journey
By Cassandra Morgan
- 1 -
- Andy's voice -
"Me Tarzan, Her Jane!"
The first 500 times or so I said it, it might have been amusing. The
last 500, people were laughing at me, not with me. But that was okay. I
was happy. The music was loud, and the alcohol was flowing, and everyone
at Mama Leon's nightclub was happy. Lights flashed. Laughter sounded.
People smiled.
It was Roleplay Night, which is always a good time at Mama Leon's. Think
of it as an R-rated costume party. Among me there were blue Avatar
creatures and Hobbits and Star Wars troopers. There were pixies and cops
and superheroes. Hookers and pimps and demons. Think of it like
Halloween with a hard on.
Molly and I came here twice a month for Roleplay Night, the first and
third Saturday, and we had a grand time. No one cared who won the
ribbons, but the costumes were taken quite seriously by the crowd. You
drew your assignments, and then you had two weeks to prepare, and then
you had Dress-Up Night to try to impress your friends. As an old college
theatre student, I loved it.
So here I was, in a loin cloth, while my wife, the magnificent Molly was
Jane. Okay, okay. I was more of an ironic commentary on Tarzan. I was
short, and I was a little skinny. But to everyone else, that seemed to
just enhance the statement. Why does a guy raised in the jungle have to
be a muscle man? Why can't he be a little guy with shaggy hair beating
on his chest? Yeah, it was funny.
Molly? Molly looked more like a sleek jungle creature than I did. She
was exotic, tall and strong, regal in her bearing. As a former college
basketball player, she's a tall girl, and she's been in a weight room or
two. She led Ohio State's team in rebounding for two years in a row.
She's 5-11, much taller than my 5-7. She's beautiful, with long brown
hair and green eyes and a smile that will melt your heart.
Tonight, though, she wasn't smiling.
Molly and I met in college, one of those weird attractions no one would
have anticipated. For one thing, we were called "the Rainbow Warriors"
by our classmates. I think it's because people stunned to find out we
weren't gay. Like I said, I was in the theatre, and I was a small guy,
and I roomed with Jeffrey, who was obviously gay. She was an athlete,
and a tall girl, and assertive. Stereotypes still exist. So they thought
we were both same-sex dedicated. Truth was, neither of us had a problem
with gay people; we just weren't.
So everyone was taken aback when we started going out, and jaws dropped
when we become a twosome. We met in chem lab, and she made me laugh, and
before you long, our own chemistry had taken over. No one kissed like
she did. No one cuddled like she did. I never heard anyone laugh like
she did. No one was more giving. I never liked being away from her. Me?
I made her laugh, I guess.
We were both nearing 30 now, eight years later, and we were still
desperately in love. I know. it sounds sappy, right? But it's true.
We moved to Cincinnati after graduation and found work as an insurance
writer. I did some work in the local Little Theatre, but I never got a
lot of satisfactory parts. There seemed to be a clique there that I
wasn't part of
Instead, we discovered Mama Leon's, a bar near the river that catered
to, shall we say, alternative lifestyles, and we had been hooked since.
It was a place to get lost in. If you liked bondage, if you liked
roleplay, if you liked dressing like the clergy, it was your spot.
For me, it was amazing how role-play made more assertive, more assured.
Nothing like an assigned role to let one's inhibitions out. And it's
amazing how turned on you can get with a performance.
Over the last couple of months, I had been a rock star. I had been
Prince Valiant. I had been Valmont. I had been a gunslinger and Sonny
Bono and George Washington and Gomez Adams.
Every time, I had a blast.
Often, Molly did, too.
Not tonight, though.
Tonight, Molly's lips were tight, and she didn't laugh a lot. Something
was bothering her. Nothing ever bothered Molly. But tonight, something
was. She didn't want anything to drink. She didn't want to dance. She
didn't joke around. Even our friends, James and Brittney, the two
dressed as Samson and Delilah, noticed she wasn't herself.
I took her hand. I looked seriously at her. "What's wrong?"
"We'll talk later," she said. "I don't want to complain."
"Come on, Moll," I said. "I'll have a lousy time if you don't tell me."
"What's your problem, Molly?" said Brittney, an elementary school
teacher who was a close friend of hers. "You need to talk?"
Molly rolled her eyes. She started to say something, then stopped, then
cleared her throat and started again.
"Okay," she said. She hesitated. "I'm probably being silly, but I hate
the roles they give for women here. They're so meek. Jane, so two-
dimensional. A groupie? A barmaid? Betsy Ross? What? Am I supposed to
sew all night? Give me a break."
The roles were an old sore to her. So I tried to calm her down.
"Well, a lot famous literature is sexist," I said. "Look at Juliet. Look
at Gone With the Wind. Even the Little Women were little."
I laughed. She didn't.
"I'm thinking about stopping this, Andy," she said. "I don't want to be
your accessory. Women are real, too. It isn't that hard to get both of
us a decent role."
"Ah, it's just parts, sweetie," I said. "It doesn't matter how we dress.
It really doesn't."
She looked at me and started to say something, then stopped. I should
have paid more attention.
"Easy for you to say," she said. "You get to be the star."
"Next time, it'll be better, Molly. You'll see."
"It had better be. I'm tired of being arm candy."
"But you're so sweet," I said.
She swatted my arm and grinned. And the sun came out and the birds sing.
When Molly smiled, they always did.
- 2 -
- Molly -
By the next morning, I was out of my funk. I felt like I had acted silly
with my tantrum the night before. It just stewed me the way women were
disregarded in a lot of great stories.
I woke up with Andy's, um, groin pushing against me. That was always
nice. I rolled over, and we made love in the morning, sweet and
unhurried, like two lovers who knew the other's moves. We had a picnic.
We held hands. We made love again.
Then, two days later, on Monday, we got our roles in the mail.
Uh-oh.
"An athlete and a cheerleader," it said. I saw Andy cringe in
anticipation.
"Molly, it isn't so bad," he protested. "You were a college basketball
player. Why don't you wear your old jersey? You can be the athlete and
I'll be a cheerleader. They have male cheerleaders, you know. It'll be
fun."
I shook my head. The idea just didn't appeal to me. I was tired of this
role-play stuff all of the sudden. Not to be a baby, but I wanted
something that was more exciting. I wanted to be in charge.
I sulked for most of the morning. I thought of the great women of
history: Cleopatra. Marie Curie. Maggie Thatcher. Eva Peron. Why
couldn't they pick one of those?
Andy said we could find another role-play bar. We could skip a round or
two. Take a break. Whatever I wanted. I loved him for that.
Just before dinner, it came to me. It made perfect sense. It was one of
those light bulb above the head moments.
"I have an idea," I told Andy. "Now hear me out, because I've thought a
lot about this. You ready? Remember when you said it did't matter what
we wore? Okay. I want to be a football player. I want you to be a
cheerleader. A girl cheerleader."
"Don't be funny," Andy said.
"I'm serious," I said. "I want to be the main person. I want my
cheerleader to hug me and fuss over me. I want her to leave lipstick on
my face. I want to leave a hickey on your neck.
"No one pays attention to women's basketball. But everyone loves Peyton
Manning. Or Tom Brady. People high-five them. People slap their backs. I
want to be treated like that. I want to be the guy."
