gtru1981

Legendary Member
Joined
Feb 15, 2013
Posts
170
Media
0
Likes
1,723
Points
363
Location
Charlotte (North Carolina, United States)
Sexuality
90% Gay, 10% Straight
Gender
Male
Hi Everyone, it has been a minute since I posted a story. I just wanted to warn people of my stories, for whoever read my story of Patrick and Cole.

1. Yes, my stories are very long. I like to be as detailed as I can, fleshing everything out. If you don't like that, I would suggest skipping this story. The story isn't just about sex, it has a story behind it.
2. This story came after watching Hulu's "Fire Island" and another story I read on here, that really inspired me to write another story.
3. This story is told from two perspectives, from both brothers. Each chapter is told by one of them.
4. I already wrote a whole bunch of chapters, as I been working hard on this story, adjusting it, trying to make it a really good story.

______________________________________________________________________________________________________________

My Straight Brothers Week at Fire Island.

Chapter 1: How it all Started (Anthony's Point of View)

There I was, stirring at the watermelon martini, the waiter just handed to my friend Henry. A second later, the waiter handed me my lychee martini. It was a beautiful Thursday summer evening, in Manhattan and I just finished having dinner with my besties at Elmo on 7th ave. I had the fried chicken, while Timmy, one of my best friends, had the classic meatloaf. Rodrigo, my other bestie, had the salmon, while Henry was just having a liquid dinner. We gathered tonight, to plan our 4th of July annual trip to Fire Island, coming up this weekend. This would be the first time in two years we would be going to Fire Island since the start of the pandemic lockdowns that hit the city extremely hard, back in March of 2020.

A little about myself, before I get into the story. My name is Anthony Caruso, but everyone calls me “Ant”. I am 28, gay, and born and raised in New York City, well, the South Shore section of Staten Island. I am one of seven in my family, 3 girls and 4 boys. My father, Vincenzo Caruso, aka Vinny, was born and raised in Bensonhurst Brooklyn. My lovely mother, Eleni Alexopoulos, was born and raised in Astoria Queens. My mother is a famous NYC news anchor, aka, Rosanna Scotto from Good Day New York, on Fox 5 NY archrival for another network in the city. My father comes from a long line of proud FDNY firefighters. My great grandfather, my grandfather, my father, and my 2 brothers are firefighters. It’s in our blood.

As I said before, I am one of seven in my family and the youngest. I came out at the age of 16, when my brother Tommy and my mother walked in on me blowing our next-door neighbor, hottie Chad Deluca, who was the captain of our football team at St. Joseph high school at that time. You would think, my family finding out me being gay would be a scandal, however it wasn’t. My brother Tommy, the one I am closest to, who I shared a bedroom with for years, is considered the black sheep in our family. Like I stated before, being part of the FDNY is a family tradition. Tommy, my 30-year-old brother, the star of our family growing up and the golden child of Staten Island. He was a star athlete and student, captain of our high school Football, baseball, and basketball team. Graduated in the top 3 of his graduating class and was offered multiple scholarships to schools like Duke, Boston University, and University of California, Berkeley, to name a few.

As you haven’t figured it out yet, Tommy is one of the main protagonists of our story. Tommy had it all, athletic, brains, and looks. All the boys in our family range between 6’1 to 6' 4, with the nice olive skin of being of Sicilian and Greek descent. Tommy was the tallest of all of us, at 6’4 and extremely good looking. However, once the golden child, things would take a turn, where he ends becoming the black sheep of our family. It all started his freshman year at BU, where he would meet Claire Friedman. A one-night stand and 9 months later, little TJ was born. This would lead to both Tommy and Claire dropping out of BU and heading to Long Island, where Claire was from. The betrayal would come after, as a rift would come between my father and brothers and him. Tommy should have joined the FDNY, like everyone else in our family. Heck, even though I am a senior software engineer manager for Warby Parker, I still work part time for the FDNY EMT team on the weekends. However, Claire had power over him, resulting in him becoming a cop on Long Island. This became such a scandal, not only in my family, but the neighborhood and Staten Island in general.

Fast forward to a few weeks ago, when Tommy walked in on Claire, the mother of his now 3 sons, getting railed in the kitchen by the hot, tall, and hung Puerto Rican UPS guy. Come to find out, Claire and Luis, the young 23-year-old driver, have been having an affair for a while, since the start of the lockdowns. Tommy tried to make it work, however, it was revealed that Claire ended up getting pregnant by the affair. So here we are now, me having dinner with my friends, when Tommy calls me, stating he has arrived at Penn Station.

“Hey guys, we will have to put this on hold until tomorrow. Tommy just arrived at Penn Station, and he is going to crash at my place for a while.” I said, while dropping money on the table.

My thirsty friends all perked up when I brought up my brother’s name. Like I said, even at 30 years old, he was still extremely good looking, the dimples would drive my friends crazy, when he smiled. As Rodrigo, Timmy, and many others have said, “my brother oozes sex”. The thing about Tommy, ever since he discovered I was gay at 16, he has been a major supporter of the LGBT community. While I am very close with my family and my siblings, my relationship with Tommy was on another level. We always had each other’s back. I remember, when same-sex marriage became legally recognized in New York on July 24, 2011, Tommy was with me and my friends, celebrating at Stone Wall. Same thing as well in 2019, when we celebrated the 50th anniversary of the StoneWall Riots, he was there, with his cop friends from Long Island to celebrate.

As I got off the 34th street subway station, I saw my brother across the street, waiting for me under the famous Madison Square Garden sign. However, the usually happy, chipper, life of the party person I knew, wasn’t. He looked deflated, sad, and lost. We hugged one another and got into an Uber to head to my apartment in Long Island City. Once home, Tommy went to go take a shower, as I was preparing the guest bedroom for him. Once he got out of the bathroom, in his pj pants and tank top, he sat next to me on the bed. He lowered his head to my shoulder and started to cry. My brother has been defeated.

After a few minutes, he looked up and saw my suitcase on the side and asked me if I was going somewhere. I told him I was planning on going to Fire Island for the 4th with the guys, but I could cancel if he wanted me to stay. He said no, he would just stay at my apartment and be depressed. I went into the kitchen and on our 4th of July group chat, I told my friends, I probably wasn’t going to go because of Tommy. Timmy and Rodrigo chimed in right away and told me to bring him. I knew those thirsty queens would want him around, they have been wanting to ride his dick, since the day they met him. However, it was Henry, who’s house we will be staying at, texted me on the side, and told me to bring him along.

I went back into the bedroom and asked Tommy if he wanted to go to Fire Island, to get away from everything and have fun with us. He was very hesitant at first, since it would be him, surrounded by a bunch of horny gay men. However, after thinking about it, he agreed and I informed the group, Tommy would be coming with us. Lord, I hope everything goes well.
 
Chapter 2: On our way to Fire Island (Anthony's point of view)

It was Saturday, July 2nd and we just arrived at the Sayville Ferry terminal, to head over to Cherry Grove for our weeklong 4th of July Fire Island trip. We wanted to get there early, since after 2 years of Covid restrictions, we knew this weekend was going to be super busy, especially with the great weather we are supposed to have. As we boarded our 10:25 am ferry, the boat was already packed. Tommy was in total shock, as everyone on the boat was pretty much naked. Everyone from the twinks to the bears, were wearing the least amount of clothes. All you saw were guys in mini shorts, swim mini briefs, or jockstraps. Tommy was memorized about how ripped a lot of the guys were. I again had to remind my friends that my brother was off limits, as he is straight and just looking to have fun.

