Hesitantly Doug entered the shop. He was nervous and was
sure everyone was watching him. But, as he looked around he
saw nobody paying any attention to him so he stepped farther into
the little boutique. It was a specialty shop and Doug was sure
he could get what he needed here. It had taken him a long time
to work up the courage to get this far and he wasn't going to
back down now.
"Can I help you?" said the pretty young sales clerk.
"Uh, well, I'd like to look around first," Doug responded.
"O.K., just call if you need any help, I'll be right over
here if you need anything." And the clerk turned and left him to
wander around the store by himself.
Doug's heart was pounding as he drifted among the isles of
clothing. He had always wanted to check out this tall girls shop
but he had been too afraid in the past. Now he was determined to
go through with it, and he had the hardest part over. He was in
the store now and nothing would stop him from completing what he
had set out to do today.
Towards the back of the store Doug found what he had been
looking for, the lingerie section. He quickly selected a Platex
Thank-Goodness-It-Fits brassier in size 38 nearly B. He looked
at the package and made sure it was the right bra. It was, and
it was in the color he wanted, black, so he turned to the next
isle.
He found the Platex panty girdles and picked out a thigh
high style and made sure it was size 7. With both foundation
boxes under his arm he looked around a little more and found some
pretty lace trimmed garter belts. He picked one out with red
satin trim and added that to the growing collection of packages.
Next he journeyed deeper into the store and began examining
the rack containing slips. He selected a black lace trimmed
nylon tricot slip in size 38 tall. After assuring himself that
it would fit properly he picked out a pair of sandalwood nylons
stockings and headed for the sales counter.
"Did you find everything you wanted?" Inquired the pretty
young girl.
Doug stammered for a second, cleared his throat and then
said, "Uh, I think so. Perhaps you could recommend a nice
inexpensive outfit to complete this ensemble."
The clerk looked up from the sales tickets she had been
checking and examined the items he had placed on the counter.
"Well, let's see now. Pretty underthings here deserve a pretty
dress. Did you want a skirt and blouse, or is a dress more in
line with what you had in mind?" she inquired.
"I really hadn't thought about that," Doug returned, "What
do you suggest?"
The clerk was making her way through the isles and Doug
followed close behind. He had left the other articles on the
counter and was startled when the girl turned and held a dress up
next to him and said, "This would look pretty with what you've
already picked out."
Doug turned red as she held the dress against his body. He
wanted to protest, but could not find the courage to deny what
the clerk had inferred. The clerk noticed his embarrassment and
tried to ease it somewhat, "Don't worry. We get lots of men in
here who like the items we sell. If it doesn't bother me, why
let it bother you."
He thought about it for a minute and felt a little better
with her confiding in him in such a frank manner. "Well, it's
just that I never, well..., I mean I never...,"he stammered.
"Don't worry about it. If you'd like, you can try
everything on in back. We have a special room and no one will
disturb you."
Doug couldn't believe what he was hearing. "Uh, are you
sure?"
She draped the dress over her arm and said, "Come on,
follow me." Then she turned and headed back to the counter and
picked up the other packages he had selected earlier. She
continued on to a curtain hanging at the back of the store and
held it open for him.
Doug stepped through and then the clerk entered and pointed
towards another door. "Right in there, no one will disturb you.
If you need any help, just press the little buzzer and I'll come
back and help however I can." With that she handed him the dress
and other articles, turned and left Doug standing there by
himself.
Hesitantly, he thought about it and then hurried to the
door. As he pulled the door open he was somewhat surprised to
find such a large dressing room. Inside he found that he could
bolt the door and he quickly did so. He crossed over to the
dressing table and laid the items down.
Doug looked around the room and found that in addition to
the dressing table, there was a stand with half a dozen different
wigs and another dressing table with all kinds of make up on it.
He quickly removed his clothing and hung them from a
hook next to the table. Standing there naked he began to
shake as he removed the lycra panty girdle from its box. He
had selected the thigh high type to help hide his maleness
and quickly pulled the garment from the box. Nervously he
put one foot into the panty and then rapidly slipped the
panty over his other foot. Before pulling the garment up he
pulled his testicles back between his legs and pressed his
thighs together to hold them there.
He then pulled the panties up and adjusted them to the
contours of his body. Next he removed the brassier from its
carton and noticed his hands were shaking badly. He had a little
difficulty fastening the clasps because of shakiness, but managed
to get them hooked properly.
He removed the slip from its hanger, pulled off the tags and
then slid it over his head. The feeling of constriction from the
bra and panty girdle gave him a sense of pleasure. The coolness
of silk against his body from the slip sent shudders of delight
throughout him.
Before trying on the dress he admired his own reflection in
the mirror and marveled at how well he could mimic the female
form. He was delighted with what he saw and then picked up the
dress from the table. After unzipping it full length, he stepped
into the dress and then adjusted the shoulders and bust to his
figure.
With difficulty he managed to get the zipper all the way
back up and was just admiring the fit when he heard a knock at
the door. He recognize the clerks voice when she said, "If
you're ready, I've picked out a couple of accessories that will
go very nicely with that outfit."
Doug was scared! He hadn't planned to try the things on in
the store. And now here he was completely dressed in the clothes
he had been wanting so long and someone was at the door. Slowly
he stepped over to the door and drew the bolt back.
The young clerk briskly entered the room and placed some
jewellery items on the table. "My but that's a pretty outfit.
I'll bet you'd really like to wear those things out of here."
Doug was too stunned. "I don't think that's possible. I'd
get into trouble for sure."
"Well listen," she continued, "I'll be closing the shop in a
few minutes and you can come by my place. Here, try a couple of
these wigs on and I'll be back in a few minutes." With that she
left Doug alone to ponder what had just happened.
He picked up the necklace she had left on the table and
fastened it around his neck. After slipping the bracelet on his
wrist he realized he had not tried on the nylons or garter belt
yet so he pulled up his dress and slip and fastened the flimsy
garment around his waist.
Doug removed the nylons from the container and gathered one
up in a ball and slowly fitted it to his leg. After hooking the
garters to it he began to put the other one on and was just
fastening it when the clerk returned. Since he had forgotten to
bolt the door after she had departed, she walked in as he was
fastening the other nylon.
