Anally Yours by Anonymous

Anonymous

The Call

Another call clicked in. "Hi, you're through to technical support, Matt speaking, how may I help?"

"Keep looking at your monitor, act normally," said the voice, "This is Caroline."

He almost froze, his line manager. What had he done to warrant a call from Her? Out of the corner of his eye he noticed Her at Her desk in the far corner, watching him.

"I've found you online," She said through his headset, "red head boy."

He felt his the blood rush to his face, his IC profile, how embarrassing! No, wait, She couldn't be sure it was him, his face wasn't on it.

"Tell me Matt, have you ever had a woman put her strap-on in your bottom?"

"No Ma'am," he stuttered, randomly tapping a few keys to look as though he was dealing with a regular call.

"Fingers and tongues?" She asked.

Just deny it he thought, but before he knew what he was doing he had replied "yes". She had this power, the look, and the tone, which could make anyone do anything without question nor hesitation.

"Hmmm... and what about anything bigger? Toys, things that happen to be lying around?"

"Yes Ma'am," he replied in his most professional tone, surprising himself with the way he had regained his composure, "although nothing too big."

"Nothing to stretch you, you mean?" Her voice said in his ear.

"That'd be correct Ma'am," was his response; now almost convincing himself it was a normal customer on the other end of the line, not his imposing boss.

"Well that will change. This Saturday, tomorrow, you are to come to my house. The usual work time. Bring your overnight things. And two other things besides, are you listening carefully?"

"Yes" he breathed.

"You are to shave yourself smooth around your genitals and between your buttocks. Secondly, you are not to masturbate at all, is that clear?"

"Of course Madam."

There was another click and the line went dead, but he carried on talking, for appearances.

"That's not a problem, I'll have the packaging delivered to you as soon as possible. Good bye."

Breathing out, his mind swam. He could feel himself hardening; strange as his foremost memory was of complete shock and terror! Without a glance at Caroline, he finished his shift, though he could almost feel Her eyes on him until he left the office.

...

Saturday dawned, and as per Her command, he arrived at Her house at 9am. The night before he had shaved himself smooth as She requested, squatting over a mirror so he could both see and reach between his buttocks, marveling at how his anus looked surrounded only by smooth soft skin. Throughout the temptation to take his constant erection in his hand had been almost impossible to fight off, and although he knew She would not know, he still couldn't bring himself to disobey Her. The power She held, it was incredible he mused. In the end, he had fallen asleep, his erection remaining until he stepped in to the cold shower as the day dawned.

Her house was large, set back from the road and behind a tall stone wall. Ivy climbed the walls of the house. Beautiful yet imposing, fitting, he smiled to himself. Pushing the doorbell, he stepped back from the door and waited. He had chosen to wear a plain black t-shirt, boxers and jeans. Keep it cool and casual; don't look nervous he had repeated to himself over and over. It seemed like hours had passed when the door opened and there She was. No less imposing for being removed from the work environment, in fact quite the opposite; Queen of all She surveyed. And right now, that was he.

"Come in," She said in Her sharp business-like tone, turning and walking back in to the house.

He stepped inside, closing the door behind him. Nervous now, he knew this was it. He followed Her in to what was a large comfortable drawing room, where She had sat in an old green leather armchair, arms and legs crossed.

"Undress" She said.

He felt himself blushed, but Her look compelled him to act, and he slowly kicked off his shoes and socks, placing them neatly to the side. Next came his t-shirt, followed by his jeans. Sure he must now be bright red, he took in a deep breath, hooked his thumbs into his boxers, and pushed them to the floor. She didn't say a word, but beckoned him over with a finger, gesturing for him to stop when he stood directly before Her, legs shoulder width apart. Leaning forwards She reached out and took his penis in Her hand. He was amazed that even now, nervous and embarrassed as he was, it was semi-erect, and the warmth of Her palm caused it to stiffen still further.

Lifting his cock, She reached between his legs with Her other hand, taking his scrotum in to Her hand, squeezing it gently but firmly. Then She took each testicle in turn between thumb and finger and rolled it.

Looking up She spoke again, in Her commanding tone, "turn around, and bend over."
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He did so, his cheeks red, heart racing. Suddenly, as he felt Her gaze upon him, he felt utterly exposed. She could see every part of him in minute detail, and as the cool air ran over his freshly shaved skin he shivered. He felt the tip of a nail on the small of his back, and She drew it slowly, oh so slowly, down between his buttocks. He couldn't help but gasp as She crossed his anus, then continued down his perineum.

