5-Year Plan

This may appear a little long, but I felt it better to submit it all in one versus broken into pieces.

There is some sex (nobody under 18) but it is mostly a Fetish love story.

50% is true. Too true.

Enjoy

.......

She's so high above me,

She's so lovely,

Like Joan of Arc,

Or Aphrodite. Tal Bachman

5-Year Plan

I looked out the window. In the distance were the tops of the trees of my favorite stand of mostly deciduous hardwoods. It was only last week I skipped through that forest. It was my special place for my imaginary adventures. The summer had been hot and dry. There was a smattering of dry leaves on the ground. My hiking boots crunched and crinkled the leaves when I kicked outward. The smell of fungi was funky yet pleasing. I picked up a maple leaf. Inspecting it closely as it had shrunk around the edges, I slowly squeezed my hand. It disintegrated into a powdery debris. I blew the dust off my hands, watching the larger fragments catch what little wind penetrated the overhanging canopy. They would do their own dance and then settle gently to the ground. These were the sights, smells, and touches of my childhood. A distant sound broke my reverie. It was a crow or raven. "​​Caaw, Caaw, Harr, HARRY"

​It was my grade 8 teacher, Mrs. Lewis. "Harry, pay attention. Class, we have your guidance teacher, Mrs. Sinclair, here today to make an announcement. Mrs. Sinclair."

"Thank you, Mrs. Lewis. Hello class. This is an important year for you. You will all have to make some important decisions in the next few months. You will all need to select your courses for high school and then get set up for college. I call this--Making a 5-Year Plan. Your 4 years of high school and your first year of college. Now I know this might seem daunting but I will be seeing each one of you individually to help with your decisions."

'What the fuck did she just say?' I thought. I am 14. Just your average kid still dreaming of the summer past. 'A 5-year plan?'

At supper, my mom asked how school was. I was quiet. "Was it a tough a day?"

I picked at my food and muttered, "Yeah. My teachers talked about making a 5-year plan. They say I have to get ready for high school and college. I don't know what I am going to do 5 days from now, let alone 5 years."

"Oh, Honey, I think your teachers are right. You really have to get ready for your future."

"Really?" I was surprised mom didn't side with me.

"Your mom is right, Harry," dad added. "You have to get ready for the job world."

"Job?" this 'family' talk wasn't going well.

"Yes son. Starting with a part time job perhaps when you turn 15.".

"Can I be excused. I am not feeling well."

....

Chapter 2: Year 3 of my 5-year plan.

Grade 11: My 5-Year plan is on track. High school is going well. My strongest subjects are the Maths and most of the Sciences. English was my weakest (as you can tell from my poor writing style). I was looking forward to getting into a business/accounting college program.

There is a big problem with 5-year plans--the unexpected. Kate was my unexpected event. She became my girlfriend. It was wonderful. She was a brown eyed, long-haired brunette, "Girl next door" type with C breasts. Perhaps she was a little chunky which probably made her a only 6 or 7. She was also funny and very smart. Even stronger in the Maths. It was a wonderful time for me. We first had sex after our 18th birthdays. It was magic. I was in love.

Another thing Kate and I liked, was people watching and grading them. As an example, I remember seeing a guy who I thought was a 10. "Look. On your left, a guy who's a perfect 10."

Without turning her head, she said, "No, he's only an 8. His shoulders are too narrow."

"You didn't look at him."

"Yes, I did. I used the 'lady look' not the 'guy gaze'."

"Okay, you have got to explain that."

"The 'lady look' requires you to keep your head still and move your eyes only. Not like you guys who move your head sideways, even up and down like you are laser guiding a missile."

We dated for two years. She was a lot of fun. The one downside was that my marks began to suffer. Nothing terrible, but slipping from A's to B's. Kate was going to a university to study Honors Math. That school was my third choice but I enrolled there as well. Just to be close to her.

Chapter 3: Year 5 of the first 5-year plan.

First year University. Being close to Kate was wonderful. But after a night of partying and great sex with Kate, I had a massive hangover. Coming slowly to my senses the next day, I started to re-evaluate my college choices. I was aware that I was possibly going to flunk out. But the worst part was that even if I did turn my marks around and graduate; my best job prospects would be in teaching. I hated kids! Not little kids, but the likely snot nosed, indignant and indifferent kids in school.

I transferred to a business college 6 hours away. My relationship with Kate took a hiatus and eventually a break-up. I thought of another 5-year plan. This one was easier. Three more years of college and two years of career building. No time for girls in my plan.

