WEDNESDAY
The next morning, I arrived at school as usual and went to class. By second period, I noticed something strange—a few pretty girls actually made eye contact with me in the hall, and a few even said, “Hey” at me and smiled as they walked by. Initially, I was surprised and didn’t respond, but after a couple of times, I nodded, or said “hey” back.
When I was at my locker, before lunch, I waited, as I always did on Mondays, Wednesdays and Fridays, for Dana to walk by. For most of senior year, seeing her walk by was one of the highlights of my week. Today, however, instead of just walking by me without a glance, she stopped and came over to me. She looked great, as usual.
She put her hand on my shoulder, leaned into me so that I got a strong whiff of her scent and whispered in my ear, “I hope you don’t mind, but I mentioned some of your hidden talents to some of my friends. I think it might be a good thing for you and maybe it will make up for my bad behavior.” She squeezed my shoulder and pulled away. “Tomorrow at 5, again,” she said, maybe a bit louder than necessary.
“Yeah, see you then,” I croaked, as she walked away.
I was still overcome by her presence as I watched her ass wiggle down the hall. I realized that everyone in the hall was watching me, so I tried to pull myself together and go to lunch.
I joined Fred and Gina at our table. Gina started in on me right away.
“What the fuck is with you? You’re like some sort of man-slut,” she hissed.
“What are you talking about?” I asked, feigning ignorance.
“Look, I know what happened with you and Dana.”
I shot a look at Fred, who sputtered, “I didn’t say anything.”
Gina jumped in, “No, he didn’t have to tell me, it is all over the school. I was in the girls’ room, and everyone was talking about how you and Dana had done it, and that she said that you were quite the stud.”
I had to smile. Dana really did control the social network here. She could have said that I had horns and a tail, and people would have believed it.
“Why is that any of your fucking business?” I asked Gina. “I know that this whole thing is out of the blue, but can you blame me? You don’t get to tell me who I can date, or sleep with.”
She stood up and said, “I just thought you were better than that, that you wouldn’t just become whatever with Dana after the way she has treated us.”
I responded, “Look, I have been basically a social outcast forever here, and now things are going my way, for whatever reasons. I plan on taking advantage and making up for lost time.”
Gina turned and stormed out of the cafeteria.
I turned to Fred and asked, “What’s her problem?”
He looked at me, as if I was the crazy one, shrugged and started to eat his sandwich. We ate together in silence, and I could sense the eyes of everyone in the cafeteria staring at me.
Before going home, I decided to stop at the coffee shop for a latte. I entered the shop, and savored the spicy coffee smell. I ordered my drink, and while it was being made, I noticed that it was pretty crowded, groups of high school kids drinking and goofing around, older people working on their laptops and one old guy, just sitting and drinking coffee. I saw this one cute redhead sitting alone, staring into an iPad, drinking coffee. She had a pile of textbooks on the table.
I realized that one thing that I hadn’t had the nerve to do yet was to ask a strange girl out. Someone who wasn’t already set up to sleep with me, for example. I remembered the advice I had gotten at the lake house, to be confident and not scared. So, I decided to challenge myself and to ask this redhead out for a date. If she said, no, at least I had tried, and I figured it would get easier each time. And if she said yes, then I would have a date with a cute girl.
I got my latte, screwed up my nerve, took a deep breath and went to her table.
“Excuse me,” I asked, “can I sit here?”
She looked at me with surprise and swiveled her head around.
“Why?” she asked, “there are empty tables.”
“Because I wanted to meet you,” I said, with as much bravado as I could fake.
She blushed, and said, “O.K., I guess, have a seat.”
“I’m Jack,” I offered, sticking out my hand.
“Fiona,” she said, shaking my hand.
I sat down and gave her a closer look. Red hair, shoulder length. Light brown eyes, fair skin, nice looking. Irish, probably. Nice tits, it appeared. She was watching me look at her.
“I go to North,” I said—”you?”
“South,” she said. “So, I guess we have to hate each other,” she joked.
“Not necessarily,” I said, trying to make conversation. “What year?” I asked.
“Senior,” she responded.
“Me too.”
