Why I'm Auntiedolly
Why I’m Auntiedolly
My journey in cross - dressing.
It started when I realised that my older sister’s knickers were so much prettier than my boring underpants so I thought I’d wear hers instead. My mother quickly that this was wrong of course but I really couldn’t see why so I used to borrow them whenever I could.
This went on for some time until my elder cousin came to stay one summer. She was 17 and wore bras, suspenders and stockings which I lost no time in trying on by raiding the laundry basket. I remember my mother wondering why I was so long in the bathroom.
With me well on the way to being a cross dresser and not just a knickers wearer I was at a loss when my cousin returned home so it was my mum’s clothes which next interested me.
Like most adult ladies of the time she wore girdles and stockings and substantial bras as well as underslips. I’ve been a fan of stockings and girdles ever since.
As I grew older her clothes started to fit me as a growing lad and I took every opportunity to dress up in her things including her dresses, skirts and blouses.
This phase went on for some years and thinking back, I was lucky not to be caught. It was a close thing sometimes.
When I was 16 I was sent to stay with my Auntie Dolly one summer while my parents were away on holiday. Not an unusual arrangement in the 60s. Dolly had been widowed during the war but was still a handsome slim lady who always dressed with style. I was itching to see the contents of her laundry basket!
The first opportunity came soon and I quickly had a pair of her knickers on.
As she lived alone Dolly was not used to having anyone else in her bathroom and there was no lock. Yes, you guessed it, in she walked to find me in her knickers – horrors!
I spluttered something about getting mixed up between her knickers and my underpants and went bright red.
To my utter surprise she just looked at me and smiled “Oh don’t worry yourself” she said “I’m quite used to boys like you. Your uncle was just the same and I find it quite exciting”
She went on to tell me how much cross dressing had been a part of her married life and how she quite missed it since my uncle had been killed.
“Would you like to dress up properly” she said, and I admitted that I would of course.
“Come along to my bedroom and let’s see what we can find for you”
Well, within 15 minutes, with Dolly’s help, I was fully dressed in a bra, suspenders and stockings, knickers, a full length slip and a nice cotton summer frock. She also found me some shoes with a 2 inch heel.
It felt absolutely glorious but she hadn’t finished with me yet!
“Sit down here and we’ll put on a little make-up” and in no time I had lipstick, eye shadow and lashes, and a little colour in my cheeks. She back-combed my hair for me (it was quite long – 60s remember) and asked me to stand in front of the full length mirror.
I was amazed at the sight of this pretty young girl looking back at me. I thought I’d died and gone to heaven.
I spent all day dressed Au Femme with Auntie and we talked about my uncle’s interest in cross dressing and how she missed him. She had never remarried.
When bedtime came round she again astounded me by saying “I’d better find you a nightie to sleep in” but her next comment, after a long pause, completely floored me.
“You know; I told you how I miss John” (my uncle) “Would you like to come into my bed tonight?”
I couldn’t say a thing but turned and walked into her room where she produced a nightie and asked me to keep the stockings and suspenders on as “That always excited John”
I undressed and put on the nightie but kept the stockings as instructed.
My heart was beating madly (as if it hadn’t been all day) as I slid between the sheets and watched as Dolly herself undressed and donned her own nightie before joining me.
You can imagine the rigid state of my cock by now. I had had an erection basically all day of course but Dolly hadn’t mentioned any possible intimacy with her until now. The member was painfully rigid!!
This was my first time in bed with a woman or girl. I’d never got beyond snogging and fumbling before and I was eager to go “all the way” straight away. Dolly realised this of course and she actually said “You can fuck me as soon as you like”
I quickly lay on top and she guided my throbbing prick into her already wet and waiting pussy. You can imagine I didn’t last long – about 20 seconds. My first time with my cock all the way into a gorgeous woman – so much better than wanking. You’ll remember your first time of course – it never leaves you.
“Now you’ve got that out of your system the next time will be for my pleasure”
She spent half the night showing me how to give her pleasure with my lips, tongue, fingers and cock and I brought her to several orgasms as well as coming several times myself (the joys of teenage) We finally fell asleep as dawn was breaking.
I spent the whole week dressed Au Femme with Dolly and sleeping with her every night until it was time to return home. I was, of course, sad to go but she made me up a parcel of her underclothes “To remember me by and I hope to see you very soon”
This was the foundation of my lifelong passion for cross dressing and the completion of my sexual education and all thanks to my gorgeous Auntie Dolly.
It goes without saying that that was only the first of many visits to her home. Indeed my mother always said how nice it was that I was so attached to my auntie.
As the years when by I grew up, met and married my wife – the darling of my life – but never stopped visiting with my auntie for dressing and sex - no, not just sex, I was genuinely in love with Dolly. I have to say that she was a better fuck than my wife, much as I love her, but Dolly had much more experience of course and there was the added thrill of wearing stockings and suspenders while I fucked her.
Sadly my wife made her opinions on the subject of cross-dressing quite plain so I never had the joy of sharing it with her.
Sadly Dolly passed away many years ago but was sexually active until she was into her seventies and even after that she always delighted in the company of her “niece” and could always be relied on for a glorious hand job.
I continued dressing alone and in the closet until the coming of the internet and the revelation of how many there are like me that delight in wearing lingerie and dresses. I’ve had a few encounters with other CDs but nothing even comes close to my friendship with my darling, luscious, sexy, fuckable Auntie Dolly.
So that’s why my name is Auntiedolly on line; in memory of her and all the pleasure she gave me.
