Me: May I direct your dressing just a bit?
Jen: Since you asked like a gentleman 😉
Me: To begin with, may I see three pairs of boy shorts among which I might choose?
Me: (picture or description)
Me: And tell me, generally, what you feel sexiest wearing?
Jen: Well, I have light pink boy shorts…I think I may have worn these last time we went to dd. those are my only true boy shorts. I also have a pair of turquoise panties with line colored lace from v.s. which are like skimpy boy shorts.
Jen: Those feel really nice. Both are equally sexy to me.
Jen: I feel sexiest wearing something skimpy with something conservative….like low cut shirt with pants or longs leave shirt with short skirt. And red lipstick.
Me: I like conservative…. Thinking….
Jen: Okie dokie.
Me: Actually, may need to be le trapeze. Don’t think I can get out in time for DD.
Jen: Oh my! I’m down to try something new.
Me: I live to thrill.
Me: Conservative…. Possibility 1. Dress for the most corporate interview you have clothes for.
Me: Possibility 2. Jeans, a top that lets me see your cleavage while we are drinking first.
Me: (no bra?)
Me: Possibility 3. Slacks and a blouse.
Me: Possibility 4. Something else?
Me: Your thoughts?
Jen: I like one and two. Very exciting
Me: Let’s both ponder that. I like 1, because – well maybe I’ll just interview you for a job.
Me: Of course, I could do that with 2, too…
Jen: I’ll have fun pondering. I might dress up tomorrow and try both
Me: Pics, please!
Me: And if you were to indulge my request for pics, you’d need to send them by e-mail, since Google Voice doesn’t receive pics by text. Just fyi. 😉
Me: How’s your thinking going?
Jen: Hehe, I still like either
Me: I think I may interview you….
Jen: That’s a good idea
Me: Do you want the gig? And how much? I would like to see what you propose to wear in advance. Lay it out for me, and send me a picture by email? Please?
Jen: I do. I would love to work for you. Why not start the interview process now. I will email you photos this evening.
Me: Delicious. I’d like to see the panties and bra you propose to wear on you, if possible.
Jen: Absolutely! I am prepared to do what ever is necessary for this position.
Me: Good girl. At what time will you be in a position to comply with this request? And may I see a hint of what you’re wearing now?
Jen: Absolutely! Around 10pm tonight. I know that is technically after hours. I hope that is ok….
Jen: I will impress you. You won’t be disappointed.
Me: Good. As soon as you’re in a position to do so, I’d like you to send me pictures of your mouth, your eyes, and your breasts, pushing against whatever fabric currently contains them. And your crotch. Please.
Jen: I’ll get right on that.
Me: Good girl.
Jen: Please check your inbox and you will find the requested photos. I cleared my schedule in order to fulfill your request.
Me: Oh my. Very good work. Very good indeed. Alas, you understand that I’m a demanding employer, and that good work will be rewarded with more work….
Jen: That is expected with such a prestigious employer. I am prepared to impress you again and again.
Jen: Something has cone [sic] up and I will be unavailable for the next hour or so. I hope you understand.
Me: That’s fine. Email awaits you.
Thank you very much. This is very promising.
Thank you, both for the quality of your work and for its timeliness.
May I ask for just a couple more things (for now)? First, I’d like to see a selection of your lingerie from which I might select. Modeling, though welcome, is hardly necessary.
Second, I’d like to hear your orgasm. We discussed this previously, but it fell by the wayside. If you’re in a position to give me that tonight, preferably (but again, not at all necessarily) narrated, explaining what you’re doing, what you’re thinking about while you’re doing it, that would be lovely.
Finally, your ass: I need to see it, in whatever position, whatever covering (or none) you think best.
Thank you for your continued interest.
You texted me that you’d be away for an hour. It’s been two.
I’d like to see your lips wrapped around something, please – a finger? a bottle? a banana?
I’d like to see one of your nipples, if I may.
And I’d like a photo of your knees on the floor, as they will be when you kneel before me in just two night’s time.
Of course, all I asked for before as well remains outstanding.
Finally, I’d like just a few words – if you would, please describe the sensation of receiving cunnilingus from the most skilled performer you’ve ever experienced. I’m not asking who it is, or seeking praise in the unlikely event it’s me. I’m asking what the best felt like. (Not even what s/he did – just what it felt like.)
Your three requests are attached. The audio is not accompanied by my commentary, as I find it hard to speak when I am highly aroused.
[In addition to these photos, she attached this recording of her orgasm.]
Wow. You’ve outdone yourself. I’m quite pleased. Thank you.
I am very sorry for my late relpy [sic]. You are a demanding employer indeed.
The sweetest, most delicious cunnilingus feels like floating up into a place/state of mind that is a need and a fulfilling at the same time. My mind is blank and fuzzy.
I awoke to three lovely presents this morning. Thank you.
When you have a moment, may I see your thighs, with a glimpse of your panties, and your hand somewhere in the picture?
Also, a full length picture of you in the clothes you wear today. As well as you in just your underwear, if circumstances permit (but only if they permit).
Finally, every hour on the hour today, or as close to then as possible, I’d like you to take a break from whatever you’re doing just to imagine my cock in your mouth.
Would you do these things for me, please?
Me: Thank you for last night’s efforts. An e-mail awaits you this morning. N.
Jen: Good morning! Pardon me for breaking character. So that is my limit for being told what to do. Interesting huh? Is my limit a lot smaller than other women you’ve played with? I’m interested in hearing your thoughts about this. Xoxo
Me: Sorry to hear we reached your limit so quickly. Most of the women I “play” with have no limit. 😉 It’s enjoyable for them, each step of the way.
[lest you worry, all photos – and her orgasm – posted with Jen’s express permission.]
Thank you so much for sharing all of this (& thanks to jen as well). I love watching interactions between other people.
My takeaway is : picture of knees on the ground: great idea
She is lovely N. Lovely.
I know, right?