Category: Sissy Story


Hey gurls, for today I want to publish a nice illustrated true story by Slutty Chrissy…
For all the sissies who loves gloryhole stories ;)
Chrissy also produced one of the videos posted a long time ago: #501 – Sissy trainer by Slutty Chrissy
Enjoy your read and also visit Chrissy’s blog: http://sissychrissytgcaptions.blogspot.com

Gloryhole first timer

by Slutty Chrissy

This is a true story of an experience I had last week. I hope you enjoy!

It all started this past Thursday on my lunch hour. I was feeling especially girly that day and I decided to make a detour to my favorite little adult bookstore/lingerie store.

I walked in and slowly browsed around, looking at the lingerie and dresses, just enjoying the feel of all the different fabrics and the unique, incredibly sexy smell that is a combination of stripper perfume and sex toys, with just a hint of dirty old man thrown in. There is nothing hotter than that smell. Well, almost nothing – but let’s not get ahead of ourselves. I picked out a cute little black dress, a pair of matching velvet and lace panties and a black teddy with a skull print all over it.

I went back to work, and snuck into the bathroom to try on my new teddy. I spent the rest of my day wearing a teddy and thigh high stockings.

I felt so sexy, I just wasn’t ready to go home when I got off work. I headed to a local strip club – I figured maybe a lap dance could be fun – some hot stripper noticing that I was wearing lingerie under my clothes should be sufficiently humiliating for a sissy like me.

I wandered around the strip club’s adult boutique for a while – looking at their lingerie and sex toys. I was getting ready to head to the main club when I realized they had a “movie theatre.”

I had been to this club before they remodeled and they had a bunch of booths and a small theatre with 2 TVs and some couches and since I hadn’t checked out their new theatre I thought “Why not?” I was expecting a small room with a couple of couches and a TV or two, but what I found was a row of booths.

I took my time strolling down the hallway, noticing the tell tale stains on the floor of each booth – some dried, some fresh – and noticed the hard plastic chairs hastily shoved into each booth. When I reached the end of the hall I noticed that the chair in the last booth was plush and inviting. Since none of the booths were in use I grabbed the comfy chair. I quickly stripped off my boy clothes and threw some money in the video machine.

I scrolled through the videos until I found one of this hot brunette bimbo with huge tits, servicing three cocks at once. I was so jealous of her – not jealous of the men getting their knobs polished, but jealous of this bimbo who had 3 cocks all to herself, and I had none. I turned a little in my chair to get more comfortable… and that’s when I saw it. What I had wanted to find for so long – a gloryhole!

Before this club had been renovated there were no gloryholes and they strongly discouraged “cruising.” I never expected to find one now. I stared in stunned silence. Holy crap! A gloryhole! And then the cruel twist of fate dawned on me – the theatre was empty. There I was all dressed up, horny as hell and ready to suck only inches away from that magic portal that would deliver cum-filled cocks. But there were none to deliver. I resigned myself to my circumstances, pausing for a moment to wipe my finger in a fresh cumstain on the floor, tasting the bitter salty sweetness of some stranger’s seed. I found a full condom on the floor too and dumped its contents on my chin, loving the feel of it sliding down my neck and pooling on the fabric of my new teddy.

But then I heard the theatre door open. I kneeled down on the floor (putting my stockings into another puddle of jizz!) and put my eye up against the gloryhole. Someone entered the booth next to mine. I was so excited I didn’t know what to do. I had never done this before! I sat back in the chair and waited – paralyzed in excitement and fear. I saw an eye peering through the hole and decided to give him a show. I did the sexiest little dance I could muster, then bent over and wagged my tight ass at him. When I looked back the eye was gone, but I hadn’t heard him leave, so I stuck a finger through the opening and gave him that “come here” motion. As soon as I pulled my finger back there it was. A cock. Some anonymous stranger’s cock. I did what any good sissy would do and wrapped my lips around it.

He was a little soft at first, but I quickly felt him harden in my mouth. I bobbed up and down on his cock, licking his shaft, slobbering all over him. I took him all the way in my mouth until my face was pressed against the hard plastic wall of that booth. He began to pump in and out of my mouth, face fucking me like the dirty little whore I am.

