|Let's Make a Deal
by BroDoSis ©
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....'
I looked up at Lisa and said, 'Shhhh!' She smiled and closed her eyes again. Then I really went to work on her. I took her fully exposed clit between my lips and gently sucked it, occasionally running the tip of my tongue over it rapidly. As I worked her pussy over, I looked up to see she had pulled her nightshirt up over her tits and was stroking and squeezing them as I ate her virgin pussy. After a few more minutes, her body started to jerk uncontrollably and Lisa clamped a hand over her mouth, not trusting what noises she might make. Most of my face was slick with her pussy juice now and I was using my entire head to get my little sister off, lapping at her entire mound like a dog. She was loving every second of it, too. I must admit I was enjoying myself, as well...With her other hand, she pulled my head into her groin. Then she came in a long series of spasms that shook the bed. Red faced and panting, she tried to catch her breath. I lingered at her groin, taking a good long look at her cunt. I wanted to remember it's every feature and nuance forever.
'Oh my god, that was awesome!' She recovered quickly. She sprang up onto her elbows and said, 'Now you! Show me how to do it to you!' as she glared at the erection in my shorts. There was such an innocence about her eagerness that it in no way came across as aggressive or slutty. Her tits were still fully exposed and her nipples were sticking out from their tips like bullets; her wet pussy glistened from in between her open legs. At this point, there was no holding back; I was in for the long haul. How far would this go...
I looked over at Lisa with the same look she had given me: I trust you. Without getting up, I slipped my boxers off and tossed them onto the floor. Lisa was floored. She had obviously never seen a real live penis before; my dick was almost 10 inches long and very thick when fully hard. Boy, was it ever fully hard. She looked simultaneously afraid of it and fascinated by it...'How did you get so hard?' she asked. Maybe she thought it had to be stimulated directly, I don't know.
'I guess I'm pretty...excited, Lisa. This is what happens when a guy gets really turned on.' I sat before her on bended knees as she examined my dick. 'Are you sure you want to do this, Lisa?' I wanted her to suck my cock very badly just then. It was getting harder to remember why I thought this was so wrong just a little while ago...
She looked worried. 'Oh, yes, I do...I've just never seen a guy's...penis before, for real...What should I do? Please; I want to learn.' I slid over to where Lisa was lying propped up on her elbows. I leaned over her and straddled her stomach; my hard dick bounced inches in front of her face. 'Oh, my god...Kenny, I'm so nervous...I don't want to hurt you!' she said, staring at the hole at the tip of my cock.
'Don't worry, Lis. You won't hurt me.' I slipped up even farther until I felt my balls brushing against her tits. I reached behind her and grabbed her pillows and bunched them up behind her head. Now it was just a matter of Lisa moving her head a bit and it would be in her mouth...I wanted it in there badly. 'Ok. Ready?' I asked. I knew I'd have to take this slowly. She nodded. 'Take it in your hand, near the bottom.' Her hand trembled visibly as she gently grasped the base of my cock. 'Yes. Now start licking it; that's it. Perfect. You need to get it all nice and wet with your spit. Ahhh. Good. Hahhhh....'
Lisa held my massive erection at the base of the shaft and licked it's entire length along the bottom. Slathering it with her saliva, she had yet to take it into her mouth. Still, it felt like heaven. 'Now. Don't force it, but see how much of it you can take in your mouth. Ahhhhh...yeah.' She parted her lips and opened her mouth wide. It wasn't quite wide enough. Lisa's delicate mouth was so small it barely opened wide enough to let the girth of my cock penetrate it. Her jaw was open to the limit. 'Uhhh...alright. Just relax, I'll do some of the work for a while until you get used to it. Ok?' I looked down at my sister, her mouth filled with my hard, thick cock, for an OK.
She looked up at me. 'Mmm-mmm!'
I slowly and gently started to move my hips back and forth, moving my penis in and out of her mouth in small strokes. She put a hand on my ass and helped guide me in and out of her mouth. Her teeth were killing me, raking across the top and bottom of my dick. 'Try using your lips a little more...yes, just like that...Uhhhh...Lisa, that's good...Yeah...You do it so good...' My big dick moved further into her tight mouth with every stroke; soon she was taking in about 6" comfortably. Lisa started moving her head back and forth; soon we developed a gentle rhythm. She was doing it. My sister Lisa was sucking my dick. She let go of my cock and gently cupped my balls, feeling them curiously. 'Oh, yeah that's good...Easy...oooooh, yeah...'
