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Crystal's StorySite storysite.org

Hard Times

by Gingerfred Man

 

Prologue – Boring Historical Perspective

This story takes place in the future, at a time when the effect of
U.S. politicians' pandering to special interests and senior citizens,
the only demographic that actually votes, is fully realized. A new,
second depression has hit the United States and much of the world.
People are out of work and hungry. But, of course, not every aspect of
the economy and every individual would be suffering. People would
still spend their meager resources on what really mattered to them.
Like "Panty Boy" magazine, whose circulation actually increased during
hard times.

And even in the worst economy, some people still make money.

 

Chapter One – Opportunity

When I graduated from high school, I had no prospects for a job. I was
not alone. No one I knew had prospects.

The New Depression had depressed us all. Mom and Dad, thank goodness,
had paid off their mortgage during good times, but unpaid taxes were
threatening foreclosure for my unemployed parents.

My name's Brendan Casey and I was especially challenged for
employment. At five foot five and 130 pounds, I was unqualified for
the only kinds of jobs, "lifting-things" jobs, that people seemed to
be getting those days.

If it hadn't been for my mother's sister, we would have probably
starved. Aunt Tiffy seemed to have plenty of money and was very kind
to share it. We didn't ask where she was getting the money and didn't
even care if it was legal. I knew it had something to do with my
cousin Jeremy Murphy, who was a year older than I and rumored to have
a good-paying job.

I hadn't seen Jeremy in a couple of years, but I liked him a lot.
Small like me, he had a lot of chutzpah and a great sense of humor.

I wondered why no one spoke of what Jeremy actually did to earn the
money that was supporting two families. But I was about to find out.

A week after my high-school graduation, I received some incredible
news. I had a job!!!!

No one got jobs those days. Especially runts like me. But not only had
Jeremy arranged for a job for me, he told my mother that I would be
making as much as he was in a short time.

I was stunned. Then joyous. I never got to the skeptical stage, but I
should have.

 

Chapter Two – Vicki

Jeremy sent me a bus ticket and even some money for food along the
way. What a great guy! The fact that I had not received a job
description was a minor inconvenience.

Jeremy gave me his address and asked that I arrive at 6 p.m. on a
given day. I was so excited that I kissed my family goodbye and
arrived three hours early.

I stood in front of a lovely, posh, condo complex, gave my name to the
guard and was waved through to walk to Jeremy's apartment.

I wondered what the heck Jeremy was doing to make so much money, at
19, in a depressed economy. Whatever it was, I would be doing it soon
too. And making money.

Wow!

I took a deep breath and knocked on Jeremy's door. No response. I was
early. Maybe Jeremy wasn't home. I decided to sit and wait. But then I
heard footsteps. I was very excited. The door opened and there
stood…..a babe! A beautiful babe. Wearing a sheer peignoir robe, black
stockings and very high heels. The peignoir was opened to reveal the
cleavage of a large set of perfect titties. The babe's hair was
blonde, with lots of tight curls. Her face was a masterpiece – cute,
sweet and expertly made up, though the lipstick was a bit smeared and
she seemed a little disheveled. 

The shocker was that it was Jeremy's face. 

Oh my goodness!

I was speechless, but Jeremy wasn't.

"He" squealed very loudly and hugged me hard. "His" voice was sweet
and feminine.

"Brendan, it's wonderful to see you! I'm so happy you're here. You're
early, but that's all right. Did you have a good trip? I can't see you
right now, Honey, I'm working, but let me set you up in your room.
Follow me."

Dumbfounded, I did so. I watched my male cousin wiggle his way through
the house and shamefully, I got an erection. A big one. That would be
fodder for an analyst one day. If people could ever afford analysts
again.

Jeremy was chattering, "I think you'll like your room. You can watch
TV and there's food in the fridge. I have to get back to Rolf and
Sven, my two Swedish businessmen friends. I always say I'm only going
to make love with one of them, but I can never choose. They're such
dolls and they complement each other. Rolf likes my 'pussy' dry and
extra tight, so he always fucks me first while Sven watches. Sven
likes my pussy wet and sticky, so he always goes next. After that, we
just let things happen. "

I guess Jeremy noticed the look of horror on my face, but at first, he
took it as jitters.

Then he said, "Wait a minute, Honey. Didn't anyone tell you about my
job? Oh no, they didn't. Those cowards. I'm a hostess at the 'Panty
Boy Club' resort. It's a wonderful job. They made me over into a
beautiful, desirable girl and I couldn't be happier. Oh, Honey, don't
worry. We all keep our clitties and balls. See?"

Jeremy opened his silky peignoir and showed me a very nice, pink
package of cock and balls. Standing tall. Jeremy led me into a huge,
feminine, beautiful room with a private bath, king-size bed and home
entertainment center. The luxury of it in those times was stupefying.
Then he kissed me on the forehead, handed me the remote control and
sissy-ran back to Rolf and Sven.

I sat on the bed and began to tremble. My cousin was a faggot and all
my dreams had been dashed. How could I go home and tell everyone I
failed? I could never tell anyone the truth. But how could I give this
luxury up?

Horrible sounds of faggotry were coming from Jeremy's room. I had to
get away from it, so I ran to the kitchen. Wow! A full pantry and
refrigerator. How long had it been since I had seen that?

I considered having a sandwich. There was fresh bread and meat. Lots
of meat. And butter. I hadn't seen butter in quite a while. Mostly we
just ate rice and beans.

My stomach was turning, but how could I pass up that food? I made
myself a big, thick roast beef sandwich on two slices of sourdough
bread, with lettuce and tomato. It was heaven on earth. And I drank
two cans of Diet Pepsi as I considered my plight. 

Maybe I could get a different job at the resort. Maintenance or
bartending or something. Yeah, that was an idea. I would ask Jeremy
when he was done "working." His "work" sure was noisy. How could my
cousin allow someone to do that to him? Yet, he seemed so happy.

Eventually, Jeremy sent Rolf and Sven on their way and he joined me in
the kitchen. 

"Did you get something to eat?" my beautiful cousin asked.

"Yes, thank you, Jeremy," I said.

"Sweetie, why don't you call me 'Vicki?' I'm really not 'Jeremy' any
more and never will be. I'm a girl now and I love it."

I felt like regurgitating my roast beef sandwich and "Vicki" noticed.

"You're nervous about the change and about being with men," she said.
"Trust me. You'll get over that and love what you do. And you'll live
well, support your family, and make them proud."

I doubted that.

Vicki said, "That sandwich wasn't enough for you. Let me fix you
something."

She got up, moving easily in five-inch stiletto mules and began to fix
me an omelet. With three eggs! More eggs than a family would use in a
week.

"Aren't you eating?" I asked, as she set the omelet before me.

Vicki smiled. "I'm full, Honey. I must have swallowed a quart of Rolf
and Sven's cum. I'll have something later. Now tell me everything
about everyone back home."

I did. And that made her sad. She really was a sweet, caring person.
And the sexiest human being I had ever met.

Despite myself, I was very aroused in her presence. Her legs were
spectacular and the evil thought of doing things with Vicki that Rolf
and Sven had done with her just wouldn't go away.

Vicki was very wise. "Don't worry, Honey. You'll get a wonderful job
tomorrow when we meet my boss, Mr. Rodgers. Then you can help your
family and yourself and everything will be better for all of us."

I was hoping that Vicki meant something like a maintenance job or
something, because I could never be a "hostess" like her. Never.
Still, I had a painful erection caused by something, and it wasn't
dreams of unclogging toilets and sweeping floors.

Vicki noticed. "You poor kid. Look at you, all hard and throbbing. And
I haven't even offered you any relief. What a terrible hostess I am.
And what you must think if me. Now stand up and pull your zipper down.
You need a proper milking."

I couldn't! She was my cousin! I was scared.

Vicki said, "Don't worry, Honey. I'm not going to do anything bad. I'm
just going to help you clear your balls a little so you can think
about your future more clearly. Now, stand up."

I gulped and complied. My poor cock was outrageous. Vicki lovingly,
but efficiently pulled down my zipper, then pulled my pants and
underpants down to my ankles, revealing a respectable cock and balls.

Vicki whistled. "I haven't seen that package since we were little.
You'll be even more popular with equipment like that. Men like sweet,
innocent, shy, big-cocked sissies best."

I thought that the idea of men admiring my cock and balls would make
me lose my erection. Instead, I seemed to get even harder and warmer. 

Vicki began to stroke me, playing with my foreskin with her right hand
and cuddling my sore, needy balls with her left. "Yep, you'll be very
popular with the guys. They'll pay big bucks for the beautiful, shy
sissy in the red dress, with long legs in silky stockings. They'll go
wild when they see this pretty thing between your legs. <stroke>
They'll want to kiss it and put it in their mouths. <stroke, stroke>
They'll want to kiss it and lick it and suck your pretty pink balls.
<cuddle> Then they'll make you cum in their mouths, because you're so
pretty and sweet and feminine. And you'll cum hard <SPURT> just as you
are now. Ohhh! So much cum! You really needed that. Another big one.
That's my girl. That's my Tina!"

