First experience as a high school CD slut
My senior year in high school 1989 was one of my favorite years of my life. I had my first car, first girlfriend, and first experience as a fully dressed cross dresser. During spring break in late March my freinds and I would hang out at a neighbor’s house a few doors down from my house..his name was Kevin. He was late 20’s had a hot wife and would buy us beer, and let us watch porn at his house Saturday afternoons and evenings while his wife worked (we always thought she was a stripper and he eventually told us all that she was). So basically we’d Hang out with him watch some porn on VHS tapes and after I would (and I’m sure my freinds would) go home and jack off as soon as I found a private place. The only difference was I would take a pair of my sisters or moms bra and panties and wear them as I masturbated. I loved to stand in front of a mirror and do it..my sister had two dresses that fit me perfectly and I would occasionally sneak 1 of those out of her closet and wear it. I had been doing this since I was 10 years old and the urge just kept getting stronger. On a Saturday in late March I had an experience that would change my world forever.
It was about 2 in the afternoon and Kevin came over to help me and my dad carry some furniture into our house. After we finished the job in about 20 minutes, kevin asked me if I could come over and help him out. I of course said yes, hoping to watch some porn. As we were walking to his house he said he just got 3 new videos and his wife was out of town with their baby to visit her parents so he new he wasn’t getting laid the next few days. We got to his house I sat on his couch and he popped the video in the VCR, and went into the kitchen and said he would bring me an old Milwaukee beer. The video came on “Naughty Nurses 2” was the name of it (I’m a Nurse now so maybe this was my inspiration). I remember the opening scene was two girls doing each other with a black guy watching and stroking his big cock. Kevin came back into the room handed me my beer and said he likes to wear jessica’s (His wife) panties when he watches porn. I remember almost feeling a sense of relief knowing that I wasn’t some kind of freak or gay because I liked to do the same thing. I told him how I would wear my sisters or moms panties sometimes and actually would put on my sisters bras sometimes. He told me I can go into the bedroom and the top drawer in the dresser was where his wives panties were and I could put a pair on if I’d like. He then pulled the waistband down on his sweatpants and showed me the pink panties he was wearing. He said she has a bunch and I could just pick a pair. He said it’s cool to know he wasn’t the only one that like wearing girls panties. I laughed and got up and went upstairs to their bedroom.
I remember thinking to myself as I walked up the stairs that this was wierd, I was nervous but extremely excited. When I got to the bedroom I walked in, shut the door and went to the dresser I opened the drawer and there were dozens of colored satin panties and cotton panties. I picked out a pair of red satin panties took my sweats and underwear off and put them on.. I was totally hard and felt totally nervous. I opened the 2nd drawer and there were all kinds of bras and tops. I picked out a black bra and took my sweatshirt off and put the bra on.. I remember my hands trembling as I snapped the back hooks on.. I’m now standing in their bedroom in a black bra and red panties. I walked into the bathroom which was attached to the bedroom and looked at myself in the mirror. I alway was skinny as a teenager and about 5’7”. Everyone said I had girl legs and a girl butt which I hated as a teenager but love now as people still all these years later tell me I have better legs and ass then most women lol. So I stood in front of the mirror admiring myself for about 20 seconds.. I was so turned on. I walked back into the bedroom and peeked into the closet which was open. I noticed a black duffle bag on the floor and looked into it. The was dresses, hairspray a curling iron and a short red wig and a blonde wig inside. I reached down and picked up the short red hair wig. I had never put a wig on so I wanted to see how I looked in one. I went back into the bathroom and put the wig on and looked in the mirror. I was completely amazed and aroused at how sexy I looked and felt in the wig. I pulled my panties down and began stroking my hard cock for about 5 seconds and had to stop lol .A few seconds later I heard the bedroom door open and heard Kevin ask if I was ok in there? I immediately felt lightheaded, my stomach started turning, and my hard on was gone. This was gonna be the most embarrassing moment of my life. I just wanted to cry...