Her other hand disappeared behind my back. I couldn't see what she was doing with it; but her sucking intensified suddenly and I guessed that she was playing with her cunt. As she worked harder, the blowjob she was giving me got louder and louder, with the sounds of sucking and kissing and heavy breathing filling the room. She was a natural; occasionally she removed my dick from her little mouth and licked, kissed, and jerked it off. After a few more minutes, I'd guess she had about 8" of my huge cock in her mouth and throat. I was freely fucking her face now; I reached down and guided her head over my stiff dick. I felt the semen rising inside me. It wouldn't be long...
'Oh. Oh...Lisa, I'm gonna come...' I moaned down at her.
She pulled my cock out of her mouth and jerked it frantically as she looked up innocently and asked, 'Kenny..what do I do? I don't know what to do!'
It was going to happen soon. 'That's...up to you, Lisa...Do you want it in your mouth or...unhhhh...somewhere else....Ohhh...Don't stop...Tell me quick...'
'In my mouth, Kenny! I want to see what it tastes like!' She immediately took it back into her mouth and began long, deep sucking strokes. I guess if she doesn't like it, she can spit it out, I thought. Then it was happening. I tried to control my thrusts as it began, but it was difficult. I pushed up against her face and shot what must have been a huge, thick wad of hot cum into Lisa's mouth and throat. She whimpered slightly as she tried to swallow all of it, but it was just too much for her. As my spasms subsided, I pulled back a bit; my cock slipped out of her mouth, still gushing cum. Thick, ropy strands of white goo fell on her nightshirt and tits. She swallowed hard and licked semen off of her lips; I guess she thought it was OK because she quickly slipped my dick back into her mouth and sucked the remaining jizz from my prick.
Lisa wiped her chin and hand with her nightshirt. I moved off of her chest and lay down beside her. 'Man, that was intense!' She leaned over and kissed me on the cheek. 'Was I really good, Ken? Did you really like it?' She got up and slipped off her soiled nightshirt as she walked over to her closet.
'Lisa, that was fucking fantastic. If I didn't like it, I couldn't have stayed hard.' Lisa had pulled an oversized t-shirt from a drawer and pulled it over her head. I took one last look at that beautiful young body...'I certainly couldn't have come if I didn't like it. How about you? You didn't mind the end when I...'
'No! It was fun!' She was giddy with excitement. She glanced down at my limp cock. 'It tasted...I don't know...OK, I guess, nothing great...I can't believe I made you come!'
She lay back on the bed. I couldn't believe it either...
The next day, we met in the early afternoon and studied all day long. Neither one of us mentioned the night before, but the vibe between us was much cooler than it ever was before. Lisa seemed more comfortable around me; more comfortable in general; today she wore a knee length yellow flowered sun dress. This was a first. Even our parents were impressed that Lisa was helping me study and we weren't fighting! If they only knew...
We took a few breaks, but basically studied into the night. I gave out first. 'That's it, Lis! I'm done! My head can't take anymore of this!' I slammed my workbook closed, got up and paced around the room. 'It's fucking midnight!' Lisa was calm. 'Well, I guess we could call it a night...but do you think you're ready for the test?'
'What do you mean? We've got all day tomorrow, too! The test is Monday...Oh, man, Lisa...are you thinking what I think you're...No! No way!'
She had that now-familiar adamant look in her eye again. 'Yes way, Ken. I want to learn one more thing...I think you know what it is. We've come this far...You can pass this test if we work for a few hours tomorrow...Teach me just one more thing and I'm yours. All day tomorrow, too..' She wanted me to fuck her. This I would just not do. I would not take my sister's virginity.
'Lisa: I am not going to...You're a virgin! That is a line I will not cross. We can't go there...I won't go there!'
She ignored my protests. 'It would be a real shame to have done all of this work; to have come this far, only to quit...and you're so close, too...' Linda slowly pulled up her knee length sundress as she spoke. She held it up around her navel. Again she wore no panties. Her exposed pussy lips protruded slightly from her near-hairless mound. God, I really thought we were done...