Tina?

No way.

But that stroking and the narration were certainly exciting.

 

Chapter Three – Tina?

At seven o'clock, Vicki said, "I have a date coming over for the
evening, Sweetie, but enjoy the rest of the apartment and your room.
Tomorrow morning, we'll take you over to Mr. Rodgers and nail down
your job."

She kissed me sweetly and I went to my room. I didn't want to be there
when her "date" showed up. I didn't want to look at any of her actual
"dates."

Looking around the room, I had to say it was very nice. I didn't see
why I would need a vanity area, but I loved the king-sized bed, the
private bath with sunken, doublewide tub and the huge TV. What grabbed
my immediate attention, though, was the stack of "Panty Boy"
magazines, going back three or four years.

"Panty Boy" had brought men's secret adoration of sissies out of the
closet and had made its publisher, Nick Nickerson, a billionaire. Nick
loved the good life, personally selecting the newly eighteen cuties
who dressed in gorgeous lingerie, and painted their faces for the
magazine's cumstorm-producing "pictorials." In every issue, there was
always at least one delicious, 30-plus-picture pictorial of a young
creampuff posing and stroking himself to cum after creamy cum, and
another, longer pictorial of a different pretty boy being loved, in
cummy detail, by a "Daddy" with a very large cock. Men bought the
magazine by the millions. In hard times, sales actually went up! And
the cover price of $10.95 (an enormous sum during the New Depression)
stayed constant. Men were willing to pay anything to forget their
problems and think about the soft love of a sissy, forgetting their
woes for several delicious, cummy minutes.

I began to look through the latest issue. I had seen the magazine
once, when I was about twelve and my Dad had left his stash carelessly
in full view. I remembered cumming in my underpants, the first time I
had ever orgasmed, as I flipped the glossy pages and saw a little doll
named "Lori" take what looked like a Genoa salami attached to a hairy
man's crotch, into her tiny, pink bottom. The look of ecstasy on her
face kept me awake several nights as I thought about making love to
her and making her popsy shoot cream, like mine did as I touched it
and thought of her. I also had brief, shameful thoughts about being
Lori, lying on my back as a man brought me to screaming, helpless
ejaculation. But I suppressed those thoughts as being gay. Right after
I emptied my balls.

I opened the latest issue to the table of contents. "Karen in her
boudoir, preparing for her man" was the first "pictorial," then a
photo article about Nick Nickerson's latest extravagant party at his
extravagant mansion (the Panty Palace) in Fromage, Wisconsin. Then an
article on some new Italian penis-extender car, a "pigskin preview,"
and the coup de grace, an extensive pictorial entitled, "Cynthia
completely satisfies her lover…..and herself."

I was sure the TV remote was somewhere and I could watch arm wresting
on ESPN5 or something, but I decided to look at "Panty Boy" a bit
first. It was suddenly very hot in that room, so I stripped naked to
read more comfortably.

Unlike some magazines where the model starts out fully clothed, then
strips for the camera, "Panty Boy" girls often wear nothing, then add
lingerie to stunning effect. "Karen" was the cutest boy I had ever
seen and his naked body was slim and girlish. His little peener was
about three inches long, achingly erect and complemented by a gorgeous
wrinkled bag of walnuts. Karen was looking into the mirror, holding a
sheer, white nightie against himself and suddenly she was a sexy,
desirable, girlish babe. The camera loved Karen as she made up her
lovely features, then slowly slid on sheer, white stockings and
impossibly high stiletto sandals. Her little sissy clitty was stiff in
every picture. And my boyish rammer was equally erect. Karen began to
stroke herself as she looked at a framed picture of a handsome young
man. The photography was excellent. And timely. It caught the first
exquisite jet of spunk as it flew from the angel's cock, as well as
her ecstatic face, in perfect focus. The next six pictures showed
Karen in the sweet agony of crushing orgasm, and the small lake of cum
that formed on the doll's flat, downy tummy, right below her pulled-up
nightie. In the last two pictures, Karen is shown licking her cum from
her manicured fingers as she again looks longingly at the boyfriend's
photo. Every man who looked at those pictures was imagining that he
was Karen's boyfriend. Opening her door. Watching her react to his
arrival. Squealing and running to embrace her lover. Then surrendering
her wondrous body to her boyfriend's every lusty desire.

How could any living man look at that pictorial and not cum? I was
living, so I made a big cummy mess twice. On the first picture, where
she lay on her back tickling her testicles, then on the third picture,
in the sequence where she was cumming and scrunching her pretty face
so cutely. Oh, Mama. And I hadn't even looked at the hardcore
pictorial yet.

I decided to wait a bit and let my bag refill. I turned the TV on,
flipping through all 218 channels, none of which had anything good on.
In the next room, Vicki's date had arrived, and they were grunting and
gasping on the other side of the wall. For some reason, I wasn't as
disgusted as I had been with Rolf and Sven.

What the heck. I picked up Panty Boy again.

That article on the Panty Palace parties was really stupid. It was
just pictures of Nick Nickerson with a pretty sissy on each arm. The
panty boys were wearing evening gowns, slit up the sides, with silky
stockings and big heels. They certainly were pretty, even the ones who
were still wearing boyish haircuts. There were all kinds of
celebrities at the parties, and I don't mean the Hollywood Squares
kind. They were A-list celebrities, all with at least one lovely sissy
on their arms. And later, in their beds.

Enough of that. I wanted to see Cynthia "completely satisfying her
lover."

I was not disappointed.

Cynthia was a girlish little angel with a heartbreakingly beautiful
face, slim body, budding little titties with big, puffy nipples, and
the best looking ass I had ever seen on anyone, male or female. She
was sitting at her vanity stool in her boudoir, brushing her long,
straight, blonde hair. Her little willie, barely three inches, was
stiff and dripping as she considered her perfectly made-up beauty in
the mirror. She was wearing only a purple basque, with ruffled garter
straps, connected to seamed, tan stockings. Her long, delicious legs
ended in purple, five-inch-stiletto-sandal mules, encasing her
perfect, painted toesies.

In the next picture, Cynthia's lover had arrived. He was an older man,
magnificently hung, naked and rampant, standing behind her and kissing
her neck to Cynthia's very obvious pleasure. The man then removed a
beaker of cold cream from the vanity table and used it to lubricate
Cynthia's heavenly bottom with two rude fingers. The girl was shown
spurting her cream for the first of what I hoped would be many times.
I was erect yet again and I lay down on my bed to turn the page. 

With the lovers still both standing, Cynthia's beau entered her tiny
hole from behind, making his huge cock disappear in a feat worthy of
the world's finest magician. Cynthia's face was a tableau of
submission and the pleasure that surrender engenders. In the next
picture, both lovers were cumming hard. Cynthia's pretty face was
scrunched as her little pricklet shot its sticky, girlish juice. The
man was in paradise as his cum ebbed from his lover's bottom,
drenching her silky thighs.

That wasn't all of the pictures, but that was all for me, folks. I
blew yet another load of my plentiful, 18-year-old gooies. No wonder
Dad bought the magazine. No wonder all those men did. It was heaven on
earth to think about being, I mean fucking, one of those sissy
treasures.

Then I noticed something for the first time. Vicki had left a nightie
draped over a chair, obviously for me. I certainly didn't need it.
Naked would have been a fine way for me to sleep. Plus, that was a
girl's garment and I was there to get a maintenance man's job. I went
into the bathroom to wash all my cum off. Returning to the bedroom, I
was seized with the notion of just holding the nightie against me. To
see it there. What it would look like. Just that.

So I did.

It was a white little lacy thing, and very short. Barely covering my
package. For some crazy reason, I was hard again as I looked at
myself. Then I decided to just try it on. 

Well, it wasn't like Frosty the Snowman's magic hat. I didn't begin to
dance around or anything. But it felt very good. Very good. And I
looked even better than it felt. Pretty, sort of. I began to have very
naughty thoughts. What if the man in the Panty Boy pictorial saw me
dressed like that? Would he want to fuck me? Would I let him? How
would that feel? Oh, no…..I was cumming again! It was an awful, gay
cum. But it was so intense that I doubled over.

Exhausted, I got into bed, turned out the light and fell asleep.

I was awakened at 8 by a very cheery Vicki. "How wonderful! You wore
the nightie. You look very pretty in it, Sweetie."

I was completely and permanently humiliated. My cheeks were burning
with shame.

Vicki acted as if me wearing feminine clothes was the most natural
thing. "Let's go, Tina. Breakfast is ready and we have lots to do
before your noon appointment with Mr. Rodgers."

The need for breakfast overwhelmed my shame. I wished that Vicki would
stop calling me Tina. But French toast and bacon made me too weak to
resist.