I stood in the bathroom, my legs were shaking, I felt sick to my stomach. Next thing I know Kevin is looking into the bathroom. There I stood wearing his wife’s red wig, black bra and red panties. He looks me up and down and said holy fuck you look hot! I told him thanks and was ready to apologize for going thru the closet and other drawers but before I could say anything he told me I should put some of his wife’s makeup on. The counter in the bathroom was cluttered with makeup and lotions and perfumes. He then walked to the closet and brought the duffle bag to me and said I could pick out a dress if I’d like to and see how I looked in it. He said he was going back down to get another beer and asked if I wanted another one. I told him sure. He said he would be back. After he left I found some eye liner and started to put it on. Only one other time had I put on makeup and it was like a year before so I wasn’t real good at it. My hand was shaking so I remember putting it on too thick and looked like Alice Cooper lol. The second eye was better and went on thinner. I then found some darker red lipstick which really looked good on me. I put some of the lipstick on my cheeks and rubbed it back towards my ears. I remember looking at myself thinking I looked like a porn star. I started to get so aroused and hard. I reached into the duffel bag and pulled out a slinky black and silver dress with spaghetti straps.. I remember putting it on and feeling so sexy and slutty.. I looked like a stripper! There was also a few pairs of thigh highs in the bag so I grabbed some black sheer ones and put them on. This was the first time I ever put thigh highs on and I have been hooked ever since. So there I stood 3 o’clock on a Saturday afternoon, a high school senior, dressed in a bra, panties, red wig, black dress and thigh high stockings. I had never felt as sexy and sexual as I did at this moment in my life. Then suddenly I thought to my self.. what is going to happen next? What do I do now? Do I go downstairs dressed like this and watch porn? What sort of intentions does Kevin have? I was suddenly very nervous once again.
I stood in the bathroom not really knowing what to do. I was thinking I would just get undressed, wash my face off and go back down. But I looked so hot I really didn’t want to. A couple minutes passed and I was kinda just pacing around the room looking in the mirrors at myself thinking how hot I looked. Kevin then yelled up the stairs asking if I was still dressed? I told him yeah and he said “ awesome! Come down and watch this movie” I walked out of the bedroom and slowly down the stairs. I remember the sounds of the sex scene on the TV as I walked into the room. Kevin was sitting in his recliner looking at me. I glanced at the tv and saw two brunettes having a threesome with some guy. Kevin was just staring at me telling me how hot I looked and I should be a porn star. I definately considered that a compliment. I remember walking in front of him to go sit on the couch and I noticed he had his hand inside his sweatpants and was grabbing his cock..I sat on the couch and grabbed my beer which was on the end table between the recliner and where I was sitting. I remember crossing my legs as I was sitting trying to be as feminine as I could. After about a minute of silence (other then the sluts getting banged on TV) Kevin told me to stand up so he could look at how good I look. I knew things were about to get very interesting....
I stood up and took a few steps over towards the recliner. Kevin was sitting back, his hand was still in his pants but he was now obviously slowly stroking his cock. I stood there nervous, shaking a little and he was just looking at me, admiring my body and face. He told me to turn around so I slowly did. Now I'm staring at the tv, and Kevin is behind me sitting in his recliner. After about 10 seconds he tells me how hot my legs look in the thigh highs. I then suddenly feel a hand rubbing my right inner knee/ lower thigh area. Kevin tells me to step back towards him a little bit. My legs were now against the recliner. The hand was now moving up my inner thigh and his finger was now rubbing my balls through the panties. Between the sensation of the finger and the sex on tv my girly cock was rock hard..I suddenly didn’t feel nervous anymore, I was aroused and totally into the moment. He then lifted up my dress and told me to bend over which I did. He started rubbing my ass with his hand and smacked it a few times telling me what a sexy slut I was. I looked over my shoulder and he now had his sweatpants pulled down to his mid thighs.. I totally forgot he had the pink panties on which were also rolled down to his thighs. He was stroking his cock and breathing heavy. He then pulled my panties towards the left part of my ass. He took a finger and ran it down my ass crack and back up to the small of my back he then pulled my panties down exposing my little girly ass. I now started stroking my cock with my right hand.i remember looking back at him as he was staring at my ass stroking his cock. He then licked his finger and ran it down the crack of my ass and then started rubbing my hole with his finger . The sensation of the pressure on my tiny hole almost made me come. I had to stop touching my girly cock or I would have exploded. He then pressed his finger inside me and I felt an uncomfortable burning sensation and let out a moan. He told me he was sorry but I told him it was ok. I told him to wet his finger again if he wanted to. He then suddenly moved forward in his recliner and with both hands took my panties down to my ankles. I felt so hot and aroused. I stepped out of the panties and kicked them off to side. He told me to bend over which I did and he lifted up my dress and with both hands and just stared at my ass for like 10 long seconds. I never felt so vulnerable, slutty and excited ever in my life..
