Chastity Resort: Part 3

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by handyrandy9


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


Part 3…

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…”


“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.

“Wow, you look gorgeous honey.” I said, my mouth open and eyes wide. The black shiny material contrasted her pale, smooth skin deliciously, making it look silky smooth and milky like cream. Just looking at her made my groin ache.

Anna slinked over to the bed and told me to lay back with my arms above my head. She reached down at the top corner of the bed and pulled out a loop of fabric. Then she attached one of the nylon restraints from the bag to it and secured the other end around my wrist. She proceeded to do the other side as well. Then she moved to my legs and did the same with my ankles. I was now spread-eagle on the bed, securely tied to all four corners. Completely naked except for my chastity cage, of course. That was about to change.

Anna snuggled up beside me on the bed and stroked her hand through the hair on my chest. “How would you like it if I took that cage off?” She asked.

“Really!? I would love it!” This was a surprising turn of events. I thought we would just be using the toys on her, but here she was about to finally set me free.

Anna moved between my legs and kneeled on the bed. She bent over and dangled the key over my cage. Her breasts hung down provocatively in the camisole. She brushed them against my chastity device, pushing it deep into her cleavage. “Are you sure you want me to unlock it?” She asked with a puppy dog look on her face.

I groaned. “Yes, please!”

“OK, since you asked so nicely.” She slipped the key into the lock and twisted. The lock popped open. “There!” She said triumphantly and sat back on her heels. “Now what?”

“No, you know what I meant! Take it off! Please!”

“That’s not what you asked for!”

“You know what I meant! Please take it off!” I pleaded.

“Hmm, how about an orgasm first? For me, of course. Then I’ll let your little friend out to play.”

“Fine,” I groaned impatiently.

“Fine?! Hmm, maybe I’ll just leave it on if you’re going to have that attitude!” She snapped the lock closed again.

“No, please, I’m sorry. I was just—I’m just not thinking straight. Of course we can do it your way. Whatever you want honey.” At this point, I knew she was serious. I had better do what she asked.

“That’s better.” She picked up the face dildo. “What do you say we try this out?” Not waiting for an answer, she grabbed my hair, lifted my head, and slipped the strap behind. She adjusted it so it was tight against my chin, with the dildo pointing straight up. It was about 5 inches long and curved forward in the direction of my nose. She giggled. “Is this right? It looks kind of funny.”

“I-I think that’s right. That’s the way it’s supposed to look.” To say it was weird to see a cock protruding from my face would be an understatement; it was downright humiliating. Not to mention it was bigger than my real cock.

Anna straddled my waist with her pussy against my caged cock. I could feel the heat from her pussy. She leaned forward and slowly kissed her way up my chest. When she got to my neck, she looked directly into my eyes, lifted her head, and kissed the tip of the dildo with her soft, pouty lips. My eyes widened as the rubbery head slipped past her lips and into her mouth. She continued downward in a single motion, taking nearly the entire dildo into her mouth, never breaking eye contact. She moaned softly before pulling back up, her lips drawing out as they slid up the shaft. She let it fall out of her mouth and it bounced on my chin.

Anna stood over me on the bed and slipped her thong off slowly. She paused for a moment, towering above me. From this angle, I could barely see her face past the swell of her breasts. They swayed as she stepped forward until she was right over my face. She slowly bent her knees and dropped down. Her pussy grew closer and closer, until all I could see was it and her thighs. She parted her lips wide with fingers from both hands, causing her clit to become exposed and stand out, already erect. I could see her pussy was quite moist as she teased herself with the tip of the dildo. After passing it from her clit to her slit several times, she lowered herself down and the dildo slowly penetrated her. She went halfway down the shaft before lifting back up and then dropping down completely.

“Mmmm,” she moaned, rotating her hips slightly. “That feels so good. It’s been almost a week since I’ve had your cock in me. I think even this small dildo is deeper inside me than you would be.”

My stomach felt like butterflies at this point. She was right; even though the dildo was the same girth as my penis, it was at least an inch longer than my meager 4″ member.

