We used to have a maid come to clean our house in the morning. At that time, I was a horny teenager and, having discovered the world of sex a few years back, an avid masturbator. The sight of that young maid bending over or reaching up while cleaning the house would send blood rushing to my perpetually hard penis.
She was in her mid-twenties with a slim build. She usually wore rather loose clothes while cleaning so I didn't have a good idea of what was hidden underneath, but what I saw was good enough for me. Long brown hair and medium-sized tits, pretty face. Good enough for a 15-year old male.
I was forever dreaming of having sex with her or at least an adventure of sexual nature. Whenever I would masturbate, I would think of scenarios involving me and other hot-looking girls I had seen recently or on TV and very often, I would end up ejaculating my the maid in mind.
I decided that just fantasizing was not enough any more and I would start making daring plans to really get her involved. These plans would usually melt away immediately after I reach orgasm. However, with time, I became more and more determined with the idea of having some sort of sexual contact with her. I was pretty sure that she would not agree to have sex with a 15 year-old boy who was her employer's son. I had some streak of exhibitionism in me and thought up of a plan where she would stumble accidentally across me while I was choking the bishop. That plan, however, didn't seem satisfactory to me as I wanted her to know that I fancied her.
So I aimed for the direct approach. I decided that I would come to her with my erection sticking out and ask for some 'help' down there and see what kind of help she would provide. That sounded bold to me at 15 years old so I thought of testing the waters first by letting her see me with an erection and noting her reaction to it.
The next morning I woke up with a massive erection and the urge to pee hard, just like every morning. I could hear the maid already at work and waited until she was busy cleaning the area between my room and the bathroom. My plan was to get out of my room in my pyjamas and make my way to the toilet, allowing her a look of my super-hard manhood. To make the situation look more genuine, I would pretend to be still sleepy and not quite aware of what was going on down there.
By the time she reached the area near my room, I was about to burst. The thought of showing her the tent in my trousers and the urge to pee kept my penis hard and was starting to hurt. I tried to compose myself and look bleary-eyed although I was ready to run across to the bathroom.
I opened the door, got my erection out of the room and shuffled to the toilet. The maid had her back to me and was unaware of my presence. She was busy with the vacuum cleaner and hadn't heard me coming out of my room. I didn't want to have been waiting to relieve myself just for her to look the other way so I said a sleepy good morning but she still didn't hear me. I purposefully knocked against a furniture which made a high pitch noise and caused her to turn around. I mumbled a hello and got into the bathroom, not before seeing her start replying and stop short as her eyes moved from my face and down to the pole I was sporting in front of me. Her eyes were glued to it as I got inside.
Once in there, I looked down and found that my tumescent penis was pushing my pyjamas so far out that there was actually a gap between my waist and the elastic band. Oh, I forgot to mention that I do not wear any underwear while sleeping. So while I could see the base of my penis from the top, I wasn't sure if the maid from that distance could also see it.
My manhood today is not enormous; most writers here claim theirs to be above average by far. I am 15 cm long measured from underneath, on a good day, like that one; from experience, I would say this size is average. In terms of thickness, I like to think that it is above average - it does look quite meaty looking down at it. At that time, however, I was just 15 and don't think that I was already fully grown in that department.
Back to the story. I proceeded to pee noisily with some difficulty. How does one pee with a massive erection pointing skywards and the urge to pee and a woman just outside keeping up that erection?
Anyway, my bladder now emptied and feeling very relieved, I was slowly losing my erection. I thought that this was a good time to get out. So far, I thought that I hadn't done anything that could get me in trouble. I had to pee urgently and had morning wood and the maid just happened to be there. Now, if I got back to my room looking more decent, that story could hold.
So I did and this time, even with the vacuum cleaner running at high volume, the maid caught me leaving the bathroom and her eyes didn't stray away from my crotch. I didn't know if she heard me pee but I didn't think she heard me get out. She was probably keeping an eye on the door hoping to catch me again in an aroused state. By the time I got back inside my room, my semi-erection had turned into a fully-fledged one!
I decided to take matters in hand literally and stroked my foreskin up and down my swollen purple head. I wasn't trying to last but rather hoping for a quick release. The tempo increased and I squeezed my pelvic muscles a few times to bring my orgasm closer. I felt it building up like a tsunami wave and just as it was about to peak, I squeezed my muscles one last time and that brought the wave crashing down and sweeping everything away. My swollen organ became bigger and as hard as steel and it felt as if the head was about to explode but it was sperm which exploded out of it, shooting out like an express train out of a long dark tunnel, wagon after wagon...
More trains to follow...