There has to be some way out of this. I dress the next day in a fairly short skirt, so that it will be easier to get done what needs be done, because I figure that if I wear jeans or something like that, it'll just increase our chances of being caught. And being caught is what I worry about most, regardless of what you mean by "caught." By somebody else, by Trevor, who's bound to notice my incongruity with a regular girl, or the very idea of "catching," whatever it is, I'm terrified.
Thong panties are uncomfortable, I now realize, but they're part of the ritual, as well. The in- and-out strategy, I think, which doesn't make me feel much better. Trying to wear them with heels is giving me a definite wobble in the way I walk, and I can see guys watching me. At first, I think they might be waiting for me to fall over, but then I realize that they're keeping their eyes on my hips, and my ass. If they knew who I was, they probably wouldn't be so attentive."
In my classes, I can feel people staring at me. Eventually, during government, the teacher leaves to fetch an overhead projector, and one of the girls turns to me.
"So, Trevor finally got his way, did he?" she says, and points to her mouth. I look down at my notebook, and nowhere else. "From what I hear, sounds like he had a pretty good time with those pigtails. You don't look the type, I'm surprised."
The girl sitting next to me chimes in. "It's the librarian complex. The quiet, shy girls are always the sluttiest," she says, and I can see that the guys in the class are making motions and mouthing things to each other. The teacher returns with the overhead, and class goes as usual.
Later, in the library, I sit, too nervous to read, with my legs crossed, and try to think my way out of it. I'm just too afraid of Trevor; I'm still too shy to say anything. I couldn't say two words to this guy before, even if they were "excuse me," how could I say anything to vindicate myself now?
Within a couple of minutes, Trevor shows up, and puts his bag on the table. I get up and try to smile, and say "hi, Trevor." He walks over to me, and I start to say, "listen, maybe we," before he grabs me around my waist and pulls me closer to him, before kissing me. I put up my hands in protest, for a second, but resist the urge to push him away. I'm deep red again, and when he pulls away, I'm speechless. He reaches down and pulls on my cheeks, nearly lifting me off my feet.
"I got you some more presents," he says, and he reaches over with a hand and unzips his bag. He takes out another stuffed animal, and this one is a... worm? It has glasses. "For my little bookworm," he says, smiling. It's cute, and odd, and I smile at it. Then he reaches into the pouch on the side of the bag and pulls out my other present. My mouth hangs agape. It's a squeezetube.
"Excited?" he says, and before I have a chance to respond, he's kissing me again. My eyes are wide open, as he reaches under my skirt and starts to fondle my bum. He takes me by the shoulders, and turns me around. I don't know what to do with my hands, so I just put them up, fingers curled, and he reaches down to touch my thighs. He pulls up on my stockings, and then takes me by the hips and pulls me towards him again. That's when I feel it. Something hard pressing up against my tush, from underneath Trevor's jeans. He pushes his hips up against me, and thrusts at me a few times, and I'm shaking with embarassment. I start to formulate a plan, before it's too late.
I manage to turn and face him, and I reach up to kiss him a little. He holds my head and returns the kiss, full force. Once he's let go, and my head is spinning, I drop down onto my knees. For the third time, I'm looking up at Trevor for a very specific purpose, and I undo his fly. I reach in to pull him out, and have a hard time, so Trevor drops his pants, and then his boxers. He's full-mast, and his hands are on the back of my head. I lean forward and take him into my mouth, again, and start to suck with earnest. If I can get him off this way, he won't be able to, well, you know.
I suck and suck, and I slurp on his cock, and he gets into it, and starts to thrust himself. I start to feel the twitching and jerking, and the precum splashes onto my tongue, and so I go faster, and massage him up and down the shaft with my hand. He's almost there, and I get ready, but he thrusts forward all the way, and I gag. He holds my head there, and I know he's almost there, so I flick at the underside with my tongue, try to move my head as much as he'll let me, but I can barely move at all. He doesn't cum, and my stomach is all the better for it, but he pulls away then. He looks around me, at my tush, which is sitting on my feet, and he walks around behind me, and takes something from the bag. I don't have to guess what.
He kneels down behind me, and pushes me down by my shoulder, and I put my hands on the floor. I'm on my elbows and knees now, almost sitting on my feet, and he has me pinned down with a hand on my back. He opens up the tube with a click, and I hear him squeezing it out. Then he lifts my skirt up, and squeezes out some more, and moves my thong aside, and a finger presses to my rosebud, and it feels warm, but cold.
"You ready, Sara?" he says, and moves forward a bit.
"Trevor..." is all I can say. My mind is racing. I don't know what to think. Should I tell him?
He lifts up my skirt more now, and I feel that it's held up by his body. I look around for something, anything, to take my mind off what's about to happen, but there's nothing to say or do. In a moment of sheer panic, I feel him put his member up to my bum. A little bit of force, and I feel it start to open up, welcoming this intruder.
