Hump And Pump Two Gem Likes To Play

Each weekend Gem introduced Dexter to another experience, Dexter never sure of what she was doing, sometimes having anxiety at her ideas, but he had to admit, his sexual satisfaction was always high.

This past weekend she tried to run vibrators on his cock while still in his boxers, but the cock kept moving around. Gem told him to get rid of them before leaving to return with white cotton panties for him to don. He refused, he wasn't wearing woman's clothing. No way, no possible way.

"Anal whore, I'm trying to play here. Look, when I tried with you in the boxers, your cock kept moving around so I couldn't do what I wanted. See the panties? Put them on and they will keep you from moving and I can see if you like what I want to do."

Dex finally put on the panties. She smiled, 'good anal whore' coming with the smile as she reached inside the panties to play with his cock. Dexter thought she was going to masturbate him but all she did was get it hard enough to point it straight up, facing his navel. She sat on a chair, using two vibrators cocks up and down the panty covered cock, his cock remaining in position even as it grew in erection.

"Oh, I got an idea!"

Dexter was barely thinking as the sensations were running through him as she lowered the panties to pull out the cock in his ass. She had him spread his cheeks as she pushed the cock lengthwise, so it rested in the crack. When the panties were pulled up, it was snug enough to keep it resting against the outside of his ass hole.

She returned to the two in the front, Dexter soon moving around as he tried to rub his cock into the two moving up and down it. He reached down to grab them.

"NO!"

He stopped, this being the first time she raised her voice at him. She didn't look happy as she looked at his hand and then him.

"Anal whore, I'm playing here. Keep your hands away and let me play. If you don't like what I'm doing, say so. If you grab, I'm pissed, and if I'm pissed, I'm leaving. Make up your mind what you want."

He went back to keeping his hands away from where she played, Gem almost immediately going back to moving the vibrations up and down at different times, different pressures, and different styles, sometimes the length against his cock, sometimes just the tip against the cock.

Dexter had no idea where it came from, but his climax had him spew up his chest and stomach as he dropped to his knees. She reached down to do more, his sensitive body making him shake at the sensations before another climax came over him, this time he lay on the floor, deeply breathing as he tried to recuperate from the experience.

After his shower, he found his boxers and new panties on the bed, offering him the choice of what to wear. He took the boxers and later they went grocery shopping. Back home, she helped him put them away, learning more about how his kitchen was laid out.

"You wearing boxers or panties?"

"Um, boxers."

"Ah."

She put the produce away with no other response. He looked at her tight ass as she bent over, having some ideas of his own.

"Why would you ask that?"

"I had an idea for play time, but we can do it some other time."

"So you want me to go change into them?"

She looked at him, no mischievous look on the face.

"No, Dexter. I wanted to play, you didn't wear them for me to play. If we play later, we'll have to do something else. If you want."

"I can go put them on for you."

"No, I don't want you to do that. I want you to put them on for yourself, to indicate you want to play with more ideas. You had that chance and selected boxer. Don't worry, we can do something else if you're ready later."

She was adamant he was not to go change for her, not now. He could only wear the panties if he wanted to, not because she insisted on using them in play time. She had no desire to do to him anything he didn't want done. Dexter loved what she did so far, now feeling a bit guilty he was wearing boxers, not panties. Just the way Gem hoped he would react.

They played twice more before bedtime, nothing mentioned about his wearing boxers the entire time. After dinner, he knelt naked before her as she lifted her dress up and sat down so he could lick her to satisfaction. Dexter was getting used to this position and scenario, more so aware past times of intercourse were disasters. At least Gem was willing to allow him to satisfy her.

Sunday had Gem smiling as Dex came into the kitchen wearing only the panties he refused to wear the previous day. She brought two cheap ones from a bargain bin in case he refused, but it appeared he was willing to try anything as long as she kept up her experiments giving him more experiences.

When he took her out to brunch, she made sure a vibrator was secure in his ass and put another one next to his cock inside the panties, the switch facing up. Dex wore sweatpants with an elastic waist at her request, not knowing what she planned.