Vicki was wearing a very risqué, see-through nightie. Her boobs were
spectacular. Her hips were wide and her waist waspish. "How did you
get that body?" I asked as we were putting the dishes in the washer.

Vicki smiled. "Hormones and minor surgeries. You should know. Your
mother's been giving you hormones for about three months now."

My heart sank. Oh no! Mom said those were allergy shots and that they
had side effects, like itchy nipples and softer skin. My nipples had
been itchy at first, then I seemed to be adding a little flesh under
them. How stupid I was.

"You didn't know! Geez, I told your Mom to tell you everything. Well,
no harm done, since you know now. In about six months, you'll have a
body just like mine."

Horror! Disaster! Huge, unexplained erection. What was happening to
me? Well, whatever it was, I resolved to put a stop to it. After I got
my manly maintenance job. Dressing manly and doing maintenance things.
With big, heavy boots. And lots of keys. On a thick chain.

Vicki hustled me off to my room, where she insisted I take an
immediate shower. When I got out, she showed me how to pat myself dry,
not rub. 

Then she began doing horrible things to me. Things I hated. She
slipped a pair of special, boy's panties on me, with a pink,
translucent sack designed for a "package" like mine. I didn't know
they made such things and my shame was almost as big as my erection.

Stockings came next. My first stockings. White and silky. With a long,
sexy seam. And a ruffled, silky white garter belt. Oh. I was so
humiliated when I spurted my sticky cream, just from putting on those
stockings and seeing myself in the mirror wearing them. Vicki didn't
seem surprised in the least. She cleaned me up, gave me fresh panties,
and showed me how to put on my make-up, insisting that I pay attention
to technique. I <blush> came helplessly into my panties when I saw how
pretty I was. Very pretty. I was turned on by my feminine self. Vicki
smiled knowingly as she helped me change my panties again, cleaning me
with a wet facecloth and towel. 

Was everyone affected like that, or was I a simpering little sissy
faggot?

Vicki spent the next hour helping me learn to walk in three-inch
heels, half the height of hers, but precarious for me. Then she put my
first (and I hoped last) bra on me. I really only had A-minus cup
titties at the time, but the bra made me feel very girlie, as did the
way the heels made my bottom jut out in lewd invitation.

Vicki helped me apply perfume, then slipped a pretty pink dress over
my head and pulled it on me. It fit me perfectly and showed off my
legs to a tee. I was "on the verge" again, a condition that I feared
would be permanent whenever I was in girlie clothes. 

Vicki showed me my beautiful self in the mirror and, to my amazement,
I sighed with pleasure.

"You're gorgeous, Tina," my sweet cousin said. "Now let's go get that
job."

Docily, I took the tiny purse she offered me and followed Vicki out
the door.

 

Chapter Four – Mr. Rodgers

Mr. Rodgers was the manager of our "Panty Boy" Spa and Resort. It was
one of 20 such operations in the country and, like the rest, was
almost printing money.

Mr. Rodgers was a good manager who took care of his customers and the
sissies who worked for him. And the sissies took care of him. All day
and all night.

If Mr. Rodgers had a limit in his love for sissies, no one had seen it
yet.

I was very nervous when Vicki and I knocked on the boss's door at
precisely the appointed time. I had to admit that I appeared to be a
feminine knockout, an opinion obviously shared by the six or seven
wolf-whistling men we saw on the way to the office. But I knew I could
never do "sex things" with a man. Any man.

Mr. Rodgers called for us to enter and I got an immediate surprise. A
delicious little creampuff was sitting on a man's lap and they were
kissing hungrily. They were the only two people in Mr. Rodgers'
office, so I assumed the man was he. I was right. 

The girl was a doll – lots of tight, blonde curls, big, kissable lips
and wide, sky-blue eyes. Her perfect, sexy body filled a white summer
dress, with big, black polka dots. She was wearing white stockings,
with a satin garter belt and pretty white, five-inch-stiletto sandals.
And she had been wearing skimpy pink panties, but they were circling
her right ankle at that moment. The girl was holding her skirts up to
her belly button and Mr. Rodgers had his big, manly hand around her
lovely cock, skinning it sweetly as they kissed.

<Gulp>

Vicki and I waited patiently as Mr. Rodgers stroked and kissed that
heavenly babe through a series of little grunts and squeals, followed
by her short scream and trembling, geyser of a cum. The girl's eyes
rolled back in her head as she gave herself over to pleasure, spurting
a copious amount of sticky cream onto the office floor. She looked at
Vicki and me, smiling proudly, then fell to her knees between Mr.
Rodgers' legs. She extracted his naked cock, then began to lick, suck,
stroke, kiss, tickle and tongue it to his obvious delight.

Suddenly, as his cock was being worshiped, Mr. Rodgers seemed to
notice us. "Oh, hi, Vicki. You know Emily."

"Hi, Emily," Vicki said.

Emily grunted hello as she sucked and licked.

"And is this your pretty cousin?"

I blushed at the compliment and panicked that he would want me to do
"things" to him like poor Emily was doing.

Vicki said, "Mr. Rodgers, this is Tina. Isn't she pretty?"

Mr. Rodgers looked at me in fair appraisal. Not a leer. A
businessman's eye.

"Yes, Vicki. She is. Tina!"

"Yes, sir," I said warily.

"Tell me about yourself. Take your time doing it. Start with first
grade."

Wow. I guess he was seeing if I was articulate. Fortunately, I am. I
began to tell my life story, but was very distracted by Emily and Mr.
Rodgers' activities.

As I got to the story of my hamster in third grade, Mr. Rodgers had
stood Emily up. Amazingly, Mr. Rodgers hadn't cum yet and his huge
tool was red, thick, stiff and angry. I guess he was listening to me
as he parted Emily's perfect bottom cheeks with his thumbs and began
tonguing her tiny hole. The sweet girl, who hadn't uttered any actual
words in my presence, began to squeal and cum once again. Mr. Rodgers
continued his delicious sissy meal until Emily was in a complete
dither. Then she turned and carefully, sat on his cock, taking the
monster into her asspussy one inch at a time. Mr. Rodgers grunted with
pleasure as his cock filled the little doll's entire love tube. I was
telling them about my merit badges when I was a scout in seventh
grade, and Emily's squealing made me increase my narration volume. 

I had barely mentioned eighth grade when Mr. Rodgers groaned and
filled Emily's tight hole with a gallon of his hot, sticky cum. What a
mess! As they kissed post-coitally, cum was running out of Emily's
bottom onto her thighs and Mr. Rodgers' lap. Emily gathered her
panties, waved goodbye to Mr. Rodgers, Vicki and me, and left the
room.

Mr. Rodgers waved goodbye and sat facing Vicki and me – his cock limp
and drooling goo. "That's very interesting, Tina. Now take your
panties off and lift your skirts."

I couldn't. I wouldn't. I did. But I wouldn't let him touch me.

Mr. Rodgers said, "Vicki tells me you don't want to have sex with men.
That's good. I don't want any gay panty boys. I want you to learn to
accept your girlishness, then want the pleasures of men. But I wanted
to see your response and I see that what you saw excited you."

I blushed. The shame. He was right. I was hard as stone and my
cockhead was drenched with pre-goo.

He motioned for me to come to him. I froze. I looked at Vicki, who
smiled and nodded, then I clicked and clacked over to him, panties
down, skirts up, exposed.

I was terrified. I didn't want to go home in shame and unemployed. But
I wasn't letting this MAN fuck me.

Mr. Rodgers saw my fear and said, "It's OK, Honey. Being a panty boy
is about surrendering to feminine pleasures. You're not ready yet, but
you would injure yourself if you left yourself that stiff and
unmilked."

He was right. My balls ached. Then he put his warm, skilled hand on me
and gave me sweet relief.

"It's OK, Tina," the understanding man said as he made me gasp and
pant. "You're hired. We'll put you on the payroll today and start
training you. Then, about eight weeks from now, you'll discover your
sexual destiny. Whatever it is. You're so pretty and sexy. I hope
you'll want to visit me some times and let me take you to bed. Emily
will be in my bed tonight, all night. I'll take her to heaven again
and again. Would you like that, pretty girl?"

I wouldn't. It was disgusting. So why did I whimper and cum and cum
and cum?

 

Chapter Five – Training

When Mr. Rodgers said I would be put on the payroll, he wasn't
kidding. I was making more money than the total of everyone in a
six-block radius back home. And I was a big hero to the family I was
supporting with that money. I was sad that I would have to give it all
up in eight weeks, because I knew "doing it" with a man was out of the
question. So I would just try to hang on as long as I could before
they figured that I wasn't about to join their faggish little circle. 

Still, I had to admit, everything so far had been incredibly good.

I didn't like being whacked off by that Mr. Rodgers bossman guy. Doing
that as if he owned me or something. Like I was his possession to do
anything he wanted. Surrendering. Submitting to him.

