Gwen the Ugly Duckling

Gwen bid me a good morning. I lay there sleepily watching Gwen playing with my cock. She reminded me that it was a Saturday. She asked me if I had made plans for the day. I shook my head. She told me that she had plenty of food and even wine at her house and that she would be able to cook for me during the day, so it was best if I just spent the day relaxing with her. She asked me if this was a good plan. I meekly nodded my head. Gwen smiled and began to suck my cock once more.

I realized that Gwen's idea of relaxing was for the two of us to spend the entire day together having sex. I didn't want to burst Gwen's bubble and hurt her feelings as she seemed to be deliriously happy. I decided that to grant Gwen her day of sex was no hardship on my part and that after this day we would part company and just remain friends once more.

My cock was becoming hard once more. I decided to take the initiative this time. I grabbed scrawny Gwen and pulled her onto her back. I looked at her. It was hard for me to be affectionate to Gwen as I had no physical attraction whatsoever to this rodent like waif of a woman, so the day would have to be about raw sex. I sat on Gwen's tiny abdomen and stared at her totally flat chest. Her nipples were really long though, almost two inches in length. They looked bizarre, just like the rest of this pixie.

I began to rub my cock onto Gwen's huge areolas and nipples. Gwen giggled. She took one of her long nipples between her fingers and thumb and pushed the entire length of it inside of my cock head until it disappeared from sight. It looked bizarre and interesting and it also felt really good. Gwen realized that she had turned me on. She giggled some more and began to twist her nipple back and forth inside of my cock. She laughed and said, "my nipple is fucking your cock". I laughed at this comment, finding it humorous.

I pushed myself further up onto Gwen's chest. I grabbed Gwen by her lank, oily hair and pulled her head towards me. I then slapped her rodent like face with my cock several times. Gwen giggled again. She moved her head back and forth and opened her mouth, trying to catch my cock in it as I continued to cock slap her face. She succeeded. My cock head plopped into her mouth and she firmly wrapped her thin lips tightly around it. She looked up at me with her eyes twinkling and my cock resting in her mouth.

I told Gwen that she had to take all of my cock into her mouth. I began to feed it into her and soon all of my cock was stuffed inside of her greedy little mouth. Gwen didn't look entirely comfortable. Her eyes bulged and watered and she was gagging slightly, but I insisted that Gwen stay this way for several minutes. Gwen was totally obedient and submissive, as I expected her to be.

Even though she was in some discomfort, she just lay there quietly with all of my cock jammed into her mouth, her buck teeth exposed and protruding into my pubis. I found it to be quite a sexy sight. For good measure, I began to twist forcibly Gwen's large nipples at the same time. Gwen endured it all with just the merest sign of a whimper. I realized that I may be able to have some fun with her submissive tendencies. I grabbed Gwen's head and pushed it even tighter against my pubis, to the point where Gwen was gagging frequently.

I released my grip and let my cock slip out of her mouth. A large string of saliva hung between my cock and Gwen's buck teeth and she looked up at me with an attempted smile. I told Gwen that I sometimes liked my sex to be on the rougher side, but that she shouldn't worry as I would not hurt her. Gwen nodded and smiled. She then asked me if I would like some breakfast. I replied in the affirmative.

Gwen started to get dressed. I told her to take her clothes off, as we would be spending the entire day together totally naked, even for meals. Gwen laughed and said that this was fine with her. I followed the scrawny naked Gwen downstairs to her kitchen. Gwen had a lovely house. She had obviously been very frugal and had purchased a nice property in a desirable area, which would have been above my means.

I opened the French patio doors to her garden to get some fresh air. I stood in the doorway naked, admiring her neat garden. The back garden was quite private and the house itself was only partially overlooked by the neighbors to the east. I asked who her neighbors were. Gwen told me that a young lesbian couple had just moved in next door. She said that they would probably be able to see me standing naked in the doorway and then she laughed saying that they would not be interested in seeing a long dangling cock anyway.

Gwen sneaked up behind me and put her hands through my legs and started playing with my cock as I stood naked in the doorway. This really turned me on and I became rock hard instantly. I spun around and picked up the frail Gwen. She threw her arms around my shoulders and wrapped her legs around my waist, her pussy just hovering over my cock. I manipulated Gwen into a position where my cock was accessible to her pussy. I gently lowered her onto my stiff, swollen rod and began to thrust my cock roughly into her pussy. Gwen gasped and groaned as my entire cock thrust in ad out of her pussy rapidly.

I walked around the kitchen carrying Gwen who was wrapped around me with my cock stuffed inside of her. I fucked her roughly as I walked around with her. She was so light it was easy to carry her and fuck her at the same time. Gwen's face was pressed against mine and I could see her eyes rolling around her head as she was experiencing one orgasm and another.

I decided to be a bit risky. I would out of the patio doors carrying and fucking Gwen and began to wander around her back garden. Gwen shook her head to say no, but laughed at the same time as she realized that I wasn't going to pay her any notice. I wandered around the garden with Gwen wrapped around me, pumping her tight little pussy full of cock.

