An Introduction to Crossdressing Pt 4 - Sex Stories

An Introduction to Crossdressing Pt 4

... around me, I continued to feel quite feminine. As I was waking, I squirmed around some and soon realized that Jackie was sporting morning wood. I found this reversal of roles for me quite amusing and quickly decided to take full advantage. Laying on my right side, I lifted my left leg and using a couple fingers, I quickly lubricated my hole with saliva, penetrating it easily. With my leg still up, I reached down and grabbed hold of his cock and guided it to my entrance. Once he started to slide in, I pushed back as far as I could, hoping my movement and his stimulation would get him going. I started a slow back and forth, trying to gently wake him but unfortunately, it seemed that Jackie was a heavy sleeper. It looked like I was going to have to take things into my own hands. I rolled backwards on top of him and then moved into a reverse cow girl position and slowly started working him deeper and deeper. All the movement seemed to bring him around some and as I really started getting into it so did he. Jackie grabbed my ass cheeks, pulling them as far apart as they would go which allowed me to get him even deeper. I was riding him about as fast as possible for a couple of minutes before he came off the bed jamming himself into me while yelling that he was cumming. That final thrust pushed me over the edge and I just shot all over the bed and then collapsed, panting like I had just run a marathon. While we were recovering I asked him, between pants, if he liked his wake up ...

... call. He started to laugh and said that it was great and if he could have me wake him that way every morning. Jackie said he was going to take a shower and I figured that I should actually let him take one so since I was starting to get a little sore from all our fun. I had dozed off while he was in the shower but woke up when he walked out of the bathroom with a towel wrapped around his waist. Jackie asked me if I thought we ought to get dressed for the day and I quickly said, 'That is why we are here, so yes!' He then reminded me that our only female clothes were quite dressy for the daytime but I didn’t care; we were there to dress and be girly. I told him that I would take a quick shower and then we could help each other with make-up and clothes. We found that we were not quite as good as the ladies at the shop but we did a decent job and didn’t look like streetwalkers, so we were happy. We headed out for a late breakfast at a little diner just up the road and after ordering, we mapped out our evening plans. We decided on three different clubs that all were fairly close by our hotel and all three entertained LGBT clientele. The plan was to start at the one furthest away and work our way back towards the hotel. We also decided that we would stay together and if the opportunity arose to add a third or fourth party, we would gladly do so with protection. After finishing our late breakfast, we called back to the shop to see if we could get back in for a makeup refresher for the ...