Valentines
By Cheryl Lynn
This is a work of fiction and a follow up of my Eve stories. Please read
them before this as it will make for a better story. I have resurrected
and old character that I loved, Thelma Vitner from "A Christmas Story,"
which I thoroughly enjoyed. It may be downloaded for personal pleasure
all other use prohibited unless approved by the author. If you do not
enjoy forced feminization and humiliation, do not read. Again, this
story is not for the squeamish and sensitive reader. You have been
warned. Comments appreciated at
[email protected].
Valentines
Ever since Halloween Harold's life took a downward spiral. The holidays
had seen his manhood devastated by a series of unwanted events. First he
was tattooed then festooned into a fake vagina and artificial breasts.
The tattoos would never come off and the prosthetics he was told would
stay attached at least three months. Then for New Year's Eve he was
abused by four boys.
His only good break came the first week of the New Year, when his mother
discovered that nail polish remover would dissolve the glue holding the
prosthetics to his body. The relief he felt knowing that he wouldn't
have to go to school with those awful attachments was palatable.
Watching his mother remove them, however, had been traumatic. The fact
that he could now masturbate was a great relief. His mother had also
signed him up for therapy sessions after his ill fated Halloween
experience.
His mother, a single parent, worked as an assistant HR director in a
small company. As such her benefits package was small and health care
coverage limited. She could only afford to send her child to see his
therapist once a month. She was shocked and appalled when he came home
late Halloween night when she discovered what had happened. When that
was followed up by his Christmas antics, she was beginning to wonder
whether or not her son's adventures were actually forced upon him. If
she had known what he did New Year's Eve, she would have had serious
doubts.
She had no delusions about her son. He was a wimp, had been all his
life, and his few friends were definitely of questionable character.
They were Goth's and in her mind, no man, no real man would wear
lipstick and eye makeup even if it was black. So when her son showed up
tattooed and reeking of alcohol and sex at Halloween, she wasn't
altogether surprised. Hanging around a bunch of weird guys that wore
makeup was bound to wear off on her wimpy son. She also knew that he had
a habit of stretching the truth.
It had been almost impossible to get a well qualified therapist to see
him during the holidays but managed to find one who would see him. Her
name was Thelma Vitner PhD. She was a tall severe looking black haired
woman in her mid-to-late forties. She wore her hair in a tight bun
fastened to the back of her head, a beak like nose and thin lips. Her
eyes were a deep blue, cold and imposing like an iceberg. She dressed
conservatively, usually in black, navy or grey business pants suits with
starched white cotton blouses. She had a very commanding presents and
Harold's mother was impressed upon meeting her.
"This woman knew what she was doing," his mother thought as soon as they
met. When Thelma told her that she had extensive experience with, as she
put it, "delicate boys," and sponsored a summer camp for kids just like
him, she was sold.
"Harold, I want you to go with Doctor Vitner and tell her everything
that happened. You can trust her and I expect you to tell her nothing
but the truth," she instructed.
Harold was intimidated by the doctor but reluctantly followed her into
her therapy room. She told him that every thing he said to her would be
held in the strictest of confidence and even a court order couldn't make
her say anything. He felt better hearing that but still felt very small
in her presents. He felt like a little kid being sent to see the
principal.
After the first session Dr. Vitner told his mother privately that Harold
had some major issues to deal with and that he needed to see her every
week after the holidays. When his mother said she couldn't afford to
send him in weekly, Dr. Vitner replied that she would only charge what
the insurance would pay. Greatly relieved, she happily agreed to put
Harold under her care.
As they left the office, his mother heaved a sigh of relief. "That woman
is heaven sent. If anyone can help my Harold, she certainly can," she
thought.
Thelma sat back in her black leather chair with a big smile. "I haven't
had a sissy to work on in ages. This one is going to be so much fun
since most of the groundwork has already been laid. He obviously hates
everything that happened and that's the challenge. Those tattoos were
marvelous touches. I might have to consider doing the same to my future
clients," she thought.
Ooo
Thelma sat in the shadows in a back corner of the room. The New Year's
Eve party was getting into full swing. Mrs. Dalmatian and her precocious
little boy, Delbert, had just left her table. Across the room Harold sat
wearing his little girl costume looking miserable. Thelma was all smiles
as she gathered up her things and left.
"Oh what a wonderful way to bring in the New Year," she thought walking
to her car. "That Mrs. Dalmatian is such a prude and so malleable.
She'll see to it that Harold gets introduced to those young men. I can't
wait until our next session to find out what he has to tell me. Not only
that but I think it will only be a matter of time before I get my hands
on little Delbert. With that curly brown hair of his, I bet he will make
a lovely sissy dolly for his mother."
Ooo
Harold was in Thelma's office Thursday after New Year's Day. He was
lying down on her leather couch crying as he described what had happened
at the party. He denied wanting to participate in the party especially
as a diapered little girl. He felt that his mother was humiliating him
with her stupid costume ideas. Every one of her costumes wound up
getting him into nothing but trouble he told her.
"Harold you have to stop blaming your poor mother. She only wanted to
have fun and putting on costume parties is a common event. Many families
do that during the holidays. You should be happy that your mother wanted
you to participate. What happened after you donned a costume was
circumstantial. You only have yourself to blame for putting yourself in
those situations. Like Christmas Eve, you knew as soon as you walked
into that house that there would be nothing but trouble. Yet, knowing
better, you aggravated the situation by not telling the truth about
yourself. Just like on Halloween, if you had simply told that biker you
were a guy before he took you off, nothing would have happened. You see
dear, it's your own fault," Thelma lectured.
"Bu....but....I...I didn't have time....I....I wasn't able to say anything," he
sobbed in response.
"Harold no matter what you say, deep down you know that's not true. If
we are going to get anywhere with your therapy, you have to be honest
with me and yourself. Now answer me either 'yes' or 'no' to the
following questions. I don't want to hear any 'buts' or other response,
understand," she said.
