After a few different outfits, he said, while jerking off, that he’d also like for me to see if I could take pictures of him ejaculating….

Now, I have no problem with nudity or sexual behavior. As long as it doesn’t involve blood, too much pain, poop, and or urine. But, I did not expect this situation. Then, after a bit of trying to accomplish an orgasm, he asked for my help…

I Do Not play without my boyfriend. I repeat, I DO NOT PLAY WITHOUT MY BOYFRIEND…. I had established this earlier with him. BUT, that is not what he meant when he asked. He wanted me to put on some of his sheer nylons because he has a thing for them. WHEW!!! I thought it was going to get uncomfortable.

After his request, I obliged and put the nylons on. He started to stare at the nylons and then back to the porn on the screen…  during all of this I was still snapping pictures. He had frequently stated that he had not played with himself like that in front of anyone before, and I could believe that. He seemed nervous a lot of the time and kept his eyes closed for most of it. After a bit more time, he had asked if he could touch the nylons… I had no qualms about this so I, once again, obliged. I put my foot on the couch next to where he was sitting and he started to touch my foot. It was almost as if he was petting the nylons. As I kept snapping photos, I began to rub my foot on his leg and he kept petting part of my shin. As time went on, eventually he stopped and stated that nothing was going to happen. So, I stopped taking pictures and checked my phone.

When I checked my phone, it was after 12 and I had to be up in the morning to get the kids off to school and go to work. So, I started to pack my stuff and collect my belongings.

Now, time to dish on a conversation from earlier during the night… While I was applying his makeup we chatted about sex, anal, and toys. During this conversation I expressed how my boyfriend encourages me and my sexual side, and of how I kind of lived under a rock until him. My boyfriend introduced me to an app for my phone that has dirty sex stories you can read. .  Well, as I was talking I mentioned this one story where a chick went on a date with another chick… or so she thought. Well, during the course of the story, the one chick put on a strap-on and mounted the other chick who still had a dick. So, long story short, I mentioned that I kind of wanted to try that, putting on a strap-on and giving it to somebody. Not thinking about what had just come out of my mouth, he just looked at me and proceeded to ask something I had never been asked before… He asked me if I would do that to him… UMM HUH??… my only response was that you never know what could happen.

Umm, even though I had that thought, I have no idea if I could actually bring myself to go through with it. After, I responded I asked if they actually make strap-ons with double side that way the wearer could get enjoyment out of it as well. He informed me that they do exist.

Well, after I got back into my vehicle and was ready to head out, my boyfriend called me. I explained what all took place that night, well I tried to anyway. Our conversation was cut off by my gps, I was unable to hear him a lot of the time and had to get him to repeat almost everything he said, and I was trying to concentrate on my driving. So, eventually, we said goodnight and got off the phone.

The next day, however, I sent what all happened as well as telling about how our friend had asked me to strap it on and give it to him… Yep, my boyfriend was just as surprised as I was about that request. Honestly, I had no idea what my boyfriend would say in response to that. Well, his response came back and it was almost just as interesting. My boyfriend said he’d probably be okay with it if he was there and could take pictures.

My boyfriend is amazing and I am so very lucky to have him. As far as the request from a friend and the response from my boyfriend, I still don’t know if I could go through with it. I think that I should think about it more and talk to my boyfriend some more as well.

One last thing… YOU NEVER KNOW WHAT COULD HAPPEN.