Maybe ... the cheerleader?

“You don't have to do this!” I stammer softly, wondering how I lost control of this situation. How does this young woman know about things that I couldn't even talk to my wife about?

“I know I don't have to,” Alison bats her eyes deliberately, “but Mr. P, you said it yourself last time, sometimes you need a little extra something to get you good and hard again, huh?” Her small hand rests lightly on my arm and she looks at me coyly. “Come on, Mr. P, choose your favorite scenario and let me make it real.” There is something genuine about my young tenant that I cannot refuse.

“I guess ... maybe the one with the cheerleaders...” Any concern that I might have had about taking advantage of Alison is instantly dispelled when I see her eyes light up in excitement.

“I thought you liked that one.” She pauses for a second before taking my hands in hers. “OK, Mr. P, imagine this then. There are three High School cheerleaders who have fallen into the hands of your football team: a Latina with a big rack who looks like she knows just how to please a man, a trembling blonde with a tear-streaked face and a tiny Asian girl with barely budding breasts who's even younger than the other two.” Alison leans forward to whisper conspiratorially, “that one's a virgin for sure, Sir.”

“No thanks,” I laugh at the eager teen, “I like my partners all grown up, but the frightened blonde sounds tempting.” Over the years I'd seen quite a few cheerleaders in tears because of some crisis or another; usually involving a boy but sometimes on seeing a bad grade or when they are given a detention. Of course, as a public servant, I couldn't really take them in my arms and comfort them the way I was tempted to. This is different and I let my imagination run wild. It is way too easy to picture finding the frightened young woman in my private office with a couple grinning linemen waiting for my approval.

Especially when I was still teaching, more than once I'd jerk off imagining what it would be like to have a cheerleader to play with. When we were younger, Fran would sometimes wear a cheap Halloween cheerleader costume, but as we got older it seemed a little weird to fantasize about women so much younger than me. Alison though is perfectly happy to let me play out this wicked fantasy of mine. She nods silently and then takes a deep breath as she puts herself into the mindset of the terrified young woman.

“Oh, thank God!” She exclaims excitedly, “Please Sir, you have to stop them; they have Valentina and GiGi back in the locker room...” her confidence ebbs when she sees the way I'm looking at her. “No ... Oh no, not you too.” I turn to the side and speak to the imaginary players who just brought me this offering.

“Yup, this one will do just fine.” I take Alison's arm firmly just above the elbow, “You men enjoy the other two. You deserve a reward after that game you played today. But hey,” I remind my imaginary team, “remember - you can do anything you like, but make sure they don't have any bruises where their parents might see.” I pull Alison closer and reach behind her neck to grab her by her hair. It's too bad she doesn't have a cheerleading uniform to complete the fantasy but having her already naked certainly speeds up the process. I love the way her hands push weakly against my chest as I tilt her head up to meet my mouth. Alison plays the frightened cheerleader perfectly; she even has what looks like tiny tears sparkling in the corner of her eyes.

“What are you going to do to me?” Her lips tremble less than an inch from mine as she looks up at me hopefully, “please, just let me go. I won't tell anyone.” There is something about having this lovely teen pleading with me, that sends waves of desire straight to my cock. It's too easy to imagine myself taking advantage of a hapless cheerleader brought to me like this.

“Oh no, my dear,” I pull her in for a kiss, content at least for now, with feeling her stiffen in my arms even if her sweet lips don't respond to the kiss. “I'm not going to let you go. I'm going to fuck your pretty little cunt until I've completely tamed you.” Once I have a firm grip in her fine hair my other hand slides down over the swell of her belly and through the tangle of golden curls until I find her wet sex. Her hand follows mine grabbing my wrist, but I've already reached my intended target and her attempts to pull me away is as ineffectual as her tearful pleading.

“I'll scream!” Her threat is a little late, she should have been screaming all along, and I lower my lips to hers again. This time though, as we kiss, I push two fingers into her pussy and when she gasps in shock and excitement my tongue plunges into her mouth so I'm exploring inside her from both ends. For a moment Alison seems to forget that she is supposed to be my **** captive and her tongue dances with mine, but just when I think she's surrendered she tears herself away with an angry gasp. “Stop it!”

“Well,” I tease her softly as my fingers wiggle as far as they can reach up inside her, “There's no hymen for me to rupture, so that's good news for you. Ms. Wilson thought a good girl like you might still be cherry like the little China Doll she sent us, but honestly I'm just as glad that you're not.”

“What?!” The surprise on Alison's face is only part acting.

“Didn't you know, Slut?” I ask as I put my own little twist on Alison's scenario. “It's a tradition between us and Central.” I explain as I finger her a little harder. “The winner gets to enjoy some of the losing team's cheer squad. Why do you think Coach Wilson sent you three down the wrong hallway?” I have to chuckle as Alison's eyes widen in understanding. I was beginning to think she would always be a step ahead of me, but not even her wicked little brain imagined that the three cheerleaders might have been offered up as the payment for a lost wager. “No one's coming looking for you, and no one will believe you if you try to tell them what happened.” I'm not sure if her weak moan is Alison pretending to be the betrayed cheerleader or if it just her trying to hold back her excitement.

“Don't do this, I'm not a slut, I've only ever slept with my boyfriend.” By now juices are trickling from her sex all over my fingers and dripping onto the floor, she is as ready as she'll ever be.

“Who is this stud of yours?” I ask firmly, “does he make you feel good like this?”

“Kyle Willard,” Alison is ready for me this time, “he's the middle linebacker who took out your #34.” I pretend to remember the play that knocked my halfback out of the game, maybe a linebacker that blindsided him and just about took his head off. With a shrug, I turn my attention back to the Alison as she cowers before me like the trembling cheerleader.

“My player will get over his concussion.” I tell her with a chuckle. “Hell, he might be balls deep in that little Asian hottie right now.” I turn my attention back to Alison who seems as affected by the illusion to the other cheerleaders getting gangbanged as she is by anything I have done so far. “Is this Kyle a good lover?” I ask again and I see the answer on her face. “That's OK. I'll show you how a real man fucks a pretty thing like you.” I spin her in my arms and push her roughly until once again Alison is on her bed; this time face down with her ass raised slightly at the perfect angle for my cock. “By the time I'm done with you, you'll never be satisfied by a boy again.”

“No, you can't!” She cries out when she feels my cock probing between her cheeks, and then when I start pressing into her, she adds in a soft whimper. “Oh shit, you're so big!” I am lost in this fantasy of fucking the luckless cheerleader. Alison's pussy is as tight as ever, but it is her moans as she plays out the role of the ravished victim that has me almost ready to shoot out a second load in under an hour. “Ugh ... uagh ... Oh please, Mister ... agh ... not like this ... please ... Oh No ... NO .... NOOO!” Alison must have been as turned on I am because it takes almost no time before her moans take on a distinct note of an impending orgasm. “Oh fuck ... you're fucking that hot young cheerleader ... fucking her so hard ... so hard ... so-o-OH FUUUCCCKK!”