Chastity Resort Pt. 03

"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!"