Cuckold vacation

Updated: Feb 26

I couldn't believe my luck. My wife was next to the bed and we were talking about our day before drifting off to sleep when she broke the news.

"I think it could be fun." She had said. I had brought up the idea of a vacation to a nudist resort a couple years back. she had been adamant about her initial response. "No way!" She'd said. "No way I'm parading myself around a bunch of naked horny disgusting men all week!"

After months of recent pressure and pleading, it looked like something had changed her mind. "It would be like the beaches we went to on our trip to Europe, but for the whole week."

"What made you change your mind?"

"Well, you know how the nude beaches we've been to have made me feel...objectified. They let anyone into those things and the men are always so...unrestrained."

It was true. The men were always ogling the women, following them along the beach, and making lewd comments. They never did anything to hide their inevitable erections either.

"Well, I found a different kind of resort." Anna continued. "This one respects women by keeping the men more in check. Everyone goes through an entrance assessment to weed out the perverts and single people. They guarantee the women will feel safe and the men are behaved."

"How do manage that?"

"That's the, uh...different part that you'd have to get used to..."she said nervously. She rolled towards me on her side and draped her soft, naked leg over mine. "In order to keep the men...subdued..." She caressed my stomach lightly and trailed her finger toward my manhood as she continued. "They have all the men wear a chastity device." With that, her hand reached its destination and she softly cupped my balls.

"What?! No way am I doing that! Nuh-uh." I said immediately.

"Honey, just think about it! It's the only way you're ever going to get me to go to one of those resorts. This way we can relax and have a good time without worrying about other people bothering us." She moved her hand back to my chest and brought her leg up until it was pushing gently against my balls. "And besides, hasn't it always kind of been your fantasy?"

She had me there. Soon after we got married I'd confided in her about my submissive side. For the past few months we had really been playing it up. Nothing too extreme--she would take charge during sex and I'd let her do whatever she wanted to me. More accurately, I'd end up doing whatever she wanted me to do to her. She really liked to be in control. One of her favorite things to do was tie my hands behind my back and tease me relentlessly. She even went so far as to make sex all about her during these fantasy sessions. She would force me to bring her to orgasm and sometimes deny me a release completely. At least for a day or two...she never let me go too long.

"Yes, that's my fantasy with you." I replied. "But you said you could never actually lock me in chastity. Besides, at a resort is totally different."

She smiled slyly at me and returned her hand to my manhood. "About that...I've really enjoyed how submissive you've been lately in bed. Giving up your orgasms for me at will. Watching you get all horny and frustrated when I tease you. Knowing that there's nothing you can do about it until I decide to let you cum. I was thinking it might be time to take it to the next level. What do you think?" At this point she was whispering sexily. Between the things she was saying and her warm breath in my ear, my penis began to harden in her hand. "I'll take that as a 'yes'." She whispered coyly. "Besides, saying no wouldn't make me happy...and you want me to be happy, don't you?"

"Of course I do honey." I stammered as my erection grew to full attention.

"Then it's settled! We're going to the resort!" She squealed, squeezing my dick tightly before rolling over away from me. "What about this?" I asked, pointing to my erection. She glanced over her shoulder at my throbbing cock, laughed, and said "Don't worry, it will still be there in the morning."

I tried in vain to ignore my burning erection as my mind raced. What the hell had I gotten myself into?

I turned the car off the paved road and on to a narrow gravel drive leading to the resort. It was a further 5 miles before we reached the welcome center. I was relieved to finally be here. The drive had only taken four hours, but she had not made it an easy one. Or an easy week for that matter. It had been 3 days since she revealed her plan to me, and we hadn't had sex since 2 days before that. We both liked to take a small break leading up to a vacation...the anticipation made it all that more exciting once we finally arrived at a new place and made love. It always started off our vacations on a high note and led to lots of wild sex for the duration of the trip.

she had been sure to wear her most "comfortable" clothes for the car ride; yoga pants and a tank top. I'm sure she'd picked her outfit just to provide the most torment for me. Her light gray tank top had spaghetti straps and one of those built in "bras" that gave her just enough support, but not so much that her breasts didn't jiggle and bounce over the bumpy roads as they strained against the thin material. At 34d, her breasts were firm, yet very soft, and just heavy enough to create a beautiful, tear drop shaped profile in her shirt. And the pants, well...

