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MY SISSY CHASTITY LIFE by Throne (46 pages)
🕑 Added 2022-05-17 19:05:27 +0000 UTCMY SISSY CHASTITY LIFE by Throne
I couldn't believe Philomina had talked me into this. Not only had my zaftig blond girlfriend gotten me to use a depilatory to remove all my body hair, but then she convinced me that it would be erotic fun to lock my cock in a chastity cage. The device was as large as my penis is when it's flaccid but wouldn't let it grow beyond those dimensions. As soon as she had it on me, she got an unfamiliar glint in her eye.
"Let's test it," she said.
"Can't you just take it off me?"
"What fun would that be, silly? Let's make a game out of this. First, I'll find out how well it works."
"Well, okay, I guess. But then it comes off, Philly."
"Sure, Thomassa."
"Hey, my name is Thomas."
She put a finger to my lips. "That's not how the game is played. I'm now in control of your sex life, so you have to do whatever I say. And you can't object to anything I do, like calling you that instead of Tommy."
I stuck out my lower lip and must have looked sulky. Philly just laughed.
She said, "Time to make sure your pecker prison does the job."
We were standing there, facing each other. I was naked, which showed off my slender body, the absence of any hair below my eyebrows, and that damnable cage. My girlfriend was fully clothed. Her snug sleeveless top and tight slacks clung to her exaggerated curves. I wanted to touch her big breasts and overly full bottom but that apparently wasn't part of this strange game. She got her plump fingers on my nipples and began to tease them. I gasped and arched my back, pushing my smooth narrow chest toward her.
"Looks like somebody enjoys this," she said.
"I can't help it. That's very... stimulating."
"And it demonstrates how well your cock-lock works." She gripped my encased member. I could feel the warmth of her soft hand where my skin protruded between the bars. She tickled my scrotum. Her other hand continued to play with nipples. She had me panting and feeling weak in the knees. Giving a tug on the chastity, she led me down the hall. "I have a sudden urge to be in my bedroom."
"But... how can we... do anything... with me locked up like this?"
"Love will find a way, Thomassa," she assured me. "Like you can try that technique you've always refused to use. You know. The one you keep telling me is icky and unmanly."
"You know how I feel about that," I said, my voice breathy. "There's no way I would ever..."
That was as far as I got before she stopped, moved in, and got her mouth on my neck. Philly began to nibble and suck, while gently twisting one of my nipples. It nearly made me swoon. If I didn't get some release, I was afraid I would faint.
"Well," I conceded, "maybe I could just give you a quick kiss down there."
"Hmmm," she mused. "What did I do with that key? I sure hope I can remember where it is."
"What? You wouldn't leave me like this. Would you?"
"Maybe yes and maybe no, Mr. In-Danger. I think a few orgasms would jog my memory."
We were in the bedroom. She got out of her slacks but left on the top. There was no bra under it and her nipples were making twin bumps through the thin material. Philly lay back on the bed and lewdly spread her shapely legs. Even though I didn't want to, I got between her feet on my knees. As I lay down on my belly, I was extra aware of the hard metal chastity. My hands went to her chubby thighs. I wriggled forward, until my nose was only inches from her lightly furred mound, with her rippled pink nether lips right in front of my eyes. I inhaled the scent of her womanhood, the fishy odor making me wrinkle my nose. I thrust out my tongue and got my first taste. It really was like chicken. Feeling helpless in my naked state, with no body hair, and my pride and joy under lock and key, I began to lick in earnest. Philly sighed contentedly. Soon that changed to moans of pleasure. She got wetter and I had to slurp up the excess juices and swallow them. That led quickly to a shuddering climax, with her vocalizing more than she ever had when I was on top of her having penetrative sex. It took my girlfriend several minutes to resume breathing normally.
"That was delightful, Thomassa. "Like I had taken a lesbian lover."
"Hey, I'm a guy."
"You're a guy who owes me at least one more ride on his tongue, if he wants me to even think about freeing his pickle."
