I Am Going to Help You Pt. 03

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More adventures in chastity.
759 words
4.28
7.2k
4

Part 3 of the 4 part series

Updated 06/15/2023
Created 04/17/2023
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"I am going to help you. Do you trust me?"

Why shouldn't I have? Besides the fact that I had forgotten her name. And that I had only met her a few hours before, and we were already in bed. She had cum three times, I hadn't. She wanted me to. I wanted to and would have done almost anything.

"Good," she said, smiling, as she crawled down to my crotch.

She removed the condom and tossed it away before diving onto my cock. Oh God! I thought as she enveloped me. I was overdone and needed release. It was like she knew exactly what to do. She brought me closer and closer...

"I am going to..." I moaned.

"Good!" she repeated, barely stopping before diving back in.

That little delay held me back a second, but only just. I was getting closer and closer and...I exploded. She just kept going until I finished my release and sunk back.

"That was..." I started as she rested her head on my chest.

"Yes!" she said. "Again?"

Again never stopped. That was five years ago, and we were never far apart since. Over the next few weeks, I learned her name was Carol, making sure never to forget that, and a lot more. She was the perfect woman for me. She was just perfect in every way. Even today when she laments that being over 30 is the beginning of the end, I truly believe every word when I tell her that she just grows more beautiful.

Everything about her is perfect. Her shoulder length brown hair. Her perfect green eyes over a perfect smile. Even her pouty face just melts me. And to be blunt, her perfection goes down even further. Imagine the most perfect set of tits you can. Hers were better.

She knew I jerked off with pictures of her. She even supplied them. When we finally moved in together, she simply offered to help if she caught me. More often than I cared to admit, she also finished me off with her mouth after sex. It was a double-edged sword. I took so long that she was willing to forgo condoms. I didn't complain. But I knew she wanted me to finish naturally more often.

If you've followed my tale, you might see where this is going. If you haven't, you should know that for the last month, I have been locked in a chastity cage after Carol caught me masturbating at the wrong time and place. She kept the key in a chain around her neck, dangling between her breasts. In the last month, she unlocked me six times. A weekly washing, and twice to quickly jerk off. The first time I came in minutes. The second, she decided I took too long and made me lock back up.

"How long will this last," I asked her as I threw back another drink.

It was Wednesday, date night of sorts. Before that meant drinks and drunken coupling. Now, it meant drinks and me eating her out to a few orgasms before she ground against me in my sleep. Torturing me.

"It is starting to grow on me, Mark" Carol said with a smile. "But I think maybe you have earned your lesson..."

With a kiss and with a great big smile on her face, she led me to the bedroom, every few feet she removed some clothing until we were both naked. Except for my cage and her key.

She removed the key, unlocked me, and put the cage on her pillow. I needed no encouragement. I kissed her and thrust my cock into her. I was more than ready.

"Slow down there, big boy," she moaned before resuming our kiss.

I respected her and slowed down. But I was in need. This wasn't love making. This was fucking. I needed to fuck her. And fuck her hard. I was getting closer and closer and....

She came. "Oh, God! Oh, God! Oh, God!" she moaned.

I had rarely made her cum twice in a row like that. I was in heaven. And was getting closer and closer and....

"That's enough!" she yelled as she pushed me off, and out.

"What?" I cried.

She smiled, kissing me, deeply, passionately. We held the kiss for ages, but the whole time she was holding me back.

"I am going to help you. Do you trust me?"

"Of course"

"Here you go!" she cooed as she broke our kiss and handed me my cage back. "We should do that again!"

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3 Comments
AnonymousAnonymous4 months ago

The flashback at the beginning of this SHORT chapter confused me at first.

Now when she teased and denied him, he protested of course. But if he puts the cage back at her request then he HAS consented. Else he is soft in the head. J.

InfiniteXaosInfiniteXaos7 months ago

Seriously? She hands it back to him? Yeah I'd be done with her. She asks him to trust her but doesn't in return.

AnonymousAnonymous10 months ago

Oh fuck that bitch you don't get to lock me up for a month, then when were fucking hot and heavy, tell to me to stop fucking you when I'm about to Explode. Oh fuck no that's not happening, you Shove back into her pussy with all your might, bottoming out hard, then Continue tell you cum in the her pussy. Then you roll off her and start packing your bad to get the hell out of there..

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