Chastity Resort Pt. 04

"Well, it wasn't so instantaneous with us," Anna said. "I was dating a different guy when I first met Tim. I had no idea I was supposed to end up with him until 2 years and a couple guys later." My fingers were lightly massaging the softest part of her inner thigh, just next to her pussy.

"But you knew, didn't you, Tim?" Lisa asked. "You didn't date anyone that I can remember."

"Nope. I always knew it was Anna." My fingers brushed against her outer lips.

"I always did like you better than those other guys," Lisa complimented me. "What did you ever see in that Troy guy, Anna? He was such a jerk!"

Anna blushed. "Lisa, you and I shared a dorm room! I think you know it was mostly physical." I was dumbfounded. Both that she would admit that, and that it was true. "But there's more to a relationship than that. Besides, Tim here makes me happier than anyone else. Especially lately!"

Now it was our turn to kiss. By this time my hand was all over her pussy. My middle finger trailed up and down her slit as we kissed. She matched my moves with her tongue against my mouth. As I dipped my finger between her lips, she flicked her tongue against mine. We teased each other for a while this way until I was no longer sure who was leading; was her tongue following my finger, or was it the other way around? I drove my finger in her as far as I could and she circled my tongue with her own.

"Hey, get a room, you two!" Lisa laughed.

I broke away, aroused more than I was embarrassed. I couldn't wait to get back to our room and give her a real orgasm!

Just then I heard a voice with a heavy accent behind me. "Hi! Is there room for two more?"

"Sure, come on in!" Chad said. He looked at me and winked.

Two women made their way around the pool behind us and stood between me and Chad. I looked up and squinted into the sun. It couldn't be! I found myself staring up at the silhouette of the busty blonde from the yoga class. She bent and sat next to me, her large boobs dangling over the water as she felt for the seat under the churning water. She found the rock ledge and her full breasts smashed against her knees as she dropped into the seat. The ledge she sat on was higher than mine, causing her breasts to sit mostly out of the water. Only the bottom curve was out of sight. The waves gently lapped at her large, erect nipples. I gulped and turned back to Anna, only to find a disapproving look on her face. I pulled my hand away from her pussy, but she quickly yanked it back. I continued working her under the water.

We found out the women were sisters on holiday from the Netherlands. We made small talk for a while, but their English was not very good. I knew Anna must be getting very hot from all the fingering I was doing under the water. I was teasing and flicking her clit by the time Lisa suggested we head back to the resort.

I was so relieved to finally be leaving the torturous company of the beautiful busty woman beside me that I forgot I wasn't wearing swim trunks. As I stood to exit the pool, I turned to say goodbye to the women. Only when the busty woman's gaze fell to my caged cock did I remember my condition. She giggled and turned to her friend. She also caught sight of my shriveled penis through the small clear cage and snickered. I rushed out of the water without a word. As I wrapped a towel around me in embarrassment, I turned just in time to see the busty woman actually stand up and give Chad a hug, pressing her breasts into his chest. She sat back down and they said a few more words, her eyes hovering on his oversized red chastity cage dangling in front of her face.

Lisa came up behind me and yanked the towel from my waist. "No sense hiding now!" She and Anna laughed and toweled off. I wanted to get out of there fast. I walked a few yards up the trail and sat on a rock to wait for the others. Anna followed me.

"You OK honey?" She asked with a concerned look in her eyes.

"I'm fine," I lied.

"I meant what I said back there. I'm glad we're together. You're perfect for me." She hugged me, still naked.

"I know, babe, I don't question that. I'm just so incredibly horny after all this."

"Oh, my horny little man!" She said in a baby tone. "I'm gonna take good care of you tonight!" She whispered in my ear. "REAL good!"

My heart skipped a beat and my cock twitched. Did that mean what I thought it did?! Was she finally going to let me cum? She turned away from me, grabbed her shorts, and stepped into them. She wiggled her hips in an exaggerated manor as she shimmied the material over her thighs. When she got the waistband up to her ass, she made a big show of trying to stretch them over her bubble butt. She yanked and wiggled, causing her ass cheeks to bounce and jiggle wildly as the tight waistband lifted her soft flesh. Finally, she pulled slowly and steadily upward and her round butt popped into the shorts with a final, satisfying bounce.

"Whew!" She looked over her shoulder at me and ran her hands over her curvy hips. "I didn't think all this ass was gonna fit!"