'Lisa. Stop it. I'll flunk the test. I give up. I will not fuck you. I won't.' I wrenched my gaze from her crotch and turned to leave.
Lisa spoke softly. 'Kenny, you don't...It doesn't have to be...in my vagina...right? We can do it another way. I mean I want to learn about other ways, too...'
I wasn't sure I heard her correctly. 'What...are you talking about?'
'Well, I mean...why can't we have anal sex?'
I couldn't believe my ears. 'Anal...? Lisa! Jesus Christ! You're crazy!' I was thinking about the size of my cock and her virgin asshole, but at the same time, a small voice spoke inside my head and said, 'This'll be it, Kenny; one more lesson and you'll pass the test. Besides, she'll hate it anyway and it'll be over quick.' Still, I wasn't sure.
I heard another, more sinister voice, as well: 'Do it. Fuck her ass. Your dick is so big it'll split her in two; it'll teach her a lesson. Payback for the little bitch for extorting you and your 'services'. Hm. I had to admit, this was an appealing angle as well. OK then.
Lisa had turned around and bent over slightly; she stuck her perfectly shaped butt in the air. She now spoke in that new low, breathy voice of hers. 'Have you ever done it before?' I looked into her cute little brown eye.
'Yeah...but...it's sort of a 'not-for-beginners' thing...'
She was stroking her ass cheeks sensually, enticing me. 'Don't you like it?'
I stood in stunned silence. In Lisa's way of thinking, this made perfect sense. This way, she could remain a virgin. I laughed out loud. 'You...you're crazy! You know that? Crazy!' But her little brown butthole looked so inviting...I stood rooted to my spot.
'I agree with you, Ken. I want to stay a virgin, too.' She ran her fingers across her cheeks and stopped them at her butthole. 'Let's do it this way, Kenny; show me what anal sex is like. Then we're done. This will be my last lesson with you.' She gently stroked the area around her anus. From where I stood it looked like she had slipped the fingernail of her little finger into the hole.
'I must be fucking nuts...' I muttered as I walked slowly over to where Lisa stood, still bent over and leaning next to the couch. I put my hand on her ass and first stroked it, feeling the creamy soft smoothness, then squeezed. She was gonna get it, alright. She was gonna get it but good. But I needed to test her. 'Lisa. You may have heard; this is not for every body, you know.' I put the tip of my index finger on top of her little pinkish-brown hole. 'Some people hate it.' I licked my finger, covering it in slippery saliva, and pushed it against the tight opening. 'Some just can't do it at all; they say it hurts too much.' I worked about one inch of my finger into her anus. 'Are you sure?'
'Yes, Kenny. I know you won't huh...hurt me. And you're mmmmmmm such a good teacher, I know you'll do it right...Ahh...more...more...go ahead... Mmmm hmmm...more...ooooohhh...' After a few seconds, I had my finger in her ass all the way up to the third knuckle; if she could take this on her first time, maybe she could take a little bit of my dick...certainly not the whole thing.
'But Lisa...You know how big my cock is...Do you really think it will fit into this tiny little hole? My finger barely fits!' I just wanted her to know what she was asking for.
'Ahhhhh...It feels kinda good...Really good...I don't know if it'll fit all the way in but uhhh I want to find out...Ohhhhh....Go over and look under the bookcase. There's something there that might help.' I slowly slipped my finger out of her butt and walked over to the bookcase in the corner. I reached into the small space underneath the lower shelf and produced a small bottle of baby oil.
'Damn, Lisa. Ok...you want it, you got it!' When I returned to the couch, she was completely naked and was sitting on the couch on all fours. Her big beautiful boobs hung down tantalizingly and her entire pink pussy smiled at me from behind. It was glistening wet as she waited for me. I walked over to her and pulled off my jeans and briefs. My cock was semi-erect; I walked over to Lisa's face and I didn't even have to ask. She took my hardening cock into her hot mouth and began giving me head again, just like I taught her. In seconds, I was hard as a rock. She stopped sucking and took a good look at my massive tool. Lisa looked as intimidated by my erection as she was before. 'You sure? Tell me now; once we start I might not be able to stop...' This was a lie, but I was still testing her resolve. 'I don't want to hurt you.' Well, not too much, anyway...