By the time we arrived in Cherry Grove and settled into our house, a few of us already had a few drinks. Tommy and Henry took shots of tequila on the boat with some other guys, while the rest of us were drinking White Claws. The house we were staying, is a beautiful 5 bedroom and two and a half baths, located right in front of the beach. The house is huge, at over 3,000 square feet, which includes a heated pool, hot tub, and an outdoor sauna. Tommy, I, and Henry all got our own rooms with a queen size bed, while Rodrigo and Timmy got rooms with two twin beds. The house has been in Henry’s family for over 100 years, so it’s the reason why we can have it whenever we want and don’t have to pay to stay there. He decided to relax for a bit, before heading out to Pine Pantry, to stock up on supplies for dinner tonight. Rodrigo is a great chef, working at the famous Gramercy Tavern, as their head chef.
Word was already spreading quickly around the island that my straight and extremely good-looking brother was on the island. When I was in college and up until the lockdowns, I use to bartend at many of the popular gay bars in the city, so people know who I am. To make matters worse, Tommy was wearing some tight-fitting swim trunks that revealed a lot, especially his muscular firm ass, along with a tight-fitting tank top. He would blush, as we were walking, as he was getting cat calls, but seem to really love the attention. After we returned from the grocery store, we decided to head to the beach, to swim, relax and watch all the cute boys.

Once at the beach, Tommy started to get more comfortable, even though pretty much everyone was naked on the beach. Tommy ended up taking his shirt off and decided to get into the water with Timmy and Henry, as Rodrigo and some other friends we knew, sat on the beach.

“God, your brother is a Greek Adonis, everyone is talking about him!” Said Trevor, a friend I knew.

“He already has a hashtag on TikTok, Insta, SnapChat, and even Grindr. #snagthestraighthottie.” Rodrigo said, while showing me the hashtag.

“Lord, I am so glad I douched for this trip, wouldn’t mind having daddy pound me hard!” Brian, another friend said while licking his lips.

Tommy was slowly leaving the water and heading back to us, when I noticed, every horny guy was eye fucking him!

“Look at that cock sticking to those trunks! I am guessing the whole family must be blessed and cut!” Rodrigo said, as he slapped me on the back.

“Can you hand me my towel Ant?” Tommy asked, as he was dripping water from his tan, muscular body and everyone was at this point was in ah, while he was totally oblivious lol.

Just then, a gorgeous, around 6’2, 8 pack abs, blonde hair swaying in the wind came up to us, well mostly towards my brother.

“Hi, my name is Travis and my friends, and I need an extra guy to complete our volleyball game we have going on? Would you be interested in joining us?

“That would be fun, I love beach volleyball. Ant, do you and your friends mind, If I go play volleyball with Travis and his friends?” Tommy asked.

“Go do you boo-boo! It's your weekend to get away and have fun!” I said with a grin.
 
Chapter 2: On our way to Fire Island (Anthony's point of view)

It was Saturday, July 2nd and we just arrived at the Sayville Ferry terminal, to head over to Cherry Grove for our weeklong 4th of July Fire Island trip. We wanted to get there early, since after 2 years of Covid restrictions, we knew this weekend was going to be super busy, especially with the great weather we are supposed to have. As we boarded our 10:25 am ferry, the boat was already packed. Tommy was in total shock, as everyone on the boat was pretty much naked. Everyone from the twinks to the bears, were wearing the least amount of clothes. All you saw were guys in mini shorts, swim mini briefs, or jockstraps. Tommy was memorized about how ripped a lot of the guys were. I again had to remind my friends that my brother was off limits, as he is straight and just looking to have fun.

By the time we arrived in Cherry Grove and settled into our house, a few of us already had a few drinks. Tommy and Henry took shots of tequila on the boat with some other guys, while the rest of us were drinking White Claws. The house we were staying, is a beautiful 5 bedroom and two and a half baths, located right in front of the beach. The house is huge, at over 3,000 square feet, which includes a heated pool, hot tub, and an outdoor sauna. Tommy, I, and Henry all got our own rooms with a queen size bed, while Rodrigo and Timmy got rooms with two twin beds. The house has been in Henry’s family for over 100 years, so it’s the reason why we can have it whenever we want and don’t have to pay to stay there. He decided to relax for a bit, before heading out to Pine Pantry, to stock up on supplies for dinner tonight. Rodrigo is a great chef, working at the famous Gramercy Tavern, as their head chef.
Word was already spreading quickly around the island that my straight and extremely good-looking brother was on the island. When I was in college and up until the lockdowns, I use to bartend at many of the popular gay bars in the city, so people know who I am. To make matters worse, Tommy was wearing some tight-fitting swim trunks that revealed a lot, especially his muscular firm ass, along with a tight-fitting tank top. He would blush, as we were walking, as he was getting cat calls, but seem to really love the attention. After we returned from the grocery store, we decided to head to the beach, to swim, relax and watch all the cute boys.

Once at the beach, Tommy started to get more comfortable, even though pretty much everyone was naked on the beach. Tommy ended up taking his shirt off and decided to get into the water with Timmy and Henry, as Rodrigo and some other friends we knew, sat on the beach.

“God, your brother is a Greek Adonis, everyone is talking about him!” Said Trevor, a friend I knew.

“He already has a hashtag on TikTok, Insta, SnapChat, and even Grindr. #snagthestraighthottie.” Rodrigo said, while showing me the hashtag.

“Lord, I am so glad I douched for this trip, wouldn’t mind having daddy pound me hard!” Brian, another friend said while licking his lips.

Tommy was slowly leaving the water and heading back to us, when I noticed, every horny guy was eye fucking him!

“Look at that cock sticking to those trunks! I am guessing the whole family must be blessed and cut!” Rodrigo said, as he slapped me on the back.

“Can you hand me my towel Ant?” Tommy asked, as he was dripping water from his tan, muscular body and everyone was at this point was in ah, while he was totally oblivious lol.

Just then, a gorgeous, around 6’2, 8 pack abs, blonde hair swaying in the wind came up to us, well mostly towards my brother.

“Hi, my name is Travis and my friends, and I need an extra guy to complete our volleyball game we have going on? Would you be interested in joining us?

“That would be fun, I love beach volleyball. Ant, do you and your friends mind, If I go play volleyball with Travis and his friends?” Tommy asked.

“Go do you boo-boo! It's your weekend to get away and have fun!” I said with a grin.
Can't wait for more.
 
  • Like
Reactions: Jjjay94
Chapter 3: Tommy’s meets a new friend (Tommy’s point of view)

As I was walking away from my brother and his friends to join Travis and his crew to play volleyball, I looked back to see if Ant was mad or disappointed. Yes, I came here to get away from my shitty life and relax and have fun. However, I came here to spend time with my younger brother, the only person in my life I can truly trust and hasn’t shunned me, like the rest of my family. The one thing I realized about the gays and especially Fire Island, they love to wear their bikini briefs. For the next 3 hours, I had a ton of fun playing volleyball with Travis and his friends, when Ant came up to me and informed, he was going back to the house, to relax by the pool and get ready for dinner. He dropped off my wallet and cell phone and reminded me to be back at the house around 7:30 for dinner or call us if I make other plans.

“We will take GREAT care of your brother honey, don’t you worry!” The guys told Ant, as they were giggling and waving their hands, when Ant was walking away with that smile I knew very well.

We kept playing for another 30 minutes, when everyone decided to call it quits and head back to their places to relax before tonight's shenanigans. I decided I needed to cool off and told Travis I was going to take a dip in the ocean, so he decided to join me. After getting out of the water, we both sat there, talking, while drying off. I discovered that Travis was 33 years old, originally from Toms River, NJ. He is a personal trainer and has a lot of famous celebrities as his clients. His partner of 3 years passed away due to Covid, in the beginning of the pandemic since he was a nurse. I told him about how I was recently set to get divorced, since my soon to be ex decided to have a baby with the UPS guy. At one point, Travis placed his arm on my back and started to caress it. I didn’t mind, until he was trying to get his fingers to go inside my shorts.

I got up and informed Travis, I should get going. He asked if I wanted to grab a drink before we both went our separate ways, which I agreed. As we were headed over to the Pavilion for a quick drink, I was stopped dead in my tracks. There, at the community showers, were 4 of the guys that we were playing volleyball with. One had his hands in the air, holding on to the top of the shower wall, as another was on his knees, with his face deep into his butt cheeks. When he came up to take a breather, he then took turns sucking off the other two. One was on the right and the other was on the left. I was amazed by his throat skills, as the two guys look very hung and thick. It caught me by surprise and Travis noticed it and laughed.

“Welcome to Fire Island! This is just the G rated stuff you will see this week!” Travis laughed, as he patted my back.

I stood there for a few seconds, watching this interaction between the four, as the light skinned black guy, who was very blessed down there, gave me a wink and blew a kiss to me. We got to the bar, and the bartender recognized me right away.

