Weekend on the Water Ch. 02

Story Info
Our weekend takes a turn when Mistress introduces a surprise.
3.2k words
4.32
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11

Part 2 of the 2 part series

Updated 06/08/2023
Created 10/24/2017
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"What a beautiful morning! Wouldn't you agree, slut?" I looked up from my breakfast, expecting to see my former-girlfriend-turned-Mistress staring out the kitchen window. Instead, I found her staring at my naked body, objectifying me in all the best ways.

We were aboard her father's private yacht. Both of our respective families were on vacation for another day, so Mistress intended to make the most of our private time together; I was more than happy to play along. I was eating the breakfast she had cooked for me: scrambled eggs, a slice of toast, fresh cut apple slices, nothing that required a fork and knife to eat. This was by design of course, as I had only one free hand.

I sat in the dining area of the kitchen, on a chair fixed to the floor. My ankles were individually cuffed to the chair legs, and my left wrist was cuffed behind my back to my right upper-arm, rendering my left hand useless and severely limiting what I could do with my right arm. I was completely naked, and while it was not visible, a medium-sized butt-plug was seated securely in my ass. It had a large gem set on the end of it, which always brought a smile to her face when I bent over for her.

Just as I was finishing the last bite of toast, Mistress walked over and stood behind me. One of her hands found my neck and gently grasped the front of it, the other possessively stroked the side of my face. She herself was wearing shiny thigh-high latex boots, a short latex skirt, and a matching top that really showed off her pronounced cleavage. As I swallowed the last bite of breakfast, she leaned in close and whispered in my ear: "Remember how I said today was going to be more for you? Well...what could a submissive slut like yourself want more than to please his Mistress?" I tilted my head back to look at her, but she grasped my neck tighter.

"I have a surprise for you today. Come out onto the deck with me. It should be here any minute." With that, she uncuffed me from the chair, then used a single pair of handcuffs to bind my feet together, and used the extra pair to cuff my right wrist to my left upper-arm. I stood up, and she walked me as fast as my cuffed ankles would allow onto the front deck of the yacht. I took in the ocean around me. It was actually quite a nice morning, sunny, warm, not a cloud in the sky. Nobody else out there...

Just then I saw a speedboat heading towards us from off in the distance. I looked at Mistress to see if she had noticed. She had a calm look on her face, which slowly turned into a smile.

"Ah, there's the surprise now," she said. "Are you ready to meet Sir?"

My blood immediately ran cold. I was one of the most painfully straight people you would ever meet, and I thought Mistress knew that. Nothing appalled me more than the thought of submitting to a man, or doing anything remotely sexual with a man, for that matter. I turned to Mistress to share my discomfort with her, but she was ready for my objections. She forced a large ball of cloth into my mouth before tying it in place with a strip of cloth. I struggled against my restraints, but they held fast, and I was completely helpless to run, to object, or to do anything Mistress did not wish me to do.

Finally, the boat reached us, and went around the back of the yacht. Mistress pushed me down on my knees, facing the front of the yacht, so I would not be able to see Sir until she wanted me to. My heart was racing. Would she really make me...

I heard heavy footsteps behind me, drawing near. I tried to turn to see who it was, but Mistress held my hair tight, then forced my head down to the deck, so I could see no more than a foot in front of me. Two boots entered my limited field of view. After a brief pause, Mistress relaxed her grip and informed me that Sir had arrived. I slowly lifted my head to get a first look at Sir. My eyes traced from the boots, up the tight jeans, the loose-fitting sweater, and the face, which had the sun more or less behind it, revealing a mere silhouette.

Sir was not particularly tall. I took note of shoulder-length blonde hair, and gentle curves around the face. Sir appeared to be clean shaven. I also noted that Sir had fairly slender legs, which for some reason surprised me. The most shocking thing about Sir was the voice, which I heard for the first time at just that moment.