"Good, the first question, did you tell that biker you were a boy when
he accosted you at the store? No, okay, did you voluntarily drink booze
at that bar? Yes, alright. Did you fight back or put up any real
resistance to what they did? That was a 'no,' correct. At the Community
Center or Christmas party, did you tell that young girl you were a boy?
No. Didn't you think, once you were in that house, there might be
trouble? Yes. When that girl put that prosthesis on, did you fight back?
Again, a no. Didn't that cabbie suggest that you were a call girl? Yes.
So if you knew he thought you to be a prostitute, wouldn't he want some
kind of sexual favor for the ride? Again a yes. At the New Year's Eve
party, weren't there a lot of people around? Yes. Do you think they
would have stopped those boys if you had yelled out or even asked for
help? Yes. Alright Harold that's enough for today. I'll see you next
week. Please tell your mother I would like to see her for a minute,
thank you," she said completing her test.
Harold's mother left the office shaking her head. The good doctor told
her that her son was in deep denial. To prove her point, she played back
the recording of her 'yes' and 'no' test.
"Every answer indicates that he knew what he was getting into Mrs.
Jacobs. Harold as much as he may deny it, voluntarily put himself in the
positions he found himself in. In every case, he didn't put up anything
but a token resistance. It is my opinion that Harold is a transsexual
and so bound by convention, cannot admit it, even to himself. How else
can you explain his sexual activities with men or why he allowed himself
to be put into those situations? Deep down, he wants to be the daughter
you never had Mrs. Jacobs. To prove my theory, I want you to exchange
all his male underwear for frilly nylon panties and camisoles, the
lacier and beribboned the better. At first I'm sure he will complain and
fight you but I guarantee by this time next week, you won't hear a peep
of complaint. You need to be firm. Bring out his inner self and this
will be the first step in curing your son. You must be firm dear. We
need to bring him along slowly. Let him rant and rave but insist that he
wear his panties and camisoles. You'll see, trust me," Thelma told her.
Somewhat dazed by what the doctor had said, Harold's mother agreed to
the treatment. She dropped him off at the house then left to do some
shopping. She had doubts about her son becoming her daughter. The more
she thought about it, the more she liked the idea. A daughter would be
so much easier to get along with.
"Well if my son wants to be a girl then who am I to argue? Doctor Vitner
obviously knows what she's talking about. After all, she is the expert.
If I were a boy, I think I would fight tooth and nail before I would
wear girl's clothing. I'll know shortly what kind of son I really have
according to the doctor. Come to think of it, Harold always bitterly
complained when I gave him feminine costumes but after a bit, he seemed
content," she thought as she pulled into the parking lot.
While Mrs. Jacobs was shopping, Harold sat in his room. His mind was
replaying what happened during his therapy visit. "I sounded like I
volunteered to do that shit. Why wouldn't she let me explain what
happened? You can't answer those questions with just a 'yes' or 'no.'
It's like asking someone if they are still beating their spouse. I'm
going to have to explain what happened at my next session. Oh well, she
gave me a CD to listen to, so I might as well play it. She said it would
ease my anxiety. Oh crud, it's one of those nature recordings. Let's
see, the first track is 'Summer Thunderstorm,' then 'Coastal Waves.'
Might as well listen to it, I don't have anything better to do."
When Mrs. Jacobs arrived home, she found Harold in his pajamas asleep.
The sound of a tropical rainstorm filled her ears. "That's strange. I
don't remember him having that CD. He always listens to that horrible
rap music," she thought.
She decided to let him sleep while she emptied his draws of every
stitch of underwear. Then she neatly folded his new lingerie, matching
the panty with the coordinating camisole. As she left the room, she
picked up his recently discarded boxers from the floor. Her next stop
was the laundry hamper.
Ooo
The next morning Harold pitched the expected tantrum. When his mother
walked into his room, panties and camisoles were scattered all over the
floor. He was ranting, demanding to know where his underwear disappeared
to. She let him carry on as she gathered up the scattered lingerie. She
dumped the pile of panties and camisoles on the bed.
"Harold that's enough! Now sit down and fold your underwear neatly and
put it back into your dresser," she demanded pointing to the pile of
clothing.
"Tha....that's not my stuff!" he snapped back.
"Oh yes it is and you will do as I say or I get my belt," she countered.
His mother had always intimidated him. She was a big woman and when she
took that attitude, he knew he couldn't win. Reluctantly he sat on the
bed and picked up a pair of yellow nylon brief cut panties between his
thumb and forefinger. He acted like the flimsy garment was going to bite
him. Then, as if a switch was flipped, he spread the garment our before
him. The nylon felt soft and smooth, semi-transparent with white rose
floral lace inserts at each hip. The waist band was a white floral
elasticized lace.
"These aren't that bad. They look similar to my briefs except so much
lighter and smoother. I don't wear briefs anymore but these look
comfortable. Maybe I should wear them just to see what they feel like.
No, I can't do that. These are for girls," he thought.
Harold's mother sat down beside him and took the panties from his
shaking hands. "Dear Doctor Vitner said you should wear these to help
you. I don't understand it all but she is the doctor and you will wear
these panties and camisoles until told otherwise. Now this pair is by
Vanity Fair and the style is called a brief. It goes with this yellow
camisole. Isn't it pretty? Notice the "V" lace insert at the bodice and
delicate eyelet lace on the straps. Each of your panties has a matching
camisole and it is important that you coordinate your lingerie. This is
how you fold each pair and put them into your drawer. Now you fold this
pair," she instructed handing him an emerald green camisole and panty.
Harold wanted to protest but only managed to grunt and mumble as he
neatly folded his lingerie. When he came to the last set, his mother
told him to put those on then get dressed while she made breakfast. They
were an iridescent purple with ivory lace detailing. The panties were a
high cut style with a rose lace front panel.
"Mother I don't want to wear these. They are for girls and I'm not a
girl," he weakly protested.
"It doesn't matter what you want Harold, its doctor's orders. I suggest
you take it up with her during your next visit," his mother said ending
any further argument.
Ooo
Over the next week Harold was very careful not to do anything that might
reveal that he was wearing panties and camisoles to school. He was
pretty much a loner at school but now he avoided his few friends
whenever possible. Initially he was very uncomfortable wearing panties.
