Milky Boy Ch. 01

In the way of background, I am a 48 year old male. I'm in good shape for my age and have been married for 27 years to my college sweet heart. Like most couples at this stage of our lives, we have struggled with keeping our sex life interesting and active. Over the years we have explored my many fetishes, dappled in BDSM and most recently, enjoyed the excitement that comes with a slut wife/cuckold relationship. I have always been sexually submissive and enjoy submitting to a strong, beautiful woman. While I am still interested in all of these areas, it has been a continual struggle to keep my wife's interest on the front burner in any of these areas. So once again, I found myself seeking some new interest to generate sexual excitement in my life – unfortunately this one did not directly involve my wife.

We live next door to an 18 year old girl (Lauren) who is a senior in high school. Lauren baby sat our children on several occasions when they were younger, but not anymore. We always paid Lauren well for watching our kids, so she was aware that we had some disposable income. Lauren is one of those girls who is "18 going on 25", she has always been very self-confident and mature for her age. She is also very beautiful and has a fun, if somewhat pushy at times, personality.

Lauren's family is not as financially secure as we are, and she is always lamenting the fact that she needs money. Normally she is seeking cash to buy things for herself, Christmas presents, etc. Now that she is a senior however, her main focus has been saving money for college. She is a bright girl, but probably will not qualify for a scholarship at the prestigious school she her sights set on.

Based on this knowledge of her needing cash, I hatched a plan. I felt it was a long-shot, but what the heck, right? I was horny and she needed money, sounded like a good match to me! We had her e-mail address from some joke e-mails she had sent us a while back. I set up a new/factious e-mail account and e-mailed her an anonymous "proposal" on how she could make some extra cash.

Without using her name, or revealing mine, I told her in my first e-mail that I was a well-to-do middle age man looking for some sexual excitement. I went on to say that she could make some quick, easy cash if she was interested. The amount was up to her, and if interested, reply to this e-mail. I hit the "send" button and anxiously awaited her reply.

I signed back on a few hours later and was pleasantly surprised to find a reply already from Lauren. She said she was "cautiously interested" but wanted to know more details. I could tell she thought I was some kook and she was concerned about her safety. She made a point however of confirming that she was in fact in need of some cash.

I hit "reply" and wrote her the second e-mail of the evening. To calm her fears about safety, I told her I was married, had kids, lived in a nice neighborhood, etc. I then laid out my proposal on how she could make some money. I told her that for every time she jerked me off I would pay her $50 cash, for every time she wore nylons and high heels and let me jerk off while kissing her feet, I would pay her $75 in cash, and for every blow job she gave me, she would get $100 in cash on the spot. I stressed that there would be no sexual intercourse. I also told her that when, where and how often she "relieved" me was entirely up to her; she was in charge. She could opt for once a week or three times a day, depending on how much cash she needed. The only stipulation was that she had to make me cum in order to get paid. I told her if she was interested to write me back and we would arrange to take the next step, if not, we would drop the whole thing right here. I nervously hit the "send" button and hoped that she was still on line and more importantly, that she would be interested in my proposal.

As luck would have it, she was still on line as I got her reply back in minutes! Instead of telling me to "fuck off" or "drop dead" as I was afraid she would, she merely asked more questions. I could tell she was interested, apparently the lure of the cash was stronger than I realized for her. She said she was "okay" with what I suggested, but wanted each level raised by $25. So she wanted $75 for a hand job, $100 for me to kiss her nylon clad feet, and $125 for a blow job. She wanted to know where I lived and asked my name – she signed the e-mail with her real name, Lauren. She added a post script to the e-mail by saying "I hope you have a lot of cream, because I plan on milking you at least daily!"

Her quick and sexy reply excited me greatly. Now for the crucial disclosure, it was time to tell her who I was. I immediately wrote her back and told her it was me, her next door neighbor. I stressed that if she wanted to back out now that she knew who it was, we would drop the whole thing and never mention it. I told her my wife had no idea I was doing this and that we both needed to be very discrete. I jokingly signed the e-mail "The Milk Man". I also gave her my cell phone number if she wanted to talk instead of sending e-mails.

I no sooner hit the "send" button when my cell phone rang next to me on the computer desk. I answered and Lauren in a very sultry voice said "Is this the Milk Man?" I answered yes and she continued "I think you need to talk a walk around the block Milk Man, and don't forget your $75!" She then terminated the connection. I hurriedly went downstairs and told my wife I was going out for a walk, that I needed a little fresh air. She barely looked up from her book and said "Fine, see you when you get back."

I grabbed $75 from my wallet and headed out the front door for my "walk". As I passed Lauren's house I noticed her car was gone from the driveway. I rounded the street corner and saw her car parked at the curb a short way up the street. As I got closer the passenger door opened and I hopped in. "Hi Milky boy" she said, "got my money?" I told her that I did and with that she started the car and pulled away. She was very business like and was definitely taking charge of this situation.

She drove us to a nearby strip shopping center a few minutes away and pulled behind the stores where no one would see us. After shutting the car off, she looked over at me, nodded to my crotch and said "Well, take it out Milk Man, let's see what you've got." I unzipped my jeans and pulled my cock out of my boxer shorts. I've never considered myself large in this department, but at least thought I was an average size. Apparently Lauren thought otherwise. "Is that as big as it gets?" she asked with a snicker. I told her it would grow a little more once she started stroking it and she replied sarcastically, "We'll see about that!"

She reached in front of me and took some hand lotion out of the glove compartment. Squirting a little in her pretty hands and adding a glob on the head of my cock, she began to lube my shaft, rubbing it up and down. I very quickly got hard the rest of the way and in no time was close to cumming. Within a minute or so I shot my load high into the air. I had not cum in several days, so I had quite a nice load. God it felt good! My cum landed all over my pants and Lauren's hands were covered in it. "Well that didn't take long at all, did it Milky Boy? This is going to be easier than I thought!" she said with a smile. Then she simply said "Pay me. Put the money in my purse." I pulled the $75 out of my pocket and tucked it into her purse.

Lauren realized at this point that she didn't have anything to clean my cum up with, so she merely wiped her cum coated hands on my jeans. "Next time, as in tomorrow, bring a towel or some napkins for my hands. Better yet, get a supply of latex gloves and keep them with you – I may decide to use those so I don't have to touch your weenie" she chuckled. When she had finished wiping her hands on me, she started the car and headed back to our street. "Make sure you keep your cell phone with you and on all day, every day. Also check your e-mail several times a day, every day. I'll be contacting you either by cell or e-mail and let you know when and where your next milking will be" she directed me. She pulled over and let me out down the street from my house. "See you tomorrow Milky" she said as I got out of the car.

Before I closed the door she asked "How many times do you think you can cum in a day?" I told her it depended on how tired/stressed out I was, but on average could cum at least three times a day. "Better get some sleep then, because I have a feeling we're gonna raise your average!" I smiled and confidently told her that I was ready for whatever she could handle. "We'll see," she smiled coyly, "we'll see."

I walked back to my house with a satisfied smile on my face. I silently congratulated myself for setting this whole thing up and was already looking forward to my next "milking".

Comments welcome.