the babysitter

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this thread is about a guy called jack. hes a single parent with a 13 year old daughter and he needs some help with the upkeep of the house. we need people for the babysitter applicants and if you can think of any other characters you want to join as just say.

jack is a tall (6ft7) guy with short brown hair and brwon eyes. his skin is nicely tanned and his face is cleanshaven.
 
holy shit

that's one tall fuckin dude!!
his 13 yr old needs a babysitter?
she must be immature!
 
idea for the daughter

Make her an 18 year old baby sitter. I will be a dad and I will interview her to see if she qualifies to sit my child.
 
Applicant.

OCC:

OK, I'll be myself here. I am Sienna, an applicant for the babysitting job.

I'm 5'1", blonde shoulder length hair, hazel eyes 34b-22-34 figure and I need the work.

When is my interview?
 
Helllo Sienna

Thank you for coming over to my home to discuss being a baby sitter for my son. As I look you over not quite leering, hard to tell if I am a dirty old man or just trying to get a first impression. Please have a seat tell me more about yourself. I am curious how you are at disciplining a child also are you familiar with helping a child to bath. And lastly just how bad do you need money I am sure you realize that baby sitting does not pay that well. Do you have any boy friends? Are you proud of your body you should be you are a beautiful young lady? I am sorry am I embarasssing you I am sorry. Tell me I am curious about how teenagers think....do you find me attractrive?
 
Sienna.

I sat in the living room looking around. Then he asked me questions. One of them was about bathing his son and I thought that was unusual because the add said he was 13 years old.

The house was very very tidy and there seemed to be no presence of a teenager around. I only wanted the job because it was going to be easy watching over a kid. To me thats all a rowdy 13 year old boy would be.

He asked if I thought he was attractive? Well, he certainly looked OK to me but maybe a little wacky as some older guys usually are.

He kept looking at my thighs and smiling then asked if he could take my coat and if I wanted coffee.

"Do you have coke?" I asked.

"No I'm clean out of soft drinks....sorry" he replied.

A house with a teenager and no soft drink?
 
"Sienna you are very pretty and seem smart but quite I repeat as I sit next to you on the couch. Tell me if my son did not behave as you wish what would you say to him?" Why is she so quite I hope I have not frightened her. "Sienna my son is becoming a man and has an interest in women and will no doubt look at you and stare at your body and undress you with his eyes.....would that embarass you? I hope you are not shy he really needs a young lady to be nice to him but show discipline. Do you know what I mean?"
 
Sienna

As I sat beside him, he began to explain what his son was like and how he was growing into a man. The fact that it sounded like he was setting me up as some kind of sexual prey for his sons own desires seemed freaky enough. I still didn't believe there was a son. I felt as if I was lured into this man's home for is own sexual gratifications. He put his hand on my thigh and that was enough for me to realise what was going to happen here. I wish these guys would be honest and just say to me that they fancy me like crazy and just want their way with me.
 
Being more direct

"Ok lets try this suppose my son Jay is not doing something you told him to do (homework, cleaning, getting off computer what ever) how do you behave to him and what do you say." why is she so quite does she not believe I have a son? I like her and I am sure he will too but I must try her out first it is only fare. Ok lets give her a tour of the place and test her out. "Where are my manners I have not shown you the place. This is the kitchen....bathroom.....my room...and my son's room. Now you do really need this job right? I assure you it will pay very well.... Ok now lets have a test. You wait here and I will call you back to the room. Remember I am Jay. " You leave and in a few minutes I call you back in. "OK now when you come back pretend you did not know I was here. " You walk into the room. My clothes are on the floor. I am under a sheet masturbating to a magazine.
 
Sienna.

The man shown me around the house and then we got to the supposed son's room. It certainly looked as if the room was used by a teenager. The usual college football banners and super hero posters including one of a topless super model. Then he told me to wait outside the room while he pretended to be Jay, his son. I played along with it because it looked fun just doing what he wanted me to do. I wasn't taking him serious about all this because I still wasn't convinced.

"You can come in now." he shouted. I walked in and noticed him hiding under the duvet cover. "OK I'm misbehaving.....show me what you would do." he said with a muffled voice. I folded my arms and thought about it smiling and then walked over to the bed.

"Ok you little brat!" I shouted, playing the part he obviously wanted me to play. I grabbed the duvet and threw it to one side.

Oh my gawd! There he was with a magazine in one hand and his cock in the other, jerking himself off like crazy. My eyes popped out of their sockets like organ stops.

"Well.......what.....are you.....going.....to do?" he asked.

All that I could do at that moment was watch him. I had never seen a middleaged man jerking himself off before!!!
 
Is she aroused or angry?

Sienna is so hot. Look at her walking into the room. I am getting more excited from seeing her than from this stupid magazine. She does a nice job role playing the situation and seemed real surprised to see what I was doing when she move the sheet. Now that she has seen my cock and what I am doing I wonder if she is shocked or surprised. She still has not said anything. Well her eyes are popping out thats a sign of something. Lets see where this leads.... "Hey!!!! I know you are supposed to be watching me and shit but what right do you have doing this! Are you angry with me? No? Ya know between you and me I have only seen pictures of naked women and they look sort of ...fake like air brushed you know? Umm I was wondering ummm... if I could like see your breasts or something...I promise I will not tell my dad you showed me...and if you want I will let you watch me jack off ...or maybe you could like ..............suggest something...cause well I like have never really "been" with a woman...I have like kissed and stuff and gotton to like third base but ....you know." Well that should do it, I do not care if she is angry or if I made her hot I just want to see how she responds. I am so hot for that body of hers...just got to stay in character....for Jay's sake.
 