Before I knew it I was alternating between swallowing his cock and begging him for his cum. LOUDLY begging. Like some desperate gutter slut who had to have it to survive. Like a junky needing a fix. I felt him jerk in my mouth and then the first spurt of his hot sticky load showered down the back of my throat. Wave after wave filled my mouth, until I couldn’t keep up and I began drooling cum down my chin.

When he had finished depositing his cum in me, he pulled his cock back through the hole and left the theatre. I slumped on the floor, spent from my first gloryhole blowjob. I sat there, with yet another load of cum on the floor soaking into my panties, my random stranger’s cum beginning to dry on my chin, neck and chest. It was a glorious feeling and I took in my surroundings. On the screen some random pornstar was blowing bubbles with the cum that had just been deposited in HER mouth.

Only this time I wasn’t jealous. I had my own cumload to play with. So I joined her.
I then got dressed and headed out, cum still glistening on my chin and neck, the acrid salty taste fresh in my mouth.

It’s time for a new sissy story today ;)
This is a premiere story by Artful Tongue…
Exclusively on this site, A New Adventure (Part 1) ;)
Enjoy your reading gurls!

A New Adventure (Part 1)

by Artful Tongue

Ever find your self on a new adventure, but it wasn’t exactly new, because you have been fantasizing about it extensively? I have and I am here to tell you, it… is… a… trip. Mine started the day I walked into All Things… Kat was tending bar, dressed in a sexy nymph outfit, leggings, short earth colored soft material skirt, a fun loose fitting shirt, hair all wild and tossed and tall and slender. Electrical charges shot up and down my spine, and the energy I saw immediately charged my groin.

“Wow, this girl is charged,” Little did I know where this adventure was going to take me exactly, but it really didn’t matter to me as the charge was what it is all about, and the charge here was stupefying.

Auburn hair, green eyes, tongue-lisously slim with a flowing hourglass shape accented with a full set of breast, greeted me as we exchanged a quick glance up and down each other’s bodies.

“Hello there sweetheart, I’m Kat, or Katherine, what can I get you tonight?”

To think I had just stepped in off of the street that cold, bitterly exhausting dusk to warm my feet, hands and have a quick glass of wine before moving on to the boredom of my railroad flat?

“How about a glass of pinot noir,” was my slow response as I took in as much as I could of those green eyes and auburn hair. Oh, and that fragrance that she left me with nearly put me over the edge. I knew right then and there that whatever adventures I could have with her I would, and I would go on them willingly.

We talked animatedly for a few hours, exchanging little stories of our life journeys, what we liked, what we didn’t like, and even touched base upon sensuality. The conversation from hello till she started to close up shop was incredibly flirtatious.

It was so flirtatious when she told me she was closing up for the night, that I was welcome to stay, and that I would have to accompany her to the office to do the days paper work, an affirmative shake of my head yes was all I could muster. I just hoped I didn’t droll so much that I turned her off.

Grabbing the bottle of pinot Kat topped off my drink, slide her hand across my fore arm, up towards my upper arm gently squeezing and saying in that low whispery voice that was driving me nuts, “I’ve got to lock the front door, turn the light off and then we’ll head upstairs to the office, ok baby. If you’re not comfortable let me know. The last thing I want to do is make you uncomfortable.”

“”I like you, I like talking to you and am really glad that I dropped in for a drink. It’s really been fun, so why not, let’s see where this conversation takes us.”

Walking around the bar as I was responding, Kat walks close to the bar scooting the stools back in under the bar and when she gets behind me a feel her hands grab me by my midsection, I feel her breathe on the back of my neck as she whispers, “I have to ask if you are comfortable as there probably is going to be some very unexpected things happening upstairs, and lord knows I am really into having fun, and for some, fun is a bit different than fun is for others. I hope our sense of fun overlaps, and over laps a lot.”

