The Job-Hunt
by Suzi (Johnson) Thomas
It was a really tough job market out there - I had recently graduated
college, and going on as many interviews as I could schedule, without
success. My girlfriend hadn't had nearly as much trouble, and had landed a
well-paying job at an advertising firm. And since we were living together at
least I had a roof over my head. I had paid my way through school with a
combination of scholarships, loans and part-time jobs, but I just couldn't
find anything now. It was already well into August, and the only
contribution I was making toward our expenses was the little I made at three
part-time jobs.
"Dammit, Jennie," I said to her one evening, "today had to be the most
frustrating day of all. I had three interviews, but they were all the same
`Sorry, but we don't think so. We'll keep your resume on file if something
should turn up later.' Right, like they didn't trash them as soon as I
left." "Don't worry, hon," she said, "I'm sure something will turn up soon."
"I don't know," I said, I think I'm a victim of discrimination or
something." "What makes you say that?" she asked, "you're not a member of a
minority group - I think you're overreacting." "I don't think so, from
something I overheard today. I had just walked out of the last interview and
I heard one guy I was talking to say to the other, `Too bad - but I didn't
expect it from his name.' I think if I had been a woman, I would have gotten
the job. They were ready to interview a girl named Robin, not a guy." "I
still think you're overreacting; you probably misunderstood what he said."
Well, it was three weeks after that night, and still no job. But now I
finally had some evidence to support my suspicion. I had just come back from
a long interview, and I had really hit it off with the interviewer. I was
telling Jennie about it: "Then he said to me, `Robin, I think you'd be
perfect for the job, and what I'm going to say is off the record, OK? I'll
deny I ever said it, but ... well, my boss set down strict guidelines for
hiring. We can hire guys who are in the top 5% of their class, but because
we need to hire more women, we can hire them if they're in the top third.'
See, Jennie, I told you so - I'm being discriminated against!" She
sympathized with me, but just encouraged me to keep on trying. Another three
weeks of no success had me pretty depressed, and we decided to watch some TV
to cheer up. I hit the ON button on the remote, and what was playing but
"Tootsie". Dustin Hoffman trying to make it as a guy, but achieving success
only after he dressed up as a woman. "Boy, that's the right idea," I
remarked, bitterly, "if you can't beat 'em, join 'em." Jennie looked at me
strangely for a minute, then said, "You know, Robin, you'd make a
better-looking girl than he does." "That's ridiculous," I said, "I could
never get away with that - people would spot me in a minute." She didn't say
anything, and I switched channels, ending the conversation right there. .
A few days later, we were lying in bed together, having just made love, when
she brought it up again. "Remember what we talked about when we saw
"Tootsie" the other night?" she asked. "Yes, I do - your silly idea that I
could get away with dressing like a woman." "Well, I still think I'm right,
that you'd be cuter than Dustin Hoffman." I really didn't feel like talking
anymore about it, but she continued, "I'd be willing to bet I'm right."
"Sure," I said, "bet what? You know I'm broke, and besides, its really a
dumb idea. There's no way I'm going to dress up and go out as a woman."
"Well," she replied, "we could bet washing the dishes for the next month."
Both of us hated to wash dishes, and we rotated the chore every night. "As
much as I'd like to not do dishes for a month," I said, "because I know I'm
right, there's no way I'm going to make a fool out of myself." "What if
there were a way, you could try it without any risk? she asked, "would you
still be willing to bet?" I was tired by then and I said, "Sure, no risk,
whatever you say." "So do we have a bet?" she persisted. "Yes, yes, OK, we
have a bet," I said, and we fell asleep without any more conversation on the
subject.
I didn't think about the conversation the next day, and I made us a cold
dinner, waiting for Jennie to get home. She had called and said that she was
stopping off at her sister's house and would be a little late. It was almost
eight o'clock when she finally got home, and I told her, "I was starting to
get worried about you," and I gave her a big hug and kiss, relieved that she
was alright. "It took me longer than I thought it would," she said, "but we
finally got done." "Done?" I asked, "what were you doing?" "Getting ready
for our bet," she said. I noticed that she had two shopping bags with her.
"What's in the bags?" I asked her. And she proceeded to lay out her plan:
"There's an office Halloween party coming up, and that's where I'm going to
win our bet. There'll be a million people there, clients, agency people,
friends, vendors, and hardly anyone will know anybody. I spent the evening
at Patty's getting your costume." I hadn't taken her bet seriously last
night, but obviously she had! "What do you mean, my costume?" I said,
suspecting the worst, and her answer confirmed it: "You can dress up as a
woman for a Halloween party without any risk - lots of guys do. And since no
one from the office knows you - no risk, just like you agreed to." I tried
to argue her out of it, but there was no way she was going to cancel the
bet. I resigned myself to the fact that she had the costume I was going to
wear in the shopping bags. We sat down and ate, and we avoided the topic
until she said, "C'mon, be a sport, you did agree to the bet, and its only
for one night for the party. I don't want to make you feel bad, though, so
I'm willing to cancel the bet, if you insist." "No, we made the bet," I told
her, "and guys just don't cancel bets. I'll go along with it, though I'll
feel silly as hell, and everyone will know I'm a guy. Besides, when I win
the bet, I'll enjoy watching you wash dishes every night for a month. Who
knows, maybe you get to like it, and you'll want to wash them all the time!"
"Fat chance, buddy," she retorted, "and I still think that you'll be the one
with dishpan hands! Speaking of which, its your turn tonight."
Sighing to myself, I got up and washed everything while she went inside.
When I had finished, I joined her, and she turned off the TV she had been
watching. "You know," she said, "you really have to try your best not to be
discovered, if this is going to be a fair bet." I said that if I did
anything that would deliberately made me win, I would lose. "Is that fair
enough for you?" "Well, almost," she said, "but not quite." "What do you
mean, not quite?" "Girls learn how to be girls as they grow up, years and
years of becoming ladies," she said. "You can't just learn it overnight. To
be really fair, you should practice." "C'mon," I said, "fair is fair, I
agreed to one night, not `years and years of practice'. Besides, there's
only two weeks until the party." "OK, I'll settle for two weeks of
practice," - although I hadn't agree to any practice at all! - "let's get
started, there's no time to waste." She took the shopping bags in one hand,
and my hand in the other and led me upstairs.
