Gwen the Ugly Duckling

Anal

I have always had the ability to get along well with most people, either socially or in a working environment. This has been a great asset in my life to date. I am a very sporty and athletic person and I keep myself in good physical shape. Women tend to find me attractive. Regardless of what people say about beauty being skin deep, physically attractive people tend to progress in life easier. I had found this to be the way for me.

Having said this, I am also quite a sensitive person, and empathetic to the feelings of others, particularly those less endowed by nature. I used to work with one such person, a young woman by the name of Gwen. At the time, Gwen was in her early thirties. I had worked with her for just over a year and like everyone else in the office, I paid very little attention to her.

I hate to use words as harsh as ugly, but Gwen would have to be described as very plain at best, but more accurately, unattractive. She was a nerdy, geeky type of girl in both looks and actions. She was about 5 ft 6 in tall and extremely skinny to the point of being cadaverous. Her legs were like twigs and her arms were equally as painfully thin, terminating in long, slender bony hands. Gwen had no womanly shape at all. She had no hips, a tiny scraggy butt and her chest was as flat as a pancake. She weighed no more than ninety pounds.

Gwen was extremely pale to the point of being as white as alabaster. It was as if she had never seen daylight. She had a very thin face with a long, protruding, bony nose, on top of which sat a large pair of dark rimmed, thick lens glasses. Her hair was mousy color, mid length and extremely lank and oily in appearance, as though it was in need of a good wash. Her mouth was quite large and her lips were very thin, exposing a very prominent pair of buck teeth which often protruded over her lower lip. Unfortunately, all of these features made her “rodent looking”.

Nature had not been generous to Gwen in terms of looks and physical attributes. Most people similarly bestowed tend to promote their better features as much as possible with good use of make-up or stylish clothing. Not Gwen. She wore absolutely no make up and her dress sense was abysmal to say the least. She would wear blouses, slacks or unflattering skirts which only highlighted her areas of deficiency. Even her shoes were unflattering, often displaying her thin bony feet when they were better hidden.

So having worked with Gwen for over a year, I could honestly say that I had hardly taken the time to get to know her. She was mostly invisible to me and to everyone else as far as I could see. One thing that I was aware of though was that I would sometimes catch her staring at me. If I turned and faced her eye to eye at these moments, she would quickly and shyly lower her gaze and begin to fidget. I believed that Gwen had a crush on me.

Gwen had a very introvert personality and she was extremely lacking in self confidence. In team meetings she would barely say a word. When she did speak, she would often stammer and correct herself. When I spoke in the meetings, I would find her gazing at me quite intently, and hanging on every word that I would say and somewhat pompously, I found this to be amusing. Some of my colleagues also noticed this. They would tease Gwen and refer to me as her boyfriend. Gwen would turn bright red and scurry away, which encouraged them all the more to be thoughtless to her feelings.

So life went on as usual within the office. I being one of the movers and shakers and Gwen studiously making her contribution in the background with minimum fuss and attention drawn to her. Gwen was far from being a social butterfly. She never attended any of our social functions and as far as I knew, she had never had a boyfriend. Apparently, she had confided to a female co-worker that she was still a virgin at age thirty, and fairly unhappy about that.

A social gathering was looming. One of our colleagues was leaving and we had decided that we should organize an evening dinner out. I took charge of getting the crew together. As I went through my checklist of attendees, I realized that I had not included Gwen. I had probably thought that it was futile, as she would not bother to show anyway. On this occasion however, I decided to give Gwen the benefit of the doubt.

I walked over to her office and knocked on the door. Gwen swiveled around in her chair and gazed at me through her thick lens glasses. I said “hi” and Gwen immediately turned bright red. I told her about the leaving party and invited her to come. Gwen said that she was unsure of her availability. I told her that I would really like to see her there and gave her a big smile. Gwen blushed some more and said that she would give it some thought. I left her office considering her a lost cause.

The day of the leaving party soon arrived. Everyone was arriving at the restaurant and taking their seats. To my total shock and surprise, Gwen came walking the exchange izle in to the restaurant also. Gwen went to sit at the end of the table. I called her name and shook my head and offered her a place next to me. She smiled politely and sat next to me.

