Roles Reversed
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Roles Reversed free porn video
ROLES REVERSED
by "c.c."
I'm a high-ranking official in the Administration of a large mid-western
University, and though I've always had an interest in Tranvestism, I know
I'm just too manly-looking to cross-dress successfully. So for years, I
just went along fantasizing.... Till I met Gloria.
Gloria is a good-looking, well-educated woman about my age who makes ends
meet with a variety of part-time jobs around the University; She works in
my office from time to time, she schedules events for some of the Women's
Athletic Association... and she's a fill-in House Mother for the Lesba-
Delta Sorority! It was in this capacity that she first came to my
attention.
Gloria reported to me one day about a problem... and how the girls of
Lesba-Delta wanted to solve it.
"We caught a young man spying on his girlfriend's Initiation," She said,
"And we certainly don't want him telling all his friends about it. In
fact, the less he says about the whole experience, the better. So we
threatened to report him to you, Doctor--unless he agreed to attend our
Mixer Dance... in Drag!"
Well you can imagine how my interest perked up at that! But I tried to
keep my cool.
"Won't that be a bit disruptive?" I asked innocently. "Having a man in
dresses at your dance?"
"Not a bit," Gloria said, "He's a handsome but rather soft-looking guy,
and what the girls have done to him already--shaving his body, setting his
hair, experimenting with makeup and various outfits--well, let's just say
they've been very successful in changing his appearance into that of an
attractive young co-ed. And that's what I need your help for."
"My help?" I hoped I still looked innocent.
"That's right. Like I say, we threatened to report him to the Discipline
Office - your office--unless he goes along with this. But I don't think he
ever imagined we could make him look quite as feminine as we have. And as
a result, he's getting just the teensiest bit rebellious. Of course,
there at the Lesba-Delta House, we can always spank him when he gets
sulky, but we want him to be on his best girlish behavior at the Dance,
and we thought the best way to ensure that would be to have you there as
well; when he knows the University Discipline Official is there, watching
his every move, he'll try extra hard to look and act like a proper young
lady to keep from getting caught. Well, Doctor, can you help us out?"
I wouldn't have missed a chance like that for the World. But I was
already thinking about what else I could do... wondering if there wasn't
some way I could see some of my fantasies acted out -- safely, by proxy -
- while I watched and engineered things. So I answered:
"Yes, on Three conditions: First, call me Richard; Second, if I go to the
Dance, it'll be as your Date; and Third, I want to take you to Dinner
tonight."
And Gloria agreed to all three.
Over the next week, in fact, she and I went out twice. I found her a very
agreeable companion, and in the back of my mind there was always the
thought: If she was willing to feminize one man....?
The night of the Dance arrived at last, and I had Gloria point out her
cross-dressed victim to me as soon as we entered. What I saw was a cute,
very shy-looking young lady in a quiet but rather short dress, with well-
styled blonde hair and alluring makeup that accentuated her soft blue
eyes and full, pouty mouth, set in a demure face crowned by girlish
ringlets.
"His name's Dana," Gloria confided to me, "and that's what we call him."
"Follow my lead," I whispered, and walked up to the boy/girl, who was
obviously hoping no one would notice him. "So this is the young woman you
were telling me about," I said loudly, "Pleased to meet you, Dana."
He looked panic-stricken. Gloria was puzzled, but she said, "Er-that's
right, Dr. Rosen, this is the girl."
"Gloria tells me you need a little part-time work," I said commandingly,
"A few hours a week of light office duties, and I have the perfect
opening."
"That's right," Gloria, still unsure where I was going with this, went
along, "I told Dr. Rosen you'd be glad to help out."
"I-uh-er...that is... " His soft, frightened voice passed easily for that
of a girl, and he gave Gloria a cowed, submissive look, as if unsure what
she wanted but afraid to displease her. "Th-that's right, Dr. Rosen, if
you'll just let me stop by your office some time I'll--"
"No time like the present," I boomed, "let's get you to my office and get
you signed up. It's just across the Green, and we can get the
preliminaries out of the way in a few minutes. Be back here at the dance
before the fellas miss you."
In short order, I had them in my office and Dana was filling out Part-
Time Employment forms. I had Gloria read me the Number off Dana's Student
ID, entered them in the Master Computer, and when his real statistics
came up, I quickly changed the Male designation to Female Then I read off
his address, phone number and other statistics. Numb with worry that I
might notice his true sex and get him expelled, he confirmed it all.
"Fine," I said, punching a few more buttons, "You're on the Payroll now
as a part-time Office Temp. Just one more detail," I led them to a white
screen in the next office and had Dana stand in front of it. I already
had the Camera set up, but when the light flashed, I thought the poor
girl-boy was going to jump out of his dress.