"Here," she said as she crossed the room to him "always hook
the straps through your panties. That way if you need to take
your panties down, you don't have to undo everything." With that
she unhooked the garters and threaded the straps through Doug's
panty. After she had it properly adjusted she reattached it to
the nylon and saw that he was finishing the other nylon.
He quickly dropped the slip and smoothed the dress down as
the clerk selected a pretty auburn wig and removed it from its
stand. "Let's try this one," she said as she motioned for him to
set down in the chair in front of the dressing table.
Doug meekly obeyed and she expertly fitted the hair piece in
place. After adjusting the wig, she stepped back and allowed him
to see the full effect in the mirror. He could not believe what
his eyes saw. The reflection in the mirror was beautiful! Even
without make up the red head returning his gaze from the mirror
looked ravishing.
As the clerk picked up a stick of foundation make up she
said, "My name's Cindy. What's yours?"
"Doug," he responded quietly as she began smoothing the
foundation on his face and neck. Quickly and expertly she
blended the make up in with her finger tips and then selected a
light green eye shadow for his eyes.
"Green will go good with that wig," Cindy stated as she
brushed the light powder on his eyelids. "We don't want to
overdo it though. Here, see if you can apply this lipstick
properly," she said as she handed Doug a tube of rose petal lip
gloss.
Slowly and carefully he traced the outline of his lips with
the tube and then pressed his lips together. When he finished
Cindy was holding a small Kleenex for him to blot his lips
with. "Thanks," he said as he took the Kleenex and completed the
task.
Cindy picked up a brush and made minor adjustments to the
wig as she inquired, "Have you been doing this long?"
Doug answered tentatively, "Privately I've enjoyed dressing
as a woman for a couple of years now. But this is the first time
I've ever had the opportunity to share it with anyone else.
That's why I came to this boutique. I wanted to make sure I got
everything in the right size. I must admit, I was quite
surprised with how well you put me at ease in here."
"We get lots of guys in here that are into women's clothes,
but you're the first one I've ever given special attention to,"
she said.
Cindy finished with the brush and was satisfied with the
look. "One last thing, we'd better get some shoes for you.
Follow me and we'll try a couple pair on." She headed for the
door and Doug followed after taking one last look in the mirror.
Amazing he thought, absolutely amazing. He followed her out
the door and back to the store. Cindy was standing near the
shoe department and asked him what size shoe he wore. Doug told
her the male size he normally bought and she went over to a rack
and pulled a box down. "Here, let's try these," she said as she
opened the box and removed a pair of woven straw sandals.
Doug sat down and slipped the sandals on. It took him a
second to figure out how the straps laced around his ankle and
then he buckled them and stood back up. "Perfect," he said as he
admired them in the floor mirror.
"Come on then, let's go. I'll get your other things and put
them in a bag. You can change back if you want to at my place."
With that Cindy disappeared in the other room for a minute and
then reappeared with a boutique plastic bag in hand. Doug
followed her as she headed for the door and waited patiently
outside as she turned the key in the lock and dropped the keys in
her purse.
"I'm parked right around the corner. Let's go across the
street for a quick drink before we take off."
"Gee, I don't know if I'm ready for all this. Maybe we'd
better just get going," he said.
II
Doug woke from the dream covered with perspiration and with
a tremendous hard on. He was in his own bed and could sense his
wife's' body next to him. He thought about the dream and could
recall every detail as if he had really lived the experience. It
disturbed him that he had had the dream again. This was the
third time this week alone and each time it was the same.
If only he could see how the dream ended he thought. Or
better yet, if he could really experience it. Doug got up from
the damp bed and quietly padded out to the kitchen. As he
prepared the coffee pot for the morning ritual, he lit a
cigarette and pondered the dream again.
The aroma of caffeine invaded his nostrils and Doug snubbed
out the butt as he reached for a cup. While pouring the hot
liquid he heard Cindy stirring in the bedroom and knew she would
soon be joining him.
"Have that dream again?" Cindy inquired as she joined him at
the kitchen bar. She was the image of his perplexing nocturnal
adventure and he only nodded affirmatively as he avoided her
gaze. "Come on honey, talk about it. It might help if we can
work it out together. I love you dear."
"I don't understand it Cindy," he started, "Why am I having
this same reoccurring dream? What does it all mean?"
"Doug, I love you very much. Maybe if we actually acted out
the dream, it wouldn't bother you anymore." Cindy peered deeply
into his eyes questioningly as Doug turned toward her.
He considered her suggestion and then responded, "I really
don't know. We've been married for two years now and why does
something like this start affecting me so much? I'm no
homosexual and I've never had thoughts like this before. Why
now," he inquired.
"Look," Cindy began, "it's Friday and we have the weekend
ahead of us. Let's make reservations at a motel in town and just
get away from here for awhile. The change will be good for us.
And," she lingered for a minute, "perhaps we can explore this a
little farther."
Doug considered the idea and then stated, "I'll call from
work and make the arrangements. Maybe you're right." As he got
up from the bar and started for the bathroom to get ready for
work Cindy hugged him tightly and placed an affectionate kiss on
his ear lobe.
Doug put the dream from his mind and quickly showered.
Cindy was busy in the bedroom when he left for work and the rest
of the day was quite normal for him. During his lunch hour from
the parts department he worked in, he called and made the
reservations at a Holiday Inn on the outskirts of town. "Maybe
Cindy's' right," he muttered to himself as he hung up the phone.
Doug arrived home shortly after five o'clock to find Cindy
waiting in the living room with three suitcases setting next to
the door. "What's this?" he inquired.
"I hope you didn't forget to make reservations. These are
our bags, let's go." With that, Cindy grabbed one of the
traveling cases and headed out the door.
Half an hour later the two were climbing the carpeted stairs
to their room at the motel. As Doug placed the luggage on the
traveling stand Cindy darted into the bathroom and said, "I'll
get a bath ready for you and then call room service for a few
drinks while you relax and unwind from the day."
Doug nodded and absent mindedly flipped on the television
set. A few minutes later Cindy reappeared and informed him every
thing was ready. Entering the bathroom, he noticed she had drawn
a hot bubble bath for him and had placed his shaving gear on the
counter next to the sink. After removing his clothes and easing
into the foamy liquid, Doug heard her requesting a bottle of
champagne from room service.
Cindy came into the bathroom and sat on the edge of the tub.