In short order, I found myself standing naked in the middle of the bedroom,
watching Jennie pulling clothes out of one of the bags. "I wasn't exactly
sure about sizes, so I got a whole bunch of Patty's things - she's more your
size than I am." It was true - I'm quite a bit bigger than Jennie, while her
sister Patty is nearly as tall as my 5' 9" and has a larger frame than her
petite sister. I have a very slender build, though, for a guy, and I guessed
that we were probably about the same size. As often as Jennie and I had made
love, it still felt strange to be standing naked in front of her while she
was doing something else, and I found that I was getting an erection. When
she saw it, she laughed, and began to stroke it, teasing me, "don't tell me
that thinking about dressing as a woman is turning you on?" "N ...no, don't
be silly, its just be naked while you're still dressed," I said. "Well, we
have to do something about this," she said, continuing to stroke me, "or
else you'll have a bulge in your panties." She knelt down in front of me,
and took me into her mouth, quickly bringing me to a climax, while thoughts
of how I would soon be dressed disturbingly ran through my mind.
"OK, now that THAT's out of the way, slip into these," she said, handing me
a pair of white panties. They felt strange going on over my legs, and
nestling around my groin, but I told myself that was to be expected - these
weren't exactly my usual jockey shorts! Jennie helped me put on a matching
white bra, stuffing the cups with a couple of pairs of her panties, after
she fastened the hooks in back. She sat me down on the bed, and, as I
followed her instructions for putting on pantyhose without causing runs, the
bra felt really weird on my chest. The pantyhose felt even more strange,
covering my entire legs with the feeling of the sheer material. "These are
just regular daytime things," Jennie said, "I hoped that I'd be able to
convince you to practice." She was really serious about winning this bet, I
could see, and had planned the whole thing out. I stood up, feeling the
tickling sensation of the nylon against my leg hairs, and pulled the slip
she handed me over my head. She settled it around me properly, making the
smooth nylon rub over my whole torso. She then lifted a pink and white
striped dress over me, and I raised my arms so it would slip down into
position. I began to button up the front of the shirtwaist dress, fumbling
because the buttons were on the "wrong" side. "Well, you don't have much of
a figure, dear, but at least everything fits pretty well. Except for the
waist, of course." My waist did stretch out the waistband of the dress, and
I said, "see, I told you this wasn't going to work."
"Don't worry, we'll take care of that when the time comes," she said, "after
all, not every woman has a perfect figure." I didn't have a chance to ask
what she meant, because she was handing me a pair of medium high heels to
put on. The swishing, swirling feelings of the feminine materials against
each other and my body felt extremely strange as I walked over to the bed
and sat down to put on the shoes. "You're lucky my sister has big feet," she
commented when I had put them on, and tried to stand up. I almost fell over
because of the tilt they gave my body, but Jennie steadied me. "OK, practice
walking around a little," she said. I did, feeling more silly than ever when
she began to coach me on how to walk in a ladylike manner. "A little more
hip sway, but not too much," she said when I exaggerated to my hip motion..
"You're not going to be a hooker, just a real lady."
She made me wear the clothes until it was bed time, and I had almost gotten
used to the heels, but not to the feeling of the soft, silky clothes against
me. I had an erection again, unusual for me, since I was strictly a
"once-a-day" guy, and the oral sex Jennie had given me would have ordinarily
finished me off for the night. Were these unusual clothes, and the way they
felt on me the cause of it, I wondered. Jennie helped me get undressed, and
I managed to hide my cock inside my robe as I went in for a shower. I came
out, and Jennie went in for hers, and I found myself touching the things I
had been wearing. I heard the door open, and feeling my face flush at almost
being caught touching the feminine finery, I shut off the light. She hopped
into bed next to me, and asked me, "that really wasn't so bad, was it?" "N
... no, I guess not, just strange is all." "Well, remember your promise, you
have to practice every night until the party," she said, curling up against
me. "You really did look pretty cute in the dress, not to mention in your
bra and panties," she teased. "Oh, cut it out, I looked exactly like what I
was, a guy in drag. You know, I'm more convinced than ever that I'm going to
win this bet." "We'll see," she said, kissing me goodnight and turning over,
"we'll see." I lay awake for a while waiting for my erection to go down,
thinking about how the clothes had felt on me. The sensations of the smooth,
silky clothing persisted in my mind, and a random thought came to me, about
how lucky girls were to have all those nice-feeling things to wear, while
guys had all the masculine, rough fabrics. My hardon never did go down as I
lay there, but I eventually fell asleep anyway.
Jennie got up early to go to work, and I slept until about eight-thirty,
when I had to get up to go to one of my part-time jobs. I saw the clothes I
had worn still lying on top of the covers, and I picked them up to put them
away. The silky panties seemed to have a life of their own as the smooth
material caressed my hand, and I sat there, just experiencing it, until I
realized that I would have to hurry to get to work on time. I put in my four
hours of filing and got back home at about two o'clock. The work I had been
doing was mindless, and the only reason they had me as a part-timer was
because the secretaries hated doing it. I did a few chores around the house,
as I always did; since Jennie was earning the money it was only fair that I
do most of the housework - except for the splitting of the dishwashing, that
is. I finished most of it up, and had gotten to the bedroom, where I was
going to make up the bed. I saw the clothes still laying there, and with the
best of intentions, I started putting them away. I hung up the dress in the
closet, but then I was faced with the dilemma of where to put the undies. If
I put them in Jennie's drawer, they'd mix in with her things and could cause
a problem when she rushed to get dressed one morning. I didn't want to leave
them laying around, so I made room in my underwear drawer, neatly folded
them up and put them in there. Again, the smooth material sent strange
sensations through me, and as I walked out of the room, I found myself with
another erection. "This is ridiculous," I said to myself, "women's undies
are only exciting with women inside them." But a nagging voice in my head
raised a disturbing doubt about that: "Are you sure?"
I dismissed the voice, and began to prepare dinner for us. When Jennie got
home, she asked me how my day had been, and I told her pretty much the
usual, commenting on how the secretaries at work had been giggling to each
other about something for most of the time I was there. "Probably just
girl-talk," Jennie said, "somebody fooling around with somebody, or someone
having problems with a boy-friend." We had dinner, and then Jennie said,
"Time to practice, sweetie, you promised." I groaned, but followed her into
the bedroom. Jennie looked around for the clothes, and I explained where I
had put them, and why. She didn't say much, just, "how thoughtful." I
stripped again, and feeling the beginnings of an erection, I quickly pulled
on the panties. She hooked up the bra, and in just a couple of minutes, I
was dressed in the same outfit as last night. But this time, my cock was
rock hard inside my panties. Fortunately, the tight fitting panties kept it
pressed up against my stomach unseen. Jennie taught me how to walk around
more gracefully, and told me how to sit like a lady. "No, no, keep your
knees together, and cross your legs at the ankles. You're not ready to learn
how to cross your legs yet," she scolded. I tried to concentrate on
everything she said, reminding myself that I had promised that I would do my
best. Later that night, after we had showered, we made passionate love, and
the aching I had been feeling from walking around in panties all night, with
the silky material rubbing on my cock, finally subsided.
