--- The "Not a Loser" ---
I wasn't a complete loser back in high school. Well, at least I don't think I was. I mean, sure I wasn't a jock and I wasn't exactly popular. And ok, I admit I was a bit on the pudgy side. Alright, alright, I was... fat. But I wasn't obese, just want to make that point clear. At this point you're probably thinking I was a typical teenage geek, probably the president of the chess club or something. Well, I sucked at chess and I did not play Dungeons and Dragons. The truth is, I was really just a nobody. That's why I say I was not a loser back then, I tend to associate losers with the nerds.
I was just a typical teenage boy going through high school with a small group of close friends. My grades were average and I didn't particularly stand out to be popular or to be bullied. I was just this 5'7" average height, fat, and unnoticeable guy. I had no friends of the opposite gender, but that didn't stop me from ogling and drooling over them. Yet I never had the courage to go beyond leering, like asking them out or something. I did go to my senior prom, no date of course. However, I did go and that was the point. See, I was not a complete loser. I can honestly say those teenage years were forgettable and uneventful. Until the end of my senior year...
Summer was approaching and I was planning on playing video games and lounging around before going off to college when my parents told me the young couple down the street was looking for a babysitter. I mean, really? Who'd ever heard of a male babysitter? However, being a "not a loser" with nothing to do while others my age were probably out partying or taking prep courses for college, I decided at least I could make some pocket change.
The neighbors were an Asian couple, the mother was in her mid-20s, I think 26 to 28, and she just gave birth to a baby girl, Anna. For a while she stayed at home and took care of her, however now the kid was a few months old, she wanted to get back to working. I think she was a school teacher once, but with the child still so young, she was doing part time work at home as a copy editor and needed someone to help out during the day. There wasn't much of an interview, they knew my parents and I easily got the job.
God, I'll tell you this. She was one motherfucking hot milf. After working there a couple of days, I instantly regretted it because I just couldn't contain myself. I mean, you'd think being 18 I would be more attracted to teenage girls, but I'll tell you... there is something... so tempting about a young mother. They come off more... mature, sophisticated, ... I... I can't really explain it? It's like the difference between a woman and a lady, if that helps.
Also, it wasn't just the personality, but physically too. You know people get all excited about a blossoming young teenage girl, but a woman in her 20s is much more complete in their physical development and well... much more ripe. She was about 5'4" and like most typical Asians, slim and petite. With a thin waist and wide hips complimenting those round supple tits, she was a bitch made for breeding. Often I found myself breathless as I stared mindlessly at her cleavage. Since she was still breast feeding her baby girl, those swollen melons were larger than what her typical clothes could contain.
Unlike typical Asian women with pale skin from avoiding the sun, Anna's mother had a nice tanned glaze. I think it was the cultural norm of SoCal and the American outdoor lifestyle. Hey, I don't have a problem with that, do you? Hell yeah, like a nice oven roasted piece of meat, her olive color skin left me mouthwatering every time I saw her. And just to top it off, instead of a typical long straight silky hair, she looked exotic like an untamed lioness with that wavy black lock.
It was excruciating working there and seeing her every single day after school, even if it was only for a few hours at a time. Whether deliberate or not, she didn't make it easier either. Several times she caught me staring blankly at her magnificent tits and responded with nothing but an innocent smile. Then there were the times she would bring me snacks while I did my homework in the baby's room and gently rub my shoulders as we small talked. Come on... either she was just a natural cocktease or it was all a sadistic deliberate act. Either way, I left the house each day with balls bluer than the marble sea.
Being a horny teenager at the time, it wouldn't surprise you if I confess that I ... well... I uh... you know... fap myself to porn. And since working for this couple, boy I found myself constantly filling my waste basket with used tissue by the box load. It didn't take long before I started specifically looking for videos involving Asian women on the internet that matched her exact features.
The longer I worked there, the more sexually frustrated I became. And the more sexually frustrated I became, the more aggressive and filthy were my taste in porn. I went from an innocent young man who would get off on just softcore to a deviant pervert exploring all sorts of things from bdsm, to choking, slapping, and humiliation. The more I divulged into this depravity, the more I fantasized plowing that young mother for all she was worth. On several occasions while fapping to porn with women that resembled her, I found myself mumbling quietly, "Take it, take my cock! You love being fucked by your teenage babysitter, don't you?"
Oh, it was just a fantasy of course, I mean I still didn't have the courage to ask a girl out, let alone know how to approach a woman sexually. Then one night as I was stroking myself hard with sweat dripping off my forehead and my heart beating like a heart attack, I came across one nasty video called "Kidnapped Bitches Motel Fuck."
Holy fuck! I've never seen anything like it as this naïve Asian girl reluctantly took on 6-7 massive hard cocks in a motel. They tied her up, slapped her around, and ravaged the shit out of her every hole while she whimpered and cried until ultimately submitting to the total debauchery and begged for more. What made it even more amazing was the actress in this video looked very much like Anna's mother with her toned slim build, broad hips, firm titties, tanned olive skin, and long wild wavy hair. In fact... she looked "exactly" like her. Though the resemblance of the face during close ups was uncanny, the actress in the film had spit, cum, and tears smeared all over her make up that I could not be 100% sure.
For several days, that video became my #1 go to video each time I came home from the babysitting gig. I fapped myself constantly to the scene while picturing my cock deep in this milf bitch's cockteasing cunt. It helped reduce the sexual frustration for a while until summer came around. Knowing school was out for me, she asked me to go over earlier and spent even more hours per day alone with her and the baby. And as if it couldn't get any worse, the little slut of a wife began dressing more casual since I was there the whole day. I was going insane, not just the blue balls, but I had to know... whether that was her in the video.
So one day, as we were chatting in the kitchen at the dining table, I asked her why she hired me for this job as it was unusual to hire a male babysitter. In a casual tone, the young mother replied while sipping her iced tea in her tight tank top and blue sweat pants with her wavy silky hair in a ponytail, "Well, you know a lot of these young girls are naïve and... slutty. I didn't want Anna's father getting any temptations..."
"Wait... so you mean you think he would cheat on you?" I retorted in surprise.
Pausing for a second, the juicy milf then responded, "Well, no... I mean... I don't know, things happen. It's just better to be safe."
Pretending to be offended in a jest, I snapped back, "Oh... so that's why you hired me? Because I'm safe? I'm so fat and ugly, you would not be tempted?"
