Chastity Resort Pt. 06

"Ohhhhh....ohhhhh, noooooo!" I whimpered. I yanked at the straps holding my wrists and rotated my hips, trying desperately to touch my cock against something, anything!

"Please, touch me!!" I begged, to no avail.

"That's called 'edging'," Anna said matter-of-factly. "Did you like it?" She stroked the sides of my pelvis slowly, causing my turgid cock to strain for release. Another bubble of cum seeped out of the tip of my purple cock head.

"What the--why did you do that?!" I was nearly speechless.

Anna lay beside me and propped her head on my arm. Her free hand circled my groin. "It's meant to prolong pleasure. It keeps a man from shooting too soon and ruining the sexual encounter prematurely. This way you can stay aroused and perform longer. Isn't that what you want? Don't you want to spend as much time with me as possible?"

She knew what she was doing. "Of course, honey, but--" I started.

"Then this is the best way, trust me. If done properly, it will eventually feel almost like an orgasm. Especially after 5 or 6 edges."

"5 or 6?!" I groaned with frustration. Anna circled my cock with her fist, nearly obstructing it from view with her single hand. Only the thick bead of cum was visible above her fingers. She stroked me again slowly, until I felt the familiar stirring in my balls and the filling of my shaft. She must have sensed the nearness of my orgasm, because just when I reached the point of no return, she stopped.

"No, no, no, no, no!" I cried as my cock tried desperately to tip over the edge. This time it twitched once, then relaxed completely. A small stream of cum ran from the tip and fell onto the back of Anna's hand as she caressed my stomach. My cock was literally leaking cum with no orgasm. My balls were so full there was simply no more room for all that pent-up fluid.

"There, there..." Anna cooed. "We're almost ready for Lisa. Just once more..."

My breathing was rapid and I was beginning to sweat. "I don't think I can take any more!" I cried with a whimper.

"If that's true and you want to stop, just say so. We can stop. But know that it's right back into the cage for the rest of the day. You won't get the release I'm offering you until at least tonight. We have a busy day planned."

Talk about a rock and a hard place. If I was to get locked up again right then, I would have gone crazy, I'm sure of it. I was nearly insane with arousal and frustration. Suffering through another 'edge' was the lesser of the two evils.

"Ok," I gulped. "Keep going."

Anna smiled. "That's what I want to hear!" She began kissing my neck as her hand found my recovered penis once again. This time she stroked it ever so lightly, with just her thumb and two fingers. It grew impossibly hard under her light touch and nearly throbbed out of the grasp of her fingers. A steady stream of precum was oozing from my dick and adding to the small pool of cum on my stomach.

I tried my best to stay silent as Anna worked me into another frenzy. Maybe if I was quiet she wouldn't know when I was about to orgasm and I could blow my full load.

"Tim, you have to tell me when you're about to cum." Anna whispered in my ear. Was she reading my mind? "If you have an accident, you'll ruin all our progress and we'll have to start over. Everything so far will have been a waste."

I groaned at the thought. I closed my eyes tightly and fought off my orgasm. I sure didn't want to endure another week of Anna's teasing without a release first. I tried to control my thoughts, but images of Anna kept flooding my mind. I thought of her when we first arrived at the resort, in her skin tight yoga pants and her cleavage spilling out of her thin tank top. I thought of her ass squeezed into those shorts as I hiked behind her in the desert. And I thought of the way her ass rippled as I fucked her from behind with that huge strap-on not 30 minutes ago. It was all too much.

"Stop! Stop! I'm going to cum!! Don't touch me!!" Anna dropped my cock, and I squeezed my groin muscles hard. I gasped and winced as I fought back a mighty orgasm. After what felt like an eternity, the urge slowly subsided and I relaxed my body, slumping into the bed.

"Bravo!" I looked over to see Lisa standing at the bedside. "Nice work, you two!"

"I did as you said," Anna said proudly. "I brought him right to the edge three times!"

"I'm surprised! Usually it doesn't go so well the first time. Most of the wife caves and lets her man have an orgasm, or he can't control himself and has an accident. Good job, Tim, you must really want this to work!"

Something like that, I thought. Oh, how I wished Anna had caved.

"I bet you're dying for some relief, right Tim?" Lisa asked.

"Yes, please!" I begged.

