Tommy’s Coming (Cumming) of Age - 8. Tommy’s Fantasy Cums True

Tommy had no idea what he meant by ‘fucking supplies’. As they pulled into the CVS parking lot Jay suggested Tommy wait in the car. “Since two guys buying condoms and other supplies together might be announcing their intentions I would prefer the good people of Mystic not know I am soon having a romp with a ‘twink’. Tommy chuckled at his being referred to as a ‘twink’. He had often seen ‘twinks’ on porn videos where an older guy was fucking a young innocent looking young man or vice-versa

Jay returned from the store, got in the van and handed Tommy the shopping bag. Tommy found a box of “Trojan Ecstasy condoms, two tubes of K-Y, a two pack of something called Fleet and two pints of Ben and Jerry ice cream: Chunky Monkey and Strawberry Cheesecake.

“What is Fleet?”

“You my friend will soon find out. I want a clean fuck, if you know what I mean. I do not know what is special about Ecstasy condoms, but since they were the most expensive I assumed they were the best.”

When they returned to the house they quickly put the ice cream in the refrigerator freezer compartment and ran upstairs. Jay spoke, “My friend, before we do it I want you squeaky clean inside. Take off your clothes and come into the bathroom. Now lie down on your side with your knees bent. I am going to gently insert the tip of the container in your ass. Then I will slowly squeeze the bottle and empty its contents into you. Then you lie there as long as you can. You will suddenly have an urge to go. When you cannot hold it in any longer sit on the toilet and let it loose. You will then be clean and ready for what you really want.”

Tommy laid as instructed. Jay kneeled and removed the cap from the applicator tip. It actually felt good when he gently shoved it in the ass. Tommy felt the stream of liquid filling him. Jay left the bathroom. At first it seemed like nothing had happened. Then quickly Tommy had the urge to go. He held it in as long as he could. Just as he sat on the toilet seat a hearty stream blasted out of his ass. As he watched the toilet flush he was glad that stuff that was going down the drain would not be there when Jay fucked him. He then took a quick ass area shower.

Naked Tommy walked into the bedroom. An equally naked Jay was sitting on the camping mattress. Jay asked, “Are you ready?”

“I fucking am!” He continued, “Of course I researched the best way to have a first fuck on your computer. It was suggested that the top lie flat on his back and the bottom kneel over him. That way the virgin bottom will be less anxious and uptight since he will be in full control.”

Jay opened a condom package and laid on his back. “Here, roll it on me.” Tommy examined the condom and then placed it over Jay’s hard dick. He had seen YouTube condom putting on demonstrations and rolled it down as he remembered making sure it went to the base of Jay’s dick. Both jay and Tommy were surprised that the condom was very loose, like it was purposely too big. Jay thought it might be defective. He examined the box it had come in. There was a picture of the condom showing it was large at the head and tight at the base. He now understood the construction. It was designed to not be tight over the head and possibly restrict sensitivity and pleasure while being tight at the base to hold it firmly in place. Jay explained this to Tommy. Both had deflated some during the condom inspection.

As soon as Jay said, “Are you ready?” both dicks immediately sprang to extreme hardness.

Jay opened the tube of K-Y and spread a generous amount on his condom covered dick. He then turned Tommy around and placed a gob on his finger. He gently massaged it around and into Tommy’s virgin ass hole. Tommy moaned with delight. Jay laid on his back and Tommy kneeled facing him. As he squatted down he felt the head of Jay against his hole. The inexperienced and naive to fucking, other than with an ice cream scoop handle, teenager plunged down onto the hard dick. He had often watched porn movies with guys showing pleasure as a dick was savagely thrust into their hole. He did not realize such treatment only gave pleasure to experienced holes. Tommy’s quick movement that shoved Jay’s dick into his virgin ass resulted in excruciating pain. He jumped up and stifled a scream of anguish. Jay stood and wrapped his arms around the trembling young man. “Take it easy my friend. Hard fucks are for experienced asses. We need to move slowly and tenderly. Hopefully you did not rip and damage your hole. We must go slowly.” Jay then took a tissue and gently rubbed it against the tender hole. He was relieved that there was no blood on the tissue, just K-Y. “Let’s take a short break to help the pain subside. Sit down. I’ll get some ice cream. Which do you want, Strawberry Cheesecake of Chunky Monkey?”