Two laminated cards slid out of a machine seconds later, and I handed one
to Dana. "Your Security ID," I said, "I'll keep the second Photo ID in
our files. And I'll expect you Monday Afternoon."
"Yes sir," he said meekly.
On the way back to the Dance, I said "Remember Dana, working for me will
involve some Campus Security matters. So if you miss work for any reason,
I'll have to send the Campus Police around to your home and classes with
that picture of you. So be sure to call in if you have to miss for any
reason."
I had him! Gloria looked at me wonderingly, but said nothing. Till we got
back to the Dance; then, after we socialized a bit, she got me alone and
asked, "Richard, just what are you doing to that poor boy? Now he thinks
he has to dress up as a girl for a few hours every week and do your
Office Work."
"He does," I said, still trying to hide my enjoyment, "You said you
didn't want him bragging about this to his friends, and I thought this
was the best way to prevent just that. Don't worry, I'll let him off
after a few days. But by then, he'll be so worried about getting in
serious trouble, he won't dare breathe a word of this to anyone."
Gloria gave me a close, careful look, but said nothing.
Over the next few months, Gloria and I kept seeing each other as Spring
turned to Summer. I grew more and more attracted to her, and (I thought)
she to me. Sometimes she would see Dana working around my office, in his
makeup and short dresses, and occasionally she would ask me when I
planned to end his extended transvestite penalty, but I always put her
off with some excuse.
As for Dana, the unfortunate young man seemed to resign himself to his
fate. I was careful not to put too many demands on him, beyond telling
him that Slacks were not permitted on the Office Staff, and though I
ordered him to do a lot of bending and stooping work (which ensured that
he wore panties at all times) I tried not to pressure him too much; I was
really enjoying living out my fantasies vicariously with this cross-
dressed serving girl, and I didn't want to ruin it.
So things went quite well for me. Then Gloria and I started getting more
serious about each other. Things came to a head one evening when she was
having Dinner at my place. Afterwards, we started petting, but just when
I thought I was going to get her into Bed at last, she broke off.
"I'm sorry, Richard," She sighed, trying to catch her breath, "But I just
don't want to make love with you, then get up and go home. And I have to
spend almost every night this month at the Sorority House."
"I understand," I tried to sound patient, "but when do you think we
might...
"I'll find a way." She smiled and kissed me again, fully, sensuously,
then came up for air. "And when I do, you'll never forget it!"
A week later, she had the answer.
"I was booking a place for the Women's Wrestling Team," Gloria called me
from her office, "And I found the most wonderful cabin: Just an hour's
drive away, but totally isolated and set deep in the Woods, next to a
river. We can spend a long weekend there getting to really know each
other."
"Sounds great," I enthused, "I'll pick you up Friday afternoon and--"
"Sorry," She interrupted, "But I- have waay too much to do Friday, and
I'm not sure when I can get away. But if you could go there ahead of time
and get the place ready, I'll bring Steaks and Champagne... and a cute
little nightie!"
"I'm practially there already," said," Anything I should bring?"
"We-ell," She hesitated, then apparently decided something, "I should
tell you... I -- well, I'm kind of turned on-by-by men without any body
hair. Oh, I know it's a lot to ask a macho type like you, but a guy with
smooth skin really..."
"Say no more!"
As I put down the phone, I thought I noticed the short-skirted Dana
giving me a funny look, but I was too preoccupied with visions of Gloria
to give it much thought.
Friday, I picked up the directions to the Cabin from Gloria's Desk, and
by late Friday Afternoon I had followed the torturous route out the
winding back roads, over the gravel trail through the woods and to our
cabin by the stream. It was perfect! Quiet and isolated, with clear water
lapping on the bank. As soon as I got out of the car, I pulled out my
cell phone and called Gloria.
"It's lovely," I said, "But I forgot: I don't have a key."
"That's all right," Her voice crackled out of the receiver at my ear,
"I'm a ways off yet, and shouldn't be too long. Why don't you 'go for a
Swim or something while you're waiting?"
"I didn't bring my suit."
"That makes it an even better idea!" And she rang off.
I looked at the inviting water, feeling grimy from the trip, and thought
how sexy it might feel, with my smooth body and all (I had-used a
depilatory all over, followed by plenty of soothing lotion the night
before!) to go skinny-dipping in the clear river. Minutes later, my
clothes were folded neatly on the bank, and I was rinsing myself off in
the bracing waters, lathering myself with scented soap, then swimming a
few hundred yards upstream and drifting slowly back, without a care in
the world.
Or so I thought.
