House Boy - Part One
My name is Dorian Simmons. As my story starts, I am dreaming. I am on a
merry-go-round. Around and around I go, faster and faster. My head feels
like a children's toy top, spinning dizzily. As I whirl around in
circles, the blood flows to my crotch.
I wake with a euphoric throbbing between my legs, and to find my fianc?e
Elise under the covers. The suction on my cock so intense, it feels like
she's trying to drain the life out of me. Half in dream world, and half
awake, I groan as my entire body tingles. I shudder and twitch, as
ejaculation comes. Spurt after spurt of vanilla tapioca shoots from my
penis, filling my girlfriend's warm, moist mouth.
"Good morning darling," she said, looking up at me with a devilish
smile. She licks away a drop of semen on her chin. Tossing her gorgeous
blonde ringlets out of her eyes, she crawls on top of me, kissing me. I
grimace as I taste my own cum. Yuk!
No matter how gross, I did not stop her from sticking her tongue inside
my mouth. I would do anything for Elise.
This beautiful, shapely creature is only 22-years old, and a fashion
model for the Ford Modeling Agency. The way she licked her lips,
reminded me of the way she'd done the same thing in a toothpaste
commercial she'd just taped for television.
"Did you like that my sweet?" she purred, wrapping her arms around my
neck and holding me close.
"Oh my god, you are spoiling me," I sighed happily.
I am the luckiest man in the world. Elise is simply stunning. She has
the face of Heidi Klum and the body of Beyonce? high cheekbones? million
dollar smile? pert nose? and a body that knocks men off their chairs
when she struts the runway at fashion shows in Milan, Paris and New York
City.
"Come on sleepy head," Elise said throwing aside the sheets. "You said
you only wanted a little nap. We're supposed to meet Larry and Harmony
at the club at nine."
I watched her pert and perfect B-cup breasts bounce as she hopped from
bed. Her gorgeous heart-shaped ass swayed sexily as she crossed her
bedroom and opened a walk-in closet. On top of being the most beautiful
woman I'd ever met, Elise's family was filthy rich. At 22 she owned her
own loft right in the heart of Manhattan, courtesy of her father, who'd
made all his millions in computer chips out in Silicone Valley.
"All right," I said, wiping my eyes, and heading toward the shower.
Under the water, I remembered how we'd arranged to set up my friend
Larry with one of Elise's model friends, a brunette beauty from
Australia named Harmony.
I'd grown up with Larry Shapiro in New Jersey. We'd gone to
undergraduate school together at NYU. After graduation I'd taken a job
working for Elise's father selling computers to large manufacturing
plants, while Larry enrolled at Columbia's Law School.
Physically he was a big guy, with broad shoulders and a lot of smarts.
He came from old money in Newport, Rhode Island, and had helped me
numerous times with my grades in college. That said, he was a bit nerdy
looking - balding at 23, with wire frame glasses, and a nose that looked
two sizes too big for his body. He always bemoaned the fact that he got
all the good grades while I got all the pretty women.
In an effort to help Larry out, Elise and I had arranged this blind date
for him with Harmony. Unfortunately, when we got to the club, and the
four of us were seated, I could tell right away that things were not
going to work out. Harmony looked like a 21 version of the Victoria's
Secrets model Stephanie Seymour, only with an accent like Nicole Kidman.
She paid Larry absolutely no attention, and seemed utterly focused on
Elise. As the music pounded in the nightclub around us, and the lights
flashed, and Harmony laughed and chattered away, poor Larry sat there
sipping his Coke looking miserable.
Around 11:00 p.m. Larry had had enough. When the girls went to the dance
together, he told me, "I'm going to get out of here."
"Don't go! You haven't even danced with her!" I cried.
"Forget it Dorian," Larry said pushing his glasses up his long nose.
"It's not going to work." He looked at me with some irritation, possibly
imagining all the fun I was going to have with two beautiful high-
powered fashion models to myself.
"We're still going to play racquet ball Thursday, aren't we?"
"Yeah, I guess. Call me. I've got a new cell phone number." He opened
his wallet, withdrew a business card, and jotted a number down on the
back.
"All right buddy," I said taking the card. "I'm sorry about tonight."
"Don't worry about it," Larry sighed. "You're the one that's always had
all the luck with the ladies."
Luck was right. After Larry left, the two girls sandwiched me on the
dance floor. With Elise in front of me and Harmony behind me, their
bodies undulating against my pelvis and backside, they practically raped
me right there in the club under the flashing lights.
After a couple of drinks and a few dances the three of us went back to
Elise's loft, where I lived out every man's fantasy of spending the
night having sex with two gorgeous women.
I didn't actually make love to Harmony? that might have been pushing
things too far? but just to see her naked, and making out with my fianc?
as I finger fucked Elise, and she masturbated me with one hand, and
Harmony with the other, was utterly mind-blowing.
The next morning while the girls were showering together, I dug out
Larry's card to rub it in a little about my fun night. Funny. I thought
he'd written his phone number on his own card - but it was actually on
the back of someone else's card. Printed on the front it read:
"Mistress Alexia, Behavior Modification Specialist, (212) 494-3894."
Mistress? Behavior modification?
I dialed Larry's cell number on the back, and said, "This card you gave
me last night, with your number. Who's Mistress Alexia? Are you seeing
some kind of a prostitute?"
Larry got all flustered, and apologized, saying he didn't realize he'd
given me that card. "No, no! It's nothing like that at all."
"Then what's this all about Larry? It's okay. You can tell me." The poor
guy. He couldn't get a woman, so he was seeing a hooker. A pro-Domme.
"Someone at Columbia gave me the card. I never even called her. I
swear!"
Yeah sure. He seemed so upset, I just let it drop. When I told him about
my night with the girls, it only compounded his misery.
Still, I didn't throw the card away. I kept it in my wallet, and every
few days I found myself pulling it out and looking at it. Mistress
Alexia. Behavior modification. Curiosity was driving me crazy.
On my computer at work I Googled "Mistress Alexia" and "New York City."
All of which led me to a profile on a web site called www.collarme.com.
Unfortunately there was no picture. Just a short written profile and the
same phone number:
Mistress Alexia
Behavior Modification Specialist
Strong, strict, but loving Domina seeks generous, submissive bad boys in
need of corrective treatment. Specializes in bondage, corporal
punishment, feminization, humiliation and anal training.
I am not looking for a boyfriend - just well paying slaves that I can
use and abuse at my whim. So please don't even go there. I am bisexual
and prefer women for emotional relationships and males for teasing and
torturing.
Possible house boy position available.
Call today for your free consultation. (212) 494-3894
Free consultation!? I read the profile over and over, examining each
detail. What did she mean, she preferred women for emotional
relationships? The more I looked at it, I found myself thinking of
Mistress Alexia as the ultimate challenge for my charms as a Casanova.
I'd conquered Elise and countless other attractive women. In my mind I
built a cozy fantasy of meeting this black leather goddess and taming
her? till she fell madly in love with me. Me. Dorian Simmons.
By Wednesday I could stand it no longer, and during my lunch break I
dialed the number. 212-494-3894. I got a machine. Damn. I called back.
Constantly, every two hours, till finally Wednesday night around 10 p.m.
someone picked up.
