Confessions of a Teenage Slut

Confessions of a Teenage Slut

By Greg and Maddie





Warning: This story contains very disturbing content. Sensitive readers should go elsewhere if they are easily offended.

First, let me say that Maddie is a dear friend of mine. We have been together for a while now. When she learned that I write stories, she offered a tale that I just had trouble passing up.

Yes, I know Maddie was taken advantage of. But she asked me to put all of it in this story about her life. So before the self-righteous hypocrites out there jump all over me, just remember that this account was entirely her idea. Was it therapeutic, maybe? I am just the typist, really. We both enjoyed working together on this, and besides, I think she turned out alright. I am sorry the story runs a little long, but Maddie didn’t want it chopped into chapters. I did make her promise that if the response was good, we would write a follow-up. I had a difficult time deciding how to limit the story to just this much. Maddie has a very colorful history.



My name is Madeline, but everyone just calls me Maddie. Ever since I can remember, I’ve always needed to be the center of attention. My earliest memories were of wanting to be watched or noticed. Growing up, I was an only child. It was just Mom and me, but there was always some guy around. My real father, if you could call him that, was never there. I’m pretty sure Mom might not even know exactly who he was. My mom had always worked in bars and restaurants as a barmaid or waitress. She always had to have a man around, even though they never stayed long.

Mom had an attractive body. She was a MILF before the term was even used. She had a slim figure and large breasts. She was always a stickler for having her hair done regularly. It didn’t matter if we had the money or not; her hair was a first priority. She always wore low-cut tops on the job. She knew her tips would be better if men got a good look at her. This is probably how she got to bring so many of the guys home.

For as far back as I can remember, men were always there. Mom told me when I was little that these were my uncles. I didn’t really know or care that much what that even meant. I knew she would be happier when there was a guy around, but it usually ended in a big fight.

My mom’s looks would always attract men, but her domineering personality would always chase them away. I’m sure if I talked to a shrink, he would tell me my need for attention has something to do with not having a stable father figure around. I never knew any different and just got used to having someone new around every couple months.

My earliest memories are of these different men in our lives. Mom had evening work hours and sometimes left me at home with some of them. I was always really friendly, and I got along really well with most of them. Mom was probably too trusting with a few of them. I’ve never told her that more than a couple had given me baths or had walked in on me while I was getting dressed for bed. One guy liked to help me pick out what to wear and usually watched me try on different outfits. I used to pretend to have a fashion show for him. I always seemed to have a desire to please them. I guess I thought if they liked me and mom, they would stick around longer. While mom was at work, I spent many evenings cuddled up next to one of them on the couch watching TV.

There was one particular guy I really got attached to. His name was Derrick. Mom had met him at work as usual and started bringing him home. He came by occasionally in the evenings when Mom had to work. He was good at fixing things, and since we were always in low-rent apartments, there was always something around that needed repairing. It was always a hassle to get the landlords to fix anything.

He and I would often wrestle on the floor of the living room. He liked tickling me and giving me rides around the apartment on his back. He had me call him by some silly horse’s name while we were doing this. Sometimes we would just lie on the floor and play a game where he would search my body for a new tickle spot. I would just lie there as his hands moved around on me. I would fight back the urge to laugh. Other times he would lay right on top of me and pin me to the floor like a great monster. I would have to find a way to wiggle out from under him. We had a great time doing this.

Derrick and Mom used to make a lot of noises late at night when she got off work. The apartments were usually small, and my room was usually right alongside hers. I was curious one time and quietly snuck into the hallway. Mom’s room only had a single light on. I saw them on top of each other. Mom’s moaning concerned me at first. I was afraid they were mad at each other. I remember watching at the edge of the door for some time, and of course I saw most everything they were doing.

I think that was maybe the first time I realized that a guy’s cock was used for things other than peeing. After a bit, I guess I figured out that they weren’t angry. At one point, Derrick sat up and kneeled on the bed. Mom started sucking on the end of his cock. I remember trying to figure out why she would be doing something like that. While she was doing it, Derrick happened to look over towards the door and saw me standing there. He made no effort to cover anything up and continued thrusting at my mom’s face. He sort of held my mom’s head in place with a hand on top of her head and then sped up what he was doing. Mom couldn’t move, turn, or move her face, so she just let him continue. Soon, Derrick went even faster. He looked right at me and let out a loud groan. I got scared at that point and ran back to my room, pulling the covers over my head.