"But, Molly. I don't want to dress as a girl...."
"Why not? You're an actor, aren't you? Actors play all kind of parts. In
Shakespearean times, all the girl parts were played by men. You told me
that. What was so challenging about playing a guy raised by monkeys? But
this! This is a challenge."
"Yes, but ..."
"If anyone could carry this off, it's you. It'll be fun. You'll be
pretty. Your hair is long enough. You're lean enough. You have nice
legs."
"Molly..."
"Besides," I said in a voice she meant to finish the argument, "you've
done it before."
He looked at me. He looked like he wanted to know what I meant, but he
didn't want to know. You know?
"I don't know what you're talking about," he muttered.
I had him now. I grinned. "Andy, I talked to Jenny. I know you used to
dress up in your sister's clothes. I've known it for a long time. It's
okay, but you've been in skirts before."
He opened his mouth. No sound came out. His eyes looked like he was a
trapped animal.
"Molly, that was just acting stuff," he finally said. "I also dressed
like Batman. I dressed like James Bond. I dressed like Darth Vader."
I smiled. Checkmate.
"You wore a lot of dresses, too," I said. "And panties. And nighties.
Admit it, Andy. For God's sake, Jenny said you were Snow White for an
entire summer."
He sagged visibly. There was no talking his way out of this.
"No," he said quietly. "It wasn't Snow White. It was Belle. From Beauty
and the Beast."
- 3 -
- Annie -
And so our routine adjusted, just a bit. We still went to Roleplay
Night. We still drank and sang and laughed.
But I was the girl now.
Molly was the guy.
It started the next morning, a Tuesday. Molly called me into the
bedroom. She had several of her dresses on the bed. There was panties,
bras, shoes. She was serious about this.
"To get into character, you're going to have to lose the body hair," she
said. "What little of it you have. Then we're going to try some stuff
on. This stuff is a little tight on me. It should come close to fitting
you."
I protested again, but she wouldn't hear of it. She handed me a pair of
bright red panties with a ribbon on the front. "Start with these,
Annie," she said. "Please be my Annie."'
There was a pleading look in Molly's eyes. This was important to her.
And, yes, I was an actor. I could do this.
I took the panties from her and sighed. It was time to get in costume.
I slid the panties up my legs. They were cool and slick. I became erect
instantly. Molly smiled, but she didn't say anything. She turned me and
slid the bra over my shoulders. "God, you really do need to use Nair,"
she said. "And we're going to have to get you some tits."
I looked at her.
"No, not your own," she said. "Some breast forms. Why? Do you want your
own?" I teased.
"No," I said, weakly. I don't think she believed me. I don't think I
did, either.
She had me dress in a blue sundress. Hose. Heels. She took lip gloss
and applied it to my lips. She played with my hair. I felt as if I was
falling from a plane. This was wrong. This was out of place. Molly was
right. I had done some of this in high school, but I never wanted to be
a girl. I never wanted to go outside. I never wanted to be pretty. It
was just joking around,
Why, then, was I so erect?
There was an eroticism in putting on her clothes. Had I felt this when I
was a teenager? I felt ... pretty. My hair fell into my eyes. For all my
protests, I liked this. I liked the feel of it.
It is so much work being a girl. Makeup can take hours when you don't
know how to do it. Hair can take longer. Bra straps cut into you.
Pantyhose can be too warm. But there is a sensualness to dressing as a
female. From the first, I admit, it felt pretty good. Maybe that's why
British comedians like to cross-dress. It feels so nice.
Sure enough, two weeks later, I walked into Mama's as a cheerleader,
complete with pom-pons. There were barrettes in my pig-tailed hair
(long from my rock star and Tarzan days) and gloss on my lips and liner
on my eyes. I had a blue-and-silver uniform on. I was wearing pantyhose
and breast inserts. I was Annie.
And I was about to die.
I kept asking: How did I get into this? The whole time I was sliding the
dress over my head, the whole time I was curling my hair, I was
scared. But, yeah, I admit I was a little excited. It was a delicious
acting job. It was a challenge. And the panties felt wonderful, tight
and soft. The skirt rustled. The air tickled my neck.
As we entered the bar, we moved slowly, as if all eyes were on me. But
it was a costume party, a dress-up night. Who cared about some guy in a
cheerleading uniform? Hell, most nights at Mama Leon's, a lot of guys
wore cheerleading outfits.
As we walked through the lounge, Dorothy and the Scarecrow approached
us. It was Brittney and James, fresh out of Oz. James looked me up and
down and laughed out loud when he saw me. Brittney shushed him. "I think
you look pretty, Andy," she said, and somehow that seemed worse.
"...It's Annie," Molly said. "Not Andy. Annabeth, I call her. Isn't she
a babe?"
James laughed louder. I thought he was going to shout and point, for
God's sake. Even Britney giggled. I blushed at the eyes on me. Odd.
James was dressed as Scarecrow and Brittney as Dorothy, and they were
laughing at me. No one suspected that James was really an animal - hey,
he was a car salesman - or that Brittney was a farm girl, but with me,
everyone assumed I was a cross-dresser and this was my excuse to wear a
dress in public.
But again, clothes are clothes. It's amazing how fast you get used to
them, how long before you don't think about them. If a couple of guys
hadn't asked me to dance, I would have been fine.
Later, though, Molly put her arm around my shoulder and drew me into
her. It felt nice there. Warm. I could play this role. I could let her
be my guy. She leaned down and kissed my forehead.
"Thank you," she said.
"Thank you," I said.
Even in the wrong clothes, we made a nice couple. With her cleats, Molly
was a head taller than I was. She had on eye black, the war paint that
players wear, and her hair was slicked back as s\if by sweat. James and
Nicole, fairly close friends of ours, oohed and ahhhed over her. Me? I
got my butt pinched by James a few times, but I'm sure it was all in
fun.
We danced. We talked. Molly leaned over and kissed me, and it felt as
wonderful as ever. I felt her hand on my butt. I grinned.
It was as if no one else was at the club. Not James and Brittney. Not
the bartender. Not the other players. It was just my football player and
me. I sure hope he scored.
He did. That night, Molly lay me down on our bed. She told me to keep on
the cheerleader outfit. She kissed me. She caressed my neck.
In the bedroom, it was her show. Molly was in charge of our lovemaking.
She spread my legs and touched me. I look at her, not saying a word,
just submissive as I lay there. She reached underneath me and caressed
my butt. And then she did the most amazing them.
She stuck her finger in my bum.
"I love you, pretty girl," she said, pushing deeper. "I love you."
I looked at her, and the world seemed out of focus. It felt so wrong,
and it felt so right. She kissed me and continued to finger my asshole.
It felt naughty, intimate, erotic. I tightened my cheeks. Was it to keep
her finger from going deeper, or to keep it from getting away?
There was an urgency to Molly that night, a hunger. She rode me for most
of the night, pinching my nipples, probing my ass. She clearly was the
aggressor. Her vagina was so wet, so wonderful. It was our Honeymoon all
over again.
And so our lives changed, along with our roles. Two weeks later, Molly
was Robin Hood and I was Maid Marion. Then she was Othello and I was
Desdemona. Then she was Dracula and I was Mina Harker. She was Leia, and
I was Hans.
