As a fifteen year old (sixteen in four months) I was a hard worker. I come from a middle class family but was never given any thing for free. I had to work. If I wanted a new bike I had to raise the money my self. My parents were not unreasonable, if they knew I had a savings project on the go they would inquire about my progress. At some point in the process they would normally pony up a portion of the money as long as I had made an honest effort to secure the needed cash. They said it was a good learning experience and it assured that my purchases were not frivolous.
I would do just about anything to raise money. My jobs included a paper route, cutting grass, shovelling snow, running errands for old ladies, buying old bikes fixing and painting them to resell at a profit and, well you get the picture.
This story has connections with a couple of my jobs.
One January day we received a tremendous amount of snow over night. The paper I delivered was the morning addition. I started my route at about 5:30 in the morning and finished about an hour later. As I was eating my oatmeal I heard on the radio that school had been cancelled do to the heavy snow fall. Most of my friends would be ecstatic when they got their sorry asses out of bed, me, not so much. For me it meant a long hard day of work. While my friends got together and played video games I would be breaking my back shovelling the sidewalks and driveways of my regular customers.
When I left the house I was disappointed to realise that there was no way I could ride my bike. It was also evident the I could not wake my mom to drive me as that would be imposable to do as well. The last thing I wanted to add to my list of things to do was push my mom’s car out of the snow.
This was going to be a very long day. I set out to deliver my papers and along the way, as I anticipated, I picked up several snow shovelling jobs. My route took me an extra hour and a half. Between the snow and talking to my customers about what they wanted shovelled (some wanted only side walks some wanted drives some wanted both) I got to the last house on my route. This customer was always the worst. He was always standing there when I approached his house as his dog let him know I was coming. He was always dressed impeccably in a suit and tie and was never happy about the time. On one occasion he threatened to change papers unless I switched my route so he was first to get his paper. I tried to explain to him that when I got the route everyone new when their paper would arrive and that his was a fairly new subscription and it was not fair for my other clients to all of a sudden change. This was difficult as this gentleman was quite intimidating.
On this particular day he was again standing at the door with his barking dog, extremely pissed off because I was so late and in no uncertain terms let me know it. Then this pretentious bastard ask me to shovel his drive so he could go to work. I informed him that I had several other requests for the same service ahead of him. He then offered me my double rate (which I doubled before telling him my cost) to shovel two tracks and the berm at the end of his drive.
He said I have a four wheel drive and I just need to get out and you can finish the job later. To which I agreed. I was going to make a shit load of money, YIPPY.
I finished his job and returned home to check in and maybe have quick cup of tea with my mom before she went to work.
Back out into the winter wonderland I went. I had completed all of my jobs except the last and was exhausted. It was mid afternoon when I finally saw light at the end of the tunnel. Once again as I approached the house the dog started barking. The front door opened and Mrs. Patterson called me up. She told me to make sure I came up to get paid when I was finished.
She was still in her house coat and apologized by saying
“Hey it’s a snow day I’m not going any where”!
I finished her drive and side walk and approached her door for payment. Again the barking dog. She asked me to step in so she could get her purse and not heat the outside. I looked at the dog and she said don’t worry he is just a noise maker. I stepped into her house being carful to stay on the mat. After being outside the house was stifling hot so I removed my hat and gloves. The dog seemed like he did not want me to stay on the mat as he jumped up on me, almost knocking me down on several occasions.
Mrs. Paterson retuned fumbling with purse and trying to settle the dog. When she looked up she said
“I’m sorry you have been out there all day you must be exhausted. Take your coat and boots off and I will make you some hot chocolate.”
I tried to protest but she would not relent.
I removed my boots then my coat. I was soaked to the bone after so many hours of shovelling. She took my coat and hung it over a chair and asked me into the kitchen. I was about to sit down when she said
“Hold on don’t sit I’ll be back in a second.”
She came back into the kitchen holding a silk robe not unlike her own.
She said “Go into the bathroom and take your clothes off and put this robe on, I don’t want you to stain my chairs. I’ll put your clothes in the dryer that way you can have dry clothes when you go back out into this terrible weather.”
I was a little uncomfortable but as she was an older woman it would have been like refusing an order from my mom. I did as I was told. When I came out of the bathroom with my clothes in hand she said “Ok now you can sit and I will be right back.”
I sat at the table with “Joey” the dog not leaving my side. When Mrs. P returned she said I hope you don’t mind but I make my coco from scratch. I had no idea what she was talking about. She went about getting the ingredients together and that was when I realised what a good looking woman she was (I was fifteen and nervous, give me a break). I watched as she stretched up into some cupboards and bent down into others. When she had every thing put together she turned and I noticed her robe was just slightly looser that it was and I could see she was wearing a white see through negligee underneath.
We sat and talked. She was impressed with my entrepreneurship and I learned that her husband was the same with several different companies offering several different services.
Mrs. P got up to put our coco together, brought it over and put the cups down. She said do you want marshmallows (stupid question) added them and said I’m going to have a little special one you interested. I said sure! She left the room and returned with what I know now was a bottle of Grand Marnier. Her robe was open just a little more and I could see her negligee stopped at mid thigh and I could also see just a little of her cleavage.
