Daydreams & Distractions ☼ Not Sure I Should

Not Sure I Should
A Daydream & Distraction by Redbud

  •  Couldn’t help having some fun with this common fantasy. This was indirectly inspired by Ximena’s story Like a Virgin. If you take your Christianity seriously, you might want to skip this little bon bon.

“Where are you going?”
“Where are you going?” he asks again.
“I forgot my backpack.” She walks ahead of him in a pleated plaid skirt and white blouse. She’s waifish. Her hair is shoulder length, blonde and straight. Her legs are slender. What else do you want to know? He’s memorized all of her. He’s masturbated mornings and every night imagining her. Her breasts harden him. He stares at her in class.

“Let’s walk together.”
“I’m not sure I should,” she answers shyly. They walk out of the school’s cloister and into a darker, arched entryway through the stone building. He skips ahead of her. They’re hidden from view. Closed oaken doors divide the walls to either side the entryway.

“Kiss me.”
She stops. She looks behind her, holding her bible tightly to her breasts. She looks ahead. She blushes. “I’m not sure I should.”

“Just a kiss.”

She glances both ways again, then stands on her toes, bible between them. Their kiss begins gently, but ends passionately. Her throat is flushed. His cock is swollen. Her presses his hips against her. She pushes him away with a hand at his chest. She bites her lip before she lowers her eyes and hurries around him. He watches the swishing hemline of her skirt.

He catches up with her. “That was nice.” They walk out from under the archway, then left following a cobblestone walkway. “I was just wondering–” She’s holding the bible against her breasts. Her nipples are showing. “Can I hold your hand?”

“I’m not sure I should.” Her voice wavers. She glances at him, askance. Then she offers him her hand. Her heart is beating hard, so his his. They walk round the back of the chapel and he pulls her between two flying buttresses. She leans back against the cool stone as his palm presses at her belly. “Can I– I just want to–” His hand rises toward her breasts.

She lowers the bible, both hands, to her hip. “I’m not sure I should.” Her voice shakes.

“I just want to feel–” His hand closes over her breast. She closes her eyes, head back and arches.

His other hand, reaching round, presses into the arch her back. He draws her narrow hips against his own. He’s dizzy. Her breasts are as soft and firm, resistant and giving, and more maddeningly contradictory than he had imagined. Her hard nipple presses into the center of his palm. Oh God but he wants more. He begins to unbutton her blouse. “Let me just– I just want to–”

“I’m not sure I should,” she whispers as his lips find her nipple.

Her eyes close. Her hands close around his head. Her bible rests on his back. She groans. He fingers touch her bare thigh. She pushes him away. Her nipple is glistening, red and flushed. Her breast heaves. She shakily tucks her breast under her blouse but doesn’t button.

“I liked that,” he says.
She bites her lip, skitters forward, gives him a kiss, then hurries past him. Her stomach is floating away. He follows.
“You’re beautiful.”
“Thank you,” she answers.
“I really mean that.”
They walk into another long arched hallway that passes through a second building. Anyone could see them. But there’s a little nook with a small stone opening that begins an old spiral staircase made of stone. He tugs her by the waist toward the opening.
She hesitates. “I don’t know.”
He tugs then pushes her ahead. She ducks. He follows, watching her bend over. They’re part way up the stairs. They’re hidden. No one uses the staircase but students wanting to go unnoticed. He stops her, hands on her hips, and kisses her ass. She bends forward, one hand on the twisting step above her, its tread worn round by centuries of use, the other holds her bible to her belly. He can smell her wetness. He lifts her skirt. God, is she beautiful. He kisses the smooth round design of a woman’s hips. He starts to pull down her white panties but she quickly turns around and sits.

He’s going to spurt in his pants.

He quickly unzips the black slacks of his uniform and releases his cock. God, he’s been dreaming about this moment. He’s had orgasms just imagining her lips so close to his cock. “Just–” he swallows. “Can you–”

She gazes at him, then at his cock, lips parted, her bible in her lap. “I don’t know if I should!” She fingers the knee of slacks. She glances up at him again. He cups that back of her neck and draws her lips to his cock. Her eyes widen. Her lips are rounded by the bulb of his erection before his cock fills her mouth. He moves back and forth. His hand guides her head as she sucks.

