Chastity Resort Pt. 05

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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!


Part 5…


“Why don’t you go ahead and lie on the bed and I’ll show you what Lisa gave me,” she said with a gleam in her eye.

“I thought we were going to sleep? I’m tired.”

“Not just yet. I want you to see this. I think you’ll really like it…” Anna teased, pushing me toward the bed. I lay on my back and she left the room. I was alone! I raised my hand to my still erect cock and paused. Should I? She wouldn’t know if I gave it a few quick strokes. It had been so long! I hadn’t even touched myself in 3 days. It would feel so good to wrap my fingers around and have a few strokes…

I nearly had myself talked into it, when Anna reappeared. I quickly dropped my hand.

“Silly me. What was I thinking?! I can’t leave you unrestrained like this.” She quickly lashed the nylon straps around my wrists and ankles, securing me to the bed. She started to leave, and then unexpectedly turned back to me. She bent at the waist with her butt sticking out and planted a big wet kiss on the underside of my stiff cock.

“Be right back!” She said cheerfully.

I looked down at my throbbing cock. The saliva from her kiss shone brightly on the red skin. I groaned. Here I was again, tied to the bed in total frustration, unable to touch myself. I had been so close!

True to her word, Anna returned in a moment and sat on the side of the bed. She had the bag Lisa had given her.

“Are you ready for an experience like you’ve never had before?” She asked.

“I-I guess so…does this mean I’m going to get some action?” I asked hopefully.

“Definitely.” She produced a blindfold from the bag and tied it around my head. “Can you see?”

“Not a thing.”


I heard her moving around and then I felt weight on my chest. She had straddled me and was facing my feet. She bent over and slipped something around my waist, then around my thighs. Her pussy must have been close to my face; her familiar scent filled my nose. I lifted my head and stuck my tongue out as far as I could, hoping to catch a lick. I searched for my target blindly. Just when I was about to give up, the tip of my tongue caught something. I wasn’t sure what; she was too far away. I strained as far as I could and got another taste. From her position bent over with ass out, it must have been her ass.

“Anna…” I pleaded.

“Yes, Tim?” She didn’t move.

“Anna, please…” I stretched and licked again. Still no movement.

“Tell me what you want. No- plead with me, beg me.”

My head dropped on the bed. That wasn’t fair; she would enjoy it more than me. But I did want her. I had to taste her.

“Please let me lick your pussy, Anna. I want to taste you.” My cock was absolutely throbbing. It must have been leaking pre-cum like a faucet.

“That’s not very convincing…”

“Please honey! I NEED to taste you! I’m so hungry for you, for your pussy.” I stretched and licked again. It was definitely the crease at the bottom of her ass cheek.

“That’s getting better… I’m considering it…” She still refused to move.

What did she want from me? “Anna PLEASE! I’ve never wanted to eat you out so bad! Your smell is driving me crazy. You’re so close, but I can’t reach…this is torture!! If you don’t let me lick your pussy, I’ll go crazy!” I was practically in tears I was so frustrated.

“That’s what YOU want. What’s in it for me?”

I couldn’t believe her. “I’ll make you cum! You’ll cum sooo hard, I promise! I want to give that to you, I want to make you orgasm! I want you to feel satisfied! Just look at my cock, it feels like it’s going to explode! That’s how much I want you!”

She didn’t say anything, but she did slowly inch her way back towards my face. Her pussy must have already been leaking juices onto my chest; as she moved her pussy slid smoothly and made a wet sound.

I strained my neck and slammed my tongue between her moist lips and down her tunnel as far as I could in one quick motion. She responded with a loud moan. “Ohhh, god!!”

I worked my tongue in and out like a small cock, twirling and flicking it while it was inside her. I could just reach the front of her lips, but fell short of her clit.

“Back up babe,” I mumbled between licks. “I can’t reach your clit.”

“No…make me cum this way. If you really want this, you can make me cum without my clit!”

I didn’t know if I could, but I was sure as hell going to try. Anna had never orgasmed from penetration alone; at least not any time I had fucked her. I always thought she was like most women and needed clitoral stimulation to orgasm.

