Chastity Resort Pt. 03

Anna slept for about an hour, exhausted from her explosive orgasm. I, on the other hand, was wide awake, thinking about my new found arrangement. It was a lot to take in; I still wasn't sure exactly how far Anna wanted to take this. I expected she would break by the end of the week and let me have some relief of my own.

Anna showered quickly to freshen up, and then dressed for the evening. Well, dressed is a relative term. The only thing she wore was an ankle length green flower-print sarong around her waist, which left her breasts hanging freely in the open.

"Ready?" She asked. "Or do you need more time to get ready?"

"Very funny." I tugged playfully at her sarong and she slapped my hand away.

"Hey," Anna said, taking my hands in hers and facing me. "I need to tell you something before we go..."

"OK..."

"Lisa and I were talking this afternoon while you were napping at the beach and, well... I don't know how to bring this up. It's not a big deal, really."

"What is it?" I asked nervously.

"Well, remember when Chad said he had worn a chastity device before?"

"I remember."

Anna continued, "I thought that was weird, so I asked Lisa about it. I guess she and Chad are into some kinky stuff themselves."

"Like what?" I asked, not knowing where this was going.

"Well, pretty much what we've been playing with. Female domination, chastity, control."

What were the odds of that? I thought. "And what did you tell her?" I asked Anna.

"Just that we've started exploring it recently. I said we were just starting out, and that this trip was the first time we have really tried anything. She was very nice about it. She even offered me some pointers since we're new."

"I don't know how I feel about you sharing our sex life with them." I said, surprised.

"Lisa and I used to share everything in college! We don't have any secrets. It will be fine, trust me." She hugged me close and gave me her sexy eyes. "Besides, I want to make sure I'm doing this right. She really sounds like she knows what she's doing. Now, let's go. We're going to be late!"

The sun was low in the warm afternoon sky as we returned to the boardwalk to meet Lisa and Chad for dinner. We found our destination, a little seafood restaurant, and discovered our friends were already seated at a table.

"How was your afternoon?" Anna asked Lisa as she gave her a quick hug before sitting down.

"Relaxing. We ended up soaking in the hot tub in our room and doing some shopping on the boardwalk."

"That sounds nice! I wish our room had a hot tub!" Anna commented.

Chad was quick to offer, "You guys are welcome to come over and use it sometime."

"Yes!" Lisa agreed. "We'd love the company! There are only so many things to do by ourselves, especially after the boardwalk closes down at night." She squeezed Chad's arm and grinned. We all knew what she was referring to.

The rest of the meal was casual and uneventful. The food was good and the drinks were even better. Everyone was having a few; after all, it was an all-inclusive resort and it was just a short walk to our rooms later. Anna and Lisa hit it off like the old friends that they were, and Chad and I made small talk. I discovered he was a personal trainer (go figure) and that's how he and Lisa had met. She taught a yoga class at the gym he worked at. I could have guessed Lisa was into yoga...she was fit and toned everywhere, with that perfect tight "yoga butt".

The night was still young when we finished eating, so Lisa suggested we go to a bar down the boardwalk where they have live music and dancing. We made our way out of the restaurant and down the dimly lit boardwalk. The bar had a tropical theme with open walls facing the beach, strings of lights hanging from the thatched roof ceiling. Chad and I left the ladies at a table and went to get some drinks.

"How do you like it here so far, Tim?" Chad asked as we waited. "Is it what you expected?"

"I didn't know what to expect to be honest. Anna is having a great time, and I'm glad she ran into Lisa. I'm still adjusting really." I glanced down at the cage on my crotch.

Chad laughed. "Yeah, I know what you mean. The first time we came here, being in chastity took some getting used to. That's for sure. It really opened Lisa and me up to some new things though." He turned and leaned back with his elbows on the bar, watching the crowd in the room. The way he was standing had the effect of pushing his hips forward, causing his large red chastity device to protrude from his waist obscenely.

A couple of gorgeous young ladies walked by at just that moment. Their heads turned as they passed, keeping their gaze on Chad as long as possible before giggling and turning away. He didn't even seem to notice.

"What kinds of new things?" I asked, trying to keep talking.

"Oh, the same kinds of things Anna tells us you are trying out... female-led relationship, chastity, that sort of thing. Well, I don't do the humiliation thing, that's for sure." He chuckled at that. My face grew red...I couldn't believe Anna had told him about that!