"This one is just adorable!" exclaimed Sir. The voice was not exactly the masculine baritone I had expected. It was actually quite feminine. Sir took a step back, and I got a better look. Sir had a very feminine face.

"Slut, this is Sir. You will address her as such," Mistress informed me. "Do you understand?" I was not exactly sure how to react. Mistress had said "her". I tried to wrap my head around what was happening when Mistress demanded of me once more if I understood.

I nodded my head "yes" unable to respond through the gag, which she then removed from my mouth. I watched as Sir removed her sweater, revealing the frame of a slender woman with small, but definitely notable tits. Being traditionally a fan of large tits, I found myself somewhat surprised at just how much fun I thought her tits would be, and became slightly more aroused. At the same time, I had a slight problem.

"Mistress," I began. "You know that I am very straight. I don't exactly know how comfortable I am referring to her as Sir. It makes me feel like I am submitting to a man." Immediately, Sir spoke up.

"Trust me. You'll feel a lot more comfortable with the idea when I'm fucking you in the face with my strap-on." Her words made me instantly horny, awakening some strange part of my inner submissive, the part that absolutely loves when the dominant takes on the traditionally masculine role. There's just something absolutely exhilarating about the thought of being subjected to that, and I found myself readily replying "Yes, Sir," before bowing my head.

"You've trained this one well," Sir chided to Mistress. "I can't wait to see just how well..." Sir turned and smiled cruelly at me, playfully twirling a lock of her hair. "Let's get him set up."

20 minutes later, I found myself in a room in the lower deck of the yacht. It appeared to be a sort of multi-purpose room, and Mistress had a very specific purpose for it. I was bound to a large, sturdy cushion shaped like a narrow, upside down "V". My legs were tied spread in leather restraints on one side, and I was bent over, my wrists restrained in similar restraints at the bottom of the other side. I was still naked, and completely helpless. Off to the side of the room, Mistress and Sir were talking quietly to each other. Before long, they seemed to come to an agreement on what they were discussing, and turned to face me.

Mistress was wearing a fairly large strap-on. It was pink, and had a smooth, plastic surface. Sir was wearing a strap-on as well, but this one had a few grooves in it, no doubt to help induce pleasure. Neither of them were wearing anything else. Then, they walked towards me.

I struggled against my restraints for a moment more, before watching them take their place at either end of me. Mistress stood behind me, applying lube to her strap-on and my ass. Sir stood in front of me, carefully adjusting her strap-on and wincing every time she moved it just right. There was something odd about her strap-on, but I couldn't figure out what it was.

Suddenly, I felt a pressure building up against my asshole, and heard Mistress giggle. Then I felt her hands on my hips as she slid her girl-cock into my ass, and gently forced it in as deep as it would go. I moaned aloud, and at that moment, Sir shoved her girl-cock in my mouth, pushing it into my cheek. I pulled against the restraints, trying to escape this humiliation, which only seemed to entertain my captors. Mistress slapped my ass and wriggled her cock around inside me as Sir gently pulled her hips back and pushed them forward again, sliding her cock almost out of my mouth before pushing it back into my cheek.

Mistress began fucking me. While she gently caressed my sides and ass, and slowly forced her cock in and out of me, Sir had ideas of her own.

"I'm going to teach you to suck cock proper," she grinned a wicked grin. "I know you'll never use these skills on a man, but trust me. Dominant women love a whore like you who can suck cock like a proper slut. While we might not actually feel it, we can tell." She pulled herself out of my mouth, letting loose a buildup of drool, which she collected on the tip. "I am no exception. A good little bitch who can suck me off right might just get a reward. Now, show me what you can do."

She held her cock inches from my face. I was somewhat distracted from Mistress thrusting herself into me, moaning with the pleasure of my emasculation, but I leaned my face forward as far as it would go and wrapped my lips around the head. I rocked my head back and forth, sliding my mouth from the tip to a few inches down the shaft. After a few seconds of this, Sir grabbed my hair and forced her cock to the back of my mouth, and down my throat, holding it there. I pulled hard against my wrist restraints, gagging on her cock and needing to draw a breath. Finally, she pulled back out of me and rested her cock on my head as I gasped for air and coughed, tears running down my cheeks.