Occasionally the crotch would slide and wedge between his balls and that
was painful. More often than not, they would ride up into his ass crack.
Those situations were not only uncomfortable but difficult to adjust in
class or in the halls. He made sure to wear his husky cut blue jeans or
cargo pants and sweatshirts to school. Towards the end of the week he
stopped complaining to his mother just like the doctor had said he
would.
In Dr. Vitner's office she had him drop his pants and pull up his
jersey. He was wearing a soft orange panty with white lace hemming and
matching top. "Harold there is nothing to be embarrassed about showing
me your pretty panties and camisole. I have seen your cute tattoos so
this shouldn't be that bad. So how do they feel? Are they as soft and
sensual as they look?" she said smiling.
"Eeeerrrrrr, ye....yeah....I guess so bu....but I would like my boxers and tee
back. These....this aint right," he stammered.
"Not right dear? How could they not be right? They're just underwear. So
what if they are pretty? You're not going around flashing your undies to
anybody are you? No, so what's the problem? No, you keep wearing them.
They will help you overcome your innate sexuality," she replied.
"If you say so but....but I won't like it," he mumbled as he pulled his
pants back up.
"That brings me to another change I want you to make. Those bulky rough
looking trousers and sweatshirts have got to go. They make you look like
somebody asking for trouble. You don't want to get into any more trouble
do you? No, I didn't think so. I'll talk to your mother in a bit and see
what we can do about your options. Now tell me, have you been listening
to your CD every night when you go to bed? Yes, that's a good boy. I
have another one I want you to start listening to. It's like the other
but the music is a little different. Okay, I think we are making
headway. Try to keep an open mind about the changes I am asking you to
make. In the long run you will thank me, no matter how strange they may
seem at the moment. Now please get your mother for me," she said.
"Mrs. Jacobs I have some good news. Harold is coming along better than I
though he would. How has he been at home?" the doctor asked.
"Doctor Vitner, you were right. When I brought home his new lingerie he
put up a fight but just like you said by the end of the week, not one
complaint. I'm still not sure what you are leading up to with his
treatment but must admit that you have been right so far. I'm glad to
hear that you think he is making progress," his mother replied.
"Like I said in our last meeting, Harold is suffering from deep seated
gender issues. To cure him we have to bring him along slowly, baby steps
if you wish. First we have him adjust to wearing frilly panties and
camisoles. If he doesn't rant and rave about having to wear such girlish
attire, we move on to the next step. Which brings me to that next step;
you need to replace all his bulky jeans, trousers and tops with more
feminine ones. I suggest low-ride girl's jeans in blue, pink and white.
He can wear the blue and white ones to classes. Save the pink for at
home wear for the time being. Get him some nice women's slacks that he
can wear anytime. For tops I would suggest some unisex sweaters and man
cut blouses. I know this is a lot to ask but here, this is a card from a
friend of mine. She has a lovely boutique and will give you a twenty
percent discount on whatever you decide to purchase. Lara has a lovely
range of clothing, lingerie and shoes. Speaking of shoes, get rid of
those ugly trainers he's wearing. Lara will help you there. Well, it
looks as if our time is up. Do you have any questions?" she stated.
"Doctor, I'm not so sure about all this. I deeply care for my son and
want what is best for him. Are you sure this will work? Are you sure he
has a gender issue? I know he was never very masculine but this?" his
mother asked.
"Yes, Mrs. Jacobs, I'm sure. If he had absolutely refused to wear his
panties and camisoles and gone commando, that would have proved me
wrong. He will probably raise a stink about his new clothing but like
last week, he'll stop complaining. Trust me, my methods work. You're
stressed by all this. I have a CD here that will help. Put it on when
you go to bed, it will help you sleep. See you next week," she declared.
Mrs. Jacobs looked at the card as they were leaving the doctor's office.
"Lara's Boutique, Everything the fashionable woman needs in one place,"
the card read. On the back of the card was the doctor's rubber stamped
name.
"Might as well give this place a try, I sure could use a twenty percent
discount," she thought.
"Lara honey, this is Thelma. I'm fine dear, just called to give you a
heads up. I have two new clients coming your way, a mother and her son.
Yes, the same deal as usual. This one, Harold, is older than my normal
clients and will have to be handled with kid gloves for a bit. I only
took him on because of unusual circumstances. He had a series of
accidents, quite involuntarily, that make him a viable subject. I'll
give you all the details later. Just be your doting adoring self for
now. He's just getting the basic starter set. I already have him in
panties and camisoles. No, it's a little too soon for bras and girdles,
maybe in a week or so. Alright, you know what to do. Call me when they
leave. Bye," she said.
Ooo
"What are we doing here?" Harold asked as they pulled into a space in
front of the boutique.
"Just stopping to get you some new pants and shirts like the doctor
ordered dear," she replied.
"Bu....but this is a girl's shop. I don't want to go in there!" he stated.
"Harold Jacobs this is where we are going and you will behave yourself.
Understand!" his mother snapped.
When she used his full name, Harold knew that she meant business.
Reluctantly he accompanied her into the shop. Seeing all the feminine
finery spread all about unnerved him and he broke out in a cold sweat.
"I so don't want to be in here much less anything they sell," he
thought.
"Hello, may I be of assistance? My name is Lara and this is my little
establishment," Lara said as Mrs. Jacobs and Harold entered her
boutique.
Lara was a statuesque red head with sparkling green eyes. She was
wearing a shimmering red satin peasant blouse and black wool pencil
skirt and three inch black patent leather heels. She stood about five
foot nine in her heels and had a very pretty face. Harold felt his penis
stiffen as she approached them. Red heads with green eyes had always
been a favorite fantasy of his. Lara was a dream come true.
"Yes Lara, Dr. Vitner sent us to see you about...about getting some new
pants and tops for my Harold here," Mrs. Jacobs said handing her the
doctor's card.
"Oh yes, the doctor and I are old friends. I have discreetly assisted
many of her clients. Let me lock the door so we can have some privacy.
