The first time I dressed and had sex with a man
This is a true story of the first time I had sex with a man dressed.
I was sitting in a bar one night. I was wearing jeans a t shirt and work boots. I was 30 years old. I was at the bar for an hour and met this older guy in his 60's. we started talking and shooting pool. We sot a few games and were drinking beer. The bar was closing and he said, hey, I have a pool table in my finished basement at my house, you're welcome to come over. I have beer there too. I was pretty much half drunk and said, sure. his house was down the street so we walked there. We went down his basement and it was all fixed up wit a small bar and a couch and tv, and a couch. We drank a few more beers and shot a few games of 8 ball. I was bending over to take a shot and I heard him say, you have a really sweet ass. I just ignored him and took my shot. Then he asked me how tall I was and how much I weighed. I told him, I'm 5' 9", 145 pounds. He said, you really have a feminine body, have you always been thin? I said yes. We sat on the couch and he asked me if I knew what crossdressing was. I said that I'd heard of it. He said, I'll bet you would look so hot dressed. Would you ever consider trying it? I was pretty drunk and said, I'll try anything once as I laughed. He said, no, I'm serious, would you? I said, I guess I would. He told me that he had a friend that used to dress for him but had moved out of state and left his clothes there. You and him are the same size and his clothes will fit if you want to go upstairs to the bedroom, I have them in a box in my closet. Come on, he said, let's go upstairs. So we went to his bed room, I sat on his bed and and he went to the closet and pulled out a pretty big box. He said there was some pretty clothes in there as he opened the box. He was taking everything out and laying them on the bed. Wigs, dresses, high heels, lingerie, toys and lube. I was looking at all the sexy clothes and started getting excited. Once he emptied the box he asked me if I liked the clothes. I said yes I did. Stand up he said, and let me see your body. I stood up as he asked. Now take off those boy clothes so I can see your sexy naked body. He sat in a chair across from me and watched me strip. I was embarrassed but I was kinda drunk so I didn't care and I was getting turned on. Once I was naked he smiled and licked his lips and said, You look great, spin around so I can see all of you, and I did. I had some body hair on me and he said, come into the bathroom with me and he ran the bath. I'm going to shave your body smooth like a real woman so when you dress for me you'll feel like a real woman. He shaved me from the neck down and then toweled me dry. He had some perfume he put on my body. He said, I want you to smell nice for me. Then he took me by the hand and we went back to the bedroom. He told me to stand there as he picked out the outfit he wanted me to wear. 5 inch stillettos, Thigh high laced top stockings, a lace garter belt, a thong with a pouch for my cock, a lace bra that had cup silicone fake tits, a black spandex minidress and a long haired black wig. He sat me down and before I got dressed he put some light make up on me and some lipstick. He told me to stand up and he dressed me in that outfit. Then he said, come look at yourself in the full length mirror. When I saw myself I couldn't believe that was me. My cock started to grow in my thong. I had a hard time walking in the heels but after a while I started getting used to them. Come on, lets go back downstairs and have another drink and shoot some more pool. As I shot pool he was taking pictures and video of me. Come on and sit on the couch with me. Come closer I don't bite. I was nervous. I had no idea what was gonna happen next. He pulled me close to him and put his hand on my thigh and I could swear my cock grew another inch. He ran his hand from my knee to the top of my thigh and I could feel my thing getting wet from my precum. Sit back for me he said, and open your thighs. I did whatever he asked me to do, I felt like I was in a trance. I didn't seem real what was happening. He got on his knees in front of me and hiked up my minidress. then he slid off my thong and my hard wet cock from the precum was inches from his face. I could feel his hot breath on my cock as he got closer to it. He grabbed my shaft very softly and licked the precum from the tip. Then he kissed it and cupped my balls as he sucked my hard cock deep into his mouth. I could feel my hips strarting to buck forward. I was moaning and didn't think I was gonna last much longer before I came and then he stopped. He said kind of forcefully, Stand up and bend over my pool table you little slut. I