"Hello, this is Mistress Alexia."
Gulp. My throat went dry. "Er., hi. My name is..." Suddenly my mind went
completely blank! "Dorian! My name is Dorian."
"Did you see my ad Dorian?"
"Yes. I-I saw your profile on the internet," I stammered. "I called
about the free consultation."
"So what are you into? Bondage? discipline? cross-dressing? do you like
getting fucked?"
"No! I've never done any of those things before."
"Then why are you calling me?"
I really didn't know why. I was just curious.
"Okay. Let me explain something right up front. I am an extremely busy
woman. I don't have time for players. Are you familiar with Charlie
Brown's on 20th Street? I go there every Monday night for dinner."
Charlie Brown's was a moderately priced steak house on the east side.
"Be there this Monday at 7:00 p.m. If you have the balls to show up,
we'll chat. If you decide not to come, fine, no big deal, but I will
block your number and never speak with you again. Ever. And that's
final. Understood?"
"I'll be there!" I said enthusiastically.
Thursday, I was so excited about my date with Alexia, when I met Larry
at the gym to play racquetball, I couldn't help but tell him about it. I
had to tell somebody.
"You did what?" Larry exploded. "Are you out of your mind? You're
engaged to one of the hottest women in the world, and you made an
appointment with a Dominatrix?"
"It's just a consultation!" I replied, serving the ball.
Larry swung, sending the ball whizzing against the wall. "You're an
idiot!"
"I'm just curious!" I cried, swinging my racquet, sending a sizzling
shot to the corner, making Larry dive for the ball.
Somehow Larry made the shot, hitting a light tap, that I would have had
to run for. I didn't even bother. Larry was so damn competitive.
"My serve," Larry said, bouncing the ball. "What do you hope to
accomplish by meeting this woman?"
I shrugged, and said, "I don't know. I really don't know. I'm just
curious to meet her. We'll meet, chat, and that will be the end of it!"
I couldn't wait for the rest of the week to go by. Normally I looked
forward to weekends because I got to spend them with Elise and I could
not wait to be in her bed. But for the first time since I met Elise, I
felt distracted. All I could think about was satisfying my curiosity
about Mistress Alexia.
So when Monday finally arrived, I put on my best pair of dark slacks, a
new pullover shirt, and even blew dry my long, straight brown hair. I
admit, no one has ever accused me of being the sharpest knife in the
drawer, and I'm not the biggest, most muscular guy in the world, but I
was blessed with one asset that opened a lot of doors for me: a pretty
face.
From the moment the host seated me in a booth with Alexia, I could tell
she was delighted by my appearance. We she first saw me, her face lit up
like she was just coming off a diet and I was a juicy T-bone steak.
Whereas she seemed pleased, I admit, I was less than impressed. Mistress
Alexia must have been at least twice my age. I guessed about 45. And
overweight. She had short brunette hair cut in a man's style, a bland,
round face, and a ghostly pale complexion without a stitch of makeup.
Although she wasn't wearing black leather, she was wearing a black
button-down shirt and a pair of dark slacks.
"How old are you?" she began.
"Twenty-three," I said.
"My goodness," she said looking flustered. "You're still a baby. The men
who call me are usually quite a bit older."
So our conversation began.
Before our entrees arrived, I learned that Mistress Alexia had known
from childhood she knew she had an overly strong, domineering
personality. She said she felt she was born to be a leader, but felt
stifled in most jobs she'd ever hard, because she had a hard time taking
orders from men. As she became more dominant in her sex life, she simply
integrated it into her career, and became a professional Dominatrix.
"My clients are mostly married men. Much older than you. In their 40's
and 50's. Boys your age can't afford me. My subs tend to be professional
men. Doctors, lawyers, accountants, dentists? I even have a police chief
that I see and a politician. Some come from as far away as Washington
D.C. and one flies in from Dallas every month."
I listened in fascination. All right, I could see why Mistress Alexia
hadn't posted a photo on her profile. But once she opened her mouth, I
admit, I was mesmerized. She was right. There was something very direct
and forceful about her way of speaking, her mannerisms and her body
language. The woman had power, and a superior intellect.
Her eyes narrowed as she looked me over. "So tell me sweetie. What
brought you to my web site?"
"Actually a friend gave me one of your business cards. He said it was by
mistake. Did you ever meet a guy named Larry Shapiro?"
"No," she said cutting her prime rib. "But then again, a lot of men
don't use their real names. So tell me. Why did you call?"
I blushed and sipped my iced tea. "I don't know exactly. I was curious
mostly."
"Do you have any sexual fantasies?"
I'd always wanted to screw Elise up the ass, but she was squeamish about
the whole idea, so I'd given up trying. "Not really?"
"Do you have a girlfriend?"
"Yes. I'm engaged actually. To a beautiful woman. Have you ever heard of
Elise Nelson?"
"The Ford Agency model?"
"Yes. She's my fianc?e."
Alexia's eyes widened and she shook her head. "Very impressive, indeed.
She's stunning." She wiped her mouth with her napkin. "What is she like
in bed?"
I shrugged, feeling a little smug. "Oh, she's wonderful. Incredible. We
have the best sex."
Alexia's brows furrowed. "Then what are you doing here? With me?"
I didn't know actually. I tried to remember my thoughts on viewing
Alexia as a challenge, but couldn't quite duplicate my train of thought.
"Most of the men that I see come to me because their wives won't do
certain things."
"Like what?"
"Like dressing them up in lingerie."
I blushed deeply. "Why would a man want to do that?"
"Have you ever tried it?" she smiled sweetly. When I shook my head
vehemently no, she grinned and said, "Then you don't know how exciting
it can be till you've tried it. Women's lingerie is all very tactile.
Silks. Nylon. Lace. They feel very arousing against your skin?
particularly when you're not used to such fabrics? and especially
because it's all quite forbidden to men. I'll bet you would look
adorable in a merry widow, garter belts and stockings."
My face got so red, she laughed at me gaily.
"You look so cute when you blush," she grinned.
When we were finished eating, as we walked out the front door of the
restaurant, Alexia said to me, "So, I guess you're going home to your
girlfriend, the super model?"
"No. We don't live together. I'm heading home to my studio apartment
uptown."
"Hm?" Her eyes narrowed. "How would you like to walk me home? maybe come
in for some coffee? We can chat a little more. I like just around the
corner."
I gulped, and found myself saying, "S-sure!" And I didn't even drink
coffee.
She lived a block away in an apartment on the sixth floor of a tenement
building on 8th Avenue. Once inside she said she would give me the
"grand tour."
The living room was tastefully decorated, with polished wooden floors, a
pit group of cream corduroy couches and lots of plants and art deco
prints by people like Maxfield Parish and Picasso. She had two bedrooms.
Her room had a huge king-sized mahogany bed, and the other she'd
converted into what she called her "dungeon."
She flipped on the light. There was a simple single bed in the room, a
matching bureau, and a large, ornately cared wooden cabinet with double-
doors. She unlocked the cabinet, and opened it up, revealing rows of
paddles, crops, chains and implements I had never seen before. Giving me
only a quick peek, chuckling at my open-mouthed stare, she closed the
doors and locked them back up.
Making herself a cup of coffee and giving me a glass of soda, she led
the way to her living room, where we sat side by side on the love seat.
