Sylvanna The Great

In January of 2005, I went to Peanuts for the third time, and saw her sitting at the bar. I had been there on other trans nights, but couldn't work up the nerve to approach any of the girls. This time was no different.

I went up to the bar to order a Rum and Coke, and the older woman dressed in a vinyl
bustier on the stool next to me moved her leg against mine. She had a sly smile on her face, and a Martini in her hand. I looked over and smiled back, and that was when she slid her hand up my leg onto my crotch.

I instantly got hard under her slowly roving hand, and after a minute or so, she turned to face me and crooked a finger for me to come closer. I moved my ear next to her lips so I'd be able to hear her over the music.

"That's a nice one, little boy. Is that for Mommy?" I nodded.

"Good. Mommy needs a ride home, are you ready to take care of Mommy?"

"Yes. But I have a drink coming and ..." She cut me off with a quick squeeze and a nibble on my earlobe.

"Mommy doesn't give a fuck. Mommy just wants your special gift before one of
"these filthy whores see what you've got in your pants. Pay for your drink
"and let's go."

I left $20 on the bar, and she took my arm in hers and led me to the door.

"Where's your car?" I led her quietly to my car in the parking lot, as we
walked, she kept rubbing my arm with her immense tits that were nearly
spilling out of her top. I let her in first and I noticed she secured the
seatbelt around her waist, but put the shoulder strap behind her. By the
time I crossed over to the driver side, she was turned towards me and running
her hands over her lycra-covered crotch.

It was a cold night, so I started the car and turned on the heat. When the
dome light went off, she leaned back against the door.

"Wait, don't drive yet. I want to see it first." I paused, looked over at
her, one hand on her crotch, the other pinching her nipple, and her tongue
licking her lips. I carefully unzipped and pulled out all 7 inches of thick
pink pride.

"Ohhhh....that's a nice one, Mommy is going to have a good time with that."

"Now kiss me, I want to see if you taste as good as you look."

I leaned over to her, and one of her hands went behind my head, while the
other grabbed my raging cock. As soon as my lips touched hers, her tongue
slid across my lips and into my mouth. I started to suck on it greedily while
she pulled me in closer.

She pulled her mouth away and used her hand to drive my mouth to her exposed nipple. I licked all around her immense aureole.

"Suck the nipple." I did.

"Harder." I did.

"More." I did. And the I tasted the thin liquid spilling from her.

"Oh, that's good baby, drink Mommys milk. I've been ready to burst all night."

I was sucking for all I was worth, when I felt myself starting to come. So
did She, she moved one hand around my cock-head, and the other around my
throat, pushing me away from her.

"You don't get to cum until I say so, do you understand me little boy."

She held my cock under the head so tightly I would have gasped if I could get any air past her other hand. I just nodded and she held me there until the moment passed. When she felt me relax she let me go, and I sat back in my seat.

"You cum when Mommy says, where Mommy says, and how Mommy says. Mommy is going
have to teach you how to behave for Mommy."

I started to put my cock away but she wouldn't let go.

"No. Mommy wants to make sure you stay hard for the ride home. Now drive."

I pulled out of the parking lot and she directed me to a small house a couple of
miles away. Using the remote in her purse, she opened the gate and I pulled in
and shut the car off. She had been lightly stroking my cock for the entire trip so I
was still thick with desire for her.

"Now come around and let Mommy out of the car properly, little boy."

I came around to her side, and opened the door. She had already removed her
seat belt and offered one hand to me. I took it and she elegantly slid out
and stood. She was at least 6 inches taller than me in her heels, and
probably still and inch taller without them. She immediately took my cock
back in her hand, and pushed one nipple out of the bustier with the other.

"Have a little drink before we go in. Suck hard. Make a little noise, I have a
neighbor across the street who enjoys the show. He's been waiting for me to come
home for hours probably, with his wretched little pee-pee in his hands."

I started sucking, hard and felt her massaging my cock with one hand while another
started playing with my nipple. After a few seconds her delicious milk started
spraying in my mouth. She gave my nipple a hard pull when she wanted me to stop, and I pulled my mouth back and gasped.