I could only close my eyes and try to breathe calmly. If she kept up this teasing, I feared i would literally go crazy. I was completely out of control of my own body and there was nothing I could do about it. I was beginning to physically hurt from having so much pent up frustration with no way to release.

The walk back was the longest miles of my life. Anna made sure to walk in front of me the whole way. There was no escaping her delicious bouncing ass. If I tried to drop back, she did too. On hills she was sure to slow down so I would have an extended view of her thighs and glutes flexing and straining as she climbed. On the faster open stretches, she swayed her hips more than was necessary, which caused her butt to rise and fall with a squeeze and a bounce on every step. Her long, wavy ponytail swung back and forth, mimicking the side-to-side swaying motion of her ass. I imagined her bent over on a rock alongside the trail with me behind her grabbing her hair with one hand and her hip with the other, just giving her my dick for all I was worth. My balls ached with the thought.

Finally, I saw the resort ahead. It was approaching evening at this point, so we decided to stop at the boardwalk restaurant for dinner. I was absolutely spent; not from the walk, but from the mental anguish I had been through. I sat through the meal barely saying anything, a blank expression on my face. I was broken.

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

For all her teasing and tormenting, Anna was beginning to finally understand the effects on me. Back in our hotel room, she realized something needed to change.

"Tim, honey, I think I might be pushing you too hard."

I sat on the couch, listening.

"I don't think this is working anymore. You're supposed to feel more and more desire to please me, and you have until today. But now I feel like you've hit a plateau. You've given up, haven't you?"

I nodded.

Anna snuggled up next to me on the couch and looked into my eyes softly. "We just need to figure out our particular rhythm. This is part of the learning curve. I don't want this to be unbearable torture for you. I want you to LIKE denying yourself for me."

"I do, Anna. I'm just having a hard time adjusting. Maybe we need to ease into this more slowly. It's only been a week since I've submitted my orgasms to you; I can give you more than that, I'm sure of it. But at this resort with all these beautiful naked people, and seeing you do everything you can to tease me...it's too much."

Anna smiled. "Well now, I could be teasing you a LOT harder, believe me! I know just how to work you..." She cupped my swollen blue balls and rolled them in her fingers. I winced from the pressure. "See? I have all sorts of tricks I can pull out once we work up to it."

I groaned and pulled away from her grip.

"Look, I'm going to ask Lisa what I should do for you." Anna offered.

"No! She'll only make it worse!" I cried.

"It's her JOB to guide people through this! She will know how to help us, I know it. Now, why don't you just relax and watch some TV while I go talk to her?"

I was too worn out to argue.

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

About 10 minutes later, I heard a knock on the door. I opened it to find Chad standing there.

"Hey buddy," he said. "Mind if I come in?"

"Sure," I stepped aside and he entered, taking a seat on the couch. I grabbed us a couple of beers and joined him.

"Anna says you're having some trouble adjusting."

"Well, yeah, isn't that normal?" I asked.

"Of course!" Chad chuckled. "I remember in the beginning with Lisa; she would tease me relentlessly until I couldn't think straight. One time she tied me to a chair and played porn in front of me for 3 hours while she went out shopping. She came back and I was a mumbling, stuttering fool! She still didn't let me cum for a week after that!"

"How the hell do you handle it?" I asked. "I feel like I'm going crazy!"

"I'll tell you. The key is to rethink everything you've been taught about sex. Completely erase it, start over. You need a hard reset!"

"How do I do that? What am I supposed to reset TO?"

"It just takes time. And patience. Everything in you will fight it. At times it will seem unbearable. But you'll be grateful in the end, when you're living out your true purpose in your relationship with Anna."

"And what is that?"

"As servant. Pleasure-giver. Sacrificial lover. Whatever you call it, the result is the same; your entire sexual purpose is to please her and make her happy. That, as counterintuitive as it may seem right now, will ultimately give you more pleasure and happiness than you've ever felt looking out for yourself, having orgasms at-will. Men are weak when it comes to sex. Culture tells us differently; that men are strong and powerful in bed. In reality, it's women who hold all the sexual power. Once you understand that, everything will fall into place."

I thought for a moment. "I do really enjoy submitting to Anna. It's exciting and liberating. When she orgasms, I feel like more of a man than when it's just me."

"Yes! Now you're getting it. Her orgasms are what lead to your fulfillment in the bedroom. They are what makes you feel like a man, right? Your own orgasms are insignificant, fleeting. She doesn't need your orgasm to feel like a woman."

