I will never forget the day Carrie enter my secret world. It was the summer I was 17, I had been dressing my sisters clothes since I was about 8yo. In more recent years I had started buying a few of my own clothes and lingerie nylons and make-up. It was a Saturday and I was home alone and decided it would be a good day to dress and be girlie, excited about my day I waxed my legs and bikini line painted my nails a soft pink and took a relaxing bath with lavender bath beads, feeling very sexy I started my make-up knowing I would be alone all day I went all out. After I was done I went to my special cabinet in the attic and began to pick a wardrobe for the day. First was a very sexy purple panties and bra ensemble followed by suntan colored nylons, a short white cotton skirt, and a pink cotton t-shirt, and 3" pumps and also a mid back length sandy blonde wig. After dressing I looked in the mirror feeling very proud of the transformation, looking very feminine and passable I went to the kitchen and raided my parents liquor cabinet and maid a screwdriver.
Sitting on the patio I heard the door bell ring almost in a panic knowing no none had ever seen me dressed I ran to the bedroom. . I had forgotten about my invitation to go boating with their family. It was Carrie was the girlfriend of my buddy Mikes older brother, seeing my car in the drive and hearing the music in the house she assumed I was home and possibly in the bathroom she came in the house. Walking through the house quietly the kitchen the living room down the hall by the open bathroom she made her way to my room opening the door I was in absolute shock as was Carrie, " WHAT THE HELL ARE YOU DOING?" embarrassed I almost began to cry, laying on my bed I horror she began to smile at me after the shock wore off "Do you do this often?" I smile back at her, " Only when I am alone, " I like it" she said. She walked over to my bed and sat down next to me " You look really cute" not knowing what to say I said " Thank you" and smiled at her. " I hope you won't tell anyone about it, PLEASE". Smiling she responded " Tell anyone I want to see just how good of a girl you really are or should I say bad", with a puzzled look I asked what she meant , " I want to help you with your make-up and have some fun", feeling more comfortable now I smiled at her " You would help me with my make-up" she agreed and it was of to the bathroom. She worked her magic on me.
Back out on the patio I asked her what she had in mind as far a playing, knowing I had always thought she was a hot little number. " I am going to teach you how to be a girl" excited that I now had someone that knew my little secret " What are you going to teach me ", " It's a surprise" and off into the house she went, after being gone for what seemed like forever she returned with an evil smile and drinks for both of us. " We were supposed to go boating today but I just talked to Gail and the boat is not running for some reason", I know I forgot all about boating today as you can tell", " So I invited Gail over here to barbecue" gasping for air I almost fell off of my chair "YOU WHAT" I screamed, " If you want to be a girl I am going to show you how to be with a guy", " Know way Carrie, I cant I never have", " It's ok Gail is bi-sexual and I think he will like you allot like this" feeling aroused and scared at the same time I protest her idea " know way Carrie I have never been with a guy and don't plan on it" knowing deep inside I have looked at Gail before and find him to be quite a catch and often wondered if he would be interested in being with a cross-dresser. " it doesn't matter what you want if you don't I will tell the world your dirty little secret" , " You wouldn't dare", " I sure would". " If you want to dress like this have fun with it sweetie", "The thought of being with a guy scares me to death", " Don't worry I will be right there with you". Now very excited and scared I am almost looking forward to this day. Carrie says" What do you call yourself when you are dressed?" " I never thought about it", " How bout Amanda?", " Amanda I like that", " Well Amanda I guess we had better teach you a few things then" Carrie moves close to me " First you need to know how you touch a man like a woman" she takes my hand and gently puts it on her leg and begins to move it softly up and down her leg.
Sitting on the patio I heard the door bell ring almost in a panic knowing no none had ever seen me dressed I ran to the bedroom. . I had forgotten about my invitation to go boating with their family. It was Carrie was the girlfriend of my buddy Mikes older brother, seeing my car in the drive and hearing the music in the house she assumed I was home and possibly in the bathroom she came in the house. Walking through the house quietly the kitchen the living room down the hall by the open bathroom she made her way to my room opening the door I was in absolute shock as was Carrie, " WHAT THE HELL ARE YOU DOING?" embarrassed I almost began to cry, laying on my bed I horror she began to smile at me after the shock wore off "Do you do this often?" I smile back at her, " Only when I am alone, " I like it" she said. She walked over to my bed and sat down next to me " You look really cute" not knowing what to say I said " Thank you" and smiled at her. " I hope you won't tell anyone about it, PLEASE". Smiling she responded " Tell anyone I want to see just how good of a girl you really are or should I say bad", with a puzzled look I asked what she meant , " I want to help you with your make-up and have some fun", feeling more comfortable now I smiled at her " You would help me with my make-up" she agreed and it was of to the bathroom. She worked her magic on me.
