My Qualifications to Write About Crossdressing
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An Introduction To Crossdressing Pt 4 free porn video
In Part 3, Jackie and I had our way with each other for the first time and then headed to the shower to ‘clean up’.
As I was removing my feminine attributes - the wig, makeup and lingerie - it occurred to me that even without those items I still felt rather girly. Previously whenever I would change out of my lingerie back into my man clothes, my attitude would change as well. Maybe my attitude hadn’t changed this time since I had dressed all the way and given myself completely as a woman. Whatever the reason really was didn’t matter; all that mattered was that I wanted to be this way all the time.
As I slipped into the shower behind Jackie, I dropped to my knees, grabbing his cheeks and spreading them wide so I could give him a proper cleaning. Feeling my tongue slip across his little star, Jackie leaned forward and pushed back simultaneously, giving me better access to bury my face deep. As you can imagine, this did wonders for his quickly hardening cock. When he started stroking himself I pulled myself up, turned to face the shower wall and begged him to please finish up inside me. As he eased into my still-stretched hole, I could feel him starting to shake with his second orgasm of the night.
When Jackie finished shaking, I backed him up against the wall, making sure that his cock couldn’t leave. I grabbed his left hand and brought it to my left nipple and had him lightly squeeze and twist. His right hand I brought to my cock and had him slowly stroke it while I ground my ass on his half-hard cock. With all these sensations working at the same time, I was right on the edge rather quickly but didn’t want to come just yet. I pulled his right hand off of my cock and had him play with my right nipple while I ever so gently stroked myself, keeping my orgasm at bay.
I guess my continuous grinding on his cock started getting Jackie a little fired up and he started to suck and nibble on my neck. Then he started working my nipples harder and pumping his hips forcing his hardening cock further into my bowels. I quit stroking myself and just let him have his way with me and before I knew it, I was having one of the best orgasms of my life. As my orgasm started to subside, my knees weakened but Jackie held me up while he pounded my ass for another minute before he came again.
We both slid down to the bottom of the tub and our shower slowly became a bath. With me laying on top, with my back to him and his softening cock still inside of me, I switched the water to fill the tub. We just laid there relaxing and petting each other. While we were soaking, I told Jackie how much I enjoyed being a girl for him and hoped he didn’t mind me acting so feminine. He said it was all part of the week-end and to have fun with the whole experience. We eventually found our way to the bed and within minutes, we were both fast asleep.
Waking up in a strange bed with someone new that I was cuddled up to was an exciting experience. With Jackie behind me, spooning me and his arm 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 afternoon. Heather said that they were booked for the day but if we were willing to add a fifty she was sure she could get Amanda to stay late and take care of our makeup. We agreed to the deal and were told to come to the side door at six which left us about five hours to kill and we decided to go to the shop for more clothes.
When Jackie and I got to the shop, we headed to the clothing side immediately, acting like two giddy school girls. As I was looking for the shortest possible skirts, Jackie was looking over the shoes trying to find the highest heels. Heather stopped by to see if we needed any help and I asked her for suggestions for a top to go with the super short black skirt I found. She found me a sheer red blouse that would go great with the red corset underneath and I went to try them on while she helped Jackie with his shoes.
I removed my dress and put on the blouse, loving the way it looked so sheer that I could see my nipples just above the corset. Then I pulled up the skirt and saw in the mirror that it just barely covered my ass and if I bent over even a little, there was plenty to see. I walked out of the dressing room to show Jackie my outfit and to ask him what he thought and he was walking around in six-inch heels like a pro. He turned to check me out and his mouth hung open and all he said was, ‘Wowww.’ I took that as a good sign and then asked Heather where the stockings were so I could get some red and black thigh-highs to go with my new outfit.
As I was perusing the stocking collection, Jackie strutted over in his black stiletto heels and started fondling my ass under my skirt. As he started rimming my hole with his middle finger, he told me that my new outfit was quite sexy and he wanted one to match. I told him that if he kept up what he was doing, mine would be dirty before I even paid for it, so he led me into the changing room and dropped to his knees. It only took about a minute before I was cumming in his hot mouth and he didn’t spill a drop.
After Jackie stood up, he leaned in and gave me a great kiss along with half a mouthful of my own cum. As he walked away, he looked over his shoulder and said that he would prefer his outfit to be all black. When I started to regain my strength, I changed back into my dress since I didn’t think a see-through blouse was appropriate for the daytime. I then walked around and picked out all the parts of Jackie’s new outfit and brought everything to the cashier. I paid for everything since Jackie had already treated me last time and then we headed out for a late lunch.
When we got back to the hotel, we both took quick showers and then put on our new outfits. By the time we were finished getting dressed, we had just enough time to get to the shop for our makeup to be done by Amanda. She took her time on each of us and did a superb job for which we tipped her well. It was about 7:30 as we were leaving the store and it was getting pretty dark so we decided to head to the first club and get something to eat before the evening really got started.
