Literotica, Sex with Strangers

Literotica: Teacher Takes a Dare

“I’m so turned on right now,” she typed back to him. “I’m so hot. I can’t believe I got this way just from chatting with you.”

“It’s because you’re being naughty. You’re doing things that you shouldn’t be doing. It goes against the rules that you live by,” he responded. “Besides, you know how incredibly aroused I am right now just from talking to you.”

That really excited her. She had never done this before, but she was home on winter break and really bored. She was a teacher at the local high school and still had another week before returning for the spring semester. It was almost lunchtime and she was still in her pajamas.

She found herself at an erotic stories website reading a story about a woman doing sexual dares.

She had emailed the author to tell him that she liked the story. The next thing she knew, she had downloaded an internet messenger service and was actually talking online to the man. He claimed to be a teacher too, but she just assumed that was to make her more at ease.

“Are you ready for your dare?” he asked her.

She had been waiting for this, anxiously looking forward to it and dreading it at the same time. She took a deep breath and replied, “Yes. I’m ready.”

“Okay, for your first time, we’ll make it easy for you. What are you wearing right now?” he asked her.

“A long sleeved flannel PJ top and bottoms,” she typed back, wondering why he needed to know that. If this was about to turn into typical horny guy cybersex that she had read about, she was going to be really disappointed.

“Okay, we can work with that,” he replied, “Long pants I assume? Button front shirt?”

“Yes and yes. It’s freezing cold outside here.” She commented back.

“Okay, here we go. This is easy for you. Unbutton the top. Undo all of the buttons, so that when you stand up, it separates and opens.”

“Okay,” she typed back to him, “hold on a minute.” She nervously unbuttoned her PJ top. The warmth from her body escaped as the two sides separated. Her fingers were actually shaking as she typed back that she had done what he asked.

His response was rapid. “Pull the shirt open. Imagine that you are on a webcam with me. Tease me. Slowly pull it apart showing me inch by precious inch.”

“I’m doing it,” she typed back feeling a little silly but excited to find out how far she would go.

Again he was quick in response. “If you’re really excited, I want you to slide your hand down inside of your pants. Tell me how excited you are.”

She slowly slid her hand across her belly to the elastic top of the pajama pants. Her shaking hand slid underneath the pants and inside of her panties. She could feel the intense heat against her cold fingers. She was so hot that it was like she had steam coming from deep inside of herself. Using her one free hand, she responded, “I’m so hot down there.”

“Tell me exactly. You don’t know me. I’m an anonymous man. Let yourself go and say it.”

She let her fingers slide down between her legs. The second she touched the outer lips of her pussy, the moisture came gushing out. Instantly her fingers were covered in slickness that she had never experienced before. “I’m so wet,” she managed to type one-handed.

“That’s it,” he wrote back. “That’s what I wanted to hear. Now, rub your pussy until your fingers are covered with your juices. Then pull your hand away, slowly rubbing your clit as you do. Then, I want you to rub your nipples, covering them with the juices from your pussy.”

She had never had this type of conversation with anyone before. The language was rough and skipped no corners. He was direct in telling her what to do. She was growing to like it.

She did as he asked, her nipples growing harder than before, partly from arousal and partly from the moisture now on them meeting the cold air of the room.

His message appeared on the screen, “Now I want you to stand up and go the door of your apartment. Open the door a crack and look around. If no one is around, open the door wider and take a look around. If the coast is still clear, open the door completely. Then I want you to stand in the open doorway and stretch your hands in the air above your head. No matter what happens, I want you to count to ten. I’ll wait here for you to tell me about it.”

She stood up, and on shaking legs walked to the door of her apartment. It was mid-day and the sun was shining. Most of the people living in the complex should be at work right now. She looked out the peephole and didn’t see anything, so she opened her door. She cautiously looked outside and seeing no one around, she opened the door wide.

She stepped into the doorway and slowly raised her arms above her head. As she did this the pajama top opened wide at the bottom, exposing her bare stomach. Her full breasts were half exposed as the gap widened.

She felt totally on display. Her nipples were still covered, but she felt naked. She did a slow count to ten and went back inside to her computer. “Wow. I did it,” she typed. “I want to do more.”

“Okay, I’m proud of you,” He replied. “Now this time, slide the back of your bottoms down until your bare ass is showing. Go back outside. Slowly turn around so your ass is showing to anyone that can see it. Then turn back around. If you still don’t see anyone, I want you to pull the shirt back until both of your breasts are exposed. If you still feel comfortable, I want you to caress your breast and tug and pinch your nipples.”

His words were really arousing her now. She couldn’t wait to try it. She told him to hold on and she went back to the door. She slowly turned her body in a circle, showing her bare smooth ass to anyone that might walk by. When she turned to face the parking lot again, she reached up and pulled her shirt open, baring her breasts to the world. She pinched and tugged on her erect nipples. She wanted to reach down between her legs and touch herself, but she reluctantly came back inside.

On impulse, she stripped completely naked before sitting back down and replying to him. “I’ve taken off all of my clothes.

I’m completely nude right now and as soon as I finish typing this I’m going to start touching my pussy.”

