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Holiday Humiliation
Warning: Contains some forced same sex sexual acts.
I'm 30 and my girlfriend, Jules, is 29. We've been living together for about a year and decided to treat ourselves to a five-night spring cruise, thanks to the days off we'd both accumulated from work. We both work in the same office.
It still amazed me how I managed to get Jules. It's like I won the lottery. In my mind, she is way above my pay grade, so to speak. We were also so different. Admittedly, I'm a left-leaning person, and she is definitely right-leaning. She's not a churchgoer but definitely a Christian with all the right-leaning baggage that comes with it, in my opinion. We never talk religion or politics. I just tend to nod in agreement with her strong views when the topics come up.
I tend to be a homebody, whereas she gets up and goes to the gym daily. Most days, she has worked out and is the first to the office, while I laze in just on time. She has the physique of a bodybuilder, hard and tanned. For work, it's high heels and trim-fitting pantsuits. Occasionally, she'll wear a dress. After work, it's the polar opposite: tracksuits, ball caps, and athletic shoes.
I'm a far better cook, so she disappears before dinner, normally for a run, while I cook. Actually, I do most of the cleaning, laundry, and household duties as well, which seem to suit her fine.
In the bedroom, she is in charge, always directing me for her satisfaction. Don't get me wrong. I'm fine with all of this, and it's natural to me to follow along.
I had packed and prepared for the trip. I also had to work late the day we were set to leave. Jules offered to go home, gather our bags, and pack herself something she left to the last minute. The plan was for her to pick me up from work in a taxi to get to the airport, then to the cruise ship.
All went as planned. We boarded the ship in the evening, dropped our bags in our room, and immediately went to dinner in one of the ship's restaurants. Completely beat from the day's travel, we made it back to our stateroom. It looked just like it did in the pictures I'd seen, but instead of a queen bed, there were two doubles. Thinking, "Oh well," we both crashed.
I awoke in the morning to find Jules had already gotten up and left. That's when I noticed a large paper gift bag on the bed with a note: "Put these on and meet me at the gym. Jules."
Looking in the bag, I was shocked. I didn't know what to do. The outfit was a white shirt with nautical red and navy trim, navy women's shorts, white women's panties, socks, and a pair of women's navy Keds sneakers.
Panicking, I searched for my bags for clothes. Apparently, Jules had disposed of the clothes I travelled in and repacked my bag with women's tops, shorts, tights, socks, underwear, and another pair of Keds, bright red.
I was horrified. She knew my secret, my most carefully guarded secret, something that I'd hidden all my life from everyone.
What the fuck, I thought. I had no choice but to put on the outfit. Feeling humiliated and embarrassed as I slipped into the silky panties, everything fit perfectly. I laced up the Keds, which kicked in my arousal. I got hard as a rock. I hesitated and waited for my erection to subside. I couldn't go out dressed like this, but I had no choice. Summoning all my courage, I checked the ship's guide map for the route to the gym.
I hesitated at the gym door but entered. Inside, several men and women were working out. Jules was near the front on a rowing machine, her blond hair tied back in a ponytail, looking stunning in a black workout top, matching black tights, and white Keds. I had never seen her wear Keds before. This was a feminine departure from her normal style. She had always worn ugly dad-style sneakers.
"There you are!" Jules called out loudly as I entered, drawing everyone's attention. As people looked me up and down, I could see their quiet amusement. I was thoroughly embarrassed and humiliated. I heard a couple of men talking and laughing, adding to my humiliation.
Jules got up from her machine and approached me. "Let's go. I need a shower." I followed her back to the room, trying to ask what was going on, but she just shushed me. We entered the room, and she motioned for me to sit while she went into the shower. The minutes waiting seemed like hours. She finally finished and returned, silencing me with a finger before I could speak.
"I found your perve collection last week," she said firmly, her voice dripping with contempt. I instantly knew what she meant. I had collected a couple thousand porn pictures of women and men wearing similar outfits and sneakers in various sexual acts. I also had panties and a pair of ladies' Keds that I used to masturbate. I dropped my head, ashamed and embarrassed.
She sneered at me, her eyes narrowing in disgust. "You perverted little freak. All this time, you've been jerking off to pictures of sissies in girly clothes and sneakers? Hiding it from me like some disgusting secret? Well, guess what. It is disgusting. You want to wear women's panties and sneakers? Fine. For this entire vacation, you'll be my sissy bitch! You'll wear all those pathetic women's clothes and sneakers I've packed for you, and you won't argue or make a fuss. This is your punishment for every lie you've told by omission. I'm going to make sure you feel every bit of the shame you deserve."
"So, what is it specifically that gets you off on this stuff? The clothes? The sneakers? Are you gay? Do you like to get fucked in the ass, or are you just a fag cross-dressing cock sucker?" she asked, her tone mocking and accusatory. She's known I'd experimented with a guy in college. I had let that slip one evening after too much alcohol.
"All of it... mostly the sneakers. It gets me off," I whispered.
