Blog : Slave Jenny and Mistress Vanessa, Part 1: The First Encounter

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8/21/2023 8:34 am

Slave Jenny and Mistress Vanessa, Part 1: The First Encounter

This is very long. It's 12 to 15 minutes reading time.

Note: This is a work of fantasy for adults 18 years of age or older. It was written for the enjoyment of the author and any readers who might also enjoy it. It’s not based on reality, it’s not intended to depict reality, and it’s not intended to be emulated in reality.

I’m so excited and so aroused. This will be my first experience as a woman and as a submissive. I’ve fantasized about being a woman as long as I can remember. I’ve fantasized about being a submissive as long as I’ve known about sexual dominance.
I started with wearing lingerie. Then women clothes, then makeup. Now I have a pedicure, fake fingernails, and chin-length hair that I can wear in cute women’s style or in a man’s style. I work remotely and spend most of my time at home as a woman. Five times I’ve ventured out in public as a woman for brief periods. So far, I don’t think anyone has guessed that I’m trans. Tonight I hope to take the next step.
I’m carefully applying my false eyelashes, makeup, and lipstick. I’m wearing a pink skater skirt, a white silk blouse, and strappy pink high-heeled shoes. Underneath I have a white push-up bra and lacy white bikini panties, garter belt, and stockings. My hair is styled girlishly; exactly how the hairdresser showed me. I’m accessorized with dangly earrings, a cute gold pendant necklace, gold bracelets, rings, and a gold anklet.
Looking in the mirror, I think, “beautiful.” It’s a good thing I’m not wearing a tight skirt, or the throbbing erection sticking up through my panties would be on display for everyone to see. Time to head to Vanessa’s.
Vanessa will be my mistress for the night. I’ve met her several times, I’ve checked out her background, and a friend knows where I’ll be. Believe me, I’m not the kind of girl who’s going to let just anyone tie her up. It’s 7:40 p.m. I wasn’t supposed to be here until 8. I’ll just sit here until 8, although I don’t know if I can stand the anticipation. At 7:45 Vanessa called, “I see you out there, Jenny. You may come up.”
“Yes, ma’am,” I excitedly reply.
She answers the door in a little black cocktail dress, red pumps, and she’s as exquisitely accessorized and made up as I am. “Sorry I’m so early, Mistress” I tell Her.
“It’s OK,” she replies. “You look absolutely adorable!”
“Thank you, Mistress. You look very beautiful yourself.”
She leads me into the living room, and I take a seat on the couch. I’m so nervous I’m almost trembling.
“Would you like a glass of wine? Or maybe a Cosmo?”
“A Cosmo would be wonderful,” I smile sheepishly. “I’m so nervous I’m about to burst.”
She flashes a big smile. A few minutes later she comes back with a Cosmo for me and a glass of pinot grigio for herself. Mistress is a statuesque six feet tall. She’s very well-toned. She’s on hormones and has pretty, round hips and perky B-cup tits. She’s of Italian descent and has long, silky, coffee-colored hair, beautiful big chocolate eyes, and lovely olive skin. She’s 100-percent passible. In fact, she turns the men’s heads when she walks down the street.
On the other hand, I’m five-foot-six. At 102 pounds, I’m about as shapely as a broomstick. I exercise and there’s no flab on me, but I wouldn’t call myself toned. I have clear, light, soft skin and like to think I’m cute when I’m all made up. My skinny butt also looks cute when I’m naked or wearing tight shorts. I’ve never seen any heads turn my way in public, and on close inspection I’m not sure how passible I am. I just hope Mistress likes me.
We make some small talk while having our drinks. I’m almost gulping mine. She comes over and sits by me. She takes my drink and sets it on the coffee table. “Slow down there, Slave. I don’t want you too relaxed.” We both giggle.
Mistress puts a muscular arm around my shoulders and pulls me in for a long, erotic kiss. My flaccid penis immediately springs back to attention. She must sense this because she reaches down and starts rubbing my stiff six inches through my skirt. We both sit back and finish our drinks in one swallow. Without saying a word, she stands up, takes my hand, and leads me to the bedroom.
Before their first encounter, Vanessa made Jenny agree to a Mistress/Slave Contract. The first provision was that when they were together, Vanessa was the Mistress and Jenny was the Slave. The Slave must follow every command and every rule given by the Mistress. Failure to do so would result in punishment as severe and the Mistress deemed necessary.
The second provision was that when serving as Mistress, the Mistress’ first responsibility was for the safety and wellbeing of the Slave. That responsibility even superseded the Mistress’ safety and wellbeing.
