Dexter had a kink with no idea how to deal with it.
Dexter had friends, but no one to talk to about the kink. It started as a child, using his hand over and over for his pleasure, vibrators coming later after he saw an adult movie where it was used. He never tired of the pleasure he had.
In his teens, he had a few girls who wanted more than his personality, the acts being fumbles and messes without any pleasure for the girls. Dexter went to college where he had another opportunity with the same result. By the time he turned nineteen, he had to admit he loved using one hand to pump a vibrator into his ass and his other hand humping his cock.
In college a few girls wanted some fun, he would say he loved anal, the girls in each situation looking upset and taking off before he could tell them he loved anal in his own ass, not theirs. By the time Dexter turned twenty-one, he no longer had an interest in having sex with girls, aware they would think him a pervert and tell everyone. A few men as well tried since he had lots of girls around but never used them for sex, but Dexter had less use for guys than he did with girls.
Dexter could never talk to his parents or anyone in the family about sex while growing up and couldn't talk about his kink, his source of pleasure two or three times a week at least. He dated while knowing it wasn't going anywhere, but at least his parents' girlfriend pressure eased by showing interest to a girl.
His non-kink release was working out before going to work for the day, to sit at a desk all day, reading reports, doing meetings, and being bored. At the fitness center, he felt better as he did his routine and watched some of the women doing theirs. He only watched, never approached, so no one was worried, the women aware they were watched, a few times doing things to show off their toned bodies.
One morning he had a revelation. Four women were there every morning and after their workout, would shower, dress, and go to work. Well, three would. For some reason he never saw the fourth leave once she went to the woman's locker room.
It became a game for him to determine how she left as she wasn't an employee and the only two exits were in his line of sight. No matter, four worked out, three were dressed and leaving for work, the fourth not seen.
He suddenly realized why he never saw her exiting. He was seeking the one who did the workout, well-toned, beautiful, who kept to herself, doing her routines before setting a book on the treadmill to read as she ran, headphones on the entire time.
He finally linked her with the stoop shouldered, frumpy girl who left for work. He was so shocked he stopped to stand before her as she looked at him while moving around him. He moved in front of her again.
"I'm trying to get to work."
The voice was sexy, even toned, and a pleasure to hear. Dexter blinked.
"I have no desire to stop that, but I really want to know why the change?"
She looked at him and he explained she had a killer body when working out but, well, she was not the least sexy in her outfits. Why look that way? He was rewarded with a very nice smile and twinkles in the eyes looking at him.
"As a sexist pig, you like seeing the killer body. Thank you for the compliment."
He was almost offended being called a sexist pig, but she didn't seem to use it as an insult, so he let her continue.
"Simple, men at work also like the killer body. Most of the women using this asset don't go far without the men more wanting the body nearby than the mind capable of doing the work. Thus, I dress like this, the sexist pigs ignore my body and look at my work which so far has brought me some promotions and responsibilities some of the other women wish they had."
Dexter nodded, telling her it made sense. She smiled, walked around him, and left.
He waved goodbye to her each morning for a week before she finally waved back. Each night he hauled out his vibrator and thought of killer bodies and frumpy outfits while achieving his pleasure. He finally asked her out. She agreed, also telling him her name was Gem to her friends.
Dexter dressed with care, making sure the vibrator in his ass was secure, met Gem at a restaurant where he almost shoved the vibrator out of his ass at the beauty before him. She laughed at his reaction, telling him that was why she worked as a frumpy. He shook his head, guided her to a table and they talked for three hours.
It progressed quickly, kissing on the second date, cuddling and kissing on the third. On the fourth date, as they cuddled and kissed, he pulled back, aware he didn't want to blow this relationship but aware she'd toss him out if she found out. He couldn't do sex like normal, his cock wouldn't operate without a vibrator going in and out of his ass. He tried to leave, shocked as she shoved him into a chair, straddling him to keep him there. She demanded to know why he found her so horrible as to simply want to walk away without even an apology.
