Elements of a date (one possibility)

1. Charlotte will arrive in jeans and a t-shirt. No underwear. No bra. She will kiss me (I will kiss her) hello. We will have a drink. I will send her to the ladies’ room to change. I will have selected a bar with copious restrooms.

2. Charlotte will remove her jeans and t-shirt, and will step into the matching lingerie we chose together. She will place the We-Vibe remote control vibrator in her panties, against her clit. She will put on the short dress I’ve selected from her wardrobe. And she will bring herself close to orgasm, but not come, recording herself for me, and sending me the recording from the bathroom.

3. She will emerge, her fingers redolent of her cunt, her face flushed, looking spectacular. We will drink a second drink. During which time, I will be sure to smell her fingers, and to connect the vibrator to my phone. I will hand her one of my earbuds – I’ll keep the other in my ear – and will play for Charlotte some audio. Maybe the recording she just sent. Maybe a previous orgasm. Or edging. As we listen, I will experiment with the We-Vibe – dialing it up, dialing it down. Having it go steady, pulsing, starting, stopping. I’ll experiment with her responsiveness. See what she can tolerate. See what she can’t tolerate. Maybe I’ll make her come at the bar. More likely, I’ll make her wish I would make her come at the bar, make her desperate to leave the bar, so she can come.

4. We will away to a hotel. I will continue to toy with her toy as we ride in a cab, or as we walk.

5. Once checked in, I will ask Charlotte to kneel before me. “Are you ready?” I’ll ask her. “Tell me what you want.” I will make Charlotte enumerate her hopes for the evening. Explicitly. In detail. Perhaps as I stroke my cock, perhaps as I tease her mouth with it as she speaks.

6. I will grab her head, her hair, and feed her my cock as I hold her mouth down on me, as I strain to reach her throat with my cock. I will fuck her face. Maybe for a minute. Maybe for ten. Maybe for longer. Perhaps by now I will have bound her wrists behind her. Or blindfolded her. Or both.

7. If her wrists are bound, I will untie them. I will stand her up, and, using my hand to grip her throat, I will press her back against a wall. Or maybe I’ll lift her onto a desk, so she is standing before me. Still blindfolded.

8. “Play with your pussy for me,” I will say. Blindfolded, disoriented, dripping wet, needy, aching, throbbing, Charlotte will comply. Perhaps with her fingers. Perhaps with her vibrator, which I might hand her.

9. As she approaches orgasm, I will ask tell her to stop. My cock will be painfully hard, in my hand. I will have her resume. I will stop her. Start her again. Stop her again.

10. “Jump down,” I’ll say. “Come sit on my cock.” I will demonstrate to Charlotte just what it is to be nominally on top, but to be fucked, to be topped, as I bruise her hips with my hands as I drive her back and forth, up and down on my cock. If she nears orgasm, I’ll pull her off my cock, or press her down on it so I’m deep inside her cunt, still, as she pulses around me.

11. “Get up,” I’ll say. “Move to the bed.” If she is even slightly slower than I would like her to be – which seems nearly certain – I’ll toss her to the bed, flip her over, and hold her wrists above her head as I bind her wrists again. My hope is there will be a headboard to which I can fasten her wrists, that it will be high enough that her arms are a bit uncomfortable, that she will be unable to move much. I will bind her legs, bending them at the knees, looping rope around her calves and shins, affixing them to her thighs. Perhaps I’ll yank her chicken-winged legs apart, and further restrain her, so she is truly immobilized.

12. I will check her blindfold. Make sure it’s properly situated. I’ll check the ropes, make sure they’re taut, but not tight, so she can move just a tiny bit, but so she can’t REALLY move. I’ll kiss her. Hard. “Good girl,” I’ll say. “Are you ready?”

13. “You are not to come without my permission,” I’ll instruct her. “Do you understand?” She will nod. “I didn’t hear you,” I’ll say. “Yes! I’m ready!” “I’m ready for….?” “I’m ready for you to do whatever the fuck you want with me, to me.” “Good girl,” I’ll say. “Good girl.”

14. I will taste Charlotte’s cunt. I will tease it just a little, with my lips, my fingers, my beard, my tongue. Maybe I’ll tease her asshole a little too. Slide a finger in each of her holes as I lick her clit. Maybe she’ll ask to come. Maybe she’ll beg. Regardless, I’ll deny her.

15. I’ll step away. I’ll leave her, writhing, wet, needy. Maybe I’ll have a drink. Maybe I’ll stroke my cock. Maybe I’ll talk to her. Maybe I’ll sit, watching her, silently.

16. After as long as I can bear to wait, I’ll bring the magic wand to her cunt. I’ll turn it on, so she can hear it. I’ll hold it close enough that she can feel the vibrations near, but not on, her flesh. She’ll lift her pubis toward the wand, which I will retract.

17. Finally, finally, I will bring the wand down on her cunt. And I will not remove it until she has said “red.”

18. We will lie around for a few minutes. We will head downstairs for a drink. She will, again, be wearing her remote control vibrator. Which I will be playing with. Perhaps while asking her to read (this?) to me.

19. We will return to our room, where I will lie lazily on the bed, as Charlotte feasts on my cock until I say red. And readers of this blog know that I have quite an appetite for the oral attention of a beautiful, talented woman. We’re talking hours. Literally. 

20. Charlotte will want me to spend the night. Which would be lovely. But which is often hard to manage given my… life. But if I can swing it, subject to my “I don’t sacrifice family time for dates” rule, yes, yes, I will do that. And subject her to my very loud snoring. More likely, though, we will loll around for a few after I finally fill Charlotte’s mouth with my cum, and I will kiss her goodbye. Perhaps after eliciting one more “red” from her with my tongue and fingers.

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