"There," she pointed. "That's where we check in." The building was very beautiful, surrounded by palm trees and shrubs typical of central Florida beaches. As we walked toward the brightly painted building, I couldn't help but stare as she walked slightly in front of me. Her purple yoga pants were those relaxed fit kind, the kind that are tight around the ass and upper thighs and then fan out down the legs. Anna had one of those round, bubbly asses that had a way of filling out whatever material she squeezed it into. At 5' 5" and 140 pounds, she was far from overweight--but she had just the right amount of cushion in just the right places. Her waist was average at about 28", but it gave way to curvy, shapely hips and deliciously thick thighs. She was quite proud of her ass; she was always doing squats and exercises to maximize what God gave her. But it wasn't hard and overly was soft and supple, with a round, full shape that caught your attention and kept it there. Her thighs were soft and full to match.

"Hey," she said, snapping me out of my trance. "There will be plenty of time for that later." She winked and playfully slapped her butt, causing it to jiggle in the skin-tight confines of her thin yoga pants.


"Right this way."the woman from the front desk, led me down a hallway off the lobby and into what was basically a doctor's exam room. Anna had been taken another direction by another woman. We were to be individually assessed by the staff before being shown to our room.

"Please strip naked and put on this gown. The examiner will be in shortly."

I did as instructed and sat on one of the 3 stools in the room. Soon, an older woman in her late 40's dressed in nurse's scrubs entered, followed by a much younger woman dressed in street clothes.

"Hi, I'm director Miller and this is our newest trainee, Aimee. She's going to assist me with your entrance exam if that's OK."

"Sure," I said nervously. I had no idea what all this was going to entail.

Director Miller proceeded to ask me about 20 questions about my relationship with Anna, whether or not I had ever been to a place like this before, etc. Finally, she started covering some of the resort rules.

"Our resort is uniquely run in a way that is female friendly. Do you know what that means?"

"Not really."

"We find that men are generally much more comfortable in a nude environment than women at first. So to help women feel at home, there are separate rules for each gender. For men, this a clothing restricted resort, meaning you are required to be nude from your head to your feet at all times. Women do have the option of covering up, except when actively swimming in the pool or beaches. We encourage them to go nude as frequently as possible in order to experience the full resort atmosphere, but don't require it."

"Why can't men cover up?" I asked, surprised.

"90% of men who want to go to a nudist resort never get their partners to agree, so we let the women set the rules here. They feel more comfortable if they retain some control of the environment...and their men." She smiled. "To that end, we also employ the use of male chastity devices. Have you ever worn one before?"

"Um, no."

"Well, it should only take a couple minutes to apply. I need to start with the next exam, but Aimee here can finish up. Please stand and remove your gown, and we'll get you fitted."

I was shocked. "Y-you do it?" I stammered.

"Yes, that way we ensure a proper comfortable fit. I'll be back to check on you."

Director Miller left, and Aimee turned to the cabinets behind her and gathered some equipment. I stood and nervously removed the gown.

Because I was now standing, when Aimee rotated her stool back to face me, her face was right at my crotch level. Aimee paused when she first saw my shaved pubic area, her gloved hands in mid-air on their way to their destination. I thought I saw a smile in the corner of her mouth as she continued.

