The Flight of the Ugly Swan -- Chapter 1
Even the unattractive get lucky sometimes.
I am ugly. There's no point in pulling any punches about that. I am so ugly that I could make a train take a dirt road. I am so ugly that I have to sneak up on a toilet to take a crap. I am so ugly that the doctor slapped my mother when I was born. Those are just three of the many insults that my brother routinely hurled at me as I grew up. He was just two years older than me and was just being a typical brother, but because it was (and still is), true that I actually am ugly, he may have contributed to the shyness and bitterness and low self esteem that lead me to become a forty year-old virgin -- type female. I wish that I could tell you that this will be an ugly-duckling-becomes-beautiful-swan tale, but if there's a swan waiting to come out of me, it's late and it's ugly anyway.
You've heard the expression "Sweet 16 and never been kissed"? Well, I was probably never sweet and I reached 18 before I was ever kissed and neither of us were all that thrilled about that, being that my prom date was bullied into taking me to the 'let's-make-the-walflowers-even-more-unhappy' event by his mother, who was friends with my mother. That night was a disaster. I chose the wrong dress, not knowing it would feature all of my worst features. But since no dresses come with bags for covering ugly faces, I suppose there was no right dress. When he brought me home, after three boring hours of watching other couples have a good time, he kissed me on the lips with all the enthusiasm one would display when kissing a bag of potting soil. But enough about the distant past.
At the beginning of the events of this tale, I was 'Bitter, 40 and never been fucked'. It's actually easy to accomplish that when you combine a wan complexion, oily facial skin, a bulbous clown nose, Dumbo ears, bodiless frizzy hair, rheumy eyes, coke-bottle eyeglasses, excess facial and body hair, an overbite, low cheek bones, micro-boobs, hips that ballooned with every ounce of excess body fat and even my toes are ugly. Add the fact that I'm uncoordinated, clumsy, socially awkward, inept, incompetent and just generally have nothing to offer a man except the fun of tolerating a shrewish attitude. This would all have been so much easier for me to tolerate if I was stupid, but I actually have a brain. I guess when they were passing out great looks I must have heard, 'great books' and I showed up at the library.
The only bright spots, with any man in my life, came from my brother-in-law, Charles. I was still living with my parents, in the basement of their home, so, when he visited with my sister, Janice, from their home in Wisconsin, he would always hug me when he arrived and again when he left. These hugs usually included a squeeze of one ass cheek and he was so sneaky that nobody else ever saw it. I was so thrilled by the liberty he was taking with me that I never said anything about this, even though I considered it to be cheating on my sister. Maybe that cheating part added to the thrill.
He also would sometimes give me a backrub, which never seemed to bother my sister because it would happen on the floor in front of her, while we were all watching a movie together and he would usually also rub her back. The first time it happened, she encouraged him to do it and encouraged me to let him. I think she just wanted to rub in how lucky she was to have him, but he gives great back, I was always grateful and I always got wet. Unfortunately, their visits were few and far between, because it was a long, two days of driving to New England for them. This visit was even shorter than normal because they were going on to a vacation elsewhere.
Long before the events I will soon get around to relating, when I was a bridesmaid in their wedding and was wearing a pretty dress. Charles complimented me on the beautiful shape of my legs. I guess that I wasn't completely ugly, but damn few men could look past the train wreck, that was the rest of me, to find the one asset that wasn't included in it. I became smitten with him then and was very envious of my sister that day. I often featured him as the hero in my fantasies after that. He would sweep me off my feet, take me to bed, tenderly pop my cherry and then we would live happily ever after, in orgasmic bliss.
About 20 years later, during their previous visit, it almost seemed that they might break up. Janice is a real drama queen and often acts kind of hoity-toity. I could tell that their marriage was becoming progressively less interesting to both of them. That changed with the visit that I promise I'm about to relate to you. They both seemed much happier and more in love with each other.
When they visited this time, both welcoming hugs from the happy couple seemed unusually warm and gropey. Truth be told, any physical contact with any other person was enough to both fluster and arouse me, but those hugs were something else. Janice hugged me first and her hands seemed to fondle me a bit and I could have sworn that she humped my thigh a little. When Charles hugged me, his hand lingered on my ass, as he pressed my chest against his, until I was sure he could feel my nipples harden and I know I felt a bulge against my belly. The two of them really lit a disturbing fire in my honeypot.
