Chapter 4

Then everything changed, or at least that’s about the time Jennie took my blinders off and let me see the world as it really is. It all started with school, or at least what happened just a week before school started. I was out in the front yard washing the car when Jennie’s mother walked up. I was startled and nervous, partly because I was worried she had found out about me and Jennie, but also because she was a really fine looking older woman.

Sure, Jennie was cute and hot, like a lot of girls, but you know it’s different with older women who have really filled out in all the right ways. Her mother was maybe 30 or 35, or so Jennie thought, but had kept herself in shape. And she had a nice shape, with nice firm breasts that were always begging for me to look closer, and the perfect ass and legs. You could tell how hot Jennie was going to look in a dozen years, and the sight of her mom made my mind go blank for a moment.

As she approached all I could think of was how tall and sexy she was, with her long wavy curls falling down to her shoulders and her tight fitted top that somehow left the bottom half of her bouncing tits totally uncovered. Her nipples were hard and pointed right at me and I almost melted right there on the driveway. She was a beautiful older woman who I prayed to god would drag this next door neighbor boy behind the house and force him into an afternoon of sex. But no, she acted all clueless about what she looked like to me in her shorts and skimpy top and just starting talking.

“Taylor. Hi. It’s good to see you again. Say, I was wondering about the upcoming school year. I know you’re going to be a senior at the same school Jennie’s going to. She’s going to be a freshman. Isn’t that exciting? You kids grow up so fast. But I was wondering if you could help her out, like show her where everything is and how everything works. Would that be alright?”

There was a lot more of this, Jennie’s mother prattling on about all sorts of stuff, but it really just came down to her wanting me to look after her little girl. Boy, if she only knew. Then out of the blue I said something I later would really regret. “Well, if you’d like, I could walk her over there sometime this week, before school opens, show her the place, like administration and the gym and stuff.”

“Oh, that would be perfect. Why don’t you come over tonight and ask her? Or maybe I’ll ask her and then phone your dad. I’ve got his number. Would that be alright?”

So it was settled, and with her mom’s blessing Jennie and I took off two days later, walking to the school in mid-morning on a hot summer’s day. As we neared the school grounds I pulled her in, one hand down to push into the rear pocket of her shorts, happy to think that I’d be able to have her sit on my lap during lunch period and make all of my friends envious. My senior year was definitely looking good.

We walked around, found an unlocked gate, and I did a standard tour of the campus. Then we saw a side door of the main building that had been left ajar and with a quick look around we went in and walked the cool and empty hallways. Up on the second floor we found a large science classroom with windows that looked out onto the main courtyard.

It was there that I let Jennie know I couldn’t wait any longer, and she didn’t put up any kind of fight. When I pushed down on her shorts she stepped back to remove them, panties and all, before tossing them by the teacher’s desk. She pulled off my favorite peach colored blouse but had me help undo the back snap of her totally unnecessary bra and had it join the shorts. And there she was, completely naked and arranging herself over my throbbing boner, freed from my shorts and poking straight up from where I was sitting in a chair.

I had thought of pulling a large old bedsheet off of a pile of stuff on the side of the room so we could use it as a kind of bedding on the floor, but Jennie straddled me right there on the chair, allowing me to pull in on her naked ass and help her ease down onto my cock. On my bed she had total control, sitting up on her knees and riding me like a horse. With me sitting on the chair, Jennie couldn’t just stand over me and lower herself down since her legs didn’t quite make it all the way down to the floor. Instead, I had Jennie wrap her arms around my head and lean into my chest while I held her legs up at her knees. That way I had total control, holding her up while impaling her twat on my entire length as I slowly moved her up and down my cock.

That was fine for the first few minutes, just another new way to pump myself into her. With her tits rubbing against my stomach, her head leaning into my shoulder, I was having a great time. When my arms got tired I just let go, pushing her ass down onto my lap, shoving her twat down on the entire length of my cock. Again, great for me, but then Jennie gasped out the words, “On the floor. Can you lay down?” I got the idea immediately. Without losing my place inside of her, I slipped off the chair and down to the dusty floor, me laying on my back and Jennie’s legs folding on either side of my hips.

Now Jennie really took over, riding me up and down, playing with the depth of my cock, lost in the fuck that had become all about her. I could easily reach up to massage one of her bouncing breasts, the other hand down lower to play with Jennie’s clit, all the rest of me focused on the wonders of being sucked up inside of this hot little girl. That was one of the few times we climaxed together.

Jennie wasn’t pounding down on me so much as riding my tip, up high on her knees, pushing down over the first few inches of my cock and then up to where I popped out, then back down and sucking me back it. We were both into it, Jennie starting to give out some low grunts and moans, then finally screaming out, loud but short high pitched screams of delight, collapsing onto my chest and grinding into me even as I poured a full load of cum inside of her.