Thankfully she did not turn on the T.V.
"You're submissive, I can tell," she said.
"What are you talking about?" I sputtered. Me? Submissive?
"I have a sixth sense about these things. You do the whole straight,
model thing as a cover-up. You really want to serve a strong, Dominant
woman like me. That's what brought you here. That's why you called."
I laughed out loud. "You don't even know me!"
"I know your type," she said smugly. "I'm willing to bet I know you
better than you know yourself."
My mind was spinning like a merry-go-round. "I'm not submissive."
"Okay, I'll prove it. Hm? I bet I could make you do anything I want.
Anything. And you'll do exactly what I tell you to do."
Feeling nervous and apprehensive, I tried to laugh off such a wild
accusation. "You don't know what you're talking about!"
"Don't I?" she said, eyes narrowing, focusing on me like lasers. "In the
snap of my fingers I can make you do whatever I want."
"This is getting crazy?" I said growing scared.
Alexis's demeanor hardened, and reminded me of my crusty old grandmother
just before she got ready to scold us for coming in the house with muddy
clothes.
"Stand up!" she said quietly, but firmly.
"What!?"
"You heard me. Get up. Or get out!"
On wobbly knees, feeling a bit like a robot, surprised by my own
actions, I did as I was told.
"Now take off your clothes," she said sipping her coffee, hiding a
smile.
"WHAT!? I don't even know you!"
"Shut up! Stop jibber-jabbering and just do as I say. Take off
everything. I want to see what you look like naked. Let's see what your
girlfriend sees in you. Do you have a big cock? Let me see."
Astounded by what was happening, fingers shaking, I began to pull off my
shirt.
"Everything. Undershirt too. Take it off. Now your shoes."
I couldn't believe I was doing this. I wasn't submissive! Yet I found
myself pulling off my socks, then my pants? till I was down to a pair of
Hanes boxer briefs.
"Panties too," she said.
"They're men's underwear!"
"Just shut up and pull them down," she said, sipping her coffee as I
pushed my briefs down to my ankles and stepped out of them.
Sitting back comfortably on the couch, Alexia studied my body from head
to toe, while I stood there trembling with nervousness and excitement.
Turning red, I tried covering my privates with my hands.
"Don't hide it," she snapped, pushing my hands aside. "Let's see what
you've got. Goodness. It's rather disappointing. Rather small."
Mortified, I croaked, "It gets bigger."
"Let's see. Play with yourself. Get it hard."
"Alexia! Please! Enough is enough!"
The black clad woman lounged on the couch, sipping her coffee. "This is
hardly anything at all. I'm just trying to figure out how you're able to
keep a top model like Elise Nelson happy. You're not very tall or very
masculine. You don't have any hair on your body at all. No muscles. And
you can't even get a hard-on. Not very impressive."
"I can get hard," I said through gritted teeth.
"Then do it!" she said smiling sweetly, looking up at me.
Hanging my head, my heart pounding, I began to touch myself in front of
this 45 year old, pudgy, ordinary-looking woman with an attitude, who
sat there grinning triumphantly.
I couldn't believe I was standing naked in front of a woman I'd met only
hours ago, masturbating! My heart raced, I felt scared to death, but at
the same time I admit, I felt strangely aroused. I pulled on my organ a
few times, and in a matter of seconds I was fully erect, and stroking
myself proudly.
"Goodness. Is that it?"
"What do you mean, is that it!?"
"Oh I'm sorry honey. I don't mean to hurt your feelings or anything. But
trust me, I've seen hundreds of hard cocks in my day and yours is?
pretty? it's got a very nice shape? but you're quite a bit less than
average. What is it? About three inches?"
"It's bigger than that!" Four inches. I knew because I'd measured it.
Alexia giggled, and said, "Honey, I was right. You're a sissy.
Especially with a piece of equipment like that, you could never service
a real woman. The only thing you'll really ever be fit for, is serving
some woman or man as their submissive sissy."
At that point I stopped touching myself, and instead, having my
masculinity so degraded?I hid myself with my hands. Plus, calling me a
"sissy" struck a raw nerve. When I'd grown up, on a couple of rare
occasions, some of the jocks in the locker room in junior high school
had teased me about my small size and nicknamed me "peanut." I'd been so
humiliated, to this day I will not eat anything with nuts.
"Okay, I've seen enough. You can put your clothes back on and go home
now."
"What?" I said, standing there, feeling like a complete fool.
"Do I have to repeat myself constantly with you?" she said with some
irritation. "Let's go Little Missy, you can pull your panties up and
leave."
I gulped, and did as I was told. I was so nervous, my erection quickly
dissolved. Doing my best to hide my crotch from her view, I quickly
pulled my pants up and finished dressing.
"I can't believe you got me excited like that? insult me? and then just
tell me to go home," I said feeling grumpy. "Is that it?"
"Yes, that's it for tonight," Alexia said languidly. "When you get home,
I want you to call me. Do you understand?"
"You do?"
"There you go with the questions again. All you have to say is, Yes
Mistress," she corrected.
"Yes Mistress," I repeated.
"You mind as well start learning the proper etiquette if you want to see
me again. You do want to see me again, don't you?"
"I don't know," I said with some irritation. I still couldn't believe
how easily she had manipulated and belittled me. "You're leaving me very
frustrated."
This seemed to be music to Alexia's ears. She grinned happily. "Good.
Glad to hear it. Now go."
We hugged, and I kissed her full on the mouth. Nor did I give her just a
peck. I held it as long as she let me, till finally she pushed me away.
Her eyelashes fluttered almost prettily, and she giggled like a young
girl. My kiss surprised her, but not in a bad way. She looked a bit
flushed herself, and later would admit to me she wasn't used to getting
kissed by "pretty, young boys."
My mind in turmoil, I took the subway back to my place. I sat there in
the rattling subway car, replaying everything over in my mind. Maybe
Alexia was right. Maybe I was submissive. I couldn't believe how easily
she'd gotten me to do her bidding.
As soon as I got back to my apartment, I took all my clothes off,
climbed into bed and called Alexia on my cell.
"Good, good, I'm glad you made it home safe. Where are you? In your
living room, or?"
"I'm in my bedroom."
"Are you naked?"
"Yes, I am," I blushed, and started to fondle myself.
"And I'll bet your playing with yourself."
"Yes," I gulped.
"Ah? young men and their libidos. Eventually we will have to do
something about that. But for now? you want to masturbate, don't you?"
"Yes," I whispered.
"Well, go ahead. Play with your little pee pee. Only you are not allowed
to cum until I give you permission."
"All right." I winced as she referred to my endowment as little. Amazing
what a single word can do to a man's psyche.
"The proper response is, yes Mistress Alexia!"
"Yes Mistress Alexia!" I said as I played with myself.
"Good," she purred. "Now. I have a question for you. Do you want to see
me again?"
"I?I?" I didn't know. She had me so out of sorts, I was a bit scared of
her actually. She'd insulted my masculinity? called me a submissive.
"Can I cum now!?"
"No! Not until you answer my question. Do you want to see me again?"
"Yes!" I cried. I'd tell her anything she wanted to hear just so she
would allow me to ejaculate.
