The Chaperone Pt. 02

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.

After about an hour, enough beer had been consumed for the guys to be a little less gentlemanly. George gave Sarah a playful slap on the ass whenever she passed by and Ben purposefully dropped things on the floor so that Sarah would have to bend over giving him (and half the room) a clear view of her panties. I stood up and the room fell silent. The guys had been waiting for me to take things a step further and I wouldn't disappoint them.

"So I've been talking to Damien here," I indicated a guy next to me, Damien "and we agreed that for every beer he drinks Sarah will remove one article of clothing". Once again the color drained from Sarah's face. She shook her head but all the men cheered.

"Yeah Sarah!" shouted George

"Come on, Sarah," shouted Ian. I could hear the lust in his voice.

"Damien has already finished three beers so Sarah, time to start stripping," The room fell completely silent all eyes on Sarah. I held my breath, not sure if she would comply. My modest little Sarah. I now had her stripping before a room full of horny men. Part of me felt ashamed of myself. But the other part of me convinced myself what I was doing was for Sarah's own good. I doubted she'd be sneaking out to any more parties in the future.

Slowly Sarah kicked off both heels. They lay in a pile in the corner. Then, after a second's hesitation, she slipped off her skirt. It fell around her ankle. The panties I had chosen were see through, exposing her neat little bush which I'm sure captured every one's attention. Damien hastily started jugging his next beer. Ben dropped the remote control and raised his eyebrows expectantly at Sarah. She bent over quickly but we could all see that delicious ass crack wiggling tantalizingly at us.

Another twenty minutes Damien stood up and announced he had finished his next beer. We all turned to Sarah who had been sitting in a chair in the corner her legs crossed tightly looking very uncomfortable. She stood up nervously and pulled her shirt over her head. Her breasts sprang forth, the first time I had seen her bare breasts. Her nipples were large and very kissable, as though they were begging me to suck them. She crossed her arms across her chest looking embarrassed, still keeping her legs crossed.

"Fuck!" gasped Ian, "Sarah your tits are amazing." He quickly excused himself to the bathroom. When he finished Damien went too. I think we all knew what they were doing but were too polite to say anything.

Then Damien finished his fifth beer. Sarah stood up, then turned to me her expression pleading. But I had downed quite a few beers myself and wasn't going to be moved. I shook my head letting Sarah know there was no way out. She wriggled out of her panties which fell around her ankles. I bit my lip to keep a cry of lust from escaping. At first there was silence then I made my way to the front of the room where Sarah was standing. Before she realized what I was doing I snatched her panties off the floor. Just like last night they were dripping, saturated with her juices. She blushed and hung her head as I fingered her wet panties, sticky like I knew the inside of her thighs must be. Then I handed it to George who passed it around the room. Sarah began to sob with embarrassment.

By now, I felt a little bad. Things had gone a little farther than I had intended when I first created the plan. But obviously, from the state of her panties, she was enjoying every minute of it. I wondered what else she would enjoy.

"Now" I said "Sarah is going to provide the evening's entertainment. She will take any requests/ questions you ask as long as they do not involve touching you," I sat down in my chair and waited for the men to go to town.

Sarah's POV

I was standing completely naked in front of a room full of virtual strangers (and Kyle) and I was 100% sure this was not a dream. Sure, this had been a fantasy of mine as far back as I could remember. But now that I was actually experiencing it, I had no idea what to feel about it. Kyle just sat there, in the armchair sipping on a beer. His expression was still unreadable but his eyes hadn't left my body since I had removed my panties.

"Hold your tits up for us," one man asked. I did so, holding a breast with each hand. They were too large and spilled over a little causing the men to cheer.

"What size are you?" another person asked.

"D," I said my voice trembling slightly.

"Let go of your breasts and jump up and down," That request came from Ian. He had a smirk on his face and I knew how much he was enjoying this from the bulge in his pants. I closed my eyes and jumped several times. My breasts bounced with me almost comically, like a girl in a porn movie. Some of the other guys in the room adjusted their pants to hide their own boners. The knowledge that I was turning them on was also turning me on. The insides of my thighs were sticky with my juices.

As though sensing my thought patterns one of them called "Hey Kyle spread her legs will you? We want to see her cunt!"

There was a gasp at his terminology but all the men stared at Kyle waiting for him to heed the man's request. Wordlessly Kyle got to his feet and walked over to me. He picked me up and spread my legs so that my pussy was on display to everyone.

"Jesus, she's getting off on this," one of the men said in wonder.

"She certainly is," Kyle whispered in my ear. I bit my lip to keep from whimpering. Kyle took his hand and rubbed it against my thigh then raised his hand to the group so everyone could see how wet I was. I was so horny I thought about grabbing Kyle's hand and forcing it on me but he gently lowered me to my feet and returned to his chair wiping my juices off on his pants.

"So Sarah, how often do you masturbate?"

"Uh," The truth was quite often "Not that much."

"How many times a week?" demanded Ian.

"Uh...every day," The room exploded in more cheers and whistles. I hung my head.

"What do you think about when you masturbate?" But I shook my head. I refused to answer any more questions. These strangers already thought I was a slut. How could I confess my innermost fantasies to them like that?

Kyle got to his feet slowly. "I can answer this one," he said "Sarah here is a very naughty little girl. She thinks about guys eating out her wet, dripping pussy. And she also thinks about guys eating out her tight little ass. And guys fucking it." I pressed my hands over my face to hide it from view.

"Hey Sarah," I recognized Ian's voice "Do you ever think about Kyle fucking you? In your cunt or your ass?" There was silence.

"Answer the question Sarah," It was Kyle. He said it quietly but I could still hear his voice shake. Slowly I nodded and removed my hands from my eyes. Kyle, satisfied, returned to his seat.

