I started chatting with an older woman online and from the chat, I could tell that she had submissive tendencies. As we chatted more and more, I began to drop subtle words to see if she was open to them. I would say something and based off her response, I would say don't make me put you over my knee when we meet. Her response turned over time from mmmmm to what would you do to me if you did?
Our chats began to take the Dom/sub roles. Yes Sir, became her usual response and my chats took on more of a Dom/sub roleplay where I would ask her her would she do something for me when we meet......would you go take off your panties if I asked you in a bar?.....would you let me finger you at the bar, make you cum?.....each response was always If you like, Sir.
I was finally able to meet her and she was given instructions as to what she should wear and how she should address me. The day came and we met at the hotel bar I selected and she was indeed dressed as asked. Her 5' 8" 150 pound frame (a little chubby, but very sexy) was indeed in white thigh highs (signaling her submissive virginity) short leather skirt, white lacy thong, and push up lacy white bra under a v-neck button down. Very sexy, yet submissive, and very needy looking.
We sat at the bar and after some flirting and small talk, I slid my hand under her skirt and ran my hand higher until my fingers gentlystroked her thong covered, wet pussy. I said to her to go remove her thong and when you return I will tease your clit until you cum.
She left for the bathroom and when she returned, she handed me moist, white, lacy, thong. I placed my hand on her thigh and told her to move up on the stool and spread her legs slightly for me. She did as commanded and I slid my finger along her slit. She was very wet and as I did I could see her bite her lower lip and close her eyes. I leaned into her and said, "do you want me to make you cum here?" She said, Yes Sir, please make me cum.
I slid my finger in her and she gasped loud enough for the woman next to her to turn and look. I started to pump my finger in her and she kept her eyes closed while licking her lips. I told her to open her eyes and look to see if anyone was watching me finger fuck her. She squeezed her legs shut and leaned forward and said that the man in the booth behind me was watching. I said to open her legs wider or I would take her in the back alley, strip her and fuck her there.
She spread her legs wider and I continued to finger her and told her to look at the man until you cum. Knowing that she was being watched made her get close to orgasm quickly. Sensing this, I stopped fingering her. She groaned and said, "please, Sir, make me cum." I said that I would but that she would have to pay for closing her thighs before. She said, "Sir punish me as you wish, just make me cum."
I started to stroke my finger in her and noticed the man watching and the woman next to her sneaking peaks. Soon, she closed her eyes, gave a silent moan and had her orgasm. I paid our tab and said to her that it was time to go as she needed to be punished.
