Celebrate Locktober and No Nut November with a chasti­ty enthu­si­ast who pushed his lim­its to answer the ques­tion: how much servi­tude is too much?

Follow this man on his exper­i­ment of pleas­ing five mis­tress­es — what excit­ed him and what he learned from it.

I usu­al­ly don't accept guest posts but make excep­tions to show­case oth­ers' unique per­spec­tives — like read­er tes­ti­mo­ni­als and tales from male escorts and submissives.

Enjoy!

In many kinds of sex play, you're encour­aged to try more. More toys. More posi­tions. More fetish­es. More every­thing. For me, a lot of this explo­ration comes from my male chasti­ty pledge. If Mistress wants to try tying me up, who am I to stop her?

Usually, you'll find one and stick with them for a while (or for­ev­er), then move on to a dif­fer­ent one. If more is always bet­ter, then sure­ly more Mistresses are bet­ter than one?

I decid­ed to find out.

Mistress One – The Standard Chastity Experience

My cur­rent Mistress is Mistress Tracy. We both write for Lock the Cock, so our con­ve­nient arrange­ment lets us share and test kinky ideas.

Even though­mosty of our rela­tion­ship is pro­fes­sion­al, she doesn't let me off the hook when we leave the office. I'm her slave, and like any good Mistress, she takes full advan­tage of that fact.

In an aver­age week, my respon­si­bil­i­ties to her can include:

• Shopping trips.
• Preparing her house for vis­its from oth­er men.
• Pleasuring her sexually.
• Cleaning and housework.
• Cooking meals for her.
• Helping out her friends.

All in all, it's pret­ty stan­dard stuff for any­one into chasti­ty. Mistress is in charge, and it's our job to keep her hap­py. Fail, and she won't hes­i­tate to dish out punishments.

Finding a Second Mistress

When I first pitched the idea of hav­ing mul­ti­ple Mistresses to Mistress Tracy, she wasn't par­tic­u­lar­ly pleased (and nei­ther was my penis by the end of the day). She ini­tial­ly con­sid­ered it an insult, think­ing that I was say­ing she wasn't good enough, dom­i­nat­ing enough, or keep­ing me busy enough.

That high­lights the first issue with the exper­i­ment. In male chasti­ty, you're expect­ed to serve or even revere your Mistress. But how can you real­ly do that if you're divid­ing time between dif­fer­ent ones? Maybe that's why I've nev­er seen any­one try this before.

Either way, when I was final­ly giv­en per­mis­sion to explain myself, I laid out the plan. It was an exper­i­ment, not a per­ma­nent arrange­ment, and she'd be involved through­out. A smirk flick­ered across her face as she agreed. One that made me shudder.

Naturally, she already had a few Mistresses in mind, so a few phone calls lat­er, every­thing was set up.

Mistress Two – The Submissive Sweet Spot

At first, hav­ing two Mistresses wasn't any­thing extra­or­di­nary. For the most part, I did the same things I did for Mistress Tracy, but twice as much. It wasn't until a few days in that I start­ed to real­ize the ben­e­fits of this kind of arrangement.

Submissive men like to serve. It's fair­ly self-​explanatory to any­one who's been around the chasti­ty fetish. However, a part that often goes undis­cussed is how much men like to serve. Usually, Mistresses want time to them­selves. To go out with their friends. To fuck oth­er men. Naturally, this means that they aren't pay­ing atten­tion to their slaves.

So what does a sub­mis­sive man do when there's no dom­i­nant in sight? Well, pret­ty much what you'd expect. Going to the gym, doing hob­bies, or in my case work­ing at Lock the Cock. But for some of us, this time is a bit like a wait­ing room, and all we real­ly want is to get back to serv­ing our Mistresses.

With two, this isn't as much of a prob­lem. The night I fin­ished plea­sur­ing Mistress Tracy, only to be imme­di­ate­ly sum­moned to my sec­ond Mistress to per­form the exact same ser­vice, was one of the most thrilling of my life.

Mistresses Three to Five – How Much Is Too Much?

After a week of serv­ing two beau­ti­ful women, I was some­what wor­ried about adding the third. Meeting all of their demands was sure to be a challenge.

It was gru­el­ing. Every wak­ing moment was spent meet­ing the needs of my three Mistresses. There was no time for rest — no time for recov­ery. That was sub­mis­sion in its truest form.

Weeks three and four saw two more Mistresses tak­ing the reins, and it was clear that this was far too much for one slave to han­dle. The pun­ish­ments became more severe as I lagged fur­ther and fur­ther behind in my tasks until I was prac­ti­cal­ly at break­ing point.

Unfortunately, it wasn't over yet.

As a final cel­e­bra­tion of my com­plete and total fail­ure to keep all five Mistresses hap­py, they con­spired togeth­er to deliv­er one final ver­dict that I'd remem­ber for­ev­er. By the end of the night, my tongue was exhaust­ed, my fin­gers raw, my cock throb­bing with desire, and my ass bright pink. They may have been sat­is­fied, but I def­i­nite­ly wasn't.

So Are More Mistresses Better?

It took a while to sort my thoughts after the expe­ri­ence. While five Mistresses were def­i­nite­ly too much to keep hap­py, my fail­ures did lead to more pun­ish­ments and a night that I'll prob­a­bly nev­er expe­ri­ence again. If this became a per­ma­nent arrange­ment, then per­haps the low lows would be bal­anced by the high highs?

I think this set­up isn't often dis­cussed, though, because it sim­ply didn't add any­thing to the chasti­ty expe­ri­ence that you can't do with just one Mistress. Almost every­thing that can be gained by adding more Mistresses can also be achieved by your Mistress sim­ply invit­ing friends to be part of your chasti­ty dynam­ic. While her oth­er part­ners are plea­sur­ing her, you can be plea­sur­ing her friends. While she's spend­ing time with a group of friends, you can be serv­ing them all drinks.

There are plen­ty of ways to add more sub­mis­sion to a chasti­ty dynam­ic (we dis­cuss plen­ty of them in the Lock the Cock blog), but I think more Mistresses just isn't one that I'd rec­om­mend to others.

About the Author: Andrew Schroeder

Our guy walk­ing the walk, Andrew is a long-​term cage wear­er who found LTC when shop­ping for devices ear­ly in his jour­ney. So he's gone from cus­tomer to consultant.

He taps out arti­cles that dis­cuss the lifestyle. From debunk­ing myths to offer­ing com­men­tary on the most-​debated chasti­ty top­ics, Andrew S is inspired to write because of his ardor for the caged life.

“Pardon the pun, but there's a lot of cock and bull infor­ma­tion about male chasti­ty and the peo­ple who par­take in this lifestyle. My want, and why I write for LTC, is because I believe we need more straight-​talking, expe­ri­enced voic­es to speak up about their jour­neys with chasti­ty. People who are famil­iar with the lifestyle and com­mu­ni­ty. People who want to help those who are new and interested."

This is a spon­sored guest post.

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