I doubled, tripled my efforts. I launched a full out assault on her pussy. My tongue penetrated, flicked, slid, danced and twirled. I could just reach her perineum with my lips, and I kissed and sucked it hard. She moaned at that. After 15 minutes, my head dropped back on the pillow, soaked with sweat.

“I don’t know if this is going to work,” I said, out of breath.

“Well, you better find a way to make it work. Otherwise, I’ll hop right off and you won’t taste my pussy for a week!”

I groaned, still resisting.

Anna sighed. “How about a little encouragement?” I heard a lotion bottle open and a few seconds later I felt her hands on my groin, circling my genitals.

My head sprung forward to lick again, and Anna laughed. “Ha-ha, that did it! Wow, look at all this precum! There’s so much it looks like you already shot your load. Can you feel that?”

She grabbed my taught dick between just her thumb and forefinger and slapped it lightly against my stomach. Indeed, I heard a wet smack and felt the warm fluid as she smeared my swollen cock head in it.

“Show me how much you want to cum by making me cum!” She commanded.

I didn’t think I could try any harder, but somehow I did. I felt Anna’s solitary finger rubbing up and down the underside of my penis. She circled the head with the lotion, giving just enough stimulation to drive me crazy, but not enough to bring me to orgasm.

I moaned and mumbled incoherently as I worked her pussy. She began rocking her hips in time with me. Her pace picked up slowly; this was going to be a long build without access to her clit. That was her magic button; I knew how to work that. I was in unfamiliar territory.

Eventually, after what seemed like an eternity, she showed signs of an impending orgasm. Her breath shortened and her hips began rocking faster and faster. She was clenching her pussy around my tongue rhythmically. Suddenly she clenched down hard and held it; this was it! I forced my tongue in and out past her clenched pussy muscles like a small penis. She cried put and pushed back hard. Her entire pussy slammed against my face. My nose was pressed between her ass cheeks and she was grinding her clit on my outstretched chin. My tongue was buried as far as it could go and her pussy muscles milked it as her orgasm overtook her in waves.

“Ahhhh!! Ahhhhhh!! Ohhhh God!!” She moaned and cried out.

As her orgasm subsided, she went limp and eventually fell forward on my body. She lay with her head next to my groin and her pussy still splayed out across my face.

“That was incredible! I honestly didn’t know if it could be done! I haven’t cum from penetration alone since sex with Troy!”

Well, that solves that mystery, I thought. It must have been his larger penis that gave her vaginal orgasms; I knew my small 4 incher wasn’t capable of it.

I was resting my head on the pillow enjoying the strong sweet scent of her orgasmic juices, when I felt a strange sensation on my cock and I heard the distinct “click” of a lock. She had locked me up! That lotion! It must have been the numbing cream! Damn!

“Hey! I thought I was going to get some action?!” I asked in a panicked voice.

“Oh, you are. But not with that little dick. You get to fuck me with this!” Anna swung her leg over my head and spun around to sit beside me.

I looked down my body to discover what Anna had put around my waist earlier. Around my midsection, about halfway between my belly button and the top of my locked cock, was the biggest dildo I had ever seen. The thick, flesh-like appendage extended high into the air, bobbing slightly side to side from its own weight. It wasn’t like the purple vibrator Anna had used the night before; no, this one looked as real as they come. It was made of life-like gel and even had veins and ridges like a real penis. It had to be at least 9 inches long and flared into a large mushroom shaped head at the end. I was speechless.

“Wha-wh…but…ohhh…what is…” I couldn’t even formulate a complete sentence.

Anna squealed and patted my chest. “Isn’t it exciting?! Lisa gave it to us! What do you think?”

“It-it’s so big!” I exclaimed. The base was so wide that I couldn’t see my own penis or even my chastity cage past it.

“Oh, it’s not THAT big.”

Was she serious? I wondered just what her standard was exactly. Then I noticed something. “Why is the head so wet?”

Anna blushed. “I may have been getting it lubed up while you were licking my pussy…with my mouth.”

“You 69’d me with a dildo?!”

“I guess so,” she laughed.

I didn’t know how I felt about this…I obviously wished she had been sucking my dick instead, but then again, could you blame her? When she had that kind of choice…and I was curious…Ann must have picked up on that.

“Umm…wanna see it?” Anna asked nervously, stroking my chest.

“I-I guess so…” I gulped.

