Loading...I stood in the shower, allowing the hot water to caress my body in an attempt to wake myself up. The thought of another long day at work wasn’t helping the situation, but at least it was Friday. “Get through today and enjoy the weekend,” I thought.
I stepped out of the shower and immediately realized I had forgotten to bring a towel into the bathroom from the bedroom in my morning fog. I dabbed away the worst of the water with the small hand towel we kept in the bathroom and then hurried, still mostly wet, into the bedroom.
Trying to be quiet so as not to wake Jenna, I grabbed a towel to finish drying off. Unfortunately, the thing I had between my legs foiled my plans, as it seemed to be doing quite often lately.
“Clack clack clack!” The pad lock on my chastity device knocked against the plastic tube encaging my dick as I was vigorously drying off.
“Mmmm…morning babe,” I heard Jenna mutter weakly as she rolled over in bed. Just enough light from the morning sun was coming in through the windows for her to see me.
“You should go back to sleep, you have a big exam today. Get your rest,” I said, still keeping my voice down despite the fact that she was awake.
She and I were both “night owls,” staying up until 2 or 3 in the morning playing video games, binge watching TV shows, or just plain screwing around with each other. I unfortunately had to be into work at 8am on weekdays, and still haven’t adjusted my sleep schedule. Jenna was still in college, a 5th year senior, and bartended on the side.
In case you couldn’t already tell from the fact that my penis was locked up in a hard plastic tube, Jenna and I had a very unusual sexual relationship. The chastity tube was actually my idea. It was a fetish I’ve had for a very long time, and it actually took some convincing to get her to play along. But once she did, she found that she liked it more than she thought she would.
We met a few years ago through some mutual acquaintances and hit it off immediately. Sex was plentiful and I got along better with her than anyone else I had ever known. Once we were comfortable enough with each other, she revealed that she had some bisexual feelings. She had never done anything particularly serious with another girl, but was interested in trying it.
Not long after, I revealed my ultimate sexual fetish to her: chastity. I couldn’t remember when I first developed an interest in it, but it quickly became one of my greatest sexual fantasies. I often watched femdom “cuckold” porn in which a man, caged by his lover, would be forced to watch as she was utterly dominated by other men while he had no hope of release in his little cock cage.
I still remember the day I brought her into my fantasy world. I saved up a little money and purchased a simple plastic chastity device online. I marveled at it when it arrived. I was so excited by it that I actually had to masturbate before I could become flaccid in order to get the device on. It was a tight fit, but the chrome finish and pad lock hanging on the front were major turn-ons.
I wore it the entire evening until Jenna got home from her bartending shift. I showed her the device and presented her with the key. She was reluctant to take it, but finally relented. She wasn’t as “into” the whole key holder domination thing as I was, and we got off to a slow start. Eventually she started to come around to have some fun with it. I would eat her out in hopes of getting release, but she would often just cuddle up with me and go to sleep afterward.
It was frustrating…but exactly what I wanted. Then she started coming up with some more creative ideas. She would join me in the shower and tease me relentlessly with her naked body. She would press her breasts together and encourage me to “fuck her tits” by holding them against the device while my cock strained within it. She’d kiss the tip of the device, and then suck on it, looking up at me with her big blue eyes while I’d be unable to find any relief. It was exactly what I wanted.
Whenever she would release me, I’d fuck her like a rabid beast. I think that is where she got the most enjoyment. She’d build up my sexual energy by having me go three or four days without release, then allow me to unleash it on her.
After about a year of that, we arrived at that fateful morning. I stood in front of her in my device, towel drying myself after a shower. I knew she was naked under the covers as she turned to look toward me, but I couldn’t let my mind focus on that. The device on my cock was already tight, as today was my 10th day without release, the longest she had ever kept me in it. Four days was the longest I was locked up before this, as it was the longest she could usually go without sex. That was often the determining factor as to when I got released.
Jenna climbed out of bed as I started to dress. She pulled her shoulder-length blonde hair into a ponytail using a hair tie she kept around her wrist and stretched her arms high above her head. Her perfect C-cup breasts pushed forward, giving me a great view. She then took a trip to the bathroom without bothering to cover herself up, leaving my poor cock raging within its cage.
I put on my boxers and pulled up my pants as she returned to the bedroom. I barely got to zip up my fly as she moved in and pressed her naked self against me.
“I have a BIG surprise for you tonight,” she said seductively, moving up close to me and embracing me. She gave me a long kiss on the lips and bucked inward, forcing my cock cage against her stomach.
“What kind of surprise?” I asked, knowing there was no way she would let anything slip out.