The rest of the week passed pretty much the same way, although we made love
every night, instead of the more usual, every other night or so. When we got
up on Saturday morning, Jennie said, "You know, Robin, I'm beginning to
think you might win that bet, after all." "What make you say that," I asked.
"Well, you've been practicing every evening, but, I don't think you are
going to fool everyone like I thought you were. There's just not enough time
to teach you everything you'll need to know. I'm ready to concede right
now." "No, that wouldn't be fair," I said, "I really am trying, you know."
In the back of my head, I was beginning to understand something else, but I
guess I was just trying to convince her that I was being a good sport.
"Well, we can keep trying, but we'll have to step up the pace a little." I
said I was, and she said, "then, you'll have to spend all weekend at it -
are you still game?" Again I agreed, and she said, "you can't wear the same
things all weekend, but I don't want you to wear your costume, either. I'll
run over to Patty's and get some fresh things, I'm sure she won't mind." So
while I was having a couple of cups of coffee, she went out, returning with
another shopping bag of stuff. "I got some sexier things this time," she
said. "Maybe you'll get into it more with more feminine frillies. Here, why
don't you go put these on while I have a cup of coffee." This was the first
time I had dressed by myself, and when I saw what she had brought back, I
immediately got turned on. I went into the bathroom and shaved as she had
said I should.
The undies were all black, and very frilly indeed. I slipped on the panties,
and I felt myself almost ready to come from the satin feel on my cock.
Without even thinking, I sat on the edge of the bed, and jerked my cock into
a gushing orgasm. There was no denying what had just happened now - wearing
panties was a definite turnon for me. I was wracked with guilt and doubts,
but I knew I had to keep this hidden from Jennie. I slipped my arms through
the straps of a longline black bra, which fortunately fastened in front. I
zipped up the bra, feeling the tightness of it as it molded my upper body.
The next thing I picked up was a black girdle, that had four garters hanging
from the bottom. It looked as though it were half as wide as I needed for it
to be able to fit over me, and I struggled to pull its tightness up over my
legs and waist. It reached up to the bottom of the bra when I finally got it
all the way up, but I felt like I could barely breathe with it on. There was
a pair of very sheer nylon stockings which I carefully rolled up over my
legs and managed to fasten to the garters, once I figured out how they
worked. Just then, Jennie came into the room, and looked at me. "God, this
girdle it tight," I said, "how do you women ever stand it?" "We have to
suffer for fashion, dear," she laughed, "and I think you're going to have to
suffer a little bit more." "What do you mean?" I asked. "Your leg hair shows
through the stockings, and I'm afraid you'll have to shave your legs." "Now,
wait just a minute," I protested, "I never agreed to anything like that!"
"But if you're going to do your best, you can't have hairy legs, and
besides its not like you go to a gym where anyone else could see you." She
proceeded to take off my stockings and marched me into the bathroom. I
half-wanted to protest some more, but also wanted to feel how the stockings
would feel against my hairless skin.
Oh, how wonderful they felt - my sleek legs being encased in the sheer
nylons. "Are you starting to feel sexy," Jennie teased, but not waiting for
a reply, she led me back into the bedroom. "I borrowed a cocktail dress from
Patty," she said, fastening a flared crinoline petticoat around me waist,
then putting a black satin dress over my arms and head. "Great," she said as
I stood there in the short, sexy dress. "The girdle and bra shaped you into
the perfect size for the dress." She placed a pair of very high-heeled black
patent leather pumps in front of me, and I stepped up into them. She walked
me over to her dressing table, helping me adjust to the 4" heels and said,
"We're going to go all the way today, a real makeover." She stood in front
of me, and first attached false nails onto my fingers. Then she began
applying all kinds of cosmetics to my face, gluing on false eyelashes as the
final step. Then she pulled a curly brunette wig out of a bag, placed it on
my head, and brushed it out a little. "My God," she said, "I said you'd be
better looking than Dustin Hoffman, but I never expected this!" She stepped
away from in front of the mirror, and what I saw reflected back nearly
knocked me off my seat - there was a gorgeous woman looking back at me. I
couldn't believe my eyes - I couldn't recognize myself at all. I sat there,
stunned. "I ... y ... you made me ..." I was at a loss for words. "Stunning,
that's the only word for you, stunning," Jennie supplied. She helped me
stand up on the heels, and walked me over to the full-length mirror. The
image there was even better and more powerful than what I had seen in the
face-only dressing mirror. From the curly hair to the spike-heeled feet,
there would have been no doubt in anyone's mind that this gorgeous creature
was anything but a woman.
Jennie stood next to me, and we were mostly a study in contrasts, the petite
blonde and the tall brunette, one dressed for day, the other for evening.
But there were similarities as well, the womanly figures, the sleek,
stockinged legs, the definitely female faces. She turned to me and put her
arms around me, then, hesitating for a split second, kissed me hard on the
lips. "I've never kissed a woman before, and even though I know its you, my
mind tells me that's what I just did." I looked deeply into her eyes, and
said, "But I'm still the man who loves you, underneath all this, you know."
Her hand moved down and brushed the front of my skirt, feeling the erection
beneath the feminine coverings. "D ... does dressing like this turn you on,
Robin?" she asked in a quiet, low voice. I didn't know what to say, and I
hesitated before answering. I had finally admitted to myself that it did,
but I wondered what effect it would have on our relationship if I admitted
it to her. We had always been honest with each other before, but I knew this
was a potential crisis situation, and there was no way for me to predict the
outcome. Believing that honesty was the only way to go, however, I said, "I
can't explain it, and this is something I've never even thought of before,
but it is exciting, Jennie, very exciting." She weighed this in her mind for
a moment, and then she said, "Robin, I ... I can't explain it either, but
kissing you dressed like that was, is, exciting to me, too. I've never
wanted to kiss a woman before, but seeing you like that, knowing that you're
a man underneath the clothes, its gotten me all hot also. I don't know if
its a one-time thing or something more but, ..." She stopped talking when I
kissed her, and with our arms around each other, we hurried over to the bed.
Without stopping to take off any clothes, we began to make love to each
other. The sensations I was feeling from the clothes I was wearing were
heightened as I touched her, and in just a minute, she had maneuvered my
cock out from under my things, and had impaled herself on top of me. It
couldn't have been more than thirty seconds later when I felt myself
starting to come, and I felt Jennie's body shudder with the force of her own
orgasm.
