The last day of our trip started much like the previous. Allie was awake and energized by the time I woke up, doing her hair and makeup completely naked. While she was still beaming, her words were less kind this morning. “Good morning my bad boy. I’m not sure why you are the one sleeping in when I’m the one getting fucked all night.”
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I quickly pulled myself from the bed and apologized. “What can I do for you, Allie?” I asked obediently. “Can you come clasp my necklace?” she asked. “Easy enough” I thought to myself. I positioned myself behind her and began to fumble with the small clasp. This was the first time all trip she was wearing my chastity key necklace and I was excited to see her wear it.
As I worked to get it clasped, she pushed her ass backwards and wiggled it against my cock. “You were very bad yesterday, cumming without my permission is a big no-no.” Despite getting off yesterday, my horniness had not subsided in the least and this was driving me wild.
“You missed out on quite the show last night, I think Tomas permanently resized me. Do you think I’d even feel your cock if you fucked me right now?” she teased with a giggle. I had no words as she continued to rub her ass against my locked cock and I loved the humiliating comments. The smell of my wife was intoxicating and I was melting. She had me wrapped around her finger.
“Are you going to clasp my necklace or not? We have places to be!” she said, snapping me back into focus. I managed to secure the clasp and she turned to face me, the key to my cage hanging between her perfect tits. “Pool time, today will be the most fun yet” she said with a smile.
Allie had grown very comfortable at the resort and decided her necklace would her only attire on our last day. I followed close behind her as we headed to the pool, watching her ass lift and drop with every step.
As we reached the pool, it was packed with all of the husbands, wives, and boyfriends. In addition, the unpicked men from day 1 were also there. Tomas and AJ were standing together near where we had sat the day before and Allie made her way over to them. She jumped into Tomas’ arms and kissed him passionately while his hands squeezed her bare ass. He squeezed tightly, pulling her cheeks apart and giving me a quick view of her tight little ass hole.
When he put her down, she turned to AJ and greeted him with a smile. Like Allie, the men were also naked today and I could see her struggling not to stare at AJ’s cock. “Tomas told me your cuck messed up last night” he said in his deep, booming voice. “He will make up for it today” he added with a mischievous grin.
Allie giggled and told him I’d do whatever I needed to do to atone. “Tomas told me you can be quite dominant AJ, don’t hurt him” she added. AJ smiled his devilish smile and put his hand on Allie’s cheek, pulling her head up to his and kissing her deeply. She looked so small in his big hands and seemed like she was melting from his touch.
I wasn’t sure exactly what was discussed the night before but it looked like Tomas and AJ would both be satisfying my wife that day. As they kissed, AJ’s cock was brushing against her and I thought I could already see that my wife was getting wet. They broke their kiss and AJ gave her a sharp smack on the ass. She smiled lustily at him and I could tell she liked the dominant vibe he was giving off. The three of them entered the pool and I watched them mingle from a nearby lounger.
They flirted, kissed, and touched each other for what felt like hours in the pool. Allie bounced around excitedly between Tomas’ grip and AJ’s and I could tell she was excited to fuck them later. They were picking her up and carrying her around and throwing her over their shoulders, poking her ass up in the air for all to see. The physical chemistry was obvious and I could tell Allie loved being manhandled by them.
For a few minutes they had settled down and were talking in a tone I couldn’t quite hear. Allie exited the pool and made her way over to me, reaching out her hand as she stood in front of me. “Come with me, I’m ready to take them both back. AJ likes lingerie and said we should go change into our sluttiest attire and wait for them. He heard about your pink frilly panties and said you should dress up too.” I was totally embarrassed by this but tremendously aroused. My face red and cock straining in my cage to get hard, we made our way back to the room to get ready.
“Help me get ready!” Allie commanded as we entered the room. “You’ve only got panties to put on, mine has a lot of straps and they’ll be here soon!” I wondered what set she was talking about, I hadn’t noticed any lingerie that Allie had packed and I couldn’t recall anything strappy in her collection.
She reached into her bag and laid it out on the bed. “I bought it before the trip so they could fuck me in it” she explained. It felt odd that she had bought lingerie for other men to fuck her in but I was fully embracing being a cuck and loved that answer. “They will love you in it”, I replied warmly. Allie smiled and turned to me, “You’re a much better cuck than I thought you’d be. Now let’s get ready, we need to be ready by the time they get here!”
She stepped into the outfit, a bodysuit that was almost entirely straps. It was crotchless and the straps crossed up her body to barely cover her nipples in an “x” pattern. There was a strap at the waist that connected to two garters that snapped in place around her thighs.