She let her hand slip into the warm water and slowly swim its way
towards Doug's' naked thigh. Just as she made contact with his
groin they both heard a knock at the door. "Must be room
service," Cindy said as she stood and scooped up the clothing
Doug had dropped on the rack above the toilet.
Cindy had pulled the bathroom door shut when she opened the
door to the hallway to allow the bellhop to bring in the cart
with the champagne. After thanking the bellhop she handed him a
twenty dollar bill and said, "I'd really appreciate it if you
could dispose of these items immediately." With that she handed
the bellhop the clothing she had brought from the bathroom with
her.
The bellhop smiled quickly as he tucked the bill in his
pocket and took the articles she held in his direction. He then
disappeared as she closed the door behind him and locked the
door.
Cindy carried the champagne and two glasses back into the
bathroom and sat them on the floor next to the tub. She removed
her blouse and skirt and tossed them out onto the bed as she
lowered herself to edge of the tub again.
Doug admired her ample breast and the way they strained at
the skimpy brassier she was wearing. Cindy filled the glasses
with the bubbly liquid and then handed one to Doug. As he
started sipping the drink, Cindy picked up the razor from the
counter and lowered it into the tub. Doug looked at her
inquisitively as she reached into the water with her other hand
and grasped his ankle.
"Enjoy every minute of this, Doug. I love you and want you
to be as happy as I can make you." Cindy said as she slowly
began drawing the razor along his leg. Doug started to protest
but she merely handed him another glass of champagne and
continued with her task.
Moments later she had finished one leg and was busy with the
other while Doug helped himself to another drink. When she
stopped to admire her handiwork, she noticed he had dozed off and
was sleeping with his arms folded behind his head. Carefully and
ever so gently she began shaving his underarms and was able to
complete the task without awakening him. Satisfied that she had
done properly, she left Doug nap a little longer while she went
into the other room and set about arranging the rest of her
surprise for him.
Doug opened his eyes and felt Cindy massaging his flaccid
penis. The water was now tepid and most of the bubbles had
dissipated. "Boy, I must have really been tired. How long have
I been in here?" Doug asked.
"Not long, honey. It's a little past eight. We ought to
get dressed and go down to the lounge for something to eat. Come
on and I'll help you." Cindy stood and handed him a towel. Doug
quickly dried off and then followed her out of the bathroom.
Looking around the room, Doug was unable to find any of his
clothing. He picked up each suitcase and noticed they all felt
empty. "What'd you do with my things?" he inquired.
"Everything you wore in here is gone. I've packed enough
for us for the weekend." With that, Cindy handed Doug a pair of
pastel lycra spandex panties and watched the expression on his
face. Slowly the look of terror was replaced with a peaceful
smile as he reached out and took the garment from her hand.
Tentatively Doug placed one foot in the panty and then
quickly stepped into them with the other foot. As he began
pulling the slinky fabric up his body he felt a sense of urgency
compelling him onward.
After adjusting the hip huggers, Doug looked at Cindy and
noticed she was holding a matching brassier for him. He put out
his hands to accept the bra and Cindy threaded it over his hands
and up his arms. As he positioned the boned-underwired cups to
his chest, Cindy cinched the garment from behind and hooked the
clasps.
Doug admired her selection. The bra fit very comfortably.
It was a deep plunge, under wire affair with stretch straps and
lace trim everywhere. Before he could inspect the garment any
farther, Cindy was wrapping a combination garter belt, waist
cincher around his midsection.
It too, he noticed, matched the pastel panties and bra. On
each of the elastic garter straps was a small silky ribbon
hanging from a little ribbon bow. Cindy had finished hooking the
hooks and was trying to zip up the zipper. "You'll have to hold
your tummy in as much as possible. I got this a little tight in
order to give you a little better figure." She said.
Doug had a hard time believing what was happening, and, he
had an equally hard time holding his stomach in enough for Cindy
to get the girdle affair zipped up. But somehow she managed and
then stepped around in front of him.
She started threading the garter straps through his panties
and Doug was quick to follow suit with the other leg. After the
eight dangling straps were properly adjusted by Cindy, she handed
him a pair of smoke colored nylons and then went over to the
dresser.
Doug was busy sliding the smooth silk up his freshly shaven
legs and didn't notice Cindy removing the wig from a hat box. He
was enjoying the slick feeling the material produced against his
bare legs. As he donned the second nylon he became acutely
aware of the erection between his legs. The feel of slippery
legs, the under wire bra and the constriction of lycra spandex
panties were too much for him.
"I thought that might happen." Cindy said as she observed
Doug's predicament, "so I've got a little idea how to handle that
problem."
Cindy crossed the room to Doug and rolled his panties down.
She then stepped behind him and reached through his legs and
grabbed his testicles. As she tugged them back she forced his
rigid cock back and held it against the two smaller sacks. Next
she applied pieces of surgical tape to the head of his penis and
pressed the ends to his crotch. She put one more long piece of
tape across the length of his hard on and pressed the end of it
deep into his anus.
"O.k., now adjust your panties and I'll bet that'll take
care of it," she said.
Doug pulled the panties back up and smoothed them in place.
He couldn't help but admire the appearance of a feminine pubic
mound and glanced at Cindy. She was smiling at the effect of her
handiwork and said, "Here, put this slip on and we'll see what a
little make up will do." With that she handed him a dainty satin
slip of the same pastel color.
Doug quickly slid the slip over his head and let it drop
down his body. He liked the way the lace trim bodice draped
over his bra, and the way the cool, soft fabric felt. As he
smoothed the garment in place with his hands his body became
charged with a tingling sensation.
Cindy had him set in a chair beside the dressing table while
she sat on the edge of the bed and began by trimming his eye
brows with a small pair of tweezers. After she had thinned them
considerably she picked up a styling pencil and lightly filled
out a soft, feminine arch.
After completing the eyebrows, Cindy dabbed small amounts of
light aqua colored powder to the tops of his eyelids and then
blended it with a cotton swab. Next she applied a Cover Girl
foundation to his cheeks, forehead, chin and neck. She also
blended this with a cotton ball and then applied a light coating
of powder to the same areas.
