Loading...“Hello Jack”, Linda said dully to the man staring into his mail compartment. Jack was about 6″ tall. It was obvious he was in good shape. He was handsome, Linda thought but it was hard to see because of his macho attitude. “Oh, hello Linda”, the man said back to the blond haired lady he shared a duplex with. Jack lived just up the stairs. Linda lived on the bottom floor. They shared a common area that had become an irritation for both of them.
There was a front door that opened into a common area. It was a small foyer with a straight staircase running up the right hand wall that went to Jack’s place. Straight and to the left led you to Linda’s front door. Just as you came in the front door there were two mail compartments doors mounted in the wall.
“You forget something?” Linda asked as she noticed Jack staring into his empty box.
“Nah, just hasn’t come yet.” he replied.
“I haven’t seen Amy around in awhile.” Linda mentioned causally.
A little irritated, “yeah, you won’t be seeing Amy around here anymore. We’re kind of done.” Jack replied.
“That’s a shame, I really liked her.” Linda said.
“I’m sure you did.” Jack kinda mumbled as he closed the empty box and headed up stairs.
As he passed Linda he noticed she was wearing yoga pants and a tight top. She was curvy girl but obviously worked out. Normally Linda was the type of woman Jack would go for except… she was such a bitch. Ever since he moved in she had rode him about the common area they share. If he left his bike in there to long, she complained. If he tracked a little mud in, she complained. If he forgot to lock the door, she complained. Lights on, shoes left by the door, finger prints on the wall all brought down her wrath. Really, it was no big deal, she just liked being a bitch!
When he got into his place he went straight to his computer. He looked up a tracking number of a package he was expecting. The screen said it had been deliver but his box was empty. “No problem,” he thought, “it will show up soon.” He leaned back wondering if he should have stuck around to see if the mailman had put his package in Linda’s box. The thought made him chuckle.
It was about this time a day Jack really missed Amy. They had been dating for almost a year. She spent more time at his place than she did at hers. Amy was fun. He enjoyed spending time with her. She was a pretty hot catch actually. Brown hair, a little on the slender side but had a great tight ass. And that’s were the problem was. Jack and Amy had a great sex life but it was a little bit vanilla for Jack. Jack got it in his head he wanted to have anal sex with Amy. Amy was absolutely against the idea, which just made Jack want it more. He tried all the usual persuasive lines. “It won’t hurt if you relax” “A lot of women like it” “Some woman can cum from just anal sex” “Don’t you trust me?” “It’s built to stretch” “I’ll only stick the tip in”. The more Jack pushed the subject the more irritated Amy became. Finally, she realized Jack wouldn’t let it go, so she let him go. He hadn’t seen or talk to her in over two weeks.
The package Jack had been waiting for were a few DVDs he had ordered. He started thinking about Linda accidentally getting his package. He smiled again as he thought about the look that would be on her face as she read the DVD titles. Anal Destroyer, Anal Assault, and Taking it All. With that amusing thought in mind Jack pushed away a few of the dishes that had piled up since Amy left and started making dinner.
The next day when Jack got home Linda was at her mailbox. She reached in and grabbed a brown box. “Jack, this looks like it’s yours.” she said as she pointed to the label. Jack grinned and took the box. “Thanks,” he said as he headed up the stairs. As he passed Linda he noticed She was staring at the floor. He looked back and saw that he had tracked a little mud in on his shoes. He looked at Linda then proceeded up the stairs. “One day you are going to clean up your mess, Jack.” “Oh shit, Linda. It’s just a little dirt.” he said irritated. “Be a good girl and sweep it up, will ya?” He told her as he disappeared up the stairs. He knew he shouldn’t push her buttons like that but, damn, did she deserve it.
Soon Jack was opening the box Linda handed him. If she only knew. When he looked inside he saw his three DVDs but there was another box as well. He saw a bright yellow paper in the box too. The paper explained that when he had ordered the three DVDs he got a surprise random gift for free. He opened the small gift box to find a male chastity device. “What the fuck?” He thought. The device had a ring that went behind the balls, with a very small cage attached and a small chrome cap that looked like the top of a salt shaker. He studied it for a minute then tossed it aside. He grabbed a few beers and sat down to watch his anal porn.