I rolled her over into the wall, pinning her there, continuing the fuck with fast but short and deep strokes, loving the feeling of Jennie’s pussy enveloping me as my balls flooded her with hard jets of cream. It was wonderful, one of the best fucks and orgasms we had ever had together. But that’s not why I remember that day.

We were just lying there, enjoying the cool feel of the hard wood floor, the soft warmth of each other, talking about nothing in low tones, and I couldn’t have been happier. Then Jennie pulled back, acting startled, her eyes widening at something she saw over my head. I looked back and there was this face, some guy smiling and looking down at us from the doorway of the classroom.

I rolled over and got up on my knees, my softened dick hanging free, and tried to put on a brave face. “Hey, what’s up? Nothing for you here, so get lost.”

“Oh, I think there’s plenty for me here.” The guy walks in, an older man, wearing some kind of vest with an insignia or badge and some kind of belt with keys and a baton or something at his side. I thought he was a cop or something, but quickly figured he was just a guard, maybe school security. “You and your little girl have no business being here now, you know that, don’t you? Trespassing on school grounds. That’s a no-no dude.”

I was trying to think of something to say, all while looking around for my shorts, when a second man with a similar fake-guard kind of get-up walked in right behind guard number one. He was a little taller and wider, with a beard and sunglasses and cap on. Even with the sunglasses it was obvious his gaze was directed at Jennie, now huddled naked in the corner behind me. “Yeah, no trespassing, but maybe we’ll let you off light this time.”

“Um, sorry, and we’ll leave. We’re going right now.” I stood, trying not to be too embarrassed by my own naked ass, torn between wanting to guard Jennie and wanting to make it to where I had tossed my shorts and shirt.

The first guard, the clean shaven one, made my decision for me. “Go ahead, get dressed.” Fine, but as I stepped over to where my clothes were piled, he walked deeper into the room and right behind me, cutting me off from Jennie. The second guard was right behind him, putting a wall of flesh between me and Jennie as she remained silent and naked in the corner of the room.

I immediately knew I had screwed up but froze, unsure of what to do. The first guard again acted for me, turning around and walking over to Jennie, still kneeling in the floor, one hand over her chest and wide eyed and wondering what was about to happen. The guard extended a hand and Jennie reacted as though she was with a group of friends in the back yard, taking the man’s hand and allowing him to pull her up onto her feet.

“Damn, bitch,” the guard said, looking her up and down. “You are one hot little number. Saw you giving your man a lap dance from over in the other building but I didn’t know you were so fine.”

This actually got me to move in and say something, but I had only gotten out “Hey, you can’t,” when the second guard, as wide as the rows between the desks, stepped forward, cutting me off and keeping me from going any further.

I didn’t see it happen, but the first guard had somehow loosened his belt and pulled his dick out, bringing Jennie’s hand down to his crotch and telling her what he wanted. “You have such a pretty little mouth. Like you have a built-in pucker. It wouldn’t hurt to just give me a little kiss, would it?”

Without a word Jennie, shaking and with only a quick glance in my direction, went down on one knee and leaned in to do as instructed. I didn’t have a good view of the action, but the man groaned as Jennie brought his cock into her mouth, then slowly went down onto his knees, one hand holding Jennie’s head with the other down to feel her breasts, all the while pushing in with his hips. “That’s it, girl. You’re doing fine, like sucking on candy.”

That should have been it, a couple of quick blowjobs and then gone, but the guys wanted more. After a minute of enjoying Jennie’s lips and tongue, that first guard began pulling her head in, pushing his cock in deeper, face fucking Jennie into some deep throat action. Of course she couldn’t keep that up for long, quickly choking, finally forcing herself back and away from the man’s cock and hands.

As Jennie turned away and tried to catch her breath, the guard bent down to kiss the top of her head, telling her that everything was okay. “That’s fine. You did fine girl. You just wait here.” Here he stood, pulling his pants up and taking a step over to where the large bed sheet covered a pile of what turned out to be books on the shelf by the windows. “Jim, help me here man.”

The man blocking me from Jennie gave me a look, a glare I could feel through his dark glasses, and went over to help the first guy pull up the sheet and walk it over to the large flat surface of the teacher’s desk in the front of the classroom. It took all of ten seconds, during which the first guard spoke out, to all of us, but directed at Jennie. “There we go. We’ll fold this sheet over a few times. Not quite a feather bed, but a hell of a lot better than what your boyfriend made you go down on.”

