Six Month

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Anal rape. Or was it?
6.8k words
4.23
295.7k
139
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Part 1 of the 2 part series

Updated 11/01/2022
Created 11/21/2002
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Who am I??? Once I was very sure of who I was, where I was going and what I wanted. I thought I knew myself well. So, who am I??? Well, my name is Alyson. I am 25 year old Penn State graduate. I work at a Fortune 500 company. I grew up in a good loving upper middle class home and once considered myself an intelligent strong independent career women but life has a way of redefining us.

It all started when I broke up with Tom, my fiancée and my boyfriend from College. We had been together for nearly 7 years and had planned on getting married but 2 month into our engagement I realized that we had grown apart since college. I had become quite a career women jet setting across the country. I had been working for only 3 years but had already been promoted to assistant manager. My ex-fiancée however had a much more difficult time adapting to the real world. He was brilliant in school but had a hard time in the business world and talked constantly about going back to school. To make a long story short, I realized we wanted different things in life and so I initiated the breakup. Nevertheless it was still very hard for me to take. I still loved him but realized I shouldn’t marry him.

Being a women of the new Millennium and watching too much “Sex and the City” I decided what I needed was a hot passionate purely physical fling to get me over Tom. There was a guy from work who fit the bill perfectly. His name was Richard. A suave good looking charismatic charmer in his late twenties with quite a reputation at work as a lady killer. He always flirted with me and I knew he had his eyes on me, but since I was with Tom nothing ever came of it. I put Richard in the category of guys that are great to have fun with, but for any women to take them seriously would be to invite heartache! That was for weaker lesser women who cling helplessly to men. For me this would be strictly for fun!

That week I ran into him at Happy hour were a group of us from work go every Friday. I had a tight skirt on that accented my butt and lean tone legs which I consider to be my best assets. I work out regularly at the gym and am very proud of sexy shapely posterior and long tone muscular legs. I do wish I had a little more up top being only a B-cup. Richard and I began flirting shamelessly. Richard is a charmer and has a way of making a lady feel very sexy and beautiful. The way he looked at you, the way he smiled with a hint of danger and lust. We stayed after most of our co-workers left. The bar we were at doubles as a happy hour bar and a dance club. As the night wore on, Richard and I found ourselves gyrating sensually on the dance floor and boy could he dance. Tom hated dancing and was very analytical and cerebral but Richard loved to dance and was very passionate and physical. I could feel Richards hard muscular body as he held me close as he ground against me. The music was booming in my ears, I was tipsy from the drinks and he felt so hot. He would run his arms sensuously against my bare shoulders and arms as we danced.

We ended up back at my place all over each other. He was such a sexy lover and licked me all over from head to toe. He went down on me for what felt like an hour and brought me to numerous orgasms. He also had the biggest cock of any man I had ever been with! I must admit I was intrigued by what it would be like to be fucked by such a large penis, which I soon found out. I wasn’t able to take all of him inside but the thickness of his cock really did increase my pleasure so perhaps size does matter! We stayed up all night making love. Thus began our affair! We could not get enough of each other and would meet after work and have sex for hours. He was so hot I even enjoyed giving him blowjobs something I am usually not too fond of. His lean sexy abs and his big beautiful thick cock made me so hot. I was so horny when I was with him. I would dive down and take the head of his cock deep in my mouth and down my throat. I had to open my mouth really wide to encompass his thickness and I couldn’t take more then half of him but what I couldn’t fit I would rub sensuously with my hands. No I am not quite as talented as Linda Lovelace. I felt so sexy doing it on my knees while he was standing looking up seductively at him, watching the excitement in his eyes as he thrusted into my mouth. I even let him come in my mouth, something I’ve never done before. Well to be honest I didn't have much of a choice. He held my head down as he came but I didn't mind. He would spurt streams after stream of hot cum down my throat. I tried to take it all but inevitably my mouth would overflow and some of it would trickle out and down my chin. I can’t say I am crazy about the taste, it kind of burns my throat and there is a strong after tastes that stays in your mouth for hours afterwards but I was so overwhelmed by lust that I swallowed it all or a least as much as I could and even milked his cock dry by opening my mouth and letting him watch as I licked the last drops of come from his cock. He would scoop up any cum than had dripped down my chin and feed it to me. I felt so nasty.