Anna leaned forward, pressing herself against my lips. I opened my mouth and flicked my tongue across her engorged clit. It aligned perfectly. The warmth of her thighs on my cheeks and shoulders was intense. She must have really been turned on. Oh, how I wished my hands were free so I could touch her. I knew her beautiful ass was just right there, waiting to be grabbed and squeezed. My eyes were drawn up her body to her breasts, which looked larger than normal in the push-up camisole. They heaved as she breathed, faster and harder as she worked her hips against my chin.

“Oh, Tim! This is wonderful!” She grabbed my head with her hands and pulled it up, grinding my mouth against her pussy. I flicked my tongue expertly against her clit. I knew just how to work her up to an orgasm. I had had a lot of practice, especially lately. When I licked downward I could feel the dildo against my tongue. I knew it was just a dildo, but it still felt strange. The shape was all wrong. I tried to ignore that and focus on her lips. They were spread tightly against the shaft of the dildo. She began to lift her hips, moving the dildo in and out of her pussy as much as she could while still leaving her clit pressed against my lips. I kept working it, bringing her closer and closer to orgasm.

“Ohhhh,” she moaned. “I absolutely love this! I’ve never been eaten and fucked at the same time!” She quickened her pace and I matched her speed. The downward pressure on my chin meant I couldn’t have closed my mouth if I had wanted to.

My groin was burning at this point. I felt such need, such desire in my loins. My abs were tight and my hips were lifting from the bed, reaching desperately for physical contact. It was futile, of course; my cock was still locked firmly in its plastic prison. That didn’t stop my penis from straining and leaking pre-cum profusely. My balls ached both from the back-up of a week’s worth of semen and from the chastity device pulling them firmly away from my body. I couldn’t wait for Anna to unlock me and relieve all that pressure.

It was that desire that kept me furiously licking and sucking her clit, even through my own pain and discomfort. I wanted to see her orgasm so bad! Not just because I knew my own pleasure was dependent on it. I wanted her to cum just because I knew how good she was feeling.

“I-I’m going to cum!!” Anna cried out. “Oh, fuck me! Fuck me!! Oh God!” She threw her head back and slammed her pussy down, burying the 5″ dildo as far as it would go.

I put everything I had into it. I could feel her muscles spasm against my face as she came. Her thighs squeezed my head tightly, covering my ears and muffling her cries. I had never heard Anna be so loud! She was screaming and moaning like a wild woman. Her pussy flooded and her juices flowed down my chin as her orgasm slowed.

“Ahhh! Ahhh…” Anna sighed. She felt heavy against me as she relaxed. She slumped forward and her body curled up over my head.

“Mmmmmpphph!” I mumbled. I couldn’t breathe!

“Oh! Sorry…” Anna swung her leg over and collapsed on the bed beside me, spent from the intensity of her orgasm. I was silent as she caught her breath. “That was fantastic! I have a feeling that’s going be a regular thing from now on! Did you enjoy it?”

“Of course I did honey,” I said sincerely. “I loved watching your pussy stretch and the dildo slide in and out. It was hot!” I had never before seen anything besides my own cock penetrate my wife. “I was so turned on! I thought my cock might break right out of the plastic!”

“If you thought that was hot, wait until we use the purple one!” She waved the vibrating dildo in the air and laughed.

“Hey, don’t forget it’s my turn now,” I said.

“Of course, baby! That is, if there’s anything left in your balls after you leaked so much pre-cum!” I looked down and saw both the inside and outside of the penis tube was slick with evidence of my arousal. My cock was still swollen and purple, filling the tube to the point where the head was trying to squeeze out of the pee hole. Anna touched her finger to the exposed skin and gathered a large drop of pre-cum before licking it off seductively.

“Mmmm…Your frustration tastes delicious!” She teased. “Now,” she continued playfully, trailing her manicured nails across my stomach. “Why was it again you think I should unlock you?”

“What do you mean, why?? Isn’t it obvious?!” I was in no mood for games anymore. Was she really going to drag this out?

“No.” She said matter-of-factly. “I’m not sure why I should let you out. What benefit is it to me? I’ve already cum.”

I couldn’t believe it. “Are you serious?”

Anna saw the anger building in my eyes, and she smiled and took a softer tone. “Look, I’m just trying to do this right. The card in the bag had suggestions for how to ease into the chastity lifestyle painlessly.”

“Painless for whom?” I mumbled.