He liked what he read and told her so. “I wish I could see you right now. I can’t believe you’ve stripped naked.”

“I’m fingering my clit and sliding my fingers in and out of my hot pussy right now,” she replied, feeling a bit silly as she typed those words. But she was so excited right now that it didn’t matter.

He threw caution to the wind and gave her a new command. “Well then, if you’re ready to be really wild, go sit in your open doorway naked, and finger yourself until you come. Go now.”

“Going!” she typed back. She jumped up and walked quickly to the door. “I can’t believe I’m about to do this.”

She opened the door wide open this time, not even caring to look around for people that might see. She sat down on the cool concrete walkway, spread her legs wide and began fingering herself rapidly. She was so hot and wet.

Her juices were practically coating her inner thighs. Her free hand rose to her breast and she began pulling and pinching her nipple. In seconds her teeth clamped tight, her eyes closed, and she came. She came hard.

She came so hard that she moaned out loud and her ass came up off of the cement. She gave a few quick strokes against her clit until she couldn’t take it anymore and she clamped her thighs shut, holding her fingers trapped against her steaming pussy.

As she came down from her orgasm, the world suddenly returned. Her eyes opened wide as a UPS truck rolled to a stop in front of her building. She was partly hidden by the stair railing, but she had to quickly scramble backwards into her apartment and close the door.

As she lay there, breathing heavily, she felt the stairs shuddering as the UPS driver ran up them. He came straight to her door and she heard a package dropping outside. He gave a quick knock and turned to leave.

“Oh, wow!” she said to herself. “That was too damn close!” She waited until she heard his footsteps going down the stairs and his truck rumble away.

She cautiously opened the door. On her hands and knees she opened the door wider to pull the package inside. It was an order of towels she had purchased online.

Right next to the box was a small patch of wetness on the cement where she had been sitting moments ago. The UPS man had surely seen it, but hopefully had no idea that it was the wetness from her pussy.

She closed the door and dressed back in her pajamas and went back to the computer.

“Well??????” the screen said numerous times. Obviously he couldn’t wait for the details any longer.

She sat down and gathered herself together. “Well,” she began, “it was awesome. I came so hard. It was quite possibly the wildest thing I’ve ever done. I almost got caught by the UPS man.”

She told him the whole story and he pulled every little detail of it from her. At the end of the story she asked him if was turned on. He replied that he had been stroking his cock the entire time she was telling him about her experience. She asked him if it would help him to see a picture of her. He immediately agreed to the offer.

She ran to the bathroom with her digital camera. She threw off the pajamas and slipped into a short dress. Holding the camera with one hand, and using the other to pull her dress up, she snapped a picture of her bare ass in the mirror. She emailed him the picture.

He replied, “I don’t deserve to see such beauty. You are gorgeous.”

“Thank you,” she responded. “Is it helping you any?”

“It just did,” he typed back. “It was so powerful that when I came, it shot clear up to my stomach.”

She laughed at the thought of it. Men can be so…well, just like men. She told him, “Well, I’m glad I was able to help. After all, you helped through a wonderful time.”

“So, what’s my next dare going to be?” she asked him.

“Hmmm,” he replied. “How about on your first day back at work, you wear a short denim skirt and no panties underneath?”

“I could do that,” she thought to herself. “The students won’t be back on the first day anyway.”

“Okay,” she told him. “I’ll wear a University of Texas sweatshirt that I got for Christmas.”

“No panties,” he reminded her. “and if you’re really daring, you’ll take a picture of yourself mooning me in your classroom.”

“LOL,” she responded. “I don’t think I’ll go that far. No panties for sure, but I’ll have to think about the picture.”

“Fair enough,” he typed back.

On the teacher workday at the start of the second semester, the social studies department was heading off to Chuy’s for a Tex-Mex lunch. Out on the sidewalk at the parking lot, the teachers were all ready to go.

“Where’s Susan?” asked the department head. “I thought she was going with us? Let’s give her a minute or two.”

“Great,” mumbled one of the guys on the sidewalk. “We’re always waiting on the women.” He got a few of the other men to agree with him.

“Don’t even start it,” warned one of the female teachers, “we outnumber you.”

Right then, they heard a door burst open as Susan came out running toward them. The second year teacher was always a little clumsy. One time in her first year, she actually spilled an entire pot of coffee on the student reports she had been grading in the department workroom. The stain was still on the carpet.

As if on cue, she tripped and sprawled onto the sidewalk right in front of the group. The man that had grumbled about late women earlier instinctively rushed to help her up. He gathered up her things where her purse had opened onto the ground.

He picked up her digital camera and handed it to her.

“Here ya go,” he said. “You need to be careful with these cameras. You should have a case for it.”

“Yeah, I need one.” she responded. “I usually don’t have it at school anyway. I just needed it today to…ummm…take a picture of my classroom.”

As they stood up, he couldn’t help but notice the short denim skirt she was wearing and that she was brushing off her hands by rubbing them against the front of her University of Texas sweatshirt.

“No way,” he thought as he froze in place. “Could it be her?”

He’d have to wait until he could check his email. If it was her, this could get really interesting.


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