Grandmother's Sissy

by Sissy Paula (USA)

I am a life long sissy crossdresser. I had a Grandmother that I loved to visit every chance I got the opportunity. I began crossdressing at the age of 18. It started when I first slipped into a pair of my Mother's high heel shoes. I was so excited when I saw my mirrored image while wearing Mom's high heels. that it became an obsession with.

One day, I found a one piece flower print bathing suit tucked away in one of my Mother's vanity drawers. I immediately slipped into it and then sled my feet into my favorite pair of my Mother's high heel shoes. When I looked into the mirror, I couldn't believe my eyes. The bathing suit was so tight it acted like a corset and presented me with a very feminine hour glass figure. It was so exciting.

I reached down and removed a tube of my Mom's lipstick that was resting on her vanity. I removed the top, rolled up the lipstick. It was a vivid shade of red and I nervously apply it to my lips. I made many upper and lower passes with vivid red lipstick, until my lips were thoroughly covered. It was at this very moment that my sissy ways would be etched in stone. I continued this way of sissiness whenever I had the opportunity.

It's time to go back to my Grandmother. She was a full figured woman with all the curves in all the right places. She always wore dresses or skirts and always high heel shoes or wedges.

Grandmother appearance was always a dream for a sissy like me. Grandmother also loved her make up and she was very maticulas in it's application. Her hair was perfect and she had several wigs that she wore when it suited her fancy. My Mother traveled as a sales representative for a pharmaceutical company, which means I got the opportunity to stay with Grandmother.

While staying with Grandmother, I would take every opportunity to watch her put on her make up. She sensed that I enjoyed it and never objected. One day, while she was applying a vivid shade of red lipstick, I asked her what it tasted like. She stopped and held the lipstick up in front so I could see it and said, do you mean my lipstick sweetie. Yes Grandmother! Well sweetie, it has a pleasant taste but it's mostly how it feels. Creamy, soft and smooth, and it makes my lips so very delightful.

Why do you ask sweetie. Well Grandmother, i was wondering if you might put some on me. I would love to see how it feels. I see! You do know sweetie, lipstick is for girls and not for boys. Boys who wear lipstick are called sissies. I'm sorry Grandmother, I just wanted to see what it tasted like. She went back to applying the vivid red lipstick doing it ever so slowly and watching me as I watched her.

Finally she stopped and held the lipstick high enough for me to see. She watched me through the mirror and could see my eyes were glue to the vivid red lipstick. Well sweetie, if I apply this lipstick to your lips, even if it's only for a taste, it will mean you will be as sissy. Do you still want me to apply the lipstick? Yes Grandmother! Yes I do! Well, I see! Over on the bed is a small cushion, get it an bring it here. When I returned with the cushion, Grandmother had turned around. Place the cushion here then kneel. I immediately did as she said.

She held my chin and lifted my head. Sweetie, separate your lips for me. Grandmother had a pencil in her hand and looked me in the eyes. You have pretty lips, sissy lips. and today I am going to make you Grandmother's sissy. She started to move the pencil over my upper lip. I know you are a sissy. My daughter, you Mother, told me you were playing with her things. And so sweetie, if you want to be a sissy, I am going to make you a very beautiful sissy.

I will not stand for a sissy trying to emulate a girl and making a mockery of his sissy appearance. And so my sweet sissy boy, when I am finished with you, you will never want to go back to wearing boys clothing. Grandmother carefully moved the pencil over my upper lip, then over my lower lip. Stopping and looking then returning back and forth until she was satisfied. She put the pencil down and picked up a different one. Close your eyes my sweet to be sissy. Grandmother began to run the pencil over the lids of my eyes.

Sweetie, you can't be a complete sissy until your face is completely sissified with all the make up available to us ladies. A sissy cannot live by lipstick alone! She worked slowly and deliberately on my eyes. First the left then the right. She moved from pencil to brush and constantly called me sissy Paul. Sometimes, my sweet sissy Paul. Well, that's perfect. You can open your eye sissy Paul. She reached for another pencil and said; open your eyes as wide as you can.

Good! Grandmother began to pass the pencil over the lower portion of my eye. First the left and then the right. She kept going back and forth to each eye until she was completely satisfied. She leaned back. Oh my! That's perfect. My sissy grandson is going to make me the proudest Grandmother in the world. Well sweetie, it's time for the closing effect, the lipstick. I suspect you want the same shade that i am wearing.

Oh yes Grandmother! Please yes! She laughed! You are such a sissy. Are you Grandmother's sissy? Yes Grandmother! I am you sissy! Of course you are. Instead of calling you sissy Paul, I'm going to call you sissy Paula. Part sissy Paul, and all sissy Paula. Do you like that sissy Paula? Oh my! I love it Grandmother! She reached for the lipstick, rolled it up all the way then held it close to me. Is this what you want sissy Paula.

