Chastity Resort: Part 7

by Small Penis


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by handyrandy9

 

Read Part 1 – Click Here!
Read Part 2 – Click Here!
Read Part 3 – Click Here!

Read Part 4 – Click Here!
Read Part 5 – Click Here!
Read Part 6 – Click Here!

 

Part 7…

 

After the sex shop on the boardwalk (where I ate out Anna in the changing room to an impromptu orgasm) the rest of the afternoon was relatively uneventful. The four of us shopped for a while longer, then we all sat on the beach sipping drinks in the warm sun for a couple hours.

I found my sex drive was quickly rebounding after my first ever prostate release that morning. Of course, Anna’s persistent teasing helped along those lines. She was relentless; it was as if each orgasm I gave her fueled her sex drive even more. That physiology was in stark contrast to my body’s own mechanisms. Typically, the more I orgasmed, the less I wanted to have anything to do with sex. Perhaps that’s what made this new relationship dynamic work so well. Each time Anna denied my orgasm and I felt no release, my arousal increased to exceed hers, which was growing in its own right. We were like two insatiable sex crazed pleasure-seekers, continuously reaching new heights of arousal and lust. And I loved it.

The beach looked different to me that day than it had on the first day, before we met Chad and Lisa, and before I had truly grasped the concept of a female-led relationship. I no longer felt embarrassed or uncomfortable. I had a renewed sense of self confidence; I was really enjoying my new responsibilities as primary pleasure-giver in my relationship with Anna.

After a while of lying out in the sun, it was getting late in the afternoon and Lisa suggested we check out the main bar at the resort. We walked further down the boardwalk than we had previously. The bar was at the far end of the beach overlooking the sand and waves. The whole end wall of the bar opened up and the tables sprawled onto an outdoor patio covered only in strings of lights and beach-themed decorations. There was a live band playing on one end of a stage under the canopy.

About two thirds of the tables were occupied, so we didn’t have trouble finding a seat. For the next hour or so nothing much happened; we shared a large seafood sampler and threw back drink after drink as the night went on. As the sky grew darker and the stars came out, the band played louder and the tables filled with partiers rounding out their night.

The bar was also having a dance competition that night. Several competitions, in fact. Throughout the evening couples could compete in several different mini-contests of varying themes and dance styles. The big news was the prize; each winning couple was awarded a “free day”, during which the chastised male would be set free from his cage and allowed to wander the resort totally unencumbered.

Anna used this in an attempt to convince me to join her. Remember, I don’t dance. Anna had grown up dancing in competitions, and had been quite fond of clubs during her wilder college years. That was only a few years behind her now, at age 28, so she still had the moves, so to speak. And definitely the body.

“Come on, Tim,” Anna pleaded, stirring the fruity alcoholic drink in front of her. “What’s the worst that can happen?”

“Here? I’m not exactly comfortable here in my condition.” I said sarcastically, motioning towards my lap.

“Oh, nonsense! Everyone here is locked and loaded!” Anna joked.

Lisa laughed out loud. “Don’t you mean loaded and locked?”

Haha, I thought. Sure all the guys were confined to chastity cages, but they weren’t all created equally. Since the devices were color coded according to size, everyone always knew just what you were packing. Or in my case, what I wasn’t packing. And the fact that mine was crystal clear when everyone else’s was opaque…well, that was just cruel. No way was I getting up on a stage in front of everyone.

Lisa jumped in. “Look, I’ll do it if you will. And God knows I can’t dance a step.”

“Amen to that,” Chad chuckled.

Somehow, through the sheer force of peer pressure, they continued until I finally agreed.

“Just once! And I don’t have to like it,” I said grudgingly.

One of the waitresses from the resort took the stage and announced the first round of dancing. It was freestyle, and couples would be tapped out until just one couple remained as the winners. The band started playing again, and Anna grabbed my arm and led me to the dance floor. Chad and Lisa danced beside us among about 10-12 total couples.

Anna and Lisa were laughing and goofing around, but I just sort of swayed awkwardly. Eventually, Anna playfully pushed me away, and Lisa jumped in. She began screwing around and dancing as badly as possible along with me. Anna laughed, shrugged and started dancing with Chad.

It didn’t get much better, but thankfully everyone was drunk enough we ended up having a good time. We all got tapped out and took our seats again at our table.

“See, that wasn’t so bad!” Lisa joked, taking Anna’s place next to me. Anna sat in Lisa’s chair, which was so close to Chad’s that their thighs touched. She didn’t seem to notice.

“It was kind of fun I guess,” I admitted.