As I knelt on the ground securing the garters, I couldnt help but admire her perfect physique. Her beautifully shaped legs and thick thighs sitting below her perky ass that had only grown sexier as our time together went on. She had always had a slender waist and her tits were large but perky. Friends of mine would always ask about her tits and try to sneak a peak whenever she was in a swimsuit or low cut top.
“Can I help you?” Allie asked with a big smile across her face. “I….uh…. Sorry I just got distracted.” “Clearly”, she said through a giggle. “Now go put your panties on, they’ll be here soon”. I found my bag and couldn’t help but laugh at how overpacked I was. Allie, like always, was right.
The bright pink was easy to find in my bag and I pulled the frilly panties on. “The smaller cage looks cuter in the panties. You should definitely hang onto that cage, it fits much better than your old one” Allie said sweetly. It was insulting but I loved the humiliating feeling that washed over me when she said that. “Thanks princess”, I replied softly.
Our conversation was interrupted by the sound of the door to our room opening. In walked Tomas and AJ, completely naked with their impressive cocks swinging as they walked. Tomas’ cock was truly incredible and gave me pause every time I saw it. It was thick, long, and smooth.
AJ’s cock was also huge but more intimidating. It was dark and thick with a large vein running up the shaft. “I’ve seen you naked all week but you are somehow sexier in lingerie” Tomas said in his smooth accent. “Both of you, bend over the edge of the bed” AJ commanded sternly with his powerful voice. Allie and I were both a bit caught off guard at first but assumed our positions, asses poked up in the air.
My wife’s boyfriends approached us and ran their hands softly over our asses. We both cooed and enjoyed the soft touch when Smack! Allie’s ass was firmly spanked by Tomas. Smack! This time it was my ass being reddened and AJ’s large hand was responsible. The men traded places and repeated this, Allie and I both yelping upon being spanked. “Go have a seat in the corner sissy boy” AJ commanded again.
I stood up and found myself in the arm chair off to the side. From where I sat, I could see my wife’s reddened, lingerie clad ass bent over the bed with two hung men standing behind her. In that moment I wished I had had a camera so I could capture the view.
AJ undid the strap around Allie’s waist and began to blindfold her with it. “How long have you dreamt of being manhandled and fucked by two men?” He questioned as he pulled her head back and tied it securely. Not waiting for an answer, he added “I knew from the first day I saw you that you desperately desired the cock of a hung, dark man. And tonight you’re going to get it”. He almost said it in a growl and Allie let out a soft moan as he kissed her neck.
Tomas began to shift around to the head of the bed and climbed in front of Allie. She knew what was coming and her mouth opened in preparation for Tomas’ cock. AJ had shifted over some and was directly behind Allie, his cock pressed up against the back of her legs and ass.
She was lifted up by the hips and placed on the bed in the doggy position. Tomas still had not put his cock in her mouth and my wife began to beg for it. “Please Tomas, I want to suck on it, pleassseeee.” He laughed and called her his little slut, gently placing his hands around her head and thrusting his hips forward. Her jaw hung open as wide as it could and Tomas began to slowly fuck her mouth.
Even from the corner of the room I could see her pussy start to drip and run down the back of her thighs. AJ had also noticed this and ran his finger up from just above her knee, collecting the lubrication before reaching her pussy and sliding his finger inside her. They were both firm but gentle in how they handled her and she appeared to be lost in another world.
AJ slid a second finger inside her and rubbed her clit with his thumb while he curled his fingers against her G Spot. My beautiful wife bucked her hips in pleasure and moaned around Tomas’ cock. The moans turned to whimpers and she began to shake as AJ was hitting all the right spots. He was an expert with his fingers.
She spit out Tomas’ cock and dropped her head as she let out a loud moan and began to squirt. Her moan trembled and her body tensed and writhed on the bed in pleasure. AJ stood behind her stroking his massive cock and began to position himself to fuck Allie.
She pleaded with him to give her a few minutes because she was really sensitive and AJ obliged. He turned to me, “crawl over here cuck, you’re going to keep me hard while I wait.”
I dropped to my knees and crawled over, poking my ass in the air like a good sissy. As I crawled, I could feel my little caged cock rubbing against my thighs. I stopped in front of him and looked up at him stroking his enormous cock inches from my face. “Suck it” he said as he looked down at me.
I parted my lips and began to take him into my mouth. Allie would occasionally fuck me with a strap on and I had sucked her big fake cock before so I felt confident I could keep pushing him deeper into my mouth and throat. I wanted to impress him and sucked and slobbered all over his cock as I rhythmically took him deeper and deeper into my mouth.