If only I had known that Gloria had gotten suspicious of me that first
night at the dance. She had also grown resentful of my treatment of Dana.
And worse yet, Dana's girlfriend was still a member of Gloria's sorority,
and she was growing angrier still of the way her guy was forced to spend
a few hours every week in drag. And she had friends on the Women's
wrestling team!
But I knew nothing of all this, swimming lazily down the stream, thinking
of Gloria and the ways I would satisfy myself with her body. I grew more
and more aroused, just imagining a long weekend making love to her amid
these surroundings. And so absorbed in the fantasy, I didn't hear the
girls come sneaking over to the riverbank. Didn't hear them as they
spotted to me, whispered to each other and barely contained their
giggles. And I most certainly didn't see them snatch up all my clothes
and sneak them away!
No, I was just blissfully planning my romance, feeling my malehood grow
stiff in the water, when I heard my cell phone chirp from the bank.
I swam over, saw it lying there in the grass. Shouldn't my clothes be
there, too? Or did I leave them somewhere else? Feeling a bit nervous, I
grabbed it and backed into the water till it was chest deep.
"Richard?" It was Gloria. "Where are you?"
"I'm at the cabin," I said, "Or in the stream by the cabin. Where are
you?"
"I'm at the Cabin," She insisted, "And I don't see any sign of you or
your car. Are you sure you're at the right place?"
"I followed your directions," I said, "The ones on your desk."
"Oh no," her voice in the receiver sounded odd. "I hope you didn't pick
up the wrong set -- to the cabin where the Women's Wrestling Team is
staying."
I had a sudden picture of myself being spotted, all nude and smooth-
skinned, by those rowdy amazons. It chilled me more than the cool water.
And where were my clothes?
"Richard?" Gloria's voice interrupted my thoughts, "Listen, if you're at
the wrong cabin, ours is just a few miles upstream. The gravel road will
get you there as well. Only we're not as alone as I thought we'd
beggggghzzzzphzzz-" her voice broke up.
"What do you mean?" I asked, "I may be in a little trouble myself. Can
you drive over here and--"
"Bzzzphgghhzzph!" Came into my ear, "-some girls from the soPhzzttzghg--
stfzzttt"
Then silence.
I pulled myself up on the bank and started searching desperately through
the bushes for my clothes. Where were they? Had someone taken them? Could
it be the Women's Wrestling Team had gotten here already and hid them for
a joke? Once again I had the chilling feeling of being watched by
giggling ladies, amused at my nudity and my smooth, girlish skin. I felt
myself blushing from head to foot. I had to get to Gloria!
But how? My car was locked and the keys were in my pants -- wherever they
were. Then I remembered what Gloria said about our cabin being a few
miles upstream. I could walk it along the creek bank, if I was careful.
Then Gloria could call a locksmith and get into my car so I could get
dressed again.
But as I started tiptoeing through the bush, I remembered something else
Gloria had said... about other people at our cabin. Was it some girls
from the Sorority? Girls who would see me like this? The idea of falling
nude into the clutches of those immature girls-was almost as bad as being
victimized by the Lady Wrestlers. Perhaps I could sneak close enough to
the cabin to hide in the bushes and get Gloria's attention....
Then I spotted the clothes hanging on the line.
It was behind the cabin, on the other side from where I'd been swimming.
A whole clothesline, I could make out through the trees, hung with
clothes. This might be my salvation!
Cautiously, I moved through the thicket in a half-crouch, looking this
way and that, listening for' anyone around. Clothes on the line meant
there was someone here... but maybe they'd gone hiking or something. If I
could just get close enough to grab something to wear...
At last I got close enough to dart out of the woods and up to the
clothesline. To my disappointment, there were no slacks or shorts I could
wear. Not even a shirt! The entire line was hung with frilly lingerie and
brightly-colored silks, sexy nightwear,panties, garterbelts and exotic
silk stockings.
For just a second I stared at the erotic display, overcome with confusion
These were the things I had fantasized about, the kinds of attire I had
tricked Dana into wearing for my amusement. And now here I was, nude and
hairless, trying to find some practical, manly clothes, and all there was
was this thrilling, frustrating fantasy attire.
Head spinning, I fumbled through the lingerie, looking for something to
wear. The feel of the smooth satins and gossamer silks slipping through
my fingers set my tummy fluttering nervously. How would these panties
feel, covering your smooth, pale bottom? Imagine those black silk
stockings on your shapely, feminine legs, pulled taut by a frilly
garterbelt..,.
It was like living a page from a transvestite fantasy, stories I had read
so often. Imagine being all alone, nude, smooth-skinned, and surrounded
by the sexiest, most sensuous lingerie imaginable! For a moment, I was
lost in the sheer unreality of it all.