Dexter felt horrible he left that impression and told her about his kink before he realized he opened his mouth. She stood up, Dexter ready to rise to leave before she spit on him or cursed him. Instead she pushed him back down.
"Prove it."
Dexter could only blink at her. Gem shook her head at him.
"Prove you have a dick in your ass right now. Prove to me that isn't bull because you find me a horrible date."
Dexter found himself dropping his pants to his ankles, his boxers at his knees as he turned to lean into the chair, the black vibrator showing plainly.
"And that is comfortable?"
"Yeah, I'm kind of used to having something there."
He felt her fingers on his bare ass as she twisted the vibrator a bit out of his ass and then started pumping it in and out.
"It goes in nicely. Oh, a switch."
The vibrator went off as she continued to pump his ass. Dexter didn't hesitate, reaching up to stroke his hardening cock, his precum offering enough lubricant. She stopped halfway out, told him to not move a muscle if he wanted her to continue, walked away, Dexter holding his cock, hoping she'd return soon.
She did, tossing a bath towel on the chair before resuming pumping his ass as he started humping his cock. He let out a yelp of pleasure, his body shaking as he spewed his cum all over the towel. She kept up the pumping, instructing him to remain in position as she wasn't done. For the first time, Dexter was soon hard and coming a second time, his finish making him collapse to the floor, his deflating dick on full view to this beauty who was still fully dressed.
He looked up at her, her eyes twinkling with mischief, a smile on her face as she sipped her drink.
"That was cool. What else works for you?"
Dexter had no reply as he never tried anything else but laying on the floor, exposed to her as she stood above him, legs slightly apart, looking confident and assured, he wondered what was going on in her mind.
He admitted he only did the hump and pump aspect, not sure of what else to do. She tapped his deflated dick with the toe of her shoe and nodded.
"Not a problem, anal whore, I find this interesting. We will have to experiment."
Anal whore.
Dexter thought he should be insulted, angry at the name, but she said it with pleasure, not with a sneer. It was all new territory for him and the idea she wanted to experiment brought a wave of pleasure all by itself.
For the next few weeks they saw each other, Gem guiding the time together as she called him Dex in public but once at either his home or her apartment, she called him anal whore as a nickname, always with pleasure, never with a sneer so he accepted it as a nickname from her. When at her apartment, she fixed breakfast, asking casually if anal whore could get the bacon out of the fridge, Dex getting the plastic container out without hesitation. He was used to her pet name for him.
He also lived up to it, finding himself bent over as she used different vibrators he had at home on him. She called them cocks, Dex trying to explain he had no use for cocks in his ass, Gem telling him he may not, but she liked the idea of putting a cock in his ass, thus, she used cocks, and he could call them whatever he wanted. Dex would argue it more but when she used one in his ass and then another vibrator along his cock and balls while he was bent over, he lost his train of thought.
Dex woke one morning in his bed, Gem missing from the bed. He used the bathroom before seeking her out, finding her trying to operate his coffee machine. He told her it was on a timer, so she took him back to bed, this time telling him to lay on his back and pump his ass. She removed his dress shirt she wore to bed, Dex seeing Gem nude for the first time in all the times she saw him naked. With that mischievous look on her face, Dex wasn't sure what else she planned.
She used a vibrator on his cock, the erection getting to full staff. Straddling him, she inserted the cock into her pussy and slid back, Dexter's first experience of feeling a pussy around his cock. A hot, wet, willing pussy as she moved slowly back and forth, driving him nuts as he huffed and puffed with arousal while pumping his ass.
The vibrator in her hand went to his balls, back to his cock as she moved forward, and then to her clit as she moved back. For the first time, Dexter saw a woman get aroused, saw as she closed her eyes in pleasure, Dexter losing his mind at the sensations his mind and body was experiencing.
He exploded with the most intense orgasm he ever remembered having and almost passed out. He came to as she patted his cheek several times.