Anna ignored me. “Having you argue your case and convince me reasserts my authority in the bedroom. It also gets your buy-in. I don’t want this to just be MY fantasy. I will be in control, there’s no mistake about that, but I want you to WANT me to be in charge.”

“I do want that,” I reassured her. “I know you’re doing everything you can to make me comfortable with all this. It’s a lot to take in.”

“Yes, I know it is. That’s exactly why I need you to convince me to let you cum.”

“OK,” I said, thinking. “You should unlock me because…so that…so you can see how much you turn me on.”

“That’s good. What else?”

“If you let me cum, I won’t be so frustrated and irritable with you.”

“Hmm, wrong direction.” She corrected me. “The letter said your frustration will turn to a deeper desire to please me over time.”

“How long does that take? ‘Cuz it’s almost unbearable now!” As if to prove my point, my cock throbbed in its cage, still standing upright as far as it could go.

“Ha! It’s only been 7 days! You can survive a lot longer than that. Next?”

“I don’t know. Maybe because I’m your husband and you want to meet my needs?” I was running out of ideas.

Anna sighed. “It’s a good thing I’ve already decided to release you, because that was pathetic. Next time I ask, I expect you to have better answers.”

I was too excited to respond. I was going to cum! Anna got on her knees beside me on the bed, leaned over and inserted the key into the lock. Without pausing and with no fanfare, she slipped the lock off and wiggled the plastic tube down and off my cock.

As I mentioned before, I was a quick grower, getting an erection in mere seconds under normal circumstances. However, these were not normal circumstances; I had been denied sex and teased at home for 5 days. Then my cock was confined to a tiny cage and I was teased relentlessly for 2 more days, all the while pleasuring my wife any way she wanted at a nudist resort surrounded my attractive naked people. Needless to say, I achieved a full erection in record time.

Neither Anna nor I said anything for a moment. We both stared at my throbbing purple member and watched as it bounced and twitched with every heartbeat. I don’t know if all small penises are this way, but I’ve always had insanely hard erections. My cock was hard as a rock and pointing straight up towards my belly button, although it didn’t reach even half way to it.

“Wow,” Anna exclaimed. “I don’t think I’ve ever seen my little man so excited!”

“Yeah?” I asked mischievously. “Just what are you going to do about it?”

Anna leaned down and lightly kissed the mushroom head of my cock. “I’ll be right back! Don’t you dare touch your dick.” She hopped up and scurried into the bathroom, her beautiful ass and hips jiggling the whole way.

I was still tied to all 4 corners of the bed, so I couldn’t have touched myself if I tried. Anna was gone for what seemed like forever, but it was probably only 5 minutes. The entire time all I could think about was that kiss…I prayed she would continue where she left off and give me one of her amazing blowjobs. I dreamed of watching her sink my cock into her mouth until her nose touched my pelvic bone. She loved to hold me there, all the way in, sucking and rolling her tongue around, driving me mad.

When Anna emerged again from the bathroom, I did a double-take. She still wore her lingerie camisole, but she had put on a pair of cotton running shorts and had a robe draped around her shoulders.

“Hey!” I cried out. “What’s going on?!”

“Well, honey, the only good reason you could come up with as to why I should let you cum, was so that I could see how much I turn you on. But I was thinking…you don’t have to have an orgasm to prove that, I can already see it by your hard on.” Anna stood at the side of the bed and pointed to my still very erect cock leaking pre-cum.

I let out a long groan that turned into a soft whimper. “Wha-? But you said- but, I…” I found myself unable to put together a complete sentence. My mind had no capacity for thoughts other than sex right now.

“Now, I can leave you unlocked for a while so you can enjoy your erection. Or, if you prefer, I can just lock you back up until tomorrow when you can try again. But it wouldn’t be fair to let you cum tonight.”

Fair?! Anna had just ridden my face to her third orgasm of the day and I was about to be left with blue balls for the seventh day in a row! But I knew better than to argue that point. I was torn. If I wasn’t going to be having an orgasm I might as well get locked up and at least attempt to get my mind off cumming. On the other hand, it felt wonderful to be free for a while. It was like my penis was finally stretching after a long car ride.

“I guess I’d like to stay unlocked for a while.” I said, utterly dejected. Anna sensed my disappointment.