“Oh, Jesus,” he moans. She peers up at him, her perfect lips stretched. He parts her blouse. Both her nipples are hard and red. The vision is profane. She’s beautiful. She’s everything he idolizes. She’s an angel with cock in her mouth. He’s unsteady. He’s going to come in an angel’s mouth. “Oh God,” he moans. “I’m coming. Don’t stop. I’m going to… Let me come in your mouth. Please!”

She pushes him out of her mouth.

His eyes roll. He spurts once but doesn’t come. She scrambles to her feet and touches the thick release on her breast. A man has come on her! She did this to a man! She quickly searches as though for a cloth or tissue. When she doesn’t find anything she wipes her fingers against the edge of a step, blackening the gray stone. She closes her blouse and the thin white cotton darkens just above her distended nipple. She pushes past him. Her hips sway quickly left to right. He hurriedly tucks away his glistening cock follows her.

She glances back at him, her face flushed.

“Wait,” he says.

They both hurry back into the entryway with the ribbed vaults of its ceiling. She leads him right, into a long open hallway that faces another cloister on one side. The other side is hung with clothes, book bags and backpacks. She finds her own. He can see her nipples stretch the fabric of her blouse as she reaches for her backpack. He’s behind her. He presses his palm against her flat belly as her arm stretches above her. She pauses, presses back against him, feeling the broad warmth of his chest against her back. But someone will see them! She glances at him, then to either end of the hallway before she shoulders him away. She hurries.

“Where are you going?” he asks.

“Back to my class!”

“But…” Then he sees where she’s going. She turns into a bathroom. The door is wood with an arched top. She doesn’t close it. She puts down her backpack. She hurries to the sink, leans her bible against the mirror and plucks at the wetness on her blouse. She glances back at him through the half-opened door. She slowly lowers both hands to the sink. Her gaze doesn’t veer from his eyes. She leans, rising to her toes, her slim lower belly pressed against the edge of the sink, her back arched and fingertips supporting her.

He glances ahead and behind him, then he hurries inside and shuts the door behind him. He moves behind her and presses his cock against his ass. She gazes at him in the mirror, her lips parted. “What are you going to do?” she asks, breathless, questioning eyes lowered but still meeting his. He unzips his slacks, lifts her red plaid dress, and pushes his cock between her thighs. She’s wet. He can feel her slick moisture against the top of his cock, soaking her white panties. He movies back and forth and feels more: the swollen spread of her opening beneath the thin fabric, the stiffness of her clit and the cleft, the hollow, when he draws back far enough, ready to guide him inside her taut abdomen. Her eyes grow heavy, her head bows and leans, bending further, each time the head of his cock rides over her clit. Her legs widen. My God but she’s beautiful! He feels his orgasm churning, beginning to burn the tip of his cock. He reaches under her skirt to push aside her panties.

“I don’t know if I should,” she moans, voice strained.
“It’s wrong.”
“I want you.”
“I don’t know—”
He begins to pull but she stops him, her fingers in his, reaching between her thighs. “No, Sir. You can’t. It’s wrong. It’s not right. Leave the panties.”

Christ, he’s going to burst. She leans forward. The groove of her panties are soaked. He slides his cock back and forward. He groans. He shakes. He feels the nubbin of her mysterious clit with each forward thrust, then the tight drum of her panties as his cock draws back and over her opening. She’s slicker and slicker with the clear moisture of her youth. He can’t stop himself. He draws back, presses at the small dimple, then forward, then back again to press his tip against the tight cloth. She moans each time he presses. She rises to her toes and her eyes open. Her back curves as she lifts her pussy behind her. The toes of her black leather shoes turn inward, heels out.

He opens her blouse. Her youthful nipples hang down. He clasps her slender neck in one hand, hip in the other, draws back and presses. She inhales with a wheeze and rises to the tips of her toes. The head of his cock opens her, pushes, and pushes her panties inside her. The seam draws tight against her clit as he begins to pump. He can’t go deep. The panties stop him. They forbid, but he can’t stop. He can imagine there are no panties between the end of him and the wetness of her womb. He pushes and each time pushes a little deeper, her small dimple accepting him.

