Road trip/dinner with two women and some free time for dares

[wingman78]

Hi GetDare, I'm back with another request for dares! As usual I'll be providing reports (or, if requested, pictures/other proof) to those that give me tasks/dares.

Next Saturday I'll be playing taxi for two female friends (just friends, they don't know about my kinky side and I'd like to keep it that way ). I'm picking them up late in the afternoon to drive them to a concert (about 60-90 minutes away). Once there the three of us will have dinner together. After that I'll drive back on my own, arriving home around 8pm. I'll pick them back up the next day around noon.

I'm looking to have some fun during the drive/dinner on Saturday, and of course a lot of fun once I get back home Any suggestions to spice things up are appreciated. I can hide some of my toys in the car if needed.

All dares within my limits are accepted, both simple ones ("wear a plug on the trip/during dinner", "stay naked in heels at home", that kind of things) and more extreme ones that push my limits (I'm still in need of some punishment for slacking off at work all week, so spankings/CBT/enema's/eletrosex punishment/maybe a hidden public dare in a gas station toilet on my car trip/etc).

As always I'm looking forward to what you guys/gals can come up with. And if you don't have any ideas yourself you can always suggest a couple of "person above" threads for me to post in!

[wingman78]

No takers? Surely at least one of you kinky people must have some ideas for me

[bamadude01]

For all of your driving, you'll wear your choice of panties, as well as your chastity cage, and medium butt plug. You are not allowed to pee starting 2 hours before you leave. You may stop at a gas station on the way home to pee, but you must strip down to your panties to be allowed to go.

once you return home, swap to your electro gear, including cage and electro butt plug. set it on a setting that will tease/torture you. next, lock your hands behind your back, or above your head with the self-bondage timer lock, set for the max time. at this point, just let everything run.

Once you're release, get your flogger, and endure 100 spanks to each cheek for you lack of productivity at work. These should be done as hard as you can manage to make them.

At this point, you may start stroking. You will edge 25 times, while riding the Bad Dragon dildo. At this point, you may cum.

[wingman78]

Originally Posted by bamadude01

For all of your driving, you'll wear your choice of panties, as well as your chastity cage, and medium butt plug. You are not allowed to pee starting 2 hours before you leave. You may stop at a gas station on the way home to pee, but you must strip down to your panties to be allowed to go.

once you return home, swap to your electro gear, including cage and electro butt plug. set it on a setting that will tease/torture you. next, lock your hands behind your back, or above your head with the self-bondage timer lock, set for the max time. at this point, just let everything run.

Once you're release, get your flogger, and endure 100 spanks to each cheek for you lack of productivity at work. These should be done as hard as you can manage to make them.

At this point, you may start stroking. You will edge 25 times, while riding the Bad Dragon dildo. At this point, you may cum.

Thank you very much Sir, I'll do that. The plug and cage will definitely make dinner interesting! And my e-stim box has a "random" setting that's just perfect for the next part: it randomly switches between a setting that feels good enough to get me close to cumming and short pulses that get quite painful at a higher level.

Any additions from you or others are welcome!

[wingman78]

Only two days left for you to add tasks/dares/rules/punishments. I hope there will be some extra posts here!

[wingman78]

It's about time for me to leave. I put my chastity cage on (I'll leave the keys at home), plugged my ass with the medium plug and put a pair of sexy panties over that. It's a thong so I hope nobody will notice a "whale tail" when I bend over

I'm bringing a pair of nipple clamps as well just in case I feel like spicing things up even more during dinner/the drive back home. I'll check Getdare for additional tasks when I get to the restaurant, and I'll be online all evening once I get back home.

[wingman78]

The final update for now. The trip was fairly uneventful, except during dinner. Both girls were wearing low-cut, tight tops that made it near impossible to look at their breasts. Which were nicely shaped too, so by the time dinner was over my cock was ready to burst out of the chastity cage!
The medium plug wasn't that bad, my ass can take it quite easily and except for some discomfort when sitting down I hardly felt it by the time I got back home.

Once there added cables to my chastity cage, swapped the plug for an electrified version, and got my time lock from the freezer. I decided to add nipple clamps too, and after setting my e-stim powerbox to "random" on a pretty high setting I tied myself securely to a beam on the ceiling.
The next hour or so alternated between heaven and hell: the random setting sometimes produced painful pulses to my cock and made my ass clench tightly. At other times it got very close to making me cum! Meanwhile my nipples were starting to hurt more and more, and I regretted adding the clamps about halfway through.

Once I was free again I did 100 hits to each of my ass cheeks as ordered, and I'm now going to start the 25 edges with my largest dildo buried in my ass. Thanks for making my evening interesting!