AJ seemed to be enjoying my efforts as he tilted his head back and sighed, “fuuuuccckkkk”. I heard a muffled giggle and glanced over at Allie, whose blindfold was now off and she had Tomas’ cock in her mouth. “He’s been practicing on my big dildo at home” she bragged as she came up for air. The men laughed and AJ told us he could tell. He looked at Allie, “are you ready?” he asked. My wife smiled around Tomas’ cock and nodded to AJ.
“Lead me to her, panty boy” he ordered. With one hand on his cock, I arose to my feet and led him over to behind Allie. He positioned himself behind her on the bed, “Guide it inside her” he said dominantly. With my grip around the base of his huge shaft, I pointed the head at my wife’s pussy and rubbed it against her lips.
She was dripping wet and you could hear her wetness as his cock rubbed against it. I pushed the head of his cock into her and her pussy resisted until her body relaxed enough to let him inside of her. “Ugggghhhhh” she groaned as AJ opened her up.
She was being spit roasted by the two handsome men and looked like she was in heaven. Her butt was arched up in the air and her head was cocked back, accepting Tomas into her throat every time AJ thrusted forward. He quickly made his way deeper inside her until his hips clapped up against her ass. His grip was tight around her waist and she was fully in the control of the two men.
I kneeled next to them and watched closely as AJ impaled my wife over and over again. His big balls smacked up against her with each thrust and she lost the ability to suck Tomas while this was going on. She grabbed the sheets tight and moaned loudly into the bed. Allie was completely overwhelmed by his size and couldn’t focus on anything aside from being fucked.
Tomas, needing attention paid to his cock and seeing how I sucked AJ before, signaled me over to the side of the bed. He met me there and pushed me to my knees in front of him, grabbing his cock and placing it on my lips. I didn’t require any more direction and began to suck him with vigor.
He groaned and muttered something in Spanish while AJ continued to pound my wife next to us. I looked just past Tomas as I worked his cock and made eye contact with Allie while she was fucked relentlessly. Her eyes were dazed and she appeared to manage a slight smile through her moaning and heavy breathing. AJ’s grunts became deeper as he sounded like he was about to shoot his load deep inside my wife.
Allie began to shake as her orgasm swelled and Tomas began to fuck my mouth with both of his hands on my head. His grunts also started and he cried out “fuck I’m going to cum!” Just as I felt his load shoot into my mouth, AJ pulled my wife all the way down on his cock and he unloaded his balls inside of her. Feeling him cum was enough to send her over the edge and she squirted again as her legs shook and her body tightened.
His big strong body collapsed on top of her petite frame and they laid in a crumpled heap on the bed. Tomas allowed me to suck every last drop of cum from his cock and finally pushed my head away when he had enough. I had tasted him all week and was once again happy to have a mouthful of his cum, even if it didn’t come from my wife’s pussy. I swallowed it down and smiled up at him as he chuckled and shook his head in disbelief.
“It’s time to leave them”, Tomas said to AJ. He pulled himself off my wife and slid his cock out from inside of her. She gasped as it left her and he gave her a parting smack on her ass. A big red hand print marking the woman he had just claimed for himself.
The men left us and I cuddled up behind my wife for the third night in a row. “You’ve been such a good husband this trip” she said in a tired voice. “Take my necklace off and unlock yourself. You can fuck me tonight as a reward.”
I couldn’t believe what I was hearing and once again fumbled with the clasp in excitement. The necklace was removed and my cock was unlocked and free in seconds. As soon as the cage was removed, my cock began to swell and harden impatiently. Allie laid in front of me, smiling back at me with a sleepy face as she poked her ass back.
I pushed my hips forward and my cock slipped easily inside her dripping wet hole. My first thrust had me balls deep in my wife and rather than moan or yelp, she giggled and asked if I was all the way in. “Usually it takes me a second to be able to take you all the way, I hardly feel you”.
This humiliation and knowing the fucking my wife just received was too much for me. I had waited weeks to fuck her and watched as she pleasured other men all trip and I was about to blow my load in seconds. “Fuuucccckkkkkk” I exclaimed as the most intense orgasm of my life washed over me.
My cock twitched and pulsed uncontrollably while Allie laughed softly and took a deep breath as if she was dosing off. “Go lock back up. You’re a much kinder partner when you’re desperate and I think you’re going to stay locked”, she said softly as her tired state was getting the better of her. Never had chastity been a 24/7 arrangement for us but at that point we both knew our sex life would be different moving forward.
I put my cage back on and gently clasped the key back around her neck. Settling into bed, I grabbed my wife tightly from behind and nestled my tiny caged cock between her cheeks. “I love you honey” she whispered softly. “I love you too” I whispered back as I pulled her in tight. We drifted off to sleep, concluding a vacation we would never forget.
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