"First I'm going to attach a base ring." She selected a plastic ring from a box on her tray and proceeded to secure it behind my balls, against my body. As she did so, her eyes drifted upward until she was looking directly into mine. It was then that I first realized how absolutely stunning she was. She had big, deep emerald green eyes with long lashes, full pouty lips, and dark reddish-brown hair that cascaded down the sides of her face. From my vantage point, I could see directly down the front of her scrubs to her ample cleavage. I gulped and averted my eyes, but not before Aimee noticed where I had been looking. She definitely smiled that time.

"Now I'm going to fit the penis tube." She turned to the equipment tray again and I noticed a selection of different styles. There was an assortment of colors and sizes, some of which looked impossibly large.

"Are some of those for uh, erect...?" I asked, my voice trailing off.

"What, these?" She pointed to the larger ones. "No, they're just for different size flaccid penises. Each one is color coded. Clear is the smallest, then white, green is average, then blue, black, and finally red for the big ones. Penises do come in all sizes; some can be quite large...or small." She smirked as she looked directly into my eyes. She picked up the largest of the devices, which must have been +6" long, and to my horror, she brought it to my own penis and held it right beside my modest size. "See, with this one you could probably obtain a full erection quite easily, with room to spare."

I couldn't believe she had said that, even if it was true. Actually, I thought my erect cock would fill most of the plastic sleeve, but flaccid it probably would look mostly empty. The girth looked to be 2 times the size of mine. She held it there a few seconds longer; she seemed to be really taking in the comparison. My face was red with embarrassment, but a strange thing happened... I felt a stirring in my balls. No! My mind panicked. All this attention was having an effect on me. I felt my cock fill with blood and it began to lift itself upward. I desperately tried to fight it off, but to no avail. Aimee stared as my penis grew to full attention, which took all of 5 seconds. I'm a very fast grower, and get very stiff very quickly. My cock was throbbing with my heartbeat and pointing straight up. "See, this large size wouldn't do at all." She was right-- my penis looked ridiculously short and thin next to the giant hollow tube she held.

Finally, she exchanged the monster size device for the green average size in the middle of the tray. She held this to my cock for a few seconds before shaking her head and exchanging it again for yet a smaller size, the white one. There was only one smaller size remaining.

"I think this small one is about the right size." She said, fully aware of the implication of her words. I was mortified-- here was an extremely attractive young woman fiddling with my privates and mocking the size of them.

"OK, looks like I'll have to apply some calming lube to get this on." She squeezed some clear gel from a tube onto her gloved hand. She quickly wrapped her fist around my cock and pumped it a few times to distribute the fluid. Almost instantly, my penis began to shrink...and shrink...and shrink until it almost disappeared entirely.

She proceeded to lift my cock with just her thumb and forefinger and slip it into the white plastic tube. She attached it to the base ring using the pegs extending along the top of my cock. Just then, Miller returned to the room.

"Let's see how you've done, Aimee." Miller rolled up to my crotch on her stool. She lifted the end of the tube and peered into the small hole in the end and at my penis inside. "Hmm, it seems a little loose. Let's try the next smaller size." Aimee removed the tube and switched it for the smallest size possible.

"Are you sure I need this one?" I groaned. "It's the smallest one."

Miller quipped back, "This is also the smallest penis we've seen today." Aimee smirked at me from behind her. "Now if you want to stay at the resort you'll have to do things our way." With that, she pulled a small metal lock through the holes in the device and snapped it shut.

"There, all finished. You can get dressed and go meet your wife in the lobby. She will have a key to the lock of she wants to use it in the privacy of your own suite."

I wasn't sure if she meant my wife would want to use the key or my cock, but I guess it didn't matter. As they stood and left the room, Aimee turned back to me, winked, and whispered, "Have a nice little stay!"

I dressed and headed down the hall to meet Anna. "How was it?!" She asked excitedly.

"Fine," I mumbled with my head down. "Let's just get to our room."


I parked the car near our building and got the bags from the trunk. she had the key card. "Suite #205. Second floor. This way." She led us to a stairway, and started up. I couldn't help but stop at the bottom and watch as she continued. I had a perfect view of her ample bottom as it rose and fell with every step. I couldn't wait to tear into her.