After locking the doors, turning the house light off and dimming the other lights Kat slides back along the bar reaches out with her right hand, grabbing my hand she pulls herself into me, never breaking eye contact, moistens her lips and starts to kiss me gently on the cheeks and then lips.

Electricity shoots down my spine and before I can get a handle on this, her tongue is probing around my lips sliding in between my lips, gently prying my mouth open with so much ease she has her tongue in my mouth and we are locked down in a full-blown French.

Stepping back she says, “Oh I see you like that.”

“Of course I do, I’m not a fool. I think you are so hot. Man all I want to…”

She places her fingertips on my lips and says, “be careful of what you wish for.”

“Ok, but I am full speed ahead.”

“Well, that sounds encouraging but why not be slow speed ahead, after all, considering the plans I have in store for you, slow speed ahead might be a better strategy.”

With that I feel her left hand come to rest upon my left thigh, she starts a soft caress that gets the blood flowing to my groin. Before I knew it she was working the crotch of my pants as she kisses, licked and even sucked me from my mouth to behind my ear.

“Let’s go baby… follow me ok… it’s time to cook the books, ha, ha, ha.”

Visually, I was soaking all of her in, as much as I could and I still couldn’t get enough. My eyes took in her ass, all of it: the fullness, the firmness, the shape, the fluidity of it, with out a doubt, all I thought about as we walked up the stairwell was: was having it for myself. The walk up to the 2nd floor wasn’t long enough. I drifted into a fantasy of us getting naked, kissing each other all over our bodies, of her going down on me, and me going down on her. I fantasied of me sucking that clit till she was dripping wet with her moistness and mine, then turning her over and massaging her ass to the point that she would take my cock in there as much as she would in her pussy, but not until I had eaten it out. I found myself licking my lips and just wanting to get to that part as soon as I could.

We got to the second floor walk a few steps and stopped in front of the office door. “Once you’re in here, I don’t know if I’ll ever let you go? Last chance to leave, in or out?”

“Oh I am so in it’s ridiculous, after you my fine Kat,” I answered firm and true.

“Ok, here we go, your life will never be the same. I guarantee that.”

Kat opened the door, from first glance an office like all others and then I noticed some of the furniture seemed suited more for a home. I liked it. It made me feel comfortable and secure all at once.

“Baby, sit here and I’ll be right back ok,” Kat directed me pointing to a nice stuffed chair. She disappeared into an adjacent room and after a few minutes return with hands behind her back, with a different skirt on, one that was floor length and accented her hips in how it was cut and fitted. All of this I admired greatly. Her breasts were on full display now as she unbuttoned a few more of the buttons showing off her cleavage.

“Ready for an adventure sweetheart?”

“Sure.”

“Ok close those eyes for a few minutes.” I did and shortly after that I heard a match light and then smelled the distinct odor of pot, followed by her exhale blown into my mouth and face. Still I kept my eyes closed as instructed. She took my right hand in her hands placed it on the arm of the chair, did the same with the left arm, slide in close to my face, gave me another breathe of pot, kissed my lips, licked my lips, placed her finger tips on my lips and said, “don’t move, keep those arms right where they are, and suck my fingers.”

And I did, in fact I thought I’ll be silly and I said, “yes mistress please allow me to suck your fingers.’

Smack! Right across my cheek with her open hand, immediately followed by, “keep those eyes closed, don’t speak and listen carefully. You agreed, you came into my bar for a reason. You followed me up to this office for a reason. You are sitting in my chair allowing me to have my way with you for a reason. I knew the moment you walked into my bar that you would comply to everything I wanted you to do. I know that you have an open mind. That you want to expanded your experiences. So this is how this is going to pan out. I am in fact going to be your mistress and you will comply. You will behave in accordance with my every whim and those whims started the moment you walked through my door. Now, this isn’t a joking matter, so when you say, ‘yes mistress’ say it when directed to and with utmost devotion. Or I will throw you to the wolves. And you quite frankly are not ready for that.”

Throughout this little talking to, I never once opened my eyes, my arms stayed on the armrest of the chair and I listened as closely as I could. With eyes closed and full attention given to Kat I hardly even noticed that she was tying my arms to the chair and my ankles also.

