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Cherry Pickers 11 Brian
Brian: While some of my class looked forward to getting fucked, re-leaving them of their anal virginity. I was an ass man myself. I had drooled over the asses of the guys I roomed with and those of the staff that I saw getting fucked. But I always imagined myself as the guy on top for those luscious bottoms. I wanted to kiss them and make love to them, but the idea of a cock in my ass terrified me and no amount of getting psyched up for a fucking made this evening any more enticing.
I had asked John if there was any way I could be a top and fuck one of my fellow class mates and attain the status of brotherhood. He replied, "There will be plenty of chances for you to pick cherries in the future and help those who have loved getting there cherries picked, but tonight, you will enter the brotherhood as all other have, or you may leave now. You will not be judged as a looser, just as a man who has come to terms with his inner being, which is not a part of this group. You will receive your full scholarship and you will go in peace".
Me a fucking looser, no fucking way, I thought. But as Matt called my name to step forward, I was almost compelled to run away, I was that frightened. When the man who had bid to take my cherry stepped though the darkness, I almost cried. Here I stood at six feet, and weighed 160 pounds. I loved any sport and competed on a non-varsity level with my friends. My treasure trail started at my belly button (an innie) and fanned out quickly to cover my pelvic area in a very dark blonde, long thick mass. Part of me wanted to trim it and the other part was amazed at how long it grew, long enough to comb. I excelled in music and could play the piano, organ and violin as knew the rudimentary workings of brass and woodwinds, although the percussion instruments, in many eyes the simplest were for me the hardest to master.
I had bonded with a senior when I was a freshman. He let me hang around with his friends and him. I realize now there was a sexual tension in the air, but nothing happened. He made it a point to look me up during my Senior Year Spring break, and after hearing that I was going to attend the same University the next year, we went to lunch. Neither of us beat around the bush as we acknowledged that we were both gay, and he grinned ear to ear when he found I was a virgin and gave me a quick tutorial in the Cherry Pickers without revealing the brotherhoods name. He submitted my name for membership and now I stood waiting.
I almost cried when I saw the man who was going to pop my cherry. At Five foot eight, I looked down on this man who had to be forty or fifty years old. He had a slight belly, receding hair line, tan legs and arms and the rest white as a sheet. My fucking luck I thought as I looked down at the floor and willed myself not to look him in the eye.
"I'm Guy," and I know that I am not God's gift to man as far as looks are concerned," he stated. I read your profile, and when I saw your body language tonight I realized you are scared to death to get fucked. I think you are a total top, just as you believe you are. But tonight you will be fucked, and you know it, and want to get this part of the initiation over," he spoke barely above a whisper into my ear.
"Most gays find life like a box full of Tupperware, too many bottoms and never enough tops", he grinned. But trust me to be a great top, you have to respect the wants and needs of the bottom. The old wham bam thank you Dan is not the way to make your bottom have as good a time as you do, and also you will find that just blowing your load without engaging your partner over time is not a successful combination for either one of you. Now I have one attribute that you will be thankful for. My cock is seven inches long, but extremely thin and torpedo shaped. If you a total top are willing to give up that virgin ass, I have the cock for the job. Having said that are you ready?"
I grinned at him, "Now that you put it that way, yea I am. Let's do it." I said. My admiration for this man had grown immensely. To bid he must have been wealthy, and for all I knew I brought the least amount at the bid. He could have walked in, not cared a thing about me, gotten his nut in a cherry ass and moved on. Yet he had taken the time to engage my mind and my body was responding in a positive fashion as my dick that had only been slightly chubbed most of the night, now proudly stood at a full thick 8 inches.
"OK you know the routine, get that fine grade A Beef Ass up there and spreadem," cause you are about to get fucked. I would have thought my cock would have deflated, but sensing the inevitable, it grew and stood proudly. Guy quickly lubricated my ass and cock and then I felt it. Jesus, how had the other guys stood it, I felt that the long thin dick must have grown into a redwood as it invaded my ass. Slowly and surely Guy pushed until I felt his pubes rubbing my ass. He started to fuck me, and while my ass never felt the love for cock that some of the guys had, the pain was bearable and I enjoyed watching his face as his cock plummeted by ass hole. Guy was more than considerate as his took slow even strokes, hitting my prostate and keeping my cocks attention to what was happening.
I knew that unlike some of the men, fucking me would not result in an eruption from my cock, but neither would I go screaming like a raped virgin from the room. I had lost my virginity fair and square on the Altar of Cock and my college would be paid for. I also knew that when I ran into a bottom Cherry Picker that my life would be golden. And so the fucking continued and I hoped Guy would soon pump my ass with his seed of life. I felt the buildup and my ass responded as it hoped that by co-operating the assault would soon end. As it did. The funny thing is I loved the feeling of cum squirting into my hole. So how do you get seeded without getting fucked I wondered?
"Thank you Guy for being so patient with me. Not many guys would bid that much money to help the newbie reluctantly losing his cherry," I said. I will remember what you told me and try to be one of the best tops you have ever met. I then leaned in and surprised myself as I initiated the long sensual kiss. We broke apart and then I pulled him into me for a through tongue battle as the room erupted into cheers and catcalls.