What can I do for you today? Some nice jeans, slacks and tops, sure
follow me," she replied leading them into the back.
Harold stripped down to his panties and camisole. He was blushing,
holding his hands over his groin and not daring to look up. As soon as
he was told to strip, his erect penis immediately shriveled and he tried
to object.
"Mom, you can't expect me to take off my clothes. Not here, not in front
of her," he said almost in tears.
"Sweetie you don't have anything to be ashamed of. Not in here, not with
me. I have seen this and much more in the past. Why I think it's
wonderful of you to let your feminine side show. Not many men are that
brave or as handsome as you. You have to try on these lovely new things
your mother wants for you. I would be devastated if you left here with
clothing that didn't fit properly and what would that say about my
store? Here, try these lovely jeans on. Pretty please, do it for me. I
think you will look fantastic in them," Lara purred.
Harold hesitantly reached out and took the jeans from Lara. They were
made of stretch denim, in a low-rider hip hugging style with a slight
flare at the ankles. The four pockets were none functional and stitched
in. It buttoned in the front and had a short zipper. They fit his thin
frame like a second skin, smoothing out his crotch, separating and
uplifting his backside. He thought they were at least a size too small
but Lara said they were perfect. The blue and pink jeans were similar
except the pink jeans had red and green floral embroidery covering the
two back pockets.
Harold protested loudly over having to wear the pink jeans. It took all
of Lara's persuasion to get him to try them on. Even then he hesitated
until his mother assured him that he would only have to wear them in the
house. He was uncertain but tried them on.
"There's no way a guy would wear these. All I'm doing is trying them on.
It's not like we are actually going to buy them or me wear them," he
thought. He had second thoughts after he had them on and Lara gently
patted his ass and whispered in his ear that she thought he was very
hot.
He was fitted for three pairs of slacks in navy, grey and black. They
were all a soft satin lined wool blend with a low waist and flared legs.
Like the jeans, they had a button and short zipper front. The cuffed
hems flared at the ankles and they had no pockets. Each pair hugged his
crotch and ass in a tight embrace. He fussed but not nearly as strongly
as he had with the jeans.
Three sweaters with long sleeves and slightly scooped neckline were
tried on next. The cream colored wool sweater had three thin horizontal
black lines across the chest. The baby blue cotton sweater had a white
star decoration and the lavender one was a soft fuzzy angora. He thought
the last one was too feminine but Lara said he would look fabulous as
she rubbed her hands across his chest. The feeling of the soft material
moving across his chest as she rubbed made thoughts of rebellion
disappear.
He had only two problems with the three dress shirts. One was the fact
that they buttoned funny. Instead of being left to right, they buttoned
right to left. The other was the material. These were made of what Lara
called micro-fiber and much nicer than the starched cotton style. He had
to agree that they felt wonderful on his skin. The three shirts in
ivory, baby blue and a soft pale pink were added to the pile.
His trainers were replaced with a pair of cordovan square toed flats
with a one inch block heel and a tassel on the vamp. Since his new
slacks and jeans had no pockets, Lara sweet talked him into getting a
cordovan leather "man" bag with leather strap. Several narrow leather
belts were also purchased.
After they checked out, Lara handed Harold a leather belt. It had blue
turquoise cabochons in a floral silver setting spaced out along its
length. The buckle and tip were in floral etched silver.
"You were such a delight today Harold I want you to have this. It will
look lovely with your pink jeans. Promise you'll wear it for me," she
grinned.
Ooo
As Doctor Vitner predicted Harold raised a fuss for the first two days.
After that he only objected when his mother asked him to wear his cute
pink jeans. At school he caught a few derogatory comments but nothing
more than the usual shit he always received. Some of the girls noticed
that he was wearing girl's jeans, slacks and tops but just giggled. They
also noted very visible panty lines.
"That gay boy should really think about wearing thongs with those tight
pants," they would say amongst themselves then giggle.
Harold for his part thought his new clothing was androgynous or at least
that is what Lara had told him. Other than his pink jeans, he actually
believed her. Since none of the bullies said anything about his clothing
in their taunts, he went about school thinking nothing of it. He still
harbored misgivings about wearing panties and camisoles but the longer
he wore them the more comfortable they became.
In late January a pretty girl sat across from him in study hall. She was
in some of his classes and he had a mild crush on her. She was about his
size with long wavy chestnut colored hair. A little on the chubby side
but otherwise had a nice figure. Her name was Gwendolyn. She had a
reputation of being the school's "busy-body." She went out of her way to
snoop into everybody's business and intrude whether or not they
approved.
They sat and talked the entire hour with her doing most of the talking.
By the time they left study hall, she was convinced that the cute gay
guy needed her help. She decided that she would talk to him again to get
some more details but had already decided what she could do to help.
After school she met up with one of her best friends, George. He was a
tall muscular senior who played defensive end. What very few people knew
was that he was gay. Gwendolyn knew because they had been next door
neighbors for years and their families were close. She had tried to get
him to come out of the closet but being a football player he couldn't
afford to take the chance. All he ever wanted was to play in the NFL and
he believed if it got out that he was gay, would never get that
opportunity. She would date George off and on to keep up the pretense
that he liked girls.
When Harold said goodbye to Gwendolyn he was walking on air. It was the
first time in his life that a pretty girl actually talked to him as if
he were a real person. Not only that but when they parted, she kissed
him on the cheek. He had been so happy afterwards that he didn't put up
a fuss when his mother asked him to wear his pink jeans and lavender
sweater for his therapy session.
Thelma was more than happy to see him wearing the tight jeans and fluffy
sweater. She complimented him repeatedly for how nice he looked. He was
glad to get the compliment or at least he thought he was. He still was
not totally comfortable dressing this way. He mentioned that he didn't
like how tight they were in the crotch and she said she had a remedy for
that. She also mentioned that his sweater didn't look quite right but
she would take care of that as well. He was hoping that she would let
him go back to his baggy cargos and sweat shirts. He also mentioned his
meeting with Gwendolyn and how much he was looking forward being with
her.
