Dear Diary,
Well, today I learned about a practice I thought had died along with the middle ages, and a lot more about my own desires…
I was sitting at the bar in that cosy little place up on the top deck. A couple of guys had tried approaching me, but they didn’t do anything for me, so I politely turned them away, saying I was waiting for someone.
A woman sat down next to me, and gave me a brief nod. As she looked down the bar to see where the bartender was, I took a quick look at her. She was blonde, slim, very pretty, maybe late twenties, in a long black dress. I could tell that, like me, her tits were pert enough not to need a bra.
The bartender quickly noticed her. “What can I get you?”
The woman glanced at my drink. “That looks good,” she said, smiling at him, “I’ll have one of those.”
“Coming right up,” he said, and turned to prepare it.
She turned and smiled at me.
“That felt brave,” she said, “what did I just order?”
“Cosmopolitan,” I replied, smiling back.
“Oh, good,” she said, “I don’t think I’ve ever had one of those!”
I nodded, and took a drink of mine.
“I’m Emma,” she said.
“Roxanne,” I replied.
“Saw you knock back a couple of guys there,” she continued, “you waiting for someone?”
“Maybe,” I said, “but not them.”
Her drink arrived, and she took a sip. Her face lit up.
“Oh yes!” she exclaimed, “that’s definitely going to work!”
I chuckled. “Careful, those are really strong.”
She looked around the bar and noticed an open table in the corner. She indicated it with her drink. “Join me?”
“Sure,” I said, and we quickly took the table before anyone else could.
The dark corner of the bar felt very intimate, almost like we were on a date.
“So,” I asked, “enjoying the cruise so far?”
“Oh, yes,” she enthused, “it’s been fun – we’ve seen a couple of the shows, and we went ashore and did the tourist stuff at the last port. Bought some tacky souvenirs and everything!”
I laughed. “It’s not a vacation without tacky souvenirs.”
The Cosmo was already beginning to loosen her up, and she leaned in closer and confided, “and we’ve been having the BEST sex!”
She blushed, and giggled, putting her hand over her mouth.
I smiled. “I warned you those were strong!”
She laughed. “I guess!” She paused a while, then said “but now you have to tell me something indiscreet to make me feel better.”
I hesitated, then told her how I had been stood up, and so ended up on the cruise alone, and how I had decided to be more daring. I didn’t tell her about changing my name – that made me sound like a crazy person.
“So…” she pressed, “and have you been daring?”
I confessed about the guy I fucked my second night aboard, and about making him hold the yellow-pages up while I blew him.
She laughed. “Wow, there’s an experience he’ll never forget!”
We started our third Cosmos, and I decided to tell her about my other adventure, with the crewman and the security guard. She gasped as I revealed each shocking detail. I noticed that her face was flushed, and her nipples were starting to poke through the fabric of her dress.
When I finished, she sat in stunned silence, then finally spoke.
“Oh, my God,” she breathed, “you’re amazing… you’re so lucky you didn’t get thrown off the ship!”
I smiled. “I know,” I said, “it was touch and go there for a while.”
She paused, then gave a shy little smile. “So do you have the photos on your phone?”
“I’m not showing you those!” I gasped.
She pointed to the neckline of my dress, which reached all the way to my belly button.
“Come on,” she implored, “I can practically see your tits anyway!”
I relented, and pulled the photos up on my phone and handed it to her.
She scrolled through them, wide-eyed. She zoomed in on a couple, lingering over the close-ups.
“You have such a pretty pussy,” she whispered, almost under her breath, and I blushed.
After she reluctantly handed the phone back, she asked me, “so what naughty plans do you have for tonight?”
“I’m not sure,” I hedged, “how about you? Where is your husband?”
“He’s back in our cabin.” She leaned in towards me, and said in a conspiratorial tone, “Greg and I have an arrangement.”
We sat in silence and sipped our drinks for about fifteen long seconds.
“Well,” she hissed, “aren’t you going to ask about it?”
“I was trying to see how long I could contain myself,” I giggled, the alcohol suddenly making me feel a little light-headed.
