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Sue read one of my other stories and sent me an e-mail stating that her deepest fantasy was to be anally deflowered. I tried to get her to help contribute to her story idea, but she declined. This is still her idea but it is my “concept” of what it meant.

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Anally Deflowering Sue-The Deepest Fantasy

By Powerone

I am a 25-year-old, redhead. I live in an East Coast big city. I am 5 feet 6 inches tall (in heels), long legs, large breasts (with nipples the size of a half-dollar) and an extremely pert ass. I am very proud of my ass and that is the reason for my fantasy. I exercise regularly, especially my ass. My cheeks are tight. Between my cheeks, my anus is pink and delicate. I take great pride in my body, especially my ass.

I had dated the same man for the last five years, but suddenly I found out he was cheating on my so I dumped him about 6 months ago. I haven’t dated since than, not because I wasn’t asked out, I just haven’t gotten over the betrayal. This has made me particularly horny lately. We had a fairly active sex life, but it was routine. While we had sex often, I refused oral sex and anal sex was a definite taboo. Some of my friends had told me they had tried anal sex (most did not get very far until they made their partner stop) but did not like it because of the intense pain. Even those that did finish refused to do it again. I guess the forbidden is what we are deepest fantasies are about.

I have resorted to masturbation lately to satisfy my lust. My vibrator has become my sex partner. I would lie in bed at night, my vibrator gently rubbing my clit as I dreamt of having sex. My latest fascination was with anal sex. I often fantasized of how I would be anally deflowered. While I would not do this in real life, it often consumed my fantasy life.

I had come home from work, ate dinner and took a leisurely bath. I put on a shirt that covered my ass and decided to go to bed. Not to sleep yet, but to masturbate again. Masturbation relaxed me before I went to sleep. There is nothing more comforting than an orgasm.

I lay on the bed and reached into the drawer to retrieve my vibrator. If was not very big, but when applied to my pussy lips and clit, it never failed to satisfy me. I put my hands into my panties and began to gently stoke my pussy, the vibrator becoming wet. I closed my eyes and began to drift off into my fantasy world. I moved the vibrator further back toward my anus. My body shivered as the vibrator, wet from my pussy, played across my tight anus. I ran it around and began to push it in. The tip slowly entered until I pulled it back out. This always happened. I wanted to be anally deflowered, but was afraid of the pain. The vibrator moved back to my pussy, slowly running up and down my slit, moving over my clit. I slowly began to fade off into my fantasy world.

I felt hands take the vibrator from my hand and turn me over so I was lying on my stomach. My hands were grasped and I felt rope being tied around each wrist. First one wrist was tied to the bed rail, than the other. The knots were tied tight.

“Who are you, what do you want?” I cried, suddenly afraid.

“My name is Michael and you know what I want”, Michael said.

“No I don’t, untie my hands and get out of here before I scream for the police,” Sue said.

“You wouldn’t do that because it will not do any good. I am here to fulfill your fantasy. I am here to anally deflower you”.

“Please don’t hurt me; I only dream about that, I don’t want to really do that. Just let me loose,” Sue begged.

“Sorry, but you made up the rules for this game. The only way you can stop me is when you cum. Until that time, you are mine to play with,” said Michael. “Let’s get you into a better position”.

Sue could feel him slide his hands under her stomach and push her up until she was on her knees. Her short shirt now just barely covered her ass, her breasts hanging down. She felt him tie more ropes around her thighs and he began to pull her thighs open.

“Please don’t, no more ropes,” she cried, as her thighs were pulled open. She felt him first tie one rope under the bottom of the bed, pulling her leg wide open. He went to the other side of the bed and began to pull the other rope, pulling her other leg wider and wider. “No more, you are spreading them too far,” she yelled, but he continued to spread her open. She could feel her ass and pussy begin to spread open. He tied more ropes at her ankles, tying them to the corner of the bed.

Tears began to run from Sue’s eyes as she imagined how she looked. Her arms were bound to the top of the bed. She was on her knees, her ass invitingly open in the air, her legs spread and tied to the bed. She never felt so vulnerable before.

She watched as Michael began to undress. Soon he was naked and Sue trembled in fear when she saw his cock. It was over 8 inches long and 1-2 inches in diameter. “Yes, it is very big isn’t it, but this is your fantasy.”

“Please, what are you going to do?” wailed Sue.

“I am going to fuck you in the ass, just like in your fantasy. I will start by sticking my fingers deep into your anus and rectum. I will than begin a slow but painful fucking of your anal tract. You will be forced to take all eight inches of my cock. Once I manage to stretch you open, I will begin to forcefully fuck you. As I fuck you harder and deeper, I will begin to play with your nipples and your pussy. When you are ready to cum, I will cum at the same time, shooting my hot load deep into your asshole. Only than will your fantasy end.”

