Cynthia Didn't Ask Me Ch. 01

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...