Her hand migrated down my chest and she gripped the base of the dildo loosely. She stroked it playfully as of it was real. Her hand looked so small on it. My cock was always completely covered when she stroked me, but there was about 2/3 of this monster still exposed. I was shocked when I saw that her fingertips barely touched.

Anna’s eyes were locked on mine, and mine were locked on the dildo as she parted her mouth and brought her sweet lips to the tip. The head disappeared slowly into her warm mouth and she continued downward in a single motion until it bottomed out in her throat. There was still 3 inches of cock between her lips and her hand.

I moaned loudly and let my head drop on the pillow. “Oh my god!”

Anna laughed and leaned down to whisper in my ear. “You ready to fuck me…big boy?”

She had never called me that before. Another moan was my only response. Anna propped another pillow behind my head to make sure I had a good view. She swung a leg over me. She had to remain standing on her foot on one side; the dildo was simply too big for her to drop down on her knee. She reached over to the nightstand and squeezed a generous amount of lube onto her hand. She rubbed it all over the dildo. “We’re going to need lots of this.” She said smiling.

My wife rubbed the soft head of the dildo along her slit, coating her pussy with the lube. She parted her lips with one hand and gripped the base of the monster with the other.

“You ready to fuck me with your huge cock?” I groaned with anticipation. It turning me on to hear her call me huge, even if I knew she didn’t really mean it. “OK, here goes…”

She pushed the cock head against her opening and dropped her pussy a little. The thick ridge of the head disappeared inside her, causing her to moan and retreat slightly. The next time she pushed down she got the head and about 2 inches inside her. She held herself there for a moment, adjusting to the size.

“Oh god! Your cock is sooo big! Just the head feels like it’s going to split me open!”

My stomach was turning at her words. I had butterflies as she slowly sank even further down the shaft of the cock-my cock. “That’s it, baby. Nice and slow. I don’t want to hurt you…” I was playing along now.

“God, Tim, you’ve never felt so good before!”

I had a feeling she meant that one. Oh well.

She moved up and down slowly, taking a little more of the shaft inside her with each stroke. Her pussy looked impossibly stretched; with each upward stroke her lips clung tightly to the thick cock as if they were trying to pull it back inside her.

“I’ve never felt so full!” She moaned. “My pussy is stuffed! I don’t think I can take any more, your penis is just too big!”

Her words were inexplicably boosting my ego even though I knew she wasn’t really talking about me. She had managed to squeeze enough of the oversized cock into her that the thinly stretched lips of her pussy were now touching her fist, which still gripped the base of the cock. That meant she had about 6 inches inside. A thick 6 inches. My eyes followed her hands as she slid them up her curvy body; over those thick hips, her soft stomach, and up to her milky-white tits. She squeezed and kneaded them, the springy flesh like Jell-O in her hands. She teased her nipples and moaned. Her eyes were closed, her head was back, and her mouth was open. She was really enjoying this.

“Are you OK?” I asked.

“Oh, yesssss! I have NEVER felt better!”

She allowed a moment for her body to adjust to the size of this new invader. Slowly, she lifted herself up until just the tip was in her, then she dropped her other leg so both knees were planted on the bed, on either side of me. This caused the large cock to plunge back into the depths of her pussy, this time disappearing a further inch. Somehow her body had found room for more.

“Ohhh, fuuuuuuuckkkk!” She cried, squeezing her eyes shut and falling forward. Her hands were on my chest and her arms pressed her breasts together as she started to ride the dildo. Down the length of her ample cleavage I could see it sliding in and out of her wet cunt. The realistic gel dildo was slick with her juices. It was as if her tight lips were acting as a squeegee, depositing much-needed lube along the lengthy shaft of this invading monster. The more she rode, the more her juices were worked up into a white, frothy coating. I had never seen her so wet.

“Unngggghhhhh, unnnggghhhhh!! She grunted. “I love your new cock, babe! I’m never going back to your little dicklette again!!”

She didn’t mean that, did she??? She left me no time to ponder; her moans, cries and groans were nearly constant now. She was slamming her hips up and down on the cock, taking as much as she could inside her before withdrawing to the tip and slamming back down again.

“Oh my GOD!! Fuuuuckkk this cock feels good! It’s touching me in places you never DREAMED of!”