"That's good, now warm up Mommys crotch with your mouth so the creep across the
street can finish."

I started licking and sucking at the crotch of Mommy's lycra
pants, forcing my hot breath onto her, and after a minute heard groaning and
grunting from a window across the street, finally capped with a breathless cry.

"You can get up now. That was a good job you did for Mommy. He paid me a hundred
just to watch this part of the show."

Once I was up off my knees, she held me by the cock and led me into the side door of the house.

She led me to a bedroom in the back of the house where all the shades were drawn, and lit by soft lights.

"Now, undress for Mommy, get on the bed, and keep that little monster hard for me.
I'm going to put on some special touches just for my little boy."

She went into the bathroom and closed the door quietly. I followed her
instructions and laid there quietly, gently stroking myself to maintain my
erection, but softly so I wouldn't come the instant she came out of the
bathroom.

She emerged in the bustier alone, panty-less and magnificent.
She had also put on a black patent leather choker, with matching thigh-high
boots. She had a matching riding crop in one hand, and was wearing
opera-length gloves that appeared to be satin. She had also put on new
lipstick in a dark purple color and added more eye makeup to match it. I was
utterly transfixed by the look of her, and gripped my cock the way she had to
avoid exploding at the sight of her.

"Do you like Mommy's outfit?"

"Yes. Oh Yes."

"Yes what, little boy?"

"Yes, Mommy."

"That's a good little boy, now Mommy has a treat for you."

She stalked slowly to the side of the bed, and used the crop to raise her
huge, hanging cock up to my mouth. I started by kissing it, then licking
around the head, the sliding my tongue along the slit, then slowly, taking more
and more of her into my mouth.

Once I had her half-way in, I felt the riding crop lightly sliding across my
nipples, first one, then the other. After a minute or two, her hips started
to sway back and forth, gently sliding her cock across my lips and tongue.

I used one of my hands to gently massage her balls, and the other against her
ass, bringing her ever more deeply into my mouth. Once I had it as deep as I
could go, I pressed one finger against the opening of her ass, and could feel
the texture of lube there. I slid my middle finger in just a touch, and she
grabbed me by the hair and pushed forward until I was gagging and thick ropes
of saliva were pouring out of my mouth and onto her raging cock.

She was rapidly tapping my balls with the crop, not painfully, but enough to keep
my erection completely sustained.

The next thing I knew, she used my hair to pull my mouth off her cock.

"Very nice little boy, you almost had me cum in your mouth. But it's much too soon
for that. Now lick all your dirty little spittle off my cock. Now!"

And I did. My hair wrapped in her glove, I licked and sucked every drop I had
deposited. Whenever she felt me starting to take her back into my mouth, she
would pull my mouth far enough off her so that only my tongue could reach her.
Then she'd let me continue until I started to lose control again, and again,
and again.

After I had cleaned her off, she pushed me back and strode into the bathroom
without a word to me. I couldn't see what she was doing, but she called to me:

"Stay on your back, and don't you dare touch yourself. You have to save your
load until Mommy is ready for it."

A moment later she came back on having added a black condom that was gleaming with lube, and a stainless steel cock-ring to her ensemble.

"Have you ever had a big, black cock all the way up your ass, little boy?"

I shook my head, and stared, utterly transfixed. While she was in the
bathroom, she had lifted her beautiful, immense breasts out of the bustier. I
was on the verge of coming just from looking at her.

"Spread your legs for Mommy, little boy, and prepare to become a man."

I did as I was told and felt her position the tip of her cock at my sphincter,
with her other hand sliding behind my neck. She lifted my head off the pillow
and drove her tongue into my mouth at the same time as driving her cock deep inside
me.

I felt myself get even harder against the vinyl bustier as my cock rubbed
against it, and she drove her long, rigid cock inside me. I wrapped my arms
around her to hold her close against me and deep inside me. After a small
eternity her tongue came out of my mouth and she instantly replaced it with one of
her nipples.