Sex with Richard was INCREDIBLE except Richard had a thing for anal sex and told me I had the sexiest ass of any gal he knew and that he wanted to have my virgin ass really bad. I told him firmly and unequivocally NO. I was not into anal sex and the answer is NO, No ifs ands or buts! I know it’s a big fantasy for a lot of guys and I can even understand why they would want it but from a women’s point of view there’s not much in it for us and from what I’ve heard it can be extremely painful. Considering the size of Richard’s cock I would say extremely painful would be a gross understatement! How many guys would enjoy a big dildo shoved up their ass? Guys would cringe at the thought. Biologically I don’t believe there is a big difference between a man’s ass and women’s, if anything it would be easy for a guy to take something up their asses considering they are physically bigger. I mean I am only 115lbs! Mention shoving anything up their asses and they run in mortal terror yet they expect us gals to bend over like good little girls and let them shove their cocks up our asses and enjoy it! I don’t think so! Just another example of the male double standard!

One of my girlfriend’s boyfriends kept pestering her about anal sex. She confided in me that she was worried he would cheat on her with someone else who would give it to him if she didn’t. She finally gave in and let him do her in the butt and she told me it was painful as hell. She endured the agony just to please and satisfy him and after that he wanted it all the time. She hated it! Turns out he ended up cheating on her anyway and they broke up. I’m not the type of women to do things just to please a man or to worry about him leaving me if I didn’t. Personally I think it’s pretty pathetic when a women does that. So no, I wasn’t about to go and let Richard or any man do me in the butt just to satisfy their kinky fantasy.

Although I had no desire for anal sex my self I must admit I was kind of excited by the fact that Richard wanted my ass so bad. It was kind of a turn on knowing he lusted so intensely after my tight little butt. He was always glancing at my butt whenever I had my back turned. I could see him in the mirror checking out my ass. It was very flattering. As a result I would always wear outfits that accented my tight rear end whenever we went out just to see the desire in his eyes when he glanced at my butt. Kind of like the way a gal with big breasts would were a low cut top and all the guys would keep glancing at her. I would stand provocatively in front of him with my back turned, my hips to one side and my butt thrusted out slightly. It use to drive him crazy and whenever we danced, more often then not I would turn around with my back to him and I would wiggle my sexy little butt against his hard cock. I remember once while brushing my hair with my back to him wearing only a g-string panty and standing provocatively on purpose with my hips thrusted back, he said, Alyson, your ass is so hot, I would give my left nut for a chance to fuck that tight virgin ass of yours. I backed up into him and rubbed my ass seductively against his crouch and whispered, is this what you want lover, do you want my sexy little ass, do you want to put that big cock of your all the way up my tiny little asshole? Would you like to do it in my virgin ass? I even pulled my g-string to one side, reached back with my hand, grabbed his penis and rubbed the head of his cock against my anus but ready to pull away quickly should he try to penetrated me. He got so excited and was breathing heavy. His eyes had that glazed lustful look as he started down at my ass. Then I said keep on dreaming lover, not in this lifetime! I know, I am such a tease. It’s such a sexy feeling of power knowing the effect my ass had on him. I didn’t leave him totally high and dry. I did turn around , get on my knees and give him a blowjob to orgasm letting him cum hard in my mouth. I confess I got a kick out of teasing him. I had no intentions of ever having anal sex but it was erotic and sexy the way he wanted my ass so bad. I equate it to us gals getting all dressed up in our hottest outfits and strutting our stuff at the nightclub. Its sexy just to see all the guys lusting after us. We may not have any intentions and of being with any of them but it’s fun to be desired and wanted. I am sure every gal understands this!

