1 comments/ 130071 views/ 5 favorites Cynthia Didn't Ask Me Ch. 01 By: OttawaLateNite For the last few years I enjoyed a platonic relationship with my female roommate Cynthia. She was a beautiful blonde who was just finishing her second University degree. In the past years she was unwittingly the star attraction to my voyeuristic tendencies over the past few years. She had begun and maintained a long distance relationship with Jason, a business major at another University. When he visited I would watch them having sex or playfully being intimate but cracking open the bedroom door. From the moment they began their relationship I had been there as well. On the morning after the first evening together I was able to watch Cynthia perform a blowjob as her boyfriend lied back in bed. I snuck from my room and watched through the already open door. I was able to see Cynthia's spit on her boyfriends cock then continue to bob up and down on his member, the new day sun shining in through the window and passing through her blonde locks. This was the first time I was given the privilege of seeing the petite breasts she possessed. I admit I found her technique of giving head to be unappealing and unsatisfying as she finished him off with a hand job. The truth is in the last two years I had never seen Jason cum into her mouth. They only saw each other about once every two months and during those times I was not with anyone, I would work my sneaky abilities to try and watch them. Over time I was able to watch the tender moments of Cynthia's blouse being removed so gently, then her bra. Jason then would carefully toy with her perky breasts before moving on to suck on the nipple. I was there to watch them fuck in only a few positions. I knew my roommate to be a mite uptight about intimacy. It was either always the missionary position or with her on top. Only once did I ever see Jason have her up on all fours, taking her from behind with gentle force. I could sense that she wasn't satisfied, but almost afraid to ask to be taken harder. I wasn't able to see her face with her blonde locks covering it, but I could hear her tiny moans of pleasure. In recent visits I had eased off in my extra-curricular activity because I had almost gotten caught a few times. Of course, over time my mind began to race of many sexual fantasies I would love to act out on her. I knew that under the right circumstance, basically her being drunk would be the only way anything could happen. We weren't particularly too compatible so I always felt the odds were against me. I had tried being nice, being flirty and even outright admitting to a "crush" on her. None of this was working. I knew that someday I would get to taste what slept one room over from me night after night. Cynthia's and Peter relationship became uneasy, but both were still casually working on it. One evening I came home around two in the morning, pretty smashed from a night of celebrating a friend's birthday. I walked in to find my roommate sitting on our futon in the dark, only the flickering image of some Meg Ryan movie that was on the television lighting the room. I removed my jacket and shoes before I sat next to her on the couch. On the table I noticed an empty bottle of wine and a near empty glass, a sampling of red wine still available. Cynthia had been crying. I really was in no mood to listen but... " What's a matter Cynthia?" I inquired half-heartedly. "Jason, that Bastard. He is so fuckin' stupid sometimes." Her words were slightly slurring. She had an argument with Jason and was in need of relief. She chose the bottle and she seemed to be feeling better. I was sitting close to her, my hand innocently touching her bare leg. I leaned forward and gave her a hug. I figured in the least she would stop crying, though I was aroused from her streaking tears. "Thank you." She quietly said. I pulled back and we looked into each other's eyes. It wasn't a few minutes that passed before I tasted the inside of her mouth. I wasn't much of a fan of red wine but savored every taste drop from her mouth. Our tongues played with each other as my hand rubbed up and down her smooth leg. I sampled the skin on her cheek, a nibble from her ear and even a bite from her neck! The night was hard to explain. In that moment I was exploding in sexuality but it never went further. As our tongues tangled together I tried going further, beginning by running my fingers at the hem of her plaid boxer shorts and trying to move them higher. My advances were stopped and once again I remembered Cynthia's prude-like attitude with the casualness of sex. My mind screamed out like a locomotive on a path for destruction. The urge to take her was strong but I still resisted. Was what I feeling natural? Was I feeling guilty for wanting to treat her how I wanted to treat her? As Cynthia's hugged my and moved into her bedroom alone I sat there frustrated and angry. Had I missed my chance? The questions soon stopped as I passed out on the futon, left alone with an empty wine bottle and my sexual frustrations bubbling to the surface. We never really talked about it much after that night. It was an unspoken event for her. It was an unfulfilled fantasy for me. Time would pass I figured and maybe another opportunity would pass my way. A month had barely passed when it finally happened. I was home on a Friday night, enjoying a couple of adult