I was talking with my friend, Tom (all names have been changed to protect privacy). I mentioned some of the stories I had read here. He related his own tale of a first time. I encouraged him to write it, but he said he's not so good with words. He asked me to write it for him in the third person.

Tom had just turned 18, graduated from High School, and getting ready to start college in the Fall. He was a normal teenage with sex constantly on his mind. However, he had long ago realized he liked men more than women for intimate moments. He had given and gotten a few hand jobs and even blow jobs, but had never made the step to get his anal cherry busted. It wasn't that he didn't want to, he just knew who he wanted to do it.

Tom had moved back to Bangor to live with his father so he could attend the University of Maine at Orono. He had lived with his mother in Portland for the last four years since his parents' divorce. His mother would never discuss why the marriage broke up, and was very upset when Tom told her he wanted to go to UM-O while living with Dad. His mother had several angry phone calls with his father, but finally agreed. It pained Tom when he left in mid-summer to get settled in as his mother was very upset.

When Tom got to his father's house, he settled in to his new room. It was spacious, and only a short ride from the campus, and a part time job he landed. But the best part of it was getting to spend time with his father. His father was barely 40 years old, but could pass for 30. He took good care of his body, healthy living and regular gym workouts. He had a healthy tan and still a full head of hair. This was who Tom wanted to bust his anal cherry. Tom had long suspected his father was gay, and that was the reason for the divorce.

Tom knew it would take some work to get what he wanted. His first step was to adopt a relaxed attitude toward nudity. After his shower, he walked down the hall to his room buck ass naked. The first time his father saw him, he remarked he shouldn't walk around like that. Tom replied that he wasn't ashamed of his body, and his father shouldn't be either. After all it wasn't like there was anybody else sharing the house. His father accepted, but cautioned on being more discreet when company was around, and advised it might be something Tom might not want to mention to his mother. Tom assured his father "Anything going on in your house, Dad, is none of Mom's business. I'm not here to be her spy. Relax it's all just between us." His father seemed to accept it. Tom began leaving the bathroom door open when he showered, and sleeping in the nude in the summer heat with the bedroom door partially open "for air circulation".

His father accepted the style, and began to relax his own attitude. Tom had noticed his father checking out his body several times. He swore he could see an erection in Dad's pants when Dad passed Tom's naked body in the hall. After a week, Dad also started to display more nudity. The first time Tom saw his father's cock, his knees nearly buckled. If they had, it would have been a perfect time to fall right into Dad's crotch. Tom went to his room, stripped, laid on the bed, and started to stroke his own meat. He looked at his rigid 6" while thinking of his Dad's swinging dick, as big flaccid as Tom's erect. As he continued to stroke, he got the feeling he was being watched. As soon as he shot his load on his own chest, he got up to go wash off in the bathroom. His Dad was just retreating into his own bedroom, and there was a slick spot on the floor outside Tom's door. His father looked back over his shoulder at Tom. Tom took the opportunity to openly smear the cum on his chest as he watched Dad's cute ass disappear.

The next night, Tom got off of work early. He arrived home about two hours before his Dad would expect him. There was a strange car in the driveway when he got there, but he didn't find Dad in the house. Looking out into the back yard, Tom noticed two guys in the swimming pool standing close to each other. He grabbed a trio of beers out of the fridge, and headed out to the pool. As he quietly approached, he could swear something was going on between his Dad and the other guy in the pool. He cleared his throat causing his father to jump backwards, stumbling, and going underwater. When he surfaced, he was sputtering and spitting water. Tom and the other guy each laughed. Tom mentioned he brought out some fresh brews. Neither Dad nor the other guy made a step to get out of the pool. His father introduced the other guy as Mr. Brown, one of his friends. Mr. Brown nodded hello. Tom asked how the water was. Mr. Brown said great. Tom noticed two men's swimsuits on the far side of the patio. He asked if they would mind him joining them. Mr. Brown shrugged, but his father asked if Tom had some work to do first. Tom replied no. His father said okay. Tom asked " Should I go get my bathing suit, or just go naked like you two?" Mr. Brown laughed and Tom's father blushed. Since nobody said no, Tom began to slowly peel off his clothes. Taking his time, he waited till after he took off his shorts and underwear to bend over to take off his shoes and socks giving the guys a clear view of his ass hole. When he dove into the water, he came up beside his Dad. He casually brushed his father's cock only to find it already rock hard. As Dad jumped back, a new plan hatched in Tom's mind. He figured a little attention from Mr. Brown might stir his father up a little. Swimming over to Mr. Brown, Tom ducked beneath the surface and swam through Mr. Brown's parted legs from the back to the front. He surfaced right up against Mr. Brown who quickly closed his arm around him underwater. Tom gave his dick a playful squeeze and quick evaluation. Not as bid as his father's meat, it was still respectable. As he looked at Mr. Brown, Tom realized this was the kind of guy he would probably pick up cruising for a quick suck, but tonight he just wanted to tease Dad. Tom turned back toward his father and noticed his scowl. Tom wasn't sure if the scowl was because of Mr. Brown's interest in Tom, or because Tom had foiled Dad's fuck plans for the night.