did as he asked. He stood behind me cose with his hands on my waist and then I could hear him undo his pants. He got on his knees behind me and slapped my ass cheeks and the tingle felt soooooooo good. Then I felt the tip of his tongue touch my asshole and I moaned like a bitch. He took his hands and spread my ass cheeks wide, slapping them now and then. My asshole was wet from his spit and then he put his index finger inside me. Then another finger. He was stretching my tight asshole. I was moaning and precum was leaking from me heavy. He used my precum to lube me up. The he stood up behind me and lubed up his cock with his sspit and my precum. he took his hands and rubbed my lace toped stockings and I felt him right behind me with his cock head. I felt it press up against my asshole and he slowly pushed deeper and deeper till he was all the way inside me. He grabbed my hips and pulled me closer to him. Then he slowly started to pull out but left his cock head inside me. Then he pushed his way back in. He did this over and over and faster and faster. It felt so fucking good. I felt like I was going to cum but he didn't touch my cock and neither did I. It was intense and I never felt this feeling before and then I started to cum hands free and I coucld feel my asshole gripping his cock as I came. I heard him grunting and he shot his load deep inside my ass. I collapsed onto the pool table and he was still inside me. He kissed my neck and pulled out and I could feel his cum leaking from my asshole down onto my balls. My cock was throbbing and I was spent. It was the best sex I'd ever had. After a while we sat back on the couch and I sat on his lap and hhe kissed me. He felt me up as we kissed. Then I felt him pushing my had back to his cock. He was hard again. I sucked him while he fingered my cum filled asshole. Then he sat back and I climed on top of him. He slid his cock inside me and I kissed him while I bounced on his cock. Then he started to cum and i came too at the same time hands free cumming all over his stomach and chest. I eventually got dressed and he asked me if I would like to be his steady gurl, no strings. Just sex buddies. I said HELL YEAH. I would visit him once a week. That went on for over a year until he moved out to California by his daughter. I've been dressing ever since then. I LOVE getting dressed up and having sex with men. And I always cum hands free.
Miki - 2020
I was sitting in a bar one night. I was wearing jeans a t shirt and work boots. I was 30 years old. I was at the bar for an hour and met this older guy in his 60's. we started talking and shooting pool. We sot a few games and were drinking beer. The bar was closing and he said, hey, I have a pool table in my finished basement at my house, you're welcome to come over. I have beer there too. I was pretty much half drunk and said, sure. his house was down the street so we walked there. We went down his basement and it was all fixed up wit a small bar and a couch and tv, and a couch. We drank a few more beers and shot a few games of 8 ball. I was bending over to take a shot and I heard him say, you have a really sweet ass. I just ignored him and took my shot. Then he asked me how tall I was and how much I weighed. I told him, I'm 5' 9", 145 pounds. He said, you really have a feminine body, have you always been thin? I said yes. We sat on the couch and he asked me if I knew what crossdressing was. I said that I'd heard of it. He said, I'll bet you would look so hot dressed. Would you ever consider trying it? I was pretty drunk and said, I'll try anything once as I laughed. He said, no, I'm serious, would you? I said, I guess I would. He told me that he had a friend that used to dress for him but had moved out of state and left his clothes there. You and him are the same size and his clothes will fit if you want to go upstairs to the bedroom, I have them in a box in my closet. Come on, he said, let's go upstairs. So we went to his bed room, I sat on his bed and and he went to the closet and pulled out a pretty big box. He said there was some pretty clothes in there as he opened the box. He was taking everything out and laying them on the bed. Wigs, dresses, high heels, lingerie, toys and lube. I was looking at all the sexy clothes and started getting excited. Once he emptied the box he asked me if I liked the clothes. I said yes I did. Stand up he said, and let me see your body. I stood up as he asked. Now take off those boy clothes so I can see your sexy naked body. He sat in a chair across from me and watched me strip. I was embarrassed but I was kinda drunk so I didn't care and I was getting turned on. Once I was naked he smiled and licked his lips and said, You look great, spin around