After he had watched enough to get him off, and down a few beers he remembered the chastity device. He picked it up again. He noticed how small it was. He placed it up to his dick. He was surprised that it looked like it would fit, because he had just cum he told himself. What the hell he thought. It took some doing but he got it it on. The device was only about an inch long with a half round cap at the tip. Jack noticed there was a part at the base that when closed, it locked it on. There was a small key hole to unlock it. Jack looked in the box and found the key before he snapped it shut. He looked down at how tiny and pathetic his dick looked locked up in the tiny steel device. He laid his head back on the couch and fell asleep.
Jack awoke with a uncomfortable pain in his crotch. He reach down to make an adjustment only to be blocked by the steel chastity device. The device was blocking him from getting his morning hard-on. He laughed when he realized he had left it on and that he couldn’t grow at all with it on. He grabbed the key to unlock it. But, to Jack’s horror, the key didn’t fit the lock. He tried every way he could think but it wasn’t the right key. He spent an hour trying to get it off but it wouldn’t budge. It was too tight to pull off. The steel was to close to his skin to cut or break. Jack was in full panic mode. Worse he was already late for work, so he had to wear it, for now.
It had been five days since Jack had trapped himself in the chastity device. It was driving him crazy. He was seriously thinking about going to the hospital to see if they could remove it but he knew he would die of embarrassment. Jack knew a lot of people at the hospital because Amy worked in the ER as a nurse, no way would he let them know he locked his dick up, especially in a one inch cage. He had already called the DVD company but they claimed they didn’t know what he was talking about. He thought he would sue them except he’d have to go to court and tell about it.
When he came home that night Linda was in the foyer. Jack noticed she was wearing very tight yoga pants and a tight half top. She looked great. Jack seem to notice more women looking great since he trapped himself. He was horny as hell and he didn’t know how long he could take it. As Jack walked in Linda bent over to pick up some mail that fell on the floor. He got a great look at her curvy latex covered ass. His dick tried to spring to life only to be blocked again. “Augh!” he growled. “Something wrong?” Linda turned around to ask. Jack ignored her. He grabbed his mail and turned around to leave and ran right in to Linda. He almost knocked her down. “Why the hell were you standing so close?” he barked. “Calm down, Jack. ” she replied with a huge grin on her face, “no one got hurt. I was just looking at all the dirt you tracked in again.” Jack was in no mood. He pushed past her and headed up stairs.
“The key to happiness is cooperation,” Linda said as he was walking away. “That really is the Key.” She emphasized the word Key. Jack made it up a few more steps before he turned to look back at Linda. She had a grin from ear to ear. Then it all came clear to Jack. Linda had gotten his package, added the chastity cage and switched the key.
“You bitch!” he yelled. “I’ll have you arrested!”
“For what?” Linda answered innocently but with a little laugh.
“You know for what. For this damn cage.”
“I’m not sure I know what you mean but if you got yourself into some sort of trouble, you did it.”
Jack thought for a moment. His head was spinning. He did put it on himself. He couldn’t even prove she has the key. He had no proof she was involved.
Well, you’ve had your fun. How about that key?” Jack said in a softer tone.
“I’m not sure what key you are talking about but, I guess, if you would do a few things for me I might be able to find a key… to something… that may help you.”
“Forget it'” Jack barked as he turned to go up the stairs.
“Ok, I did notice when I ran into you just now there was something hard at about crouch level. It felt like hard gauge stainless steel. The kind that can’t be cut unless you can use a torch but you wouldn’t want a fire near there. It also felt like a device that might have a lock that would break if messed with too much… but what do I know.”
Jack stopped again. “What if I come take the key from you? You couldn’t stop this man.” Jack said with as much macho as he could muster.
“Oh, I imagine the kind of key you would be looking for would be very small and impossible to find… if it was even on the premisses.”
Jack knew Linda was right. “What do you want? Money, an apology? Ok, I’m sorry I’ve been rude to you.”