She inhales sharply. She’s going to come. The sudden, unexpected draw of the fabric, hard against her clit curls her toes. “I’m not sure–” she gasps. “Please, Sir! I’m not sure– I’m not sure I should!” But she does. She can’t stop it. The stiff bend of her back breaks with each spasm. Her thighs drip.

He holds her shoulders.

He pushes as hard and as deeply as her panties let him. His spurts come in quick, sharp thrusts. She stares at him, mouth open, surprised to feel the warm spurts inside her, shooting through the thin cotton of her panties. She feels them in her womb. She closes her legs tightly but the spurting warmth doesn’t stop. He fills her. She shudders.

“Please–” he gasps. “Don’t move. Just a little and I’ll– I’ll be done.”

“Does this mean I have to obey you?” She feels a final spurt. “Does this make me your wife? Do I have to bend over whenever you tell me, Sir?”

“Yes,” he groans.
“Does this mean we have to marry?”
“Would you, again?” she asks, biting her lip, gazing up at him in the mirror.

He reluctantly withdraws from her warmth. Her panties are dripping, creased and caught inside her, wadded, soaking her insides with sperm. “Sir? Does this mean I’m pregnant. I feel all warm inside.” She presses her legs together and swivels her hips as if she had to pee. “Can I pull my panties out?”
“But they’re making me pregnant, Sir.”
“Open your legs.” With his he finger he presses them further inside. She rises to her toes and grips his arm. “Good.” He raises his other hand. “Now be a good girl and suck my thumb.”
“It feels funny inside.”
“Just suck and never mind that.”
“Yes Sir.” She sucks and begins to swivel back and forth on his finger.
“Good girl.”
She gazes as she sucks. It doesn’t take long before her eyes roll with another orgasm. “That’s it.” He removes his finger and thumb. “Come on that sperm.”
“Thank– Thank you, Sir,” she says, hiccuping with orgasm.

“Now what about your class?”
“I gave all my students assignments, Sir.”
“But don’t you think you should be getting back to them?”

She reaches round him, presses her soaked pudenda against his thigh and bites his neck. She licks beneath his chin. She bites his earlobe. He feels her wetness through his slacks. She draws his ear to her lips with a fistful of hair. “But Sir, I’m all wet down there. I’m so, so wet. I’m–” She gazes up at him innocently. “I’m not sure I should.”

☼ Will Crimson October 15 2011

Categories: Consensual, Copulation, CP, Erotica, First Time, Impregnation, Insemination, Oral Sex, Pursuit, Quickie, RedBud, ReluctanceTags: , , , , , , , , , , , , , ,


  1. vanillamom

    oh, my, gAQS… geeze i just …Will…

    *blinks, clears eyes*

    hawt, hawt, naughty hawtness…

    okay, time for my bed…

    (thank gawd!! and You, Will, thank YOU!)



  2. paul1510

    such a naughty story, especially as the impression given was that they were both students.
    There was a couple like that in my last year at school, the science master and the art mistress, great teachers. but definitely an item.
    They got married the next year.
    At fourteen my imagination wasn’t quite as lurid as yours, thankfully!
    I leave to your imagination what would have happened had it been!

  3. vanillamom

    So Will, you know i read this before bed and it kinda blew my sox off…(hmm, and suddenly i was nekkid in my bed and and and…)

    well, you can fill in the blanks, i am sure.

    And i woke up with this story in my head, wholecloth. Just finished writing it, but i’ve been on a binge lately (writing binge, that is) so it won’t come out until Tuesday…but i’ve pinged back here to your story…)

    Thanks for a very erotic night!


    • vanillamom

      wish i could be concise…but of course, this is me so …*laugh*…

      the *image* that most stays with me is the panties…the lead up, the way it unfolded…the end of it…

      but the overall impression is the stop, the starting…the push=pull of want, need and propriety…

      i felt it was a teacher with a student btw…the older guy, but not OLD, ….maybe a younger teacher just feeling this for the first time for a student…

      and it was sooooooooooooo hawt.

      not my usual triggers, but it was really well done…the (as aisha says) “holding the tension”…was in perfect balance.


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