The third provision was that either party could nullify the contract and end the Mistress/Slave relationship at any time, except when the slave was being punished. The exception for punishments exists because punishments can be harsh and painful. The Slave might choose to end the relationship rather than endure the punishment. This would render the threat of punishment ineffective and erode the Mistress’ dominance. The contract also spelled out many rules and details of the Mistress’ and Slave’s duties.
“What position does a slave assume?” she asks.
“On her knees, Mistress?”
“That’s right, Slave. On her knees.” I lower myself down on my knees. “Slaves also wear a collar and wrist cuffs.”
I put my arms up and she puts pink leather cuffs on my wrists. Next, she puts a pink leather collar on my neck. She attaches a leash and drapes the chain across my back. The feel of the cold steel is exhilarating. She lifts her dress, drops her panties, and puts her rock-hard cock on my lips. I kiss the tip and run my tongue around it, tasting the salty pre-cum. Wow! I lick the shaft several times and then plunge my mouth down on it just like I practiced with my dildo.
I’m tasting my first dick and loving it! Up and down, in and out. She’s thrusting. I’m bearing down, taking care not to bite. All the way down, deep into my throat comes her thick eight inches. She grabs me by the hair and starts face fucking me, pounding her thick member down my throat. I’m choking and gagging. Being a slave isn’t always fun! But when I look up and see the ecstasy and joy on Mistress’s face, and know that I’m causing it, I realize I’m the one who really has the power.
She pulls her dick out, pulls me to my feet with my leash, and leads me over to the bed. She lies me on my back and ties my arms spread-eagle to the bedposts. She lies down beside me and starts passionately kissing me. “For a first-time slave,” Mistress says, “you’re doing quite well. So far.”
“Thank you, Mistress.”
She starts kissing me again while unbuttoning my blouse. She pulls my blouse open, makes me arch my back, and reaches behind and unclasps my bra. I’m regretful and ashamed that I don’t have any tits for Mistress to play with. She doesn’t seem to mind. She pulls my bra up and starts fondling, licking, and sucking my nipples. I’m so turned on. At the same time, she reaches down, grabs my dick, and starts stroking it. I think I’m going to explode. Mistress senses this and squeezes my balls gently but painfully. That stops me from climaxing.
Now Mistress puts pink cuffs on my legs, just above the knees. She pulls my legs and butt into the air and ties them to bedposts too. I’m totally exposed and completely vulnerable. I realize now that I’m completely hers. Nothing I do or say can change that. I’m about to receive what I’ve so long desired, and so long feared. I tremble in anticipation and apprehension as I lie back and try to relax, knowing that I must take whatever comes. She starts rubbing my butthole, first with a dry finger, next with a lubed finger. “This will loosen you up and make things more fun for both of us.”
Mistress brings out two butt plugs. One was about the size of my pinkie finger, the other was about twice as big. She thoroughly lubes the small one and starts massaging my hole with the tip. She inserts the tip and then pulls it out. She inserts the tip again and pulls it out again. Now she quickly jams the plug all the way in. I gasp at the sensation and my dick juts skyward. She straddles my chest and puts her heavy schlong on my lips. I pull the tasty delight in my mouth and work on it as the plug loosens my asshole. She moves off, goes back to my butt, and removes the plug. She squirts a bunch of lube into my hole, lubes up the bigger plug, and more gently than last time inserts that into me. Now I am full!
She takes my cock in one hand any my balls in the other. She strokes the shaft and then punishes the balls. Stroke and punish, stroke and punish. I’m about to go insane. Being a slave isn’t always fun! She puts her hot mouth on my dick and goes down once and then twice. On the third time I have the most powerful orgasm of my life, spasmodically squirting four or five times. She lifts her head up, raises her eyebrows, and gives me a look that says, “Now you’ve done it.” she leans over and dribbles the huge, sticky load all over my chest and stomach. She grabs my balls, squeezes painfully, and asks, “Do slaves get to cum without permission?”
“No, Mistress.” I whimper.
“Do slaves get to cum without permission?”
I yelp in pain as she squeezes harder. “No, Mistress. I’m sorry!”
“You’re going to be a lot sorrier. What do you think happens to slaves who cum without permission?” she asks while still exerting her painful grip.
“Th-they get p-punished,” I sob.
“That’s right, Slave. They get punished.” She releases my nut sack and swats me hard on the butt. She pulls a small, hard rubber paddle from the bedstand. I grit my teeth in pain as she swats me about 15 or 20 times with the evil tool. I know my ass is bright red. Then Mistress straddles my chest again and slaps me on the left cheek. The slap isn’t hard, but it does sting. Tears spring to my eyes. She slaps me on the right cheek. Left right, left, right, my head is spinning and I’m crying uncontrollably. Being a slave isn’t always fun!