The next day, I said nothing about what I had seen. Mom was offered a double shift and had to work late that day. She asked Derrick to stay that evening and watch me. Just before bed, I was in the bathroom taking a bath. Derrick knocked on the door and just came right in. He said he had to go pee real bad and was sorry that he couldn’t wait. I was sitting in the tub all soaped up and he just came over to the toilet and unzipped his pants. He undid his pants in the front and exposed his cock.

It was a lot brighter in the bathroom than it had been in the bedroom the night before. His thing was huge. He didn’t make any effort to shield my view, and of course my eyes were glued to the sight of a full-grown man’s penis. He shook it a couple times and then for no apparent reason dug in his pants and brought out the whole thing, balls sack and all.

I wasn’t sure what to do at that point. I just remember sitting there waiting for something to happen. It just hung there, all red and bloated-looking. Derrick looked over at me a couple times and just smiled. He rubbed at his balls for a few seconds, and then pee started to come out the end. Derrick just stood there and drained himself. After he finished, he let it hang there for a long time. I thought he was going to pee more, but finally he just shook the whole thing a few more times, and that seemed to be it. Carefully, he put the entire thing back in his pants and flushed the toilet. He left the room without saying another word.

I don’t really remember being that shocked by that event, mostly because he did it in such a casual way. I do remember thinking, “Oh, well, there it was again; no big deal.” As it turned out, it didn’t matter anyway.

Later that same night, something happened. I was asleep when the shouting woke me up. It was very late, but Mom and Derrick were both in my room. I had never heard Mom so mad. I was scared to open my eyes and pretended to still be asleep. She was screaming for Derrick to get out. I thought she meant just my room, but it was worse. In the morning, when I woke up, Derrick was gone. I never saw him again, and Mom refused to even talk about him ever again.

There were other male friends of my mom who came and stayed, but mom now watched them like a hawk. If they ever started paying attention to me, Mom would find a way to get rid of them. I thought she was just jealous of me.

A couple years later, we moved to a nicer apartment complex. The apartment was much better, too. It was closer to my school, and it was an easy walk for mom to work. The apartment was on the third floor. The stairs were really a pain after a while, though. Mom made fast friends with the complex manager. His name was Mr. McMillon. He was probably in his fifties. He lived alone in one of the apartments. I don’t think he owned the place. I think he just collected the rent, did minor repairs, and kept the place clean. Mom certainly knew how to catch his roving eye. Anytime he had to come to our apartment for a leaky faucet or a problem with the drains, she made sure to have on a low-cut top and tight jeans. I thought it was funny watching him try to concentrate on the repair job and not trip over himself while keeping one eye on mom’s jiggling boobs.

It was not too long before a second-floor apartment became available. Normally they would have gone for more money, but somehow mom was offered the place for exactly what we were paying for the third-floor unit.

A couple days after moving in, I realized that Mr. McMillon’s third-floor unit was directly across the small courtyard from our place. Our windows all faced the courtyard. One night, after taking a shower, I walked into my room. I was at my dresser getting ready for bed. In the reflection of the mirror, I could see Mr. McMillon standing in the middle of his living room window. Suddenly, he stepped to the side behind the curtains. I kind of chuckled because, with the light on in the room behind him, his outline was clearly visible.

I still had a bath towel wrapped around me. I had not seen the need to close my curtains as of yet. Being on the second floor, I had not figured anyone could see in; besides, the curtains were very thin anyway. I never thought about it till later on, but Mr. McMillon had probably just installed them prior to us moving in. They seemed brand new. Anyway, my wicked little mind quickly devised a plan.

Leaving the light on, I casually walked over and locked the door to my room, then went back and stood in front of the mirror again. I rewrapped the towel again, now just around my waist. I stayed facing the mirror and pretended to be fiddling with my hair. I knew Mr. McMillon would not be able to see my boobs unless I turned around. I was still going through puberty and didn’t have much size just yet. Still, I had progressed out of the training bra size and was growing by the month. I figured I’d tease him as much as I could.

I stayed facing the mirror with my arms up, slowly brushing my hair. I made several moves as if to turn around, then stopped. Bending over, I reached into a lower drawer to get a pair of panties. I held them up to inspect them. Actually, I just wanted my watcher to think I was getting ready to put them on and would soon drop my towel. I stayed close to the mirror and pretended to be checking my eyes. Mr. McMillon was still standing behind the curtains. His outline showed constant movement near his waist. I knew he was jerking off. It was thrilling to know that I was turning him on sexually.

It was finally time to give him a show, so I turned around, putting my bare breasts in plain view. I sat down on my bed and pretended to be checking my toenails. I let the towel around my waist ride up my thighs.

I was not ready to show my bush just yet. Besides, I think by this point he had already climaxed.