"I thought so," Alexia purred in the phone. "I don't think you can
afford me, and you're much too young to take on as a client, so I have a
proposition for you."
"What kind of a proposition," I squeaked as I continued stroking like
mad.
"Well, if you saw my ad online, you know that I'm looking for a house
boy. You're kind of cute, and I have a feeling you'd make the perfect
sissy house boy. That way you can still see me, it wouldn't cost you
anything, and I can train you, so that when you get older, and you meet
a nice Dominant woman, you'll be able to serve her properly."
I had no idea what she was talking about. "What would I have to do?" I
asked through gritted teeth. I wanted to cum badly, but was trying to
hold back.
"So do you want to be my sissy house boy Dorian?" she whispered sexily.
"I-I don't know," I hesitated, masturbating like crazy.
"You'd get to take part in sessions with my submissives," she said
softly. Although Alexia was not attractive, she had one hell of a sexy
voice! "You'd get to take a peek inside my world. See what I do to men.
You'd get to watch me dress them up? beat their ass? and fuck them."
"Can I cum now!?" I asked frantically,
"Answer the question first. Do you want to be my house boy?"
"Yes!" I cried. "Yes, I'll do it! Now please let me cum!"
I heard her pause, and chuckle. Making me wait, teasing me to the
limits, gave her great satisfaction. It was all so surreal, Alexia had
me so worked up, normally I would have cum by now, but somehow she had
control of me, even through the phone line!
"All right little Missy, go ahead. Have your little spurt."
As soon as she said "go ahead," I came. Powerfully too. So hard that it
shot all the way to my chin. Nor did I have to say a thing. Alexia knew
exactly what was happening just by listening to my shrill cry of
pleasure.
"My, that was quick," she purred. "And right on cue." She laughed
softly. "And you don't think you're submissive. Do you feel better now?"
"Yes," I said gasping for breath. I'd made a mess all over myself.
"Call me on Wednesday night ten o'clock so we can discuss your duties.
I'll be waiting to hear from you. Good night, little Missy."
I lay there in a puddle of my own cum, wondering what I had agreed to.
House boy? What was that? As I hung up the phone, I felt somewhat
grumpy. She'd gotten me so horny, I'd wanted to cum so badly, I would
have agreed to jump off the Brooklyn Bridge.
The next day at work I must have screwed up a half dozen times on
different projects. I just couldn't keep my mind on what I was doing.
All I could think about was the previous evening with Alexia.
Was I crazy? Fooling around with a professional Dominatrix? Especially
an overweight one that was twice my age. She wasn't even pretty! And
yet, every time I thought about her, I got an immediate erection.
As she'd requested, on Wednesday night I called Alexia at exactly 10
p.m.
"You're on time," Mistress Alexia purred into the phone. "That's good.
So. Is your little pee pee hard?"
Actually it was. "Yes," I admitted.
She chuckled into the phone. She took it as a sign over her control over
me, and loved it. "Good. But you're not to masturbate this time. In
fact, you're not to touch yourself until I see you again."
"When will that be?" I asked, almost frantically. What did she mean, I
wasn't allowed?! I'd masturbate as soon as we hung up, if I damn well
wanted to.
"Hold on there little Missy. We need to get a few rules cleared up
first. You do still want to be my House Boy, don't you?"
I gulped, unsure what I was getting into, but certain that it must
include lots of wild and kinky sex. "Y-yes? Alexia. I mean, Mistress
Alexia." At the time, I had no idea how those few words would change the
course of my entire life.
"Good," Alexia said, obviously delighted. "Now just to clear up some of
the ground rules. Rule #1, is quite simple. You do exactly what I
command you to do - or our relationship is at an end. There are no
questions asked. No need for discussion. This is not a democracy. When I
tell you to do something, especially in front of a client?you do it?and
you do it right away. For all intents and purposes, you are my slave.
It's my way or the highway. If I tell you to do something and you give
me an argument? I will tell you to leave? and there will be no coming
back. For instance, if I tell you I want you at my house on Friday and
it's your skinny little girlfriend's birthday - I don't want to hear
about it. No, is not in your vocabulary. Disobey me, and I will hang up
on you - or ask you to leave. Our relationship will be at an end. Is
that understood?"
"Yes?" I whispered.
"Rule #2. Everyone addresses me as Mistress Alexia. But you, as my House
Boy?I want you to call me Mommy."
Mommy? How odd. "Yes... Mommy."
"Excellent. Be at my house this Friday night at 9 o'clock sharp."
Friday night I traditionally went over to Elise's right after work. We
ordered pizza and rented a movie and sort of slid on into the weekend
together. "On Friday nights I?"
"What did I just say?!" Alexia practically screamed into the phone. "Do
you want me to hang up on you right now!? Are you some sort of a retard?
After only five minutes are we already at an end?"
"NO!" I cried. "It's nothing. I was just thinking out loud about
something I was supposed to do. I can re-schedule it. It's not a
problem."
"Good," Alexia growled. "Because on Friday night I have one of my
favorite submissive clients coming over. He's a wealthy older gentleman,
in his 50's, and a surgeon. All I want you to do is sit and watch. He
will pay me an extra $100 just to have a cute young boy sitting there in
the room, watching me beat his ass."
Her voice grew conspiratorial, as she added, "I'll split the $100 with
you, so you make $50 out of the deal. And you don't have to do a thing.
Just sit there and watch." She chuckled. "I promise you, you'll find the
evening much more entertaining than renting a video."
"Sounds g-great," I said, my voice cracking like a teen going through
puberty.
"Good. Now remember. No touching yourself until Friday. As my House Boy,
you're not allowed to touch yourself unless I give you permission. And,"
she said evenly, "all I will have to do is look at you?and I'll know if
you've been a good boy or not."
"I'll be good," I said, wondering how I would be able to wait two days.
I normally masturbated twice a day. Once in the morning when I woke up,
and again before I went to sleep.
"You'd better be. See you Friday," she said, and hung up.
What had I gotten myself into already? What was I going to tell Elise?
My beautiful Elise!
I did what any man would do in this kind of situation: I lied.
I made up a story and told Elise that my parents had invited me to their
place in New Jersey for dinner on Friday night, and that they had
something important to discuss with me. What exactly, I didn't have a
clue, and would have to concoct later.
After I made up my phony excuse, and Elise sighed and said, "Okay,"
after I hung up the phone, I groaned. Something had just been lost in
our relationship. I'd never lied to her before. Not blatantly like this.
A month ago I would have never considered giving up an evening with
Elise. She was the love of my life Elise? the girl of my dreams? the
woman I wanted to marry and spend my life with. And yet, I just did. I'd
lied to her just to spend an evening with a Dominatrix and a 50 year old
pervert that liked getting his ass beat.
Actually, it turned out he liked quite a bit more than that?
On Friday night, I ring the bell in the lobby of Alexia's building, and
she buzzed me in. "It's open," came a scratchy metallic voice through
the intercom. I went upstairs and found the door to her apartment
unlocked.
My pulse rate shifted up a gear as I stepped inside her living room. No
one was in sight. I tapped on the closed door of the dungeon.
"Come in," came her muffled voice inside the play room.
I pushed it open, wondering if I was going to get jumped, beaten and
robbed.