Four weeks into our passionate affair my 25th birthday came up on a weekend and Richard invited me up to his uncles lake house cabin for the weekend. He took Friday off to fix up the cabin for us and I was to meet him up there after work. I ended up working late and didn’t head up there until Saturday morning. The cabin was beautiful, right on the lake. It had a fireplace, Jacuzzi and a gourmet kitchen. It was very cozy romantic. Richard rented a boat and took me water skiing. He looked great, tan and muscular in his swim trunks. The cabin and lake were in a very secluded area so I wore my sexiest florescent G-string bikini and I thought I looked incredibly hot in it. It really showed off my sexy tight butt and legs and my lean tight stomach! I could see the lust in Richards eyes as he watched me lounge out seductively on the boat showing off my assets especially my tight ass. I would bend over seductively in front of him and rub oil sensuously over my ass. I would stand bent over on the railing with my butt sticking out for him to admire. I could see I was driving him crazy with desire. We flirted all day on the but retrained from touching each other. This was Richards idea, he said he had something very special planned for my birthday. Oh, I couldn’t wait!

We had a beautiful candle lit dinner. Richard cooked me a delicious seafood pasta dish. He is quite a chef. It was so romantic. He had soft jazz playing in the background. It was a perfect birthday dinner. I couldn’t have asked for a better. We had a few bottles of wine and I was feeling tipsy, very sexy and horny as hell. We began making out passionately and he had me naked and out of my sundress in seconds! I was so hot for him. He lifted me up and carried me to the work out room and laid me down on the work out bench. The room had mirrors all around and you could see yourself from every angle. I thought what a sexy room to make love in. Richard then produced a pair of velvet lined handcuffs and said I have a surprise for you. He wanted me to bend lengthwise over the workout bench with my knees on the ground and my stomach and tits laying on the bench. I was hesitant but he bent over and sucked gently on my nipples sending shivers all through my body and whispered trust me baby. This is your birthday surprise. You are going to love it. Overwhelmed by lust I threw caution to the wind and against my better judgement I let him hand cuff me to the bench. He licked me sensuously down my spine driving me crazy. He then slipped velvet lined leather buckles around my thigh tying them to the legs of the bench. He asked me to see if I could move and sure enough I was immobilized with my hands hand cuffed out in front of me to the front legs of the bench and by legs tied to the real legs. I must admit I felt so helpless and vulnerable but in a sexy way being tied up bent over like that with my privates totally exposed. I could see myself tied up from all angles in the mirrors. I thought I looked very hot tied up like that.

Richard then put a tape in the VCR and turned on the TV in the workout room. It was a XXX movie and it showed a gal tied up in the same position as me! The man in the movie then began to lick the girl between the legs licking every inch of her pussy. At the same time I felt Richard doing the same thing to me. I could see him in the mirror licking me. Oh god, It was so hot! The man in the movie began to lick the girls anus sticking his tongue up her bottom and sure enough Richard began doing the same thing. I’ve never had anyone do that to me but it felt so kinky and nasty. My senses were running crazy, seeing the girl ass getting licked, feeling Richards tongue probing my ass and watching ourselves in the mirror. Richard began fingering my pussy and caressing my clit while he tongue fucked my ass and I came hard moaning against the bench and tensing my body against the restraints. Knowing I was helplessly tied heightened my pleasure! As I slowly returned to my senses I heard a girl saying No, no, not there. I cleared my head and looked at the TV to see the man in the movie rubbing oil on his cock and fingering the girls ass with the girl pleading NO. He then moved up behind the girl and began to penetrate her ass with his cock. The girl was crying now and pleading for him to stop and all of a sudden I had a queasy feeling of fear in my stomach and it dawned on me what this was all about.