When she was satisfied with the softness of the skin
texture, she applied a thin coating of blusher to his cheeks and
used her fingers to fade the edges of the blusher. Happy with
the effect she was creating, Cindy removed a mascara wand from
her make up case and applied a thin coat to Doug's eye lashes.
She sat back on the bed and admired her handiwork. "Damn,
you're pretty," she remarked. Doug turned towards the mirror and
gasped at how beautiful and womanly he had become. It was
difficult for him to imagine that beneath the reflection staring
back at him was really a man.
Cindy handed Doug a pair of silver clip on earrings to put
on while she fastened a matching silver necklace around his neck.
When she finished with the necklace she bent down and hooked a
smaller version of the necklace around his left ankle.
"Just a few more details and we'll be ready, honey." She
said as she produced a dark brown wig Doug immediately recognized
from her collection of wigs at home. She slipped the trusses
over his scalp and fitted it to his head. With a small styling
brush she teased a few curls into place and patted a few others
with the palm of her hand.
"After you have your dress on, we'll take care of your hands
and then we can go." Cindy then pulled a beige ruffled blouse
from the hangers she had previously hung in the closet and helped
Doug into the garment. As she buttoned the buttons in back, he
straightened the collar and fluffed up the ruffles in front.
Doug glanced in the mirror and noticed the ruffled blouse
created the illusion of a larger bust line than he actually had.
He turned back to find Cindy holding a tweed, straight skirt for
him to step into. He pulled the garment on and Cindy zipped and
fastened the clasps in back for him. As he reached under the
skirt to adjust his slip, Cindy retrieved the matching jacket
from another hanger and handed it to Doug.
After tucking his blouse into the skirt, Doug slipped into
the jacket and turned to admire himself in the mirror. Cindy
handed him a package and said, "Here, see if you can put these
plastic finger nails on while I get dressed." She then
disappeared into the bathroom while he tore open the package.
When he finished with the nails, Doug walked around the room
and enjoyed the feel of female garments swaying against his body.
The sensations were electric and he felt ecstatic. He was still
enjoying the slick nylon charge when Cindy stepped out of the
bathroom dressed equally as beautiful as he was.
She stepped into a pair of patent leather spiked heels and
said, "Perhaps you'd better wear these lower heeled slippers. It
takes a little getting used to walking around before you'll be
able to handle high heels." She then handed him a pair of beige
leather low heeled slippers and he quickly slipped them on his
nylon covered feet.
Doug stood before her; both the picture of felinity. She
stepped closer and hugged him tightly. They kissed passionately
and both could sense the arousal in the other. Cindy pulled away
from the embrace and said, "Now for the lipstick and we're ready
to go. You can carry this little purse for effect and I'll take
mine along with everything we'll need." She handed Doug a tube
of pale pink lipstick and watched as he traced it on his lips.
When he finished applying it, she gave him a small beige handbag
and he placed the lipstick in it.
She picked up her purse and opened the door. "Well, let's
go to the lounge and get something to eat. I'm famished." Doug
followed her out the door and stood in the hallway as she locked
the door.
Pangs of guilt and apprehension invaded him as another
couple appeared down the hall. Cindy saw the fear in his eyes
and quickly linked her arm in his. "Believe me darling, no one
but I know who, or what you really are. Come on, let's go."
III
Cindy led him down the hallway and could feel his sense of
confidence returning. The closer they got to the stairway, the
more she could tell he was loosening up and beginning to enjoy the
experience.
"I'll do the ordering as your voice may give you away." They
descended the stairs and crossed the lobby to the lounge. Doug
glanced about and noticed the clerks paid them no mind. A few
guest mingled in the lobby and they too paid no attention to the
two well dressed women headed for the lounge.
The hostess guided them through the dimly lit bar to a small
table near the rear of the lounge. Before departing she accepted
Cindy's order for drinks and then disappeared amid the tingle of
glasses and music from the band.
Soon their waitress delivered the drinks and Cindy selected
entrees from the menu for them both. Before their meal arrived,
the waitress brought another round of drinks and said, "The
gentlemen next to the bar hope you'll accept these with their
compliments." She nodded towards a table with two well dressed
business men and sat the glasses down.
Doug and Cindy both glanced toward the men. Cindy smiled
and tipped her glass in the air to the men and then turned back
to Doug. "See, I told you no one could tell but me."
Doug felt a little nervous and whispered to her, "What do we
do if someone try's to hit on us?"
"Honey, this is your fantasy. Enjoy it. Just do what ever
comes naturally. But when it's all over, we're the ones that are
together."
Doug smiled at Cindy and rubbed his knee against hers under
the table. The feel of nylon against nylon excited them both and
Cindy responded by slipping her hand beneath the table cloth and
placing it on his leg.
As he finished his drink she slowly slid her hand up his leg
and toyed with the top of his nylon. Doug felt the tension of
his garter strap as she traced the outline of the fastening. He
also felt his growing erection and was thankful Cindy had been so
thorough in taping his member back.
When their meal arrived, Cindy ordered another round of
drinks and both attacked the food with a passion. As they
finished the dinner Doug saw the two gentlemen head toward their
table. He pressed his knee against Cindy's and indicated for her
to look in their direction.
Cindy looked up as the two arrived at the table. She smiled
demurely as the taller of the two asked her, "Would you two young
ladies care to dance?"
The music was slow and so was she in responding, "Why, I
think we'd love to. Wouldn't we Darla?" She looked directly at
Doug when she said that and could tell he was nervous. Then she
accepted the outstretched arm of the shorter of the two men and
accompanied him to the dance floor.
"Darla, eh? Pretty name, shall we join them?" said the
huskier fellow.
Doug placed his hand on the mans arm and slowly stood up
from the table. The two made their way between the other tables
and were soon on the dance floor.
Fighting instinct, Doug allowed the man to place his arms
around him and then tried hard to follow his lead. As if it came
naturally, Doug found out he had no trouble assuming the proper
role and soon the two were tightly pressed together.
The music drifted among them as Doug became keenly aware of
the bulge in his partners pants. He found it exciting that
another man was becoming turned on by him and he increased the
pressure of his own pelvic area against his partner. The two
danced slower, while Doug sensed the urgency of his own masculine
appendage.
Rhythmically he began pressing his hips harder and harder
against his dance partner. The husky gentlemen responded with
equal pressure and Doug found himself placing his head deeper
into the mans shoulder.