I never even asked anymore. We would get our assignments every two weeks
for what we would be a fortnight hence, and I always figured I would be
the girl. I was never wrong. I got further into the part. I emerged
myself in femininity. It was fun. It was frilly. I highlighted my hair.
I trimmed my eyebrows. I started to use adhesive to keep my breast forms
on rather than rely on my bra, just so I felt right in the shower.
Was this becoming me? I didn't care. Molly didn't seem to care. Being a
girl came easy to me, as if part of me was waiting for someone to demand
it.
Even between roles, Molly liked it when I dressed as a girl for
"rehearsal." Panties. Bra. Dresses.It became natural for me, welcome.
The lingerie felt nice. Of course it did. If two people from Mars arrive
on the planet, they're going to like women's underwear bettter. It's
softier. It's better fitting. Like Molly pointed out, I had dressed some
in high school. I liked a hem on my legs. I liked the constriction of a
bra. I loved perfume. I didn't admit any of it to Molly. But it was
thrilling There are millions of men - millions - who dress as women.
There is a reason.
Molly? She was having a blast, too. She cut her hair short. She
experimented theatrical makeup, especially in stick-on facial hair. She
bound her breasts. She drank hard liquor instead of wine. She laughed
louder, cursed more. When we went somewhere, she drove. She was the
alpha in our family, and we both knew it.
And in the bedroom? Oh, my.
Molly was always a good lover. But suddenly, she became even more
aggressive, She was always on top. She became more talkative during sex.
She was like a director of a play. Everything had to be just so.
It wasn't just her finger that took control. For instance, the week when
she was Robin Hood, she was on top of me holding down my wrists. She
mounted me roughly, and as she achieved full rhythm, she started loudly
whispering. "Pretend it's my dick. Pretend it's your vagina. Am I deep
in you? Do you like cock in you?" And, imagining it all, I thought I
would burst.
The next week, when she Othello, it went even farther. She forced me
down onto her crotch. "Suck my dick," she said. "Tell me about it. Tell
me how you're sucking my dick. Describe it."
There was nothing there, of course. Just pretend.
So far.
And yet, I whispered to her how big it was, and how thick, and I would
never be able to take it all, and how good it felt. There in the dark,
it almost seemed real. She grinded harder, frantic, desperate. There was
nothing gentle this time.
If you try, you can imagine. Two bodies grow so close together, it can
be hard to tell where one leaves off and the other picks up. Her lips on
my nipples. Her fingers in my hair. Her crotch grinding into mine.
She would trace my panties with her fingertips. She would nuzzle my bra
straps with her lips. She would stick her fingers into my mouth.
It was the most erotic sex I could have imagined.
Finally, I realized this:
Oh, my god.
I was her girl.
- 4 -
- Molly -
Look, don't get me wrong. We were just having fun. It was a little kink.
Neither one of us were ready for sex changes. We turned firecrackers
into dynamite in the bedroom.
Isn't that what roleplay is for? A little diversion? I little spice
during sex?
Just to be sure, one day Andy asked me if I liked the guy role better.
For God's sake, he said, I seemed to like wearing boxers.
I wrinkled her nose. Sighed.
"Down deep, I like being a girl," I said. "I like the plumbing. I like
being pretty. But it's fun to play, you know?"
He laughed. He was wearing a black dress. Earrings. Panties.
"I have some idea," he said.
"How about you, cutie?" I asked him. "You like being one of us? You like
guys looking at your ass? You want to suck a cock for real?"
"Molly!"
I laughed. I was happy. Molly was happy. Maybe she really had lesbian
tendencies in college. She prodded me toward felinity, always
encouraging makeup and dresses. You don't turn on a switch to absorb
this lifestyle, but I gravitated toward it naturally. Skirts began to
feel normal. Bras were a part of my routine. Looking back, it was
amazing how quickly it became the norm. And Molly seemed ecstatic to
have a girlfriend.
"Baby, I've said it before. It's just clothes, that's all. You and me?
We're what counts. I don't care if you dress like Marie Antoinette and I
dress as Zorro. By the end of the night, we're usually naked anyway. I
love you more than I love the role-play, but this is a lot of fun."
She kissed me.
"So who are we this time?" he asked.
I reached onto the table and sorted through the mail. Every two weeks,
instructions came in a yellow envelope. Sure enough, the telltale letter
was there.
I paused.
"You ready?"
He grinned. "How bad could it be compared to the chicks I play?" I said.
I tore open the letter. I fished out the contents, and I hesitated. "I
hope this one is fun," I said.
I read.
"Master and maid," it said.
"That's great!" I said said. "I've always wanted to be a Master. I'll be
good at it. You can be submissive and kiss my glove. I'll tell you what
to do!"
"Molly?" he said.
"Yes, baby?"
"Can I be the Master?" he said.
I tried not to laugh. He was standing there in a dress, all sexy,
trying to be in charge. I made a face, like something tasted bad. I
shook my head.I spoke in that deliberate tone, as if trying to explain
something to a child.
"Cutie," I said, "you're the girl. You know that. have all the panties I
bought you. All the bras. All the makeup. You're good at being the girl.
Let's play the roles that fit."
"But it's a Master, not a Mistress," he said.
"So what?" I said. "I've been the guy for two months. I'm bigger than
you. I'm stronger than you. And I can spank your ass. I was born to play
Master. Look at this muscle?"
"Molly, please," he said. "I've been a good sport. I'm worried about
being dominated."
"And you'll be sport this time, too. This is me, Annie. You can trust
me. I think you'll be pretty, sugar. We'll get you a maid's outfit and a
duster. If you want, you can practice on the dishes."
If this was a movie, this was where the music would have struck and
ominous cord.
- 5 -
- Annie -
It was Friday, in the afternoon, and Molly wasn't home from work yet. I
stood and I looked at the dress she had left on the bed and my mouth
went dry. I could not speak. I just stared at the folds of black satin,
laying there, teasing me.
I was mesmerized. Nothing had ever affected me like this. Not even the
cool, slick underwear of the last two months. Not the lipstick. Not the
nail polish.
I picked up the dress. It was light and smooth, as erotic as a
nightgown, as cool as an ice cream. I held it up against me. I felt
flush. I closed my eyes.
What was it about this article of clothing that affected me like this?
Even the thought of it hypnotized me. I didn't know why. I had never had
a maid as a kid. I never had a girlfriend dress as one. There had been
no erotic link hiding in my mind. But I couldn't deny that the dress was
magnetic, the cloth and what it represented. I could imagine serving tea
in this. Doing the dishes. Making beds. Getting fucked.
I disrobed quietly. I didn't wait for Molly's help. I draped the dress
over my head and, with some difficulty, I got the zipper up. I loved it.
The bodice hugged me like a lover. The hem danced at my thighs. The
petticoat billowed out in front of me. The choker teased my neck. The
hose were fine fishnets with a thick seam down the back. The heels were
heaven. The apron was frilly. I put the choker on, and the little hat.
The billowing petticoats.
I looked in the mirror.
I never wanted to take it off.
