The Gala Ch. 06

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Scott is milked as part of a latex adventure.
5.9k words
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Part 6 of the 7 part series

Updated 06/14/2023
Created 06/30/2021
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Chapter 6

The wooden door opened slowly to reveal a petite woman silhouetted against the dim light inside the room. "Hello, cutie pie!" I knew in an instant it was Missy, my driver from earlier in the evening. At least the voice told me it was Missy, but I did not immediately recognize her. Her tailored men's suit had disappeared, and she was now dressed head to toe in a latex bodysuit. The suit was a sexy combination of red and black with the colors of the garment strategically positioned to accentuate her figure. Crimson red accent panels highlighted Missy's rounded breasts and perfectly shaped ass, while the primary black sections enhanced her narrow waist and hourglass shape. She wore a full matching hood that left only her electric green eyes and perfectly lined lips exposed. The overall effect was incredibly erotic and stunning, and I guess my reaction to her appearance must have been obvious. "Come in, come in! No use standing out in that hallway with your mouth hanging wide open."

I obediently followed Missy's instructions, and the door closed behind me. As my eyes adjusted to the light, I took in my surroundings. Everywhere I looked, I saw nothing but latex. The walls were covered with latex upholstered in a classic button-tufted style. All the furniture, which included a large poster bed, several chairs, and a bench, were cushioned, pillowed and sheeted with latex. Curtains of latex decorated the windows. Even the ceiling of the room was a patterned latex design. Only the floor differed slightly. It was covered in black rubber, designed to be anti-skid like something you'd see at a fitness center. Simply put, I had stepped into a latex lover's paradise, and I was utterly captivated by it.

I forced my attention back to Missy. "Mistress, I'm so happy to see you again," I said. "You look quite a bit different from when I last saw you." I truly admired how precisely the bodysuit fit her feminine figure. During the van ride, I hadn't fully appreciated Missy's level of outrageous sexiness. Of course, I was now being seduced by just how perfectly Missy's suit formed to her body. It had to have been custom tailored just for her. Except for the zippered crotch, the garment looked as if the suit had been painted onto her skin. There was not a wrinkle or crease out of place, and the soft light of the room reflected from the garment's shiny surface as she moved. I could easily see the nipples of Missy's breasts bulging beneath their latex covering, and I caught myself staring for a bit too long.

"I may look different, but it's pretty obvious you like what you're seeing with those blue eyes of yours. Good to see you too, sweet cheeks. You've also changed a bit from when I left you earlier," Missy responded. She was looking me up and down with enthusiasm. "No more chastity cage, and I can see your cock and balls have had a very positive reaction to Amanda's drug regimen. That dick of yours was already a fine piece of equipment, but it has plumped up nicely since I last laid eyes on you. Very sexy." Missy slowly circled me where I stood. She reached out with her hand, playfully outlining various parts of my body as she made her way through her inspection. She completed her circuit and looked me directly in the eye. "I've been waiting here anticipating your arrival. I suppose they told you we have two hours. I'm hoping to accomplish quite a bit in that amount of time and I'm sure it will fly by. Think you're up to it, sweetie? It just seems like such a short amount of time. What do you say we get things started?"

"Your wish is my command, Mistress," I said.

"Oh, you'd better be careful, mister," said Missy. "There's more to me than meets the eye, and my imagination can be a very creative and dangerous thing. I do appreciate your apparent willingness to comply with my commands, however. Please give me that kit you're holding. You won't be needing any condoms while you're with me." I trusted that Missy was being honest and handed her the satchel containing all my condoms and the flask. Missy's mouth formed a mischievous smile. "Okay, cutie, follow me this way please."

I trailed after Missy as she crossed the room to a large armoire standing against one wall. "Our first task is to find you something to wear that's appropriate for the occasion," she said. "I think I know just what you need." Missy opened the armoire to reveal an extensive collection of latex garments hanging inside. She briefly rifled through the hangers and retrieved a pair of shiny black bike shorts. She spun playfully around and handed them to me. "Here, babe. I need you to put these on, but let me give you a bit of guidance. They have a few unique features."

I took the shorts from Missy and looked them over. They did look a bit odd.