As they continued to dance, Doug became very aware of the
mans hand pressing more firmly against his back. He could feel
his partners hand against the hooks of his bra and this only
excited him more. He did not realize the music had stopped when
he felt the mans hand slid from his back and drift across his
buttocks.
With a meaningful pat on Doug's feminine derriere, the man
said, "We'll have to do it again, Darla." And as a gentleman, he
escorted Doug back to the table.
Doug pursed his pink lips and smiled affectionately at the
gentleman as he retook his seat. Cindy was now joining them and
her partner asked, "How 'bout if we join you two and make an
evening of it?"
Doug nervously pulled a cigarette from Cindy's purse and
placed it in his lips. He was searching for the lighter when his
dance partner offered a light. As he puffed on the cigarette he
heard Cindy feign an excuse of returning to awaiting husbands
upstairs and the two men reluctantly bid farewell and departed.
Cindy signaled the waitress for the check and told Doug, "I
think it's time the two of us get out of here." Doug nodded
eagerly and departed with her after she had signed the room
number to the tab.
They arrived back in their room minutes later without
incident and Cindy was only too happy to kick off her shoes and
sink into the bed. Doug retrieved the champagne from the
bathroom and poured them both a drink.
"Well, what did you think of your dream now that you've had
a chance to act it out?" Cindy inquired.
"It was a little scary at first. And then when those guys
asked us to dance, I nearly died. Do you know he got a big hard
on and kept rubbing it against me."
Cindy chuckled and said, "Well can you blame him. Look at
yourself, you really are a beautiful woman. But right now I want
that beautiful woman to climb on top of me, or better yet," she
hesitated, "I'd rather climb on top of that beautiful woman."
Doug dropped to the bed and the two clung desperately
together. "Wait," Cindy said, "let's shed a little of this
clothing first. I've got another surprise for you."
With that she hopped up from the bed and crossed the room to
the closet. Deftly she removed two identical floor length satin
peignoir sets and returned to the bed side. "Take everything from
your slip on out off," she said as she began also stripping to
just her panties, garters, nylons and bra.
Doug was quick to follow suit. As soon as the two were shed
of their outer garments, Cindy handed one of the gowns to Doug
while she placed the other on her own body. Before climbing back
in bed she turned down the covers and then placed her small over
night bag on the floor next to the bed.
Doug laid back on the bed and realized he was extremely
excited by the wisps of nylon draped across his body. Cindy
knelt and straddled his hips. The rustle and feel of nylon tricot
was everywhere. She slowly started rocking her hips back and
forth and could sense Doug enjoyed the smooth frictionless feel
of the mingling female garments.
Gently she reached beneath Doug's buttocks and pulled the
tape restraining his testicles. When she freed his semi-rigid
cock she rolled the front of his panties down and pulled his
growing member out. After she hooked the panties beneath his
warm balls, she leaned over and retrieved two soft vibrators from
her night bag.
As Doug's penis became harder she rolled off of him and
quickly shed her own panties. Cindy then lubricated both toys
and gently inserted one in Doug's quivering anus. As she lowered
herself upon his erection she guided the other vibrator into her
own anus.
"Oh baby," Doug moaned. He was so worked up from all the
excitement of the evening he knew he would not be able to hold
back much longer.
Cindy knew he was near the edge. She sat up as straight as
she could and buried his cock deep within herself. Dougs hands
were massaging her anal cheeks as he worked the vibrator in and
out of her.
Cindy used one hand to work the vibrator back and forth in
Doug while she kneaded his nipples beneath the bra he wore. With
a violent shudder Doug shot cum deep in Cindy.
She orgasmed twice as he spent his load. They both
remained motionless for an eternity and then slowly Doug started
pumping in and out of her again. Within seconds he had regained
a rock hard rigidity that Cindy knew would last throughout the
night.
"Oh darling, darling," she moaned, "I love you so much."
Doug continued to pump as she rubbed her hands all over the
nylon and lace he wore. With each stroke of her hand the
intensity of his movements increased. The effect of lace was so
great that Cindy knew she had discovered a means to heighten the
pleasure both of them shared.
After they had both enjoyed countless orgasms they lay
cuddled together in a mixture of sensuous clothing. Cindy could
not believe the profound effect her suggestion of acting out a
dream had had on Doug. Or, for that matter, the effect it had on
her. She slowly drifted off to sleep vowing she would continue
to live his dream.
IV
Doug woke first. The realization of Saturday morning at the
motel flickered through his mind. Awareness of the lingerie he
wore flooded his senses. Cindy was still snuggled up next to him
and he enjoyed looking at their two bodies dressed similarly.
He caressed her with one hand while he caressed his own body with
the other.
She woke slowly. She was vaguely sore and suddenly
remembered why. Cindy smiled as she opened her eyes and leaned
closer to Doug to kiss him. "Feel like a morning swim," she
inquired.
Doug looked at her questioningly.
"I've got a really nice one piece suit for you. You'll love
it!" She said.
Cindy hopped from the bed and dashed to the bathroom. Doug
sat up and looked into the mirror. The wig was a little awry,
but the make up was intact. He adjusted the hair piece and
flipped on the television set.
Cindy reappeared from the other room and tossed him the
swim suit. She had already pulled on a skimpy suit and had towels
in her hand.
Doug examine the swim suit and looked puzzled. "How we
gonna pull this off," he asked.
"Strip down to just your panties, I've got another idea."
He did as she bid and then Cindy re-taped his flaccid penis
back the way she had last night. "Now, pull on the suit and
let's see."
Doug stepped into the fucia swim suit and pulled it up. The
skirted bottom hid any traces of his masculinity and Cindy helped
him adjust the blouson top. She then inserted a pair of breast
prosthesis into the built in bra of the suit and adjusted them in
their confines.
"Well, maybe," Doug mused as he looked into the mirror.
"But what about the wig?"
"You'll just have to keep your head out of the water, or
wear this swim cap." Cindy said as she tossed him a rubber cap.
She grabbed a pair of towels from the bathroom and picked up the
key from on top of the television. "Come on, it's early. We'll
have the pool to ourselves."
Doug followed her down the hall way and she was right, they
had the pool to themselves. After about a half an hour two
skinny teenagers showed up and began splashing each other in
another corner of the pool. Doug and Cindy decided they had
better not press their luck so they got out of the water and
dried off.
