Chastity Resort: Part 6

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by handyrandy9


Read Part 1 – Click Here!
Read Part 2 – Click Here!
Read Part 3 – Click Here!

Read Part 4 – Click Here!
Read Part 5 – Click Here!


Part 6…


I awoke to what felt like something poking into my lower stomach area. As I groggily opened my eyes it took me a moment to figure out what was happening. My wife was kneeling on the bed beside me, leaning over my–oh shit!! I had forgotten I was still wearing the strap-on from the night before. Anna had the fat head of the life-like dildo in her mouth and was slowly stroking the shaft with her hand.

“What are you doing?!” I cried out in shock.

She let the head slip out of her mouth, swallowed, and smiled. “What? You usually love it when I wake you up with a blowjob.”

I groaned loudly. She was still playing the game, pretending the strap-on was my real cock.

“That’s when you’re sucking my REAL cock,” I said sarcastically.

“Oh. Why didn’t you say so? Of that’s what you want, all you have to do is ask.” She said matter-of-factly.

Was this a joke? I thought. “Okaaay….Anna, would you please suck my cock? My real cock?”

“I don’t have the key, remember? I traded it to Lisa last night for THIS cock.” She was still stroking the fat dildo slowly with one hand. “I could always ask her to bring it over…”

“Ok! Ask her!” I reached for the phone beside the bed.

“She might want to stay and watch the show. Would you be ok with that?”

At this point, I would have agreed to nearly anything for the promise of a blowjob. My balls were so sore and backed up with cum I could hardly stand it.

“Yes, that’s fine. Just call her!”

Anna let go of the dildo, which bobbed and swayed as she grabbed the phone and dialed Lisa and Chad’s room number. She walked to the next room and talked so softly I couldn’t hear what she was saying. I stood and started to remove the strap-on. Anna walked back in and stopped me.

“Hey! Not so fast. Lisa said since I’m going to suck your cock that you should do something for me first.” Anna smiled seductively.

“Anything!” I groaned. “But please hurry!”

Anna sauntered back towards the bed, her hips and thighs jiggling and her full breasts swaying from side to side. She got to the bed, paused, and then turned and walked to the reclining chair by the window. I watched as her round ass rose and fell with her exaggerated steps. She leaned forward, placed her hands on the back of the chair, and stuck her plump ass out as far as she could. She flipped her hair to the side as she turned to look back at me over her shoulder with a sexy smile on her beautiful face. Her heavy breasts bounced as she turned and then hung down beneath her, round and impossibly full.

“Come and fuck me.” The words slid sweetly from between her full, pouty lips like honey and hit my ears like a ton of bricks. I was finally going to fuck my beautiful wife from behind! I was so thrilled with the prospect that it almost didn’t matter that I wouldn’t be using my real cock.

I stood and walked toward her nervously, the fake penis jutting from my pelvis and bouncing obscenely. Anna watched over her shoulder as I approached. I stood behind her for a full minute or two taking in the sight before me. My wife’s feet were spread apart slightly and planted firmly on the floor. Her thick, succulent thighs gave way to her curvy, round hips and her ample ass. I could just see the folds of her pussy below her hanging ass cheeks. She wiggled her butt subtly and the snow white orbs of tender flesh wobbled back and forth, even after she ceased her movements. Her ass was free from even a hint of cellulite; her cheeks were impossibly round and smooth. Her ass was so full that even in this bent position there was a slight crease where it met the small of her back. Her back dipped down at her slender waist before rising again under the wavy locks of her long dark hair.

I gripped the base of the strap-on for the first time and was surprised by how realistic it felt. I looked down at the large cock in my hand. I was standing a foot behind my wife, but the long, thick dildo nearly touched her. It had to be eight or nine inches long, at least. I stooped down slightly and stepped forward, squeezing the dildo between her thighs. I rubbed it back and forth along her pussy.

“Tim, I don’t think I’m ready for your big cock yet…get me wet first.”

I pulled back and dropped to my knees behind her. Her ass was directly in front of me. I put a hand on each of her thighs with my thumbs between her legs. I used them to spread her pussy lips until I saw the pink of her slit. Her opening still gaped slightly from last night’s oversized penetration. Leaning forward, I began kissing the soft insides of her parted cunt. She moaned with increasing volume and frequency as I flicked my tongue in and out, up and down, back and forth. My nose was pressed into the crack of her ass, but all I could smell was the sweet, familiar scent of her rapidly moistening pussy.

