Cross Dressing Sex Story With Aunt Joan

When I was in high school, my parents used to go away on vacation to exotic and far off places every summer. I was an only child and for them a vacation was without the kid. So they dropped me off at my father’s sister, my Aunt Joan. Aunt Joan was adopted at a young age by my grandparents and Joan was famous for always being a wild woman. She married a man once who was 40 years older than her and filthy rich. He died suddenly and Aunt Joan received millions. She was my favorite Aunt and during puberty I always used to masturbate about her.

As I got older, my summers with Aunt Joan became more and more fun and interesting. She took me around all day doing errands and hanging out with her interesting friends. Most of them were either gay, bi sexual or just plain good looking and as a teenager, the whole scene fascinated me. Such a different world from my conservative uptight parents.

The summer I turned 15, my folks went to Barbados for 3 months and off to Aunt Joan’s I went. But this year was different. Joan had moved into a huge house on the beach and there were at least 4 guest rooms to choose from. Joan took my hand and led me to the PINK room. She explained to me that this room was the only room that was finished and although it was intended for a girl, she was sure I would find it more than comfortable. And indeed it was. A large soft fluffy bed with a large mattress. A huge walk in closet, and a bay window plus a private bathroom with hot tub. Thank you Aunt Joan.

Joan and I would run her errands and go to posh shopping malls as well as fancy restaurants and she would even buy me wine for lunch. She easily won me over and I looked forward to seeing her everyday. Usually she would try on clothes all morning and I would sit near the dressing room and tell her how she looked. She looked great. She was of German decent and a large and full figured blonde bombshell type woman although not fat. She had powerful legs and butt muscles and the largest breasts I had seen up close. She could have been a porn star and she was in my mind. Everything she tried on was a size too small and she spilled out of it like milk from a glass pitcher. I had a constant hard on all summer long.

One early summer morning I woke up and began to get dressed. I noticed all the lingerie in the closet and dresser drawers in my girly pink room and decided to dress up a little bit before breakfast. I found some white thong panties with lace around the elastic edges, I slipped them on and turned around and looked at my ass in the mirror. I stuck it out just like a little slut and it turned me on a bit. Then I put on some white stockings over my legs and found some white garders to attach to them. Then I put on a small white lace bra. Just then, Aunt Joan opened the door to my room and caught me all dressed up.

“My, you look delicious” she said. “Come here and let me help you”.

My face turned red and I knew I had been caught. I just stood there.

“Now look sissy boy. If you don’t do as I tell you, I am going to tell your father that you like to dress up in panties and frillies.” Aunt Joan said.

She had me over a barrel so to speak and I did what she told me. And actually, I really enjoyed it. The thought of being my Aunt Joan’s sex slave was a dream come true for me. However I never imagined it would take this form. She had caught me in her panties and that was not the masculine image I was trying to portray. But I was just happy the relationship was turning sexual.

“I don’t like those white panties on you. White is not your color. Lets try baby blue. Come here and let me take off your panties.” Joan said.

“Aunt Joan, I don’t want you to see my penis. Can I put on the blue panties in the bathroom?” I asked.

“Of course not silly” she said. Joan grabbed me by the hair and pulled me over to her large bosom and quickly yanked down my white lace panties and took a good look at my dick. She spanked my bare bottom twice and told me never to sass her again.

“You have rather large balls for a young boy your age but your penis is not very big. I am going to call it your clit from now on. Don’t worry; from now on it will sever only as your clit. You won’t be fucking anyone with it anymore. It’s just as well sissy boy.” She instructed me.

Joan massaged my clit until it was it’s full throbbing size. Then she put on the silk baby blue panties that felt amazing as they hugged my penis and balls.

“Today we will be going shopping to buy some sexy clothes for my new sissy slut. I don’t want you stretching out my good lingerie with your oversized clit. But for now you can keep the girly clothes on and we will go shopping as women together. Won’t that be fun?” She said.

“Please Aunt Joan, I don’t want to go out looking like this. Please, I beg you. I will do anything you ask. Anything you want. But don’t make me go outside dressed like a girl.” I pleaded.

“Well, I understand that you are shy and I may not take you out today but sooner or later you are going out with me dressed like your sissy self and we are going shopping. You know you secretly want to and you know you will enjoy it so stop trying to lie to me.” She said.

“Please, not today, I will do anything.” I begged her.

“Well little sissy, there is one thing I want to do to you. I think it needs to be done to straighten out your attitude. From now on I don’t want any macho masculinity coming from you what so ever. I am going to strip you of the stupid social training you have received and make you soft, gentle, light, and as sweet as the nicest girl in town do you understand?” she said.

“I will do anything you want me to do. I promise.” I said.

“Good girl. That’s the right attitude from now on.” She said.