With towels draped over their shoulders they headed back to
the room and were just crossing the second floor lobby when the
dance partners from the previous evening came up the stairway.
Cindy saw the two men and smiled. "Morning," she said as she
recognized them.
The two men returned the smile and said "Good Morning" in
unison. As Doug and Cindy passed by them, the husky fellow that
had danced with Doug reached out and patted him on the ass as he
walked by. Doug let out a gasp while Cindy just chuckled.
"That's something I don't know how to handle." Doug told
Cindy as he closed the door behind him.
"You'll learn how to play the part." She responded while
stepping into the bathroom and adjusting the shower. "How about
we shower together?"
Doug quickly joined her. When they had finished showering,
Cindy laid out a complete outfit on the bed for Doug. Standing
with the towel wrapped around himself, he carefully examined the
items and then picked up the sanitary belt and pad.
"That will probably be more comfortable than wearing tape
all day. And it'll be a lot easier to remove when ever you need
to go to the toilet." Cindy told him.
Doug nodded in acknowledgement and slowly stepped into the
contraption. Before pulling it up all the way, he pressed his
testicles back and then wiggled the pad into place. The straps
rode high on his hips, while the end of the belt disappeared into
the cheeks of his ass.
Next, he donned the light blue nylon tricot panties and
admired the lace trim around the waist and leg bands. He
marveled at how the sanitary pad produced a feminine pubic
mound. He quickly picked up the corset and was examining the
garment while Cindy dressed.
He noticed it had heavy boned stays. The corset laced and
hooked in the back, so Doug slid the affair over his arms and
positioned it in place. Cindy stepped over and drew the laces
tight and then hooked the corset for him.
He slipped the silicone prosthesis in each cup of the
corsets brassier and then sat on the edge of the bed. While
putting on the nylons and fastening them to the garters of the
corset, Doug could feel an erection growing. He was thankful the
sanitary pad held him secure.
Cindy tossed him an embroidered lace slip and he quickly
fitted the sensuous garment to his body. "All of these clothes
fit so nicely, and they feel terrific. How did you ever get the
right size in everything?"
"You forget, dear, I've been buying your clothes for a long
time. It wasn't hard to convert your men clothes size to women's
clothing." She said.
Doug enjoyed the feeling of nylon swaying against his body
as he crossed the room to the closet. "Which dress is mine?" He
said.
"Why don't you try the blue one hanging next to the outfit
you wore last night."
Doug removed a sky blue dress from the hanger and stepped
into it. He pulled the dress on and slipped his arms into it.
As he adjusted the puffy sleeves, Cindy zipped it up for him. He
liked the mandarin collar and the way the garment clung to his
curves. "It's beautiful," he murmured.
"I thought you'd like it." Cindy handed him her bracelet
watch and he fastened it to his wrist.
She motioned for him to set at the dressing table and then
carefully began applying a light make up. "We'll skip the
mascara for daylight wear. I think this blue will match your
dress." She said as she dabbed a light powder blue to his
eyelids.
She blended on small amounts of Cover Girl foundation and
said, "We don't want to over do it or that'll just call attention
to you."
He picked up the lipstick she had set before him and slowly
traced the outline of his lips. Cindy was fastening a pair of
dangling blue plastic ear rings to his ears and Doug sat
patiently observing the process in the mirror. The illusion
being created excited him and he could feel his rock hard penis
straining at the cotton pad.
When Cindy finished she handed him the wig and had him place
it on his head. She took a small brush and teased the hair piece
until confident it looked proper. "There, I think we're done."
Doug slid on a pair of woven straw sandals and fastened the
straps around his nylon encased legs. The feel of the nylons
rubbing together as he moved his legs about was too much for him.
He hoped Cindy did not notice as he shuddered and felt a warm
liquid oozing between his legs. He was thankful for the sanitary
napkin and made a mental note to take along a spare.
When he stood up, Doug took one last look in the mirror and
couldn't believe the picture of feminity that stared back at
him. "Let's go." Cindy said as she opened the door and waited
for him to join.
"Where we going." Doug inquired as he stepped into the
hallway with Cindy.
"I thought we'd get some breakfast and then tour the art
museum." She answered.
They walked side by side to the stairs and then crossed the
lobby to the front door. Again Doug noticed that no one paid any
attention to them and he felt comfortable that he could
masquerade so easily.
"I'll drive." Cindy said as she opened the passenger door
for Doug.
They had not gotten out of the parking lot before
discovering they had a flat tire. "Damn," Cindy said, "of all
times for this to happen."
She slammed the door as she started to walk around the
vehicle to assess the situation. Doug was coming around the
front of the car to join her when he heard, "Can we be of
assistance ladies."
V
Doug and Cindy looked up to see their two dance partners
nearing the disabled car. "Hi, I'm Dave and this is Dan." Said
the fellow Cindy had been dancing with. "We'll have that fixed
in no time. Got a spare in the trunk?" He inquired.
"Oh, thank you." Cindy said as she went around the car and
placed the key in the trunk. "I don't know what we'd have done
if you hadn't come along."
Dave removed the jack and wrench from the trunk as Dan set
the spare tire on the ground. While Dave began positioning the
jack, Dan stepped next to Doug and inquired, "How's Darla this
beautiful morning?"
Doug's heart was pounding rapidly as he whispered, "Got a
little case of laryngitis."
"Aw, that's too bad." Dan responded. "Maybe you'd like to
join us for breakfast. We were just planning to go down the
street here to the pancake house. How about it?"
Doug shot Cindy a glance and saw her perk up at Dan's
suggestion. "That would be wonderful, wouldn't it Darla."
Doug nodded meekly and wondered how he would handle the
situation. Dave had finished changing the tire and was putting
everything back in the trunk. "Why don't you park your car and
we'll walk down to the restaurant. It's only half a block away."
He said.
Cindy agreed and backed the car into the slot. Dan offered
his arm to Doug and he limply placed his wrist in the crook of
Dans arm. He was glad he still had the false finger nails on as
they gave his hands a distinct female appearance.
Dave escorted Cindy as the two couples strolled down the
side walk. Doug began enjoying the attention Dan was showering
upon him. He even appreciated the way Dan held doors open for
him and treated him as a woman. He was glad Dan offered to order
for him so that 'Darla' wouldn't strain her throat.
