High School Beautiful Ch. 03

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Maddie is back in your classroom again. She has another big exam coming up, so naturally you have another… session scheduled. You’ve decided to continue your practice of double-dipping mother and daughter, so you’ll be fucking her mom later – though of course she doesn’t know that. All she knows is she needs an A, and the easiest way for her to do that is sex.

She does a strip tease for you, slowly taking off her clothes as she dances around. Finally she removes her undies and bra, pinching her nipples as she twirls to and fro. You drop your pants and lube up, preparing for the act to come.

“Maddie, have you ever done anal?” you casually ask.

“Anal… you mean you want to stick it in my…?”

You chuckle. “yes!”

“but it’s way too big! It won’t fit.”

“well, come here and I’ll loosen it up first.”

“How about we just do it like we did last time?”

You tisk. “That was just a homework assignment. This is a whole EXAM. You’ll need to do more to earn this grade.”

She hesitates, but then concedes. She moves over to you and you grab her by the waist, turning her around so her ass is pointed at you. You gently bend her down a bit. “Here, hold your cheeks apart”. She does so, giving you a good view of both her cunt and her virgin anal star. You rub a lubed finger over her pucker, then sink it inside. It is hot and tight, much tighter than her extremely tight cooter. You finger her ass, and slowly rub her clit to giver her some excitement to go with it. She gasps and begins to make pleased sounds as you continue to rub her. She moans as you slowly insert a second finger, widening her passage. You pump your fingers in and out, loosening her just enough, and making sure to lube the inside of her anal tunnel.

You pull your fingers out, and lube your dick once more. You then guide her backwards, pulling her close to your chest. You tilt her hips so her asshole lines up, and gently guide her down so her star sits against your tip. You push against her entrance, but she clenches and it won’t go it.

“Just relax” you say “it will feel good once it’s in, and it will go in much easier if you are loose.” She nods and you push again. She is still clamping too hard, but you keep the pressure up as you talk to her “It’s ok, just try to relax. Here, focus on how good this feels and try to güvenilir bahis open up” you wrap one hand around and begin rubbing her clit again as you continue to push at her back door. You can feel the muscles of her sphincter contracting and loosening as she tries to relax. You gently push down on her hips when she relaxes, but she keeps tightening up, so your tip does not make it inside.

You remain patient and continue rubbing her. She begins to pant, and ever so slowly her sphincter begins to loosen its death grip. Her asshole is pushed in a bit as your tip begs to penetrate her. With each contraction you slip another fraction of a millimeter deeper, and finally the sphincter begins to give way and your tip slides barely inside. She gasps and yelps a bit, pulling herself up, causing the brief moment of ecstasy to end as your tip exits her ass. “Ow!” she whines.

“Sorry! It will be hard at first, just try to relax. Ready?” She hesitates, but slowly lowers herself again. You have to begin the process again, and it takes a solid 10 minutes before finally your tip slides in again. She tenses and her sphincter muscles contract, but she doesn’t pull away and you hold her down so you aren’t pushed out of her. You kiss her back as you continue rubbing her clit. Her cunt is dripping with moisture now as you continue pleasuring her. Slowly she un-tenses, and bit by bit you begin sinking deeper into her.

You grab her hips and help her along, forcing her down further, causing your dick to sink deep into her. “ow ow ow OW!” she says between gasps as you sink into her. She sucks air through her teeth as you pull her up, beginning the first thrusting motion. You slowly stand up, using the motion to fuck even deeper into her. You lift her up like a doll, holding her in a hug and slowly allowing her weight to cause her to slip down and impale her ass on your dick. She squirms and complains a bit, but finally you are balls deep in her tiny ass. It clenches insanely tight around you, and the only way you can stay inside is by holding her down on you.

Her mouth is open wide, eyes bulging. “oh god its soo deep in me! Its like its in my stomach!” she mouths. She is standing on her tippy toes, with your dick buried in her ass. You lower yourself, and she follows your lead. You lie her flat on her stomach, legs together, dick still buried türkçe bahis in her. You lay on top, grasping a breast in each had and your ungulate your hips slowly. She is so tight you can’t fully thrust, as there is a lag time. You pull your dick back, and the flesh of her ass comes with it, being pulled along by suction and friction.