I wait for my white knight to rescue me, but nobody comes. A second later, and his head pops into my virgin ass, and I feel like I'm on fire. My ring tries to accommodate his huge dick, and I feel it stretching open. He tries to comfort me with a hand stroking my cheek, but he's lost his mind, and he continues to penetrate deeper. I instinctually pull away, but Trevor has a hand on my shoulder, holding me still while he fucks further in my ass. I feel my own lift up my skirt, as he breaks me in with short, frenzied thrusts, just trying to get deeper and deeper.
I'm shaking and sweating and gritting my teeth, scratching at the floor, anything to avoid the sensation of a cock up my ass. It's unavoidable, and Trevor just grunts and strains as he tries to bury it in me. His girlfriend, Sara, who's taking it in her virgin asshole, just for him. I wish I could hate him, but I realize that I've done this to myself. I wanted Trevor to stop looking for porn on the library computer in my "haven" so I could have it to myself. Well, Trevor had no use for porn now. He had two warm welcoming holes to pound his junk into, though, in a strange twist of fate, there was no third. He thought he was giving Sara, the shy, bookish girl, an ass-fucking to remember, but all he was doing was making it the worst day of my life, one fevered thrust after the next. I had never had anything so big or so hard up there, and I squeezed him with each forced spasm, as I feel my virginity slip away. I lost my virginity to Trevor Lebone, when I gave him my ass willingly! , so that he could get from me what he couldn't get from Veronica for months.
A warm place to leave his spunk.
He groans, slaps my ass once or twice, and says "Sara, your ass is so tight," like I couldn't tell. He's big, and it terrifies me what it's going to feel like to have him rooted in me, dominating me like his bitch.
"How does it feel, baby, is it good?"
My teeth are gritted, in anger more than anything now, in shame, and I want to curse him out. Sure, I'm rock hard, hidden in the skirt, but Trevor doesn't know that, and it's not my fault. I mean, after all, it is Trevor, he does have a reputation for being pretty good at what we're doing. But why should that matter?
He pushes harder down on my back, as he rubs my ass and pulls my cheeks open, and inch after inch explores more of my poor, straight boy ass. Little does Trevor know that he's banging the nerdiest person in the school, who couldn't get a date worth anything, and who was now getting plowed by the (male, unfortunately) sex symbol on campus. I yelp every time he makes it further in, and he knows that he's got me in a position where what I say doesn't matter. He's gonna give it to me, like it or not.
"Sara, it's almost all the way in!" he says, and I can't believe how stuffed I feel. Intimacy is one thing, and having him down my throat was another, but now he's feeding his cock down an entirely different orifice, and the shame is making my face beet-red. A couple of over-eager thrusts told me that Trevor wanted to bottom out, and he did, and I really wished that I had just told him and he had kicked the crap out of me instead. He wasn't moving it anymore, but that didn't matter, it was in me to the base, twitching and pulsing, while his balls rested on my thighs, doing the same.
"Thanks so much, babe. I know this has to be hard for you," he says, which is quite the understatement. Trevor may not be a bad guy, but I certainly didn't want him to fuck my ass. Yet, here we are. "I'll try to last as long as I can. It's really, really tight," he says, chuckling to himself. I guess I should be proud, I might make "Terrific Trevor" blow early.
Blow. Wad. Semen. Spunk. In my ass?
He starts to pound me, now, and I grit my teeth again and lose my breath. I don't know exactly how the nerd evolved, but I do know now that it didn't involve the stipulation that I'd have to take a shaft in and out of the bum. I don't think I've ever been hotter; it feels like the library is a sauna. Trevor, meanwhile, is having a grand old time, thrusting where no man ever should have been, banging me, a particularly unseen forbidden fruit, the wet, sloppy sounds of our misunderstood love-making filling the library around us. Even when he's not in, I can feel the lube and my "openness," and I know I'll never be able to forget the feeling.
"Oh, shit, sorry!" he says, for the second time, and I wonder if he knows I'm a boy. The thought doesn't last long, as the spasms and Trevor's tensing hands brings to life the worst moment of the worst day in my life. :"I love you, Sara," is what merciless Trevor says to me as he blows inside, and I cry, and I whine, and I moan, and I whisper breathlessly, "not in my ass," but he either doesn't hear me or doesn't care, and we're locked together as his thick cum shoots out in my bum, just to satisfy him. I'm pulling up the floorboards, mouth agape, and drooling a bit, as he empties the motherlode into my colon, and washes away the last of my dignity. He said "I love you." The semen is still boiling in me when he pulls out, somewhat still hard, and I realize I'll have to relieve myself in the bathroom eventually. I can't even move, so Trevor pulls me up, and my eyes are still rolling, my mouth is still slightly open, and I look at him, sexually exhausted after my virgin fuck. I must be giving him a look that only the most satisfied girls can give, but I'm not satisfied, I'm just full. He hugs me, and puts a finger in my ass, as he kisses me. He said he loved me. Why did I care?
