First Time In A Long Time 2

A little about myself. I am a panty wearer. I love everything about women's panties and sexy men's underwear. A few years ago I stumbled upon a very popular app, where members can share photos and began posting pictures of myself in panties and lingerie. I have been identifying myself as bisexual most of my life. But, at 54 years old, it had been since my teens that I have done anything with someone of the same sex. That all changed a couple of weeks ago.

I met a guy, Brad, who is into cross dressing and wears/owns a lot of lingerie. We met thru the app mentioned earlier. We began messaging each other on the app and at one point, I asked if he had any pictures. What I meant was of him dressed up or wearing his panties. What he sent surprised me. He sent a picture of his face! Not many men are brave enough to that on this app, me included. We chatted several times about what we like and what we wanted. He asked me if I was willing to meet up with him. I had made the decision that after too many years of fantasy, I wanted to meet up with someone! We made arrangements to meet up at a local eatery to get to know each other and see if we were compatible.

We met up on a Friday night at the agreed upon time. I walked into the bar area and recognized him immediately. We introduced ourselves and seeing as we were both as described, decided to get a table and have a beer. We started off just talking about what we each do for a living and a little bit about our past. At one point he told me that I was cuter in person than I was in the picture that I sent him. That made me feel good and then and there, I knew we were going to have some fun. We spent the next hour talking. I told him about my failed marriage and how and when I started wearing panties. He asked me if I was wearing some tonight and I told him I was! I asked him if he was and he said that indeed he did have panties on also. At one point during the conversation, he told me that he wanted be alone with me, that night. The couple at the next table overheard what he said, and he just looked over at them and said that he didn't care who knew about it!

He asked if we could go to my place, but we couldn't because my son was home.

He rode his motorcycle to the bar, so that wasn't an option. I suggested we go out to my car and drive around until we found a secluded spot. We were at a large complex with lots of stores and restaurants, so there had to be a secluded space somewhere. As we were walking to my car, we decided to have a cigarette. We were standing outside my car and he was telling me how much he wanted to get into my panties! He even asked if he could kiss me. That is something I had never done, and was something I was wondering if I could do even. There were other people walking to and from their cars, so I told him that I wasn't ready for that, in public anyway.

We got into my car and decided to drive around and find that secluded spot. As soon as I pulled out of the parking space, I decided it was time for me to show him I was serious about following through with this. I reached over and put my hand on the crotch of his jeans. He was already hard! I kept my hand on his crotch, squeezing his cock as I drove around looking for a dark corner to park. He put his left hand on my leg and started to move it up to my crotch. As I drove, he leaned over and started licking my neck and my ear. His hand found it's way to my crotch and he started rubbing my now hard cock. We were both getting very turned on! After a few minutes of driving, I found a good spot and backed in. It was dark enough that nobody walking by could see into the car, but with enough light that we could see what we were doing.

As soon as I took my seat belt off, we both leaned in I had my first ever man on man kiss, complete with lots of tongue! We made out like that for a few minutes with both of us groping each others hard cocks through our jeans! He finally broke the kiss and asked me if I knew what the best part of going on a date with a sissy was. I said "no, what".

He leaned in, kissed me again and said, "you know you are going to get a blow job on the first date!" With that he told me he wanted to see my panties, and started pulling down my zipper. He reached his hand inside, and was feeling my panty covered cock and kissed me again. I reach down to unbutton my jeans and then we both fumbled around trying to pull them down. He said to make sure that I leave my panties up though. When I was finally able to get my jeans around my ankles, he leaned in and started licking my cock through my panties. After a couple of minutes of that, he pulled my cock out of the leg hole, saying he wanted me to leave the panties on! He was sucking my cock and oh my god was he good! He was stroking me with his right as he snaked his left hand under my ass and was squeezing my ass!

As much as I was enjoying the attention he was giving my cock, I knew I wanted his in my mouth. I told him that it was my turn and had him sit up. I reached for his zipper as he undid his belt. He pulled his pants down and I leaned over and did the same that he did to me and licked his cock through his panties! I couldn't take it any longer and pulled his cock and very big balls out of his panties and for the first time in 34 years, I was sucking a cock! It was everything I remembered and even better!! He was just a little shorter than my 7 inches, but he is a little thicker. He was leaking a lot of precum and it tasted so fucking good! In that moment I made myself a promise that it would not be another 30 plus years before I had another cock in my mouth! I was loving every second of it and then a thought popped into my head and I wished I had taken my phone out so that I could have taken some pictures of me with his cock in my mouth!

I was in heaven with his cock in my mouth and was really trying to make him cum! He was breathing very heavily and I thought he was close! I asked him if he was getting ready, and he said no and said that because he was a little drunk and a little high, he wouldn't be able to cum. I was a little disappointed, but still enjoyed the hell out of it!! His cock fit my mouth perfectly and all those memories of my teen years came flooding back..

Finally, he told me that he wanted me to cum in his mouth! I sat back and re-assumed the position with his right hand playing with my balls, his left hand under my ass and his mouth on my cock! He really like to try and deep throat, so he would take me completely in his mouth until he would start gagging! I was surprised when he kept doing it and kept gagging. He would stop every couple of strokes and would tell me how much he wanted my cum! I told him that if you want me to cum, fuck my tight little ass with your finger! He put the index finger of his left hand on my hole and starting pushing it in! He got in to the second knuckle and it felt awesome! After just about a minute or two of this I was cumming, and cumming hard!! He swallowed most of my load, with some of it leaking out of the corners of his mouth! He sat back up and asked me if I always cum that much? I said usually only when getting an incredible blow job like he just gave me! He liked that answer and leaned in to give me another kiss. He stuck his tongue in my mouth and I could taste myself in his mouth!

We rested for a couple of minutes and he asked if I was ready to go again! I said, sadly no, I need a lot more time these days before I would be ready to go again. We pulled our pants up and I started the car. We drove back to where his motorcycle was parked. When we got there, we both decided that we would love to get together again. His bike was parked in the first row and when I stopped the car, it was right in front of the doors to the restaurant we were at earlier. He leaned over and we started kissing again! The kiss only lasted a few seconds, but when he got out of the car, I looked over to the doors of the restaurant and there were people standing there and I think at least one of them saw us kissing and that was hot!!

This story is 100% true and only his name was changed! If you would like to hear about our second meeting, where we spent the night together, let me know and I will write that up too! Thanks for reading!