“Aren’t you Ant’s straight brother and Eleni’s son? God, I love your mother, she is an icon!! Fierce and fabulous! You darling, are the talk of the island!”

I started laughing because people were talking about me, like they never met a straight guy before. My mother is very famous in NYC, especially with gay men, they love her. Just then, a drag queen came over and was talking to the bartender and then rang a bell and spoke to the crowd.

“Attention everyone! We have some new, drop-dead, and gorgeous meat sitting right here! A regulation hottie!” She screamed this out to the now large crowd.

“Drinks are on the house for you boys today, what will you two be having?” The bartender informed us

I informed the bartender, whose name was Adam, that I would like a Corona, while Travis had a green mojito. Travis and I kept chatting about life and such, he was a nice person to talk to, I will say. I decided to be brave and order a green mojito and Travis ordered another, along with tequila shots. At one point, the drag queen came to me and ripped off my tank top and asked me to flex for the crowd at the bar. The crowd went wild when I started to flex and the crowd started to feel my muscles, chest, and some even grabbed my ass. After my 3rd mojito, I informed Travis I had to head back home for dinner. Travis gave me sad puppy dog eyes and begged me to stay. It was during this point that he planted his hand on my inner thigh and started to caress it.
I did let Travis know, I will stay for one more drink, but had to go and if I wanted to hang out again, we should exchange numbers. I didn’t mind Travis caressing my inner thighs, or that other guys were trying to pinch my butt. It’s been a very long time, since I had sex, maybe I just like the attention, who knows, I was having fun. Travis was getting braver, and he slid his chair closer to me and started to caress my upper thigh, very close to my cock. I don’t know if it was the touching, but I was starting to get a little horny and hard and he started to notice. Without notice, Travis inserted his fingers under my shorts and his fingers were now touching the tip of my cock head. It caught me by surprise, so much, I jumped a little bit from my seat. I removed his hand and told him I was heading home.
I informed him, I hope to see him and as I was leaving, I made sure the crowd would see me adjusting my now half hard on. Oh, I got a ton of looks, looks of thirst, knowing these guys want my thick, veiny, 8.5 cock. It made me smile and threw my tank top to the drag queen and walked away, heading home.
 
Chapter 4: The next day (Tommy’s point of view)
It was a beautiful Sunday morning, and everyone was still sleeping, so I decided to go for a quick run on the beach. Once I came back from the Pavilion last night, we had a wonderful dinner and just hung out by the pool for the rest of the night. I decided to go shirtless for my run, wearing only my Lululemon Fast and Free Reflective Shorts. On my way back from running on the beach, I got a text message from Travis, inviting me and my brother and his friends to his pool party at his house. When I got home, I informed the guys, we were invited to a pool party and to get ready, we were leaving in 10 minutes.

When we arrived, I noticed there were a ton of guys, hanging by the pool, on the patio, and all seemed to be already drunk or hung over from the night before. I was looking around and was realizing everyone was pretty much naked or just in their bikini briefs. I will admit, these guys, ranging from their early 20’s to their early 50’s, all had killer bodies, which kind of made me feel self-conscious. A few hours went by, and I was having the time of my life. We played beer pong, flip cup, went swinging and by now, everyone, including my brother, were wasted. I was on the patio, dancing to some great music with Travis and a couple of his friends, when I noticed my brother walking away with a cute looking Asian guy.

“Looks like your brother is about to get some!” Travis said, as he slapped my back.

I chuckled and was proud that my little brother was about to get some action. I was thinking I was cock blocking him, while on this trip. As Travis went to get another drink, a voice behind me introduced himself as he tapped me on the shoulder.

“Hi, my name is Jacob, I think you and I are the only two sober ones here.” Jacob said, while shaking my hand.

He wasn’t lying, I only had two beers this whole time while we were at the pool party. Jacob asked me if I would like to take a walk on the beach, away from the loud music and the drunk people. I agreed, as I was starting to get a little uncomfortable, with the touching and the sexual comments. I was going to let Travis know where I was going, but saw he was occupied. Travis was making out with two guys, while all of them had their cocks out, jacking each other off.

During our walk on the beach, the sun was beaming high in the sky and the waves were splashing on our feet. I learned a few things about Jacob. He was 21 years old, a student at John Hopkins University, majoring in Medicine, Science, and the Humanities. He hoped to eventually enroll in medical school. He was here with his friends from Philadelphia, where he is originally from. A young good looking Jewish twink, with curly brown hair, a beard, and chest hair, he wasn’t like all the other super buff guys, all they cared about were their buff and hairless bodies.

“So, Jacob, how come you didn’t want to stay at the pool party, there were so many guys there, eventually you could have found one?” I asked during our walk.

“I honestly don’t fit in this type of group of guys. They are all super buff, all they care are their bodies, getting drunk, doing drugs, and having anonymous sex with any other hot guy. I don’t drink or do drugs, as you can see, I don’t have a muscular or hairless body like all those guys at the pool party. Why did you want to leave?” Jacob asked.

“Well, my brother invited me. I am in the process of getting divorced from my soon to be bitch ex-wife. I just needed to get away from things.” I stated.

We reached the beach house and thanked Jacob for the walk, as I was heading inside to take a shower, nap, work out and relax by the pool, while I had the house to myself. Jacob asked me if I wanted to get dinner later and a drink and I agreed and exchanged numbers since he never once came on to me or made me uncomfortable.
 
Chapter 4: The next day (Tommy’s point of view)
It was a beautiful Sunday morning, and everyone was still sleeping, so I decided to go for a quick run on the beach. Once I came back from the Pavilion last night, we had a wonderful dinner and just hung out by the pool for the rest of the night. I decided to go shirtless for my run, wearing only my Lululemon Fast and Free Reflective Shorts. On my way back from running on the beach, I got a text message from Travis, inviting me and my brother and his friends to his pool party at his house. When I got home, I informed the guys, we were invited to a pool party and to get ready, we were leaving in 10 minutes.

When we arrived, I noticed there were a ton of guys, hanging by the pool, on the patio, and all seemed to be already drunk or hung over from the night before. I was looking around and was realizing everyone was pretty much naked or just in their bikini briefs. I will admit, these guys, ranging from their early 20’s to their early 50’s, all had killer bodies, which kind of made me feel self-conscious. A few hours went by, and I was having the time of my life. We played beer pong, flip cup, went swinging and by now, everyone, including my brother, were wasted. I was on the patio, dancing to some great music with Travis and a couple of his friends, when I noticed my brother walking away with a cute looking Asian guy.

“Looks like your brother is about to get some!” Travis said, as he slapped my back.

I chuckled and was proud that my little brother was about to get some action. I was thinking I was cock blocking him, while on this trip. As Travis went to get another drink, a voice behind me introduced himself as he tapped me on the shoulder.

“Hi, my name is Jacob, I think you and I are the only two sober ones here.” Jacob said, while shaking my hand.

He wasn’t lying, I only had two beers this whole time while we were at the pool party. Jacob asked me if I would like to take a walk on the beach, away from the loud music and the drunk people. I agreed, as I was starting to get a little uncomfortable, with the touching and the sexual comments. I was going to let Travis know where I was going, but saw he was occupied. Travis was making out with two guys, while all of them had their cocks out, jacking each other off.

During our walk on the beach, the sun was beaming high in the sky and the waves were splashing on our feet. I learned a few things about Jacob. He was 21 years old, a student at John Hopkins University, majoring in Medicine, Science, and the Humanities. He hoped to eventually enroll in medical school. He was here with his friends from Philadelphia, where he is originally from. A young good looking Jewish twink, with curly brown hair, a beard, and chest hair, he wasn’t like all the other super buff guys, all they cared about were their buff and hairless bodies.

“So, Jacob, how come you didn’t want to stay at the pool party, there were so many guys there, eventually you could have found one?” I asked during our walk.

“I honestly don’t fit in this type of group of guys. They are all super buff, all they care are their bodies, getting drunk, doing drugs, and having anonymous sex with any other hot guy. I don’t drink or do drugs, as you can see, I don’t have a muscular or hairless body like all those guys at the pool party. Why did you want to leave?” Jacob asked.