His other hand makes it around to my front, where he touches my crotch. He reaches under the skirt to confirm his finding, but I'm too weak to protest, and I'm just fearful for my life. It's nearly flaccid, and shaved, and apparently I came at some point. He doesn't touch it, and drops the skirt, and looks at me.
"Are you gay?" he says, more bewildered than anything.
"Nope," I say, and explain the whole thing to him. Periodically, he bends me over to look at my ass, which is kind of confusing at first, but I realize he's trying to reconcile what I've got with what I've got. After I tell him the story, he looks at me sternly, and then laughs.
"So you just took it in the ass, even though you didn't like it?" he says, and shakes his head.
"Yeah."
He nods. "You're nothing like Veronica. Loosest slut I've ever seen and she wouldn't put her spit on me if my dick was on fire. You, you're different," he says, and I don't know what he thinks of me.
"So, now that you know, are we, uh, well, breaking up?"
He hugs me, again. He grabs at my ass. "Why? Nothing's changed. You're still willing to help me out, and I'm still willing to put it in your ass."
I swallow hard. I know that I don't have any other options. For some reason, I need to ask him. "Do you still love me?"
His face is strange, unreadable. "I did say that, didn't I? Well, maybe I do, maybe I don't. You're definitely cute, and your fun to be around," he says, and puts his finger in my ass again, "and you take it up the shitter for me, which is a good enough reason to love anyone."
"But?"
"But, you are, you know. We'll see. I'm not a bad guy, Sara. But I'm also not Santa Clause, or the Tooth Fairy," he says, and then laughs, "especially not the Ass Fairy. I will tell you, though, when I've got you like that, there's quite a bit of affection."
I scowl. My ass still hurts, and I'll need to get to the restroom soon to let out Trevor's proof of victory. "For my ass?"
"Yeah, yeah. And for you, I'd say."
"So, you're still going to treat me like a girl?" I say, honestly dispassionate.
Trevor walks up to me, spins me around, bends me over at the waist, and whispers into my ear, "you are a girl," before he makes me spread my legs a bit. I don't have a chance to say anything before he slams his cock all the way to the hilt, and I stand on the tip of my toes, in heels, to avoid catching the fuck, but Trevor just follows me up when I do it. He pushes down my back again, and I pull my shoulders together and put my hands on my knees, and his hand leaves my ass for a second, before he spanks me so hard I se stars. I clamp down on his cock, which was probably what he wanted, and then he starts to fuck me, again. He spanks me, once again, twice, three times, and my cheek is raw.
"Trevor, please," I say, and he grunts in response.
"Want it harder, you say?" he says, and picks up the pace, and each thrust leaves me breathless. I totter back and forth on my heels, so the only sounds are the click-clacking of my heels and the slapping of his hips against my ass. My cock lifts up my skirt, and I can feel it start to twitch with each thrust.
"Take it, bitch," he says, and starts to rotate his hips, filling me up, all around. "You like that, I see."
"Are you gonna cum in my ass again?" I say, pouty.
"Yep. But not until I get to see what a girly boy looks like when she likes it."
I already told him that I didn't like it, so I don't really know what he means, until I feel that familiar itching sensation. It starts to build, and build, and Trevor thrusts more, until eventually, I can't hold it in, and Trevor puts his hand around my neck and strokes it, as he buries himself once more, but he doesn't cum. He wants to watch me cum while he assfucks me, like a whore. My whole body shakes, and I let out a moan, fuck it, and unintentionally grind my ass back at him, as I cum across the floor. Thoroughly humiliated, but satisfied, I resign myself to Trevor, who fucks me slow and deep, until he starts to twitch again, and drops a load in my butt, as if to say that he has more control than I do.
With both of Trevor's loads in my gut, I feel it sloshing a bit. He pulls out again, and I totter on my heels, unable to stand up straight. Trevor watches carefully, as I lose control, and his cum spills out over my thighs and my balls. He swats my ass and gives me another kiss.
For the rest of the year, I hung off Trevor's arm everywhere he went, and he rewarded me with gifts of stuffed animals, and the occasional rose, and, of course, with wads of semen that filled my tummy or swam around up my bowels. He wasn't too cruel, but he wasn't always benevolent, frequently dropping hints to people that I liked it in the ass, especially when he took me aside to the library to give me just that. I got used to having his load in me as I took math tests, and the like, and people got used to the idea that the hungriest ass in school belonged to the nerdiest girl.
Of course, they didn't realize it was actually the nerdiest boy, and that I didn't have the hungriest ass, just the most accessible, for dear Trevor. I was still embarassed to let him do what he did, but I wasn't so mortified. It got easier as time went on, a bit, but his cock can still be formidable for my poor, tight bum. The rest of the year was uneventful, if you consider a lifestyle of taking it in the ass and mouth for another guy even as a confused cross dresser is uneventful, but come the fall semester, that all changed.
END Part 3