"No?" I asked, not sure what to say.

"Nah, not really my style. It just didn't fit for us, no pun intended." He pointed to his cock and laughed. He glanced over at my vastly smaller package and his tone dropped. "Sorry, man. Wasn't thinking."

Sorry?!, I thought. Who did he think he was?

"Anyway," he continued. "We got bored with the chastity thing, so we started experimenting with some...other things. And other people." He said slyly. Before he could explain, the drinks came and we returned to our table. Not a moment too soon, I thought.

Anna and Lisa were whispering as we approached, but they quickly stopped when they saw us.

"It's about time!" Lisa joked. "We were about to find some other guys to dance with!" She grabbed Chad's hand before he had a chance to sit down and dragged him onto the dance floor.

"Why do you look so down?" Anna asked, concerned.

"What? I'm not." I wasn't about to tell her what Chad had said.

"Well, good! I want us to have a good time. I really like this place."

I wasn't much of a dancer, so we sat in silence while Chad and Lisa danced. They must have danced for 4 songs before Anna broke the silence.

"Wow, they're really something, aren't they? Such a cute couple. I mean, look at her. Lisa was always fit in college, but damn! I'm jealous."

"No way! You're way hotter than Lisa. And if anyone should be jealous, it's me." I immediately regretted saying that.

"What do you mean?" Anna asked.

"Don't tell me you haven't noticed. He's a freaking personal trainer. He's ripped! And it's kind of hard to miss his ridiculous package." I said sarcastically.

"I don't know about ridiculous. Curious, maybe. Impressive. Even tempting. But not ridiculous." I couldn't believe she had said that. Her face was still and her eyes were on Chad and Lisa. Suddenly she laughed. "I'm just kidding!" She hopped off her high stool and stood between my legs as I sat, facing me. "You know I love your body! You work out too, you know. I even love your little cock." She reached down and played with my balls as she said it.

"Get a room you two!" Lisa said as they returned from the dance floor.

"I was just trying to talk Tim into dancing with me," Anna said.

"No way," I said. "You know I don't dance."

"You can always borrow Chad," Lisa offered. "He loves to dance. You wouldn't mind dancing with my hot college roommate, would you hun?" She grinned at her husband.

"Not at all," he replied. "Tim?"

"Yes, please Tim? You don't mind, do you?" Anna pleaded.

"I-I suppose.." I said, sounding very uncertain. Anna didn't pick up on my uncertainty, or she just didn't care. She squealed, grabbed Chad's hand, and pulled him onto the dance floor.

Lisa slid over into the seat next to me and sipped her drink. "This gives us a chance to catch up! You know Anna and I were very close in college. We talked about everything. She always liked you, even when you were just friends and she was dating around."

Anna and I had become friends early on as freshmen. While I was more the solitary type and didn't date much, Anna was much more social, always going to parties and events with her sorority. She ended up dating several guys over the semesters. It wasn't until we were seniors before I asked her out and we hit it off as a couple.

"She dated some losers, that's for sure," Lisa continued. "Remember Troy? With the motorcycle?" She laughed. "I still don't know what she saw in him!"

This was uncomfortable. I tried to change the subject. "What's that you wear around your neck?"

She reached between her small perky tits and lifted up a small silver key. "Oh, this is the key to Chad's heart. Which is located behind his cock," she laughed.

"But why do you wear it? It's not like you can unlock him outside your room."

"It's a symbol of our relationship. I wear it any time I have him locked up, not just here. It reminds him who is in charge. I'm sure if Anna had your key she would be wearing it, too."

I was surprised. "I didn't know she told you it was lost."

""Lost? What?" Lisa had a confused look on her face.

"The staff lost the key and that's why she hasn't been able to unlock me. They're supposed to have another one made today so I can finally- never mind." I stopped before I embarrassed myself.

Lisa laughed out loud and smiled. "Oh, Anna. You sly little girl!"

"What do you mean by that?" I had to find out what she knew.

"Well," Lisa hesitated. "I really shouldn't say anything. It's between you and Anna."

"From what I hear, Anna has already told you everything. And if you're going to be helping us with this chastity thing whether I like it or not, there may as well not be any secrets." I was getting angry. It seemed like I was the only one in the dark here.

