I was sitting in a small neighborhood coffee shop reading the Wall Street Journal. I looked up from the short menu and once again scanned the street outside the café. The tinkle of the bell over the café door interrupted my thoughts. I looked up expectantly, and shook my head slightly when the new customer turned out to be a young woman in a hurry to grab her coffee and return to the currents of strangers flowing down the streets outside. That glance inside the café, however, had given me a chance to notice something that I had missed before. With my attention so focused on the sidewalk leading to the café, I had paid little attention to the people already seated inside. I had given the tables a cursory glance when I first arrived, but since.
What I now noticed, however, was a woman seated at a small table in the back corner; her face and most of her body hidden behind the newspaper she seemed to be reading. That wasn't unusual, and was not what had caught my eye. What had caught my eye was the way she had one leg folded in front of her on the chair, in almost a semi-lotus position; except in this case, the heel of her shoeless foot was pressed close to her beneath her loose skirt. I couldn't see the heel pressing against her panties: it was too dark under the table for that, but I watched closely and noticed a slight rocking of her hips.
I got up from my table, and walked over to the woman in the corner. I noticed the newspaper trembling slightly as I got closer, and I was now able to see that one corner of the paper was heavily wrinkled; as if it had been quickly folded down and back up many times. " The news must be interesting today, I couldn't help but notice how much you are enjoying your reading." I said as I reached the table. A soft and lyrical voice replied from behind the paper, " Yes, I have been enjoying myself, but it wasn't the news as much as other things that I was observing." I sat down at her table and asked, " What other things?"
" Oh, things like how much I wanted to meet you." was the soft reply from behind the paper. " Why would you want to meet me ? " I said. The paper trembled a bit more, and in a voice just above a whisper, Jenny said, " You are a international business mogul, a successful lawyer and a billionaire. I find you fascinating." I reached out and slowly pushed the newspaper down to the table. I looked deeply into the eyes of this young woman and said, " Then here I am." It was several moments before any more words were spoken, but much passed between the us as we became lost in each other's eyes.
Jenny blushed visibly, her soft voice was still bold as she replied, " A woman learns to adapt to a life of being alone and being lonely." " Some needs are easier to fulfill than others." She laughed then and said, " Nice to meet you." I got them both a fresh cup of coffee, and moved my chair closer to Jenny's before sitting back down. I noticed that the newspaper had now been placed half on the edge of the table, with the other half hanging down toward the floor. This created a small curtain that blocked the underside of the table from view. " I am thankful that you were still reading your paper when I noticed you." I nodded toward the newspaper as I looked at Jenny and sipped my coffee.
" Well, sir, I think I have the attention of the one I came here hoping to meet. No further attention by others is needed," Jenny quipped with a smile. " I agree. You have all my attention," I said as my hand moved under the table to rest on the thigh of her bent leg. I watched her hands fold around her coffee mug as I moved my hand higher up her thigh. I could feel the warmth and delicate softness of her skin. " You have the softest skin imaginable" My voice got lower and took on a strong tone that feels to Jenny like arms holding her safe and apart from the entire world. " You may have imagined correctly, but imagination can only go so far," she said in a voice that was increasingly reflecting her emotions, despite her shyness and her attempts to control what she was feeling.
Our chat turned to her fantasy of being fucked by a big long thick cock. I asked her if she liked BIG, hard cocks that she could gag on and ride all night? She was a bit hesitant at first, then she nervously said, " yes." " I want to see you scream, moan, groan, cum, gasp and beg for more!" I replied. We arrived at the hotel room, she is dressed in a tank top and tight skirt enhanching her body. Beautiful legs, small waist, and 30B breasts with prominent nipples. I called her over and put her hands in my trousers... She never been more turned on. Her pussy was wetter than it's ever been, because I was tall, older, muscular build and rugged looks, my cock was fucking HUGE! It must be at least 9 inches long, hard, 4 inchs thick, rippling muscle, and all she could think of was me bending her over and sliding that big, juicy, throbbing cock inside her.