He found out as they sat at a booth, her hand casually sliding over to slide down into his pants, her fingers fumbling around the erection until she found the switch which she turned on. Dex reacted as soon as the vibrations hit his erection.

"You're evil."

"You're a lot of work." Gem responded, "I have to have something to keep interested. Evil works for me."

He adjusted his posture as his ass clenched the one inside it.

"I have to admit, it works for me as well."

She smiled, patting his leg as they placed their order. She ran her hand around his back, having him shift a bit so she could extend a finger to hit the switch on the one being clenched. Dex swallowed as he tried to maintain poise in public as he thought everyone in the room could hear the vibration noise. Gem assured him she could barely hear it, so he was safe as long as he was a good anal whore.

They were turned off after they ate, Dex wanting to use the restroom, Gem telling him she didn't mind as long as he didn't touch either vibrator while in there. Dex argued there was no way he could sit on the toilet without doing so. She suggested he wait until they got home if he was going to be grumpy about it all.

Not able to get himself off, he took them home where he was instructed to use the toilet as he needed, while Gem opened the door to stand at the sink to brush her teeth. Dex wasn't happy with the intrusion but was told he was in a hurry so she suggested he do his business while she brushed her teeth so they could resume playing and experimenting.

He was embarrassed as he went, the two vibrators on the counter. Gem brushed, picking up the Listerine as he stood up to wipe himself. She openly watched as he inserted the vibrator into his ass before pulling up the panties. He didn't seem to know what else to do so Gem spit out the rinse, asking him if he planned on returning the vibrator in his hand back where he found it. Gem left, aware anal whore was placing the vibrator into the panties next to his erect cock.

For four hours straight she had him cleaning his house while she played off and on, anal whore rushing to her in hopes of a release rather than more cleaning suggestions. He had no sense of embarrassment by the time the four hours were up, he was doing as she suggested, wearing nothing but white granny panties, eager to keep her happy. Gem remained clothed the entire time, reading or checking out the house itself.

Cleaning done, she walked to him, pulled him to her, and kissed him deeply. Then she went to a table, grabbed the third vibrator, and returned to kiss him again, this time running the vibrator up and down his erection. Dex was lost in the kiss, not even realizing his orgasm was upon him until he shook with the intensity.

She left him lying on the floor where he collapsed after making sure he was breathing okay and didn't stroke out on her. He recovered enough in twenty minutes to see her sitting in the chair reading a book. As usual, she kept a brown paper bag wrapper around the book although Dex had seen the title earlier. It was just her way to know which book was hers as no one seemed to use homemade book covers anymore.

He knelt before her, thanking her for a fantastic time, his body reacting as she stood up, leaning over to kiss him.

"I have to do some cleaning of my own, so I'll see you later this week if you're looking for company."

He sent her a text before she made it to the stop sign at the corner. He remained only in the panties the rest of the day without any conscious thought of getting dressed or putting on boxers.

He was so sated, for the first time, he found no desire to turn on the vibrators and use them. The idea of being so sated by Gem left him feeling elated, seeking more time with this extraordinary woman he was so fortunate to be around.

Gem got home to find notice the landlord was raising the rent next month when her lease expired. Gem could either move or pay the higher cost. She nodded as she prepared for a shower. She had six weeks to plan on what to do.

They dated twice during the week, no actual sex involved as they had dinner and talked. Dex tried for more, Gem telling him to go into the restroom, hold his fork by his cock and take a picture of what kind of underwear he wore. He did so, the boxers showing in the picture. Gem elected to go to her own apartment after they strolled around after dinner.

The second time, Thursday night, he took her to dinner again, this time proving he wore the panties. Going to the park, they went to a dark area, Gem using the vibrators on him while he wore the panties. When he came, the panties darkened with the moisture, Dex so happy as Gem hugged him for a few minutes he didn't care his pants were at his ankles, his cum dripping on them and the ground.

They discussed plans for the weekend, Dex coming to her apartment to pick her up. She was still in her frumpy clothes from work while using her laptop. Going over to see what held her interest he looked over the page, discovering she was looking at apartments, mostly studios as they were less expensive.

