Cyndi's Gown Ch. 03

Story Info
The blackmail continues and secrets are revealed.
3.1k words
4.54
12k
9
0

Part 3 of the 3 part series

Updated 06/10/2023
Created 04/29/2021
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

The next day I spent working, manning our exhibit at the trade show. Linda arrived in the booth, just after lunch, and started talking to me. "Oh Charles," she exclaimed, "You should have been with us last night! We all went to the most bizarre adult club that I have ever seen! You just wouldn't believe how incredibly kinky it was!" Linda continued with a very detailed and explicit description of the night's entertainment. "They even had a man, actually a real sissy boy, that was totally subjugated, dressed as a little girl, and made to submit to total sexual servitude and humiliation from both men and women! It was really hot!

As he beautiful eyes bore into mine, she continued. "You should go with us tonight, we are planning on watching another bizarre and erotic display!" My head was spinning! Was she taunting me - did she know that 'Cissy' was indeed me? No, I was letting my mind run away with itself - but was I? I stammered back to Linda, that I had an appointment with a customer that evening, who was quite prudish.

"Oh well, Charles", you'll still have a chance to witness my sissy in action - and even use 'her' lipsticked mouth yourself!" Linda then explained how she had won the contest, (as if I didn't know!) and that I was invited for her open house the weekend of Cissy's servitude.

I could swear she was taunting me, but again, I was letting my imagination go wild. How could she have possibly recognized me - no way - I just looked too different. "See you later, Hon," she cooed as she kissed me on the cheek, "too bad you can't join us."

I returned to my hotel around 5:00 and there was a message from Jennifer, telling me to be ready for 6:00. I quickly showered, made sure that my body was totally hairless, then applied my makeup. At precisely 6:00, Jennifer and Holly arrived. I was laced into the pink corset, that I had obtained at Carolyn's, along with the matching bra and crotchless panties. Sheer black stockings were slid up my legs, attached to the garters, and then my feet were squeezed into 6 inch black patent high heels. Holly fussed with my makeup, making me look even more exotic. My wig was carefully teased into place, and finally the humiliating pink ribbon around my penis!

Holly threw my coat over me, and both girls grabbed my arm and escorted me out of the room, down the elevator, to a taxi waiting outside the hotel. After a short ride, we pulled up to a small restaurant, got out of the taxi and entered.

The hostess greeted Holly and Jennifer by name. "Your dinner guests are waiting for you", she said as she led us to out table. Although I had almost become used to being surprised over the past several days, I was again shocked. Sitting at our table, waiting for us, were Linda and my boss!

As we sat down, Linda greeted me. "Hello Cissy, we are dying to see your little modelling session tonight. Oh by the way, I have been telling people about my upcoming open house and you, little girl, are going to be quite busy!" As the waitress came over to take our order, Jennifer unbuttoned my coat, revealing my frilly attire underneath. As the waitress looked in surprise, Jennifer pulled the coat open even further, so she could see my beribboned penis! She started to giggle, then went and dragged several of the other waitresses over to see Jennifer and Holly's trained sissy.

Since they had plans for me, the dinner was mercifully short - although every employee in the restaurant, waitresses, the hostess, the bartender, even the cooks and dishwashers, made some excuse to make a trip to our table to see the "sissy boy".

As we left the restaurant, I received quite a few amused stares from the other patrons, giggles from the waitresses and leers from the bartender. The five of us then jumped into a taxi for the short ride to Carolyn's boutique. There was a "closed" sign on the door as we arrived. Jennifer led us all around to the back door, where Carolyn admitted us.

"How nice to see you again, Cissy", said Carolyn. "Of course you remember Cyndi and Robin. Blushing, I greeted the two young ladies. Carolyn continued, "Cissy this is our photographer, Michelle, and her assistant, David." I murmured a greeting, as they both gave me an amused look.

Carolyn then explained to the people that were with me, "First we are going to have Cissy model some of the fantasy outfits, which I have designed for transvestite. Next we shall have her model some of the bondage and restraint equipment, and finally some of the 'toys' that I am offering will be used on her."

