"So you've written several dare stories involving teachers. I'm a teacher..." She said, leaving the pause hanging in the air.
"Oh? You'd like to be dared?" I typed back, knowing that it was exactly what she wanted.
"Yes." She replied, and a blushing smiley face icon appeared on my screen.
"Okay then, here's your dare!" I typed back. After thinking for a minute, I wrote, "The next time you're alone in your classroom, pull out one of my teacher stories. Read it. Lose yourself in it. Then, get up and lock the door. Turn around and pull your shirt up and flash the empty desks."
"Oh my!" she wrote, along with another blushing smiley face.
I continued, "If you're really daring and wearing a skirt, take your panties off and finish the rest of the day without them. You could even put them somewhere slightly hidden where you can still see them. Put your panties in one of your desk drawers, but leave it where a small bit of the fabric still shows. Then as you work, you'll be reminded of how naughty you are being. Now, if this sounds silly and childish to you, then it isn't going to work. You have to really want to do it. Do you want to?"
"Yes, and I'm really excited about doing it. It's a little scary." She typed back.
"Well," I told her, "you've been dared, so go complete your mission."
Two days later, Denise wrote me back with the details of what she did.
"I did it," she began. "It took me a while to get up the nerve, but it's been a really nice week this week so I've been wearing skirts. On Friday I printed out one of your stories about teachers and when I was in my office on lunch I took it out and read it. As I read it, my hand kept sneaking farther and farther up my skirt. As I got close to the end of the story, I slowly started to ease my panties off. By the time I was finished reading, they were down around my ankles and it took all my willpower not to get myself off right there!"
She continued on, "So, I got myself mostly composed again, rolled up my panties and slipped them into a drawer in my desk. I left just a bit of pink fabric visible as I shut the drawer. I must have glanced at that drawer fifty times the rest of the afternoon as I was teaching!"
"I was definitely feeling naughty. I was just glad nobody came around behind my desk that afternoon, although the thought crossed my mind a few times and that just added to the thrill."
I knew how she felt as I continued to read what she wrote, "When the final bell rang, and everyone left, I slipped the panties out of the drawer and into my purse, and drove home without them on! The moment I opened the door to my house I ran inside to my bedroom, jumped on the bed, yanked my skirt up and did what I had been dying to do all day long!"
I wrote her back and told her how proud I was. I also told her how her story really turned me on. "Mmmmm," I told her when she opened up the chat window. " I'd love to see a picture of those panties dangling out of the desk drawer...then I'd know for sure that you really did it. Even if you cheated and brought in an extra pair of panties, that'd still be daring."
"I was so nervous." She replied. "As soon as I finished and cleaned up, I unlocked the door. About five minutes later, the teacher next door came over!"
I told her again how proud I was of her, but reminded her that it was only a beginning. I asked her if she was ready for her next dare.
"Yes!" she typed back. "I'm ready to do more!"
"Okay, Denise," I typed. "Here is your new dare! I want you to have another erotic story printed out to get you into the mood. Then, lock your classroom door. Go to the back of the room, farthest from your desk. Read the first half of the story, and then remove your panties. Leave them on the floor. Then go back to your desk and read the rest.
"Oh wow!" she interrupted, "Do you think I can really do that?"
"Of course you can," I replied, "but you've really got to be nice and horny for it. This time, I want you to finger yourself until you have an orgasm. Go for it. If you're too nervous and can't bring yourself to orgasm, then put the panties in your desk and leave them there until the next day and try again. I can't wait until I hear from you!"
She agreed to the dare, and the next time I heard from her, she emailed me her story. I had a stiff cock from the moment I saw it in my inbox.
"So I did it," she typed. "I had an orgasm reading your story, right there in my locked classroom!"
She wrote, "Wow! That was really intense. I was able to do the dare just like you told me. I put my panties on a desk. They were pink and lacy. I was wearing a pink sweater and a black skirt, and black heels. It was a cold day but I have been sticking with my skirts anyhow. I kept peeking towards the door and windows to see if anyone would stop and look in and see me. I didn't see anyone, but it was so naughty and it gave me such a rush!"
Again, I told her how proud I was of her. We talked about how excited it had made her and how she really enjoyed doing the dares for me. So, of course I gave her another one.
"Your dare tonight is to wear nothing but a shirt. The shirt should be the kind that you sleep in, but barely covers your butt. Wait until its dark. Surf the net; read some stories...get really aroused. I want you wet. The kind of really hot wet that you can feel as you cross your legs. The steaming wet that as your finger slowly slips between the lips of your pussy...it slides deeply and easily inside of you."
"Oh my!" she typed.
I continued on, knowing that I had her interested. "Go out to your car. Open the door to look inside. Crawl into the driver seat on your knees. Reach over and touch the floor of the passenger side. Let the shirt ride completely over your ass and up your back, exposing you completely. If I was standing behind you I would see your full naked butt, as well as the puffy lips of your pussy."
"Mmmm," she wrote. "This is really daring."
