Melissa and I played pool one night for underwear. She won the first series two games out of three and so I dutifully went to the bathroom and took off my boxers, folding them neatly into a small rectangle which I stored in my back pocket. When I pulled up my jeans I could see my stiffening cock, clearly articulated through the thin and faded denim. I tried to control my erection, but I returned from the bathroom semi-hard. 'Give them to me,' Melissa demanded, and she put my boxers in her purse.
I won the next series and I got my reward right away. Melissa reached under her short, black cotton dress and hooked her thumbs into her black, lace thong. We were in an alcove at the edge of the pool hall and nobody could see us as she pulled her thong down and stepped out of it, standing right next to the pool table. She handed it to me and I noticed it was damp. I could smell her musk on it, and my cock sprang to full attention in my jeans. Without any underwear, there was no hiding it. 'Will you last for one more game?' she asked. 'Winner takes all, loser has to do the winner's bidding.'
Precum was coursing out of my throbbing and pulsing shaft, but I said yes. I needed to squirt so bad I couldn't concentrate and she practically ran the table on me, leaning unnecessarily far forward to take her shots so I could see her naked ass and her pussy lips. She went to the cash register to pay. 'I can't have you walking around in that state,' she said. 'But for my winnings, I want you to go to the bathroom and put on my thong.'
I tried to protest. 'Don't get yourself off yet,' she warned. 'I want to enjoy this.'
I nearly came as soon as I pulled my jeans down but I wanted to fuck Melissa so badly that I held off stroking myself in the stall. I had never put on a thong before, although we'd talked about it during sex and the idea always made me cum. Now I had her soaked lace triangle straining over my obscenely engorged head and the thin string tight against my ass. My jeans barely closed but my bulge was a bit better contained. As we left, every step was painful and also amazing.
Melissa and I kissed on the street and she ground her hips against me. I shuddered every time, it was obvious I was not going to last. We only had three blocks to go to get to her apartment in Adams Morgan but as we passed a dimly-lit park, she said, 'Let's stop here.'
We sat on a picnic table and she pulled off my jeans, licking her lips hungrily at my cock bursting out of her thong. 'Shirt off, too,' she ordered me.
I was sitting on the splintery wood surface naked except for her thong, trembling and desperate. She sat across from me with her knees drawn toward herself, showing me her pussy and ass. 'Masturbate yourself, you dirty slut,' she told me. We had always talked dirty and had fantasies like this before, but this was the first time we'd ever been outside, it was only 12:30am or so ... people were walking by.
Still, I was in no position to say no. I slid my cock out of the thong, with the g-string still bisecting my balls and rubbing my ass and I jerked myself desperately. It took no time at all before I shuddered and burst in front of her, squirting all over the table and my hand and my stomach. She loves watching me masturbate, we do mutuals almost as much as sex itself, and this was one of the best orgasms I ever had. I opened my eyes and I saw Melissa frigging her clit for all she was worth, her thighs and ass naked against the coarse table.
I slid my cum-soaked finger into her and started pulling her towards me from within, hitting her g-spot (don't worry, she's on the pill) and she lost it, moaning and wiggling, shaking and pulsing around me.
This was the beginning of all of our fantasies coming true. I started wearing thongs to work and she would have me meet her afterwards for more public humiliation. Last week, she got Tom, one of her male co-workers, to join us for a session. I jerked him off while she spanked my naked-except-for-the-thong ass. Things are really getting good.