“You’ll just have to wait and see,” she said with a devilish smile. She gave my swollen balls a gentle squeeze through my pants and then went back to bed.
Work went by at a snail’s pace. It was a slow and boring day to begin with, but it seemed even longer as my mind raced about what Jenna’s “big surprise” could be. Having to feel my cock locked up all day was a bad enough distraction, but 10 days of it along with the anticipation of this “surprise” was really killing me. Finally, 5 o’clock came around and I sped home as fast as I could.
The apartment was locked and Jenna wasn’t home. I didn’t remember her saying that she had to work after class, so I wasn’t sure where she was. When I flicked on the lights, I saw a note on the kitchen table: “Go into the bedroom. Look in the top dresser drawer.” It was in Jenna’s handwriting.
Excitedly, I ran to the bedroom. I opened the drawer, and on top of a pile of Jenna’s panties was another note, along with a pair of handcuffs ringed in black fuzz, a red ball gag, and a black blindfold. I read the note:
“Send me a text that says ‘I’m ready.” Then strip, put these on, and cuff yourself to the bed. Wait.”
I was so excited to finally try bondage that I nearly dropped the ‘equipment’ in my haste. I pulled my phone out of my pants pocket and sent the text. Then I stripped down until I was only wearing my chastity device.
I put the ball gag into my mouth and tightened it behind my head. I carried the blindfold and handcuffs over to the bed and took a seat. I looped the handcuffs around the center bed post so I could find them easily and then pulled the blindfold over my eyes. I couldn’t see or speak in my current state.
I laid down on the bed and raised my arms above my head. I found the handcuffs looped around the bedpost and then locked my wrists into them. I tugged at my restraints to test their hold, and sure enough, it was tight. I wasn’t going anywhere. The bed was an old thrift store purchase, practically an antique. The head board and bed posts were solid, heavy oak, so breaking it to escape wasn’t even an option.
Bound, gagged, and blindfolded, I laid in bed for probably 10 or 15 minutes until I heard the front door unlock and open. All was quiet for about a minute until I heard the bedroom door creak open. I laid there silently in nervous anticipation, my cock pressing hard against the inside of its little prison.
I felt a hand lightly caress my inner thigh. I felt long, feminine fingernails graze my skin and slowly move up my leg. The touching stopped just before it got to my locked-up genitals. I felt my member straining hard to no avail.
I heard what I thought was a very faint whisper before a set of lips pressed against my right thigh…then another set against my left thigh. I twitched at the surprise of there apparently being a second person there along with Jenna. Someone else now knew my dark secrets, and I was powerless to do anything about it. All I could do was lay there and enjoy it.
The two sets of lips kissed and licked their way up my thighs to my groin, and began going to work on my swollen balls. They hadn’t had a release in over a week, and were swollen as much as I had ever felt them. I could hear deep breathing and the occasional giggle from the two people working them over with their lips and tongues. One of them then moved up to my caged member. I moaned into my gag as it strained against its confines, aroused by the hot breath and sucking of the person doing the work. A tongue worked its way into the slit at the end of the tube and I felt myself shudder as it lightly touched the tip of my engorged penis.
Then, the sucking and teasing stopped. I felt two belts being tightened around my ankles and then attached to the legs of the bed down below. Suddenly, something cold and heavy was thrown on my crotch. It felt and sounded like a bag of ice. I tried to tense up but the belts around my ankles and cuffs around my wrists prevented me from going anywhere. Another bag of ice was thrown onto my crotch, and then a third one.
“Mmmhmmm!” I groaned into the ball gag.
“Shoosh and be a good boy. I promise that you’ll love what we’re about to do,” replied Jenna.
Several minutes passed as I began to lose feeling of everything between my legs thanks to the cold ice. I heard a few whispers and murmurs between Jenna and whoever she was with, but couldn’t make out what was being said.
Finally, the bags of ice were removed. I felt someone sit on the edge of the bed by my leg and then heard a light tapping sound.
“He’s ready,” said Jenna in an excited tone. It was only when she stood back up that I realized the tapping sound came from her flicking my numb balls.
Though I couldn’t feel what was going on, I could hear it. The unmistakable sound of Jenna inserting the key into the lock of my chastity device was followed by the “click” of the lock opening. She fumbled briefly with the ring and tube, but then walked away from the bed presumably with the device in hand.
I heard the “zip” of a bag opening across the room and the clank of metal. Jenna returned to the side of the bed and sat down. Feeling was starting to return to my nether region as she slid a new ring around the base of my cock. I wanted to resist so that I could enjoy my freedom before being locked up again, but the restraints made sure that I could not.
