Chapter 7 deals with three stories that i thought i'd bundle together as they didn't seem to be a chapter by them selves. I know that i'll probably get a bit if flack for one of them, but it happened and rather than change it to be more palatable i wrote it as it really was. Three different stories from three different times of my life. I hope you enjoy them and don't judge me too harshly.
THE GOOD, THE BAD AND THE UGLY.
I had been living interstate for a couple of years now when I first met Tracy.
An extremely pretty skinhead girl with amazing eyes, in her late teens with a nice rounded bottom and small petit breasts.
I was quite taken by her, even though she didn’t fit my sexual preference.
She made her living, according to her, from the generosity of older wealthy men, and as I didn’t fit that category felt I had no chance.
The more we ran into each other the more we got on, even to the point where she would run up to me and hug and kiss me at each meeting.
Streetwise and worldly beyond her years she knew how to bend me to her will. There she was making hundreds of dollars a day as a young prostitute and I was buying the drinks.
Often she would stay in my spare room overnight but always made it very clear that I was a friend and she was not going to let me fuck her, ever.
Some months later we were sitting at home watching a movie and holding hands. I’d had a bit to drink and so was in a bit of a daring mood when I turned her head to mine and kissed her. To my amazement she kissed me back and moved my hand up under her singlet to her breasts. We kept kissing as I caressed and squeezed her small soft tits. After a few minutes I went to move my hand down between her legs, she pushed my hand away got up and said “Why do you have to go and wreck it by doing that”.
I apologised but she was furious and left.
Next time I saw her she told me that I was forgiven and things continued on as if nothing had happened.
At my next birthday she took me out to this ridiculously expensive restaurant, told me not to worry about the price and had me eat and drink what ever I wanted until I was full. It didn’t cross my mind until later that all the staff seemed to know her and her likes. After the meal she paid the bill and we went out dancing until the very small hours.
I was so drunk I practically fell out of the cab on our arrival home.
“Come on you big drunk, lets get you into bed”, she said.
I flopped onto the bed on my back laughing.
First she pulled off my shoes and socks, then my shirt and finally my pants and undies. Pulling the covers up over me she kissed me on the forehead, turned off the light, undressed, climbed in beside me and kissed me again. “Happy Birthday” she whispered.
I kissed her passionately, then moved my head down and sucked her erect nipples.
She had a firm hold of my cock and was squealing with excitement.
Under the doona down her head went, her moist mouth finding my foreskin and expertly working it, moments later she was back up kissing me once again.
Taking my hands she rubbed them across both of her breasts and then down over her stomach until I could just feel the top of her pubic hair. She kissed me again and moved my hand lower, at first I was confused as to what I was touching and then it hit me.
I was holding her small erect penis.
Tracy was a boy not a girl.
It was the most memorable birthday present I’d ever had. She blew me and fucked me. I fucked her and drank her cum.
She was amazing.
The next day she moved in with me. She continued to work but now she bought the drinks instead, and we spent 2 wonderful years together until she got restless and moved on.
I never revealed her secret to anyone and we remained the best of friends until she passed away in a motorcycle accident years later.
At just under 17 years Dwayne was smaller than most guys his age.
Soft features, the cutest dimple in his chin, light brown hair parted down the middle and the tightest little bottom imaginable. I wanted him, he obsessed me.
Even though I had other cocks that I was sucking at this time I wanted his. Not just to suck, hell I would have been pleased to just see him naked and touch him, but that was out of the question as he never got undressed in front of me and always slept in his shorts and shirt.
Before I left his house one night I arranged the curtains in his bedroom so that a small slit was open to the outside. I said goodnight, rode my pushbike to the side of the house and returned to position myself at his window.
I waited, the toilet flushed, I heard the door open, the light flicked on and there he was standing alone in his room as I peered in. He lifted his shirt and removed it, stepped out of his shorts and removed his boxers, finally after all this time there he was in front of me completely nude, seconds later the light was off and I slinked away into the night.
Over the next year or so I peeped on him at every opportunity, sometimes seeing something other’s not.
Two years passed, I'd shown him how I could go into a trance, but even though he asked me to wank he never once touched me or let me touch him. To say I was frustrated was an understatement, and I was no closer to having him than the day we met.
Anyone else I would have discarded long ago.
Winter came and the family was all out watching him at football training as I used a copied house key, let myself in through the back door, climbed up into the roof crawl space and edged my way along until I was looking down through the steam extractor right above the bath.
I heard the car arrive in the driveway and moments later the sound of the family filing through the front door.
Not long after Dwayne entered the bathroom turned on the light and began to fill the tub. My cock was out and my heart was beating like a drum as he stepped out of his mud soaked football uniform, and facing away from me stepped into the bath. Just the sight of his small round perfectly formed boys bottom nearly made me cum. He placed a face washer over his cock so my view was still blocked and slowly began swaying left and right so the motion of the water and material brushing against his penis excited it. I could see his cock fattening, it was now flopping heavily from side to side. He lifted the cloth off, and my god had it grown since I first spied it through his window. About the width of an empty toilet roll, nearly 7” long and pubic hair blacker and glossier than any I had seen before.