"I thought so," she said with a cruel smirk. "If you haven't seen, there's another pair for you in your bag. I'll be wearing Keds as well, so everyone knows they're women's sneakers. We'll match like a pair of girlfriends, won't we? How fitting for a sissy like you."
At this point, it was clear that Jules was in charge and had no intention of us having a typical couple's vacation. Her contempt for my fetish was obvious. She was determined to humiliate me the entire time, using my secret desires as a weapon against me. I had no outs. She had planned this meticulously. She found my cache last week giving her ample time to buy all this stuff.
She got dressed, laced on her Keds, ignoring me completely, and left. She came back late afternoon, still ignoring me, changed into a short tight navy dress, still in the white Keds. "Come on, it's dinner time." We entered the restaurant, where she took her time, ensuring people noticed her and, consequently, me in my feminine outfit.
I ate silently, as did she. After dinner, she commanded, "Go back to the room. I don't want to see you." I did as ordered, spending the evening reading until I finally fell asleep.
It must have been around 10 when I was awoken by a noise at the door. It was Jules and a man. They were kissing and talking dirty when the man noticed me in bed.
"What's the deal looking at me?" he asked Jules.
"Oh, just ignore him. He's my sissy bitch," Jules replied nonchalantly, her voice laced with disdain as she glanced at me like I was nothing more than an annoying piece of furniture.
They flopped onto the other bed, kissing and making out in front of me. "Oh Carl, you're so fucking hard and big," she said as she stroked him over his pants. She stood, slipped off her dress and underwear, then pulled Carl's pants down, revealing his huge, thick cock, already hard and veined, standing out imposingly with a slight upward curve, the bulbous head flushed purple and glistening with a thin sheen of precum. She eagerly began to stroke it, her fingers wrapping around its girth (easily eight inches long and almost as thick as her wrist), sliding up and down the shaft with deliberate slowness, the veins pulsing under her touch as she twisted her hand at the base, making him groan with deep, throaty pleasure. He sat on the edge of the bed, and Jules knelt down naked except for the white Keds, taking the swollen head of his cock into her mouth. Her lips stretched wide around it as she sucked hungrily, her tongue swirling over the sensitive underside while her hand pumped the base, wet slurping sounds filling the room. She bobbed her head deeper, taking more of his length until it hit the back of her throat, gagging slightly but pushing on with enthusiasm, her saliva dripping down his balls, which tightened and drew up against his body as his arousal built, his musky scent mixing with her eager breaths.
Watching from my bed, I felt a mix of humiliation and arousal, my own cock now hard and twitching uselessly under the sheets. Jules performed with a skill and passion she'd never shown me.
After a couple minutes, Jules pulled back, her lips glistening, and laid on the bed, spreading her legs wide to reveal her shaved pussy, already swollen and slick with arousal, her inner folds pink and parted invitingly, a faint sheen of moisture coating her smooth skin. Carl positioned himself between her thighs and slowly pushed his large cock inside her, inch by inch, stretching her tight entrance until he was buried to the hilt, her wetness gripping him tightly as she gasped in delight. She moaned loudly, her eyes locking onto mine with a triumphant, vengeful smirk, knowing I was watching. He began thrusting deeply, his hips slamming against hers, making the bed creak rhythmically as his cock plunged in and out, her slick heat pulling at him with each withdrawal, the juicy sounds of their bodies mixing with her breathy cries.
Jules wrapped her legs around him, pulling him deeper, her tanned calves flexing as her white Keds bounced in the air with every powerful stroke. She arched her back, her breasts heaving, and urged him on with dirty encouragement: "Fuck me harder, yeah, just like that, show my pathetic sissy what a real man is."
They engaged in a lengthy, enthusiastic fuck, switching to doggy style, where he pounded her from behind, his hands gripping her hips as his cock slammed into her repeatedly, her moans turning into cries of ecstasy while waves of orgasm washed over her. Her body shuddered, her inner muscles squeezing him tight in hot, pulsing waves. Finally, he pulled out, stroking himself until he erupted, shooting thick streams of hot cum across her pussy, ass, and back, ropes of semen splattering her skin in white, viscous trails that cooled and thickened quickly. Jules laughed breathlessly.
When they were done, Jules laughed again, thanked Carl dismissively, and he left without a backward glance. She didn't even acknowledge me. She slipped the sneakers off and pulled the sheets over herself, the room reeking of sweat, sex, and his cum still smeared on her skin. I lay there, the mix of emotions swirling inside me: jealousy, utter humiliation, and an undeniable feeling of complete submission and exposure as she drifted off to sleep, leaving me to stew in her disgust.
Jules kicked my bed. I looked up, I was exhausted from barely sleeping. Her hair was wet from the shower. "We're going to the gym, hurry up," Jules declared without a hint of remorse or concern for my feelings, her voice sharp and dismissive. She opened my bag and tossed me a pair of black tights, white panties, and a white T-shirt, then asked with a smirk, "Are you going to wear the red ones today?" I shook my head no, too ashamed to speak. "You will before this cruise ends," she assured me with a knowing look, her eyes gleaming with malicious satisfaction at my discomfort.