No way.

I felt sorry for that Emily girl. How could she get fucked like that
by a man and act as if she enjoyed it? Didn't she have any pride? And
she was incredibly pretty. Of course, if she weren't a panty boy, she
would just be a schlumpy-looking, drab guy, like I used to be.

There was that to consider.

Oh, yes. I was pretty. Oh, yes. Pretty beyond my wildest imaginings
and prettier every day they trained me.

Thank goodness, the training wasn't about sex. It was about femininity
and about working in the hospitality industry.

I learned all about hair, nails, make-up and clothes – all kinds of
femmy things, including walking on huge heels and all the feminine
mannerisms. But I also learned about mixing drinks, cooking, serving
drinks and food and dealing with customers. Useful stuff and very
skillfully taught by a 20-something panty boy named Ashley who could
have won every beauty contest in the world by a landslide. 

Ashley was a terrific instructor to me and three other "girls," Haley,
Courtney and Chelsea. Like me, the "girls" looked like every man's wet
dream, especially Haley. Her mother and father were immigrants from
Thailand. Haley was very smart, achieved great things in school, and
then was unable to get any sort of job. Her long, straight, black
hair, slight, slim build, perfect, nearly hairless skin and classic
Asian beauty made it difficult to remember that, like me, she was just
a guy doing a girlish job.

Courtney and Chelsea seemed ready to make lots of men as wet as their
dreams. Haley and I were the reluctant ones.

Ashley, to her credit, didn't try to influence us sexually at all,
aside from giving Haley and me a lovely milking twice a day. Ashley
sent Courtney and Chelsea off for their milkings to Robbie Burnside,
who ran the spa's gym. Robbie was big and broad and handsome and
muscular and hairy and eager to ease the pain of the trainees. Haley
and I wanted none of that, though we did find that our femininity had
us so painfully aroused that we probably wouldn't have survived
without those delicious milkings. Several times a day, whenever Ashley
thought we needed it, we would stop training and take a milking break.
Courtney and Chelsea would go off to some faggoty rendezvous as Haley
and I stripped to our pretty lingerie, presenting our red, throbbing,
needy cocks for Ashley's tender attentions. 

Haley was so beautiful. I loved to watch her being milked as I waited
my turn. Her penis was miniscule, the size of a "ladyfinger," but it
stood straight and proud. Her little hood of a foreskin was peeled
back to reveal a perfect, pink prickhead. The sight of the goo oozing
from her girlish peehole had me frantic with excitement. And her
gasps, pants, whines and moans during the loving strokes often made me
cum hard and wet.

If the preliminaries didn't make me cum, surely the sound of Haley's
girlish squeals as globs of sticky goo fled her bitsy balls did the
trick. Sometimes I would look at Haley's pretty face as she made her
messies. It was always scrunched in ecstasy, but when she opened her
eyes, she would lock them with mine and smile prettily at me.

Although I always came at least once watching Haley's milking, I was
hard and ready for Ashley's glorious attentions. Even if I had come
moments before, Ashley's warm, soft hand on my prick brought me to
full attention. Throbbing. Needy.

Haley always paid rapt attention to my milkings, which excited me even
more. I'm proud that she gasped with wonder and delight when she first
saw my big, fat prick and huge, hairy, cum-filled balls. When Ashley
milked me, she would often tell me how much men appreciated a
well-hung panty boy (as well as a teeny-weeny sissy like Haley).
Ashley would use her pretty fingers skillfully as I would sneak peeks
at Haley's once-again-rigid member. 

Haley was very excited by the sight of my big splitter. She told me
once that the sight of such a masculine thing on such a pretty girl
was very arousing. Sometimes she would lick her lips as she watched me
squirm and moan under Ashley's care. My cock would leak furiously and
then – and this is the embarrassing part – I would usually squeal like
a girl as sticky cream leaped from my cock in thick, hot ropes. To
this day, I don't know why I started doing that. It just seemed right.

I guess Haley agreed, because the sight of my goo always brought her
to another screaming crisis as she stroked her peener to an explosion
of girlish goo.

After those sessions, I always seemed to want more of something, but I
didn't know what it was.

Those two little tramps, Courtney and Chelsea spared us the details of
their "milkings," but the cum drooling down their thighs from their
bottoms and the occasional drop of shiny substance on their lips or
clothes suggested that much more than the proper sort of medically
necessary milking was taking place with that Burnside gorilla. And who
knew how many others.

Perhaps you've deduced that Haley and I felt morally superior to our
two beautiful, but trampy classmates. We did.

Ashley would gently suggest now and then that a milking from a man
would be ten times as satisfying for girls like us, but we wanted no
part of that. Uh uh. Haley and I had a vow. Although the memory of my
milking at the hands of Mr. Rodgers had been very exciting. But we
were going to resist all manner of faggotry, no matter what. 

It felt so much better to be part of a support group. 

Not that I wasn't getting support from my cousin Vicki. She was
wonderful to me, housing me in her spare bedroom and comforting me
about my misgivings.

My titties were growing very well and I was pushing a B-cup. My body
was taking on a lovely, feminine appearance and, truth be told, I
loved the way I looked. I sort of, a little bit, kind of enjoyed some,
a few maybe, of the stares and wolf whistles I got from almost every
man I saw. But I wasn't going to suck their smelly cocks. Or take them
inside me. Or even touch their cocks or kiss them! ICCCCCKKKK! 

I think I began to compromise my very sound and worthwhile principles
during our fourth week of training, when we were learning about the
proper wear of evening gowns. 

Ashley was wearing a tight, white strapless number with a high slit
that showed the world a great body with a fantastic pair of legs. Her
long hair was arranged in a nighttime predatory mane and her evening
make-up embarrassed me by making me get fresh panties twice in the
first hour of class. Panty "accidents" were common among the four of
us, but I knew this would be a particularly difficult day for me. 

I couldn't stop looking at the other girls, but also at myself. I was
wearing a red sequined stunner with a high slit that showed off my
black-stockinged legs, which ended in red strappy, five-inch-stiletto
sandals that revealed my red-painted toenails under the stockings.
Looking at myself in the mirror made me gasp and cum yet again. I
couldn't help it! I was so beautiful and those clothes rubbed me so
sensuously. Thanks goodness Courtney had also cum once that morning
and Chelsea and Haley twice each.

Speaking of Haley, I think seeing her radiant girlish beauty in a
black, spaghetti-strapped evening gown was the most exciting sight of
my life to that point. Besides the sight of myself, of course.

When the two little tramps went off for their milking break with
Robbie that morning, I took a bold step. 

"Ashley, would it be all right if I milked Haley, instead of you doing
it? I mean, if it's all right with you, Haley."

Haley beamed. Wow, she was beautiful! "I would love that, Tina. Please
unzip me," Haley said.

My heart skipped. We unzipped each other and stripped to our lingerie
and big heels.

I stood behind Haley and reached around her right hip. I reached into
her panties and touched her little peener. It was about the size of my
little finger, but it was stiff and dripping madly. Haley shuddered
with pleasure as Ashley looked on with approval. I had never touched a
cock before and I was concerned about the gayness of it all. But Haley
was so darned feminine! And so pretty. And my goodness, she was acting
as if I were the sexiest person alive. 

Haley leaned back into me and whimpered with lust as I rubbed her tiny
cockhead with my painted fingertips. Oh my! My own cock was enflamed
and hard as diamonds. Was I going to……oh no. I needed fresh panties
yet again.

As I was spasming and spurting hot cum, Haley turned her head and
kissed me. 

Now THAT was exciting!

I had never kissed a boy. But Haley wasn't really a boy. Anyway, who
gave a fuck? It was fantastic. She smelled wonderful. Her lips were
the sweetest candy I had ever tasted. And she came in jerking spasms
as my tongue tipped hers for the first time.

Haley turned and we kissed face to face. I lifted her tiny body in my
arms, holding her by her pretty bottom as I kissed her and rubbed my
half-hard, drooling cock against her stockinged left thigh. Haley was
whimpering and rubbing her cock against my stomach as she kissed me
and pushed toward her next orgasm. 

I had never been half as excited in my life. And ashamed. Some. A
little. About being dressed as a girl and doing sex things with a
lovely girlie boy. But I would get over it.

Haley and I kissed and rubbed through three gushers each and I wish we
had stopped at three. Partly because we felt like wet dishrags after
and partly because Chelsea and Courtney caught the last act of our
drama as they sissied back into the room from their little sodomy
session.

Haley and I lost a smidge of our moral superiority, but what we gained
was worth it. I believed I was in love. 

And at least I wasn't sucking some man's icky cock. Hmmmppphhh.

The rest of that day we tried on around ten more evening gowns and
were so excited that we had to have three more milking breaks. Sharing
my body with Haley was divine.

As the day ended, the most wonderful coincidence occurred!