“Now my little captive one, open those eyes.”

When I did Kat stood in front of me with only that beautiful floor length skirt on. She had coconut oil in her left hand and was pouring some out into her right hand, placed the bottle down and rubbed her hands together. Cupping her breast she asked, “do you like these girls? You may speak.”

“Yes mistress I do.”

“Good because here they come.”

Kat walked across the floor, straddled my legs, started to lower herself on to the seat of the chair by bending her knees till they were on the cushion and then slide up towards me bringing me those beautifully full oiled breast.

“Kiss those nipples my little submissive one.”

I did.

“Just kiss, no sucking yet, and please control the amount of tongue. Ease into loving my nipples, ease into loving my breast, ease into loving all of me, because if you start slow now, what you have to go through next will be so much more exciting. Again, you may speak.”

“Yes mistress, I wish to ease into everything with you.”

“Oh my little compliant one, did you just say you wanted to ease into everything with me? That is so good of you because you have no choice now. Not only are you my little submissive and compliant one, you are going to become my little slut whore. You will be quite the slut whore, one that you have never been before. Oh you are going to give your body to me to do with it, in whatever way my desires lead me. How’s that sound my little compliant one?”

“Yes mistress your desires and my compliance.”

“Ok, here’s your first reward for being so agreeable.”

With that she lowered herself down to my groin, unzipped my pants, forced them down over my hips towards my knees and then ankles and started to work on my cock, which by the way was quite hard and full.

First she got a good dose of coconut oil on her hands and then started messaging my cock with full firm strokes. Never did she take her eyes off of it. She also didn’t speak much except for the occasional, “oh, I see you are excited, ready,” and, “umm, maybe now I’ll suck that little monster.”

Then she lowered her head and started to kiss my tip of my cock. She even puckered up and started to lube the entire head with her lips. After a few minutes it became apparent that Kat was in no hurry to suck it. She was quite happy using the techniques she was. As she lubed my head up her left hand slide up and down my shaft working my cum up from my cocks treasure trove of sperm resources.

After a few more minutes she lifted her head and said quite matter of fact, “my little compliant one, my little submissive one, do you think you can treat my clit the way I have treated your cock? You may speak.”

Yes mistress I think, no, I know I can.”

“Good, after all this, and so many other things, this will be expected of you, if you are to be my little slut whore. My little slut whore who just wants to pleasure who ever I wish for you to pleasure.”

Kat said all of this as she walked behind me and continued to tell me about our future together as she blindfolded me, “you see my little slut whore. I have been waiting for you to walk in to my bar. In fact as I said, I knew what you are all about the moment I laid eyes on you. Now I wonder, do you see the same thing in yourself that I see in you?”

By now Kat had positioned herself in front of me again. I could tell as I felt her legs brush up against the outside of my legs. She lowered herself onto the seat cushion again and leaned into me and stepped up so she was standing on the seat cushion.

“Now my little submissive slut, my little slut whore, the task is to treat my gurl clit, that’s gurl spelled g-u-r-l, treat my gurl clit the same as I treated yours, after all you may not realize this but this is the first day of your training.”

Kat braced herself with her hands on the top of the backrest of the chair, I could feel her weight shifting forward, and then I felt it, and it all made sense, and I didn’t have any problem with what was about to go down. In fact I was the most excited I have ever been. I felt the tip of her gurl clit greet my lips in a soft sweet gesture of here I am soft, firm, erect and wanting your lips all over my tip and head.

‘Oh mistress,” slipped from my mouth, “yes, you may speak” was Kat’s response.

“Oh mistress, I want your gurl clit deep in my mouth, I want to feel you fuck my mouth so deep. I want your cum, I want to taste you, I want to be your personal slut whore who is a total fuck toy for you, and who ever else you may want me to please.”