Kevin took both his hands and spread my ass cheeks apart exposing my little pink hole. He then slowly blew into my ass then spit on it. He then took a finger and slid it inside me. At first just the tip to his nail bed then slowly forced more of it in until I felt his bottom knuckle I started gyrating my ass back and forth and once again was stroking myself. He was calling me his little princess slut and telling me what a dirty little girl I am..I was stroking my self feverishly and told him I was gonna cum! He then pulled his finger out of my tight ass and told me to turn around. I stood up straight in front of him and lifted my dress with my left hand so he could watch me stroke my girlie cock. He had his pants down to his ankles and was stroking his cock...after about 5 seconds of staring at him stroking I told him I was cumming! He took his left hand and pulled me onto him so I was knee to knee with him me still standing over him. I started moaning and let out a yell as I exploded over his lap and onto his hand as he was stroking his cock. My legs were shaking uncontrollably and I was panting and sweating. I stared at him then he grabbed my right hand and made me grasp his cock. At this moment was gonna just go for it and suck my first cock..I got on my knees, still shaking, and began stroking his cock like I’ve seen the actresses in the movies do. I felt so slutty! I looked at Kevin in the eyes and began to move my face, mouth open, towards that 6 inches of cock. Right before I was about taste my first cock of my life.he said he was cumming and a thick stream of man cum shot into my eye!! I immediate moved my face back and he was moaning as thick streams of white cock juice shot out of his penis. It was something straight out of a XXX movie. After all this we kinda looked at each amazed at what had just happened...
I remember running up the stairs, into the bathroom taking my Girl clothes off and standing in front of the sink scrubbing the makeup (and cum) off my face. I felt guilty, embarrassed, and questioned my sexuality. Was I gay? I like girls and am attracted to girls. But there was something thrilling and sexual about dressing up like a girl and being a slut. After about 15 minutes of cleaning my face, my one eye red from the cumshot. I went downstairs not knowing how to act or what to say. As soon as I got downstairs Kevin told me that I was awesome and that he had a great time playing with me and it was cool, as in no one will know about it. He preceded to tell me his he and his wife ( who is 22 and hot) have threesomes with other guys and girls and also have done some swinging. He said he has played with other guys and and his wife loves it. He really reassured me that what we did was just some kinky playing and there’s nothing to be ashamed or embarrassed about. That made me feel a lot better. I went home and went upstairs and laid in bed thinking about what I had just done. I pulled my pants down, grabbed a hustler magazine and started masturbating. The odd thing was all I could think about was how hot looked as a girl and couldn’t wait to do something like that again.. little did I know that the following week I would once again find myself dressed up like a slut, being a little teenage porn princess....
It was about 2 in the afternoon and Kevin came over to help me and my dad carry some furniture into our house. After we finished the job in about 20 minutes, kevin asked me if I could come over and help him out. I of course said yes, hoping to watch some porn. As we were walking to his house he said he just got 3 new videos and his wife was out of town with their baby to visit her parents so he new he wasn’t getting laid the next few days. We got to his house I sat on his couch and he popped the video in the VCR, and went into the kitchen and said he would bring me an old Milwaukee beer. The video came on “Naughty Nurses 2” was the name of it (I’m a Nurse now so maybe this was my inspiration). I remember the opening scene was two girls doing each other with a black guy watching and stroking his big cock. Kevin came back into the room handed me my beer and said he likes to wear jessica’s (His wife) panties when he watches porn. I remember almost feeling a sense of relief knowing that I wasn’t some kind of freak or gay because I liked to do the same thing. I told him how I would wear my sisters or moms panties sometimes and actually would put on my sisters bras sometimes. He told me I can go into the bedroom and the top drawer in the dresser was where his wives panties were and I could put a pair on if I’d like. He then pulled the waistband down on his sweatpants and showed me the pink panties he was wearing. He said she has a bunch and I could just pick a pair. He said it’s cool to know he wasn’t the only one that like wearing girls panties. I laughed and got up and went upstairs to their bedroom.