She dressed in front of me, not caring that I saw her naked, as though my presence was utterly irrelevant. I couldn't help but admire her thin, well-muscled body and pert, firm breasts as she slipped into her fresh workout outfit: a tight black tank top and matching leggings that hugged her curves perfectly. She laced up her white Keds with a casual flick, ignoring me completely. I dressed in silence, the women's tights clinging to me, the oversized T-shirt barely long enough to cover my groin, and finally the Keds. We headed to the gym.
At the gym, Jules completely ignored me, engaging in lively conversation and laughter with others as she worked out, her ponytail bouncing with each energetic move. She flirted openly with a couple of guys, her laughter ringing out like she was having the time of her life, while I awkwardly used a few machines, feeling out of place and painfully aware of my getup. My cheeks burned as people glanced my way, their smirks and whispers amplifying my shame. When she finished, she left without a word or even a backward glance, leaving me to trail after her like a lost puppy back to our room.
Dinner that evening was tortuously quiet. We ate and headed back to the room. She said nothing and read on her phone for a while, then went to sleep. I had another restless night, thinking I couldn't wait for all this to be over.
Breakfast with more silent treatment and then the gym.
That afternoon, we went to the ship's pool deck. Jules lounged in a skimpy bikini and her white Keds, drawing admiring stares from a group of fit, young, tanned men. She flirted shamelessly, laughing at their jokes and touching their arms, her voice loud enough for me to hear from my spot a few chairs away, where I sat awkwardly. The only saving grace was that I was able to take off the Keds and be barefoot for a while.
"Oh, ignore my little sissy over there," she said dismissively when one guy glanced my way, her tone dripping with scorn. "He's just here to carry my towel." The men chuckled, and she leaned in closer to one, whispering something that made him grin.
That same guy was getting really friendly, and Jules was lapping it up. She asked him to apply sunscreen. His hands took liberal feels as he slowly applied the cream. A couple of drinks later, he lay next to her, and they started to kiss. Jules looked at me, smirked, and pulled a towel over their waists. I could see the towel bobbing up and down between them. She was giving the guy a handjob. It went unnoticed by others around the pool except for me. The humiliation burned.
After a particularly silent and tense dinner where she flirted outrageously with the waiter, calling me "her sissy" to his amusement, she didn't return at all. I lay awake in the stateroom, jealousy gnawing at me, until she stumbled in the next morning just before dawn. She reeked of sweat, cologne, and sex, her dress disheveled with dried cum stains splattered across the fabric, stark white against the navy material. "Had a real night out with a real man," she said with a cruel yawn, not even looking at me as she peeled off the dress and collapsed into bed. "Better than wasting time with a pervert like you." The scent lingered in the room, a constant reminder of her disregard, leaving me humiliated.
She slept most of the day. I had gone and ate lunch and dinner by myself. It was kind of refreshing not to be scorned. To my relief, she didn't bring any more men to our room that night.
Our last full day was a repeat of the gym, pool, and dinner. The only thing that changed for me was having to pick another humiliating outfit from my bag. The red Keds loomed large in the bottom of the bag.
That night we ate, and I returned to the room after being dismissed. She returned to the room a few hours later with not one, but two men: the same large guy, Carl, from before, and a smaller, younger man who looked about twenty.
"There he is," Carl announced with a booming laugh, pointing at me as I sat up in bed, confused and anxious, my heart pounding. Jules fixed me with a cold, contemptuous gaze, her lips curling in disgust. "This is Herman, Carl's stepson. He's gay and has never been with a man. I told them my little sissy bitch would be happy to oblige with a blowjob." I started to shake my head in protest, horror rising in my throat, but she cut me off sharply, her voice laced with venom. "Yes, you will. I know you love to suck cock or would you prefer to be fucked in the ass. Now get dressed in your girly costume and those pathetic Keds. We want to watch you suck his cock like the perverted freak you are."
Trembling with a mix of dread, I picked up the clothes I had worn during the day and went into the bathroom. I slipped into the silky panties, feeling them hug my skin snugly, then pulled on the tights and T-shirt, finally lacing up the navy Keds. My cock hardened instantly, tenting the front of the tights embarrassingly, betraying my excitement amid the humiliation. Great, now everyone would see just how much this was turning me on, like the pathetic sissy she kept calling me.
When I emerged, Jules sneered at me, her eyes raking over my outfit with open revulsion. "Look at you, all dolled up in your girly sneakers, hard as a rock already. Pathetic." She turned to Herman and commanded, "Pull down your pants." Unlike Carl's imposing size, Herman was awkward, thin, and a rather homely guy. He pulled down his pants and shorts, exposing his uncut penis. It was quite thin, his erection modest but throbbing eagerly. I suppose the thought of getting his cock sucked had gotten him ready. The smooth shaft was about four inches long with a slight upward curve, the foreskin partially retracted to reveal a glistening pink head with a bead of precum at the tip, his small scrotum hanging loosely below. He sat on the edge of the bed, looking nervous but excited, his slim legs spread awkwardly.