Feeling was starting to return as she slid a metal tube over my cock and heard a loud, metallic “click” when it connected with the ring. I was locked back up and there was nothing I could do about it. She gave the new equipment a few tugs to ensure that it was on tight. More whispers and giggles between the two girls followed.
Suddenly, I felt one of them lay down next to me while the other climbed onto me, straddling my stomach. I could feel warmth of an incredibly turned on pussy against my abs. A set of hands reached up and pulled the blindfold from over my eyes…
“Hello babe,” Jenna said seductively, leaning in very close to my face as she lifted the blindfold. The gag in my mouth still prevented me from talking. Jenna was wearing only a matching, lacy black bra and panty set. She bent down and kissed me through my gag, running her tongue around it along my forcibly parted lips. She sat back up, gently grinding her hot pussy into my stomach.
“This is my friend Tasha, say ‘hi’ to Tasha,” Jenna commanded. The girl lying next to me leaned in and rested her head on my chest. She had raven black hair and was wearing heavy makeup. Out of the corner of my eye, I could see that her arms and shoulders sported a number of tattoos.
“Hi handsome,” she said with just a hint of a Russian accent. Her shiny, dark hair and dark brown eyes contrasted Jenna’s blonde hair and blue eyes perfectly.
“She works with me at the bar and agreed to help me fulfill a few of our fantasies…” Jenna said with a devilish smile. She raked her nails across my exposed upper chest and bit down hard on her bottom lip.
“Lean up for a second, hon,” Jenna asked as she nodded her head toward my crotch. She moved to the side as I lifted my head as far as I could, just enough to see the shiny metal of a new chastity device.
“This cost me quite a few nights worth of tips, so you better appreciate it,” she explained as she slid her fingernails along the tube. Full feeling had returned to my cock and it was pressing against the cold metal of the new tube. “It’s made of hardened stainless steel and is held in place by a built-in cylinder lock at the top here. It’s completely unpickable and the steel is virtually indestructible. You’ll never get out of it without the key…” she explained seductively as she held up the key on a thin chain around her neck.
“Come up here, Tasha,” Jenna said as she moved back to straddle my right thigh. Tasha moved to straddle my left thigh. Tasha was wearing a tight, black leather bustier that pressed her enormous D-cup breasts forward and crotchless latex pants that clung to her long, trim legs. Her pussy was only barely covered by a black thong.
She and Jenna moved towards one another and began making out. They kissed softly and gently at first, but it became harder and more intense as they went. Jenna pulled Tasha close to her so their breasts were forced together. Jenna reached one hand down and began massaging my balls while they continued to make out.
If there was ever a moment where I thought it’d be possible for my cock to break out of that cage, it was right then. The steel held firm, however, and all I could do was bite hard into my ball gag for relief.
Suddenly, Jenna broke away and spun so her back was toward me. She repositioned herself onto my chest while I felt Tasha follow suit, straddling my hips and groin. They went back to making out as I could feel the warmth of Tasha’s pussy on my dick even through the tube. As they made out, Tasha rubbed her pussy all over my tube and the surrounding area. I could feel the wetness of her yearning pussy leaking through her thong and onto my skin.
Jenna bucked up and down on my chest while they made out. Her pussy was radiating warmth and wetness like I had never felt before. Slowly, she slid further up my chest until her panty-concealed pussy was right against my face. I wanted to stick my tongue out to lick it, but the gag made it impossible. I could no longer see the action, but based on Jenna’s position and the noises she was making, she had kissed her way down Tasha’s neck to bountiful breasts.
Jenna then leaned back, now practically sitting on my face. She unhooked her bra and dropped it off the side of the bed. Tasha moved in right away and began sucking on Jenna’s perfect tits. Jenna couldn’t help but let out a quiet moan of pleasure. She was slowly grinding on my face as Tasha sucked, using my nose, chin, and gag to massage her pussy. I could feel and smell the wetness, wanting badly to get my tongue involved.
Tasha’s teasing was also unbearable. She was doing the same slow grinding as Jenna, except over my caged cocked. It was certainly putting the steel of its new prison to the test, as any lesser material may have broken as hard as it was getting.
The two girls traded between making out and sucking each other’s breasts for what felt like an eternity. All the while, Jenna’s pussy was over my face, teasing me with what I wanted but could not have.
“It’s time…” Jenna said as she jumped off of me and onto the floor. Tasha grinned and put her long, dark hair up into a ponytail. Jenna walked over to a large duffle bag on the floor and dug around for a moment before pulling out exactly what she was looking for: a strap-on dildo.