Oh yes Grandmother! She laughed! You are such a sissy. Now tell grandmother what you want? Oh Grandmother, please put your lipstick on me. Please, please, please. Are you Grandmother sissy. Oh yes I am. I am your sissy Grandmother and please, please put on me your beautiful red lipstick. She reached out and placed her hand on my chin and lifted my slightly. Part you lips slightly sissy Paula and Grandmother will totally cover your sissy lips with her vivid red lipstick.

Grandmother began with the upper lip and slowly passed the red lipstick back and forth. then moved to the lower lip and did the same thing. I was in heaven as I watch her passing the red lipstick over and over my upper and lower lips. Do you like this sissy Paula? Oh yes I do Grandmother. Please don't stop. She smiled and kept applying the lipstick to both upper and lower lips. She leaned back keeping the tube of lipstick in full view so I could see it. Well my sweet sissy grandson, that's perfect.

Oh Grandmother! Could you put some more on me. You like it that much. Oh yes! She leaned forward, held my chin and started applying the red lipstick once more. Sweetie, when your mother told me about you playing with her things, I already suspected you were a sissy. Every time you came to see me you always asked if you could watch me put on my make up. I figured a boy who likes to watch his Grandmother put on her make up must be a sissy.

So, I began to buy some feminine sissy clothing for you. I purchased many items of lingerie, including a training bra, panties, garter belt and several pairs of nylons. I also purchased a white petticoat and a very beautiful pink flower print flowing dress. Also, a very pretty pair of pink high heel shoes. Now sweetie, I think it's time for me to stop applying the lipstick and to get you dressed in all those pretty sissy feminine things I purchased for.

Now I have chosen a wig for you, but I want to sissy dress you without the wig to get a complete sissy image of my grandson. Afterwards, I'll fit the wig and style it. And when all is completed, I will have you my tube of lipstick and permit you to apply it yourself.

And so this is my story, fiction. I am a sissy crossdresser who loves make up, especially lipstick. I also love all the feminine apparel. i hope someone likes my story.

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Dec 20, 2020
Dress me too grandma!
by: Anonymous

You made me feel like I wanted someone to dress me up too!I love wearing women's clothes! In fact I'm wearing a brand new pair of pink panties right now. Loved the story.

Nov 06, 2020
by: Mama's boy

Grandma and mom provided me with luxurious lingerie especially nylons and smooth silky undies. High heels too. Next sexy makeup to disguise my male features. Wigs also and I was very feminine looking. Mom provided lots of ass kicking drugs to lessen my inhibitions but after awhile I looked so fucking hot that my mom and grandma wanted pleasuring. My cock always got nice and stiff when dressed up like a whore. Looking all sexy and frilly in my lingerie and makeup mom and grandma took turns sucking my sissy clitty and getting me ready to fuck. So deliciously nasty and looking seriously sexy mom fed me Cialis and amphetamines to get me hard and ready to rock and roll. Grandma fucked my ass ass and mom took my hard cock in her juicy wet cunny. So incredibly sweet to pump my mom's pussy and slowly grind my stiffness deeply in moms pussy.

Oct 26, 2020
miss her
by: Anonymous

My grandmother passed away from cancer when i was 8 yrs old. i ws the oldest grandchild and went with her and my grandfather almost always during summer vacation. She was my first love. When she went into the hospital i would go into her closet and play/smell her nylons and panties. I am now in my late 60's and still can see the scene and Still love the scent of a womens nylons/pantyhose and panty scent of a pussy. omgoodness i am getting wet for sure stephaniecurl

Oct 16, 2020
Grandma s sissy mom's bitch
by: Mama's boy


Sep 05, 2020
Very sensual
by: Rick

I Love and admire sweet sissy girls.Oh baby I would lick and suck on your buddigng nipples gentley nibbling them feeling them stiffen .Then I lay you down and slowly slide your silky panties down and kiss your clitty licking it to full hardness sucking you good my tongue then will push deep into your sissy pussy as I eat you out getting you nice and wet with my tongue so you can except my hard throbbing cock , I lean in and kiss your sweet lipstick covered lips as I thrust forward my cock opening up your tight boy pussy Oh Baby your pussy is the finest pussy around so warm and tight you wrap your legs around my waist as I pick up the pace pumping my cock in in out in long strokes I look deep into your beautiful eyes as I unleash a powerful shot of my seed deep inside you baby long steady streams of my cum fill you just then your clitty erupts shooting all over my admedn umm we almost came together baby . I Love sissy crossdressing boys 💋

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