The evening was a great success, not in the least for Gwen. After a slow start, Gwen chatted animatedly with me and the rest of the group for the entire evening. I have to say that I felt instrumental in integrating her into the team socially. It was a quiet but fun evening and most people left the restaurant reasonably early. I offered to give Gwen a ride home and she accepted.

I tried to make Gwen feel at ease during the car ride to her house. Gwen and I chatted amicably during the entire journey and she often punctuated her conversation with little nervous burst of giggles and blushes. We arrived at Gwen’s house and I told her that I would walk her to her door.

We walked along her garden path and I put my arm around her in a friendly fashion. Gwen fell silent, but I could feel her pushing herself even closer to me. I was aware as to not overstep the mark and have her wrongly believe that I was hitting on her. We arrived at her doorstep. I held her thin bony hands in mine and gave her a peck on the cheek, bidding her goodnight. She squeezed my hands tightly in hers and with somewhat teary eyes, she sniffled and giggled nervously and wished me a goodnight also. I turned and left. I waved to her from my car as I departed and she waved back at me animatedly.

After that day, our working relationship was never quite the same. Gwen was far more visible to me in the workplace. It was as if she was deliberately making the effort to bump into me as much as possible. She would take breaks at the same time as me and she would come to see me more often in my office. I also noticed that when we were talking together in close proximity, she was way more touchy feely than before, often resting her hand on my arm or shoulder.

I realized that Gwen was hitting on me in her geeky, introvert way and I wasn’t sure how to react. I definitely did not want to hurt her or push her away, as I had been proud of myself for integrating her more into the office team and I didn’t want to destroy this good work. On the other hand, I did not want to encourage her into thinking that she had a chance of a relationship with me.

I carried on as normal, responding very positively to Gwen’s subtle advances, often giving her affectionate but formal embraces, which she seemed to enjoy immensely. Looking back, I can see that Gwen took all of these actions as signs of encouragement. It was obvious that I was rapidly becoming an object of fixation and desire for poor nerdy Gwen.

The evening of the office Christmas party had arrived. It was at a night club down town and we had a full turnout for the event. Gwen was there, looking as dowdy and bedraggled as ever, but she had become a slightly more confident person, especially in my presence. I wasn’t in the best of sprits that evening. My social life was at a low ebb and my health was suffering somewhat. I was taking really strong pain killers for a soccer injury that I had sustained.

I was rather glum but tried to make the most of things. I stood by the bar for the entire evening, drinking way more than I should have done. Gwen would often stand next to me and chat during the evening. It was as if I could not shake her anymore. I recalled the movie “Fatal attraction” and I started laughing. I became more and more drunk, which in combination with the pain killers was not a good thing.

Gwen was taking advantage of my stupor and she started to snuggle up tightly against me at the bar, chatting away animatedly to me. I nodded back to her and said very little. Gwen suggested that we sit down in one of the quiet snug alcoves nearby, which contained comfortable red leather love seats.

I meekly followed Gwen and plonked myself down in the seat. Gwen sat next to me and snuggled up very closely to me. She pushed her face very close to mine as she talked and I could feel her breath on my skin. I was now at the stage where I could not comprehend everything that she was saying to me, so I politely nodded most of the time.

Gwen placed her right arm behind my back and placed her left hand, somewhat nervously, on top of my left thigh. She started to stroke my thigh, moving her hand up and down along its length. Gwen stopped talking and nestled her head into the crook of my neck. She continued to stroke my thigh with her hand.

I could feel her hand creeping further up my thigh as she rubbed it. It got to the point where I could feel the tips of her fingers pushing into where my cock was folded inside of my pants. Gwen continued stroking my thigh and each time, the tips of her fingers would push more forcibly into my hidden and folded cock.

I could feel Gwen’s the family pile izle heart beating faster as she nestled closely to me. She was obviously excited about the fact that she was touching my cock, albeit through the material of my trousers. I had no will to stop her. Gwen became even bolder and she began to rub her fingers along the length of my package. She began to feel for my cock through my trousers, pulling at it and pinching it between her bony fingers. I could feel an erection growing and so could Gwen, which encouraged her to play with my package even more.

