Dressing for Grandma
I remember growing up in the 60's how my step-grandmother wore those open bottomed girdles. 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 minded and didn't hide a bit of nudity either. When I was 18 or 19 I stayed with her many weekends after my grand father passed away. She would wear those girdles, like I said. I loved them She didn't wear the full ones that had the bra, only the shorter ones. Many times she had me join her in her bedroom as she dressed as she loved talking to me. As you can imagine I loved watching her come from the bath, removing her robe, and then pulling on her girdle and bra. 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 ion the bed wearing them and stockings, her bra on and I would get peeks of her, she never wore panties, never. Once when she was outside gardening I went in her room and undressed, searched her drawers for her 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. It was the way it held me and how aroused I became. I sat on the bed like she did and carefully put on her seamed silk stockings. I looked at myself in her mirror. I thought with my smooth hairless body I looked like the young 18 year old girl, the girl my parents always wanted. Here I was dressed in sexy lingerie, I had to admit I looked very sexy. I was very aroused.
Then all of a sudden I heard my grandmother say, "Oh my, aren't you the sexy little girl!.
I was in shock, but oddly she didn't yell at me or become angry. I started to cry. I was embarrassed and frightened she would tell someone, or punish me with a spanking. In that dark place of my mind, I had to admit I actually kind of liked her bare bottomed spankings, but I never told her I did.
She asked why I was wearing her girdle and stockings. I shrugged my shoulders but after more questions I admitted 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.
"Well, G, your arousal is obvious. Now that's not very girlie," She said with a grin.
She sat quietly for a moment and said,"This will be our secret. I have so many girdles, so many very exciting ones, you might like them. Would you like to try some of them on? Maybe we could have a fun dress up day?"
I shyly nodded. She told me it was okay and not to be embarrassed, many boys loved dressing in girls clothes when they are young 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 had helped my uncle when he was my age too. She caught him like she caught me, I knew my uncle was Bisexual, but the excitement of what she was saying was so amazing. Tears had been running down my cheeks, she kissed them away telling me she loved me and only wanted to help me discover who I really was.
She told me we could play dress up together, both of us trying on different lingerie items all afternoon and staying that was all day 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 excited.
We spent the day trying on girdles and stockings, I was so excited and aroused, She would look at me and I would turn away, embarrassed by my erection. She would tell me I should be proud to be such a handsome boy, and that I could look like a very sexy young girl too. My hair was longer and when I gazed at myself in the mirror, I did see a girl.
I was amazed watching her undress and be 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. While we cooked dinner and ate, she began telling me about her son, my uncle and how she helped him with his fetish of wanting to dress as a woman.
Grandma then said, "If your going to want to do this all weekend, then you must bathe in a bubble bath and let me shave what little hair you have. You must also let me trim your toe nails. You put a run in my stockings and I hated wasting them, they're 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.
"Mmmmm, I made a soft moan.
Hearing my moan of pleasure, she squeezed my penis teasing it, saying, "You're naughty."
Grandma's hand lingered under the suds, she held my penis and continued to squeeze it softly until it was fully hard. I wanted to cum, I was so close but the she let go of me and stood up.
After I was finished bathing she cut my nails, then she said she would put nail polish on them,
I balked and she said, "Pretty little girls need those things, and I will make you a very pretty girl."
I blushed.
"Grandma said "You will love it. You're a girl now."
I loved how she said that to me, I was so excited. But then reality hit me. I worried about my fiends and what they would think. My father, what would he say? Did she really mean I was a girl, and not a boy?
Grandma looked at me, "No need to worry about that now G. All of this will work out, I promise."
It was now bed time and 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 the dark brown nipples of her large breasts. Her panties were shear as well, her hairy mound clearly visible. I watched as she pulled them up, the fabric clinging to her body tightly, creating a camel toe. I yearned to touch her, to run my finger in her cleft, maybe my tongue.
My Nightie was was pink. I was shy about the color and mine was equally transparent. I first pulled up the panties and my penis with my arousal was very obvious Next 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 very hard and my penis was so erect it was sticking over the top of the elastic waist.
Grandma looked at me and said, "you're my sexy little girl now."
I was blushing. I could feel a 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 as she snuggled close. I could feel her body against me.
She was holding me tight and whispered, "If I needed to relieve yourself it's was okay, I know an aroused little girl needs that."
I was so nervous to do that. I shook my head and said, No Grandma, I'm okay.
She held me around the waist and when I heard her slow deep breathing I slowly 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 I flt her stir.
"You are a naughty little girl for sneaking, for not doing it when I said you could"......then she said, "Cum for me."
