Wait

Story Info
Tom wants Jen to be in charge. Oh dear.
3.6k words
3.98
64.3k
17
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

Jen had a twinkle in her eye as she skipped down the road next to Tom. It was a beautiful shirt-sleeve day, just a small amount of breeze – the first day of Spring. They held hands, he leant over and kissed her and laughed. "Why are you so happy today?"

"Just an idea" she replied. "I've something to show you when we get home".

They were very happy together these days. Careers were going well, they were in love and the sun was shining. Sex was good. Tom had encouraged her to explore and had pushed her, little-by-little, further than she had imagined she'd go. They trusted each other and enjoyed their compatibly kinky natures. For a little while now, Jen had been thinking about how she could turn the tables and take the lead. In a way that he would enjoy of course, but she wanted to prove something. They sat at a table outside a café on the high street and ordered lunch. When the waitress had gone back inside she took his hand and pulled him across the table to her. "Tom", she whispered, "Would you like me to make one of your fantasies come true".

"Of course." He replied confidently and easily, smiling and kissing her on the lips.

"You'll have to promise to do anything I say."

Jen needn't have worried about his reply. Tom pretended to consider, but he already felt a thrill of pleasure at the idea. She knew that he fantasised about relinquishing control. There was very little that she didn't know about this side of him. She loved to coax these desires out of him when they made love. She would stop when he was most turned on and whisper into his ear. "Tell me what you're thinking."

"OK, anything you say, I promise".

"That was easy." Jen kissed him again and winked as the waitress reappeared with a tray. "I'm not sure you know what you've just let yourself in for."

When they got home she didn't waste any time. "Take off your clothes". Tom started – this was unusual – but he was excited too. With a flourish he threw his shirt over the banister as she steered him into the bedroom.

He reached for the top button of her blouse but she pushed him away. "Oh no, not yet Tommy", she said, mock-stern. She glanced down at his already rigid manhood. "Very good, turn around". He sighed with pleasure as she wrapped the black scarf over his eyes and tied it tightly behind his head. "Let's see how you enjoy this".

Five minutes later he was bound securely to the four corners of the large bed. "Don't run away", she giggled as she left the room. He could hear her upstairs in the kitchen, but very soon she was back in the bedroom, opening one of the drawers of her cabinet. "There are a couple of things you should know about this little game" she said, trying to sound matter-of-fact. "The first is that it might last a very long time." She kissed his forehead above the blindfold and ran her fingers across the length of his shaft, making him shudder and twitch upwards. "The second is that, although the game has a pleasurable aim, you might not enjoy it all the time. Sorry about that Tommy – but the good news is that I will enjoy it very much!" She bent down and flicked her tongue where her fingers had been moments before. He moaned, already close to ejaculation.

Jen undressed, watching him all the time. She could tell from his short breaths how turned on he was. This was good. Slowly she straddled his chest and Tom felt the moisture between her legs as she gently took his cock in her hand, behind her back. "You've told me before about how you like to be teased" she whispered, stroking his nipples erect. "How you would like me to control your orgasms". She kissed him fully and pinched his nipples a little harder. "I'm going to make your fantasy come true, Tom. I fear you're going to realise how misguided you've been." She lifted herself from his chest and playfully bit each of his nipples in turn, before taking his penis briefly in her mouth. He felt the delicious warmth and release welling up inside him, but she was already away and the feeling subsided. "Don't move" she ordered, more steel in her voice now. "Don't you dare move a muscle. If you come you're in deep, deep trouble."

Slowly, very slowly, she lowered herself onto his upright cock. He gasped as he felt her wetness and heat envelop him. "Don't you dare come" she barked. "OK, these are the rules." She held him very still between her legs. "You're not going to have an orgasm for a little while. Certainly not today, probably not tomorrow. Maybe not for a week. Even a month. Let's see. All you have to do in the meanwhile is pleasure me whenever I want and earn your next orgasm. You're going to come when I decide the time is right." Tom thrust upwards but, quick as a flash, she was off the bed and hissing in his ear, "You're in big trouble for that."

One by one she untied each of his ankles and re-attached them to the top of the headboard, exposing his ass. She found her panties, discarded on the floor, and shoved them roughly into his mouth, tucking the last corners of white cotton material inside. "Close your mouth" she ordered and reached for the roll of tape with a sigh. Her eyes rolled upwards and she felt the wetness once more between her legs as she laid the tape over his lips and picked up the cane placed next to the beside cabinet. "Now I'm going to hurt you Tom" she teased in a singsong voice. "I'm going to make you cry." He felt a thrill again, something close to fear, but he was aroused. He didn't know how far she would go, but all he could imagine was pleasure.