To be continued. . . .
As I was removing my feminine attributes - the wig, makeup and lingerie - it occurred to me that even without those items I still felt rather girly. Previously whenever I would change out of my lingerie back into my man clothes, my attitude would change as well. Maybe my attitude hadn’t changed this time since I had dressed all the way and given myself completely as a woman. Whatever the reason really was didn’t matter; all that mattered was that I wanted to be this way all the time.
As I slipped into the shower behind Jackie, I dropped to my knees, grabbing his cheeks and spreading them wide so I could give him a proper cleaning. Feeling my tongue slip across his little star, Jackie leaned forward and pushed back simultaneously, giving me better access to bury my face deep. As you can imagine, this did wonders for his quickly hardening cock. When he started stroking himself I pulled myself up, turned to face the shower wall and begged him to please finish up inside me. As he eased into my still-stretched hole, I could feel him starting to shake with his second orgasm of the night.
When Jackie finished shaking, I backed him up against the wall, making sure that his cock couldn’t leave. I grabbed his left hand and brought it to my left nipple and had him lightly squeeze and twist. His right hand I brought to my cock and had him slowly stroke it while I ground my ass on his half-hard cock. With all these sensations working at the same time, I was right on the edge rather quickly but didn’t want to come just yet. I pulled his right hand off of my cock and had him play with my right nipple while I ever so gently stroked myself, keeping my orgasm at bay.
I guess my continuous grinding on his cock started getting Jackie a little fired up and he started to suck and nibble on my neck. Then he started working my nipples harder and pumping his hips forcing his hardening cock further into my bowels. I quit stroking myself and just let him have his way with me and before I knew it, I was having one of the best orgasms of my life. As my orgasm started to subside, my knees weakened but Jackie held me up while he pounded my ass for another minute before he came again.
We both slid down to the bottom of the tub and our shower slowly became a bath. With me laying on top, with my back to him and his softening cock still inside of me, I switched the water to fill the tub. We just laid there relaxing and petting each other. While we were soaking, I told Jackie how much I enjoyed being a girl for him and hoped he didn’t mind me acting so feminine. He said it was all part of the week-end and to have fun with the whole experience. We eventually found our way to the bed and within minutes, we were both fast asleep.
Waking up in a strange bed with someone new that I was cuddled up to was an exciting experience. With Jackie behind me, spooning me and his arm 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 afternoon. Heather said that they were booked for the day but if we were willing to add a fifty she was sure she could get Amanda to stay late and take care of our makeup. We agreed to the deal and were told to come to the side door at six which left us about five hours to kill and we decided to go to the shop for more clothes.
When Jackie and I got to the shop, we headed to the clothing side immediately, acting like two giddy school girls. As I was looking for the shortest possible skirts, Jackie was looking over the shoes trying to find the highest heels. Heather stopped by to see if we needed any help and I asked her for suggestions for a top to go with the super short black skirt I found. She found me a sheer red blouse that would go great with the red corset underneath and I went to try them on while she helped Jackie with his shoes.
I removed my dress and put on the blouse, loving the way it looked so sheer that I could see my nipples just above the corset. Then I pulled up the skirt and saw in the mirror that it just barely covered my ass and if I bent over even a little, there was plenty to see. I walked out of the dressing room to show Jackie my outfit and to ask him what he thought and he was walking around in six-inch heels like a pro. He turned to check me out and his mouth hung open and all he said was, ‘Wowww.’ I took that as a good sign and then asked Heather where the stockings were so I could get some red and black thigh-highs to go with my new outfit.
As I was perusing the stocking collection, Jackie strutted over in his black stiletto heels and started fondling my ass under my skirt. As he started rimming my hole with his middle finger, he told me that my new outfit was quite sexy and he wanted one to match. I told him that if he kept up what he was doing, mine would be dirty before I even paid for it, so he led me into the changing room and dropped to his knees. It only took about a minute before I was cumming in his hot mouth and he didn’t spill a drop.
After Jackie stood up, he leaned in and gave me a great kiss along with half a mouthful of my own cum. As he walked away, he looked over his shoulder and said that he would prefer his outfit to be all black. When I started to regain my strength, I changed back into my dress since I didn’t think a see-through blouse was appropriate for the daytime. I then walked around and picked out all the parts of Jackie’s new outfit and brought everything to the cashier. I paid for everything since Jackie had already treated me last time and then we headed out for a late lunch.
When we got back to the hotel, we both took quick showers and then put on our new outfits. By the time we were finished getting dressed, we had just enough time to get to the shop for our makeup to be done by Amanda. She took her time on each of us and did a superb job for which we tipped her well. It was about 7:30 as we were leaving the store and it was getting pretty dark so we decided to head to the first club and get something to eat before the evening really got started.
To be continued. . . .
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- 18.05.2020
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