Ashley told Haley and me that due to overcrowding in the Panty Boy
dorm (where Haley, Courtney and Chelsea were staying), Haley was going
to be moved out. Ashley had mentioned this to my cousin Vicki, who
immediately offered her home to Haley, if I wouldn't mind sharing my
room with her.

Cowabunga! Sleeping in the same bed every night with Haley for the
next four weeks – until they fired me for not sucking men's cocks –
that was the best news I had ever heard.

As icing on an already sweet cake, the spa had previously moved
Haley's things and set them up in my room, so all we would have to do
when we got home would be….get to know each other better.

When training ended that day, I grabbed Haley's hand and walked her to
Vicki's apartment. We tottered along in our short skirts, sexy
stockings and big heels, holding hands like sissy sweethearts involved
in a torrid love affair, which is what I guess we were.

Vicki was there waiting for us and gave us both big hugs and welcoming
kisses. I already lived there. What was Vicki welcoming me to? Hmmmm.

Vicki made her excuses about a pressing engagement (some guy pressing
her against a wall and fucking her tight bottom, no doubt) leaving
Haley and me alone in the house. With privacy. No one else around.

Every second you waste in life is gone forever, so I picked Haley up
in a Rhett Butler carry and took her into my bedroom. She was
squealing happily and kissing me the whole way, so I guess she didn't
want to waste time either.

I set Haley on the bed, then undid my skirt. I pulled my top, then
skirt over my head and shimmied my pretty panties down, exposing my
ramrod cock to Haley's welcoming eyes. Haley had only managed to get
her blouse unbuttoned and panties off, but that was OK for the moment.
I had much to explore, but much time to do it.

What was I going to do? Should I fuck her? 

Haley lay there on her back, her breathing exaggerated. I saw
something in her eyes that is the one thing men prize above all in
their women. Submission. 

I could have done anything with Haley then and she would have loved
it. I made a mental note that it bode poorly for our vow that she
would surrender to me like that. What if a man had her on her back
like I did? Her pretty lips parted for a kiss. Her body an open
invitation.

I had bigger fish to fry though, so I set about the delightful
business of making love to the sexiest person alive.

It occurred to me that I had never seen Haley's bosom. So I softly
removed her bra.

No real titties were in evidence; only puffy little nipples that
begged for kisses. They were sexier than those half-grapefruits bad
breast surgeons attach to some poor girls.

I decided to see if Haley liked having her nipples kissed. I teased
her a little, moving slowly toward her chest with my mouth. Watching
her reaction as I puckered my glossed lips to kiss her sensitive
titty-flesh. Then feeling her spasm as I licked the tip of Haley's
right nipple. 

She liked it.

So I kept doing it. I gave her right nipple a gentle sucking, then did
the same to her left nipple. My darling's eyes got wide, she cried out
and began to spurt her spunk. One jet was so powerful that it hit my
cheek.

I had "male" cum on my cheek. Yet, I didn't die. Maybe there's no
curse with all of that after all. 

I decided to find out. I kissed Haley's nipples sweetly all through
her world-rocker cum and its aftershocks. Then I kept kissing her
until, gasping for air, she erected once again.

Drawing a breath and crossing a mental bridge, I kissed my way to
Haley's privates, then began to lick off all of her sweet cum from her
tummy, cock and balls. 

It was delicious and once again, I wasn't struck down. Haley looked as
if she were having a near-death experience though. I guess a pretty
girl (me) licking the cum off your most sensitive parts can be most
arousing. She actually screamed when I took her cock and balls into my
mouth and adored them with my tongue.

It wasn't like doing it with a man, OK? Haley was mostly a girl. But
what did that make me?

I slurped her little popsy happily and when she grunted and filled my
mouth with an amazing amount of sticky cream for a little girl, I
swallowed every drop.

Something had just happened there, yet I was trying to convince myself
that it had not.

Haley, for her part, wasn't worrying about such things. She shucked
off the rest of her clothes, except for her hose and heels, and pushed
me onto my back. She lay on top of me, all 98 pounds of her, and
kissed me as if I were Ed McMahon telling her she won the sweepstakes.
Then that bad girl unhooked my bra and gave me a dose of my own
medicine. I had played with my nipples in the shower a little, but
it's always completely different when someone else "does" you. Haley
licked and tormented my nipples until I was in sexual agony. To make
things worse, she was massaging my balls the whole time. Well, I was
more than ready for a bone-crushing cum, but when my eyes filled with
tears as I spurted thick, hot globs and I screamed like a Brownie at
camp, that surprised me.

Was I going to be girlish like that forever? Were the effects
reversible? Did I want them to be?

Haley was distracting me a bit from all my introspection by sucking my
cock That was very distracting, especially since she seemed to be so
good at it. So very good at it. How she ever got my big rammer into
that tiny mouth was beyond me. But there were other surprises in
store.

Though I was grunting and panting, the part of my brain that was still
in my cranium was telling me that I was soon going to be depositing a
big load into a very pretty mouth.

Not so. When I got to my maximum cock girth, Haley stopped sucking me
and began to kiss my lips. It was dangerous to leave me in that
condition, but I kissed her back. Then she got up and went into the
bathroom.

She was in there for several minutes. I was a little concerned, and
called out, asking her if she was all right. Haley called back that
she was fine. Then I started feeling sorry for myself. I had that big
erection and no place to put it.

Moments later, my problem was solved.

Haley got on top of me and kissed me tonguily. Then she rolled off me
and onto her back. She reached under her legs, and boosted them up to
expose her lovely, precious bottomhole. 

Did she want…?

Her eyes answered. They begged for a fucking. Hard and wet.

My cock regained all its vigor as I mounted her, covering her with my
larger, though feminine, body.

"I made myself wet for you, Tina," Haley moaned. "Baby oil."

Oh.

I entered her with first one finger, then two, to make sure she was
open enough for me. She wasn't. There was no way I would be able to
get into her tiny body with my big equipment. But she would not be
denied. She whimpered with pleasure as my fingers explored her warm
place, kissing me with a lust I had never experienced. 

I breathed, "I don't want to hurt you, Baby. I love you."

Haley hugged me. "I love you too, Tina. Now please fuck me!"

Geez. 

Fearing failure, but excited nonetheless, I rubbed my cockhead all
around Haley's little panty-boy pussy. It felt wonderful to me already
and Haley seemed to be on the verge of another monster cum herself. I
pushed a little and didn't kill her. Except with pleasure. 

Haley loved taking my cock. I managed to get about half the head
seated in her anus and she dug her nails into my back, shuddered and
came. In the act of orgasm, she moved her bottom toward me and the
entire head was engulfed. 

That set her to crying and begging for more cock. Wow! I pushed and
more slipped in. Haley cried out and I stopped.

"Are you all right, Sweetheart?" I asked with real concern.

"Not until the rest of it's in me," my brave little trooper said.

I obliged, sheathing my sword to the hilt and making poor Haley almost
faint with pleasure. 

The girl was beautiful, was my roommate, loved sex and loved me. The
fact that she was a guy seemed irrelevant, especially considering the
femmy state I found myself in.

Stunned that I had gotten my whole meat into her bottom, I felt down
there to reassure myself of the miracle. It was confirmed and Haley
seemed to feel all pleasure and no pain.

I began to move in and out of her, slowly at first, then with
increasing speed, heat and fury. We kissed like hungry wolves, grunted
and whimpered, squealed and moaned, then, as one, we felt the mother
of all orgasms send its first gentle signals, followed by bigger and
more insistent ones. We were over the edge, our toes had been blasted
off with pleasure, our guts replaced with furnaces set on high. Every
molecule of cum left my body and entered Haley's gorgeous rectum.
Simultaneously, she drenched her own stomach with more cum than I had
ever seen all in one place. 

It was glorious, ladies and gentlemen, and it was only 7:30 p.m. on
the first night of four weeks we were to room together. 

They were an incredible four weeks.

Haley and I were molten with love. We gave each other at least ten
killer orgasms every day and night. I learned to enjoy every square
millimeter of Haley's body and she mine. I would spend at least a half
hour every day eating out her bottom before I fucked her. NEVER, did I
think I would do that, but she adored it. So I did it with great zeal.

I fucked Haley three or four times a day too. She was an angel of
love, eager to please and capable of extraordinary pleasure-giving.
Unfortunately, Haley wasn't really able to fuck me very well. Her
little pospy was so small that I could hardly feel it. But I certainly
felt her tongue in my bottom as she licked me to multiple orgasms
every day. She was also very skillful in using her pretty fingers to
give me a prostate massage to even more orgasms. 

All that and I was getting paid a huge amount of money. Supporting my
family. Loving Haley. Would I ever see her again after they cast us
out for failure to make love to men? Even if I did, we wouldn't have
all the femmy stuff we had. Beautiful lingerie. Good meals.

But that was a small price to pay to avoid a life of faggotry, wasn't
it?

Still, I was getting pretty depressed about the situation until,
during the last week of training, we began dancing lessons.