The first few swishes of the cane were no more than playful slaps and a pleasing tingle spread through his buttocks. She grabbed his stiffening cock in her left hand. "Enjoying this a bit too much are we?" The cane fizzed through the air and he gasped through his nose as the pain began to increase. She was gently massaging him whilst the strokes continued, harder and harder. He couldn't control himself any longer, but suddenly her hand was clenched around his balls instead of his shaft and gripping tight as the cane now whipped into his thighs. She twisted and he screamed. She delivered two more cruel blows to each buttock, staring at the tears as they trickled down his gag from beneath the blindfold and stroking herself to climax. She let out a yell and threw the cane to the floor.

Five minutes later he was still tied to the bed, but the gag had been removed and his legs released. Still throbbing and whimpering from the pain in his balls and ass, he returned her kiss with passion. Inexplicably his beaten penis began to stiffen once more as their tongues brushed each other. "I'm proud of you so far Tom" she said, "but you need to know that this is just the beginning You have a long way to go to earn your next orgasm". He gasped and squealed as he felt ice applied to his cock and balls. She kissed him again but by now he had shrivelled to nothing. "I need to know that there won't be any cheating". Something hard and cold sheathed over his penis, and for the first time he felt the dread thrill of real fear.

"What's that Jen?" he said, trying to sound as casual as possible. There was a tightening around the base of his shaft and a metallic click.

"That's your new underwear you silly man" said Jen, massaging his balls with both hands. "I'm going to keep you all locked up for a while to teach you a lesson." Tom tried to stutter a reply, but nothing came out. "You lie there and think about it for a bit" she continued. "I'm going upstairs for a glass of wine and when I come back you're going to make me come with your tongue." He heard the bedroom door close behind her.

Tom had fantasised about sadistic women before, but he had no idea how readily Jen would take to the role. The slightly frightening thing was that she really seemed to get off on his predicament. The next week became an increasing nightmare for him as she delighted in finding new ways for him to 'earn' his next orgasm.

On Monday she tied him to the bed again and removed the device. He brought her to climax twice with his tongue and she pretended to reward him by taking him inside her once again, but she pulled away when he was close, re-applied the ice and then the cruel metal contraption. This was only the second day, but Tom was already begging for release.

On Tuesday she told him they would play a game. She tied him naked and upright to the banister at the foot of the stairs with his legs apart and released his member which was erect within seconds. The game was called No Pain, No Gain. She took two small elastic bands and wound one around each of his testicles so that they both stood out proudly from his scrotum. She found a heavy chopstick in the kitchen and explained the rules. Tom was required to say "Please mistress, whip my balls so that I can be allowed to come". Jen would then apply strokes to each of his balls in turn, until she chose to stop. If he could manage this five times then he would be allowed his release. Of course there was no hope of succeeding in this game. On the fourth turn she whipped him mercilessly until he begged her to stop, whilst touching herself in front of him. After she came she threw the chopstick down, roughly pulled off the elastic bands and snapped the device back in place before gagging him again with her panties and tape. She whispered the single word "loser" into his ear as she went upstairs to collapse on the sofa, not to reappear for an hour or more.

The strange thing was that although the chastity device was an ever-present reminder of his predicament, Jen was capable of carrying on her everyday life entirely normally. On Wednesday he didn't see her at all as she was out of town at a concert, although he did receive a steady stream of provocative text messages. One said enjoying doing this 2 u so much. maybe never release u. touching myself now xxx He presumed she was joking, but the cold metal beneath his trousers was all too real.

On Thursday she was in a particularly playful mood. She knocked on his door early in the evening and immediately had him on all fours, licking her to climax in the hallway. He repeated this feat whilst she sat on the sofa watching TV. "You're doing well Tommy" she purred. "You know, tonight might be the night". After dinner she took him to the bedroom, kissing him passionately and feeling his crotch. She undressed him, tied his wrists gently to the bedposts with two silk scarves and released him from the restraint between his legs, using the little key that always disappeared as soon as the device was reattached. Snuggling up next to him she began to touch herself. "Darling, this turns me on so much". She took his cock in her mouth and knew that he was already almost at the point of explosion. Fondling his balls, she continued, "Tonight is when I planned to let you come". She ran her tongue around the tip of his penis again and he spasmed with pleasure and expectation. "You've been so good". She inserted the tip of her finger in his anus and he almost screamed with lust. "I know you want to come so badly..." She massaged his balls very gently and the finger slid further in "...but I'm afraid I just enjoy seeing you like this too much. you'll have to wait longer I'm afraid". Within seconds the ice was applied and the metal was back in place, whilst Tom whimpered, his eyes moist. "Don't be such a big baby" she laughed.