Towards the end of the garden we were in full view of two or three of her neighbors' houses. I stayed in this vicinity for quite a while, as if wanting to be seen. Gwen was having so many orgasms that she seemed to have lost the will to complain or worry about where we were and who could see us. I fucked Gwen hard as I casually walked around at the end of the garden.

I looked up to the closest neighbor and saw the two young lesbian women looking out of the bedroom window and taking in the show. They were attractive women too. I laughed to myself at my outrageous exhibitionist behavior but I was so turned on by it also. I continued to walk around the same patch pumping my cock into Gwen. I could see the two women smiling and they remained in clear view, obviously with no intention of hiding, as they viewed the show. I kept Gwen's back to them so that she wouldn't see them and so that the two lesbians would be able to see my cock thrusting in and out of Gwen.

I gave the two women a good show for between five and ten minutes and I thought that I noticed them taking some photos on their cell phones. I also saw the rustle of curtains in other windows of the other houses, but if anyone was watching, they were doing so discreetly. This exhibitionist activity had me so excited that I ejaculated inside of Gwen at the end of the garden. Gwen shook her head and laughed. I lowered Gwen to the ground. I took her hand and we slowly walked back through the long garden naked and in full view of the two lesbians.

Inside of the house we erupted into fits of laughter. Gwen made us a great breakfast and once we had finished it, Gwen wanted to get back to the sexual activities with haste. Although I found nothing attractive about Gwen, she was very adept at sexually stimulating me and she constantly had either her hands or her mouth on my cock. She was besotted with my cock and she wouldn't leave it in peace for a second during the entire day.

I ask Gwen if she had any rope and she scurried off naked to find some. She returned with some rope and I told her that she had her chance to be in control last night but today, I would be in charge. Gwen smiled at me and nodded. We both migrated back to the bedroom. I picked up Gwen and threw her onto the bed with ease. She lay there on her back, naked, looking up at me.

I stood by the bedside and I pulled Gwen towards me by her ankles. I lifted up her legs by her ankles and inspected her small, bony feet. Her feet were quite tiny, but she had long slender toes. I lowered her feet to my cock and told Gwen to play with my cock with her feet. She complied and she rubbed and tugged away at my cock with her small nimble feet. Her long toes were able to grab my cock almost like fingers and Gwen laughed as she attempted to give me a footjob.

I grabbed my cock and placed it on the sole of Gwen's right foot, noticing that my cock was as long as her tiny foot. I also noticed that my cock was as thick as her painfully thin ankles. I am reasonably well endowed with a long and thick cock and this may part of the reason that Gwen had taken such an attraction towards it. Gwen continued to work away at my cock with her feet as I watched.

I decided that it was time to use some restraints on Gwen. I had always wanted to indulge myself in some bondage activity and here was my opportunity. I tied both of Gwen's frail wrists to the top rail of her metal headrest as far apart as possible. I then lifted her legs up high and over her shoulders and I tied her left ankle to her left wrist and the right ankle to the right wrist, so that her legs were spread-eagled far apart and over her head. I noticed that Gwen's panties were lying on the floor. I picked them up, scrunched them into a ball and stuffed them into Gwen's mouth.

I stepped back and looked at my handiwork. Gwen looked frail and helpless at the best of times. Now, she looked incredibly vulnerable. Her tiny frame was trussed up to the headrest. Her little bald pussy was exposed and vulnerable and fairly close to her face, and pointed straight up to the ceiling. I smiled and felt a surge of excitement rushing through me.

I bent down and began to lick Gwen's pussy. Gwen watched intently. I could hear her soft moans and her pussy began dripping juices almost immediately. I stuck out my tongue and pushed it a deep as I could into her pussy. At the same time I pushed both of my thumbs into Gwen's asshole. I could feel her shudder as I continued to push my thumbs into her asshole and I pressed my face hard against her bony pubis. I took her clitoris between my teeth and nibbled on it, gently at first, then biting it more aggressively. I was becoming very aroused, as was Gwen.

I sat on my haunches and I began to stuff my fat cock into Gwen's prone and exposed pussy. I took my time. The action was very close to Gwen's face and she watched wide eyed as I sunk my swollen cock deeper and deeper into her pussy. Once I had sunk all of my thick cock snugly into Gwen's vulnerable pussy, I sat there on my haunches, quietly looking at Gwen's face. Gwen was totally wide eyed. She would stare at her pussy with my cock stuffed inside of it and then shift her doe eyed glance up to my face for a few seconds and then look back at her pussy once again. Gwen did this constantly, shifting her eyes from her pussy to my face and taking in both views.

I began to thrust my cock deeper into Gwen and more aggressively. Gwen groaned and her eyes rolled back in her head. I now pounded Gwen's pussy hard and fast. Gwen was helpless to do anything except watch the action, which was quite close to her face. I could feel Gwen tremor with orgasms as I fucked her. I also loved the action as I plunged my cock deeper into the helpless, spread-eagled Gwen.