How long did my reverie last? I don't know. Finally, I shook off my
dream-state and tried to concentrate on the problem at hand. Fantasizing
about cross-dressing might be one thing, but it'd be a very different --
and embarrassing -- matter altogether to be caught by College Girls in
such outlandish attire! I finally saw a scarf that might double for a
small towel. But then--
"What's this?" The hard, female voice cracked behind me like a physical
blow! I jumped and squealed.
"Looks like some Thief-Pervo trying to make off with our stuff!" the
second voice was equally female and just as butch. I glanced guiltily
over my shoulder to see two tall, well-built college girls in jeans and
cut-offs regarding me with a mixture of anger and grirn amusement.
"Well he does need it!" One of them giggled, her eyes running up and down
my naked body as a third girl came up the path.
"That doesn't give him the right to steal from us," Her chunky, curly-
haired friend replied.
"Hey, nice butt!" The third girl, tall and willowy, with long, flowing
hair joined us now. Speechless, I clasped my hands shyly over my privates
as she took her time staring at me. "And shaved smooth," she approved,
"Where'd you find him?"
"This thing?" Curly-hair jerked a thumb disdainfully at me, "Caught the
little she-male trying to steal our clothes!"
"He'd look cute in them," Her blonde friend mused, "Maybe with his hair
curled and some makeup." She cupped a hand under my bottom-cheeks and I
jumped. "But you know, he looks kinda familiar..."
Suddenly overwhelmed with panic, I turned and ran. I couldn't let them
recognize me! Imagine the shame: caught nude and smooth-skinned, stealing
clothes from coeds! I had to get away! Reckless with fear, I bolted
through the woods toward the stream. If only I could jump in the water,
maybe they wouldn't follow me!
But I never made it that far. I keep myself in pretty good shape, but I
was no match, barefoot and naked, for three fully-dressed female athletes
in tennis shoes. Long before I got to the stream, I felt strong, feminine
hands on my arms, pulling me back. I jerked, flailing my arms wildly,
felt my hand connect with something, and heard the curly-haired girl
swear.
"So you'd hit a woman? Well we'll just see how you like it!"
Suddenly they were all over me, pushing me to the ground, pinning my
arms. One of them threw herself over my legs, her full, firm breasts
pushing them to the ground, while another pulled my arms over my head and
pinned them under her knees, trapping my head in the vise of her thighs.
As I looked up in horror, the third one -- the willowy blonde, smiled
down at me and sat squarely on my face!
"Don't smother him, Trina," The dark-haired girl said, her voice muffled
in my ears by her thighs on my head, "Just cut off his air till he
decides to quit struggling. Josie-" She spoke to the chunky, curly-haired
one pinning down my thighs, "Can't you keep him from bucking like that?"
"Sure!" She giggled. Suddenly I felt a strong hand grip my genitals.
She didn't even have to squeeze. I went limp immediately, paralyzed with
fear and humiliation.
"Now," She snapped, "Do you still feel like hitting women?"
"NO!" I tried to shout under the soft, feminine butt pressing down on my
face.
"Are you sorry now? Will you do as we say7 will you?" She squeezed, ever
so slightly, and I nodded my head frantically under the blonde's bottom
till she "Ooo!ed" with pleasure.
"Okay," She rose to her feet and I gasped for air, "Let's dress him up in
those female clothes he wanted so bad."
"Not so fast," Josie declared, "First he gets punished for hitting me."
"But I didn't mean--" That was all I got out before I felt three pairs of
hands -lifting me across two female laps. The feel of my bare crotch on
Trina and Josie's soft thighs thrilled me for just a moment. And then--
WHAP I
A strong female hand landed smartly across my defenseless rear. "OwwwV' I
cried.
WHAP! WHAP!
"00000HI EEEKKI 000001" Time and again the gloating, vengeful girls
pounded pain into my pratt, till I thought 'I could feel it swelling!
"Keep, it up," Lorna, the third -girl brought soft drinks and watched
with amusement, "By the time we're through, I want this little wimp
begging to serve us!"
And that's precisely what they accomplished. By the time those butches
finished spanking me, I was sobbing helplessly, tearfully admitting to
stealing their sexy lingerie, swearing to do whatever they asked if they
wouldn't have me arrested. I told them who I was, where I worked, and
everything else they wanted to know. I promised them the use of my fine
car and expensive home, my money and credit cards, my wardrobe, even my
personal services, just to avoid the public disgrace of being dragged off
to jail this way.
