Becoming Hers Ch. 07

"Yes, please. Put it in," Alex whimpered. She laughed and started working two fingers into his ass. Once she felt him relax, she took her fingers out and put the tip of the purple cock against his entrance.

"Beg," was all she had to say.

"Please. Please fuck me in the ass." Alex begged without hesitation. He had no shame and knew what she wanted.

Karen laughed her cruel laugh and obliged, sliding the head of the strapon into his eager asshole. It was bigger than her fingers, but Alex delighted in the full feeling as she slowly worked it in. It went far deeper than her fingers ever had before, but she took it slow and gentle, giving his body time to adjust.

"Look at that hungry asshole," she said as she bottomed out. Alex could only moan in response as he felt her hips press into his behind. She put her hands on his hips to steady herself and started pulling back. Alex could feel the emptiness where her cock had been, but it was quickly filled again. She wasn't used to being the one fucking, so it was a bit awkward at first. Still, the end of the dildo teasing her clit kept her going.

Soon, she was fucking Alex's ass with a steady rhythm. His long-forgotten cock was rock hard and bouncing back and forth as she pounded him. The feeling of her hips hitting him as she bottomed out was incredible. He felt it through his whole body. He had never been fucked like this before, and his brain was struggling to process it. Like the vibrator on his chastity cage, he knew it felt good, but didn't really understand it yet.

After a while, Karen had him lie on his back and lift his legs. He felt as vulnerable as before, being so exposed, but welcomed the feeling of the dildo pressing against his ass. Karen watched the expression on his face as she slid the cock in easily.

"Ohhh, that's adorable. You blush when you get fucked," she said as she kissed him. This made him blush even more. Karen started fucking him and grabbed his lubed up cock. She slowly jerked him off as she fucked him, enjoying watching how blissful his face was.

Alex was ready to cum in seconds, but Karen stopped before he came. She wanted to fuck him a bit longer. Using the strapon was challenging for her, but she was still enjoying herself. She leaned in so her face was over his. "Fucking you like this," she said, "really makes you my bitch."

"I guess it does," Alex said, smiling. His face was still flush, and his body bounced with every thrust of her cock.

"Open your mouth, bitch," she said sweetly. Alex did so, letting her spit fall into his mouth as she fucked his ass. He thanked her after swallowing, which made her so happy that she kissed him deeply and possessively as she buried her cock in his ass. When she had enough of fucking him, she started jerking him off again.

"Pretty please may I cum?" He breathlessly asked.

"And what if I say no?" she asked.

"I wouldn't cum?" Alex asked. She could see the panic in his eyes and loved it.

"You may cum," she said.

Alex's whole body tensed as he came. Karen never stopped fucking him, and he could feel his asshole tighten around her cock as he convulsed, sending jets of cum all over his chest. He cried out in pleasure as she kept pumping his cock and his ass, draining him of two weeks of pent up frustration. By the time he was done, there was a trail of semen from his chest to his cock.

Karen kept fucking him slowly as she fed him his cum, which he eagerly ate. When he was done, she slid the purple cock out and gave him a kiss.

Karen took off the strapon and laid back on the bed. She spread her legs and said, "I hope you don't think you're done yet." Alex could see how wet she was and didn't need any prodding. He dove right in.

He could taste and smell the mixture of sweat and pussy juice as he lapped it up. He was where he belonged, servicing Karen. His needs were met, but he needed to make sure hers were too. Karen came quickly, having been teased for so long by the strapon. When she was done, she had him go shower. By the time he came back out, she had cleaned up the room and was ready for bed. They kissed and cuddled into a blissful slumber.

—

The next morning, Alex was still uncaged. He wasn't sure how to proceed, since they still needed to talk about their arrangement. Karen didn't bring it up in the morning as they got ready for work, so he decided the time wasn't right. When he got home from work, she was already waiting for him.

"It's been two months," she started. "We should talk."

"Yeah, we should."

"So, what did you think?"

"Well, what did you think?" Alex asked, blushing. He wasn't sure how to tell her what he was thinking.

"I liked it... a lot. But I want to be sure you're okay with it."

The conversation went on awkwardly for a bit until they both admitted that they liked it. Neither one wanted to seem too eager, but Karen admitted she liked being able to cum whenever she wanted and Alex admitted he really liked having her take charge.

"So, you're sure you want to keep going?" Karen asked.

"Yeah, but let's not do it forever. Maybe another six months and then check in?"

"Sure, that works for me," she smiled. "I thought you'd say yes, so I got you a present." She said as she handed him a small wrapped box. He tore open the paper, opened the box, and found a metal chastity device.

"It's sized to you," she said. "I had to guess on the measurements, but I'm pretty sure it's right. Go, try it on!"

Alex took the device and went upstairs to put it on. It took a couple tries, but the design of it was good. It was a series a metal bars encasing his cock, and was perfectly sized so he didn't have space at the end of the tube, unlike the plastic one. It didn't give him room to grow, but it would make peeing a lot easier. When he came back out, Karen was in the bedroom waiting for him.

"It looks nice! It should be easier to clean than the old one, and the stainless is medical grade, so you don't have to worry about it smelling."

"That's... good," he said.

"Since you'll be wearing it all the time."

"Oh, I see. Right."

"So do you like it?"

"Yeah, it's nice." He said, less than enthusiastically.

"You miss the pink, huh?"

Alex hesitated for half a second before being honest. "Yeah, it grew on me more than I thought it would."

"Take a look in your underwear drawer."

Alex, confused, did. Inside, he discovered his boxers had been replaced with panties of all types. Some were plain cotton while others were more skimpy and sexy. There were even a few thongs.

"I thought you would be a little disappointed. I liked you being cute and just a little girly, too. So now, when you're in chastity, you can wear those. I put your boxers in the basement in case you're ever out of chastity — which I doubt will happen much."

Alex was surprised at how happy he was to see those. He hadn't realized how much he liked that little bit of girliness, considering how humiliating it was at first.

"Go, put some on," Karen suggested.

Alex picked out a pair of red satin panties and slid them on. The feeling of the soft fabric on his legs quickened his pulse, and the way it hugged his package somehow felt right. His chastity cage was a small bulge in the front and he could feel the soft fabric between the bars. His cock tried to grow, but it didn't get far in the new cage. The steel was much less forgiving than the plastic had been.

They kissed as Karen massaged with his balls through the fabric. "Those look good on you," she purred in his ear. "But I'm home from work and you haven't given me my foot massage or made me cum yet. Do you want to cum at all in the next six months?"