beverages, skimming through a couple of adult websites. Cynthia came in through the door absolutely hammered immediately dropping her attaché case she used for her part-time job in a real estate firm. She was wearing a beige business suit jacket and beige skirt, no stockings and butterscotch looking knee high boots. Cynthia looked extremely hot. She smiled and looked my way almost falling to the ground. Her hair was wet from the light drizzle of rain outside on this spring night. Before the door even shut I knew tonight I was going to get her, one way or another. I helped her over to the couch; she slumped down, lying over the length of the sofa. " One of my co-workers wanted to fuck me," she said. "Really," I responded back " and why are you here instead of with him?" Her mind was floating all over the place. "Because...Help me with my boots," she demanded in a polite way. I really didn't want to, one of my vivid fantasies involved Cynthia against the wall, only wearing these boots. She was lying on her stomach, only the skin from the back of her knees was showing. I was immediately aroused and decided to take a chance. I unzipped one boot and then the next. Each time my hand would graze her soft white skin. With a subtle moan in each touch I knew I could proceed. "I'll give you a massage," "Hmm. Sounds so good." She slurred back. Before she even agreed I began working at her feet. She was very happy in her moans but very hard to understand when she talked. I would continue based on her moans and sighs. I began moving very fast, still savoring every taste and touch, but knowing it didn't matter, I would feel her from between her legs soon. I started by licking her feet, sucking one two at a time and then moved up past her ankles. Cynthia was very happy asking me to touch massage her legs as my tongue glided upon her skin. When I arrived behind her knee I focused on her right leg. As I moved the moans got louder. Both my hands explored her thighs, my left hand creeping closer to just under her beige skirt. I moved up and lay onto of her, smelling her damp hair from the rain and playfully licked her ear. She smiled and drunkenly laughed. "Your skirt is coming off NOW..." I told her in no uncertain terms. She nodded yes and smiled. I moved back down and unzipped her skirt and took off her skirt. "That feels so gooood!" She remarked with glee. I traced my finger up her leg, up around her ass to the top. I slipped my finger underneath her thong and slowly moved my finger down her ass crack, pulling the "floss" from the area I wanted to go. As I reached her asshole I stopped and gave a quick fingering then moved further south. I leaned in close to smell her, giving a bite to her tender ass cheek. "Bite harder next time." Cynthia asked. The further down my index finger went the warmer it got. I flashed back to the first morning I watched them together, the warmth of the morning sun shining upon her soft, white breasts. I wondered the difference between how her breasts felt against that morning sun and how my finger felt passing her warm asshole to her moist, tender pussy. "I want to cum. Make me cum." She said in reply to my finger around her wetness. I once again leaned forward upon her. "I'll make you cum sweetheart but I'm going to use my lips." She smiled, turned her head back, parted her lips and kissed me. "Tongue fuck me NOW." I instantly pulled her arms above her head and forcefully moved on her. "I'll tongue fuck you when I want. I call the shots." She seemed to be slightly shocked but I went on with my business. There were no more questions. I would have what I wanted. I lifted up the finger that politely touch her pussy and pushed it at her face. "Lick it!" She took more than a few seconds to lick my finger clean, my image of her beginning to change. "Get used to that taste you tease." Cynthia didn't respond except for to clean my finger of her must. I moved down and removed her petite, black panties, leaving her only with the clothes on her upper half. After taunting her with more kisses up from her feet to her upper legs I was disheartened to see that see had either fallen asleep or passed out. I slapped her ass. "God Damn It! Don't you pass out on me Cynthia"! She didn't respond much but it didn't matter. I was so close to my fantasy coming true that I wasn't going to stop. I couldn't stop. I was so close and I doubted a moment like this would ever arrive again. To steal a line from the movie "Swingers" it was time to stop acting like the guy in the PG-13 movie who the audience hopes gets the girl and begin to act like the guy in the R rated flick, the guy the audience isn't sure they actually really like yet. I decided I was the gut the audience wouldn't cheer for! I stood up and removed all my clothing. I was as hard as I could get. I leaned forward and captured the image of my dick on the tips of her lips. I moved down to her legs and rubbed the tip of my cock on her soft skin. Being so incredibly turned on I stopped feeling that I might explode. I then took my hands and spread apart her ass cheeks and placed my tongue at the top of her ass and ran it down her ass crack. When I got to her asshole I wiggled my tongue with abandon, enjoying every moment in her taste. The feel of her soft cold ass and the warmth of her pussy and ass excited me. As my face became wetter from her pussy, the rain hit the window