"You'll probably notice there's a hole in the shorts with reinforced edges," Missy explained. "You'll also see a tube-like sleeve hanging inside the shorts. The hole is the front of the garment, and the tube is in the seat. We're going to lube you up a bit before you try to slide into these. Since the shorts are extremely form-fitting, that will make it much easier. As you put them on, make sure the inner sleeve is pointed down and positioned between your ass cheeks. You'll also need to force your cock and balls through the front hole."

As I listened and continued to inspect the shorts, Missy handed me a bottle of lube.

"Take this and rub it over your thighs, cock and ass, and make sure you get plenty of it in that cute ass-crack of yours." Missy chuckled as she took back the shorts to allow me use of both hands.

Again, I followed her instructions, spreading generous amounts of lube around my crotch and thighs, making sure my cock and ass were well lubricated. Missy gave me a towel to dry my hands and then handed me the shorts. As I the latex began to slide over my thighs and hips, I felt an immediate surge of arousal. The lube made everything slippery, and I struggled a bit to keep a firm grip as I pulled. I was surprised by how good it felt as the shorts formed to the shape of my body. There was an incredible feeling of sexiness as the latex glided into place. The shorts gripped the contours of my ass, and the edges of the cock hole squeezed pleasantly around my dick. It was as if my midsection had been surrounded by its own special cocoon. I relished the sensation of the extra lubricant inside the shorts and the bulge of the sleeve against my asshole. I found myself chuckling because I was being sexually aroused by a pair of shorts. My cock started to harden in response. Blood pumped into my shaft, and the lube that now coated my skin glistened in the light. The latex definitely had me under its spell.

"I see you're already enjoying yourself, mister" Missy said. "That swelling cock is giving you away. I take it you must be a fan of latex?"

"I've always liked it, yes," I said, with a slight tone of embarrassment caused by my growing erection. "I really don't have much experience with it, but I've always thought of it as incredibly erotic. Both the feel and smell are a big turn-on, and I also think latex has the power to make a body look very sexy, whether male or female."

Missy gently spun me around to look me over. "Excellent observation, professor. Now let's get this sleeve where it belongs. I understand you're a bit partial to ass play?" Missy said with a wicked smile.

I was caught by surprise. I really didn't know what to say. "Well,... I guess there's no keeping secrets from you? How in the world do you know that?" I could feel my face flushing with embarrassment.

"Nope. No secrets. Your background has been more-or-less turned into an open book for all of us to read. Claire generously provided us with a detailed write-up of all your sexual proclivities - both normal and not-so-normal. You're quite the naughty boy." Missy laughed. "First, turn around." As I did, Missy pulled on the waist of the shorts directly above my ass crack. "Let's make sure that cute tush has plenty of 'slide-ability'" Missy squeezed forcefully on a bottle of lube, and I felt a cool flow of liquid running down my crack. "Now get down on your hands and knees for a moment. I've got a small dildo that I'm going to use to slide that sleeve up your ass." I quickly knelt down on all fours and soon felt the pressure and squirm of the dildo sliding into the sleeve of the shorts. After a little fiddling and twirling, helped by the extra lube in my ass crack, I felt Missy position the sleeve and then use the dildo to slide the sleeve up my ass. The dildo was not large, and I enjoyed the feeling of having my ass invaded. The slippery lube just added to my pleasure level. Unfortunately for me, toying with my ass was not Missy's current mission, and the dildo was quickly withdrawn. "There! Now your ass has its very own ready-made condom."

Between the sensory feel of the latex and Missy playing with my asshole, my dick had become rock-hard. There could be no doubt about whether I was turned on. My shaft had thickened and stood poking out the front hole of the shorts. I relished the way the shorts felt on my body, and my mind began racing with thoughts of what Missy had planned for my ass. I found myself wishing for a mirror so that I could see how I looked.

"I think I'm going to have to do something about that cock of yours before too much longer," Missy observed. "But I need to make a few more additions to your wardrobe first." She reached again into the armoire and retrieved several items. I saw that Missy now held a neoprene ball stretcher and a full-coverage latex hood. "I'd like you to put on this ball-stretcher. Then I'll help you with the hood."