I looked back at Richard and sure enough he had a bottle of oil and was rubbing it all over his huge thick cock which looked even more enormous in my present predicament. He had that smile of danger on his face except now I really felt scared. I should of seen this coming! Why else would he want me tied up in such a position. I didn’t even think to question the position so caught up was I with the romantic dinner and all. I could kick myself. I should of known better. Richard was a man use to getting what he wants, the way he forced my head down when he came. I was getting more scared by the minute. I said NO Richard. I’m not into that. Untie me now! I mean it! This is not funny. Let me up now. He just smiled and said dreams do come true my little tease! God, I’ve been playing with fire all this time and now I was about to get burned! I told him I’ll scream if you don’t untie me NOW! My voice broke as I said it and I didn’t sound nearly as tough as I wanted to! He just continued smiling that evil grin of lust and desire. He said softly, go ahead baby. We are in the middle of nowhere. There is no one here to hear you. I wanted your ass from the first day I laid eyes on you little cock tease. Did you have fun flaunting your sexy little ass on the boat today? I don’t see you wiggling your little ass now do I. I am really going to enjoy fucking that tight virgin ass of yours Alyson. I felt cold oil drip down my ass and he began probing my tight anus with his fingers forcing one then two into me. I couldn’t believe this was happening! I screamed and told him to stop. This is rape! I’ll call the police and have you thrown in jail! He just kept working his fingers in me. He was stretching my anus sending streaks of pain through my body. He removed his fingers and I felt the head of his hard cock against my anus. The girl in the movie was sobbing and moaning now while the guy pounded against her, dilating her anus with his cock. I could see Richards cock at the entrance of my ass in the mirror. It looked so HUGE against my tiny anus. He would literally split me in two. I struggled helplessly against my restraints as panic began setting in. Richard began pushing hard against me and white hot pain flashed through me as the big head of his cock penetrated my virgin ass. I screamed out loud in pain! Despite my best efforts not to I began crying. I began begging him to take it out and I hated how weak and whiny my voice sounded to me. My ass began spasming violently against his invading cock. The pain was so intense, unlike any I have ever felt! I begged, please Richard, take it out, it hurts, it really hurts. You’re too big! You’ll really damage me! He just smiled and said, Alyson, your ass feel so hot around my cock! I am going to fuck your beautiful hot sexy bottom with every inch of my cock and you’re going to learn to take it all! Every inch of it up that hot tight virgin ass of yours. With that he began forcing his cock deeper and deeper into my rectum sending unbelievable pain shivering through my body. I could see his huge cock disappear inch by inch into my widely dissented anus. It looked impossible that it could fit there. He sank every inch of his thick cock into me tearing me apart. I felt like I was going to be split in two! I could feel him in the middle of my stomach as he impaled his huge cock mercilessly into my body, violating me and sodomizing me completely. I began sobbing uncontrollably while cramps wrecked my abdomen and burning pain ripped through my rectum and anus. I was stretched and filled to the limit. I couldn’t believe how my fantasy weekend became such a nightmare! I begged Please take it out, please Richard, I’m so sorry I teased you. Please I am begging you. Please stop, it hurts so bad! Richard ignored my cries of pain and began licking my back telling me how incredibly hot my tight oiled ass felt around his cock. He gripped my hips hard and thrusted deeper into me. I could see images of him sodomizing me brutally from all angles in the mirrors! Three other guys had joined the first guy in the movie and they all took turns pounding the helpless girl’s ass. The girl was sobbing just like me and the guy would pull out and cum all over her face, while another guy quickly took his place in her tortured ass.

Richard began pulling out half way only to trust back deeper and harder in to my bowels. Pain ripped through me with each thrust as he fucked my ass without restraint. I could feel him hitting my insides deep within my belly. I cried helplessly with each thrust of his cock hoping my torment would end soon. Richard fucked my ass for what seemed like an eternity. The intense pain in my ass subsided to a throbbing burning pain but each thrust still caused sharp flashes of pain deep within me where the head of his cock was battering deep within my belly gaining entrance to recesses far within my body. After what seemed like an eternity Richard began jack hammering into my bowels causing me to scream out again in pain and I felt him beginning to cum. He unleashed what seemed like endless streams of cum deep within my defiled bowels. He gripped my arms hard as his body tensed in orgasm. I could feel his cum filling my bowels, spurt after spurt of his seed. I could see his face in the mirror with an expression of pure ecstasy as he ejaculated into my ass. When his orgasm finally subdued, he collapsed on top of me and whispered into my ears how great it was and how sexy hot and erotic my ass was. I wanted to KILL him. He slowly withdrew his cock from by tortured ass leaving my dilated hurt and exposed. Sensing I was not about to forgive him, he left me tied up and exposed there on the bench. Through teary eyes, I could see my anus red swollen and dilated in the mirror from the punishment it received. I was still sobbing uncontrollably. What a birthday this turned out to be. I looked up at the TV to see three , four maybe five guys all standing around this poor girl ejaculating all over her pretty face! What pigs guys can be and I found out first hand tonight just how much! Richard came back with his bags packed. He told me that was the best sex he ever had. I was too hurt to respond. He handed me the keys to the handcuff and left.

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