Chastity Resort Pt. 08

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Free day from chastity. Anna takes it a step further w/ Chad.
5.6k words
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Part 8 of the 8 part series

Updated 06/07/2023
Created 02/09/2016
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"I don't know about this..." I said nervously.

Anna stepped back and looked my naked body up and down. "You look good, babe. Great, actually! What's the big deal, anyway? It's not like anyone else here is wearing clothes!"

"It's different," I insisted. "This is a chastity resort. All the guys are wearing cages...I know it's not much, but when I'm the only one NOT caged...you feel more exposed."

"How do you even know? It's not like we've ever done this before!" My wife laughed.

She had a point. And what did I have to lose? It's not like I would see any of these people at work on Monday. I'd probably never see them again, except maybe Chad and Lisa. So I might as well have a little fun.

Anna grabbed her beach bag, I grabbed a towel, and we headed out.

The walk down to the boardwalk was like any other morning. Nevertheless, I was quite nervous. Was it just my new vulnerability, or did a lot more heads seem to be turning as we walked by the other beachgoers? I felt like all eyes were on me as Anna led us to a couple of chairs. I hastily sat down and laid my towel over my lap.

Anna adjusted her lounge chair flat and layed down, face up. Her eyes were hidden behind dark sunglasses, so I wasn't sure if she was watching me as I stared at her or not. But I couldn't take my eyes off her. Her long wavy brown hair lay over her shoulders and trailed down her chest, framing in her large, soft breasts. Her pink nipples were peeking out of her locks and you could see the swell of her very full boobs as they fell slightly to her sides from their own weight. Her soft, flat stomach gave way to curvy hips and thick, delicious thighs, between which was nestled a small tuft of trimmed pubic hair. I was so engrossed I didn't notice Lisa and Chad walk up beside me.

"Good morning, guys!" Lisa said cheerfully. "What are you up to today?"

Anna rolled towards me and looked up, her breasts falling together and her hips rising off the chair. Her top leg dropped forward, giving us a fantastic view of her thick leg curving around to her backside.

"Just relaxing, waiting for you. And this guy has been oogling me for 20 minutes straight!". She tugged at the towel on my lap playfully. I gripped it tightly, embarrassed to know I'd been caught.

"Haha!" Chad laughed. "I don't blame him!" Lisa slapped his arm.

"Anyway..." Lisa smirked at her husband. "You up for some morning beach side yoga?"

"Sure! You coming this time, honey?" Anna asked.

"N-no, I don't think I...I don't think I should...right now..."

I glanced at my crotch, which was sporting a small tent under the towel.

Lisa laughed. "Yeah, might want to sit this one out!"

Anna stood and put her hair in a ponytail. With her arms raised above her head, her breasts jutted out and jiggled back and forth as she tied her hair up. I gulped and felt my dick throb.

"Now no funny business while I'm gone. No touching MY property now that it's unlocked!" She pointed at my lap. "I'll be right over there, and I'm keeping an eye on you, mister." She leaned down and kissed my cheek.

Anna, Lisa, and Chad walked about 100 feet down the beach and joined a small group of people gathered there. They spread their towels on the sand and started stretching.

As Chad turned sideways, I was shocked at first at what I saw. Then I remembered that he, too, had won a cage-free day of total nudity with no chastity device required. That meant his impressive manhood was on full display. Even though I had seen him nude a few days before at the hot tub in their room, I was stunned once again at the sheer size of his endowment. His thick cock hung down past his large balls in a slight arch. It must have been 6 inches long at least, and he was completely soft.

They all sat on their towels, with Chad between the two ladies. As they moved from position to position, I tried to think about something else, anything, to keep my mind off the display before me. As Chad moved and posed his muscular, tanned body, his flaccid penis swung and swayed obscenely. It looked so heavy and thick as it jutted out from his stomach impossibly far. It looked like something you'd find attached to a porn star.

And Anna, posing right next to him with her round, plump ass and hanging breasts also on display...only served to remind me of what I had seen the night before...my wife dancing all over Chad, her panty-clad ass bouncing on stage, smothering his face between her boobs. And him-- grabbing her butt and sliding his caged cock along her naked pussy as she gyrated in his lap...God, it was hot! I felt strong pangs of arousal. Even though I'd had a huge ruined orgasm the night before (unintentionally), I was just as turned on as before. It was as if that release hadn't counted at all.