The next afternoon, Charles was watching TV, in a small den in the basement, so I decided to see if he would like some cookies and milk. He was the one person in the world that I would think to make such an offer to, because he never ever took me for granted. As I came to the room, I saw that he was lying on his back on the short couch (dare I call it a loveseat?) and had his feet up on the armrest. Since it was a warm Summer day, he was wearing shorts and the floor lamp in the room was shining right down the gap between his shorts and his left thigh. I could clearly see the edge of his small sexy striped briefs, but I could also see the wrinkled skin of his hairy ball sack and, more importantly, his briefs only partially covered the brown shaft of his flaccid cock and about 3/4 of the pink head, just barely concealing the hole that I knew must be on the end. I'm guessing his cock was only about 3 inches long and not very thick at the time. Maybe about as thick as my ugly big toe.
This bit of voyeurism may not seem all that special, but for me it was a first. I lead such a sheltered life, that I had managed to make it to age 40 without ever seeing a man's cock live. I've seen the occasional photo and a few limp dicks in scenes from movies, but never closeup and never so well lit. I tried to avert my eyes, but I just wanted to stare at that mysterious marvel.
I cleared my throat and drew his attention from the movie to ask about the cookies and milk. He looked me in the eye and said 'yes' and gave no indication that he knew his cock was exposed to my view. When I came back with the snack tray, I got a big surprise, literally. His cock had grown to maybe five inches long and the shaft was much thicker and paler and more pinkish. Most of the much larger head was now exposed and it was more purplish. I could even see the tiny slit at the end. I stood frozen staring at it for at least a minute while he continued watching TV as if he hadn't noticed my arrival. When I could finally tear my eyes away, I gave him the tray and he looked right at my eyes as if his privates weren't public at the moment. I got all flustered and left the room in a bout of shyness. I needed to think about what just happened and to do something about the wet stain that was growing on my panties and threatened to flow out through my shorts.
I changed my panties and put a mini-pad in them. It was a good thing that I did, because, for the rest of the day, I was in a state of high arousal. The image of his cock kept flashing in my mind and I could only barely glance at him during dinner for fear that his gaze would pierce me and make me blush or even have an orgasm on the spot.
That night, I lay in my bed thinking about what I'd seen. In the privacy of my room, I could dwell on the feelings I had earlier felt. I wanted to slide my hands down his thighs and fully expose his magical pink living treasure. I wanted to stroke it. Sniff it. Lick it. Tear my clothes off and jam it in my pussy. Feel it shoot man-juice into me. Feel it change my sexual experience status from over-aged virgin to finally well and truly fucked.
Alone, and naked in my bed, my fingers traced circles around my nipples until both were hard enough to cut glass. Then my one special hand, the hand that knew how best to please me, trailed down to my pussy. I knew that I was already wet and I loved starting out already wet. I knew that my clit was already protruding from my folds, but I left it alone. My favorite middle finger went to the far end of my slit, where my juice was oozing out and down between my ass cheeks.
My bishop was already in place in my ass. I had slipped my secret black plastic lover in when I changed my panties earlier. The little guy had been with me for many years since I rescued him from the trash after my brother had blown up the kings and queens of both colors with fire crackers. I loved to keep him in me, for extra sensation, when I was in the mood. Sometimes I used one hand to play with him while the other attended to my pussy, but tonight my nipples were on fire and they needed to be pinched and pulled, as I dipped my middle digit into the flow of liquid lust.
With just the slightest touch, my pussy lips opened like stage curtains, all but pulling Mr. Middle and Mr. Pointer into the wet hole behind them. Not too deep, because I did not want to lose my virginity to my own fingers. They stayed long enough to get thoroughly drenched and then rose to wrestle the little wet weasel as visions of Charles' man-meat pulsed in time until I shuddered with delirious ecstasy, barely able to keep the sound of my release contained, so that Charles and Janice would not hear me, as they watched a movie in the room next door.
I came to the conclusion that Charles must have deliberately exposed himself to me. If only I could let him know how grateful I was. I went to sleep with a smile on my face and a plan.