She laughed, and knocked hers back, quickly gesturing to the bartender to bring two more.
“Promise you won’t be shocked if I tell you?” she asked.
“No.”
She laughed again. “Well, I’m going to tell you anyway.”
She paused as the drinks arrived, and took a long, slow sip.
“It’s really quite simple,” she continued, “I go out for the evening, do something naughty, then go back and tell him in great detail about it.”
“That’s it?” I said.
“Well, he gets to fuck me while I tell him,” she whispered.
“So he likes the idea of being inside you after another man?”
“Oh, no, he doesn’t allow me to have anyone else inside me,” she explained.
I chuckled. “And how does he hope to enforce that?”
“Oh, quite simple,” she replied, matter-of-factly, “I’m wearing a chastity belt.”
I blinked. “Come again?”
“A chastity belt.” she repeated.
“You mean,” I paused for a second, “you mean like a heavy, wrought-iron, padlocked, medieval contraption?”
“Well, they’re very light, and stainless steel these days, but yes to the padlocks.”
I giggled, unsure if she was kidding.
She took my hand, and placed it against her midriff. Under her dress, I could feel a cold, hard band encircling her waist. She slid my hand to the front, and I felt that another band extended downward toward her crotch. Where they joined, there were a couple of lumps.
“Wanna see?” she asked, suddenly.
I nodded, and she jumped to her feet, grabbed my hand, and dragged me off to the ladies’ room.
The gaps under the doors of the four stalls were incredibly wide, so it was easy to see we were alone. She quickly pushed me into the furthest stall, and I closed the lid and sat down. She had to squeeze closely against me to get the door closed, and her breast brushed against my face, sending a tingle down between my legs.
She stood back against the door, and slowly hitched her dress way up under her boobs, revealing long, beautiful legs, slender hips, a perfect flat stomach, and a chastity belt. It was shiny chrome, a belt cinched high around her waist, and a strap running from the belt down between her legs, which widened over her pubic mound, then narrowed where it covered her pussy.
I reached my hand towards it. “May I?”
She nodded, “of course!”
I stroked the smooth, cold metal, then tried to get a finger behind the strap. It was tight – there was no way she’d be able to get a hand down to her clit.
A thought occurred to me.
“Can’t you just pull the strap to one side to get at your pussy?”
“Try it,” she said, and lifted her foot up onto the toilet roll holder.
With her leg up like that, the strap looked like it could easily slip aside, so I took hold of it between her legs and pulled. It didn’t move. I tugged hard enough that Emma had to steady herself against the wall, but it still didn’t shift. I looked up at her questioningly.
“There’s a dildo and butt plug in there,” she said, proudly.
I was stunned. I pulled down on the band and took a closer look. Indeed, I could see the very base of two shafts disappearing up inside her.
“Isn’t it uncomfortable?” I asked.
“It’s ok. I mean, I wouldn’t want to run a marathon in it, or anything, but I can handle it for a full day. You’re supposed to be aware of it the whole time. You know, so I remember that there’s only one man allowed in.”
Suddenly, we heard the bathroom door open. We both glanced down at our feet, then looked at each other in panic – with the large gap under the stalls, whoever came in would easily be able to see there were two people in this stall. Emma leaped into my lap, astride me, wrapping her legs around my waist to get them off the floor. Her dress was still hitched up, so I found my hands on her smooth, firm ass.
Her arms were around my neck as we held each other tightly in silence.
Footsteps came towards us. Of all the empty stalls, the newcomer had to choose the one right beside us! We heard her shuffling around, the rustle of clothing, then a plump foot came into view under the partition. Large, grey granny-panties slid down to cover it, and I stifled a giggle. There was a grunt as the woman sat down, then a pause, then the loud sound of urine gushing into the bowl.
I lost it, but Emma had anticipated me, and slapped her hand over my mouth, and was giving me a fierce glare, her nose almost touching mine. This only made it funnier, and soon I was rocking gently back and forth, snorting through my nose, tears streaming down my cheeks.