I had seen maid's outfits, of course. What guy hasn't? They were so hot
to look at. But they were better to wear. I had never had an attraction
to a role like this. I honestly wanted to go out and get a job cleaning
hotels.
When Molly finally came home, I was standing in front of the mirror,
trying to get my hair in a bun high on my head. I smiled shyly when she
came in. Her mouth dropped open.
"Oooh," she said.
"Exactly," I said.
"Annabeth, you are a vision," she said. "I'm getting a phantom boner
looking at you."
"Don't make fun, Moll," I said. "This...this is perfect."
She took me in her arms. "You were made to wear this dress," she said.
"Darling, you are beautiful."
And I was.
Did you ever go somewhere and immediately felt at home? Did you ever
drive a car that seemed to fit you, That dress was that to me. It was
snug, and it was sexy. As I practiced my curtsies, I felt it was created
for me, And me for it.
We swept into Mama's later that night, and every head turned. My dress
was black, as were my collar and my leash, I walked behind Molly, who
was stunning in a leather halter and leather pants and bold makeup. The
instructions called for her to a Master, but she was dressed as a
Mistress, and the effect was startling. At more than six feet, counting
her stilettos, she looked like an ancient queen. I trailed behind her,
on my leash, my head slightly bowed, and I could hear the erections go
"boing" as we walked.
This time, James didn't laugh. Britney, either. They just stared, like
dogs staring through window of a butcher shop.
They were dressed like John and Yoko. And nobody ever told them there
would be days like this.
"My, God, Annie," Brittney said. "I'm going to have to do a woody check
on James' crotch."
"Don't bother," James said. "I'm at attention. You're going to put
Viagra out of business."
I smiled and looked at the floor. There were pillows there. I sat on
them as Molly sat tall in the chair beside me. I wrapped my arm around
her right leg. This was where I belonged.
The night flew by. I was at home. I was content.
This time, when men asked me to dance, I did. Even James. He held me
tight and spun me, and I felt alive, crackling on every nerve end. He
leaned in. His hand brushed my butt.
"You're gorgeous," he said. "I want to be with you."
"Excuse me?"
"I imagine your lips on my cock, Annie. Would you to suck me? There, I
said it."
There was something slick about James, something disingenuine. I didn't
care for him, to tell the truth. A rattlesnake salesman, I think they
call it. He's the last guy in the place I'd let hold my wallet. If there
was a pet mouse in the room, I'd pet it. He'd feed it to something.
"James! I'm married!"
"Please..."
I spun. I walked toward Molly.
Between you and me?
I may have been smiling at the attention.
- 6 -
- Molly -
That night, I started kissing Annie in the back of the cab. There was a
lustfulness to her, to us, a desire that I had not felt before. It was
raw, and it was basic. She melted into me like she had finally
surrendered her gender. She was my girl.
We locked lips through the front door, and up the stairs, and into the
bedroom. Her hands were on my body, my breasts, my legs. I wished they
were real breasts for the first time. I unzipped her, and let her dress
fall the floor.
I pushed her to the bed and held her wrists down while I lowered my face
and kissed her. I let go of my wrists. I smiled.
"Touch my cock," I said. "Please, baby."
Annie knew this game. She smiled. She reached down, as if she was
expecting to feel the usual emptiness but to lie about it. Instead,
there was a definite bulge there. What?
She sat up, pushing me off of her. I laid back.
She undid her leather pants and tugged. And sure enough, there it was. A
long, thick, lifetime penis. It was shaped like a real cock. It felt
like a real cock. I was wearing a panty to hold it in place, and it
jutted out long and strong.
"When did you buy a dildo?" she whispered.
"Today at lunch," I said. "As long as I was eating, I thought you
should."
Annie laughed. Amazingly, like its was the most natural thing in the
world, she bent down. She kissed it gently. She looked up at her, and
she lay back, and she took it in my lips. She swirled my tongue around
the knob. This was wonderful. It didn't feel gay. It felt ... nice. For
the first time, Annie said, she understood why so many women loved
giving head.
She began to bob her head, taking in more all the time. I put my hands,
gently, on Annie's head and wrapped her fingers in her hair. She was
learning what it felt like to suck a guy's cock, to feel the skin go
from being someone else's to part of yours, to feel it claim you.
She sucked harder, and deeper, and wetter. I writhed in the bed as the
internal knob rubbed against my clitoris. I was getting close.
And then it spasmed, and fluid came pouring into her mouth.
She started to cough as the fluids flowed into her throat.SheI had no
chance to swallow anything It spilled into my pubic hair and onto the
bed.
She looked at me as if asking a question.
I grinned. "It's called a Squirter," I said. "You fill it with fluids,
and the pressure builds till it comes. How is it?"
"You could have warned me," she said.
"I'll warn you this time," I said. "Now turn over, and let's see how it
works on your cute little butt."
She looked at me to see if I was serious. Seeing I was, she rolled over
onto her side. I grinned against her, kissing the back of her cheek. I
lifted one of her buttcheeks and probed the opening. She gasped. I had
lubed it thoroughly, but her butt wasn't used to being an on-ramp, only
an exit. I pushed harder. She whimpered.
Slowly, I worked it in, thrusting in rhythm. Naturally, I couldn't feel
the tip. But I felt her bottom against my grown. I felt my breasts on
her back. I gripped her shoulders and pushed deeply.
IT was heaven. It was complete surrender. She was demanding now, pushing
against me, grinding and gripping. She never felt like more of a woman
to me.
Finally, it squirted again, and she came into my palm. I considered
making her eat it, but I rubbed it into her chest instead.
"Nice, kitten?" I said.
"Nice, Mistress," she said.
Just saying, my heart had skipped a beat when she called me Mistress.
- 6 -
-Annie -
It was still early when I woke. I took Molly's arm from around me and
gently lifted it. I slid out of bed and moved quietly across the room.
I grabbed my panties and my bra, discarded on the floor.I picked my
maid's dress off the chair in the corner. with my petticoat. I didn't
bother to look for my chocker, my collar on my leash. Not when we were
at home.
It was 4:30 a.m. now. Time to make the doughnuts. I tiptoed across the
room, bending over to pick up a heel here, a heel over there.
For four days, I had done the same thing. I woke up before dawn to get
started. I had makeup to put on. I had breakfast to prepare. I had a lot
of work to do before waking Molly at 7:15.
This was right. This was proper. The debut night of Maid Annie was fun
and sexy, but there are chores that come with being a maid. No one knew
that better than me. This was my house, and damn it, it was going to be
clean. I was going to do what I was required to do.
I went into the bathroom and examined my underwear. Still fresh. We took
it off before we did anything last night. I had draped my dress and
petticoat over the chair.
I looked in the mirror. My hair needed work. I had to do my eyes and my
lips. I blinked.
I dressed quietly. I did my makeup. My ass was sore.Too much Squirter
last night. For a woman, man, could Molly fuck. I think it's the
athlete in her. Just my luck. I'm getting nailed by a jock.
Finally, I was presentable enough to be walked in on. I padded
downstairs. There, I put on the kettle. Eggs Benedict today? Maybe an
egg-white omelette? Pancakes?
I decided on the omelette. I put croissants in the bread warmer. I put
the coffee pot on.