Later on, as we lay next to each other, Jennie said that she felt like she
had a new girlfriend, and I gave her a hug. "But, you know," I said, "we
can't stay in bed all day, I still have so much to learn if I'm going to be
able to carry this off for a whole night at the party." So we got up, and
for the rest of the day, Jennie tutored me on the fine points of femininity,
walking, sitting, eating, everything I would need to know in order to pass
undetected as a woman. That night, when it was time for bed, she helped me
out of the things I had been wearing all day, and though they had been tight
and restraining, and it really felt good to get my girdle off, I missed them
when they were gone. I started to walk into the bathroom carrying my robe,
but Jennie stopped me, and handed me a babydoll nightie set. "Maybe you
should keep practicing," she teased, and taking it from her, I smiled and
gave her a kiss. After my shower, I dried myself off and pulled the frilly
panties on, again feeling the wonderful sensations flooding over my cock.
The feelings spread to my entire body as I slipped the short nightie on. I
looked in the mirror, and even without the curly wig and the makeup, I felt
feminine and wonderful. Jennie said, "you look cute in that, and I'm glad
that `one-size-fits-all' is good for you." "Me, too," I responded, "and
speaking of `one-size-fits-all' ", I took her hand and placed it on my
erection, nestled inside my panties. We hopped into bed, and again made
love.
When I woke up the next day, I lay there thinking for a while about what had
happened, and what might be in store for the future. I decided not to worry
about anything, but rather to just let things work out themselves. I got up,
feeling the soft nylon surrounding my body, and went downstairs to make some
coffee. As I sat there drinking it, I found myself automatically sitting in
a very lady-like way, crossing my legs as a woman would. I looked down at my
shaved legs, which, of course seemed strange, and remembered how the nylons
had felt yesterday. Jennie walked into the kitchen about twenty minutes
later, and I had a brief feeling of anxiety, wondering how she might react
this morning to seeing me without makeup and my masculine haircut. But she
cut my worrying short when she came over and kissed me, and said, "I love
you, I really, really do!" After she had her coffee, she announced that it
was time for today's training to start, and we went into the bedroom to
dress.
She decided that I should wear regular daytime things today, and she gave me
a set of pink undies, which I immediately put on, savoring the feeling of
nylon against my groin and chest. She looked at me and giggled, and when I
asked her what was so funny, she told me that my chest hair didn't really go
too well with the pink bra. I felt myself blush, and she hurried over and
hugged me so I would understand she wasn't making fun of me. I took off the
bra, and we went into the bathroom where I shaved my chest, which truthfully
had never been all that hairy. Putting the bra back on felt better than
before, though, and she gave me pantyhose and a skirt and blouse to put on.
Next, she applied a cosmetics for a more natural daytime look, and placed
the curly wig on my head. When she moved aside to let me look, I could
recognize myself, but the face I saw was clearly feminine. "I think you
should wear heels again," she said, "because that will be the most difficult
thing to get used to." I didn't mind a bit, though, because I loved how
they made my legs look in the sheer pantyhose, and how they helped me walk
with a feminine sway. We didn't spend the whole day in training as such,
though we did spend some time looking through some of her magazines, but
concentrated on doing some things around the house so that Dressing would
become a more natural thing for me. She also taught me a little about makeup
so that if I had to fix myself up at the party I'd be able to do it. The
hardest thing, I think, was remembering to try to keep the pitch of my voice
higher than normal, so I would sound, as well as look, like a woman.
The rest of the week went by pretty quickly, with me dressing up each night
for more practice. Actually, I wore panties all week, and a nightgown she
had bought for me every night. I practiced putting on basic makeup a few
times, and actually got to be fairly good at it. Then it was finally
Saturday, and in the early afternoon, Jennie said that it was time to start
getting ready. "But its so early, it won't take us that long." "Don't be
silly, dear," she said, "we're barely going to be on time, even starting
right now." She drew me a bubble bath, and I relaxed in the scented water
for a while, until she came in and said that I should shave my legs and
chest. I did that while I was still in the tub. I got out, and was ready to
start shaving my face, when she suggested that, since we were going to be
out for hours, and I didn't want five o'clock shadow to appear, I should use
a hair remover lotion. She put the liquid on me, and I felt a strong
tingling as it did its work. I waited about fifteen minutes, sitting there
while Jennie took her own bath and shaved her legs and underarms. I hadn't
done the latter, and when she looked quizzically at me, I just nodded, as if
to say sure. She lathered my underarms, and carefully shaved me. I don't
have much hair on my arms, but she decided that what I did had to go as
well. I washed off the hair remover from my face, and we went into the
bedroom. I felt more naked than I ever had before, with all my hair gone,
but I realized how feminine my smooth, hairless body made me feel.
"Just out of curiosity," I asked, "what exactly is my costume going to be?"
Jennie had made me promise not to look in her closet or the shopping bags,
and I hadn't, as much as I had wanted to. "Well, I guess I can tell you now,
since you'll be finding out anyway," she said, "you're going to wear the
costume Patty had for last year - Scarlett O'Hara from `Gone with the
Wind'!" The memory of the beautiful gowns in the movie immediately flooded
my brain. And then I remembered the difficulty Scarlett had with getting
herself down to a figure that would fit into the gowns! Oh, God, I thought,
what did I get myself into with this silly bet?
Well, the first thing I found myself getting into was a pair of long satin
bloomers, with lots of ruffles of lace, around the whole garment. When I put
them on, the silky feel almost drove me crazy, and Jennie just smiled when
she saw the reaction I had. Next came the corset, and this was unbelievable
if you've never worn one. Jennie laid it down on the bed, and I slipped my
arms through the top straps and lay on top of it. Then she began to lace up
the back. It extended down from the top of my hips, and the first few
eyelets weren't too bad. But then as she moved up toward my waist, the boned
corset began to pull me in tighter and tighter. Jennie sat on top of me, and
pulled with all her strength to close the corset back together. "Stop," I
said, "I just can't get that small," but Jennie just kissed me on the back
of my neck and whispered, "but you have to, or the gown won't fit." She
continued lacing me unmercifully, and I tried to get accustomed to breathing
without being able to really draw in air. The confining corset, I could
feel, was molding me into the shape it wanted, irregardless of the body it
was enclosing. Even when my waist had been pulled all the way in, the tight
laces compressed the flesh of my chest, pushing the excess up toward the
bra's half-cups. I didn't realize how much there really was there, until
after she had finished the lacing and I stood up. "I think that with just a
little more," Jennie mused, and she went over to her underwear drawer and
removed the padding from one of her bras. She worked one into the bottom of
each cup, pulling up on my gathered flesh so that it then rested on top.
When she had finished, I walked over to the mirror, still trying to get
enough air to breathe, and saw the result. There was the sweep of female
hips, and my waist must have been drawn in at least six inches. But, best of
all, there was the swelling of breasts as my own flesh rose out of the half
cups of the corset top looking like real breasts. The cups pushed me
together creating cleavage, and Jennie said, "fantastic, I was a little
worried because the gown is kind of low-cut."