We reached the room and I dropped the bags. she squealed and turned to me, throwing her arms around my next. "I'm so excited! This place is gorgeous!"

"Not as gorgeous as you, babe." I drew her to me and kissed her passionately. She fluttered her tongue around mine and caressed the back of my head. My hands dropped down her back and rested on the shelf created by the swell of her ass. I felt my trapped cock grow in its cage. It must have pressed against Anna stomach, because she broke our kiss and pulled away.

"Oh, right! Can I see it?" She asked.

"I-I guess. It's kind of embarrassing."

"Well I'm going to see it eventually. And so is everyone else."

She dropped to her knees in front of me, unfastened my belt and lowered my pants. She hooked her thumbs in the waistband of my boxers and yanked them down. The chastity device popped out wildly and bounced inches from her face.

"Oh, wow!" She giggled. She reached out and slowly moved the device around, studying it. "Does it hurt?"

"No, it's a little uncomfortable. It's weird to have something pulling my balls away from my body and trapping my cock. It feels heavy."

"I think it looks hot. And kind of cute. Can it get hard in there? You have some room you know."

I looked down and sure enough my flaccid cock filled only 1/2 the length of the 2" clear plastic. You could easily see the size and shape of my cock. I groaned and sank onto the bed.

"What's wrong honey?" she curled up beside me and played her head next to mine.

"Most of the other cages were solid colors. Everyone will be able to see right through mine."

"Um, it is a nudist resort. I'll be completely naked you know."

"Yes, but it's humiliating to wear this thing, it's like my dick is on display. Somehow it's worse than being totally naked."

"Wait, why is yours clear? Why didn't you just pick a solid color?"

"I didn't have a choice. They were, um... color coded by size."

she lifted her head and looked up at me with a knowing, sly look. "So what size is your little man sporting?"

I didn't know how to answer. On one hand, I didn't want to admit the truth. On the other hand, she knew about my humiliation fetish tendencies...but she had never explored the issue. I wasn't even sure she remembered.

"There were 5 or 6 sizes...they were all solid colors except this one. I guess because it was the smallest." My heart was racing as I admitted my shortcomings.

her mouth gaped open surprised and she gave me what might have been a genuinely disappointed look. "Oh...really?"

"That's not a problem is it? You've always been happy with my size, right?" I was getting nervous about her answer.

She smiled and dropped her hand down to cup my caged cock and balls. Her hand easily covered my entire package. "Of course, babe. I love my little man." She kissed me slowly and deeply as she rolled my balls around with her fingers. I knew her palm was lying right on top of my cock, but I felt nothing through the plastic. All I felt were her nails tracing around my scrotum as she made out with me. She moved to my neck and kissed it softly. Man, she really knew how to tease me and get me all worked up.

"Oh, the past 6 days have been torture. I want you so bad." I moaned.

"I want you too. It's so hot thinking about that nurse embarrassing you today."

I pulled back slightly, shocked. "Y-you remember that?"

"Remember what?" She whispered, kissing my ear lobe. "Do I remember how you wanted me to humiliate you? How you asked me to talk about your cock...and how small it is?" I moaned loudly at that, which she took as a sign of agreement. "You thought I wouldn't remember," she continued. "But how could I forget? Every time we have sex I'm reminded of just how small you are. I think you know that, right?"

"I-I'm average I think." I don't know if I was trying to save face after the woman I loved told me my manhood was small, or if I was playing along, drawing more words from her.

"Ha! Average? I don't think so sweetie. Even if you were, that wouldn't be anything to brag about. No woman dreams of an "average" cock. No, I love you honey, but we all have our shortcomings, so to speak." By this time my cock had filled the plastic tube and was straining desperately for an erection. Instead, it just caused the base ring to pull my balls forward painfully.

"Ooh, I guess your cock agrees. It's giving you away; even of you won't acknowledge I'm turning you on."