“Well, my brother invited me. I am in the process of getting divorced from my soon to be bitch ex-wife. I just needed to get away from things.” I stated.

We reached the beach house and thanked Jacob for the walk, as I was heading inside to take a shower, nap, work out and relax by the pool, while I had the house to myself. Jacob asked me if I wanted to get dinner later and a drink and I agreed and exchanged numbers since he never once came on to me or made me uncomfortable.
Damn So Hot now. I guess he will fuck Jacob for a very first time and later on He will bottom for Travis. Before he leaves he will get gang bang by a whole bunch of them. Thanks for your time. Can't wait for more.
 
  • Like
Reactions: gtru1981
Chapter 4: The next day (Tommy’s point of view)
It was a beautiful Sunday morning, and everyone was still sleeping, so I decided to go for a quick run on the beach. Once I came back from the Pavilion last night, we had a wonderful dinner and just hung out by the pool for the rest of the night. I decided to go shirtless for my run, wearing only my Lululemon Fast and Free Reflective Shorts. On my way back from running on the beach, I got a text message from Travis, inviting me and my brother and his friends to his pool party at his house. When I got home, I informed the guys, we were invited to a pool party and to get ready, we were leaving in 10 minutes.

When we arrived, I noticed there were a ton of guys, hanging by the pool, on the patio, and all seemed to be already drunk or hung over from the night before. I was looking around and was realizing everyone was pretty much naked or just in their bikini briefs. I will admit, these guys, ranging from their early 20’s to their early 50’s, all had killer bodies, which kind of made me feel self-conscious. A few hours went by, and I was having the time of my life. We played beer pong, flip cup, went swinging and by now, everyone, including my brother, were wasted. I was on the patio, dancing to some great music with Travis and a couple of his friends, when I noticed my brother walking away with a cute looking Asian guy.

“Looks like your brother is about to get some!” Travis said, as he slapped my back.

I chuckled and was proud that my little brother was about to get some action. I was thinking I was cock blocking him, while on this trip. As Travis went to get another drink, a voice behind me introduced himself as he tapped me on the shoulder.

“Hi, my name is Jacob, I think you and I are the only two sober ones here.” Jacob said, while shaking my hand.

He wasn’t lying, I only had two beers this whole time while we were at the pool party. Jacob asked me if I would like to take a walk on the beach, away from the loud music and the drunk people. I agreed, as I was starting to get a little uncomfortable, with the touching and the sexual comments. I was going to let Travis know where I was going, but saw he was occupied. Travis was making out with two guys, while all of them had their cocks out, jacking each other off.

During our walk on the beach, the sun was beaming high in the sky and the waves were splashing on our feet. I learned a few things about Jacob. He was 21 years old, a student at John Hopkins University, majoring in Medicine, Science, and the Humanities. He hoped to eventually enroll in medical school. He was here with his friends from Philadelphia, where he is originally from. A young good looking Jewish twink, with curly brown hair, a beard, and chest hair, he wasn’t like all the other super buff guys, all they cared about were their buff and hairless bodies.

“So, Jacob, how come you didn’t want to stay at the pool party, there were so many guys there, eventually you could have found one?” I asked during our walk.

“I honestly don’t fit in this type of group of guys. They are all super buff, all they care are their bodies, getting drunk, doing drugs, and having anonymous sex with any other hot guy. I don’t drink or do drugs, as you can see, I don’t have a muscular or hairless body like all those guys at the pool party. Why did you want to leave?” Jacob asked.

“Well, my brother invited me. I am in the process of getting divorced from my soon to be bitch ex-wife. I just needed to get away from things.” I stated.

We reached the beach house and thanked Jacob for the walk, as I was heading inside to take a shower, nap, work out and relax by the pool, while I had the house to myself. Jacob asked me if I wanted to get dinner later and a drink and I agreed and exchanged numbers since he never once came on to me or made me uncomfortable.
Good sigh that he knew he exchanged numbers with gay guys. It means he wanted something.
 
Chapter 5: Pool Party: (Anthony’s point of view)
I was deep inside him, the Asian bottom I met at the pool bar 15 minutes ago.

“Oh, shit, yes,” I murmured. “Shit, you can take it deep!”

I was in one of the bathrooms at the house, pumping my cock deep inside this slut I just met. I rolled him over on his back, grasped his legs over my shoulders, and continued to fuck him harder and deeper, until I blow my huge load inside of him.

As I walked outside to find my friends and brother, I never even gotten the name of the guy I just had sex with, but it felt good to be back at Fire Island. I looked at my phone and saw a few text messages from Tommy. He stated that he left the party and went back home to relax and for me and the guys to have fun! I found Henry by the bar, making out with some random guy, as he had his fingers inside his shorts. I bumped into him, to get his attention and he told the guy too fuck off lol.

We both scoped the party out, as it had grown to over 300 guys. It legit became a sex party. On the bar, we saw 4 guys standing on it, fully naked with their erect cocks, pointing to everyone. A bunch of other guys were pouring liquor down the front and back of their bodies. There were other guys sucking the booze from their erect cocks and another group in the back, sucking it from their butt cracks. Henry then pointed to the porch, where a group of 12 guys were all having sex with one another. At this point, we wanted to find the others and leave the party. As we were walking around the huge crowd, we heard Timmy.

“Take me. Give me your thick black cock! I can take it, YES, YES, FUCK ME!!!”

There, on a towel, in the grasses by the fence, was Timmy, getting pounded by a 6’1, lean muscular, older black guy. He was probably in his late 30’s or early 40’s. The guy’s massive balls began to slap against Timmy’s smooth ass as they fucked. His magnificent cock thrusting backwards and forwards, up and down, in and out. They gasped and sighed together, as my own cock hardened in my briefs. Henry noticed my cock rose vertically erect and began to slip out of my shorts and slap against my stomach, leaking precum.

Henry grasped my hard erect cock and began to stroke me, gently at first but would increase his urgency. I clenched my cheeks together, as I knew I was about to cum again. This is the first time Henry, and I ever did anything sexual. We have been friends since our freshman year at NYU and throughout the years, only hooked up once, during our freshman year.

"Oh, God, I am about to blow my seed inside you!" The guy who was fucking Timmy said, as he grabbed

Timmy’s throat and now was hovering over him, as his kept blasting load after load into my friend.
The sight of seeing my friend, dripping in sweat, getting railed, and having this beautiful bull blasting load after load into his hole, did it for me. The sight of seeing this guy’s cum, dripping from Timmy’s hole, made my cock start blasting my load over my stomach and chest.

"Fuck, my cock!" I yelled

"That was great, Ant! I love the way your cock throbbed in my hand, as you were cumming!” Henry whispered into my ear, before letting go of my cock and licking the cum off his hand.

As we collected ourselves, we found Rodrigo and left the pool party, heading over to Cherries, one of the main gay bars of Fire Island. When we got there, the bar had double the crowd size of the pool party. Go-Go boys everywhere, dancing on top of the bar and tables, wearing nothing but a small towel covering their cocks. The towels were so tiny, you can clearly see the guys, like the hot Dominican and Puerto Rican boys dancing, with their thick and fat uncut cocks hanging past the end of their towels. Timmy and Rodrigo couldn’t help themselves and decided to cop a feel of their delicious cocks.

The group eventually parted ways and it was just Henry and me at the bar ordering drinks, while a sexy frat boy type GO-GO Boy was standing over us and began to rub his thick cock over my face, pausing at my mouth as I licked the tip of it. Before I could engulf his cock into my mouth, he got on his knees and whispered to meet him in the Meatrack. I looked at Henry and gave me the “Go get it” look and he said he was heading back home, since he had a lot to drink and was crashing from taking Molly at the pool party.

Once at the Meatrack, I got on my knees and took the dancer's cock in my mouth. After 5 minutes of bobbing up and down on this dancer’s cock, I watched as he pulled me away and slid a condom over his cock and turned me over and slapped my ass.

"Fuck me! I want your cock!” I said, waiting for him to enter me.