Emma changed tactics. She pulled her hand away and replaced it with her mouth. Her soft, warm, yielding lips, the delicious taste of her, the heat of her breasts pressing against mine pushed all other thoughts away. I kissed back, first just gently, then with passion, my tongue forcing its way past her lips, probing inside her. My hands began to stroke her buttocks, feeling the thick cord between her cheekss that held the back of the chastity belt together. She had one hand on the back of my head, fingers tangled in my hair, but the other slid between us, into the deep plunging neckline of my dress, and onto my breasts. She cupped one firmly, then found the nipple between her finger and thumb and gently teased it to hardness. She gave it a sharp tweak, and a thrill shot down between my legs. I dug my finger nails into her ass and kissed her harder.
Somewhere on the edge of my consciousness, I heard the toilet in the next stall flush, and the sounds of the woman leaving. Once all was silent, Emma pulled her face back.
“I think it’s clear,” she whispered.
I darted my head forward and stole another kiss. “Come to my cabin?” I said, hopefully.
She nodded and climbed off me. She straightened her dress and we exited the cubicle and quickly cleaned our faces in front of the large mirrors.
We practically sprinted down the hallways, and took the stairs down to my deck rather than wait for the elevator. I frantically fumbled in my purse for my keycard, then we burst into my cabin, tumbling on top of each other onto one of the single beds.
She was on top of me, kissing my mouth, my throat, then pulling apart the top of my dress to get at my breasts. She kissed and sucked and nibbled on them until my entire body was tingling, and my pussy felt like it was going to burst into flame.
With an effort of will, I heaved her off me and got to my feet. I kicked my shoes off, then slid my dress down over my hips to the floor, so that I stood there in just my skimpy g-string. I gave a quick twirl so she could admire my toned ass, then turned her around by the shoulders so I could unzip her dress.
I pulled the zip down slowly, and kissed my way down her spine, past the frustrating steel band of the chastity belt. She had delicious little dimples above her ass, and I gently licked each one, then slid the dress off her.
She turned to reveal her breasts to me in all their glory. They were slightly larger than mine, firm and proud, the small, pink nipples pointing upward. I cupped them both in my hands and drew little circles on the buds with my thumbs. Emma’s eyes half closed, and she gave a soft moan.
I took her face in my hands and pulled her towards me, and we were kissing again, slow, sensuous kisses, probing each others’ mouths, sucking lips and tongues. I felt her rock-hard nipples against my breasts and the hard, cold steel of her chastity belt against my pelvis. I grasped the belt firmly in my hands and lifted her off her feet with it. She gasped as the dildo and butt-plug pressed up inside her, the strap dug into her flesh, and the flat plate on the front squeezed her clit. She wrapped her silky legs around me, putting her weight onto my hips, and we continued to kiss, my head now back, her face above mine. My fingers groped at her crotch, desperately trying to find a way into her past the cruel metal.
“How do I get this thing off?” I mumbled into her mouth.
“You could ask Greg,”
“How?”
She climbed down and grabbed her phone. She handed it to me, after opening a text message to him.
I typed my cabin number, then ‘BRING THE KEY’. Then I lay back on the bed, spread my legs wide, and snapped a photo of my crotch. The flimsy fabric of my panties left little to the imagination, and the outline of my shaved pussy lips was clearly visible, along with a dark stain of my arousal. I hit “send”.
I tossed the phone aside, then pushed Emma back onto the bed by the tits, pinching her nipples at the last moment so they were yanked out of my fingers as she fell. She squealed in pleasure and pain, then I was on her, grabbing her ankles and spreading her legs wide. My tongue lapped at her exposed skin around the strap, pressing into the hollows at the top of her legs, and trying urgently to get to her cunt. The scent of her juices was driving me wild. She groaned in pleasure and frustration, her fingers tight in my hair, pulling my face into her.
There was a sharp rap at the door. I jumped up and flung it open wide, not bothering to cover myself. A tall, handsome man in a dark suit stood before me. His eyes swept down over my nakedness, then over my shoulder at his wife lying on the bed, her legs still spread wide.