We ordered more drinks and talked, enjoying the live music and the warm sea air. The fact that we were all nude enhanced the experience; that free and unencumbered feeling was part of the draw of a nudist resort. Well, we were naked except for the string bikini bottoms that Anna and Lisa still wore. And of course, my and Chad’s chastity cages. None of which was visible above the table; my view across the table consisted of my wife’s beautiful, perfectly shaped hanging breasts and Chad’s tanned muscular chest just inches from her. God, why were they sitting so close to one another?!

“Tim…Tim?” Anna asked.

My eyes jumped up from her tits to her eyes. “Huh? Sorry…”

Busted.

Anna smiled. “I guess my little guy is coming back around!”

All three of them laughed at that; my face reddened.

“I asked if you wanted to switch partners again. That way I might actually have a chance of winning with Chad!” She reached across her body and squeezed Chad’s arm, leaving her hand resting on his large bicep. She slipped her other arm between his arm and his body so she was effectively hugging his arm. Her arm across her chest had lifted her boobs, and they now rested on her forearm, the soft flesh spilling over. They looked absolutely amazing; I wanted nothing more than to reach across the table and grab a handful. I felt that familiar stirring in my groin.

“Sure,” I gulped. “Why not?”

I was too busy watching my wife get up, distracted by her jiggling boobs, to realize I was in no condition to be standing up myself. As Lisa pulled me to the dance floor, my cock was hard in its cage and standing out from my body. My balls were pulled tight, and were once again a deep red/blue in color, despite having been drained that morning via a prostate massage.

The MC announced that they were going to “turn up the heat” for this round. That meant the band took a break, and techno/house music began playing over the speakers. I tried to hide my attempted erection behind folded hands, but Lisa was having none of that.

“Ah-ah! If I have to dance, so do you. Besides, I can help hide that, even with my small ass!” With that, she took my hands and placed them on her narrow hips. She trailed a finger along my cheek, and then spun around so her small athletic ass was pressed against my groin. My cock strained in its cage, pushing back against the thin bikini covering Lisa’s tight ass.

I stood motionless for a moment as Lisa started wiggling her body against mine.

“I-I don’t know about this!” I said nervously over the music.

“Nonsense!” Lisa laid her head back on my shoulder and leaned in until her lips were nearly brushing my ear. “We’re just having a little fun! Besides, it looks like your wife is having some fun of her own…”

Anna! I had forgotten she was dancing with Chad! I looked around and found them a few couples over. I couldn’t believe my eyes! Anna was bent over just inches in front of Chad, her barely-covered, thick ass wobbling back and forth as she shook her hips from side to side. Her thin white bikini bottom, which was already 2-3 sizes too small, was wedged so far between her deep ass cheeks it basically looked like a thong. The thin straps dug into her soft hips as she gyrated mere inches from Chad’s dangling chastity cage. And dangle, it did! The long, curved red tube concealing his impressive manhood arching out from below his toned Adonis muscles, over his large, swollen balls, and down towards my wife’s inviting ass. The side view I had of their bodies was incredible; my eyes trailed back from Chad’s manhood, over the swell of Anna’s big butt, along the dip in the small of her back, and down to her large, soft breasts swinging beneath her. The sight turned me on more than I could have imagined. Chad moved his arms from the air and reached forward towards her— Damn!! My view was obstructed by another couple!!

“Hot, isn’t it?” Lisa ground her ass against my straining cock and spoke into my ear. “They’ve got ME all worked up…” Lisa grabbed my hands and slid them up and around her body and held them over her breasts. She gave them a squeeze, giving me permission to do the same. Her tits felt so much different than Anna’s; smaller, firmer, daintier. I instinctively kneaded them in my hands. They were probably a B-cup, easily contained in each hand, whereas Anna’s D’s spilled over when I palmed them. I had only touched a few women’s breasts in my life and none other than Anna’s during the 7 years we had been together.

My cock was positively throbbing in its cage, painfully stretching and pulling the ring behind my aching balls. Lisa was relentless with her grinding; her ass may have been smaller than my wife’s, but it was firm and she knew how to work it. The small 2 inch tube of my chastity device was wedged between her taught ass, and her cheeks were rubbing against my tender balls.

Just then Anna and Chad came back into view. Anna had turned and was now facing Chad, dancing a distance from him, affording him what must have been a fantastic view of her body as she moved and swayed smoothly. I don’t know what had transpired in the time they were out of view, but whatever it was the effect on Chad was obvious. His large cock tube now arched up and straight out from his body; his own balls being pulled and tormented by his own desire. His desire for MY wife! I felt a pang of jealousy. Anna, for her part, seemed oblivious to the large phallus pointing at her as she continued to gyrate and sway in front of Chad’s roaming eyes.