These are good hours for me, the maid and her morning moments. I can
think about how my life has changed. I can think about how Molly's has.
I can try not to wonder about the days to come.
I still can't believe I'm a girl, but I've worn the same dress for four
days. I would never be caught without makeup. I do my chores like a good
girl. I vacuumed yesterday. That makes it laundry day today. I've
started watching soaps.
No one blackmailed me to do this. No one has threatened or coerced or
tortured me, the way the stories all say. I do this because it seems I
must. If this was a story, I mused, the dress would be magic. The
bartender would be a wizard. The taxi driver would be a hypnotist. Molly
would be a scored woman bent on revenge. We would be trapped in a town
where the husband was feminized.
But this was life. And I did this because, well, it felt I should do
this. It was where I was comfortable. It was my place.
There were soft footsteps behind me. Molly? She was up already? That's
not right. I hadn't even put the eggs on yet.
She walked into the kitchen and poured herself some coffee. She sat.
"Mistress," I said. "I would have brought you your coffee."
"Annie?" said Molly. She never called me Andy anymore. I don't even
think she thought of that as still my name. "Can we talk?"
"Yes Madam," I said. "Of course."
"Sit," she said. "Please. You've been in that dress since Saturday
night. What's going on with you?"
"Nothing, Mistress," I said, glancing at the floor.
She reached over the table and lifted my chin. She looked into my eyes.
"Tell me," she said.
I felt a tear run free. I calmed myself.
"Mistress, I cannot stay out of these clothes," I began. "I don't know
what it is. I didn't feel like this when I was a cheerleader, or when I
was Maid Marion. I was just playing a part then. But from the first time
I saw this dress, from the first time you mentioned it, it has
captivated me. It's just cloth. I know that. But love the whole package.
I love the chores. I love the dress.. Is that horrible. Do you hate it?
Do you hate me"
Molly smiled sweetly.
"If you love it, then wear it, you ninny," she said. "You're my love. Do
you think I care what thread you wrap yourself in? Do you think I care
if you do chores? It's great. Most of your insurance accounts are self-
renewing. Money is no problem. So let's be happy, okay?"
"It's a strange fetish, Mistress."
"Nah," she said. "It's harmless. You don't hurt kids. You don't abuse
innocents. You don't cheat. You just take it up the ass."
I looked at her, and she smiled.
"Tell you what, Annie. We'll get you some more uniforms today. One for
every day of the week. Some work shoes. Or some heels. Whatever you
wish. We'll pierce your ears. If you want a makeover, I'll make an
appointment at the salon. I can't get you boobs yet, but we can make an
appointment if you want to."
I looked her. She was wonderful. She could see my soul, and she knew
what mattered to me.
"I'll always love you, Annabeth," she said. "I'll never hurt you. I'll
always protect you."
In the days ahead, I was to doubt that. But I would never forget how I
felt when she said it.
- 7 -
- Molly -
"I know what drives Annie. She's a girly boy. If you ever left her,
she'd end up with some guy from Cleveland. But what drives you in this
relationship?"
Brittney and I sat in booth at O'Riley, having drinks and potato skins.
It was inevitable that our lifestyle would come up. But I wouldn't have
thought it would come up so quickly. I wouldn't have thought that
Brittney would be so dismissive of Annie.
I sipped my Scotch.
"Me? I'm just a guide, Brittney. I'm just trying to help figure out who
she is."
"Bullshit, Molly. You like this shit. You like her doing all your
choires. You like telling her what to do."
I smiled.
"Yeah, I admit it. There is a part of me that gets off on the power.
It's like tapping not he side of a fish tank and making the goldfish
scatter. I like deciding what we're doing for dinner. It's fun.
Brittney fiddled with a potato skin.
"Damn, I wish you could still smoke while you drank," she said. "So,
aren't you tired of the little sissy yet? You're not a fucking lesbian."
I shook my head. Everyone wanted to know about our sex life.
"It really doesn't matter," I said. "I like Annie in skirts. I like her
in the kitchen. She's pretty. She's a gentler soul that she used to be.
If anything, she's just too damn nice."
"Well, at least she doesn't fuck around on you. James will put his dick
in anything, I swear. The goldfish isn't even safe. He'd probably even
fuck Annie."
I laughed. Everyone knew that James tom-catted around town. If we voted
which husband would come down with Herpies, it would be him.
"Why do you put up with it, Britt? Really?"
"Really? I don't know. He's good in bed. And he owns all of our ropes.
Most of our chains."
"Ropes? Chains?"
"Yeah, we dabble a little. We're up to the 51st shade of gray."
I laughed again. There was an earthiness to Brittney that I found
refreshing. Everything was a joke. But this was the first time I heard
of her and bondage.
"You know, Brittney. I admit it. Being a Mistress is a thrill for me,
too. I like benign charge. I like the rush. I like dressing her up like
a Barbie doll. You know, we went to a men's strip club the other night.
Dicks everywhere. Black dicks, brown dicks, white dicks. Big as the arms
of babies. I never could have done that in the old days. But this time,
Annie just sat and watched. I think she liked the view. She even touched
one."
Britney giggled. "You know, she really is a gay caballero."
"Don't say that Britt. I thought you liked her. You're always so nice to
her."
"Molly, be real. that's how all of us are. We gossip like hell. We're
nice, because we all know gay people those days. But we laugh. We talk
about her dress. We talk about her leaving lipstick on underwear. Hell,
we talk about you, too. How you're turning into such a guy you might
smoking cigars."
I almost fell out of my chair laughing.
"If I was a guy you'd fuck me," I said.
"No," she said. "But I'd let you put me in a dog cage."
It was a good moment, a relaxed moment among friends. Good drink. Good
conversation.
"So, Britt. Are you ready to see some permanent chances in Annie?"
"Permanent?"
"Yeah. I thought about another set of pierced ears. Maybe a Minnie Mouse
tattoo. Maybe boobs."
"What?" Her eyes got wide.
"Yeah," I said. "It's time she cant put her tits in a drawer at night.
I'm thinking a C-cup. I know a lot of sissies get Hindenburgs. But I
just want something she can't hide when she goes to the grocery story,
but not something as big as my head. Something that's fun to lick."
"Molly, you perv!" Britt laughed. "But I bet the fag likes them."
So everyone thought Annie was gay, huh? We might have to work on that.
- 8 -
- Annie -
Some days, you have to stomp out the forest fires.
Take Tuesday. I had just finished the dishes, and the washer buzzed that
it was finished, and I had to load the clothes into the dryer, and I had
to vacuum, and the toilets needed scrubbing, and I had to cut the
chicken for dinner. Soon, I would have to fold and iron. Any second now,
the dry cleaning would come.
The doorbell rang as I had an armload of clothes. So I put it on the
washer, and I rushed to get the door. I was sure it was the cleaners. I
didn't give a second thought as to how I was dressed.
It wasn't the cleaners.
It was Jenny.
My sister stood in the doorway, a bottle of wine in her hands. My
sister, who shared cake with me. My sister, who had shared a room until
puberty hit. My sister, whose clothes I dabbled in as a teenager.
I opened the door, standing there in front of her in a blue maid's
dress. My hem felt short, My God, why did this keep happening to me?