"Have a drink, baby, I need you to last for a while while I enjoy that tight ass
of yours."

I sucked until her thin milk started seeping into my mouth, and sucked even
harder once it did. Every few minutes she'd pull one nipple out and replace
it with the other, all the while encouraging me to suck harder. I felt like I
was gaping wide open, and felt lube and sweat sliding down the crack of my
ass. Every time I started to buck up against her, one of her soft, gloved hands
would grip my cock-tip until the near-orgasm would pass.

I was nearly blind with desire, her sweet warm milk filling my mouth, her cock
driving away all sense of time, when she reared up, pulled off the condom,
pulled my head forward and I opened my mouth to receive all she had to give.

She erupted into my mouth with a deep grunt that I could feel across my lips.

"Don't you fucking swallow little boy, or I will beat your little bitch ass to
death."

That was all the warning I needed, I did everything I could to keep every drop
in my mouth. It felt like half a gallon was filling my mouth. She pulled her
cock back so only the tip was in to make more room. I held on to her ass and
she held my head in place. Finally, she pulled out, with one last, long string
of cum mixed with saliva connecting us. She rubbed the string off her cock
against my bare cheek, laid my head back down, and kissed me, deeply.

She started to suck, and I let the entire load drain back into her mouth. Once she
had gotten most of it out of my mouth, she sat up, still between my legs, and
began to drool it down her chin, and onto her gleaming breasts.

"Lick it until I shine little boy. Lick it until nothing is left of Mommys love
for you. And swallow all of Mommys love, and if you do a very good job,
I'll let you cum, maybe."

I sat up, and swallowing the cum that was still in my mouth I licked her chin,
and her breasts, and cleaned the vinyl bustier it had spread down. The I
started licking clean the sweat from her breasts, the salt from her arm-pits,
and finally went back down to her cock, getting every final drop of cum from
her there.

"You are so ready, aren't you honey? You did such a good job of cleaning up
Mommy, and drinking her love and milk, you could probably cum just from Mommy
telling you to, couldn't you?"

"Yes, Mommy, my cock hurts with how much I love you. Use your mouth, use your hand,
use the crop if you have to, please let me show you how much I love you!"

"Alright then, darling, Mommy will tease your filthy little babies out of you, and
then you'll eat them out of Mommy's hand, wouldn't that be wonderful?"

"Yes, Mommy." I put my hands behind me, and leaned back with my erection
pointing straight at this goddess. She put one gloved hand around my balls
and started stroking the shaft with the other.

"That's a nice hard-on you've saved for Mommy. Now when I say 'Cum for Mommy',
you're going to let that load loose into Mommys pretty glove. Won't that be
nice?"

I nodded, her hands moving faster and squeezing harder.

"I bet you thought you were going to fuck Mommys perfect Ass tonight, didn't you?"

I nodded, my breathing starting to match her stroking.

"Well, maybe someday you'll earn the right to spill your filth inside Mommys
bottom, but not tonight, baby. You're going to have to bring Mommy nice gifts,
like lingerie, and jewelry, and shoes, and take Mommy out for nice dinners,
and make sure she has enough cash to have fun when her little baby boy isn't around
to entertain her."

"Yes Mommy. I'd love to do all that for you."

"I know you would baby, some night very soon, you'll have to come over and lick
Mommys hole until it glistens, would you like that you dirty little boy?"

"Yes Mommy. I want to spend hours with my tongue up inside you!"

"That's good baby, I'd hate to have to pimp you out to the freak across the street,
so make sure you clean my asshole properly every single time, ok?"

"Yes Mommy."

"Has Mommy told you her name yet? What you can call her when we're at someplace
nice?"

"No Mommy."

"It's Sylvanna, now cum for Mommy Sylvanna, I can feel it throbbing in your balls."

I closed my eyes, and started to strain.

"Open your eyes, you always worship Mommy Sylvanna with your eyes no matter where
we are or what we're doing, do you understand, you evil, filthy little boy?"