He got out, sat on the edge of the bath and masturbated until cum shot up and over his shoulder, I on the other hand had cum as soon as his cock was first uncovered.
It then took me over an hour to inch my way back and quietly leave the house without raising any suspicions.
Now I was more determined than ever to have him, my obsession had become quite manic. Now that he had reached puberty he was more than capable of doing to me all the things that I wanted, but it was patiently clear to me by now that he was a hundred per cent straight and the first guy that I was not going to be able to conquer.
Fast forward two months and we’re in my snooker room playing pool when I drop two sleeping tablets into his drink.
We continue to play as he gets groggier and begins to stumble.
“I think you’ve had quite enough to drink”, I said. “Come on, off to bed with you”.
Half walking and half stumbling into my bedroom, he collapses on the spare bed with a bang.
“Oh well, let’s get these shoes off”. I said. Removing one and then the other. Next I removed his socks, lifted his tee shirt up and over his head and can’t resist quickly kissing his nipples. Not the slightest protest came from him as I continued to undress him, first his pants and then his underwear.
I ran my hand from his lips down across his chest and stomach through the thick mass of black pubic hair, down over his soft cock and balls between his legs and right up to his tight bum hole.
I was losing it. This situation was now overtaking my mind and reasoning. I lifted his naked body up. He was like a rag doll. I kissed him on the mouth and ran my tongue all around it’s inside. I licked his neck, under each arm, sucked his nipples, chewed first one ball and then the other and finally had that that I had yearned for all these years in my mouth, sucking so hard that you would think that I was trying to pull the sperm right up and out of his testicles then and there.
Turning him over I spread his legs, pulled his cheeks as far apart as I could and pushed my tongue into his ever so tight hole.
I plunged a finger in, my god he was tight.
Rubbing my cock up and down between his cheeks his entire ass was now covered in spit and pre-cum as I first edged his ass open with the tip of my penis and then forcibly pushed the entire length into him. Not a word left his lips as I pounded unmercifully away in him. Still impaled on my cock I picked him up and shifted positions, his arms and legs just hanging limp at his side as I rammed my cock into him even harder finally Cumming so much that I could feel it running out of him, down my cock and over my balls. It was only when I finished and pulled my dick out that I noticed it wasn’t cum but blood.
I began to panic as I tried to clean him up and redress him. Finally I had him back in his clothes and in bed.
The next morning I heard him get out of bed and go into the bathroom, minutes later he came back into the room crying, looked me straight in the eye and said “You fucking cunt”, turned and left. That was the last time he ever spoke to me. My idiocy and obsession had wrecked one of the best friendships I had ever had in my life.
I was, in hindsight just lucky as hell that he kept it to himself and didn’t call the police.
It was my final year at high school and the list of my conquests was pretty long. Much longer if you also counted the anonymous men whose name’s I never knew. There was one guy at school though, because of his severe facial deformity that I had steered well clear of.
It wasn’t that he was a bad guy and if you could get past what he looked like he really was quite nice, it’s just that I liked pretty and he sure the hell wasn’t that.
Still, ever since I had spied his cock out of the corner of my eye while showering in gym class many years ago I had been fascinated by the thought of him, and deep down in my heart I always had a secret, if somewhat repressed desire to be with him.
I will call him Tran.
About six foot tall. Just turned 17. Skinny as a rake and originally from Vietnam, he had been adopted by an older couple as a small child. One side of his face was quite normal while the other looked somewhat melted. No one really spoke about what caused it, but from what I understood it was a birth defect and his family had abandoned him.
I’d never had an Asian guy before and loved the idea of adding one to my list. I loved their little button noses, the shape of their eyes, the colour of their skin and the way they all seemed to be brilliant but slightly vulnerable at the same time.
I asked him, and he agreed to come to my house and help me with my maths, as I was failing badly.
I must say that I was pleased how easy it had been for me to convince him. My parents were also happy that I was trying to get help with the subjects I was having trouble in. And he seemed to be delighted that someone had shown an interest in him and invited him to stay over for a night, even if it was only to help with homework.
He arrived a bit before six and after Mum had fed us we retired to my room to study. I really wasn’t interested in homework but went through the process anyway, and to be fair, some of the tricks and different ways of solving problems that he taught me were quite helpful. In fact if I were really truthful, I would say that the evening was quite a success up to that point.
After the study session we sat on my bed watching some show that I really wasn’t paying attention to.
Around ten thirty I told him it was probably about time to go to bed and he nodded.
I set his bed up and asked if he needed more blankets, but he declined. Turned the lights down and proceeded to undress.
He sat on the end of his bed watching me.
