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Mommy's Darling 2: Playing Dressup free porn video
Mommy's Darling 2: Playing Dress Up - By Billie Lovelace
At twelve, I was deeply conflicted. On the one hand, I was a normal
boy. At school I liked sports, roughhousing, and teasing girls. On the
other hand, mother hated masculine aggressiveness. So at home I was
more girlish. I played the piano, did housework, and spent hours with
mother -- brushing her hair, polishing her nails, and helping her in
and out of her high heels. It was so confusing. I wanted to be like
other boys. And I wanted to please mother. But it seemed I couldn't do
both.
From time to time mother would coax me into wearing lipstick, rouge,
and eye shadow. She'd call me "mommy's darling" and add earrings and a
necklace. Then she'd kiss me and fondle my nipples. She was never nicer
to me -- never more affectionate and approving -- than when I was like
a girl.
Still, I was approaching puberty and my testosterone level was
increasing. Though I was able to repress its effects at home, school
was another matter. It was as if all my masculine aggressiveness had
been pent up and released at school. I fought with other boys and was
constantly getting into trouble. Once mother got a telephone call from
the principal informing her that I was among a group of boys who had
been teasing and harassing girls -- lifting their dresses, pinching
their bottoms, and touching their bosoms.
Mother was furious! When I got home she told me I was grounded for a
month. If I didn't change my ways, she'd put me in a home for juvenile
delinquents. After this, she didn't say another word. She wouldn't
even look at me. This went on for one day, then two, then three, and
approaching a whole week.
I felt terrible. Mother's silence - her refusing even to look at me, as
if my mere image hurt her eyes - was worse than physical punishment. I
desperately longed to please her, to once again have her smile at me
and hug me and kiss me and make me feel loved. But her stony silence
continued - as did my misery.
Then one day, when I returned from school, mother called me into her
bedroom. It was the first time she had spoken to me in a week. Feeling
like a huge weight had been lifted from my shoulders, I bounded up the
stairs. When I entered her room I discovered she wasn't alone. Mother
was standing up. Seated at her vanity was her friend Margie. Both were
wearing heavy makeup, form-fitting sweaters and skirts, and ultra-high
heels.
"Come here, dear," said mother with an inviting smile. She gave me a
warm maternal hug. "Margie and I were thinking, sweetie, how much fun
it would be to help you play dress up. You'd like that, wouldn't you
dear? Playing dress up in mommy's pretty clothes? Wearing lipstick and
perfume and jewelry and high heels? Learning to sit and walk like a
lady? Learning to curtsey and serve as our maid? You'd like that,
wouldn't you? It would make mommy so happy to see you play dress up in
her pretty clothes. And Margie too."
I was trapped. After seven days of silence and disapproval, I
desperately wanted to please mother and regain her love and affection.
At this point I'd do anything she asked -- and she knew it.
The thing that really got me, though, was that when mother first coaxed
me into wearing lipstick she said it would be a little secret between
us. But now she was bringing Margie into it! It was humiliating enough
to play dress up in mother's pretty clothes. It was especially
humiliating to have to do it in front of Margie.
For years I'd had a crush on Margie. In the last year or two I'd even
started dreaming about her. She was incredibly sexy. Underneath her
form-fitting dresses and sweaters Margie wore what were called "bullet"
bras. They accentuated her cleavage and made her large, intimidating
breasts look like missiles. I couldn't get her out of my mind. Recently
she seemed to be teasing me -- making her bosom jiggle and shake as she
minced about in high heels and a tight skirt. Then she'd look for the
telltale bulge in my trousers and give me a knowing wink and a smile.
Mother was waiting for my answer -- and not patiently. She placed a
finger under my chin and lifted it so my eyes met hers. Her stern glare
scared me. "I asked you a question!" she snapped. "And I expect an
answer. Now, do you want to play dress up for Margie and me, or not?"
Desperate for maternal love and approval, I knew what I had to say.
"Uh, uh, um, yes, mom, uh, I'm sorry, mom." I stammered. "Yes, I'd like
to play dress up with you and Margie. Uhmmm, and uh, uh, uh, pretend
I'm a girl and serve as your maid. I'd more than like it -- I'd love
it!"
The women looked at each other and smiled. They took me to mother's
closet and removed all my clothing. Then they looked me up and down. It
was so humiliating, standing in the buff before two well-dressed,
heavily made-up and perfumed women who towered over me in sky-high
heels -- especially as they scrutinized my naked body.
Margie looked at my manhood and smirked. "You know, sweetie," she said,
"I've never seen one that small -- even on boys younger than you. You
don't want to let the girls see it, honey. It's too teeny. They'll
just laugh and tease you about it -- and make you feel bad. A pee wee
like that'll never satisfy a lady. It's too small. Your mother's right,
dear, maybe you should have been a girl."