We mentioned the names of people we knew at the other school, and realized that we had both been on our schools’ math league team. It was clear to me that Fiona was about as socially inept as me, which, strangely, made me more comfortable. We chatted about school, and college (she was going to be going to a very good school on the West Coast), and before long, we were finished with our coffees. It was time for me to put up or shut up. I asked her to go to a movie with me that night. She seemed surprised, but agreed. We made arrangements for me to pick her up, exchanged cell numbers and went our separate ways.
I went home, and Sarah was sitting out at the pool with some big, muscled guy, who she introduced as Dave, one of her friends from college. Sarah’s bikini left little to the imagination, and I briefly flashed on her naked before rushing that image out of my mind.
I asked her if they minded if I swam some laps, and they didn’t, so I changed into my suit and started swimming laps, thinking about what had gone on at school. When I came out of the pool, Sarah and Dave were gone. When I went up to my room to change, I could hear them going at it in her bedroom. I was happy for her. I went upstairs, went on line for a while, then showered and changed for the date.
I picked up Fiona at her house on the other side of town. She looked very nice, conservatively dressed, but I could tell that she did have a pretty good body. We went to a restaurant for a quick bite before the movie, and we both labored to make conversation. We went over some of the same areas as earlier, and discussed our families, schools, and the like. At one point, our hands briefly touched, but she pulled back, as if shocked. Which was not a good sign. We then went to the movies and found seats about halfway back. Of course, we had to share an armrest, and we kind of jockeyed for position, finally ending up with my arm on the bottom and hers resting on top of mine. The movie was O.K., and after, I drove Fiona home. I tried to kiss her goodnight, and she turned her face, so I kissed her on the cheek. I drove home, a bit frustrated.
It was about 11 when I got home. Dad was talking to Sarah with the TV on.
“How’d it go?” she asked.
“Not sure,” I responded, “actually, not so great, I think.”
Sarah responded, “It was good that you did it, maybe next time will be easier.”
“Yeah, I guess so,” I responded. We chatted a bit longer, then Dad went upstairs.
I went to my room and checked Facebook. I sent out a friend request to Fiona, and to Dana, and was about to go to bed when my phone went off. I had a text, but it was not from Fred, as I expected.
It was from Cara– “Jack, get over here now. I need you.”
It had been a long day, and it hadn’t ended well. Plus, I had school tomorrow. I thought about the fact that I was about to turn down likely kinky sex with a beautiful college girl and texted back, “I can’t now, sorry.”
A minute or two later, she responded, “Really? Don’t make me do this myself.”
There was a picture attached, and when I downloaded it I was looking at a closeup of Cara’s shaved pussy, with her middle finger stuck inside.
I closed the picture and responded, “On my way.”
I decided that school the next day was not a big deal. I went down stairs, and Sarah asked me what was going on.
“I think I just got a ‘booty call’ text from Cara, so I figured I’d go there and check it out.”
Sarah laughed, and said, “Cara, unbelievable. So, Jack, the night won’t end in frustration, I guess. Just be careful.”
“Yeah,” I responded, rushing out the door.
I got in my car and started driving to Cara’s house. My phone rang, and it was Cara. I put it on speaker and put the phone on the seat.
“Are you on your way, Jack?” she asked, sounding a little drunk.
“Yes, I’m in the car,” I responded.
“I thought I could convince you.”
I laughed, “You can be pretty persuasive.”
“When you get here, no one is home. The door is open, so come on in. My room is at the top of the stairs.”
“Got it,” I said, navigating the car over the dark roads, driving as fast as I could.
“I’m naked,” she growled, in a low, sexy voice. “My pussy wants you bad,” she moaned. “Tell me what you are going to do to me when you get here,” she pleaded. “I’m a very bad girl and need to be punished.”
I figured that I had to play along. “You are a bad girl,” I said with a snarl, “I’m going to put you over my knee and give you a spanking.”
I heard her sigh and say, “Yes, I deserve a spanking. Then what are you going to do?” she asked.
I had no clue what to say, but I figured I needed to say something, “I’m going to tease your pussy until you beg me to fuck you,” I said, trying to sound like I had a plan.
“Oh, yes,” she moaned, “Then what?”
“Um, then, when you are begging me to fuck you, I’m not going to. I’m going to tease you more, until you can’t take it anymore and are crying and on your knees pleading for me to take pity on your unworthy pussy.”
“Yes, Yes,” she panted.
I continued, “Then, when I am satisfied that you are sorry, I’m going to shove my rock hard cock into you and pound your pussy until you scream with pleasure and cum.”