"Ok, Anna, come down here with me." Lisa sat on the bed beside my waist, and Anna on the other side. Lisa lifted my leg so it bent at the knee and my foot was flat on the bed near my ass. Anna did the same. Next, Lisa produced what looked like a lumpy dildo with a sharp curve at the end.

"Tim, do you know what this is?" I shook my head no. "It's a prostate massager. It will stimulate the internal parts of your penis that never get touched. The prostate gland helps produce and store semen. This will help to coax that out and relieve some pressure. Is it ok if I continue?"

I was desperate for some relief, so I nodded yes. Lisa proceeded to apply a generous amount of lube to the device. She placed it at my asshole and I jumped with surprise. She pushed slowly and firmly until the rounded head of the massager popped into me and slid past my sphincter. It felt extremely weird as I had never done any ass-play before. This was a week for a lot of "firsts". As Lisa slid more of the narrow device inside, I began to feel a strange sensation of arousal, but unlike any I had ever felt before. Eventually, she must have touched my prostate; I felt an incredibly pleasurable wave wash over me and a sudden increase in pressure. Then, a slow and steady feeling of release. I looked down and was shocked to see pulse after pulse of cum flowing from my penis, which had softened considerably. It was the strangest thing to see cum pouring from my semi-hard cock while feeling no orgasmic sensation.

"See, Anna?" Lisa said. "He was so backed-up that a simple insertion has him flowing like a river. Normally, you won't get quite this response, but it depends on how often you milk him."

"Milk him?" Anna asked with a laugh.

"That's what it's called. It's not an orgasm, but there is still a release. It's more relief than pleasure for him."

That was an accurate description. Lisa began to roll the massager around, hitting my prostate from every angle. The effect was incredible; it was as though I was having a constant low-grade orgasm. Very low level, almost no pleasure at all. It also served to coax out even more cum. Soon, there was a large pool collected under the tip of my now completely soft penis. There was so much it began to run down my side and onto the bed.

Finally, the flow stopped and Lisa could produce no more. She withdrew the massager slowly and I felt a weird void as it was removed.

"Tim, why don't you describe how you feel?" Lisa asked quietly.

"I feel...I feel very relaxed. Like a weight has been lifted."

"And your state of arousal?" Lisa prodded.

I glanced at Anna and my eyes fell to her full, hanging breasts and her wide curvy hips. I could see the small triangular patch of dark hair emerging between her thighs. My erection quickly returned as I gazed at her.

"I'm...I'm still horny. How is that possible?" I asked, surprised.

"A prostate massage releases most of your semen, but not all, giving you physical relief. But it alleviates almost none of your hormones, leaving you still aroused and wanton."

"If anything," I replied, "after all this attention, I'm MORE aroused than before! But it's much more bearable."

"That's exactly what we're going for," Lisa stated triumphantly.

"Oh, good!" Anna squealed. "This is fantastic!"

Lisa continued talking to Anna. "You'll want to eventually extend the time between his milkings. As you have more frequent and intense edging sessions, you'll find his tolerance for orgasm denial increases."

"Orgasm denial?! Wait a minute, what's that?" I felt a panicked sensation starting.

Lisa sighed and shook her head. "This is a lot to take in at once..."

"No, go on," Anna insisted. "I want to know."

"Well, the male orgasm is purely recreational. It serves no medical or necessary purpose. A man doesn't NEED to orgasm. He can produce sperm and expel it naturally without ever cumming. In fact, in the context of a female led relationship, male orgasms are usually reserved for special occasions or rewards. Orgasms only serve to derail a couple's sexual progress and reduce intimacy."

My heart skipped a beat and there was a lump forming in my throat. No cumming?!

"Of course, every couple is different. Some women enjoy watching a man ejaculate and they get pleasure from it. But it's always at the discretion of the wife whether or not her husband orgasms."

"That makes sense," Anna nodded. "Right, Tim?"

Everything in me wanted to say "no", but when my mouth opened I heard myself say, "Yes, I guess so." What was happening to me??

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"Are you almost ready?" Anna called to me from the living room of our suite.

I quickly finished drying off and joined her. "Let's go," I said.

Anna stood and headed for the door, completely nude. It would be the first time she was out and about the resort without something covering her bottom.

"You're not wearing anything?" I asked, surprised.