Abruptly She stood. "Follow me," She commanded, and set off out the room and up a wide staircase.

He followed, painfully aware of his nakedness, mind racing; what was going to happen now, what did She want him for?

He followed Her in to a large bedroom, a king-sized oak bed dominating the room. She turned to face him, eyes taking him in,

"On the bed, on all fours. Face the headboard and don't move."

He climbed nervously on to the large soft bed, and positioned himself, his bottom facing Her. This is it he thought, the fantasy; he couldn't believe what was happening. Her voice came from behind him,

"Put a hand back between your legs."

He did so, and felt her apply something cool and slippery to his fingers; lube he realized.

"Get yourself ready," is all She said, and he flushed again, the humiliation!

Moving his fingers to his anus, he tentatively slid a finger in to himself, exploring the warm soft walls of his rectum. He placed the tip of a second finger against his hole and pushed it firmly in to join the first, feeling the walls of his bowels become slick with the lube. He pushed them in as deep as he could, then withdrew them, and placed his hand back next to the other, his anus closing up again, the light reflecting off the lube smeared around its entrance. Behind him, he heard Her pull down Her jeans and knickers in one movement, then the sound of Her stepping in to the strap-on harness. She moved on to the bed behind him, close up, the material of Her t-shirt brushing his skin.

Placing a hand on each of his buttocks, She pushed them apart, exposing and spreading his small puckered opening. For a brief moment he was struck by doubts; did he really want this?, but as soon as he felt the tip of the dildo push against his opening, he knew. As he felt Her pushing steadily in he moved back against Her, uttering a low moan as he felt the shaft sliding deep in to his rectum.

She didn't say a word as She began to fuck him. Building up the pace, She expertly, opened up his virgin body, until the full length of the strap-on was disappearing between his smooth buttocks and in to him. She got faster and deeper, holding his hips and encouraging him to move with Her, letting her right inside him. His rigid cock swung to and through as he pushed back to meet her every thrust, and he moaned deeply as he felt Her fill him. Together, their breathing quickened, and her grip on him got tighter, pulling him harder back on to Her, wanting every inch of the shaft in him. Finally She spoke;

"Yes, yes, yes," She repeated, rolling her hips as she came, grinding her clit into the base of the strap-on, forcing it right up inside of him.

As Her orgasm subsided, She stopped moving, and rested, the shaft lodged deep in his rectum. He uttered a deep moan as She slowly withdrew from him, he felt as though a part of him was being taken away. His rectum felt empty, unnaturally so, as if She belonged in him. He did not move until She instructed him to turn around and face Her

He moved on to his back to face Her. She had put her plain white cotton knickers back on, and was standing by the bed, a small silver dildo in one hand.

"Pull your knees up and apart," She instructed him, in Her usual business-like tone. Handing him the dildo, She continued,

"Masturbate for me, one hand on your cock, the other moving this in and out of your bottom."

He blushed, but her stance and tone had the same effect as during office hours, and he had to obey. He nervously moved the dildo to his exposed anus, pushing it gently inside, surprised at how easily his body accepted it; it's cool shiny length sliding easily in to his lubed hole. His other hand moved to his cock, and he was surprised again as he took it in his hand, it had never felt so stiff, throbbed so strongly, now he truly meant the meaning of 'rock hard'. Unable to tear his eyes away from Hers, he slowly began to masturbate, his hand moving steadily up and down his own shaft, while the smaller silver one he moved rhythmically in and out of himself. Her gaze moved to between his spread legs, taking in his genitals, buttocks and anus, and he felt himself hoping fervently that She was not disappointed, that he was pleasing Her, that She would deign to take him again.

The minutes passed by at a crawl, until finally he felt orgasm approach. A small smile played over Her lips as She noticed his balls tighten, his breathing quicken, but no more.

"Keep going," She uttered as he looked at Her questioningly, and he obeyed, his hand pumping his cock faster now, the small dildo a blur as he pushed it as deep as he could inside, pulled it out, and pushed it back again. He closed his eyes and tilted his head back and he neared the brink, the waves shooting through him of previously unimagined pleasure making his whole body feel on fire.

"Keep your eyes on me," She spoke again, and again as if he had no free will of his own, he looked back at Her, locking eye contact.

And so, as he came, his penis spasming in his hand, the muscles in his anus contracting tightly, he felt Her looking right in to his very soul, and he knew he was Hers.