They sat in a restaurant, Gem and Dex laughing as they chatted with each other. Dex thought himself the luckiest man in the world, here with a beautiful, sexy woman who had a great sense of humor, intellect, and a creative streak, especially when it came to helping him experience his kink more and more.
Dexter March had, since he was young enough to find pleasure from his own body, loved anal. The problem was that by the time he was old enough to find girls, he was so used to pumping something into his ass while humping his hand, any attempt to do normal sex only made a disaster. He was resigned to know it would always be his ass and hand until he met Jemima 'Gem' Baxter at a fitness center.
He never thought of a relationship, but he liked her so well, he openly told her about his kink. She in turn wanted proof, got it, and since had helped him explore new ways to gain satisfaction. He loved his anal, she even called him anal whore as a pet name, but every week his orgasms seemed epic when she got done experimenting with some new technique. All she wanted as an equal number of orgasms.
Which brought them to the restaurant where she insisted they celebrate a full month of him having his cock in a metal tube. All he had to do to be free was give her four orgasms, so far he only managed to bring her off twice.
Then she did a prostrate rub when he complained, Dex getting a small orgasm out of it, but it still counted so now he had three to give her to get the tube off. As far as it taking a month, she did inform him all he had to do was give her an orgasm a day for four days and he'd be free of it. He wasn't sure why he always seemed too preoccupied to do so.
Gem knew why, knew the tube she put on him had qualities he'd like, such as vibrations she controlled with a remote, same as the vibrator currently in his ass. He usually used a vibrator with a switch, she used one with a remote so she could play with either side, driving him half nuts with arousal when the tube and vibrator both went off.
In the past month, Gem wasn't sure if her favorite anal whore knew what she was doing. If he did know she was slowly having him want to wait on her, give her more attention than himself, he didn't seem to care. Then again, when she used all these new toys on him, including bondage, he was at first anxious, but now accepted her actions.
She moved in to his house, officially taking over a spare bedroom, yet most nights she spent in Dex's bed with him. He was comfortable around the house nude or just in a pair of panties as a new normal for him while she dressed in whatever manner she desired. That he had to be on his hands and knees and use only his mouth to give her orgasms was a new normal. That when she appeared with the strap-on, he would automatically bend over a chair, offering his ass for penetration, a new normal.
Gem was happy with him, he was happy with her. Considering he never really had a girlfriend, never had anyone before who he could talk to about anything, Dexter thought of doing more with her. Gem wasn't interested in engagement or wedding rings.
"You keep playing and I'm going to dribble onto the chair."
Gem smiled at him.
"And there's a downside to this? I can't wait to hear it."
"You're evil, pure evil."
Nothing he hadn't told her several times. She was enjoying living up to his expectation of her being evil for him.
"You're a lot of work."
Dex smiled, aware of how she knew this. Even in the beginning of their friendship he was happy with his fucking his ass with one hand and humping his cock with his other hand. He never thought of other ideas until Gem did them, Dex usually just having to enjoy the sensations as they overwhelmed him while Gem did the ass pumping or cock humping.
"We could skip dessert, go home, and you could show how evil you are."
"We usually skip dessert and if you don't know how evil I am to you by now, you're too occupied with your own love of anal."
Exactly what Dex wanted, a chance to prove he was an anal whore who loved what she did to him. They left ten minutes later, dessert not even considered.
Dex was breathing hard as the cock slid slowly, too slowly for him, into his ass. He wanted to thrust but that only meant Gem stopped fucking his ass to spank him before resuming her own pace. At first, the spankings had been light, but as she did more over time, they got harder. By then, his warmed ass felt good no matter what kind of spanking she gave him.
He tried, but he finally started thrusting as his urges overcame what Gem wanted, Dex not aware that was exactly what Gem was waiting for him to do. Since establishing anal whore had no problem with being spanked lightly or harder as she currently did to him, Gem looked for many ways to make him do things she told him not to do. Right now he thrust back and forth quickly, his breathing deepening as it became more rapid.
Reaching under his hip, she felt moisture at the tip of the metal tube surrounding his cock, now sure he might have another orgasm even if it wasn't going to be the intensity he loved. She simply pulled out, donned a padded rubber glove, and smacked his ass cheeks five times each, the impact leaving an impression each time.
Then she centered the cock, putting on just the first two inches. Dex immediately thrusting for more, Gem simply moving off so only two inches remained.
"Nice try, anal whore, but you know better. You want option one or option two?"
She had to wait several seconds before his brain caught up with what was happening to him other than not being fucked in the ass.
"Wha.a.a.t? What did you ask?"
"I asked if you wanted option one or option two. You keep moving so I can't get a good rhythm to give you a good time."
That was a bald-faced lie although Gem wasn't sure Dex realized it. The fact Dex was so into anal and loved it so much, meant he was willing to experiment with Gem who only encouraged it. Gem liked the fact the more she experimented, the more Dex did as he was told, the more he did as told, the more she experimented. She could fuck his ass with the strap-on for a few hours, but she preferred he felt like he wanted to earn the privilege.
"What are the options?"
"One and two. Considering I'm still waiting for my own orgasm, you don't get any more details until we do the option."
She moved the cock so it was inside him for one inch, the gasping hole eager for more action. His ass started moving on the cock but not thrusting. Dex was aware now to not thrust when Gem didn't like it.
"Option one."