"Rule number one of sucking off Sir," she stated firmly. "Do not, ever, use teeth, unless I tell you to. I don't know if you noticed, but this strap-on is double-ended. There's a large part of it inside me, and when you use teeth, I can feel it. When you use teeth, you will be punished." As I opened my mouth to acknowledge my understanding of her words, she shoved her cock right back in. "Don't talk. Just show me that you understand." I resumed my work, blushing with embarrassment. "Mm..." she moaned. "That's how you do it. Keep going, you dirty whore. I'll let you know when we're done."

At that moment, Mistress had apparently had enough being gentle, and began to fuck me a little more forcefully. My moans were stifled again by Sir's cock, and my own cock became a little harder with the increased force. It hurt a little more, but there was also a stronger feeling of pleasure. As Mistress fucked with more vigor, I found myself being uncontrollably shaken back and forth. I was completely and utterly her bitch, to be used and abused and fucked however she saw fit.

Sir continued to force me to suck her cock, and seemed to be satisfied that I was doing it properly. "I have a pretty great idea..." she mused. She pulled her cock out of me and walked over to whisper with Mistress as she continued to fuck me. I couldn't see, but I heard Mistress elicit an evil chuckle.

Sir took her place in front of me once more and grabbed my hair. "Ready?" she asked Mistress.

"Let's do it!" Mistress replied enthusiastically. Mistress started fucking me hard, as rough as I could possibly take it, rocking my body back and forth with the force of her thrusts, and forcing me to take in her entire length. Sir thrusted her hips as well, fucking my mouth and starting into my throat. My moans and cries of agony and pleasure were choppy, frequently interrupted by Sir's cock blocking my air. As they continued to fuck my holes with all the force they could muster, Mistress called out to me.

"Here's the fun part of all this. Well, one of the fun parts," she paused her speech a moment to take a breath while she continued to rail me. "I am not going to give you permission to cum, even though you are going to. We'll make sure of it." Any noise of disapproval I made was immediately blocked out by Sir's cock sliding up and down my throat. "Do you know what we're going to make you do when you do cum?" asked Mistress. "Even if you could respond, I wouldn't tell you." She paused her speech once more to take another breath. "It's a surprise!"

Before long, the pain I was feeling was starting to outweigh the pleasure. When I was worried I couldn't possibly take anymore rough fucking from Mistress, she grabbed my already hard cock and jerked it. It did not take very long, between the pleasure I got from being made into their bitch, the pleasure I got from the anal stimulation, and the pleasure from my cock being jerked, that I had a very powerful orgasm, releasing a substantial load. Mistress and Sir slowed down, before finally allowing me a break from their relentless fucking.

Sir stood triumphantly before me, legs apart, hands on her hips, her cock hanging loosely between her legs, my drool still dripping off it. Mistress had walked to a cabinet on one side of the room with what I could've sworn was a small container. I looked back up at Sir who asked me "What do you say, bitch?" I hesitated for a moment before looking down and replying, "Thank you, Sir." Despite the wonderful orgasm I had just had, I found myself instantly aroused at the thought.

"Don't thank me just yet," replied Sir with a grin. "You have one more lesson." Just then, Mistress returned with a strange device. It consisted of a medium-sized dildo closely modelled after a cock, and a hole on the top near the base, as well as one on the side. On the other side, there was a small switch. About halfway down the shaft was a strap, which had an odd shape to it. I soon found out exactly how the device worked.

"Open wide," ordered Mistress. I did as she requested, and she inserted the head of the cock into my mouth, and pushed it until my lips hit the strap. She made a few adjustments until she was happy with the end result.

