Sissy Boi Stories

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Sissy Boi Stories
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My name is Sam. I grew up in a small town of Avonshire. I was ...
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I arrived home, from work, on the Bank Holiday weekend, of Easter. The following week, I was taking days off that were owing to me, so the forecasts were good, and I was happy. As I entered the house, I heard chatter, and recognized my mom and aunt Marilyn’s voice.
“Hello son, look who is here.” mom spoke, as I gazed at aunt Marilyn. I had always and still am, very fond of her, and fantasized about her, when in bed and in the shower. I know it is wrong, I told myself, but that was my secret.
Mom: “Aunt Marilyn, is here, to ask you, if you would like to spend some of your days off work, at her home.”
Me: “Yes, I will accept the offer mom, and thank you aunt Marilyn.”



Well we sat down to a meal and my aunt slept over that night, so we made an early start in the morning.
Aunt Marilyn: “Did you sleep well Graham, as we got into the car?”
Me: “Not really aunt, as I was excited about this stay with you. ”
I waved my mom goodbye. The journey took us about ninety minutes, and arrived in Park Close, a cul-de-sac, with six bungalows there. It was a tranquil area, and in the countryside. I liked the closed in hedges of the lanes, we drove down, were beyond the hedges, laid open fields of grass and crops.
My valise case (a small travelling bag), just carried my bathroom kit, a few underpants and tops, a pair of blue jeans, a white ladies blouse, full sleeves with a Peter Pan collar, a pair of white knickers and ladies beige slacks, with a button and zip, side fastening.
Aunt Marilyn, showed me around and where everything was. Then we left, to go for fish and chips, to eat at Tally’s. On return, aunt took a shower, and offered me to take one after her, which I did, to freshen up.



About an hour later, aunt, telling me, as I was reading a woman’s magazine of hers, that she just be over the road, to chat to her friend for awhile.
Me: “ Yes aunt, go ahead, is it okay if I do this crossword aunt?”
Aunt Marilyn: Yes sweetie make yourself at home.
I was still with a bath towel around my waist, male sarong style, not female, with it covering my bust.
Once aunt left, I had the urge to peek into her boudoir, and there on the bed, was a lovely shade of pink, nightdress. Oh gosh, as I stared at it, but dared not touch it, in case aunt had placed it, in a certain way. Weakness of a man overcame me, and I found myself holding it up in front of me, then dropping the towel, to the carpet, and stood in front of the mirror, and with a rampant erection, as I had not mastur-bated for about five days. Oh gosh, as I was now mesmerized, then it touched the top of my pe-nis. Oh no, as I hoped my precum had not stained it.
Then to my horror, my aunt’s voice at the door, saying, ” if you like it so much, why not put it on.”
Me: “ I can explain aunt Marilyn. Please don’t tell my mom.”
Aunt entered the room, locked the door, and came toward me.
Aunt Marilyn: Now my teenage niece, we best get you into your nightdress, and early for bed.
Taking the nightie from me, slipped it over my head, not mentioning my arousal.