Nothing surprising, but it still shocked me, the guy openly admitting to what he wanted from Jennie. Jennie had already stood up and began walking my way, but again the big guy, Jim, took a step over and put a hand on her shoulder, and with a quick look at Jennie’s naked form he lowered his other hand to her ass, cupping one cheek and leading her over to the desk.

“That is one fine little ass you have. Such a pretty little girl.” The guard then leaned down, bending low at the waist to smell Jennie’s hair, pulling up on her ass with the one hand and feeling up her tits with the other.

I made a move, said something ineffectual like, “Hey, but...” and the big guy just raised his head from Jennie’s head and looked at me, then pulled his hand away from her ass, pulled up the baton from his belt and flipped it around a few times, then pointed it at me and in a real firm voice said, “Sit, or would you like me to shove this up your ass?” I’m embarrassed to say that I sat and shut the fuck up.

Jennie was shivering, and not from the coolness of the room, plenty of summer heat radiating in from the windows. But she knew what she was going to have to do. The big guy, Jim, guided Jennie by her ass over to the teacher’s desk, and when the first guard told her to sit on the desk, with a little help from Jim’s two large hands and without any hesitation she just hopped up. She was obviously nervous, her eyes wide and in shock, but still fully aware of what was expected of her.

The two men gave me a quick look, big Jim shaking his head in a warning against me trying anything stupid, and then turned their attention back to Jennie.

They took their time, feeling her up, commenting on her body, even leaning in to kiss her head, lick her tits, and talk low to her, letting her know she was beautiful and the embodiment of every man’s desire. For just a minute Jennie snapped out of the trance she was in, putting up her hands to cover her chest and saying, “Please don’t. Please.” Pretty ineffectual, but the men should have gotten the idea. Her reluctance at what she knew they were about to do probably only turned them on even more.

Then the first guard made a big gesture of dropping his pants, pushing his belt and all down to his ankles and pulling out his cock, still gleaming from the mouth job Jennie had started on him just a few minutes before. He used his hand to open her knees a little wider, her feet dangling high above the floor.

Pushing his hips in, levering Jennie’s thigh’s out wide, he pulled in on her legs, pulling her ass to the very edge of the desk while grinding his crotch into her wide open bush. These guys were plenty tall, a good head above me, and the edge of the desk was actually below their hips. So this tall but slim guard had to bend his knees out and lower his body while pulling up on Jennie’s ass to come even with her crotch. Kind of comical, but no way was I laughing.

With Jennie pulled tight to his groin, he reached out and took one of Jennie’s hands and brought it over to where his cock pushed up between her thighs. Jennie just sat there, looking down at where the guy had her playing with his cock, open mouthed and breathing in gasps and obviously overwhelmed with what we had been caught up in. The guard liked this, seeming to enjoy playing with Jennie as he had her hand moving up and down his cock, his two hands reaching down to play with her breasts. After a minute of this he reached out to Jennie’s shoulder, pushing her back, making her lay back on the layers of sheet that covered the desk. “Just relax. Let me do the work baby doll. I’ll make you happy.”

I thought he’d just fuck her, push it in and get off inside of her, but the guard was obviously a real sadist. “That’s it. Hold my little man. Now I just want you to rub me up and down your slit. That’s it, rub it up and down. Bet you like that, right? Nice and wet. Bet you want what I’ve got.”

I had a clear view from where I sat, the big guy named Jim standing just to the side and watching the show while holding Jennie down at one shoulder. That’s how I could see Jennie using one hand to hold the first guard’s cock, rubbing him as though trying to jack him off, but also following directions and moving the leading hood of his piece up and down through the middle of her hairy slit.

“OK. That’s enough. You want some now, right? Well, you put it in. Show me where your little box is. That’s it. Rub it around. Now push your hot little ass in to me and suck me in.” And she did, though with a bit of help from the guards. Jim pushed in on Jennie’s shoulder and neck while his friend pulled in on one of Jennie’s knees, Jennie’s back and ass sliding with the sheet right into where she had positioned the guard’s long dick.

The guy was long, maybe a little bigger than I was. He got a gasp out of Jennie when he popped in, and his own reaction was loud and clear. “Oh, fuck man that’s good. Haven’t felt anything this tight in years. No way I’m going to last very long inside this piece of pussy.”

This is when the games stopped and the man just went into full fucking mode. He pulled Jennie’s knees up and pulled her ass completely off the desk and began pushing into her, another inch with every thrust. This went on for a couple of minutes, the guys’ cock disappearing into Jennie’s open legs only a dozen feet before my eyes, pulling back a little more slowly, then pushing in again.

Then he paused, as though trying to catch his breath, then pulled Jennie’s knees up and said, “Here girl. Raise your legs up. That’s right, up onto my shoulders. Let me get all the way into that hot little hole of yours. Just hold your legs up and I’ll do the rest.”

