Sharing My Brother's Fleshlight (And Other Adventures)

[jamiejag88]

January 2019

So I have a confession to make...

My older brother is separated from his wife and has been living with me since October 2018. I’m bi and my brother is straight. My family is very accepting and supportive of me over the last 10 years or so.

My big bro and I have a great relationship, and I’ve enjoyed spending time with him. When we were growing up, he taught me how to jack off and through high school, we jerked off many times together. Later, we even had a threesome with one of his college girlfriends. It was all very hot for me, but we have never really talked about any of it since it happened.

And I won’t lie, it’s been great seeing him around the house in all different states of undress. Just this morning, he walked into the kitchen naked to get coffee, his dick and balls on full display. We’ve seen each other naked before so to him, it’s not a big deal. I love how when he gets out the shower he walks around the house with only a towel around his waist, allowing me a great view of his furry belly and treasure trail. Or how when we watch TV, he wears only his basketball shorts, putting his hairy legs up on the coffee table with his arms folded behind his head, giving me a great view of his cock outline and his hairy pits. It drives me fucking insane!

So, back to the confession. A few weeks ago, I went into his room to grab my phone charger that he always steals from the kitchen counter. Laying on his desk chair was a fleshlight. I was curious as I’ve never used one before. I’ve seen many PornHub and Xtube videos of guys fucking them. This one was shaped like a pussy. I picked it up and slid my finger inside, feeling the bumps and ridges, and I just couldn’t help myself. I took it in my room, lubed up and fucked it. It felt amazingly awesome, and a little dirty. I shot my load, cleaned and dried it off, and put it back where I found it.

Since then, I have “borrowed” it dozens of times. Lube, fuck, cum, clean, dry, replace and repeat. It feels so hot knowing that our dicks are fucking the same fake pussy and that he has cum in it over and over again, just like me.

So way early this morning, my brother left for a weekend trip. I woke up horny as usual, so I went into his nightstand to borrow his pussy toy. I stuck my cock in and felt warm wetness. I realized that he had used the fucking thing just a few minutes earlier and hadn’t cleaned it out. Holy shit! I was fucking his sloppy seconds. I could feel his cum cover my dick. It was so fucking hot, using my big bro’s cum as lube. I quickly ejaculated into it, my load mixing with his. I put it back the way I found it, not wanting to clean it and give myself away…

 

[jamiejag88]

First time Jerking Off With My Brother - 2005

The story you are about to read is true. It involves two brothers bonding over jerking off. Nothing sexual happens between them.

One afternoon I walked in my older brother's room to and caught him jerking off. He was sitting in his desk chair, his left hand holding a magazine, his right hand around his dick.

"Hey asswipe!" he greeted me. "Try knocking next time. Close the door so mom doesn't see."

My brother is super hot, tall and muscular with hairy arms and legs and a furry belly to match. He was a basketball player and wore basketball shorts and tank tops that showed off his hairy pits. We are what my family calls “Irish Twins” as I was born 11 and a half months after he was. So for a few days each year, we are both the same age. He can be a bit cocky and arrogant, but he’s a lovable goofball. We always had a good relationship and still do to this day.

"What are you doing? Studying?" I asked jokingly.

"Yeah, her tits. Thanks for interrupting asshole." He paused, looking up at me. "You just going to stand there and look at me?" he asked, his dick hard and still in his hand.

I just stood there, with a mischievous grin on my face. I started to walk to the door.

"Come over here little bro," he said. "Let me show you the right way to do it."

And with those words, I left my inhibitions behind. I walked over to him, pulled down my shorts and sat on the edge of his bed. My dick was hard and ready.

"Watch and learn," he instructed, laughing. “Look at this.”

He shared one of my dad's Penthouse magazines that he had snatched from the shed. It was the 12 Pet of the Year special.

"You like what you see?" he asked, showing me a brunette with big tits.

I lied. I was enjoying watching him more.

We both sat there stroking our dicks. His hand moving up and down his cock, fast and hard, and then slow and calmer. He would alternate.

“Fuck, I’m horny. I haven’t cum for a few days,” he said.

“How often do you jerk off?” I asked.

“Usually every day. You?”

“Yes, but usually in the shower, that way nobody walks in on me,” I said smirking.

“Gross! You shoot your load in the tub that I shower in. That’s fucking disgusting.”

I laughed. The awkwardness had quickly worn off. It was now just two bros enjoying a good jerk off.

“Your dick looks a lot like mine,” he said. “What are you, about 7 inches?”