There were six long garters hanging down from the bottom of the corset, and
Jennie sat me down while she rolled stockings up over my smooth legs and
fastened them snugly, snaking the elastic straps through the bloomers. I
looked down and saw the mounds of my breasts, the tent created in the front
of my bloomers by the huge erection I had, and Jennie kneeling at my feet.
She looked up at me lovingly, and caressed my cock, then told me to stand
up. I did, but she stayed where she was, reaching into my bloomers to free
my cock from its satin prison, and she proceeded to suck me to climax. I
held here head tightly against me after I came, and the feeling of love
passed strongly between us. She stayed there for a moment or two, then said
in a husky voice, "we'd better get moving." She got my petticoat out of the
closet, a voluminous bulk of crinoline and lace. "There's no easy way to get
into this, but just step inside, and try to move your feet until they're on
the floor. I stepped inside the waistband, and sort of walked my feet
forward until they had cleared the crinoline tent. Jennie buttoned up the
back of the waistband, which fit perfectly around my corseted waist. From
the waist down, all I could see was the bulky petticoat, spreading around me
like a pyramid of snow, extending down to the floor. I twirled back and
forth, delighting in the feeling of the rougher petticoat material swishing
against my silken stockings and panties. The only things left were the shoes
and gown, and after she had helped me into emerald green highheels, the
petticoat was raised off the floor an inch or so. That had worried me,
whether I was going to keep tripping on it, having forgotten that my heels
would lift me into the air. I stood there looking in the mirror, when I
heard a soft rustling sound behind me. Jennie had gotten the gown out of the
closet, and I bent down a little, raising my hands so that she could lift it
over me. It was a beautiful emerald green velvet, lined with satin, and it
slid down around me with a silky woosh-sound. I closed my eyes, not wanting
to look until Jennie had fastened the back buttons. When she said she was
finished, I opened my eyes, and saw the lovely gown around me, my breast
tops rising above the neckline, and the long sleeves fitting around my arms,
ending in green lacy cuffs. The gown fit perfectly, and Jennie had to
practically drag me away to put on my makeup. She worked quickly, and with
the final touches of thick black lashes and a long wavy wig, I was ready.
She put a costume jewelry necklace around my neck, and clipped matching
earrings to my lobes. Again, the sight of myself had me speechless, and
Jenny sprayed a little perfume on me, completing my journey to femininity.
When I was able to speak, I asked Jennie what costume she was wearing, and
she told me that she was going to be a flapper from the '20's. She got
herself into her things pretty quickly, and stood next to me in front of the
mirror. Again, we were a study in contrasts, her short, slinky dress against
my elaborate gown, her unfettered body versus my shaped and restrained one.
But there was no doubt about it, when you looked at us, all you saw was two
beautiful females. I must admit, my face was not a soft example of feminine
perfection in the classic sense, but rather a striking, handsome one in the
female sense of handsome. We got together the things we needed, and were
almost ready to go when I said to her, "Jennie, I have a problem. I know no
one will be able to see it under my petticoat and gown, but I am as hard as
a rock underneath. I'm worried I won't be able to control myself with my
bloomers rubbing against me all night." She didn't even hesitate, and she
crawled under my gown, and took me into her mouth. She was really turned on
by seeing me, and I felt her rub herself against my ankle as she brought me
to a climax with frenzied sucking and licking. She had disappeared beneath
my clothes, and the sensation of coming was almost like a surreal dream. She
came as well, and she rested her face against the bare tops of my thighs for
a minute or two. When she finally reemerged, we hugged each other, then she
suggested that I needed something to prevent accidents for the rest of the
night. She went into the bathroom for a minute, then into her undie drawer,
and came back with a sanitary napkin and a belt to hold it on. "This should
do the trick," she said, and she disappeared under my gown again. I felt her
pulling down my bloomers and fastening the belt around me, then pulling back
my now-limp cock between my thighs. She held it in position with the napkin,
then pulled my bloomers back up to hold the entire thing in place. We were
now ready to go, and she placed another napkin in the purse I was going to
carry, "in case you have an accident later, dear. We girls always have to be
prepared for that."
She drove us to the catering hall where the party was going to be held, and
on the way, I admitted how apprehensive I was. "You know, I'm still worried
that I'll be found out." "So what," she said, "don't forget its Halloween
and everyone is in one costume or another. Yours is just more elaborate than
most." Her words comforted me a little, but I still had mixed feelings -
some guilt at dressing as a woman, some fear that I would be discovered and
ridiculed, and, of course, some wonderful feelings about the touch of these
clothes on me. When we got there, and walked into the party, there were at
least a hundred people already there, and I asked her, "how many people do
they expect?" Her answer, "at least a couple of hundred" made me shudder a
little - here I was dressed as a woman in front of that many people, but on
the other hand, with that large a crowd, I thought I could manage to stay in
the background. We went inside, and over to one of the bars to get a drink.
Before I could ask for a beer, Jennie ordered two strawberry daiquiris for
us. I sipped the sweet-sourness of the drink, and said, "this is awful! I'd
rather have a beer." She laughed, and said, "Sure, and slug it out of the
bottle like you usually do? Try to remember, you're a lady, and you have to
act like one." I smiled sheepishly at her, acknowledging that she was right,
and we began to circulate. It seemed that our exotic costumes were
attracting a lot of attention, and we were almost immediately surrounded by
a group of men. The contrast of my elaborately gowned body with Jennie's
obviously near-naked one had the guys in a state of heat. They were
performing the mating-dance ritual, competing with one another for our
attention. "That gown certainly shows off your figure," one of the would-be
Lotharios said to me. "Thank you, so much, kind sir," I simpered, laughing
to myself at the one part of my "figure" that would knock him for a loop if
he saw it. Music was playing in the background, and he asked me if I would
like to dance. He was a pretty good-looking guy, dressed in a vampire
costume, but I begged off with a "not right now, thank you". I really wasn't
all so sure of myself in heels that I was ready to try to dance in them!
Jennie decided that we should break up this little group, and asked me if I
wanted to "powder my nose". I took the hint, and we walked over toward the
ladies room. Suddenly, it hit me - the ladies room. That was definitely
unexplored territory as far as I was concerned, and I said that to her.
"Don't be silly, no one will know - those guys certainly had no clue about
you."
There were only a few women in the room, and I immediately headed for a
large stall designed for handicapped people. It was large enough to
accomodate a wheelchair, and I needed to room for my gown. It still felt
strange sitting down to pee, not to mention just trying to maneuver around
my gown and petticoat so I could sit. I noticed that the whirlwind activity
and conversation had taken my mind off how I was dressed, and my cock was
still laying back limply; it seemed that I might be getting used to this a
little bit. I fixed myself up, and joined Jennie in front of the makeup
mirrors. She whispered that I could use a light dusting of powder and a
reapplication of my lipstick. I managed the powder OK, and was very
carefully applying the lipstick, when another woman walked over and stood
next to me. "My goodness," she said to me, "isn't that costume killing you?"
