Let's Make a Deal

No doubt about it; Lisa's the brains of the family. She was doing very well in her first year of college and had a solid career path lined up ahead of her. Me, on the other hand, I wasn't doing so well. I had dropped out of high school 4 years ago and was having a hard time getting anywhere in the job market. A few weeks ago, however, a friend had offered me a job working in his company; all I needed was a high school diploma or some equivalent. I had decided to go for a GED, a high school equivalency certificate which was the next best thing to a high school diploma. A few weeks ago, I decided to ask Lisa for help. This wasn't easy for me; we had a real sibling rivalry built up after years of her achievements in school and my, for lack of a better term, under-achievements. I really resented the fact that it was easy for her. But I decided to rise above and see if she would help me study for the test.

Lisa was very shy and what most would call 'bookish'. She wore glasses dressed very conservatively. She has pretty eyes and...well, I guess that's it. She had never really dated in high school or college. She seemed more focused on her education than her social life. I guess that's why she was excelling, and I wasn't.

I was pretty cordial to her for a few days, then I asked her. She laughed at first. 'You really expect me to spend time helping you out with this? After all the crap I've taken from you about how 'smart' I am and how 'boring' I am, and how I 'have no life'? Now you want my help?'

I poured on the sugar. 'Lisa, I'm really not the same guy any more. I can see how you were right all along. I need your help so I can really change my life. Will you help me? Please?' She saw I was serious. 'I'll beg if I need to...' She smiled at me. Finally!

'OK. But we'll have to make some kind of a deal. And it's got to be something big, too! You've got a lot to make up for and you're really going to owe me for this!' She wagged her finger at me as she spoke.

'Anything, Lisa! You name it! Let me know and it's yours. I promise. Thank You!'

We worked out a schedule for when we could prep for the test. Then I kissed her on the forehead before I went off to work. I think this really threw her; she blushed and shooed me away, embarrassed. She looked really cute just then; it was a shame that she didn't really seem interested in guys. She was very awkward and self-conscious around guys, especially my friend Larry. I think she had a crush on him. Larry thought so too, but he found Lisa too 'plain', too 'quiet'.

Our first tutoring session went well. It was tough for me but Lisa was a good teacher; patient and thorough. I didn't bring up the 'deal' that we still hadn't finalized because I was afraid to hear what she might want...a year of free car washes? A date with my friend Larry? I knew she had been talking about having her bedroom painted; god that would suck. But I'd do it, I was a man of my word. I just wasn't going to be the one to bring it up...Lisa did. I should have known she wouldn't forget.

'So, Kenny; about that 'deal'...I think I might know what I want you to do...but I have a few questions first.' Her eyes darted nervously about the room as she spoke.

'Shoot! Ask me.'

'You said you'd do anything, right?'

'Yeah, I think I did...why?' Man. This was going to be rough, I could feel it.

'Did you mean it? Anything?'

'Well, yeah! I told you, I need to pass this test bad! What've you got in mind, Lisa? C'mon! 'Fess up!'

'Well...I...' There was a long pause. The suspense was killing me. 'I want to think about it some more...We'll talk again tomorrow night.' She had a very serious look on her face as she gathered her books up and started to walk away.

'Aw. Lisa, that's not fair! You gotta tell me!' I called after her to no avail. For the next 24 hours or so I wondered just what menial chore I'd have to do for her for the rest of eternity to pay her back not only for her help with my test, but for years of spitefully denigrating her about who she was. I guess I had it coming. At our next session, we sat on her bed. In the middle of an exercise I closed the book we were using. 'Lisa...are you going to tell me what it is that I owe you? It's torture not knowing...or is that your plan? Making me sweat?'

'No, Kenny. It's just not easy to...come right out and...say. I mean...' She was clearly very uncomfortable.

'Look, Lisa--say it! We'll both feel better! Really!' God, it was driving me mad!

'OK. What I was thinking...' Her voice dropped down to almost a whisper. 'I was...I want you to teach me some things.'

I looked at her confused. What the hell could I teach her? How to replace her alternator? She was dead serious and really nervous. 'Teach you? Lisa...what do I know to teach you that you don't already know?'

'Sex.' My head felt like it was just smacked with a mallet. She had never said anything like that to me before. No wonder she was so uncomfortable.

'Oh...well...um, OK,' I said, trying to act very mature and matter-of-fact. 'I guess after we finish with this stuff you can ask me anything you want...but jeez, Lisa; you're in college and--'

She interrupted me calmly. 'No, Ken. I don't want to talk to you about it.'