I had to fight off the urge to touch myself. Anna was preoccupied with yoga and no doubt sneaking glances at Chad. She wouldn't notice if I just gave it a quick tug or two, right? I literally had not touched my own penis since first being locked up five days ago. Not even to piss--I had to do that while in the cage. And every time Anna wanted to fool around, I was first tied to bed.

I looked nervously around the beach. There were only a couple people around...no one would notice. I lifted the towel from my lap and peaked underneath. My dick was red and swollen, the head looking like a small viper staring back at me. I sighed and dropped the towel and threw my head back. I couldn't do it. I honestly didn't WANT to do it, that is what surprised me most. Anna really had a hold on me with this female-led relationship thing. I was shocked, but I was actually enjoying chastity. I didn't want to mess this up, not with the sex between us better than it had ever been.

I laid back, closed my eyes, and tried to forget about it. After about 10 minutes I realized my dick had gone completely soft, thank God. The yoga group was still going strong. I decided to get some drinks for everyone so I wouldn't just be sitting there staring at naked bodies and getting all worked up again.

I stood and began walked back toward the boardwalk. As I approached the stairway, I cursed under my breath when I noticed one of the beach attendants "standing guard". Sure enough, when I got to her, she asked me to remove my towel.

"Just a reminder, sir, male clothing is prohibited in public spaces."

I hesitated for a few seconds, with my hand on the towel, before reluctantly removing it and hanging it over the railing. The woman couldn't help but glance down, and a smile (or was it a grin?) appeared on her face.

"Thank you. Have a nice day!"

"You, too," I mumbled.

As I made my way down the boardwalk, totally free and unencumbered by a chastity cage, I was acutely aware of everyone I passed eyeing me up and down. Most were probably just curious as to why I wasn't caged like every other guy there. At least, that's what I told myself.

I noticed a group of young women sitting in an outdoor patio of a restaurant; they looked vaguely familiar. As I approached, one by one they looked up and stared as I passed by.

"That's him! That's the guy from the elevator the other night!"

"Hey!" I was close enough for one of them, a pretty little blonde, to grab my arm and stop me. "Why are you...free?" Her girlfriends laughed.

My face turned red as I stammered, "I-I won a contest. At the bar. Last night."

"What kind of contest?"

Another girl from the back piped up. "I bet it was a small dick contest!"

The table erupted in laughter. My face turned bright red. I was frozen in place, facing their table, my small soft dick pointing out at them over my balls. It didn't hang down like Chad's had; not at all. My small testicles barely hung down at all and my wrinkled penis sat atop them, jutting straight outward. The attention from them, even though it was negative, was somehow enjoyable. I've always liked Anna looking at me nude...something about it turns me on. I guess I have an exhibitionist side. I could feel their eyes on my body, checking me out up and down. I felt so exposed.

"Come on, what was it really?"

"Dance...a dance contest." I managed to say with a lump in my throat.

"Well, at least you can dance! You need a skill like that for the ladies!"

"It was...I won for being...I won the worst dancer of the night award."

More laughter.

"Wow!" One of them exclaimed, a busty redhead. "Small dick AND a bad dancer?! Good luck with that!"

I don't know why, but I offered up more info. "Actually, I'm married. To a very sexy woman who loves me very much."

No laughter on that one. "All right, good for you! We're just messing around...having some fun. No hard feelings?"

I smiled. "Nope, it's all good. My wife is the only one I have to please anyway." With that, I turned to make my escape.

Behind me I heard one of the girl call out. "Hopefully she doesn't like big dick!" The sound of laughter faded behind me as I walked away.

-------------------------

As I walked back to our spot on the beach carrying a bucket of beers, I had a strange confidence come over me. I couldn't stop thinking about the girls teasing me earlier; it should have embarrassed me, and it did a little, but at the same time, I liked it. I should have been infuriated at their insults, especially against my manhood, but I wasn't. After all, I liked it when my wife teased me, why not others as well? And they had all been soooo hot, I knew I would never have a chance with any of them, yet they had been paying me attention.

I saw in the distance that everyone had finished yoga and returned to our chairs. It looked like Chad was rubbing lotion on Lisa's back. I got excited at the thought of doing the same to my own wife; it had been two days since I had last touched her, other than with my tongue. I thought of how she had let me rub lotion all over her tits that first day on the beach...God, I hoped she would let me do that again today, with my cage off!

