My first time with a man
By
Heidi

I could feel him sliding his limp cock out of my new formed ass pussy and making me a sissy girl that I have wanted to be my whole life. I know from that point on, my life was not going to be the same. But first let me tell you how I got to this point in my life.
I think I was around eight when I first trying on my moms clothes. I just wanted to see how they felt on me and o my god I was in love with silk panties. I know from then on I needed to try on more things. I was like most young sissies by trying on panties, pantyhose, and bras. I would go in to the bathroom and in to the hamper to get my mom’s things and put them on and walk around in my room at night or when my mom was not home. This went on for many years. I started wear more and more things. Went from the simply things to wearing skirts, blouses, and heels. I even started to try on make-up. I did not do a good job of it be I tried.
I did not have a dad so I did not know any better about being a boy. My mom would make me do the dishes, and clean the house when I got older. Some days I would get home run from school and change in to my girl clothes to do the chores she gave. I wanted to feel and look like my mom when I was doing them. One day she came home early from work and caught me dressed in her things and went nuts and yelled and told me to go up to my room and take off her things and stay there for the rest of the day.
I went to my room but I did not have the hart to change so I did not till she came in and found me still in her things. She yelled even louder and even pulled me over to the bed. She then put me over her knees and pulled up my skirt and spanked me or some time and ever time she did she would tell me not to dress in her things. After she was done she told me to stand and get undress and she stood there watching me. She then put me to bed and told me we will talk about this in a few days.
It was a few days later but I still dressed that few day. When she came home that day we talked for a few hours about why I was dressing and why I should not. She told me she had made a few phone calls to some therapists and she wanted me to go and talk to them. So off we went to talk to them about m dressing. My therapist was a lady and a good looking lady if I can remember. When we talked the only thing that was racing though my mind was how nice her clothes looked and I wish I could wear the clothes she had on every day. She would wear the most amusing outfits, skirts, blouses, dresses, and heels. I would think to my self what she ad under her clothes, was it silk, lace, or something different. Some days I would wear panties or even a bra at time when it was cold to the chats. I would think to my self, was she wearing the same type that I was wearing? This would want me to dress more and more looking at her and talking to her about my crossdressing.
At this time I was around 13 or so and dressing more and more and taking more changes when dressed. I would wait to change for the last minute before mom would get home. I would go out at night for walks down my street or sit in the back yard. Every day in school that I did not have gym I would steal my mom’s panties and wear them. I would think to my self was any ant of the girls wear the same panties. I would run home and change in my clothes to do the chores that I had to do. I would feel so good and when I had to change back to being a male I would want to cry.
When I turned 14, mom had discovered me dressed around a dozen times or so. By then I did not care if she did or did not find me dressed. I just wanted to be a girl so bad. I started to go to the mall and buy my own clothes and underwear. I would find money for my clothes by doing odd jobs around the neighborhood, Cutting grass, raking laws, washing cars, or anything that would be in money. The climax of my dressing was when my mom was going to have a coworker come over to finish some work. She came home and found me dressed and screamed. I told her I was not going to change and did not care what she wanted. That was the last thing I can remember before being dragged up to my room for a spanking that left my ass so red and sore. The next few hours it was so uncomfortable that I could not sit down and it was painful to sit for days.
The next day came fast and I could not tell what was going to happen with mom and I. I did not sleep the well the night but mom came in around 7 or so to wake me up. I had changed in to a silk nighty that I got the day before to sleep in. when she came in and found me in it she just shock her head at me and told me to meet her down at the kitchen table in a few minutes. She threw me my robe to put on and told me not to change. I walked down stairs to find her at the table sipping her coffee. I sat across the table from her and she did not say anything to me few what seemed liked for hours, but it was not. She started slow at first by asking why I made her so made last night. Then the questions came about my dressing and why I did not want to change. I told her with tears coming down my face that I wanted to be a girl.
After I stopped crying she told me to go up stairs and draw a bath and clean up and she would be up in a few minutes to talk to me and told me she had to make a few calls. I did what I was told and in a few minutes mom was sitting on the edge of the tub. She told me to clean real good because that is what girls do. If I can’t stop you from dressing as a girl, I am going let you be one and I am going to call you Heidi from now on. Now after you dry off put on this lotion and come in to your room. That stated she left the bath room.
I did what I was told and went to my room. There I found on my bed a new dress with panties, pantyhose, bra, and shoes. In the next room I heard mom tell me to get dressed and come in to her room. It felt great when I slid the silk panties, pantyhose, and bra on like I did so many times before but this time was different knowing this was going to be my new life. Mom laid out a nice flower print dress that fell just short of my knees with short sleeves. When finished dressing I had to look in the mirror and could not believe how I looked. I was a girl now in my house with mom knowing and being ok with it.
I walked in to mom’s room and did a spin as I entered. Mom took one look at me, and said you look great Heidi. What a warm feeling come over me knowing mom just called me Heidi. She sat me down in front of her make-up vanity and said at my age all girls start to wear make-up. Then she started to apply foundation, pink blush, black mascara, and blue eye shadow on my face. When she finished with my make-up, she put on a wig on me and let me see my self in the mirror. I could not believe what was looking back at me; it was the girl I wanted to be.
That day, mom was teaching me how to walk in heels, talk, sit and acted like a girl. The next started out the same but mom told me she was going to the beauty solon to have my hair, nails, make-up done and ears pierced. I know I was going to love this day and I did. The lady’s at the shop were great to me and treated me as a girl. We then went to the mall and picked out my new clothes, silicone breast forms and everything else I needed to be Heidi. I think that was the best day till I meet John.