Now I was more confused than ever. 'Then what...'

'I want to do...things...' Her eyes met mine and she had to see the look of stunned disbelief on my face.

'I know all about sex. I've just never done any of it... I guess you've been right when you've said that I had no life. And I know you've had experience...I thought you could show me what it's like.' Lisa looked like she might burst into tears at any second. This was difficult for her. 'I mean...I'd like to find out what it's like with you...my brother, before finding out...you know, with someone I hardly know and stuff...' I didn't want to upset her, but what she was talking about was crazy! She was my sister! She was obviously really mixed up about some things and it was my job to help her straighten her head out.

I treaded lightly...'Look, Lisa...I can understand your curiosity if you've never had any...experience before. But for us to...We can't, Lisa! It's not right.' Her eyes had welled up with tears as she listened. Great. My refusing was hurting her feelings. Man, she had some serious issues...She started sobbing. I tried the only way I could think of...'Lisa, c'mon...It'll happen! You know it will! You just need to get out there and date some more...It's just a matter of---'

Sniffling, she interrupted again. 'Kenny, you said anything. Anything! This is what I want! I thought about this long and hard! You can't go back on your word!' Her words were coming out choked through the tears. 'Forget your test! Forget it! If the deal's off, then the deal's off!' Now she looked at me angrily. The tears were replaced by an angry scowl and she waited for my move.

'Lisa. It's wrong. Please don't do this. I need this diploma and...'

'We made a deal. And you promised.' She wasn't budging. She looked pissed.

My mind reeled. How could I fix this? Compromise? Was I insane?

'Whew...Um, I don't know what to do here, Lis. I can't do it; I mean...well,' I exhaled loudly. 'What..'things' did you have in mind?' I was utterly amazed as my penis began to stir in my pants. What the?

Lisa still had that pissed off look on her face. She paused. 'Things. You know. What you do with a girl when you're...fooling around; what the girl does to you...I know what happens; I just want to know what it's like... '

'Kissing? Petting? That stuff?' I offered. Keep it simple...If I were actually going to entertain this notion, I wanted to get off easy. My dick seemed to be feeling just the opposite...What the hell was going on?

'Yes, and other stuff. C'mon, Kenny, you know what I'm talking about. You're stalling. What is the first thing you try with a girl when you're...messing around?' Her voice had steadily risen over the last few minutes; I motioned her to quiet down. It was pretty late and our parents were asleep a floor away, but to get caught discussing such things...

'I...Jeez, Lisa...I guess it would be feeling her breasts. Yeah.' I simply could not believe it, but I had a semi-erection and it was growing by the second. I shifted on her bed, trying to accommodate it; hoping Lisa wouldn't notice. Then, in what seemed to me like slow motion, she took her glasses off, reached over to her nightstand and flicked the 3-way light to it's dimmest and started unbuttoning her blouse. I couldn't believe my eyes. 'Lisa...man...I'm...' The sight of her boobs packaged tightly in her bra stopped me short. I had never ever seen Lisa in anything even close to revealing; not even in a bathing suit, not since we were little kids. The way she dressed nowadays, one would even wonder if there was any kind of body under her clothes at all...but good lord, they were fantastic. I guessed 36-C. As my eyes drank them in a combination of shame and excitement, she reached behind her back to undo her bra strap. I tried to speak and failed miserably. My god, I was about to see my sister's tits...

They were fantastic. Perhaps the most beautiful breasts I had ever seen up close and in person. And they belonged to my baby sister...They stood out from her naked chest proudly and hung ever so slightly; their nipples hard and a vibrant pink. Open up any issue of Playboy or Penthouse; this is what you'd see. Who knew, I kept thinking; who knew...

She sat before me, trembling in anticipation. She took a deep breath and said, 'Now show me. Show me what you do.' I knew she was looking at me, and I tried to look up at her face, but...they were magnificent.

My voice was a hoarse whisper. 'Lisa, this is crazy. I can't...' And yet, I began to think that perhaps I could just touch them for a bit, we had a deal and all that. As my hand reached with one trembling hand for one of her perfect tits, one part of my mind seemed to detach completely from my consciousness. I realized that yes, I wanted to touch it, very badly...My cock was completely hard and throbbing. 'Lisa...I'll do this much for you, but that's it.' I heard my own voice tremble. 'We can't go any further than this...Ok?' She ignored me.