On Jules' sharp command, "Get on your knees, sissy, and show us what you're good for," I dropped to the floor between Herman's thighs, the carpet rough against my knees. Remembering my past experiences from college, I leaned in, wrapping my lips around the warm, velvety head of his cock. The taste was salty and musky, a mix of skin and arousal that filled my mouth as I slid my tongue along the underside, tracing the sensitive spot where the head met the shaft and gently pushing back the foreskin to expose more of the smooth tip. I took more of him in, my lips tightening around the thin shaft, bobbing my head slowly at first, then picking up pace as I sucked with deliberate pulls, hollowing my cheeks to create suction. Herman groaned softly, his hands fidgeting at his sides, clearly overwhelmed by his first time. His breathing quickened, and his thighs trembled slightly as heat built in his groin, making his cock twitch in my mouth with eager throbs.
Jules and Carl began their own act of passion on the other bed, completely disregarding me like I was invisible. Carl's large frame loomed over Jules as he stripped her, then himself naked, his thick cock veined prominently, springing free and hard, the shaft rigid with prominent ridges and a flared head already leaking precum. She moaned loudly as he slowly entered her slick pussy, engulfing him. The wet sounds of their bodies slapping together echoed through the room, her wetness coating his length as he thrust deep and hard. Jules locked eyes with me briefly, her expression one of triumphant scorn, before turning back to Carl with a passionate kiss, her hands clawing at his back as he pounded into her relentlessly. "Fuck me harder, Carl. Make me forget all about that worthless sissy over there," she gasped, her words cutting like knives, emphasizing how little our relationship meant to her now.
I focused on Herman to drown out the humiliation, using my finger to press firmly on his taint, rubbing in small circles to heighten his pleasure and hasten his climax by building that deep, tingling pressure. His small body tensed, his balls drawing up tight against his body as he bucked his hips slightly. He tensed, shuddering with a whimper, his cock pulsing four or five times as spurts of hot cum shot into the back of my throat. I swallowed the thick, slightly bitter fluid reflexively. His shaft softened gradually in my mouth, the warmth fading as his shaky breaths filled the air. The act made me feel even more degraded, like a tool for their entertainment. Jules laughed derisively from the other bed mid-moan, knowing Herman had just blown his load in my mouth.
Herman, inexperienced but eager, wanted to return the favor. Jules nodded dismissively, still riding Carl's cock with abandon, her breasts bouncing as she ground down on him, her body rubbing against him in sweaty, heated rhythm. "Go ahead, let the sissy get off. It's the least he deserves for being such a good little whore." Herman pushed me back onto the bed and fumbled, pulling down the tights to free my aching erection, throbbing desperately after days of buildup, about six inches long with a pronounced vein along the top and a flushed, sensitive head. His technique was sloppy and awkward, his mouth too tentative at first, teeth grazing my shaft lightly as he tried to mimic what I'd done, his tongue lapping unevenly at the head and occasionally bumping the sensitive underside. But the pent-up tension from the cruise's constant teasing overwhelmed me. I tensed up, my balls tightening as waves of pleasure built, my body contracting in hot bursts, and I came hard into his mouth, groaning despite myself as my cock spasmed, shooting warm jets of cum he struggled to swallow, some dribbling down his chin in sticky trails.
Herman slept in my bed and Carl with Jules the remainder of the night. What must have been a couple hours later, I awoke with Herman rubbing his penis between my ass cheeks trying to get in my ass. I pushed him away, but he persisted. He was horny again and wanted more. There was no way he was going to fuck me in the ass, but I didn’t want Jules or Carl waking with all the fussing he was making. I rolled over and stroked his cock. It wasn’t long before he was dripping precum. I used my thumb in a circular motion, concentrating on his penis head. It was getting nice and slippery, and it was an easy job getting him to cum. Most of the cum was in my hand, which I wiped on the sheets, and I quickly fell back to sleep.
In the morning, the room's air was thick with the scent of sex and sweat. Carl and Herman left, with Herman mumbling a shy thanks that I was too humiliated to respond to, my face burning as Jules watched with a smug grin.
Finally, we were going home. We showered. Jules looked at me with final, contemptuous authority and simply said, "Red." My only clean clothes left were light gray tights, white ankle socks, a plain white T-shirt, and the bright red Keds, which screamed femininity from a mile away. The journey home was a blur of self-consciousness, every glance from strangers feeling like it was aimed at me, the red Keds broadcasting my feminized state like a neon sign of shame.
Back in our apartment, I closed the door behind us, and Jules immediately announced, her voice cold and unyielding, "You'll be moving into the guest bedroom. If you want to stay here, you'll please me however I want, and you'll wear nothing but women's clothes and your Keds sneakers while at home. Got it, sissy?" With finality, she removed her own Keds, popped them into the trash, and declared, "I'll never wear Keds again."
This new arrangement was the culmination of the power shift that had occurred over the cruise, our relationship now defined by my total submission and her absolute dominance, the Keds a constant symbol of my degraded reality.