"Annie, is it?" she said. "You look beautiful. I thought I should drop
by and check on you. See how you're doing."
I let her in, a little embarrassed as how I was dressed. I made her
coffee. We sat on the couch. I didn't say anything.
"So you're living as a woman, Annie?" she said. "I talked to Molly. She
told me you were into cross-dressing as a domestic."
"Well, cross-dressing isn't totally correct, Jenny. "I'm dressing as a
maid. Well, that's just as bad, isn't it?"
Jenny laughed.
"I don't care, honey. The world is filled with transvestites. It figures
I would know one of them. Even if it's my brother."
I sat on the couch. I crossed my legs, a feminine gesture. I stuck a
loose strand of hair back where it belonged. I couldn't help it. Every
move I made these days was more like a woman.
"Jenny, am I a transvestite? I mean, really. There isn't anything wrong
with it. I know that. But don't most transvestites start as young
children? Five or six?"
"You'll find this out. Annie, that there are transvestites who emerge at
all ages. There are 80 year old men who get caught in their wives'
pantyhose. There are toddlers who dress in Mommy's clothes."
I told her how this had happened so fast. I told her about the role-
play, and the evolution to being a maid, about Molly's newfound
aggressiveness.
"So where do you go from here, Annie?"
"I haven't thought about it, Jen. I get up and make breakfast, you
know? I'm just surviving. I don't spend lot worrying about the future."
Jenny looked me. "Let me ask you this flat-out, Annie. Are you gay."
I hesitated.
"I like the way guys look, Jen," I said. "I touched a penis the other
night, and all I wanted was to kiss it. I think about someone in me. I
still like sex with Molly, when I can get it. But I could go both ways.
I'm sure of it. But I never have."
She looked long at me.
"You don't sound happy."
I thought about it. Was I happy?
"I'm content, Jenny," I finally said. "I have my place. It's weird when
I think about it. but when I get up in the morning, I feel like I ought
to be in a dress. I feel like that's who I am supposed to be.
"For now, that's enough."
- 9 -
- Molly -
Fro some reason, I would have expected a brothel. Lots of red and gold.
Cheap perfume and painted ladies.
Instead, she saw an elegant banquet hall. High chandeliers. An elegant
stairway.
She sat in the foyer and awaited for her appointment with Mistress
Teresa. They knew of her at Mama Leon's. Mistress Teresa was the most
well-respected mistress in Cincinnati. Molly had sought her out
specifically. She needed to learn about her husband.'s new lifestyle.
She needed to learn about her new lifestyle, too. She had bought a $200
bottle of wine as a tribute. She wished she had spent more.
Another stereotype vanished when Mistress Teresa came into the room.
She was an elegant looking woman, like the former tennis champion of a
country club. She carried herself like loyalty. She reached a hand out
and shook Molly's.
"I'm Terry," she said.
"Uh...Molly," I said.
"I have a good feeling about you, Molly," Mistress Teresa said. ''Most
Mistresses don't bother to meet with their elders. They just wing it on
instinct and gut feeling. It's why so many of them mess up. It's an
awesome responsibility."
"It...is?"
"Yes, my dear. Think about it. Your sissy certainly works very hard. She
is very dedicated. Her hours are grueling. But, honestly, there isn't a
lot to her job that requires thought. You clean the plate. You get the
wrinkle out. You sweep up the dust. There is not a lot of morality being
decided in her life.
"But as the mistress? You are responsible for her physical, her
emotional, her psychological well-being. You have all the financial
burden. You have all the sexual issues for you both. You have to decided
punishment. You have to know how much punishment to inflict, and how
much to withhold. Even when you don't want to, you have be mean if
that's what your sissy needs. You have to know when to kiss...and when
to bite."
Mistress Teresa leaned back and poured herself a cup of tea. She poured
milk into it.
"Everyone thinks it's about how many times you decide to you spank her,
and then you eat cookies," she said. "It isn't like that. Now, you
should know this. There are a thousand interpretations on being a
Mistress. Some will be angry and mean, and some sissies eat that up.
Some will be gentle and kind, and other sissies eat that up. Some
sissies need a strong hand. Some mistresses need a weak one. You have to
seek your own balance. You have to spoon out love and discipline, wisdom
and guidance, sex and understanding."
"Mistress Teresa..."
"Terry."
"Terry, I'm not sure what to do. My husband has an unbelievable pull
toward this sissy think. She gets up, she does her chores, she is great
in bed, but there is a sadness about her. I sense she is still
unfulfilled. Am I doing something wrong?"
"Do you love her?" Mistress Teresa said.
"More than anything," I said.
"That's what matters most," Mistress Teresa said. "Or it should. The
women who want to use lifestyle this to fuck another man, or to get
someone to blow their boyfriends, or who want to torture their former
lovers, they are all off track. I suspect many of them are the products
of the imagination of transvestites who want desperately someone to take
control of their lives. The true relationships that have a chance of
lasting? Love binds them. The honest desire for both parties to get what
they want. The strength to administer it."
I started to say something but Mistress Teresa held up her hand.
"Now, that doesn't mean it's a stroll through the park. Sissies do
hunger for discipline. Many of them want punishment. And because of
that, they are happiest when they are being disciplined. That's why I
have a 12-step program. Would you like to hear it?"
"Of course, Mistress."
"You know, you are very pretty. Have you ever considered life as a
submissive?"
I smiled.
"No, Mistress," I said. "I think we have enough of those in our house.
But it's very flattering."
"Shame," Mistress Teresa said. "You have a very spankable ass. By the
way, sweetie,did you know that there is sperm in your tea?"
"What?" I said, sitting upright.
"I'm just teasing, dearest," Mistress Teresa said. "Or am I? What good
is power if it doesn't give you the right to laugh? Oh, well, there are
miles to go and asses to whip. Let's get on with it, shall we?"
- 10-
- Teresa -
Step One: Transvestism
"You know, of course, that there are subs who don't wear women's
clothes. Although why they wouldn't want to, I have no idea. But the
common thing that all submissive have is that they crave humiliation.
"Now, you say your sissy wears women's clothes on his own?"
"That puts us ahead of the game. No need for forced feminization. No
adapting. Because for our type of sissy, there is no substitute. It's
odd. In other cultures, the traditional Japanese, the middle Eastern,
transvestites wear the traditional women's garb of their cultures.
People think all transvestites want to wear western style women's
clothing. But it isn't about the clothes. It's about being a woman. It's
sincere flattery.
"There are those who say that sissies are parodies, and that in their
way, they are sexist. I don't buy it. They wear the prettiest, the
finest, the softest. Because of that, most women are much more
comfortable around them that men. I think a good sissy is a compliment
to a woman. They'd have babies if they could.
"Now, Molly, I would always keep your sissy in dresses. Or skirts. If
she likes wearing a maid's uniform, as you say, then make sure she wears
a lovely gown when she goes to dinner. Make sure she sleeps in a
nightie. She's halfway between sexes, You have to stress the female
half, because in her mind, she deserves to be one of them, to suffer the
way we do.
"That's where we come in. To help them suffer."
Step 2: Accessories.
"There are many subtle touches to being a sissy, Molly.