I held out my hand, and he dropped a small gold key into it.
I jumped back up onto the bed and worked on the two padlocks, first detaching the crotch strap, then opening the belt.
Emma stood up and removed the belt first, then squatted slightly. She pulled the strap down, and I watched the thick dildo and putt-plug emerge with a satisfying squelching noise. She gave a sigh of relief. As I expected, she was shaved, but unlike me, she had a thin ‘landing-strip’ of pubes above her clit.
Her husband sat down on the edge of one of the beds.
He spoke for the first time and patted his lap. “Are you ready?”
I looked questioningly at her.
“Whenever I persuade another woman to remove my belt, I have to be punished,” she explained, “and if that woman wants to have me, she has to accept the punishment too.”
I had ceased to be shocked by anything today, so I asked, “what’s the punishment?”
Her husband answered. “A sound spanking.”
She nodded, then got on her knees beside him and draped her naked body over his lap. I stood back to watch.
He began spanking. It didn’t seem very hard, but I could soon see her bottom reddening. From the slow way her hips were rolling, it seemed like she was quite enjoying it, and just watching thrilled me in a way I hadn’t known I could be turned on.
Then he paused, his hand gently stroking her cheeks. She tensed, knowing what was coming next. He lifted his arm up high, then brought his hand down with an almighty slap on one cheek. She yelped in pain, her legs kicking. He delivered twelve hard spanks, alternating cheeks, and she cried out at each one, but didn’t try to escape. Finally, he let her up, and I saw tears in her eyes as she held back sobs, her hands rubbing her sore bottom. I wondered if I could take this punishment, but I knew I would try – my pussy ached for her.
“I think you need more, don’t you?” he asked. She nodded, sniffing.
“Why?” he asked, gently.
“Because I’m a dirty little slut,” she whispered, contritely.
“That’s right,” he said, patting his lap again.
“Oh, God”, I thought, “now what?”
She positioned herself over his legs again, but this time with her legs wide open. He stroked her pussy gently, even slipping a finger briefly inside her, then slapped her hard, right on the cunt.
She shrieked and slammed her legs closed. He waited patiently, his hand trapped between her thighs. Slowly, she opened up again, and seemed to steel herself. He slapped again, and she gave a howl of pain, but kept her legs open. He delivered a total of six slaps, then gently stroked her pussy while her sobs subsided.
Eventually, she pulled herself together and stood up. Her face was wet and her mascara smudged.
“Your turn,” she said to me, with a wicked little smile.
“I don’t think I can take that,” I confessed.
“Oh, but you must!” she exclaimed, “If you don’t, I can’t have you, and I want you SO badly!”
I wanted her more than I’ve ever wanted anything in my life. I wanted to feel her thighs clamped tight around my head as I sucked on her clit, I wanted to feel her tongue inside me, I wanted to finger her wet pussy, then feel her lick her juices off me…
I had no choice, and I took my place over her husband’s lap.
He began the same as with her, warming my bottom with a volley of small smacks, the thin string of my panties between my cheeks creating no obstacle. I was surprised how erotic it felt, as the heat of the spanking spread all over my body. I could feel the vibrations in my pussy lips and in my nipples, which were just brushing the fabric of the blanket on the bed.
Then he paused. I knew what was coming, and I braced myself.
He leaned down and whispered in my ear, “no matter how much you plead, I won’t stop unless you say ‘mercy’, ok?”
I nodded. With his free hand, he took one of my arms and pinned it against my back. His other hand lifted off my bottom and I tensed.
SLAP
It hurt much more than I expected, and I gave a shriek.
“No, oh my God, stop!”
He slapped again, on my other cheek.
I yelled and squirmed, but he pressed me down and spanked me again and again.
Deep down, I realized how liberating it felt to yell and scream for him to stop, knowing that he wouldn’t, that he would make me take it all. Despite the pain, I felt like I might cum at any second.
Then the twelve spanks were over, and he let me up. I was sobbing uncontrollably, and Emma took me in her arms and held me tight, one hand gently rubbing my bottom. I hoped he wouldn’t insist on the final phase. I glanced over at him, hoping for leniency, but he patted his lap.