Back out on the patio I asked her what she had in mind as far a playing, knowing I had always thought she was a hot little number. " I am going to teach you how to be a girl" excited that I now had someone that knew my little secret " What are you going to teach me ", " It's a surprise" and off into the house she went, after being gone for what seemed like forever she returned with an evil smile and drinks for both of us. " We were supposed to go boating today but I just talked to Gail and the boat is not running for some reason", I know I forgot all about boating today as you can tell", " So I invited Gail over here to barbecue" gasping for air I almost fell off of my chair "YOU WHAT" I screamed, " If you want to be a girl I am going to show you how to be with a guy", " Know way Carrie, I cant I never have", " It's ok Gail is bi-sexual and I think he will like you allot like this" feeling aroused and scared at the same time I protest her idea " know way Carrie I have never been with a guy and don't plan on it" knowing deep inside I have looked at Gail before and find him to be quite a catch and often wondered if he would be interested in being with a cross-dresser. " it doesn't matter what you want if you don't I will tell the world your dirty little secret" , " You wouldn't dare", " I sure would". " If you want to dress like this have fun with it sweetie", "The thought of being with a guy scares me to death", " Don't worry I will be right there with you". Now very excited and scared I am almost looking forward to this day. Carrie says" What do you call yourself when you are dressed?" " I never thought about it", " How bout Amanda?", " Amanda I like that", " Well Amanda I guess we had better teach you a few things then" Carrie moves close to me " First you need to know how you touch a man like a woman" she takes my hand and gently puts it on her leg and begins to move it softly up and down her leg.
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"WOW Carrie I don't know if I am going to make it you are driving me wild", Don't worry Amanda we have a while until Gail gets here you can cum if you want you", she then gets on her knees in front of me and reaches up my skirt and pulls my panties and nylons down exposing my already hard penis. " Isn't that cute" and she take it in her hand and moves her mouth toward it, almost instantly I explode when it enters her mouth. She slowly strokes me and continues to suck me until I am almost exhausted from the excitement. " There now we can get back to making you a girl"
Before I knew it the doorbell rang again, Carrie said " Wait her I will get it", nervous and excited I didn't move, a million thought going through my head run, hide, die, I hear a voice " Amanda this is Gail ", I almost fainted, as I stood up and turned around I could see a puzzled look on Gails face, he knew who lived and I had never mentioned anyone name Amanda. " It's very nice to meet you". " Would you care for a drink?", " Sure ", In the kitchen shaking from excitement I attempt to make drinks. When I return I notice a strange look on Gails faces " Kyle?", "Yes" this is what I do when I am alone , "Damn you look good", Thank you", I return to my chair and to my amazement , We continue chatting and after a few minutes. Embarrassed and excited I remember what Carrie had taught me. Carrie said " Gail this is Amanda's first time being dressed around anyone and she has never been with a guy before". Carrie say' s " I want to teach her how to be a girl are you guy's ok with that?" Gail agree' s quickly.