"Oh, its a little tight," I said, "but it really makes me feel so feminine!"
I caught Jennie's eye in the mirror, and saw her holding in a giggle. "No
doubt about that, dear," the woman said, "I saw all the Romeos around you
two before. Say, wasn't that guy gorgeous, the one who's the vampire?"
Jennie took me off the hook and joined the conversation, "Yeah, he was
really cute." "I wonder how big he is," the woman responded, nearly knocking
me over with her words. I had no idea that women's conversations about men
were as graphic as men's were about women. "Oh, I never worry about that,"
Jennie quipped, "its not how big it is, its what they can do with it, after
all!" They dissolved in giggles, and I tried to recover and join in. The
woman left, still laughing, and Jennie and I were alone for a moment. "I had
no idea that you girls were that gross," I commented. "Well, don't you think
its fair?" she asked. "You guys talk about tits all the time, don't you?" I
had to admit that she was right, and we went back out to the party.
The next couple of hours passed in a blur as the party swirled around us,
and then the crowd started to thin out a little. Then Jennie said, "Oh, oh,
here's my boss, Mr. Harrison," as a tall distinguished looking guy walked
over. "Seems like we should have come to the party together," he said to me,
after Jennie introduced us. "I hardly think so, suh," I said in my sweetest
southern belle voice, "after all, you are a Yankee!" He had on a blue Civil
War officers uniform. "Well, I personally think that we should end the `War
between the States' ," he said, and before I could answer, he took my hand,
kissed it, and led me over to the dance floor. I didn't have much choice
about it, and I almost gave it away by raising my left hand to lead. I
covered up by patting my hair, and soon found myself twirling around the
floor, following his lead. He asked me about myself as we danced, through
the first song and into the second, and we chatted for a while. Finally, the
song ended, and again kissing my hand, he led me back over to where Jennie
was standing. "I think your friend is absolutely charming, Jennie, I'm so
glad she came with you tonight.And I'm holding you personally responsible
for making sure she keeps our appointment." He said goodnight and walked
away. "You seemed deep in conversation, Robin, what was he saying? And what
did he mean, appointment?" "Jennie, you're not going to believe this, but we
have a big problem. He was asking all about me, where I worked, where I'd
gone to school, and when I told him I hadn't found a job yet, he insisted on
making an appointment for an interview for next Friday. I couldn't refuse
him, since he's your boss. What a mess!" "Well, don't worry, we'll think of
something, some excuse or something by then." We decided to leave since the
party was breaking up, and Jennie drove us home.
"I guess you realize that I won the bet," were the first words out of
Jennie's mouth when we walked into the apartment, "nobody had a clue all
night." "I know, you're right," I said. "I didn't believe for a minute when
I agreed to the bet that I'd ever be able to pull it off," I admitted,
pulling her close to me in a hug, and kissing her, "but I did have a
wonderful teacher." She closed her eyes and kissed me back passionately,
then murmured, "I love the taste of your lipstick." We stood there kissing
for a while, and then we moved toward the bedroom, arms around each other's
waists. "You're a beautiful Scarlett O'Hara," she said as we fell onto the
bed together, "and I want you right now!" She lay me down on the pillows,
and raised my skirt and petticoat, laying on top of me with the velvet and
crinoline crushed between us. We rubbed our bodies together for a while, and
the sensations from the clothing and her body surged through me. She lifted
herself away, and removed my bloomers and the sanitary napkin that was
restraining me. My cock sprang to attention and she pulled off her dress and
panties, leaving her wearing only thigh-high stockings and heels. She moved
back on top of me, and I spread my legs so that she could fit between them.
My breath was coming in short gasps, from her weight on top of me, and from
the tightly laced corset, and I stopped breathing entirely when her wet
pussy devoured my erect cock. I wrapped my stockinged legs tightly around
her, and I could feel my high heels digging into her back. I had the
sensation that the cock that joined us was hers, and I felt so very, very
feminine as she pumped away on my womanly body. A bolt of electricity surged
through my body, starting at the groin, and exploding in my head as I had a
magnificent orgasm, and her whispered, "yes, yes, y-e-e-e-e-s-s-s," told me
that she, too, had come. We lay there for a while, just like that, as I
didn't want to let her get out from between my tightly wrapped legs. Then
she helped me up, and, with great reluctance, she began to get me undressed.
She helped remove my makeup, and we crawled into bed together, naked, and
made love again, this time less furiously, but rather with a deliberate slow
sweetness. As we lay there, drifting off to sleep, I almost started to
mention the problem with Mr. Harrison, but decided that I didn't want
anything to spoil what had been a perfect night.
The next morning we talked about how wonderful the party had been for a
while, then when I thought the moment was right, I brought it up. We were
sitting there in our own robes when I said, "Jennie, I really think that
we've got a big problem here. Mr. Harrison all but told me that he wanted to
hire me, but he'll be really pissed off when he finds out that he was fooled
and was dancing with a guy. I mean, he was being so gallant, kissing my hand
and all, he'll go right through the roof. Maybe I can cancel the appointment
and say that I found something else." "I don't know, Robin, that would sound
fishy I think, since you told him that you've had no luck at all. He might
get mad at me, since he said I was personally responsible for delivering
you. That's all we'd need, for me to get fired." I agreed, since it was
Jennie's earnings that were keeping us from being starving homeless people.
We talked back and forth for a while, trying to figure some way out of the
dilemma, when Jennie said, "this is hopeless. I can't figure out any way to
solve this, unless ..." "Unless what, Jennie?" "Unless you keep your
appointment, silly." "But I can't do that - I just know he'll be pissed off
when I walk into his office in a suit," I said. "Not if its a woman's suit,"
she replied. "Now wait just a second," I said, "I agreed to go to the party,
that was one thing, but this is something else entirely. I'll never get away
with it." "Sure you will, he'll be expecting to see a woman, and that's what
he'll see. You can go in for the interview, and that will be the end of it.
Simple, one hour and it'll get us off the hook." We had our first argument
about it, because I felt that it was much too risky - if Mr. Harrison would
be pissed off to find out I was a guy, how pissed off would he be if he
caught me trying to pass myself off as a woman when he was interviewing me?
Jennie believed that I could get away with it, but my confidence level
wasn't anyplace close to that high. Finally, she used the ultimate female
argument - she burst into tears, and what could I do but agree to try her
plan?
"Listen," she said a while later, "we've got a few things going for us.