Warning: Contains some forced same sex sexual acts.
I'm 30 and my girlfriend, Jules, is 29. We've been living together for about a year and decided to treat ourselves to a five-night spring cruise, thanks to the days off we'd both accumulated from work. We both work in the same office.
It still amazed me how I managed to get Jules. It's like I won the lottery. In my mind, she is way above my pay grade, so to speak. We were also so different. Admittedly, I'm a left-leaning person, and she is definitely right-leaning. She's not a churchgoer but definitely a Christian with all the right-leaning baggage that comes with it, in my opinion. We never talk religion or politics. I just tend to nod in agreement with her strong views when the topics come up.
I tend to be a homebody, whereas she gets up and goes to the gym daily. Most days, she has worked out and is the first to the office, while I laze in just on time. She has the physique of a bodybuilder, hard and tanned. For work, it's high heels and trim-fitting pantsuits. Occasionally, she'll wear a dress. After work, it's the polar opposite: tracksuits, ball caps, and athletic shoes.
I'm a far better cook, so she disappears before dinner, normally for a run, while I cook. Actually, I do most of the cleaning, laundry, and household duties as well, which seem to suit her fine.
In the bedroom, she is in charge, always directing me for her satisfaction. Don't get me wrong. I'm fine with all of this, and it's natural to me to follow along.
I had packed and prepared for the trip. I also had to work late the day we were set to leave. Jules offered to go home, gather our bags, and pack herself something she left to the last minute. The plan was for her to pick me up from work in a taxi to get to the airport, then to the cruise ship.
All went as planned. We boarded the ship in the evening, dropped our bags in our room, and immediately went to dinner in one of the ship's restaurants. Completely beat from the day's travel, we made it back to our stateroom. It looked just like it did in the pictures I'd seen, but instead of a queen bed, there were two doubles. Thinking, "Oh well," we both crashed.
I awoke in the morning to find Jules had already gotten up and left. That's when I noticed a large paper gift bag on the bed with a note: "Put these on and meet me at the gym. Jules."
Looking in the bag, I was shocked. I didn't know what to do. The outfit was a white shirt with nautical red and navy trim, navy women's shorts, white women's panties, socks, and a pair of women's navy Keds sneakers.
Panicking, I searched for my bags for clothes. Apparently, Jules had disposed of the clothes I travelled in and repacked my bag with women's tops, shorts, tights, socks, underwear, and another pair of Keds, bright red.
I was horrified. She knew my secret, my most carefully guarded secret, something that I'd hidden all my life from everyone.
What the fuck, I thought. I had no choice but to put on the outfit. Feeling humiliated and embarrassed as I slipped into the silky panties, everything fit perfectly. I laced up the Keds, which kicked in my arousal. I got hard as a rock. I hesitated and waited for my erection to subside. I couldn't go out dressed like this, but I had no choice. Summoning all my courage, I checked the ship's guide map for the route to the gym.
I hesitated at the gym door but entered. Inside, several men and women were working out. Jules was near the front on a rowing machine, her blond hair tied back in a ponytail, looking stunning in a black workout top, matching black tights, and white Keds. I had never seen her wear Keds before. This was a feminine departure from her normal style. She had always worn ugly dad-style sneakers.
"There you are!" Jules called out loudly as I entered, drawing everyone's attention. As people looked me up and down, I could see their quiet amusement. I was thoroughly embarrassed and humiliated. I heard a couple of men talking and laughing, adding to my humiliation.
Jules got up from her machine and approached me. "Let's go. I need a shower." I followed her back to the room, trying to ask what was going on, but she just shushed me. We entered the room, and she motioned for me to sit while she went into the shower. The minutes waiting seemed like hours. She finally finished and returned, silencing me with a finger before I could speak.
"I found your perve collection last week," she said firmly, her voice dripping with contempt. I instantly knew what she meant. I had collected a couple thousand porn pictures of women and men wearing similar outfits and sneakers in various sexual acts. I also had panties and a pair of ladies' Keds that I used to masturbate. I dropped my head, ashamed and embarrassed.
She sneered at me, her eyes narrowing in disgust. "You perverted little freak. All this time, you've been jerking off to pictures of sissies in girly clothes and sneakers? Hiding it from me like some disgusting secret? Well, guess what. It is disgusting. You want to wear women's panties and sneakers? Fine. For this entire vacation, you'll be my sissy bitch! You'll wear all those pathetic women's clothes and sneakers I've packed for you, and you won't argue or make a fuss. This is your punishment for every lie you've told by omission. I'm going to make sure you feel every bit of the shame you deserve."
"So, what is it specifically that gets you off on this stuff? The clothes? The sneakers? Are you gay? Do you like to get fucked in the ass, or are you just a fag cross-dressing cock sucker?" she asked, her tone mocking and accusatory. She's known I'd experimented with a guy in college. I had let that slip one evening after too much alcohol.
"All of it... mostly the sneakers. It gets me off," I whispered.