I didn't like her tone but by then felt even more vulnerable than before. I went back to using my mouth. She instructed me to get my lips on her clitoris and apply some suction. It took longer this time but, in the end, she had another satisfying finish. Philly made me stay down there and lavish kisses on her wet pussy while she relaxed. My cock was still straining to be free.
"Listen," I finally told her. "This has gone far enough. You can let me out of this awful thing right now."
"I might do that, if I had the key."
"Are you kidding?" Panic rose up inside me. "Where is it?"
"I was afraid you might have a bad attitude once we got started. So, I put it in the hands of someone we both know."
That puzzled me. Who could she mean? "One of your girlfriends?"
"She is now. We got to talking about you and found we both had the same issues, one of which has just been resolved."
"You don't mean... Jessica?"
"Bingo. You got it on the first guess."
"But she's still angry at me for how we broke up. The way I dumped her for you."
"She was mad at me, too," Philly said. "But after some heart-to-heart conversations, we're BFFs. I'm sure you could get the same results if you had a chat with her." She paused before adding, "Though she might want some of what I just got, to make up for how you wouldn't do it for her the entire time you were together."
"Do you expect me to go crawling back to her and offer to do... that?"
"Oh. I hadn't thought of the crawling part. That would be good. Especially since you were cheating on her with me. And lying to me at the same time, saying you weren't seeing her anymore, even though you were. Bad boy. Now you owe us both a lot of apologies, backed up by a lot of crawling and begging and licking. Especially licking. I didn't know how much I was missing." She fanned her hand in the air, over her vulva, as if she still needed cooling down in that area. "Now that I know, you can make up for lost time."
I was beaten and sounded like it when I asked, "How long is it going to take before I get unlocked?"
"That depends on how happy you make me. And Jessica." She chuckled. "Your EX might need to see you squirm a bit before she softens her stance. In fact, I wouldn't mind some squirming myself. But right now, let's get you wearing what Jessica and I agreed would be the perfect thing to remind you all the time that you're serving a sentence for lying and cheating. Can you guess what it is?"
She got up and stood by the bed, smiling down at me. In that moment, Philly was more desirable than ever. Her wide hips called to me but I couldn't answer. My balls throbbed.
I said, "I don't know."
She went to her dresser and took out a cellophane wrapped package. It held seven pairs of panties, in as many different pastel shades, each with a day of the week printed onto it. After tearing off the wrapper, she took out Wednesday's, which were pale yellow. They were made of some slippery material, as I found out when she handed them to me.
Philly suggested, "They'll feel wonderful against your hairless crotch. Try them on, Thomassa."
I was suddenly irate instead of intimidated. I sat up and scowled at her. She responded with an amused expression. That told me how ineffective my emotional state was. My shoulders sagged. I bent up one leg and fitted my foot through the panties, then did the same on the other side. As I worked the tiny garment up my legs, I learned she was right about how they would feel against my smooth skin. Once they were over my bottom and snugged up against the chastity, I was even more aware of it. She got on the bed again, pushed me onto my back, and straddled my hips. Philly brought her bare pubes down on my locked penis and did a sort of improvised lap dance. She reached down for more nipple play. In seconds she had me writhing under her and whimpering. I hated what she was doing but didn't want it to stop. The level of frustration she provoked was maddening. When she dismounted there was a wet stain on the front of my panties.
"There you go," she concluded with a smile. "I've left my scent on you. Now you'll not only look like a girl down there, but smell like one too." She giggled uncontrollably.
I had to keep the pants on. She made me sleep over with her, so that I could snuggled up against her from behind, my neglected cock, in its cell, against her big round bottom. She drifted off to sleep while I lay there trying to think my way out of that insane dilemma. There was some more teasing in the morning before she sent me home. I dressed for work but, as per her insistence, put on the Thursday panties. After my first few sips of coffee, I needed to empty my bladder. That was when I found that standing to pee was not an option. At work I had to use the lavatory booths and sit down to relieve myself. I also had to be cautious not to lower the panties far enough for anyone to see them under the stall door. They were a very light shade of red.
Back at her place, she informed me that the two of us would get together with Jessica on Friday night, at my EX's place. I was not looking forward to that.