The dance seemed to go on forever, but in reality it must have only been five or six minutes. Both Chad and Anna and Lisa and I got tapped out at the same time. This time Anna didn’t leave Chad’s side, not giving me a chance to reclaim my seat next to her.

“Whew! That was hot!” Anna fanned her face. I had a feeling she wasn’t talking just about the heat.

“Tell me about it,” Lisa said. “Tim here couldn’t keep his hands off me!”

I was dumbfounded. My face turned bright red and I stammered for words. “W-what?? I didn’t–I never–”

“Really, Tim?!” Anna feigned shock. “Have I got you so horny and desperate you’re grabbing at other women now?”

“No, I–”

Anna laughed. “I’m just joking! I’m sure it was just innocent fun. Besides, we’re all friends here…right?”

“Sure…” I decided to play along to downplay the incident.

“I didn’t mind,” Lisa offered with a smile. “Although, shouldn’t you be allowed to even the score, so to say?” Lisa asked Anna mischievously.

“What, do you mean like this?” Anna dropped her hand out of sight under the table and Chad jumped a little.

What the hell?? Did she just grab his dick?! I didn’t know what to think. Feelings of jealousy were rising quickly.

“No, more like this,” Lisa, too, reached under the table and I was shocked to feel her small hand grip my chastity cage.

Chad and I looked at each other tentatively, before he finally shrugged and picked up his beer. I looked over to Anna, who was grinning and sipping her own beverage. Neither she nor Lisa removed their hands. In fact, Lisa began to absentmindedly rub her fingernails along my swollen balls. My heart raced as I wondered if Anna was doing the same to Chad.

Somehow, we continued to talk as though nothing were out of the ordinary. Just two friendly married couples at a nude male chastity resort handling each other’s husband’s genitals under a table. Typical Friday night, right?

The night was getting late and the glasses were piling up on our table. Everyone was soon tipsy and comfortable. Eventually, the girls had brought their hands back above the table, much to my relief. Between Lisa’s meandering fingers and thoughts of Anna exploring Chad’s caged manhood, I was going mad with lust. It was all I could do to keep engaged in the conversation; all I could think of was sex and how desperately I wanted to cum. It had been so long since I’d had a real, satisfying orgasm. So long. At some point, Anna had commented that the night air was getting chilly, and Chad had gallantly draped his muscular arm around her shoulders. She snuggled in close to him, and his hand dropped down and grazed her right breast. Again, she didn’t let on that she was aware, even as her breast jiggled when he would talk with his hands, waving them around and slapping against her soft flesh. Her nipple on that side grew hard and stiff from the repeated stimulation.

Just when I couldn’t take any more of the sexual tension and was going to excuse Anna and myself for the night, the MC took to the stage once again and announced the last dance competition of the night. This would be the last chance for a couple to win a “free day” and be allowed to roam the resort without a cock cage for an entire day.

“Ok, come on!” Anna said excitedly.

“No way…” Lisa said. “If I get up there again I’ll fall over!” Indeed, her speak was quite slurred.

“Tim?” Anna offered.

“No, thanks. I’m done, too.”

Anna turned to Chad. “Come on then, big guy. Let’s go have some fun!” Chad glanced at me and I nodded in approval. Anna had drunk as much as the rest of us and she was still raring to go! She still had it from her college days.

As they walked to the dance floor, the MC made a change.

“Come on up to the stage, dancers! This is going to be the hottest, wildest dance of the night! Only for the best and bravest among you!”

This warning served to pare down the participants to just three couples (well, Chad and Anna were not a couple of course, but no one knew that). Anna led Chad onto the stage, undeterred.

“This last dance is for the ladies only, if you know what I mean…” The MC continued as another worker brought up three chairs and spaced them out on the stage facing the crowd. “What do you say, do you wanna see these hot young ladies put on a show?!”

There was cheering and howling from the very drunk crowd. I was speechless; I sat there in silence as the realization of what was about to happen sunk in. Would Anna really go through with this? Surprisingly, a deep part of me wanted her to do just that.

The crowd continued to howl as the guys took their seats and the women stood beside them.

“The way this is going to work,” the MC explained as the crowd quieted down, “The ladies will all dance at the same time. After the music stops, you’ll cheer for your favorite team. The couple with the loudest fans will be crowned winner!” There was relative silence as everyone waited for the music. Everyone was sizing up the contestants. I did a quick inventory myself.

Couple One was about our age, late 20’s. She was dirty blonde, tall and thin, with small breasts and no curves to speak of. She reminded me of a runway model, very hot in the face. He was also thin, and sporting a black chastity device, which was the second largest size.

The female of couple Two was Asian. Long black hair tied up, dark skin, fairly large fake boobs, and curvy hips, but no ass really. She was also very hot overall. Her man was black, with a blue chastity cage. Third biggest, but still larger than the green average size cage, and way bigger than mine.