Now it was back to “this cock”, not “your cock”.

Anna leaned back and placed her hands on my thighs behind her. This thrust her pelvis forward, giving me an unobstructed view of the oversized weapon stretching out my wife’s once tight pussy. On each down stroke I could see her inner lips disappear as the cock pushed them inside her. This also pulled on and stimulated her clitoris, which was so engorged that it actually protruded outward.

“Ahhhhhh!! I-I’m gonna cum!! Oh god! Oh god! Fuck, yes, yes, yesssssssss!!” Her wild cries trailed off as she impaled about 8 inches of thick cock into her sopping pussy. She was bottomed out, grinding the huge head against her cervix. Her clit was pulled down so far it nearly rubbed against the shaft of the cock. I had never seen anything so hot in all my life!

Her thighs shook as her orgasm rocked her body. I could see her pussy spasm around the thick pole it held captive. Up her body, her breasts rolled and jumped as her body convulsed with passion. Her head was thrown back and she panted through her open lips. She came for what seemed like an eternity.

As her orgasm finally subsided, she struggled to catch her breath. She rolled her hips slowly, massaging the tender insides of her satisfied pussy with the thick dildo.

“Mmmmmmm…” She moaned, her eyes closed. “That-that was… I don’t know… I’ve never…”

“I’m glad you liked it!” I smiled up at her.

Anna looked down her body at the huge cock still buried inside her. She slowly lifted her hips up until the dildo flopped out and smacked against my chest. Her wild movements had loosened the strap so that now it lay flat against my bare chest. It reached from my pubic bone to the bottom of my ribs.

Anna leaned down and we kissed. Her breath was hot and heavy. I could tell she was absolutely spent from such a powerful orgasm. She broke the kiss and sat back down, straddling the shaft of the dildo. She absentmindedly slid her pussy along the length as she spoke.

“Thank you, honey,” she said sincerely. “That was the best orgasm I’ve had all week. Now tell me honestly…how are you feeling?”

I had to think about it for a minute. “I-I guess I feel fine. I’m still incredibly horny. Watching you orgasm like that, talking dirty and hearing the things you say… wow, babe. I never knew our sex life could be like this. I’ve never been so turned on!”

“Good! I’m glad I can turn you on so much!”

“Yes…about that…” I hinted. “I’m DYING for some relief! My balls feel like they’re going to explode!!”

“Tim, I’m really proud of you for being so selfless this week and holding out for so long. I’ve never came so much in my life! I think you’ve earned some relief.”

“YES, thank you!!” I breathed a huge sigh of relief and grinned ear to ear.

“I want to help you, I really do. I hate to see you actually physically hurting like this… but…” She paused nervously.

“But what?” My heart nearly stopped.

“Well, see… I talked to Lisa, and… well, she said she would only give me this dildo if I gave her something in return…”

“What did she w—” my voice trailed off as I noticed it; her necklace, along with the key to my chastity cage, was gone! Her neck was bare!

“No! No…” I whimpered in frustration. “Why would she DO that?!”

“I’m sorry, honey, really I am! She said she could tell how much you like this and that you haven’t reached your breaking point yet. But maybe she was wrong…maybe you want to go back to the way things were,” Anna said it almost as a question.

It took everything in me to remain calm. I tried to rationalize the situation. Come, on! I thought. I can’t go a single week without an orgasm?! Anna deserved more than that!

“No,” I gulped, fighting back tears. “She was right. I really do like sacrificing for you, even though it’s the hardest thing I’ve ever had to do. As long as I get to see you so happy, that’s what matters.”

“Oh, honey, that makes me happy! I wouldn’t want to throw out all this progress for nothing. I promise you’ll get some relief tomorrow; Lisa has a plan. I love you so much!”

Lisa has a plan? I thought. What does that mean?

Anna didn’t give me a chance to ask. Instead, she slid further and further up the dildo, with longer and firmer strokes, until she was rubbing her clit on the ridge below the head. “I want to do something for you,” She said. “I can’t give you an orgasm tonight, but I can give you one of mine.” With that, she lifted herself up and straddled my face. “This one’s for you.”