She couldn't wait to see it, but was apprehensive and a little scared also. As she unzipped my pants to whip it out I took her hand and led her to the bed. This older man had the biggest cock she had ever felt. I wasn't all about the cock. I knew how to please a woman in every way possible. I was like a walking, talking Sex God to her... So, rather than get straight to the fucking like she wanted, I led her to the bed, slowly took off her top and her bra, and began kissing and sucking on her hard nipples. I laid her down, pulled off her skirt and lace panties, spreading her legs wide. She was completely naked and she hadn't been exposed like this in front of a man since college, but she wasn't embarrassed. I loved her body, the scent of her perfume mixed with the scent of her pussy and the adrenaline that was rushing through her body making her tremble from head to foot. I kissed and licked her all over, from her neck to her nipples, then down across her stomach to her thighs. She arched her back in pleasure as I slid my fingers inside her pussy and begin licking and sucking her clit all at the same time.
She was having second thoughts, if she could actually handle it. It was so BIG and THICK! The head was already glistening with pre-cum, the shaft so thick it looked ready to explode. I started licking, sucking and massaging her breasts and nipples. I slide my fingers in her and start fingering her pussy again. She starts gasping, pleading for me to stop. “ Please. Let’s just forget it. I’m sorry if I gave you the wrong idea. but I’m just not ready. I’m sorry, so sorry. Please!” I grab her thighs and start spreading her legs apart again. She grabs my head, trying to get it off of her mouth, probably so she could whimper and beg one more time. I force my tongue into her mouth and continue kissing her, waiting a few seconds before removing my lips from hers.
“ Please. Please, I can’t. Please. Please. I can't .” She pleads. “ I know, you want to be with a older man? You also told me how much you fantasized about being fucked with a big long thick cock, didn’t you?” “ Please, John. I wasn't serious I was flirting.” Jenny struggled furiously to relieve herself of my weight, but I held her down as my hands begin to roam over her body. " John, stop," she yells. I ignore her pleas, my hands roughly exploring her breasts before moving down over her waist to the curve of her hips. " No!" she wails as I shove two fingers back into her tight pussy. She grabs my wrist with both her hands and tries to push my hand away, I continue my rough assault thristing into her hard and deep. She gasps as she feels me slide a third finger into her.
She was moaning and groaning, " OOOOOOHHHHHH! AAAAAAAHHHHHH! OOOOOOHHHHHH! MMMMMMmmmmm!" in sheer pleasure at what I was doing to her, her slippery cum squelching as I push my fingers deeper, the sound of my tongue exlploring her turning her on like nothing ever before. Just as she feels like she was about to cum I stop, raising myself up and finally taking out my beast of a cock. It was like a snake, so large that even though it was rock hard it couldn't stand up. I wielded it like a sword, and, for the first time in her life. She sat up and, in complete awe of me, begins sucking on my cock. It was so big it barely fit in her mouth, and her poor attempts to deep throat ended with her gagging - to the joy of me. She had never gagged on a cock before! She sucked it like she had been cock-starved for a long time. Just the head filled her mouth, making her pussy even wetter. She couldn't wait to feel the hard long thick snake sliding into her, and I must have read her mind because I pushed her back down on the bed, rolled her over, pulled her up onto all fours, spread her butt cheeks wide and, quickly fingering her pussy once more.
She suddenly feels the huge long and wide cock sliding up and down the crack of her ass. She feels my hairy sweaty thighs aganist her inner thighs, my big, sweaty cock was rock hard. The heat from the monster thick rod spreading through her thighs as I continue to push towards her wet pussy. My cock pushs aganist her pussy, aganist her small tight wetness, pushing, I was grunting ' uuuuuhhh! uuuuuhhh!' then I feel my large bulbous cock head push past her labia. The head pushing into the mouth of her vagina, as the pain starts to tear through her body. OMG! WHAT A MONSTER! Her pussy has never been so stretched. It slids in slowly, forcing her to scream, " OMG! OMG! IT HURTS! PLEASE! PLEASE IT HURTS! OMG!" and gasps out of genuine pain. " Noooo. Noooo," Jenny half screams as I steady myself, then I clamp my hand over her mouth as I thrust into her, the pain tearing through Jenny's body as the long thick hard cock pushs part way into her small tight wetness, her body going stiff with the shock, with the excruciating pain.