Year 1 of my second 5-Year plan.

The first weeks at my new college was when I knew I was in the right program. But the pretty girls were everywhere. I couldn't help getting constant erections. At times this could be embarrassing and distracting. I came up with a unique solution. Cock cage. I purchased a top-of-the-line cage restraint. But this wasn't the full solution. The trick was where to put the key. I would have to clean my cock and cage at least once a week. When this happened, I would also masturbate before putting the cage back on. But I would play games with myself and clean the cage more often so I could relieve myself. I first put the key in my night table drawer. That was just too convenient. My next spot was in the bathroom. That was a failure since I could toss one off there. The next was the top shelf in the kitchen cupboard. Another failure. The best was inside a cup of water in the freezer. Unfortunately, after three hours thawing time, the rusty key and my poor will power caved in again.

I was still thinking 'where was the best place?' My thoughts went to: safety deposit box--banking hours were too restrictive; my roommate--too awkward and embarrassing; a relative--not even close. Then I came up with the best solution--Wicked Wendy. She was a part-time evening student in her mid 30's. I got her name from my roommate who knew a friend who knew a friend. Wicked Wendy turned tricks on the side. A hooker.

I called her and asked to see her. She had me come around on Wednesday at 10:00 pm. She was a 'working' single mom and her kids were in bed. She brought me to her basement where there was a couch and bed in the middle of the room. She told me what the prices were; blowjob--$50; fuck--$75; and, kinks extra.

"Well actually, I have a weird request." I explained my situation. "I need someone to hold my cock cage key who is discreet. I need that person to release me once a week. Would that be something you would be interested in?"

Wendy considered this. "That is the weirdest, wackiest thing I have ever heard. And, I have had lots of kinky requests." She seemed to think carefully. "Once a week, you say."

I gave her the hygiene excuse, but she saw through that bull shit answer. "Sure hygiene" came her sarcastic response. "Okay, tell you what. $50 a week for that privilege. But I cannot do that during my prime earning hours. Come around at 5:00 am on Saturday morning. My kids won't be awake yet."

"Okay. I would like to start two Saturday's from now." That gave me extra masturbation sessions.

"Okay, deal. That will be $50 today."

I wasn't expecting to pay today but I gave her the money. This turned out to be both the best and worst decisions I have ever made.

My first visit I arrived promptly at 5:00 am. My anxiety had me waking in plenty of time. I pulled down my pants exposing my somewhat larger cock restraint. She unlocked it.

"Are you going to take the cage off now?"

"No, I am going home to clean it there. Here's your money." I would later do my thing with my thing, then re-lock.

"That's the easiest money I have ever earned. See you next week."

This went on for six or seven weeks when one Saturday morning Wendy asked, "You're welcome to take it off here."

"No, I'm good."

"I actually am kind of curious. If I let you see my boobs, will you take it off here?"

While Wendy was in her mid-thirties and her hard life made her a 4 or 5 at best, a naked boob was a naked boob. "Okay. Can I use your washroom?"

"Oh, Honey, there's isn't anything I haven't seen before. You can take it off here."

"Between my normal morning erections and the tightness of the cage, I am going to need to run some cold water over it first."

"Okay, first door on your right. Don't make too much noise."

After quietly running the water, I was able to extract the cage and I returned to stand in front of Wendy. My hands were in front of my genitals. "Ah-hum" I cleared my throat and nodded towards her chest.

"Oh right." She quickly removed her top and her breasts were saggy and pointed down and outwards on her chest. Not the best I have seen, but in my condition, they did the trick. My cock jumped upwards in micro seconds.

"Fuck. What a cock! What are you doing hiding that beautiful thing?"

I was impressed that a hooker would like it. I started to explain the 5-year plan idea, but I quickly noticed she didn't care. I pulled up my pants and left.

She wanted to see my cock every week. One Saturday morning she said, "I don't normally give discounts, but since you are such a good customer, I am going to throw in a free hand-job."

Over time it turned into blow jobs at no extra cost. After months of blow jobs, Wendy told me, "Next week bring a condom." She smiled the sweetest hooker smile.

The next week I returned from her washroom with my sheathed phallus, Wendy shouted, "What the fuck are you doing?"

"I thought we were going to have sex?"

"College boy I am going to have to give you a superior education. First, never be so brash with any woman. Now you are going to have go down on me to earn it. Make me cum in 10 minutes and you may get lucky." I hesitated, not sure If I wanted that no matter how horny I was.