“Ok, open that mouth, suck my cock you little cock sucking slut whore, from today on, you will be my personal little slut whore who loves tranny cock, shemale cock and even straight cock. That’s it baby suck that cock. Here let me take it out a bit, work the head, that’s it work it till you feel cum rise and slip out of the tip. Suck it, yes suck it, yes, yes, yes suck it, that’s it you little submissive slut whore cock sucking sissy.”

And with that she backed off a bit and manually pleasured herself till a bit of cum appeared on the tip.

“Have you ever eaten cum, my slut whore, have you?”

“Yes mistress, I have.”

Whose cum have you eaten, and do not lie to me I will know.”

“My own mistress, in fact your cock is the very first cock I have ever had in my mouth. That is the truth mistress, that is the truth.”

“I believe you. And because I do you may have some of my cum.”

And again her cock was directed to my mouth.
“That’s it, glaze your lips with my cum, yes, that’s correct, now pucker up, yes, suck now – don’t shallow yet, glaze those lips more sweetheart. Rub your lips over the tip, that’s it nice and easy, see now you are learning how to really love a cock. Oh believe me the time when you can be a nasty cock slut that wants totally control of hard juicy cock, that day is getting here sooner than you think.”

I would learn to love it when Kat went off in her long sexually explicit diatribes. God it got me so much harder, wanting to be taken. Kat knew how to use her voice. All of the sweet tones and soft whispering voices that she accessed, all of it made me want to be an unadulterated fuck toy.

She continued: “Lick a bit off. That’s it my little cock slut. I can see clearly, that you are going to be quite the wonderful cock-sucking slut. Here, lift that sweet little hetro-fuck face so I can suck tongue with you. That’s it, lick those lips full of sweet cum,” and with that she was on top of me, tongue gliding over my lips, darting into my mouth, full mouth sucking down on full mouth, tongues rubbing up against each other, and the tongue suck where your partner clamps down on your tongue with suction and gives you a tongue blow job. I loved it and I loved all of it.

I did rub Kat’s cum all over my lips. I licked her cum from my lips, bringing it to my mouth, tasting her bitter-sweet fuck juices as I liked to call them. The little we shared glazed both of ours mouths, and both of our mouths glided freely across and over each other. The cum we shared got my cock even harder as pre-cum started flowing immediately. When Kat saw that, she carefully scooped some up on her fingertips and offered it to my mouth.

“I want to see how much you like cum, slut whore. Are you going to be a cum slut also? Here let me help you get more of this creamy cum.”

She worked my shaft up and down milking more of my juices from my cock and drained my cum onto her fingertips and finger. Lifting her hand to my mouth she spoke firmly yet encouragingly, “open that sweet cum loving mouth of yours my little slut whore. Here get your cum, that’s it suck your cum from my fingers, suck my fingers like they are my cock, my friends cocks.”

I did, and I did knowing full well that I wanted more and more. I did knowing that I wanted Kat to make me the biggest, best, most enthusiastic slut whore who loves cum and cock that she could make me into.

I sucked the cum from her fingers and licked it off of her palms with the enthusiasm that any cum slut whore’s mistress would be proud of. I wanted her fingers to be perpetually covered with the bittersweet tasting nectar of cock and I wanted her fingers to fuck my mouth with total abandon. I wanted to be Kat’s personal super slut cum whore solely because I wanted cock, I wanted gurl cock, because I knew I wanted to be the ultimate sissy cock slut offering my mouth, my tongue, my hands, my cock and my ass to Kat and her friends to use and abuse as their own personal fuck toy.

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Well today, for the start of the new week…
It’s time for a new master story by Mr. S… ;)
Another story of total submission to your master ;)
Enjoy your read!

Breakfast in Bed

by Mr. S

It’s Sunday morning and we sleep in a little late. Your alarm wakes you at seven AM by gently buzzing a vibrator tucked in your panties. It’s a neat system I built so that you always wake before me to start your domestic chores. You gently leave bed without disturbing me and mince down the hall to your bright pink bathroom.

Nothing special to do on a Sunday; just shower, shave everything, replace makeup, fix your hair, and change into a different babydoll outfit than you slept in. A little perfume and you’re done by 8. Off to the kitchen.