I couldn’t see Jennie’s face, her head being turned away from me, but her legs went up, her feet not even making it to the guy’s shoulders. With one hand under her ass and another up to cup one of Jennie’s breasts, the guard got back to it, fucking Jennie as though he had just won her in a card game. Jennie turned her head up, her mouth open and gasping, grunting out with every loud slap into her twat from the guy’s relentless pounding. She even put out a hand to touch the hand holding up her ass, but the guy didn’t seem to notice.

The action went on for a few minutes more, the room empty of sound but for the wet action of the ongoing fuck, the slapping together of their bodies and the gasps of breath from Jennie with each thrust in. Then came a loud groan and some choice words from the guy pounding into Jennie’s hole as he realized he was about to reach his limit.

“Oh my God, shit but this cunt is tight, like she’s sucking it out of me. No way I can hold back.” And here the guy brought both hands down to support Jennie’s ass, pulling her hips and ass up high off the desk to be even with his crotch. His hips quickened in their movement in and out of Jennie’s open thighs, their bodies slapping together, Jennie herself just barely supported on the desk by her head and shoulders.

After another minute of this hard animated fuck the guy dropped Jennie back on the desk. He leaned into her open thighs, pulling her in tight to his crotch as he collapsed down onto her naked body. Hands under her ass cheeks, his head way above hers on the desk, all I could see of Jennie as the guard continued to pound into her was her legs, rising and falling on either side of his hips as though she was unsure of where to put them.

The fucking only got more intense as the guard began to climax. Except for Jennie’s waving legs it really looked like he was fucking the desk as he yelled out to nobody, “Oh shit, oh my fucking God I’m cuming. Suck it up bitch. Just feel me fill you up.” And a lot more of that, telling us all how he was filling this slut up with everything his balls could pump into her. He lay there on top of her for another minute, his hips occasionally giving up a couple of short fast jerks before settling just a little more deeply within Jennie’s naked thighs.

The guard finally straightened up, slowly standing up and giving Jennie some air. The guard was still deep inside of her, and he did his best to move his softening length in and out of Jennie a few times, but he finally stepped back, not bothering to pull his pants up. Jennie pulled her knees up and rolled to face the far side of the desk, but the guy was done with her, merely slapping her upturned ass and speaking to his partner. “Damn, but you’ve got yourself a real treat for yourself there, Jim. Hot, wet, and ready to please.”

Jennie had curled her legs up onto the desk, but now the second guard, the big guy, Jim, stepped over from the side where he had been quietly waiting his turn. “You are a beautiful little girl, you know that?” Jim said as he reached out to massage Jennie’s ass. When she didn’t respond to what he obviously thought was a complement, Jim just reached forward and pulled her back to the edge of the desk, but with her ass up and tits down into the thin layer of cloth that separated her from the desk.

Even with her bare ass pulled off the edge of the desk, Jennie’s legs hung down but still didn’t quite reach the floor. As she slid off the desk and down to touch ground, Jim stepped in, pushing his crotch into her back, hands down to play with her ass. Then he reached down and cupped her ass cheeks with his two hands, pulling Jennie up and laying her face down on the desk, arranging her knees under her like she really was just a little baby doll. Then he bent over, kissed her cheek and said, “You just lay there little girl. It’ll be alright.”

Jim unbuckled his belt and pushed his pants and equipment down, his dick getting stuck in the folds of cloth for a moment before springing forth and pointing straight out and over Jennie’s ass. Jennie didn’t see it but I did, and I hate to say it but I grew hard at the sight. Not at some desire for the guy’s cock but because of what I knew he was going to do inside of Jennie. Jim wasn’t quite as long and curving as me or his partner, but his piece of meat was a good deal thicker, at least half again as much, and with a blunt tip on his cock that looked like a small fist. He rubbed it a few times, took his time in arranging Jennie’s ass, feeling her up, playing his hands up her thighs and through her twat, enjoying his position and what he was about to do with her.

Jennie got her first feel of her unwanted beau when Jim pulled Jennie up onto her knees, having her position herself like a dog on the desk, then pulled her ass back into his waiting cock. He pushed his raw piece of meat through her butt cheeks a few times, perhaps worrying her that he was going to pound himself into her back door. She suddenly came to life, breathing hard and fast and trying to crawl across the desk, but the first guard was there with a hand to hold her back. Jim quickly wrapped his large hands around either thigh, picking Jennie’s ass and most of her body fully off the desk. It was like he was just picking up a toy doll, one hand coming all the way down and back through Jennie’s crotch to guide his cock to it’s rightful place within the cum-wet folds between her thighs. And then he pushed in.