As she bent over to put a dollop of GM. Into my cup I caught a quick glimpse of her breast We were sitting at her glass top kitchen table and when I looked down I could see that her robe hung to ether side of her thighs, exposing the hem of her negligee and more disturbing her long athletic milky white legs. We started to talk about more personal things like hobbies, sports we liked, TV,ect. The whole time we were talking my eyes defied my brain and continued to drift down to the table top. I could feel my cock start to swell. Then came a dreaded question for a fifteen yr old virgin especially while talking to an older lady (she was 32).
“How about girl friends” she asked.
My face reddened and my eyes immediately dropped out of embarrassment; not good as I got another eye full of leg. I had to shift as I was now fully hard.
She said “I’m sorry I didn’t mean to embarrass you.”
I was mortified but she saved me by suggesting another cup of coco. I replied in the positive and she went about her preparations. I excused myself and went to the washroom, not to piss but to throw cold water on my face and to try to get my penis to relax.
When I returned to the table she was adding the marshmallows.
Another Special she asked with a wink, I could only nod.
She came back with the GM. And her robe was almost completely open. As she poured I could not help but to stare. Her breasts were not large but absolutely beautiful. Firm and perky, with nice little areoles and nipples the size of pencil erasers. When she returned from replacing the liqueur from the bar her robe flowed out behind her giving me a full look at her negligee. Again I could not help myself, but this time I stared with my jaw hitting the floor.
She said “you must have a lot of girl friends, as hard working and good looking as you are.”
I told her that because I work so much there are a lot of girls that aren’t interested.
Human nature had taken over once more, and in my embarrassment my eyes again dropped. While I looked at the floor she moved her hands down and lifted her negligee so I could see her matching panties.
I had no idea what to do, stare, avert my eyes, look at her? So I stared at my coco.
Mrs. P said you know what you are going through is completely normal. I have seen you looking at me and it is ok, actually I’m flattered. Had she seen my hard on?
I asked “do you think my clothes are dry”
“I doubt it” she said and followed with the question “do you like how I
When I stared to stammer she stood and came over to where I was sitting and dropped her robe.
Stating “it’s a simple question, one I don’t have to ask. The table is glass and I can see you just as well as you can see me. A silk robe doesn’t hide much.”
She said “you’re a good kid and a good looking kid and I would like to give you something special for all your hard work. Would that be ok”?
HO god was my debonair response.
She took my hand and said “come down stairs with me.”
As we descended my mind was flooded with emotion, testosterone and fear.
We walked down a hallway into a game room complete with a pool table, pinball machine, large screen TV, stereo, and all the other toys. She asked me to sit on the couch and walked behind the bar. She took two Mike’s hard lemonade from the fridge and handed me one.
Mrs. P said “relax”
This was silly, as I was sitting there with a silk tent in my lap. I am not overly well endowed, just under six inches with average girth. Having never had a sexual experience it really was the last thing on my mind.
Mrs. P asked if I would like to see her without her top on (not that much was left to the imagination) and I could not respond. I just sat there.
She came over to me and asked if she could kiss me. This was just unfair; with her hands on each side of my face she moved in and gave me the sweetest kiss, so soft I just about blew my load.
So do you want to see my boobs?
I with my most studdly response I nodded speechlessly.
Mrs. P stood before me and pulled her negligee over her head.
I sat with moon eyes roaming from her petite breasts down to her now visible bush. A nice trim Mohac covered by a translucent bikini bottom.
“I would like it if you would touch me” she said.
I finally got my shit together and said “that would be great and I would like you to touch me too.”
She took my hands and placed them on her excited tits.
I said “Mps. P my thing really hurts.”
Call it your cock she replied
“My cock hurts” I said.
She took her hands and opened the robe. She stood staring at my member and I thought HO god she doesn’t like what she sees. My hands reflexively left her breasts to cover myself. She grabbed my wrists and put my hands back on to her under ripe avocado’s
She told me in a commanding fashion that from now on I was to listen to her and do as I was told. I nodded.
Mrs. P pushed me back on the couch leaning forward so my hands did not leave her breasts. She reached down spread my legs and with her nails put her hands just north of my ass hole. She slowly moved her hands and started lightly stroking my scrotum.
I have never felt such pain. I thought my whole penis was going to explode and I would never be able to have sex (much less write my name in the snow). Her hands moved up over my shaft and touched the under side of my head. That was it. I exploded. She did not have hold of my cock so I came everywhere, on my face, my hair, my chest, on the robe and lastly on my stomach.
How many times could I be mortally embarrassed in one day.
Mrs. P looked at me and said “Wow that was awesome can I kiss you again.”
I thought how many stupid questions can this goddess ask me? I just nodded once again. She went to work on me and licked every ounce of my cum off me. She was half way up my neck when I could feel my self getting hard again.
Mrs. P I asked “could I maybe feel between your legs? I have never done that before.”
Again I could not hide my embarrassment as she laughed. She said “I’m sorry I am not laughing at you I am laughing because not only are you going to only touch me but, you, young man are going to do much more than that.”