“No money, and you will take your apology back as soon as you get the key. He’s what I want. I want you to clean this foyer. Scrub every inch of it. I want you to remember doing it so maybe you will keep it clean. And I want you to treat me, and other women with respect. So I have some conditions to help you understand how to do that. Meet me here at 8 am Saturday morning.”
Jacks mouth fell open. “Saturday is three days away! I can’t take this thing that long. You bitch.”
“See Jack, you don’t get it but you will. Take the time to think about it. I’m mean you really won’t be busy doing anything else.” She made a little jacking off motion in front of her crotch, laughed then disappeared into her place.
Three days later Jack was waiting in the foyer at 7:30 am. He was beyond frustrated. He had not had a hard-on in over a week. He never thought he would be so frustrated. Knowing he couldn’t have sex made him want it worse than he ever did before. Linda showed up 10 minutes late. “Car trouble,” she giggled as she shut the door to her place. Linda explained to Jack how she wanted it cleaned. She expected him to get on his hands and knees and scrub every inch of the floor. Jack listened, rolling his eyes a few times. When Linda finished she paused.
“One more thing, Jack. The other day you told me to be a good girl and clean-up your mess. I really think you need to get a different perspective so you can understand how disrespectful you are.” That said, she pulled out some clothes and handed them to Jack.
As Jack examined the clothes he started shaking his head. “No! No, I will clean the room but not in this.” he threw the clothes down.
“Alright then, see ya later.” Linda said as she started to go.
“Wait, wait… can we at least lock the door so no one can come in? And can you wait in your place until I’m done?” Jack said with his head facing down.
“Door locked, yes. But I’m staying.” Linda said as she folded her arms.
Jack went up stairs to change. When Linda saw him coming down the stairs she burst into laughter. Jack was wearing a small tight tank top shirt that came down to his belly button. He had on a bright neon pink thong and high heel shoes. As soon as he saw Linda he turned red with humiliation.
“This is ridiculous! You are such a Bitch!”
“Now, now, that kind of talk I is what got you into this mess.” Linda looked Jack over. He was in pretty good shape. Good muscle tone, no belly, tight ass. “Those panties fit pretty good, Jack. I thought there would be more of a bulge.” She said as she giggled.
“You know why it isn’t bigger. Let’s get this over with.” Jack demanded.
After scrubbing the walls, the doors and the stair railing, Jack started on the floor. He got down on his knees and started scrubbing. Soon he had it halfway finished. He was so busy working hard he had forgotten Linda was there. He didn’t notice she had walked up behind him. Linda got a good look at Jack. He was bent over so far she could see the g-string in his crack. His asshole could clearly be seen on both sides of it. His balls had worked loose from the sting and were hanging free. She laughed.
“Click” Jack turned to see Linda snapping picture of him. He tried to jump up but stumbled on his heels. “Click, click, click.”
“Stop that!” he yelled as he steadied himself. “Delete those now or I will break your phone, you bitch!'” Jack was mad.
“Oh, these automatically upload to the cloud. Breaking my phone won’t help.” Linda just stared at Jack daring him to act. “You know that bitch word is getting old. It’s going to cost you this time. After you finish here you can clean my place too.”
Jack started to object but realized he couldn’t win. His dick was still locked and now she had pictures. Linda motioned for Jack to look down with her eyes. He looked down to see his balls hanging free. Embarrassed, he quickly tucked them behind the small fabric hiding his cage and went back to work.
After Linda made him do several areas over to her satisfaction she brought him into her place. Her place was pretty clean already. Jack was relieved because he just wanted this over with. Linda told him to wash the dishes, then she disappeared into her bedroom. When she returned she was wearing a shear robe that was easy to tell she only had on panties underneath.
“This is what I wear inside, I hope it doesn’t bother you?” she paused then laughed. “Oh, that’s right, you can’t be bothered. Little did Linda know that Jack’s dick was working hard to get free.
“Alright Jack, I’ll be in the living room. Go ahead and finish the dishes.” She raised a bell to show Jack. “If you hear this bell come see what I want.” She gave the bell a little wiggle. “Almost done, Jack.” She said with a wink.