harder. I pushed my tongue in her ass, trying to get in as deep as possible. Small drunken, delirious moans came from Cynthia. This was only the beginning... Cynthia Didn't Ask Me Ch. 02 Knowing my tongue was visiting the most exotic local on her body sent a shiver of power through me penetrating rational thought and sensitivity. This moment we would share together but I would own it. The experience of her asshole on my lips and flickering tongue played the ultimate pleasure play on my own realized fantasy. I lifted my self off her, removing myself from her virgin outlet. I lifted from the futon, my muscles exploding in strength and force. “Let’s get you into your bed.” I told her. When she was on her feet, barely standing, using her right arm to hold herself up, wrapping it around my neck. She was looking down, her left hand rubbing my cock. She looked up and gave me an inebriated smile. I slipped my tongue in her mouth and let her enjoy the taste of her own ass. Cynthia playfully pulled away smiling. “You licked my asshole.” I stuck my tongue back in her mouth as she swung the hand she was fondling my balls with to my neck. Slowly I had Cynthia walking with me down the short hallway into her bedroom. She was stumbling backwards, my hands firmly gripping onto her soft ass. I looked up, the rush of memories from her past penetrations flirting with me. The moonlight caressing the room as my lips did hers. I was passing the threshold, the place I usually stood or crouched, watching her boyfriend play with her body. I was no longer watching the movie but acting in it. And not only was I acting in it but I was the writer and the director. Cynthia’s body hit her bed, her lightly blonde pussy hair exposed to me. She smiled and spread her legs to me, running her fingers down her inner thighs. “You want to fuck me too?” she asked knowing the answer. “No. No.” I said, “The question is, are you ready to be fucked?” Cynthia shrugged her head left and right telling me no. “I want you to make me cum and then I want to make you cum.” She slurred. “I’ve heard the girls cum when you fuck them. Our rooms are next to each another.” “Do you like the way the sound?” I asked. Cynthia nodded yes. “I hear you when you finish fucking them too. They like you fucking them.” I stood next to the bed and pulled her closer. Her open pussy was inches from what I offered. I smiled, leaned forward and undid her accessible blouse. I started kissing and licking her heaving stomach. “Hmm. That’s so nice.” She politely responded. Her bra that covered her small, perky breasts hooked in the front easily clicked open when my teeth grabbed hold of the flimsy garment. Laying down on top of Cynthia’s fresh body, my cock even closer to entering her, my hands physically manipulated her breasts. I whispered, “I’ve seen your breasts before.” Not realizing I was telling the truth Cynthia responded accordingly, laughing. “When?” she asked. “Every time you and Jason would have sex I watch.” I said with a disgustingly sinister smile on my face.” Cynthia opened her drunken eyes quickly to that comment. “Way.. Wait a minute. I knew something was going on. The creaks at door; the door opening when I knew it was closed.” “I knew you’d enjoy knowing that.” “Fuck you. You invaded…” her sounds muffled by my hand over her mouth. “No.” I firmly responded, physically maneuvering her over, flipping her before ripping her blouse and bra completely off. “What are you doi….?” She tried to ask. I twisted her back over so Cynthia was on her back. Without responding I quickly opened her small dresser drawer next to her queen-sized bed and removed a pair of handcuffs. I grabbed her wrists and cuffed her to the headboard. Peter had bought them but to my knowledge had never used them. “I’ll fuckin’ scream.” She tried to threaten. With a firm grip I used both hands to hold her head firmly. Staring into her eyes I informed her of the situation. “Do you love Peter?” I asked. She quickly whisperingly replied “yes.” “I took photos in the living room with you sucking my dick.” I told her, obviously lying. “Either I keep them for myself or Pete gets a copy!” “Please don’t. I love him. Please destroy the pictures.” Cynthia was near to tears, her head spinning from the events and the consumed alcohol. “I know. I know, you love him, I get it!” I leaned in close. “He won’t know or will he?” I toyed in response. I started by biting at her wrists, the cold of her new metal bracelets on my forehead. Looking down, my hard cock rubbed against her hardening nipples. I continued leaving bite marks down her sensitive arms. Each bit Cynthia let out a whimper. “Tell me you like it when I bite you.” “I like it.” She responded almost crying. I licked her lips and began kissing her hard. Though her mouth was accepting of my tongue I still forced it in. In long stokes of tongue lashes I licked across her face. Her eyes were shut, giving me the impression she was beginning to love the assault. “Open you eyes Cynthia.” When they opened, her drunken blue eyes could see in close my erect member. I was kneeling next to her face, my cock above her face. I lowered down and placed my dick on her shut lips. Rubbing back and forth, I got more lubrication by the pre-cum spilling gently from my cock head. Soon she parted her lips. When her tongue began to lick my taste from my cock I almost lost the rest of my “authority”. Her