This is a continuation of The Chaperon. Reading them in order is not necessary.
*****
Sarah
I had no idea what to expect the following morning. Thinking about the previous night- the outfit, flirting with Ian but most of all the spanking- made me want to curl up in a fetal position out of sheer embarrassment. But some part of me relished the feeling of his strong hands on me, taking control of me, dominating me. And had he been enjoying it to? Or was that just my drunk, overactive imagination?
I didn't wake up until about two in the afternoon and when I came downstairs Kyle was waiting for me at the breakfast table. He looked up when I came in, his expression blank and unreasonable.
"Kyle I-"
"Me first Sarah," he didn't raise his voice but I still flinched at the disapproval in his voice.
"Your behavior last night was out of control. And since it's my job to keep an eye on you, there are two options. The first option is I tell your dad. Everything, including the fact that you were about to hook up with some guy you just met. And don't act stupid Sarah. I know what was going to happen. The second option is that you accept the punishment I give you."
"What's the punishment?" I was secretly hoping for another spanking. I hope it didn't show on my face.
"Nope. Decision first, details later," Well, it wasn't really a decision. I knew that if my dad was informed, I'd be locked away in a tower until I was thirty. There would go the rest of my summer. On the other hand, I trusted Kyle. And since he had been pretty wild in his own teenage years, I figured maybe he'd give me a break.
"I'll accept the punishment."
"Good," Kyle said, looking pleased "Now all you need to know for now is that tomorrow night you'll be accompanying me to a party" A party? What kind of punishment was that? He refused to answer any more questions, but simply insisted I drink water to prepare for the "long night ahead".
I didn't get any more details until around seven o'clock when Kyle called me upstairs. He was standing outside my room and said "I laid out an outfit for the party. Go see if it fits"
The "outfit" in question looked like something a hooker might wear but I wanted to cooperate so I put it on. A pair of see through panties (my cheeks flamed at the thought of him picking out panties for me), a miniskirt that exposed my panties and a tight shirt that clung to my chest making it look as though someone had slipped melons in my bra. I felt extremely self-conscious, like I was naked.
"Well let's see it," Kyle called through the door. I thought about protesting but once again did not want to be seen as being uncooperative so I opened the door. Kyle's eyes widened when he saw me and he hungrily looked me up and down. For a moment, I saw a look of pure lust on his face and began to feel a mounting pressure between my legs as I grew wet and sticky. Then, quickly, it was gone.
"Perfect!" he declared "Except one thing. No bra".
"What?" I blushed, mortified at the thought of my large breasts being on display for him, and everyone to see. I wouldn't be able to walk two feet without them bouncing.
"All right, then the deal's off," He looked dead serious. I went back into my room and removed my bra. As I suspected my shirt barely stretched over my shirt. My hard nipples very clearly showed through the material and I crossed my arms over them to prevent them from bouncing. When I showed Kyle he nodded his approval then turned away making me even more self-conscious. I couldn't believe I was standing here with every inch of my body on display for him.
"Here," Kyle handed me a pair of brand new stilettos. I had never seen heels that high. I had a legitimate fear of breaking my neck while wearing them but put them on anyway feeling my breasts bounce obscenely with every movement. I sensed Kyle's eyes staring but when I looked up he was staring determinedly away.
I didn't believe that Kyle would actually take me to a party dressed like this until we were actually in the car. I walked to the car quickly, my breasts swinging with every step. I looked around to make sure Ian or Lori hadn't seen me but thankfully their driveway was empty. Even once we got in the car, I thought Kyle was just going to drive around to scare me. Then we pulled into the driveway of a red brick house. Several other cars were parked in front and the lights were on, indicating people were home. Kyle turned the car off and I grabbed his arm, terrified.
"Kyle," I pleaded, "Don't make me go in there!" I felt naked, humiliated. Kyle shrugged, impassively.
"You're the one who wanted to dress like a slut. You should be thanking me. Now let's go before I have to come over there and drag you inside."
The thought of being dragged anywhere in this skirt was enough to get me to move. Kyle rang the bell and it was answered like a handsome scruffy looking guy with shaggy hair and an Avenged Sevenfold T-shirt. He and Kyle exchanged some complicated hand shake and he held the door open for us. Kyle walked in and I followed. I felt the guy's eyes on my ass as I passed him and struggled to take small steps to reduce the bouncing of my breasts.
Right away I noticed the "party" (there were only four other guys besides the host) was all guys. They stared at my appreciatively as I stood next to Kyle, my hands across my chest, but thankfully I didn't recognize any of them. Then I heard my name.
"Sarah," Ian was standing in the doorway to the kitchen, a beer in hand. I looked at Kyle, furious, but he only smirked.
"Guys," he called "Meet Sarah. My slut and our server for the evening. Whatever it is you want, another beer or a back massage, Sarah's your girl. And don't be afraid to look. Sarah loves it when people stare. As well as a few other things" The guys cheered including Ian. I felt mortified. Kyle had been right about one thing: it was going to be a long night.
Kyle
The first hour of the party I watched Sarah carefully. I left her alone and most of the other guys did the same. They were all good guys, none of them would have done this if they had thought I had brought Sarah here without her consent. It had actually taken some convincing for some of them. But once I mentioned she was over the legal age and her bra size, they agreed to help a guy out.
Inviting Ian was, in my opinion, a stroke of genius. He was a cocky bastard and I knew Sarah was shy around him. Having him witness her degradation would make her humiliation complete.