"I thought so," she said with a cruel smirk. "If you haven't seen, there's another pair for you in your bag. I'll be wearing Keds as well, so everyone knows they're women's sneakers. We'll match like a pair of girlfriends, won't we? How fitting for a sissy like you."
At this point, it was clear that Jules was in charge and had no intention of us having a typical couple's vacation. Her contempt for my fetish was obvious. She was determined to humiliate me the entire time, using my secret desires as a weapon against me. I had no outs. She had planned this meticulously. She found my cache last week giving her ample time to buy all this stuff.
She got dressed, laced on her Keds, ignoring me completely, and left. She came back late afternoon, still ignoring me, changed into a short tight navy dress, still in the white Keds. "Come on, it's dinner time." We entered the restaurant, where she took her time, ensuring people noticed her and, consequently, me in my feminine outfit.
I ate silently, as did she. After dinner, she commanded, "Go back to the room. I don't want to see you." I did as ordered, spending the evening reading until I finally fell asleep.
It must have been around 10 when I was awoken by a noise at the door. It was Jules and a man. They were kissing and talking dirty when the man noticed me in bed.
"What's the deal looking at me?" he asked Jules.
"Oh, just ignore him. He's my sissy bitch," Jules replied nonchalantly, her voice laced with disdain as she glanced at me like I was nothing more than an annoying piece of furniture.
They flopped onto the other bed, kissing and making out in front of me. "Oh Carl, you're so fucking hard and big," she said as she stroked him over his pants. She stood, slipped off her dress and underwear, then pulled Carl's pants down, revealing his huge, thick cock, already hard and veined, standing out imposingly with a slight upward curve, the bulbous head flushed purple and glistening with a thin sheen of precum. She eagerly began to stroke it, her fingers wrapping around its girth (easily eight inches long and almost as thick as her wrist), sliding up and down the shaft with deliberate slowness, the veins pulsing under her touch as she twisted her hand at the base, making him groan with deep, throaty pleasure. He sat on the edge of the bed, and Jules knelt down naked except for the white Keds, taking the swollen head of his cock into her mouth. Her lips stretched wide around it as she sucked hungrily, her tongue swirling over the sensitive underside while her hand pumped the base, wet slurping sounds filling the room. She bobbed her head deeper, taking more of his length until it hit the back of her throat, gagging slightly but pushing on with enthusiasm, her saliva dripping down his balls, which tightened and drew up against his body as his arousal built, his musky scent mixing with her eager breaths.
Watching from my bed, I felt a mix of humiliation and arousal, my own cock now hard and twitching uselessly under the sheets. Jules performed with a skill and passion she'd never shown me.
After a couple minutes, Jules pulled back, her lips glistening, and laid on the bed, spreading her legs wide to reveal her shaved pussy, already swollen and slick with arousal, her inner folds pink and parted invitingly, a faint sheen of moisture coating her smooth skin. Carl positioned himself between her thighs and slowly pushed his large cock inside her, inch by inch, stretching her tight entrance until he was buried to the hilt, her wetness gripping him tightly as she gasped in delight. She moaned loudly, her eyes locking onto mine with a triumphant, vengeful smirk, knowing I was watching. He began thrusting deeply, his hips slamming against hers, making the bed creak rhythmically as his cock plunged in and out, her slick heat pulling at him with each withdrawal, the juicy sounds of their bodies mixing with her breathy cries.
Jules wrapped her legs around him, pulling him deeper, her tanned calves flexing as her white Keds bounced in the air with every powerful stroke. She arched her back, her breasts heaving, and urged him on with dirty encouragement: "Fuck me harder, yeah, just like that, show my pathetic sissy what a real man is."
They engaged in a lengthy, enthusiastic fuck, switching to doggy style, where he pounded her from behind, his hands gripping her hips as his cock slammed into her repeatedly, her moans turning into cries of ecstasy while waves of orgasm washed over her. Her body shuddered, her inner muscles squeezing him tight in hot, pulsing waves. Finally, he pulled out, stroking himself until he erupted, shooting thick streams of hot cum across her pussy, ass, and back, ropes of semen splattering her skin in white, viscous trails that cooled and thickened quickly. Jules laughed breathlessly.
When they were done, Jules laughed again, thanked Carl dismissively, and he left without a backward glance. She didn't even acknowledge me. She slipped the sneakers off and pulled the sheets over herself, the room reeking of sweat, sex, and his cum still smeared on her skin. I lay there, the mix of emotions swirling inside me: jealousy, utter humiliation, and an undeniable feeling of complete submission and exposure as she drifted off to sleep, leaving me to stew in her disgust.
Jules kicked my bed. I looked up, I was exhausted from barely sleeping. Her hair was wet from the shower. "We're going to the gym, hurry up," Jules declared without a hint of remorse or concern for my feelings, her voice sharp and dismissive. She opened my bag and tossed me a pair of black tights, white panties, and a white T-shirt, then asked with a smirk, "Are you going to wear the red ones today?" I shook my head no, too ashamed to speak. "You will before this cruise ends," she assured me with a knowing look, her eyes gleaming with malicious satisfaction at my discomfort.
