I remember growing up in the 60's and how my grandmother wore those open bottomed girdles. She was a German woman who came alone to American as a young girl. She loved fine clothing and wore the best dresses, skirts, and blouses; and of course lingerie was always part of that. She was very open about sex and nudity. When I was 18 I stayed with her many weekends after my grand father passed away. She wore those girdles, like I said. I loved them, although she didn't wear the full ones that had the bra, only the shorter open bottomed ones. Many times she had me join her in her bedroom as she dressed, she loved talking to me. As you can imagine I loved it too. Watching her come from the bath, removing her robe, and then pulling on her girdle and bra excited me. She had large breasts and was of course a natural woman. I was always amazed at her beauty, but those girdles always aroused me.
She would sit in them only, with her bra on and I would get peeks of her, she never wore panties, ever. Once when she was outside I went in her room and undressed, searched her drawers for those girdles and stockings. I was not thinking clearly and never thought she might catch me. It felt so good when I slipped the girdle on.....the way it held me and how aroused I became intrigued me.....I sat on the bed like she did and carefully put on her seamed silk stockings. I looked at myself in her mirror and thought with my smooth hairless body, I looked like the girl my parents always wanted, dressed in sexy lingerie.....I must admit I was so incredibly aroused....
Then all of a sudden I heard my grandmother say....."Oh my.....aren't you the sexy girl.!" Oddly she did not yell at me or become angry, but I began to cry. I was embarrassed and frightened she would tell mom and dad, and punish me with a spanking. (actually I liked her bare bottomed spankings)
She asked why I was wearing her lingerie and I said I loved them. I loved the feel and look. I had always loved watching her getting dressed and was excited by it too. She looked down the front of the garment and said my arousal was obvious.
She sat quietly for a moment and said....."This will be our secret. I have many girdles....so many very exciting ones"......you might like them.....would you like to try them on....wear them all day?" I shyly nodded I would. She told me it was okay.....not to be embarrassed......many males loved dressing in girls clothes when they're younger and even as they got older. For some it was a phase of exploring in their youth, others would find it something that they never let go of. She said had helped my uncle when he was young also when she caught him like she caught me. I knew my uncle was gay, but the excitement of what she was saying was very exciting. Tears had been running down my cheeks and she kissed them away, telling me she loved me and only wanted to help me through this desire.
She told me we could play dress up together, both of us trying on different lingerie items all afternoon if we wanted too. She also told me she had some very nice baby doll nighties we could sleep in if I wanted. I never saw them before, but I was again intrigued.
We spent the day trying on her many girdles and stockings, I was so excited and aroused, she would look at me and I would turn away, embarrassed by the erection I had. She would tell me I should be proud to be such a handsome boy, and that I could also look like a very sexy young girl too...
I was amazed watching her undress until naked and then seeing her dressed so elegantly and sexy.....we did that all afternoon. When it was dinner time she gave me a sort robe to wear, actually too short, I think she loved the view. We cooked dinner and ate, she was telling me about my uncle and how she helped him with his fetish of wanting to dress as a woman, then she said, "if your going to want to do this all weekend, then you must bathe in a bubble bath and let her shave what little hair I had and let me trim my toe nails." She said I had put a run in her stockings and she hated wasting them as they were expensive.
After dinner I slipped out of my robe and got in the bath and washed myself. She made sure I was very clean as she said boys don't wash their bottoms very well and she did not want me dirtying the panties of her nightie. I had never worn panties before so I was excited and scared I would be called a sissy if anyone found out. She washed me thoroughly, it made me excited. I was nervous she would say something, but her soapy hands felt amazing. She even squeezed my penis teasing me saying I was naughty.
It was bed time by now and she had cut my nails, then she said she should put nail polish on them, I balked and she said pretty girls need those extra things too. I blushed and she said I would love it. She went in her drawer and pulled out two nighties, one pink and one white. She made me stand there naked as she put on the white one. It was transparent. I could easily see her dark brown nipples on her large breasts, and mine was pink. I was shy again about the color....mine was equally transparent. I first pulled up the panties and my penis and its arousal was so obvious, then I slipped the short gown portion over my head. I looked at my reflection in her mirror and was in awe of how I looked. No body hair, nails painted, my boy nipples erect and my penis was so hard it was sticking over the top of the elastic waist. She looked at me and said I was her sexy lgirl now.....I was blushing. I could feel the flush wash over me. I had been aroused all day and needed some release, but was afraid to touch myself.
We went to bed and she insisted two girls should sleep together.It was warm and cozy in her bed.....she snuggled close. I could feel her body against me. She was holding me tight and whispered if I needed to relieve myself it was okay as she knew an aroused girl needed that. I was so nervous to do that.....so I shook my head and said I was okay.....she held me around the waist and when I heard her slow deep breathing I slowly and softly began squeezing myself. It felt so good. I was breathing so heavily..... but I needed to finish. I began stroking and pressing and all of a sudden she said I was a naughty girl for sneaking, for not doing it when she said I could......then she said, "Cum for granny little one".....and I did. I washed my thin panties with my arousal. I was wet, soaked. My hands were wet and the sheets. She turned and put on the light and said I was naughty for staining her bed and nightie. She made me get up and remove all my clothes.I was so embarrassed....then she motioned me over and to lay across her lap as she spanked me. I became aroused again, my penis was throbbing. I tried to hold back the urge to cum again, but I couldn't. I felt my penis explode as I whimpered, hearing her say....."Oh my.......aren't you the naughty girl"