I could hardly believe that this timid, introverted waif of a woman was rubbing my cock through my trousers in a fairly public place, even though the alcove had some privacy. Gwen sat there snuggled up tightly to me prodding and squeezing my cock through my trousers with her long bony fingers. She was saying some things to me which I could not always comprehend.

After about twenty minutes of this I decided that it was time for me to leave as I was feeling much the worse for wear. I stood up and told Gwen that I really should be on my way home. I started to move in a very unsteady fashion. Gwen asked me how I was getting home. I told her that I was driving. Gwen told me that this was not going to happen and she took out her phone and dialed for a taxi.

The taxi arrived and Gwen and I flopped in the back in a heap, giggling like kids. The taxi arrived at the destination very quickly. I was in bad shape and Gwen helped me into the house and up the stairs. She then dropped me on the bed in a heap and she started laughing. I looked around and I asked her where I was as I didn’t recognize any of my surroundings. She told me that I was at her house and that I could rest here in her bed that night as I was not in a fit state to go anywhere else. I told Gwen that I should be getting home but Gwen was really insistent that I should stay and she forcibly pushed me back down onto the bed. I lay there in an exhausted state of surrender.

Gwen began to untie my shoe laces. I asked what she was doing. She told me that she was getting me undressed for bed and that I would never get a good night’s sleep if I was fully clothed. She removed my shoes and socks and then began to unbutton my shirt. She completely unbuttoned my shirt and pushed it off my body, rubbing her hands over my chest as she did so.

Gwen then unloosed my belt, pulled down my zipper and pulled my trousers down off my legs. I lay there wearing only my underpants. I felt certain that at this stage that Gwen would say goodnight and pull the sheets over me, but she didn’t. Gwen knelt on the bed between my legs. She placed her hands on the elastic waistband of my underpants and very slowly she began to peel them off me.

Gwen slowly pulled on the waistband of my underpants and rolled them down. As she did so, my cock flopped out directly in front of her long thin nose. Gwen paused briefly, stared at my cock and grinned broadly. She then rolled my underpants off my legs and discarded them. I was lying there naked with Gwen between my legs, staring at my long, flaccid cock.

Gwen reached up and took my cock into her right hand and squeezed it very firmly. She stared at my cock intently as she rubbed it slowly. Gwen looked up at me and said, “do you know that this is the first cock that I have ever touched? ‘ She continued, “I was always hoping that yours would be the first cock that I would experience”. She giggled and said, “I can hardly believe that you are lying here naked and I am holding your cock in my hands”.

Gwen wrapped both of her thin cadaverous hands around my cock and squeezed it tightly. She held my cock about an inch away from her face. Gwen then told me that she had often wondered what my cock would taste like and she giggled like a schoolgirl as she said it. Gwen said that she would now taste my cock and laughed some more. Gwen pushed out her long tongue and began to lick my large purple cock head as if it were a big popsicle.

After several minutes of licking my cock, Gwen opened her mouth wide and pushed my large plum like cock head into it. Gwen lay there, contentedly sucking on my cock, her eyes looking huge through her lenses as she looked up at me. I was tired and drunk and my head was spinning. I tried to lie there calmly and relax as Gwen sucked away on my cock.

I looked at Gwen as she sucked my cock, realizing how unattractive she was. Her rodent like teeth protruded onto my cock shaft as she sucked it and it appeared almost as if she was biting my cock. Her long prominent nose stood out on her face and her lank oily hair was draped over my balls as she wholeheartedly sucked away on my cock. Every now and then Gwen would pull my cock out of her mouth to tell me how lovely it tasted and then greedily push it back into her mouth once more.

As I lay there watching Gwen sucking my cock, I realized the first lady izle that she was still fully dressed, still wearing the blouse and slacks that she had worn for the party. I mentioned it to Gwen and she laughed, saying that she should also get ready for bed. Gwen stood up and peeled off her blouse and slacks. She was wearing no bra, but didn’t need one as she had no tits whatsoever, just two very large, dark nipples surrounded by unusually large areolas which were almost black. She peeled off her panties to reveal a shaved pussy.