After a few minutes, Anna interrupted me. “Mmmm, OK. I’m soaking wet now thinking of getting fucked from behind after so long. Get up here and give me that big dick!”

I stood up and pressed the dildo against her pussy. I smacked it against her lips, eliciting a wet splashing sound. She really was wet. I teased the cock along her slit, spreading her juices along its length.

“Ohhhhh,” she groaned wantonly. “Stop teasing and give me that dick!”

I placed the head of the strap-on against her entrance and paused. “Tell me what you want,” I prodded, nervous with anticipation of what I was about to do. “I want to hear you say it.”

“Ohhhh, god…I want to feel your big dick inside of me. I NEED your cock deep in my pussy! Please Tim…Fuck me from behind with your huge cock!”

I pushed forward and the large head slipped past her outer lips. I pushed until I felt resistance a couple inches in. That was her point of no return. I pulled back and pushed again. I worked the cock in and out of just the entrance of her pussy, never going past the point of resistance.

“Oooohhhh…push it in…please! It feels soooo big, I need to have it! Give me that cock!”

I had never heard her so vocal, and never so dirty. Her tongue was really loosening up on this trip. I grabbed her hips for leverage and pushed firmly against her resistance until the wide mushroom shaped cock head slid past her cunt muscle with a ‘pop’.

Anna gasped and clenched forward. “Oh my god!” She cried. I pulled her backwards, forcing more of the cock inside her.

I continued forward, sliding about 6 inches of the dildo into her. I pulled back and she moaned again. “Ohhhh, it feels like you’re turning me inside out! This is incredible!”

I started fucking her slowly using 6 inches of the thick cock. My hands were on her soft, wide hips pulling her ass back and forth to match my thrusts. Suddenly, she rocked back hard, forcing all but the last inch of the dildo to sink into her cunt. She screamed with pleasure. “Aaaaaahhhhggggg!!!!!”

Her round, soft ass cheeks were pressed against my pelvis. This is it, I thought with excitement. This is what it’s like to fuck doggie-style. I moved my hands to her fleshy backside and kneaded her ass. I rocked gently against her, grinding 8 inches of cock inside her tight, wet pussy. She was still unable to squeeze that final inch into her moist cunt.

“Is this what you wanted?’ I asked, squeezing her ass hard. “You want me to play with your big ass while my dick is buried inside you?”

“Oh, god, yes! This is what I’ve been dreaming of!”

At least we both agreed on that. I dreamed of having my wife like this just about every time I saw her wonderful ass. Who cared if it wasn’t my cock?! This was as close as I could ever hope to get, and Anna was definitely enjoying it more this way.

“Your ass looks so good, babe. I’ve literally had dreams about this.” I pulled the cock out of her slowly until just the tip was in her, then slammed it back in with one motion.

She gasped and cried loudly. “Ahhhh! Your cock is so big! Fuck me with your huge penis!” She hissed through clenched teeth.

And fuck her I did. In and out with long, hard, fast strokes. I was mesmerized as I watched 8 inches of cock slam in and out of her wet pussy. Each time I drove into her, her ass slammed against my stomach and jiggled wildly before bouncing off again. The motion sent ripples over her soft flesh all the way up to my hands gripped tightly to her slim waist. My own cock, my real cock, swung wildly back and forth in its plastic cage as I pounded her. My heavy aching balls slapped against my thighs with a sharp pain on each stroke, and my cock cage grazed my wife’s clit as it swung forward. I knew my cock must be leaking precum like crazy, but with Anna’s copious amount of juices running out her pussy and down my groin, I couldn’t tell her moisture from my own.

Anna began bucking against me more and more, and I knew she must be close to cumming. I could read the signs, even if she had never cum from penetration alone.

“Ahh, ahh, ahhhhhh! I’m going to cum on your big cock! It’s splitting me in half!”

“Yeah, baby!” I encouraged her. “Cum on my cock! Squeeze my dick! Show me how much you love my big cock!”

Anna’s cries got shorter and shorter until they stopped completely and she slammed her pussy back and held her ass against me. I grabbed her hips and pulled tightly, grinding my dick inside her. My caged cock swung like a pendulum below.