And of course there was Anna and Chad. They were an unconventional couple; she was obviously very curvy and soft, with a round ample ass, large natural breasts, beautiful pale complexion throughout, and long brown wavy hair. He was athletic and muscular, a personal trainer by trade. Dark and handsome, with a square jaw and probably 5% body fat. And of course, that monster cock hiding inside the oversized red chastity cage. A visually unconventional couple, but there was something about seeing them up there, side by side. They had a certain chemistry between them. A mutual appetite. And loads of sexual tension.

The song finally started with a slow, methodic beat. Nothing too exciting happened at first. The music switched and the pace picked up. The women were watching each other as they danced around their partners. The music switched again, and the women were all at various stages of straddling their partners at this point. The first two were almost in their man’s laps, but Anna appeared to be holding back. She was facing Chad, straddling him, but holding herself up as she rolled her hips back and forth and swayed her breasts. He smiled up at her with his hands respectfully hanging down at his sides.

The tall blonde moved awkwardly, and didn’t have a good sense of what she should be doing. The Asian woman seemed to have the moves, but she wasn’t very graceful about it, jerking and pausing at times. Anna, on the other hand, was smooth as glass. She swayed and rolled her hips, causing her ass to undulate hypnotically back and forth. Still in her bikini bottoms, she was the only one wearing any sort of clothing, but the way the thin material framed her curvy ass and clung to her butt made it look even hotter.

The Asian turned from her man and sat in his lap facing the crowd. She was grinding her pussy on her man’s crotch and working her tits with her hands, causing the crowd to howl and whoop.

Anna took note and switched up her moves. She faced the crowd, bent at the waist, and gave Chad an eyeful of her ample booty. It was the same position she had taken earlier on the dance floor, but this time she leaned all the way forward and touched the floor. Her ass was pointing straight up as she wobbled it from side to side, the low waist of her bikini unable to cover her ass crack, which protruded a good two inches above the waistband. She looked so hot. The crowd cheered.

Anna stood and placed her hands on her knees, pushing her tits out toward the crowd. A couple guys in the front yelled out. She looked over her shoulder at Chad’s big smiling face before taking the next step. My throat tightened and I couldn’t breathe as she backed her ass up and dropped it soundly into his lap. She ground it back and forth and he threw his head back in ecstasy.

Lisa broke my trance. “Wow, your wife is good! Chad seems to be enjoying his lap dance, don’t you think?”

I nodded, unable to sort all the emotions I was having. I was sick with jealousy, my stomach was in a knot watching my wife wiggle her ass on another man. But it also turned me on more than I could imagine.

I winced as Lisa slipped her hand back onto my caged cock. My penis was so sore from trying to become erect, but not being able to. And my balls were so, so tender. Lisa slowly rolled and massaged them in her fingers as Anna had done previously to “relieve some pressure”. It felt as if my entire groin region was about to explode.

“You know she wants to fuck him, don’t you?” Lisa asked matter-of-factly. My cock jumped at her words and she squeezed by cage playfully. Of course I knew my wife wanted to fuck him. I hadn’t allowed myself to admit it until now, but it was obvious. We all knew it.

“I knew it from the first day we met you on the beach. I could see it in her eyes. And in his. He has an effect on her, doesn’t he? He does something for her, he has something she needs, something she wants…so desperately.” Lisa continued to massage my balls as she spoke. Anna turned to face Chad and straddled his lap again as she adjusted her bikini, which had wiggled it’s way deep between her ample ass checks. She pulled it down and across her butt in a futile attempt to cover herself. It struggled to contain even half her ass, her silky-smooth white flesh spilling out from the bottom and over the top at the same time. She gyrated her hips and the crowd cheered.

“You know what it is, right? What your wife wants?” I looked at Lisa, but couldn’t speak, my face white as a ghost. She leaned in and whispered in the sexiest voice possible, “She wants his huge, thick, meaty cock!” She picked up my caged dick and bounced it as she said the words, a reminder of what I did NOT have. I felt pre-cum practically flowing from the smashed tip of my dick.

Lisa laid her head on my shoulder and continued stroking my inferior caged manhood as we watched the remainder of the lap dance.

Anna was working the crowd now, and Chad. She would wiggle her ass above his crotch, still not making contact, and the crowd would yell and cheer. When she slowed to run her fingers through Chad’s hair, they were quiet. She shook her beautiful ass again and they cheered. She teased her ass up and down in his lap, grazing his chastity tube with her bikini-clad pussy before pulling away again. Chad had an almost animalistic look on his face; I knew he wanted nothing more than to reach out and grab her, to grind his cock against her.