I gently took one breast in my hand. I searched Lisa's face for any sign of her changing her mind; I found none. I started softly massaging it. I could hear her breathing now. My fingertips instinctively went for her large, hard nipple and started lightly pinching it. Lisa gave a little gasp and closed her eyes. I slid over a bit closer to her and continued my stroking, pinching, massaging. After a few moments she asked, 'Is that all you do, Kenny?' in a voice that had deepened considerably. She knew the answer was no.

'Lisa! Please don't make me do this!' I looked at her plaintively, shaking my head. She just stared back at me, waiting, her eyes half-closed. This is insane, I thought, as I reluctantly bent over and put my mouth over the nipple. I molested it with my tongue and bit its tip gently between my teeth. I sucked on it lightly and kissed all around it. She had put her hand on the back of my head, cradling it to her boob. Lisa was breathing heavily as I suckled her tit. Her eyes were still closed. I reached up with my other hand and began fondling the other breast. Lisa whispered 'Ohhhhhh,' up into space.

After a few more minutes of this, she whispered, 'Then what, Kenny? Hhhhhhh...Then what do you do?' While still sucking her titties, I reached down and slid my hand up her inner thigh towards her crotch, not really thinking clearly anymore. But suddenly, Lisa stopped me...Thank god...Was she having second thoughts? Was this a test? A trap? God, I hoped she didn't hold it against me that I had gone as far as I did. I knew she couldn't go through with it...

Lisa slipped off the bed and stood up. She unfastened her belt, kicked her flats off and undid the zip to her slacks. My jaw was in my lap. She stripped to her white cotton panties. I was in shock: my baby sister was a beautiful young woman; slender hips, tight, lean legs, those wonderful tits...She hopped back onto the bed and returned to the same spot next to me, kneeling. 'Then what? Go ahead...' she said, closing her eyes. I looked down into the crotch of her underwear. The little mound was so pretty; so perfect. Her inner thighs were creamy and smooth, inviting...my hand somehow found its way onto her upper thigh. It felt like velvet in my hand.

Lisa closed her eyes again. 'Show me, Ken. Show me what happens,' she said, widening the gap between her knees considerably as my hand slipped up towards her pussy. I could see clearly what I was doing but it seemed so unreal; so dream-like. I touched the center of the crotch of her panties with the tips of my fingers. I could feel her pussy lips through the thin fabric. Lisa's mouth opened and she took a few harsh breaths. 'Show me...show me....hhhhhhh....' I began to rub my sister's cunt through her undies.

'Oh...ohhhhhhhh....uh.....Ohhhhhh....' she moaned as she lay back onto her bed and spread her legs for my probing fingers. A small dark stain appeared under where I was gently rubbing; my fingertips were starting to get slippery from her pussy juices soaking through. I massaged her mound over her moistening panties with one hand and massaged her tit with the other as she lay spread-eagle in front of me. The way her hair fell around her head as she lay there, the sexy expression on her face as she writhed at my touch, the fantastic young body that lay before me; I could not believe at that moment that I had ever called this girl 'plain'. My dick felt about to explode as I brought my sister's almost naked body to climax. Her hips started to gyrate as I rubbed through her panties at her hardened knob...Goosebumps covered her arms and legs. She arched her back suddenly and grabbed a tit in each hand, squeezing them roughly...and came. She bit her lower lip as her orgasm ripped through her; her hips bucked up and down wildly as I strained to keep my hand in her crotch. I wanted to finish her off completely. After about 30 seconds, she lay still, her breathing coming back to normal. 'God, Kenny....That was wonderful...'

Reality came flooding back to me with the sound of her voice. What had we just done? This is something we could never 'un-do'; there was no turning back from this. I climbed off the bed and stepped over our books, delirious. Lisa gazed over at me. Her eyes immediately fell upon my hard cock bulging through my pants.

'Wait--we're not done!' Lisa reached an arm out lazily toward me.

'Yes, Lisa. Yes we are,' I said as I walked out of the room and closed the door behind me. My legs were shaking. I entered my room and got undressed. Climbing into bed, I could not get the thought of Lisa's newly revealed, beautiful young body out of my head. I reached down to caress my still-hard penis. If you stayed in her room, it might've been Lisa doing this to you now, I thought as I jerked myself off. I struggled to tell myself that I had done the right thing by leaving; but as I masturbated I was fixated on my younger sister's perfect, unspoiled body. I came into a t-shirt and fell into a fitful sleep.