Tommy replied, “I think I would feel better standing. Chunky Monkey would be great.”

When Jay went to get the ice cream Tommy leaned against the wall. He held back the tears as he stood there. He had anticipated this moment for over a year. Every guy being fucked on the porn sites seemed to love it. His friends from Utah and Koki from Japan both had pleasurable encounters. Here he stood with a sore ass and a soft dick.

Jay had put on a T shirt and soon returned with Chunky Monkey and two spoons. He had worn the T shirt since there was a possibility his upper body might be observed through the kitchen window. Since the two had shared deep kisses and each other’s cum he did not think sharing a container of ice cream would be strange.

Both leaned against the wall as they shared the ice cream. When Jay placed his hand on Tommy’s back and gently massaged it the young man’s instinct was to push him away. But out of respect for his friend he let Jay continue. Gradually the physical touch felt good. He turned with his back to Jay and leaned into his friend. Jay continued to massage Tommy’s back and shoulders. He moved his hands to the front of the young man and massaged the chest, with emphasis on the nipples, and abs. As Jay moved his hands down Tommy moaned with pleasure. Jay gently wrapped his hand around the soft dick which immediately responded. As Tommy’s dick grew the pain in his ass was replaced by a feeling of contentment throughout his body.

“I want to try again.”

Jay’s massaging and stroking of his friend had brought him to full hardness and horniness. Still wearing the original condom he realized it had not slipped off when he had gotten soft. The special design with a tight base had held it on. “This time just let my dick enter your hole. Do not attempt to force it down. Just let it in and then wait while you ass adjusts to the new experience. Only when you feel comfortable let it slide in a little deeper. When I am about half way in and you do not feel pain move up and down giving yourself a half fuck. If, and only if, you feel no discomfort go down so I am deeper in you. When you ask for it I will begin thrusting.”

Tommy did as instructed. He let Jay’s head invade him. He felt discomfort but no pain. He leaned back and took in more of the dick. Again discomfort but no real pain. He moved up and down getting a half dick fuck. With each movement he went down a little deeper. To Tommy’s surprise he realized Jay was as deep as possible. He slowly moved up and then back. Having his ass invaded felt weird but did not hurt. A smile came on his face as he raised himself up and then pushed down completely engulfing Jay’s rock hard dick. Jay’s realized it felt too good. He looked up at Tommy and said, “If you keep that up the party will be over for me. Let’s take a short break. Tommy slowly raised himself and he felt the dick popping out of his hole.

Tommy smiled as he whispered, “That was an amazing feeling.”

Jay replied, “I think a change in position will even give you more pleasure.” Jay then rolled up the thin camping mattress. “Lay on you back with your ass high on the roll of the mattress.”

Tommy did as suggested. Jay then knelt between the long legs of the teen placing them on his shoulders. His ass was now completely exposed. Jay leaned forward and pressed his lips against Tommy’s. The young man responded by opening his lips and sucking in Jay’s tongue. Then Tommy raised his arms and wrapped them around Jay. Jay reached down and adjusted his dick which had filled the condom with precum aiming it directly against the hole. He then slightly pressed in. Tommy did not protest. He pushed in deeper. Tommy responded by attacking his mouth with his tongue. Jay pressed in as deep as he could go. Tommy screamed a whisper, “Amazing.” Tommy had a special feeling. He had read about ‘that spot’. Evidentially Jay’s dick had found it. Jay very slowly and tenderly pulled half way out. He then caringly thrust back in. He pulled back and again moved back in.

Jay could hold off no longer. With his next deep thrust his dick exploded filling the condom. Tommy felt the pulsating of his friend’s dick that was deeply buried in him. Since their bodies were pressed together Tommy could not touch himself. With desire to finish he began belly fucking Jay as the two tightly embraced. Jay mimicked his movements which put more pressure on the young dick. As he felt his juices rise Tommy tightened his grip on Jay and attacked his mouth with his lips and tongue. The essence of twink spewed between the two stomachs. Jay collapsed onto a totally drained teenager. Each could feel the heartbeat of the other pound against their chest. Finally Jay suggested they shower. Jay stood and reached for Tommy’s hand. The young man, still in a state of euphoria, at first had difficulty rising and standing. The two, hand in hand, walked to the bathroom. Each gently washed the other. Jay turned Tommy and gently cleansed the area he had just invaded.

