Cherry Pickers

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The Cherry Pickers 2

Coach: My name if Jerry, but I've been called Coach for so many years that sometimes it takes me a second to realize who "Jerry" is when the name is called. I'm 49 years old. Next year I will be able to retire after 28 years of teaching. I've always been interested in sports and played football in high school and college, though I was a little guy. The kicking team became my specialty, and helping decide the crucial games in high school in our favor got me a full scholarship at a small college.

I've always been aware of my sexuality, knowing that I was more attracted to men than women, but I found at in college that I could function with a woman. Majoring in PE, and wanting to coach in high school, I knew that I had to fight the urge, and married a wonderful woman, Ellen, the summer after we graduated. Luck had it that we there were teaching positions at the same high school; she 12th grade honors English and me History and Coaching. Exactly one year from our wedding day, July 4, 1976, our first son, Gerald, Jr. was born. A born jock, he seemed to be straight, and then our second son, Josh born in March of 1996. Josh was a complete surprise as Ellen's periods had always been irregular and we used a fertilization drug to conceive Gerald. Gerald was a little surprised to be a brother at age 20, and kidded me about being a stud. All went well until four years ago when I was called in a panic to her classroom. An ambulance arrived, but it was too late, Ellen had an aneurism, and died on the way to the hospital. For the next four years I lived the life of a monk, being Dad, Mom and parent to Josh.

Two years after Ellen's death I met Bob in the Country Club sauna. One of the perks of being the Head Coach was free membership in the club. From the tents in our towels, there was no doubt where the conversation was leading. Bob was older than I and very good looking with salt and pepper hair, and a chest rug that while primarily black had a shock of white hair in the middle. I kidded him that his chest made him look like a dog I once owned. The desire was there, but as he had recently remarried, and because of my job, I shied away taking things to the next level. Bob sensed my concern and was happy to have me as a buddy. One day we talked of retirement. I told Bob that soon I would have to make a decision about my career. The state system would allow me to retire with full retirement after 28 years, but with Josh entering college, Ellen's insurance money would probably be spent educating him. While 50 would not be old, I was scared at the prospect.

It was then that I learned about the Cherry Pickers. Bob was on the board, and the man who ran the day to day operations would be retiring in a year. Over the last couple of years, Bob figured out that I had been a "married gay man" and had not stayed from my wife. After extracting a promise sealed with a kiss, he told me the history of the "Cherry Pickers". The group was composed of gay, married gay and bisexual men. I could be hired without becoming a member, but to become a member, I would have to become a newbie like the rest of the men attending for the first year and submit to the initiation process, which would result in having my cherry popped. I stood there for a minute or without speaking. Embarrassed that he had gone too far, Bob looked down, and seeing the tent in my pants said "I take it that you have thought it over and your head says YES." Josh would stay with his older brother for the summer as Gerald had graduated college was gainfully employed.

Three days before I was to go to Cherry Hills, the estate of the Cherry Pickers, Josh and I played a game of doubles with Bob's daughter Mary and his step-son a former student of mine, Frank at the club. I was rudely awakened at 3 in the morning as Bob relayed that Mary had basically raped Frank. Bob was upset with Mary, but Frank's mother was convinced that Frank had lured Mary to his bed. Bob and I were pretty sure that Frank was either bi or gay. Frank and I had exchanged cell numbers and I called him the next morning.

I have never seen a person as lost as Frank when he called. Although he had finished his senior year in college, he was so naive, especially about his looks. Here stood a young man 6'3", blue eyes, 33 inch waist, red headed, and covered head to toe in red down, which on his chest, around his cock and on his ass, had to be described as red fur. My cock wanted to be at full mast every time I saw him. He seemed not to have a clue that most people men and women followed him with their eyes, in a lustful gaze. Being his former coach, I had seen him in all stages of undress, and his torpedo shaped uncut cock, with what appeared to be a tight foreskin excited me. Once, when he crashed at my house, I saw his cock hard, and yes torpedo is the best description for it as it is three times wider at the base than at the tip. A man getting fucked by that cock will know he has been fucked, no mushroom head here, just the head hiding behind a long foreskin, that did not appear to fully retract when hard. Low hangers, containing two large orbs completed the package, and all of this including his hairy ass and crack, was fodder to may jack off sessions for me.

I wasn't sure, but I am pretty sure that my son Josh is gay. Josh at age 17 is no slouch standing at five eight, and weighing one hundred seventy pounds, not fat but certainly not skinny. He had huge nipples and a beautiful 8 inch hard cock that I got to see several times when I went into his room to wake him. Josh many times slept on top of his always made bed, with little on, and being just two guys in the house, we knew that morning wood happened. . If I entered his room and he was asleep, I gaze at the mushroom head of his hard cock, looking like a totem pole growing from his curly thick black pubes. His ball sack hung low with two egg sized nuts. Damn he was hot, and if his ass was up, it was smooth except for a hairy trail down this crack, and oh yea, he had jet black hair, blue eyes and white skin. I worked hard not to want to take him into my arms and kiss him, but, as his Dad, I knew I couldn't.