Philly enthused, "I can't wait for her to see you in chastity and panties. Friday's color is pink. You'll look like a true sissy, instead of the male chauvinist pig you used to be."
"Now honey," I said, trying to sooth her. "You know I wasn't that bad."
"No? Did you brag to your buddies about how you were seeing both of us at the same time? Did one of them maybe blab to Jessica about it later?"
Oh no. I hung my head. "Sort of," I admitted.
She gave me a 'so there' look of triumph. "Which is why you're also going to wear a pretty pair of elastic-top stockings when we have our threesome with Jessica. I'm sure she'll appreciate that extra touch of submission on your part. And I found a pair that are pink, to go with your panties. This is going to be SO much fun. And it might give some closure to us girls."
"Yes, Philly," I agreed, more defeated than ever.
That led to trip to the bedroom, where I had to give her a trio of orgasms. Afterwards she put lotion on her fingertips before lazily tantalizing my nipples for a long while. My testicles ached. I would be glad when this was all behind me and my cock was free again. I was already thinking of the next girl I could make a move on.
Friday arrived. I was nervous all day at my job. The possibility of one of the guys getting a peek at my panties haunted me. I didn't dare to slip up in any way. If someone caught a flash of color through the crack between the stall's door and the frame, I would be doomed to secret whispers and endless rumors.
That evening, Philly had me strip down to get ready. She made me use more hair remover before I showered. When she got into the shower behind me, I remembered the times she had done that, pre-lockup. Her soapy hands roamed over my body, sending me into fits of urgent cravings. Afterwards, she supervised me putting my panties back on and rolling the stockings up my legs. It didn't help that she was still nude from the shower, her blond hair not yet blown dry, looking like a chubby Venus rising from the sea. I was allowed to put fresh street clothes on over my embarrassing lingerie and then we set off for Jessica's, with Philly driving and me on the passenger seat, hands folded politely on my lap, ankles crossed as if I was a modest girl, my pose courtesy of Philly's orders.
When we arrived, the girls exchanged warm hugs. It was agony to see them with their bodies pressed together. Jessica is full-figured like Philly, with an even more fully upholstered backside. Philly's blond locks created an appealing contrast to Jessica's raven tresses. They were both dressed to emphasize their outstanding contours. I had to strip down to my girly underthings for an extended examination. Philly explained how sensitive my chest was, and Jessica had to try it out for herself, which reduced me to a quivering mass of tingling erogenous zones. My EX was fascinated my how my cock bulged against its confinement and couldn't keep her hands off it. At last, I was made to stand in the corner while they sat on the sofa, where I could see them. The two exchanged grievances about me, which foreshadowed how bad my situation was.
At last Philly said, "If my calculations are correct, Thomassa owes you bigtime. You need something to pull your sex life out of the funk he put it into when he walked out on you. I recommend plenty of mouth-to-twat resuscitation."
"That sounds about right," Jessica said, eyeing me with bad intent. "I haven't gotten off since then. There's a guy who's interested in me, but we haven't hooked up yet. So, I'm in need of lots of tender loving tongue-care." She got behind me and gave my bottom a hard smack. "But maybe I should vent first. Let off some pressure. Philly, honey, would you go to the kitchen and get me the blue rubber spatula that's on the counter? I picked it especially for this occasion. It has a strip of metal inside that makes it particularly stiff."
Philly joked, "The spatula is stiff but Thomassa isn't. At least, not any more than that cage allows."
She went and fetched the kitchen utensil, soon to be repurposed as an instrument of discipline. I was made to bent over and grip the seat of a kitchen chair. My panties were pulled down and went as far as my calves. The girls ogled my rear end. Jessica poured them each a glass of sparkling wine. They clinked them together in a toast to me receiving my comeuppance, while I remained in my shameful and awkward pose. Then Jessica took up a position behind me. She slapped the spatula against the palm of her hand. Then she used it on my exposed rump. I yowled when it smacked me. Then I bit my lips, determined not to make any more noise. That lasted only until the second blow, which made me yelp and left me whimpering. She peppered my buns with over a dozen strokes, then took a break to sip her wine and share thoughts with Philly about how my bottom was coloring up.