After drying each other which resulted in rising dicks Jay suggested they go to the kitchen and finish the pizza and the other pint of ice cream. Wearing only T shirts they leaned against the kitchen counter feeding each other slices of pizza and sharing the Strawberry Cream Cheese Ben and Jerry’s ice cream. With a twinkle in his eye Tommy took his spoon and placed a dab of ice cream on Jay’s dick. He then kneeled and licked it clean. The physically fit older man responded and Tommy was soon deep throating his friend. Jay pushed him away. “Let’s save it for more serious activity.”

Tommy: “What do you have in mind?”

Jay: “How is your ass?”

“Painless and anticipating.”

Without another word the two ran up the stairs. Tommy laid on his back with ass raised on the mattress roll as Jay rolled on another condom and applied lube where appropriate.

Since Jay had cum less than thirty minutes earlier this fuck was prolonged. After a period of missionary position fucking Jay moved Tommy to his knees with ass exposed for a doggie style romp. This was followed by the strong Jay fucking Tommy standing with the young man against the wall held by Jay. They returned to the missionary position and once again Jay exploded into the willing ass. Jay then leaned down and took Tommy’s piece deep to its eight inch base. Immediately Jay had a mouthful. He leaned forward and while kissing Tommy gave the youth back his cum.

Following quick showers the two laid next to each other on separate camping mattresses sharing a blanket wearing only smiles.

Sometime in the middle of the night Jay felt something warm on his dick. With no surprise he realized Tommy was sucking him off. Jay pretended to be sleeping as he enjoyed the warm lips. He let his juices flow into the eager mouth. Tommy then leaned in a kissed Jay. In the twilight from the moon shining in the window Jay watched Tommy jerk off and then clean himself with tissues.

As the sun streamed into the window Jay woke. He observed the sleeping twink who had kicked off his blanket and displayed a glorious eight inch morning woodie. When Jay returned from his morning piss Tommy was awake laying on his back with his extended dick pointed up.

Tommy’s first words of the morning were, “Where is the other Fleet box?” Returning from the bathroom Tommy rolled up his mattress and laid on his back. Over an hour later they were at the Mystic Diner each having the Hungry Man breakfast special, (two eggs, two pancakes, home fries, sausage, bacon and ham) a meal that would certainly replenish their bodies and souls.

Returning to the house Tommy unloaded the lawn mower from the van and Jay got out garden tools. For two hours Tommy mowed and trimmed while Jay cleared brush and prepared flower beds.

When Jay suggested a break Tommy‘s dick responded in anticipation. Within minutes the two sweaty men were in the bedroom with Tommy on his back.

Following more yard work the two ordered take out grinders (what ‘hoagies’ or submarine sandwiches are called in Connecticut) and ate them sitting outside on the steps to the back door. When Jay asked Tommy if he was up to some quick fun the teen smiled and walked into the house.

Following an afternoon of yard work Jay gave Tommy the choice of dinner at a seafood place serving lobster or a steak house. Tommy chose the steak. After dinner on the way back to the house they stopped at CVS to buy more Trojans, K-Y, Fleet and pints of Ben and Jerry’s. The evening, night and morning followed the schedule of the previous day except with no pain or discomfort.

On Sunday morning they painted the walls of their love nest which would be the bedroom of young Sean. Tommy had been afraid someone might overhear him at the restaurant. Now he opened up to Jay telling him everything about his experiences over the past four years. He was relieved that he could finally share his adventures with someone other than his Skype friends in Japan and Utah. Jay shared his life story that was less interesting. His only man to man experience had been some messing around in high school with a couple of his fellow basketball team members and his three years fucking his college roommate. The only woman he had ever been with was his wife who had no inhibitions when they made love.

Jay then admitted that he had enjoyed inspecting the cum filled tissues left in his home office waste basket. Tommy was proud that he had impressed his friend with the quantity of cum. He would have been mortified if anyone else had found his glad rags.

Following a day of painting three rooms and numerous happiness breaks they departed for home. The following Wednesday as the moving truck was loaded he gave little Sean and Bobby goodbye hugs. As the family prepared to get into the van Mrs. Forster gave Tommy a hug and thanked him for being a good role model to her sons. He and Jay shook hands and then Jay pulled him into an appropriate to be seen by all man hug. Sean called out, “Tommy, We hope you will visit us.”

Tommy had the feeling that would never happen.