“Ohhh….fuck……yes, yes, yes!!!” Anna panted as she came harder than I’d ever seen her cum before. Her ass shook as her pussy spasmed. I imagined I could feel it, feel the contractions of her orgasm around my own cock, feel her pussy milking my dick as she came. Of course, I felt nothing in reality, just intense pressure in my balls swinging between my legs.

Anna’s legs gave out from under her and she fell forward onto her knees in the chair. I fell with her, still grinding and pumping the dildo as if it was real and I had orgasmed also. Finally, when her movements had stopped and her body went limp, I slowly pulled the dildo out her tired and spent pussy. It slipped out with an audible slurping sound.

“Wow!” I heard a voice say. I turned towards the sound to find Lisa standing in the doorway to the bedroom with a big grin on her face. “That looked like fun!”

“Hey!” I cried. “What the–? What are you doing here?!” I was equal parts angry and embarrassed. I tried my best to cover the strap-on with my hands, but it was too big.

“I came to return your chastity key, of course. And Anna promised me a show, but I didn’t expect that!” Lisa walked towards us, my key in her outstretched hand.

Anna turned, sat on the chair, and took the key from her. She grabbed the dildo still attached to me and used it to pull me closer. The dildo lay against her cheek and across her shoulder as she reached around me to unfasten the straps. She tossed it aside and gently cupped my swollen balls.

“Now it’s your turn,” she said looking up at me. She rolled my tender balls in her fingers. “I assume you still want that blowjob?”

“Y-yes, please!” I tried to contain my excitement. I was finally going to get some pleasure of my own!

“Now, you know…if we do this I’m in control, right? You have to trust that I know what’s best for us. Best for you.” Anna continued to fondle my swollen balls gently. My dick was straining hard against its cage, standing out from my body as much as it could. This caused the ring behind my sack to pull my balls forward with tremendous pressure. They were turning a deep purple color as Anna played with them. I winced.

“Of course honey, whatever you say!” I would have agreed to anything as long as she unlocked my cock. My groin was on fire!

Anna glanced at Lisa, who was standing off to the side. Lisa nodded, and Anna placed the key into the lock, turned it, and pulled the lock through the holes in the chastity device. My cock immediately sprung upward and grew with record speed. Anna didn’t even have a chance to slip the tube off my dick before I was fully erect. No matter; my penis, although fully engorged with days of pent-up energy, didn’t fill the girth of the tube. The 2 inch long device extended just over halfway down the length of my skywards pointing shaft.

Anna easily slid the tube off the end of my cock. Without saying a word, she stared up into my eyes and kissed the underside of my sensitive purple head. Just this simple touch caused my cock to twitch involuntarily and a large bead of precum to escape my slit and roll down until it hung suspended from the ridge below my head. She lapped up the clear fluid with the tip of her tongue and swallowed it. She licked her lips and kissed again, this time slipping the tip past her parted lips.

I moaned loudly and my eyes rolled shut. My knees quivered and felt like they would give out.

Anna stood from the chair and pointed towards the bed. “Why don’t we go over there so you can relax?”

I scurried to the bed, my rigid cock bouncing tightly in front of me. I lay down and propped my hands behind my head as Anna knelt beside the bed and resumed her blowjob. After so much teasing and so long without stimulation, the slightest touch felt wonderful. She licked my swollen balls and sucked them into her mouth, causing both a wonderful tingling sensation as well as an aching deep within. They were impossibly full and ready to unload. Even after working just my balls for several minutes, my dick was leaking copious amounts of precum. Anna moved to the base of my shaft and sucked the underside with her soft, full lips. She ran her mouth up and down the lower half, staying far from the overly sensitive head. She was teasing me.

“Oh my god, Anna, that feels amazing!” I breathed. I glanced down and saw a pool of sticky precum forming on my lower stomach and a string of fluid stretching to my pulsating cock. My dick twitched and throbbed angrily, fully engorged and thicker and harder than it had ever been.

After several minutes of this indirect teasing, she finally took me into her mouth. She slid her lips over the head and pulled my dick upright, before continuing down the shaft until she had effortlessly engulfed my entire member. Her nose nestled against my stomach. I felt her stick her tongue out and flick it along my balls. She had as much as possible of my sex in her mouth.

“Wow!” I heard a voice from across the room. Lisa!! I had completely forgotten she was still there! She was sitting in the recliner, watching this entire production unfold.