Tasha and I watched as she slid out of her soaking wet panties, briefly exposing her swollen pink pussy lips, before putting on the strap-on. It had black leather straps with a medium-size (probably 5-6 inches) purple dildo on the front. The dildo itself was tapered into the rough shape of a penis, with the “head” pointing upward just slightly. I recognized it from porn as one made for massaging g-spots and prostates while fucking.
Jenna hurried back to the bed with the purple dildo bouncing in front of her. She practically tackled Tasha onto the bed to my left and they picked up where they left off, making out and grinding into each other.
They stopped briefly as Tasha rolled onto me, her face close to mine. She was straddling me, her pussy once again up against my chastity cage. Jenna moved in behind her and began to unlace Tasha’s bustier. It feel free as Jenna pulled it to the side, dropping it off the edge of the bed. Tasha’s massive breasts were now firmly against my chest. Even from there, they felt heavenly. They were so soft and pillowy…not to mention the largest I had ever seen and felt in person.
Tasha’s face was only inches from mine. She winked and made a sexy biting motion as Jenna slid off her thong down below. I could feel as Jenna hung it from my restrained foot.
Jenna worked her hands slowly up Tasha’s sides as she positioned herself behind Tasha. Jenna was kneeling between my spread legs right behind Tasha’s ass.
Tasha inhaled sharply as Jenna penetrated her. Seeing this was almost too much to bear. I bit hard into my gag as my cock filled every molecule of space within its cage. I felt like my balls were going to explode if I didn’t get release soon.
After a few, slow thrusts to get started, Jenna began to fuck Tasha harder from their doggy style position. It was one of our favorite positions whenever we had sex, and now I had to watch Jenna do it to another girl while I could do nothing to relieve my frustration.
Jenna got into a good rhythm as Tasha moaned grinded against me. She was pressing her breasts against my chest with each thrust while kissing, biting, and sucking on my neck and shoulders. She ran her fingers through my hair and would occasionally dig in with her fingernails. The combination of pleasure and pain was absolutely thrilling.
It seemed like hours passed as I could only lay there in frustration watching and feeling two beautiful women fuck on top of me. Tasha cried out and moaned as she approached orgasm, with Jenna fucking harder and faster. I looked over Tasha’s shoulder to Jenna who was focused on the task at hand. Her blonde hair and ample breasts were bouncing along with each thrust. It almost seemed like she was a natural at fucking women.
“I’m going to cum! I’m going to cum!” Tasha cried, her eyes closed and her mouth agape, tears of pleasure flowing down her face, taking much of her makeup along with them.
Suddenly, Jenna stopped and pulled out. She helped position and angle Tasha’s waist just above my locked-up cock. I felt a hot liquid explode out of Tasha’s pussy, all over my poor, frustrated dick.
“Mmmph!” I moaned into my gag. Tasha was a squirter!
Almost as if she had passed out from the pleasure, Tasha rolled off of me to the side as she tried to catch her breath. She was still gasping and moaning from the fucking she just endured. The warmth from her squirted juices only increased my frustration as I could feel it seeping through the openings of my chastity device onto my cock and balls.
Jenna had the biggest smile as she just stared at me. She then crawled up toward my face, stopping with her pussy just shy of my neck and the strap-on, still wet and smelling of Tasha’s pussy, pressed against my cheek.
“Not a word, you hear?” Jenna whispered to me. I nodded in agreement. She reached down and unhooked my gag, tossing it off the side of the bed. She lifted the strap-on, allowing her pussy, which was exposed beneath, to press against my lips.
“I hope you’ve had fun so far…” Jenna said, eyes closed and hips bucking to rub her pussy over my lips.
“Mmm!” I moaned excitedly into her pussy as I continued to lick.
“I found the kinky forums you go to online. You were still signed into my computer from that day you forgot yours at work. You forgot to clear the browsing history so I looked at all of your posts and, well, learned a LOT about the things you like. The chastity was one thing, but wow! To be bound…forced to watch…I thought we could have some fun with it,” Jenna explained through quiet gasps as I hit all of the spots in her pussy with my tongue that I knew she liked.
“But if we were going to do what you liked to do, I was going to get a few things too. You know I always wanted to fuck a girl, and as you can see, I really enjoyed it. I also wanted to be part of a threesome, and now I’ve done that as well,” she continued.
She repositioned herself on my face and began stroking the strap-on as if it were an actual cock.