Chad was making a lot of sense to me, even in my blue balls induced foggy state. "That does make sense..." I said hesitantly.

"It will get easier as time goes on. Just remember to focus on your wife. The more frustrated or horny you are, the more you must seek to please her. It starts with you."

We finished our beers in relative silence, before Chad told me the plans for the rest of the evening.

"Anna & Lisa are waiting for us at our suite. What do you say? A night of drinking and relaxing in the hot tub to take your mind off things?"

That did sound good after a long day--no, a long week. "Sure. Sounds fun."

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

When we arrived we found Lisa and Anna already in the Jacuzzi. "Hey guys! How about some more beers?" Lisa asked.

We grabbed some drinks from the fridge and joined the ladies in the bubbling water.

"How are you feeling?" Anna asked me, concerned.

"Much better, actually. Chad helped me put things into perspective."

"That's my Chad!" Lisa smiled. "Amazing, as always." She threw her legs over his and leaned back. "How about one of your amazing foot massages?" She hinted. Chad began to rub her feet under the water.

"Great!" Anna said. "Anything you'd like to share?"

"Not really," I said slyly. "I'd rather show you." I leaned in and kissed Anna passionately. She wrapped her hands around my neck and returned the kiss. Not hearing anything from our friends, I glanced behind me. They were making out as well.

What the hell, I thought. I shifted my weight into a low seat in the hot tub, and Anna slid her body on top of mine so she was straddling my lap. Her hands caressed my chest. After a few minutes, she dropped her head onto my shoulder and I gently kissed her neck. When I reached her ear lobes, she let out a moan; that always drove her mad.

From my angle, I could see Chad and Lisa over Anna's shoulder. Lisa removed the necklace with Chad's chastity key on it from her neck and her hands disappeared under the water. A few seconds later she laid Chad's red chastity tube on the edge of the tub. She sat beside him, both hands in his lap, as they continued to kiss.

I was instantly jealous. Chad was free, his cock loose in the water with his wife stroking and playing with him. He spread his arms across the edge of the Jacuzzi and leaned back. Lisa kept working her hands under the water.

By this time, Anna was grinding her pussy against my caged cock. Because of the plastic tube and the heat of the water, I felt nothing. Just pressure in my aching balls as my cage moved around underneath her. She placed her hands on the edge of the tub behind me, which caused her breasts to dangle provocatively between us. I fought the impulse to grab them right away. Anna moaned as I kissed her. Just when I could hold off no longer and was about to touch her hanging tits, Lisa cleared her throat.

"Ah-hem! This hot tub is getting...hot!"

Anna slid off my lap and sat next to me, embarrassed. I understood; we had never fooled around in front of anyone before.

"Chad," Lisa continued. "Why don't you fetch us some cold drinks?"

"Sure thing, babe." Chad stirred in the water. As I glanced at his chastity cage lying on the edge of the pool, I realized Anna was unaware that Lisa had removed it. I stared with anticipation as Chad's body slowly emerging from the water. His tan, defined abs gave way to his toned Adonis muscles, which in turn pointed the way to his manhood. The water was high enough that the entirety of it could not be seen; the wide, girthy base arced downward and the end of his cock was somewhere under the water. Nevertheless, it was enough of a shock to cause Anna to gasp aloud. Lisa laughed in response and I caught Chad hide a smile as he walked past us and out of the hot tub.

When Chad returned, there was nowhere for him to hide. Not that he should want to. Not with a tool like that. He had two bottles of beer in each hand and walked slowly up behind Lisa. As he did, Anna and I had a straight-on view of his long, meaty cock. It slapped against his thighs as it swayed from side to side. It had to be 6 or 7 inches long soft, with a large circumcised mushroom head on the end. When he got to the hot tub, he sat on the side by his wife with his legs hanging over the edge in the water.

"Here you go." Chad handed me two bottles and I gave one to my wife. She took it from me slowly, never looking away from Chad's member. His cock hung down between his parted legs, at least twice as long as his oversized balls.

Finally, Lisa broke the awkward silence. "Tim, Anna, meet ALL of Chad." She laughed.

"Good god! I've never seen a cock so big!" Anna exclaimed.

"Not even your old boyfriend Troy's?" Lisa asked. "I thought you said he was packing in college."