"Hey Sarah, why don't you turn around and show us your ass?" Another request from Ian. He was enjoying this way too much. But I did as he ask, bending over while keeping my cheeks firmly together. There was booing.

"Noooo, spread your cheeks Sarah. We want to see your little bumhole."

I did so, feeling the air on my ass and praying my ass was clean enough to pass inspection. One by one each of the men came and took their turns looking at my ass making comments as they did so.

"What a tight little hole."

"Mmm, my dick would just rip that apart."

"So sweet, I'd love to suck on that."

When they had finished I stood up again my face red from the blood flow and the humiliation of having to show my most intimate parts to a room full of strangers.

"Sarah," It was Ian again "Do you orgasm a lot?"

"Not that often. Hardly ever actually" There was a flurry of surprise. Clearly a girl who was so horny should not have a problem orgasming. Kyle also looked surprised.

"Maybe you should try it here," suggested the handsome guy that had opened the door "So we can see if you're doing it right." I looked at Kyle but he only said "Show them Sarah."

I closed my eyes trying to pretend I was in the comfort of my own bed but I could still feel the stares on me as I began to massage my clit while slipping two fingers into my pussy. I felt them slide in easily and whimpered with satisfaction. Then, as though I had lost all self-control, I began finger fucking myself moving my body back and forth my breasts also bouncing. I suddenly felt Kyle's breath against my ear.

"Touch your clit more Sarah," I listened to his advice and almost fell over as the sensations poured through me. He continued to whisper (whether the room could hear him or not I don't know), "That's it Sarah. Fuck, you're such a beautiful girl. I've wanted you since the first night you arrived here, wanted to take your ass, your pussy every fucking inch of you. It's been driving me crazy." My movements became more frenzied and I felt the pressure mounting. I heard Kyle's heavy breathing and knew the affect I was having on him. Then I felt his lips on me as he placed his mouth just under my ear and kissed gently. I came suddenly the force of my orgasm almost knocking me over. I felt Kyle put his hands on me to steady me as I felt my body shudder with my release. I kept my eyes closed and lay there in his arms for several moments. The room was silent.

Kyle cleared his throat. "Well guys, Sarah's had a long day, I think I better take her home."

"Wait," Ian said "We have one more question"

Kyle's POV

"So here's your question Sarah. Do you like sucking dick?" Even after all that she had been through Sarah still blushed at the question. She was such a sweetheart.

"I guess so."

"Are you good at it?" Sarah looked surprised. She shrugged.

"Well why don't we be the judge of that?" Ian asked "Why don't you suck Kyle off?"

Every dick in the room was hard after Sarah's performance including mine. I was so hard it was almost painful. Honestly, I expected Sarah to say no but instead she dropped to her knees then turned to face me. Her face was red and flushed and her eyes sparkled. She kept her eyes locked on mine as she unzipped my fly and took out my hard member. I gasped with excitement as she expertly stroked it several times before taking the entire length of it in her mouth and began sucking.

Within seconds I could answer Ian's question. Yes Sarah was good. Too good actually. It took all my willpower not to come right then and there. I began thrusting my hips back and forth and heard her gag on my dick but when I looked down her eyes were still staring playfully up at me. Finally, she took my dick out of her mouth then playfully licked the tip. I immediately shot my load all over her face and tits to the applause of the other guys. I wished we were alone.

The ride home neither of us said a word. What could we say? We had left soon after my orgasm each of the guys giving me a pat on the back or a fistbump. Sarah had gotten hugs from all the guys of course especially Ian who told her to call him first chance she got.

When we got home, I immediately went upstairs to my room still trying to process the events of the night. Part of me felt guilty. Why kind of person degraded an 18 year old girl like that? But the other part of me told me to turn around, march downstairs, yank those panties off Sarah and fuck her until she came in my arms again.

Watching her masturbate before had been intoxicating. I had relished whispering in her ear seeing her shudder with each vibration of my voice and knowing that it had been my kiss that had sent her into ecstasy. I heard a noise behind me. Sarah was standing in the doorway.

She was completely naked but this time made no attempt to cover her body. Her breasts hung there proudly, and her pussy glistened. She stepped closer to me.

"Thank you Kyle," she said. And then she kissed me.

It was electrifying, something our bodies had both been craving since we had first seen each other. Our tongues mingled together and our bodies hummed. My cock stirred to life pressing against my jeans until the sensation became almost unbearable. We stopped kissing so I could fumble out of my clothes. I felt her eyes roam my body taking in my chest, and my large dick. We resumed kissing, as she began to stroke my dick furiously. I pulled away.

"Sarah," I said breathing heavily "I want to show you things you've never seen before. I want to make you feel good." I spread her legs and looked her in the eyes meaningfully so she would know my intentions. Then I lowered my mouth and took her pussy in my mouth. She was just as wet as I expected. I eagerly licked up her juices- her pussy, her clit and the inside of her thighs as she thrashed around me whimpering. I used my tongue to tease her slowly licking her clit till she was on the brink then pulling away. When I felt her growing close I pulled my mouth away chuckling.

"No, no, Sarah. We haven't even started yet. I'm going to make you feel so good baby," I gave her another lick then told her to turn over. The expression on her face told me she had not been expecting this.

"Turn over," I repeated. Sarah looked away embarrassed.

"Kyle," she said "What if you don't...like it? What if you think it's gross?" How could I explain it to her? Every inch of her body was perfect, every curve, every hair, everything. She had nothing to be self-conscious about. I wanted to explore all of her, taste all of her, smell all of her. There was no way I could explain this so I flipped her over and spread her cheeks.