Going Out

This is a follow up to my previous post about going shopping and meeting Pam. We made plans while having a few drinks the night before to go out on the town the next night. She asked me what I had always wanted to do when I thought about going out in public. I told her I had thought about anything from going to the movie, dinner, concert or just hitting some clubs. Although not some wild club. She threw out a couple of ideas that sounded good and that she would think about it more. She told me just to relax and come dressed and confident she would take care of the rest.

I got through calling on customers around 3 and Pam was going to pick me up a little after 5. I got back and got dressed thinking about the possibilities for the night. Pam called and said she was in the lobby. I touched up my makeup for the hundredth time and headed down. On the way down I thought about the previous day of how nervous I was just to go through the lobby but now I was looking forward to it. I came out and spotted Pam and we hugged and I told her how much I appreciated her doing this. She said no problem. Then she told me she had invited someone else along and was that ok. I said if her friend was ok with my situation I was ok plus having three girls is better than two. She smiled and said it was a guy friend of hers. I was a little taken aback. I then thought why not. We walk out and he was waiting in the car to pick us up. I started to get in the back but Pam told me to get up front with Kevin so we could meet. We introduced each other which was a little awkward do we shake hands like guys or what.

We headed out to a headed out for a few drinks. Luckly Kevin was a cool guy. They knew several other people at the bar and introduced me. I would say hi. Kevin told me not to be so shy from my looks not many people would know and being dressed people didn't notice my voice as much. So I started interacting more and it was a blast. I was standing there talking with a group and Kevin walked up and put his arm around my waist asked joined the conversation. My mind started racing thinking wow he is sure trying to sell me but it felt so good for him to do that. After a while Kevin and I were in our on conversation. I asked him how Pam suckered him into this night. He said he had known her for several years and they would get together once a month or s to catch up. I asked him had they dated or what. She said they didn't but she was a good friend who listen to him a lot. I asked if he dated a lot. He said that was something Pam helped him with a lot. I laughed and said a good looking guy like you shouldn't have problems getting a girl. He said he didn't but his issue was that he was bisexual and that turned off both guys and girls. He said Pam thought we should meet so we knew other people struggled. I told him I was not sure if I was bisexual because I had never been with a guy. He said real quick that he was not looking to have sex with me when Pam invited him. I said good because that was still a big leap for me.

Pam came up about this time and asked if were ready to go down the street for dinner. A few other people joined us as well. As we got close Kevin was in front talking to someone else. I caught up with him and grab his arm and said I needed to sit with him so I would have someone to talk to. We had to wait a few minutes for a table. Pam came up and said she needed to go to the girls room and asked if I wanted to join her. I was thinking I need to go but was one of those things I hadn't thought through of going to the women's restroom. On the way I asked her how this was going to work. She looked at me realizing this was a first and laughed. She said just to walk in grab a stall lift my skirt and pull my panties down and sit and pee and laughed again. Of course all the stalls were taken and we had to wait. It all went smooth. I worried about nothing.

When we got back the group was being seated. Kevin saved Pam and I me a spot next to him. I noticed Kevin like to touch you when he talked. He would be putting his hand on my arm or hand when talking. After dinner we headed out to do some dancing. I told them I was a horrible dancing as a guy and would probably be even worse as a girl. They both got a big laugh. We got a booth when we got there and ordered some drinks. The music was real loud and you had to lean in close to someone and talk. In a few minutes Kevin asked if I wanted to go dance. I smiled and laughed but he just grabbed my hand and lead me to the dance floor. I was thinking the whole time I am fixing to make a fool of myself. He definitely was in the lead. He had my hand telling me what to do. After a while I got the hang of it. After a few songs we decide to rest so he took me by the hand back to the booth. I will admit it felt good in a strange way to have a man take me by the hand like he was protecting me. We where seating there talking and enjoying the music and talking when I noticed he had put his hand on my knee lower thigh. It did feel good. I just loved how he was treating me like a women. I know it is a fantasy but it the moment it feels good. We would go dance a while then sit and rest. He kept putting his hand on my leg I caught my self caught up in the fantasy and I started touching him more. Once when Pam and I had been dancing with him when we were going back to set down she gave him a kiss on the check. So the next time when it was just him and me I gave him a kiss on the check and thanked him for showing me a great time and letting me live my fantasy. He smiled and said he was having a blast. Shortly after that he got up to go to the boys room and gave me a kiss on the check and told me not to leave even though we were in his car. After a while we decided to head to a coffee shop relax a little and visit. As we got up to leave he grabbed my hand and walked me out. It felt so good. We decided on the way just to go to Pam's place and watch a movie. We stopped by a RedBox and rented one and headed off.