"Now stop your crying, bad baby," Josie smirked, "And we'll let you dress
up in the frilly feminine underthings you've always wanted to wear."
No! I wanted to protest, I didn't want to wear those things! Not like
this, anyway. Not really. Or did I?
Whatever the case, I meekly submitted as the girls escorted me to their
cabin, pulled out a videocamera, and proceeded to dress me in a lace-
trimmed garterbelt, dark stockings, heels, and an ultra-feminine apron,
tied in the back with a big flouncy bow. They tied another big bow in my
hair, then applied makeup to my face, giving me red lips, drawn in a
sensuous pout, demure, blue-shadowed eyes with gracefully-arched
eyebrows, and pretty pink cheeks. They even painted my nails and put
rouge on my nipples and bottom!
Thus arrayed, I had to curtsey prettily and thank the girls for letting
me look do sweet. . . all captured on tape. I spent the next hour
practicing a feminine walk, a simpering voice, and every ultra-swishy
mannerism they could think of.
"The rest of the Wrestling Team will arrive later," Dark-haired Lorna
said, "And you'll prepare and serve Dinner for us. Don't worry, we'll
swear them all to secrecy... if you serve us properly."
All the while I fixed Dinner, my three captresses amused themselves by
making me perform silly chores, copping sly feels, pinching, stroking my
legs, and deliberately arousing me till my poor penis (Which I had
planned to enjoy with Gloria about now) rubbed maddeningly against my
silk apron skirts.
"Don't you feel silly like tht?" Blonde Trina teased, "A pretty girl like
you with that silly little thing sticking out under your apron?"
"Little is right," Josie sneered, "I really think this thing would be
better off as a girl. Maybe I could get some of my friends at the clinic
to permanently remove his body hair and swell up his breasts."
"Wouldn't he, look just so cute," Lorna chuckled, "Gadding about the
woods all nude like we found him... only with big breasts and a round,
feminine bottom? Trying to hide that ridiculous little thing in front?"
"She'd look sexy cleaning her apartment in that frilly apron," Josie
mused, "Getting it ready for our parties and such."
"And then, waiting on us and our friends." Trina copped another sly feel
and giggled when I jumped and squealed. "And if we get her to looking
really feminine, maybe we could find other uses for her. Tonight should
be good practice-- oh, here they are now."
The door opened and I gasped in dismay as more girls from the Wrestling
Team came in. But that's not all?Gloria was with them! And Dana! And
Dana's girlfriend!
"Gloria!" I squawked, "Get me out of this!"
But to my surprise, Gloria ignored me, walked straight over to Lorna, and
kissed her, a full, unmistakably passionate kiss, right--on the mouth!
Then she turned to me and smiled.
"Get you out of what, Richard?" She asked innocently, "Isn't this where
you've really always wanted to be? I hope so, because I'm afraid you're
going to be wearing female attire for some time to come."
As the other girls came in, laughing and joking about my appearance, I
felt myself chill and blush at the same time. And I noticed Dana was
dressed just as I was!
"That's right," Dana's girlfriend explained, "We got Dana to help us out
tonight in exchange for getting him out of his transvestite servitude.
But yours is just beginning, Doctor Williams. Once we've taped you and-
Dana performing for us, you won't be in a position to deny Gloria
anything."
"But don't worry, Pet," Standing with her arm around Lorna, Gloria looked
me up and down approvingly. "I won't be too, hard on you. You'll get to
keep your job and your outward male appearance, though you'll be required
to wear lingerie underneath your business suits. And your duties as Male
Maid for me and my friends will only take a few hours a week... just like
Dana was working for you. And who knows? If you're really sweet, and a
very good girl, I may make things a little easier on you. Once your
breasts are enlarged, perhaps we could even take you on vacation with us.
We'll see."
"But for tonight," Josie commanded, "You're ours. And for starters, I
want you to mince over to your sister-maid Dana and give her a big, wet
kiss."
I looked over at Dana, who was every bit as feminized as I was, but
smiling with satisfaction. Disconsolate, I scampered to him, my thoughts
a jumble of confusion.
Goodness! I wondered, How did I ever let myself get into this fix? Me, a
wealthy, successful man, turned into the half-naked, half-gendered Maid
to a clutch of lesbians and bisexuals! Is this really what I wanted all
along? Oh dear, no time to think about that. Must concentrate on acting
feminine and serving prettily.., if I ever want to get out of this, it's
my only hope!
Quivering, heart pounding, I embraced the feminized, Dana. As our lips
met and his hand gently caressed my nipples, I closed my eyes in a vain
attempt to shut out the flashes of cell phone cameras?.
thEnd!
Libbie
- 07.08.2020
- 20
- 0