Aunt Marilyn: “Pink, does become you, Jane, Very cute indeed. You shall wear it tonight and if you make a mess in it, you will hand wash it, and you will wear another one of my nighties, each night, until you leave. You see Graham, I mean Jane, as I unpacked your valise earlier, I noticed a certain few items, that only could belong to a girl wearing them, so to confirm it, made an excuse to leave you alone for awhile, to discover you, in a compromising position, which I have done. Now my sweet young niece, we best go and watch the film on DVD, ” THE WOMEN.” Tomorrow morning, you shall wear what I put on my bed for you. Any argument or protest, then your mom will be contacted. Do you understand Jane?”
Aunt Marilyn: “ Now, when you need to use the bathroom, you will sit down to pee. You are now my niece, a girl. We are going to have such fun, while you are here. Oh you’re going to see some change in you. ”
I sensed my boyhood, being overtaken by a new ultra-feminine existence, while at aunt Marilyn’s.
What a wonderful way to get caught.
Lovely story, could use some sharpening up concerning your writing grammar but I did love it. We all want an aunty like that, to be told what to do to bring our feminine side out. Kisses hon.
Beverly
had a similiar experience ,but my aunt had a strapon that she used very well it vibrated on her pussy as she laid the wood to me felt great.
Could of been oh so much better and longer.
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When I was eighteen my father remarried. I just loved my new
stepmother and was glad that dad had found someone. In a short time Martha had changed my
father from a rough and tumble typical macho dad into a kind and sweet gentleman. I
thought the change was best for all concerned. He had lost his beer gut, had improved his
posture and had become very respectful of women.
Martha had him cleaning the house, cooking meals and doing personal
tasks for her and I. My father had even offered to shine my shoes and boots for me. Well
it was really Martha who had offered his services but he didn’t refuse. He did look a
little embarrassed about it, but when Martha said “Eliot, ask her if you can take
care of her shoe wardrobe.” He asked and once a week he checks to see what needs
care. He polishes and cleans any shoes that need it, cleans the soles and powders the
insides. What’s really cute is the little apron he wears when he is working at home.
My little brother Mike really has a problem with Martha. He hates her
and thinks she is turning Dad into a sissy. I tried to tell him that her and Dad’s
marriage is their business and not his, but he won’t listen and just will not be nice
to her. I have told him to be careful around her “she isn’t going to take your
crap Mikey”. He just laughs it off.
Mikey is just fourteen and a bit of a brat. Our mother and I both
spoiled him. He is used to getting his way and has always been able to manipulate the
women around him. Martha is different she seems to be able to run the men in any direction
she wishes. I had the feeling my father had already learned this and eventually Mike would
also.
I was eighteen and lived at home but as an adult I pretty much can
come and go as I please. My father had objected to my freedom but Martha told him
“She is a young woman, and as a woman in this house she will do as she pleases!”
I couldn’t believe it when my father said “yes ma’am” So I was free to
stay at my boyfriend’s house on the weekends, and often did. I was in college and was
working part time so I wasn’t home all that much.
I was just leaving one Friday night when I heard Mikey and my
stepmother really going at it in the kitchen. Martha had assigned Mike some task that he
thought was beneath his worth and they were discussing it. I could see that Mikey was
going to lose this argument. I just waved by-by to them and left. My weekend didn’t
go well I had a fight with my boyfriend and returned home Saturday afternoon.
When I walked in I was surprised to see my father and stepmother
talking to a girl of about twelve. She sat next to Martha on the couch. My father sat in a
straight chair across from Martha and the girl. The young girl was dressed in a pink party
type dress she was nervously crossing and uncrossing her pretty little ankles. My eyes
were drawn to her white ankle socks with the pink trim, on her feet were a pair of black
patent Mary Janes. She sat with her hands folded in her lap her head was bowed down as if
she was looking intently at her hands. She never even looked at me when I walked in.
“And who is this charming little thing?” I said. Martha
smiled and said, “This little cutie is your younger brother.” “Oh my
GOD” I said, “It is him, oh he is adorable. How did you do it?” Martha said
it was easy and it was the best way to train an unruly male. Then she said “It has
worked wonders on your father.” I looked over at my father and he was busy looking at
his folded hands also. Then I noticed that my dad was wearing what looked to be a pair of
ladies pant boots and judging by the cut of his pants ladies slacks.
“Stand up dad” I said. And my father dutifully stood. He
kept his eyes down, as I looked him over. I fingered the zipper on the side of his slacks,
felt the fabric of his almost a shirt blouse and traced the line of his bra across his
back. I heard his intake of breath as my hand felt the smooth panty line of his posterior.
“Nice” I said. “Now you Mikey stand up sweetie pie.” Sweetie pie stood
and he too kept his eyes down, must be a guy thing. I took Mike’s hand and pulled him
to the room’s center. I stepped back and just looked.
The dress was the focal point. It was pink with white ruffled trim.
It was as feminine as a nursing mother. The puffed sleeves were short with a ruffled edge.
The hem was well above the knee and the stiff white petticoats stood almost straight out.
I reached out and felt the boys leg, “Oh Mikey, you shave your legs.”
“That’s so sweet”. He blushed from; I swear his legs to his ears. Martha
had styled his boyish hair into a mostly feminine style a large pink ribbon was pinned to
the upper side of his pretty head. He wore soft make up and was about as humiliated as a
boy could be. I turned to Martha and asked her if I could borrow the new girl for a while.
She said, “Of course dear, enjoy her.” I turned and started up the stairs to my
room. I looked back at Mike and said “get my bag dear and follow me.”
Mike seemed glad to get out of the living room and the dominating
presence of his stepmother. In my room he broke down, “you’ve gotta help me
sis.” I said “your smart mouth got you into this fix my pretty one. You had
better keep it shut or GOD knows what she will do next.” Now lets talk. “You
better face it girl, you are going to be in dresses for a while. The best deal for you is
to get to dress your age. You really are quite pretty and dressed like an early teen you
will be a very pretty young girl. Dressed like you are, well you are a very pretty