"I can't think of a single shortcoming you have," I said honestly.

"Oh, that can't be true. There must be something you would change about me if you could. Even a little? You can be honest." Anna traced her fingers around my chest and gave me her best puppy dog eyes.

"No, babe, nothing. When I think of the perfect woman I picture you." It was the truth.

Anna blushed slightly and smiled. "That's so sweet. What is it you like the most? Physically."

"Well, your face is beautiful and your eyes are so piercing blue. I love to run my fingers through your long wavy hair. It contrasts your smooth fair completion so well."

She giggled and nuzzled up even closer to me, pulling her leg up until it pushed upward against my balls. The slight pressure that caused made my cock strain even harder in its plastic prison. "What else? This is fun!"

"I love the way you can look so damn cute and hot as hell at the same time. You've got that girl next door look, but with a body that just begs to be fucked." With that, I pulled Anna up and onto me in a quick swoop. She leaned down and we kissed like horny teenagers. My hands moved from her soft curvy hips up the sides of her trim waist and found the rounded swell of her breasts. she moaned into my mouth and I knew I had her. My hands moved to the front of her thin tank top and her breasts filled my hands. I massaged them gently, but avoided her nipples. I loved to tease her.

She broke the kiss and leaned back. She cupped the underside of her boobs, lifting them up, and asked "What about these? They could be bigger." She jiggled them a few times and the exposed flesh at the top wobbled like Jell-O. Her nipples were hard and clearly visible through the thin gray material.

"No way. Any bigger and they'd be droopy. They're the perfect handful."

"That's not saying much with the size of your hands..." She smirked and ground her ass against my caged cock. She slid her hands down to her hips and squeezed them. "And my hips...?" She prodded. I loved how her hips widened in this sitting position and the way her thick thighs spread across my stomach. Even with her legs spread, her purple yoga pants were so tight against her pussy I could see the small flower print of her panties through the thin material.

"God, I love your curvy hips. You know I can't keep my hands off them." It was true, I was always wrapping my arm around her when we walked, resting my hand on her hip and my arm across the top of her bubbly ass.

She moved her hands behind her and put on a pouty face. "But I know you think my butt is too big." She feigned a frown.

"Ha-ha, that's funny!" I couldn't believe she had gone there. "You know how perfect I think your ass is. You have just enough muscle from all those squats, but they're hidden under all that soft round bubble butt layer. That's what gives you such an awesome walking booty." She knew exactly what I meant. I had told her many times before how sexy she looked as she walked, her ass cheeks rising and falling rhythmically, even rolling left and right with each step at the top and bottom of their travel because there was just too much meat there to contain. Honestly, the way her ass danced when she walked truly was mesmerizing. I know it probably sounds like I'm describing a fat ass, but hers was a true "phat" ass. It wasn't flabby or out of round. And remarkably, there was zero cellulite dimples. Most women understandably have at least some dimples when their muscles flex, but not Her She was blessed with perfectly smooth, unblemished skin not just on her back side, but her whole body.

"Hmm, I'm not sure I believe you." she continued to frown as she climbed off my lap and stood by the edge of the bed. She looked back over her shoulder at me and rose up on her toes as she caressed her ample cheeks with her small hands. I knew exactly what she was doing. Her butt was her most sensitive erogenous zone...there was no faster way to turn her on than for me to play with her butt and thighs. I swear she could almost orgasm from an ass massage alone.

