The Ugly Duckling

by Lee Obrien

17 Jun 2023 4512 readers Score 9.1 (100 votes) PDF Mobi ePub Txt


The Ugly Duckling

Chapter 1

I stepped out of the shower and caught a glimpse of myself in the mirror. Damn, I did look pretty good, if I do say so myself. My freshly washed jet-black hair hanging just down to my shoulders, I had recently let it grow to that length. My dark eyes sort of sparkled each time I batted my long eye lashes, I could still see my dimples, though they were covered by a two-day growth of a neatly trimmed beard. I scanned further down, two quarter sized nipples stood proud of the light coat of black hair the covered my well-defined chest and flat stomach. Continuing down to my freshly trimmed bush above my flaccid 4” cut dick and plum sized balls. Finally, my muscular legs were covered with the same dark fur as my chest. I turned my ass toward the mirror and looked over my shoulder, round and plump, again, I was pleased at what I saw. I’m sorry, I don’t mean to sound so vain, but I haven’t always looked like this. I am proud of how the hard work I have put in the last couple years is finally starting to pay off.

My name is Tyler James Wilton, to say that I was a surprise to my parents would be an understatement. My parents wanted to have kids shortly after they married but had trouble getting pregnant. The doctor had even suggested that they check into adoption if they wanted children. They were thrilled three years later when my sister was born, they were told that she would probably be an only child. They happily raised their daughter and walked her down the aisle when she was 22 and six months later, they were even more excited to learn they were going to be grandparents. Life threw one of its famous curve balls when a short time later, mom told my stunned father, that he was going to be a dad once again. This was certainly not in the plans for my 50-year-old father and 48-year-old mother. Yep, I am 23 years younger than my sister and my nephew is 5 months older than me. By the time I was five, I had two more nephews that are only a few years younger than I am.

I was what you could call a chubby baby, but as I grew, I never lost my baby fat. To make things worse, I was shorter than all the other kids my age. While this was cute when you are under ten years old, when you get to be a teenager, you are just the short, fat kid. The fact that your parents are both over sixty and dress you like they would have, if they had had you twenty years earlier when they planned, you are soon the kid that everyone makes fun of. By the time I was in jr. high school, I of course needed glasses and once again, mom chose a pair just like the ones that my dad was wearing. I was an easy target for all sorts of teasing.

I met Andy Shaw in first grade, and we became fast friends and remain so to this day. Andy and I were physical opposites, while I was short and fat, he was tall and skinny, my dark hair and skin, his pale skin and blonde hair. But as our classmates continually reminded us, we did have one thing in common, we were geeks or nerds or whatever other similar term they chose to use that day. As we got into high school, our main goal was to make it through the day with just two or three insults. We both developed thick skin and kept our heads down and we both excelled in our schoolwork.

Just as I had accepted my nerdiness, I was suddenly hit with my next difference, that I was sure would bring me more ridicule. I started to notice that I was more interested in checking out the guys in the locker room than I was watching the girls walk down the hall. Shit, I might as well just leave school now if this little secret got out. I could just hear all my classmates saying here comes the short fat kid that wants to suck cocks. I was relieved when I made it to my senior year and the only person who knew my secret was Andy. I had told him last year when he was trying to work up the nerve to ask a girl in our class to a dance. He was a little surprised but assured me he would keep my secret and he did.

A few weeks after the school year started, one of our teachers assigned us a project that we had to complete with another classmate. Instead of letting each of us pick our own partner, he decided who we would be working with. Instead of me working with Andy, I was going to have to work with Kyle McCain. Kyle was the leader of a group of guys that Andy and I referred to as the jock squad. Reggie Thomas, Travis Reed, and Matt Munson filled out the squad. I can’t say they bullied us, but they were usually the first to make what they thought were clever comments about us whenever they got the chance.

Kyle was the star quarterback on the football team, so of course, he was a 6’, blonde hair, blue eyed Adonis. I had used the memory of him walking naked to the shower after gym class to jack off, more than once.

Reggie also played football but was also the captain of the basketball team. He was a gorgeous ebony skinned Greek god, 6’2” with a slim build and a smile that lit up the room every time it appeared.

Travis was the track star with thick muscular legs, he was also 6’ tall and had the pale skin of the stereotypical redhead. I can’t explain why, but my heart would skip a beat whenever I saw him and Reggie walking next to each other. It must have been the contrast of their smooth skin, one of my favorite fantasies was of them wrestling each other naked.

Speaking of wrestling, that is where Matt fit into this group. He was 5’10” and had the stocky build of a wrestler. He had brown hair and eyes and filled a singlet pretty well, with nice bulges in all the right places.

My mouth went dry when I saw Kyle walking toward me after class.

He said, “hey Tyler, I guess we get to work together on this thing, how do you want to get started?”

I swallowed hard, “I guess we could meet at my place after school, my parents don’t get home until after six.”

He smiled, “that works, I have three little sisters at home that wouldn’t leave us alone if we went to my place.”

I thought to myself, ok, that wasn’t so bad, maybe he is an ok guy. We set up a time and I gave him directions and we headed off to our next class.