My eyes snapped open to the sight of her tongue flicking over her lips as she
squeezed my balls with one hand, and covered my cock tip with the other.

I came buckets, and she eventually had to use both gloved hands to catch all of it.

With one hand, she covered her cock with my cum. She used the other to spread my
sperm over the top of her tits. When she was done doing that, she put her gloves
in my face and I licked them until they were clean.

Once that was done, she laid on the bed next to me, and let me clean her cock
and tits. I was drained, exhausted, and out of breath. She pulled me close to
her and I began to kiss her neck and nibble on her earlobe.

"That's nice sweetheart, but it's barely midnight. Give Mommy a gift and I'll
give you a nice surprise."

I found my wallet in my pants on the floor and took two hundred out. I put the bills
in my mouth and laid them on her still-huge cock, giving the tip a little lick
before returning to my perch on her shoulder.

Without a word, she moved the money from her cock to a drawer in the bedside table,
she turned to me and gave me a long, deep french kiss.

"Okay baby, time for you to get dressed. When you're done getting dressed,
go to the closet and get my long, black, leather coat."

I did as I was told and by the time I was done she was standing next to the bed with
her arms extended by her sides, waiting to don her coat. She took a business card
out of a small, almost secret, pocket which had her name and number printed on it.

On the back was the hand-written address of her house.

"You've been a good little boy, but now you have to do some things to prove how much
you love Mommy, ok?"

"Good, kiss Mommys cock and tits, and then put my tits back in the bustier, then
button the coat for me."

I did as I was told, lingering over her cock and each nipple, but not long enough
to drain anything out of them.

"Now you're going to drive me back to the club, and wait in the car. I don't want
any of those whores defiling my little boy, and I may need to bring another
guest home, would that be alright?"

I nodded. She grabbed the gate remote on the way out, and as she was waiting for me
to open the car door for her, she lifted enough of the coat to expose her cock and
the steel ring around it to her neighbor. I heard a sound like a foot stomping from
across the street. I wondered if he ever slept, or just waits for Mommy to come
in and out of her house at night.

On the drive back to the club she gently stroked my cock with one gloved hand,
remaining silent for the entire trip. When we arrived she put her hand out, palm up.

"Mommy needs twenty for the cover, and another twenty for a drink while she waits
for any special friends that are waiting for her. If I bring someone back, I'll
have told him you're my son, and you like to drive me at night to keep me safe.
Don't say anything, just watch the show in the mirror, and don't get in a wreck,
Ok, sweetie?"

I nodded, and she undid her seatbelt and gave me a long, sweet kiss for my reward.

After another half hour, she returned to the car with an older, muscular black man.

I unlocked the door for them, and helped Mommy Sylvanna into the rear seat. Her gentleman friend let himself in on the other side.

"Home, baby" she commanded, and I started the car and pulled out, as I did I could see her opening her coat and her cock was erect once again. Mommy never ceased to
amaze or impress.

Her 'date' quickly lowered his mouth onto her cock. I adjusted the mirror to catch
all the action, and as it passed over Sylvannas eyes, I could see her looking at me
in the mirror. I drove carefully back to her house, frequently glancing up at
the mirror as he slurped and sucked. Every time I looked at Sylvannas eyes she
was gazing at me in the mirror even as she pushed his head farther down her cock.

When we arrived at her driveway, she clicked the gate open and I pulled in. I came
around to her side of the car and as I opened the door I put my hand on her shoulder
to keep her from falling out of the door.

"Martin, you need to stop long enough for me to get out of the car, or I'll splash
down your throat right now and you'll have to crawl back to the club."

The slurping stopped and there was a final pop as his lips detached from her.
As she got out of the car I looked across the street and saw the open window, with
the barest outline of someone seated just inside it. From where he was he could see
her outfit, with her boobs spilling out of her top, her engorged member, and the
cock-ring gleaming from the nearest street light.

Martin crawled out of the car and resumed sucking her while on his knees. I could
see just enough of the man in the window to know he was rocking back and forth,
probably stroking himself. Mommy gently slapped Martin across the cheek with just
three fingers, and once again he stopped sucking. She led both of us into the house,
locked the door behind us, and she pointed to the couch.

