Thanks for feedback <33
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Thanks for feedback <33
Did he pay for your time as well as the shopping items?
I can give you a customer's perspective ... I don't do the sissy thing, but overall I'd say you did amazing!
I think I can give you ideas for the text thing. The important thing to get here is that texting between sessions really breeds loyalty, and feels really personal. Instead of thinking of it as "needy", look at it as an opportunity to be exploited, you just have to control it. Otherwise, you risk losing him to a woman who does get the texting thing Here's the thing -- you're the dominant, he's the submissive, he *wants* you to take control. So, if you're okay with some texting (I.e., if you want to keep him as a loyal customer, maybe you don't really care), taking control will actually be even more fun for him. Here's a quick example:
"Sissy texting time is Tuesday and Thursday from 8:00pm to 8:10pm. You get your mistress for 10 minutes, then no more texting. And if you want to text, your first text MUST be a picture of you in the panties I told you to get last time. Only exception is to schedule time with me".
He will love it. He'll love that he has an assignment with the picture (although, obviously, assess what his turn-ons are, maybe pics are a hard limit for him, maybe the pic should be of panties but not him in it), he'll love that he texts only at the pleasure of his mistress and she has assigned him a time. And you've now completely controlled texting time to 20 minutes total, and you know the exact times (obviously, change that how you want, maybe it's only 5 minutes a week -- just make sure he knows he can text to schedule a paid session anytime). And you can take this as far as you want:
"Sissy texting time is Wednesday from 8:00pm to 8:15pm. Your first text must be a picture of you in your sissy outfit, and it must show your cock. You have to tell me how many times you've jerked off this week, and I'll decide if you get to do it anymore, based on whether the picture is good enough."
Now you're making him jump through more hoops. You can use this text to generate more business with him, if that's what you want. So if he does text you, you can respond: "Okay, you don't get to jerk off again until you come see me, and it better be this week, or you'll be sending me pictures of you with a buttplug inserted next time."
Other things that work really well, for little investment from you: "okay, if you want to jerk off again this week, then tomorrow you need to go to Frederick's (or whatever), send me pictures of 5 different kinds of slutty underwear. I'll pick one out, and then you'll wear that to our next session." This is going to take tons of his time and feel to him like you've spent hours with him, but it's all just a few seconds for you ... then make sure you get the session booked after! Which will be easy, because his head will be whirling, he will be begging for that next session, there may not be anything for you to sell :) And at a price that you feel compensates you for your in-session and few minutes of out-of-session activities with him.
In short, if you like this guy as a customer and want to keep him, texting is your best friend, he will be loyal, his little weekly assigned text window will be the highlight of his week, he'll think about sessions with you a lot. And he'll like it better if you control how he may interact with you, and you'll like it better, because it strictly limits text time, and you can figure out ways to use it to get that next paid session sooner ... at a rate that compensates you fairly for the entire interaction. It's not "neediness", it's a market demand that you can control and fill in just a few minutes a week, and use to close more business, and you should look at it that way. Some of the best dommes I know work this way ... the key is that you feel like you're getting fairly compensated overall, and that while he's getting turned on, you're using it to close the next session and keep him loyal.
Anyway, just a bunch of ideas you can play around with, depending on how your connection is with him
Chefkitty, You did great! That sounded like fun, I hope you got paid for your time, too.
Radius, I'm totally stealing your suggestions. :)
lol good!
I came up with a bunch of ideas for next trip but was hoping other folks who had done this would chime in!
Do you have a way he can pay you without meeting? There are lots of 'assignments' you can give him for a fee, to supplement time together. Have him shave his legs, wear toenail polish, wear bras, and send you photo proof. Have him purchase a butt plug/vibrator and forbid him from touching his 'clitty' unless he's got it up his 'sissy pussy.' The lingerie shopping was a fantastic idea! Next time you can ask a salesperson for help finding lingerie for him so "he'll stop wearing mine." Give him a girl's name (like Candy, Missy, Kelli, etc) and only use that name with him. Remind him frequently of his status as a girly sissy slave, not a man. While out together, point out men you think are handsome, and ask him which boys he thinks are cute. Flirt with 'real' men in front of him. Treat him like a girl friend, never like a guy. Put lip gloss on him in public. Get your nails done together. Only allow him to watch "tranny porn." Have him talk like a teenage girl (OMG like totally fer sure!) Have him wear perfume instead of cologne.
Lastly, talk to him about his fetishes. The more you know, the more buttons you can push, the more he'll enjoy himself, and the more he'll continue to pay.
Having one sissy customer on cam really wears me out, and all he did was hang out in my free chat and email about his assignments. I didn't realize how much work it would be to keep up an extended RP like that, so props to you to doing it IRL. It sounds like you did amazing–he is lucky to have found you! And I also just wanted to say I am loving Radius's take on it–great ideas, I might have to "borrow" a couple, adapted for camming! I think just limiting him to certain windows where he can email or hang in my chat will help both of us.