Dear Mistress Elaine,

I happened to see your ad while I was browsing for -shall I say- a particular type of encounter? I’m interested, my name is Alison Tailor, but please just call me Allie. I’m not particularly experienced with BDSM, though, if I were to speak bluntly I might say that this wouldn’t be my first time getting tied up. I apologize if this email is worded strangely or way too formally, I promise I’m not stuffy or weird in real life. Anyway, I’m not entirely certain how is supposed to go, but, I’d like to become one of your clients.

Kind regards,

Allie Tailor

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Dear Allie,

I wouldn’t sweat the word choice, email etiquette when asking for fetish service isn’t exactly a thing. You would be amazed how many emails I get, mostly from men,  that consist of little more than a time, a place a price (usually lower than what I ask for) and dick pic. Honestly, it’s like they don’t even know who’s in charge. So, you have nothing to apologize for. Also, if I’m being honest, I find your need to justify your word choice quite cute. If you ask me, it suggests a certain air of insecurity, and I’m very good at making sweet girls like you feel more secure. Attached is a spreadsheet containing my schedule, as well as a list of prices for my services. Please do fill it out at your leisure and provide a picture of yourself, so I know with whom I’ll be toying. I look forward to the first of many meetings.

- Mistress Elaine

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Mistress Elaine,

I’m really sorry to bother you, but I don’t see the pricing on this spreadsheet. Is there maybe another attachment not included?

Regards,

Allie

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Mistress Elaine,

I found it, I’m sorry. I forgot to check at the bottom for other tabs. I always do that. I’ve attached the filled out version of the spreadsheet here. Forgive me for questioning you.

Regards,

Allie

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Allie,

Your apology was cute, but do bear in mind that I’m a real person. I’m not some iron willed cruel dominatrix 24/7. If I’m being honest, even to my clients I’m not that cruel, unless they ask me to be. You’re allowed to be human around me. Unless, of course, you’d rather be something else. Perhaps a sweet kitten or obedient puppy? But, I’m getting ahead of myself. The time you’ve suggested sounds good to me. I’m excited to see what you’ll have me do to you.

- Mistress Elaine

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Dear Mistress Elaine,

That was wonderful, really. I’m not exaggerating here just wow. Thank you for being so patient with me and all, I know at the start I was shaking like a leaf but you really helped me feel a lot better as soon as things got started and also wow, it was really hot. You’re really hot, and also talented and okay it feels weird going on about you like this but it was super, super fun and I’d really like to do that again if you can send me your schedule for maybe two weeks from now? Also, I just wanted to say thanks for being nice and easy to talk to outside the ropes too. I was nervous you’d be all business, but you were really fun to talk to. Also the aftercare. Thank you for that. I really needed it and it was really nice. I’m rambling now so I’m going to cut this short. See you again soon, hopefully.

Warmly,

Allie

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Allie,

I’m glad you enjoyed it, genuinely. Part of the reason I became a domme to begin with was to make people feel good, physically and emotionally. It’s a breath of fresh air from my day job that’s for certain. But I digress, I’m very glad you felt safe enough around me to let me do all that to you. And also, by no means is it weird for you to compliment me, in fact I think it’s quite welcome, please do go on, sing my praise like you did the other night. I’ve earned it, after all. And, for the record, I found you to be a great conversationalist as well. It’s nice to have a client who can do things other than act as a foot-stool (though I wouldn’t be opposed to that with you.) Attached is the schedule. I look forward to our next meeting.

Tantalizing,

Mistress Elaine 

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Dear Mistress Elaine,

Here’s the schedule. Also, okay I can compliment you some more. For one, you’re really attractive. That long dark hair of yours goes very well with those stunning green eyes. And your skin is just so gorgeously smooth and practically luminescent. Honestly I don’t know how you’re that pale without being pasty but it works very well. And those muscles, holy crap. I wasn’t expecting you to be as wiry as you were but wow, I kept thinking about how you could easily just pick me up and throw me probably, if you wanted to. Also from what I could see you have a really nice figure. Anyway, looking forward to our next session.

Warmly,

Allie

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Allie,

That’s quite enough on the flattery. Not that I don’t appreciate it, but I was kidding when I requested compliments. I look forward to our next session.

- Mistress Elaine

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Mistress,

Did I get you a little hot under the collar with that email? Is my Mistress really that easily flustered by a pretty girl saying nice things about her?

Allie

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Mistress,

No response? Well, that’s fine. I’ll see you next week.

Allie

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Dear Allie,

I know I told you this in person, but I can’t stress enough how important it is that we keep what happened last night between us. I am not a prostitute, anything resembling sex is not something I offer to my clients, officially or unofficially. In fact, in a strange way I feel almost guilty or manipulative for even having agreed to have sex with you. I hope you understand that while I made an exception for you in the heat of the moment due to our rapport, this is not something that should leave the bedroom, and I must insist that if you feel at all taken advantage of or misled that you tell me here and now. 

Regards,

Mistress Elaine

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Elaine,

Listen, I know you’re beating yourself up about all the stuff that happened last night, but I promise you that you didn’t take advantage. If anything I took advantage of you, I’m the one who asked and also the one who insisted we share a few glasses of wine before starting. So, I’m sorry about that. If you don’t want to see me again I understand, but, well, I’ve really enjoyed both our sessions so far as well as our correspondence. I hope we’re still on for next week like we discussed in person. And, well, if possible I’d like to have sex again. If you won’t do that as Mistress Elaine, I’m happy to meet you as just regular Elaine for it.

Warmly,

Allie

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Allie,

I appreciate you saying that, thank you. As long as you’re aware of how unorthodox it is and will not go spreading the word, I am okay with continuing as we have. I am uncertain whether I’m comfortable engaging with you like I did last time once more, but I would be lying if I said I didn’t thoroughly enjoy myself. I would be lying if I didn’t say what we did was a much needed breath of fresh air to pull me out of a certain funk I’ve been in for some time now. We’ll talk more in person. I look forward to next week.

Best,

Elaine

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Mistress,

You continue to wow me. I have some personal affairs to attend to over the next several days, but I’ll be in touch.

Your slut.

Allie

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Allie,

I’m glad you enjoyed yourself. You know the drill, keep things quiet. And please, please tell me if at any point you feel I’ve taken advantage, even if it’s days after a session.

Regards,

Mistress Elaine

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Mistress,

Guess who’s free? Got times available next week?

Allie

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It’s good to hear from you Allie, see schedule attached. Sorry for short reply. On mobile.

- M.E.

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Elaine,

Thank you once again for last night. Also, thanks for agreeing to go out with me I guess? Is thanking someone for that weird? Probably. Either way, I hope you know I’m really, really, looking forward to our date. If I’m being honest, I’ve liked you for some time, I get the feeling you have too. 

Yours,

Allie

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Allie,

I would be lying if I said I hadn’t liked you for some time as well. I suppose it was obvious from the moment I agreed to sex with you that this wasn’t just a regular client/mistress relationship. While I’ll miss the extra income (especially the tips), I’m glad we can move this away from the dubiousness we were in before. See you next week.

Warmly,

Elaine

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Allie fuck I’m so sorry. I know you’re not gonna be able to read this but I just I need to talk to you and I can’t and it wasn’t supposed to be this way. I’m so stupid I fucked up so bad I was supposed to get you off and they’re taking you away from me and I can’t. I just. Please, please please please hang tough. I don’t know what to do I’ll find some way to save you and then you can hate me forever that’s fine I probably deserve it but please please please be safe and alive and okay in there.