No. The door opened, and there stood Mistress Alexia in her full
regalia? a skin tight pair of shiny black pants, knee high boots with a
4" stiletto heel, and a black leather corset, from which spilled her
volumous breasts. In her hand she held a black riding crop.
Before her, hands restrained up over his head, dangling from a chain
hooked to the ceiling, was a naked, blindfolded, balding, 53 year old
surgeon named Bernard.
His ass was crisscrossed with red welts. As I watched, she grinned
broadly, quite merrily, as she brought her arm all the way back, like a
pro at Wimbledon getting ready to whack a tennis ball. The riding crop
sliced through the air, leaving another bright red stripe across the
poor man's sweaty derriere.
He screamed into a ball gag that was strapped around his head.
"Our guest has arrived," Alexia said softly. "Close the door."
I did as told, the sound of which perked up the blindfolded man's ears.
Beads of sweat burst from his forehead. Suddenly his whole body seemed
to be glistening with perspiration.
"Yes," Mistress Alexia whispered into the man's ear, while grinning at
me. "She's finally here. Just like I told you." She?
The man tried to say something, but his words were garbled by his gag.
"Yes, exactly," Alexia chuckled, and gave him another red stripe with
her crop.
The man shrieked, his whole body tensing.
Alexia strode across the room to me, and lowered her voice. "He thinks
you're a woman. He'll be even more excited when he finds out you're
really a man. So don't say anything to give away your identity. Just
lift the register of your voice a little bit, and speak softly if I say
anything to you. And? go put on the clothes I've laid out for you on the
bed."
I glanced at some sort of a frilly pink costume, with huge crinoline
skirts. "Where should I get changed?" I whispered. The bathroom?
Her eyes looked me up and down in complete amusement. "Right here
darling. It's not like I haven't seen you naked before. Take off
everything and put on the things I've laid out for you, including the
heels."
"You said I would just have to sit and watch," I hissed quietly. "I've
never?"
Alexia's eyes stopped me from saying another word. "Just go with it. I
promise you that you are going to enjoy every minute of this."
I gulped, and found myself saying, "Yes Mommy."
"Now where were we," Alexia said, and went back to heating up Bernard's
bottom with her crop.
Pulling off my shirt, I looked at the articles of clothing neatly laid
out upon the bed. The dress looked like some sort of fairy costume. My
face reddened as I noted a pair of pink fishnet stockings.
"Are you enjoying all of this my pet?" Alexia said to the bound man, who
could only mumble into his gag in response. "Good. Twenty more then."
In between swings of her riding crop, she watched my every movement. A
look of lust flashed across her eyes as I stripped down to my boxer
shorts.
"Take off your panties too," she said to me, then leaned closer to the
man's ear and pretended to whisper so that only he could hear, but I
heard every word. "You should see what my girlfriend is putting on for
you. She is going to look so pretty. So sexy."
I blushed as I stepped out of my underwear, and hurriedly picked up the
dress, trying to figure out how to put it on, to cover my nakedness.
"Step into it," she told me. Her arm swung again. WHACK!
I stepped into what looked like a ballerina's costume. It fit tight as a
woman's one-piece bathing suit around my upper body? only it was
crotchless. Several layers of fluffy pink crinolines stood out from my
waist like a tutu. The crinolines just barely hid my crotch, making me
feel strangely exposed. Nor was there any underwear or panties on the
bed.
"The stockings next," Alexia instructed as she continued beating the
man.
I sat on the edge of the bed and lifted my leg, pointing my toe like I'd
see women do on T.V. and pulled a pair of thigh-high fishnet stockings
up my leg? the sensation of which sent goose bumps rippling up my spine.
Oh my! I never would have expected women's stockings to feel so good? so
sensual.
Alexia grinned at me, reading my mind.
I reddened in response.
"Now fix the garters to the stockings."
I lifted my puffy skirts and found four little stretchy belts with tiny
snaps at the bottom dangling around my thighs. When I couldn't figure
out the little eye-hole snaps, Alexia put aside her crop and assisted
me.
"Like this darling," she said fixing the first snap. "Now you do the
next one. That's it. Good." With a grin, she took a handful of my
crinolines and grabbed my soft cock, squeezing it, and giving it a few
strokes. She laughed out loud, as my penis sprang to attention. "You
seem to be enjoying your new dress, just fine. Now step into your
shoes."
I stepped into my first pair of 3" heels. Like the rest of my costume
they were pink, with little bows over the toes.
"Now come here my pretty." Gripping my erection, she pulled me across
the room to the dresser. I followed awkwardly in the heels, my ankles
wobbling like I was on stilts.
At the dresser was a mirror. I looked ridiculous, with this feminine
pink fairy costume with its theatrical layered taffeta tutu, just barely
covering my privates, but short enough to reveal my garter belts and
stockings.
Alexia took a curly blonde haired wig from a styrofoam stand, ran her
fingers through the locks - and then fit it on my head! She straightened
it, and then looked at me approvingly.
When I looked into the mirror, I couldn't help but gasp. The addition of
a female hairstyle actually did make me look like a girl!
Lifting a pair of lipstick from the dresser, Alexia told me to pucker,
and painted my mouth a pasty pink. "It's a shame we don't have time to
do your whole face. Maybe next time." Hurrying, realizing her sub was
straining to hear what we were doing, she brushed a quick swoosh of red
rouge across each of my cheekbones, and then returned to her submissive,
who she'd left dangling.
"Let's get you down from there," she said, hitting a switch on the wall.
The chain came down, and she removed his wrist restraints.
Meanwhile, I stood mesmerized by my appearance in the mirror. I couldn't
get over how good I looked as a girl, even if it was in this ridiculous
sissy costume.
"All right Tinkerbelle," Alexia said to me as she removed her slave's
gag, "stop admiring
yourself in the mirror. Go sit." She nodded to one of her dining room
chairs that she had placed in the center of the play room.
Concentrating on each step in my heels, I made my way to the chair and
sat, feeling my skirts billow out around me. I placed my hands in my
lap, pushing them down, covering my erection.
Alexia placed a second chair facing mine. She sat on it, and ordered the
naked submissive surgeon over her lap like a naughty child. As I
watched, she proceeded to give him an old-fashioned, open-palmed
spanking on his red, tender bottom.
After ten swats, he was squirming quite noticeably and whimpering
loudly.
Through it all, Alexia kept up a steady stream of chatter. "You really
like that don't you, slave?"
"Yes Mistress Alexia!" Bernard groaned.
She stopped for a minute, and reached between his legs and pulled back
his penis, which was quite hard and surprisingly big for a 53 year old
man. It had to be 8" long, twice the size of my own, and the first I'd
ever seen aroused like this close up. She gave it a playful, teasing
stroke, and then continued spanking his red bottom.
"My girlfriend loves watching me punish naughty boys, don't you
girlfriend?"
"Oh yes," I whispered.
"She's getting quite excited aren't you darling? Lift your skirts
darling, let me see your clit? let me see if it's getting wet."
I lifted my puffy skirts, revealing my small stiffy. As she'd commanded,
I hadn't masturbated since Monday, so I was incredibly horny. I wanted
to touch myself in the worst way, and Alexia knew exactly what I was
thinking, because she shook her head "no," and bid me to lower my
costume.