"It IS a nudist resort," she laughed. "Besides, do you WANT me to cover this up?" She spun and grabbed her ass with both hands, giving me a quick show as she squeezed her soft cheeks. She looked so hot.

We left the room and started walking to meet Chad & Lisa on the boardwalk. I was definitely nervous as we approached them after my morning "experience" with Lisa. In the heat of the moment, so to say, her presence hadn't bothered me. But now...

"Hey, you two!" Lisa exclaimed as we arrived. "Grab a seat. We were just about to order."

Anna and I sat and looked over the menu quickly as the waitress took Chad & Lisa's brunch order. When she was gone, we all sat in awkward silence for a moment. Loss broke the quiet.

"This morning was fun, right?!" She laughed as she looked from Anna to me. I felt my face turning red. "Oh, don't worry...I told Chad everything."

Great, I thought. Fantastic.

Chad looked at me reassuringly. "Don't worry, man. The first time Lisa uh, "relieved" me I was hella embarrassed. It's only natural."

"He did great," Anna said, squeezing my thigh under the table. She left her hand there.

"I heard you got a little something as well!" Chad smirked at Anna. Now it was her turn to blush.

"Well, I wouldn't call it 'little'"..." Anna said, sheepishly.

Lisa and Chad both chuckled at that. I wanted to crawl under the table.

The rest of the meal was largely uneventful. Thankfully, the conversation quickly turned to non-sexual topics and soon I had almost forgotten I was even at a nudist resort. Of course, the occasional naked passerby on the beach or boardwalk snapped me back to reality. It really was fun getting to know our new (and old) friends. They seemed like a great couple, someone we would normally hang out with back at home.

Brunch ended and the girls decided they wanted to do some shopping. We began walking down the boardwalk. It was reminiscent of the boardwalk at Atlantic Beach or Navy Pier, albeit on a smaller scale. We browsed around souvenir shops, T-shirt shacks, and snack counters. Before we knew it, it was early afternoon.

"Oh!" Lisa exclaimed. "Yoga starts at 3 o'clock!"

"I completely forgot about that!" Anna said, disappointed. "I didn't bring any shorts. Oh well, maybe tomorrow."

"Nonsense! We'll just pick up something cheap from a shop," Lisa suggested. "Chad agreed to join in and I'm not going to miss that! This lug is about as flexible as a board!" She playfully slapped Chad's taught abs. He winced in mock pain.

We followed the ladies into a clothing shop and hung out by the entrance while they looked.

"So," Chad started. "You're probably going to run out of this place at the end of the week and never look back, am I right?" He grinned.

I laughed. "Hardly! This place has been great, a real eye-opener. I was just telling Anna last night that our sex life has never been so amazing."

"That's great! Anna seems to be enjoying herself as well."

"Oh, I KNOW she's having a good time!" I joked.

We turned to watch them in the store. They were at a rack of bikinis, still within earshot.

"What about this one?" Lisa asked? She was holding something in front of her that I couldn't see.

"Ohhh, I love it! So cute! I hope they have another one." Anna started flipping through the rack.

"Here's one!" Lisa said.

Anna checked the tag. "Haha, that won't work."

"The ties are adjustable...just try it. They have to match."

Anna sighed. "I'll try it. But that's a small...I usually wear at least a large."

I gulped as they walked to the changing rooms at the back of the store. I still hadn't seen what they were trying on.

Our wives emerged a few seconds later and began walking towards us at the front of the store. Chad and I looked at each other as they approached, smiling.

They were wearing matching white string bikini bottoms. The front was just a small triangle of cotton material.

"What do you think?" Lisa asked as they twirled around before us.

My mouth literally dropped open when Anna turned around and I saw the way the bottoms fit her shapely ass. Or didn't fit. The thin, clingy white material struggled to contain her big round ass. It was stretched tightly across her soft flesh, curving up over the top of each cheek and meeting again in the middle, where the cotton scrunched and pulled down exposing the top of her ass crack. This also caused the thin material to ride deliciously up her ass exposing at least 1/2 or 3/4 of her round butt.

On the other hand, Lisa's small athletic ass fit in the bikini perfectly. There was just the right amount showing at the bottom, and the top formed a wide, full triangle that covered her ass. She had a fit body, so she looked good; but it was like looking at any one of a hundred asses on the beach.

"That looks...amazing!" Chad said. I wasn't sure which woman he was referring to. I had an idea, though.

