My first dressing up

Continued CD story with my mom

I was asked by one of my readers to add more to my story with my mom and how I was finally groomed to be a sissy. 

my mother knew I liked to dress up in frilly gurl clothes and she provided my first outfits of my own. I found out there would be more to come. 

I was obsessed with seeing her naked. She was more and more open as years went by. She would leave her bedroom door open after showering and I would find myself sneaking peaks of her getting dressed. She would see me and walk over with a smile and close the door. Of course I would go in my room and Jack off. 

One day I was home with her alone. I came up the stairs and peaked in her room. She was lying naked in the bed touching herself. I stared in the room and watched. It was so hot. She heard me and told me to come in. I was nervous but I wanted to do this. I walked in and sat on the bed by her. She smiled and took my hand and ran it over her moist pussy. She showed me how to touch her. She suggested I get out of my shorts and we might be able to play and enjoy this. I didn’t hesitate but I was nervous I had a big hard on. I sat back on the bed and continued to strike her soft bush. She reaches over and takes my cock in her hand. She smiles and says that is so much bigger than your dad’s. She strikes it and I am so out of my mind. She has me lay down on the bed. She climbs on me and lowered herself down on my cock. She sighs and begins to slow fuck me. I am not sure I can hold out I had never been inside a women before. She took her time stopping to keep me from cuming. 

finally she tells me to fuck her harder she arches her back and screams so loud. I can’t hold back and cum so hard in her. When we lay back she smiles and whispers to me to go down and clean my cum from her pussy. She says with a smile you will be doing this so many more times in the future. I wasn’t sure what she meant I thought it would just be me and her. This continued on for a few years and I loved every minute of it. 

One day she calls me up and says she needs help in the florets shop where she works. I need a little money since I was going to college at that time. I go over to the shop and she introduces me to her boss Dewey. He is a very nice fellow and we get on great right away. One evening Dewey calls me and says he needs help at his house. I drive over there not thinking much of it. He invites me in and has me help with some boxes he needed moved. After we are done he offers me a drink which I agree to. We are sitting in his family room and he smiles at me and say your mom tells me you like to play dress up. I am a bit embarrassed and I said no one was suppose to know  He comes over closer to me and says don’t be embarrassed it is ok. You are special and I like that about you. He takes my hand and guides me in his bedroom where I see a beautiful outfit is laid out on the bed. He says go ahead try them on. Also there is some nice makeup and things in the bathroom. I look at him and I just know now I am going to have an interesting evening. He leaves to fix us a drink as I pick up this really hot bra and panty set in black lace. I quickly take off my clothes and put on the sexy underwear. There is I slick black dress and I put that on. I put on some hot nylons and 4 inch black heels. I feel so fem in the outfit. I go in the bathroom and see the makeup laid out for me. I fix up my face and we’ll I am transformed. I can’t believe how I feel. I feel so warm and excited.  

I walk out of the bed room and dewey looks at me and smiles at me. You are so hot. What should we call this beauty he asks. I say well I love Jennifer. So Jennifer it is so I have been Jennifer for a long time now. Dewey hands me the drink and we go over to his couch. Now a little a bit about Dewey. He is in his 50’s short blond hair well groomed with slight beard and mustache. He works out so he is thin but strong. About 6ft 170lbs. I have been checking him out for a while lol. We drink our drinks and we chat for a bit. Not sure where this is going but hoping Ii might go where I want it. I have liked girls and of course my mom but over the past couple years I liked being a girl which lead me to think about men. I had seen some gay mags a school and even was in the habit of jerking off with them. There was also a football player across the hall I liked to hang with and I sometimes thought of being with him. He liked to pick me up and toss me around. I was slight and easy to play with. He once caught me jerking in my dorm room and had a handful of my cum when he caught me. He just smiled and left the room. Sad right. Anyway back to Dewey. He took my drink from me and placed his hand on my face. He said your mom said you would be a cutie but I am happy that you are hotter than I thought. 

He leaned in and he kissed me for the first time. Oh my I wasn’t expecting how I might feel. I kissed him back and opened my mouth so he could French me. I felt myself relax and found I wanted this so bad. We kissed for a while and he took control and I let him have me. I wanted to be so compliant and surrender to his desires. It was the first time I felt like a girl. 

I unbuttoned his shirt and took it off. He had a beautiful body with chest hair. I found that was a real turn on. Even today I prefer bear men. I licked down his neck and took his nipples into my mouth. I sucked on them. I knew this was turning him on. Slowly I ran my tongue down his body to his pants. I undid his belt and unbuttoned the waist. Slowly sliding the zipper down. I was breathing so heavy. At this time. I so wanted this I thought. I ran my hand over his shorts where his very hard cock was peaking out. I looked up to him and smiled. He smiled back and his hand reached down and pulled his shorts down. I was looking at this beautiful long cock. I wasn’t  sure what to do with it but I knew what I would want so I took it into my hand and began to rub it up and down. He was about 7inchs but thin. It was uncut which I had never seen one like that. I pulled the foreskin down and so I saw the big head. The slit was wet with precum. I licked it not knowing how it would taste. I found it tasted salty but not bad. I licked the head over and over wanting to feel II in my mouth. I opened my mouth and started to let this beautiful piece entering my mouth. It was so hard to take it at first but I wanted to please him. I gaged when it got down to my throat opening. It would take me a few more times doing this to open my throat wide enough to take it all the way in. Dewey was really getting excited as I felt his hands grab my head and he fucked my mouth. I licked him over and over again I didn’t want to stop. He finally stopped me and gathered me up and carried me into the bedroom. He told me to take off my clothes. I stripped for him as he lay on the bed. My body was tingling. I laid down next to him and we cuddled and kissed. He told me to turn over on my tummy. He went down and pulled my panties off me. He spread my legs. I felt his fingers on my ass. Playing with me. Fingering my hole one finger at first than two and finally three fingers.  He push them deeper in me. He pulled them out and I felt him squeeze something wet in my hole. My body was in flames. I didn’t want him to stop. He finally started rubbing his cock between my ass cheeks. Than he leans down and whispers in my ear. I am going to fuck you bb be ready. It will hurt at first but pleasure will come soon after. I tried to relax but I could feel his hard head slowly opening my hole. He started to push harder and I felt like I was going to break open. It hurt so but I wanted him to be happy so I took it. Farther and farther he entered me till he was all the way in. He stopped I felt his hot breath on my neck. He raised up and pulled his cock out slowly. He stopped just before leaving and than bam hard right back in. He kept doing this over and over. He kept saying how tight I was and loved the feel of fucking his girl. I finally was able to get a rhythm going to keep up with him and matched his strokes. He was now fucking me so hard. He started calling me his beautiful cum slut. His little girl who he was going to fill me with his seed. I loved the feeling of getting fucked and talked dirty to. I was becoming his slut. I didn’t want it to stop. He fucked me harder and harder yelling at me to fuck him like the whore I was. He told me he now owned me. I fucked him back as hard as he was fucking me. He finally raised up and I could feel his cock throbbing in me he was ready to cum. He yells here you go you hot cunt take my seed bb. He pushes all the way in and I feel the cum fill my ass.  He is shaking and fucking me till it stops. 

He pulls out and puts his wet cock by my face. He says suck me you filthy whore clean off my cock. I take it in my mouth and lick it and suck every last drop. I was spent. We lay there for a while. He turns over and looks me in the eye. You are worth every Penny I paid for you. I realize than my mother had sold me to him. I was his now I would spend every night pleasing him. He would have my mom over and I found myself servicing her as well but that is the next chapter. 

Hope you like this friend