The dancer made me get on all fours, as he started to slap my ass and finger my tight wet hole. After a 10-minute pure pleasure of him teasing my hole, I felt his cock entering me. As a top he was dominant and one of those guys that liked to feel a long stroke on his dick and when he was almost pulled out, he would slam back inside me, which drove me crazy with the sensation especially as I could feel his nuts swaying forward as he went deeper into me with each thrust. He fucked me for what seemed like forever, occasionally he would let up and force me to suck his cock.

“Use your ass to make me cum” he demanded.

“Take it deep! Slam down on my cock!” He spoke.

I kept working on his cock and he commanded me to fuck it harder and harder. I rode him hard until he was ready to cum and then he took over, grabbed my hips, and pulled me down as deep as he could go before blasting his seed into my hole. I was in ecstasy, as he blasted a good 5 loads into me. After he knew, he was done feeding my hungry hole with his seed, he slapped my ass, got up and said he hoped to see me again and walked away, back to Cherries. I needed a few minutes to compose myself, before heading back to the bar. As I was scoping the place out, looking for my friends, I was shocked at who was looking at me. I froze, I wanted to run, however he already saw me. There, in the crowd, across the bar, was my ex-boyfriend, the one that broke my heart, Lee Thompson.
 
Chapter 5: Pool Party: (Anthony’s point of view)
I was deep inside him, the Asian bottom I met at the pool bar 15 minutes ago.

“Oh, shit, yes,” I murmured. “Shit, you can take it deep!”

I was in one of the bathrooms at the house, pumping my cock deep inside this slut I just met. I rolled him over on his back, grasped his legs over my shoulders, and continued to fuck him harder and deeper, until I blow my huge load inside of him.

As I walked outside to find my friends and brother, I never even gotten the name of the guy I just had sex with, but it felt good to be back at Fire Island. I looked at my phone and saw a few text messages from Tommy. He stated that he left the party and went back home to relax and for me and the guys to have fun! I found Henry by the bar, making out with some random guy, as he had his fingers inside his shorts. I bumped into him, to get his attention and he told the guy too fuck off lol.

We both scoped the party out, as it had grown to over 300 guys. It legit became a sex party. On the bar, we saw 4 guys standing on it, fully naked with their erect cocks, pointing to everyone. A bunch of other guys were pouring liquor down the front and back of their bodies. There were other guys sucking the booze from their erect cocks and another group in the back, sucking it from their butt cracks. Henry then pointed to the porch, where a group of 12 guys were all having sex with one another. At this point, we wanted to find the others and leave the party. As we were walking around the huge crowd, we heard Timmy.

“Take me. Give me your thick black cock! I can take it, YES, YES, FUCK ME!!!”

There, on a towel, in the grasses by the fence, was Timmy, getting pounded by a 6’1, lean muscular, older black guy. He was probably in his late 30’s or early 40’s. The guy’s massive balls began to slap against Timmy’s smooth ass as they fucked. His magnificent cock thrusting backwards and forwards, up and down, in and out. They gasped and sighed together, as my own cock hardened in my briefs. Henry noticed my cock rose vertically erect and began to slip out of my shorts and slap against my stomach, leaking precum.

Henry grasped my hard erect cock and began to stroke me, gently at first but would increase his urgency. I clenched my cheeks together, as I knew I was about to cum again. This is the first time Henry, and I ever did anything sexual. We have been friends since our freshman year at NYU and throughout the years, only hooked up once, during our freshman year.

"Oh, God, I am about to blow my seed inside you!" The guy who was fucking Timmy said, as he grabbed

Timmy’s throat and now was hovering over him, as his kept blasting load after load into my friend.
The sight of seeing my friend, dripping in sweat, getting railed, and having this beautiful bull blasting load after load into his hole, did it for me. The sight of seeing this guy’s cum, dripping from Timmy’s hole, made my cock start blasting my load over my stomach and chest.

"Fuck, my cock!" I yelled

"That was great, Ant! I love the way your cock throbbed in my hand, as you were cumming!” Henry whispered into my ear, before letting go of my cock and licking the cum off his hand.

As we collected ourselves, we found Rodrigo and left the pool party, heading over to Cherries, one of the main gay bars of Fire Island. When we got there, the bar had double the crowd size of the pool party. Go-Go boys everywhere, dancing on top of the bar and tables, wearing nothing but a small towel covering their cocks. The towels were so tiny, you can clearly see the guys, like the hot Dominican and Puerto Rican boys dancing, with their thick and fat uncut cocks hanging past the end of their towels. Timmy and Rodrigo couldn’t help themselves and decided to cop a feel of their delicious cocks.

The group eventually parted ways and it was just Henry and me at the bar ordering drinks, while a sexy frat boy type GO-GO Boy was standing over us and began to rub his thick cock over my face, pausing at my mouth as I licked the tip of it. Before I could engulf his cock into my mouth, he got on his knees and whispered to meet him in the Meatrack. I looked at Henry and gave me the “Go get it” look and he said he was heading back home, since he had a lot to drink and was crashing from taking Molly at the pool party.

Once at the Meatrack, I got on my knees and took the dancer's cock in my mouth. After 5 minutes of bobbing up and down on this dancer’s cock, I watched as he pulled me away and slid a condom over his cock and turned me over and slapped my ass.

"Fuck me! I want your cock!” I said, waiting for him to enter me.

The dancer made me get on all fours, as he started to slap my ass and finger my tight wet hole. After a 10-minute pure pleasure of him teasing my hole, I felt his cock entering me. As a top he was dominant and one of those guys that liked to feel a long stroke on his dick and when he was almost pulled out, he would slam back inside me, which drove me crazy with the sensation especially as I could feel his nuts swaying forward as he went deeper into me with each thrust. He fucked me for what seemed like forever, occasionally he would let up and force me to suck his cock.

“Use your ass to make me cum” he demanded.

“Take it deep! Slam down on my cock!” He spoke.

I kept working on his cock and he commanded me to fuck it harder and harder. I rode him hard until he was ready to cum and then he took over, grabbed my hips, and pulled me down as deep as he could go before blasting his seed into my hole. I was in ecstasy, as he blasted a good 5 loads into me. After he knew, he was done feeding my hungry hole with his seed, he slapped my ass, got up and said he hoped to see me again and walked away, back to Cherries. I needed a few minutes to compose myself, before heading back to the bar. As I was scoping the place out, looking for my friends, I was shocked at who was looking at me. I froze, I wanted to run, however he already saw me. There, in the crowd, across the bar, was my ex-boyfriend, the one that broke my heart, Lee Thompson.
I wanna know more about Tommy than his Brother, I would like to know how Tommy 's gay sex for the first time.
 
  • Like
Reactions: Jjjay94
Chapter 6: Sunday Night (Tommy’s point of view)

It was Sunday night and Tommy was relaxing in the jacuzzi. After leaving the pool party earlier in the day, he worked out, swam in the ocean, talked to his sons and now was listening to his favorite podcast, while drinking a bottle of wine. He wasn’t expecting to see the guys, until the following morning, as he had a surprise for them. While he is glad, he came, he now knows how women feel, when they walk by construction sites or anywhere else in fact. He didn’t mind the comments, the touching of his upper body, or the occasional butt grabbing, he did not feel comfortable when guys would grab his cock, on those occasions that it did occur.

As Tommy was relaxing, naked in the jacuzzi, he was caught off guard, when someone called his name. When he opened his eyes, standing in front of him, was Henry.

“What you are doing back so soon, thought you would be out all night, having fun. I can hear the craziness when I take out my air pods.” Tommy said with a surprise look.

“You know me, that really isn’t my thing, I had my fun, but I rather just relax now.” Henry said, while realizing Tommy was naked and giggled.

“Well, hop on in, it's very relaxing and I have wine lol.” Tommy said.

I really liked Henry, I always thought he was a wonderful, caring, and sincere person and a great friend to my younger brother. I got out of the jacuzzi, Henry didn’t care I was naked in front of him, and went back to the kitchen, to get another glass and bottle of wine, while Henry was taking his clothes off. When I returned outside, Henry was already in the jacuzzi. We ended up chatting, laughing, and drinking wine for a while, while watching the lovely clear skies overlooking us.