Frank: Upon arriving at Coach's house, I found Josh packing his bags to go spend the summer with his brother Gerald. Coach was going to work at an estate called Cherry Hills, and would be for the summer a member of the Cherry Pickers. He was excited as this might lead to a career change with him becoming head of running the estate. This year would be different, as he planned to enter on the same level as the other new guys so he could see what the workers encountered. Instead of living at the main house or in one of the cottages, his room would be in the NEWBIE barracks, and if I choose to attend, we would be close to each other, doing the same things, although he would technically my boss.

Before I agreed, Coach asked me if I was a virgin. Hanging my head, I said, "Coach you know the answer, I fucked Mary last night, though I was asleep."

Coach countered, "Frank, I'm going to be blunt, have you ever had sex with a man?"

I blushed and said "No Coach, I haven't". Not knowing what else to say I hung my head. I felt Coach take his hand, and place it on my chin as he raised my head to an angle where he looked me directly in the eye.

"Frank, I am probably wrong, but having known you for four years in high school, and observing you yesterday, answer me truthfully, are you either bi or gay?"

"Coach, I functioned with Mary yesterday, but I was dreaming about a man" Coach did not say a word, but kissed me and responded,

"Frank, I am also a virgin in the male sex department. Before taking the job at Cherry Hills, I found out that there will be gay and bi men exclusively at Cherry Hills. If you want a full scholarship, are you prepared to lose your virginity in an initianton ceremony?"

Cherry Hills was about two hours from home. After being on the road an hour, Coach asked if I wanted to make some spending money over the course of the summer. "Hell Yes, Sir", I replied. He pulled his truck into the parking lot of a medical complex, and we entered the "Fertility and Reproductive Specialists". I didn't know what to expect, but Coach explained to me that if I wanted to jack off, and didn't mind the thought helping others who could not have children, I could cum and get paid for it. Coach during his marriage and after had been making regular deposits. After reading the literature, I thought that being a test tube baby would disqualify me. Because of being a test tube baby I was interviewed gave my birth date, name and social security number. A few minutes later, I found that at one time I had been a sperm in that very bank and that my medical records were in order, except for current health questions which I passed in flying colors.

I consented to be photographed from the neck down and first clothed and later in all stages of undress, including my cock, which had a mind of its own, and loved the session as precut oozed through the foreskin. The photographer was built, and let me know he appreciated my body and cock.

We arrived and were shown to the barracks. There were 10 new guys that year, and we covered the height range from 5'6" to 6'6", with every combination of hair, body shapes and cock lengths, soft or in the morning with wood. Work was from 7 am to 4 pm with an hour for lunch, provided by the staff. All of us had varied duties, and I drew the dream job four hours in the morning working in the Cherry Trees and four in the afternoon tending the tennis courts, pool and putting green for the wealthy who came down to visit over the summer. These men would help with the cherry trees and all aspects of the farm. One of the perks was that the pool had a no suit rule, so I got to see all of the men, staff and new guys in their glory, and many sported had cocks. Everyone checked each other out, and wood was the natural state.

Even though the new staff had to be virgins, I figured out quickly that the returning staff was not, when quite by surprise one day I went into the changing room and found a camp counselor, John bent over a table with Mr. Smith, head of finance, kissing him as he slid his cock in and out of John's apparently not so virgin ass. Damn I popped a boner, and could only stare in lust as John got fucked...all the while wishing it was me. The fucking went on for at least ten minutes with the pace getting faster and faster as the forty or fifty year old man pounded John who was screaming "deeper, deeper, harder...fuck my goddamn ass..." Mr. Smith was twisting John's nipples and the slapping of balls against ass was a sound that I wanted to feel.

Later that evening I saw John who matter of factly asked, "So what did you think about me getting my ass plowed?"

"You knew I was there?" I asked with a shaking voice.

"Hell yea. And now I want to know at the end of the Cherry Popping Festival do you want to have your Cherry Popped and become a member of the Cherry Pickers?" The fringe benefit of a scholarship was wonderful, but the idea of having sex with hot men was what I really wanted.

John told me that whether I agreed to get my cherry popped or not, I would still qualify for a scholarship, but would not be invited back to work again, and would lose my chance to be a member of the group if I refused this honor.

Me refuse? I was in heaven. I had been paid to jack off, had seen guys fucking and getting fucked and was now being asked to get my cherry popped and join a group of gay men. What was there to think about? Times had changed since the founding of the organization, but for many of the members, being married with children, this secret society made life bearable. The Cherry Pickers, at least the ones I had seen were some of the best looking, men and many were some of the wealthiest and most powerful men in the nation if not the world. Hell, I wanted to be fucked, and the idea of joining this group with the fringe benefits was more than I could imagine.

John told me the details would follow, but that it was a group initiation and that if I felt uncomfortable at any time, I could leave, but would not be invited back. I did not tell him that Coach had leaked a little of the information to me already, as I did not want to jeopardize his career.

The weeks flew by and I could not wait for the moment of truth when the newbies would have their Cherry Popped. In the newbie barrack it was all we could talk about as each of us witnessed the horny members of the returning staff fucking, sucking or making love to men their own age or younger, or vice versa. While I thought I knew many of those in attendance, the really top men of wealth and power would not arrive until two or three days before the initiation.

End of Chapter 2