sissy.” He sobbed and said “But I can’t dress like a girl. What will my
friends say?” “What will they say
when they see the outfit you have on now?” I asked. He just shook his head and sobbed
quietly. Now listen Mikey, “you look really cute this way, and I like the why you
behave much better than you did when you wore pants.” 
“If you behave like a nice little girl maybe you can be in clothing that
suites your age.” “I will talk to Martha if you promise to be a sweet girl, if
not then, well I guess you know what will happen when your friends see you.”
“Here you can read this copy of Cosmo, we can get you some Teen Beat or Seventeen
later, when we go shopping.” “Shopping?” was all he said. “Now Mikey,
let’s teach you how to do girl.” “Stand up sweet heart, oh that is so
precious, you are just the most darling little sissy ever.” “Ok girl, walk for
me, walk in front of the mirror.” “Watch me, hold your hands down, keep your
upper body straight, take shorter steps.” “The main thing is to remember your
are a young lady now, carry yourself as one.” “You practice for a while and I
will go and talk to Martha.”
I got downstairs to find my father at Martha’s feet. He had a
very complete pedicure kit out and was in the process of doing a spa pedicure on her.
“Ooh that looks yummy,” I said. “Maybe your foot girl could do me
later?” I asked. “Of course dear” was Martha’s response. I sat next to
her and brought up the subject of Mike. “Martha I have convinced Mike that you intend
to keep him dressed like a girl child and send him to school in a party dress.”
“I also convinced him that it would be best for him to dress as a girl his own age,
since he will be staying as a girl.” A big smile crossed over Martha’s face.
“You devil you.” She said. “I was only going to embarrass him a little over
the weekend.”
“Well we can’t pass up this opportunity to help the boy
become a better person.” “Can we?” “I will need to take him
shopping.” I said. Martha said, “use your fathers credit card.” “Get
the new girl everything she needs.” Oh and dear keep her in the party dress for the
shopping trip.” It will help her remember to behave.”
It was a very contrite little girl that made the trip to the mall
that day. Mikey was the picture of embarrassment as we walked to the car. He sat quietly
and sobbed gently as I drove the car through town and eventually the mall. Mike hesitated
getting out of the car. I held the door for him and handed him his little black patent
purse. I almost couldn’t go through with it when I saw the look of terror in his
eyes.
The mall was filled with teenagers I knew Mike must know many of them
and that he was in abject terror of being seen. Mikey’s little shoes made a darling
little girlish click clack as he walked along. I know that the feminine sound must have
been horror to his ears. I remembered how much I loved the sound of my shoes when I was a
little girl. I smiled at the thought of my bratty little brother hearing his hard little
heels screaming “sissy” in his ears. He moved over to my side in an effort to
not be seen by the group of girls hanging out in front of a shop called Rave.
Rave seemed to be just the kind of shop the new Mikey should check
out, so I guided the thoroughly humiliated boy into the confines of this bastion of
teen-age femininity. We heard it at the same time, “Mikey?” “Oh my God, it
is you.” I turned to see a grinning pair of teen-age girls. “What gives
Mike?” “Did you lose a bet or something?” Before Mike had a chance to make
up a story I said, “Mike is being punished, and will have to spend a few weeks, maybe
even months as a girl.” “She needs a new wardrobe, do you think you girls could
help us shop?” “She will need panties, bras, skirts, shoes and make up for a
girl her age.” The two teen girls were just jumping at the chance to add to the
humiliation of Mikey.
By know we had drawn the attention of a couple of sales clerks and
two more girls who were being filled in on Mikey’s plight. It seems Mike had a
reputation as being a hellion around the girls at school, the group of girls thought
Mikey’s punishment was fitting his crimes just fine. I gave one of the girls the
credit card and said “Have fun.” “I am going for coffee and I need some
shoes myself.” “Meet me at the makeup counter over at Macys when she is all
fixed up.”
I found a darling pair of flats for myself and was on my second Latte
when Mikey and his new best girlfriends showed up. Mikey no longer had on the pink dress.
He did have on a pink short all outfit with a white tee under it. The tee was all girl
though with dainty lace at the neck and sleeves. He still wore his Mary Jane's and ankle
socks and carried his little girl’s purse. The finial indignity was the pink ribbon
Martha had pinned in his boyish hair. The girls carried bags and bags of things from Rave,
Wet Seal and Forever Young all the new miss needed now was make up and some shoes. Macys
had a great shoe store for a girl like Mike and I just knew that a nice sit down make over
in full view of the store would be the ticket to remove the last vestiges of Mikes
manhood.
“Did you girls find suitable underwear for her?” “Oh
yes, in fact she is wearing her first bra and the clerk at Victoria’s Secret gave her
something special.” Mike was turning beet red. I leaned in real close and said
“Tell me what she gave you sweet heart.” “A ribbon” he said. One of
the girls whispered in my ear and told me that the girl at Victoria’s Secret and tied
a wide pink ribbon around Mikes penis and pulled it back between his legs, for a nice
girly panty line. She showed me how the ends of the ribbon were just visible at the hem of
his darling shorts. We took Mike to the make up counter and left him to the mercy of the
make up consultant while the girls and I had a coffee and watched the crowd form around
Mike and the make up girls.
With in thirty minutes Mike was finished and the girls and I could
not believe the transformation that had taken place. Mike was lovely, he was no longer a
boy even the girls who had teased him so much seemed to accept him as a girl. They hugged
him and held his hand as we all went upstairs to the shoe shop. The girls had engaged him
in the secret world of girl talk and their whispers and little girly asides were designed
to include him. I knew Mike was aware of this change and that he realized he had crossed a
line.
I watched as Mike and his new group of girlfriends squealed in
delight at the adorable cross strap sandals Mike was trying on. I saw the disbelief in
Mike’s eyes as he heard his own words “Sis can I wear them home, please.”
“Sure sweetie but we need to get you some nice school shoes too.” The group of
girls ran to the next display and I could see that my little brother was in a discussion
with his friends about the merits of a pair of clunky-soled Mary Jane's as opposed to the
burgundy loafers. “Honey get them both.” “Oh sis you are the best.” Mikey was now a girl and the enormity of his new
situation was just beginning to hit home. My little sister had a problem.

