As Jessie was walking around her local adult novelties store, her eyes landed on a lone package right next to the cash register. It contained what looked like a simple cock ring, but it was a lot thicker than the other ones next to it in the store. She picked it up, closely inspecting the package.

“Ah! I see you’re interested in the ‘Keeper-Upper’!” the cashier said in a cheery manner. “We’ve only got one left in stock, and they’ve been flying off the shelves!”

“Huh, oh! Yeah!” Jessie says, looking down at the ring once again. “What’s so special about this one?”

“It vibrates, and its tight grip will keep your partner erect for hours!” The cashier explains, leaning in towards Jessie a bit.

“Hours, you say? Well, okay! You’ve sold me!” Jessie exclaimed, passing the toy over to the cashier. “I’m sure my partner and I will love this!” She swiped her card, and the cashier handed her the toy back. “Oh! And what’s your name? You’ve been very pleasant today!”

“The name’s Xen! It’s been a pleasure to make your acquaintance.”

“Thank you, Xen!” Jessie said as she walked out of the door cheerily.

Jessie made her way home, ready to surprise Sakura with her new gift! She pulled into her driveway, and jogged into their home. Sakura was watching TV on the sofa when she saw Jessie pop open the front door. “Hey Sakura!” Jessie said, beaming.

“You look really happy!” Sakura commented, “What’s gotcha going?”

“I got you a little gift!” Jessie said as she pulled out the cock ring.

“Ooh! ‘Keeper-Upper’! That looks exciting!” Jessie smiled brightly, enjoying seeing Sakura excited by the gift. “I’ll have to test this out right away; hopefully it holds true to its name!” She said as she chucked.

“I hope so too!” Jessie shouted out after Sakura, who was already running to her room with the package to give it a test run.

As soon as her room’s door was closed, she jumped onto her bed. She eagerly tore the package open, releasing the toy. It was an extremely thick cock ring, with a tight hole in the middle of it. It was translucent, and it appeared to have several layers of material inside of it. She was extremely intrigued by its design, and was already starting to get slightly erect by just looking at it. She rubbed her paw over her crotch, stroking herself for a couple of minutes until she found herself fully hard. She grabbed the ring, and carefully stretched it over her penis, just barely managing to squeeze it past her growing knot. After she got it past, she sat the ring down at the lowest point of her shaft. The pressure of the ring was causing her to get even more erect, and her shaft and knot both steadily grew in size.

Then after a couple of seconds, the outer layer of the ring snapped and unfurled, causing the inside of the ring to expand across the entirety of her mass, tightly encapsulating her shaft. The toy then snapped shut at the top, completely sealing itself atop Sakura, leaving a hollow and stretchy chamber by her penis’ tip, similar to that of a condom. The base of the ring still had a very strong elastic grip on her penis, behind the knot. Sakura looked at the toy, confused. “Huh…” She wondered to herself. “Cock rings don’t usually do that… do they?”

The new sleeve then started to vibrate vigorously. She twitched and reflexively moaned out; the vibrations around her entire shaft were causing her to get even more aroused. She started to uncontrollably leak pre-cum into the sleeve near-instantaneously.

She proceeded to stroke herself with the sleeve on, feeling the vibrations already getting her close to a climax. The tight grip it had on her shaft was causing her to feel extremely sensitive, and the vibrations were pushing her over the edge just on their own. After just a minute of light stroking, she couldn’t herself back anymore. She forcefully ejaculated into the toy, watching as her semen shot into the material at the tip of her penis. She lay back in her bed, panting from all of the sensations. But then she began to feel some rather unpleasant sensations too.

The toy wasn’t stopping its vibration, and her penis was extremely sensitive from just ejaculating; causing it to feel overstimulated. She decided that now would be a good time to remove the toy, as her shaft was feeling very uncomfortable. She tried to get her paws underneath the base sitting past her knot, but she found that it was still extremely tight. The tightness of the base ring and the constant vibrations weren’t gonna let her get flaccid any time soon.