"Start with makeup. It's a must. No, not garish makeup. No one wants a
clown version of a woman. We want elegant strokes. As a woman, you know
how many years it took you to be in charge of your own face. Now, you
have to help her - and you always call her her.
"Jewelry is important. Some Mistresses don't think about it. But a
necklace, a ring, an ankle bracelet is the perfect punctation to our
statement.
"Now, are you part of the tattoo generation? Personally, I am not. But a
great many mistrasses like to ink their sissies. A nice pair of
lipstick-colored lips, maybe. A unicorn. Just word "Sissy." I would
advice against tattoos that show, but that's me. I'm an old fuddy-duddy.
There will be other things you can use to brand her."
You know the best identification. It's a new birth certificate. Change
her name to Annie legally, and the formality of it will suck her dry.
Change her last name to your maiden name, and it will stagger her. What
was it? Rourke?
Step 3: Exposure.
"This is very important, Molly. Annie will not want to be seen, but she
must be. No matter what she says, she longs for people to know who she
is, what she is.
"You are not embarrassing her here. Well, some maybe. The important part
is that you're freeing her. One her friends and her family know, they'll
talk, and they'll giggle, but then they'll accept. She's a sissy. It's
natural.
"Make her go into public. Make her answer the door. She'll fight you,
because sissies avoid the light. But once they're there, they bask in
it. Remember, they aren't just transvestites. They aren't looking for a
home with a fence and a good man. They want to wash stains out of
underwear.
Does she have a work office? No? Shame. That's a good place for
exposure. The golf club. The sports bar. Make sure they know she's a
sissy. If they want to think she's a cock-sucker, let them. It's more
degrading that way.
"I always remember this: If in doubt, go wtih the thing that will
embarrass your sissy the most. Or punish her. It isn't about you. It's
about her. Sometimes, you have to spank even when your hand is tired,
dear. Sometimes, you have to open the window shades and let the world
see in."
Step 4: Breasts
"Has Annie asked for breasts yet? She will.
"A discussion? That's how it starts.
"In a sissy's life, there is no more permanent alteration that is more
desired. A vagina leaves no bulge. Shaved legs can be covered. But if a
sissy has the swells in her bosom, the world is going to see.
"To me, the breast is the most womanly of organs, even more than the
pussy. What is more maternal than a baby nursing? It is a miracle. It
really is. Now, you have a decision to make. You can get hormones, or
you can get implants
"The hormones are more natural. Healthier, I think. But they take time.
And they remove his ability to get hard. Implants would give him tits
quickly, and they'd let him get hard.
"A sissy wants breasts. Sometimes, they desire quite large ones. I'm
more conservative myself. If its' left up to me - and isn't it always? -
then I think a B are a C cup. Leaver her wanting more, you know.
"Now, this is important. Tits are important. A vagina isn't.
"There have been Mistresses who have forced a sex change on their
sissies. It's a fun idea, but it's bad to carry out. If you give a sissy
a pussy, you give her status. She becomes a woman, which is far above
her station in life. You make her an equal.
"But as a guy? She's a sub-species. Better to keep her dick and make fun
of it. Better to threaten to castrate or have SRS. But don't do it."
Step 5: Chores
You say Annie takes to them? That's good.
"The truth of it is, you will have a far greater adjustment than she
well mentally, We all want to help. Don't. It's her job, and her
gratification comes when you make her do it. Make sure she keeps a list
of her chores each day.
"Let me ask you this: Was Annie a good housekeeper before he as a sissy?
No? I didn't think so. Men are slobs. Remember this: It isn't housework
that your sissy likes. It's discipline. It's being forced to do the most
menial taks in a home. Scrubbing the toilet. Washing the dishes.
Vacuuming the dirt off the flipping floor.
"She will be happy when you make her do this. She may "forget," so she
will be punished. That's usually about the punishment more than it is
the chores. Her chores will be more important to her than food, than
water, than oxygen.
"Do remember this. Maids work very long hours. If breakfast is served by
7, say, then they have to be up by 6, maybe 5:30. Yet, dinner isn't
served until 6 p.m. or so. By the time the dishes are washed, you're
looking at a 14-hour day.
"So give her some breaks. In the afternoon. Or a day off. She won't ask
for them. She'll just keep working. But find her some time off. Right
after you get her more cream, damnit!"
Step 6: Penis size
"Now, I have talked bout love and support. Now, you need to embarrass
your sissy a bit. She lives for that.
"Now, what is the object of all male vanity? It's the penis, of course.
No one brags about how big their foot is, or how long their fingers are.
But there is such a source of pride with most guys, such a vanity.
"Take that away from your sissy. Talk about his cockette. Or his
dicklette. Call it a clit.But never let him forget he isn't a real man.
"How big is Annie? Average? Most men are, by definition. And if six
inches is average, that means that for every 10-inch porn star there is
out there, there is some guy with a two-incher. So tell him he's small,
even if he's average. Look, most men don't measure theirs, not unless
they are porn stars. Most men depend on their women to brag on the size
of their dicks. So stop. Talk about how small it is. Keep him humble.
"Besides, if Annie really wants big dick, why, she can find one
somewhere else."
Step 7: The Cage
"As long as we're talking about the penis, my dear, have you considered
a cock cage? No? For heaven's sake, why not?
"No, don't think of it as punishment. Think of it as putting her orgasm
in your hands. Something that important shouldn't be left to a sissy,
should it?
"Now, I'm not of a mind to let it rot. Everyone in my family has their
day of the month when we play. I even have one I let put it in me, but
I'm soft-hearted.
"You'd be surprised. With most sissies, the cock is the last thing they
surrender. Guys like their dicks. And that's why we must control them.
Otherwise, most sissies would be like chimps at the zoo.
"Better to cut them off. But that's messy. So lock them up. And hide the
damn key."
Step 8: Punishment
"A lot of self-made Mistresses like this one. They get to spank. Whips.
Belts. Canes. Ropes. They go out of their way to find something wrong,
and they flay ass when they find it.
"I believe in the carrot-and-stick myself. I spank with my hand, because
it's more personal. I will threaten a great deal. I will scold.
"Now, you have to decide where you are going to let her sleep. In a
spare bedroom? On the floor? In your bed? Think carefully. If she shares
your bed, there is a message that still has equal footing there. I
wouldn't advise the floor. If you have a spare room, make it a maid's
quarters. But it's up to you.
"You aren't here to be cruel, Molly. You are here to guide. Don't get me
wrong. Spanking is fun, and it's needed. Taking privledges away is
important. Making someone go to bed without food works. Tightening her
corset works well.
"But remember this. A disapproving look can be devastating to a sissy.
She lives for your happiness. If she doesn't earn it, she'll be
devastated. Spanking at least gets Mistress's attention. So does
bondage.
Here's a thought: Don't be a jailer. Be a mommy.
Step 9: Sex Toys
"I'm all for them, as long as they are used at your direction. I love
handcuffs. I like whips,the small ones. Paddles.
"Dildos. There is a place in heaven for whoever invented the dildo. I
woman, I imagine. The butt plug? Invaluable as far as stretching out her
rear.
"What do you use? The Squirter? Nice. I have a nice double-headed blue
one. Very long and then. Scratches those itches. There are also units
that vibrate. But you do have to mount her. You have to let her know
that she is the one who is getting penetrated most nights.
