A mother discovers her son dressing up in her clothes

This story is written by an adult fantasy.
I really had been expecting to be shopping most of the
morning, but I got to the mall and miracle of miracles,
not only did I find a place to park close in, the mall
wasn’t at all as crowded as I had expected. I got in
and picked up the few things I needed, and headed home.
One of the things I had to get was a couple of new
bras. It just seemed that the elastic in the ones I had
were wearing out. I sort of calked it up to their being
more cheaply made, every thing was any more it seemed,
being made in China or wherever.

I pulled into the drive and I didn’t open the garage,
since I was going to have to pick up my daughter
Christy from cheerleader practice later that afternoon,
so there wasn’t much point in putting the car away. I
grabbed the shopping bags from the back seat and went
into the house going in the kitchen door. The house was
quiet and I thought that I was alone, Christy being at
practice and our twelve year old boy had told me he was
going to a friend’s house.

I breezed through the kitchen and up the stairs and as
I got to my bedroom, I stopped. The door was shut. I
never shut the door if I’m not in my room and I though
that this was very odd. I set down my packages and
slowly opened the door, not really knowing what to
expect. What I found, was my son, dressed in my
clothes, skirt, blouse, heels, sitting at my dressing
table, applying lipstick to his lips.

He saw me immediately in the mirror and jumped up,
knocking over the dressing table bench. He was
stammering and was a beet, beet red with embarrassment.
Lord knows I was at a loss for words, but I had to say
something. For want of anything better to say, I told
him to pick the bench and sit down. I went out into the
hallway and retrieved my shopping bags. I put them on
the bed and then sat down on the edge of the bed facing
my son.

“How long have you been doing this Bobby? I asked.

“Um, well… for awhile.” He mumbled.

“You like wearing women’s clothes?” and felt
immediately stupid for such a dumb question. Not
waiting for an answer, I said, “Stand up and let me see

He stood, awkward and a little unsteady in the heels,
but, I had to admit, he made a fairly cute girl. I had
him turn and his legs I noticed were shaved and
passably shapely in nylons, and he had a nice little

“Lift your skirt,” I said in a tone more stern than I’d
spoken to him before.

“But Mom…”

“You lift up that skirt, or I’ll do it for you.”

Hesitantly, but by the tone of my voice knowing that he
had no choice, he reached down and pulled up the hem of
his skirt, stopping about mid thigh.

“All the way.” I said. And he continued, exposing
panties and garter belt. He had good taste in lingerie,
he’d chosen a pair of sheer black bikini’s and matching
lace garter belt and lace topped black stockings, all
mostly new and expensive. It was the kind of “hither
come fuck me” ensemble that I wore when I knew I was
going to be having fun.

I noticed then that my little boy had an erection. His
cock, not very large, was stiff and straining the sheer
black nylon panties. I reached over and pulled the
panties down. Now he was standing there, panties about
his ankles, his little hard cock exposed. I saw that
not only had he shaved his legs, but he’d shaved his
genitals too.

Looking at him, scared, exposed, humiliated, I found my
self breathing hard, my heart was beating fast and I
could feel myself getting wet. The sight of his little
boy naked dick, surrounded as it was by my perfumed
lingerie was making me as hot and wet as I had ever
been. “Oh my God! I want to fuck my son.” I thought,
“What kind of mother am I?”

“Come here and sit next to me.” I said and patted the
bed beside me. When he did, I made him keep his skirt
hiked up so I could still see his little stiff cock.

“Mommy isn’t mad about you wearing girls clothes,
Sweetie, but Mommy is mad that you we wearing some of
my best clothes. You’ve stretched out my bras and I had
to buy new ones. Now, if you are going to dress as a
girl, then you are going to have to dress as I tell you
and in the clothes that I tell you, is that
understood?” All the while I was saying this my hand,
that had started out resting on his kneed and run up
the inside of his thigh and I had half turned and now
had his balls in my hand in a soft grip. He was
breathing hard and his little cock was twitching and I
could see the first drops of pre-cum.

I told him to sit still and not move. I went to the
bedside table and took a condom from the drawer. I
opened the package and unrolled it over his dick and
then cupping his balls in one hand and stoking him
lightly with the other, he came quickly with a
whimpering spasm and fell against me crying. A mother’s
tenderness rose up in me and I put my arm around his
shoulders and with the other hand milked his cock of
the last of his cum. As he sobbed, I asked softly, “Do
you want to be Mommy’s little girl?” He sniffled out a
yes, head down and his face red with shame.

“Well then,” I said, “let’s take these clothes off and
put you into something more appropriate.” I unbuttoned
the blouse and slipped it off his thin shoulders, and
unhook the black lace bra and slipped it off of him. I
ran my hand across his chest and gave his nipple sharp
little pinch and was rewarded with a moan of pleasure.
When I had him stripped, I told him to fold and put
away my clothes and when he was done, to stand there
and wait for me.