My journey in cross - dressing.
It started when I realised that my older sister’s knickers were so much prettier than my boring underpants so I thought I’d wear hers instead. My mother quickly that this was wrong of course but I really couldn’t see why so I used to borrow them whenever I could.
This went on for some time until my elder cousin came to stay one summer. She was 17 and wore bras, suspenders and stockings which I lost no time in trying on by raiding the laundry basket. I remember my mother wondering why I was so long in the bathroom.
With me well on the way to being a cross dresser and not just a knickers wearer I was at a loss when my cousin returned home so it was my mum’s clothes which next interested me.
Like most adult ladies of the time she wore girdles and stockings and substantial bras as well as underslips. I’ve been a fan of stockings and girdles ever since.
As I grew older her clothes started to fit me as a growing lad and I took every opportunity to dress up in her things including her dresses, skirts and blouses.
This phase went on for some years and thinking back, I was lucky not to be caught. It was a close thing sometimes.
When I was 16 I was sent to stay with my Auntie Dolly one summer while my parents were away on holiday. Not an unusual arrangement in the 60s. Dolly had been widowed during the war but was still a handsome slim lady who always dressed with style. I was itching to see the contents of her laundry basket!
The first opportunity came soon and I quickly had a pair of her knickers on.
As she lived alone Dolly was not used to having anyone else in her bathroom and there was no lock. Yes, you guessed it, in she walked to find me in her knickers – horrors!
I spluttered something about getting mixed up between her knickers and my underpants and went bright red.
To my utter surprise she just looked at me and smiled “Oh don’t worry yourself” she said “I’m quite used to boys like you. Your uncle was just the same and I find it quite exciting”
She went on to tell me how much cross dressing had been a part of her married life and how she quite missed it since my uncle had been killed.
“Would you like to dress up properly” she said, and I admitted that I would of course.
“Come along to my bedroom and let’s see what we can find for you”
Well, within 15 minutes, with Dolly’s help, I was fully dressed in a bra, suspenders and stockings, knickers, a full length slip and a nice cotton summer frock. She also found me some shoes with a 2 inch heel.
It felt absolutely glorious but she hadn’t finished with me yet!
“Sit down here and we’ll put on a little make-up” and in no time I had lipstick, eye shadow and lashes, and a little colour in my cheeks. She back-combed my hair for me (it was quite long – 60s remember) and asked me to stand in front of the full length mirror.
I was amazed at the sight of this pretty young girl looking back at me. I thought I’d died and gone to heaven.
I spent all day dressed Au Femme with Auntie and we talked about my uncle’s interest in cross dressing and how she missed him. She had never remarried.
When bedtime came round she again astounded me by saying “I’d better find you a nightie to sleep in” but her next comment, after a long pause, completely floored me.
“You know; I told you how I miss John” (my uncle) “Would you like to come into my bed tonight?”
I couldn’t say a thing but turned and walked into her room where she produced a nightie and asked me to keep the stockings and suspenders on as “That always excited John”
I undressed and put on the nightie but kept the stockings as instructed.
My heart was beating madly (as if it hadn’t been all day) as I slid between the sheets and watched as Dolly herself undressed and donned her own nightie before joining me.
You can imagine the rigid state of my cock by now. I had had an erection basically all day of course but Dolly hadn’t mentioned any possible intimacy with her until now. The member was painfully rigid!!
This was my first time in bed with a woman or girl. I’d never got beyond snogging and fumbling before and I was eager to go “all the way” straight away. Dolly realised this of course and she actually said “You can fuck me as soon as you like”
I quickly lay on top and she guided my throbbing prick into her already wet and waiting pussy. You can imagine I didn’t last long – about 20 seconds. My first time with my cock all the way into a gorgeous woman – so much better than wanking. You’ll remember your first time of course – it never leaves you.
“Now you’ve got that out of your system the next time will be for my pleasure”
She spent half the night showing me how to give her pleasure with my lips, tongue, fingers and cock and I brought her to several orgasms as well as coming several times myself (the joys of teenage) We finally fell asleep as dawn was breaking.
I spent the whole week dressed Au Femme with Dolly and sleeping with her every night until it was time to return home. I was, of course, sad to go but she made me up a parcel of her underclothes “To remember me by and I hope to see you very soon”
This was the foundation of my lifelong passion for cross dressing and the completion of my sexual education and all thanks to my gorgeous Auntie Dolly.
It goes without saying that that was only the first of many visits to her home. Indeed my mother always said how nice it was that I was so attached to my auntie.
As the years when by I grew up, met and married my wife – the darling of my life – but never stopped visiting with my auntie for dressing and sex - no, not just sex, I was genuinely in love with Dolly. I have to say that she was a better fuck than my wife, much as I love her, but Dolly had much more experience of course and there was the added thrill of wearing stockings and suspenders while I fucked her.
Sadly my wife made her opinions on the subject of cross-dressing quite plain so I never had the joy of sharing it with her.
Sadly Dolly passed away many years ago but was sexually active until she was into her seventies and even after that she always delighted in the company of her “niece” and could always be relied on for a glorious hand job.
I continued dressing alone and in the closet until the coming of the internet and the revelation of how many there are like me that delight in wearing lingerie and dresses. I’ve had a few encounters with other CDs but nothing even comes close to my friendship with my darling, luscious, sexy, fuckable Auntie Dolly.
So that’s why my name is Auntiedolly on line; in memory of her and all the pleasure she gave me.
2 months ago