Mother and Margie then began dressing me up. They had a happy, laughing
time helping a young male into bras, garter belts, nylons, and high
heels. Though I wouldn't admit it, I loved the touch of their hands
and the silky feel of the pretty lingerie. I tingled with excitement as
the silky caress of satin and lace brought out the more feminine side
of my personality.
Still, I had mixed feelings. After all, I was a boy and boys aren't
supposed to turn on to wearing their mother's pretty clothes. But there
was a growing heaviness in my groin as I struggled to keep my balance
in mother's high heels. "Look how his pee wee responds to lingerie,"
Margie said to my mother. "Small as it is, it's getting a bit bigger.
Must be he likes dressing up as a glamour girl. Don't ever let him tell
you otherwise. The body doesn't lie. Deep down our little ruffian isn't
so macho after all!"
They added lipstick, rouge and eye liner; then clip-on ear rings, and
bracelets, perfume, and a wig. Then they taught me to walk like a lady
in heels. At first I felt like a toddler clinging to his mother and
another big, bosomy woman as he tentatively takes his first steps.
"Tiny steps, dear," Margie said. "Shorten your stride. You can't walk
like a boy in heels. You've got to be dainty and ladylike. Put one
foot right in front of the other -- and put your toe down first, then
your heel. Mincing ladylike steps, now. And swing your hips -- like
mommy and I do. Be sexy, sweetie. Imagine you're a woman. Walk like we
do. Release your inner female."
I took her advice. I pictured Margie's sexy walk and tried to imitate
it. I pulled back my shoulders, thrust out my chest, and seductively
wriggled my hips. Before long it was starting to work. I was girlishly
mincing about without any help. Granted, I wasn't nearly as graceful as
mother and Margie. I was tottering a bit, but I wasn't falling down. I
was making progress and they assured me that with practice I'd get even
better. If I kept at it, Margie said, I'd soon be effortlessly mincing
about 5- or 6-inch stilettos, just like mother and herself.
Dressing and walking like a woman was now making me feel like one --
gentle, delicate, sweet, submissive, and oh so eager to please. I loved
the sound -- the sexy click-clack-click -- of my high heels as they
struck the floor. I nearly swooned at the sibilant swish of my
stocking-sheathed thighs as they seductively caressed each other with
each mincing step. I liked the tug of my bra straps and garters
against my skin as I moved, as well as the silky caress of lingerie on
my breasts and my "pee wee."
But nothing thrilled me more than the broad smiles and approving words
of mother and Margie as they watched me girlishly mince about in
makeup, lingerie, and heels. "That's it, darling." "You're so pretty."
"What a sweet little boy. I could just eat you up." "You're too pretty
for a boy, dear, you really should have been a girl." "You're so nice
as a girl, dear. Much more lovable than as a boy." "Don't you wish you
were a girl, honey? I do. We'd have so much fun if you were a girl."
Mother had never been so genuinely affectionate and approving. For the
first time in a long time I felt she really loved me. And I so
desperately wanted to please her and have her love me and kiss me and
hug me and call me her darling.
After this I was putty in their hands. They made me model my pretty
outfit for them and practice a number of ultra-feminine gestures and
mannerisms. I learned how to carry a purse and sit and cross my legs
like a lady. Then they taught me to curtsey and serve as their maid.
They smiled with approval and praised me for being so sweet as I
performed a delicate little curtsey and served them wine and cheese.
"Isn't this fun, darling?" mother asked after I'd picked up the dishes
and taken them to the kitchen. "Don't you just love playing dress up
and serving as mommy's maid?"
Once again I knew what I had to say, whether I liked it or not. But the
strange thing was that I was really beginning to like it -- both for
the tingling in my groin and for mother's affection and approval.
I curtsied and said, "Yes, mom, I just love it."
"Love what?" Margie asked.
"I love playing dress up and serving as mommy's maid."
Beaming with pride, mother took me into her arms and kissed and
caressed me and told me how pretty I looked. Then Margie did the same.
It's humiliating for a male to be dressed and caressed as a female for
the amusement of women. It's also exquisitely erotic. I was thrilled as
their roaming hands intimately found their way into my lacy bra and
panties. And I never got over it.
That night, as I lay in my bed, I worried about what Margie had said
about my penis. Maybe it really was too small. Maybe I should have been
a girl. Margie and mother seemed to think so. And maybe being a girl
wasn't so bad. Mommy and Margie made me feel sooooo good as a girl. But
even a boy with a small one -- a "pee wee," as Margie called it -- is
still a boy. Isn't he?
In fact, it was only years later that I realized that Margie was
deliberately planting seeds of doubt. She was hoping I'd feel so shy
and inadequate as a man -- so afraid of being ridiculed for my "pee
wee" -- I'd never make advances to women. And she was largely
successful. Though I've since learned I have a normal sized penis, I
still feel like a boy -- a small, submissive, feminine boy -- when I'm
with a good-looking, glamorous woman in spike-heeled shoes. The lessons
of childhood -- even the false ones -- are hard to shake.
To be continued
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- 13.12.2021
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