I was familiar with ball-stretchers from my sessions with Clair. I learned long ago that having my sack stretched during sex was a huge turn-on. This particular stretcher caught my attention though. It was longer than anything I'd ever tried before. Normal stretchers were two or three inches, and I knew I could handle them, but this one had to be at least four or five inches long. That was going to be a serious stretch, and I doubted I could make it fit. Missy watched as I struggled to feed first one testicle and then the other through the tube shape of the stretcher. The task was made even more difficult because of the swollen state of my ball sack. As I worked my sack into the tube, I soon discovered the stretcher was large and flexible. By grabbing loose skin and feeding it through the stretcher, I finally managed to coax and pull both of my balls into place. The stretcher greedily accepted the girth of my sack, and I began to appreciate the full stretch and grip of the neoprene tube now encasing my balls. I was forced to stop and take a deep breath. The stretcher's downward pull was intense, creating distance between my ball sack and my body. The pulling sensation amped up the level of my arousal. My cock swelled and gorged with blood, the tissues throbbing and stiff with fluid.

"Very nice!" Missy remarked. "Don't you be tempted to touch that straining dick of yours, mister hot rod. It's all mine. But before I get busy, we've got one more item to add to your wardrobe. Kneel down, babe, right here in front of me, and let's get you into this latex hood."

My hands worked in cooperation with Missy's to stretch and pull the latex hood over my head. I found myself intoxicated by the overwhelming smell of latex. I took a series of deep breaths, taking in the sexy odor from the hood surrounding my face. After a bit of adjustment, the eyes and mouth openings of the hood seated into place. I was captivated by the way the tightness of the hood pushed against my skin. I felt the hood's mouth opening pressing around my lips, forcing them slightly outward in a sort of pout.

"Now don't you just look delicious!" Missy said again. "I've managed to make you into the perfect little latex sub!"

I did feel sexy and incredibly alive. It came as a surprise just how much I was enjoying being dressed in this costume. The shorts were squeezing on the base of my cock and the intense pull of the ball stretcher was making it feel even better. I also got a quick reminder of the sleeve inserted up my ass if I moved in any direction. The hood was confining, but comfortable, and I liked how it changed the sound in the room. I was so aroused I could feel my heart beating in my chest.

"Now. Let's get down to business, shall we, sweet cheeks?" Missy said. She led me across the room toward several pieces of furniture. I found myself standing in front of a large wooden sawhorse, its broad top upholstered in shining latex. "I'd like you to lay your torso onto this bondage horse, please," Missy instructed. I moved closer to one end of the horse, noticing the edge had been contoured to accept the curve of my abdomen. As I bent to lay down, I was jolted as Missy reached between my legs and grabbed my stiff cock. She quickly pulled the end of my rock-hard dick down toward the floor. "We've got to get this giant equipment of yours out of the way and into the right position. Now go ahead, honey. Bend over and lie down." I laid first my stomach and then my chest against the horse, as Missy's hand continued to apply downward pressure to my cock, pointing the head toward the floor. As I settled into place, the latex upholstery felt cold against my skin. I enjoyed how my abdomen fit perfectly against the curved edge, while the opposite end nestled just under my chin. My head hung over, and I was now staring at the floor. "Good boy! Perfect! I was hoping I had made the right length adjustment to the horse," said Missy. "I estimated your body size pretty well, if I do say so myself."

Missy then began to move around me. I could see her feet as she passed back and forth. "You don't have any objection to me tying you up now, do you, babe?" My heart leapt into my throat with anticipation. This whole situation was getting better by the minute.

"Uh, no Mistress. Absolutely not." Even as I spoke, I felt pre-cum begin to ooze from the tip of my cock. Missy was pushing all of the right buttons.

Using black latex binding strips, Missy first tied each of my arms down the front supports of the horse. I relished both the visual scene and the feeling as I saw her wrapping the latex around my arms as if I were a mummy. The wrap was tight, but not uncomfortable. The strips stretched if I tried to wiggle, but they were surprisingly secure. Next, she moved on to my legs, bending each at the knee and tucking them next to the sides of the horse. She wrapped each leg, beginning at the ankle and moving up the calf and then around the thigh. This secured each limb to the rear supports of the horse. To make absolutely certain I was immobilized, Missy added a third wrapping around each knee which fastened them to the center crossmember. As she finished, I imagined I must look something like a strange motorcycle rider strapped into racing position.

"How do you feel, Scott?" Missy asked.

"Surprisingly comfortable, and very turned on, Mistress," I said.