The other dancers were still going, but my eyes were locked on my wife and Chad. Anna lifted Chad’s arms from his sides and placed his hands on her hips. She leaned forward, smashing her big soft tits in his face. She rubbed them back and forth as she continued to tease his cock with her ass. She leaned back and much to my surprise, she guided his hands up her body and to her hanging breasts. He smiled up at her and kneaded them in his large, manly hands. Anna reached down and pulled the strings of her bikini loose as the crowd cheered. She stood and pushed her hips forward, pulling Chad’s head to her stomach with her hands. After several seconds of her grinding his face against her pelvic area, he must have grabbed her bikini with his mouth, because as she pulled back, the material fell away, exposing her perfect, round bubble butt to the entire bar. They went crazy.

“Fuck, your wife has a hot ass!” Lisa exclaimed. My leaking cock could attest to that.

Anna bent forward, briefly flashing her pussy to the crowd behind her as she dragged her boobs across Chad’s face again on her way down to his lap. She dropped her now bare pussy squarely onto his chastity cage, and began rubbing her sex up and down the long red tube containing his monster cock. Chad could wait no longer and reached around to grab big handfuls of Anna’s plump ass. He pulled her along his encased shaft, no doubt insanely frustrated that he was confined and could feel almost nothing on his cock. Despite this, he put on a good show, pushing his cock tube up into her pussy lips and grinding it against her wet slit.

Anna threw her head back and her long, wavy brunette hair cascaded down her arched back, just as the music came to a stop. She fell against Chad and appeared to say something to him as the crowd yelled, but I couldn’t be sure.

“Wow, great job ladies!!” The MC took the stage again. “Whew, is it hot in here or is that just me? Let’s hear it for contestant number one!”

The crowd cheered rather softly as the tall thin blonde smiled nervously. The second woman got a bigger reaction, but it was still reserved. By the time they started cheering for Anna, she was standing beside Chad looking nervous and somewhat embarrassed. He had his hand around her waist in support, his arm resting on the shelf of her ass. The crowd had emphatically declared Anna the winner.

“Our winner of the lap dance contest is…”

“Anna,” she said timidly.

“Anna! And who is your lucky man that will be enjoying a day of freedom tomorrow?”

“My friend, Chad,” Anna answered.

“What a lucky friend indeed! Hopefully that friendship comes with benefits, am I right?” The MC asked Chad with a wink.

Chad just smiled and he slapped Anna’s butt playfully and hugged her to him, causing her face to redden slightly.

“All right, thanks for playing along with us tonight, I hope you all had fun. You can all leave the stage, except for contestant one. Also, will the following couples join us on stage?” The MC scanned the audience and pointed directly at me and Lisa and another couple. I shook my head no and planted my feet, but Lisa yanked me up before I could say anything. I was quite obviously aroused and the last thing I wanted was to go up in front of everyone. But it was too late.

Lisa must have taken pity on me, because she didn’t try to move my hands, which were firmly planted in front of my straining cock.

“Congratulations, each of you have been chosen as winners in the ‘worst of show’ category! You’ll be joining our winners tomorrow in total nudity!”

The crowd laughed, as did most of us on stage. Lisa grabbed my arm and raised it above us in victory, exposing my swollen cock in its clear cage to the crowd. My face turned three shades of red as I heard laughter from the front row. I looked down to see a woman pointing me out to her friend before they both laughed out loud and covered their mouths. A group of young women at the next table over let out a mix of cheers and laughter as they one by one raised their pinkie fingers to me. A couple of them made the universal “small dick” symbol with their thumb and forefinger.

My first reaction was to run from the stage, but I didn’t. I didn’t even try to cover myself. Their attention, even of a humiliating and emasculating manner, was attention none the less. And I was so desperately horny. Knowing I was exposed on stage for all to see…I had never considered myself an exhibitionist, but maybe there was something to it. A part of me enjoyed the humiliation.

———————————————

Anna and I said our goodbyes and headed off to our room, my straining cock attempting to point the way. As soon as we were inside our suite with the door closed, Anna grabbed my arm, turned me to her, and kissed me. This was no peck; it was very aggressive and passionate. Anna pulled my head to hers and pressed her mouth and tongue against mine. After a couple minutes of making out, still just standing in the kitchen, Anna reached down between us and gripped my chastity cage, rolling it around between her fingers. I winced and groaned loudly.

“What’s wrong?” Anna pulled away with a look of concern on her face.

“What’s wrong?!” I was shocked. “What’s wrong is my wife just gave a very public lap dance to another man, my cock is locked in a cage so I can’t even get an erection, and all I want to do is cum!” My quivering voice was a mix of intense frustration and desperation.

