Hump And Pump 5 Dexs New Life

It was a hell of a month for Dex wearing that tube, Gem getting him aroused and denied almost daily. He licked her to seven climaxes during the four-week period, getting them even in the number of times one came over the other. Gem liked the fact his technique was improving as his normal attempt at oral was blasé at best. While aroused, he had more gusto into the effort.

Dex also found himself wearing the stockings more, plus an occasional wearing of a black see-through nightgown going midthigh on him. He tried complaining but it did no good as Gem simply asked him why. Wasn't he the one who wore panties all the time? Did she ever tell him to do so? No. Wasn't he the one who wanted to see how it felt to wear stockings against his legs? Did she ever tell him to do so as often as he did? No.

Why did adding a nightgown such an issue? Dex had no reply to sound like he was right and should complain. That he loved the way Gem experimented on him while he wore the panties was the only reason he did so, but Gem refused to accept any fault for that, even offering to not experiment anymore. That wasn't of any interest to Dex who loved how this worked out.

Dexter was an anal whore when he met Gem, found she sparked his interest in many ways. When the relationship deepened and it was time to spend the night, he tried to leave while knowing any attempt at 'normal' sex was always a disaster. He was so used to pumping a vibrator into his ass while humping his cock with the other hand, he couldn't even get an erection while the girl lay naked, desire waiting for fulfillment.

He even confessed twice he loved anal, the girl taking off so quickly he never had the chance to say it was his ass he wanted fucked, not hers.

When he attempted to leave Gem, she simply slammed him back into the sofa, demanding to know what the problem was, Dex finally admitting. Instead of tossing him out, she demanded to see how his ass was filled to prove he wasn't bullshitting her.

Gem not only didn't toss him out, she tossed down a towel and had him hump and pump in front of her. The next morning, discovering the act was the only one he was familiar with doing, she set about experimenting, trying different things.

Six months later she was still experimenting on him. Dexter was usually naked around the house or wore panties instead of his normal boxers as the panties gave Gem ideas of things to do to him. The experiments almost always left him in a satisfied heap of pleasure.

Gem moved into his house and took over his life, bit by bit, subtle bit by subtle bit, Dex not finding it strange to be nude while she was dressed, not finding it strange to kneel while she sat, not finding it strange to see what she planned for them for the day, eager to go where she wanted or do what she wanted.

A visit to an adult store meant Dex had more toys to be used on him. Instead of the small personal vibrators he always used, Gem used different sizes, slowly building his ass to where he wanted larger size cocks. Yes, he even referred to all of the dildo, vibrators, and strap-on, as cocks, Gem's preferred word over his usual vibration name.

It was, after all, just a name.

Gem simply had to appear with one in her hand or the strap-on attached and Dexter was over a chair or table, ass out, ready for whatever she desired. Begging for cock up his ass or his ass abused for her enjoyment was the norm, a norm he never thought about but didn't find unusual anymore, not with all the pleasure it brought.

Gem always offered him options, Dex never thinking he was being forced into this submission. She offered him the chance to do a hump and pump for a free cum, but, if he failed to cum in fifteen minutes he had to wear the tube for a month. He was used to it for a few days or a week, but Dex always came with a hump and pump, had always cum for years, and saw no way to lose.

Except he lost, had to attach the tube and hand her the key.

He had no idea how he lost, he did his own fucking of his ass while jerking off with his hand, all within view of his girlfriend who read a book. He had no idea Gem had switched the cock in his ass for one of his original personal sized ones, his ass now accommodating an almost normal sized cock. In fact, the smaller one was barely felt while it was pumped in and out of his ass.

Gem handed him the nightie one day, telling him to put it on, Dex not even thinking twice as he modeled it for her before the large mirror.

"I look stupid in this."

"You do, anal whore, but you're not wearing it for looks. I want a maid I can order about and punish as needed. That means we bring in someone else or you do it. So, got a girlfriend you want to share all this with, or you want to play maid?"

Dex was familiar with doing maid work, he and Gem usually sharing the cleaning and laundry and cooking. So, what the heck, why not?

It was a tough day for him. Nothing he seemed to do was right, Gem insisted she be called either Madam or Mistress as the maid wasn't going to call her by her first name. Twice he missed the title, twice he was spanked, his ass flexing for more but Gem was well aware of how far to go before he could have his own satisfaction.