"Don't worry, Honey. Everyone uses a condom. Maybe sweaty. I may even let you lick my arm pits."

"Yuck."

"Just kidding, but I wasn't sure how kinky you are. Time's a ticking, get-a licking."

I lowered and the smell overtook my senses. I touched her labia gently with my fingers. Rubbing her slick juice, I lowered. I stuck out my tongue and began to lap at her pussy. I forced my tongue deeper and stroked her clit with my thumb. Then putting my lips around her clitoris, I tried to do the alphabet between her pussy and clit.

"Just as I thought. Let me teach you how to do it properly. A good cunt licking and your cock will get every woman to climax." She gave me an excellent education.

"Okay College boy. Enough for today. You've got a nice weapon but you probably don't know how to use it. Next Saturday morning, I am going to teach you Sex 101. I would throw the fuck in for free but the lessons are going to cost you an extra $25 a week. That will be the best money you will have ever spent." Wendy taught me to fuck properly. I had been the slam bam type. She was right. It was my best 'college course' plus homework was fun. As I was leaving, she said, "Be here at 4:30 next Saturday. We are doing an 'in-depth' study."

As much as Wendy helped me improve my carnal techniques; ironically, the best thing Wendy helped teach wasn't sexual. It was getting use to waking up at 4:00 am. I was now doing this every day. My productively in those 4 to 5 hours was mind blowing. I got so much work done at this hour. No distractions. My grades improved to A+ in 5 out of my 6 courses.

Year 3 of the Second 5-Year plan

This is my senior year. Still using Wendy's services. I share an apartment off campus with my flat mate Tony. My girlfriend from high school gave me the ranking of--6. I am tall but not dark or handsome. We have both moved on and there aren't any plans to reconnect. Tony on the other hand is definitely hotter than me. Personally, I find it difficult to rate guys. But he scored with a babe that was a 10+. Andria was blonde, blue eyed "Barbie" like. Definitely D's or better. Drop dead gorgeous. So, he must be at least a 9.

Andria came over to 'study' with Tony late into the evening. I retired to my bedroom to give them some privacy and to go to bed early. I am enjoying the productive, pre-sunrise mornings but that means hitting the sack earlier than normal. Going to the bathroom, I happened to catch some movement from Tony's room. His door hadn't latched and was about six inches open. I saw a flash of white which I quickly recognized as Andria's lingerie on her hot body. I didn't want to perv on them so I returned to my room and called it a night. I couldn't help but hear the sexy sounds coming from their room.

The next morning, I awoke at my normal 4:00 am. It had become second nature. Most times I awoke before my alarm. While making my coffee I had remembered to wet the paper filter first before adding coffee grounds (preventing the dreaded collapsed coffee filter). Tony's door was still slightly ajar. I couldn't help glance in that direction and I saw a pair of eyes staring back. Trying to act cool, I raised my cup and nodded my head. I thought I heard a light giggle.

I turned back to my room where I proceeded to get my day started. By 7, I had finished all my assignments and even studied for an exam for the next week.. Going back to the kitchen, I noticed Tony and Andria's books on the kitchen table where they had 'studied'. It was Math. Tony was in an Economics program so that made sense. I glanced to see that they hadn't got far. If I had a babe like Andria over (and if I wasn't locked up), I would be studying her body, too. I quickly added some answers in the margin in pencil. Hopefully it would help them.

Over the next two weeks, Andria was over three more times. I helped with the homework each morning. The last morning, she came out at 4:00 am to thank me. She came out naked. I looked into her eyes and refused to lower my head (Thank you, Kate, for teaching me the 'Lady look'). I asked her if I made too much noise. "No" she said she was a light sleeper.

Weeks later, I would see Andria walk by periodically on campus and she always made a point of calling out to me. Later I got a text from an unknown number. It was Andria telling me Tony gave her my number. "Can you tutor me?"

"Sure."

"Wednesday night at your dorm room?"

"That's not good, how about the library at 4:00 pm"

"I could thank and pay you better at your room or mine (She sends me a picture of her hot torso in a tight tube top)"

Even though she was no longer seeing Tony, I re-emphasized, "'The Library 4:00."

"Okay."