On Friday Tom saw a darker side to Jen. She had him strip and stand on a chair upstairs in the lounge. She handcuffed his hands behind his back before putting a rope noose around his neck which had been tied around one of the big wooden beams in the ceiling. "Don't fall off now" she teased as she undid the chastity device and kissed his quickly-growing member. There he stayed for the rest of the evening, whilst she spread herself on the sofa, drank wine and touched herself, first with her fingers and then with a large vibrator. He felt humiliated and couldn't understand why he was almost constantly hard the entire time. Naked and purring she taunted him from below. "Tomorrow is when you really get the chance to earn your orgasm Tommy". She repeated this several times. She seemed happy to lie for hours, smiling up at him, occasionally stroking his erect shaft and bringing herself to climax after climax.

On Saturday they went shopping in the morning, Tom secretly infuriated that she could carry on as if nothing was happening. Every time they passed a pretty girl he would be aware of his metal prison. Once in a while Jen would stroke his ass or press up to him when they kissed, but aside from that it could have been any day of the year. Sometime around late afternoon Jen called to Tom to come up from the basement where he had been working. "OK, this it it – your chance to earn it. It's been nearly a week now." She made him take off his clothes. By now this had become normal, but Tom still felt his cock struggle against its cage as soon as he dropped his trousers. "I wanted to take you to the point where you would do anything for release. Now we're going to test that". She took him upstairs and tied his hands together, hoisting them above his head over the high beam. Jen pulled down with all of her weight until he was on tiptoes and secured the loose rope. She blindfolded him and released his prick which immediately sprang up erect. "There was only one way I could think of to test you" Jen whispered in the hard voice that she had adopted more and more often. "I'm going to whip you until you beg me to stop – but I'll only stop when you ask me to humiliate you in front of one of my friends". She grabbed his cock and began to pump as his breathing quickened. "I know how much you hate that idea. Get ready to beg".

She let go of him and marched across the room to where her video camera was set up on the tripod. "I'm filming this Tommy" she called before stroking his aching manhood once again. "So, how much do you want to come after your week of chastity?" She stepped behind him and picked up the small whip from the table where she had left it before lowering her trousers. With her left hand between her legs she flicked at his buttocks a few times, watching him squirm and gasp. "Tell me what you'd do to be allowed to come" she whispered as she slashed him across the ass with more and more force.

He began to moan. "Anything".

She stopped and took his cock in her hand again "Anything?" She pumped him for five, maybe ten seconds and then released the whip again, across his back, across his thighs.

"Anything Jen, humiliate me".

She whipped harder and harder, stroking her wetness and gasping for breath. "Say it again. Say it more clearly".

Tom screamed. "Jen!" He couldn't cope with many more blows. "I want to come so much. I'll do anything to come. I want you to humiliate me in front of your friends."

She lashed his buttocks again and again, fingering herself and panting. "Thank you Tommy". She crumpled on the floor as she came. "Tomorrow Tommy, tomorrow."

On Sunday Tom woke up early, with Jen nuzzling him and stroking his legs, thighs and chest. "Today you're going to earn your orgasm" she sighed into his ear. "You've earned it. You're going to come so hard it will all have been worth it". She fondled his balls and led his hand between her legs. "Make me come, Tom".

By lunchtime he was inside the large wardrobe in the bedroom. Jen had removed all the clothes and handcuffed his hands behind his back. The noose was back around his neck and attached to the high clothes bar. The evil device was still in place. "I don't want any screaming today" she said as she took a pair of panties from the wash basket and stuffed them in his mouth, securing it, as ever, with a large piece of tape. Tom was not sure what was going on, but Jen had been assuring him all morning that if he went along with everything then he would be allowed his orgasm. There was a knock at the door and Jen slid the door across in front of him, waving before the darkness was complete.

Tom could hear footsteps upstairs but had no idea who had arrived. His sense of time was confused, but he reckoned on having been in the wardrobe for half an hour or so before he heard the bedroom door open. The wardrobe door slid back a little. It was Jen. "Guess who's here?" she sang, and pulled the door back fully so that light streamed in. The feeling of humiliation was immense. Naked, bound and gagged, locked into a chastity device and now staring at Marie-Stephanie, one of Jen's best friends. Both girls had stripped down to their underwear.