"He was, or at least I thought he was. It wasn't anything like that though." Anna said hesitantly. She looked at me apologetically. "Sorry, honey. I know you don't like it when I talk about old boyfriends."

"That's ok," I lied, trying to play it cool. "It's in the past, right?"

"Yeah..." Anna said halfheartedly. She finally managed to avert her eyes away from Chad's dangling appendage.

"Why did you dump Troy anyway?" I asked Anna, trying to bring her back to the present, and perhaps fish for a compliment as well.

"Over time I realized we didn't have anything substantial in common. We stopped going out, stopped 'dating', really. It became all about the sex. You can't build a relationship on only sex, no matter how amazing it is."

My face burned with embarrassment.

"Oh, no, honey! Don't get me wrong," Anna tried to save herself. "Our sex life is amazing, too. Especially lately. You're the whole package, babe." She reached into my lap and grabbed my caged manhood with her hand. "I wouldn't trade you for the world. No one makes me happier."

I smiled at my wife, feeling redeemed. My cock was trying desperately to grow hard. Her hand was caressing me under the water, but of course I felt nothing through the plastic tube. An involuntary moan escaped my lips.

"I know! Why don't we get your cage off? After all, you're the only one wearing anything!" Anna said.

"No, that's OK." That was the last thing I wanted right now.

"Nonsense! I know you're dying to be free." Anna insisted.

"Yes, join us in our nudity, Tim," Lisa laughed. "Besides, Anna's seen my man now...it's only fair I see hers, too."

Anna smiled slyly and I knew I wasn't going to win this debate. Maybe it wouldn't be so bad; I was under water after all. And if I could just avoid getting a boner Lisa and Chad wouldn't know how small my cock really was. Maybe I was a grower? I tried to reassure myself.

Anna was having none of that. She slid off her seat and onto her km need in the water in front of me. She took hold of the key around her neck, leaving the necklace on, and slowly slipped under the water, her eyes on mine the whole time and with her sexiest look on her face. I felt her fumble with the lock briefly, then remove the chastity device. She didn't emerge right away; instead, I felt an incredibly warm sensation around my soft penis, even warmer than the bubbling water of the hot tub. It was her mouth!! I couldn't believe it! After a week of zero physical contact, my wife had engulfed my cock and was swirling her tongue around the sensitive head! All hopes of avoiding an erection faded; my penis grew rock hard instantly while Anna held it in her mouth. I could feel it sliding further back her throat as she held her nose pressed against my pubic bone. When I was fully hard, Anna slowly pulled back and my cock slowly escaped her lips. She gave the tip a kiss and emerged from the water.

Her long brown hair was swept back and droplets of water ran down her beautiful smiling face. She took her place beside me again. "Why don't you go get the next round, Tim?" She squeezed my thigh.

"Yes, Tim, I'd like another beer please." Lisa smirked.

What the hell, I thought. Everyone already knows my secrets and fantasies. I stood with my hands covering my crotch and made my way to the kitchen. Lisa whistled jokingly at my bare ass.

I stalled as long as possible in the kitchen, trying to let my erection subside. But it wasn't going anywhere.

"Hurry up, babe," Anna called from the other room.

I grabbed the 4 bottles from the counter, sighed, and turned to leave. As I walked across the living room and approached the others on the deck, their conversation turned quiet and I saw 3 sets of eyes staring at me. My face turned bright red; I wanted to turn and run. In contrast to Chad's long, thick swinging cock, mine looked almost comical; it was as hard as a rock, fully engorged and pointing straight up at my belly button.

I hurried into the water and slid down beside Anna. Thankfully, Chad had also re-entered the water while I had been gone.

"Now you've met all of MY husband," she joked Lisa.

The conversation was mostly platonic for the next hour or so. I was enjoying being free from my cage, even though I wasn't allowed to touch myself and Anna wasn't helping me out either. It was just good to stretch out for a while. Finally, Anna suggested it was time for us to leave.

"Oh! Before you go, I have something for you!" Lisa jumped out of the hot tub and went to the bedroom to retrieve something. She called back a minute later. "Anna, come in here...I need to show you something."

Anna rose to her feet and stumbled to the Jacuzzi stairs. She must have tripped on the first step, because she tumbled backwards and right into Chad's lap. She laughed and apologized. "How clumsy! I haven't had that much to drink, I promise!" She threw her arms around Chad's neck and playfully kicked her legs out of the water.