When Gem came out of the bedroom, dressed for dinner, Dex as still previewing what she had. He looked up.

"Some of these places are as much as a mortgage."

"Yeah, well, I got six years of school to pay for and can't afford any of it. That was why I am looking at a studio. I own a suitcase of clothes and little else."

It was feasible since Dexter had no idea what her finances were but did know she graduated from college. He also did but his family already paid all the bills.

"I know of a great place." Dex told her as he shut down her laptop. "I have a three bedroom, two bath place which could handle someone else. Even got room in the garage for a car."

"Thanks, but you'd get bored with me before I was settled, and I'd have to find another place. But thank you."

The date consisted of him insisting he'd not be bored with her, adamant it would be great to share the house with someone he got along with and could talk to about almost anything.

The weekend showed he was eager to show her what he remembered of previous times, this time making Gem smile and hug him when he undressed to show pale yellow panties. If she was going to prefer him in panties, he thought two were not enough, buying a package of ten of pastel colors, all with a bit of white lace trim. Gem fussed over him for the surprise, Dex thinking he would have to have more ideas like this.

Saturday afternoon, Dex drove them to an adult store, amazed as he and Gem went in to see other types of vibrators. He had never been in a store like this before, the selection more than he ever thought as he and Gem, hand in hand, strolled around the aisles, looking at the packages.

The lady behind the counter was helpful, explaining about the double headed one for both users to fuck themselves at the same time, at the strap-on so the woman could have a cock attached to her, to artificial vaginas for those who tired of using their hands.

Gem openly dismissed the first two based on the cocks being too large for the ass being used. The lady brought out a strap-on kit, with four different sizes to attach and use. Dex had it set aside, Gem calling him an anal whore hopeful. He laughed but they went home with a large bag of goodies to use on him. At least he hoped she would.

Gem opened the strap-on kit, soaping and washing it before using it. The sight of her wearing the harness and screwing in a cock was enough for Dex to lower his panties to his knees, and bend over a chair, ass high for usage.

"Good grief, anal whore, two weeks ago you were happy with a hump and pump action. Now, you see a cock on me and you're almost ready to burst at the seams."

Dex looked to see he was semi-hard without being touched. He hoped the new experience was worth this excitement. Gem dipped the end of the cock into the jar of petroleum jelly, lined up, and pushed forward, the hole spreading to receive the latest intrusion. Gem soon moved into a rhythm, the cock buried deep, almost out, buried deep, almost out, buried deep and when he was used to it, she changed the rhythm while also adding a slap to his ass when she pulled out, smacking it each time she pulled out, thrusting hard each time she went in, the ass grasping for more.

Dex proved he was a happy anal whore, spewing on the chair without any touching of his cock.

"Stay still, anal whore, I'm not done fucking your ass."

Dex wanted to collapse but stayed up at her command. She kept thrusting, slowly rotating her hips against his now red spanked ass cheeks, the leather of the harness giving him a burn. He ignored it as his cock started back to life.

After cumming a second time, she withdrew completely, telling him to clean his mess as she sat on another chair a few feet away, watching him kneel and start licking whatever he found from the chair. He looked over to see her seated, still clothed, the cock pointing upwards from her groin. She grinned at him.

"Get it done and you can clean this before it dries."

He sped up his licking, checking for any signs of cum still around before crawling to lick and suck the cock that had been in his ass.

"Damn, anal whore, with that kind of suction power, I may have to fuck my pussy with this just to see you do a great job!"

He groaned at the idea.

"Happy to help with that." Dex said as he ran his tongue around the end.

Twenty minutes later, all rested and hydrated, Gem had Dex come over to her as she sat in a chair. Dex was still only wearing the yellow panties as she attached the harness to him, tossing a towel onto a comfortable chair before sitting at the edge, her dress at her waist, her trimmed pussy exposed to him.

Dex wasted no time, fucking her with gusto, not even thinking, as the harness rubbed against his own cock, he could be using his own to fuck her with. Gem came, her body shuddering with pleasure, her eyes closing a bit as she felt waves over her. She was still recuperating when she felt a tongue, opening her eyes to see Dex licking her juices from her pussy and thighs. She lifted her legs for him, Dex not hesitating as he licked her ass, probing her hole for more juice.