Jennifer, Holly, and of course, Linda and my boss, were invited to sit, relax with a drink, and enjoy the photo session as Robin and Cyndi led me to the back changing room.

For the next two hours, I was photographed in every imaginable costume that a crossdresser would enjoy wearing or costumes that admirers of crossdressers would enjoy seeing. Erotic lingerie, corsets, bridal gowns, cocktail dresses, skirts, blouses, babydoll nightgowns, little girl party dresses, cheerleader outfits, school girl uniforms, frilly little baby dresses- just about every costume for every fantasy! Of course, I was also made to model the mandatory transvestite French maid uniform.

As I finished the costume portion of the photo session, a very striking female, accompanied by a tall muscular man arrived. Carolyn led them over to me. "Cissy, I'd like you to meet Mistress Gwen and Master Philip. They will be posing with you for the next part of the session, modelling my new leather wear line, as well as demonstrating my bondage equipment and other devices."

Again, I was led to the back room by Robin and Cyndi. This time, I was laced into an extremely heavily boned leather corset and matching leather panties. The panties had a zipper that opened from the front of my crotch area up and over my butt, so I could be exposed in any manner my Mistress or Master desired. Finally, 8 inch black patent high heels, with locking ankle straps were placed on my feet. I could not walk back into the main room without Robin and Cyndi holding each of my arms. The shoes were absolute murder! Thankfully, I was allowed to sit.

For the first hour of the bondage device photo session, Mistress Gwen and Master Philip modelled Carolyn's extensive line of leather wear, while I was restrained in every way possible, with Carolyn's line of bondage devices kneeling, bent over a sawhorse, standing and lying in a spread-eagle position, and even suspended! I was gagged, blindfolded, and totally subjugated for the cameras, as Mistress Gwen and Master Philip demonstrated Carolyn's complete line of whips, paddles and canes!

The final part of the photo session was devoted to Carolyn's toy and device products. First of all, I was photographed alone, in various B & D devices - chastity belt, with a self contained butt-plug, leather cock and ball sheaths, hoods, and cock rings. Next, Carolyn's very unusual and innovative humiliation and sexual submission devices were brought out.

Carolyn then turned to everyone in the room and announced, "This section of the catalogue is going to be a separate supplement, only available to select customers. To really show-off these devices, actual sexual submission is required and I will tightly control, just who receives this supplement." I could hear comments from the observers, "Oh Hot!" exclaimed Holly.

"This I've gotta see", said Linda.

I was then bent over the sawhorse again, with my wrists restrained and my legs spread wide open and restrained at my ankles. Mistress Gwen then strapped on a black leather belt, with a huge dildo. A bridle was placed over my head, along with a bit in my mouth. As the camera started clicking, Mistress Gwen thrust the dildo deep into my ass, while pulling on the reins of my bridal. Tears ran from my eyes as she fucked me deeply. All I could do was moan as the bit in my mouth kept me from talking or complaining. I heard Jennifer exclaim, "Oh I love it! I'm going to try that on her, next time we get together." After several shots of my being reamed by Mistress Gwen, I was released from the sawhorse.

The next device looked something like a kneeler, one sees in a church, but all similarities ended there. Coming up from the front, were three small metal posts. One post was precisely in the middle, with the other two located on each side. I was made to kneel in the device. The middle post had a small cup, that I rested my chin in, while my wrists were secured to the two side posts. A harness was placed over my head, which prevented me moving my head from the chin rest. Carolyn then turned to the observers. "Ladies and Gentlemen, my latest invention- a three way face-fucking bench. As you can see, the slave's head is held immobile, while her two hands are also available. This allows a continuous face-fucking of the slave. As her mouth is being fucked, two other cocks can be masturbated to near completion, by her restrained hands. If the slave is properly motivated by her Mistress or Master, she will receive continuous forced feedings of cum, from as many men who are present."

I heard Linda exclaim, "I'm gonna buy one of those, for our weekend!" Everyone laughed at her enthusiasm, as Michelle photographed me in this insidious device.