"Now for the fun part,'" I replied, "Next, I want you to sit down in the driver's seat. If you feel safe and really horny, I want you to spread your legs wide. Slide your fingers across your thighs until they reach your pussy, and then...finger yourself until you come again. If you really feel safe, pull the shirt above your breasts. I want you to show as much of your body as you can. Can you do that for me?"
"I will," she wrote back. "I can barely wait until tomorrow."
When I got home from school a few days later, I checked my email and found her reply.
"As for the car dare," she typed, "I did it last night and even though it was cold, I did it anyway! I was wearing my white and pink 'Hello Kitty' nightshirt which I wear a lot and it's really short. I sat in bed on my laptop chatting and getting really worked up. It was about midnight when I decided I was ready for the dare! My pussy lips are thick normally and when I get excited they swell up even more...and I was already soaked. If someone had come by then I'm not sure I could have refused them!
I put on a pair of black slippers and walked out to the driveway. My nipples got hard as soon as the cold air hit them. I was trembling as I opened the driver side door and crawled inside. I got up on the seat on my knees and then leaned over towards the passenger seat to touch the floor like your dare instructed me. I wasn't even thinking about the gear shift being there and it brushed against my pussy a couple of times which I have to say was not an unpleasant feeling! At one moment I realized that if I wasn't careful and my knees slipped I could probably slip right onto it and that thought made me even wetter.
I thought about the picture I must be making for someone if they had happened to walk by. Fortunately it was dark and I live in a fairly quiet neighborhood. After a few minutes, I was really worked up and ready for the second half. I sat down low in the driver's seat, and reclined the seat back as far as it would go. Then I pulled my shirt up over my warm and swollen tits and leaned back and spread my legs wide.
It was probably 45 degrees outside but honestly I wasn't feeling cold at all. My mind was numb as I lay back and tuned out the reality of what I was doing. I started fingering myself, closing my eyes, imagining the whole time that someone had walked up and was watching me there. I imagined it was someone that I would be totally embarrassed if they caught me. I imagined that this person had quietly opened my car door, reached one hand to my chest to hold me in place and then the other one between my legs, guiding my fingers around my clit and then deeper.
In moments I had come, and in my daze I had totally forgot to bring something to put on the seat! So needless to say I got my seat a bit wet. After a few minutes I finally started to get really chilly so I pulled my shirt back down and staggered back inside of the house. I made some hot chocolate and got a warm shower before bed. Thank you for daring me to do that!"
I've progressed to the point now that if I see that I have an email from Denise, my cock immediately goes rigid. She did such a good job of describing her dare that I was trembling while reading it.
So, of course, after we discussed it, I gave her another dare. This time I told her to go get some dinner at a drive-thru. She had mentioned that she had an egg vibrator, so I put it into the dare.
"I want you to do whatever you need to do to get yourself in the mood," I told her. "Then I want you to insert the egg, or put it up against your swollen clit and push your thighs together if that helps to hold it. If not, you'll have to use your hand. I want you on the verge of an orgasm just before you order your food. If there are cars in front of you, I want you to crank up that vibe until you're on the very edge of coming...so that when you get your food at the window, you'll still be feeling spasms."
"Oh my, I'm already wet with this one." Denise typed.
"Good," I told her. "Then you're really going to enjoy this. If the drive-thru lane is empty, you can go ahead and get your food, but keep the vibe on. Turn up the radio if it helps to hide the noise. After you get your food, drive forward to "check your order" and stop about ten feet from the window. Once you're there, you are allowed to have your orgasm."
This time, I got a response the very next day.
Denise wrote, "So anyhow last night I was in bed, chatting on the laptop, in my Hello Kitty shirt, getting pretty excited, and I started craving some cookies and ice cream. I told the person I was chatting to I'd be back in a few minutes. I got my egg and slid it in and grabbed my keys and purse and the remote for the egg and ran out to my car.
As soon as I turned on the engine, I turned on the egg. Luckily for me it's not a very long drive to McDonald's and the streets are empty here at 11pm. Still, by the time I pulled up to the empty drive-thru I was pretty worked up. I was breathing hard as I tried to order the 3 chocolate chip cookies and a hot fudge sundae, but I got it ordered with just a little stammering!
So then I pulled up to the window, it was a guy working the window, and he was definitely checking me out! I was so glad my shirt was just long enough to cover me so he couldn't steal a glimpse of my pussy!
That would have been embarrassing....but I was breathing so hard and not even thinking about my chest. My nipples were pushing right up against the material of my shirt!
He was smiling big time as he handed me my food and watched me lean over to get it. I paid him and pulled up about ten feet to check my order. I had rolled my window back up and I checked my mirror to see if he was still watching, just as the egg pushed me over the edge! Oh wow! I must have looked like I was having a seizure by the strength of it.
I sat there for a minute until I could focus again, and then finally drove back home. I slipped the egg out, climbed back into bed, and ate what had to be the most delicious cookies and sundae I can ever remember!!!"
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