"Oh yes, her pussy is soaking," Alexia said chuckling, spanking the man
harder and faster.
The poor old gentleman howled, and cried out, "Can... can I p-please?
see what? she looks like? Mistress!?"
Alexia stopped spanking, and grabbing his swollen testicles, said, "You
want me to take off your blindfold?"
"Yes Mistress! Please Mistress!"
"If I do, you're going to have to pay for it. You're going to have to
kiss and lick her feet."
"Yes Mistress. Anything Mistress!"
"Anything?" Alexia chuckled. "You shouldn't ever say anything to me?
because you don't know what I might do to you. Now get up! Get off my
lap."
The Domina pushed back her chair, and bid the man kneel in front of me.
Slowly, teasingly, she removed his blindfold. He only got one quick look
at me, then Alexia shoved his head down to my feet and ordered him to
"Take off her shoes! That's it? Prince Charming? now I want you to kiss
Cinderella's pretty feet through her fishnets. Kiss them, and suck on
her toes. Worship them."
She stood and strode across the room to the big, tall wooden cabinet in
the room and opened the double doors. Inside among the rows of crops and
paddles, was a leather harness that she began fitting around her waist
over her pants.
"Do you think my girlfriend is pretty?" she asked, tightening the
straps.
Between kissing my feet and sucking on my fishnet covered toes, the man
cried, "Oh yes Mistress! Quite beautiful. Thank you Mistress! Thank
you!"
Alexia flashed me a grin, then fit a very life-like looking 8" dildo
into a metal ring in the harness over crotch. It hung there between her
legs, looking quite real, and quite frightening. I couldn't imagine what
she was going to do next!
"Tell my slave how old you are? Doreen."
"I'm twenty-three," I said softly, trying to disguise my voice.
While the submissive surgeon lapped and licked both of my feet, Alexia
pushed her chair out of the way and knelt behind the naked man.
"Ahh? so young. So innocent," she sighed.
I watched in wide-eyed amazement as she opened a jar of lube and greased
up not only her monstrous phallus, but the poor man's rectum. His back
arched and he squealed as she slid a finger inside.
"Time for your prostate exam doctor," she giggled. "Ooh? you've got such
a nice tight ass. I fuck it every month, and yet it still stays so nice
and tight for me."
She positioned the head at his tiny opening. With a jerk of her hips,
the bulbous head disappeared inside the man's bottom. He stopped kissing
my feet, and wailed in a high pitched shriek.
"Relax? don't tense up? or it will only hurt more."
"It's so big Mistress!"
She chuckled. "Very perceptive Doctor. I thought it was time we moved
you up to the next size. You can take it. Don't you want to impress our
guest Doreen with how much dick you can take up your ass?"
With that she rammed her hips forward another inch. The poor man was
writhing in agony, making me feel truly sorry for him. I'd never seen
anything like this in my life, and could not imagine what the poor old
fool must be feeling. Undoubtedly he was in pain, compounded by the
humiliation of having me watch his defilement.
With both hands on the man's hips, Alexia plunged the last few inches
into the man's ass, and paused, letting the poor, gasping, groaning man
have a minute to collect himself.
"Have you ever seen a man take it up the ass like this before?" Alexia
said looking me straight in the eye.
I swallowed the lump in my throat. "No m'am? er, I mean, Mommy."
The poor surgeon was breathing hard, blowing hot air across my moist
toes.
The woman smiled wickedly. "Men love it! Don't you!" she said, slapping
Bernard on his bright red ass. "You just love getting fucked, don't
you?"
"Yes Mistress!" the man squealed.
She began thrusting her hips rapidly back and forth, driving the
lifelike cock in and out of the kneeling man's small opening.
"It's a shame your wife doesn't know how to use a strapon," Alexia said,
then slowed her pace, and began grinding her hips back and forth,
undulating sensually. "Maybe I should give her a call sometime? what's
her name? Lilith? Hello Lilith? this is Mistress Alexia. Did you know
your husband loves getting fucked up the ass? Who knows, maybe when I
tell her? then you can get fucked like this every night by a big hard
cock. You'd like that slave, wouldn't you?"
I watched in utter amazement as the man's cries of pain had begun to
turn to sighs of pure pleasure. "Oh yes Mistress!" he moaned
uncontrollably.
She grabbed the man by the ear and jerked his head up, so that he was
looking me straight in the eye.
"Look at her!" Alexia commanded. "Look at her while I'm fucking you."
"Yes Mistress!" the man gasped. His face showed pure fear, humiliation?
and ecstasy.
She yanked hard on his ear, forcing him up off all fours, so that he was
kneeling in front of me, while Alexia knelt behind him, her hips pressed
against his bottom and her 8" extension fully embedded inside her slave.
Whispering in his ear, she said, "You want to touch yourself, don't you
slave?" She grabbed the man's hips and began thrusting back and forth,
slapping her pelvis against his sore, red ass.
"Oh yes Mistress! Please Mistress may I touch myself!"
He knelt there before me, and I noticed that his previous erection had
shriveled and grown soft as she impaled him.
"Go ahead! Play with it! Show Doreen what a nice big cock you have."
Immediately the man took his long, thick penis in both hands, and began
to fondle himself. In seconds it grew into a surprisingly thick, hard 8"
erection. The faster she thrust her hips, the harder he got, till a
little drop of clear cum glistened on the tiny slit at the tip.
She wrapped a forearm around his neck, forcing him to arch his back.
"You want to cum, don't you?"
"Yes," he gasped.
Behind his shoulder, Alexia winked at me.
"Before I let you cum? you have to do something for me."
"Yes Mistress Alexia, anything!"
Alexia leaned back, driving her cock deeply, chuckling. "I want you to
lick Doreen's pussy. Will you do that for me? If you lick Doreen's sweet
pussy? then I'll let you cum."
"Oh yes Mistress!"
Alexia laughed and told me, "Lift your petticoats darling? the doctor
wants to give you a pap smear with his tongue."
My legs tensed, afraid the doctor would truly lose his mind. Then I
lifted my skirts, revealing my slender erection standing straight up.
If there had been springs on the doctor's eyes, they would have popped
out of his head.
"It's very pretty little clitty, isn't it?" Alexia whispered to the man.
"Oh my yes," Bernard said, his body trembling with anticipation.
I looked at Alexia sharply, feeling somewhat betrayed. I'd expected to
sit here and watch her do a BDSM session with one of her clients?not
become a part of the routine. I'd never done anything even remotely like
this before? wear women's clothes? watch a man get beaten? fucked? and
now to show another man my penis? especially when it was fully aroused!
This isn't what I had signed on for!
Her lips behind her slave's ears, Alexia said softly, "Go ahead darling?
I know you want to lick Doreen's pussy. Go ahead. Then mommy will let
you cum."
With her hand on the back of the man's neck, she pushed the doctor's
face into my crotch. His mouth went wide open, and his lips landed on
the head of my cock like a giant suction cup.
"Oh my god!" I cried out as the man's warm, moist mouth slid all the way
down my explosively excited shaft.
Alexia held onto the man's hips, and continued to fuck him mercilessly,
as she looked me straight in eye. "I told you that you were going enjoy
it tonight. You seem to be having a good time. How do you like being my
House Boy? You're the lucky one. You get treated good."
