Chastity Resort Pt. 06

This is a continuation of a multi-part story. If you don't start with part #1, none of this will make sense.

*****

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.