First, your appointment is for first thing in the morning, so I'll be able
to get you ready and go in with you. Second, he's not a real morning person,
so he won't be as sharp as usual. Third, we have another week to work on
you. That's a big help. We'll have to get you an outfit to wear, but I can
always give it to Patty as a Christmas present, so it won't really cost us
much." What she said seemed to make sense, so I told her that I guessed it
would be OK, and that she should pick up the outfit for me. "We can't do
that," she said, "you'll have to try it on, to make sure it fits right and
looks good. I can't be running back and forth to stores all week, there's
too much else to do. We'll have to go shopping today, so you can try things
on before we buy one." Again I balked, arguing that I couldn't go shopping
and try things on in stores. "Well, if you're going to pull this off," she
countered, "you'd better be able to pass yourself off as a woman! And
remember, there's no Plan "B"." So, about two hours later, I was nervously
getting out of the car at a shopping mall, dressed in the pink and white
shirtwaist dress I had worn the first time I'd dressed. Luckily it was a
warm day, late Indian summer weather, and I didn't have to wear a coat,
which I didn't have anyway. I was wearing the white undies and pantyhose,
and when we got into the mall, I heard the clicking of our heels on the
marble floor. This time, dressing hadn't excited me, because of the risk I
was taking. Halloween was over, and if I were found out, I envisioned myself
in jail or something for being in drag in a women's dressing room. We went
into a department store, and hurried past the cosmetics section, with the
sales people offering everything from samples of perfume to full
demonstrations of cosmetics, into the women's department. "First, you'll
need your own undies," Jennie said, "because I'll have to return Patty's
stuff within a couple of days." She went through racks and racks of bras,
panties, and other "unmentionables", selecting a few things for me to try
on. "One good thing," she said, "is that we girls share dressing rooms all
the time. No one will think it unusual for the two of us to go inside one
together. She picked out a few things in her size, and we went over to the
dress department. "I think that a suit might be better than a dress," Jennie
suggested, "because everything will go together, and you won't have to worry
about about something not fitting quite right, because they'll be
separates." She picked out a couple of suits and blouses, and we headed off
to the dressing room. My biggest fear, that the attendant would spot me, was
allayed when I saw that she was only concerned with counting how many
articles we were taking inside. We went into the cubicle, passing women in
various stages of undress, and closed the door. "I'll bet this is every
guy's fantasy, seeing lots of women in their undies," Jennie whispered to
me. "Well, its certainly better than a sharp stick in the eye," I teased
back, as I was undressing. She poked me in the ribs and said in a mock
serious tone, "just remember who brung you to the dance, buster!" I quickly
stepped into the panties that she handed me, and tucked myself back. She
slipped the matching bra around me and fastened it, stuffing the extra
panties that I was using into the cups. She handed me a white half slip, and
then a silky white blouse with a lacy ruffle around the neckline. I tried on
the skirt from the first suit, then the one from the second. "No, these
won't fit your waist properly," she said. We'll have to get something to
pull it in. Wait here a second." With that she went out, and I never felt so
alone in my life. I was like a spy in enemy territory. She came back in just
a minute or two with two things, a padded panty girdle and a waist cincher.
She fastened the cincher around me, and the hook-and-eyes pulled my waist
in. Then I put the panty girdle on, compressing my waist even more, but
adding a little padding to my buns. The skirts fit now, and I put on the
jacket. "Well, I think either of these will do," she said, "which one do you
like better?" One of the suits was a navy blue, the other a nice green. "I
think the green one," remembering how much I had loved the green velvet
gown. "I agree, and besides, Patty already has a blue suit, so when we pass
it along, she'd like the green one more."
I changed back into my own things, and we headed to the shoe department. I
was again a little worried about being so close to someone, but Jennie
reassured me, "don't worry, if its a guy, he'll be too busy concentrating on
trying to look up your skirt." It was a guy who helped me, and Jennie was
right. I was almost tempted to let the loser look ALL the way under my
skirt, but I restrained myself. I picked out a pair of green suede pumps
with a 2" heel that went perfectly with the suit, and after we paid for
everything, we hurried home.
The next week was another blur, and before I knew it, it was Thursday night.
"We'd better get a few things done tonight, so we'll be OK in the morning.
She glued on extension tips to my own nails, saying that it was better not
to have to worry about a stick-on nail coming off. When she had all ten
fingers done, I was amazed at how much more natural they felt. She manicured
my nails then, shaping the extensions and applying a subdued medium red
polish. I was surprised when she started putting polish on my toenails, and
I said, "why bother, he's not going to see them?" "Trust me, you'll feel
more feminine with them polished," and when she finished, I found that even
this hidden sign of femininity did make me feel more girlish. I took a nice
long bubble bath, and shaved my legs and underarms. My face I would take
care of in the morning.
When we went to bed, Jennie surprised me with a slinky black nightgown that
I hadn't even seen her buy, and we slid into bed together, our silken
covered bodies sliding against each other as we made love. I tried to be
careful, but as I was getting ready to come, my long nails dug into her
back. This seemed to excite her even more, and we lay there, out of breath,
for a while until we fell asleep. The next morning was a panic, in
retrospect, as two girls tried to get ready at the same time, but by the
time we were ready to leave, I felt pretty confident that I was going to be
able to pull my masquerade off. I wished, though, that I could have been
wearing a heavier makeup, feeling somewhat naked and exposed with a natural
daytime look, but Jennie patted my padded fanny and reassured me that I
looked great.
The moment of truth arrived all too quickly, and Jennie brought me into Mr.
Harrison's office, whispered, "Good luck," and left, closing the door behind
her. "Good to see you again, Robin, glad you could make it," he started.
"Why don't you sit here on the couch, where you'll be comfortable?" He
proceeded to interview me, sitting next to me on the couch, and I noticed
that he couldn't keep his eyes off me, focusing most often on my breasts and
legs. I answered all his questions easily, having been on so many interviews
already. "You know, Robin, I have to admit something. I thought you looked
wonderful at the party, and you look just as nice today." "Well, thank you,
Mr. Harrison, its very nice of you to say that," I replied. But the sleaze
wasn't finished yet - he put his hand on my nylon-covered knee, and said, "I
find you VERY attractive, and I'm sure we can find a job for you here." His
hand moved slowly up onto my thigh, under my skirt. The son-of-a-bitch was
making a blatant pass at me, and was about eight inches away from
discovering my secret. My first impulse was to haul off and belt him, but I
controlled myself and stopped the upward movement of his hand. "Mr.