Soon after, Dad suggested it was getting late, and they should get together again soon. Mr. Brown was the first to pull himself out of the water. Tom got a good look at his body. A trimmer version of his own father, Tom drooled over the dick and ass now fully visible to him. However, when his father followed suit, Tom almost shot his load. His father's dick was rock hard and red, desperately needing attention. Tom hoisted himself out of the water exposing his own erection. Mr. Brown chuckled lightly as he looked at three naked guys with bobbing erections. He suggested we move the party inside, but Dad said not tonight. When he bent over to pick up his swim suit, Mr. Brown made sure both guys got a full view of his pink pucker.

Tom went up to get a shower and dress. When he came out, he noticed his father's door was closed. He tiptoed over to peek through the keyhole. His father was sitting on the bed, still naked, beating his meat off. Without hesitation, Tom opened the door and walked in. For the second time that night, his father jumped in surprise. He quickly covered up his groin as he growled "Don't you knock." Tom said "Don't worry, I've watched you jerk off through the keyhole several times. You know you shoot a great load. Just wished I was sucking your dick at the time so I could taste it." His father laughed "I should have suspected you would turn out like me." Tom reached over and pulled the sheet out of Dad's lap. Getting on his knees beside the bed, Tom gabbed the swollen dick as he lowered his mouth. His father pulled back in shock "I'm not sure if this is right." Tom responded "It's more than right, it's needed from the looks of this cock. I know I scared off your fuck mate for tonight." Dad relaxed and laughed "You had him about ready to rape you, you know. I didn't know if I wanted to punch him out or hold you down for him."

Tom pushed him back onto the bed, and began to swallow his dick. Wanting to show his best talents, Tom took his father's full length all the way down in one smooth motion. His father moaned. Tom pulled his mouth back until his lips were closed over just the rim of his father's head. He then slid the full shaft back into his throat setting up a steady fucking motion. His father was squirming. Despite his best intentions, Tom knew his father would not last long after the night of teasing and the initial hand job. Soon he was rewarded with a blast of thick, hot cum. He gobbled down every precious drop.

As his father relaxed, Tom moved up and straddled his chest, presenting his dick to his own father. Never one to turn down hot meat, his father quickly took him in his sweet hot mouth. Tom liked to fuck his suckers in quick jabs. His father didn't seem to mind, so he keep up a steady pace. He was soon feeding his own cum to his Dad.

Laying down encircled by Dad's arms, Tom was in heaven. He leaned over and kissed his father full on the lips tasting his own cum. His father pulled him back up on top and started running his hands over the boy's body. When he reached Tom's ass, he playfully parted the cheeks. Tom moaned. His father whispered, "Oh, you like it in the ass too, son." Tom said "I don't know, I'm still a virgin there. I want you to have my butt cherry." His father pulled him up a little, and said "You're really a virgin?" Tom smiled and said "Only in my ass. Everything else is well used." Tom sat up with his ass pressed on his father's resurging dick, grinding slightly. Tom pleaded "I really want you in me." His father stopped and after a few seconds said "No, not tonight. I need to do something first." Tom's heart fell, his father was rejecting him. However, Dad put his arms around Tom and pulled him back against his chest. He said "No ass breaking tonight, but I do want you to sleep with me for the rest of the night. Tomorrow night I'll have a surprise for you."