She dressed in front of me, not caring that I saw her naked, as though my presence was utterly irrelevant. I couldn't help but admire her thin, well-muscled body and pert, firm breasts as she slipped into her fresh workout outfit: a tight black tank top and matching leggings that hugged her curves perfectly. She laced up her white Keds with a casual flick, ignoring me completely. I dressed in silence, the women's tights clinging to me, the oversized T-shirt barely long enough to cover my groin, and finally the Keds. We headed to the gym.
At the gym, Jules completely ignored me, engaging in lively conversation and laughter with others as she worked out, her ponytail bouncing with each energetic move. She flirted openly with a couple of guys, her laughter ringing out like she was having the time of her life, while I awkwardly used a few machines, feeling out of place and painfully aware of my getup. My cheeks burned as people glanced my way, their smirks and whispers amplifying my shame. When she finished, she left without a word or even a backward glance, leaving me to trail after her like a lost puppy back to our room.
Dinner that evening was tortuously quiet. We ate and headed back to the room. She said nothing and read on her phone for a while, then went to sleep. I had another restless night, thinking I couldn't wait for all this to be over.
Breakfast with more silent treatment and then the gym.
That afternoon, we went to the ship's pool deck. Jules lounged in a skimpy bikini and her white Keds, drawing admiring stares from a group of fit, young, tanned men. She flirted shamelessly, laughing at their jokes and touching their arms, her voice loud enough for me to hear from my spot a few chairs away, where I sat awkwardly. The only saving grace was that I was able to take off the Keds and be barefoot for a while.
"Oh, ignore my little sissy over there," she said dismissively when one guy glanced my way, her tone dripping with scorn. "He's just here to carry my towel." The men chuckled, and she leaned in closer to one, whispering something that made him grin.
That same guy was getting really friendly, and Jules was lapping it up. She asked him to apply sunscreen. His hands took liberal feels as he slowly applied the cream. A couple of drinks later, he lay next to her, and they started to kiss. Jules looked at me, smirked, and pulled a towel over their waists. I could see the towel bobbing up and down between them. She was giving the guy a handjob. It went unnoticed by others around the pool except for me. The humiliation burned.
After a particularly silent and tense dinner where she flirted outrageously with the waiter, calling me "her sissy" to his amusement, she didn't return at all. I lay awake in the stateroom, jealousy gnawing at me, until she stumbled in the next morning just before dawn. She reeked of sweat, cologne, and sex, her dress disheveled with dried cum stains splattered across the fabric, stark white against the navy material. "Had a real night out with a real man," she said with a cruel yawn, not even looking at me as she peeled off the dress and collapsed into bed. "Better than wasting time with a pervert like you." The scent lingered in the room, a constant reminder of her disregard, leaving me humiliated.
She slept most of the day. I had gone and ate lunch and dinner by myself. It was kind of refreshing not to be scorned. To my relief, she didn't bring any more men to our room that night.
Our last full day was a repeat of the gym, pool, and dinner. The only thing that changed for me was having to pick another humiliating outfit from my bag. The red Keds loomed large in the bottom of the bag.
That night we ate, and I returned to the room after being dismissed. She returned to the room a few hours later with not one, but two men: the same large guy, Carl, from before, and a smaller, younger man who looked about twenty.
"There he is," Carl announced with a booming laugh, pointing at me as I sat up in bed, confused and anxious, my heart pounding. Jules fixed me with a cold, contemptuous gaze, her lips curling in disgust. "This is Herman, Carl's stepson. He's gay and has never been with a man. I told them my little sissy bitch would be happy to oblige with a blowjob." I started to shake my head in protest, horror rising in my throat, but she cut me off sharply, her voice laced with venom. "Yes, you will. I know you love to suck cock or would you prefer to be fucked in the ass. Now get dressed in your girly costume and those pathetic Keds. We want to watch you suck his cock like the perverted freak you are."
Trembling with a mix of dread, I picked up the clothes I had worn during the day and went into the bathroom. I slipped into the silky panties, feeling them hug my skin snugly, then pulled on the tights and T-shirt, finally lacing up the navy Keds. My cock hardened instantly, tenting the front of the tights embarrassingly, betraying my excitement amid the humiliation. Great, now everyone would see just how much this was turning me on, like the pathetic sissy she kept calling me.
When I emerged, Jules sneered at me, her eyes raking over my outfit with open revulsion. "Look at you, all dolled up in your girly sneakers, hard as a rock already. Pathetic." She turned to Herman and commanded, "Pull down your pants." Unlike Carl's imposing size, Herman was awkward, thin, and a rather homely guy. He pulled down his pants and shorts, exposing his uncut penis. It was quite thin, his erection modest but throbbing eagerly. I suppose the thought of getting his cock sucked had gotten him ready. The smooth shaft was about four inches long with a slight upward curve, the foreskin partially retracted to reveal a glistening pink head with a bead of precum at the tip, his small scrotum hanging loosely below. He sat on the edge of the bed, looking nervous but excited, his slim legs spread awkwardly.