Not long at all Jack heard the bell. When he came in the room Linda was sitting on the couch. Her robe was all but open. “Get me a glass of wine, sweetie.”
“Ok” Jack turned to go.
“Ahem!” Linda cleared her throat.
“Yes, ma’am” Jack said humbly.
After bringing several glasses of wine to Linda, Jack relaxed. Though he thought Linda had gone to far he did realize he had treated her badly. Also, she was making him so horny the way she was flaunting her flesh. If only he could get his hand on his dick for some relief.
Jack heard the bell again, grabbed the bottle of wine and headed into the living room. As he turned the corner he froze. The bottle of wine fell out of his hand onto the hardwood floor, spilling out a little. Jack didn’t care. His ex, Amy, was sitting next to Linda on the couch staring and laughing at Jack in his little outfit. Jack ran as fast as he could in his heels back into the kitchen. He heard both girls roaring with laughter.
Shortly, Linda showed up. “Listen Jack, I know you are embarrassed but you treated Amy worse than you treated me. Now is your chance to show her you’ve changed your ways.” She tugged at Jack’s thong as she said it. “Now, I’m going to ring that bell in a minute and you better bring Amy a glass of wine and clean up that mess you just made. Besides, Amy has seen you naked and she has already seen your little outfit. You can’t even leave without going past her. And you would still have your cock lock to deal with.”
Soon Jack heard the bell ring. He took a deep breath and headed in. He couldn’t look Amy in the eyes but he could hear her giggle. He gave her a glass of wine and refilled Linda’s. Just like in the foyer he got down on all fours and started to clean up the wine. This gave the girls a great view of his ass and asshole.
“He cleaned the foyer?” Jack heard Amy ask.
“Yep, the whole thing. He’s such a good girl” Linda replied as they burst into laughter.
Jack wanted the ground to open up and swallow him. He had never been so embarrassed in his whole life. He had let a woman trick him into locking up his own dick and then parading her power over him to his woman. At least cleaning gave him something else to concentrate on. Then Jack felt his thong snap. He leaped to his heels to find Linda behind him. He also realized she must have cut his thong because it fell to the floor. He quickly covered his cage with his hands.
“Oh, don’t be modest now,” Linda said as she sat down next to Amy on the couch again. “We’ve been staring at your exposed asshole for the last five minutes.” Jack turned even redder with embarrassment.
“Listen, you might as well let us see it. I can’t unlock it unless you let me see it.” With that Jack slowly lowered his hands. Both girls took a second to comprehend how small the cage was then they burst into more laughter.
“Oh my, Amy, how did you put up with that? I mean it’s just a tiny nub of a thing.” Linda giggled.
“I don’t know, I knew it was small but I guess I never saw it in the light before.” Amy replied as they went into another fit of laughter.
Jack could see they were pretty drunk but he had had enough. “Ok, ok, you’ve had your fun. Now stop being a bitch and get it off.” Jack demanded.
Linda’s face went straight. “That’s going to cost you a spanking, Jack. I thought we had learned something today.”
“Do you think I’m going to sit here and be humiliated all night? I’ve got some pride left.”
“We were almost done but we’ll have to see what we can do about that male pride. Seems you would have understood by now that you can communicate you feelings to women without insulting them. I guess we have a little more to teach.” with that Linda patted her lap.
Jack hesitated. Linda looked down at his cage then up to his burning red face. “Not in front of Amy.” he pleaded.
“Do you really think your in a position to make demands?” Linda asked.
“No.”
“Ahem?”
“No, Ma’am.” Jack sheepishly said.
Amy watched with amazement at how easily Linda was handling Jack.
Linda Patted her lap again. This time Jack, with his head down, took a position across Linda’s lap. Linda reach down to take her slipper off.
“Whack!” Jack thought it would be worse but it did sting a bit. Linda kept spanking Jack’s ass and each stroke seemed harder than the last. Jack held out as long as he could but eventually he couldn’t stop from making a noise with every whack. Then he couldn’t control kicking his legs and squirming on Linda’s lap.