Now panicking a bit, she grabbed the front of the toy, and attempted to pull it off of herself. In doing so, the material tightened around her penis, causing the vibrations to feel even more sensitive. After pulling it out just a few inches, she couldn’t take it anymore. She was already on the edge of her second orgasm, and only a few minutes had passed since her first. She tried to hold back the orgasm, but the vibrations wouldn’t let her hold it back anymore. They forced her over the edge, causing her to ejaculate into the sleeve once more. Sakura stared at the sleeve briefly, realizing that this toy wasn’t gonna simply let go.

“Ahh… Jessie, would you mind coming in here?” Sakura muttered out as the sleeve’s vibrations kept her weak. “I could really use your help!”

“Give me 15, I’ve gotta finish something up!” Jessie said as she sat on the couch, awaiting the climax of her favorite TV show. Little did she know that Sakura had already climaxed twice.

Sakura laid on her bed, making her best effort to not further stimulate her member. “Maybe if I stop interacting with it, it’ll stop vibrating!” she wondered. She stayed still; the unrelenting toy continuing to vibrate strong, causing her mass to continuously twitch from the pleasure. It slowly brought Sakura closer and closer to another climax, until once again, she found herself unable to hold it in anymore; unloading her semen into the sleeve. She was locked in an endless orgasm loop with no clear way to free herself. Any attempts to remove the sleeve would only arouse her more. And Jessie still wouldn’t be in to try and help her out of the predicament for another 11 minutes at the very least. She began to feel weak, the toy draining her of her semen and her stamina alike. She blushed hard, starting to give in to the sensations.

After Jessie finished up watching the TV, she knocked twice on Sakura’s door, and proceeded to open it slowly. She found Sakura lying on her bed limply. The only thing that wasn’t limp was her erect penis. The sleeve was still vibrating, and Sakura had already dumped a considerable deal of semen into its tip. Jessie walked over to the bed, watching Sakura as she trembled from the unrelenting stimulations. She then took a good look at the sleeve. “Huh…” Jessie said, confused. “Where did this sleeve come from: I thought I got you a cock ring!… and why are you twitching so much?”.

Sakura tried to say an elaborate sentence, but all she could mutter out was “It… expanded… won’t – come off…”. Jessie then reached her paw out towards the sleeve. Sakura tried to say something or pull away, but she found herself too weak to do so. Jessie lightly touched the sleeve, immediately noticing its extremely strong vibrations and its tight grip around Sakura’s shaft. Even just feeling Jessie’s soft touch on her member brought her right into another orgasm. Sakura twitched weakly as both of them watched her experience her climax; the sleeve’s tip beginning to bloat from all of the collected cum. Sakura still lay weakly: the sleeve continuing to drain her stamina even more.

“Oh! I’m so sorry!…” Jessie apologized, seeing that Sakura wasn’t exactly enjoying her predicament. She took a closer look at the toy, noticing the sleeve’s base locked tightly around her knot, and the tip containing all of Sakura’s ejactulatory fluid since she had put the ring on. There was quite a lot of it, definitely much more than from just two orgasms.

“Please… get it off… ahh”. Sakura moaned, already feeling aroused once again. Jessie reached over, and brought her paws to the base of the ring. She tried to get her claws underneath the base in an attempt to stretch it off, but it was just too tight against her throbbing shaft to break the seal between it and Sakura. She then tried to get a grip on the exterior of the sleeve, but it clung so tightly to Sakura that she couldn’t pry any part of it off of her. Jessie’s clawing was already getting Sakura close to the edge once again.

“Sakura, can you still stand up? I think I’ve got an idea!” Jessie said, excitedly.” Sakura, shivering, propped herself up, and slowly moved her legs to the side of the bed. She stepped down onto the floor, trembling an unreasonable amount. Jessie gazed at her empathetically, and then walked up next to her. “Grab on the edge of the bed, and hold still!” Jessie said. As soon as Sakura had a firm grasp on the bed frame, she grabbed the tip of the sleeve and pulled. Hard. Sakura stumbled forward a bit, her paws keeping her from flinging straight into Jessie. Jessie pulled the bulb of the sleeve about seven inches away from her tip before feeling an extreme resistance. The pulling of the sleeve was just tightening its grip around her penis, causing the vibrations to dig even deeper. Sakura winced, unable to vocalize anything. “Gah… come on!!” Jessie said as she pulled even harder, stretching the toy out another two inches. Sakura began twitching terribly, and moaned out, shooting her semen through the stretched sleeve. Jessie felt the warmth in her own paws, and she grew even more emotional, just wanting Sakura to be free of this curse. She pulled as hard as she could, stretching the sleeve out even more. Sakura shook uncontrollably. The vibrations were ringing through her, unrelenting.