It was now 1 am and Henry and I had just finished 3 bottles of wine and were having just a genuine great time. At this point of the night, he was sitting right next to me, as he was graciously listening to my sad story of getting divorced and how I fucked my life up. I went on to tell him how my life has been ruined. I became a dad at 19, never fully experiencing the whole college life. I never went on Spring breaks, never slept with as many women as I could have and ruined my relationship with my family. This was the first time, as I started to cry and fully embrace the disaster that is my life.

“I just feel like a complete loser! I missed out on so much stuff!” I said, while weeping into Henry’s shoulder.

I went on to say, “I gave up a lot at 19. I could have been a model, an actor, could have been picked up by the Yankees as a pitcher. Heck, you know how many times I was asked to do porn?”

“Fuck that bitch! Dude, it's not like you’re in your 50’s or 60’s! You’re 30 years old, still at your prime. Sometimes I wonder if you don’t realize just how talented, smart, and FUCKIN HOT you really are? Yes, you may have missed out on a lot of stuff in your 20’s, but you’re still young and can change things around. What about that offer from my dad, about being head of security for his hedge fund company? The pay is sick! What did he offer you, like $450,000 a year, plus bonuses!” Henry said.

A few weeks ago, Henry reached out to me about his dad’s job offer, since his dad was thinking of me for the position, since his longtime associate decided to retire and move to Florida. I didn’t give it much thought, that was before I found out the evil bitch, got impregnated by the UPS guy. I love Henry’s family; both of our families are very tight. Our parents still vacation together, even after Henry’s mom passed away a few years back. I laid my head backwards on the jacuzzi, after pouring my heart out and just sat there, thinking of how my life went. We sat quiet for a minute or so and suddenly I felt Henry’s hand caressing my leg.

I don’t know if it was the wine or I was just horny as fuck, but I let him keep caressing my leg. It felt good, the touch of someone else. I raised my head, and I watched him for several minutes as he kept feeling my leg. The water from the jacuzzi was dripping from his pecs, abs, and hair. The night felt so peaceful and calm, with the breezy wind picking up and the beaming of the stars from up above.

I was looking into his beautiful blue eyes while he was caressing my leg. There was always this weird chemistry between us, chemistry that seemed to be locked and hidden away all these years. I never thought something like this would happen. Since I was a married straight guy, there wasn’t any chance something was ever going to happen, between Henry or anyone else, when it came to messing around with another guy. However, like I said, as I was stirring into his eyes, something changed, as I slowly moved his hand to now my hard and pulsing cock.

I felt my cock was getting harder. My heart was pounding into my chest. We both laid our heads back, closing our eyes, as we both started to breathe heavily. I felt Henry's hand, slowly go up and down my throbbing cock. He tugged it downward and it flowed back up, hitting my stomach with a loud thump. I feel Henry slowly bringing his thumb and starts to tease my cock head and could feel him teasing my piss slit, that was starting to ooze out precum.

I start to get lost in his bliss, now stroking my cock hard and faster, up, and down. I move one hand up and start feeling my pecs while Henry now gets closer and with the other hands, starts to massage my balls in his hand.

“Oh fuck!" I moaned

Then out of nowhere, I snap out of it and realize what is happening. I pushed Henry away from me, got out of the jacuzzi, with a major hard on and headed back into the house. I couldn’t believe what just happened! I let a guy touch my cock! It felt amazing, but I AM NOT ATTRACTED TO GUYS! I head to the bathroom, turn on the water in the shower, wait for the room to get steamy from all the hot water. I get into the shower and start to soap my body by rinsing myself of what just happened. With my face under the shower head, which was blasting a lot of hot water, I didn’t hear Henry open the door. Within seconds, I see the shower curtain move and in comes Henry. I turn around, still with a massive hard on and Henry quickly gets on his knees. WTF!
 
Chapter 6: Sunday Night (Tommy’s point of view)

It was Sunday night and Tommy was relaxing in the jacuzzi. After leaving the pool party earlier in the day, he worked out, swam in the ocean, talked to his sons and now was listening to his favorite podcast, while drinking a bottle of wine. He wasn’t expecting to see the guys, until the following morning, as he had a surprise for them. While he is glad, he came, he now knows how women feel, when they walk by construction sites or anywhere else in fact. He didn’t mind the comments, the touching of his upper body, or the occasional butt grabbing, he did not feel comfortable when guys would grab his cock, on those occasions that it did occur.

As Tommy was relaxing, naked in the jacuzzi, he was caught off guard, when someone called his name. When he opened his eyes, standing in front of him, was Henry.

“What you are doing back so soon, thought you would be out all night, having fun. I can hear the craziness when I take out my air pods.” Tommy said with a surprise look.

“You know me, that really isn’t my thing, I had my fun, but I rather just relax now.” Henry said, while realizing Tommy was naked and giggled.

“Well, hop on in, it's very relaxing and I have wine lol.” Tommy said.

I really liked Henry, I always thought he was a wonderful, caring, and sincere person and a great friend to my younger brother. I got out of the jacuzzi, Henry didn’t care I was naked in front of him, and went back to the kitchen, to get another glass and bottle of wine, while Henry was taking his clothes off. When I returned outside, Henry was already in the jacuzzi. We ended up chatting, laughing, and drinking wine for a while, while watching the lovely clear skies overlooking us.

It was now 1 am and Henry and I had just finished 3 bottles of wine and were having just a genuine great time. At this point of the night, he was sitting right next to me, as he was graciously listening to my sad story of getting divorced and how I fucked my life up. I went on to tell him how my life has been ruined. I became a dad at 19, never fully experiencing the whole college life. I never went on Spring breaks, never slept with as many women as I could have and ruined my relationship with my family. This was the first time, as I started to cry and fully embrace the disaster that is my life.

“I just feel like a complete loser! I missed out on so much stuff!” I said, while weeping into Henry’s shoulder.

I went on to say, “I gave up a lot at 19. I could have been a model, an actor, could have been picked up by the Yankees as a pitcher. Heck, you know how many times I was asked to do porn?”

“Fuck that bitch! Dude, it's not like you’re in your 50’s or 60’s! You’re 30 years old, still at your prime. Sometimes I wonder if you don’t realize just how talented, smart, and FUCKIN HOT you really are? Yes, you may have missed out on a lot of stuff in your 20’s, but you’re still young and can change things around. What about that offer from my dad, about being head of security for his hedge fund company? The pay is sick! What did he offer you, like $450,000 a year, plus bonuses!” Henry said.

A few weeks ago, Henry reached out to me about his dad’s job offer, since his dad was thinking of me for the position, since his longtime associate decided to retire and move to Florida. I didn’t give it much thought, that was before I found out the evil bitch, got impregnated by the UPS guy. I love Henry’s family; both of our families are very tight. Our parents still vacation together, even after Henry’s mom passed away a few years back. I laid my head backwards on the jacuzzi, after pouring my heart out and just sat there, thinking of how my life went. We sat quiet for a minute or so and suddenly I felt Henry’s hand caressing my leg.

I don’t know if it was the wine or I was just horny as fuck, but I let him keep caressing my leg. It felt good, the touch of someone else. I raised my head, and I watched him for several minutes as he kept feeling my leg. The water from the jacuzzi was dripping from his pecs, abs, and hair. The night felt so peaceful and calm, with the breezy wind picking up and the beaming of the stars from up above.

I was looking into his beautiful blue eyes while he was caressing my leg. There was always this weird chemistry between us, chemistry that seemed to be locked and hidden away all these years. I never thought something like this would happen. Since I was a married straight guy, there wasn’t any chance something was ever going to happen, between Henry or anyone else, when it came to messing around with another guy. However, like I said, as I was stirring into his eyes, something changed, as I slowly moved his hand to now my hard and pulsing cock.

I felt my cock was getting harder. My heart was pounding into my chest. We both laid our heads back, closing our eyes, as we both started to breathe heavily. I felt Henry's hand, slowly go up and down my throbbing cock. He tugged it downward and it flowed back up, hitting my stomach with a loud thump. I feel Henry slowly bringing his thumb and starts to tease my cock head and could feel him teasing my piss slit, that was starting to ooze out precum.

I start to get lost in his bliss, now stroking my cock hard and faster, up, and down. I move one hand up and start feeling my pecs while Henry now gets closer and with the other hands, starts to massage my balls in his hand.