"A good hostess is a good dancer," Ashley said wisely. I knew I wasn't
going to be anyone's hostess, but I played along.

We four students were wearing strapless cocktail dresses with
petticoats – very fifties – and we looked, as always, mega-babish. We
even had the elbow-length white gloves, which made me feel even
femmier. In fact, my girlishness was threatening to stomp out the
flame of my masculinity. But that would never happen, because I knew
there were certain awful, faggish things I would never do with a man.
And Haley agreed with me. 

I was wondering which of the girls I would be dancing with when the
classroom door opened and in walked – MEN!

Four very handsome men in black dinner jackets. James Bond-like men.
Very handsome. Which I'm only saying so you have an accurate
narrative.

We hadn't had men with us in training before, but I guessed we needed
them for dancing.

Not for much else though. I mean, I had Haley and she had me. So why
did I need that guy named Alex who introduced himself to me and asked
if he could have the next dance? He was tall. Even in my five-inch
heels, my eyes were about even with his lips. They were nice lips.
Very masculine. And he was very muscular. Sort of handsome too, I
guess.

I looked over at Haley and a guy was asking her to dance too. He was
shorter than Alex and not as good-looking. That was good, because I
didn't want him or Haley to have any ideas.

I certainly had no ideas, other than getting this dancing stuff over
and getting Haley back to Vicki's place for an all-night shagging.

I agreed to dance with Alex because I guessed I had to. Part of
training and all that. It was a good thing my Mom had taught me to
dance. She always led, so following was easy for me. Dancing in
five-inch stilettos was no real challenge either, since those were
really the only shoes we wore.

Alex put his right hand around my left hip and held my right hand in
his left one. I put my left hand on his shoulder. And then I began to
tremble. I was terrified of something, but I didn't know what. 

Alex noticed. "Are you all right, Tina? I hope you're all right. Shall
we stop?"

Gee. He was pretty sweet and considerate. I controlled myself a bit
and said, "No, that's OK. Let's dance."

Alex smiled. Omigosh! It was a dazzler of a smile. Then he said, "I'm
so glad. I've seen you around and I've been dying to meet you. You're
the most beautiful girl who ever came through this place."

I gasped.

Then I was really afraid. Alex's compliment was like a sausage pizza
to a starving frat boy. I was stunned by the impact it had on me. I
felt my inhibitions leaving my body. Mentally, I grabbed at them
frantically and hauled them back in.

Still, I sort of glowed with the praise. Could he really mean it? I
mean, I knew I was beautiful, but the best ever? Wow.

He had to know what that had done to me. I was blushing hotly, which I
knew he could see. I was also fiercely erect, which he couldn't see
through my petticoats, but I knew it. And I was ashamed.

Ashley turned the music on. A slow one, darn it, and we began to
dance. Alex was a smooth dancer and he kept looking at me. Like he was
crazy about me or something. Did I have that effect on men? I blushed
some more,

I looked over at Haley and she appeared to be in a like predicament.
Be strong, Haley, I said to her telepathically. 

"Let's dance a little closer ladies and gentlemen," Ashley said. "This
isn't a Catholic school formal."

That was no problem for Chelsea and Courtney, who were dancing as if
they wanted their partners to ravage them on the dance floor. But
Haley and I moved closer reluctantly. Alex was gentle, but insistent
until, Mamma mia! Despite the petticoats and dress and Alex's tux, I
could feel Alex's iron bar rubbing against my own. Through the
clothes. Rubbing.

I wanted to pull away, but feeling his cock against mine as I smelled
his aftershave and danced and rubbed against him……. I was only human.
Alex saw the need in my eyes and when I turned my chin up a quarter
inch, he kissed me.

GAY ALERT!!!!!

Sirens went off in my head. Then trumpets. Then only little bells –
soft little bells. Tinkling. As he kissed me.

He was a good kisser and my body, not my mind, liked it a lot. When he
slowly entered my open mouth with his tongue, I lost it.

My eyes got wide, I squealed and I began to spurt my cream all over my
panties and petticoats and pretty dress. A monster cum! An evil, gay
cum. That I broke off, along with the kissing, as soon as the last
glorious tingle left me.

I stepped back and away from Alex, my breast heaving. Shame masked my
face. I dared to look at Haley and she was also kissing her young man
and clearly in the throes of a four-star cum.

What was wrong with us?

OK. Everyone has lapses. That was ours. We hadn't actually done
anything awful. Hadn't touched those big, hard things of theirs. Or
<horrors> taken them into our mouths or bottoms. So we were
redeemable.

Ashley asked me if I were all right, then pointed up a grim fact to
both Haley and me. "Your partner just gave you a wonderful treat. Are
you going to let him suffer?"

Haley and I looked at each other. Then she nodded at me. I said, "I
guess not. Fair is fair."

Ashley didn't have to do much with Courtney and Chelsea. They were on
their backs on the floor, panties off and pretty pink bottoms stuffed
with their dance partners' cocks.

<Gulp> The fact that Haley and I had our gloves on was a little
comforting. I went over to a very horny-looking Alex and unzipped his
fly. I put my gloved hand into his pants and pulled out a beauty of a
cock. Fat, long and hairy, with ridges and thick blue veins on either
side. Thank goodness I wasn't actually touching it – my gloves were.

Alex's cock was very hot and very moist. He whispered to me, "That's
very exciting, Tina. You're a beautiful, sexy girl. Unnnnhh. That's
very exciting."

Alex seemed to be enjoying my manual caresses very much. To be polite,
I was giving him a very nice hand job. Just to be polite, though it
was exciting me just a little. His moans told me that he enjoyed it
very much. I guessed that I could bear doing that if he would just
hurry up and do his nasty business. But then he started that darned
kissing again. I wanted to tell him to stop, but his lips were in the
way, so I just let him kiss me. I probably should have put up more of
a fight, especially when he put his hand under my skirts, pulled down
my cummy panties and eased one, then two, then three fingers into my
pretty bottom. Instead of protesting, all I did was cum. As if I
weren't saving any body fluids for my old age. Hard and spasmy. 

Oh, I was in heaven.

But it was wrong.

Wrong.

Alex made a huge mess all over my gloves and arm and pretty dress and,
it appeared, the same fate had befallen poor Haley.

Avoiding faggotry can be challenging.

Alex gave me several more hot kisses and I feared he would begin
taking more liberties with me. Fortunately, Ashley declared milking
break over. She was such a taskmaster.

We danced on without further incident and when the men had to leave
right before our next milking break, Haley and I were vastly relieved.
We didn't want those men thinking they could just kiss us and finger
our bottoms until we nearly split our guts in orgasm. Why would we
want that? They probably wanted lots of other things too. They were
probably gay. I mean, we were men and they were men. Yuck!

That night as I was fucking Haley's beautiful bottom, she and I
renewed our vow to avoid faggotry at all costs. Even if we were fired.
And unemployed. And had to leave each other. And give up all our
pretty things. And all our monster orgasms.

There was a principle at stake.

Wasn't there?

 

Chapter Six – Graduation

We finished up our training on a Wednesday and I was filled with
dread. I didn't want to give certain things, especially Haley and her
sweet pootie, up. But I was a hetero male. Forever.

I decided to sort of take it one day at a time and see if there were
some middle ground to be explored.

There was no graduation ceremony as such. Ashley told us that Mr.
Rodgers would just talk to us and congratulate us. No sex required,
she assured me.

Chelsea went in to see Mr. Rodgers first. Chelsea looked spectacular
in a lovely black minidress that looked even better since she went
blonde. Ten minutes later, Courtney, in a pretty white sundress and
white stockings, was asked to go in. Chelsea must have left by the
rear entrance, I thought.

I was wearing my favorite frock. It was pink with flouncy skirts and I
was wearing my seamed pink stockings and strappy, pink, stiletto
sandals. When summoned, I walked in confidently and saw – an orgy.

Not messing around, Chelsea and Courtney had stripped completely
naked. I had to admit, their bodies were svelte and girlish, with
excellent B-cup titties and middle-sized cocks, both of which were
drooling the residue of at least one recent cum.

Mr. Rodgers had stripped completely naked too and he had a beautiful,
muscular, hairy, masculine body. Why hadn't I noticed that when I had
seen him fucking that Emily girl eight weeks earlier?

Anyway, Mr. Rodgers was in a chair. Chelsea was on her knees giving
his balls a proper bathing and Courtney was sitting on his thigh,
kissing him hungrily as she stroked his huge cock to a torrent of
precum. 

I stood and patiently watched this disgusting display, but tried to
think of other things. My cock would have none of it. It was red,
stiff and needy as it tented my skirts.

Mr. Rodgers eventually groaned manfully, then blew wads of cum 18
inches into the air and onto Chelsea's face and Courtney's hand. The
girls giggled gleefully. Courtney got on her knees to help Chelsea
lick the boss clean, as they stiffened him once more for their own
delight.