“Tasha is a new bartender and we hit it off right away. I found out she was bi-sexual, and then we planned this night. I couldn’t wait to fuck her, and her being a squirter was just icing on the cake. She didn’t believe me when I told her I had you all locked up in a little chastity cage, but wanted to see it. I think we made her night as well,” Jenna said as she looked over at Tasha, still writhing around in ecstasy.
I began working my tongue extra hard and sucking on her clit. She had to stop talking for a second as she gasped from the pleasure.
“…you’re so eager, I’m glad you’re ok with all of this,” she said with a smile. She brought her hands up to her exposed breasts and began kneading them in her hands and playing with her nipples. “I didn’t expect to cum just yet, but…ah…I won’t…ah…complain…”
She was close, so I went into overdrive with my mouth. Her juices were dripping down over my cheeks and chin. Jenna’s eyes closed tight and she pinched her nipples hard as an orgasm tore through her body.
“Hunnnn…” She moaned as she arched her back. Her eyes shot back open as she gasped for breath.
“Now you’re the only one left…” Jenna said, breathing heavily. “I’m not sure if you’ll like this, but we’re going to try it out.” She winked and moved back away from my face.
“I…” I tried to speak but was silenced with a quick slap across my exposed balls.
“Quiet!” Jenna reprimanded.
I swallowed hard as I knew where Jenna was going. She unhooked the belts around my ankles and motioned for me to lift my legs, bringing my knees toward my shoulders. Jenna began massaging my balls and looked up at me with a smirk. The entire area was still soaked with Tasha’s hot juices.
I closed my eyes and gritted my teeth as Jenna positioned the tip of her strap-on dick just outside my defenseless ass hole. Hopefully, Tasha’s leftover juices would provide enough lubrication…
Jenna was gentle at first as she pushed slowly forward, the strap-on penetrating my virgin ass. While it was common with others interested in chastity, I had never thought of being ass fucked before. The strap-on stretched me to my limits. The feeling was an odd mix of pressure pleasure.
“Gooooood boy, taking it all in like that…” Jenna teased. “Now we go a little faster…”
Just as she said, she began speeding up. Each time, it felt like I was going to be torn in half but the pain was mixed with a strange sensation of pleasure.
Soon, Jenna was fucking just as wildly as she had with Tasha. I grunted between each thrust, experiencing a wide range of emotions as I could do nothing but lay there and take it.
“This…is so…much fun…” Jenna said between vigorous thrusts. “I might…invest in…a two-way…dildo so…we can…both…be pleasured…”
My grunts and moans were getting deeper and heavier. I’m not sure if I could handle doing this again.
“Haha!” Jenna giggled. “Look…at all that…precum…” She paused the fucking momentarily, giving me a few seconds of relief. “If you cum like this, it’s the only way you’ll ever get to cum again!”
I wanted to protest, but she went right back to fucking my ass with every ounce of vigor she could muster. I focused on her bouncing breasts and the intense look on her cute face to distract myself as much as I could.
Just as she realized, the precum was a sign that I was close to erupting. I hoped she was kidding about only letting me cum this way from now on…
“Jenna…Jenna…I…Uh…” I tried to beg her to stop, but it wasn’t happening.
“Shut up and take it!” she commanded, increasing the intensity of her thrusting.
“No no no no NGNNNN!” I groaned as I felt something like an orgasm in my nether region. It wasn’t as powerful as an actual orgasm, and didn’t come with the feeling of relief that an actual orgasm would bring, but I could feel a mountain of cum erupting from me nonetheless.
“Hahahaha!” Jenna laughed, running a finger along my spiraled steel chastity tube to collect some of the cum. She lifted her hand up to show me and a string of cum followed it.
“You are such a little sissy! Oh my god!” She exclaimed excitedly. She wiped her finger on my thigh and then unhooked the strap on. She tossed it off the side of the bed and crawled up in between me and Tasha, who was lying next to us enjoying the situation.
I was panting to catch my breath, with my asshole feeling like it was on fire. While I felt the 10-days’ worth of cum erupt out of me, I didn’t feel the relief a normal orgasm would have brought. It was both disappointing and a great turn on simultaneously.
Jenna brought one of her legs up and put it across my stomach. I could feel her still-hot pussy against my side.
“I think this was a success,” she started. “I think we’ll keep doing this. Tasha is on board, and you will be too. I think we need to buy some more toys. You won’t get out of the cage other than to clean it sometimes. And I’ll just keep right on fucking you, it’s so much fun.”
I tried to bring my arms down, forgetting momentarily about the handcuffs. I wanted to hold Jenna close, because as terrified as I was, I was also in heaven…