The next day I was in a constant state of anxiety. I had tried to go over the material for my test on my own during the afternoon with disappointing results. I just couldn't do it. Of course, the previous night's events were still on my mind and they provided a major distraction, as well. But I was just not cut out for studying. I wouldn't be able to get that job and I'd be stuck working at the garage forever unless I played Lisa's game. I was torn...I guess I did get a little bit carried away that night, but deep down I still felt it was wrong. Both for me and for her. But, had I really done wrong? I mean, I never really did touch her genitals directly; her panties still covered them...I had debated these things all night. I needed this job; I needed it bad. I had three days left and Lisa was the only one who could help me. I'm going to try to talk to her one more time. That's all I can do, I thought. It was around midnight, and I could hear her tv was on in her bedroom. I lightly knocked on the door.

'Come in...' she called. I walked in and immediately saw that she was wearing a short nightshirt as she lay on her bed watching tv. In the past, she never would have invited me into her room; and if she was ever seen just before bedtime, she was usually wearing a big thick robe that covered her pj's. She was lying on her stomach, the shirt ending just high enough so her ass cheeks were exposed. I could see so much of them, I guessed that Lisa was wearing a thong. She made no move to cover up. 'Hi, Ken.' was all she said. She wasn't even looking my way. She was playing hardball.

'Lisa...I don't know what to do...I need your help...But I can't play by your rules. I think you're a little confused about some things right now and--'

'I'm not confused about anything Ken. You're the one who's confused; about a deal we made yesterday. I'm sticking to it. You want something from me; I want something from you. It's perfectly fair.' She was still looking at the tv, appearing disinterested in our conversation.

'Perfectly fair! You...extortionist!' She knew who was in control here. I had no choice. I gave in. 'OK, Lisa. What is it you want? I give up. You've got me where you want me. Now what?'

She looked up at me; her body shifting on the bed so that her nightshirt rode up a bit more. She wasn't wearing a thong after all. She wasn't wearing anything under that shirt!. Her entire naked ass was exposed. This didn't seem to bother her at all. In fact...she must have been waiting for me to give in! She had an impish grin on her face as she said, 'Oral sex. Tonight, you'll show me oral sex and tomorrow I'll spend the afternoon with you studying. That's what I want.' She looked up at me with a look I had never seen from her before. Power. It was her terms or nothing.

'Oral...you mean me...doing you or, you...' I just couldn't even imagine this.

'Both.' She sat up in her bed facing me with her knees bent, legs apart. I saw Lisa's naked pussy for the very first time. I stood in shock looking at her thin, glistening lips showing through her soft and sparse 19 year old bush. She knew the power she could have over a man. I could feel myself start to lose it again as my dick stirred in my shorts. Her pussy was beautiful. Pink and perfect, with very little hair surrounding it. I thought, just for a second, that it could be worse...she could've wanted me to rotate her tires or something...This was a pussy that, had it not belonged to my little sister, I would have loved to go to town on. My cock was at full attention in seconds. I couldn't hide it in my boxers. She had to have seen it growing as I stared at her cunt. I was momentarily mesmerized by it.

'Um, you want me to...show you, er...first?' I asked weakly.

'Sure.' She reached over and snapped her lamp to dim again. She left her glasses on; this she wanted to see. 'How should I sit? Should I lay down or...'

'Just stay put.' I climbed into bed and moved in between her knees. As I moved in closer to her pussy, Lisa looked down at me with a look that said 'I'm trusting you.' That actually meant a lot to me. I tried to look reassuring. I guess she had to trust me to have started this whole thing...suddenly I felt a bit more like her brother than I did the night before. And here I was, inches from one of the prettiest pussies I had ever seen. It was just so damned small and cute and delicate...I slipped my arms under her thighs and pulled her legs open farther.

She lay back on her pillows and closed her eyes. I kissed her lightly on her cunt lips once; then again. Then, during the next kiss, I slid my tongue around the thin lips a little bit. Licking lightly up and down her slit, I lingered a bit at the sheath covering her clit. She moaned as I worked my tongue into her pussy; yes, she was a virgin. I knew it. I continued licking her lips. 'Oh, Ken...that feels so beautiful...' Her clit was hard and swollen now; her juices were flowing freely. I felt a hand at the back of my head, urging me on. I increased the pressure of my licking, working hard on her clit. 'Oh my god, Kenny...This is even better...oh...than last night....mmmm....'