I sat up on the edge of the bed and touched a hand to her ass. She backed up toward me, causing her ass to bounce as she parked it just inches from my face. I slowly began caressing a check with each hand. She bent forward and back slightly as I explored her leggings-covered posterior. My hands roamed down the sides of her hips, and up the backs of thighs until they rested in the crease at the base of her glutes. I lifted upward and felt the weight of her round cheeks in my hands as I jiggled them back and forth. My thumbs rested in the inside of her thighs, lightly grazing the lips of her pussy.

she moaned with desire. "Oh, Tim, you know how to drive me wild!" She spun around to face me, which put her pussy level with my face. I looked up into her half-closed eyes as I grabbed her ass firmly and pulled her pussy mound right into my lips. She grabbed my hair with both hands and pulled my face tight to her. I breathed in deeply, her sweet intoxicating aura filling my nostrils and making my head spin with lust. I kissed her mound softly, circling around her clit, teasing her. I had to taste her. And she had to be tasted.

She stepped back and turned so her back was to me, hooked her thumbs into the waistband of her tight yoga pants, and shimmied out of them in the sexiest way possible. She was left with a pair of white cotton panties that were probably 2 sizes too small. As she stood up straight again, the panties gathered in the deep crack of her ass, one side disappearing almost entirely and leaving half her ass hanging out. She faced me, slipped her panties to the side, and walked her pussy right into my waiting mouth. All thoughts of teasing aside now, I devoured her pussy. Licking, sucking, smacking, kissing and flicking my way over her sex, I worked from the back to the front to the back again. she was writhing against my face, smearing her abounding juices all over my face. I drank her in like a savage. I couldn't get deep enough, fast enough, wet enough. After only 1-2 minutes, her orgasm started. It didn't build slowly and gently; no, it hit like a freight train. Her knees buckled and she fell forward on the bed, trapping my head under her. I licked and sucked ever more fervently, grabbing her panty-clad ass in both hands and pulling her in as tightly as possible. She grunted savagely and ground her pussy against my mouth. After what seemed like an eternity, Anna slowed her movements gradually, shuddering as she came down from the most powerful orgasm she'd ever experienced. She rolled off me and onto the bed, panting heavily, her eyes closed and mouth gaping open. She looked absolutely stunning with post-orgasmic glow.

I knew better than to rush her, but at the same time my cock was throbbing with pain. I looked down at my swollen purple balls and trapped penis. It too was purple and swollen, the head trying to squeeze itself through the pee hole at the end of the tube.

I lay next to her and she sighed deeply and smiled. "That was...amazing! I had no idea a person could cum that hard! Your little penis could never have done that"

"Well, I'm glad my mouth is useful to you!" I said with more than a hint of sarcasm.

"Hey! I don't like that tone, little man! I might just never let you cum again! You know better than to talk back to me in bed!" Yes, I did. All too well. For our last anniversary I had treated her to an all-day pampering session that led to me pleasuring her for 2+ hours that night. In the morning, I had asked for some relief of my own. She was extremely disappointed in my lack of sacrifice and self-restraint and didn't let me come for 2 weeks.

"I'm so sorry honey! I loved giving you so much pleasure, even if it was only with my mouth. But look at my cock! I haven't cum in a week and I'm busting out of this stupid cage! Please unlock me! I need to cum so badly!!" I slipped to my knees beside the bed between Anna's legs and pleaded with her. "I'm desperate!"

Her gaze softened and she raised herself on her elbows to look at me. "That does look painful. I'm sorry hun, you know how I get carried away sometimes. Give me the key and I'll unlock you."

My face fell in disbelief. "What?!" I cried. "I don't have a key! They said they gave you the key!"

"No, they never gave me the key."

My head dropped onto the bed, and I cried out in frustration, "Nooooooo!" My sexual appetite was through the roof, with no way to relieve it or bring it down.

"There, there baby. I know how frustrated you must feel. I've teased you all week with no release and now you've just eaten me to the best orgasm of my life! You must be ready to explode!" She paused and looked at the clock on the bedside table. "But it's 6:00, and the front desk is closed...we'll go see about getting your key first thing in the morning."

I moaned, dejected and beaten down. I crawled onto the bed between her legs and laid my head at her thighs, inches away from her wet and tired pussy. I breathed in the rich scent of her orgasmic juices, and wondered how I would make it through the night.

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