I went into Christy’s room and took a pair of cotton
panties from her drawer. It was an old pair with a
little flower print, and searching through her bras,
found her old training bra, now outgrown by two cup
sizes. A pair of white knee socks, a pink tee and a
little pleated skirt, finished the outfit I had in
mind, The only thing I didn’t have were the shoes.

I went into Bobby’s room and searched until I found his
penny loafers. Those would have to do for the moment. I
went back into my room and Bobby was standing there
naked just as he’d bee told. I sat him down at my
dressing table and with cream and tissues, cleaned of
the way too heavy make up he’d slathered on. Once I had
that off, I reapplied a little light foundation and
some mascara, then finished with a faint pink lip
gloss, explaining to him what and how I was doing this
and telling him that he was forbidden to use any more
make up that his unless I gave him permission, then I
had him dress in the clothes I’d picked out and from my
closet brought out a wig that I’d inherited form my
sister. A little brushing out and it was prefect.

I stuffed his little bra with a couple of pantyhose and
stepped back to admire my handiwork. He looked pretty
much like any preteen girls just beginning to bud out.
“Come on,” I said, “we have some shopping to do.” There
was panic in his eyes, but I grabbed his hand and
pulled him out the door, snatching up my purse as we
went. Then it was down the stairs, out the door and
into the car.

I backed out of the drive and headed back toward the
mall. Bobby was slouching down, but I told him to sit
up straight. I knew he was scared of being seen and
would be mortified if anyone he knew saw him. And
knowing this, knowing that I had complete power over
him, was turning me on. He would do anything now, and a
lot of possibilities entered my head all of which made
my cunt tingle.

When we got to the mall, I wasn’t so lucky as the first
time and had to park a distance from the entrance.
Bobby was being reluctant, not wanting to go into the
mall where he knew he’d likely run into friends from
school hanging out. I wasn’t in the mood since we had
only a little time before I had to pick up Christy, so
lifted up the back of his little skirt and gave him a
hard swat on the bottom.

“You listen to me! You straighten up and be a good girl
or I swear, Mommy is going to pull down your panties
right here and now and give you a spanking that you’ll
not soon forget.” I said it loud enough that that it
was over heard by a man a row of cars over and when I
glanced over he was smiling at me.

Bobby was aware of that too and realized that I was
serious and that having his bottom tanned in public
would be far worse than what ever might befall him in
the mall. We walked on and entered the mall, I had to
tell him several times to straighten up and not slouch
and lift up his head. The first shop we hit was the
shoe store.

I told the clerk that I needed to get my “niece” a few
pairs of shoes and we spent some time on picking out a
pair of flats and a pair of Mary Janes and a pair of
heels with a demure one inch heel which she and I
agreed was the best for a young girl to start out in.

Then, we went into a department store and we picked out
a selection of panties and bra’s, some sox; anklets,
knee highs and a couple pair of tights, stockings and a
garter belt and a couple of nighties. The clerk was
very nice and she helped fit Bobby’s new bras,
reassuring my Niece” that she would be filling out in
no time. Then we wandered over to the Junior Miss
department to picked out a couple of outfits.

After having Bobby try on and model several, I decided
on a simple school girl kind of outfit with pleated
skirt, white blouse and blazer, a more casual skirt and
blouse, a dress with A-line skirt. We stopped at the
make up counter and I had the girl there give Bobby a
make over and she was so happy to introduce this young
girl to the joys of make up. We bought a few things,
foundation and mascara, and eye shadow and liner and a
lipstick. The last thing we bought for “her” was a

Loaded with our purchases, we headed for the parking
lot. With luck the traffic would be with us and I’d be
on time to pick up Christy. As we were almost to the
mall doors, I ran into a neighbor who lives a few doors

“Elise!” she called.

“Mary. Hi. How are you?”

“Oh, good you know. Who is this?”

This is my niece, Sharon,” I extemporized, “My brothers
eldest who is going to be staying with us for a while.
Sharon say hello to Mrs. Walker.”

Bobby managed to get out a “Nice to meet you.”

“She’s very shy.” I said.

“Well Honey, that’s OK. You’ll have to come down and
visit me and we’ll just have a girls afternoon of it
and get to know each other.” Mary said to Bobby and
then look at me said, “Sweet little thing.”

I made my excuses that I had to run and pick up
Christy, promising that we girls would all get together
for and afternoon. As we were going out the doors a
group of middle school boys were coming in, some I
recognized as friends of Bobby’s. They gave him a look
but didn’t recognize him and we heard some “Hey
Baby…” kind of noises from them. I’d turned my son
into a little hottie.

We got to the car and Bobby began to panic.

“Mom, I can’t let Christy see me!” he cried.

“Why not Sweetie?”

“Cuz, well, she…”

“She’ll think you’re a little sissy right?”


“Well, Honey, you are a little sissy. You are Mommy’s
little sissy girl. And you do want to be Mommy’s little
girl, don’t you?” I asked.

“Oh yes Mommy, I do.” He piped up.