I knew what she was implying. Her last orgasm of the night was going to symbolize my own. I was to think of her pleasure as mine, to feel release through her. Of course it was a rouse… her orgasm wouldn’t relieve the pressure in my balls nor the pit in my stomach. But I was so aroused I didn’t care. Here was my beautiful, sexy wife kneeling over me, offering her delicious pussy to me. How could I resist? I wanted it too much.

As her well-fucked pussy approached my face, I was taken aback by how different it looked. Her outer lips and clit area were red and puffy, while her inner lips, which were normally tight and hidden from view, hung down loosely. Her vagina actually gaped open slightly, a sight I had never seen before. She laid her pussy across my mouth tenderly and said, “Be gentle, babe…I’m a little sore.” More words she had never uttered before.

From the looks of it, she was more than a little sore. That huge dildo had wrecked her! My mind raced as I tried to imagine what she would feel like around my penis right now. That only served to remind me I wasn’t going to be feeling anything myself tonight. I pushed the thought aside and focused on my task.

Anna’s pussy was soaked with juices and from the way her pussy gaped opened they ran down freely into my mouth. Her taste and musk only served to raise my excitement exponentially. I loved the way she tasted. I breathed deep and took in her aroma. My lips rubbed across hers as my tongue made its way up her stretched love tunnel. It felt much differently than it had 30 minutes earlier, before she had fucked the dildo. Her muscles no longer gripped my tongue like a tiny penis; hey were relaxed and loose. My tongue circled around, feeling the insides of her pussy one side at a time, no longer able to touch all sides at once.

“Here, let me help you with your orgasm,” Anna reached down and fondled her clit as I licked her. She rolled the tender nub with her finger and moaned. She began to work her pussy harder and faster against my face. I could tell this would be a quick orgasm.

“Oh, Tim… your tongue feels so good! Can you feel how loose my pussy is?”

“Uhhhh huhhhhh,” I agreed, wanting to finish this as quickly as possible so I could get some relief from my aching balls. The pressure was unbearable and my cock strained hard against the plastic that enclosed it and held it captive. My dick burned from trying to become erect and not be able to. I had to kill my arousal, and the only way to do that was to get Anna off my face.

“Anna, I want you to cum on my face…” I tried to coax her orgasm along. “Fuck my face with your wet, used pussy. Show me how much you want this.”

“Mmmmmmm,” she moaned, rubbing her clit faster. Her orgasm approached faster and faster, until finally her pussy clamped down on my tongue and I knew I had her. Or she had me. Whatever.

Her orgasm was somewhat muted, no doubt from the series of intense orgasm previously. It seemed to come from deep within her.

When she was finished, she slid off my face and stood beside the bed. She kissed the plastic tube holding my desperate cock, giggled, and shimmied out of the room. I tried not to, but I couldn’t help but watch her delicious, round ass bounce as she walked away. God it looked so good. I gritted my teeth. I looked down my body to see my cock raised as high as it could go, pulling the ring around my balls and causing them to take on a deep, purplish/blue color. My dick looked like a sausage squished in its clear prison. I closed my eyes and slowed my breathing, trying to fight off the feelings of futility and frustration.

Anna emerged wearing just a tiny black thong. She untied me from the bedposts and I stretched my sore arms and legs. I reached down to remove the obscene dildo from my waist, but Anna grabbed my arm and stopped me.

“No…” she had a meek look on her face, as if she was embarrassed. “Honey… would you mind wearing it tonight? While we sleep? If not, I understand…”

“Why?” I asked, shocked by her request.

“I just… I think it would be fun.” She leaned in and kissed my earlobe. Oh no, she was using her sexy charms again. “I-I want to feel your big cock against me tonight, babe. Don’t you want to slide it against my ass?” She guided my hand to her bubbly ass and I squeezed a handful.

Oh, god! The idea turned me on. I didn’t respond. I simply turned off the bedside light while Anna rolled over, and I nuzzled up behind her. The dildo pressed against her ass, sliding deep into her crack. It reached above the top of her big butt and was smashed between her lower back and my abdomen. My own caged cock rested against the back of her thighs. It all felt incredibly weird.

Anna wiggled her ass against me, but I felt almost nothing. I placed a hand on her hip and rubbed her ass slowly as we drifted into a deep, much needed sleep.


To be continued…



One comment

  • pantywaist-ken

    All we small dick deserve are edging – good story


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