Things are getting more intense.
After the botched date with Marie, I have begun to accept that my love life is basically going to be restricted to Katie and Charlotte milking me when they feel like it. And being their submissive servant.
It's different than when I fantasized about being dominated, but I am getting used to the routine. Charlotte's point about using orgasms and release from my chastity as a reward or punishment for good behavior has really worked. It's weird, like truly weird, but I can see it in myself. I am becoming more obedient, less rebellious.
Part of that is just accepting that they are in control. Part of it is not wanting to botch the chances of getting out of the cage and getting a hand job. And once I accepted I was no longer in control of my cock and my sexual urges, well... they've occurred less often.
I know I can get out of the cock cage if I want to. I big set of bolt cutters will do it. Or a hacksaw though I don't think that would be a good idea. I might even be able to slide my balls out from the clamp, though... I think I'd run the risk of permanent damage from that.
But if I do that those two lesbians will take it out on me in ways I don't want to imagine. Katie can be an incredible bitch and just hurt me for no reason. She loves to humiliate me. Charlotte is more methodical about it, using pain and pleasure to train me and shape my behavior, and it actually works.
If they lose patience with me, they will release the videos they have and the evidence they've gathered and I will be in jail for at least a couple of years and be a registered sex offender. So I leave the cage on. They are in control. It's getting easier and easier to accept as time goes on.
Katie is erratically mean. Ultimately, Charlotte is more dangerous.
A couple of weeks ago she came over to Katie's.
"Lenny, you smell. You have to take care of yourself better. Just because you wear a cock cage doesn't mean you can let your hygiene lapse. And Katie tells me you are not cleaning her toilet. You want to clean her toilet with her tongue?"
"Charlotte, please have mercy. I will clean more often. I will do her toilet. But... you know I might do a better job if I was allowed more orgasms. More than once every two weeks? Or maybe... you could even allow me to have a bit of sex, like real sex? I'd be motivated and sure to do a better job."
I was trying to negotiate with them. With Charlotte. I could see that she believed in the reward and punishment methods, and they had worked with me (I hated to admit it), and was trying to use that to my benefit. Maybe get some more freedoms by negotiating what I would do for them.
"Sex huh. So instead of a hand job you want actual penetration, I guess." Charlotte seemed to be thinking.
My heart leaped-- she might be considering it! And it seemed like maybe she was even considering being the one that would allow the penetration! I know Charlotte is bisexual, and she doesn't mind sex with guys, so maybe she would actually fuck me!! That would be such a win-win!
She looked at me kind of sexy, checking out my body (I was kneeling at the time). Her hands roamed and fingers touched between her legs. I could feel my cock getting hard in my chastity cage, which is never a good thing.
"You want me to fuck you?" She asked.
I nodded. "That would be wonderful, Charlotte. I... I had a date a little while ago but had to end it early because I couldn't... perform. You know. So. If you were to give me some relief, I know my behavior, my cooperation would be excellent."
Charlotte stood and ran her hands along my shoulders, touching me sexily. My cock kept getting hard and hurting and getting softer then getting harder and...
"You aren't thinking of actually letting that guy fuck you," Katie said. "You get his sperm in your pussy that will be the last time I eat you."
"Well... no... on the other hand, he wants me to fuck him," Charlotte said. "Hands and knees, Lenny."
I got on my hands and knees, disappointed. She was going to do another milking of me. Oh well.
The two girls left the room for a moment. When they returned, Charlotte was naked. Oh god, I've seen her naked before, several times in fact, but she is soooo incredibly hot. I turned my head away. Just seeing her breasts and pussy made my cock hard and there was noooooo room for it.
And.... while I was looking away, Charlotte did something. In another minute I felt something pushing against my asshole. Was it that awful prostate stimulator she had used once or twice?
She was kneeling behind me. I could feel her thighs against mine. Her legs on the inside of mine, pushing mine wider.
Katie sat on the sofa, legs crossed, watching me with an amused look.
The thing pushed against my asshole harder. It was much, much larger than the prostate stimulator they had used.
I grunted.
"Relax, Lennie. Push out-- it will be easier going in. It will hurt less."
I pushed like I was trying to poop, which did relax my sphincter. The object pushed further in. I moaned and groaned in pain, it was big, really big and spreading me wide and hurting.
"Charlotte, please... that hurts..." I begged.
She suddenly thrust with her hips.
As I screamed in pain from the sudden penetration, I realized what was happening. She was wearing one of their strapons, something the two girls used in sex sometimes. Charlotte was going to fuck my ass with a strapon.
I was being pegged.
Oh, fuck... I'd never been pegged before and I knew it could be exciting but this fucking hurt. Like the worst possible bowel movement one could have, and worse. The prostate probe they'd used before was tiny compared to this thing.
Charlotte shoved again and I yelped again. I could feel her naked hips pressing against my ass cheeks and I hoped the phallus had gone all the way in. But no... another shove and I grunted involuntarily. That dildo must have been the largest those two girls owned, and it was deep inside my rectum. It was displacing and pushing my bowels around.
"Ohhh..... fuck.... Please..." I begged.
"OK," Charlotte said and pulled back on the artificial cock.
"oh god oh god oh god..." I was panting when she shoved the cock back in, deeper.
I could feel my sphincter clasping the dildo, being stretched and pulled with each thrust. The insides of my rectum were protesting-- they weren't designed to take something this big.