I squirmed and writhed in the chair. It shocked me to realize, that even
though I'd never been sexual with another man before, not having
masturbated all week, I was about to explode! "I'm about to cum!" I
cried out.
Alexia's eyes narrowed. "Don't you dare! You will not cum," she said
firmly.
"But I want to really bad!" I cried out.
An angry scowl on her face, the woman reached out and grabbed one of my
nipples through the ballerina costume and dug her long nails into it.
"You control that nonsense," she said. "It's not your turn." Grinning,
pumping her hips like she was doing a dance, "It's the doctor's turn."
With his lips bobbing up and down on my cock, Bernard tried to say, "Oh
yethpth!"
"You can cum doctor," Alexia said calmly, "Any time you are ready. Just
shoot. Go ahead. Just shoot that big load you've been saving up for me
for the past hour. Just let it go."
Quite on cue, his voice box warbled on my erection as Dr. Bernard
Williamson, the chief head neurosurgeon at Mount Sinai Hospital, shot
his creamy fresh load across a towel placed strategically on the floor.
It made a sound like a sudden, quick patter of rain on the roof? and it
was gone.
When my own voice rose shrilly, as I too thought I was about to cum -
Alexia twisted my nipple like it was a TV dial and she trying to turn me
OFF. She didn't even have to say anything - she warned me with her eyes.
"Don't you dare," Alexia said, as the doctor simpered and hit high notes
like the flute in an orchestra, "Not until I give your permission."
The doctors head began to slow it's up down pistoning on my throbbing
third blind eye.
"When is it my turn?" I whimpered weakly? trying hard not to pout. My
penis was throbbing, on the verge of ejaculation. For a minute I was
afraid it might just go off all on its own.
Grinning devilishly, Alexia said, "When I decide. Don't worry. You'll
get your turn. One of these days."
One of these days?
Alexia pulled on her slave's ear, lifting the man's head out of my
crotch.
The doctor eye's eyes wavered as he fought to catch his breath. He was
still in the orgasmitron? still coming down.
"Push your skirt down," Alexia chided me. "It's not nice for a lady to
show her pussy in public."
"It's not a pussy," I said to her.
She tilted her head, and said, "I'm sorry honey. But yes it is. If
you're going to be my House Boy. That's going to be my pussy. I can read
you like a book. You are the perfect little sissy, only you don't quite
realize it yet. But you will. You will."
Alexia chuckled merrily. The woman obviously enjoyed her work.
"Bernard, go clean up in the bathroom, while Doreen gets changed."
Nodding gratefully, both of us feeling awkward and embarrassed, we
stood, me with my hands pushing down the front of my crinoline skirts,
hiding my disappointed and softening penis.
The doctor, trying to wipe the silly grin off his face, without the
slightest hint of embarrassment, smiled at us both, and hurried out of
the room and down the hall to where he'd left his clothes in the
bathroom.
Alexia began unclip my garters and pulling the shoulder straps down on
my little fairy costume. "Come on Tinkerbelle, take that off. Keep your
wig on, and put this on for now," she said, handing me a woman's short
white silk robe from Victoria's Secrets.
"Why can't I just put on my clothes?" I asked.
"I don't want Bernard to see you dressed like a man. It might freak him
out. At the moment, to him, you're a woman with a penis. Let him think
that for now. I don't want him to become gay. He is married, and I'm not
out to completely destroy his marriage. I couldn't do that to another
man's wife. I don't know what you think about taking money for this kind
of service? but that's all this is to me? is a service. We're giving a
married man expensive chocolate, that he is willing to pay $300 an hour
for?because his wife only feeds him vanilla."
I nodded, and did as Alexia bid. It felt strangely comfortable to wear a
woman's short white silk robe, and to be naked in an apartment I'd only
visited once before. The only thing that was uncomfortable, was the wig.
It fit around my head like a beanie that was two sizes too small.
After the surgeon was cleaned up, and back in his very dapper looking
dark grey suit and striped tie, Alexia suggested we sit in her living
room for a few minutes and "discuss the session and decompress."
But first Alexia took me into her kitchen and showed me where everything
was located so, "You can serve us the next time you come." She provided
the glasses and I poured us three glasses of wine.
As we sat, sipped and chatted I couldn't help but notice how Alexia's
demeanor slowly changed, almost like a chameleon changing colors. She
softened from Dominant Mistress back to the woman I'd met at Charlie
Browns. Still quite powerful, but no longer in high managerial gear.
"You've really never done anything like this before?" Bernard asked me.
Now dressed in a designer suit, he looked every bit a professional and a
gentleman. Hard to believe that only 20 minutes earlier he'd been on his
hands and knees getting fucked by the woman seated to his left.
"This was all a first for me," I blushed.
"She's a true virgin," Alexia smiled.
"You've never done drag before?" Bernard asked.
"Oh no! This was a total surprise."
"Well you make a very convincing girl," the man said admiringly. "You
should think about doing drag shows. You really should. You've got very
feminine features."
It made me feel odd to have a man look at me that way - like I was a
woman, and not a man. "I-I don't know, this is all kind of new to me."
"She's adorable," Alexia smirked, "and the sissy bitch knows it too."
All I could do was sip my wine and stare at the floor, wondering where
this was all leading.
"So what did you think of what Mistress Alexia was doing to me?" the man
asked curiously.
I shrugged. "I really don't understand it all. I mean, I don't
understand why anyone would want to be beaten or spanked? I don't like
pain."
"Yes," Alexia said, "but you admit, you were aroused the whole time that
you were watching, weren't you?"
"Yes," I blushed. "I guess I was."
"I know it might sound hard to understand," Bernard explained, "but pain
has a way of making everything more sensitive? more intense. Even the
humiliation. I admit, it was a big turn-on for me just having you watch?
and then?" he blushed slightly himself, "? that was the first time I've
ever gone down on another man before."
"It was a first for me too," I said nervously.
Alexia's eyes narrowed. "You both certainly seemed to enjoy yourself.
And you both needn't worry about it. You are not gay. I made you do it.
All right? Don't even think about it any further than that."
We both nodded and sighed. Shortly afterwards Alexia led Bernard to the
door. They whispered a few things I couldn't hear, she patted him on the
bottom, they kissed each other on the cheek, and he was gone.
Leading me back into the dungeon, Alexia explained some of my additional
house boy duties, which included cleaning and putting away all her toys
and straightening up the room.
"Now that Bernard is gone, you can take off your robe," Alexia said,
pulling it from me and hanging it up in a closet. "You can do your
chores naked. So I can look at you. At those cute little buns. And at
your teenie weenie peenie."
It felt odd to be nude, while she was fully clothed. My entire body
flushed with embarrassment.
"Can I take off this wig?" I asked.
"Yes you can take it off."
"My hair is not that bad," I said. "I don't know why you made me wear a
wig."
"It was for your own protection. What if you run into the doctor at the
hospital some time? Do you want him to know it was your pussy he was
slurping?"
I hadn't thought about that. "I suppose not?"
