Dressing for Grandma

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 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 wear those girdles, like I said, the open bottomed kind. I loved them She didn't wear the long ones that had a 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. It was arousing to see yourself like that.

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."

I went home and thought about the weekends experiences. I struggled with much of it, but I was very aroused with it too. I feared what would my friends say if they found out. I removed the toe nail polish as soon as I got home and was relieved to feel normal. I felt like a boy again. It was Thursday when my mom told me grandma had called and wanted me to stay with her this weekend as she had more work she needed help with. I froze, shivering from the "work" she was referring to. But then I realized my cock was swelling, I was feeling that wonderful feeling of arousal washing over me. My mom had gone out and I was laying on my bed reading. My cock was hard thinking about the past weekend and how after all the dressing up had made me feel. I thought about our little game and how grandma knew I was horny from it. I knew she loved seeing me that way and took pleasure in denying me the release I hungered for and even more in punishing me when I touched my cock and came.

I loved being home alone with the freedom to masturbate without anyone around to disturb me. I could be naked and moan as much as I wanted. As I was laying there I began to wish I was with grandma, she would have me dressed in something sexy and feminine. Knowing my mom wouldn't be home for hours, I decided to snoop in her draws and see what kind of lingerie she had. I had peeked before, looking for naughty things. I had even tried on her girdles once or twice. I was lost in my own arousal and was wanting to feel something soft and silky rubbing against my cock. I opened a drawer that had mom's panties. There were so many kinds, cotton, nylon, bigger fuller style, and bikini's. I grabbed the pale blue bikini style and rubbed it against my cock. It felt amazing. I stepped into them and pulled them up my thighs and over my butt. They were tight and my hard cock created a large lump in the front. My hands brushed over my cock as it oozed pre cum. I wanted to try on the others too. I was so excited as I danced in front of the mirror. The next pair I put on were larger. They were what my mom always called her granny panties. I loved the fabric, but I wasn't sure they would be as sexy as the bikini panties. I pulled them slowly up my thighs. The silky material felt amazing as it covered my young hard cock. I reached down and held it, squeezed it and watched as the pre cum created a wet stain on the loose fabric. Letting go I turned to look at myself in the mirror. The waist was pulled up over my hips and my cock was tenting the front. The panties were full cut so they draped over my cock which stood straight up tenting them outward. I loved how I looked in them, but I loved how I felt in them even more, even though they were a loose on me.

I was standing in front of the mirror admiring myself when I heard a knock on the window. It scared me and I jumped back, covering myself with my hands. I was caught. Mr. Wagner from next door was looking right at me through the window and was smiling. He motioned me closer, wiggling his finger. I shook my head and ran to my room. He knocked on my bedroom window and told me to come to the backdoor. I was petrified and so confused about what to do. But being seen by him seemed to arouse me as my cock was harder now than before. I felt so vulnerable. Slowly I went to the backdoor. Mr. Wagner was standing there waiting for me, and I hesitated standing there naked except for my mom's panties that were tenting outward. I was filled with anticipation and fear.

"Open the door and let me come in...sissy boy," Mr. Wagner said.

I was so embarrassed, but I unlocked the door.

He stepped in and asked, "Does your mother know you look so cute in her undies?"

I shook my head no.

"Would she be upset if she knew?"

I shrugged my shoulders not really knowing how she would feel or what she would do.

"Well...if you can keep a secret...I can too...you do look so pretty in those panties."

My cock pulsed with those words. I was so hard and all I wanted to do was reach down and squeeze it. He had obviously been out for a jog, he was sweaty and was wearing his running shorts. He was also aroused as I could see his cock was tenting his shorts as mush or more than the panties I was wearing. He reached out and caressed the wet spot that had formed around the head of my cock. He squeezed it and I moaned.

"You like that...don't you?...Did I catch you before you had a chance to cum?" He asked.

I nodded again.

"When's your mom going to be back?"

I again shrugged my shoulders and said, "Not for a while...maybe about dinner time," I replied.

"Good...we have sometime."

He reached out, grabbing my arm and said, "Take me to your room."

Leading him to my bedroom I knew he was looking at my butt, I knew I had a cute bubble butt and I was loving the attention. I was feeling so vulnerable and yet powerful. As soon as we entered my room he told me to stand and touch the front of my panties, to rub my cock. I gladly complied, I needed to feel those feeling, I felt like I was going explode. I stood there silently rubbing my hard cock.

"Pull it out the leg hole...let me see it...but keep your panties as they are."

Mr. Wagner was rubbing the front of his track pants, he was sighing and moaning as I exposed my hard cock slowly. First just the head and then more, until I had the panties pulled all the way to one side, I liked teasing him.

He ordered me, "Come here...right here."

He sat on the edge of my bed. I stepped in front of him, inches away from him as he pulled his cock out of his shorts and began stroking it. Pre cum was oozing from the tip as his moved up and down the shaft. I loved seeing his cock so hard and aroused. Then he stopped stroking himself and put his thumbs under the waistband of my panties. In one quick motion he pulled them to my knees, my cock popping out, pointing at his lips as he licked the tip. My cock twitched as he pulled back from me. I was so aroused. Mr Wagner dropped to his knees and took my cock completely in his mouth. I came so fast as he bobbed his head up and down.