We both looked down at my desperate cock bobbing between us, locked in its plastic prison.

“If you didn’t want me to dance with Chad you should have said something,” Anna said. “I asked you if it was ok.”

“No, no, it’s not that…” I hesitated sheepishly. “It’s just… I can’t…”

“Can’t what?”

Before my brain had a chance to weigh the consequences, I blurted out, “I can’t stop thinking about you having sex with him!” I immediately regretted saying it aloud.

Anna stepped back, shocked. “What? Why are you thinking about that?”

“Lisa said it was obvious you two have… chemistry, and the way you were dancing up on him…” I hung my head.

“Oh, honey, that’s crazy!” Anna laughed. “We were just having fun! I would have danced with you the same way if you weren’t so shy! Besides,” she continued, “You’re my husband. I love you. I wouldn’t do anything you wouldn’t want me to.”

“Really?” I asked.

“Of course not! You know I would never go off and sleep with someone else behind your back! Our sex life has never been better, remember? You’ve made me so happy and you’ve been so… so attentive to my needs this week!” Anna smiled her sexy smile and continued to roll my sore aching balls in her hand.

I just looked at her, wanting to believe her, but I couldn’t get my mind off the way she had been grinding her pussy against Chad’s manhood on stage earlier. Anna must have sensed my hesitation.

“Tim, baby…you need me to prove it to you? You want me to show you? Show you how much I love you? How turned on you get me?” She was caressing both my caged dock and the back of my head, while her lips brushed against my ear as she whispered softly, “You want me to show you hard I can get you? How hard you make my pussy cum?”

That was it. I groaned and my knees buckled slightly. Anna caught me and I leaned on her as she led me to the bedside. She kissed me again, softly, and then slowly guided my lips to her neck. I continued to kiss as she pulled my head lower, into the smooth valley between her milky white breasts. I turned from side to side, kissing further and further along each silky mound until my lips found her swollen nipples. One at a time, I took them into my mouth, rolling the firm nub around on my tongue as I sucked with my mouth. Anna moaned and ran her hands through my hair, guiding my head from one glorious breast to the other until she was ready to proceed. I kissed my way down her soft, taut stomach. My own stomach was flittering with butterflies and my head was spinning as I caught a whiff of her scent. My eyes closed and I dipped lower, burying my nose in her small tuft of dark pubic hair. I kissed the soft spot just above her slit and was about to finally reach my mark when Anna pushed me back onto the bed.

“Not just yet,” she wagged her finger at me. “It’s my turn to play now.”

She motioned for me to rotate in the bed, and I assumed my new normal position. I was shocked when I realized I had automatically brought my hands above my head and spread my feet, waiting to be bound to the bed posts.

Anna smiled. “Haha, that’s a good boy! You’re learning fast.” She proceeded to tie my wrists and ankles to the restraints. I was now once again bound and at her mercy.

She got on her knees between my feet, leaned forward, and began kissing and licking my engorged balls. I looked over her shoulder to see her shapely hips and her plump ass sticking up in the air. God how I wished I was behind that big beautiful ass right now.

“Oh, Anna,” I groaned in pain. “Please let me out! I’ve been trying to get hard for so long it hurts!

Anna took the key suspended around her neck and traced the sharp metal teeth along my swollen testicles. “What do you mean, you’ve been ‘trying for so long’? We’ve only been playing for 10 minutes…what had you all worked up before that?” She smiled wickedly.

“Please…” I moaned.

“Was it watching me dance? Did you like watching me move my body on stage like that, in front of all those people?” She inserted the key into the lock and twisted. I moaned again. “Well?” Anna continued. “All you have to do is tell me what got you so horny and I’ll let you out…”

“Anna, please…” I begged. My cock was purple and smashed in the clear plastic tube. It ached like a sore muscle, only 10 times worse.

“It had to be more than that…was it the other girls dancing?” Anna mused, circling my rigid cock with her fingernails. “No, they weren’t really your type. Maybe it was what you said earlier…you know, about Chad?”

Anna had a fake puzzled look on her face. I had to get free. Whatever the cost.

“Yes, that was it!” I cried in pain.

“What was it again?” Anna slid the lock out of the chastity device until it was just barely holding it shut. “What was it about me and Chad that turned you on so much?”

I was sweating now. I gulped and yelled out, “I can’t stop thinking about him fucking you!”

Anna slipped the lock out and my dick instantly sprung upward and was fully erect. The chastity tube reached halfway down my meager 4 inch prick.

Anna slipped the narrow tube off effortlessly. “Yes, that was it!” She smiled.

I threw my head back in relief and lay there for several minutes, enjoying the feeling of a simple, unrestrained erection. Who knew just getting hard could feel so good?!