“Oh fuck!" I moaned

Then out of nowhere, I snap out of it and realize what is happening. I pushed Henry away from me, got out of the jacuzzi, with a major hard on and headed back into the house. I couldn’t believe what just happened! I let a guy touch my cock! It felt amazing, but I AM NOT ATTRACTED TO GUYS! I head to the bathroom, turn on the water in the shower, wait for the room to get steamy from all the hot water. I get into the shower and start to soap my body by rinsing myself of what just happened. With my face under the shower head, which was blasting a lot of hot water, I didn’t hear Henry open the door. Within seconds, I see the shower curtain move and in comes Henry. I turn around, still with a massive hard on and Henry quickly gets on his knees. WTF!
More pls. Love this story. I think Tommy wanted to have sex with gay guys intentionally cuz he shouldn't be naked in the jacuzzi around gay guys, He knows how HOT he is and all gay guy are thirsty for him.
 
Chapter 6: Sunday Night (Tommy’s point of view)

It was Sunday night and Tommy was relaxing in the jacuzzi. After leaving the pool party earlier in the day, he worked out, swam in the ocean, talked to his sons and now was listening to his favorite podcast, while drinking a bottle of wine. He wasn’t expecting to see the guys, until the following morning, as he had a surprise for them. While he is glad, he came, he now knows how women feel, when they walk by construction sites or anywhere else in fact. He didn’t mind the comments, the touching of his upper body, or the occasional butt grabbing, he did not feel comfortable when guys would grab his cock, on those occasions that it did occur.

As Tommy was relaxing, naked in the jacuzzi, he was caught off guard, when someone called his name. When he opened his eyes, standing in front of him, was Henry.

“What you are doing back so soon, thought you would be out all night, having fun. I can hear the craziness when I take out my air pods.” Tommy said with a surprise look.

“You know me, that really isn’t my thing, I had my fun, but I rather just relax now.” Henry said, while realizing Tommy was naked and giggled.

“Well, hop on in, it's very relaxing and I have wine lol.” Tommy said.

I really liked Henry, I always thought he was a wonderful, caring, and sincere person and a great friend to my younger brother. I got out of the jacuzzi, Henry didn’t care I was naked in front of him, and went back to the kitchen, to get another glass and bottle of wine, while Henry was taking his clothes off. When I returned outside, Henry was already in the jacuzzi. We ended up chatting, laughing, and drinking wine for a while, while watching the lovely clear skies overlooking us.

It was now 1 am and Henry and I had just finished 3 bottles of wine and were having just a genuine great time. At this point of the night, he was sitting right next to me, as he was graciously listening to my sad story of getting divorced and how I fucked my life up. I went on to tell him how my life has been ruined. I became a dad at 19, never fully experiencing the whole college life. I never went on Spring breaks, never slept with as many women as I could have and ruined my relationship with my family. This was the first time, as I started to cry and fully embrace the disaster that is my life.

“I just feel like a complete loser! I missed out on so much stuff!” I said, while weeping into Henry’s shoulder.

I went on to say, “I gave up a lot at 19. I could have been a model, an actor, could have been picked up by the Yankees as a pitcher. Heck, you know how many times I was asked to do porn?”

“Fuck that bitch! Dude, it's not like you’re in your 50’s or 60’s! You’re 30 years old, still at your prime. Sometimes I wonder if you don’t realize just how talented, smart, and FUCKIN HOT you really are? Yes, you may have missed out on a lot of stuff in your 20’s, but you’re still young and can change things around. What about that offer from my dad, about being head of security for his hedge fund company? The pay is sick! What did he offer you, like $450,000 a year, plus bonuses!” Henry said.

A few weeks ago, Henry reached out to me about his dad’s job offer, since his dad was thinking of me for the position, since his longtime associate decided to retire and move to Florida. I didn’t give it much thought, that was before I found out the evil bitch, got impregnated by the UPS guy. I love Henry’s family; both of our families are very tight. Our parents still vacation together, even after Henry’s mom passed away a few years back. I laid my head backwards on the jacuzzi, after pouring my heart out and just sat there, thinking of how my life went. We sat quiet for a minute or so and suddenly I felt Henry’s hand caressing my leg.

I don’t know if it was the wine or I was just horny as fuck, but I let him keep caressing my leg. It felt good, the touch of someone else. I raised my head, and I watched him for several minutes as he kept feeling my leg. The water from the jacuzzi was dripping from his pecs, abs, and hair. The night felt so peaceful and calm, with the breezy wind picking up and the beaming of the stars from up above.

I was looking into his beautiful blue eyes while he was caressing my leg. There was always this weird chemistry between us, chemistry that seemed to be locked and hidden away all these years. I never thought something like this would happen. Since I was a married straight guy, there wasn’t any chance something was ever going to happen, between Henry or anyone else, when it came to messing around with another guy. However, like I said, as I was stirring into his eyes, something changed, as I slowly moved his hand to now my hard and pulsing cock.

I felt my cock was getting harder. My heart was pounding into my chest. We both laid our heads back, closing our eyes, as we both started to breathe heavily. I felt Henry's hand, slowly go up and down my throbbing cock. He tugged it downward and it flowed back up, hitting my stomach with a loud thump. I feel Henry slowly bringing his thumb and starts to tease my cock head and could feel him teasing my piss slit, that was starting to ooze out precum.

I start to get lost in his bliss, now stroking my cock hard and faster, up, and down. I move one hand up and start feeling my pecs while Henry now gets closer and with the other hands, starts to massage my balls in his hand.

“Oh fuck!" I moaned

Then out of nowhere, I snap out of it and realize what is happening. I pushed Henry away from me, got out of the jacuzzi, with a major hard on and headed back into the house. I couldn’t believe what just happened! I let a guy touch my cock! It felt amazing, but I AM NOT ATTRACTED TO GUYS! I head to the bathroom, turn on the water in the shower, wait for the room to get steamy from all the hot water. I get into the shower and start to soap my body by rinsing myself of what just happened. With my face under the shower head, which was blasting a lot of hot water, I didn’t hear Henry open the door. Within seconds, I see the shower curtain move and in comes Henry. I turn around, still with a massive hard on and Henry quickly gets on his knees. WTF!
Henry was a lucky guy to see Tommy naked and played with Tommy.
 
  • Like
Reactions: Jjjay94
Chapter 6: Sunday Night (Tommy’s point of view)

It was Sunday night and Tommy was relaxing in the jacuzzi. After leaving the pool party earlier in the day, he worked out, swam in the ocean, talked to his sons and now was listening to his favorite podcast, while drinking a bottle of wine. He wasn’t expecting to see the guys, until the following morning, as he had a surprise for them. While he is glad, he came, he now knows how women feel, when they walk by construction sites or anywhere else in fact. He didn’t mind the comments, the touching of his upper body, or the occasional butt grabbing, he did not feel comfortable when guys would grab his cock, on those occasions that it did occur.

As Tommy was relaxing, naked in the jacuzzi, he was caught off guard, when someone called his name. When he opened his eyes, standing in front of him, was Henry.

“What you are doing back so soon, thought you would be out all night, having fun. I can hear the craziness when I take out my air pods.” Tommy said with a surprise look.

“You know me, that really isn’t my thing, I had my fun, but I rather just relax now.” Henry said, while realizing Tommy was naked and giggled.

“Well, hop on in, it's very relaxing and I have wine lol.” Tommy said.

I really liked Henry, I always thought he was a wonderful, caring, and sincere person and a great friend to my younger brother. I got out of the jacuzzi, Henry didn’t care I was naked in front of him, and went back to the kitchen, to get another glass and bottle of wine, while Henry was taking his clothes off. When I returned outside, Henry was already in the jacuzzi. We ended up chatting, laughing, and drinking wine for a while, while watching the lovely clear skies overlooking us.

It was now 1 am and Henry and I had just finished 3 bottles of wine and were having just a genuine great time. At this point of the night, he was sitting right next to me, as he was graciously listening to my sad story of getting divorced and how I fucked my life up. I went on to tell him how my life has been ruined. I became a dad at 19, never fully experiencing the whole college life. I never went on Spring breaks, never slept with as many women as I could have and ruined my relationship with my family. This was the first time, as I started to cry and fully embrace the disaster that is my life.

