Wow, where do I start. I guess I'll start with who I am. My name is Tina and I am 19 years old. When you hear the rest of this you will be shocked I am 19, but I am. I live at home with my mom, her boyfriend.
I go to the local college and I am a liberal arts major. This year I took a summer job working in the office of a small insurance firm. My dad knows the owner and got me the job. That's how this all started.
The office is small. 7 people. Our boss, 2 guys in sales, a woman who does books, a tech guy, a woman who does marketing, and me. It's a small close knit group. Half of what they say to each other would be grounds for sexual harassment suits. No one cares, it's all funny, but it contributed to what happened. I answer phones, act as receptionist, and do whatever they ask me to do.
The day it all started was just a normal day. We were expecting a client. It was someone everyone in the office knew except me. Having just started I had not met him yet. His name was Dave.
He showed up around 10. Now, I know he is 52. When I saw him I thought he was 40 something. He was not super handsome, but he was better than average. He was tall, a bit overweight, but in that way you'd think you don't want to fight him.
What stood out was he was funny. From the moment he walked in he had me laughing or giggling. He was a flirt but not in a creepy way. I could see why everyone liked him. We chatted, laughed, he met with my boss, he came out, we chatted and laughed some more. Then he left. Nothing unusual.
The next day he sent an email to me. Nothing wild, just a normal welcome aboard, nice meeting you, looking forward to working with you. I responded saying it was fun meeting him and I hope to see him again. That was the starting point. Right there. That's when I invited him in.
He responded that he would not be back for a while but that we could chat by email if I wanted. I said I'd like that. I actually liked the idea. I had free time in the office and chatting with this witty guy would be fun. I gave him my personal email and text and told him to stay in touch.
During that day he sent me a few funny things. Nothing out of the ordinary for me but they were things that obviously required thought and an understanding of my sense of humor. I was enjoying the conversation and light flirting.
The next day few days there were good morning emails from him. We'd chat during my slow periods. As our chats went on he got a little more personal and a little more flirty and sexual. I did not mind. Through our conversations I felt we were really getting to know each other.
One particularly slow day he asked what I was doing. I said nothing, that the office was slow today. He said I should spice it up.
I asked how and he said, "You're a pretty girl, I am sure you could spice up any room."
I replied and asked how he suggested I do that. His response was that he could think of something.
I asked him to tell me, and he asked if that was a dare.
I hesitated. I'd played truth or dare in high school, it was always sexual. Was this conversation going that way? I figured what the hell, a dare or two might be fun. So I said yes, I dared him to tell me how to spice up my day. In return he said only if I promised to do it. I told him I promised. After all, he was not here and no one could force me to do anything.
He said. "Before I dare you, tell me what you wore to work".
I was feeling flirty so why not. I guess you want to know about me. I am 5'2 125. I have long brown hair to the middle of my back. I am told I am pretty. I don't have that angular straight line face models have. Mine is more round girl next door.
I was wearing a blue pleated skirt and a cream blouse. He wanted more. How long was the skirt, how many buttons on the blouse, was I wearing stockings, and what I was wearing underneath. This was a little fun. He was in another state, so what harm in telling him. I told him I was wearing a matching thong and bra, white with pink lace. He responded appreciatively.
He said, "Here is your dare. Pull your skirt up so you are not sitting on the back. So you can feel your ass against the seat. Let the front fall where it may."
The dare was pretty easy. My desk was where everyone could see me, but people were busy and no one was looking. I agreed and while sitting pulled my skirt up as far as it would go. Then I scootched up just enough to pull my skirt out from under me.
Just as I did that I looked to my left. One of the sales guys, Tom, had seen me. I felt my heart jump. I also had to admit it was hot. My skirt front was about 2" from my crotch and I was caught pulling it up.
I quickly told my friend what happened. He asked how it made me feel getting caught. I had to admit it was a rush of excitement. Even though I'm 19 and don't have a lot of experience, I always liked being looked at.
Here I was showing off in the office. My heart was beating faster. I was very nervous but I had to admit it was also fun. I told him exactly how I felt. He asked me if it was a turn on knowing I'd been caught. It was and I told him. He asked me if the sales guy was still checking me out. I looked over. He was looking at me but all of a sudden he turned and looked away. I pretended I didn't notice.
I told Dave he was looking at me. I took a makeup mirror out of my desk and put it on top in a position where I could see Tom. I could see he kept on checking out my legs as I sat there. Again I told Dave what was happening. He again asked me how I felt about it. I started to see a pattern. Every time he asked me about something he asked me how I felt about it.
I told Dave exactly how I felt. He asked if I was ready for my next dare.
I was intrigued now. The last one was fun. Tom was still checking me out. I wondered what next dare would be. I told Dave I was ready. He said I dare you to scratch your upper thigh almost all the way to the band of your panties pulling your skirt up as you go. I thought about it. I knew Tom kept looking. I knew if I did the dare he would see me do it. The idea both scared and excited me.
I told Dave okay. Dave responded for me to tell him when I'd done it and what, if any, was the sales reps reaction. I still had my make up mirror on my desk. I dropped my hand to my thigh and started scratching my thigh. The sales rep saw me and just watched. I could see him by looking in the mirror. He kept glancing away hoping I wouldn't catch him but he looked more and more.
Slowly I slid my skirt up as I scratched. As I did, Tom looked away less and less. I could feel the front of my skirt slide up. It was pretty much in my lap. As my hand moved up I was exposing more and more of my leg. Since I wasn't sitting on my skirt I also was exposing the side my ass. By the time I got to the top Tom was just staring at me. I pretended not to notice.
I pulled my hand away I let my skirt fall back into place. The side dropped down but the front stayed almost up to my waist. If someone came to my desk they would see my panties. I'm not sure if the sales rep could see them from where he was.
I told Dave would happened. Again he asked me how I felt. I told him I was extremely nervous but that was really fun. He asked me again if I was turned on. I had to admit my pussy was wet. I just told him it made me feel sexy. He asked if I wanted my next dare.
I knew that I shouldn't. I was feeling excited and hot but I said, "that's enough."
Even though I said it, I knew I wanted more, but I was glad I said it. We reverted back to our regular chat.
When it was time to leave, he said, "One more dare."
I doubted I'd do it, but asked what it was. His dare was for me to only wear skirts and dresses from now on and no matter what, not to sit on the back of them. Always have my ass directly on the seat.
I replied, "We'll see," and headed home.
The next day I started to get dressed. I looked in my closet. Dave's words came to mind. What the heck, I thought. I pulled on a short skirt and top.