At the Library I helped her study, Math. She is in the Theatre Arts program which is normal considering how stunning she is. I try to teach her that Math can be approached as a game. Example: you are bowling with 10 rows of pins. Row 1-1; row 2-2; all the way to row 9-9; and 10-10. You throw a strike. How many pins did you knock down? Answer is 55= 5 groups of 10 + 5. 10 +(1+9) + (2+8) + (3+7) + (4+6) + 5.

I show her another trick that applies more to her field. You are offered a contract from a director who routinely films $100 million box office grosses. He offers you a) $250,000 + 25% of net profits or, b) $250,000 + 2.5% of gross sales. Which should you choose? While b) is the better answer. The best answer is: c) You prepare your Oscar winning acceptance speech because you picked me as your business manager.

After moderately laughing, "Let's take a break." Andria stretches sexily. I stayed focused on her eyes (thank goodness for my cock cage. It makes it easier). She has flirted with me most of our study time. Reaching forward to grab a pencil shows me extra cleavage. I try to change tactics, "I know another game that my ex-girlfriend and I played. " She looks puzzled and I carry on, "it's called the 'Lady Look' rating game"

"Okay, wait, You had a girlfriend?"

"Yeah, 2 years. Broke up in first year"

"You're not gay"

"No, why would you ask?'"

"You never check me out. I am making an extra effort to have you notice me. Usually, I don't have to try this hard."

I change the subject, "The rules of 'Lady Look' game: We both have to keep looking at our text book; I have to rate a guy who walks by and give him a grade. If I am more than 1 mark off--you are the expert on guys--I owe you a beer. And if I move my head at any time, I also owe you a beer. You do drink beer don't you?"

"Love it"

"Then you pick a girl and rate. If you are more than 1 mark off, you owe me a beer. Also, if you move your eyes away for more than 2 Mississippi's, you also owe me a beer. Ladies have an inherent advantage in sneaking peeks. Are you game?"

She nods. I begin with, "Let's start with an example of grading--Tony is a 9."

"You'd have owed me a beer--he's a 7"

"Good. Tough evaluator. Okay here is a picture of my ex-girlfriend."

"She's pretty--9"

"Nope, only a 6. The picture doesn't show the extra few pounds she's carrying"

"Okay, this sounds like a fun game. I think we are both tough judges. I'll keep that in mind." Andria surmises.

"Okay, ready"

"Bring it on"

"3 o'clock; guy in the blue sweater--he's an 8. I would have said 9 but you're too tough."

"Close--he's a 7. Shoulder's too narrow."

"You owe me a beer. That was 3 Mississippi's."

"Fuck, 8 o'clock busty red head--9"

"You owe me another beer--she's a 7. Would have been a 9 if they were real."

"6 o'clock guy in the extra tight jeans--7"

"How can I see someone behind me?"

"Drop your pencil and pick it up, but you only have 2 Mississippi's."

"Ha! you owe me a beer--only a 5. Jeans are pre-washed"

"Ouch, you are tough. Let's end the game on this last one. 12 o'clock--10"

"12 o'clock, that's straight ahead--I like you but you are only an 8. Yes. you owe me another beer."

"I wasn't talking about me. Can I borrow your purse?" I point to inside her purse and she nods.

"Are you transgender. Is that why you're not checking me out?"

I take out her compact mirror, pointing her way. "I see a 10, what do you see?"

She blushes and says she is an 8 at best.

"You were probably an 8 when you were 8. It was kind of a test to see if you were too into yourself."

Now she points "There's a 10!" I follow where she points. "Aha, you turned, you owe me a beer. Fun game."

We start to pack up and she waits for me. I tell her, "You can go on ahead, I want to check out some books"

"No, we have some beer to drink."

We go to the campus bar and both have a burger and a couple of beers. We talk. "Have you had any girlfriends since Kate."

"No, I am concentrating on school."

"No hook-ups or sex since?"

"I have my outlets. Just no serious relationships." I start to tell her my 5-year plan. No one normally comprehends.

She listens to my entire speech then nods. "I actually understand. I have a similar plan. I don't call it a 5-year plan, but this is something I have wanted since I was a little girl. I want to be an actress. I only enrolled here to make my parents happy. Don't tell anyone but I am leaving for New York end of semester. I may even leave after the last college play. I have a small part. They don't give Freshmen big parts. I am going to give it about 5 years to see if I can make it."

"Are you going to give up men, too?"

"You are joking right. I am not that crazy. Here comes our waitress. Wait, I think her right nipple is showing." I turned and no Jen, our waitress, was fully attired to my dismay. "Jen, my friend just lost and he owes me another beer."