“I like it when you call me Mommy. I think you are
going to turn out to be a sweet little girl. Yes, your
sister is likely going to tease you, but I think that
she’ll see having a little sissy sister around will
have its benefits for her too.”

“What… what do you mean Mom?”

“You know what we did on the bed? How Mommy made her
little girl cum? Didn’t that feel good?”

“Yes Mommy.” he replied, blushing slightly, sight of
which caused a rush of lust in me.

“You’d like Mommy to make you feel good again, yes?”

“Yes Mommy; please.”

“Such a polite little girl, Mommy likes that. Well,
just as Mommy makes her little girl feel good, Mommy
makes your sister feel good too. And your sister makes
Mommy feel good. Wouldn’t you like to make your Mommy
feel good?”

“Yes Mommy.”

“Of course you do, and Mommy is going to show you how.
And you and your sister and Mommy can all have great
fun together. Won’t that be nice?”

“Yes, Mommy. But Mommy…”

“Yes Honey?”

“What about Daddy?”

“Well, I can’t say he’s going to be pleased to lose a
son, but I don’t think that he will be too disappointed
when he realizes that he’s gained another daughter.”

“What do you mean, Mommy?”

“I’ll let your sister explain that one to you.” I said
with a laugh.

We got to the high school and as I pulled into the
parking lot by the gym to pick up Christy, I glanced at
the clock. Damn! I was almost fifteen minutes late and
I just wasn’t in the mood for a teenage girl snit over
“being abandoned again…” well, I did have a

I pulled up to the curb and there was Christy in her
little cheer girl outfit. She looked so cute and I had
to force the though of our most recent afternoon
together out of my mind. “God’ I thought, “My daughter
is having sex with both her parents, my son is
submissive transvestite… this family sure isn’t going
to make the cover of Good Housekeeping.”

Christy got into the car and it was all attitude with
“Thanks Mom for being on time.” And She turn around and
saw Bobbie in the back seat, “Who’s thi.. OH MY GOD!”
Whirlling around, “Mother, what the fuck is this?”

“Christy! Watch you language!”

“You don’t mind my language when you’re licking my
clit.” She replied petulantly.

“What ever! So what’s with Bobbie dressed in drag?”

“Well,” I said “Bobbie has decided that he’s more
comfortable being a girl than a boy.”

“That is just so weird.”

“It does take a bit of getting used to, but, doesn’t he
look cute? Just like a little doll. You used to love
playing with dolls and now you can play with a Bobbie.
It really will be fun to dress him up and of course we
can make him do anything we want, because, well because
he’s a little sissy.”

I could see a malicious little gleam developing in
Christy’s eye as the thought of having her brother
completely under her thumb developed in her mind.

“But what about Dad?’ she asked. “He’s going to flip.”

I turned and looked right at Christy, “I think that you
Father will come around when he realizes that he has
another daughter who’ll be willing and wager to suck
his cock.”

“Oh.” She said meekly. “You know about me and Daddy?”

I Laughed. “Of course I do Honey. And Daddy knows about
our little afternoons together too. We were talking
just the other day about how nice it would be for
someday the three of us to get together.” I could see
that Christy was at once shocked and intrigued with the
threesome idea. I’d let her think about it for awhile
and we’d talk about it later.

We finally made it home and I pulled into the drove.
“Christy, take your sissy brother upstairs and have him
put his new clothes away. You can look through your old
stuff too and give him the things that don’t fit you
any more.”

“Oh alright. C’mon you little queer.” Christy whined.
She got out of the car and opened the rear door and
grab her brothers had and pulled him out of his seat.
“Oh Jesus! Mother!” she yelled.

“What is it? And what did I tell you about your
language?” I said with not a little exasperation in my

“Well look!” she said, pointing to Bobbie. She had
lifted up Bobbies skirt so I could see that Bobbie
little cock was hard again.

“Oh dear.” I said. Seeing that something had to be
done, I went over and snatched Bobbies panties down to
his ankles. Grabbing him by his arm, I spun him around
and proceeded to spank his bare bottom. A half dozen
hard slaps were sufficient to bring him to tears and
his little prick shriveled.

“Bobbie”, I said to him sternly, “You are only to get
hard when you are told you can. I can’t stand you being
a naughty little girl and if you disobey me again I’ll
put you over my knee and paddle you with my hair brush
next time. Do you understand me?”

“Yes Mommy,” he sobbed.

I turned to Christy, who was smiling, haven taken
obvious delight in seeing her brother punished. “Take
you brother upstairs and you two get ready for dinner.”

As they started to go I called, “And Christy…” She
stopped, and turned, looking at me with the look that
only a teenage girl can give her mother. I gave her a
knowing smile and wink, “Make sure that your brother
behaves, won’t you?”

With that she gave me a smile and then turned and
pulling her brother after her, they headed upstairs.

I went into the kitchen then and began to get dinner
together and it wasn’t long before I heard the front
door open and in walked my husband. Walking over to
where I was standing at the counter, he cupped my butt
with one of his hands and giving me a kiss on the
cheek, he asked, “So Baby, what’s new?”

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