" John, you're hurting me. Stop!" I groan as I push into her, I feel her pussy was well lubricated. I feel a part of her liked it. I thurst hard into her driving the head of my cock aganist her cervix, “ OMG STOP! STOP! OH PLEASE STOP!” Jenny screams. " Oh! Baby, your sooo tight. My God, ssssoooo tight!' I pull completely out of her.
Then with the head barely touching her lips, I drive my hips forward using all of my might. For a brief moment, her lips resist, and then split to allow the thick instrument to enter her, slamming through her tight vaginal canal and driving itself aganist her cervix on the second thrust. Women are not meant to be stretched like this, so I wasn’t surprised when her whole body jerked in response to the white hot pain of the thick instrument slicing into her small tight young pussy as she emitted a screech " OMG! OMG! AAAAAHHH! "
She screeched " AAAAHHH! TAKE IT OUT! AAAAAHHHH! " Pulling back several inches, I saw blood covering my cock, and dribbling down on to the bed. Then I drive forward again, slamming the head right up against her cervix again. I draw back and start ramming the tight young woman as she howls pitifully " OMG! AAAAAHHHH! AAAAAYYYY! AAAAHHHH! " I knew, she was experiencing blinding pain, the feel of her small tight pussy milking my cock sent shivers of excitement through my body as I slammed into her. The intense pain took her by surprise then in a moment she feels my large balls resting against her pussy flesh and she knows she has taken all of me. The feeling of fullness was incredible! She was proud of herself. She had taken all 9" of me. I begin to pull out then quickly thrust hard and deep into her. Building a rhythm gradually taking longer and deeper strokes until I had sheathing and unsheathing of my full 9" on each stroke. Her pussy still resisting each thrust, clamping down in a vain attempt at stopping each subsequent penile impalement.
Tears were pouring down her face as her tight canal was stretched, scrapped and torn by the sustained ramming I was inflicting on her. Gradually, the continued ramming of my cockhead gave to the back of her pussy causing it to give a bit. It felt great, having her tight young pussy grasping the entire shaft including the base of my cock, convulsing from the trauma, continuely spasming as her whole body heaves from the sobs and screams she was emitting " AAAAAHHHH! AAAAHHHH! OOOOOHHHH! PLEASE STOP! Pleeesssse Sttttttoooopppp! " I groan into her mouth as I continue slamming into her like a pile driver. My fingers digging into the flesh at her waist and she cries out " AAAAAHHHH! AAAAHHHH! OOOOOHHHH!. “ John,” she cries pathetically, her hands at my face as she tries again to push me away. I fucked my young vixen for several minutes, loving the tightness, and getting off on her screams.
I feel my orgasm approaching and start slamming harder into her, enjoying ramming the fuck out of her pussy. I drive all the way in, holding it there as the volcanic explosion pumps my warm semen into the crying woman. I hold my cock there for a few minutes, feeling her pussy struggling to expel me. After a few minutes, I pull my cock out and look at the blood and sperm dripping out of her split open pussy, as it still twitchs from the trauma it had just endured. She sobs heavily for a few more minutes, I roll Jenny on to her stomach. I grab her waist pulling her up onto her knees, her tight virgin ass in the air begging to be fucked. The feel of fucking a young woman's small tight virgin ass is undescribably.
