Dreaming of MebyMr. Unsexy©
You know, to this day I still don't know why I did what I did.
Okay, I know exactly why I did it. I was overcome with passion. I felt it so strongly that it couldn't be resisted. And when it's right there in front of you tied in a little bow, you won't walk away. You just won't. And introduce heavy amounts of alcohol into your system. Yeah. No way you'd refuse it then. Especially then.
Right now I'm sitting in my cell writing to pass the time. Hell, I've been writing. About a number of things. About historical events. About scientific concepts. Many things I've learned about in the year I've been here. Anything but her.
But tonight I think I'll go ahead and write about what I've been avoiding. That night that changed everything.
Well I can't really fault that one night. It was a while before. A long build up to that point. Let me explain.
I had a friend, Daniel. He was awesome. He would've done anything for me, and I for him. but in the end I fucked it all up for his sister. His sister Sara. My friendship gone for an eighteen year old girl, a girl seven years my junior. But goddamn, she was something.
I still remember nights we'd hang out at his house drinking. Watching movies. Playing games with friends. And Sara would come out, only in a long t-shirt and shorts, and no other guy batted an eye but me. Why I've no clue.
God she was so sexy. She had such a great body. But more of what she had was her face; she was beautiful. Deep brown eyes, I mean intense. You couldn't look her in the eye for very long even when you wanted to. Nice kissable lips, and soft, gorgeous hair. Just perfect.
Anyway, it was one particular night of hanging out. Drinking. Playing games. She came out in that outfit she slept in. I decided right then and there that I was going to have her. I had to. I couldn't take masturbating thinking about her one more time. I had to fuck her.
Of course, it didn't happen that night. But I started being closer to her. Talking to her more. I recall a night when Daniel was passed out on his bed and she and I talked all night on hers. This was when I realized that she wouldn't let me in those tight little shorts. Too conservative. But that doesn't mean that we can't try certain things...
The next night that I stayed there I had a plan. I'd drink just enough to keep up with Daniel until he'd pass out. He couldn't really handle his alcohol though he'd brag that he could, which was perfect for what I had in mind. With him out, I'd wait for Sara to fall asleep herself. And this is where my brilliant plan starts. I wait for her to fall into a deep sleep during which i sneak into her room and touch her, pleasure her, at least something to her until she hints that she's about to wake up, and I split.
It's not as stupid as it sounds, really. So long as you're careful and know that your target sleeps deeply, you're set. Or so I thought.
So we're drinking away, and I can tell that he's about gone. He's babbling on about conspiracy theories and rattling off terrible jokes. The only problem is that Sara isn't home. Sure, It's not too late but it still disorients me.
10:00. No Sara. Daniel is lying in bed, not quite asleep yet but very close.
10:30. Daniel is out. Unfortunately, so is Sara.
11:30. I hear the door open. Two female voices whisper and the door shuts, then footsteps. I see a figure sneak down the hall into Sara's bedroom and I grin an enormous smile knowing that it's finally here. Finally I can do something about this terrible desire.
I hear rustling and other such movement for about ten minutes until silence fills the tiny apartment. Oh, I forgot to mention that after their father died they used the money he left to them to get this place, while she got a job to help Daniel with the bills. This, however coldly, was a factor in me deciding to do what i was set to do tonight.
It's about an hour later when I am able to brave the hallway and sneak into her bedroom. The door is almost closed and i gently push it open. I rise to my full height to see her sprawled on her back on her bed, not even blanketed. Immediately I know what she was doing; She and her cheerleader friends were out drinking, or something. Because she's still got that cheerleader skirt on. And no top. Just in her bra and skirt and panties.
And I swear to god my cock's about to explode.
So I sneak to the edge of her bed and look over her body: her legs are slightly spread; underneath the blue skirt i can see white panties. Looking up that flat stomach I can see her bra, which must be tight fitting because I know her breasts are bigger than that. I am filled with even more excitement when I see that the bra has a clasp in the front between her tits. And that slow way that her chest heaves as she breathes is not helping any.
I am now beside her, kneeling on the floor next to her midsection as she dozes away on her bed. The first thing I do, and I know; really really stupid, but I can't help myself; I kiss her lips. She still has that lipstick on and that light eyeshadow on and I just couldn't help it. It was a light kiss though, and nothing near enough to wake her. Now my breath comes out in segments and it's a wonder I don't start hyperventilating.
Her right arm is over her stomach. Being across from me, it presents my first challenge. My first obstacle to tackle before giving her an orgasm.
Ever so gently I take her wrist and lift her forearm. Slowly I move it to her side, and it all seems to go well until I place it on her side when -
And I'm set to bolt. My head is screaming at me to take off. But my blood is boiling. My crotch is screaming about as loud as my head is, and for some reason I stay. And she resumes her sleep. And I can't even breathe a sigh of relief for fear of waking her.
So I calm myself, which seriously takes a good five minutes, before I resume. Once I'm cool, I lay my hand on her stomach. I rub the soft, warm skin and it drives me nuts. I rub it a little faster until I remember her state and slow myself, gradually slowing before I come to a complete stop. And I look at that skirt. That fucking skirt. God, I think that dismissed a good percentage of my carefulness right there. Gently I rubbed her thighs over the skirt's fabric and moved my hands over her pubus. I rubbed it and it felt so good that I don't think I'd have stopped even if she'd have woken up. Still though, she didn't. And once I stopped that, I ran a hand down the skirt between her legs to rub her crotch, still over the skirt. I didn't feel any warmth(yet) and I eventually worked my way to her bare inner thighs.