Lisa thought for a moment. "OK, ok. The truth is...they never lost your key. It's probably time you learned the truth about this place. It's not just a 'women-friendly nudist resort'. Truth is, it's a chastity resort."

"I've never heard of such a thing. What does that mean?"

"It means all the men in here are in some stage of chastity. Some for the first time, like you. Some are more experienced, like Chad." Lisa paused, gauging my reaction. "In fact, Chad and I are more like...mentors. We help other couples learn the ropes and make the most of their time here so they can continue their new lifestyle when the return home."

My head was spinning. So many questions raced through my mind. Did Anna know all this? She must. Why did she lie about the key? How long had she been planning this? Was Lisa part of her plan? What was going to happen next? Would she EVER let me cum again?

Lisa saw that I was starting to panic. "Listen," she said gently, placing her hand on my thigh. "This is good for you guys. Chad and I are happier than we have ever been. Don't you want Anna to be happy? She looks happy here now."

I was so shocked by this new information; I had forgotten that Anna was dancing with Chad. It was easy to spot them; Anna's long green sarong waved back and forth as she swept her hips from side to side. It was sheer enough you could easily make out her ass beneath it, rolling back and forth to the music. Chad's hands were resting in the small of her back, just above her swaying ass. Her arms draped loosely around his neck. They were talking and smiling like old friends. I wondered what they were talking about. Was it anything like my conversation with Lisa?

"Your wife is beautiful," Lisa said, nonchalantly rubbing my thigh lightly. "You're lucky to have her."

It was true. I had married above my station, so to speak. I knew she had dated some very attractive guys in the past. And here she was dancing with one now. I looked down at Lisa's attractive body and her hand, moving slowly on my leg.

"Anna confided in me about your fantasies." Lisa said.

"All of them?" I gulped.

"All the ones you guys are aware of so far." She smiled and her hand moved to my inner thigh until it was actually touching my balls. "I know how good you are at eating pussy," she whispered. "I know that you like being denied orgasms. And I know about the humiliation." Her mouth was against my ear now. "I know you have a small penis, and it turns you on." She trailed her fingers down the short length of my penis tube. My cock twitched and the cage began to lift up. "I saw you looking at Chad earlier. Are you jealous?"

"What?! No-"

"Don't lie. It's OK. Most men are intimidated him. Some women, too. Do you think your wife is?"

"Hey, don't talk like that!" I had my limits.

"Sorry. I just couldn't help noticing the way they are dancing."

Chad and Anna had drawn closer together. With her arms around his neck, her bare breasts hung down and rubbed against his smooth chest as they danced. It looked like her nipples were enjoying the stimulation. He was a few inches taller than Anna, but the length of his chastity device meant the tip of it was hanging down directly in front of her pussy. His cage was pulled away from his body; was he actually getting hard dancing with my wife?? The plastic cage bobbed between them, brushing against her body as they moved.

I felt a strong pang of jealousy and a sickening in my stomach as I thought of the implications. Was my wife turned on? Was she attracted to Chad? Was she thinking about his penis? How could she not? Did she want to have SEX with him?

Lisa broke my train of thought. "Looks like you noticed them, too." My penis was once again straining at its cage, swollen and purple. "Tim, are you getting turned on by my touch, or by watching your wife?"

To be honest, I wasn't sure. But I was afraid of the answer.

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

As soon as we were back in our room for the night, I confronted Anna. "I can't believe you lied to me!"

"I know, gun. I'm sorry, but I did it for your own good!"

"My own good? I've been going crazy with my dick locked in this damn thing and you've had the key the whole time! You could have let me out! You could have touched me, made me cum!"

"See, that's the problem right there! It's always about you! Listen, if this relationship is going to be more about me from now on, you're going to have to start making some sacrifices." She slid closer to me on the couch and put her hand on my leg before continuing. "Tim, if you knew I had the key you would have talked me into using it before I was ready. I wasn't strong enough yet to do what I wanted to do. I was afraid you wouldn't want to go through with it. With letting me control you. Don't you trust me?"

"Of course I trust you, honey." Her touch on my thigh and her arm around my shoulders was having a calming effect on me. "I'm sorry I got mad. You're right; it's your key." I gulped loudly. "It's your cock. And you can do whatever you want with it."

