Tommy’s Coming (Cumming) of Age - 10. Fun in the Sun

That summer after high school graduation Tommy worked for a landscaping / lawn care service as he had the two previous years. He primarily mowed lawns working by himself using both a riding mower for most work and a self-propelled stand up mower for tight areas. He drove a company pick-up truck and used a ramp to get the mowers off the truck. During his first week of work that summer his boss asked him to mow the lawn of a new client on a hot June afternoon. With regular clients Tommy just mowed as soon as he arrived and frequently never saw the homeowner. Since this was a new client he was told to discuss any special needs with her. Tommy rang the doorbell and a woman of about 40 answered the door. Although it was a hot day she was wearing a long sleeved top and slacks. She was a talker and Tommy learned they had just bought the house to use in the summer. Her husband lived in their condo in New York City where he was an investment banker and would be with her in Connecticut on weekends. There were no issues with the mowing and Tommy was soon working in the 90 degree (32 C) heat.

After about thirty minutes of hot mowing he saw her standing on the deck motioning for him to come to her. As he walked across the lawn he noticed she was no longer wearing long sleeves and slacks but a beach wrap that had a low neckline and short skirt. She smiled as she suggested Tommy take a break from the heat. She offered him a beer. He thanked her stating a Coke or Pepsi would be great. She went into the house and returned with a can of Coke. “Please sit and rest your hot body.” Tommy was reluctant to sit on the fancy deck chair as his bare back, chest and shorts were soaked with sweat. She saw his hesitation and said, “Don’t worry about the furniture. It’s designed for outdoor use and abuse.” As she talked she leaned forward and her tits except for the nipples were exposed. She walked around behind Tommy and placed her hands on his sweaty shoulders. “Your body needs to relax from this oppressive heat.” As she said this she massaged his shoulder. Tommy shut his eyes. Sitting in the shade with a cold drink in his hand while his shoulders were rubbed felt wonderful compared to the hot seat in the sun on the mower. Suddenly Tommy realized she had leaned forward. Her tits were against the back of his head and her hands had moved down and were now massaging his nipples.

Coming back to reality he announced, “Thanks for the cold drink, time to get back to work.”

As he rode on the mower in the blazing sun many thoughts went through Tommy’s mind. He realized she was most likely coming on to him. If it had been a straight guy he would most likely be riding something other than a mower right now. Then he thought about a video he had seen the previous day.

The condensed version of the video story line: A plumber wearing shorts is working under a sink with legs stretched on the floor. A big breasted house wife is watching him. Soon she is rubbing her foot on his crotch, opening the fly and sucking a humongous dick (in porn the girls have big breasts and the boys giant pieces). The doorbell rings. A delivery man has a package from Amazon. She invites him in and soon is on her knees in the kitchen servicing two large dicks. Doorbell rings again, pizza delivery, soon she is again on her knees now servicing three large dicks. Doorbell rings again. A man in black holding a Bible offers to save her soul, soon she is again on her knees now servicing four large dicks. After a little of ‘this and that’ she is on her back on the kitchen table. While religious man fucks her pizza and delivery are at opposite sides of the table each getting a hand job from her while they lean in and kiss each other. Meanwhile plumber, who has the biggest dick, watches and strokes himself. He then moves in and plants his dick head against the hole of religious man. He shoves in bare back and fucks religious man while religious man fucks the lady. The video continues with everyone getting a taste of all.

As Tommy continues to mow his dick gets harder and harder as he thinks of those guys in the video. Finally he convinces himself, ‘If those guys had so much fun fucking, why can’t I?’ When he completed the mowing he loaded the mowers on the truck. He opened the truck door and took a Magnum BareSkin condom out of the small day back pack he carried. Putting the condom in his pocket he walked around to the deck. With an innocent smile on his face he said, “I’m really hot. Could I please have another Coke? Also, would it be OK if I just sat here in the shade while cooling off?” As she went into the house to fetch a Coke he sat, leaned back placing his arms behind his head exposing his trimmed arm pits, spread his legs, shut his eyes and thought about the plumber pounding the ass of the religious man.” His dick came to full attention squeezed in his shorts. The precum spot would have been visible if the shorts had not been drenched by sweat.