"It makes me feel good to watch it go from pale to pink."
"You'll like it even more then you turn it bright red."
Jessica was happy to do exactly that, not hurrying, and making my suffering last a good long time. When she stopped, I was blazing back there and knew the pain wouldn't abate anytime soon. It would certainly be present while I was making the first installment on paying the debt of sexual service that I owed her. Like Philly had done, she undressed only from the waist down. Was denying me the sight of their magnificent busts part of their psychologically cruel revenge? She pinched my ear and walked me to her bedroom. The setting was familiar but the circumstances were much changed. She got in the middle of the mattress, with her legs accommodatingly wide. The dark triangle of her pubic bush was split by a deep groove, bordered with fleshy lips. I sniffled as I got into my increasingly familiar new position and laid on my tummy.
She said, "I hope you don't mind that I didn't wash up down there. I figured I shouldn't have to make any extra effort, after the way you treated me. Don't you agree?"
"Yes, Jessica," I said miserably. "I'm sorry that I..."
My EX ended my sentence by sitting up, grabbing the hair at the back of my head, and pulling my lower face against her unwashed pussy. She held on as she dropped back, assuring that I couldn't retreat. In that smothering hold I began to lick furiously, wanting to please her enough that she would allow me some reprieve. She ground her moist pubes against my nose and mouth, getting plenty of her secretions on me. After that she eased up only enough to allow me to snatch brief gulps of air when not gulping down the juices from her snatch. Jessica took much longer than I was used to with Philly, to reach her initial orgasm. When it came it was a bed-shaker and plenty sloppy. The second and third climaxes each took more time than their predecessors to achieve. When it was over, we were both spent, though in different ways and with all the satisfaction on her part and none on mine. My poor cock felt like it was being crushed in its inadequate containment. Thank goodness the cage wasn't any smaller. My nuggets seemed like my scrotum had been filled with gravel and they were being ground against each other. Why was I aroused by having to go downtown on a female who despised me? I guessed it was from being celibate as long as I had been. To add to my torment, she allowed me to stretch out on top of her, but told me to keep my face turned to the side, because I had 'pussy breath'.
Over the ensuing weeks the girls had fun sharing me. Sometimes they would lie side-by-side and make me switch back and forth between them, which led to prolonged sessions. To the panties and stockings, they added, when we were at one or the other of their places, some girly tops, usually close-fitting and with spaghetti straps. Those multiple indignities went on until they announced that I was at last due to be unlocked. My relief was indescribable, so I won't attempt to describe it. Let it suffice to say that I intended to never see either of them again, once I was cage-less.
The big night arrived. They said that they didn't want be getting rambunctious once I was freed, so they needed to cuff my ankles and wrists to a kitchen chair. I didn't like that but, between having my spirit broken over the weeks, and not wanting to give them any excuse to postpone the big event, I went along with it. Once I was helpless, they amused themselves by applying more hair remover to my Man Zone. It seemed unnecessary, since I was about to return to my old life, but I had no choice except to permit them to enjoy a final insult to my masculinity. Off came the cage and on went the depilatory. They let it do its work and then wiped it away, unavoidably leaving me aroused. I strained at my restraints, to no avail. Jessica went to her fridge, opened the freezer, and returned with a cold pack. She pressed it against my straining erection, causing it to shrivel down to almost nothing.
"Why are you doing that?" I demanded, some of my old bluster returning, with freedom so imminent.
"So we can get your new chastity on you."
"NO! You said I was done with that."
"We said you were done with your cage. We never told you we wouldn't be replacing it with a smaller one."
"Smaller? You can't do that!"
"Who's going to stop us, cheater boy? Hmmm? We've decided to continue with your sissy lessons, to protect the rest of the women of the world from your nasty habits."
"It's not fair," I protested loudly.
"What's not fair is how you treated us. Thomassa," said Philly, "you should be thanking us for helping you to reform."
"As part of that," Jessica went on, "we're going to switch to calling you Thomassina. It's more girly, to go with the expanded wardrobe we've been amassing for you."
"No, no, no," I said, on the verge of tears.