My nerves started to kick in on the walk home from school, how was this whole thing going to go? I was looking forward to being around him, but I was also a little worried that he would be pissed that he had to work with me. Maybe I was getting too worked up, we just had to get this project done and then we could both get on with our lives. A few minutes later the doorbell rang, and I led Kyle to the dining room table so we could get to work. We got our outline done and a good plan to complete the project and an hour and a half later he was headed out the door. It would take three or four sessions to complete the project, so we set up our next meeting. I was relieved that everything went well, we just did the assignment and Kyle didn’t tease or insult me at all.

We were on the last night of working on our project and finished well before my parents were due home. We had moved our study sessions to my bedroom, as that is where my computer and printer were. As the report was printing, I was both relieved and disappointed that we were done. I was surprised that Kyle didn’t once tease me, he actually did his share of work on the project, and our strengths complimented each other well. Andy had told me that he was stuck with Matt, who was clueless about how to do the project, so Andy did most of the work.

The pages finished printing and we put them in a notebook, and we were ready to hand it in tomorrow.

Kyle flipped through the pages and smiled, “it looks pretty good Tyler, I think we’ll get an A for sure.”

I smiled back, “yeah, it did turn out well.”

I started to get a little nervous as he just sat there and stared at me for a few minutes.

He finally spoke, “can I ask you a question?”

I shrugged, “I guess.”

He said, “if you don’t want to answer, I will understand, and I won’t tell anyone, I promise.”

My stomach flipped, what was he going to ask me. I stuttered, “Um, ok. What is it?”

He asked, “what is the deal with you and Andy?”

I looked at him, “what do you mean?”

He continued, “well, you guys are always together, you seem really close.”

I said, “we are just friends, that’s all.”

He nodded, “oh, it just seems like there is something more.”

I said, “in case you haven’t noticed, we aren’t exactly popular. I guess we are the only friend each other has.”

He said, “I’m sorry, I didn’t mean to imply anything, it’s just that I have never seen either of you talking to any girls.”

I chuckled, “yeah, the girls don’t tend to flock to goofy looking nerd types.”

Kyle chuckled too, “yeah, I guess not.” He paused for a minute, then said, “If I am wrong, I’m sorry, but I thought it seemed like you were checking me out in the locker room after gym. I was just wondering if you guys were gay.”

I felt the heat rush to my face, I am sure I was as red as a tomato, without thinking I blurted out, “Andy is not gay.”

He looked at me, “ok, but you…”

I quickly looked away, “but nothing, I just… no I mean, it’s not that. Oh hell, I don’t know what I am. Shit, you don’t care anyway.”

Kyle turned to me, “it’s ok, Tyler, things can be confusing sometimes.”

I turned back to him, “let’s just drop it, we have the project done, you can leave, and we can get back to our lives.”

He asked, “have you ever done anything with a guy?”

I shook my head, “I haven’t done anything with anyone.”

He moved next to me on the bed, took my hand and put it on his crotch. I was shocked to feel his cock was already hard, this caused my own dick to spring to life. My heart was beating out of my chest as I looked Kyle in the eye, I didn’t try to take my hand away. He slowly reached down and unzipped his pants and pulled his hard cock out. I just stared at it and started to stroke it up and down, a drop of precum formed on the purple, mushroom shaped head. Kyle’s dick had swelled to at least 7 inches and curved slightly downward. He looked at me, as my eyes were locked on the cock that my hand was wrapped around.

He said, “you can lick it, if you want.”

I must have been waiting for permission, because as soon as he said that my tongue was slurping up the precum that was now running down his shaft. I took him as deep as I could, gagging slightly, I heard Kyle moan as I worked his dick. I fumbled with his belt and got his pants unbuttoned and pulled them to his knees. I stroked his cock as I started to suck on his nuts, one at a time. Kyle had his hands on the back of my head and continued to moan as I did my best to please him.

He said, “damn dude, you are going to make my cum.” He pulled me off his cock and asked, “can I fuck you?”

My mind was racing, I just had the cock of the hottest guy in my school in my mouth, and now he wants to fuck me. I just reached over to the nightstand beside my bed and grabbed the bottle of lotion, that I had used the night before to jack off, with visions of Kyle in my mind. He turned me over and leaned me over the edge of my bed and pulled my pants down, squirting the lotion into the crack of my ass. I felt his finger start to work over my hole, my rock-hard dick rubbing across the sheets of my bed. He ran the head of his dick up and down my crack, then paused at my entrance, then slowly pushed in until his nuts were resting on my ass cheeks. I heard myself moan as he started to thrust in and out, any doubt that I was gay was quickly going away, I was enjoying this too much to not be gay.

Kyle picked up speed and his breath quickened, and he panted, “I’m going to cum.” He pulled his dick from my ass and shoot his load across my cheeks. Once he had finished shooting, he slapped his cock across my ass a couple time and wiped the last drops of cum on me.

I was still laying across my bed with my pants around my knees, I realized that I had shot my own load of cum onto my sheets. I was catching my breath as Kyle pulled up his pants.

He gave my ass a slap and said, “thanks, I needed that, my girlfriend hasn’t been putting out lately and remember butterball, this stays between us. If you tell anybody, I will make your life hell.”

 

To be continued…

by Lee Obrien

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