“Emma,” I gasped, still sobbing, “I can’t take that!”
“Please,” she begged me, “you can do it, I know you can, and it will make what comes after SO much better, I promise.”
I sniffed, and nodded. I laid over his lap, resigned to my fate.
“Emma, please remove your friend’s underwear.”
She crouched down behind me and pulled my panties off, then took hold of my ankles and spread my legs wide. So there I was, completely naked, spread, lying over a strangers lap waiting for him to punish me.
Like with Emma, he put his hand between my legs and gently fingered my pussy, stroking up and down the lips, dipping briefly inside me, then lingering over my clit. I let out an involuntary moan, and I heard Emma chuckle.
Then his hand lifted and I clenched my cunt. The pain stunned me, searing across my labia, lights flashing in front of my eyes, my clit stinging. I leaped to my feet and grabbed my pussy, hopping from one leg to the other.
“Oh, shit, no!” I yelled, “no way!”
Emma quickly grabbed me by the shoulders. “You can take it,” she coaxed, “only five more, I’ll help you.”
Pushing through the tears, I turned to him. “I can only take it if you don’t hit my clit, ok?”
Greg considered, and exchanged a quick glance with Emma, then nodded, “ok, agreed.”
I rubbed my pussy some more, then resumed my position over his legs. Emma crouched on the bed in front of me and held my hands tightly, her face down right by mine, whispering encouragement.
SLAP
I screamed, and my legs snapped shut. His hand pressed tightly on my cunt, and I managed not to leap up. I counted to five, then slowly opened my legs. I realized my fingernails were digging into Emma’s palms, and loosend my grip. Emma left me one hand, but I noticed the other slip between her legs.
“Ready,” I gasped.
SLAP
I screamed again, but managed to keep my legs open. His fingers caressed my lips again.
SLAP
I yelled out, but it didn’t hurt as much – my lips were starting to go numb.
“Only three more,” whispered Emma.
I realized that, despite the pain, I loved this.
He delivered three more, stinging, burning, beautiful, thrilling slaps to my red-hot cunt, and my yells turned into moans.
“More,” I gasped, “hit my clit!”
He began to rain down hard slaps on my cunt, further down so that he spanked my clit. I felt the orgasm rising from the pit of my stomach, and I clamped my legs tight around his hand. He pushed his thumb inside me and rubbed my clit hard with his fingers. Even more heat radiated out over my body. I squeezed Emma’s hand as hard as I could, and my whole body began to shudder and convulse. His thumb pressed against my g-spot, and he pushed his other hand under me and grabbed a nipple, and the orgasm stepped up a level, harder than I’d ever had before. My vision went black, and I could barely breathe, panting into the blanket.
I opened my legs a little as it subsided, allowing Greg to start stroking and teasing my pussy lips. I moaned in ecstasy.
I looked up at him. “Please fuck me,” I begged, climbing off him.
He glanced over at Emma, who must’ve nodded, because he began to unzip his fly.
I turned to Emma, and dove onto her, pushing her down onto her back. Kissing her hard, hungrily, I pushed my hand down between her legs, and finally found the prize I’d yearned for. I slid my fingers into her cunt, and she moaned into my mouth.
Her hand went between my legs, and spread my pussy lips wide, and I felt Greg’s cock nudge against them. I backed towards him, welcoming him into me, and let out a long, deep sigh as he slid his hard length into my sopping wet hole. He gripped my ass as he began to fuck me, slow, smooth and firm, and I slightly rocked back and forth in time to him.
I closed my eyes and focused on the wonderful sensation of being penetrated by his big cock, feeling his balls against me with each stroke, forgetting about everything else. He minimally shifted his hips with each stroke, so that sometimes his cock pressed against the back of my canal, sometimes against my tingling g-spot. Then he pulled back and held his cock steady, just the very tip inside me, his hand firm on my ass, resisting my futile attempt to push back, then he suddenly plunged into me. I grunted loudly, and he did it again, and again, his balls now slapping hard against me.