“I’ve never seen anyone take a whole cock like that before!” She said, amazed.

Anna withdrew her mouth from my pole and smiled. “Well, it’s kind of easy with a small one like this. It doesn’t take a lot of effort.”

I groaned at her demeaning comment.

“I can barely fit the head of Chad’s dick in my mouth, much less the whole thing!” Lisa continued. “Wow…” Her voice trailed off.

“Do you want to try?” Anna asked, to my surprise. Was she really offering my cock to another woman? “I don’t think Tim minds, do you Tim?”

I shook my head ‘no’. I couldn’t believe what was happening. Lisa walked over and knelt on the bed, on the opposite site from Anna. She reached out and tentatively touched my swollen member. I moaned at her touch. It was the first time anyone had touched me other than Anna in 7 years.

“Go ahead, help yourself,” Anna encouraged Lisa. “Just make sure you don’t get him TOO excited!”

Lisa wrapped her dainty hand around my cock. Even with her fist pressed against my pubic bone, her fingers covered my entire shaft and half the head. Her thumb and fingers overlapped.

Her unfamiliar touch elicited another drop of precum to form on the tip off my penis. Lisa looked at Anna, who nodded approvingly, and then leaned in and licked it off.

She stroked my cock a few times. “Here goes,” she said, and leaned forward. Her hand slid down as her mouth enveloped my penis. She didn’t pause until her nose was touching my body as Anna’s had. She looked up at me, her hazel eyes big and round. Slowly, she slid back until my cock sprang from her mouth and slapped against my stomach.

I had been so engrossed watching Lisa deep throat my dick, I barely noticed as Anna pulled my arms over my head and attached them to the straps still affixed to the top of the bed. I pulled, testing them. I was once again immobile, at the mercy of these two naked women.

“I’ve never swallowed a man’s entire cock before,” Lisa said.

“Haha, I told you it was easy!” Anna laughed. “You can keep going if you want.”

“No, I’d better go get ready for the next phase. You keep working him like we talked about.” Lisa stood and left the room. I stared at her toned athletic ass as she walked away until she was out of sight. Turning back to Anna, I realized she had seen me staring.

“Like what you see?” She asked with a sneer.

My face was red from having been caught. I tried to change the subject. “What does she mean, ‘the next phase’? I don’t think I like the sound of that.”

“It’s a good thing, I promise. You remember how you said you liked being aroused and wanting me? And how if you had an orgasm that would go away and you wouldn’t feel those wonderful things anymore?”

It seemed as though she was twisting my words. She had started to slowly drag her fingers across my pulsating cock, and it was clouding my thoughts.

“Yeah…I guess I remember.” I just wanted her to keep touching me at all costs.

“Well, Lisa said there’s a way for you to get relief from all that pent up frustration, but still keep your desire to please me. Isn’t that great?” Anna teased the head of my cock. Precum oozed out in an almost continuous flow now.

“Yes honey,” I panted. “I’d like that. I need a release. Please–the blowjob…you promised!”

“Oh, this?” Anna leaned down and placed her open mouth above my desperate cock. “Is this what you want?” She grazed the tip with her lips, causing my dick to jump and a wad of precum to practically shoot out. “All you have to do is agree to Lisa’s plan. Agree to your release; but it has to be on MY terms!”

I groaned and thrust upwards trying to get more contact with her warm mouth. She pulled away and shook her head in disapproval. “Uhhhhh, ok!!! I’ll do whatever you want! Just keep going!!!” I continued to thrust and squirm.

Anna smiled and lowered her mouth to my aching cock. The next few minutes were heavenly; she sucked and licked with such passion and desire. I knew from the way she pleasured me that she too had missed the contact between us. Her blowjob was slow and purposeful; it was as if she was making out with my penis.

My balls tightened and tried to withdraw into my body, ready to deposit their voluminous load, but they were stopped by the chastity ring. Without being able to retract my balls, my body delayed the start of my impending orgasm longer than normal. Usually I would have blown by now, but I was involuntarily resisting, hovering on the brink of orgasm without plunging over.