“I just feel like a complete loser! I missed out on so much stuff!” I said, while weeping into Henry’s shoulder.

I went on to say, “I gave up a lot at 19. I could have been a model, an actor, could have been picked up by the Yankees as a pitcher. Heck, you know how many times I was asked to do porn?”

“Fuck that bitch! Dude, it's not like you’re in your 50’s or 60’s! You’re 30 years old, still at your prime. Sometimes I wonder if you don’t realize just how talented, smart, and FUCKIN HOT you really are? Yes, you may have missed out on a lot of stuff in your 20’s, but you’re still young and can change things around. What about that offer from my dad, about being head of security for his hedge fund company? The pay is sick! What did he offer you, like $450,000 a year, plus bonuses!” Henry said.

A few weeks ago, Henry reached out to me about his dad’s job offer, since his dad was thinking of me for the position, since his longtime associate decided to retire and move to Florida. I didn’t give it much thought, that was before I found out the evil bitch, got impregnated by the UPS guy. I love Henry’s family; both of our families are very tight. Our parents still vacation together, even after Henry’s mom passed away a few years back. I laid my head backwards on the jacuzzi, after pouring my heart out and just sat there, thinking of how my life went. We sat quiet for a minute or so and suddenly I felt Henry’s hand caressing my leg.

I don’t know if it was the wine or I was just horny as fuck, but I let him keep caressing my leg. It felt good, the touch of someone else. I raised my head, and I watched him for several minutes as he kept feeling my leg. The water from the jacuzzi was dripping from his pecs, abs, and hair. The night felt so peaceful and calm, with the breezy wind picking up and the beaming of the stars from up above.

I was looking into his beautiful blue eyes while he was caressing my leg. There was always this weird chemistry between us, chemistry that seemed to be locked and hidden away all these years. I never thought something like this would happen. Since I was a married straight guy, there wasn’t any chance something was ever going to happen, between Henry or anyone else, when it came to messing around with another guy. However, like I said, as I was stirring into his eyes, something changed, as I slowly moved his hand to now my hard and pulsing cock.

I felt my cock was getting harder. My heart was pounding into my chest. We both laid our heads back, closing our eyes, as we both started to breathe heavily. I felt Henry's hand, slowly go up and down my throbbing cock. He tugged it downward and it flowed back up, hitting my stomach with a loud thump. I feel Henry slowly bringing his thumb and starts to tease my cock head and could feel him teasing my piss slit, that was starting to ooze out precum.

I start to get lost in his bliss, now stroking my cock hard and faster, up, and down. I move one hand up and start feeling my pecs while Henry now gets closer and with the other hands, starts to massage my balls in his hand.

“Oh fuck!" I moaned

Then out of nowhere, I snap out of it and realize what is happening. I pushed Henry away from me, got out of the jacuzzi, with a major hard on and headed back into the house. I couldn’t believe what just happened! I let a guy touch my cock! It felt amazing, but I AM NOT ATTRACTED TO GUYS! I head to the bathroom, turn on the water in the shower, wait for the room to get steamy from all the hot water. I get into the shower and start to soap my body by rinsing myself of what just happened. With my face under the shower head, which was blasting a lot of hot water, I didn’t hear Henry open the door. Within seconds, I see the shower curtain move and in comes Henry. I turn around, still with a massive hard on and Henry quickly gets on his knees. WTF!
At the end. Anthony watches his Hot Brother Tommy getting fucked by a bunch of guys.
 
Chapter 7: Monday, the 4th (Anthony’s point of view)

It was 1 pm when my ass finally woke up. It was the 4th of July and last night we got in at around 5 am. The night was a total blur, not going to lie. I got really fucked up but had a great time. I danced, made out with a whole bunch of hot guys, and just had fun. As I stumbled into the kitchen, where I saw Henry. One by one, we all sat around the table, as Henry placed pancakes, with eggs and bacon and mimosas in front of us.

“Where is Tommy?” asked Rodrigo, as he was stuffing pancakes down his throat

“Oh, I got a text from him when I woke up. He said he was going to take a ferry back to the mainland but will be back later today.” I informed the group

“Guess us fruity queens must have scared the poor straight guy off!” Timmy said and then all of us except Henry burst out laughing.

“Henry, what happened to you last night? We couldn’t find you?” Rodrigo asked
As we all stirred at a very quiet Henry, he sat there with a total blank look on him and didn’t seem like himself.

“Oh nothing, I left early and just relaxed and went to bed early. Had a migraine.” He finally said.

“I call bullshit! I know you, Henry! You got some last night!! Migraine is always code you had a booty call! I shouted to the group, as I slapped my hand hard on his back.

The group all went into a laughter, as Henry turned bright red. He never did say anything else. That afternoon, we all relaxed by the pool, played board games, and had fun. We all wanted to be ready and fresh for tonight’s crazy party, the infamous Fire Island 4th of July Pine underwear masquerade party. It is a very famous, but notorious party, where everyone is just in their skippiest underwear and face covered. TONS AND TONS AND TONS AND TONS of sex, especially downstair in the dark rooms.

“So, what happened with that douchebag Lee?” Rodrigo asked me, while we were at the pool.

“Nothing, he saw me, and I happily gave him the finger and informed the bartenders he was there. Asshole got kicked out moments later.” I said, with an evil chuckling grin.

Later in the afternoon, everyone was getting ready for tonight’s shenanigans, picking out the sluttiest underwear, and making sure we douche properly, as we all expected to take a couple of loads tonight. As we were all in the living room, we invited a few more of our friends over and started to take shots of tequila. Suddenly, Tommy opened the door, and he had a quest. I looked at our guest and spit out my recent shot of tequila. All my friends gasped, as standing next to Tommy, was Alexander Rivera.
 
Chapter 7: Monday, the 4th (Anthony’s point of view)

It was 1 pm when my ass finally woke up. It was the 4th of July and last night we got in at around 5 am. The night was a total blur, not going to lie. I got really fucked up but had a great time. I danced, made out with a whole bunch of hot guys, and just had fun. As I stumbled into the kitchen, where I saw Henry. One by one, we all sat around the table, as Henry placed pancakes, with eggs and bacon and mimosas in front of us.

“Where is Tommy?” asked Rodrigo, as he was stuffing pancakes down his throat

“Oh, I got a text from him when I woke up. He said he was going to take a ferry back to the mainland but will be back later today.” I informed the group

“Guess us fruity queens must have scared the poor straight guy off!” Timmy said and then all of us except Henry burst out laughing.

“Henry, what happened to you last night? We couldn’t find you?” Rodrigo asked
As we all stirred at a very quiet Henry, he sat there with a total blank look on him and didn’t seem like himself.

“Oh nothing, I left early and just relaxed and went to bed early. Had a migraine.” He finally said.

“I call bullshit! I know you, Henry! You got some last night!! Migraine is always code you had a booty call! I shouted to the group, as I slapped my hand hard on his back.

The group all went into a laughter, as Henry turned bright red. He never did say anything else. That afternoon, we all relaxed by the pool, played board games, and had fun. We all wanted to be ready and fresh for tonight’s crazy party, the infamous Fire Island 4th of July Pine underwear masquerade party. It is a very famous, but notorious party, where everyone is just in their skippiest underwear and face covered. TONS AND TONS AND TONS AND TONS of sex, especially downstair in the dark rooms.

“So, what happened with that douchebag Lee?” Rodrigo asked me, while we were at the pool.

“Nothing, he saw me, and I happily gave him the finger and informed the bartenders he was there. Asshole got kicked out moments later.” I said, with an evil chuckling grin.

Later in the afternoon, everyone was getting ready for tonight’s shenanigans, picking out the sluttiest underwear, and making sure we douche properly, as we all expected to take a couple of loads tonight. As we were all in the living room, we invited a few more of our friends over and started to take shots of tequila. Suddenly, Tommy opened the door, and he had a quest. I looked at our guest and spit out my recent shot of tequila. All my friends gasped, as standing next to Tommy, was Alexander Rivera.
Hot hot hot but you didn't say what Tommy and Henry did thou...
 
  • Like
Reactions: Topgun4U69