This is all being done, mind you, in a very careful way. I mean just what I've gone over, from me entering the room to now, it's been an hour. And I am in a complete reverie. She makes no noise, no movement, no complaints. And I keep on going, loving every second.
So I'm touching her inner thighs for a while when I decide that the skirt's got to go. Very very carefully I take the skirt's ends into a thumb and forefinger on either side of her thighs and I pull down, very very slowly. Believe it or not, they come off with no complaint. None whatsoever. To tell you the truth, looking back on it, I can't believe that worked myself.
I've pulled the skirt down to her knees when she stirs again. Now I pause; still I know that I have to bolt when she wakes up, but now a new problem has risen: what will she say about her skirt? will she assume it rode down? Probably. Who'll she suspect? If I get back to bed in time, why would she think me to have done that? And while I think about this, she drifts back into her peaceful slumber.
So I look up and I see her crotch; her beautiful pussy just barely covered by her small little white panties. I feel them over her pubus and they're cotton. My fingers run down and I feel her lips, and god I almost shot off in my pants at the sensation. They felt so hot, even through her panties, and I involuntarily licked my lips as I rubbed at them. So I slowly guide my hand up her stomach to her chest where I run my fingers in little circles over her left breast. Almost immediately I know where the nipple is and I go for it. Clandestinely, of course.
I rub over the covered nipple and I feel it stiffen. I cannot suppress a slight noise from my mouth and I stop, looking desperately at her face. She can't wake up now. No way. I'm in too far. There is no way I am stopping now, and if she wakes up I have no idea what I'll do. But she does not wake up, in fact doesn't even make a noise or movement to respond and slowly I resume my activity, staring at it lustfully as it forms underneath the bra. I can see the shape but not it itself and I decide that I'm going for losing the bra as well.
I stop what I'm doing and I gently undo the clasp between her breasts; the cups fall to the sides and her breasts rise as gracefully as bread, her nipples bright pink and standing up, nearly as stiff as I am. I bend down and kiss her right nipple and suck on it gently, gently, so gently that I barely can feel it responding and still, nothing.
Pulling myself together, I move my head away from her chest. That was nice. Really nice. But not worth this experience ending. Besides, there are other areas to explore.
My hand finds its way down Sara's stomach to her panties and I rub softly over the lips. I groove my fingers gently into their outline and move slowly, very slowly, up and down between them. I keep this up for a good half minute before I start to feel something. At first I can't tell what it is but it doesn't take me long to realize that her panties are getting damp. I'm getting her wet. Again, for a single moment I lose it and start to press my fingers into her. Almost immediately I stop but before I do I hear a moan. Such a sexy moan. I let out a loud sigh before looking to her face to see if she was awake like I should be doing. But now my passion is slowly overtaking my caution. Less and less the possibility of her waking up occurs to me and even less important are the consequences. Right now she's just a body; a gorgeous plaything for me to touch. And my fingers keep on in her panties.
Now I'm looking at her face and see her breathing heavily. She's panting and amazingly she's still asleep. I can see beads of sweat slowly slipping down her dormant visage. Still though, her arms and legs are motionless. But I'm not sure for how much longer.
What I'd give for some fucking sleeping pills. These are the things that you don't think of when you concoct ideas like this. The little details, scenarios, and helpers that just never seem to occur to you, but when you're in it, you curse yourself for not thinking of it.
Sara's panties are really wet now; her legs are starting to rise up and her arms stretch back. She's still asleep but I don't know for how much longer. To tell you the truth though I don't care. I think I'm going to ride this until it's gone. Maybe she's wanted me. Maybe she'll want to finish. She might be in such a state when she wakes up that she needs to fuck, plain and simple. And I'll be here, only happy to oblige.
This was the bullshit going on in my head. In my alcohol fueled, lust driven head. This wasn't just wishful thinking. This was probability.
I watch her breasts heave up and down more violently as I probe more into her crotch through her wet panties. She starts moving about more now, arching her back, digging her fingers into her pillow, stretching and bending her long legs erratically. Her skirt's fallen to her ankles by now, and her legs are spread wide open. Now I have the courage to just slip my hand over her panties and move them up underneath. And when I do, I feel how wet she is.
I mean it drips off of my fingers, I've got her so hot. The fluid flows slowly across her skin down to the mattress, and she's loving it without even knowing it. I wonder what's going on in her dream.
Everything is gone from my mind now, other than her body and what I'm doing to it. Her nipples are standing straight up. Sweat glistens all over her. Sara's face has a contorted look of pleasure on it, except her eyes aren't clenched, they're sleeping. And I feel like the luckiest guy in the world.
I run my fingers over her pussy, and I have to do something to it. It's so wet. It's exuding an incredible amount of heat. And the lips are so soft.
So I do it. I stuff two fingers up inside her. And it feels amazing. And she moans out loudly.
And I'm ready.
I start fingering her viciously as I start jacking myself off.
And I look at her face.
And her eyes open.
To be continued...