“Oh, yes, that is what I want,” she sighed.
My cock was already rock hard against my pants as I pulled into Cara’s driveway. I ran into the house and up the stairs to her bedroom.
As promised, Cara was lying naked on the bed, with the phone in one hand and her other hand fingering her crotch. Her puffy nipples jutted out from her small, shapely tits and she moaned softly as she gently pleasured herself.
I ripped off my clothing and without another word, I sat on the bed, and said, “Take your hand off of there. Only I can give you pleasure tonight, but you have been a very bad girl, and you need to come here for punishment.”
She crawled over to me looking contrite, and positioned herself on my lap, her perfectly shaped ass, and her tattoo, offered up for me to mete out my discipline. I noticed some bruising on the smooth pale skin of her ass. My cock pointed to the ceiling, wedged between her hip and my stomach.
“Yes,” she said softly, “I need to be punished.”
I slapped her left butt cheek pretty hard, so that I could see the red outline of my fingers before it faded, and she sighed, with what sounded like pleasure. I alternated slapping her cheeks, gradually increasing the power of my strokes, and she arched her butt up to meet my hand, growling, moaning and sighing as I hit her. I slipped my left hand between her legs, and it was drenched by her juices as I began to finger her pussy while spanking her until she was on the verge of climax.
I figured, what was good for the goose was good for the gander, so I said, sternly, “You miserable slut. You may not cum until I tell you to,”
When she didn’t answer right away, I smacked her ass hard, and said, “Did you hear me?
She quickly and meekly responded,”No, I won’t cum until you tell me to.”
I told her to get off my lap and lie on the bed, and she complied.
I looked at her slim body and shaved pussy and then buried my face in between her legs, drinking in her scent and feeling her juices. Then, I remembered my “promise”, so I slowly began to lick her and finger her until her ass began to lift off the bed and pressed her bare pussy against my face. I kept going slowly, occasionally flicking my tongue against her clit, causing her to moan and writhe wildly. I gradually increased my pace, and she did, too, until she was bucking against my face and I held on to her ass. I reminded her that she was not allowed to cum and she started begging me to fuck her,
“Stick it in,” she yelled, “fuck me with your cock, now, please,” she bellowed.
But I would not. I needed to be a man of my word. I slowed my pace a bit, and brought her down from the verge of climaxing, then slowly increased my tempo until she again was lifting her hips to my mouth. I then started to tease her asshole gently with my fingers, slick with her juices, when she pressed down and my finger slipped into her asshole up to the first knuckle. She screamed and began to buck up and down so that on the down strokes my finger went further up her ass and on the up stroke, my tongue flicked against her clit ring and clit.
I essentially stayed still while her hips did the work of bringing her to close to an orgasm, so I said, “O.K., you can cum now,” and she reached a screaming, shaking orgasm.
“NOW, PLEASE, FUCK ME,” she screamed.
I stood up, and said, “Not until you get on your knees and beg.”
She leapt off the bed and knelt before me, with a crazed look in her eye and said, “Please, please fuck me now.”
My cock was sticking out and vibrating. I decided to see how far she was willing to go.
“Are you sorry?” I asked, not exactly sure what she needed to be sorry about, but playing the game.
“Yes,” I’m sorry,” she said, and bent down and kissed my feet.
It was getting stranger.
“Your apology is accepted, but first you must kiss my cock.”
She leaned forward and gently kissed the tip. “Is that good?” she asked, meekly.
“Yes. It was acceptable,” I said, “now what do you want?
“Please, I’m begging you, please fuck me with that cock.”
“Get on the bed and spread your legs wide,’ I demanded, and she did as told. I looked at her skinny, sexy body, with her dripping pussy and I crawled up and rammed my aching cock deep into her. Once I entered her, she wrapped her legs around me and was, as last time, a wild woman. We fucked harder and harder until I told her that she could cum again, and I screamed out and let loose a river of semen as I collapsed on her chest, panting, and my heart racing.
We recovered briefly, when Cara said, “That was great. I wasn’t sure if you had that in you, but you played the role quite well. Sometimes I like to be told what to do, but it doesn’t work unless the guy can pull it off. Now,” she continued, reaching into her night table drawer and pulling out a condom and a tube of something. “Have you ever done anal?”
“No,” I admitted, “I’m still kind of new at all of this.”