"Oh dear, the last thing I need is for a girl to get interested in him.
I've got to find out more about this Gwendolyn," she thought.
As Mrs. Jacobs and Harold left their appointment, Thelma got on the
phone. "Yes, may I speak to Gwendolyn please? Hello Gwendolyn I'm Doctor
Vitner and I am Harold's therapist. He mentioned meeting you and seems
very keen on you. So I was wondering......" she began.
"Welcome back to my humble shop Mrs. Jacobs and oh, Harold that outfit
is just precious on you. I see that you wore the belt I gave you too.
How sweet. Come here dear and give Lara a great big hug," she greeted as
they walked in. By the time she broke the hug, he was beet red.
"So what can I do for you today?" she asked breaking the embrace and
stepping back.
"Harold is complaining about the tightness in the crotch of his new
pants. We were hoping that you could recommend something," his mother
responded.
"Sure I can fix that. Here let me lock the door and let's go in the
back," she said.
This time she had him strip down to his panties. His embarrassment was
even greater as his high-cut red panties revealed more than he wanted
them to. Lara hushed his complaint even before he said it.
"Harold those red panties are so cute and look marvelous. I wish more
young men were brave enough to wear such flattering styles," she said
giving him a peck on the cheek.
He stood dumbfounded, holding a red panty girdle with a bright red satin
diamond front panel embroidered with silver thread in a delicate fern
pattern. Several others in different colors were stacked on a nearby
table.
"Wh....what a...am I suppose to do with these?" he stammered. He knew what
they were and was confused as to why a boy would ever wear them.
"Put them on of course silly. It's either wear a panty girdle or a gaff
if you want to be comfortable in your new pants. If you would rather
have the gaff I could get some for you but you'll have to take off your
panties. I understand that dancer's gaffs can be painful. You will have
to tuck your manly equipment back up inside your body to wear one. I
wouldn't recommend them, that's why I brought the girdles. They will be
more comfortable. With a girdle all you have to do is push your
equipment back between your legs," she explained.
The thought of sticking his balls back up inside sent a shutter of
distaste running up his spine. It was very painful when that bull dyke
shoved them up back inside and he didn't want to experience that pain
again. Reluctantly he turned his back and stepped into the girdle. It
was a tight fit and he struggled to pull it into place.
"I....I think you...you got the wrong size. This thing is way too tight," he
complained.
"Oh no darling, it's a perfect fit," Lara admonished with a straight
face. It was difficult not to laugh as she looked at him. The girdle had
pulled his sex flat against his groin and the slightly padded bottom
gave him a round butt.
"Now that I've given you a nice girlish bottom, I need to get the top
looking as good," she thought before saying, "Now doesn't that seem more
comfortable than wearing a gaff? No, it's the right size. All you have
to do is sprinkle some talcum powder on the inside before you put them
on. They will slide up real easy then."
"Errrrr, I guess so," he replied not understanding why he had them on in
the first place.
"Why am I doing this? I shouldn't even be here. This thing is so tight
how can she say it's comfortable? The only choice I have is to wear this
or a dancer's gaff. I don't want to wear that," he thought. When they
left the store Harold had seven new girdles in almost every color of the
rainbow plus white, black and beige.
That night he played his new CD. It was a music montage of Celtic
themes. Many of the songs were hauntingly sweet. He thought he heard a
soft feminine voice in the background but dismissed the idea. In her
room, his mother listened to her new CD. It was also a music montage but
of 70's soft rock. She thought she heard a voice but paid no attention
to it. Her day had been exhausting.
Ooo
As the doctor predicted, Harold bitched and moaned about having to wear
the tight girdles. By the third day he didn't utter a single complaint.
However, he did begin complaining about how his shirts and sweaters
bunched up against his chest. Mrs. Jacobs took it all in stride. The
more she looked at him, the more she thought about how he would look in
a dress. When that thought passed through her mind, she shook her head
and went back to doing whatever it was she had been doing. Now, she
found herself really wondering what he'd look like with a better figure
and in dresses.
School started off wonderfully for Harold. Gwendolyn sat next to him in
study hall. This time she did it deliberately unlike the last time when
it had been the only seat available. The chatted the entire time and she
made his day when she asked him if he was going to the school
Valentine's Day dance. He never had the courage to ask a girl to any
dance, much less, have a girl ask him. With his heart skipping in
happiness, he said that he hadn't asked anyone yet.
"Oh goodie, I am so glad to hear that. I was hoping you weren't already
going with someone. Like, I mean, it's this Saturday night. Do you want
to go? You do. That's wonderful. I have the perfect outfit. Be at my
house no later than four so we can be at the dance by six," she said as
the bell rang, handing a piece of paper with her address on it.
He was a bit confused about having to meet her so early but didn't
worry. "I have a real date for the dance," he thought as he picked up
his things.
During his Friday therapy session, he would have talked the entire time
about Gwendolyn and his upcoming date. Dr. Vitner had to make him get
back on topic on more than one occasion. She was trying to find out how
he felt about his new girdles and if he was having any problems.
"How could I have any problems when Gwendolyn asked me to the dance?" he
replied.
"Please Harold I am very happy for you but let's get back to how you
feel about your new girdles. Don't they make your jeans and slacks fit
so much better? You don't mind wearing panties and camisoles?" she
asked.
"Oh I forgot I'm even wearing lingerie and girdles but....oh my gosh! I
can't wear that Saturday. I'm going to the Valentine's dance," he
replied beginning to panic.
"Settle down Harold. Don't upset yourself for no good reason. Are you
planning to rape that poor girl?" she responded.
"What! No! No, I would never do something like that! I'm not like that,"
he said raising his voice.
"You don't have to shout Harold. I can hear you perfectly well. My point
dear, is that, unless you take your clothes off, Gwendolyn will never
know. Now that we settled that, are you having any other problems?" she
stated.
"No, not really except for maybe my shirts seem to be bunching up on my
chest. It's a bit uncomfortable but I can live with it," he said visibly
relaxing.
"Have you given any thought to wearing a bra dear? It would make your
shirts hang much more naturally," she said watching him closely to see
his reaction.