It had been around four years since the first day as Heidi. I was living ever day as Heidi and I was being home schooled from mom. We also moved from a small town to a city were mom fond a new job. Over the years mom would have a few boyfriends but nothing would last to long when she told them about me and that made me sad. She told me that was ok because we had each other. Then she meet john. John was around 40 I think. After a few dates she told him about Heidi. He told her that he did not care because his bother was gay and also dressed.
Mom was out of town for a few days when John stopped over to see her. I told him that she was gone and asked him to come in if he liked. He slid past me and asked me how I was today. I was still in my nighty and told him I was going to go my bedroom and change. John was looking hot that day to me. He was 6 feet tall with dark tan skin with deep blue eyes and dark hair. I was feeling horny as hell that day and wanting to have sex soon. Looking back now I was hoping he would be my first.
I started to get dressed in a short skirt, low cut top to show off my breasts, with a nice lace bra, silk thongs, and black thigh-hi stockings. I applied me make-up on and did my hair and looking in the mirror and I was looking good. I walked down stairs to find John sitting on the couch, when he seen me he looked for some time and told me that I looked great and if I was going anywhere today. No, not till later for work I told. Then I saw him smile. He told me to sit down and we could talk some.
We were talking for sometime about anything at the same time he was getting closer and closer to me. He put hi arm around me and lend in to kiss me but I stopped him. I told him I could not do this to mom. He recognized I wanted to have sex with him before I know it. The way I was dressed told him that. In the back of my mind I know I wanted also. He started to kiss me on my red silk lips. At fist I tried not to kiss back but after a few kisses I gave in and started to kiss back.
He slid his hand down my body and in to my top to feel my waiting breasts. At this time I could not stop him and did not want to. My breathing was getting faster. He felt me up and kissing me at the same time. What a feeling it made me feel just like a girl, having a guy like John getting me hot. I know at this point I was going to have sex with him. He slid my hand down to his pants so I could feel his hard cock trying to get out. I felt how big it was and was thinking to myself that is why mom likes John so much, and now I will have him.
John toke me by my hand and lead me to my room. There was no stopping him or me now. He turned around and told me to get on my knees and take his cock out. I unzipped his pants and his cock fell out just in front of my mouth. It must have been seven and half to eight inches long and three inches wide. It had a nice mushroom head that was waiting to be sucked by my mouth. John put his hand around it and held it up and told me to kiss it and suck it. I bent over to kiss the head as I did it jumped in pleaser. It felt so natural when I slid his cock between my red lips. I slid half way down then back to the head many times. I could hear John moan and know I was doing a good job. After some time John was pushing his cock in my mouth and I went down on it. At one point when he was deep in my mouth he toke control of my head and made me deep throat him several time. Each time I would loose my breath and gage.
After he was done making me suck and deep throating him he pulled me up and toke me to the bed. He laid me down and told me I will now make you the girl that you want to be. He slowly started to undress me starting with my top. After playing with my breasts he moved down to my skirt and toke that off to show my black thigh-hi and thong. He told me he saw that I wanted him and now seeing what I had on he know it. He slowly kissed my thighs, and moved his hands all over my body. At this point I just wanted John inside of me, to take my virgin sissy pussy. He flipped me over and moved my thong over to one side and started to lick my pussy and it felt so good. When he finished licking me I was so wet and horny. He then told me to stay there and not to move and left.
When he came back in I felt John put two KY jelly fingers around my pussy and slid one then two inside of me. I had to jump when he did this because I never felt this before. He slowly went around and inside of my pussy to make it loose and easy for his big hard cock to slide in. it felt so good I started to moan and wiggle. I cried out to him; john fuck me please fuck me I want you inside of me now. Hearing that made him even harder and felt him move up to place his cock next to my waiting pussy. Now just relax Heidi let me do all the work taking your manhood to womanhood.
Then I felt his head start to slide in my pussy. Has he slide it in it started to burn and hurt me and I told him to pull out. He stopped pushing in but did not pull out. My pussy started to relax and started to like it. Then he started to push in deeper and deeper then with one final thrust I felt his long shaft hit the back of my pussy and his balls against me. He has just taken my virginity I was thinking to my self but the feeling did not last long. I felt him start to pull out slowly and then back in so gently. He just kept fucking me like this for some time till it felt good and easy to slide in and out. He started to fuck me harder and harder and it made me moan louder and louder.
At one point he pulled out and flipped me on my back. He put my legs on his shoulders so he could easily get to my pussy and fuck me. I felt is cock next to my pussy has he lifted me up. He did not take it easy this time and just rammed it in the full length of eight inches and it toke my breath away. He just started to hammer away on my pussy like there was no tomorrow. It felt like it was forever but it was only about three minutes or so. Then with one last big thrust as far in as he could get I felt him stop and his hot cum fill my now pussy. He jerked and shook a few times and he fell on top of me. I heard him whisper in my ear welcome to your new life as a woman. Hearing this I know from this point on, my life was not going to be the same. He pulled out his soft cock out and I could feel his cum slide down my ass and on to the bed.
The day was not done with both of us. We went out of lunch and dinner then back to my bed for some more fucking. He fucked me three more times that night. Each time he fucked me it lasted longer and longer. In the morning I wanted to thank John for making me a woman. So I went down on him sucking and licking him till he could not take in anymore and had to cum in my mouth and he made me swallow.
John stopped over a few more time to see mom and myself. He even fucked me few more times even one time just before mom got home. The last time we fucked, he told me he went to fuck a mother and daughter. I do not know if mom found out about us but she did ask one day how I liked John. I told her I liked him with a grin on my face.

story by: heidiho1

Tags: true story sex story

Author: heidiho1

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