Lisa looked back at me and said 'Just put a little bit in; go slow and I'll tell you if it hurts. If I want you to stop, I'll tell you. OK? Please?'
'OK...' I poured the oil into my hand and spread it over my cock. I stood behind where she was on the couch and positioned my dick up against Lisa's ass. I slid it's big bulbous head all around her hole, spreading the lube around; brushing it against her cunt and causing her to gasp. 'The main thing you have to remember here is: Relax. OK? Here it comes, Lisa.' I put the head of my cock against her tiny butthole and pushed. She squealed. 'Remember, Lisa: relax. Relax all of your muscles. Concentrate.' I felt her butt open a bit. My cockhead pushed harder. There. It's tip was pushing the hole gently open. I was very careful and took my time. If I didn't watch it, my fat cock could really do some damage. 'That's it...relax...Take deep breaths...good...' My dick was about one inch in; Lisa seemed to be OK...God, it felt great.
She suddenly held one hand up in the air. 'Stop! Ken! Wait!' I stopped, ready to pull out. 'Just hold it there, don't move...Ahhh...Hold it...' Lisa moved forward a little, then moved back...I could feel her anus opening around the head of my dick. Now it was in about 2 inches. 'Uhhhhh! Oh, God!' She groaned.
'Lis? You want me to take it out? Tell me and I'll stop. OK?' Her little movements felt really good; my penis had never been into a hole this tight before.
She was panting. 'No! Just...Let me...Oh! Let me do it...Mmmmmm....' Now she had worked about 4 inches in and she was at the fattest part of my dick. She had the muscles of her ass completely relaxed and I couldn't quite believe what I was seeing. My petite little sister was taking almost half of my monster cock into her virgin asshole. Now every microscopic movement she made was heavenly; I started to move just a tiny bit myself, and soon we were making even more progress. Lisa moaned through clenched teeth. 'Arghhhhhh...Ooooh...Yes, OH, YES!' Past the most difficult part, Lisa started to move more freely back and forth. I poured a little more oil on the top of my dick and suddenly we were fucking. I was fucking her ass! Damn! I never would have dreamed she could have taken the majority of my cock in her tiny virgin butt. This session was really bringing out the animal in Lisa, as well...
'Ahhh, Kenny, fuck me, fuck my ass...Oh! Oh! Yeah! Oh, I love it!' I held her ass with both hands and really started fucking her hard. I pulled her on and off my cock like a rag doll. She obviously enjoyed it. 'MmmmMmmmMmmmm!' she hummed. She bent around to look at me. I almost didn't recognize her; she was so transformed by lust. She squeezed a tit while she said, 'It doesn't hurt at all, Kenny! It feels sooooo good...Do it....Ahhh...Do it harder...'
I lost control and gave into the sexual frenzy. I was really slamming her butt. Lisa tried to answer but could only manage a series of high pitched whimpers. Her boobs were flopping about uncontrollably. Lisa reached between her legs and alternated between playing with my nuts and her own clit. She forgot about my balls soon enough and concentrated on massaging her cunt. I think Lisa came then; I felt her sphincter muscle clench and she howled like a dog, shaking and sweating. I just kept on fucking; Lisa put her head down on the couch and her butt in the air and it sounded like she was weeping. Soon I felt my own orgasm approaching. 'Uhhh...Gonna cum, Lis...Want it in your ass? Tell me...' I was also sweating profusely now. My thrusts became fewer and harder, Lisa whimpered a loudly with each forward thrust.
Finally, she said, 'My ass! Cum In my ass! Oh, Kenny! OH, KENNY! CUM!' Lisa came again as I shot my load. I released huge load of semen, this one deep into my sister's asshole. It was suddenly very hot in the depths of my sister's nether regions...Spent, I pulled out. Cum seeped out of her hole as I withdrew my cock; her asshole gaped open after my dick was gone. What a mess. We'd have a bit of work to do cleaning up the couch before going to sleep tonight...We lay back on the couch, her head leaning on my shoulder.
Lisa spoke first. 'Thank you, Kenny. Now I know. I feel like a different person...' I was still catching my breath. 'Lisa, I...That was fucking amazing. I guess you were right. I shouldn't have fought you. I didn't have to make this as hard for you as I did. I just didn't want to hurt you...I didn't want us to do something that was wrong.'
'We didn't, Ken. We didn't.'
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