"A bra? Boy's don't wear bras," he automatically responded.
"Are you sure you haven't given the idea some consideration? Tell me
honestly now. I won't be judgmental," she asked.
"Well, I have thought about wearing a bra for a couple of weeks but the
idea is just plain stupid. Isn't it? I'm a boy and boys don't wear
bras," he softly replied blushing.
"Harold you have worn bras before. So the idea isn't stupid. There is
nothing wrong in wearing a bra, millions of people do. If a bra makes
your shirts and sweaters look so much better, what is wrong with wearing
a bra? It's just another piece of clothing. I was talking to Lara the
other day and she said she thought you would look right handsome in a
bra," she replied.
"Lara she's pretty....did she really say that about me?" he responded.
"Harold I don't lie and if I said she said something, it's true. I think
she likes you. She keeps telling me how courageous you are for letting
your feminine side show through. Why don't you tell your mother to take
you there after our session? Ask her to buy you a couple of bras. If she
thinks the idea as stupid as you say, she won't do it. Just ask her and
see if what I'm telling you is true or not," she answered.
It wasn't until they were in the car that Harold asked her to take him
to Lara's boutique. When she asked him why, he hemmed and hawed a bit.
Finally, he admitted that he wanted to buy a bra to make his shirts fit
better. She gave him a funny little smile but agreed. That wasn't the
answer he was hoping for deep down in his gut but couldn't bring himself
to say no. When Lara gave him a big hug and kiss on the cheek any
further doubts were gone in the fluttering of his heart.
They left the store an hour later with seven new bras. They were all
underwire, slightly padded up-lift satin and lace confections in an "A"
cup. Lara made sure that the colors matched the girdles he had purchased
earlier. As he was leaving Lara made sure to give him another big hug,
kiss on the cheek and pat to his round butt.
Harold was very happy that they had stopped by. His penis was twitching
in the tight confines of his yellow girdle. Lara's exquisite perfume
lingered in his nostrils and he wasn't even thinking about the new
yellow and white lace bra he was wearing. When he went to bed he put on
his new CD and with a happy smile fell asleep. His last thought was,
"This was one great week. I can't wait to take Gwendolyn to the dance."
Ooo
Harold sat in his room trying to decide what he was going to wear over
to Gwendolyn's. On his bed were red nylon hip hugger panties, red
girdle, matching camisole and new red bra. The bra's silver embroidered
fern pattern on the cups matched that of the girdle's front panel.
"I don't want to wear this, especially on my first date with Gwendolyn,"
his gut told him but his mind said otherwise. His mind was telling him
that the lingerie would make him look sexy and appealing. With trembling
fingers, he pulled the panties up his smooth legs. He had kept shaving
them despite misgivings as after a few days, the stiff bristles would
itch to the point of distraction. The new hair growth would also snag on
the lining of his slacks.
He had no trouble hooking the bra behind his back after having to do it
so many times last month. With his lingerie on, he stepped into his
charcoal slacks. The feeling of the champagne colored lining going up
his legs sent a thrill of pleasure racing up his spine. He quickly
buttoned the white micro-fiber dress shirt and tied a thin black tie
around his neck. Sitting on the bed he pulled a pair of thin black socks
on and stepped into his shoes. Grabbing his black sport's jacket and his
man bag, he was ready to meet his date.
"Great, you're here. Come on we have lots to do before we go," she
greeted with an ear to ear smile.
She grasped his hand and led him into the house where she introduced him
to her mother. "Mom, this is that special boy I told you about, Harold.
Harold, meet my mom, Joyce," she said.
Joyce was an older version of Gwendolyn who greeted him with a bright
smile. "It's so nice to finally meet you Harold. Gwen has told me so
much about you. I can't begin to tell you how happy you are making our
families."
"Okay mom, we have a lot to do, do you mind?" Gwendolyn broke in.
Not waiting for an answer, she grabbed his hand again and led him into
her room. "Okay, strip," she ordered as she shut the door.
"Errrrr....wha....what? Strip? Right here, right now?" he stuttered in
confusion.
"Sure how else are you going to wear the outfit I picked out for you?
Don't worry you're going to look great when I finish with you," she
stated.
"Bu.....but I..." he started to say but she stopped him.
"Harold you don't have to pretend with me. I know all about your little
secret. I know you're shy and timid but I really want to help. Here let
me unbutton that shirt for you," she said as she pushed his jacket off
his shoulders.
Harold stood frozen in place. "She knows my secrets!" his mind screamed.
Before he could react, she had unbuttoned his shirt.
"What a lovely camisole and your bra is so pretty. What lovely
embroidery. I don't have anything nearly as nice. You're so lucky," she
said as she pulled the camisole down.
Harold began to hyperventilate as she began undoing his slacks.
"N....n...no.....yo....you. Stop...please...what are....are you doing?" he gasped.
"Calm down Harold. We have to do your hair and makeup first. Now, stop
gasping and calm down. I'm not going to do anything to hurt you. Kick
off those shoes and get out of those slacks," she firmly said.
In a daze Harold complied. His head was reeling and to make matters
worse, had no idea of what to do. A pretty girl had seen him in his
lingerie and was talking about hair and makeup. He was extremely
embarrassed but with his slacks around his ankles could do nothing. He
felt faint and was happy to sit on the padded cushion of her vanity
stool.
He was getting his breath back as she was combing out a lock of his
hair, coating it with setting gel and winding it on a hot roller. He
started to raise a hand to stop her. She swatted it away with her rat
tail comb.
"Harold, sit still and let me finish this. I promise you will like it.
Don't make me hit you again," she stated. Subdued for the moment, he let
her roll his long hair onto the rollers. He could feel the heat from the
rollers on his scalp and started to complain.
"Harold, like I said, sit still and behave. I know your secret and I
promise when I'm finished no one will recognize you. Promise, now behave
and let me do my thing," she firmly said.
