Chapter 2

Jess and I continued daring each other for a while. Not many were as extreme as my thong display, but Jess did love getting me in situations where I could be caught - once she dared me to wear a thong to work, and then jerk off into a cup, and then take that cup back to my desk and drink it. I had a brick red face, but got hard again as that salty taste touched my tongue. I dared Jess to keep herself on the edge for a whole day, rubbing herself every hour while having small elastic bands around her nipples, and I forbade her from wearing a bra. That night as she jumped me she told me that she felt eyes on her all day making her hotter and hotter, sure that her colleagues could see how turned on.

The next big step forward was a weekend where we didn’t have any plans. We were sitting on the couch watching TV - a wasted afternoon. Jess suddenly looked over at me.

Jess - Come on, let’s go out, let’s do something. Anthony - Okay, where do you want to go? Jess - let’s make that a surprise. Actually. I have a dare for you. While we are out you have to do what I say. For each time you disobey me you’ll have a punishment when we get back. But if you do everything I say, I’ll do whatever you want when we get back. Anthony - Okay, you’re on. You know I’ve been dreaming about your ass though, you know what I’ll want for my reward!

Jess winked at me, and licked up my cheek, until she reached my ear where she whispered “You’ll have to earn it”. We jumped in my car and headed straight into town. I was wearing normal clothes, jeans and a shirt, but Jess had a tartan thigh length skirt with knee high socks, and a white shirt, and was looking hot. As we arrived in town she grabbed my hand and took me directly to New Look. Jess took me directly to the underwear area, and started looking through the thongs. She would hold each one up to my hips, and loudly critique it, saying things like “This would look good, it would really make your ass look good”. I could feel my face start to heat, and my heart raced. As Jess held each pair against me she would take the opportunity to brush her hand against my cock, which was starting to stiffen in my jeans. Jess selected three choices, a pink lacy thong, a red glittery thong, and a white pair that was barely more than two strings tied together, and led me over to the changing room.

Jess - Go into that room, take everything off and try the red pair on. Call me when you’ve got them on

I grabbed them off her, and tried to slide into the changing room without anyone seeing me, hiding the underwear in my hand. I stripped off, and pulled the red pair up my legs and settled them over my hips. I felt the back slide between my cheeks, as my now hard cock popped out the top.

Anthony - All done. Jess - Well, I want to see. Open up the curtain. Anthony - No way, that’s not happening. I can’t do that in public! Jess - Uh-oh, that’s one. I guess I’ll have to come to you then.

Jess joined my in the changing room, and in a loud voice told me how cute I looked. I was begging her to be quiet, but she kept on saying how cute I was. She then whispered in my ear “If you want me to be quiet you better get on your knees and get your tongue been busy”. I couldn’t stand it, I was so humiliated, although you wouldn’t know it to look at me, I was harder than ever. I immediately dropped to my knees and pushed her skirt up. She didn’t have anything underneath her skirt, so I started tracing her pushy lips with my tongue. She grabbed my hair and pulled my head against her, pushing my tongue inside her. Jess rode my head for a while, until I felt her juices starting to run down my chin.

Jess - I want to spank you now. Will you lie over my lap? Anthony - Yes mistress.

She sat down on the bench, facing me to the mirror at the back, looking into the reflection of my eyes. She started my reaching under her own skirt, getting her fingers wet with her juices, and then wiping them all over my ass. As she moved her fingers around she would occasionally buzz against my anus. I whispered up to her

Anthony - Please, not inside me. Not here, not like this Jess - Okay, but that’s two now. And I’m going to give you an extra five. Anthony - Yes mistress. Thank you mistress.

Jess took the palm of her hand, and squeezed my right cheek, rubbed it up and down, and then lifted her hand away, and brought it back down in a firm spank. I closed my eyes as my body rocked forward away from her hand, before I felt her repeating the process with my left cheek. She spanked me five times on each cheek before leaning down and whispered in my ear, telling me to open my eyes and look at her in the mirror. As I opened my eyes, to my horror I saw the curtain behind me was now slightly open. I couldn’t see anyone through the gap, but the risk made me moan as Jess spanked me again, my cock rock hard against her lap. In a panic I moved my feet, trying to subtly close the curtain. Jess continued to look in my eyes, palming my ass, smiling broadly at me, as she said in a husky voice “that’s three, now youre mine”. Jess finished up my spanking, ten on each cheek, before standing up and kissing my cheek gently