saliva would drip from the head of my cock when it would slide past the last of her mouth, dripping down her soiled cheek. I leaned against the wall and squatted over her face. “What are you doing?” she asked with horror. “Keep your mouth open.” I told her in no uncertain terms. Cynthia’s mouth opened wide and I placed my shaven ball sac past her lips. “Use lots of tongue” I reminded her. I continued to bob up and down, the feeling as grand as if I were entering her with my penis. Her bare tongue against my freshly shaven skin bringing me overwhelming joy. Soon I found myself lowering my body onto her, sucking her tits, kissing her belly and then biting her inner thighs. With no resistance from Cynthia she pulled her own legs back as I pulled, exposing her tiny little asshole into the air. What surprised me more was that her tongue had found its way to licking around my asshole. I grinded against her tongue and began licking her wet pussy. One of hands held onto her ass, my index finger at the entrance of her asshole. Each lick of her mound left me with my nose at her ass entrance. I knew she didn’t enjoy tasting my ass, even the second hand taste of her won ass dis-pleased her. I kept moving my hips, enjoying listening to the sounds of her lips sucking on my hole. “I can’t do this anymore.” Cynthia mumbled from under my ass. I dropped her legs down to the bed and slightly re-positioned myself. Using my weight I forced my asshole on her mouth. “I want you tongue in my ass. Do it!” Cynthia tried to struggle but soon learned the taste of my inner ass. Cynthia was beginning to struggle from the lack of fresh air. This excited me, my asshole suffocating her pretty mouth. After having her moisten my inner being I lifted myself from her warm, filthy face. “You loved it” I exclaimed knowing she knew to respond back. “I loved it!” she responded back in near tears. I moved over and flipped her on her stomach. I moved onto of her and rubbed my cock against her ass cheeks. “Beg Cynthia.... Beg.” “Please fuck me.” Cynthia responded, again with no passion, I reached between her legs and spread her pussy lips apart. She was wet and willing as I slid into her. “Ohhh. Jesus. Please fuck me.” She responded. I knew that she did not want my cock on moral grounds, but somewhere, and she knew it, she wanted this invasion. “Jesus has nothing to do with.” I responded in my next thrust. There was unison from the first penetration. Our bodies moved together getting sweatier, providing our bodies with a natural lubrication. “uhh. uhh. uhh. Uhh. Uhh.” were her only responses every time I pushed forward. I leaned up and unlocked her from her shackles to the bed. I held her arms down with my hands and still forced myself on her from behind. “ Let me grab onto you.” she mentioned. I continued to force down her arms. “Tell me you love me.” I managed to exclaim, running out of breath. “Uhh. I…Love..Uh..Uhh. Oh Ya.” “TELL ME!” I said. With that I began thrashing at her, slamming myself deeper into her. “I love you! Oh God I love you!” Cynthia exclaimed. For the first time I believed her. “I love you. Fuck me. Uhh. Uhh….” For ten minutes I violated Cynthia from behind, the sheets between her legs soiled with her sexual fluid and sweat. During this time I recalled my favorite experiences in watching her and her visiting beau. I told her of every moment, every tender touch, every tiny grunt and every time she spit on his erect penis. I also informed her of my knowledge in activities she didn’t like to participate in. As time passed I leaned up and dragged her up onto all fours. “I watched Jason try and fuck you like this. You’ll enjoy this more!” Cynthia pushed up her hips just that much higher knowing she was about to be treated like and animal from behind. I ran my hands up and down her sweaty back then slapping her sweaty ass. I leaned down, kissed her juices, licked her asshole and got into position. I placed the head of my cock at her asshole. When I began to enter she was surprised. “What are you doing?” she enquired. I didn’t respond, instead pushing Cynthia’s top torso down on the mattress and handcuffing her to the bed. “I thought we could enjoy this together but I guess not.” With her naked ass in the air I penetrated her asshole. My throbbing cock kissed her inner asshole with love and care and force and power. “Oh God. That hurts.” I ignored her once again. I pushed my thick cock in, feeling like I was home for the first time in years. Her force wanted to push me out but also held me in. My hands held a strong, rugged hold on her wet ass. I grabbed her flesh tightly to allow her penetrated hole to feel all of me. I began moving in and out, her pussy juices keeping my stiff cock oiled up in her tense space. I knew it wouldn’t be long so I kept fucking her. “uh, uhh, uhh, uhh. Uhh. Oh ya, uhh, Uhh, UHH. Keep going, Oh yaaa.” At this point I couldn’t control myself. I fucked her in & out, in &out and wanted to spill into her newly stretched asshole. “Oh God, please. Uhh, Uhh, UHH, UHH. Oh Cynthia, UHHH.” That was it. I felt every muscle in my body tense as her asshole filled with my white offering. I looked over at the doorway, almost able to see myself in the past, holding my rigid dick, cuming into a towel. Cynthia was crying. “I fucking hate you.” I punched my semi-hard dick back into her slippery asshole. “Uhh. Uhh. I..hate…uhh. oh ya..”