After about five or six slaps on each cheek, she stops. She gets a tissue and wipes my eyes and nose. “Will you cum without permission again?”
“No, Mistress, no!”
“Will you misbehave again?”
“No, ma’am. I promise.”
“Good,” she says. “You’ve very to slavery so this was a light punishment. Next time will be very unpleasant.”
Mistress pulls the plug out of my butt, squirts more lube in my hole, smears lube all over her shaft, and sticks it in. Even though I’m stretched and well lubricated, I wince and moan in pain as the large protrusion enters my rectum. The pain eases to an uncomfortable pressure as more and more of her enters me. After a while, to my relief, it stops. A moment later, I’m surprised to experience more discomfort as she goes in deeper and deeper and deeper. When will this stop? How big is this thing? Is it somehow growing? Finally, I feel her hips against my butt cheeks and know it’s all the way in.
She slides it back a little, and plunges it back in. She slides it back farther and plunges again. And again, and again. The pressure is gone, and it starts to feel fantastic. Suddenly I realize I’m hard as a rock. I start pushing my ass forward on her cock every time she plunges. I don’t know who’s enjoying it more, Slave or Mistress. I bite my lip as she pounds away, thrust after thrust. Every nerve in my body is tingling. I hear myself moaning audibly “Please cum! Please cum!” My dick is so hard it aches. Part of me wishes she’d climax and stop. Part of me hopes it never ends.
She drives it deep and then stops hammering. I open my eyes and see that Mistress is panting and sweating profusely. I realize I’m doing the same. “I must look a mess,” I say.
“Slave, you look lovely.” she pushes it in as deep as she can, leans forward, puts her arms around me, and we kiss long and heavily.
She finally, mercifully, pulls it out. “Whew!” I say with a big smile. My ass feels like … I don’t know what it feels like. It feels like I really have to poop. It feels like I just took a huge poop. It feels like a train drove through it. It feels like a just ran a marathon. It feels like there are a million tiny faeries in there dancing. I’m a lifeless mess. And we’re just getting started.
Mistress unties my legs. I now realize how stiff and aching my lower back, hips, and legs are. She gets up and heads for the bathroom, leaving my arms still bound. “Don’t go anywhere,” she calls playfully. I want my arms so badly. I want to move. I want to touch myself. I want a drink of water. Being a slave isn’t always fun! I hear Mistress in the bathroom washing herself. She comes out a minute later and I can see that she touched up her makeup. She comes to the bed, releases my arms, and hands me a glass of water. I drink greedily.
“I couldn’t untie you,” Mistress says. “I didn’t want you playing with your little pee-pee.” I blush. She massages my shoulders and arms. “Do you need to use the restroom?”
“I think I have to poop.”
“You think you have to poop, or you have to poop?”
“I don’t know.”
“Unless you’re sure, don’t try. Believe me, it’s best.”
“Oh, Mistress, I believe you. I believe anything you say.”
Mistress rolls me on my stomach, pulls my arms behind my back, and fastens my wrist cuffs together. I’m helpless again. She rolls me on my side and pushes my head down to her cock. I kiss it, lick it, and then take it in my mouth. I go up and down on it for a few minutes, then I let it slide out. I alternate kissing it and rubbing my face against it many times. My lord, how I love that wonderful thing. “May I have it again, Mistress?” I ask sheepishly.
“You’re getting it whether you want it or not,” Mistress answers with a devilish grin. She puts me face down on the bed and puts a large throw pillow under my pelvis. I feel more lube being squirted in my ass, followed by her finger, followed by the throbbing hunk. The pain and pleasure of the initial entry are once again surpassed by ecstatic delight. Thump, thump, thump her hips crash into my butt. It feels a bit different this time. Bigger, deeper, it feels like my whole body is being stretched to accommodate the swelling mass. I’m moaning loudly as my cock rubs against the pillow. I could easily climax, but I’m afraid of what my punishment would be. I’m trying to decide whether cumming would be worth it when I feel her love stick throbbing and pulsating as she blows her large load into me.
My ass involuntarily squeezes her out as she goes flaccid. I feel the warm fluid running out of my butt crack and down my thighs. I’ve never felt so exhilarated or so fulfilled. Knowing that I gave my Mistress so much pleasure is more pleasurable to me than anything I’ve ever known. I also know now, for the first time in my life, exactly what I am and exactly who I am.
“Thank you, Mistress. Thank you so, so much.”
“You’re welcome, and you are amazing!”