so I can see all of you, and I did. I had some body hair on me and he said, come into the bathroom with me and he ran the bath. I'm going to shave your body smooth like a real woman so when you dress for me you'll feel like a real woman. He shaved me from the neck down and then toweled me dry. He had some perfume he put on my body. He said, I want you to smell nice for me. Then he took me by the hand and we went back to the bedroom. He told me to stand there as he picked out the outfit he wanted me to wear. 5 inch stillettos, Thigh high laced top stockings, a lace garter belt, a thong with a pouch for my cock, a lace bra that had cup silicone fake tits, a black spandex minidress and a long haired black wig. He sat me down and before I got dressed he put some light make up on me and some lipstick. He told me to stand up and he dressed me in that outfit. Then he said, come look at yourself in the full length mirror. When I saw myself I couldn't believe that was me. My cock started to grow in my thong. I had a hard time walking in the heels but after a while I started getting used to them. Come on, lets go back downstairs and have another drink and shoot some more pool. As I shot pool he was taking pictures and video of me. Come on and sit on the couch with me. Come closer I don't bite. I was nervous. I had no idea what was gonna happen next. He pulled me close to him and put his hand on my thigh and I could swear my cock grew another inch. He ran his hand from my knee to the top of my thigh and I could feel my thing getting wet from my precum. Sit back for me he said, and open your thighs. I did whatever he asked me to do, I felt like I was in a trance. I didn't seem real what was happening. He got on his knees in front of me and hiked up my minidress. then he slid off my thong and my hard wet cock from the precum was inches from his face. I could feel his hot breath on my cock as he got closer to it. He grabbed my shaft very softly and licked the precum from the tip. Then he kissed it and cupped my balls as he sucked my hard cock deep into his mouth. I could feel my hips strarting to buck forward. I was moaning and didn't think I was gonna last much longer before I came and then he stopped. He said kind of forcefully, Stand up and bend over my pool table you little slut. I did as he asked. He stood behind me cose with his hands on my waist and then I could hear him undo his pants. He got on his knees behind me and slapped my ass cheeks and the tingle felt soooooooo good. Then I felt the tip of his tongue touch my asshole and I moaned like a bitch. He took his hands and spread my ass cheeks wide, slapping them now and then. My asshole was wet from his spit and then he put his index finger inside me. Then another finger. He was stretching my tight asshole. I was moaning and precum was leaking from me heavy. He used my precum to lube me up. The he stood up behind me and lubed up his cock with his sspit and my precum. he took his hands and rubbed my lace toped stockings and I felt him right behind me with his cock head. I felt it press up against my asshole and he slowly pushed deeper and deeper till he was all the way inside me. He grabbed my hips and pulled me closer to him. Then he slowly started to pull out but left his cock head inside me. Then he pushed his way back in. He did this over and over and faster and faster. It felt so fucking good. I felt like I was going to cum but he didn't touch my cock and neither did I. It was intense and I never felt this feeling before and then I started to cum hands free and I coucld feel my asshole gripping his cock as I came. I heard him grunting and he shot his load deep inside my ass. I collapsed onto the pool table and he was still inside me. He kissed my neck and pulled out and I could feel his cum leaking from my asshole down onto my balls. My cock was throbbing and I was spent. It was the best sex I'd ever had. After a while we sat back on the couch and I sat on his lap and hhe kissed me. He felt me up as we kissed. Then I felt him pushing my had back to his cock. He was hard again. I sucked him while he fingered my cum filled asshole. Then he sat back and I climed on top of him. He slid his cock inside me and I kissed him while I bounced on his cock. Then he started to cum and i came too at the same time hands free cumming all over his stomach and chest. I eventually got dressed and he asked me if I would like to be his steady gurl, no strings. Just sex buddies. I said HELL YEAH. I would visit him once a week. That went on for over a year until he moved out to California by his daughter. I've been dressing ever since then. I LOVE getting dressed up and having sex with men. And I always cum hands free.
Miki - 2020
5年前