“No, please, your cock is too big to stick in my ass. Fuck my pussy instead,” she begged.

He moved onto the bed and began to run his hands down her back toward her ass. Her body trembled in fear. She knew that soon she would be stripped naked. He moved his body over the top of her ass and she felt his hands move down toward her breasts. He grasped both of her breasts in his hands. The kneeling position she was bound in allowed him free access to her hanging breasts. He forcefully grabbed each hanging tit, squeezing before his fingers began searching for her nipples.

“OHHHH, that hurts, please not so hard, be gentle.”

“You will soon learn that with pleasure also comes pain. My cock and hands will force your body open allowing me to pleasure myself in your ass. As my cock is squeezed by your silky insides you will be stretched wider and deeper than you thought possible. This will cause you exquisite pain. Eventually the pain will mingle with the pleasure and you will cum with my hard cock up your ass, milking the hot cum from my cock.”

He twisted her nipples, making her gasp as he pulled her coral aureoles and forced her stiff nipples to become erect. She tried to move to escape the cruel fingers but the tight bondage only allowed her to sway her swinging breasts back and forth. Michael began to milk her hanging tits, gasps coming from Sue’s mouth as he manhandled her breasts. His fingers began to unbutton the shirt, allowing his hands access to her naked breasts. He pulled her shirt up over her back. Sue turned red in humiliation, as he looked at her bound body, her naked tits hanging down, waiting his punishment.

“No more, I am so embarrassed. You are stripping me naked as I am bound here”. She felt him cut her shirt from her body, she was now naked from the waist up and only her panties covering her ass.

“What a nice ass” and he again moved over her body so he could begin again to tease her nipples. She could feel his erection resting in the cleft of tight ass cheeks. He began to pinch and pull her nipples, Sue gasping in pain.

“OOOOWWW, that’s too hard, Ouch, stop,” she cried reacting to a cruel pinch of her delicate nipples. Her nipples grew harder and longer from his insistent torment. She began to buck under him, her face flush with shame and humiliation. Her ass moved sensuously against his cock, her panty-covered ass caressing his cock, making it grow harder and longer.

His fingers tightened on her rigid nipples and Sue winced in pain, closing her eyes and crying out in pain as it became unbearable. She cried out, “please, that hurts so much” only made Michael tighten his grip harder and he began to twist her nipples in a counter clockwise motion. Sue trembled violently in Michael sadistic grip. If she could only endure the pain for a while longer, he might stop.

All of a sudden the pain in her nipples diminished. She looked down and saw her nipples pinched tightly in Michael’s fingers, yet the immense pain she felt before was almost all gone. She realized that she was beginning to deprive sexual pleasure from the pain. She turned red in humiliation as she began to enjoy the pain that was only a few minutes ago, sheer torture.

Michael was watching Sue’s reaction to his breast torture and noticed the change in her demeanor. He released his tight grip on her nipples and began to flick her nipples with his fingers, acting like little floggers and pinched the pink areola, Sue moaning and crying out little gasps of pleasure from the manipulation.

“I told you that with pain comes pleasure,” said Michael, Sue’s ass rolling sensuously against his cock. He released his grip on her breasts, forcing a groan from Sue as she felt empty. He got off her back and kneeled up behind her. She began to regain her composure and she trembled at the idea of Michael staring lustfully at her panty-covered ass. She began to sob as his hands returned to her helpless, bound body, this time moving sensuously over her ass cheeks.

“Please no more” she begged. His hands moved over her cheeks, squeezing the flesh between his fingers moving lower between her legs to grasp and squeeze her thighs. Sue cried out in anguish as his hands moved toward her pussy. He would soon feel how aroused she had become when he felt her wet pussy. Her hands gripped the bed rail tightly as his hand moved over her pussy, pushing his finger through her panty-covered pussy lips.

“OOOHHHH, please, don’t, stop, AAAAAH, not my pussy” she moaned as panties became soaked from her sexual stimulation. Sue closed her eyes and breathed through her nose. She could not stop him from having his way with her, but she was determined not to enjoy it. Her resolve was quickly smashed as Michael began to lower her panties down over her ass. When he reached her tied thighs, he cut them off, leaving Sue withering on the bed.

Sue turned red in shame and humiliation as she imagined how she looked, bound face down, naked with her legs spread wide and her pussy and anus opened for Michael to see. His hands spread her cheeks wider and wider opening her anus to his gaze. He held her open for long minutes, staring at her pink anus. He wasted no time in continuing his ruthless ravishment of her body and she could feel his breath on her anus and then suddenly she jumped in surprise as his tongue began to bathe her naked anus.