My cock was stiff as iron and throbbed with my heartbeat as I lay there. I finally opened my eyes to see Anna with her head on my thigh, just staring at my erect penis. I love when she looks at me; it really turns me on for some reason. To be totally vulnerable and exposed like that.

“It really is magnificent, you know…”

“It is?” I asked, surprised. She had never said anything like that before.

“Of course. I mean, it’s not the biggest… by far… but it’s the stiffest I’ve ever seen.” She pushed my rigid cock sideways and watched it spring back and forth in the air above my stomach. “Most of the cocks I’ve seen don’t get this hard.”

“Really?” My ego swelled with pride.

“Really. I mean, I think the big ones are too heavy. But yours is just so HARD!”

I groaned at her backhanded compliment and reveled in her humiliation of my small penis. I was really starting to get into the SPH (small penis humiliation) aspect of this chastity thing. A drop of pre-cum oozed from my member. My wife smeared it around my mushroom head with her finger.

“Now…back to what we were talking about. Why is it that the thought of me and Chad together turns you on?”

“What?! I don’t know why we’re still talking about this!”

“I just want to know what you’re thinking. Besides, I think you LIKE talking about this.” My cock betrayed me by releasing another large drop of pre-cum. Anna used it to lubricate my shaft and began running a single finger along the ridge, from top to bottom, at a slow, agonizing pace.

“Oh, Anna…” I moaned.

“I just want to know what you’ve been fantasizing about. What you picture when you think of…you know, of Chad… ‘fucking me’.”

I gasped and a trickle of pre-cum escaped my tip. Anna smiled.

“Is it his toned, muscular body against me? Is it his dark tan skin against my white smooth body?” Anna was still running her finger along my throbbing shaft. “Or maybe it’s not quite so PG. Maybe you like imagining him kissing me. Or squeezing my ass. I know he likes my big round butt…I’ve seen the way he’s been looking at me all week.”

At this point my cock was leaking a steady stream of pre-cum and I was arching my back, desperate for more contact against my aching dick. But Anna kept her touch against me light, teasing me.

I moaned out, “yes, that’s it! I want to watch him play with your ass!” I couldn’t believe Anna had dragged that out of me, but it was true.

“I knew it! He’s been staring at my butt all week! That little pervert!” Anna started stroking my dock between her thumb and forefinger. I squirmed on the bed.

“Now, when you picture him playing with my ass, is he hugging me? Is he sitting down? Or…?” Anna kept prying expertly, saying exactly the right things to get me to say what she wanted to hear. She was good.

“No…” I was writhing on the bed. Her stroking and teasing, however slow, was steadily bringing me closer and closer to orgasm.

“So is he behind me or something?” Anna added another finger, increasing the pressure of her strokes. My dick was slick on all sides with pre-cum, from base to tip.

My breathing was short and rapid and my whole body was tense. “I’m so close…!” I whispered fiercely.

Anna continued stroking without changing pace. “Honey, what do you see? What is Chad doing to me?” She looked up with big innocent doe eyes.

I was in absolute agony; my balls were drawn up tight against the chastity ring behind them and my cock was a deep shade of purple. Images of Anna dancing on Chad’s lap flashed through my brain and I tried to use them to push myself over the edge of orgasm, but Anna’s teasing touch was holding me back. I fought my body, trying to will myself to cum through sheer force! I could literally feel cum working its way into the shaft of my penis.

Finally, it was too much. I would have said anything just to cum at that precise moment. Words exploded from my mouth.

“He’s fucking you!!!! Chad’s fucking you from behind with his huge cock!! He’s slamming into your big ass and stretching you out!! Oh–oh GOD!!!” I screamed out as my orgasm came on hard. It welled up from deep within me like a fountain and washed over my entire body, racing toward my groin and intensifying and focusing to the point where I thought my dick would explode! My entire existence surrounded the crescendo of pleasure arising in my groin, working its way from my rock hard balls, through the base of my turgid cock and up the engorged shaft to the swollen purple head, and then….nothing! Anna let go!

But it was too late. Without any form of stimulation or even physical contact, my orgasm lingered on; the peak drawing out and continuing to intensify until suddenly, 5-6 seconds after Anna had removed her hand, my dick relaxed and fell against my stomach. The tension in my body switched off like a light and a long, thick wad of cum oozed from the tip of my penis. It continued in a slow and steady stream for at least 8-10 seconds, without pulsing or twitching, until there was a large pool of cum on my stomach and it was running down my side to the mattress below. I had never seen so much cum. It was easily twice the amount I normally cum.

Yet, I had felt nothing. No pleasure. No sense of release. No diminish in my state of arousal. I had just watched my body completely evacuate itself of a week’s worth of semen without a hint of orgasm. It was as if I had watched myself simply take a piss.