He had to clean off the dining room table, get the pledge and rag, to make table and chairs shine. It would help if Madam didn't play with the remotes, the tube on his cock vibrating while the cock in his ass was moving according to what button was pushed. Any sign he wasn't happy meant a bondage item add to restrict his movements.

By dinner time, the maid was looking like he was about to cum just by being looked at, desire in his eyes, lust felt within his body. His ass was spanked more times than he tracked, the tube and cock seemingly nonstop unless they did stop, the maid almost begging for more.

Gem ignored all that while closely watching his reactions. She wasn't going to have him a cross dressing fag but have him simply aware he would want to wear whatever she desired, no matter what it was she desired. He long ago was used to licking up his own cum, Gem not even having to tell him. She figured he'd suck up someone else's cum without a problem but she didn't really want someone else's cock so that would only be theory for the foreseeable future.

"Maid, you missed a spot."

Maid came out to see what was missed but Madam simply shook her head and walked away. Maid sighed, redoing the cleaning of the shelf and its objects. It didn't help Madam came over with a Ping-Pong ball paddle to spank the ass held in position while the maid cleaned,

"Yet again you refuse to use a title. A good maid learns its place and does so with respect." The paddle hit the already sore ass, but the remotes had both tube and cock going at full speeds, the maid almost wiggling the ass as it was punished.

"Sorry, Madam, maid won't forget, Madam! Ow! Madam, maid has learned its lesson, Madam!"

Gem stopped to lightly scratch at the bruised ass, the maid done with the cleaning and now sighing.

"Thank you, Mistress, for correcting maid. Maid thanks Mistress for the attention."

Gem stared at him. Madam while being punished, Mistress while being pleasured. That was weird. It was also something she wanted to explore.

The nightie came into play several times during that month, Dex finally getting the title down pat, always using it when speaking as the maid to the Madam of the house. Or Mistress which more frequently seemed to be his preferred title for her.

During all this time he was only allowed a prostrate massage once, dribbling cum while not having the orgasm he really wanted. He had only four more days to go for his release, for Gem always kept her word of when she was releasing him.

With three days to go, Dex came home to tell Gem the tube had to come off. She snacked on celery while simply looking, waiting for a reason. He was being sent to attend a convention tomorrow along with five other executives. He would be gone when his time was up, so he needed it off before he left.

Gem saw no reason to accommodate his request, she was willing to unlock him when agreed upon. If anal whore preferred to wait a few days longer, that was on him. Knowing where they were going had security at the doors, Dex knew he couldn't get inside without being examined, thus he needed it off before, not after the trip. Gem didn't seem interested, simply looking at him until Dex realized he either was wearing it or had to offer Gem a good alternative.

Before he left for the convention, the tube was off, Gem making sure he had no cocks hidden in his ass or luggage. Dex was happy he'd pass through the security without causing a fuss. He was less happy with what he agreed to do when he came back. For some reason he couldn't fathom, Gem was much better at negotiating than he was, and it was part of his job.

Once home, he unpacked, put his stuff away, and carried a Tupperware container to the kitchen, placing it into the refrigerator. He sighed, what was worse, he had to use his phone to video the act of dribbling into it to prove to Gem he didn't cheat with another woman, nor did he have other men dump cum into the container. Dribbling was the proper word, for without a cock in his ass he couldn't achieve the intense orgasm desired.

When Gem came home for work, they kissed and hugged, Gem going into the bedroom to get rid of the frumpy outfit she wore at work and dress in something more comfortable which showed off her tight and sexy body.

Dex thought it was strange she removed the container, putting in a finger to taste before putting it away. Gem simply wanted to make sure it tasted of Dex's cum even if his videos would show he did it all alone.

"Madam?"

Gem looked at him, wearing just the panties he purchased. Dex was about to do his part of being allowed out of the tube early.

"Madam, may this maid have a cock in its ass?"

"Not right now. I just want to relax before dinner."

Dex held back a loud sigh, he knew this wouldn't be easy when he agreed. At the time it seemed important to not have the tube on before leaving, but now, well, it was more like he should have just taken the risk of being exposed.