Once there I sat on the couch and took off my heels. I had never worn heels for so long let alone danced in them. We got a big blanket I was on one end he was in the middle with Pam on the other end. She was leaning on his shoulder resting he put his arm around me and pulled me in also. He joked about his two beautiful women. In a few minutes Pam rearranged herself to lean on the armrest of the couch. I felt awkward at that point but the fantasy of being cuddled up felt so good. Due to the way we were sitting I had my arm on his leg. He went to slouch a little more and suddenly my arm cam in contact with his hard on. I froze in shock. He quickly adjusted a little. I was thinking WOW! He still had his arm around me rubbing back arm. My mind was racing at this point. I had always fantasized about being with a guy was this the time? I finally decided to see if he still had a hard on. I rearrange a little and moved my arm and it was still there. I must of have done it to obvious because he looked at me and said he was sorry he had no intention to make a move on me. I sort of laughed and told him it was ok in fact in was flattering and gave him a kiss on the check.

Pam woke up shortly and said she was going to get comfortable. She got up and went to her bedroom. I took the chance to go to the bathroom. So I go and think do I stand or sit? I sat. He had gotten up to get some water so I went over to get some also. We sat back down and snuggled up even more than we were before. I know it is corny but we looked at each other and he leaned in to kiss me on the lips. I froze again. After a second I was kissing him back. This went on a few minutes until Pam walked back out and we looked at her embarrassed. She smiled at us and said we could use her bedroom if we needed. We looked at each other and he said well what do you think. I thought a minute and said ok but I am not promising anything. He grabbed my hand and lead me to her bedroom. Pam called me back and told me not to do anything I didn't want to. I said I wouldn't. She said there were condoms and lube in the nightstand if it went that far. He had stopped at the bathroom and we meet as he was coming out. We went in and closed the door. We sat on the end of the bed and began kissing. He began to rub my leg and I began rubbing his. He asked what I was feeling. I said confused but excited. I told him I would prefer he not touch my cock that I wanted the fantasy of being the women. We kissed he rubbed my fake breast. I finally got the nerve up to rub his cock. I unzipped his pants and he stood up and pulled them off. It was a great site. I stood up and reached down and stroked it slowly. It felt so good with his precum starting to ooze out. He asked if he could take my skirt off so I let him. He laid me on the bed and laid on me. It felt so good to feel how excited I had gotten him. I had my legs up in the air trying to figured out the best position. After a few minutes of him on me he asked me if I wanted to try to have sex. I smiled and said yes and then kissed him. I told him Pam had said there was condemns and lube in the night stand. He got both and I help him put a condom on. I told him I had never done this. He said we would take it slow. He lubed himself and me up. He positioned me and started to rub his hard cock against my boipussy. I wanted it so bad at that point. He slowly worked his head in and it hurt so good. It took a while for him to be fully in me. When he was it was such a feeling knowing I could get somebody that work up. He slowly moved in and out. He gradually picked up the pace. After what seemed to be a long time a could see in his face and feel in his cock that he was building up to and orgasm. Soon he let it explode and it felt so great to feel his hard cock throbbing and his body tensing up the relaxing. I myself was so excited that I grabbed my cock when he started to cum I immediately shot my load.

Once we cleaned up we join Pam back in the den. More to come.