With his eyes still closed he heard, “Aren’t you a beautiful sight. Looks like you are having happy thoughts.” As he opened his eyes he saw her leaning over him with her tits hanging out more than before. “A penny for your thoughts.” She reached down and began massaging his upper leg. “How does this feel?”

“Great.”

As she kneeled her outfit fell open exposing her tits and lady parts. She unzipped his fly. He raised his ass so she could pull off his shorts and orange and blue wide stripped very brief cotton briefs. She leaned forward and with no difficulty swallowed his wet masterpiece, wet from precum and sweat. The sweat of the dick and balls encouraged her.

During the fuck that followed Tommy concentrated on the four guys in the video. Although he was a virgin to lady fucks he had seen enough videos to know what to do.

As he pulled his shorts on she placed her hand in his pocket. “Thank you for taking care of my property. I am going to call your boss and tell him what a fine job you did. I’ll ask to have you come every week.” When Tommy got back to his truck he reached into his pocket and pulled out a $50 bill. For the rest of the summer he found a $50 bill in his pocket every week. At the end of the summer his boss handed Tommy a letter address to him that had been mailed to the firm. Inside was a short note thanking him for being so meticulous about taking care to the lawn. The letter was signed by the husband. Enclosed was a check for $250.

………..

One afternoon in August as he walked into the house after work his mother exclaimed, “I am so glad you are home. I was just going to make a quick run to the Big Y Supermarket in Torrington. I need a few items so I can bake zucchini bread tomorrow morning for the community bake sale. I was afraid I might be late for book club this evening if I had to go to the market. Would you be a dear and go to the store for me? You can go now or later. Doesn’t matter as long as I have the groceries in the morning. You can eat now or warm up your supper when you return. Your father won’t be home as he is working late and then has his weekly poker game.”

“No problem mom. As soon as I take a shower I’ll be on my way.”

In the shower as Tommy washed the sweat and grim accumulated during his hard day of work giving special attention to his dick and balls. The feeling of his soapy fist massaging his dick was wonderful, as usual. As he slowly stroked he thought of the glory hole at the video store in Naugatuck. Then he suddenly had a thought. My mother has just asked me to go to Big Y Supermarket. Jokingly he thought, ‘Is this a sign that she wants me to visit the gay video store nearby. I’m driving right past it. I will go. Sorry dick, no more fun now. You will have to wait.’ Ten minutes later he was on his way to Torrington. The grocery list was in one pocket and the Magnum Bareskins in the other.

He put a $10 bill in the slot at the entrance to the ‘back room’. A green light went on and he pushed his way through the turn style. There was no additional charge and he could stay as long as he wished. He walked down a short hall and saw the shapes of three men standing and waiting. One had his eyes glued to his smart phone. Tommy immediately recognized him. It was torr8 from the hook-up web site who was also Doug from the auto supply store. Tommy did not want to be recognized. When torr8 / Doug had suggested they meet he had said no. Tommy had feared he might see someone he knew if he went to a nearby place and it had happened. He immediately stepped into the first booth and locked the door. As he sat on the bench in the small booth he considered the implications of being seen. Then he admonished himself. ‘If Doug / torr8 recognized me it would be from the auto parts store where we had an innocent five minute conversation a year ago. There is no way he would know we had conversations at the hook-up site. He never saw my face and besides he thinks that guy lives in Hartford’. A calmer Tommy walked out of the booth. Doug looked up from his phone. He smiled at Tommy. Then he walked into a booth and left the door open. Tommy assumed this was an invitation and stood across the hall from the open door. Doug smiled again as he rubbed his crotch. Tommy with no hesitation about breaking his personally imposed rule about one on one encounters entered the booth. Doug reached for the door, closed and locked it. Since this was Tommy’s first encounter with someone in a booth he was not sure what he should do. A smiling Doug placed his hand on Tommy’s crotch. He then kneeled. He undid Tommy’s belt, unzipped the cargo shorts and pulled them down. Doug gently massaged the bulge in Tommy’s black boxer briefs. He pulled the briefs down and Tommy’s dick popped out. The precum dripping head announced his great level of desire. Doug examined the dick and caressed the balls. As he leaned in to taste the precum Tommy pushed his head back. He reached for a condom in his pocket and handed it to Doug. “You don’t need this. I’m clean.”