I had noticed too. His was a bit thicker, but I was a bit longer

“About 7.5,” I said proudly. “I see you trim your pubes. Why?”

He laughed. “The ladies don’t want to go down on a big bush of pubes. That shit gets stuck in their teeth.”

My brother was straight and had only had one girlfriend, and complained incessantly that she never would do anything with him. He was girl crazy and she had found out that he had hooked up with one of her friends and she dumped his ass.

On the other hand, I was bi, and had hooked up with a few guys. I had also hooked up with a girl or two, but was more interested in dudes. It was way easier to hook up with guys.

"Dude, I'm about to fucking cum," he whispered. And boy did he! It shot all over his chest and stomach, pooling in his belly button and running down his treasure trail. He reached down and took off a sock, using it to wipe the cum off his stomach.

I came a few seconds later, busting a nice load on my belly, the cum dribbling down my dick onto my hand.

“Good job bro!” he said. “That was fun, but we can’t tell anyone. This is our secret.”

After that, we became jerk buds. We weren't blood brothers, we were cum brothers. We jerked mostly in his room, but we got quite adventurous. We were only one grade apart, and one day he walked in on me taking a piss in the science lab bathrooms and we jerked off into the urinal trough. Another time, we were riding bikes and he had a massive boner in his shorts that he showed off proudly to me. We went into the woods and jerked off. We both pissed afterwards and laughed at how the pee sprayed everywhere.

My granny gave me my own laptop for my birthday, and the first thing my bro and I did was look at porn. You had to have a lot of patience looking at porn in the days of AOL, so there was lots of time to look at my bro stroking his dick!

One day he borrowed my laptop when I wasn’t home and got weirded out after he found gay porn on my computer. He asked me about and I told him I was bisexual. He seemed cool with it and never said anything about it to me again. But our bro bonding slowly started to fizzle out after that. He also found a girlfriend who put out and started having sex with her. And soon after, he went to college and moved into his own apartment.

All good things must come to an end. But boy I do I miss those days.

But things did get interesting again. The next year, me my bro had a threesome with one of his college girl friends...

 

[jamiejag88]

Threesome with My Big Brother and his Girlfriend - 2006

As a pizza delivery boy in New Orleans, I never quite knew what to expect when I rang the doorbell! I saw a lot of naked and weirdly dressed people answer their doors. I saw lots of crazy shit and I loved delivering pizza to frat houses around the universities. Lots of hot, shirtless frat dudes. I usually got lousy tips, but the images I added to my spank bank were worth it.

One of the best experiences was my senior year of high school. I just turned 18 and had gotten a used car from my parents for my Christmas/Birthday gift. I was enjoying the freedoms that being 18 and having a car allowed, including not having to deliver pizzas in the neighborhood by bike!

Late one night, I pulled up to a house party and found a note on the door that said "bring pizza inside." I wasn't supposed to just walk in, so I rang the doorbell and knocked several times. No one came to the door and I could hear music playing inside. I was carrying six pizzas and so I finally just opened the door and walked in.

The air was filled with smoke and country music was blaring over the speakers. There were a few people dancing and making out, a few passed out on the floor and sofas. A couple of guys were playing cards around the sofa table. One girl with bright red hair just pointed towards the kitchen. I walked in and found this hot as fuck frat dude, buck ass naked, laying on his stomach on the island. 3 guys were standing around cheering him while a topless girl with nice set of tits was shaving his ass. One of the guys simply said, "He lost a bet." They were very nonchalant about the whole scenario and told me to leave the pizzas on the table. I left with a $20 tip and an invitation to come back after I got off work. Common sense didn't prevail in my teenage mind. After cleaning up, clocking out, and texting my dad that I was hanging out at a friend's house, I headed back over.

I walked back in and frat guy with the freshly shaved ass was sitting in his white boxers on the sofa. The topless girl was passed out next to him. A few of his buddies were playing Madden. There were a few people hanging out and smoking up out on the patio.

"The pizza guy’s back!" said the frat dude. He got up and offered me a beer and pizza. I took the beer and declined the pizza. "They shaved my nuts, too," frat dude told me a little too proudly. He pulled down his boxers to show me his soft dick and shaved balls. His pubes were shaved but the thick treasure trail leading up to his belly button was left intact. Instant boner. "Nice" was all I could mutter.

We all ended up back on the sofa and we watched the guys play Madden for a few minutes. The guys came in from the patio and offered me a hit off their bong. It was my first time, and I awkwardly took a hit. And then another. "Hold it." After a few more beers and another hit, I was feeling pretty good. And then my older brother walked in the room.