“You are going to learn that being nasty to women doesn’t pay, if I have to do this all night,” Linda said sternly as she spanked Jack’s ass. When his ass was fiery red and she thought she heard him sob, Linda pushed Jack off her lap and instructed him to stand in the corner with his hands by his side. Jack did as he was told, not even looking back as he took his position.
Amy looked at Jack’s red ass, “is he hurt?”
“Just his male pride,” Linda replied as she poured them both some more wine.
After about twenty minutes Linda thought it was time for the party to start wrapping up.
“Jack, I think we have a better understanding now but I need to know you feel the same way towards Amy, and all women.” Jack shook his head up and down.
“”No, I need proof before we remove your cock cage and let you free. Do exactly as I tell you in the next few minutes and I will release you. Who knows, you may even get a reward. Jack shook his head up and down again.
Linda took Jack by the hand and lead him to the ottoman in front of the couch. He did not resist. She instructed him to lay on it with his stomach. She tied his hands to the front legs and his knees to the back legs. He was basically on all fours with his legs tied open. His red ass was on clear display.
“Now Jack, what I want you to do is kiss Amy’s asshole. Show Amy you understand where your place should have been in the relationship.” Amy was surprised. Jack would barley lick her pussy, but he never wanted to do anything with her asshole but fuck it. Amy lowered her panties from under the short skirt she was wearing. She got down on all fours and backed her tight ass up to Jack’s face. She looked back and made eye contact with Jack for just a moment. His face was as red as his ass. Jack hesitated for a second and Linda slapped his sore ass hard. That was all it took. Jack started peppering Amy’s ass with kisses.
“Good Jack, but not good enough.” Linda said as she smacked his ass again.
This time Jack started kissing Amy right on her asshole. Another slap on Jack’s ass got him to stick his tongue into Amy’s asshole. Both women burst in to laughter at Jack’s eagerness to lick Amy’s asshole to stop from being spanked. Finally, Amy pulled away. She patted Jack on top of his head in an approving manner.
“Jack, the very last thing we need to talk about is anal sex. Amy told me that you are obsessed with the thought of it. Is that still something you want?”
Jack thought long and hard about his answer. “Many women enjoy it. I don’t think it’s a bad thing.”
“True,” Linda replied “but only when it’s consensual. Otherwise, it’s just degrading.”
“I don’t think it’s degrading. It’s just something fun a couple can do.” Jack answered still being careful to not upset Linda.
“Ok Jack, why don’t we stick something up you ass then?” Linda said with a grin. Amy put her hand over her mouth to stop from laughing at the thought of Jack getting it in his ass.
“No..no.. No I don’t want that.” Jack repeated as he shook his head no.
“But why? You said it wasn’t degrading. You said it was fun. Certainly if you expected Amy to do it you would be willing to do it too.”
Jack knew he was trapped. “But, she’s a girl.”
“So, everyone has an asshole. They all stretch. You even have a prostate back there to stimulate. Can you think of a reason why she can and you can’t?” Linda reasoned.
There was a long silence. Jack couldn’t come up with an answer. Then Amy piped in, “what if we just stick the tip in?” Both girls burst into laughter knowing this was the exact line Jack, and many men, use to try and talk women into anal sex. Jack knew this was the best deal he could hope for.
“Ok, but just the tip. You promise?” Jack said reluctantly.
“Of course Jack. I’ll only put the tip in unless you ask for more.” Linda said elated that her plan had come full circle. She left the room and came back wearing a flesh colored strap-on dildo with a pair of fake balls.
“Jack, Amy told me why she left you. When the postman delivered your anal DVD’s to me by accident, I knew I had an opportunity. I ran out and bought the chastity cage and this strap-on dildo. I wasn’t sure you would put the cage on but when I bumped into the other day I knew you had.”
Linda showed Jack the dildo. Jack gulped at the 8″ size. “Just the tip,” he reminded her.
Linda lubed up the dildo. Then she stuck a lubed-up finger into Jack’s tight, virgin ass. Jack grimaced at the feeling. Next Linda positioned the dildo right over Jack’s anus. She applied some pressure but it wouldn’t go in.