“Oh, babe, it’s not so bad. I promise this won’t go on forever. I just really want to get things started off on the right foot.”

Anna threw her robe aside and sat on the bed next to me. She grabbed the TV remote and turned it on. “How about we watch some TV and get your mind off things?”

She flipped through the channels until she landed on a movie that looked interesting to her.

“Hey, how about untying me?” I asked.

“I can untie your legs, but not your arms. Not yet. I’m not sure we can trust you in your present condition.” She smiled before getting up and removing the restraints around my ankles.

Anna dimmed the lights and crawled back in bed beside me. This time she lay on her stomach with her head propped on her elbows near my knees. This put her ass about a foot from my face. I found myself staring at it, unable to turn away. She was kicking her legs in the air, causing her ass checks to rise and fall as the flexed. I was mesmerized. Normally I wouldn’t be able to resist reaching out and touching her; running my hands up her smooth thighs, along the white fleshy orbs of her ass.

As it was, I couldn’t move a muscle. All I could do was look. Her shorts were the very short kind, with white piping around the hem and a slit up the side. Her legs were parted slightly and as she kicked, the shorts moved here and there enough so that every once in a while I caught a glimpse of her pussy. My mouth literally dropped open when I realized she had removed her thong.

Anna nonchalantly laid her head on the side of my stomach and brought her hand next to it. She absentmindedly swirled her fingers around until they found the copious pool of precum that had formed on my lower stomach. A thick string led to the tip of my penis, which hovered erect over her hand. As she played with the fluid, rubbing it back and forth between her fingers, the back of her hand would occasionally brush against the top side of my cock. The touch was almost nonexistent, but after so long with no contact it felt amazing.

Soon she moved her hand to my far thigh, causing her arm to rest under my cock and lift it into the air. I moaned aloud.

“Is that too distracting?” Anna asked. “I can stop.”

“No! Please don’t stop. It feels good.” I gulped as she began to softly massage my thigh. She worked her hand around my entire groin region; my lower stomach, both thighs. Her movements caused my cock to twitch randomly and bounce around uncontrollably from the stimulation. There was a near constant flow of pre-cum now; it coated the back of her hand and wrist.

My eyes fell back to her ass. I could just make out the TV above it. It was impossible to concentrate on the movie with her butt right in line with it. Every slight movement of her body on the bed caused her butt to roll and wobble. The shorts had a seam in the center, which just served to accentuate her delicious cheeks even more. Oh God, I’d never wanted to touch something so badly. It was then that I noticed her pussy lips were moist. I nearly fainted.

The next hour is best described as blissful torture. I was so incredible aroused; I had never been so turned on. I didn’t even KNOW a person could feel so much desire. It was like a drug. I craved more and more of it, even though I knew it would leave me unfulfilled and delirious.

The movie finally ended. Anna’s hand cupped my blue balls and my cock was still erect, resting on her wrist. She rolled over facing me, with her pussy taking the place of her ass in my direct line of sight. “Mmmm, I couldn’t concentrate on the movie! All this sexual tension and teasing has got me all worked up again.” She smiled down at me, past the swell of her breasts. “I’m not tired yet…tell you what. How about I put on a little show for you? You don’t have to do anything this time, just lie there.”

I had no idea what she had in mind, but I was up for anything at this point. “Sure.” I agreed.

Anna raised her hips off the bed and slid her shorts down her thick thighs and off completely. She reached over to the night stand and brought back the large purple dildo Aimee had given us. She slowly raised her top leg and bent her knee, exposing her beautiful pussy to me. She trailed the dildo across my stomach and through the various pools of pre-cum, gathering as much as she could onto the purple rubber shaft. It looked funny next to my smaller and shorter cock.

“Not that I’ll need all this lube, really. I’m soaking wet as it is from playing with you.” She ran the head of the fake cock down her soft stomach and began to tease her clit. She worked the head up and down along her slit. She pushed it slightly as it passed the entrance to her love tunnel and the head disappeared briefly into the folds. She continued this for 2 or 3 minutes, pushing the head harder and harder against her hole. She moaned loudly and breathed out.

“Ohhhhh… The head of this thing feels soooo big!”

Her words caused a knot in my stomach. “It is big.” I gulped, playing along.