“Want to try?” she asked.
“Sure, why wouldn’t I?” I responded.
I had tried so many different things in the last few days that I would have been up for pretty much anything.
“O.K., here’s what you do,” she said. “This is lube. You gently use it to rub my asshole, and gradually insert your fingers in. I will loosen up, then you put on the condom and use plenty of lube and slowly start pressing your cock in.”
“O.K.,” I responded, pretty much open to anything at this point.
“I’ll let you know when to stop,” she said. “You are big, but I’ve had bigger in there.”
She rolled over onto her stomach and lifted her now pink ass in the air, sticking a couple of pillows under her. I started to rub her slick pussy and ass hole, and she moaned softly. I squeezed some lube onto my finger and started to tease her asshole with my finger, beginning to press in, a little further each time. I felt her sphincter open slightly as I pressed in. I added more lube and went in deeper and deeper. Soon, I was able to insert two fingers and move them around in the tight hole. I reached underneath her and played with her clit while continuing my focus on her asshole. She continued to moan as I played with her ass, and pressed against my fingers, pushing them deeper and deeper. I got a faint whiff of shit, but figured that was part of the deal. I kept adding lube and playing with her, as her sphincter relaxed.
“O.K.,” she said, “put on the condom and more lube and start sticking it in.”
Which I did. I actually had to push a little to get past her sphincter, but once I did, I was able to get about half way in. It was tight, much tighter than her vagina, but not unpleasant. Cara was moaning and sighing, so I slowly began to withdraw and then press forward, each time pressing further down into her ass. I was holding her hips to brace myself, and Cara was pushing against me as we began to move faster and faster.
It was different from regular sex, but felt pretty good, and Cara was screaming every time I pressed into her ass. I reached around with my right hand and started rubbing her clit as I buttfucked her as hard as I could. With my left hand, I grabbed her long blond hair and started pulling it until her head started tilting backwards.
She yelled, “Yes!” and her sphincter squeezed my cock, forcing me to come hard into the condom. My cock began to become limp, and it slid out of her ass. I removed the full, slick and smelly condom and placed it on the night table. I then kissed both of Cara’s ass cheeks that were still sticking up in the air. Eventually, she lowered them, and I rubbed her back while she lay there quietly.
A few minutes later, she turned to me and said, in a sleepy, satisfied voice, “Thanks for coming over here. There was nobody at the bar at all interesting and I was desperate for a good fucking. You gave me exactly what I needed.”
“Any time,” I said, and meant it.
I got out of the bed and went to the bathroom, took a piss, cleaned off, returned and got dressed—Cara was still lying on the bed, butt naked, the pinkness from my spanking receding from her cheeks. I kissed the back of her head and her perfect ass and left the house, got in my car and went home, quietly going to my room so that I wouldn’t have to answer questions. It was close to 1 a.m., and I needed to get to sleep.
THURSDAY
I staggered out of bed on Thursday morning, tired, sore and smelling faintly of sex and shit. I took a long shower and dressed for school.
When I got to school, Fred said, “You look like crap—were you out drinking last night?”
I said, “No,” and told him about my lousy date with Fiona, and then the booty call from Cara.
He was both annoyed (jealous, I guess), and curious. I told him about the picture she sent, but refused to show it to him.
“What did you do with her?” he asked.
“I spanked the crap out of her, at her request, then went down on her until she literally got on her knees and begged me to fuck her, so I did, then she asked me for anal.”
“NO,” he gasped. “You are my fucking hero,” he said, salaaming at me sarcastically.
“I really can’t explain this, but I have had an amazing lucky streak, and I going to enjoy every minute,” I said.
“I would, if I were you,” he admitted.
Thursday was similar to Wednesday at school. Increasing numbers of attractive girls acknowledged my existence, and I even got unsolicited high-fives from some of the guys. I had notes stuck in my locker from a couple of younger girls looking to “hook up.” I was both enjoying and a little embarrassed by the attention.
At lunch, Gina sat alone, at another table, still, it seemed, mad at me for the sin of trying not to be totally unpopular. Fred and I chatted, as we usually did, about the usual things, without acknowledging the obvious stuff that was going on. For my part, I really wasn’t focused on anything other than my next tutoring session with Dana, or, more to the point, the post-tutoring session. I tried to figure out what Dana might have in mind, and my imagination was running wild.