My hard cock was dripping with all kinds of lubricant, so that would suffice as lube. I grab her hips making sure her ass was in the right position and I part her cheeks roughly as she cries out " OUCH! OMG! STOP NOT THERE PLEASE! ". When I rub the head of my cock against her tight puckered little anus, she went wild, struggling against me with renewed vigour as she screams desperate pleas " STOP! STOP! NOOOO! NOOO! ". I laugh, watching her struggle, listening to her screams.
Jenny relax, we talked about anal fucking and your fantasy to be fucked in the ass for the first time. Well, no better time than the present. I line my hard instrument up and lean in hard, pushing the swollen head against the resisting ring. Her entire body tenses, in an effort to resist the coming impalement with all her might. I was experienced in fucking a tight ass, to know that I would win this battle. Pushing hard, I had to hold on to my cock to prevent it from sliding off of her ass. She wiggles, clenching her sphincter and grunting with exertion as my cock head fights against her resisting ring. I feel the ring starting to give, ever so slightly. She sensed it too, and she started crying out " OMG! STOP! STOP! OMG! STOP! " from exertion and fear as the ring slowly starts to lose the battle . I push a bit harder and suddenly her anus loses the battle and parts as my cockhead forces it’s way in. Her whole body archs, her head going back as she emitts an agonized screech " OMG! AAAAAGGGG! AAAAAAGGGGG! " when her anus was forced wider for the first time in her life.
She was shocked and shudders as she trys to shake the excrucating pain from her body, yet couldn’t get rid of it. The pain was about to get worse....much worse. Once the head was in it was the beginning of the end as I was able to now push inch by inch, slowly into her rectum as she convulses and howls " OMG! OMG! OHHH! OHHH!! UUHHH! OHHH! UH-UH-UH-UUUHHHHHOOOOOOOOO" from the pain as her rectum was stretched, and forced open very deep within her. Finally I got my entire shaft in, my sweaty hairy balls resting aganist her ass. Her traumatized sphincter clenching and convulsing around the wide base of my hard wide instrument. It feels so fucking amazing, so unbelievably tight. The violation of her body, with my cockhead right up in her was sheer ecstasy for me as it was agony for her. She was insane with pain, of the invading wide rod stretching her.
I pull back and then shove it in again, causing insane convulsions from her and high pitched noises " OHHH! OHHH!! UUHHH! OHHH! UH-UH-UH-UUUHHHHHOOOOOOOOO!!!!" Her ass forces my thrusts to be slow, as it resists every inch of my shaft. That would soon change. I start ramming like a pile driver into her "AAAAAAAAAHHH, OWWWWWW"," ITS TEARING ME, TAKE IT OUT, STOP PUSHING IT IN," she screams. I start working my cock in and out, with long deep thrusts as she is screaming "AAAAAAAAAHHH!, OWWWWWW! AAAAAAAHHHHHH! OOOOOOOWWWWWW!" and crying. I rammed my hips against her ass with repetitive thrusts, WAP! WAP! WAP! WAP! battering her . Her buttocks and thighs kept quivering in response to the violation of her ass. She struggled endlessly. Her cries were pitiful "AAAAAAAAAHHH, OWWWWWW".
I continued slamming my cock into her tight gripping rectum as she howled " OHHH! OHHH!! UUHHH! OHHH! UH-UH-UH-UUUHHHHHOOOOOOOOO!!!! "AAAAAAAAAHHH, OWWWWWW" , still trying to thrash around, yet not succeeding. After another 10 minutes, I felt my orgasm coming, and planted myself deep inside her clenching asshole as she tensed every muscle in her body. I came in powerful jets of semen that fired deep into her as she cried loudly . " OHHH! OHHH!! UUHHH! OHHH! UH-UH-UH-UUUHHHHHOOOOOOOOO!!!! "AAAAAAAAAHHH, OWWWWWW" When I finished, I held it there for a few more minutes, then pulled it out.
Both of us collapsed on the bed, I rolled off of her breathing hard and she laid there sobbing." Well, your fantasies have been fulfilled." I said." The pain will turn to pleasure as you learn to relax. The more comfortable you become with my my monster cock." I said