I remember thinking to myself as I walked up the stairs that this was wierd, I was nervous but extremely excited. When I got to the bedroom I walked in, shut the door and went to the dresser I opened the drawer and there were dozens of colored satin panties and cotton panties. I picked out a pair of red satin panties took my sweats and underwear off and put them on.. I was totally hard and felt totally nervous. I opened the 2nd drawer and there were all kinds of bras and tops. I picked out a black bra and took my sweatshirt off and put the bra on.. I remember my hands trembling as I snapped the back hooks on.. I’m now standing in their bedroom in a black bra and red panties. I walked into the bathroom which was attached to the bedroom and looked at myself in the mirror. I alway was skinny as a teenager and about 5’7”. Everyone said I had girl legs and a girl butt which I hated as a teenager but love now as people still all these years later tell me I have better legs and ass then most women lol. So I stood in front of the mirror admiring myself for about 20 seconds.. I was so turned on. I walked back into the bedroom and peeked into the closet which was open. I noticed a black duffle bag on the floor and looked into it. The was dresses, hairspray a curling iron and a short red wig and a blonde wig inside. I reached down and picked up the short red hair wig. I had never put a wig on so I wanted to see how I looked in one. I went back into the bathroom and put the wig on and looked in the mirror. I was completely amazed and aroused at how sexy I looked and felt in the wig. I pulled my panties down and began stroking my hard cock for about 5 seconds and had to stop lol .A few seconds later I heard the bedroom door open and heard Kevin ask if I was ok in there? I immediately felt lightheaded, my stomach started turning, and my hard on was gone. This was gonna be the most embarrassing moment of my life. I just wanted to cry...
I stood in the bathroom, my legs were shaking, I felt sick to my stomach. Next thing I know Kevin is looking into the bathroom. There I stood wearing his wife’s red wig, black bra and red panties. He looks me up and down and said holy fuck you look hot! I told him thanks and was ready to apologize for going thru the closet and other drawers but before I could say anything he told me I should put some of his wife’s makeup on. The counter in the bathroom was cluttered with makeup and lotions and perfumes. He then walked to the closet and brought the duffle bag to me and said I could pick out a dress if I’d like to and see how I looked in it. He said he was going back down to get another beer and asked if I wanted another one. I told him sure. He said he would be back. After he left I found some eye liner and started to put it on. Only one other time had I put on makeup and it was like a year before so I wasn’t real good at it. My hand was shaking so I remember putting it on too thick and looked like Alice Cooper lol. The second eye was better and went on thinner. I then found some darker red lipstick which really looked good on me. I put some of the lipstick on my cheeks and rubbed it back towards my ears. I remember looking at myself thinking I looked like a porn star. I started to get so aroused and hard. I reached into the duffel bag and pulled out a slinky black and silver dress with spaghetti straps.. I remember putting it on and feeling so sexy and slutty.. I looked like a stripper! There was also a few pairs of thigh highs in the bag so I grabbed some black sheer ones and put them on. This was the first time I ever put thigh highs on and I have been hooked ever since. So there I stood 3 o’clock on a Saturday afternoon, a high school senior, dressed in a bra, panties, red wig, black dress and thigh high stockings. I had never felt as sexy and sexual as I did at this moment in my life. Then suddenly I thought to my self.. what is going to happen next? What do I do now? Do I go downstairs dressed like this and watch porn? What sort of intentions does Kevin have? I was suddenly very nervous once again.
I stood in the bathroom not really knowing what to do. I was thinking I would just get undressed, wash my face off and go back down. But I looked so hot I really didn’t want to. A couple minutes passed and I was kinda just pacing around the room looking in the mirrors at myself thinking how hot I looked. Kevin then yelled up the stairs asking if I was still dressed? I told him yeah and he said “ awesome! Come down and watch this movie” I walked out of the bedroom and slowly down the stairs. I remember the sounds of the sex scene on the TV as I walked into the room. Kevin was sitting in his recliner looking at me. I glanced at the tv and saw two brunettes having a threesome with some guy. Kevin was just staring at me telling me how hot I looked and I should be a porn star. I definately considered that a compliment. I remember walking in front of him to go sit on the couch and I noticed he had his hand inside his sweatpants and was grabbing his cock..I sat on the couch and grabbed my beer which was on the end table between the recliner and where I was sitting. I remember crossing my legs as I was sitting trying to be as feminine as I could. After about a minute of silence (other then the sluts getting banged on TV) Kevin told me to stand up so he could look at how good I look. I knew things were about to get very interesting....