Gwen was now making squealing noises but the sound was thankfully stifled by the panties in her mouth. I had an idea. I pulled my cock out of her pussy and began to force it into her exposed, tight asshole. Gwen looked at me wide eyed and started to shake her head to tell me no. I ignored this and plunged all of my cock deep into her asshole. Gwen was making stifled squeals and I noticed that her eyes were full of tears. I continued to remorselessly pound her tiny asshole with my thick cock.

I could feel myself reaching orgasm, so I pulled my cock out of her asshole and I ejaculated all over Gwen's face. Gwen looked up at me helplessly with her entire face dripping with cum. I sat down at the side of the bed for a few minutes to regain my composure, leaving Gwen all trussed up like a turkey. After a few minutes I returned to the bed to untie Gwen and remove the panties from her mouth. Gwen rose and went to the bathroom to tidy herself.

After a few minutes, Gwen returned. She sat down besides me and put her arm around me. She said that everything was OK and that she was fine. She told me that anything that made me happy made her happy too. The rest of the day was less action packed. We continued to have sex all through the day, but it was a milder, gentler type of sex, which I feel Gwen enjoyed more.

It was Sunday morning. Gwen made some breakfast and then I caught a taxi back to my car before heading home. Before I left Gwen's I had a heart to heart with her. I explained that what we had was a fling and that now we both need to move on with our lives. Gwen looked terribly hurt at these comments and I felt uncomfortable delivering them. Gwen dropped her head and nodded and said that she realized that it could never be between us and then she said, "but I thought for a moment..." Her sentenced trailed off. I squeezed her hands, gave her a peck on the cheek and bade her farewell.

At home I agonized about the way that I had treated Gwen. I had enjoyed a great time with her and she with me. I hoped that she would be OK. Work was as usual on the Monday. Gwen and I interacted, but not much. At home during the week I noticed that my phone would ring but when I answered there was no-one on the line. I assumed that it may be Gwen trying to call me.

At the end of the week Gwen came to my office and asked if she could speak privately with me. I said of course she could. Gwen asked me if I felt anything at all for her. She told me that the last weekend had been the most marvelous time of her life and that she couldn't get it out of her head. I asked what she wanted. She said that she wanted more of the same. I told her that she could find that, but it wouldn't be with me.

Gwen sighed. She took out her cell phone and showed me the screen. She showed me photos of me lying naked in her bed and others of her sucking my cock. I was completely shocked. Gwen told me that she intended to show them to her female colleagues who always teased her about her nerdy ways. She said that if she showed the other women in the office the photos of us then they would have a renewed respect for her, as several of my female colleagues had a crush on me (according to Gwen).

I told Gwen that she couldn't possibly show anyone within the office those photos. Gwen was quite adamant that she could. I was upset. I told Gwen that it was quite clear that she was blackmailing me. I asked her what she wanted. Gwen now became quite upset and started to sob. She told me that she didn't want it to be this way. She didn't want to blackmail me, but she had no other bargaining chips. She said that all she wanted was to spend more time with me. She sobbed and told me that she loved me, and she hoped that I had some kind of feelings for her.

I put my arm around poor Gwen and told her that we should go across the road to the coffee shop for a little while. We sat and quietly drank our coffee. I felt so sad for Gwen. I did have some feelings for her now, but I was confused as to what exactly they were. Was it pity? I looked at Gwen and told her that I was willing to compromise and that I would gladly meet up with her once a week. Gwen looked at me and said that was all she asked for and that she just did not want to lose me forever.

From that day on, Gwen and I would meet at least once per week, sometimes more. Sometimes it would be an evening, sometimes a whole day or even a whole weekend. I grew to enjoy our encounters and even looked forward to them. There was always abundant sex, which went without saying, but there was also a lot more to our times together. We would go shopping, take walks in the countryside or take in a show or a concert. We even visited some nudist beaches together.

I also got to know Gwen a whole lot better as a person. She was quite an amazing little woman. She was exceptionally well read and she knew something on just about any topic that there is. She was also the most compassionate person that I had ever encountered. She was incredibly sensitive to the feelings of others, she was almost saintly. I can honestly say that taught me a lot, not in the least the way to behave towards others.

Both of us changed a little. Gwen became more outgoing and would get adventurous with the sex, even taking on role play and bondage in her stride. She even started to use make up and to buy more suitable and fashionable clothes. She was not just making the effort for me, but for herself also. She was far more confident in work and people now took notice of her.

Gwen had already been a more "well-rounded" person than I or anyone else had realized. She had just been missing affection, passion and love. On filling this gap, Gwen developed her character in leaps and bounds. As she developed, I became more and more attracted to her.

As for me, I became more affectionate in our love making, often kissing Gwen passionately, something that I would never had imagined possible. I also became more dependent upon her in many ways. She was my guiding light and she showed me how to live my life in a better way. I am still learning.

We developed a very strong bond between each other. Seeing each other about once a week also helped to keep the relationship fresh. We developed what I would call a very healthy, physical and loving relationship between a man and a woman that many "full time" couples would be totally envious of. The relationship is still ongoing and thriving to this day. Isn't it strange how things work out? Had my ugly duckling turned into a swan?