I moaned with a mixture of pleasure and frustration. “J-just a little more! I’m sooo close….” I squeezed my eyes shut and tried to will my body to orgasm. Anna kept her pace, without increasing her speed or pressure. “Come on, baby….. Just a little more, please!!!” She ignored my pleas. Gradually, my orgasm built on its own, ramping up and intensifying until I held my breath in anticipation. This was it!! I was going to cum!!

“I’m gonna cum!!!” I cried out with a shaky voice. I could feel the cum work its way into my shaft, my cock stiffened and paused, ready to spasm and shoot, and then…nothing!! Anna let my cock plop from her mouth and sat back.

“What are you doing?!” I whipped my head up and saw my cock twitch with the initial throws of orgasm. A large blob of white semen, not precum, formed on the tip and clung there. My cock relaxed, then twitched again, flinging the thick cum onto my belly, then…no more. My dick stood there, engorged and throbbing, with a single drop of cum stringing from the tip. My balls were tight and my shaft felt like it was full of cum waiting to explode. But it didn’t.

“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??


“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.”


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.

I tried to look nonchalant as I stood in the women’s lingerie section by myself. Thankfully, before long Anna called out to me.

“Tim, can you come here? I’m not sure this one fits right.” She stuck her hand out through the cracked door and motioned me in. I glanced around and saw no one watching, so I slipped into the room and pulled the door closed behind me.

As I turned to face Anna, I was speechless. The silk turquoise top was trimmed in black lace at the top and bottom. The thin spaghetti straps were straining to support the weight of Anna’s large breasts, which would have spilled out of the low cut bra if not for the band of sheer lace across the bust. It hung loosely down her frame and ended just above her navel.

“You look…amazing!” I managed to say.

“Hmmm, I thought the top was a bit small.” Anna cupped her breasts and jiggled them up and down.

“Um, no, it’s perfect. Here, let me try.” I reached out and replaced her hands with mine. I lightly squeezed and bounced her tits in the silk top. I stepped in and kissed her like a hungry man. At first she was slow to respond, but once she realized I meant business, she put her arms around my neck and returned the kiss. Our lips still locked, I pulled her to the short bench at the back of the small changing room.

“Mmmmm, nooo, we can’t,” Anna moaned, but her body said otherwise. I dropped my hand down and began rubbing her bikini-clad pussy. She parted her legs and moaned some more. “Ohhh, Tim!” she panted.

I caressed and rubbed over the thin material until I felt moisture; I knew I had her. I pushed her gently down onto the bench. I scooted her ass right to the edge and knelt down. I lifted her left leg up and began kissing my way from her knee to the soft part of her inner thigh, then I let her leg rest over my shoulder while I did the same to the other side. Once I had both legs over my shoulders, I gazed up into Anna’s eyes as I untied one side of her bikini bottoms and pulled the material to the side, exposing her wet pussy. Neither of us said a word or broke eye contact as I dropped my head and began licking her moist slit.

Her pussy was still somewhat loose and relaxed from the two fuckings with the large dildo. I wondered to myself if it was going to stay like this. Not that I minded; I loved the idea that my wife’s pussy had been stretched and molded to a big cock.

My hands stretched up her body and found her large, soft breasts. They slipped and slid in my hands through the silky material. I found her nipples and rolled them in my fingers, causing Anna to groan under her breath.

Anna grabbed my head and pulled my face tight to her wet pussy, not that I needed any encouragement. I was enjoying this. I ate her out and made love to her pussy for several minutes before Anna’s thighs began squeezing the sides of my head and I knew she was close to orgasm. I squeezed and jiggled her boobs as I increased my speed on her pussy. My tongue flicked as fast as it could across her engorged clit as she exploded into orgasm. Her thighs squeezed my head hard muffling all sound to my ears, and her pussy spasmed and convulsed on my face.

As she gradually came down from her climax, I gently licked the juices from her around her pussy. She tasted so good; I could have continued for hours. I wanted to bring her to orgasm after orgasm, to bring her more and more pleasure until she was satisfied and fulfilled. But this wasn’t the time or place for that.

Anna stood up and pulled me to my feet. She kissed me again, this time tasting her own juices on my lips. I wiped the excess from my face with the back of my hand as Anna tied her bikini again and removed the camisole top. Without a word, we exited the changing room and headed out to find our friends, my wife clinging to my arm and smiling from ear to ear.


To be continued…



One comment

  • Another great story. I especially liked the edging and chastity situations. Expand on chastity device choices in the next chapter.


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