"Hush," Philly said as she stroked the side of my face. "Don't be such a fuss. The new chastity is still half as big as the old one."
"Half... as...?" I was in shock.
To prove the reality of their claim, they showed me what my suffering cock was about to be forced into. It was indeed 50% smaller than what I had just been liberated from, and similarly made of unyielding metal. Philly fitted the ring portion of it around the base of my male parts. Jessica got the honor of snugging the cage over my member, after giving it another thorough icing. The two parts were married together and the key that already waited in the attached barrel lock was turned. I shivered at the sound of it clicking shut. Jessica took it out into the hallway of her apartment building and returned in a few minutes, empty handed.
She said, "I gave it to a trusted neighbor, who will hold it until such time as it is needed... if ever."
They laughed and performed another of their tests to determine if the chastity was working. This time, with me stuck in the chair, they flaunted their bodies, ran their hands all over me, and ducked their heads down at the same time, to fasten their mouths onto my nipples. When they stepped away, I was a babbling wreck, my neglected balls feeling like they had been put into a vise.
After they released me from the chair, they decided that it was time for a fashion show, with me as the sole model, and selections from my expanded sissy collection as what was to be worn. I was still dazed from the shock of my exclusion from the penile early release program. They saw how distraught I was and thoughtfully made me a mixed drink. It was something orange, served in a snifter-type glass, and decorated with several slices of tropical fruit on a skewer and a colorful paper umbrella.
Jessica described it as, "A sissy drink for a sissy boy."
Philly advised, "Drink up, Thomassina. You'll need it for what's to come."
I took a swallow of the sweet drink. After two follow-up sips, I started to sense how potent it was. The girls went and grabbed what they had pre-selected for me to be decked out in. First there was a summery minidress, yellow and green and white, with patterned stockings and shiny shoes with buckles, which shared its colors. Once I was in everything, a woven straw hat was perched atop my head and its long ties were knotted under my chin. The two girls produced their phones and took pictures. I had to strike several retro poses. The whole charade was disturbing. I knew that, with my hair only to the tops of my ears, and no make-up on, I was plainly a boy in a dress. My image screamed 'sissy'. They coached me on how to move and sit and speak.
After I took that off, they showed me a pair of short-sleeve pajamas. They were made to look like a man's but cut to be worn by a woman. The result was weirdly gender-bending. They had me roll around on the bed, hug a pillow, and pretend to sleep. Then they had me bite the pillow, while acting like I was in pain, for a close-up. It didn't take much imagination to tell how that would come across if viewed by someone who hadn't been there.
Jessica said, "I think all these would be popular on some sissy webpage. Maybe we could find one where Thomassina would have her own section and be able to build up a following."
Philly offered, "Maybe watchers could send in suggestions for what else they'd like to see our cutie show herself off in."
The shift in pronouns was increasingly disturbing. It went on as they laid out my next selection. This one was a cheerleader uniform that they had picked up in a thrift shop.
"We got a good price," Philly assured me. "Didn't want it to be too much of a burden when you paid us back for all your stuff."
"But now that you're not dating," Jessica reminded me, "there's money that you're not spending to take us out. Or to just order pizza so we can stay home and get into bed sooner."
Her new best friend observed, "He did that to you, too?"
"For sure. Always tried to make it sound like a romantic evening in, with just the two of us. Now I know better about his intentions."
I didn't need them reminding each other of my past transgressions. The outfit didn't come with panties. When I tried to pantomime that something was missing, they acted like they didn't understand me. Using my newly softened voice, in its higher register, I told them what was lacking.
"Oh," Jessica said with a devilish smirk. "We thought it would be sexier if you were naked under your teeny skirt. When you do a cheer, you can show off your chastity."
"Noooo," I groaned, appalled at that idea.
Of course, the more I hated it, the further they wanted to take it. The two of them even came up with a cheer for me to do, so they could make a video. I had to bounce around like a loony and flip up my skirt in front, then turn around and bend forward while pulling it up in back, to freeze and let that shameful view linger. This was my cheer --
"Ricker-racker, firecracker, sis-boom-bah. Sissy boy, sissy boy, rah, rah, rah."
