This happened a few years ago when I was 17 and before I get into the housekeeper, I should tell you about my friend Jesse.
At the time, he was a year older than me and we lived on the same street. He was thin, about 5'10, 170lbs and had a nice big 8' cut dick. I was about the same, 160lbs, 5'9 with a 7' dick that was cut and a little fatter than his. Growing up we were the kind of teens that loved to show off our hard dicks so we would always be thinking of different ways for girls to see us naked but we would make it look like it was an accident and make them feel embarassed for barging in on us or seeing us. We both were thin with nice size dicks so we liked to show them off when we could. We got caught jerking off by his neighbour, we got caught by his sister shaving our cock and balls in the bathroom (Jesse got me into shaving our hair off as he said it made our dicks look bigger and smoother), we got caught jeking off by the girl guide selling cookies at my house..you get the picture. We had no problem jerking off together as we did it alot, we would see who could shoot the furthest, the most or the fastest. We never really attempted to jerk each other off, we just enjoyed watching each other.
Now I'll get to the housekeeper. My mom ended up going back to work during the summer holidays so she needed help around the house so my parents ended up hiring a housekeeper. She would come every Wednesday and spend about 3 hours cleaning our house, both Jesse and I were infatuated with her as she was in her early 40's, about 5'4', 145lbs, (she wasn't fat, she had a tiny bit of a stomach and a big bum) her name was Alba and she was Brazilian. She had short brown hair and her skin was bronzed as if she was always tanned. What we really liked about Alba was that she had enormous jugs, sure the gravity was taking over and they were hanging down by her belly button but they were huge, we guessed them to be like a F cup as we tried to compare them to what we saw on the internet (me being the internet tit guy, I compared them to Sylvia Panda's jugs and Jesse agreed because of the size and the colour of their skin being the same). Alba's tits didn't stick straight out like fake ballons, they did stick out but they hung down low too. Alba would always wear clothes to keep them tight to her body and from swinging around when she tried to work but as horny as the two of us were, we would always be staring at them when she was around us and there wasn't much she could really do to hide them.
Jesse who was always over either playing playstation, watching porn and surfing the net for porn was always trying to think of a plan where Alba would catch us jerking off together.
First we wanted to see if she would possibly get offended by catching us so we set her up to make it look very innocent on our part. I knew all the big tit girls on the internet so I printed out a colour picture of Sylvia Panda (the big breasted brazilian babe on the net who we thought looked alot like Alba) The picture said 'Brazilian Jugs' on the top and it had Sylvia Panda squeezing her massive tits together by a swimming pool as she was covered in oil. What we did was leave that picture out on the desk in my room and beside it we left a picture that Jesse and I took of the two of us jacking off together. We partially covered all the pictures with scrap paper and left them to be 'accidentally' discovered by Alba as we waited in the closet behind some clothes to catch her reaction.
After she was done cleaning the downstairs, she made her way to the bedrooms. My dick was already getting hard just waiting to see her reaction. Alba made her way into my bedroom as she was vacuuming, she cleaned all the carpet, under the bed but she didn't open the closet door where we were hiding because her rule was if the door is closed, she won't go in to clean it (as my mom told me if I wanted to sleep in , keep my door closed so Alba won't come in). After vacuuming, she started to tidy up my bed and dust all around, both our dicks were fully erect (and I know this as he poked me in the thigh with his!). We watched as she made her way over to the computer desk with the pictures.
She first started to pile all the paper into a neat pile as I thought (shit, I probably covered the pictures up with too much scrap paper and she missed them). Then Alba stopped shuffling paper and paused, she saw the pictures. Through the cracks of the closet door we saw her looking at the picture of Sylvia Panda, she held up the picture closer to her face and giggled, she then to our shock grabbed her boob, on the outside of her sweater, with her right hand and lifted it up and gave it a shake as if to say she has huge tits too. She let her massive tit fall and then she squeezed her shoulders inward squishing her huge tits together while looking at the picture. She put the picture back down on the desk when she noticed the picture of me and jesse. She had a shocked look on her face as it was a picture of us standing together naked side by side holding our erect dicks in our hand. She again picked it up and brought it closer for a better look. With a surprised look, she smiled and examined the picture for what felt like minutes. She did not appear to be disgusted by it or grossed out, she almost looked impressed as if to say 'wow'. At one point while looking at the picture her hand caressed her tit and it looked like she was rubbing where her nipple would be because her hand was on the outside of her clothes. Alba put the picture down on the desk, organized all the paper and left my room giggling.
Jesse and I remained in the closet until Alba left the house so she wouldn't suspect a thing. We were so horny from what we just witnessed that we ended up stripping naked in the closet and jerking off shooting our loads onto a magazine poster of a bikini babe I had lying on the floor in the closet.
We knew next time Alba came to clean the house we were going to set up a situation to make it seem like she caught us in the act by accident.
Keep an eye out for the 'The Brazilian Housekeeper conclusion'