We were visiting my Aunt Janet and some other relatives over in Pennsylvania. Seemed like we never visited them; at least, I could never remember being in Harrisburg before.

 We saw my Uncle Harold that day. Only time I ever saw the old man, he died when I was 13. He took an instant liking to me though. He didn't like anyone, that old man, but he liked me. My brother and sister were jealous when Uncle Harold gave me a brand new Baseball. It was so big to me at the time...I couldn't even hold it right in my hand.

 We ended up staying a bit later than planned. It's a three hour drive from Harrisburg to Pittsburgh, and we were planning to go there, spend part of the day, and drive back to Pittsburgh where we were visiting other relatives, my Grandma, in particular.

 First we were just there through dinner. Then it came time for supper. "You CAN'T leave now, and drive all that way hungry, Junior," they said to Dad.

 They always called Dad Junior, since he was named after his Daddy. I wondered since I was named after my Daddy, should I be called "Third"?

Grandaddy was dead anyway, long before I was born. Sometimes I wished I knew him. But then Daddy always said he was drunk a lot, and mean often. Maybe it was better not to have met the man. Daddy still loved him though, I could tell.

 "I can drive hungry," my Dad informed my Aunt. "But what about your kids, Junior? I bet they want to eat, don't you kids?" My siblings and I gave Dad the "Bambi Eyes". For once they worked. Sometimes they worked, even on Dad. Mom was easier.

 We stayed for supper. We stayed for desert. And then my sister and I played with our little Cousin, Shannon. She was Aunt Janet's Granddaughter, really our third cousin. She was also spoiled rotten. Cried if she didn't get her way. She got her way a lot.

 My brother sat at the table and talked with the men. I don't think he enjoyed it much. It didn't LOOK like much fun, just sitting there and talking. He would have had more fun playing marbles with us. But, that's what you gotta do when you grow up, I guess.

 It was getting near night. We ran outside and caught fireflies. "Glowbugs" we called them. Every once in awhile you would catch
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