Nearing the end of their meal, Doug felt Dan place his hand
upon his nylon covered leg and his eyes went wide open. Cindy
saw the look in her mates eyes and realized what must have
happened. She smiled back at Doug and said, "Enjoying yourself,
Darla?"
Doug could only manage a week nod and continued to pick at
the food on his plate. Dans hand had gotten bolder and was
slowly inching up his leg. He could feel Dan toying with the top
of his nylons and tracing the outline of the garter.
Cindy saved him by announcing, "I need to use the powder
room. Care to join me Darla?"
Doug and Cindy quickly crossed the dining room to the women's
rest room. Once inside, Doug looked around and saw they were
alone. "He's putting his hands all over me. I don't know what
to do."
"Don't be so worried honey. He can't do anything as long as
we're in a crowd. Enjoy it, and tease him a little. Surely
you've been teased by some girl in the past."
She made sense, Doug thought. "Well maybe," he started, "I
just didn't expect anything like this to happen."
"Have all the fun you want, 'cause when we go home we're the
ones that are together. I love you and I don't care what I have
to do to make you happy." Cindy stopped talking when another
women entered the room. She checked her own make up in the
mirror as she handed Doug a tube of lipstick.
They both returned to the table and Dave and Dan stood up to
hold the chairs for the women. Doug had not been seated for
more than a minute until he felt Dans' hand once again on his
nylon covered knee.
As Dans fingers began creeping under the dress, Doug let his
own hand rest upon the thigh of his partner. Dan accepted the
touch as a signal and quickly slipped his fingers to the crotch
of Doug's panties. Feeling the sanitary napkin, Dan momentarily
withdrew his hand and then replaced it on the panty covered pad.
Dan slowly began applying pressure to the pad and
rhythmically started rubbing it up and down. The feel of the
moist pad against Dougs flaccid penis caused him to get an instant
hard on and he found himself becoming quite excited. As Dan
continued to rub the pad, Dan let his own hand drift farther up
Dans thigh until he felt a familiar bulge.
Cindy and Dave had lapsed into small talk, while it appeared
Dan and Doug were slowly finishing their meal. Doug heard Dave
mention something about stepping outside for a cigar and Cindy
agreeing to join him. Dan too quickly announced he would take
care of the bill and Doug looked up to see Cindy departing with
Dave.
With the other couple gone, Dan increased the frequency of
his movements and Doug was breathing quite heavily. He grasped
Dans bulge with the tips of his false fingernails and pinched
lightly as he began stroking the stiffening member in time to the
movements Dan was applying to him.
Doug exploded warm, thick juices as he felt Dan shudder and
cease his activities with the pad. Doug squirmed slightly to
allow the last few drops to drain from him into the awaiting
sanitary napkin. For the second time today he was glad the pad
was in place as he with drew his hand from Dans crotch.
Doug had a contented smile on his face and noticed Dan was
wearing a sheepish grin. Both glanced down and saw a small spot
appearing as the tent shaped fabric of Dans trousers began to
sink back down. "I guess I'd better head back to the room." Dan
said meekly.
He left some bills on the guest check and then escorted
Darla from the restaurant. Cindy and Dave appeared to be deep in
an animated conversation and nearly missed them as they came out.
They all quickly returned to the motel where Dan bid farewell as
he rapidly crossed the lobby and bounded the stairs two at a
time.
Dave looked questioningly after him and then turned and
shrugged to Cindy and Darla. "I guess I'd better go make sure
he's alright. Will we see you girls again?"
Cindy smiled at Doug and then said, "We'll be in the lounge
again tonight. Perhaps we can slip away from our husbands again.
They're out playing golf now, and are usually too tired to go out
when they've completed eighteen holes."
Dave bid them farewell and then departed. "What ever
happened after we left?" She inquired of Doug.
"I think I have to go up to the room for a minute too. You
said to enjoy myself, and well, I just did what he did to me."
Cindy chuckled to herself and thought out loud, "You sure
learn fast." They returned to the room and before Doug had a
chance to replace the soiled napkin, Cindy crossed the room to
him and gently pushed him onto the bed.
Caught unaware, Doug fell back on the bed as Cindy bounced
on to it next to him. She rapidly slid her hand under his dress
and began massaging the panties against his napkin. He
instinctively parted his legs for her and felt the wetness from
his earlier excitement.
Cindy hiked her own dress above her thighs and straddled
Doug with her head facing his feet. She bent over to reach her
night case and he nuzzled his face against the fabric of her
panties. She continued massaging the sanitary pad against his
growing erection as she pulled one of the toys from her case.
Doug could feel his penis growing as he buried his face in
Cindy's pantied rump. He began to nibble on the tricot barrier
and could feel her vaginal lips sliding beneath the soft fabric.
His own panties strained at the pressure of his emerging hard on
pushing against the pad Cindy was massaging.
Cindy slid the leg band of his panties aside and lubricated
the object in her hand with the dampness from his pad. As he
continued to tease her with his mouth against her own panties she
slid the soft, firm vibrator into his anus. She slowly worked
the toy in and out as she increased her movement of the sanitary
napkin against his rigid cock.
Doug felt like he was in heaven. He nibbled harder and
caught her lips between the fabric of her panties as she plunged
the vibrator back and forth in his anus. The sensation of nylons
and tricot intermingling with the constraint of the corset and
her actions on his body were over powering.
Cindy knew he was nearing the moment and she released his
cock from the pad which held it. It pointed straight in the air
as she climbed from his body and quickly stripped her own panties
as quick as she could. She turned and positioned herself above
him and then lowered her body to his. Her moistness engulfed him
as she continued to plunge the vibrator in and out.
Garters snagged against garters as lace mixed with nylon and
nylon. He exploded like never before. She quivered, then
shuddered and exploded too. Wetness drained everywhere as they
continued to pump feverishly.
And then they were motionless.
Cindy sat breathing heavily as Doug grasped for air. The
vibrator was buried deep within him as he remained buried deep
within her.
Moments later, an eternity, he slowly felt himself fading.
As his penis returned to a flaccid state, she slowly withdrew the
vibrator. Cindy contracted her muscles and he popped from within
her. At the same instant she totally with drew the toy and
dropped it to the floor.