My Sunday breakfast is pretty bland by the standards of the rest of the week. Instead of a proper meal I like to have a protein shake to help me recover from the kickboxing club I work out at on Saturdays. The first step is to start water for coffee. You mix the protein powder into a glass of milk and stir until it completely dissolves and toss in three ice cubes as you know I like it cold. Just then the water is boiling and you pour it into a French press and add the correct amount of ground coffee. The press, protein shake, and a mug go onto a serving platter which you carry back to the bedroom.

You gently place the platter on my nightstand, mince around the bed and slowly crawl under the sheets. I groggily come to as you eagerly suck my morning wood. Pure heaven. I wait a minute or two and throw the covers off revealing your coy slutty smile as you suckle my cock. You pause just long enough to give me a thrilling glimpse of your makeup and then it’s right back down on my cock. Eventually I pull back from you and pour a cup of coffee.

“Did you clean yourself out yet?” I ask.

“No, Sir,” comes your immediate reply knowing exactly what that means.

“Well why don’t you go do that. I’ve got something special in mind.”

Curious to see what I’ve come up with you scamper back to the pink bathroom while I sip my coffee. You go through the usual course of cleaning yourself. Three enemas slowly administered and allowed to work their way out gently, leaving your system flushed, cleaned, and ready to play. As a final step you massage in a good dollup of lube so your boi pussy is prepared for entry. Daddy likes a clean, eager pussy.

Once ready you practically skip back to the bedroom brimming with curiosity and craving the obvious ass play I’ve got in store. You find me relaxed and sipping my coffee having not touched my protein shake. As you enter I put down my coffee mug and motion you to the bed.

“All clean… Good. Just get on all fours.”

You bend over and I’m rapidly upon you. Usually I’m fun and playful. Today, however, it’s all business from me. Within the first few pumps of my cock you realize we’re not having fun sissy sex; it’s just an ass pounding. I give you permission to suck your thumb if it helps and you do, thankful for the idea. For some reason sucking eases the pain from the jack hammer job I’m giving you from behind.

Pretty soon I’m ready and I eagerly shoot my cum deep in your sissy ass pussy. You start to turn to suck me clean as usual but I stop you by putting my hand on the back of your neck.

“Stay there. Keep your face down and ass up.” With that I walk away. Knowing how much I like obedience you sit still, ass up and ready. As I enter the room from the corner of your eye you see a funnel and the milk jug in my right hand. That’s all you get as I snap “head down!” at you and smack your ass firmly. You regain the proper position, with your back arched and used ass upward and on display. In a matter of seconds you feel the funnel ease into your butt. There’s almost no resistance as you’re well stretched from the ass pounding I gave you.

Then comes the rude part. You buck a little as I pour cold milk into your funneled asshole. I push your neck back down and chuckle. I know the cold milk is uncomfortable and crampy. I pour in just about a cup and slip the funnel out. With a quick spank I tell you to sit up. Sheepishly you look at me wondering why I just did that.

“Well, I suppose you need to expel that milk,” I tell you. You get to your feet and walk toward the door to get back to the safety of your pink bathroom but I stop you. “No, no. Not on the toilet. Here.” I hold out a glass and you daintily take it from me. “That’s it. Poop your milk out into the glass,” I encourage.

You slowly squat down with the glass on the floor beneath you. It takes a few minutes to relax and get comfortable, especially with me staring so intently. Eventually you tilt your head back and squirt out your milk into the glass. The aim is easy, enemas have become normal for you. Rapidly the glass fills with a frothy mixture of milk, lube, and cum.

Eager to clean up you stand, pick up the glass and turn for the door but once again I stop you. “Where are you going, sissy?” I ask. “I’ve got my protein shake and now you have yours. I thought we’d have breakfast together.” You slink back into bed staring at your glass of warm, cummy, ass milk. You’re struck out of silence as I click my glass into yours and happily comment,”Cheers! Drink up.” Feeling the most humiliation of your life you slowly lift the glass to your lips and start sipping. “Breakfast in bed together,” I say, “maybe we should do this every Sunday.”

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