With cum on his lips he said, "Your turn,"

He pushed me to my knees. Mr. Wagner's hairy cock was at my lips. Pulling my head to him, he pushed forward parting my lips. His pre cum whetted my lips as I opened them allowing his cock to fill my mouth. His taste aroused me.

"You will be my cock whore or I will tell your mom I caught you wearing her panties...sissy boy."

Holding my head he pounded his cock in and out and down my throat.

I was gagging as he told me, "Breathe through your nose and relax...if you want to be my good cock whore!"

Mr. Wagner filled my mouth with his seed. His cum was dripping from my lips. Looking down at me he slapped my cheek,

"You need to swallow all of my cum...not one drop will be wasted...you're my cock whore now."

I woke Friday morning knowing I was going to my grandma's. I always wake up with a hard cock, but this time it was different. I wondered what she had planned, and the anticipation aroused me. I wondered what I should wear, really knowing I wanted to wear the panties I took from my mom's drawer. I pulled them out from under my pillow and inhaled my own scent which filled them. The silky fabric felt luscious as I wrapped it around my cock and began stroking it.

There was a knock on my door and mom burst in. I tried covering myself as best I could.

"Oh My, What the...What were your doing G?" Mom asked.

I turned over, burying my face n my pillow.

Mom sat on my bed next to me and rested her hand on the back of my head.

"G, maturation is normal, I'm not upset with you for doing that. You were in your room with the door closed, maybe I should have asked to come in. I apologize for not asking."

I laid still, not sure what to say.

"G, I know you have been sneaking into my lingerie draw and trying them of, or using them to masturbate, there have been stains."

Now I was really embarrassed. I was careless, not thinking she would notice. I was stupid, I felt foolish.

"I'm sorry mom. I won't happen again," I said.

"G, I just asking you to ask me if you want to, I don't know how to say this. If you want to have one of my panties, I want you to ask."

"MOM!" I was so embarrassed.

"My mother told me about last weekend at her house. Your Grandma said you were very sexy in the things you wore."

"Oh my gosh Mom, she told you?"

"Yes G, She and I don't have secrets. She wanted me to know what she had done with you. She did not think hiding it would be good. Now turn over and lets talk."

I laid with my face still buried in the pillow. I felt mom's hand on my butt as she urged me to face her. My cock was responding to her hands squeezing and caressing. My pants were still pulled down and I wasn't sure how to turn over without losing the little cover I had from the blanket laying over me.

"You know G, I grew up with my mother and watched her with your uncle. He loved wearing feminine clothes. He borrowed mine a lot. I would get very upset with him, he never asked. But my mom always provided the safety he was begging for. She would buy him clothes and lingerie, many times nicer things that she would buy me."

She was making me feel better. I knew I wasn't alone in how I felt, but I knew my friends would never understand. I slowly turned over, trying to stay covered. When I rolled completely over moms hand was resting on my cock, with only the thin blanket laying between me and her, she could feel my cock pulse.

"Mmmmmm, G you're hard." Moan teased.

I felt my face flush. My cock pulsed again.

"Can I see the panties G?"

I pulled them out from under my pillow and handed them to her. I still felt embarrassed, but I was aroused and that empowered me. For me arousal was like a drug, once it washed over me I could do almost anything. Mom looked at the panties and the cum stains, she dipped a finger in the wet spot and brought her finger to my lips.

"Taste yourself." she instructed.

I stuck my tongue out and licked.

"Good boy G, you really have a lot of cum in these panties, did you just leak pre cum or did you orgasm?"

"I didn't cum, It just leaked as I walked around in them."

There was no way I was going to share about Mr. Wagner. I suspect Mom would be really upset with me if she found out about he and I.

Mom's hand was still holding my cock. Occasionally she would give it a squeeze. It really felt good. Her green eyes looked at me searching my face for a reaction. I closed my eyes, tossing my head back slightly as I raised my pelvis pressing into her hand.

"G, I would like to help you," She said as she began more squeezing and fondling of my cock.

I moaned as she pulled the thin blanket away, revealing my cock. Her finger dipped in the puddle of pre cum pooled on my belly. This time, mom brought her finger to her mouth. She licked her finger and then sucked it.

"Mmmmmmm...Mommy like your cum."

I didn't know what to say. I was so aroused, so close to cuming. Her hand returned to my cock. and squeezed it again. Mom quickly stood up. I watched as she reached under her skirt and lowered her panties. Stepping out of them she held them, dangling from a finger.

"Take them, I know you want them."

I nodded and grabbed them.

"Bring them to your face and smell them. Inhale my scent from the wet gusset. Taste me."

I could smell her scent filling the room. My mother's pussy was wet and her panties were drenched. I laid them over my face and inhaled her intoxicating scent. I licked the wet crotch before I sucked them into my mouth.

I felt my pants being lowered and removed as her wet lips surround my cock head. The smell of her wet cunt, the taste of her panties, and her lips sucking me sent me over the edge as I came in my mommy's mouth.