Katie was sitting on the sofa in front of me looking on with a big grin as she saw me suffering. Behind me my asshole was being stretched and dragged back and forth as Charlotte slowly increased the speed of her thrusts.
The damn thing actually made me grunt, not just from the pain but from the way it fucked with my insides. I could feel it displacing and bumping and shoving aside my small intestines and kidneys as she fucked me.
Charlotte leaned down, laying on my back. I was in no shape to appreciate the feeling of her naked breasts squishing on my back, or when she reached around and began playing with my balls.
Well, I did feel that part because she squeezed them, adding ball pain to the pain in my anus.
"Please... please stop, Charlotte," I grunted and moaned. My voice quavered because I was on the verge of tears.
"Can't. Haven't cum yet," she said, panting a bit. I guess her aggressive hip thrusting was actually somewhat exerting for her.
But when would she cum? Wait? She couldn't cum, she was fucking me with a dildo! Was she actually getting off on this? How?
One thing was for sure, she had her hands on me, was pumping and pushing her hips against me, getting the cock as deep as she could, squeezing my balls until they ached, and it was going on fast and faster.
How long this went on I don't know, but it was a while and seemed like forever. I literally had tears streaming down my cheeks as Charlotte fucked my ass aggressively.
It ended when Charlotte had an orgasm. I was in too much pain to quite realize it but she grunted, moaned and began thrusting faster until she was panting and thrusting and then suddenly stopped. The dildo came out and I collapsed on the floor, curling slightly.
"Oh jeeze," Charlotte said. "I didn't think I would actually cum, but I did."
"I want to do it," Katie said. My eyes, which had been closed, popped open. Katie was standing up and stripping off her jeans. "I want to fuck the hell out of his ass until he begs for me to stop."
I moaned, and begged. "Please, Katie... my ass... it can't take it..."
"Get your own strapon," Charlotte said. "I am gonna use this one."
What she said didn't sink in until a few minutes later when Katie mounted me from behind. She'd gotten her own strapon and positioned herself behind me. I braced myself, hands over my head. Katie's cock went in a lot easier.
It went in easier for two reasons. First, it was smaller than Charlotte's. Charlotte had used the largest they had, and this one was a lot smaller. The second reason, well, I suspect my asshole was gaping wide open and loose from the fucking Charlotte had just finished.
Katie start thrusting. I started grunting and begging. I knew that's what she wanted, so I gave it to her, hoping to be released faster.
"Please, Katie. Fuck, that hurts. You are ruining my ass. Destroying it! Oh god, please! Please let me go!"
My begging made her fuck me harder, the cock thrusting into my rectum, in and out, fast.
Charlotte positioned herself in front of me.
"Suck my cock," she said.
I looked up at her, my head bouncing back and forth from Katie's thrusting behind me. She was holding the dildo from the strapon she wore, holding it for me to take it in my mouth.
"Oh, fuck..." I said.
Katie laughed and said, "No, I am fucking you. You need to suck her!"
I opened my mouth wide and took Charlotte's cock in my mouth. It was big and only went in partway. I'd never had a cock in my mouth, not even a fake one. This one was rubber and felt somewhat natural, and it tasted awful.
It took me a few moments to realize why. It had been in my ass and Charlotte had not cleaned it off. I pulled away and spat, still bouncing back and forth from the ass fucking Katie was giving me. Her cock was going in and out a lot easier, like it was lubed. I thought she had lubed it, though it wasn't like Katie to make things easier for me.
"Take the cock and suck it," demanded Charlotte.
"But it has shit on it!" I said in a yelp that was a little bouncy because of the ongoing anal abuse I was experiencing.
"It sure does. Suck it clean," Charlotte said and pushed the cock against my lips. "Now. Do it."
I opened my mouth, and the shit slimed dildo slid in. Now I knew what was covering it, the idea and taste was ten times worse. I gagged on the thing, had a terrible time taking it in. Charlotte seemed determined to pus the cock in as far as it would go, making me deep throat.
Well, I'd never sucked cock, much less deep throat. It didn't go far and I gagged and gasped and bile came up and the whole thing was fucking miserable and almost made me forget I was still being pegged by Katie behind me.
Thank god Katie got tired. Her heart wasn't in it the way it was in Charlotte's. Charlotte enjoyed fucking me, both from the sexual thrill and simply seeing me in pain. Katie enjoyed humiliating me but that got old quickly and she stopped.
When she pulled out she said, "Go to the bathroom, clean yourself up. You're bleeding."
I stumbled into the bathroom and sat on the toilet and watched as a steady stream of blood dripped from my anus into the toilet. Applying pressure with some toilet paper stopped the bleeding fairly quickly, but not the pain. My ass was bruised and wounded and hurt with a pulsing, throbbing pain.
After 15 minutes in there I slowly walked back out. The strapons were in the trash (I think they believed they were permanently diseased from having been inside me and should never be used again).
Charlotte and Katie were on the sofa, making out, fingers between their legs. I guess torturing me made them horny.
I glanced at the girls enjoying themselves and didn't bother getting dressed; I just walked out of the condo and over to mine, where I got some antibiotic cream and pushed that inside my ass as best I could.
It took a week for my ass to recover and heal. During the first three days I couldn't sit down at work, and had trouble sleeping. My boss even commented, asking me if I was OK. I told him I had strained my back and needed to be careful with it. I didn't want to tell him my two lesbian mistresses had fucked my ass to the point of bleeding and I was recovering slowly.