Carolyn then stepped forward. "Now I want see it in actual use. Master Philip, please pose with your cock in her mouth." Master Philip stepped up to the bench and thrust his hard penis deep into my mouth. Again, the flash and clicking of Michelle's camera. Carolyn then turned to my boss, and to Michelle's assistant, David. "Would you gentlemen mind helping to demonstrate?" In a matter of seconds, both David and my boss had walked over and I now found myself masturbating them, as Master Philip fucked my mouth! Again, Michelle's camera clicking.

Much to the disappointment of all three men, Carolyn had them step away from the bench, before they had attained orgasm. "Time enough for that later, Gentlemen. I have a few more devices that need to be photographed."

I was released from the face-fucking bench and made to kneel down. Robin then strapped another device over my head. Again, it was a bridle-like harness, but directly over my nose and mouth a large soft plastic contraption was secured. Carolyn then held up a mirror, as she explained to the observers. "As you can see, this is a very realistic model of a vagina." I looked in horror at my reflection in the mirror! It looked exactly like a vagina! Carolyn continued, "For a master who desires the feeling of a hot vagina around his penis, but not having one available, I have created an alternative. It is soft and comfortable, and with penetration through the silicone labia, the master will experience the same warm erotic feeling as penetration of a real vagina. The only difference," Carolyn giggled, "is that the warm moist feeling is the slaves mouth! Give it a try Philip!"

The camera clicked and flashed as Master Philip began fucking the artificial vagina and, of course, once again, my mouth! I could smell the sensuous aroma of Michelle's perfume, as she moved in for extreme close-ups of Master Philip using the device. Carolyn, once again had Master Philip remove his hard penis from my mouth, before orgasm. "Only one more device, Philip, and this time you can cum all you want," exclaimed Carolyn.

Carolyn then removed the artificial vagina from my face. Turning to everyone in the room, she announced: "And now ladies and gentlemen, the ultimate device for those slaves who require a constant protein diet."

Carolyn led me to a device that looked like a chair, but instead of the back being full, it just had two supports coming up, one on each side. "Sit down, Cissy", she ordered. I started to sit in the 'chair, trying to figure out how to lean back, when Carolyn interjected. "No Cissy, face the other way!" I got up, and then sat down in the chair, facing the back. "Lean back, Cissy," Carolyn ordered. As I started to lean back, Carolyn slid out a long flat piece from underneath the "seat" of the chair.

I was now, lying flat on my back, with both feet still on the floor. That didn't last long, however. Robin and Cyndi lifted my legs so they were straight up in the air, and restrained my ankles to the two posts coming from either side of the chair! I was positioned like the letter "L" with my legs vertical, and the rest of my body horizontal.

Carolyn adjusted the part of the chair I was lying on, so it tilted down, attached a broad strap tightly around my waist and restrained my arms to the waist belt. Next she swung out a large funnel-like device so it was directly over my face. Attached to the bottom of the funnel was a mouthpiece attached to a short hose. The mouthpiece was then secured to my mouth.

Carolyn again turned to the observers. "This is an extremely versatile device. It allows a heavy oral protein ingestion. As you can see, the sperm donors simply have to ejaculate into the funnel, and it is injected directly into the slave's mouth. Adaptors are available to make the funnel larger at the rim, to accommodate as many donors as desired." Carolyn continued, "The appliance also allows the slave to be force fed with his own sperm." With that, Carolyn produced a sheath like device that she placed over my penis. She squeezed a small bulb that inflated an envelope, inside the device, so it was tight. Next she attached a clear plastic hose to the end of the sheath, and attached the other end of the tube to a small pump that was attached to the bottom of the funnel.

"As you can see," said Carolyn, "should there be no donors available, the slave can be continuously supplied with protein supplied by her own body. This also increases sperm dosage, even when you are fortunate enough to have donors." Carolyn then reached over, flicked a small switch. A sudden wave of ecstasy hit me. My penis was being pumped and sucked in a way that I had never felt before. It was a fantastic feeling! I only wished that I wasn't restrained like this in front of onlookers.