"Hello Tommy" laughed Marie-Stephanie. "Jen's been telling me about your little game all week". Tom went crimson. "She says you're very good with your tongue" she added and winked at him. "I've brought you a little present". She opened her hand to reveal two small clamps, a metal chain and the same two elastic bands from Jen's sadistic game earlier in the week. Tom winced. "I hear you're expecting a prize today" added the French girl.

"Yes, but he has to earn it" said Jen. As she stepped away her friend picked up a camera and began taking photographs of Tom in his helpless state. Jen attached the two clamps to Tom's nipples, joining them with the chain. She then motioned to Marie-Stephanie who smiled as she skipped over and produced a key. She dangled it infront of Tom's face and giggled before releasing his cock into her hand. Of course he was stiff within seconds. "Not yet, lover boy" Jen called over. Marie Stephanie knelt down and licked his shaft up and down, making him tense and gasp before winding the rubber bands around his balls as before.

"I can't wait to show these photos to all my friends" laughed Marie-Stephanie as the camera flashed again and again. Tom couldn't believe his eyes as next Jen unhooked her friend's bra and pulled her gently onto the bed. They began to kiss and touch each other and his cock stiffened, ready to burst. As the moans got louder and first bras, then panties were discarded, Jen got up off the bed and drew the wardrobe door across, plunging him back into darkness.

"We can leave the rest to your imagination can't we, Tom."

After what seemed like hours, but was probably no more than one, the wardrobe door opened again. Jen was nowhere to be seen, but Marie-Stephanie was grinning, wearing one of Jen's robes and waving the chopstick. Tom shook his head furiously, but she gave his nipple chain a playful tug and pouted. "Jen says you have to earn it, remember". She took his blue, punished member into her mouth. The feeling was of absolute warmth and bliss. Suddenly he convulsed in pain as she struck his right testicle. She smiled. Then the left. Three, four, five times. He tried to scream through the gag. She took him into her mouth again. Then more punishment. It was too much. Too cruel. With one more harsh flick to each ball she kissed him on both cheeks and walked out.

A minute or so later Jen walked in, wearing her overcoat and looking at her watch. She was wearing a rubber glove and carrying a red bucket. She must have spilled something. "Just going to take Marie-Stephanie to the station. Come on, quickly then." She ripped the rubber bands off his aching balls and the tape from his mouth, starting to pump his dick with the abrasive palm of the glove. "Oh, do be quick Tom, I thought you wanted this" she said impatiently, increasing her tempo. His nipples hurt, his testicles were still very sore, and now his poor manhood was raked by the yellow plastic. He came limply into the bucket. Jen wiped him quickly with the sponge before reaching for the little metal device.

"No, no, Jen. Not any more." His eyes were wide.

She smiled at him. The lock clicked. And she closed the door behind her.

Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
6 Comments
AnonymousAnonymousover 1 year ago

Oh boy I don't know her to start. But the first day that she caned his ass it would have been game on bitch. But let say he wanted to see where this was going for 3 or 4 days, at the end of that time I would have cut off her toy cage and bought her a chastity belt with two Vibrating plugs, stalled on her and tied her to the bed for a week with everything running. Just to really fuck her up, then kick her to the cerb..

InfiniteXaosInfiniteXaosover 1 year ago

She went way too far. That was simply abuse.

AnonymousAnonymousalmost 8 years ago
I agree with Overthefalls

This bitch needs to suffer like she made Tommy suffer all week. Fantasy is one thing, but beating someone's balls with a chopstick is anything but. Cut the lock then deck her with a straight right as soon as she comes in the door. Have your bags packed so all you have to do is walk away.

OverthefallsOverthefallsabout 11 years ago
Cut them off

Simple action. Takes less then 30 seconds to cut some wimpy little lock off. When she returns, try not to beat her to death. Just some pain to remind her to NEVER contact you again. No one would put up with the assault and battery she put him through. She has no love or respect for him so she's history. No other possible ending to this sorry tale.

AnonymousAnonymousabout 12 years ago

This is an awesome story. I like to think it is just the beginning of Tommy's hard prolonged whippings and denial, and humilliating servitude to her and her friends. Ohhh how i want this.

Show More
Share this Story

Similar Stories

Teased and Denied Ch. 01 Dominant wife controls willing husband's orgasms.in BDSM
The Gift That Keeps On... Husband's desire for chastity play leads to a lifestyle.in BDSM
Control of His Cock Loving wife takes control of her husband's orgasms.in Loving Wives
She Creates the Fantasy Wife catches husband; wife takes control.in BDSM
Caged Cock Tease His wife makes his chastity fantasy come true.in Loving Wives
More Stories