They forced me to practice it several times over, until they could control their hilarity enough to record it. Then I had to repeat it three more times, which they said was to assure quality control. That didn't make sense to me, but what choice did I have?
The outfits had been getting skimpier each time. Now came the most revealing of all. It was a harem girl costume, of see-through material, complete with a headpiece and veil. Once I was in it, I was covered and exposed simultaneously. As they aimed their phones in my direction I wanted to slink away and go hide. Instead, I had to do my clumsy version of a harem slave's movements, including some sinuous dancing.
How much worse could this get? My answer came in the form of the final get-up. It was a fishnet body stocking with wide mesh, no panties, and a pair of cat ears attached to a hair band. Philly drew long whiskers on my face and I was ready for one more humiliating round of photos and a brief video. They directed me to move like a cat, lick my 'paws', and stretch languorously. During the video I purred and then meowed loudly.
After they were done, I got bare-assed again. The girls were all warmed up from how they had disgraced me and captured the images. That meant a trip to the bedroom and three-on-a-bed. I had to get on my knees and kiss each girl's bare butt cheeks while I thanked them for the pretty fashions -- which I would be reimbursing them for -- and the album they had created of my androgynous persona. They made the decision to definitely post the majority of it online. In bed, I was told to take my time, with lots of pussy kissing and murmured words of romance.
"Make my kitty believe you love her, Thomassina."
"Give my nummy butterfly-kisses, along with lots of endearing words."
In the end they both enjoyed multiple orgasms, while I continued to be an involuntary celibate. Lying there, afterwards, they decided that I had been convincing enough that they could take me out soon for some shopping.
"I'm sure you'll attract some male attention."
"It'll be a good area for a pick-up."
"Not that we'll let you be picked up."
"Unless you want to be."
"Maybe if you met the right guy, it would give you a whole new outlook."
"Might shut your mouth and open your eyes."
"His mouth would be open, but he wouldn't be able to talk. Thomassina would be too busy making a new friend."
"It would be a deep friendship. All the way up to the guy's balls."
They doubled up with laughter at the mental images that summoned. It was suggested that I could also use my webpage to attract dates. I believed they were only saying those things to torment me, but I couldn't be certain.
On Saturday afternoon, they got me dressed for my first public appearance. The weather was pleasant so they settled on a frilly bare-midriff top with a padded bra underneath, and a micro-miniskirt, combined with thong panties. Cork-soled sandals with laces up to my knees completed what I was to be shown off in. They dressed more conservatively, so I resembled the younger sister with an impaired fashion sense. They teased up my hair and used some product to keep it full. Then there were just enough cosmetics to blur the dividing line between sissy and real girl, including blush, mascara to thicken my lashes, and my first ever application of lipstick, in a shade called Magenta Madness. A few puffs of cheap flowery perfume completed my makeover as Thomassina.
They drove me to a downtown shopping district, with them in the front seat and me stuck behind them. We parked on a side street and strolled one block to the stores. It was a funky section, with boutiques, cafes, a bookstore, and a place that specialized in exotic imports of jewelry and fashions and carved figures and such, along with several street vendors. I was totally self-conscious as I trailed after the girls. In my mind, everyone was staring at me. In reality, I was passing well enough that only some shoppers in the know seemed to see through my disguise. A few guys gave me interested looks, though I wasn't entirely sure if they were directed at the sissy I had become or the girl I resembled. We entered one boutique, where my companions held up several tops against my bra-enhanced torso to see if they flattered me. Every time my face got warm, I knew I was blushing. They selected a sparkly vest and paid for it with my charge card, with the first name Thomas on it, which the clerk accepted without question. I was horrified that she might want to identify the cardholder and I would be outed right there in front of a store full of customers.