Mr. Rodgers looked at me for the first time.

"Ah, Tina. I heard wonderful reports about your training. You've
become a skilled hostess with bountiful femininity and exquisite
looks."

I blushed.

"You can join the fun with Chelsea, Courtney and me if you like, but
my guess is, you won't. Still a little skittish around men. And still
a virgin, I understand. Well, no matter. You'll come to your senses.
If what Alex tells me is even half true."

That no good kisser-and-teller, Alex! If I ever saw him again……

Courtney and Chelsea had gotten Mr. Rodgers dry-martini-stiff again.
He was still sitting as Courtney carefully backed into his big tool,
sighing with pleasure as she squatted on it, taking it into her warm
place for safekeeping. Meanwhile, Chelsea was standing and offering
her stiff popsy to Mr. Rodgers' warm, wet lips. He sucked the pretty
panty boy with zeal and skill as he fucked her sissy lover's sweet
bottom.

I don't even think they noticed when I left.

That night, Haley and I made love as if we were doomed.

"They'll throw us out when we refuse to do 'things' to their guests,"
I said to Haley as she sucked my big rammer to another mouthful of
sticky cum.

"I could never suck a man's cock," Haley assured me. 

I believed her because I felt exactly the same way. 

It was true. We were doomed.

 

Chapter Seven – Not so doomed

The next day was to be Haley's and my first as "hostesses." Ashley
gave us our assignments for the day. Haley and I would be working
together as swimming pool hostesses. We were taken to the panty-boy
bathhouse and outfitted in the skimpiest bikinis I had ever seen. Mine
was electric blue, but used less material than a handkerchief. Haley's
was red, I think. It was so small that it was difficult to tell. Our
make-up and nails, toe and finger, were checked by Ashley, and we
sissied out into the pool area, nearly naked, tottering on five-inch
heels.

I was scared half to death. But my cock was stiff and throbbing. Being
98% naked in front of 30 or so rich, successful men who were wearing
only red Speedos, was arousing me despite the valiant efforts of what
was left of my fading male identity. I could see by Haley's tiny bulge
that she was also turned on.

There were lots of other "hostesses" in the pool area, but somehow I
thought that all the attention was on me. It turns out I was right. My
fair skin hadn't seen much of the sun and it was a hot, bright day.

Haley turned right and I turned left. I took a doublewide lounger and
stretched out on its comfortably cushioned surface. Maybe if I got a
bad sunburn, they would have to take me off duty for a while and still
pay me. Maybe I could still get one of those maintenance jobs.

I guess I was being a bit optimistic.

I put my shades on and awaited my fate. It arrived quickly in the form
of a man named Grant Budner.

Grant, I found out later, was in his mid-40s, married with two kids,
filthy rich and powerful, and looked as if he had stepped off the
pages of Playgirl magazine. He was handsome, toned and fit. He had a
great tan and an easy manner. He adored panty boys. And he was
standing over me holding something I desperately needed – a bottle of
spf 75 suntan lotion.

"Excuse me, Miss," the gorgeous (just stating a fact) man said. "May I
rub some of this on you before you incinerate?"

My pretty eyes were wide. My brain searched for an answer. My mouth
said, "Yes, thank you, Mr……"

"Call me Grant," he said. 

"I'm Tina."

"That's a pretty name for a beautiful girl."

I blushed. The old lines are still the best.

Grant pooled some lotion in his right hand and began to rub it on my
feet. Very well. Between my toes. Oh, please no – my cock was so stiff
the head pushed out of my bikini bottoms. I tried to cover up, but
there wasn't enough cloth. Grant moved up my legs, rubbing the lotion
onto me with very, very skilled hands.

"You have beautiful legs, Tina. I'll bet they look fantastic in black,
silk stockings."

I gasped a "thank you."

When he rubbed the lotion on the front of my thighs, I moaned. It was
wrong; it was gay. Then he rubbed his powerful, manly hands, slick
with soothing lotion on my inner thighs.

Unnnhhhh. I was once again "on the verge," a condition far too common
with me. He was just so nice and handsome and complimentary. Maybe if
I could see Haley I could gather the strength to resist. I looked for
her, but couldn't find her in the large pool area. 

Thank goodness, Grant stopped doing that and began to rub the lotion
onto my smooth, girlish tummy. "You have a beautiful figure, Tina,"
the flatterer said. "You're the most attractive girl in the place."

I blushed again. Was he serious?

Then he got to my exposed titty flesh. Only my nipples were covered by
the bikini bra. What was he going to do? Like Alexander and the
Gordian Knot, he took the direct approach. He moved my "bra" up to my
neck and began to apply lotion to my bare, right titty.

That was too great a liberty. I started to protest, but then I spotted
Haley and my heart sank. The little tramp had shattered our vow! She
was naked, sitting on a hunky man's lap with the man's cock drilling
the pussy that I thought to be my turf. Another man was feeding her
his enormous cock. And they weren't forcing her! She was obviously
enjoying herself. In fact, at one point, she even caught my eye and
smiled and waved at me. Stupidly, I waved back.

All was lost. Haley was a little faggot. And I was alone. All alone.

Not really totally alone. A very nice-looking, sweet man was on his
knees next to my lounger and he was rubbing slick lotion onto my
sensitive, new titties and tender nipples. He was doing it very nicely
and my poor cock seemed to be appreciating it very much.

And then it hit me. Like a ton of bricks. What if I just gave in?
Instead of fighting my feminine feelings, what if I just surrendered
to girlish pleasures? And the naughty needs of men?

Would it kill me? Doubtful. Would I enjoy it? The other panty boys all
seemed to and there was only one way to find out.

I looked at Grant and parted my lips for a kiss. He stopped rubbing my
titties, lubed his hand with lotion and rubbed it on my enflamed
prick, reaching into my bikini bottom to rub my balls ever so sweetly.
And then he kissed me.

It was divine. I submitted to him and let all the nasty maleness in my
body flee the premises. He rubbed my prick so nicely. And kissed me
like he meant it.

I stopped kissing him to speak. "Rub my clitty slowly, Daddy," I said.
"I don't want to cum right away. I like what you were doing around the
rim of my little mushroom."

I called him "Daddy." Where did that come from? 

He seemed to like it. I was glad he liked it.

Grant smiled. Men love the moment of surrender best and I was flailing
my white flag.

Grant got off his knees and joined me on the padded lounge. He lay on
his left side and kissed me, stroking my pricklet with his right hand.

Oh, it was divine. Then I gasped. What if he wanted to fuck me?!?!?

Then I answered my own question. I would let him.

I reached into his Speedos and felt for his cock. 

It was a beauty! Hard, long and thick. Hot and throbbing. For me.

He squirmed as I pulled his cock into free air. I could suck it later
and take it into my bottom. If I wanted to. And if it would fit. And I
wouldn't have to leave this wonderful place and Haley (the little
tramp) and Vicki and even my dance partner Alex. And all the wonderful
men who were fucking and sucking pretty panty boys all over the pool
area.

Submission to feminine pleasures and to the men who would enhance them
was the most liberating thing I ever did.

I decided to stop philosophizing and start concentrating on the man at
hand.

Grant had me whimpering with need and swooning with girlish excitement
as he increased the friction on my prick. His kissing had me in a
tizzy as well. His tongue was the best meal of my life, though I
suspected that the big thingee between his legs was going to taste
even better.

Grant had me at the edge and then I fell into the pit of orgasmic
ecstasy. Squealing like a little girl. Cumming in thick, sticky
spurts. Kissing him harder in homage to his skill and manliness.
Creaming his rough but gentle hand with my liquid tribute to his manly
beauty.

I sighed and rolled my eyes back as the waves of delight struck me.
Grant milked me dry. Then the bad boy got down there and licked me
clean! He was a little puppy for my cum. How cute! 

Of course this got me hard and randy again, but I didn't have to do
anything about it. I had surrendered to my man and the agenda was now
his.

His lips were wet with my girlish cream when he kissed me again. 

"You're so beautiful," he said. "I have a pair of beautiful silk
stockings in my room and a matching silk nightie that I think would
bring out every bit of your femininity. Shall we go to my room and see
what we want to do?"

I looked down, then looked up meekly between hooded eyes and said,
"Yes, Daddy."

Grant hadn't cum yet, but his cock twitched when I said that.

I was naked by this time and I still don't know what happened to that
so-called bikini. I slipped on my heels and Grant, with his cock still
sticking out of his Speedo, and I walked arm-in-arm to his room. Which
was actually a suite. Two floors. With a kitchen and Jacuzzi. He must
have spent a lot of time at the Panty Boy spa.

When he closed the door, he kissed me hard, slipping two fingers up my
welcoming bottomhole. He rubbed his cock against mine as we kissed and
his fingers massaged my poor, sensitive prostate. After ten glorious
minutes of that exquisite torture, I came again, screaming out his
name and clamping my ass on his fingers so hard they were bruised for
a week.