"Yes, I can see that," Missy said while giving the head of my dick a quick squeeze. I reflexively let out a quiet moan. "Now that I have you in a compromising position, I'm going to give you a preview of my plans. I doubt Claire told you about my particular fetish and area of expertise. Has she mentioned it to you?"

"No, Mistress," I said.

"Good. Then my little ass-man, you are in for a treat. For a while now, I have made it my personal goal as a Dominant to perfect the technique of prostate massage. I'm going to brag and tell you I have become quite an expert. Have you ever been through a prostate massage before, lover boy?"

I hesitated before I spoke. "Uh, no, Mistress. I have not."

"Well then. This really will be special. It's been some time since I've had a prostate virgin." I felt a sudden pressure on my asshole as the sphincter was slowly forced to open. "There are many methods to a prostate massage, but I typically begin the old-fashioned way - using my fingers is as good a way as any to get a guy's rocks off. I simply locate your prostate gland with two fingers - like this...," I immediately felt a jolt zap my cock as Missy's fingers pressed solidly against my prostate. "... and then I repeatedly make little 'come hither' movements inside your ass, curling my fingers toward your belly button over and over...."

I could not fully process the feeling being caused by Missy's fingers up my ass, but it felt fucking incredible. "Holy shit!" I called out. I flexed my arms and legs against the latex bindings. Her movements instantly stopped, removing her fingers.

Missy walked to the front of the horse and knelt down. I saw her smiling, hooded, face appear in front of me. "So, you liked that, eh sugar?" she said. "Well let me share a bit more information with you. You see, I want something that other Dominants at this Gala may not want. And I want it a LOT. What I want - more than anything - is for you to win this damn competition. To be honest, it's not just because I like you - which I certainly do. More than that, I want you to win because I'd like to prove a little something to Claire. I intend to earn a few brownie points by helping her sub produce so much cum that the other competitors can't possibly to catch up. That will improve my standing among the Dominants, and it has the added benefit of allowing you to experience a massive amount of pleasure producing all that cum.

I felt myself swallow hard. "Thank you, Mistress?" There was more than a little hesitation in my voice, and I really didn't intend for it to sound like a question. Missy giggled and gave me a soft kiss on the cheek.

"So, Scott. While you are with me, our focus will be solely on cum production. The rules of the competition don't allow us to count the competitors' orgasms when they are in private play sessions. Those numbers would be too difficult to verify and too easy to manipulate. Instead, only the total amount of cum produced matters. The beauty of the prostate orgasm is that it does not necessarily require you to ejaculate, but when done properly, it can cause cum to continuously ooze from your dick. My goal is to use the various massage techniques I've developed and see what those balls of yours are truly capable of. I expect they are capable of amazing things. I want to see a lot of cum. And when I say a lot, I'm not messing around. I'm fully expecting you to fill THIS thing to the top!"

With more than a little drama, Missy sat a glass container down on the floor directly in front of my face. It had to be at least the size of a two-liter soda bottle. I was shocked. "Uh,... that might be a bit ambitious, Mistress, don't you think?"

"No, I certainly do not. You are underestimating both my skills and your potential, blue eyes." I heard her chuckling to herself as she stood to move again to the rear of the horse. "Now you know why I don't need your silly kit of condoms. And, that puny-sized cum container they gave you would never hold the harvest I intend to pull from those magic balls of yours. So... what do you say we get busy and fill this jar to its brim, shall we?"

Missy took hold of the head of my cock and positioned it just inside the mouth of the jar. The cold glass surface of the container against my cockhead made me flinch, but my cock was already so hot and hard, the jar warmed almost immediately. I felt the gentle probe of Missy's fingers re-enter my ass. She easily located the walnut-sized lump that was my prostate, and I felt her apply pressure. She began a back-and-forth massage, just as before, slowly stroking the gland. The effect on my dick was instantaneous.

"Oh, my god!" I said, almost involuntarily.

"I will not be surprised if you cum in no time at all here, sweetie," said Missy. "I know I've had you pretty wound up. Don't let it bother you though. You've been nearly ready to squirt ever since I got those shorts onto you. It's okay, tiger. Just go with it. Give me that cum. You know I want it. We both do. This jar is empty. Fill the damn thing up."

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