Next, after ambling to the end of three city blocks, where the small businesses were replaced by showrooms for office equipment and so on, we started back the way we had come, but on the opposite side of the street. Stopping at a sidewalk cafe, the girls ordered fancy coffees and got me a bubbly water with a straw in it, as if I was kid who wasn't allowed grown-up beverages. I sullenly put the straw between my colored lips and tried not to think about being IDed as a sissy. Our last stop was at the sidewalk serving-window of a bakery, where my handlers bought several delicious smelling baked goods that I strongly suspected would not end up anywhere near my tastebuds. It was a relief to return to the car and be driven home. Our afternoon walk hadn't been long but I was left wrung out from stress, as if I had been on a forced march. Back at Philly's, I had to get naked an put on the vest, minus my bra, for more pictures, ones that made it plain that I was a guy with mascara and lipstick on, playing at being a female. The new images would join the others of my epicene self, on a website that Philly had located and of which Jessica approved. They worked well together.
The next time they said my chastity was to be removed, I didn't get my hopes up. It was like before, except that this time they tied my wrists and ankles to the head and footboards of a bed. The bed in my apartment was the only available one with the required design. It was surreal to be in my own place, where I was still allowed to retreat most weeknights so I could get to work in the mornings, but now with my frequent companions present. They boxed up some of my male clothes that they deemed to be too butch for me, so we could go to one of the thrift shops, where I would dump them into the collection box.
"No more worn jeans."
"And these two flannel shirts? I don't think so."
Once I was immobilized on my own bed, they entertained themselves with more of the teasing they loved so much to inflict. Then came the removal of my chastity and icing of my genitals. I didn't have a freezer pack, so they used a bag of frozen corn. It worked well because its loose contents made it easy to mold to the contours of my three-piece set. After my junk had been reduced to its smallest possible size, they fitted a ring around the base. Then came the rest of the device. I was astonished to see how small it was. There was only a disc, which they showed me would reduce my penis dimensions to nearly nothing.
"Size Zero," Philly said with a chuckle.
"The dick that isn't there," Jessica contributed.
"You can't," I whined, speaking in my high breathy Thomassina voice.
"Yes, we can, Trish," Philly said with confidence.
"And we will," Jessica promised.
"But first," my more recent girlfriend declared, curling her fingers and bringing her hand up to her mouth, "a farewell to your prick."
She pretended to lay 'Taps', imitating a mournful trumpet with her voice. My earlier girlfriend bowed her head out of respect for my soon-to-be-gone penis. Then they worked together to get my tool compressed to miniature size and less, before they pushed the disc down on it and attached that to the base, so the fiendish contraption could be locked. A small key did the job and then went onto a chain that Jessica ceremoniously placed around Philly's neck. After that they cracked up laughing. Then one of them got on either side of me for the most trying tease session of all, its effects amplified by how smooshed my dick was. All I could do was lie there, my libido stuck on its highest setting, almost drooling with need. Something inside me had just changed drastically.
"Aw, poor Trish." Apparently, my name had been changed again. There was a new one for each chastity. "Do you want some sex?"
I began to salivate. "Yes," I said in a strained whisper. "Please." I sounded completely like a simpering Trish. "Let me eat your pussies."
"Is that what sex means to you? No more screwing? No cheating on your lovely girlfriends?"
"Yes." It was true. I had lost touch with my former macho identity, to the degree that my only conception of bedroom action was for me to pleasure my two ladies with my lips and tongue, plus occasional digital gratification. And my sole vision of sex for me was relentless teasing with no payoffs. "Can we go to the bedroom?"
"How about if we start in the kitchen? With us out of our slacks and panties, sitting at the table, our bottoms pushed forward on the chairs and our knees wide apart? That way, you can kneel on the linoleum floor and lap us each to a sweet orgasm."
"Yes." I sounded so wispy. "Thank you. Anything you say. Just please don't stop letting me serve you."
Over the following weeks, my body hair stopped trying to grow back. I wasn't sure why and didn't bother attempting to figure it out. At work I occasionally slipped into my Trish voice and had to cough and consciously lower it. Suspicious glances became common. I began to doubt what was left of my masculinity, which wasn't much anyway. The girls had done an expert job of turning me into a sissy. I was always aware of the feminine items under my male attire at the office. I never stopped thinking about the impossibly restrictive chastity that now neutralized my dick. I wondered if I would become impotent, if I wasn't already. What a nightmare it was every time I got horny in the presence of my two zaftig owners, which is how I now thought of them, and was unable to achieve even a fraction of an erection, as had been possible with the first two chastity devices.