“Relax, Jack. Trust me, your going to love this!” Just as the words came out of her mouth enough pressure had been applied to force the dildo into Jack’s asshole. Linda watched as the tip of the dildo spread Jack’s rim open and slid in. As soon as it went in, Jack’s head popped up and he let out moans of pain.
“Just relax Jack, only an inch or two went in. The pain should go away soon. Tell you what, why don’t we let you out of your cage.” Linda handed Amy the key as Linda stayed behind Jack with the tip of the dildo stuffed into Jack’s hurting ass. Jack was still tied on all fours so Amy had to crawl under to find the keyhole. Soon, Amy had unlocked the cage and removed it. Instantly Jack’s dick became rock hard.
“Oh my,” Amy said as she saw his dick become erect. “Somebody really likes getting it in the ass.” Linda laughed.
Jack’s face turned redder. “I can’t help it. My dick has been locked up for over a week. That’s the only reason.”
Amy reached under and took hold of Jack’s dick. “I’ve never seen it this hard before though.” both women laughed again.
Slowly, Amy started stroking Jack’s dick. It felt so good he forgot about the dildo in his ass. Suddenly, Amy stopped to get a better grip. When she did Jack started trying to hump her hand. He was desperate for release.
“Hold on Jack,” Linda spoke up. “If you keep humping like that you are going to hump this dildo right up your ass. Is that what you want?”
Jack needed release. “Please Amy?” he begged.
“Answer Linda first.” Amy demanded.
It was clear that if he answered “no” he wouldn’t get any relief. “Fine,” Jack grunted.
“I promised to only stick the tip in, Jack. I need to hear you say it.” Lind asaid with a smirk.
Amy waited. She just couldn’t believe what was happening.
“It’s ok if the dildo goes in more.” Jack reluctantly said.
Linda nodded for Amy to grab Jack’s dick again. Amy placed her hand on Jack’s member but didn’t move it and kept her grip very loose. As soon as Jack felt Amy’s hand he started trying to hump it again. Linda leaned forward putting more pressure on the dildo. With each hump Jack’s asshole gobbled a few more inches of the strap-on.
“Oh my Gosh!” Linda screamed. “Jack you have all eight inches up your ass. It’s balls are touching your balls. I can’t believe you are such an anal whore. You took it all so easy.” Linda motioned for Amy to move behind Jack to take a look. Even when Amy removed her hand, Jack kept humping for a few seconds. Jack had never been so desperate to cum in all his life. It was only after Amy let go did he feel the full effect of the dildo in his ass. It hurt a bit but mostly it made him feel full.
Amy looked at the big dildo buried to the balls in Jack’s ass. She couldn’t hold back her laughter.
“This is what you want to do to me, Jack? How do you like getting ass fucked by a girl? Judging by you actions you must love it.” That’s when she watched Linda pull the dildo all the way back out until just the tip was left in. Then Linda slammed all eight inches all the way back in. Jack groaned as Linda repeated the action. Soon Linda had found a rhythm and was stroking the dildo in and out of Jack’s ass. Amy watched as Jack’s asshole got smaller when the tip came near then was stretched wide open when Linda shoved it in.
Before long, Jack could feel the dildo pushing over and over on his prostate. It made him feel like he was going to blow his load. The only thing he could think about was getting relief, cumming. He started humping the dildo back in hopes that he would somehow get some friction on his dick, but all he felt was air. The girls laughed and ridiculed him as he desperately humped the dildo with his ass.
Then it happened. Jack felt his dick about to explode. Amy recognized the noises he was making.
“Oh my gosh! I think he’s going to cum. He’s going to have an anal orgasm!” Amy yelled in complete shock but with much delight.
Jack humped furiously waiting for the moment to arrive but incredibly frustrated he couldn’t get any friction on his dick. Then, Jack stopped humping and tensed up. Linda continue to pound his ass. Amy looked under Jack to see Jack’s dick shooting more cum than she had ever seen.
“He’s cumming! He’s cumming from just being fucked in the ass!” She squealed.
“Who’s the bitch now?!” Linda screamed as she slapped Jack’s sore, embarrassed, humiliated ass.