"Baby Boy, sit there. Wait quietly. Don't touch yourself. My beautiful, black bull
has some important work to do. Don't disturb us unless I call to you."

Mommy made it a point to start calling Martin 'Daddy' and telling him how good his
big, black cock felt inside her. She asked for it harder, and faster, and deeper,
and judging from the sounds of the bed, Martin was doing everything she asked.

It couldn't have been more than ten minutes before I heard Martin grunt, call Mommy a beautiful bitch, and finish. I heard her call him a cab, and five minutes later
he left the house through the driveway side door. She clicked open the gate for
him, and sat on the couch next to me, her hand sliding up and down my thigh,
brushing against my freshly erect cock at the top of every stroke.

"Help me get out of these clothes, won't you baby?"

I nodded and started with her boots. As I started to work them down her legs she
pushed my head next to her thigh, and turned me so my lips were against them.
I started kissing, and licking, and sucking both up and down. As I got the
first boot off, she whispered to me:

"Put the boot on the floor of the closet, and them come back and do the other one.
Leave your clothes in the bedroom. Neatly."

I followed her instructions, and returned naked and erect in less than a minute.

"Now the other one baby boy."

I started licking at the top of her thigh, her cock and balls resting against my
cheek. I worked my way down, spending several minutes slowly and lovingly
removing the other boot.

"Put it away, and come back for the gloves."

I did, and returned to slowly remove each glove, one at a time, kissing her
shoulders, and biceps, and the inside of her wrist, and taking each finger into
my mouth one at a time sucking it like the last time I would ever have her cock
in my mouth. She made small cooing sounds, and by the time I returned from
folding the second glove and placing it beside the first on her dresser, she
had two fingers gently stroking her cock.

"Before you take the cock-ring off, you have to get me very wet, but don't take
me into your mouth, if you do we'll never get this off..."

I started by drooling on top of the ring, and spreading it to either side with my
tongue. After a few minutes, she lifted her cock so I could reach the underside.
A few minutes more and she pushed my head away, and slid it three-quarters of the
way to the crown.

"Take it off Mommy with your mouth. You've done so well, so far."

I gently pulled it toward the tip, and once there was room, wriggled my tongue
inside it. I was massaging her outer thighs with my hand and as it was just
about to pass over the crown, I felt her hand on the top of my head.

"Keep doing that, don't move it any further, keep using your tongue, baby..."

I looked up and her eyes were closed, and she was slightly smiling, and her
free hand was pinching one nipple, then her mouth opened and her tongue started
lolling over her lips.

"That's it baby, that lame fuck didn't take care of me, just got his rocks off
in my ass and left. Mommy needs her baby to take care of her before she goes
to sleep."

I kept sucking and licking and after a few minutes I could taste the pre-cum. I
didn't know how many times Mommy could cum in one night, but I was sure she had at
least one more load for my hungry mouth. Two minutes later I could taste her as
she splashed in my mouth.

Another minute went by, and she leaned forward.

"Help Mommy take this off."

I moved up onto the sofa and reached around her, I found the zipper in the low
light, and removed it and when her breasts were freed they dropped less than an
inch, despite their size.

"Mommy is too tired to take a shower. Martin may be selfish, but he's a nice fuck."

She rose from the couch and took me by the hand into the bedroom. I could still
smell the musk they filled the room with before I came in. She lifted the still
messy sheet, revealing a latex one beneath it. She put the cotton sheet in the hamper and threw the latex one through the bathroom door onto the floor. She
lifted the next sheet and got under it and rolled over onto her side, facing me.

She patted the bed in front of her and I got in. She rolled me on my side,
positioned her cock in my ass-cleavage, wrapped her top hand around my cock.

"Get some sleep baby, you have a lot of work to do on my morning wood before
you take Mommy to breakfast. I expect to wake up with a rock-hard cock in my hand."

And that was how I spent my first night with my new Mommy.