We move our little party into the house, in the living room I sit in the chair and Gail sat on the couch. Carrie takes Gail buy the hand and leads him in my direction, standing in front of me Carrie kneels down and unzips Gail's pants exposing his huge cock. I gasp at the size still soft, she takes my hand and puts it on his huge cock liking how it feels it begins to swell. Carrie talks my hand and begins to stroke him, knowing how I do myself it all becomes natural, as I slowly stroke him he becomes harder and more impressive in size. As I stroke Gail's huge cock instinct takes over and move my mouth toward his cock and begin to lick the head of it. Carrie puts her hand on the back of my head " Now Amanda slowly take his cock in like a giant lollipop" pushing my mouth further down his enormous shaft. I begin stroking him with my mouth, in and out he must be 8.5"s long it seems to take forever from end to the other. Amazed at the way a cock so hard can feel so soft in my mouth I begin to moan almost in sequence with Gail. Knowing I am pleasing him the way his girlfriend has just pleased me I feel more feminine than I have ever felt in my life and knowing why I enjoy dressing as a women, it is because I am meant to please men. On my knees as I continue sucking this enormous cock I feel someone rubbing my ass. Not wanting to stop now I keep Gail's cock deep in my mouth and beginning to taste something sweet yet salty, Gail begins to jerk and grabs me by the back of my head and hold me on his cock as he begins to blow his hot warm cum in my mouth, almost gagging I take all I can and force my mouth away from his enormous cock. Still cumming he cums on my hand and all I want to do is please him so I lick his warm love juice from my hand and moan as my cock is stroked in my panties. Knowing it is Carrie I look back and I smile at her. Smiling back at me " How does it feel to be a girl Amanda?" I love it, I never dreamed it would feel so good to suck a mans cock", Gail smiles at me and says " You did an incredible job Amanda" , "Thank you Gail " " You make a very cute girl Kyle I hope you will have us over again for an afternoon get together" smiling at Gail " I would like that". They both say their good buys and head for the front door. Feeling like I have never felt before I smile as they leave knowing this will never be the same for me, and hoping we will be together again soon.
Before I knew it the doorbell rang again, Carrie said " Wait her I will get it", nervous and excited I didn't move, a million thought going through my head run, hide, die, I hear a voice " Amanda this is Gail ", I almost fainted, as I stood up and turned around I could see a puzzled look on Gails face, he knew who lived and I had never mentioned anyone name Amanda. " It's very nice to meet you". " Would you care for a drink?", " Sure ", In the kitchen shaking from excitement I attempt to make drinks. When I return I notice a strange look on Gails faces " Kyle?", "Yes" this is what I do when I am alone , "Damn you look good", Thank you", I return to my chair and to my amazement , We continue chatting and after a few minutes. Embarrassed and excited I remember what Carrie had taught me. Carrie said " Gail this is Amanda's first time being dressed around anyone and she has never been with a guy before". Carrie say' s " I want to teach her how to be a girl are you guy's ok with that?" Gail agree' s quickly.
We move our little party into the house, in the living room I sit in the chair and Gail sat on the couch. Carrie takes Gail buy the hand and leads him in my direction, standing in front of me Carrie kneels down and unzips Gail's pants exposing his huge cock. I gasp at the size still soft, she takes my hand and puts it on his huge cock liking how it feels it begins to swell. Carrie talks my hand and begins to stroke him, knowing how I do myself it all becomes natural, as I slowly stroke him he becomes harder and more impressive in size. As I stroke Gail's huge cock instinct takes over and move my mouth toward his cock and begin to lick the head of it. Carrie puts her hand on the back of my head " Now Amanda slowly take his cock in like a giant lollipop" pushing my mouth further down his enormous shaft. I begin stroking him with my mouth, in and out he must be 8.5"s long it seems to take forever from end to the other. Amazed at the way a cock so hard can feel so soft in my mouth I begin to moan almost in sequence with Gail. Knowing I am pleasing him the way his girlfriend has just pleased me I feel more feminine than I have ever felt in my life and knowing why I enjoy dressing as a women, it is because I am meant to please men. On my knees as I continue sucking this enormous cock I feel someone rubbing my ass. Not wanting to stop now I keep Gail's cock deep in my mouth and beginning to taste something sweet yet salty, Gail begins to jerk and grabs me by the back of my head and hold me on his cock as he begins to blow his hot warm cum in my mouth, almost gagging I take all I can and force my mouth away from his enormous cock. Still cumming he cums on my hand and all I want to do is please him so I lick his warm love juice from my hand and moan as my cock is stroked in my panties. Knowing it is Carrie I look back and I smile at her. Smiling back at me " How does it feel to be a girl Amanda?" I love it, I never dreamed it would feel so good to suck a mans cock", Gail smiles at me and says " You did an incredible job Amanda" , "Thank you Gail " " You make a very cute girl Kyle I hope you will have us over again for an afternoon get together" smiling at Gail " I would like that". They both say their good buys and head for the front door. Feeling like I have never felt before I smile as they leave knowing this will never be the same for me, and hoping we will be together again soon.