I stood up and took a few steps over towards the recliner. Kevin was sitting back, his hand was still in his pants but he was now obviously slowly stroking his cock. I stood there nervous, shaking a little and he was just looking at me, admiring my body and face. He told me to turn around so I slowly did. Now I'm staring at the tv, and Kevin is behind me sitting in his recliner. After about 10 seconds he tells me how hot my legs look in the thigh highs. I then suddenly feel a hand rubbing my right inner knee/ lower thigh area. Kevin tells me to step back towards him a little bit. My legs were now against the recliner. The hand was now moving up my inner thigh and his finger was now rubbing my balls through the panties. Between the sensation of the finger and the sex on tv my girly cock was rock hard..I suddenly didn’t feel nervous anymore, I was aroused and totally into the moment. He then lifted up my dress and told me to bend over which I did. He started rubbing my ass with his hand and smacked it a few times telling me what a sexy slut I was. I looked over my shoulder and he now had his sweatpants pulled down to his mid thighs.. I totally forgot he had the pink panties on which were also rolled down to his thighs. He was stroking his cock and breathing heavy. He then pulled my panties towards the left part of my ass. He took a finger and ran it down my ass crack and back up to the small of my back he then pulled my panties down exposing my little girly ass. I now started stroking my cock with my right hand.i remember looking back at him as he was staring at my ass stroking his cock. He then licked his finger and ran it down the crack of my ass and then started rubbing my hole with his finger . The sensation of the pressure on my tiny hole almost made me come. I had to stop touching my girly cock or I would have exploded. He then pressed his finger inside me and I felt an uncomfortable burning sensation and let out a moan. He told me he was sorry but I told him it was ok. I told him to wet his finger again if he wanted to. He then suddenly moved forward in his recliner and with both hands took my panties down to my ankles. I felt so hot and aroused. I stepped out of the panties and kicked them off to side. He told me to bend over which I did and he lifted up my dress and with both hands and just stared at my ass for like 10 long seconds. I never felt so vulnerable, slutty and excited ever in my life..
Kevin took both his hands and spread my ass cheeks apart exposing my little pink hole. He then slowly blew into my ass then spit on it. He then took a finger and slid it inside me. At first just the tip to his nail bed then slowly forced more of it in until I felt his bottom knuckle I started gyrating my ass back and forth and once again was stroking myself. He was calling me his little princess slut and telling me what a dirty little girl I am..I was stroking my self feverishly and told him I was gonna cum! He then pulled his finger out of my tight ass and told me to turn around. I stood up straight in front of him and lifted my dress with my left hand so he could watch me stroke my girlie cock. He had his pants down to his ankles and was stroking his cock...after about 5 seconds of staring at him stroking I told him I was cumming! He took his left hand and pulled me onto him so I was knee to knee with him me still standing over him. I started moaning and let out a yell as I exploded over his lap and onto his hand as he was stroking his cock. My legs were shaking uncontrollably and I was panting and sweating. I stared at him then he grabbed my right hand and made me grasp his cock. At this moment was gonna just go for it and suck my first cock..I got on my knees, still shaking, and began stroking his cock like I’ve seen the actresses in the movies do. I felt so slutty! I looked at Kevin in the eyes and began to move my face, mouth open, towards that 6 inches of cock. Right before I was about taste my first cock of my life.he said he was cumming and a thick stream of man cum shot into my eye!! I immediate moved my face back and he was moaning as thick streams of white cock juice shot out of his penis. It was something straight out of a XXX movie. After all this we kinda looked at each amazed at what had just happened...
I remember running up the stairs, into the bathroom taking my Girl clothes off and standing in front of the sink scrubbing the makeup (and cum) off my face. I felt guilty, embarrassed, and questioned my sexuality. Was I gay? I like girls and am attracted to girls. But there was something thrilling and sexual about dressing up like a girl and being a slut. After about 15 minutes of cleaning my face, my one eye red from the cumshot. I went downstairs not knowing how to act or what to say. As soon as I got downstairs Kevin told me that I was awesome and that he had a great time playing with me and it was cool, as in no one will know about it. He preceded to tell me his he and his wife ( who is 22 and hot) have threesomes with other guys and girls and also have done some swinging. He said he has played with other guys and and his wife loves it. He really reassured me that what we did was just some kinky playing and there’s nothing to be ashamed or embarrassed about. That made me feel a lot better. I went home and went upstairs and laid in bed thinking about what I had just done. I pulled my pants down, grabbed a hustler magazine and started masturbating. The odd thing was all I could think about was how hot looked as a girl and couldn’t wait to do something like that again.. little did I know that the following week I would once again find myself dressed up like a slut, being a little teenage porn princess....
4 years ago
I enjoyed your story. Thank you for sharing it.