When he was done, she removed the strap-on, unscrewed the cock and without any fanfare, had him bend over, removing the one in his ass and inserted the slightly larger version into him. Dex was left on his hands and knees, panty just below his ass cheeks, enjoying this new sensation.

Gem moved in the following weekend, getting all her stuff inside before having Dex strip so he wouldn't work up a sweat as he helped her move in. She enjoyed seeing him in the pale blue panties, his muscular body moving boxes, helping her fill her new dresser and closet. All moved in, they celebrated by going to dinner before going back to the adult store where Gem bought a carrier full of items while insisting Dex browse other aisles. All were in a dark bag when he was allowed to pay for them, Gem grabbing the receipt so he couldn't see what was inside the bag.

Not knowing what she bought to use on him, Dex found he was excited about discovering what she planned. At no point did he wonder how she was slowly taking over his personal life, Dex wearing panties to please her, getting aroused when she simply started putting on the strap-on, happy to be naked while she remained fully dressed, elated as she had her mischievous look while telling him to do odd and end chores for her to watch as he did so. It no longer occurred to him to even question why.

Which was how he found himself later on his back on the bed, hands secured to the headboard with Velcro cuffs, his ankles above his torso also secured by Velcro cuffs to the headboard. He was happy he did workouts, so his back didn't ache too much.

Gem came in, still wearing shorts and tee shirt, a cock moving around in front of her. Without a word to him, her eyes dancing with the look he was hoping for, she slid the cock into his upraised ass, spanking it as she pumped in and out. Dex's cock was getting hard enough for her to pick up a canaster item, sliding it over the semi-hard cock and moving it as Dex found himself fucking an artificial pussy while getting his own ass fucked with a cock slightly larger than what he normally used.

As Dex closed in on a major orgasm, Gem asked if anal whore liked or love being in bondage for her, anal whore gasping a love for it, the same response to her other questions if he loved her spanking him, fucking his ass while he was in bondage. Dex could only gasp out his love for all of this, even a love for Gem for doing all this for him.

When he was really close, she stopped, the cannister moving off the hard erection bobbing in the air, the ass seeking to have more than just the tip as she stood still, letting him calm down. Then she did more, the action repeated several times as anal whore proclaimed his love for her all she did to him, how he was desperate to do as she wanted, to use him as she desired, not at all aware she was, for the first time, recording the entire action on the bed.

The more she asked anal whore of what he loved, the more he wanted more of what he loved, all geared for making Gem happy while she did was she wanted to him, openly having anal whore proclaim he loved doing what she told him to do, no matter what she wanted him to do, his voice begging her to do as she pleased with him, his body responding to the constant arousal and denial, his mind too mushy to understand what he was agreeing to do.

He finally came, screams of rapture as he came into the cannister, the straps pulling at the headboard, Gem concerned he was going to contract his muscles to the point the wood would crack. It was only after it was all over did she worry about his screams making his neighbors worry about what was going on.

Anal whore passed out, Gem releasing the Velcro cuffs which remained tied to the headboard, anal whore's legs and arms flopping onto the bed. She went into the bathroom, removed the harness, and came back with a warm washcloth to wipe down his cock and balls. She took the cannister back with her, allowing the cum to empty into a plastic container as she went back to the bed.

Ascertaining Dex was only passed out but otherwise ok, she read the instructions before attaching a metal tube to his cock, a mesh strap separating his balls. Going to the bathroom she saw copious amounts of cum draining into the container. Anal whore was going to be drinking a lot of cock cum in the next few weeks.

Then again, he was going to a lot of things in the next few weeks. He'd want the cock cage off, she'd tell him he was ahead on orgasms, and she wanted to even up the number. The cage came off when they evened up and went back on when he pulled ahead by more than three. Poor guy had no idea catching up would mean a few weeks at best, months at worse. Gem smiled at the sleeping man before her. No, not months, but she did plan on having him get more interested in what she wanted than he did now.