The Story of Annie and Sally Continues

Thanks for visiting self pleasure for women. I hope you enjoyed the first part of The Roommate as much as I did. Here is part two for your enjoyment.  Remember to bookmark this page if you want to follow Dharani’s Roomate story.

When the tempatation gets too much reach for a toy find yours and

Chapter 2

Part 2

Before the advent of Sally, Annie’s favourite fantasy went something like this -

It was after school when she and Michael, the Headmaster, were alone in his office. They’d waited all day for this moment to be together. She came into his arms as he stood in front of his executive desk. Reaching under her blouse, Michael undid her bra as Annie quickly undid the buttons. Michael caught her breasts in his free hand as they fell. His large smooth hands gently caressed her bare flesh as his fingers squeezed and teased her nipples to attention. While his hands played, he locked his mouth onto hers in a sensual French kiss.

Breaking away, Michael pulled Annie to him by her hips and wetly dragged his open mouth down her neck to her exposed breasts. Raising one to his mouth, his tongue rapidly flicked the soft surrounding skin of her nipple, his warm breath raising the flesh into a halo of tiny raised bumps. Now placing a soft kiss on her nipple, Michael hungrily gobbled it up between his lips in a soft bite and very firmly massaged the flesh into a neat hard nub.

Electric sensations shot from her nipple and her clit twitched in arousal. A soft moan came from deep within her throat. The tip of Michael’s wet tongue was now running over the flat surface of her nipple. Annie’s body shook with arousal. Then in an instant, Michael quickly sucked up her entire wet nipple with some of her breast into his hot mouth. Annie gasped with the feelings.

At this point, if Annie was in the shower she would already be fondling her soapy breasts and nipples in unison with her fantasy. If she became aroused to quickly, she’d gently press them against the cold tile wall until she calmed down enough and could begin again. The cold always dampened her arousal.

If Annie was in her bed, she would force her hands away from her breasts by gripping the headboard behind her, stretching out her naked body, taking slow deep breaths while focusing her eyes on the ceiling. If that didn’t help, she would resort to twisting the thin skin inside her upper arm, the pain would kill her arousal.

Unlike her sessions with the washcloth, during these special moments it would take all of Annie’s will power to delay orgasm and stick to her fantasy script. Her finger had the ability to deftly touch her hungry flesh in a way the washcloth never could. The Michael of her fantasy drove her pleasuring touch – the pressure, speed, place and even when allowing her to come.  

When her senses were cooled, Annie would begin her arousal again by using just her fingertips to unmercifully tickle her breasts, nipples, torso and inner thighs. She’d tickle and tease her flesh to a heightened state of arousal until she couldn’t bear it any longer. Only then her body would be able to accept what she was about to do to herself next.

Annie required a high state of sexual arousal in order to keep her mind focused on her fantasy - pretending it was Michael’s finger that rubbed the sensations of pleasure into her clit and not hers. If Annie craved an intense orgasm, she would have to pretend that it was Michael, not her, doing the pleasuring. If she couldn’t, then she would lose her desire and have to resort to using the washcloth in the shower. If that wasn’t possible, she’d miserably accept the outcome and go unsatisfied.

And so lost in her fantasy, Annie’s mind remained fixed on the things she would do to please Michael until she made him come. Stroke for stroke, touch for touch, what she did to Michael’s penis, she would do in turn to her own clitoris with her finger - mutual orgasm between fantasy and reality.

It usually ended with Michael coming in her fantasy and she coming for real -  

Michael lost himself in Annie’s breasts while her hand worked the hard length of his penis through his trousers. Now they changed positions as Michael unzipped and dropped his trousers and Annie perched herself up on the edge of the desk. Wearing only his shirt and tie, Michael stood with his back between Annie’s open legs and leaned his shoulders back against her chest. His hands reached and gripped the edge of the desk behind him.

Delivered into the cool air of the office, Michael’s engorged penis bobbed aloft as it thrust away from his body by the tilt of his pelvis from leaning back on Annie. In its excitement, a drop of pre-cum slipped from his thick glands and spun a clear thin thread as it fell to the floor. Annie’s hand went round his waist to ease the hard flesh with gentle cupping strokes from underneath. Michael begged her now to work his flesh harder to make him come.

In her effort to please, Annie slipped her other hand between Michael’s thighs from the rear to hold and massage his balls. Gripping Michael’s now rock hard penis in her other hand, she held him closer to her from behind, as she began jerking his flesh as if it was her own. Her hands were cold from the office air conditioning and their sensation on his penis aching for release only added to his thrill.

With each stroke, Annie’s fingertips lightly flew over the smooth head of Michael’s thick glands, her fingertips flicking the flaring edges of its cap. Occasionally she’d let a fingertip slip over his urethra and whenever she did, she could feel his balls tense up in her other hand. She’d gently massage his now tightening balls together along with the jerking rhythm of her other hand. She could feel he was close to coming.  

Slowing the pace down, Annie began to drive Michael wild. Her hand stopped jerking his flesh, as her other hand still continued to gently massage his tight balls. Now began the gentle assault on the head of Michael’s penis. Holding his glands with her thumb on top of the fleshy head, Annie positioned her fingertips below it along the raised ridge of flesh that ran to his urethra. Now her fingertips rhythmically worked in light backward tickling strokes under his glands and down the raised ridge along the underside of Michael’s penis. She was determined to tease out and catch more of his precious pre-cum.

It didn’t take long for more than a drop to appear or for Annie’s fingertips to smear over the tender opening and up over the thick fleshy glands of his penis. Michael groaned and bucked his hips. The intensity of her tender touches on his excited flesh were now overwhelming. He wanted Annie to dispense with the tenderness and begin jerking his penis again.

Again, Michael tried to thrust and escape her teasing, hoping to encourage her back to jerking him off. Annie would have none of it and grabbed up his penis again and gave him a shuddering thrill as she employed all five fingertips now into massaging just the throbbing head of his penis with his now very generous pre-cum. But this was not the way he wanted to roll.

With a groan, Michael thrust out his pelvis from the intensity again. His flesh throbbed with its urgency now to release its load as he gripped the desk from the wave of a sudden rush.

He couldn’t endure Annie’s teasing any longer. He needed a proper jerking. Letting go of the desk, he quickly gripped his large hand over Annie’s, squeezed their hands together over his rock hard penis and took hers along for the ride as he began to pump his flesh in short rapid strokes. With his free hand he pushed Annie’s away and scooped up his hard balls and roughly massaged them. Breathlessly, he ordered Annie to quickly put her finger into his rectum as high as it would go and wiggle it – NOW!  Michael’s penis and rectum both pulsed in unison, his muscles formed a tight ring around Annie’s finger, as he began to come.

As he did, Michael let out a small cry; his body immediately lost all control as wave upon wave of convulsive pleasure swept over him. Maintained his grip and he continued to rapidly pump their hands over his penis as three long clear ribbons of cum shot out and over the carpet.

Annie could feel the movement of it as it coursed through the shaft of Michael’s penis with every spasm. She marvelled as she watched it shoot its way out from the now crimson head of Michael’s glands – it was powerful, almost violent as the fluid shot.

The eruption ended with his fifth spasm, too weak to shoot now, Michael’s hot clear come drooled down their closed fists. Wrapping their sticky hands in his white shirt tail, spent, Michael turned to face Annie and crumbled in her arms; he buried his face in her neck as she kissed his ear, whispering her love for him.    

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