My heart sank as I approached and realized that Chad hadn't been rubbing lotion on HIS wife--it was Anna!! How dare he?!

"I got us some drinks," I said flatly, setting the beer down sharply.

Anna lifted her head and turned towards me. "Aw, thanks sweetie! I hope you don't mind, I didn't want to burn, so Chad offered to help lotion my back while you were gone and Lisa was in the restroom."

Anna was on her stomach with Chad rubbing her shoulders as he sat on the edge of the chair.

"No, that's fine," I gulped, not sure how I really felt. "I wouldn't want you to burn either."

"Anna, you have such a gorgeous complexion!" Lisa complimented her. "Sometimes I wish I hadn't tanned so much. You're so soft and fair." Anna did have very smooth, white skin, with no tan lines, blemishes, or even cellulite. And she was as soft as she looked, almost like a baby's skin. And parts of her were even softer still; all the parts I couldn't keep my mind off.

"There, all done!" Chad finished and sat down with a smile on his face. "And I agree with Lisa. You have very soft skin! You must moisturize constantly!""

Anna lifted herself on her elbows and her large breasts spilled down, resting on the wood of the lounge chair below. "Thanks," she said shyly. "Tim here loves to help me moisturize, don't you?"

I smiled in agreement and my eyes wandered from her breasts, over her shoulders and down her back, which was slick and shiny from the sunblock. Her smooth, thick hips curved out to the side and her round bubble butt protruded upwards almost obscenely. It, too, was slick and shiny and her thighs also--wait, what??! How did she get lotion on her ass?! Did Chad??...no...my mind raced thinking of the possibility. Not only had I been robbed of the pleasure of massaging my wife's amazing body, but someone else had got to do it! The more I mulled that over in my mind, the more a strange realization sunk in; the thought of him touching her was turning me on! It was hot to think of her letting another man, one she was obviously attracted to, touch her in such a personal, intimate way. In fact, I wanted to watch Chad do it nearly as much as I wanted to do it myself...what the hell?! What was going on with me?!

Chad and Lisa were now sharing a lounge chair, so Chad was lying on his side and Lisa was sitting in front of his legs. They both faced Anna, who was laying on her back. I was in a chair next to her. I glanced over her gorgeous body and was once again glad I was wearing dark glasses. My eyes popped when I noticed Chad. His cock dangled down his thigh and the thick mushroom head actually rested on the chair. His large balls also hung down obscenely, as big as large eggs. He was completely shaven, which made his package just look that much bigger. As if he needed the help. I was also laying on my side; I instinctively glanced down my own body for comparison. My balls were contracted quite far and no bigger than grapes. My short dick didn't "hang" at all; it merely sat atop my tight balls and pointed out at Anna pitifully.

"Does that sound good? Honey? Tim?" I hadn't been listening.

"What? Sorry."

"We were thinking of shooting some pool tonight. I haven't played in ages." Anna said.

"Sure," I agreed quickly. "Sounds fun." What?! I thought. I don't know how to play pool!

------------------

The next few hours were mostly uneventful. The four of us hung out at the beach for a while, swimming and sunning. A lot of the other guests were curious as to my and & Chad's lack of...hardware...so we got lots of questions about that. They all laughed when they heard I had won for being the worst dancer.

Once, when Chad and Lisa went for a dip in the ocean, a couple came up and recognized us from the bar the night before.

"You gave an amazing lap dance last night," the guy said. "Your husband must be very proud."

"Oh, I am," I said.

The woman spoke up. "Your not the one she was dancing with, are you? He was...different." She looked at my limp penis.

"What do you mean, different?" Anna jumped in before I could speak.

"The guy last night was...he had a....um.."

"A bigger dick?" Anna asked pointedly.

"Well, yeah." The woman laughed and her husband chuckled. I felt my face turn beet red and I looked away sheepishly.

"That was my friend. This is my husband, Tim."

"Oh, I see," the woman said, nudging her husband. "See, she gets to have 'friends', too!"

After they left, I had to ask Anna. "What was that about? Why did you let them think that?"

"Oh, it's no big deal. It was fun!" She brushed it off.

Chad and Lisa returned. Their bodies glistened with water as they walked towards us. Lisa's small boobs were firm and stayed firmly planted on her chest. Chad, however... his thick cock hung low and swung from side to side, slapping against his thighs as he approached. Water ran down his taught abs and dripped from the end of his dick. Shrinkage obviously hadn't affected him. I swear I heard Anna suck a breath in as she lifted her head and watched them walk toward us.