The end result was that the strap was fastened around the back of my head, sealing a large amount of the cock in my mouth. The strap also covered my nose and prevented me from breathing through it. In fact, the only breath I could take was from a hole in the tip of the cock that lead to the opening at the top on the other end, and the opening on the side. I watched as Mistress flicked the switch on the other side, which sealed off the hole on the side. Then she flicked the switch again, opening up the hole. I was confused as to what exactly the device was supposed to do. Then, Mistress procured a small plastic bottle containing a fair amount of white fluid. To my horror, I realized it was my own cum, and started to figure out that my final lesson was in fact...

"Swallowing," Sir said, slowly stroking her girl-cock. She winked at me and took a step back, as Mistress took a step forward. "Here's how this is going to work. I'm going to attach this bottle to this end here," she pointed to the opening at the top. "Then, I'm going to flick this switch, which will shut the air hole here," she pointed to the hole on the side. "Do you know where your air will come from at that point?" I looked at her with all the begging eyes I could muster. "Very good! Your air will be a reward for swallowing Sir's entire load. Ready?" I went to take a deep breath, but attached the bottle and flicked the switch faster than I had expected.

I immediately found myself no longer able to draw breath through the cock. Having no other option, I sucked as greedily as I could, feeling my own juices leak into my mouth, down the back of my tongue, and into my throat. I winced at the taste, but continued to suck like the good little whore they wanted me to be, like the good little whore I was. I watched as the small bottle slowly emptied, and I briefly met Mistress and Sir's gaze. They were watching me, and holding each other close, caressing one another's tits and taking absolute pleasure in my total humiliation. As my oxygen began to fail me, the bottle had almost emptied. I took one last suck and managed to slurp some air into my lungs.

I continued to suck in all the air that I could, small amounts of my own cum accompanying it. I looked up again to see Mistress and Sir making out in between dominant glances at me. "You know what?" asked Sir of Mistress. "He looks pretty good with a cock in his mouth, and I feel like changing pace. Want to go have some fun while he gets used to his new position?"

"That sounds decadent," replied Mistress. "I was going to remove it, but I think even sucking air through it will give him some much-needed practice." She walked up and caressed the side of my face as Sir did the same to her tits and ass. "We're going to go play for a while. I want you to stay right her and practice what Sir taught you." I tried to verbalize a reply but the cock in my mouth made it impossible, and it came out sounding somewhat like moans.

"See, he loves it!" exclaimed Sir. "One more thing..." With that, Mistress went to the cabinet again and returned with two permanent markers. She handed one to Sir, who then wrote something on my right cheek, as Mistress walked behind me and wrote something on the left of my ass. As Sir stood up, she held her small tits before my face for a moment and dangled them around, arousing me even more. Then, I felt a familiar pressure against my already lubed ass as Mistress put her favorite butt-plug back in me. I moaned again, my cock stiffening, knowing I would not be getting release for a long time. As they walked out, Mistress gave my ass a hard slap.

As they locked the door behind them, I settled in, trying to achieve the impossible task of getting comfortable. Well, as comfortable as a guy can get with a cock in his mouth, a stinging ass, and being tied up bent over. Unknown to me, my face now read "Sir's cock holder" with an arrow drawn pointing to my mouth. My ass now read "Property of Mistress" and had a defined, red hand print just below the text.

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6 Comments
kagelo1kagelo1over 2 years ago

Great one, thank you!

tulsaguy113tulsaguy113about 4 years ago
More!

Please continue this series...I love your writing!

AnonymousAnonymousover 4 years ago
Two Sides Of The Coin

loving this story so far, would really like some more

and maybe the protagonist turning the tables a little?

AnonymousAnonymousover 6 years ago
Great story! Loved the way they left him.

Great story! Loved the spot roast and the way they left him until they're ready to come back for more. Permanent marker comments were a nice touch.

AnonymousAnonymousover 6 years ago
Intor to Sir

An interesting day with some spit-roasting involved with Sir. Just too bad Sir didn't turn out to be a Shemale. That would have made for an even more entertaining twist.

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