Tom had to get up early the next day for class registration, and then had to work till 8:00pm. He was excited as he sped home. However, his heart fell when he pulled in the drive, Mr. Brown's car was there again. It was even worse when he walked into the house. Not only was Mr. Brown there, but a young kid of his own age. He was introduced to the kid as Mike, Mr. Brown's son. Tom saw all plans for tonight going out the window.

Tom's father signaled him to come into the kitchen. Tom was upset, and asked his father why there was company there when he had promised they would do something tonight. Tom's father explained "I need you to do something for me. Pay a debt for your old man. You meet John's (Mr. Brown's) son. Last year when he turned eighteen, the boy came over for a visit. He asked questions about his father and me. I tried to say we were just friends, but Mike knew it was more. He shocked me when he explained he was horny for his own father, but was too scared to make a move. He though I would be a good substitute for his father. One thing lead to another and I ended up popping his cherry. I always regretted not telling him to seek out his own father first. I know they have gotten it on since then, in fact we have had three ways together. What I wanted to know is will you let Mr. Brown be the one to pop your ass. I'll be there to help, but this will repay my debt to him. Your cherry for the cherry I took from his son."

Tom thought about it. Mr. Brown was attractive and Tom had figured he would end up getting it on with him sometime in the future. Tom said "Only on one condition, I want you there ready to be second." Dad agreed. They went back into the living room, and Tom's father said "Why is everybody sitting here. Let's get up to my bedroom and get naked." There was a flurry as four guys stumbled up the stairs pulling off clothes as they went.

When they got into the bedroom, Tom took Mr. Brown's hand and lead him to the bed. Mr. Brown looked to Tom's father who just nodded. Laying down on the bed, Tom stuck his ass up. He wasn't sure how this would go, but he was horny as hell. He felt the bed shake as Mr. Brown crawled up behind him. Expecting a gab of hot meat, Tom jumped when he felt a wet tongue lick up the crack of his spread ass. He was getting rimmed. Mr. Brown snaked his tongue tip into the puckered hole teasing it open. Tom loved it. Soon, he felt two fingers pressed against his opening. They slid in easily with the assistance of a generous coating of lube. Tom began to feel a warm glow spreading across his ass unaware of the special properties of the anal lube being used. When he started to squirm, Mr. Brown shifted position to line his erect dick up with the virgin ass. The first push was a flash of pain causing Tom to tighten up. Mr. Brown leaned over and told him to relax. Tom began to get frightened. It hadn't even entered him and it was hurting. Tom looked toward his father. Dad was getting a blow job from young Mike at the moment, but turned toward Tom. Dad pulled his dick out of Mike's mouth and crawled up on the bed in front of Tom. "Here," he said "maybe this will relax you." He popped his dick in Tom's mouth. Between the warm feel of the anal lube and the distraction of hard meat in his mouth, Tom began to relax. Mr. Brown eased the bulb of his dick into Tom's hole. Once the ass ring closed around the shaft, Tom began to enjoy the sensation. Mr. Brown pushed more of his meat into Tom gradually until the hairs on his pubes were tickling the young boy. Tom felt full, but the pain had faded. As Mr. Brown's dick grabbed and slide along the inside of his ass, Tom moaned in ectasy. Soon, they settled into a steady motion. When he reached climax, Mr. Brown drove his shaft all the way to the bottom of Tom's ass. The action caused Tom to rear up, dropping his father's dick from his mouth. Mike was right there to replace him. As Mr. Brown spurted loads of cum into his ass, Tom collapsed beside Mike. Tom's father pulled his dick out of Mike's mouth and started jacking off over their faces. Tom watched in a daze as the cum shoot out of his father's dick coating the two young guys faces. Tom turned and began to lick to fresh spunk off of Mike as Mike did the same to Tom's face. While they were occupied, Tom's father got around behind and shoved his still hard dick up Tom's ass. With Mr. Brown's cum and the lube slicking up the hole, Tom had no trouble taking it to the hilt. His father rode his ass without mercy. Before his father could come, Tom spurted his own load onto the sheets. Falling forward, he just lay there as a piece of fuck meat for his father. The sudden swelling and deep jab told Tom his father was coming deep in his bowels. The four of them collapsed on the cum coated bed. Tom felt the two loads leaking out of his ass. He might be sore in the morning, but tonight was perfect. He had helped his father in paying a personal obligation. He had finally got his father to fuck him. The added joy of the Brown's company was just going to make the next four years of college a dream.

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