He loved it.

This time, it was my turn to be the cleanup crew. I hit my knees,
right there in the entrance way to his place (we hadn't moved very
far) and took him into my mouth.

My first cocksucking. Couldn't count Haley's. That was an appetizer.
This was a seven-course meal.

It was hard, but velvety smooth at the head. The dear man's peehole
was leaking a steady stream of sissy nourishment. I licked. I sucked.
It was delicious and I loved how he loved it. I made appreciative
noises. And I made him cum! All over my face. Dripping down my chin
and neck – even forming a pearly necklace of cum. I made that man give
it up hard.

I was so proud.

Grant was so horny.

He picked me up and slung me over his shoulder. As I squealed in
playful protest, he carried me up the stairs to his huge bathroom. It
had a doublewide, sunken tub and a doublewide shower. Clearly, it was
room for entertaining panty boys. No matter. I was hot to trot and
ready for anything.

"First we clean up," Grant said. He turned on the shower, and firmly
pulled me in with him. 

In the shower, he was all over me. Kissing me. Soaping me. Pawing me
everywhere. It was wonderful. His fingers in my bottom were stretching
me, preparing me for the loss of my virginity. I couldn't wait. 

I know you already think I'm a little tart, but I made another big
cummy mess in the shower. It was those soapy fingers of Grant's
rubbing my prostate. And the kissing!

Grant grunted with satisfaction when I made a sticky mess. He loved
making me happy. What a great Daddy!

When we were clean, we stepped out of the shower and Grant dried me
off with big, fluffy towels. As if I were the most precious person on
earth. Then he dried himself off as my eyes drank in his magnificent
body. Especially his <blush> cock. 

He sat on the toilet as I stood in front of him. He powdered and
perfumed me and then, just so I wouldn't miss him when I was drying my
hair and putting on my make-up, he sucked my balls. Then he turned me
around and used his thumbs to gently part my soft globes. He smothered
my pink bottom with kisses, making me squirm and whimper. Then he
licked my tiny hole so sweetly that I managed yet another gusher of a
cumstorm. 

What a man! And he was all mine. At least for that afternoon.

Giving my bottom a playful little slap, he showed me where he kept his
cosmetics and lingerie for "guests." Though it appeared that I was not
the first (or even the 100th) of the little creampuffs he seduced, I
knew I was special to him. He said so, and he didn't seem like a liar.
Right?

Anyway, Grant went into the bedroom and left me alone in a nice little
bedroom with a fully stocked vanity table and closet full of lingerie.
As promised, Grant had laid out a lovely pair of black, seamed silk
stockings for me. The silk was cool and extremely girlish. I slid them
on and hooked them to me with a lacy garter belt. My hair was wet and
I had no make-up, but when I looked into the mirror, I erected yet
again.

I guess I liked being a man's fucktoy.

At least I was a pretty one.

I took my time getting ready, making "Daddy" wait. He had only cum
once, but I wanted him good and horny when he took my virginity.
Oooohhh. My bottomhole tingled at the thought of a man "doing" me.
Pushing into me. Spurting his hot cream into me. Making me his
property, to fuck when and how he wanted to. Ooooohhhh.

I dried my hair and fixed it up with a pink barrette and the sissiest
pink ribbon. I was going to wear a bra, but changed my mind and just
let my budding titties breathe free air. I rouged the nipples a
little, just to be naughty. I even perfumed my inner thighs and
<blush> my "pussy" hole. 

I slid on the naughtiest pair of black silk panties I could find –
they even had a pouch that fit my rather large package. Finding the
naughtiest, highest, fuck-me sandals with pencil heels (they were even
silver), I slipped them on my feet and considered myself in the
full-length mirror. I would be banned from every cardiac ward in the
country. I would be a menace to traffic in any city. Daddy would want
to fuck me until we both passed out.

I minced down the hall to the master bedroom, where I found my master
on his back, naked. He was propped up with pillows and his cock, due
to the long wait, was only at half staff.

When he looked at my forbidden-by-the-world, panty-boyish splendor,
Daddy's eyes lit up and his cock grew tall and proud. I sissied over
to him, stood at arm's length, and giggled. "Am I pretty, Daddy?" I
said. "Do you like me a little?"

Grant was only human. He sat up in bed and grabbed me. Pulling me
gently into his naked arms, he kissed me and praised my sweetness and
beauty. The sweet man placed me on my back and began to kiss first my
lips, then my perfect little titties. If I hadn't cum so much already,
I would have messed myself right then. It was heaven!

Then Daddy stopped kissing me and reached into a drawer by the
nightstand. He pulled out a new tube of something called "KY." Daddy
applied it liberally to two fingers of his right hand, then introduced
those fingers to my tight, virgin, little pucker. 

Ohhhhhhh.

Daddy kissed me as he lubed my bottom for what I suddenly wanted more
than my next breath. A good fucking!

After a few minutes, I was sobbing and begging to be fucked. On my
back. Helplessly submitting to Daddy.

Daddy said, "You're a brave little girl, Tina. I'm going to make you
very happy in more ways than one."

I didn't know what Daddy meant by that and didn't care. I was frantic
for his cock.

And Daddy was frantic to give it to me.

He mounted me, as if I were his bride. He kissed me, as if he really
loved me. Then he placed a pillow under my bottom, said, "I love you,
Tina," and pushed the big, fat head of his cock into my miniscule,
tight asshole.

I yelped at the unexpected sensation. Not pain, really. Just
discomfort. 

Daddy understood. "You're a very brave girl. I'll just rest a minute
to let you get used to it."

He was so sweet. "Daddy," I said. 

Daddy smiled. "Yes, precious baby girl."

"I love you too, Daddy. And it feels better. I want you to push it all
in and make love to me."

I think that was the moment I made Grant's A+ list.

He pushed further and that did hurt. But he rested and it was fine.
Two more slight pains, followed by pauses and he was completely in me.

My eyes were wide and I was holding my breath. I was completely filled
by a man's cock. My legs were on his shoulders. He had his weight on
me and he was going to fuck me in earnest.

Why had I ever resisted all this? I was happier than I had ever been
in my life.

Seeing that he wasn't going to kill me, except with love, Daddy began
to fuck me. Gently at first, then harder. Scraping my prostate with
each stroke. Leaning down to kiss me and, the sweet man, stroking my
very excited peener as he fucked me.

I was quite mad with pleasure. I was speaking in tongues and squealing
like a banshee. All of which fed Daddy's ego tremendously.

It also excited Daddy's cock. I had enough sense about me to give
Daddy's balls a good cuddle. They were huge and very hairy! And that
was the little extra that did Daddy in. He moaned as if he had been
shot, then grunted once for each of the seven sticky spurts that
drenched my poor ravaged bottom.

I helped Daddy by squeezing his prick with my anal muscles when I made
my own girlish mess all over Daddy's hairy belly. Our cums went on for
a good two minutes, which is some kind of record.

When Daddy recovered a little, he said, "No woman or no panty boy
ever……." And that was all he said. But I got the drift. And I was very
proud.

 

Chapter Eight – Set for Life

After that afternoon, evening, night, next morning, afternoon, evening
and night, and following morning with Grant, I was pretty sure that
things were going to be OK with me. 

Grant would have never left me if he didn't have to go back to his
business to do some merger or something. Or maybe it was his wife or
kids' birthdays or something. 

No matter. He gave me a three-carat diamond ring as a thank-you for
the best 48 hours of his or anyone else's life, he said, then set
another 48-hour date with me for six weeks in the future. And every
six weeks for the rest of his life.

He was terrific and he gave me such a good report to Mr. Rodgers
(along with a huge donation to the spa's coffers) that I was named
employee of the month!

I miss Grant when he's not here, but there are so many men out there
to sample. And sample them I do. I have dates all the time and for
every "date" I'm given a bonus in my pay envelope. Since I send half
my money home, my family lives like rajahs.

I don't need money, since the spa has set me up in my own apartment
and comped me everything. My pay all goes into a safe 401(k) plan, so
I'll be set for life by the time I'm 25. And men seem to buy me all
sorts of wonderful things, just because they admire me.

Haley and I are still sissy lovers, although we only get together
every week or so. So many men want to fuck the blonde, enthusiastic
new girl with the big cock and sweet disposition. Did I mention that I
now have long, straight, blonde, California-girl hair to go with my
new C-cup titties?

Haley has done pretty well in the men department too, as have Chelsea
and Courtney. But in all modesty, I'm the babe of all babes in this
place.

And it's a wonderful thing to be.

I even get about one marriage proposal a month. That might be nice.
Giving all my love to just one man. And some of my friends from the
spa now and then. And some of the ladies in my bridge group. And the
mailman and pizza deliveryman.

But I'll wait until I'm an old lady of at least 25 to do that.

The randy men of the world would miss me if I quit now.

 

 

 

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