Gwen stood there naked before me. She was the skinniest woman I had ever seen. She was literally skin and bone. She looked at me and said, “do you know that I am still a virgin?” She giggled nervously and said, “but I don’t want to be one anymore, will you help me?” I nodded and Gwen smiled.

Gwen climbed back onto the bed in a 69 position, grabbing my cock and stuffing it back into her mouth as she ground her little bald pussy into my face. I licked her bald pussy and pushed my tongue inside of it, feeling it dripping profusely. After a short while, Gwen flipped over onto her front. She sat on my thighs with my cock in her hands, squeezing it tightly as she chatted to me. I was still very much in a daze but my cock was now rock hard in her hands.

Gwen lifted her tiny, bald pussy up over my cock, which she held firmly in her right hand. She then began to rub my large purple cock head against her clitoris and slowly began to insert it into her pussy. I could see that Gwen was very tentative and nervous. Her pussy was also extremely tight. Slowly, my swollen cock entered into her. Gwen grimaced as she gently lowered herself onto my hard swollen cock and she watched it disappear inside of her.

I watched intently as my cock entered into her, knowing that my cock was the first to enter into her virgin pussy. Gwen seemed apprehensive and in a little bit of pain and it took some time before all of my cock was buried snugly inside of her pussy. Gwen slowly began to bounce up and down on it. I lay there offering nothing at all. Gwen’s movements became more aggressive as her confidence grew and very soon she was bouncing firmly and rapidly on top of my cock. I looked at this unattractive, nerdy girl as she straddled me, riding me like a cowboy would a steer.

Although I was rock hard, I was a million miles away from ejaculating. I was drifting in and out of sleep and also, I didn’t find Gwen to be physically appealing. Gwen realized that I was physically and mentally “out of it” and she continued to do all of the work. In my sleepy haze, I would sometimes wonder if I was dreaming or was Gwen bouncing on my cock for real. In all honesty, I had never once fantasized about Gwen, but for her, this was her dream come true and she was taking advantage of me while she had the chance.

Gwen fucked me for well over two hours as I drifted in and out of sleep. Sometimes I would be lucid and she would be pressed against my chest with her face next to mine, my cock snugly wedged inside of her as she pumped her pussy gently. Other times, she would be sat upright with her arms behind her, bouncing aggressively on top of my cock. I could feel her trembling and shaking often as she reached orgasm.

Gwen would also continually try to keep me awake as she wanted to get as much out of her magic moment as she possibly could. She constantly chatted to me as she fucked me, telling me all kinds of things, including that my cock felt marvelous inside of her. She would press her face against mine, kissing me abundantly and telling me that she loved me.

She said that she had frequently fantasized about this moment when I would be hers to enjoy. She told me that she never thought that she would ever get the chance to hold my cock and suck it in reality and then feel it deep inside of her pussy. She gabbled on and on in this total state of awe in that she was actually enjoying a sexual encounter with me and how much it meant to her, giggling all of the time like a little girl.

Eventually after what seemed to be an eternity, I ejaculated inside of Gwen. I asked Gwen if she had been taking contraception and then realized what a stupid question this was. Gwen shook her head and giggled and asked if it mattered anyway. I told Gwen that I needed to sleep. Gwen said that was fine, even though she maneuvered her body down the bed, grabbed my cock in her hands, stuffed it into her mouth and began to suck it once more. I looked at Gwen quizzically. She told me to go ahead and sleep and not to pay any attention to her and then began to suck my cock again. I drifted off to sleep watching nerdy Gwen sucking contentedly on my cock.

I woke up the next morning in a mild state of anxiety, in my unfamiliar surroundings. Gwen was lying next to me, awake. She had my cock in her hands and she was playing with it. I wondered if she had slept at all, or had she been too excited with the chance presented to her and stayed awake and fondled me all night. I somehow believed the latter to be true as she was besotted with me and maybe she thought that this was her one and only chance. I was later to discover that Gwen had taken photos of herself on her phone, holding and sucking my cock as I slept and others of me lying naked on her bed.

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