Aunt Joan took me gently by the hand and bent me over the side of the bed and told me to wait there in that position for her to return. I waited in that position for 10 minutes wondering what she was going to do to me. I began to hope that she was going to fuck me. Whatever she was going to do, I hoped she would let me cum. I was dying of my constant hard on.

Joan returned wearing black stockings and block high heel shoes with white panties and no bra. Her breasts were gigantic. She was also wearing a huge strap on dildo and I immediately had the urge to suck it.

“From now on little sissy, your mouth is going to be my personal vacuum. I am going to train you to suck whatever I command you to put your lips on. Let’s start with my tits.” She said.

I placed Joan’s left breast in my mouth and gently sucked on her nipple for 5 minutes until it was fully erect.

“You are excellent at that. Very good. You have got Aunties tits very hard. And my pussy is also very wet.” She exclaimed.

As I was sucking her tit, she slipped her nipple out of my mouth and gently slid her 8 inch dildo into my mouth. I opened my throat wide and began to suck on it just like my ex girlfriend sucked on my cock last year.

“Take it all inside little sissy boy. Make that cock feel nice and warm and wet. Use your tongue to gently massage it up and down and cup the balls with your little sissy hand.” She said.

I did as I was told and began to fall into a rhythm. I looked up at Joan as much as possible as I sucked her plastic cock.

“You still need lots of practice sucking on a real man cock sissy boy. But we have the whole summer for that.” She told me.

Joan pulled the dildo out of my mouth and walked around behind me. She spread my legs apart just a little and pulled my balls out from under me. Without warning, Joan put the head of the dildo against my blue panties and pushed in into my ass with my panty going first. She pushed it as deep into my ass as I could take it and held it there. It hurt at first and I moaned and whimpered despite myself. She pulled it out and pushed it in again, keeping it inside me. I whimpered again. She did this at least 10 times until my cries subsided and I began to feel the pleasure of it. Now I moaned in joy as the dildo entered my ass along with my silk panties.

“From now on sissy slut, the only pleasure you are allowed is in this way. With a cock in your ass. Only with a cock in your ass are you allowed to cum. Do you understand?” she asked.

“Yes, I understand.”

“That’s a good girl.” Joan said. She put her hands on my back and began to fuck me gently pushing my body back and forth on the bed that caused friction to my cock and then she told me to cum for her in my silk soft panties. I easily came all over myself in those wonderful panties.

“Now that you have had your pleasure, it’s my turn. You must learn to be selfless with your body and to give pleasure to others above all.” She said.

Aunt Joan tuned me over on my back, stripped off my cum soaked baby blue silk panties and lifted my legs into the air exposing my now limp penis. She splashed baby oil all over my crotch and her dildo and began easily slipped her strap on into my ass again.

“You must be able to take my entire cock in your ass without any thought of your own pleasure.” She told me.

She slammed the dildo as far as it would go inside of me and I cried out. She quickly pulled it out and slammed it in again. I was in great pain. Over and over she did this and faster and faster. I almost blacked out it was so painful. I began to cry and she began to fuck me harder. It felt like she was trying to dig a hole in my ass. I kept crying and sobbing. She stopped and slapped my face and told me to stop being such a pussy. I lay there crying as she left the room and then came back with a double headed dildo that she placed in my mouth.

“I want you to hold on to this to keep from crying so much. When you feel like crying, just keep sucking.” She told me.

I did as she said and she returned to ramming my ass. I sobbed constantly as I sucked the double-headed dildo. After about 45 minutes, my ass was numb and I no longer felt the pain. The muscles in my mouth were sore and I took out the dildo and just laid there while she continued to fuck my tight ass. And then she stopped.

“Well my little sissy, I have fucked the manhood out of you and from now on, you will be my sex slave. Don’t worry, I know you have always secretly wanted to be my sex slave. Just as I have always wanted you to be my sex slave. I have always secretly wanted to fuck your ass. I have fantasized about it since you were 12 years old. It was only a matter of time. I own you now and you are owned by me. From now on you will sleep in my bed at night with me dressed as a woman. You will come with me everywhere I go dressed as a woman. You will be my own personal shemale. Now I know that excites you as it excite me. It’s what we both want.” Aunt Joan said.

And Joan then got on the bed and spread her legs over my face and told me to suck her pussy and lick her clit. I did so with a fever and she came on my face several times. Her juices ran down my chin and neck and I just kept sucking her beautiful pussy. I felt a sense of peace being owned by her now. It was a relief in a way. I knew she would take care of my sexual needs and I would take care of hers. To be a teenager and get the chance to sleep with such an amazing woman was more than I could hope for.

Crossdressing sex story with Aunt Joan written by Ian. Unauthorized reproduction is prohibited without expressed permission. Contact sexstory@postinbox.com for permission.