He wasn't allowed to cum without permission, wasn't allowed to have a cock in his ass without permission, wasn't allowed to caress himself without permission. Any violation meant time added per violation, any violation during the extra time meant agreeing to be in bondage to stop violating the agreement. Dex could easily see himself in full bondage gear 24/7 while Gem continued to look sexy as usual.

The worse part was that if the total time of one month and extended time exceeded a month, Dex agreed to allow Gem to bring in someone else to use as she had been using him. Dex had agreed in writing to be the maid for her and anyone she brought home to use while anal whore used the time to think of what he wanted.

He realized this would be the toughest month of his life, not doing anything stupid, not violating any of the set rules.

It was tougher when he realized Gem had a cock in her pussy, using the remote to keep herself happy while she read a book. She came on a towel, the book on the table as she moved the cock in and out of her pussy, Dex unable to take his eyes off the action. His body wanted to experience all that, making a violation almost certain. He caught his hand almost stroking his balls and cock before pulling it away. Yes, Gem was almost cumming, but nodded to show she witnessed the action.

For a week the maid never forgot the Madam or Mistress title, always anticipating her wants and needs, absently played with his own body before realizing his actions. At the end of the week, he was kneeling before her as she put double ended cock into his mouth, a few inches inside his mouth, eight inches extending from his lips as she velcroid the strap behind his head.

On hands and knees, he pushed it into the pussy, her finger rubbing the clit as he used it to fuck her to a climax, Dex not stopping until told to which meant a second one before Gem pushed him away. She lay there, happy, satisfied, and gave him that mischievous look he loved so much.

"Undo that and suck it clean. Then clean me up, maid."

He removed it, looked at the still wet pussy, 'Yes, Mistress' coming out before sucking on the cock. He wasn't used to sucking cock, but managed to lick and suck until it had no pussy juice on it. Then he lapped away at the shiny juices still showing on the flesh before him.

Gem looked at her boyfriend as he did as instructed. This was almost too easy.

In two weeks the only sign of Dex was when they were in public, once in the house and alone, he went into maid mode, doing whatever he could to make Gem happy. For two weeks he had no cock in his ass, his body missing what was routine for years. For two weeks he couldn't masturbate yet had to get a good dribble up to add to what was in the Tupperware container. Gem made it clear she expected it to be filled to the brim with cock cum by the end of the four weeks agreed upon. Both knew it would go faster if he was allowed to cum, but rather than whine and get more time, Dex bit his lip and prayed for strength.

By the end of the month from his return, Dex was a mess in more ways than one. He was sure he was going to die a painful death if he didn't get release soon, yet any sign Gem saw that he did so, meant more time with additional ways to prevent him from achieving his desire.

To Gem, it was great that the maid was always handy, rushed to do more than its fair share of the housework, happily gave her leg massages in hopes she'd give it a reprieve, but Gem wasn't about to allow it. A month was agreed, a month is what he got.

It was all interesting to Gem. Dex didn't seem to mind being the maid, even put on the outfit without being told. One time she found the bathroom towels on the floor and mentioned it, Dex quickly leaving to tell the maid it was a total screw-up. Gem was in another room when the maid came in, curtsying to her, saying Madam wanted to talk to it. Taking the maid to the bathroom, it quickly put the towels right and came along for the spanking it so richly deserved for being so sloppy around such a wonderful Madam.

Gem found it interesting simply because Dex now seemed to like wearing the clothing, liked the spankings he otherwise wasn't happy with, liked to refer to himself as him, but the maid was always referred to as it. Even when in bed he was happy to let her guide when they cuddled and slept.

At the end of the month, Dex seemed to not even notice, happily being the maid even if the time was up. Time to sit down for a talk.

No, Dex admitted, he had no idea where it all came from. It was tough to not cheat but it seemed the more he became the maid, the more he was punished for being a sloppy maid, the easier it was to not try to cheat. He knew not why, but right now he had zero interest in a cock in his ass just for the sake of it. No, he didn't know what he wanted anymore but was willing to allow Gem to be the Mistress in the journey. Other than not being able to cum, he loved his punishment.

Gem nodded. Once she found Dex came from a family where the mother ruled the household and the lives of all in it, she knew she could do more to have him openly submissive to her. Time for her to get the strap-on and make him submit more.