“…PLEASE!!!” Sakura burst out, unable to stand the sensations anymore. Jessie clicked back, realizing the immense displeasure she was causing Sakura. She slowly brought the sleeve back towards Sakura, wishing she hadn’t subjected Sakura to that much stress. Sakura collapsed down onto the ground, defeated. Jessie knelt down to her, comforting her and embracing her.

“I’m sorry, I wondered I could… I shouldn’t have done… that”. Jessie said, looking ashamed of herself. Sakura had some tears in her eyes, but she still smiled.

“It’s – okay”. Sakura panted out. Jessie’s caring gestures were already helping her to feel a bit better. Even though she was stuck in this predicament, she wasn’t alone. Jessie softly picked her up, and cradled her, bringing her back into her bed. Just like before, she lay limply but her penis was still at full mast. Sakura tried, but could barely move a muscle. Her body was too weak to do anything besides feed the sleeve.

Jessie walked over to the toy’s packaging lying on the floor. She read it over once again. “It’s tight grip will keep your partner erect for hours”, she said to herself. “Guess that part’s actually true…” She couldn’t help but think that Xen sold her on this thing for some malevolent reason though. “Could they have known I was gonna give this thing to Sakura? Do they know her? Do they know me?” she thought to herself. She then flipped it around, and read the back. “Oh! Right here, Sakura! How to remove the toy!… It states the toy will burst open after a quart of ejactulate enters the sleeve’s tip!”. Sakura winced. “…how much is a quart again?” The look on Sakura’s face told her that it was quite a lot to ask. “Jeez, this toy is malicious”. She looked down at Sakura’s penis. While the bubble of ejactualte was getting quite plump, it was nowhere near a quart of liquid. “Okay, Sakura. I’ve got another idea. It won’t get you out right away, but it will get you out faster. What do you think?” Sakura nodded lightly and gave a look indicating that she’d do anything to get out of this hellish trap as soon as possible. “Very well”. Jessie slowly undressed herself, and then climbed up on the bed.

Jessie positioned herself atop Sakura, kneeling over her. She observed the sleeve’s tip more closely. She could definitely slip this inside herself. “Okay Sakura, I’m gonna lower myself onto you now.” Jessie said, bending her knees down and guiding Sakura’s tip into her vagina. As it touched her lips, she could immediately feel the vibrations much stronger. She flinched upwards a bit, but then proceeded to descend onto Sakura. The sensations were already making her blush, but she wanted to help Sakura by any means necessary. She wiggled the entire sleeve into herself slowly but surely. The sleeve’s vibrations were beginning to really arouse Jessie. She pushed herself lightly against Sakura’s covered knot, the sleeve vibrating vigorously against her clitoris. The toy was working wonders; Jessie was entranced by its pleasuring. Sakura, feeling the extra tightness and warmth from Jessie, was now outputting much more frequently. As soon as she hit her climax, another one was already brewing up.

Sakura twitched every twenty seconds or so, dumping over and over into the sleeve. Additionally, Jessie began to gyrate on top of Sakura. Jessie was having to put all of the work in, since Sakura was completely drained of her energy. She wanted to go for as long as possible though, hoping that her efforts would free Sakura. It was really hard for her to hold back though. Over the course of about ten minutes, she consistently gyrated atop Sakura, playing with her nipples, and caressing her tightly. Sakura’s twitching was a steady reminder to not climax until absolutely necessary, since they both just wanted this to all be over.