Harrison, I'm surprised at you, what kind of a girl do you think I am? I
know you're married, Jennie told me so, and I wonder what your personnel
people will think when I slap you with a sexual harrassment lawsuit?" He sat
back in shock, realizing the position he was in. He stammered, trying to
make excuses for what he had done, but I clearly wasn't buying it. "I just
couldn't help myself, you were so beautiful in that gown, and your green
suit reminded me of it ..." "Mr. Harrison, you are in a world of trouble,
now, because my next stop is my attorney's office!" He seemed to shrink
inside himself, and he began to beg me to forgive him and to forget what had
happened. Finally he said, "Robin, please, I'll be ruined, isn't there
anything I can do?" I loved the position of power I was in, and I realized
that women were not the weaker sex after all. But I knew that with no
witnesses to what he had done, I needed more leverage to take advantage of
the situation. "You said that you definitely had a job for me here?" "Ah,
yes, of course," he answered. "And what might the salary for this job be?" I
inquired, adding, "remember you did say anything, right?" "Would er-ah $35,
000 be adequate, Robin? I'm sure we could go that high." This weasel was
offering me $7,000 more than he was paying Robin, to save his ass.
"Oh, that sounds very fair, Mr. Harrison," I said, beginning to bait the
trap. "You know," I continued, "I may have overreacted before, I'm sure you
didn't mean anything nasty, did you?" "Oh, no, of course not," falling
deeper into it. "As a matter of fact," I said, tracing a line on his cheek
with one of my long red-tipped nails, "I found you quite attractive as well.
Maybe we can reenact the Civil War someday," I teased. Thump! He fell all
the way in. I moved my hand down from his face to his belt, and started to
unbuckle it, saying, "perhaps we should seal our agreement, don't you
think?" I almost felt sorry for him, but quickly got over it, as I unbuckled
and unzipped his pants. He stood up, took off his shoes and stepped out of
his pants. "Can we sit in your desk chair," I asked, innocently, "I love
positions of power." He couldn't get there quickly enough, and I nestled on
his lap, gazing up into his eyes. I felt his hardon pressing against my
buns, and I wriggled around on it, driving him further to distraction. While
he was lost in his fantasies, I reached over and picked up his phone.
"Jennie, dear, could you come right into Mr. Harrison's office, I need your
help." "W ... what did you do that for," he cried, and he tried to get me
off his lap. "No, Mr. Harrison, you're not going anywhere," I said. And at
that moment, Jennie came into the office, expecting the worst - that I had
been found out. She burst out laughing when she saw the two of us, and
quickly shut the door. "Mr. Harrison has made me a job offer, Jennie," I
said, rising off his lap. "Stand up, you creep," I said to him. His hardon
stuck out through the opening in his boxer shorts, but I could see it
wilting away. "he offered me $35,000, isn't that wonderful? I was going to
accept, but then I thought, you know how we girls gossip, and I just knew
that you''d find out how much more I was making than you. That wouldn't be
fair, would it?" "No, I guess not, especially under these circumstances,
sexual advances and all."
The poor bastard just stood there, realizing that we had him by the short
and curlies. "What are you going to do?" he asked, very meekly, his cheeks
burning with embarassment. "Well, first of all, I think it would be only
fair to give Jennie a raise, don't you?" "Ah, yes, of course, immediately."
I handed him his phone, "OK, do what you have to do, right now." He dialed
personnel, and said into the phone, "This is Jim Harrison. I need an
immediate raise put through for Jennie Burns, to $35,000. Yes, I said
immediately. Another company is trying to recruit her, and we can't afford
to lose her. And prepare a contract for my signature, three years for her -
I want to lock her in now." He listened for a minute and said, "of course I
want raises specified in the contract, ah, five thousand a year," glancing
at Jennie, who nodded her agreement. "Yes, five thousand a year. And I want
that contract here on my desk within the hour." Some big shot Vice
President, ordering people around, while trying to retain his dignity in
polka dotted boxer shorts. "How about you, Robin," Jennie asked, "do you
want to accept Mr. Harrison's generous offer?" This was the question I had
been dreading. We could obviously get most anything we wanted, and I really
wanted a job, but it was out of the question now for me to take it as a
male. We would lose all the leverage we had if my secret were exposed. But
if I accepted it, I would have to dress as a woman all the time. My cock
stirred inside my panties, and I knew in my heart of hearts that I would not
stop dressing when I got home today anyway. I loved being in frilly panties
more than anything. "What do you think, Jennie, I think you have a great
deal to say about this, since we'll be working together." That's what I
said, but the hidden meaning to my question was clear - did she want,
approve of, my continuing to dress as a woman? "Why, Robin, dear, I think it
would be wonderful, and exciting, to have you working here with us." I could
not have hoped for a more supportive, understanding answer.
I handed the phone back to Mr. Harrison, and he instructed personnel to draw
up a second contract for me, on the same terms. Jennie slipped out of the
office, but quickly returned, carrying her large purse. "I think we've
treated Mr. Harrison so badly, Robin, don't you?" "Yes," I said, playing
along with her, but not knowing where this was going. Mr. Harrison has a
reputation for being a real hard-nosed businessman who always manages to
come out on top. She pulled a Polaroid camera out of her bag, saying "we use
this to take a quick look at ad layouts and things, but we have a better use
for it now - insurance. Take off your clothes, you worm," addressing
Harrison. He started to protest, but Jennie cut him off, "if you don't do
what I tell you to, I'll call your secretary in to see you in your funky
boxer shorts. And you know what a gossip she is - it'll not only be all over
the company in twenty minutes, your wife will know in ten!" He had no
choice, so he silently stripped everything off, and beagn to follow our
instructions. "First of all," Jennie said, "you have to look like you're
enjoying yourself. Rub that little cock of yours until it stands straight
up." Mortified, he began to stroke himself into an erection. We then began
to pose him with each of us, first with his arm around our waists, then in
progressively more humiliating poses. We made him kneel down, and we took
turns using his back as a footrest. Then we shot pictures of him licking our
high heels, his erect cock in hand, showing how much he loved it. Finally,
we bent him over his desk and whacked his ass with a ruler, until red welts
showed up clearly all over. "Play with yourself as I'm doing this, creep,"
Jennie ordered, "make yourself cum in your hand!" He did, blushing the
deepest red I've ever seen anyone blush. "That's what you wanted, isn't it?"
I asked, and when he came in his hand, I continued, "you were probably
hoping for a blowjob, to have me taste your filthy cum - rub it around on
your lips for the final shot!" He groaned, but complied, and Jennie snapped
two pictures, one with the cum pooled in his hand, clearly having just shot
his load, and the second as his hand moved to his mouth and rubbed. "You
might as well lick it off and swallow it, you pig," Jennie laughingly
ordered.
After his final humiliation, we told him to get dressed, while we waited for
the contracts to be delivered. I spent the time planning the wardrobe I was
going to buy, and all the wonderful things I would be able to wear. He
signed the contracts, and as I was ready to leave with our copies, I said to
him, see you bright and early Monday morning, Mr. H!" "I think I'm feeling a
little poorly, Mr. Harrison, would you mind if I took the rest of the day
off?" Jennie said. He nodded his agreement weakly, and we walked out, arm in
arm.
Well, this