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 cock was throbbing. I tried to hold back the urge to cum again, but I couldn't. I felt my hard cock explode.
I whimpered.
Grandma exclaimed,"G........Oh my.......aren't you the naughty girl."
She would sit ion the bed wearing them and stockings, her bra on and I would get peeks of her, she never wore panties, never. Once when she was outside gardening I went in her room and undressed, searched her drawers for her 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. It was the way it held me and how aroused I became. I sat on the bed like she did and carefully put on her seamed silk stockings. I looked at myself in her mirror. I thought with my smooth hairless body I looked like the young 18 year old girl, the girl my parents always wanted. Here I was dressed in sexy lingerie, I had to admit I looked very sexy. I was very aroused.
Then all of a sudden I heard my grandmother say, "Oh my, aren't you the sexy little girl!.
I was in shock, but oddly she didn't yell at me or become angry. I started to cry. I was embarrassed and frightened she would tell someone, or punish me with a spanking. In that dark place of my mind, I had to admit I actually kind of liked her bare bottomed spankings, but I never told her I did.
She asked why I was wearing her girdle and stockings. I shrugged my shoulders but after more questions I admitted 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.
"Well, G, your arousal is obvious. Now that's not very girlie," She said with a grin.
She sat quietly for a moment and said,"This will be our secret. I have so many girdles, so many very exciting ones, you might like them. Would you like to try some of them on? Maybe we could have a fun dress up day?"
I shyly nodded. She told me it was okay and not to be embarrassed, many boys loved dressing in girls clothes when they are young 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 had helped my uncle when he was my age too. She caught him like she caught me, I knew my uncle was Bisexual, but the excitement of what she was saying was so amazing. Tears had been running down my cheeks, she kissed them away telling me she loved me and only wanted to help me discover who I really was.
She told me we could play dress up together, both of us trying on different lingerie items all afternoon and staying that was all day 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 excited.
We spent the day trying on girdles and stockings, I was so excited and aroused, She would look at me and I would turn away, embarrassed by my erection. She would tell me I should be proud to be such a handsome boy, and that I could look like a very sexy young girl too. My hair was longer and when I gazed at myself in the mirror, I did see a girl.
I was amazed watching her undress and be 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. While we cooked dinner and ate, she began telling me about her son, my uncle and how she helped him with his fetish of wanting to dress as a woman.
Grandma then said, "If your going to want to do this all weekend, then you must bathe in a bubble bath and let me shave what little hair you have. You must also let me trim your toe nails. You put a run in my stockings and I hated wasting them, they're 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.
"Mmmmm, I made a soft moan.
Hearing my moan of pleasure, she squeezed my penis teasing it, saying, "You're naughty."
Grandma's hand lingered under the suds, she held my penis and continued to squeeze it softly until it was fully hard. I wanted to cum, I was so close but the she let go of me and stood up.
After I was finished bathing she cut my nails, then she said she would put nail polish on them,
I balked and she said, "Pretty little girls need those things, and I will make you a very pretty girl."
I blushed.
"Grandma said "You will love it. You're a girl now."
I loved how she said that to me, I was so excited. But then reality hit me. I worried about my fiends and what they would think. My father, what would he say? Did she really mean I was a girl, and not a boy?
Grandma looked at me, "No need to worry about that now G. All of this will work out, I promise."
It was now bed time and 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 the dark brown nipples of her large breasts. Her panties were shear as well, her hairy mound clearly visible. I watched as she pulled them up, the fabric clinging to her body tightly, creating a camel toe. I yearned to touch her, to run my finger in her cleft, maybe my tongue.
My Nightie was was pink. I was shy about the color and mine was equally transparent. I first pulled up the panties and my penis with my arousal was very obvious Next 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 very hard and my penis was so erect it was sticking over the top of the elastic waist.
Grandma looked at me and said, "you're my sexy little girl now."
I was blushing. I could feel a 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 as she snuggled close. I could feel her body against me.
She was holding me tight and whispered, "If I needed to relieve yourself it's was okay, I know an aroused little girl needs that."
I was so nervous to do that. I shook my head and said, No Grandma, I'm okay.
She held me around the waist and when I heard her slow deep breathing I slowly 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 I flt her stir.
"You are a naughty little girl for sneaking, for not doing it when I said you could"......then she said, "Cum for me."
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 cock was throbbing. I tried to hold back the urge to cum again, but I couldn't. I felt my hard cock explode.
I whimpered.
Grandma exclaimed,"G........Oh my.......aren't you the naughty girl."
2 years ago