"We've never, I mean never, had sex with such urgency. I
think it was great!" Cindy said as she got up from the bed. She
picked up her panties and stepped back into them as Doug sat up.
He could not say anything. He knew she was right. He got
up and headed for the bathroom after picking up a fresh napkin
from the box Cindy had in the suitcase.
"Now you really see why the garters go underneath the
panties, don't you." Cindy called out to him.
Doug only responded by flushing the toilet and completing
the task at hand. Seconds later he stepped from the other room
and joined Cindy on the edge of the bed. "I guess the museums
out for this morning. What other little surprises did you have
in mind?"
"Oh, I've got a little idea in mind you might enjoy."
Cindy got up from the bed and opened the door. Doug
followed her out and they both headed for the car. She drove for
a few minutes and Doug realized they were headed downtown. She
circled one block a few times and then pulled into a vacant spot
in front of an adult book store. Doug smiled.
She opened the door for him and they both stepped into the
store. It was still early in the day and few other customers
were among the racks of magazines and video cassettes. Cindy
walked from one isle to the next until she spotted the section
containing literature on female impersonators. Doug stepped next
to her as she picked up one magazine from each holder and began
cradling them in her arm.
After she was sure she had one of each selection she
wandered around a bit and then settled in front of the counter
containing toys of every description. She selected a few items
and the gaunt male clerk nonchalantly dropped them into a bag.
She paid him and then turned to find Doug still browsing through
the titles she had made her choices from.
Cindy caught his attention and signaled him that she was
ready to leave. Doug replaced the magazine he'd been thumbing
through and accompanied her to the car. "I got one of each and
we can look at them later back at the motel. For now, let's head
to the mall. I have a few more things to pick up and we can grab
some lunch at one of the lounges there."
Doug was only to happy to be dressed as he was and didn't
really care where they went. He enjoyed the breeze as it wafted
gently through his wig and chilled his lace clad body. The trip
to the mall passed rapidly as Cindy drove among the week end
congestion.
She led him through the window shoppers and squalling
children to a women's lingerie shop at the end of one passageway.
It only took her seconds to scoop up oodles of pastel colored
panties and deposit them in Doug's arms. She selected a few more
packaged panties and dropped them on top of the growing armful
held by Doug.
"When we get home, I'm going to get rid of all your cotton
underwear. If what's happened to us in the last two days is
caused by these, I intend to keep you well dressed from now on."
Doug caressed the items he held and considered the words she
said. He could feel his manhood growing and realized what she
was telling him was the cause for it. As he walked behind her
the constant strain of the napkin against his cock and the
thought of such beautiful under garments caused him to become
even harder.
Cindy picked out a couple of varieties of teddies and panty
slips and also handed them to Doug. His arms were so full he had
to get a basket from next to the counter to carry everything she
was getting. When he returned to her, Cindy handed him another
armful of silk and lace.
The basket was overflowing when she finally decided to add a
few brassieres to his growing collection of feminine attire. As
he waited patiently while Cindy paid for the items he discovered
he was unconsciously squeezing his thighs together rhythmically
and was causing his rigid cock to strain even more at the pad.
He watched the young teenaged clerk carefully folding and
placing the wealth of silk and nylon in packages and he pressed
his thighs tightly together one last time. He felt the warm,
damp liquid exploded from within and fill the waiting sanitary
napkin. For yet another time today, he was grateful for the
security of the pad and hoped no one noticed the little shudder
he gave as the final drops spent from his penis.
They left the store and wandered among the mall. Doug
savored the way his softening member slid among the lubrication
of the pad and he likened the feeling to that of being buried
deep within Cindy.
They enjoyed a leisurely lunch in one of the mall
restaurants and then continued window shopping until deciding to
return to the motel. Cindy returned to the car for the last of
the days purchases as Doug sank into a chair and absently flipped
on the television set.
When Cindy returned from the car, she found Doug had fallen
asleep in the chair with his wig slightly awry. She quietly
removed it and then began sorting items from the days shopping
spree. After she had packed everything away, she took a hot bath
and then prepared one for Doug.
She awoke him with a kiss and said, "I've got a nice hot
bath ready for you. Why don't you relax in the tub awhile and
I'll pick out some things for us to wear tonight. "
He nodded and groggily made his way to the bathroom. He
slipped out of the blue dress before going in the bathroom and
draped it over a chair. He kicked off the sandals and then
padded into the bathroom clad in his dainty underwear.
He let the slip fall to the floor as he began unfastening
the garters and removed the nylons. The corset was a little
difficult to remove by himself, but he managed to shed to garment
and stood for a second looking at the reflection of his pantied
backside in the mirror. He could see the indentation of the
sanitary belt beneath his panties and suddenly realized it was
still damp.
He quickly peeled off the remaining garments and then slid
into the tub. The hot, bubbly liquid comforted him as he picked
up the safety razor Cindy had left on the side of the tub. Even
though his legs did not need it, he slowly drew the razor against
them and made sure they were closely shaven. The feeling created
by the ritual caused him to acknowledge a deep feminine urging
from somewhere within himself.
Doug pondered the emotions welling up and then asked Cindy,
"Were you serious about what you said when we were in that one
store today?"
"Definitely," she responded. "The way soft women's clothing
has excited you the last two days is fantastic. I intend to see
that you remain as happy as you've been this weekend. Besides,
who will know?"
He had dried off, and wrapped the towel around himself the
way Cindy usually did, high on his chest. He paused and gazed at
his reflection in the mirror. With all the make up washed off,
you didn't notice his eyebrows had been plucked and took on a
feminine appearance, he thought.
Cindy came into the bathroom and began preparing a bath for
herself. "I've set everything out for you on the bed." She
said. "I'm going to get cleaned up while you dress, and then
I'll slip into something and we'll go down to the lounge again
for supper."
Doug left her alone while he went out to check what she had
selected for him. He found the sanitary napkin and belt on top
of all the articles she had piled on the bed and he quickly
stepped into the garment and tucked his maleness between his
legs. Before pulling the pad into place, he sprinkled some of
her fragrant powder on it and then snuggled it against his soft
cock.
She had chosen a deep plunging front closure brassier for
him and he had little difficulty fastening the bra. He admired
the way the clasp fitted securely behind a pretty li
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