Lisa sat at the end of the chair and Chad straddled behind her. She took out the lotion bottle, leaned forward, and began rubbing the slippery gel onto her toned, athletic legs.

"You know," she said as she moved to her thighs, "there sure were a lot of people at the bar last night. They keep recognizing us. Well, they recognize Chad anyway." Lisa slipped her hand behind her and between Chad's legs. Her forearm flexed as she worked her hand over his manhood, playfully rubbing it with the lotion.

"They can't figure out who I'm with," Chad said. "Since you were the one dancing with me last night." He looked at Anna, who smiled.

"Ah, lucky you," Lisa said, leaning back into Chad's muscular chest, her hand still gently massaging his cock out of view.

Was she implying Chad was lucky or my wife, I wondered.

Anna took the sunblock from Lisa and before I could offer to help, she began applying it to her legs. She worked up her body as I stared...her hands moved across her curvy thighs and hips, up her soft stomach, and onto her large breasts. One at a time, she took them in both hands and massaged the lotion into the springy flesh and across her erect nipples. They slipped and jiggled as she kneaded them slowly. Once finished, she leaned back and sighed. As her head fell against her chair back, Chad's face came into view; his eyes were fixed on Anna's ample chest and his mouth was open slightly. He saw me catch his gaze, smiled sheepishly, and looked away. He had been lustfully staring at Anna touch herself. That dog!

Lisa hopped out of the chair and announced she was heading to the bathroom. She tossed the lotion bottle to her husband.

"Don't burn babe. Cancer's a bitch!" She joked.

I watched her athletic little ass bounce away as she cut across the sand. Chad began rubbing lotion on his arms. When he got to his shoulders, my wife shocked us both by offering to help.

"You heard Lisa, she doesn't want you burnt." She smiled and moved to the back side of Chad's chair and pushed him sideways, so she was standing behind him and he was turned towards me in his chair, his feet hanging over the edge of the chair in the sand. They were both facing me, her soft body obstructed from view by his muscular one.

Anna began rubbing lotion onto Chad's broad shoulders. He looked at me nervously, but I just laid back in my dark shades pretending nothing was out of the ordinary. Anna worked her way down his back, and then back up. His hands rested on his knees, and Anna leaned over Chad's shoulders to reach down each of muscular arms, even though he had already covered them. As she did so, her boobs, slick with lotion, smashed against the back of his neck and slipped along his shoulders as she moved. If he had simply turned his head, he could have easily slipped one of her stiff pink nipples into his mouth.

As Chad relaxed from Anna's massaging touch, his knees fell apart and his cock came into view. It was slick from the lotion Lisa had been rubbing on it previously. It was obvious Lisa, and now Anna, my own wife, was turning him on; his dick was lifted and curved away from his stomach in a long arch. It was much thicker than before and must have been almost half hard. I looked up at Anna to find her eyes fixed on his impressive penis. She glanced up and realized she'd been caught; she grinned knowing she's been caught, before looking down at my own crotch and smiling even bigger.

"Wow, now I know why they make the men wear cages!" Anna joked. I looked down at my dick and was shocked to find it completely hard and poking straight up from between my thighs. Before I could even move, Lisa appeared.

"Jesus, what did I miss?!" She looked at me, to her husband, and back again. "I leave for 2 minutes and Anna has you both worked up and ready to go?"

Anna laughed and trailed her hands across Chad's back as she took her seat again, trying to avert her eyes from his still growing phallus.

I snatched up my towel and covered my lap and peeking erection. Why the hell had I gotten so hard watching my wife and Chad? Was that normal?!

Chad swung his legs up and Lisa took her position between his muscular thighs again, obstructing his semi-hard monster from view. Thank God. Anna sighed deeply and dropped her head onto the chair.

"It not just the boys...maybe it's the heat, but I'm horny as hell." She turned and winked at me. "We'll just have to do something about that later, won't we honey?"

---------------------------------

"I'm terrible at pool!" I said, sulking as we entered our hotel suite.

Anna sighed. "I'm no good either, but it will be fun. There'll be booze..." She slipped her arms around me and pulled me close. "Besides, it might take your mind off things for a while...don't think I haven't noticed you drooling over me all day!" She rubbed her body against mine and my unrestrained dick sprung to attention between us.

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