His tongue began to bathe her body from her anus, down to her wet pussy, lapping up to grasp her clit with his lips. Her body shuddered and attempted to escape the rasping tongue, but the cruel bondage held her in his grasp. His hands reached under belly and slipped up to grasp her hanging breasts. Again, his fingers began to grasp the erect tips of her nipples and began the milking and massaging of her nipples. Sue’s body trembled in shame as she began to react to her personal degradation at the hands of Michael. His tongue continued to move from her anus, to the gaping slit of her pussy to swipe at her clitoris. Sue was sobbing small cries as her ass undulated to the oral caress of Michael’s tongue.

His tongue left her body and again, Sue again felt empty. He kneeled behind her, bathing in the sight of this beauty, naked and bound before him.

“It is time to open your ass up. I am going to start with my fingers. I am going to stick one finger in you dry. It will hurt, but I want you to bear down on it and let it enter you. You must get used to the pain. Your anus will have to open very wide to accept my big cock, but it was you that decided this.”

Sue’s body shivered as has fingers moved over the cleft in her ass and moved toward her exposed anus. She attempted to clasp her cheeks closed, but the spread of her thighs prevented it. A sudden fear shot through Sue as she realized the pain and humiliation of being fucked in the ass would be entail.

His finger began to push against the clasping little opening of her anus. The lewd anal contact with his fingers made Sue groan and attempt to squirm away, but his finger followed her limited movement. Sue gasped at the sudden invasion of her anus, struggling in her bondage to escape; however the tight ropes held her tightly. Sue soon realized that there was no escaping the cruel deflowering of her ass. Finally, she relaxed her internal muscles, hoping to ease some of the pain she knew she would be subject to.

His finger pushed in, probing forcefully against her elastic little anal sphincter. Sue moaned as the pressure increased and suddenly her tight anus opened to the finger and his finger pushed relentlessly into her unwilling anus.

“Oh no, Oh God, Not there please, it’s killing meeeeee!!!!! Aaaaahhhhhhhh” she screamed as his finger rasped dryly up her anal tract. Her cries had no effect on Michael as he continued to plunge forcefully into her anus. His finger reached deep into her rectum and began to twist her open.

The retreat of his fingers hurt just as much. As soon as it reached her clasping ring he teased it, forcing it to open wider. “OOOOWWW, it hurts, please,” she cried.

“Beg me to grease up your ass and fuck it with my cock. If you don’t I will stick two dry fingers in you.”

Sue moaned in shame and humiliation but she knew she must comply. The dry finger hurt terribly and she knew that two fingers would be extremely painful. “Please grease my ass”.

“Beg me to fuck you with my cock up your ass,” he said.

“Grease up my ass and fuck it with your cock,” she complied.

Michael took a bottle of baby oil and poured it on Sue’s naked ass. He began to run the oil over her cheeks, spreading the oil. His fingers moved some of the oil between her cheeks and over her anus. Sue cringed each time his hand moved over her naked anus. The next time his oiled finger pushed quickly and deeply into Sue’s clenching anus. His finger began to ream and probe her rubbery, virgin channel.

“OOOOOWWW, that hurts, OOOOHHHH” she cried as the finger burrowed deep into her rectum. Her body shuddered from the cruel ravishment of her ass. His finger withdrew and again sank deep into her rectum, drawing gasps of pain from Sue. The next time two fingers sank deep into her, stretching her tiny anus to spread wide. “OOOOOOW, that’s too big, take them out, it hurts, OWWWWW”, cried Sue.

His fingers pushed deep into her rectum and stopped. Sue trembled in pain. She waited for the inevitable. She knew that he would open them deep in her ass, stretching her open for the ultimate rape of her ass by his cock. She felt the fingers opening deep in her, spreading her rectal walls. She screamed in pain but Michael’s fingers continue their ruthless stretching. Her breathing became shallower as the fingers began to withdraw, stretching her open as they withdrew. They clasped together when they reached her grasping anus but again expanded her anal tract as they forced deep into her body. Sue shuddered in pain.

Michael withdrew his fingers from her ass and stared at her open anus. He fisted his cock and pushed forward, resting his hard cock on her tiny anus. It looked like it would never fit into her tiny body. He knew that Sue would feel a lot of pain before he managed to force the whole eight inches of cock deep into her ass.

Sue looked over her shoulders and saw that Michael was readying his cock to deflower her anally. She gripped the rails tightly, waiting for the initial tearing of her anus as she was forced to accept his big cock. Michael began to push into her anus, using all of his weight to force his cock into her. Michael braced his hands on her back to brace him and Sue’s clasping little asshole began to open to the crown of his cock. With a giant thrust, his cock entered her clasping rectum.

