Chapter 1: The Deepest Fantasy

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 more 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, no bra and panties 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."

"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.