Slowly, the flesh of your dick slides past her anal flesh as your dick slowly moves out of her. She moans deeply as it does so. You then reverse the process, pushing in. Her ass resists the penetration, and her teeth bear in pain as she sucks in air as you slowly sink back into her ass. Slowly, thrust by thrust, you increase your speed. Her ass begins to loosen up, and the thrusting becomes easier. It seems to be causing her less pain as well – or perhaps just more pleasure to mask the pain. She alternates moaning and letting out a soft “ouch” as she sucks in air or grimaces.

As time passes you pick up pace, and you are soon well and truly pegging her ass. It is incredibly tight, and her flesh still resists you with each thrust, but there is enough pre and she has loosened enough that you slide in and out relatively easily. You hold on tight to her body and ram your dick in and out of her. She still grimaces and sucks air, but it seems like she is beginning to enjoy it more as she loosens up.

You stand up, picking her up with you and sitting on a chair so the force of gravity shoves you as deep as possible into her body as you push your dick in. She slides all the way down, so the entire length of your dick is engulfed by her anus. You hold there, enjoying the hotness and tightness of her anus as her anal muscles contract and vibrate.

You reach around and massage her clit, sliding a finger into her pussy as you do so. Fumbling, you grab a banana from your desk, along with the unused condom she provided earlier. You continue oscillating your hips, tensing so your dick rises in her ass, then relaxing so it pulls an inch or so out. As you do so, your arms are reached around to her front, as you remove the condom and put it onto the banana. The condom is lubed, so as you rub the fruit against her lips it is easy to stick it in, along with her own lubricant. She moans as you rub her clit with one hand, using the banana as a dildo in the other. As you continue it has the desired effect, güvenilir bahis siteleri you can feel she is approaching an orgasm. You drop the banana, and hug down on her hips as you rapidly increase the pace of fucking her ass. Your dick rubs pleasantly along her vice like anal canal, and finally she pops her orgasm. The banana twitches and gets drawn further inside her pussy as her contractions begin. Her entire anus clamps down hard with the orgasm, and the increased pressure sends you over the edge, spurting a load of cum deep into her asshole. She screams in pleasure as her orgasm continues, fueled by the hot load deposited into her rectum.

You turn her head to passionately kiss her as her mouth is open in pleasure. She French kisses you and you drag a hand through her hair as your cock continues to slowly thrust deep inside her cum filled ass. She opens her legs a bit and the banana slips out, the condom coated in her juices. You reach a hand down and stick several fingers in to take the banana’s place.

You remain inside her for several minutes as your cock slowly deflates. You kiss passionately as the afterglow of both your orgasms begins to fade. You keep up some small thrusting to keep yourself erect as the two of you move to the couch, your dick still forced into her anus. You spoon as you cuddle, making out with her and massaging her body as you throb inside of her.

Finally ready to separate, you turn over so she is laying stomach down on the couch. You slowly sit up, then watch as her ass grips your dick as you slowly pull out of her. Her asshole is red, and gapes ever so slightly now that you have removed yourself. You grab the banana from the floor, and stick it into her ass slowly, pushing it deep inside, and slowly fucking her with it. You reach under and massage her clit, and a few minutes pass before she cums again, this time breaking the banana in half as it is sticking half inside her. You slowly pull the broken fruit out of her, and a trail of cum follows. You hold her legs together to catch the cum between them and stop it from dripping onto the couch. With a paper towel you wipe it up, and once you release her she goes to the private bathroom to clean herself.

~~~

Finally you come to Maddy’s paper. You smirk as you look it over. The answers are atrocious. She didn’t even try. You shake your head, taking the big red marker from your hands and twirling it between your fingers. You snap the cap off and slowly stroke out a big red A. Then, after a moment’s thought, add a + to the end. “She sure does deserve it” you muse to yourself.

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