With his hair in rollers, she began working on his face. His brows were
still thin from his previous adventures but she plucked a few stray ones
out. She worked on him steadily for an hour before she was satisfied
with his makeup. Harold had watched in dismay as his face was
transformed into that of a pretty young lady. She had done his eyes in
an Egyptian motif using thick black eyeliner extending out form the
corners, blending an iridescent blue into lavender into silver eye
shadows to bring out his eyes. A heavy coating of black mascara extended
the lashes. His lips were in a high gloss red plum color.
"Yeah, the eyes are a bit over the top but you can get away with it for
tonight. Here put these on," she said.
She handed him a pair of sheer black hose with floral lace welts to put
on. Seeing him stare blankly at them, she took one and rolled it into a
donut.
"It doesn't look you have worn stockings before so I'll show you how
with this one. You can do the other by yourself. I'm so glad you keep
your legs shaved. That's going to save us a lot of time. Just be careful
not to put a run in them. They're expensive," she said as she began
smoothing it up his leg. She folded up the edge of his girdle and
quickly fastened the hose to the garter tabs.
Harold couldn't believe what was happening and was powerless to stop
her. He wanted to stop all this but his body didn't want to obey his
wishes. When he felt the stocking going up his leg, the sensation was
almost overwhelming. Her hands, as they kneaded the nylon up his leg,
put goose bumps on his arms and a stiffy in his panties.
"Here slip these heels on while I get your dress," she ordered handing
him a pair of silver strappy three inch spike heeled shoes.
He had a bit of trouble fastening the very tiny hook into the shoe
buckle. Other than that he would have no trouble walking in them. After
all, he had walked a mile in similar ones Christmas Eve.
"Oh shoot, we have to do your nails before you can put on this dress.
Good thing a bought a new set of artificial ones the other day. Put your
hand up here on the vanity and let me get started," she said hooking the
dress on the back of the closet door.
Harold stared at the dress as she worked on his nails. The dress was
cream colored silk with a mandarin collar and straight mid-calf length
skirt. It was decorated at hem and bodice with brilliantly colored
embroidered oriental stylized birds and flowers.
She saw him looking at the dress, "I found that at the thrift store last
month, can you believe it? I practically stole it for only $18.00. No
telling how much that cost when new. It's a little big on me but I think
it will fit you beautifully. We're going to have to fill out that bra of
yours a bit though. Here give me your other hand, I'm finished with this
one so don't smear it," she said.
He looked down and saw that she had glued one inch oval extensions on
his fingers. They were painted in the same bright shinning reddish-
purple as his lipstick. He remembered to keep his fingers spread and
wave his hand from the wrist. His actions didn't go unnoticed by
Gwendolyn.
"Did I have him pegged for the fairy that he is or what. George will
fall head over heels in love with him. I just know it. They will make a
wonderful couple. I'm so glad I sat down by him in study hall. Talking
to his therapist made doing this so much easier. I still can't believe
she thought I might want to date him. Like that would ever happen. I had
some real doubts but after that talk, I couldn't wait," she thought as
she glued and polished.
With his nails dry, she slipped the dress over his head and zipped it up
the back. It fit him like a glove and looked adorable on his slim
figure. She removed the curlers and brushed out his hair into flowing
waves. Then fluffing out his bangs set everything in place with hair
spray. For a finishing touch, she pinned a black satin bow to the back
of his head.
"Okay you're done," she said as she sprayed him with a heady spice
scent.
A dazed and confused Harold sat on the bed as Gwendolyn got herself
ready. She stood right in front of him and stripped off her sweat suit.
He watched as she removed her green bra and bikini panties dumb struck.
She didn't show the least bit of embarrassment or hesitation as she
began to get ready. As far as she was concerned, he was just another
girl.
Gwendolyn was putting the finishing touches on him when Joyce called
them down to meet their dates. She had given Harold a strand of pearls
for his neck, pearl drop earrings and cabochon pearl ring. She also had
him put the makeup she used in his man bag along with a bottle of clear
nail polish in case he got a run, some tissues, a couple of tampons for
realism and a small bottle of the spice perfume.
When he heard her mother say their dates were there, he panicked again.
"Wha....what date? You're my date. What's going on?" he gasped.
"Oh get over it Harold! I fixed you up with my best friend George. You
probably already know him, he plays defensive end for out team. Look,
there is nothing to worry about, I swear. He's as gay as you are but is
afraid to let anyone know. When you told me you weren't going with
anybody, I decided to fix the two of you up. You make a beautiful girl
and he can date you without anyone being the wiser. We can't call you
Harold while you are dressed up like this. What's your fem name?" she
said.
He was so thunder struck by what she had told him that without thinking
he said, "Heather."
"That's a wonderful name, Heather, I really like it. Remember, it's
important that you act like a real girl. When we go to the little girl's
room, don't panic and sit to pee. If you can do that no one will know.
Come on Heather, we don't want to keep our dates waiting," she said
pulling him by the hand.
When they entered the living room, Joyce did a double take when she saw
Harold. "Oh my goodness, Har....errr..you look absolutely stunning, so
much prettier than that tom boy that arrived here," she said.
"Heather I want you to meet your date, George and this is my date
Jeremy," she said giving him a little push toward where he was standing.
George's hand completely engulfed Harold's much daintier one and his
smile broadened from ear to ear. Despite the heels, George was a good
head taller than Harold. His size and strength were intimidating. As
they stood looking at one another, Joyce picked up her digital camera
and began taking pictures. She had them all take several poses before
she was satisfied. In the last pose, she had them kiss their dates on
the cheek.
Ooo
The gym had been decorated in a pink and white motif. At the entrance
was a heart shaped arch constructed of pink and white balloons. As each
couple entered, the school year book photographer took their picture.
They found a table in a back corner with a red heart frilled with lace
as the center piece. Floating above it were several pink and white
balloons suspended by multi-colored ribbons. Two other couples were
already sitting there. Harold didn't know them but they were best
friends of Gwendolyn, George, and Jeremy. Harold was nervous as the
introductions were made.
He was more nervous in this environment than he had been during
Halloween, Christmas Eve or New Years. Then everybody involved knew that
he was a boy in a dress. Here, he would have to convince everyone that
he was a real girl. Talking and behaving like a girl was something he
never had to do before. He decided his only choice was to watch the
other girls and copy their actions as best he could.