“I wish I had a body like yours,” he said, catching me off guard. “I’d love to have muscles”
Removing my jeans, and getting into bed I laughed. “Well I wish I was tall like you, so that makes us even”.
He remained sitting on his bed.
“Aren’t you going to bed”, I said.
“Can you turn off the light first” he replied. “I hate people seeing my body”.
“Well I don’t care so get it off and get into bed”
I saw he was uncomfortable as he removed his shirt and I could see why. He was thinner than anyone I’d ever seen, you could count every rib on his chest and his arms were so thin I could have wrapped my thumb and finger around them.
“So your skinny, who cares”, I said.
Removing his jeans, he stood in front of me in silk boxers.
Incredibly long legs, so thin that I wondered if that they might snap at any given moment.
A slight smile crept across his face, as I said nothing while he climbed into bed. I said goodnight, turned off the light and lay still waiting for him to fall asleep, but about ten minutes later it was he who broke the silence.
“Are you going to suck my cock”, he all but whispered.
“They say that you suck”, he again whispered.
“Who said I did?”
“At school, they all say it”, he said in a stronger voice, emphasising the word all.
This was the first time that I was conscious of the fact that I was the subject of talk at school, that people were aware of my secret.
I was rattled. I didn’t like not being in charge of a situation.
“Do you want me too?” I asked with a slight quiver in my voice.
“Well, you can try”, he said.
I reached over in the dark and fumbled for his cock. I grabbed his arm and my mind froze, that was not his arm but his erect penis. “Um, err, is that?”
“Yep” was all he said.
I reached over turned the bedside light on, pushed his covers off and there poking through the leg of his boxers was a cock the size of which I had never seen before, even all those years ago in my father’s magazines.
The size of my forearm, and while it had to be a foot long I could have counted the number of pubic hairs he had. I was gobsmacked and stared at it open mouthed in amazement.
“Well?” he said.
I reached over and removed his shorts, Christ it looked even bigger out of them. With two hands I masturbated him as I guided it to my mouth and close my lips around it. No matter how I tried the most I could swallow was only the first few inches, but try I did and I sucked him like there was no tomorrow.
My mind was racing, who set up who I wondered as I climbed into bed with him. My jaw ached from being forced open so wide and I have no idea what on earth I was thinking as I rolled over and positioned his enormous cock on my asshole and began pushing back.
“Are you sure?”
“I don’t know but I’m keen to try” I blurted out.
His cock was soaked with my saliva as he nudged it forward. I felt his foreskin pull back slightly between my cheeks as the tip of his cock opened me. I felt a touch of pain, but nothing I couldn’t handle I thought. Then he moved again and about 4” slid into me in one quick movement.
Pain like I’d never felt before shot through my entire body, I thought I’d been torn open and pulled it out as fast as I could.
I thought it had hurt when I had the crap beaten out of me that time, but this was worse.
He turned my head and looked at my face; I had tears streaming from my eyes.
“Sorry”, he said.
I lay there, waited for the pain to subside then placed it once again on my hole.
“Lets see if I can take just your knob”, I asked.
He pushed it in just a fraction and withdrew it, again and again he repeated the action, each time entering me just a tiny bit more while resting in between for me to relax, until after fifteen minutes or so he had about half his full length in me.
“I’d love to go to sleep with it in you like this”, he said. “I think if I move it even a bit I’m going to cum”.
I wrapped his arms around me and just lay beside him feeling totally contented with him deep inside as he drifted off to sleep.
Some time later I reached around, felt the half of his cock that I wasn’t in me and was surprised at how soft and supple it now was, not a hard on, not a soft on, but somewhere in the middle. I pushed my ass back and felt another couple of inches penetrate me, without a full erection the pain just wasn’t there. Pushing back harder another inch entered and then another until his hairless balls were pushed right up hard into my cheeks and it felt like the other end was up in the middle of my chest. I reached around and shook his shoulder, “Hu” he said sleepily. I grabbed his hand, pushed it down between my back and his stomach until he could feel that his cock was now entirely inside my ass. Within seconds it had returned to a full-blown erection. I was stretched to capacity, and then slowly and ever so gently holding my hips he began to rock to back and forth inside me. A minute later I was convinced that I could feel this hot surge filling my insides as he kept repeating over and over in my ear, “I’m Cumming, I’m Cumming”.
The only person I ever told what happened was Kenny but within a couple of weeks it seemed to be common knowledge, at least in my year, that Tran had an absolute monster in his pants. In fact he reached a sort of demi god status with the other guys and in a few months even had a girl friend.
Years later at a high school reunion I ran into him again. He’d married that girl and had two of the most beautiful children I had ever seen.
Later that night he took me aside and told me I was his first sexual experience ever. Thanked me for letting everyone know about the size of his dick, his wife finding out, asking him on a date and letting him have his first taste of female sex.
I never told him it wasn’t me.