There are locking clothes, locking shoes. Annie won't need those. She's
addicted, from what you tell me.
"I never cared much for artificial vaginas. They insult the vagina.
Besides, if sissy has an ass..."
Step 10: Urination
"No one likes to talk much about this one, Molly. But are you into
golden showers? Brown showers? Toilet play?
"Me, neither. It's too messy. You pretty much have to do it in the
shower, and where is the fun there.
"Certainly, I understand the attraction. What could be more humiliating
than someone pissing on you? Or making you drink it? As disgusting as it
is, it's delightfully degrading. That's why it seems to be as popular as
it is. There are some guys who would rather be peed on that have an
orgasm.
"If you are going to do this, be careful. Use a funnel. Pee only a bit.
Have fun with it.
"Me? I prefer to put sperm in someone's tea. Drink up, dearie."
Step 11: Cuckoldry
"Will you take a lover? No? You might change your mind.
"That's one of the joys of our lives, sweetie. We can do what we want
with no repercussions, There are a lot of sissies who enjoy seeing a
bigger penis drive in and out of their lover. That's as embarrassing as
pee, having someone cum in their woman. Sometimes, you can make them
lick it clean. It's delightful.
"To a sissy, two women aren't as erotic as they are to guys, because
sissies don't have the dick to do anything about it.
"Warning, though. You can never go back. Fucked once, fucked forever.
Step 12: Sperm
"There are a lot of bisexual sissies writing these stories, you know.
We never know what the real number is.
"But in sissies, bisexuality is like most things. It isn't about the
act. It's about the humiliation Some guy is going to deposit his semen
in your lips. How horrible. How wonderful.
"I'll be honest. I like to watch my sissies with each other. They are so
trusting, so innocent, as that flesh pacifier goes in them. I'm getting
warm just thinking about it.
Again, it isn't about being gay. Not really. It's about being used. It's
about having someone call you a cum dump, and knowing it's true. That's
embarrassing.
- 11 -
- Molly -
A few nights later, I lay in bed. A million thoughts had tumbled through
my head after I left Mistress Teresa. She was a wonderful mentor, even
if the tea did taste funny.
Annie lay in the crook of my arm. Trusting. Giving. She had become a
sissy so quickly. It was as if I could rewind the tape, and she would be
Tarzan again. Well, Sheena maybe.
I reach down and lifted her penis, as if it were absent mindedly. I
gently stroke it. I stretch it to its full length.
"You know, Annie. This would make a great vagina."
She looked at me, trying to phrase how she could say what was on her
mind. My God, Mistress was right. She was scared of the knife.
"Mistress, are you serious?" she said.
"Well, sure. You cut it here, longways. And down here. It's such a
little dick. It won't take much."
She traced it with her fingers. I started to protest.
"Mistress. It isn't so little."'
"Come on, Annie. Lets be honest. You could floss your teeth with that
thing. It's so cute. I mean, I haven't seen a lot of them. Counting
yours, I'd say I've seen 4 1/2. Yours being the half."
Her peeny stirred a bit in my fingers. Maybe I was getting to her. I was
a little colder, a little more critical. For her benefit, of course.
''Annie, everyone can't have a big dick. It's the button dicks that lead
some guys to be sissies. It's okay. If I had been a lesbian, I wouldn't
have any; dick at all."
Annie lay still for a minute, as if still thinking about it.
"Do you regret not being a lesbian?" she said.
"Sometimes," Molly said. "But then there are big dicks. Oh, goodness. I
can't wait to get back to those."
"Get back...." I looked at her aghast.
"Annie, you don't think I'm going to live the rest of my life without
sex, do you?" she laughed. "I have needs to. You'll always have my
heart, but you'll be blowing guys, and I'll be getting piped in in my
room."
My senses overloaded. Her having sex? Blowing guys? Getting piped. Her
room? What?
"Mistress?"
"Yes, sugar."
"I don't want to blow guys.""
"Of course you do. Deep down, all sissies do. Silly girl. Sometimes a
couple of guys. I read about a game where four guys site in opposite
directions, and the sissy sucks each guy for 10 seconds. You can bet on
who wins. And who finishes second. And who finishes third. With those
lips, you would be good at that game.
"Think about it. A wonderful penis, fucking your face. Isn't it
delicious?"
I figured it was best to talk matter-of-factly about her giving blow
jobs. That way, it would be easier to accept. Deep down, I thought she
wanted that. I was going to give it to her.
She shivered. "What do you mean 'your room."'
"Oh, sissy. You need your own space. I figured we'd make up the spare
room with all of your closet space. And if you want a guy to stay over,
you can be alone.
"Mistress, we've never cheated on each other..."
"It isn't cheating, sillly. Not if you know. Not if you understand. It's
called cuckoldry. I need a normal sized cock, not that baby dick of
yours."
A tear rolled out of Annie's eye. Her resistance was useless, as they
say in the movies.
I looked sadly at her. I wanted too tell her that I wasn't going to
remove her penis. I didn't want her to sleep with guys. I didn't want
her to move out out of the bedroom. I was just doing my job.
After all, I was the mistress. And I owned her.
- 12 -
- Annie -
If was Thursday night, and I was washing the dinner dishes. There was a
particular hard stain in the frying pan, and I was scouring hard when
Molly came in. She watched me work for a while, trying to avoid getting
my apron wet, or my gray maid's dress underneath.
Finally, she cleared her throat.
"Yes Mistress?" I said.
"Annie, I'm a little bored. Let's do something different this weekend."
"Yes Ma'am. What would you like to do? The theatre, maybe? A trip to the
country?"
"I was thinking of having some people over, Annie. Your mom. Your boss.
Your sister. Jeffrey. James and Britt. Earl and Jimmy, your old golf
buddies. You know, just a few."
"Maam? I don't have any boy clothes any more."
She smiled. "You won't need them, silly. You'll be serving. Maybe in the
white maid's dress."
I flushed. My mother? Jenny? Jeffrey?
"Ma'am? I can't believe we would invite them over."
"Excuse me," Molly's voice grew louder. She never raised her voice to
me. "This is my decision, Sissy. Not yours. If I say we will invite
them, then invite them we will. You have no say in the deison."
I hung my head at my outburst. Tears streamed silently down my face.
"They'll know," I said.
"And what if they know? This is who you are now, Annabeth. You will be
in dresses forever. Why shouldn't they know that their son is a cock-
sucking sissy."
"Ma'am, I don't do that."
"Don't you backtalk to me, sissy. Now come lay over my lap. It's high
time I stopped putting up with this foolishness. Now. Down with the
panties."
I was stunned. She had never spanked me. But quietly walked to her, and
pulled down my underwear. I lay across her lap."
Whap. What. Whapwhapwhap."
Five quick, painful blows. My ass was on fire, but my soul hurt worse. I
was sobbing. The truth is, the emotional torment was far greater. She
had assumed her authority. She could spank when she wanted. She could
hurt me.
My dick was like a rock, however.
And so we had our dinner party, and I was there in my dress and heels
and makeup. I wanted the earth to swallow me. I felt like a gay teenage
coming out. I was ready to be laughed at