Michelle, started taking pictures of the device, as it pumped my hard penis. As she photographed me in Carolyn's "feeding station", Master Philip, David and my boss all walked up to the funnel, and began masturbating, again! More flashing and clicking from Michelle! The three men were beginning to moan in pleasure, and I realized that I was about to receive another forced feeding of cum! As their jerking off became faster and faster, I suddenly felt Mistress Gwen penetrating my exposed bottom again. This time, however, the dildo was not so thick but it was extremely long. With a hard lunge, she penetrated my exposed ass and started rubbing the end of the dildo against my prostrate! That did it! The pumping on my cock, the dildo massaging my prostrate and I suddenly saw thick white sperm - lots of it - traveling up the clear plastic tube, heading for my mouth. Michelle continued her photographing, as the first drop of my own cum, landed on my tongue! Seconds later, hot thick streams of it started filling, my mouth. I swallowed frantically as the sperm kept coming. Then, more sperm! Three huge loads of it, to be precise, as Master Philip, David and my boss ejaculated into the funnel. Mistress Gwen kept up her fucking of my ass, causing me to shoot another hot load of my own cum into my own mouth, as Michelle and her ubiquitous camera continued shooting pictures!

All the cum, constantly flowing into the funnel, was visible to everyone watching. Evidently it got the guys excited again, as all three of them provided three more donations of their hot cum to my restrained mouth! Finally, I was released from the "feeding station". I felt exhausted, used and totally humiliated. Carolyn helped me up. "Sit down, Cissy, you've been an excellent model," she said. "I think we shall have you model for our new catalogues, twice a year."

I was past the point of protesting. I just nodded my head quietly in acquiescence. Carolyn handed me a glass of wine, and we all relaxed and chatted awhile. I of course, spoke very little as I did not want my boss, nor Linda to identify me.

Linda turned to Jennifer and Holly. "Just how did you get this sissy to submit to all these things?" she asked. Jennifer answered, "We really owe it to Carolyn. You see, we ordered Cissy to show up here and be fitted for a corset. We didn't really know if the little sissy would really go through with it, but once he showed up, we had him! Carolyn, Robin and Cyndi took photos of him in his corset, crotchless panties and bra. However, he had neither makeup nor wig on, so he is totally recognizable in the photo. Carolyn also held one of his credit cards ransom, so we know his true identity. You see, we could blackmail him in a second, if he doesn't do exactly what we want!" Linda exclaimed, "Wow! That's fantastic! I'd love to see those photos!" Carolyn got up, went to her desk and returned with an envelope. "Here, Linda, take a look!" My head started whirring, I became flushed, and my stomach suddenly knotted up.

Linda opened the envelope, and withdrew the photographs. A look of shock came across her face, and then it slowly turned into a huge smile. Looking at me, she handed the photographs to my boss! Again, the look of shock, quickly replaced with a smile. I couldn't bear to look at either of them; my face was burning in embarrassment. Linda stood up, not letting on to the others that she knew who I was, and walked over to me. As I sat there, cowering, she gently removed my wig, gave me a kiss on the cheek, and whispered into my ear. "Looks like you will be gaining some new job responsibilities, my sissy little girl." With a throaty laugh, she looked at my boss. As she winked at him, he winked back at her - then at me!

Please rate this story
The author would appreciate your feedback.
Share this Story

READ MORE OF THIS SERIES

Similar Stories

My Feminine Side Guy becomes a beautiful sexy girl.in Transgender & Crossdressers
Trapped and Trained Ch. 01 Man is drugged, then dressed up and trained to be a slut.in Transgender & Crossdressers
Husband's Transformation Ch. 01 Husband caught wearing panties and changes begin.in Transgender & Crossdressers
The Deal Freddy's wife convinces him to dress up and go clubbing.in Transgender & Crossdressers
"Sissified": 12 Days of Sissy-mas Straight man is turned into a submissive sissy by...in Transgender & Crossdressers
More Stories