The pain overwhelmed Sue. Michael’s rough anal entry forced a cry of agony from Sue’s lips as her body tossed about attempting to escape the cruel rape of her ass. “OOOH, no, not in my ass, take it out, it hurts too much” she cried. She gasped as her ring began to ache and burn as he forced into her, stretching her virgin ring.

“Now that’s better, you’re nice and tight. Try to relax or else it will rip up your anal tract.” She groaned and her body shuddered as Michael forced his cock into her. Slowly it rasped into her. She felt her bowel spasm and throb as it forced her rectum to accept its big size. Her body jerked in pain as his cock ruthlessly inched deep into her body. He eased back out and than pushed back in. She tried to escape his cock as it slid deeper into her rectum, making her bellyache and cramp, but he grabbed her shoulders, forcing her down on his hard cock.

Sue buried her head and grasped the rail as he rammed his cock deeper and deeper up into her cramping bowels. She had never felt such agony and she begged and pleaded with Michael but he continued to force his cock deeper into her body. Her ass farted and squelched obscenely as he continued to pump his cock into her ass.

“OOOH God, pleas stop, I need to go to the toilet, stop please” her bowels cramping as he forced himself into her again. As he pulled his cock almost out of her, she was afraid she might shit herself. She arched her back as he rammed back in.

Michael grabbed her hips and began to push his cock in and out of her ass, watching her stretched anus grip his cock as he spread her cheeks wide. He forced her to roll her buttocks, massaging his cock with her silky insides. “OOOO, UUUUHH” she moaned. Michael relaxed her rectum throbs and spasms milking the head of his cock.

Sue grunted with exertion and reclenched her cheeks to stop him but he began to push back into her.

“I’m going to force my cock deep into your ass now and began forcefully fuck you.” He watched her pain wracked face as he began to push his cock into her. Each thrust pushing deeper into her ass chute. Sue thought it would never end. She pushed back, feeling her ass burn as his cock opened her ring even further. She cried out and her body jerked in pain each time it slid home each gut-wrenching stroke. Her head shot up and her back arched up in pain as his cock stabbed deep into her bowels. She grunted and moaned with each thrust, as he took her harder and harder. She struggled to accommodate his big cock. Her body went rigid as he speared her viciously as she felt his cock pulse deep in her rectum.

His hands reached under her ass and began to rub her pussy. His fingers found her wet and he pulled back the hood on her clitoris and began to pinch it, forcing a groan from Sue. “I’m going to make you cum.’

“Ohhh, please, don’t be long, it hurts so badly, I can’t stand it, cum in me and get it over,” she cried.

“You’re going to cum first or I will fuck you all day” and his fingers continued to manipulate her wet pussy and clitoris. Her ass began to push up into his cock, forcing it deeper into her unwilling ass. Sue grunted and strained in pain as his cock rammed deeper into her. He began to fuck into her ass with rapid deep strokes, making her wince in pain with each unmerciless thrust.

Sue began to feel the change in her body as his fingers continued to masturbate her. Even with the gut-wrenching thrusts deep into her rectum, her pussy began reacting to pleasure. She now began to fuck back, driving her hips back into a slow circle as he shoved his cock up her ass hard. Her head threw back as she began to feel the first contractions of an orgasm. Suddenly she cried out and jerked rigid, her body exploding into a shattering orgasm. She rammed back against Michael’s cock, forcing it deep into her ass. She could feel his cock grow bigger and stretch her anal tract wider as it began to cum deep into her ass. Her body shuddered and she let out a deep groan as he shot an enormous amount of cum deep in her clutching rectum. She felt her colon quickly fill with the hot cum. Cum poured from Sue’s throbbing pussy, soaking the bed.

Sue lay there exhausted, her rectum aching from the cruel punishment. Michael’s pulled his cock from her anus. She no longer had a virgin ass. She had been anally deflowered. Her fantasy was now complete.

BBBBUUUUUUUZZZZZZ, the alarm clock woke Sue up. She groggily opened her eyes, remembering the erotic dream she had. She had been taken forcibly up the ass for another’s pleasure. In spite of the pain, she had cum. She sleepily pushed the snooze button for another half-hour and went back to sleep.

She found herself still bound naked on the bed. She felt a body begin to spread over her ass again and felt a hard cock begin to force itself between her cheeks, forcing itself into the entrance to her anus again. It felt huge.

“Is that you Michael? I came, so the fantasy is over. Get off of me,” yelled Sue.

“Yes, that is true, but this is a new fantasy. I really like this one. My cock is over 12 inches long and 3 to 4 inches in diameter.”

Sue screamed in pain as his cock forced her anus to open and he pushed his cock deep into her rectum, making her bellyache and cramp.

To be continued