On Jules' sharp command, "Get on your knees, sissy, and show us what you're good for," I dropped to the floor between Herman's thighs, the carpet rough against my knees. Remembering my past experiences from college, I leaned in, wrapping my lips around the warm, velvety head of his cock. The taste was salty and musky, a mix of skin and arousal that filled my mouth as I slid my tongue along the underside, tracing the sensitive spot where the head met the shaft and gently pushing back the foreskin to expose more of the smooth tip. I took more of him in, my lips tightening around the thin shaft, bobbing my head slowly at first, then picking up pace as I sucked with deliberate pulls, hollowing my cheeks to create suction. Herman groaned softly, his hands fidgeting at his sides, clearly overwhelmed by his first time. His breathing quickened, and his thighs trembled slightly as heat built in his groin, making his cock twitch in my mouth with eager throbs.
Jules and Carl began their own act of passion on the other bed, completely disregarding me like I was invisible. Carl's large frame loomed over Jules as he stripped her, then himself naked, his thick cock veined prominently, springing free and hard, the shaft rigid with prominent ridges and a flared head already leaking precum. She moaned loudly as he slowly entered her slick pussy, engulfing him. The wet sounds of their bodies slapping together echoed through the room, her wetness coating his length as he thrust deep and hard. Jules locked eyes with me briefly, her expression one of triumphant scorn, before turning back to Carl with a passionate kiss, her hands clawing at his back as he pounded into her relentlessly. "Fuck me harder, Carl. Make me forget all about that worthless sissy over there," she gasped, her words cutting like knives, emphasizing how little our relationship meant to her now.
I focused on Herman to drown out the humiliation, using my finger to press firmly on his taint, rubbing in small circles to heighten his pleasure and hasten his climax by building that deep, tingling pressure. His small body tensed, his balls drawing up tight against his body as he bucked his hips slightly. He tensed, shuddering with a whimper, his cock pulsing four or five times as spurts of hot cum shot into the back of my throat. I swallowed the thick, slightly bitter fluid reflexively. His shaft softened gradually in my mouth, the warmth fading as his shaky breaths filled the air. The act made me feel even more degraded, like a tool for their entertainment. Jules laughed derisively from the other bed mid-moan, knowing Herman had just blown his load in my mouth.
Herman, inexperienced but eager, wanted to return the favor. Jules nodded dismissively, still riding Carl's cock with abandon, her breasts bouncing as she ground down on him, her body rubbing against him in sweaty, heated rhythm. "Go ahead, let the sissy get off. It's the least he deserves for being such a good little whore." Herman pushed me back onto the bed and fumbled, pulling down the tights to free my aching erection, throbbing desperately after days of buildup, about six inches long with a pronounced vein along the top and a flushed, sensitive head. His technique was sloppy and awkward, his mouth too tentative at first, teeth grazing my shaft lightly as he tried to mimic what I'd done, his tongue lapping unevenly at the head and occasionally bumping the sensitive underside. But the pent-up tension from the cruise's constant teasing overwhelmed me. I tensed up, my balls tightening as waves of pleasure built, my body contracting in hot bursts, and I came hard into his mouth, groaning despite myself as my cock spasmed, shooting warm jets of cum he struggled to swallow, some dribbling down his chin in sticky trails.
Herman slept in my bed and Carl with Jules the remainder of the night. What must have been a couple hours later, I awoke with Herman rubbing his penis between my ass cheeks trying to get in my ass. I pushed him away, but he persisted. He was horny again and wanted more. There was no way he was going to fuck me in the ass, but I didn’t want Jules or Carl waking with all the fussing he was making. I rolled over and stroked his cock. It wasn’t long before he was dripping precum. I used my thumb in a circular motion, concentrating on his penis head. It was getting nice and slippery, and it was an easy job getting him to cum. Most of the cum was in my hand, which I wiped on the sheets, and I quickly fell back to sleep.
In the morning, the room's air was thick with the scent of sex and sweat. Carl and Herman left, with Herman mumbling a shy thanks that I was too humiliated to respond to, my face burning as Jules watched with a smug grin.
Finally, we were going home. We showered. Jules looked at me with final, contemptuous authority and simply said, "Red." My only clean clothes left were light gray tights, white ankle socks, a plain white T-shirt, and the bright red Keds, which screamed femininity from a mile away. The journey home was a blur of self-consciousness, every glance from strangers feeling like it was aimed at me, the red Keds broadcasting my feminized state like a neon sign of shame.
Back in our apartment, I closed the door behind us, and Jules immediately announced, her voice cold and unyielding, "You'll be moving into the guest bedroom. If you want to stay here, you'll please me however I want, and you'll wear nothing but women's clothes and your Keds sneakers while at home. Got it, sissy?" With finality, she removed her own Keds, popped them into the trash, and declared, "I'll never wear Keds again."
This new arrangement was the culmination of the power shift that had occurred over the cruise, our relationship now defined by my total submission and her absolute dominance, the Keds a constant symbol of my degraded reality.
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