I could feel he was close to cumming, and he slowed down again, anxious to last longer. I felt Emma shifting under me, but I didn’t open my eyes. Eventually, I became aware of the delicious, musky scent of her cunt, and I opened my eyes. There it was, finally, free and spread in front of my face. Her inner lips prominent and open like a butterfly’s wings, her swollen clit peeking out from under its little hood, and her glistening hole, full of promise.
I puckered my lips and closed them around her clit, sucking and flicking my tongue over it, drawing it into my mouth, and she shuddered and moaned erotically. Her fingers slid into my hair, and guided me downwards. I licked lower across her delicate lips and down to her vagina, slipping my tongue inside and lapping her heavenly juices, then smeared them upwards all the way back up to her clit and back down.
I began to fuck her wet hole with my tongue in time to Greg’s fucking of my cunt, then I replaced my tongue with my fingers, curling them up to her g-spot, stroking it. I pressed my tongue down just above her clit and started quick, tight circles.
“Oh, yes!” she groaned.
I could feel her body tensing up under me, and her tight pussy gripped my fingers even more. As she began to cum, Greg hunched over me, grabbing my tits, his pelvis thrusting harder against my ass. I slid a hand down between my legs and cupped his balls, just in time to feel them spasm as he shot his sticky, salty load deep inside me with an animalistic roar. I kept my mouth pressed firmly on Emma’s clit, my tongue gently stroking it, then, as her orgasm subsided, and Greg pulled his shrinking cock out of me, I slid my body up her until I was lying on top of her, her arms around me, panting.
We kissed slowly, luxuriously. Emma gently stroked her hands up and down my back, caressing me, sometimes reaching to my buttocks, sometimes sliding down the side to my breasts.
“Are you full of my husband’s cum?” she whispered.
“Mmm, yes,” I murmured, “I can feel it leaking out of me.”
She gently bit my earlobe. “I want it,” she hissed, “I need it.”
“You’re insatiable,” I smiled.
She kissed me again, then rolled me over onto my back. She stroked my tits, then slid her hand down between my legs and into me. She tasted her fingers.
“I want all of it,” she insisted, “every drop that’s in you.”
I brought my knees up and let them fall apart.
“My dripping cunt is all yours.”
She climbed astride me, giving me the delicious sight of her spread pussy and little puckered asshole, and pressed her mouth against me, lapping up the cum. I lay back, enjoying the sensation and the view, relaxing, gently fondling Emma’s tits.
On the other bed, Greg sat watching his wife lick his cum out of another woman, stroking his semi-erect cock.
I watched him for a while, then beckoned him over to me. He climbed up on the bed behind his wife, and I bent my head back as far as I could and took his cock in my mouth. I relished the mingled flavours of his cum and my pussy juices on it, and ran my tongue around his head, sucking and licking. He groaned softly as his cock reached full hardness.
He pulled out of me, and offered me his shaved balls. I gently sucked one into my mouth, and he gasped, steadying himself on Emma’s ass. I teased the soft skin with my teeth and lips, and rolled the testicle around with my tongue. A big drop of precum dripped onto my face, and I knew he was ready for her, and released him.
He positioned the tip against his wife’s cunt, and I had the sensuous pleasure of watching up close as he parted her lips and slowly slipped inside her, all the way up to his balls, then slowly fucked her, his cock tugging her labia back and forth. I lifted my head to her and flicked my tongue across her clit, and she shuddered with delight.
Once Emma was satisfied she had tasted the last of his cum in my snatch, she moved up to my clit and began sucking and licking, and I settled back for the ride, cupping her tits and watching her cunt repeatedly filled. Soon I was cumming again, slower and softer than last time, the heat spreading to my very fingertips, wave after satisfying wave rolling over me.
I lay on my back and watched my new friends fuck inches above me, and thought to myself that this might be the closest I ever get to heaven…
Source: reddit.com/r/sexystories/comments/45tmpp/rachel_and_roxanne_ch3_ffmffspankingchastityoralsm
Fuck that last quarter was so hot. Please continue