Things have become much more routine, regular.
Ever since I accepted that my relationship with Katie and Charlotte is all I will have, that I can not have dates or a girlfriend, things have gone easier. My relationship with those two girls, as kinky and weird as it is, is more than a lot of guys have. Both girls are gorgeous and I spend more time around them than any other girlfriend I've ever had.
Katie and Charlotte are sharing me more and more. It's about 50:50 right now. I go next door to Katie's three times a week, after work. I go twice to Charlotte's after work, and then once on the weekend for the day. I serve the girls in their homes while there, in whatever way they desire.
Usually it's domestic work. Cleaning. Cooking. I've actually gotten a lot better at cooking, though the process was painful. Charlotte was the one who demanded that I start cooking for her. I cooked spaghetti or made chili, the two things I know how to do well. I tried a chicken dinner and that went over terrible.
"Lennie, this chicken is tasteless, plain, and dry. And these potatoes? Did you make them from powder? Fuck... Lennie, have you ever cooked in your life? For this failure, I must add a week of time to your chastity schedule."
Charlotte has a schedule for me now. Once a week I am let out of chastity and one of the girls will make me cum. Milk me like a cow.
There's a specific method they use. I am already naked of course. At the designated time and at their command, I get on all fours and spread my legs. I wait their pleasure in this position.
Either Katie or Charlotte inspects me, checking to see if my anus is properly cleaned, and then checking my balls. If I am not clean enough, they postponed the milking for a day. As a result of this schedule, I keep my anus very clean, washing it thoroughly with soap and water. Same with my balls.
If I pass inspection, Charlotte will remove the cock cage. My cock usually springs to life right then, hard and ready. But they won't milk me right then, much of the time they do something else, leaving me there, hands and knees, cock hard and waiting.
One of them comes over. Katie wears gloves when she milks me, Charlotte doesn't.
They use a sort of butt plug / dildo on my ass to get me ready. It has a curve on it so it presses against my prostate, hard. It's a weird feeling, sort of arousing but very sensitive. After precisely one minute of pumping on the prostate dildo, whomever is milking me will begin stroking my cock.
I then have three minutes to orgasm. I am expected to cum, to ejaculate, within that time.
It's not that difficult, usually. After a week of being caged and not able to play with myself, being around Katie and Charlotte, naked, free of the cage and ass fucked with that prostate dildo... I cum pretty quickly.
There's a crystal glass that Charlotte brought just for my semen. I must ejaculate into that. If I miss or spill a drop she will personally whip my ass until it is black and blue and I can't sit down for a couple of days. I've learned to make sure I get my semen into the goblet.
When I am done, Katie or Charlotte will pour the semen into my mouth. I am expected to hold it there while they inspect, and then swallow and show it is all clear.
Then my cock cage goes on for another week.
If I do well, that is.
Normally I am milked at 8 PM in the evening on Wednesdays. That's my time.
If I fail in some way, displease either of the girls, they add time to my chastity, usually in increments of a day. When I made that bad chicken dinner, for example, Charlotte added three days to my chastity cycle.
The worst I had added was two weeks. I missed a night at Katies. I had to work late, I had no choice. My boss told me to work late. I texted and informed the girls I would be late. Katie texted back and told me if I was going to be late, don't even bother. She added two weeks to my chastity / orgasm cycle right then.
Three weeks without being milked. It was miserable.
When she finally milked me, she didn't go through the ritual. Instead she had me ejaculate into the toilet.
Honestly, I don't understand why but that was more humiliating to me than anything. Katie milked me, but told me my semen was worthless and was to be sent into the sewer.
Charlotte and Katie have also begun to let me watch... or force me to watch, depending on how you look at it. I can't touch myself, and watching them makes me hard, which is painful inside the chastity cage. They do this once a week now, on Saturdays.
Each Saturday evening after cleaning the house, I am tied to a chair and left there. Usually Charlotte and Katie go out, maybe to dinner and a movie, or clubbing (they like lesbian bars). I sit in the chair bound, unable to move or go anywhere. Charlotte especially loves to tease me a bit before leaving me there.
I'm given a chance to relieve myself first, thank goodness. Otherwise I would end up peeing in the chair and I'd get punished badly for that. They have another special way of preparing me for my Saturday night in the chair. A different chastity cage.
This cage is weird-- Charlotte found it online and got one that fit me, sort of. It's a metalic tube, not as tight as my usual cage, but it has spikes on the inside. Sharp ones. Any big movements will cause my cock to get pierced, and of course, any kind of erection gets very painful very quickly.
The cock cage also has a tube that gets inserted into the tip of my cock and up into my urethra. That metal sound goes a couple of inches up my cock and effectively plugs me up.
The sound part, the metal tube in my cock, is hollow and will allow pee to drain through if I release it. The thing is designed for long term use, which is terrifying.
Katie has threatened to make me wear it full time.
It's a truly evil device.
Once on, the spiked cage has my cock poking straight out, but not erect. Any erection becomes immediately painful. The first couple of times they put it on I bled from the inside until my cock learned not to get hard, not even a little bit.
The tube inserted into my cock has a cap on the end that can be screwed on and unscrewed. This can prevent me from urinating. Katie always leaves it on. It never comes off. I am not allowed to urinate when wearing this cage.
So each Saturday night I sit in the bondage chair starting from about 5pm. I wait for the girls to come home, wearing my spiked cage, trying to make sure I don't think about them or any other girl and stay as soft as possible. My wrists and ankles are secured and I can't go anywhere but sit and wait for them to come back from where ever they go.
They come back, usually in a good mood, and usually drunk. And fall into bed. That's where the "watching" comes in.
It fucking hurts to watch them. I can't help it, it does. Those two girls go at it like they are in heat. Fingers, tongues, lips, toes, breasts, whatever. And then the toys... omg they have toys. Double dongs, dildos, vibrators, strapons-- and the latest. What they call a feeldoe.
It's a strapless dildo. One end is shaped like a small cock and goes up inside the girl that is the fucker. The actual dildo is larger and the fucker fucks the fuckee with it. No straps, the insertion keeps it in place and is also a way for the fucker to feel like she is being fucked.
It even has a vibrator in it.
It's like watching the best live porn you've ever seen. And I can't help but get hard, the spikes drive into my cock and I sit and moan in pain, whimpering, as Charlotte is laying on her back with her knees up and Katie thrusting into her, grunting as she does.
They love the fact that their sex is causing me pain. They giggle and laugh about it after they fuck, and take a look at the little trickles of blood that are seeping out of my cock cage.
Then they do it again.
I've begun to think about raping them. Some day. Somehow. Some way I will get even with them, tie them up spread their legs and fuck them until they are sore and bleeding and begging for mercy.
For now... I sit and bleed and beg for mercy instead.