Mom encouraged me to become her "lingerie boy"

For the last 55 years I have loved wearing not just silky panties, but all items of women's lingerie. It all started in 3rd grade when I began masturbating in Mom's panties. I would wake up in the middle of the night and sneak into Mom's bedroom and go thru her panty drawer to find a pair I liked to j******* in. Part of the rush was my fear of getting caught. For the next I was happy just wearing her panties, but then began experimenting wearing more of her silky lingerie.

One time in 5th grade I had come home from school and got pretty dressed up in her lingerie. I was wearina pair of her her panties, a pair of her pantyhose, one of her control panties, a short half slip, and a silky camisole. After j********** to a powerful o*****, I fell asleep on the sofa. The next thing I knew was Mom was waking me up wanting to know why I was wearing a lot of her lingerie. She told me she wanted to know and that I wasn't in any trouble. I told her everything, and how much I enjoyed the silky feel, especially when I masturbated while wearing them. During this time she had gotten a chair and was sitting near my head. As I told her why I loved wearing her underwear, I noticed that she kept opening her legs wider & wider. By the time I was done her legs were wide open & I could clearly see Mom's lacy pink panties. Mom noticed me looking up her skirt and asked me how I liked seeing her panties. I told her I loved it and then confided in her how good those panties felt when I wore them. She smiled at me and told me how "pretty" I looked wearing ladies underwear, and then asked me if I would like to go shopping with her so she could buy me my own collection panties, stockings, slips, and even bras, a long with all the other things women wore. H*** yes I replied.

When we got to a dept. store, she found a real young sales lady and told her that I loved wearing her lingerie, and would she show me everything in the store and then find things in my size. It was such a turn on to tell this woman what I liked wearing etc. She helped me pick out some really nice panties, garter-belts & hose, thigh highs & and some pantyhose, real short half slips, and some bras that fit me along with some silky camisoles. After the sales lady rang up all my things she asked my Mom if she would bring me back wearing all my lingerie so she could see me wearing them. I told Mom that I'd love to do that for her. I was so turned on at the prospect of modeling my lingerie for her, that she smiled looking at the bulge in my pants, and said, "I'll see you soon. Mom told me that from now on I'd be her "lingerie boy". I told her that was all I'd be wearing from now on...I love wearing women's underwear!!!

Mom called the sales lady and made arrangements to drop me off at her place with all the lingerie we had bought. I spent all day modeling all the silky things Mom had bought me, and she modeled a lot of her lingerie for me. We felt each other out, had all kinds of oral s**, and then she let me have s** with her repeatedly in all sorts of positions. I loved learning from her. More on Lingerie Boy put. 2

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  • Love to have f***** your tight lil pantied ass when you were in 3rd grade

  • I met an elderly man in the park last spring we got talking and he invited me back to his home and when we sat down it wasn't long before the subject of s** came up and so did my d***. to my surprise and joy he said I would look nice as a girl and I got more excited when he asked if I would wear ladies underwear for him. I asked if he had any and he said he had and it belonged to his late wife and he missed her. I felt really sorry for him.
    I said I would wear some and he invited me up into his bedroom where he went to some drawers and got a selection of knickers and other things and it wasn't long before I had stripped naked and I was trying things on and I could see that a lot of them were new so maybe not his wifes things. then I saw he was getting undressed as well and when he took his pants off he had a huge h******. he walked over to me and said you are lovely in knickers and began stroking my d*** as we stood together. I reached down and held his d*** it was hot and throbbing it felt good. he leaned closer and kissed me and I kissed him back then we were kissing and caressing each other.
    I felt his d*** between my legs and I gripped it tightly and he pushed against me I held his a*** and pulled him closer he was really aroused and so was I. I felt his d*** swell he kissed me harder and shot his c** between my legs.
    we have met up at his place since and our relationship is getting quite serious and I have stayed nights and I am now dressing fully for him and he is now f****** me regularly. I do feel guilty but I cant stop as I like the feeling of it all and I love the way he looks at me as I dress up and then he caresses me in the silky lingerie and he is very loving towards me.

  • That lucky old guy, I would love to get you in my bed, I don't think I could stop c****** !!!! Tell me more please!

  • I feel so excited when I visit him as we are having full penetration every time we get together now. He cried when he first entered me whispering that he loved me so and I must never leave him. He is so generous buying me lovely silky garments including negligees to wear in bed. We cuddle and fuss each other kissing a lot before he tells me he wants his dxxx inside me and I turn over he cremes my bottom and pushes into me thrusting that lovely erection deep inside my bottom. I feel the head of his dxxx pulling back as he thrusts his lovely member in and out of me he is so potent and he makes it last . I always know when he is about to cxx as his grip on my dxxx tightens he nibbles my ear then moans with the feeling of cuxxinx and oh! can he shoot a load so much jelly it leaks out of me for ages after.

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