The sleeve’s strong vibrations inside her vagina and against her clitoris were just now finally pushing her over the edge. She continued to caress Sakura, holding herself down against Sakura’s knot tightly. She began to shake, and then she let out a loud moan, wrapping herself tightly around Sakura. An electrifying orgasm overtook her, sapping her of all of her strength, just like Sakura. She plopped down on top of Sakura, both of them panting heavily. The vibrations were still going strong, teasing them both. As she tried to catch her breath, she began to feel the warm tight bubble expanding deep inside her. Jessie’s gyrating must’ve been distracting herself from the sleeve’s expansion, as it really was starting to feel tight against her vaginal walls. She propped herself up again after a few minutes, feeling very heavy. “Hah… This is a lot of work!” She panted out. “I think I might need to take a little break, these vibrations are killing me!”. Sakura winced and twitched again, and gave a “And you’re talking?” kind of look. Jessie looked down shyly, remembering that Sakura’s had it much worse. She looked at Sakura’s bulging knot, with the tight sleeve still seated securely behind it.

As she slowly lifted herself up, she started to feel some tension between herself and Sakura. Sakura twitched lightly, yet holding very still. Jessie lifted up a little bit more, now feeling the large inflated tip. She tugged up lightly a few times, feeling the obstruction deep inside of her. And then she realized. “Oh no… Is this thing stuck in me now too?” She tried to lift up with more force, and the bulb stayed lodged within the back of her vagina. The toy’s ejaculate chamber was stretched too tight to change its shape, and her pulling wasn’t causing it to move one bit. “Gahh! What the hell?!” Jessie yelped, trying again and again to yank herself off of Sakura. How much could Sakura have ejactulated? Each time she attempted to pull herself off, Sakura’s body shook. Jessie could feel the toy continuously inflating inside of her with every couple of yanks, making an immediate escape even less hopeful, and another orgasm all the more likely. After trying to pull up one last time, she hit her breaking point, climaxing once again and toppling back down to Sakura.

The two were in an uncomfortable state of tug of war. If Jessie just lay there, her clitoris would be endlessly teased by the vibrations coming from Sakura’s plump knot. And if she pulled up at all, the sleeve would tighten around Sakura, causing her even more discomfort. There was no good compromise. They were both trembling, the nonstop vibrations causing them to climax over and over again, locked within each other by the devilish sleeve. The thing felt huge inside Jessie. She was wondering how it wasn’t exploding inside of her. Perhaps she underestimated how voluminous a quart of ejaculate was, since she swore she’d hit that point a long while ago. The sleeve had inflated in her so much that she could barely separate herself from Sakura anymore, even if she tried with all of her remaining strength.

They both lay tied together for what felt like hours, the sensations keeping both of them in a state of unpleasant arousal. There was nothing they could do to ease themselves; both laying limp and powerless. The sleeve was still growing in size, aching Jessie greatly. They were both a steamy mess, covered in sweat. Jessie simply couldn’t take it anymore. The sleeve vibrating against her clitoris was driving her wild, and the massive bulge inside of her was beginning to cause immense pain. She gathered all of the strength she had left, and reached her arms out to prop herself up. Jessie then pulled upwards forcefully, causing them both to shake from the sensations. “Come on!!!” She moaned out, the toy not budging an inch inside of her. The sleeve barely stretched too, but it was enough to still tighten down on Sakura, causing her to twitch once again, dumping her seed into the sleeve once again.

Then all of a sudden, the toy’s tip burst open violently. Sakura’s built-up semen shot out of Jessie, coating them both in the sticky and slimy ejaculate. The sleeve stopped vibrating, and it released the pressure around Sakura’s shaft. Jessie flung back from all the pressure, landing on the back end of the bed; free from the grasp of the toy. They both lay there, panting and trying to catch their breath. After a couple of minutes, Jessie reached over and pried the base of the sleeve off of Sakura’s deflating knot, completely removing it from her. The whole ordeal was finally over. She lay back down on Sakura, embracing her in a silent hug. Sakura reached around Jessie and hugged her back. They didn’t care that they were making a gigantic mess with Sakura’s semen coating them and her bed, they were just happy to be free. Jessie and Sakura both fell asleep hugging each other tightly. Even though the toy had put them through one hell of an experience, they were content knowing that they were both gonna be okay in the end.