Tommy replied, “Please. I won’t do anything without protection.”

Reluctantly Doug opened the packet and rolled on the condom. Then to Tommy’s amazement he leaned in a swallowed the impressive dick to its base. The feeling was intense. Tommy grabbed Doug’s shoulders as the obviously experience mouth swallowed and then pulled all the way back then swallowing again. As much as Tommy enjoyed this he wanted Doug’s. As he said “My Turn” he took a step back. Doug stood and Tommy kneeled. As Tommy pulled Doug’s red briefs down his 8 inch (20 cm) dick sprang out. Tommy was thrilled that the real thing was as magnificent as the photos on the hook-up site had indicated. Skin covered half of the head. He pulled the skin forward and as he squeezed the hard piece precum oozed out the skin opening. He then pushed the skin back exposing the mushroom head. Not only was the dick long, it was well rounded. He suddenly realized that his fantasy to be fucked by torr8 would not happen. This guy would rip his ass open. He reached for another condom and placed the open end over the head. He was thankful that he had purchased magnum size as it would have been difficult to roll a regular size one over this masterpiece. Even the magnum did not roll down as easily as it had on himself. Finally with the dick protected Tommy leaned in and licked the head and shaft. Then he put the head in his mouth. He could only go down the shaft about an inch (2.5 cm) until he gagged. Dough laughed, “You are not the first guy who had a problem taking me.” Tommy tried a couple more swallows and decided it would be better if he just stroked it and watch the skin move back and forth over the head. The design of the BareSkin with its loose shaft and tight base permitted the movement of the skin while the condom was safely in place at the base near the balls. Eventually Doug reached for Tommy’s armpits and pulled him up. Doug then turned around and rubbed his ass against Tommy’s continuously hard dick. He then stepped out of his pants that were around his ankles. He took a tube out of his pants pocket and undid the cap. After squeezing out lube reached back and generously greased Tommy’s condom covered hardon. He then applied more to his ass. He then spread his legs and leaned forward placing his arms on the bench. Although Tommy had never fucked a guy he needed no instructions. Between watching many fucks on videos and his experience with the cunt of the mowing client he felt confident as he placed his dickhead against the waiting hole. As he pushed in Doug’s only comment was “fuck me boy”. He was amazed that it slipped in so easily. While not the masterpiece of Doug, Tommy knew his dick was well above average in length and girth. He was afraid he might injure Doug. As he considered pulling out Doug shoved his body back against Tommy resulting in the dick going as deep as possible. “Fuck me, fuck me hard.” Tommy lost all concerns about injury and pulled half way out so he could ram back in. “Yea, yea, go hard and deep.” Tommy pulled all the way out and plunged in as hard as possible. “Fuck, fuck.” Tommy did it again. The third time he pulled completely out and plunged in as he began unloading. As Tommy cried out “I’m cumming” Doug could feel the pulsating of the dick rammed in. With Tommy still implanted Doug reached for his own piece and with one stroke filled the other condom.

As Tommy slipped out of Doug the other turned around. He reached down and with a tissue pulled the condom off of softening Tommy. Holding it up Doug admired the quantity of spunk filling it. While holding the condom in one hand he removed his and held it up. Both had impressive loads. As Doug dropped them into the small wastebasket he smiled at Tommy. That was amazing. I want to see you again. Tommy surprised himself when he agreed to exchange phone numbers with Doug.

Before the end of summer vacation when Tommy went off to UConn and Doug returned to Central Connecticut State they met twice at a state park. They parked at a trail crossing and hiked into the woods to a hidden area off the marked trail. While Tommy never fulfilled his fantasy of being fucked by torr8 (and possibly ripped open) he with great satisfaction serviced his friend.