Alexia instructed me to clean her strapon while she put away her crops
and paddles. As I cleaned my first dildo? I could not help but curiously
examine it. Good god, it was big. Twice the size of my own piece of
equipment and much thicker. No wonder she called mine a pussy. I don't
know how Bernard could have taken it? and actually seemed to enjoy it. I
shuddered, and prayed Alexia never got any ideas about doing that to me.
I might be a little bit submissive, but I had no desire to be used that
way!
As I washed the mammoth weapon, I noticed she used a condom - which she
said was important. Everything Alexia did was geared toward safe sex.
She said she would never do anything with her clients or with me, that
was unsafe, all of which was comforting to hear.
When everything was clean and put away, Alexia told me I could get
dressed and go. The entire time I'd been walking around naked in front
of her, I'd had an erection. And now she wanted me to leave, after
making me wait all week to masturbate, and involving me in her kinky
session. I couldn't help but ask shyly, "Can I at least cum before I go?
I did as you said, and haven't touched myself."
Alexia glanced at her watch, and tapped her foot. "You have been rather
good tonight. I do suppose your little clitty does deserve a spurt."
"Oh thank you? Mommy!" I sighed with relief.
"Only, it's not going to be the way you think," she said. Leading me
back into the play room, she pulled on a plastic glove, and told me to
get up on the single bed on my hands and knees. I watched as she dipped
two gloved fingers into a jar of Vaseline. "Come on now! I don't have
all night."
Not understanding what she was up to, but fearing the worst, I did as
told and knelt on all fours. She sat heavily behind my bottom. The next
thing I knew, I felt her smear a glob of greasy goo down the crack of my
back.
I shuddered and roiled, moving away.
"Stay still!" she ordered, giving my bottom a smack with her ungloved
bare hand. A greasy finger swirled around my virgin anus. "Have you ever
been finger fucked before?"
"NO! Of course not!"
"Well, from now on, this is the way you're going to masturbate."
I let out a feminine, high-pitched squeal as her index finger began
working its way inside me. "Oh no! Please no!" I had images of her
strapping on the dildo she'd used on Bernard, and trying to use it on
me. My knees went weak.
"Oh stop it! Calm down. It's just a little finger. Didn't your mother
ever take your temperature rectally when you were a boy?"
Actually she had, as had my grandmother, and it had always been a
mortifying experience.
As her finger thrust back and forth deeper and deeper my entire body
began to tremble and shake. Then suddenly her fingertip found my
prostate, and began to massage it gently. Unable to control myself, I
let out an embarrassing coo.
Alexia laughed. "There you go. I found your G-spot. Didn't know you had
one, did you? From now on, when I give you permission to cum, you'll cum
like this?like the girl you are. Real men get to use their penis, but
you'll never be a real man, not with your little baby pee pee. Sissies
like you use their pussy hole. So you mind as well start getting used to
it."
Never having been touched that way, I had no idea that it could actually
feel so pleasurable. I'd always associated anything to do with my anus
with my bowels, and thought of it as dirty and disgusting.
After just five minutes, I was surprised to feel an overwhelming
pressure building up deep inside of me, from a place I never even knew
existed. Mommy's fingers moved faster. Unable to control myself, I began
mewing and moaning in both pleasure and unabashed shame.
I never would have thought it possible, but her continued internal
massage triggered an intense orgasm. I screamed in surprise and relief
as my body erupted. Amazingly, my penis was only half aroused, and yet
it ejaculated. White droplets sprayed across the towel Mommy had spread
under me? and my insides twitched and spasmed over and over again,
longer than any normal ejaculation I'd ever experienced.
"There you go, my little fairy princess. A nice big cum for Mommy," she
smiled. As she spoke, she continued rubbing my prostate, so that a long,
sticky stream of semen continued to ooze and dribble from the tip of my
small, soft organ, as I moaned softly in complete and utter
satisfaction.
Once she'd milked me completely dry, Alexia withdrew her finger and
pulled off her rubber glove with a snap. She stood and looked at me and
laughed, with her hands on her hips. I continued to kneels, head on the
sheets, still in euphoria, with my fanny raised.
She gave me bare bottom a sharp slap. "You are such a perfect little
sissy. See? You like being finger fucked like a girl. It's quite
obvious."
Red-faced, trying to get it together, I crawled off the bed. What had
just happened? I couldn't get over how my body had exploded?without even
once touching my penis! This woman knew more about my body, than I knew
myself!
"Clean up your mess. Put the towel in the laundry, then you can get
dressed and go."
Silently, still trying to figure out what kind of spell Alexia had put
on my body to make it behave like this, I did as I was told.
Still in a daze, I followed my over-sized Mistress to the front door. It
was almost midnight.
Alexia handed me a $50 bill. "Bernard gave me an extra $100 to have you
in the session. I promised you that I would split it with you."
Feeling guilty, for what I'm not sure, I took the bill and stashed it in
my back pocket. I guess I was officially a whore now. Every white man's
dream. Getting paid for sex.
"So you had fun?" she asked.
"Yes, very much so," I whispered, then realizing I was still using the
feminine voice I'd adopted for Bernard. I tried to lower the register of
my vocal chords, and my voice squeaked like an adolescents. "You are so
full of surprises. It was different."
"But you liked it?"
"Yes," I whispered.
"Good. Bernard was quite happy. He's one of my regulars. I see him once
a month. He wants to see you again. Do you think you would like that?"
Did I want to dress like a woman again? and have a man suck my cock? And
maybe get finger fucked? Unable to speak the words, I nodded agreement.
"Fabulous. I want you here again next Thursday night. I have another
submissive similar to the doctor. This one is an airline pilot that
likes to crossdress. I said something tentatively to him about you, and
he seemed very interested. Next time, I want you to come a little
earlier. I want you here before he arrives, around 8 o'clock. So I can
get you dressed."
"What are you going to do to me?!"
Alexia chuckled, her eyes narrowing mysteriously. "You'll find that out
on Thursday."
That was my racquetball night with Larry. I didn't even mention it to
Alexia. Sorry Larry. Insane as it sounded, Larry was going to lose out
to a cross-dressing airline pilot.
Before I left I hugged Alexia and kissed her on the mouth, and for once,
she actually seemed slightly taken back and a bit shy.
"You don't like me kissing you?" I asked.
"I'd rather you kissed my feet," she said firmly.
"Really? You don't like kissing me?"
Alexia considered this. When she didn't answer right away, I knew she
was torn. "You know that I like you, or you wouldn't be here. But my
little princess, you should understand right up front, I get enough of
men all week long. I prefer women, when it comes to my own, personal,
intimate relationships. Okay, I admit, when you were dressed like a
girl, I thought you were cute. But when it comes to kissing, I want a
real woman."
I gulped. Talk about the ultimate put-down.
Alexia saw that I looked ready to cry, and pushed me out the door. "Even
if you were to go on hormones and get the change, you are much too young
for me. I am not about to get involved with you! Not romantically. Now
give me a kiss on the cheek, and go."
I did as I was told. In the back of my mind I remembered how when I'd
first seen Alexia's card, I thought that she would be a challenge, and
that I'd be able to win her over. I suppose I had won her over in a
way?but not the way that I'd expected. Never did I imagine then, that I
would be on my knees in front of an old, overweight woman that wasn't
even pretty, as she milked my prostate.
"See you Thursday, Tinkerbelle," Alexia said, and shut the door.
To be continued?