What he didn't know was that all the girls knew his and George's
secrets. The girls all liked George and had decided to do everything
possible to make them a real couple. Now that they had met the
beautiful Heather, they were more determined than ever.
Shortly after the introductions were made, the guys all got up and went
to get them some punch and snacks. Once they were out of the way, the
girls descended on Harold with a vengeance. He was initially horrified
that they knew his secret. They assured him it was safe with them, safe
as long as he didn't do anything to hurt George. If that happened, they
would make sure the rest of his life was going to be pure hell. Once
they were satisfied Harold understood the consequences, they worked
together to give the "new" girl a cover story.
After discussing it, the girls came up with what they thought a good
cover. Heather just moved from the other side of town and lived with her
aunt, Mrs. Jacobs. Her parents had died in a horrible car accident. She
was going to the Catholic school, St. Thomas, and would transfer at the
start of the next six weeks period.
"So what do you think Heather? It's short, believable though a bit
melodramatic. At least you won't have to answer any questions about your
parents this way. If you have to, you can give out your real address and
phone number," Gwendolyn asked.
"I...I guess so. I don't want anyone to find out that I'm really a guy
under all this makeup and clothing. It'll do for tonight," he answered.
The band began playing as the boys came back. George asked Heather to
dance but refused saying he didn't know how. "That's alright, I'll teach
you. I'm a very good dancer," he said taking Harold's hand.
It was a slow song and George, pulling Harold's hands over his
shoulders, pressed his body in close. It wasn't long before Harold felt
George's manhood pressing against his thigh as they rubbed their bellies
together. He tried to back away but George only pulled him in tighter
and kissed him softly on the neck.
"Look Harold, you're not my idea of a perfect date. If I had my
druthers, you'd be dressed like me. Since we can't do it that way, we'll
have to do it this way. Now act like the adoring girlfriend or I'll get
pissed. If I have to put up with you in panties and dresses, I want you
to be super nice to me," he said giving him a firm pat on the bottom.
About half way through the dance, Harold was fatigued from all the
dancing and trying to keep up his feminine persona. The fast dances
weren't so bad. All he had to do was copy the style of the girls around
him, shaking his ass and shoulders. He was relieved when the girls all
went to the lady's room. While standing in the cue, several other girls
asked him who he was and where was he from. He replied, in as girlie a
voice as he could muster, the cover his friends had developed for him.
He wasn't use to standing in line just to use the bathroom and almost
peed on himself as he entered the stall. Pulling up a tight skirt,
pulling down a girdle and panties took time. When he finished his
business, he had to pull everything back into order.
Leaving the stall, Gwendolyn exited the one next to his. "Come on
Heather, let's grab a spot by the mirror and fix our makeup," she said.
Harold put his chunky man purse down on the counter and began searching
for his makeup. As he pulled out his compact, a tampon fell out and
rolled to the floor. He started to bend down and pick it up when
Gwendolyn whispered, "Stoop, don't bend." His movement caught the eye of
several girls waiting their turn at the counter. They just smiled
knowingly back at him.
They met the other two girls out in front of the bathroom. They all told
Harold he was doing fine but really needed some help in his mannerisms.
Several other girls joined them as they were about to go back to the
table. They all wanted to know who the new girl was. When he repeated
his cover story, they expressed their sympathies and said they couldn't
wait until he joined them at school.
Walking back to their table, Harold began to doubt the advisability of
his cover. They expected Heather to register and begin classes with them
in two weeks time. "Well it probably doesn't matter. After tonight, I
don't ever plan on seeing Heather again much less George. I can't
believe she got me into all this shit," he thought.
As the dance progressed to its end, George was getting more and more
intimate. He had his large hands squeezing Harold's round butt while
grinding his groin into his, kissing him on his neck, ears and lips
every chance he got during the slow songs. Harold didn't like it one bit
but could do nothing to stop him. He wasn't doing anything that the
other couples around him weren't doing.
He was happy when the dance ended. He was more than ready to get back to
Gwendolyn's and change back into his own clothing. Unfortunately, Jeremy
drove to a deserted spot and parked the car. It didn't Gwendolyn and
Jeremy to get into some serious petting. George didn't take much longer
to get Heather into a tight embrace and serious lip lock. The windows
were steamed opaque as the sound of zippers being undone filled the car.
Harold caught a glimpse of Gwendolyn with the top of her dress pulled
down, her "C" cups breasts revealed with her green bra shoved up above
them. His attention was forced back down as George grabbed him behind
the neck and pulled. Harold saw the large penis looming in front of his
face. He tried to pull back but George was too strong.
"Come on Heather, you been prick teasing me all night. Now it's time for
you to show some appreciation," he said loudly for Jeremy's sake. Then
more softly said, "Harold you had better do a good job or I'll be mad.
You don't ever want to see me mad."
It's not like Harold had never done this kind of thing before. He hated
every bit of it but by now knew exactly what a boy wanted. Slowly he
opened his lips and took the mushroom shaped head into his mouth. He ran
his tongue over it the sucked before swallowing more of its length. He
repeated that until he had every inch of that nine inch monster inside
his throat. With his lips pressed into George's thick pubic hair, he
gently pressed his teeth against the flesh and slowly drew back sucking
as he went and breathing. George let out a loud, "Hot damn!" after the
fifth time and erupted his seed into that delightful mouth. Harold
swallowed glad that it was over.
Instead of taking him back to Gwendolyn's, Harold was dropped off at his
house. He wanted to protest that he needed his own clothing back but
Gwendolyn said he could keep the dress as she looked meaningfully from
him over to Jeremy.
"Besides, George will be able to find your house again without having to
get directions. Now, be a good girl and get out. Come over to my house
after school Monday. You can pick up your things then. We're all tired
and want to go home," she said stressing the word "girl".
"OMG! How do I keep getting myself into these situations? How am I going
to explain all this to mother? Damn, I hate Valentines Day," he thought
as he walked up the drive to his front door.