My wrists are still cuffed behind my back, and she rolls me on my back uncomfortably on top of my arms. She strokes my cock. I shiver. “Not yet,” Mistress admonishes. “Not yet.” she gently squeezes my balls and starts blowing me. She coats my member with lube and puts some in her butt, then she straddles me and sits on my throbbing cock. She’s so tight and she feels so good! She begins lowering herself up and down and I see her tits and cock flopping around. “I’m such a lucky girl,” I think to myself.
“May I …” I ask Mistress.
She replies, “Yes. Please.”
Shaking violently, I explode in her ass. My previous climax was the best I ever had. This one is ten times as intense. My ears are ringing. I gasp for air. I never knew I could achieve so much physical pleasure.
“Let’s go clean up,” Mistress says. I can barely walk as we head to the bathroom. We get in the large shower. I wash my face and all the dried semen on my stomach, ass, and legs. We wash each other’s organs. Then we get out and dry off.
“May I make myself pretty for you, Mistress?”
“You’re already beautiful. Let’s go back to bed.” Before getting into bed, she puts the wrist cuffs and collar back on. “Slaves wear a collar and wrist cuffs.”
We lie side-by-side passionately hugging and kissing, then I roll on my back and pull Mistress on top of me. I wrap my arms around her neck and my legs around her waist, then I buck and squirm fishing for her meat with my hungry hole. “Whoa, there cowgirl,” she says with a laugh. “I think I’ve created a monster.”
“With respect, Mistress, you’re the monster,” I reply suggestively.
“It takes a little prep, Slave. You want to enjoy it.”
“But I want you in me now, Mistress!” I whine playfully.
She gets up on her knees, grabs the lube, smears some on her prick and my ass, and rams it in. “Oh, Mistress,” I say, “oh, Mistress,” as the ecstasy drowns the initial pain. I keep clinging to her with my arms and legs, and we kiss as she delights not only my asshole but every fiber of my being. As I become exhausted, I let go and lie back as Mistress violently pounds away. I’m powerless and I love it. Never have I been this elated. Never have I been this alive.
She flips me over and positions me on my knees with my chest on the mattress. Without missing a beat, Mistress is back inside me grinding fiercely. I yelp in horror and pain as she pulls it all the way and rams it back in. I bite the pillow to muffle my screams. Being a slave isn’t always fun! She pulls it out and rams it in four more times, each more painful than the last. Now she leaves it in and begins jackhammering again. The pain is gone because everything between my waist and my thighs is numb. All I can do is moan inaudibly, “Thank you, Mistress … Thank you, Mistress …”
One thing I can feel is her ecstasy radiating through her hands on my hips and her dick in my ass. I’m completely outside of myself. I don’t know how long she’s been at it. It could be 15 minutes; it could be 15 hours. Finally, I feel the trembling and throbbing followed by the colossal eruption. I sigh, my entire body sighs, as the monster deflates. I hear Mistress panting and I realize I’m freely crying tears of ecstasy and joy. She rolls off me and I gingerly lie on my side facing her, once again feeling that marvelous juice running out of my butt. I wipe my eyes and we kiss several times and I’m asleep before my head hits the pillow.
I wake up while Mistress is still sleeping. I limp into the bathroom and relieve myself front and back. Pooping is a different experience this morning. On the dresser I find the key to the locks on my wrist cuffs and collar. I unlock myself and go in and shower. In my overnight bag I have flats, a cute pair of shorts that really flatter my butt, panties, a padded push-up bra, and a powder blue V-neck T-shirt. I get dressed and admire myself in the mirror. I hope Mistress is pleased. I put on foundation, a little eye makeup, and lipstick. Just as I’m getting ready to do my hair, Mistress walks in. “Good morning, Slave,” she says. “You look as cute in the morning as you do at night.”
“I’m sorry I unlocked myself and showered without permission, Mistress. I didn’t want to wake you.”
“It’s OK,” she smiles, “this time. Next time wake me. You’ll likely never be punished for waking me. You will be punished for unlocking yourself.”
“Would you like me to make us some breakfast, Mistress?”
“All I have is coffee, fruit, and cereal. Give me a few minutes and we’ll go in and eat.”
“Yes, ma’am. That sounds great.”
We eat and talk casually until we finish our coffee, then I say, “As much as I’m enjoying this, Mistress, I have to go.” We stand and I give her a big hug and we kiss several times. “Thank you so, so much, Mistress, for the most wonderful night of my life.”
“You’re very welcome. It was wonderful for me too.”
“Can we do this again sometime? Please?”
“Of course, I’d love to. When might work for you?” she asks.
“How about tonight?”


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