“Oh, baby,” Anna cooed. “That wasn’t supposed to happen!”

My shock slowly turned into despair and I felt tears forming in my eyes.

“Timmy…I’m so sorry!” Anna clambered up the bed and snuggled up beside me, her head on my chest. “I was supposed to stop before you came, but it was too late!”

“Why didn’t you just let me cum?!” I fought back tears.

“What do you mean? You DID cum!” Anna was genuinely confused.

“No! It’s not the same at all!”

“What do you mean? I saw you cum! I mean, look at all this! You came in buckets!” Anna ran her fingers through the sticky goo on my stomach.

I groaned and whimpered. My voice was wrought with frustration as I explained. “That’s what’s called a ‘ruined orgasm’. There’s no pleasure, no satisfaction. I felt an orgasm building like a freight train and then…nothing! In fact, I’m hornier now than before!” It was true; my balls may have been empty, but my brain was still screaming “Fuck!’.

“Oh, god, that sounds terrible,” Anna said sympathetically. “But you don’t want to cum right before your free day tomorrow…it will make it a lot more interesting if you’re still nice and horny!”

I didn’t follow her logic, but my brain was still cloudy.

“I just wanted to cum so badly!” I whimpered, fighting back tears of frustration.

“Oh, I know honey. You will soon, I promise.” Anna stroked my chest and tried her best to soothe me. I was still rattled and jittery. “Remember…you can put a stop to this at any time. All you have to do is say the word and we can go right back to our old sex life…”

I honestly didn’t want that, even in my current condition. “No…I’m fine.” I gulped, not sure if I believed myself. “Well, I will be fine. I just need a distraction right now. How about some TV or something?”

Anna didn’t say anything for a moment. “I had something else in mind…” She stood up, faced the bed, and spread her pussy lips with her fingers. She was absolutely drenched; juices covered her lips and ran down both her thighs nearly to her knees. Her clit protruded obscenely between her fingers. I swear I could see it throb.

“Look what you did to me! I’ve never been so wet!” She slid a couple fingers along her slit and a thick string of moisture dripped from her folds.

“Anna, I can’t! I just can’t! Not now…” I lost the battle with my feelings of frustration… a tear escaped my wet eyes and ran down my face.

“Oh, no! I didn’t mean…no, not–I understand.” Her face dropped.

Now I felt bad. Anna stood there, pussy dripping and a dejected look on her face. Just because I hadn’t cum didn’t mean she couldn’t, right? I couldn’t say no to this woman.

“Look, if you want to do it…”

A smile spread across Anna’s face. She reached into the bedside drawer and pulled out the big life-like dildo Lisa had given her. She left the lube, saying “I don’t think I’ll need this tonight!”

My wife proceeded to straddle my thighs. She rubbed the head of the dildo in the puddle of cum still pooled on my belly, coating it in my fluid. I groaned. She leaned back and pressed the large head of the fake penis against her opening. Without any foreplay, she pushed with increasing pressure until the wide mushroom head popped inside her, causing her to jump a little. She gasped as she slowly but steadily forced the oversized dildo into her sopping pussy. Finally, she could take no more in this position. In a single slow, agonizing stroke she had taken about 7 inches of this monster toy.

“Ohhhhhhh, gooooooooooodddddd!!!! This thing feels…amazing!!!” She slid a few inches out and I watched as her lips gripped the shaft tightly.

From this angle I had to peer over my own once again fully erect cock to see the action. This served to remind me of my frustrated arousal, as well as highlight the stark contrast between my own penis and the much larger version penetrating my wife. I was amazed that not only that she was able to accommodate such a large phallus, but that she had done so on a regular basis in the past. And with a real man attached to it.

It must have been only about 30 seconds and 10-12 short strokes before Anna was clenching down on the dildo in orgasm. Her hips rolled and her tits shook as her body spasmed in pleasure. I stared silently as she experienced wave after wave of pleasure, which I had been denied earlier. Her orgasmic throws rocked my body, causing my stiff cock to slap into what was left of the cum on my stomach. The cum I had been robbed of. It had been worth it though, to see Anna just then, her eyes rolled back in ecstasy, experiencing enough pleasure for the both of us. God, I love that woman.

Neither of us bothered to clean up; we were simply too exhausted. Anna cuddled against me as we fell asleep. The last thing I remember was the sound of the lock clicking on my chastity cage. I groggily looked at Anna as she smiled and kissed me goodnight.

“I love you, babe,” Anna said, her hand cupping my caged cock. “Better get your rest…tomorrow I’m going to tease you like never before!”

 

To be continued…

 

 

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