“Hell yes, it’s big! Bigger than anything I’ve had in a long time, that’s for sure.” I glanced over at my meager 4″ prick and winced. She was right; the dildo certainly wasn’t “huge”, but it was a considerable step up from what I had to offer.

Anna closed her eyes and pleaded with me, “Tim, tell me what you see, talk dirty to me. Tell me about this cock. This real man’s cock!! Tell me what I want to hear!”

I couldn’t believe how much her jabs at me were turning me on. “Oh, Anna, you should see this dild-this cock! It’s huge! I don’t think it’s going to fit!”

She pushed hard on the cock and the bulbous head popped past the tight resistance of her pussy and slid inside a couple inches. Anna winced and her hips lifted from the bed. “Aaaggggghhhh! Soooo big!”

“That cock looks so good sliding into you.” I was getting into this now. The embarrassment of the situation was fading away. All I wanted to do was use my words to stimulate Anna, to help bring her to orgasm. “It’s not too big, it’s just right! You were meant for a cock like this, for a real man’s cock!”

“Ohhhh, yes! Tell me more!” Anna had managed to work about 4 inches of the wide, thick cock into her now. She moved it slowly, in and out, taking a little more of the shaft on each stroke.

“It’s more than halfway in. It’s already in as deep as I can go, but it’s a lot thicker! Your pussy looks so good wrapped around a big dick!” It was true- Anna’s inner lips disappeared with each stroke, only to emerge again tight and thin, gripping the shaft of the cock as it retreated. Her clit was being maneuvered back and forth from the tension the large girth was providing.

“Oooooohhh! It feels so good! Ohhhh, god! Fuck!” Anna was really worked up; she rarely cursed, even in the bedroom. “It feels so fucking good!”

“Yeah baby! Push it in!” I encouraged.

She fingered her clit furiously as she pushed hard on the dildo. The final inches of the shaft disappeared in her pussy in one long stroke. All 7″ of thick rubber cock was now buried inside her.

“Ah-ah-ah-ah!! I’m cumming!!” Anna screamed out as her hips thrashed about on the bed. She squeezed her thighs together, as if to push the dildo in as far as it could go. “Oooooh! Oooooph!” Anna came hard. I could see her pussy clenching the dildo, trying desperately to milk it. Her orgasm tapered off slowly, seemingly going on forever. Her thighs quivered and her juices ran down her leg as her body relaxed.

It was at this point Anna remembered the dildo also vibrated; she turned the switch on the base and this renewed the feelings in her pelvis. The final waves of her orgasm started to grow in intensity once again. Like a roller coaster, she was beginning to climb the next hill. The hum of the motor was not loud enough to drown out Anna’s moans of ecstasy. She moved the vibrator in circles inside her, twisting it and making sure it touched every part of her. Finally, she must have landed on her G-spot, because she gasped and pulled up on the bed. Another orgasm hit.

The buzzing and moaning continued as Anna experienced orgasm after orgasm. The intensity slowly tapered off, each one less powerful and shorter than the last. Finally, she went completely limp and stopped moving. She slowly pulled the dildo from her drenched pussy with a “pop” sound. Her pussy was red and swollen, and gaping open slightly. I could see the muscles inside. Every so often they would spasm and the gap would close momentarily, her body still recovering from the big dick invasion it had suffered.

I couldn’t see Anna’s face past the rising swell of her breasts moving with her deep breaths, but I knew she must have a huge smile. I thought about how good she must feel, how spent and exhausted her body must be. She was drifting off in post-orgasmic bliss; I, on the other hand, was still tense and horny from my prolonged arousal and denial.


I awoke some time later. I must have been more tired than I realized; I hadn’t even woken up when Anna untied my arms and slipped my cock back in the cage. The lights were off and I had no idea what time it was. Anna was on her side beside me, with her back to me.

I rolled onto my side and nudged up to her from behind. I felt the warm flesh of her ass envelope my groin and my caged cock nestled in her crack. I reached around with my arm and hugged her to me, my hand slipping between her soft breasts.

She stirred and moaned groggily, pushing her ass back against me. “I love you,” she whispered.

“I love you, too.” We drifted off to sleep.

One comment

  • jsmyzer

    Love how this story is progressing – feel like I am right there and love how he is being taken where he really wants to go.


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