"I don't know..." Anna hesitated. "It's way too small..." She looked over her shoulder and arched her back, trying to get a good look at her backside. This only served to push her ass out farther, and it bounced and jiggled as she shifted her weight and shuffled her feet to get a better view. "What do you think?" She asked me.

"Ummmm....it looks...you look...wow!" I managed to stutter out some words.

"I think that's an affirmative," Lisa declared. Anna smiled.

They paid for the "clothes" with our room numbers and we continued down the beach to the yoga area. When we arrived, I grabbed a seat nearby while the other 3 joined the class.

As the class progressed I was more and more thankful once again for my dark sunglasses. This time, there was no other distraction on the sand but my wife. My eyes were fixed on her throughout her movements. She bent, stretched, reached and leaned while I stared, drooled, dreamed and longed. The positions she was able to contort her body into were incredible and the fact she was doing so nearly nude was not lost on me. I took the time to think long and hard about how much I loved my wife, how much I desired her, and how lucky I was to have her. She turned me on like no one else.

I did a small double take when mid-way through the exercise I realized that Chad had taken a position directly behind Anna and not beside his own wife, who was beside Anna. There was no doubt in my mind he had chosen that spot deliberately. I know I would have. I thought I had a good view; his must have been heavenly. I immediately regretted not joining them. I could see that Chad was enjoying the show, as he wasn't really keeping up with everyone else and he would stop and sit out during some of the more provocative poses. For the first time all week, I detected some movement from his chastity device; he was getting turned on watching my wife! The large red cage was pulling away from his body and his oversized balls were standing out. That bastard! I didn't know how I felt about this.

My thoughts were preoccupied with images of Chad's uncaged penis from the other night in the hot tub. The way it had dangled and swung, all thick and menacing as he displayed it that night. The way my wife had been fixated on it and curious. Did she really want a bigger cock? She did really enjoy that huge dildo. But it was just roleplaying, right? She wouldn't want to...would she??

I shoved those thoughts out of my head and closed my eyes. I must have drifted off to sleep, because the next thing I know I was standing by the bed in our hotel room, watching my wife give Chad a blowjob. She paid me no attention; all her focus was on his huge prick in her mouth, in her hands. Her small hands.

The image flashed to my wife bent over on all fours, Chad driving his monster cock into her pussy. She was screaming and moaning, he was pumping faster and faster until--

"Tim! Tim! Wake up!" Anna was shaking me. I was on the beach. I breathed a sigh of relief; it was only a dream!

"Good dream?" Anna laughed. I looked down at my cage. My dick was visible through the clear plastic, a deep purple color and swollen to its max. My balls were once again tight and aching. Already?! I thought. Weren't the effects of that prostate massage supposed to last longer than this?!

Anna pulled me to my feet, planted a kiss on my lips and turned to leave, pulling me behind her.

"Come on. Lisa and Chad are waiting for us."

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We ate a quick lunch at an outdoor patio on the boardwalk and then it was off to do more shopping.

"I know where we should go..." Lisa pointed across the way to a store called Happy Endings. At first I couldn't believe there would be an adult sex shop at a resort, even a nudist one, but then I remembered this wasn't your average vacation destination. It was a chastity resort.

We made our way into the air conditioned, brightly lot store. There was all manner of sex toys on display; this was not a watered-down "intimacy" or "romantic" store. There were dildos, vibrators, clothing, magazines, videos, everything imaginable. And of course, there was a large section of chastity related merchandise. That's where Lisa led us.

"Oh my! Look at all this stuff!" Anna exclaimed. "I don't even know what most of this stuff is."

"You'll figure it out over time," Lisa said. "There's a lot of nuances to this lifestyle that keep it spicy."

Anna pulled me over to the lingerie section and she began to browse. She pulled me close behind her and placed my hands on her waist. My hands were on the thin strings cutting into her soft flesh of her sides. I gulped as I looked down and saw her big, round ass wiggling between us. The thin material of her bikini rode high up her ass, and when she pushed back my caged cock slid right into her deep crevice. I gulped and closed my eyes.

"What about this one?" I looked over Anna's shoulder to see her holding up a silky lace camisole.

"Sure, that's nice. I bet you'd look amazing in it." I said honestly.

"I think I'll try it on!" Anna squeezed her ass past me in the narrow isle and disappeared into a changing room stall.