Sienna.

He started to talk to me as if he was pretending to be his son. I stepped back and started to laugh and then realised that this guy was deeply into role-play here. I looked around the room and then back at him and his hard cock as he continued to jerk off.

"Ay...Ay! Hold it mister!" I shouted. "Don't get so excited. I know what you want. I'm not some idiot." He stopped doing what he was doing and leaned up as I sat beside him on the bed.
"This is an interview right?"

"Yes." he replied.

"So how many today?....three, four maybe?"

"No you are the first one. Please let us continue. Let me see those tits of yours. I need to get laid. I won't tell anyone, not even my dad."

"Ok.....role-play it is I suppose." I replied standing up and lifting off my sweater. He looked at me handling himself again. "Ay Ay! Lay off the meat will ya.....I'm not done yet."
 
"So you would strip for my son"

"You catch him wacking off and you take off your clothes? You some sort of a slut then? Not sure how I feel about this....yes perhaps it would do my son good." Lucky bastard gets a slut for a sitter damn all I ever had were old school marms. Ok well then lets see......I should check her out but on the other hand I would not want to leave him with a girl that would hurt him. I stop playing with myself and put my hands behind my head...cock still erect falling slowly to the left as you watch. "OK I really would like to see you naked I have never seen a naked girrrlllll before ummm....... could you like ......strip for me...and like.........slow.......peeeellleaassseee."
 
Sienna.

I stood before him in my bra and skirt. He wanted me to strip slowly. Atleast he stopped jerking off.

"Hang on!" I told him. "I just need to go to your bathroom a moment." I left the room and went into the bathroom and found a can of shaving cream and a vase of flowers. I tipped the flowers down the toilet basin and filled the vase with some nice warm water. Then I returned to the bedroom with both. He looked at me with slight amazement on his face.

"What do you need those for?" he asked. I grined at him and then calmly poured the water over his semi erect cock, followed by a continous squirt of shaving cream. "What the f....!" He sat up and just looked at me.

"Still wanna play?" I asked.
 
Wow such spirit

Well it is important that my son have someone he can trust. "Sure just be careful."
 
Sienna.

This guy was really loving it!

"You mean to say your son would want me to carry on after doing that to him?" I asked.

"Sure." he replied. I put my hands on my hips and laughed.

"You mean he wouldn't feel humiliated?"

"No, I think he would enjoy it. Don't you?"

"You know what? I just got to see this son of yours." I told him.
"I think this is all for your own entertainment here. And besides, a game is game and I came here for a job and I end up in this....this......whatever! Just tell me now, do I get to be your babysitter or do I have to wait until you've had fun with a few more applicants?"
 
Jay

"Well Sienna I do want to hire you and no there probably will be no more applicants. Lets talk money I will pay you $8.00 per hour to sit there talk on the phone eating my food and make sure Jay Jr. does not burn the house down or something. I will pay you $18.00 if you do it wearing as little as possible with the idea you will not be touched, just tease the boy. And as far as more money that depends. But I will pay you a training bonus of $800.00 for today if you will please continue with the interview and do as I ask. Now then about that strip tease for the boy??????"
 
Sienna.

$800 just to strip? That was a lot of money to me. I already stripped once in a club across town for less including what tips I picked up from the punters. I promised myself I would never do it again.

I walked to the window and looked out into the street to think about his offer. He waited for my reply and he was obviously very serious about this. $800 would do me on its own right now. I didn't need the job if I could get $800 in one go. It would pay my train fare to where I needed to go.

I folded my arms and looked at him. "If I stripped for you now for $800 would you let me have it and then leave for good?"

He smiled and looked at me. I could see his mind ticking over.
 
Jay

"Of course not, the money is for you to do as I ask I have not asked anything yet. What I desire is to decide if you are worthy of seducing my son. I will pay you for training with me for this. It merely begging with you stripping I assure you. Then come here and lay with me as I am Jay Jr. and calmly seduce the young man. Is that more clear?"
 
Jay Junior slams open the door

"Dad, I'm home!" He walks into the kitchen, tossing his book bag onto an empty chair and proceeding to the cupboard for a glass and then to the refrigerator for some soda. "I'm going over Jimmy's to play some SEGA, Okay?" He shouts up the stairs, not really waiting for an answer.

He gulps down the soda, leaving the near empty glass on the kitchen table, then grabs up his back pack and heads for the front door.:D
 
Sienna.

I heard Jay Jr. enter the house downstairs. The kid was obviously too engrossed in having fun with his friends and computer gaming. I looked at his father.

"Jay?" I enquired. The kid left, slamming the door behind him and I looked out of the window onto the street to see the immature teenager running towards his friends. "That's your son?"

He didn't look old enough to even think about being seduced.

"I don't think your son needs someone to look after his sexual needs yet." I turned and looked at his father, grabbed my sweater and headed downstairs.

"Where are you going!?" he called after me. As I was about to leave, he came downstairs to me. "I need a babysitter."

I needed a job......but not that kind of job.
 
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