A neighbor shows me how a crossdresser should feel
By: Date: 2023.07.31. Categories: Sex Stories Tags: , , ,

It all seems like a dream but here I am. on my back, legs spread and feet on his shoulders as he makes me his sissy. Up until just a few minutes ago, I was very afraid of what was going to happen to me. Now, with his reassurances and tender gentle lovemaking, I am truly enjoying this.

I should go back to the beginning and explain just how I unwittingly found myself in the situation. I moved into this small rental home just a few weeks ago. It is in a very nice quiet neighborhood where most of the people are friendly and tend to mind their own business. There are neighbors on each side and both are older gentlemen One is divorced and the other told me he was a confirmed bachelor. We have talked frequently and they seem to be very nice.

Now, I guess I should reveal my little secret. I have enjoyed crossdressing in the privacy of my own home for several years. I have done this for my own pleasure and have never been with a man, nor had I wanted to. I just enjoy being completely smooth, with my longer hair styled, wearing makeup and the feel of lingerie, heels and sexy clothing. The feeling is so wonderful but I have always been too shy and introverted to ever even imagine anyone seeing me like this.

Tonight was a Friday night like any other start of the weekend. I arrived home from work about 3:30 in the afternoon. The first thing I always do on the weekend when I get home is to run a nice hot bath, cover my body with a depilatory and add fragrant bath oil and climb in after 5 minutes. I love using a depilatory which leaves my entire body hairless and the bath oil makes my skin feel so soft and smooth. It is sensuous just feeling my smooth hairless skin. I then soak until the water starts to cool down, get out and towel myself off.

Once dry I go into the bedroom and make sure the shades are drawn, sit down on the edge of the bed and draw up my silky smooth nylons, slowly, sensuously, feeling the silky smoothness sliding up my smooth legs. I put on a garter belt and fasten the nylons. I then pull on a pair of silky nylon thongs which barely cover me after tucking my now hard cock between my legs. A nice sexy bra to cover my small tits and I feel my nipples getting so hard. I usually then put on a slinky negligee or minidress and heels before making something to eat. This usually has me so hot that I prefer to stay in this heightened state of arousal for several hours before pulling out my vibrating dildo and cum so hard without ever touching myself while riding it.

Tonight was different. Just as I was fastening my bra, I heard the doorbell. Quickly throwing on a loose shit and jeans, I made sure no one could tell what I was wearing, and rushed to answer the door. I saw Bill, the confirmed bachelor from next door, smiling and holding a bottle of wine. I asked him in and he sat on the couch while I took the bottle, opened it and poured two glasses. Giving Bill his and sitting on the chair across from him I asked to what I owed the pleasure of his visit.

At first he just smiled and told me that he wanted to be a good neighbor and thought that a couple of drinks would help us get better acquainted. I smiled and agreed. We made small talk and soon we were on our second glass. That was when he asked me to come over and sit next to him. I looked at him curiously and he told me that we should become closer friends. Before I could protest, he told me I was his kind of girl. I started to open my mouth and he said “Come over here. I have seen you prancing around here dressed to the nines and I have to say, you really have me turned on. I love CDs and you are a most beautiful one”. I stood up and he took my hand and pulled me down next to him. “I do not want to cause you any trouble so hopefully you will do as I ask.”, he said as he pulled me down next to him and gave me a hot deep kiss. I was stunned and then he said, “ Now why don’t you finish dressing, get out of those jeans and shirt, put on your sexy negligee and heels, your make up and call me when you are done.”

I was so nervous I did not know what to do except as he asked. As I got up he smacked my ass and said, “Now that is a good girl. Do as daddy asks and the will be our secret”.

I was trembling as I walked back into the bedroom. Combed and styled my hair, applied my mascara, blush and lipstick after removing my jeans and shirt and pulling on my negligee. When my makeup looked good I slipped on my heels and walked back into the living room.

His eyes were al over me as he smiled and told me what a beautiful little girl I was. Pulling me down on the couch next to him he began kissing me again. AT first I resisted but found it highly stimulating. When I stopped resisting I felt his hands on my knee then he gradually slipped up under my negligee and rubbed my crotch. I was really getting excite.

“Now, my hot little girl, I want you to unfasten my belt and pants and pull them down. Then you will see what a real daddy looks like”, he said with a big smile on his face. I have to admit I wanted to and yet I had never done this before. I unbuckled his belt, his ants and then pulled them down. He had slipped off his shoes and socks and then when I lowered his pants he kicked them off. I turn my head and his huge cock was right in front of my face. “Do you like it?” he asked. “I want you to kiss it and take it into that tweet little mouth of yours”. I started to protest but he would have none of that. He grabbed me head and guided my mouth to the head of his cock. “Now be daddy’s good little girl or I my have to punish you”, he said, “Do you want daddy to speak you?”.

I started kissing the big round head of his sock and licking it. There was a drop of precut cum on th end and it actually tasted good. I opened my mouth and took the head of his cock in, swirling my tongue around as he moaned and pulled my head down. I played me hand on the base of his cock to keep from deep throating his cock and he started fucking my mouth telling me what a good little girl cocksucker i was. After a few minutes he pulled me back up on the couch, got on his knees between my legs, pulled my panties down and over my heels, tossing them to the side. He began kissing my inner thighs, working his was up under my negligee, my tummy and then pulling up my bra while licking and sucking on my small nipples. I was in heaven, moaning and begging for more. He told me to call him daddy and I was begging daddy for more. He stopped after a minute and picked me up like a rag doll, carrying me into the bedroom and making me get on my hands and knees.

My ass in the air, he began massaging my ass while using his tongue to swirl around and then poke int my ass. I almost came it felt so good. He kept doing this until I was so ready to cum then he stopped, climbed between my legs and told me to relax as I felt the head of his big cock pushing against my tight little whole. “Relax and let daddy in to that little girl pussy and daddy promise to make his little girl feel so good”, he said as I felt the head of his cock enter me. It really hurt and he stopped while just inside allowing me to get used to his huge cock He was quite a bit bigger than the dildo I had been using, After hesitating he slowly pushed further into me until I felt his balls against me. He stopped then slowly began withdrawing the pushing deep again. The pain was being replaced with the most pleasurable feeling I had ever had. I was dressed as a woman and being used by a virile man as if I were his woman.

Once he knew how much i was enjoying this he sped up, plowing in and out faster and faster then suddenly pulled out. Just as I stared to protest he turned me over, grabbed my heels and put them on his shoulders before pushing his cock back in until I felt his balls la against my ass. Looking at me he smiled and said, “Oh my beautiful little girl. Tonight I make a woman out of you and you can continue to be my little girl whenever I am in the mood.”. This is where I started this story.

He began slowly fucking me, my legs spread wide as he leaned down and kissed me. “Wrap those smooth legs around my waist”, he commanded. I did as I was told and as kissed me and fondled my tits, he began sliding in and out, Faster and faster and I felt myself ready to cum like never before. His balls slapping against my ass, suddenly plowing so deep I sear I could feel him deep in my stomach, I felt his cock grow even larger. I started cumming like I never had before as I felt his cock twitch and I could feel his hot seed filling me. I thought I would never stop cumming and I had never felt my whole body shiver the way it was right now. It was so far beyond anything I had ever felt.

When he stopped twitching, he kept that wonderful tool of his deep inside me as I gradually came down from that magnificent high. As he softened and pulled out, I weakly protested but he told me not to worry. This was just the beginning. He collapsed on the bed next to me, took me in his arms as I laid my head on his chest and we both fell asleep.

I was now his little girl, his woman and he had made me his sissy. I was his t command. I had never felt like this before and he new how to make me his.

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