A Ruined Orgasm

Fortunately for me, I was able to chat with Ms Lee the night before she expected me to try to milk myself at work again. She told me that I was lucky that I had gotten hold of her due to her busy schedule. She proceeded to tell me that during the course of one week she would be having sex almost every other day, as well as other pleasant events such as breaking in the dildo harness I had just purchased for her.

I was nearly insane with jealous frustration as I heard about her frequent sexual adventures, all while I was entering my third month in chastity for her pleasure. While she was free to have sex whenever she desired I was reduced to begging to be allowed to try to milk myself – without touching!

When I told her that she had my penis straining like mad against my chastity sleeve she replied:

good! put plug back in then & rock if you want

When I told her that I was now chastised, pantied AND plugged for her, she replied:

lovely!  rock away and see if you can milk yourself while we talk

As she proceeded to tell me more about her sexual escapades I could feel my penis straining even harder in my sleeve.  I told her that I felt like her cuckold, denied pleasure while she was free to enjoy sex all she pleased. Sne increased my frustration even more by telling me:

if you were here, i’d be taking you with me to my sex guy, binding you, & forcing you to watch & clean us both up, while chastised and plugged. i’d make you beg me to fuck you while you were on your hands and knees and his cock was in your mouth i’d make you keep your eyes open while you blew him so you could watch that cock in your own mouth  and yes, you would be plugged at both ends –  nobody fucks you but me, though

fantasize on that for a while. rock & try to milk yourself. you may touch only the head of your cock with only one finger.  i’ll wait

I desperately tried to milk myself, but even touching myself with one finger did not do the trick. Next Ms Lee told me:

Well, honey, i want you to cum, but i want it to dribble.  SO do this: keep chastity sleeve on, but you may touch. rock the entire time. when you feel yourself just starting to cum, STOP TOUCHING and let it finish on its own.  I’ll wait.

It took a while, but I desperately needed release so I masturbated like a naughty little boy, frustrated by the restraining chastity sleeve. I couldn’t achieve anything close to a real erection, but between two months in chastity and all the teasing I was enduring I finally was able to start cuming. The chastity sleeve had just the effect Ms Lee desired and all experienced was a pathetic dribble as two months of cum was released. No pleasure, no explosive ejaculation, just a constant dribble.

Ms Lee was pleased with my performance and chatted some more as she prepared to go out for the night. She increased my frustration as she told me she expected some more pleasurable sex that night. Then treating me like her little cuckold she told me:

Get some rest. You were a good boy for me and you’ve done well