I had to clean both of their apartments, either in the nude or wearing only a tiny black apron with white lace trim. I hand-laundered all their delicate intimates, stealing sniffs of their panties before putting them into the soapy water. They caught me at my naughty olfactory ritual and decided that I should pre-wash the gussets of their panties by sucking on them. Instead of being insulted, I was grateful. It went on like that for several months, my days filled with guilt and my nights with indignities large and small. I could see no end in sight, so it was startling when Philly and Jessica took me aside and said that my day of freedom was at hand.
"That same neighbor who held your last key has the new one."
"All you have to do is go to their apartment and convince them to give it to you."
"That's all?" I marveled.
"Easy-peasy."
"Lemon-squeezy."
In a daze, also in a quilted bed jacket with nothing under it, I ventured down the hall to the designated apartment, to meet my keyholder. I envisioned myself confronting another woman, having to get my face between her legs, but ultimately winning her over and earning my release. I stopped at the door, took a deep breath, and tugged down on the bottom of my single garment with one hand. With the other hand I knocked. The door opened.
Standing there, glowering down at me, was a tall man with broad shoulders and rugged features. He had a heavy beard shadow on his square jaw and a thick mustache under his wide nose. An open leather vest revealed a hairy muscular chest. His matching leather pants featured an enviably large bulge at their crotch. The pantlegs fitted neatly into scuffed motorcycle boots.
Having rehearsed my first line, I said by rote, "I'm Trish from up the hall. Jessica and Philly's friend. I believe you have my key."
In my distracted state I had let the jacket fall open. The big man leered at my hairless chest and the device that disabled my dick. He laughed soundlessly.
"Yeah. Trish. They said you were coming. Get inside. I'm Jake." He patted his groin. "Jake the Snake. Glad to finally meet you, Trish the Swish. I'm sure we'll be damned close, especially after you leave your old place and get moved in here. Did they tell you we were going to be roommates?"
"Uh... no," was all I could manage to utter.
"Well, we are." His wide hand went to my shoulder and gave it a hard squeeze. He pulled me toward him and closed the door, which he then locked.
"I want to get you used to your new duties. Like for instance, these boots need a good polishing. You'll do that while I'm wearing them. Right?"
"Yes, Sir." I addressed him that way without thinking.
"The girls told me you like to pretend you're straight and don't want to be a sissy. I can plug into that fantasy really easy. I'm a Master and have been waiting for a while to get a soft boy like you, for a long-term live-in arrangement." He broke that last word into three distinct syllables, suggesting that he had a lot of thoughts about what it would include. "But before anything else, let's find out if that mouth is as soft as the rest of you." He cupped my chin in his rough hand. "Like right now."
Jake undid his leather pants and showed me how he had earned his nickname, which could also have been Jake the Anaconda. Oh my. He pressed down on both my shoulders and I sank to my knees. Suddenly, the manipulations of Philly and Jessica didn't seem so bad. He slapped me on both sides of my face with his long girthy organ.
"I'm straight," I said in a weak voice. "I don't want to do what you're expecting."
He peered down at me, gave a broad wink, and nodded. "I'm into your kink, Trish, but first things first. I need to get my oil drained pronto, if you know what I mean. We can start on the bondage and butt plugs later."
I touched his massive manhood with one trembling hand. I grew impressively. And grew. And grew some more. It smelled like sweat and secretions.
"Now do a good job, pansy. Otherwise, I'll have to spank your pretty ass real hard." He shrugged. "But I'll be doing that anyway. We both know you want it. I mean," he corrected with a chortle, "you'll hate every minute of sucking my tool and being put over my knee." In a stage whisper he added, "I'll make sure you get as much of all that as you can stand, and then some more. But we'll pretend like you don't want me to do it." Assuming a harsh tone, he said, "Now get your mouth all over my rod, you sniveling sissy, and start getting used to your new life."
What else could I do? I obeyed. There would be a lot more of that to come, every night and during the days on weekends too.