"Oh, Tim! You don't know how happy I am to hear that! I really do know what's best for our relationship, and for you. You have to keep trusting me. I'll do the right thing, I promise."

She kissed me on the cheek and scurried off to the kitchenette. A gift bag had been delivered while we were out to dinner. I followed her and she read the note on the gift aloud.

"I'm so happy for you and your husband! Here is a "little" care package to help you get started on your new journey. Let me know if you ever need anything.

Have fun!

Nurse Aimee"

"Isn't that sweet of her?" Anna exclaimed. "Let's see what we got!" Anna handed me the note and began to pull things out of the gift bag. I saw that Aimee had actually put the word "little" in quotes. That little-

I know what this is for!" Anna held up a dainty chain necklace. She rushed to the bedroom and I heard the drawer of the nightstand slam. Anna returned and stood before me. She slowly opened her fist, exposing a small silver key exactly like the one Lisa wore around her neck at dinner.

"Do you want to do the honors?" She asked.

I slowly took the key from her and held it in my fingers between us. It was so small and insignificant looking. But we both knew how important it really was. It signified a new era in our marriage, a new covenant between us. I would submit myself to my wife completely and she would assume total power over my sexuality. I could have easily reached down, unlocked the chastity cage, and freed myself. It was incredibly tempting. But that wasn't what Anna wanted, and I wanted what she wanted. It took every bit of willpower I had to thread the chain through the key and slip it around my wife's slender neck. I clasped it in the back and she smiled from ear to ear.

"I'm so proud of you, honey!" She threw herself into me and I hugged her naked body to mine. I could feel the cool metal of the key against my chest.

"What else do we have?" Anna turned back to Aimee's package and pulled out a set of nylon restraints. "Oooh, kinky!" She waved them teasingly. "Oh my!" She peered into the bag. "I can't believe this!" She pulled out a purple, penis-shaped dildo. Twisting the base caused it to vibrate in her hand. Anna laughed and turned a little red in the face. "Well, this might be fun!"

We had never really used toys in our lovemaking; just some light restraints for the occasions had Anna teased me. She had one of those small vibrating nubs for use on her clit, but nothing to actually penetrate her.

Next out of the bag was a small black curved dildo with a strap attached to it. "What do you think this is for?" Anna asked, pulling at the strap.

Of course, I knew what it was immediately. I had had considerably more experience with porn than Anna. "That's a face dildo. It goes around the guy's face and the dildo part sits on his chin. You know, for..."

"Oh!" Anna's face grew a smile as she thought about it. "Now that DOES sound fun!"

There was only one item in the bag for me. It was a tube of the numbing cream Aimee had used to shrink my penis down so it would fit into the chastity tube. There were also 2 envelopes, one marked "HIS" and the other marked "For HER eyes only". Anna opened the envelope and I watched as she read for a moment.

"What does it say?" I asked.

"Um, it's for my eyes only! It says I shouldn't tell you!"

"That's not fair. Mine doesn't say that."

"Yes, let's see what yours says!" She grabbed the envelope from my hand, opened it, and laughed.

"Let me see!" I said. She turned the paper so I could read it. All it said was:

'Rule #1: Do whatever your wife says.'

I looked up at my smiling wife. What the hell, I thought. I might as well play along.

"OK, so what exactly do you want me to do?" I asked.

"Hmm... Let's see..." She tapped her finger on her cheek and thought. "I know! Let's go to the bedroom and try out some of our new toys!" She threw the bag of goodies over her shoulder, grabbed my caged cock in her hand, and led me into the bedroom.

When we got there, she instructed me to lie down on the bed and wait for her. She disappeared into the bathroom. I sprawled out on the bed and emptied the contents of the bed beside me. Grabbing the purple dildo, I inspected it in my hand. It was soft rubber with a generic shape, not like a real penis. It was about twice as big around as my own cock, but considerably longer. About 7", I estimated. It grew near the end to a bulbous shape, almost like a slightly inflated balloon.

I heard the bathroom door pop open and I dropped the dildo on the bed quickly and put my hands behind my head. Anna emerged from the bathroom wearing lingerie I'd never seen before. The top was a black silk camisole with thin straps. The bottom half of the bra was solid, but the top was sheer, showing off her erect pink nipples. Below the bra the top was also sheer, with frills around the waist covering a black satin thong below.