He saw me and freaked the fuck out. He accused me of following him and swore I'd be sorry if I told my mom. He was high and had been fooling around with some blonde hair chick in one of the bedrooms. One of his buds calmed him down and said that we were all just hanging out. I tried to get up and go to my car, but the girl with the red hair took my keys and threw them to my brother. "It's cool" he said. Let's go home.

Blondie walked me and my bro to his apartment a few blocks away. We collapsed on the couch. The effects of the weed and beer had kicked in. Blondie went to the fridge and grabbed a few more beers, handing one to me and my brother. She sat down between us. A few seconds later, I felt a hand go up my shorts. Her fingers caressed my inner thigh and continued to go up. Instant boner! She started playing with my cock and balls.

I heard a sigh from my bro. I looked over, and she was doing the same to him. He fumbled about, taking off his basketball shorts and t-shirt and I quickly followed suit. It had been awhile since I saw my bro naked with his hard dick pointing straight up. We had jerked off a lot together and were quite comfortable being naked around each other. But we had never done anything sexual together. He is very straight.

She started giving him a blowjob while massaging my hard dick. She switched off and I felt her warm lips on my dick. Despite the beer and weed, I don't think I lasted but a minute or two. I gave her fair warning and blasted cum all over her face, in her hair, on the coffee table and even on my brother's foot.

"Dude!" was all he could say. He seemed proud and impressed.

She turned back to him and started sucking his dick. He reciprocated, removing her dress and panties and going down on her. They played around a little more and he fucked her right there on the couch in front of me. Her head was laying in my lap as his ass bounced up and down in the air in time with her loud moans. I was enjoying the show and my dick had sprung back to life.

“Get over here bro,” my brother invited me over. “You know what to do.”

I maneuvered my way from under Blondie and headed to the other end of the couch., Now, this wasn’t my first time fucking a girl, but I was more into guys than girls. But I wasn’t about to let this opportunity pass me up. I felt the heat coming off of our bodies as I got on top, lining up my dick with her pussy. I entered her and felt the warmness envelope my dick.

“Slower,” she said. Then, “harder.” We ended up working up a nice rhythm.

“Nice, bro! Keep going,” encouraged my brother. We fucked for a few more minutes, my balls slapping against her ass, along to the encouraging words of my bro.

I felt a tap on my shoulder. “My turn, bro. Let me show you how it’s done.”

He turned her around and fucked her doggy style over the couch for a few minutes, while I stroked my dick in the recliner.

“I’m about to cum!” he said. “Fuck!”

He pulled out and she turned over. He came in a geyser all over her tits and face. It was a massive load. I was impressed. He always shot massive loads.

Blondie hadn’t cum yet, so bro put his mouth and tongue to work and soon she was moaning and cumming. He then did the hottest thing I’ve ever seen, putting his head back between her legs and went to town. She squirmed and shivered, and his face came up covered in her pussy juice and cum. Fucking hot!

He grabbed us a few more beers while Blondie cleaned up in the bathroom. We bullshitted for a bit and passed around another joint. Soon after, I passed out.

I woke up late the next morning naked in my brothers bed wearing only one sock. I walked out the room to find my clothes. Blondie was gone. My bro was naked, making coffee in the kitchen. I grabbed my clothes off the floor.

"Clean up your mess," he told me with a big grin on his face, pointing to my dried cum on the glass coffee table. “I cleaned the couch already. Thank god for fake leather!”

We hung out that afternoon, grilled out and watched the Saints game. We never talked about that night again. I have jerked off to that memory thousands of times, and I secretly hope that he has too.

 

[jamiejag88]

Borrowing My Brother's Fleshlight - Part 2

January 2019

My brother returned from his weekend hunting and football trip with his buddies. I knew he wouldn't be in the best mood because the Saints lost. Turns out he and his friends commiserated the loss by drinking a couple dozen pints, and he was pretty wasted by the time he staggered through the door.

I was in the kitchen making a grilled cheese sandwich to go along with my tomato soup. He told me hi and walked into his bedroom to put down his gear.

I have been thinking about this moment the whole weekend, contemplating what I should do. It was the classic devil vs. angel debate. Should I leave it and let him clean out the cum? And possibly let him fuck it with our cum in it? Or should I just clean it out and just confess to what I had been doing? For most of the weekend, the horny devil was winning...

He came out of his room in just a pair of basketball shorts and entered the kitchen.

“Fuck dude, I’m tired.”

“And inebriated too, I see,” I said, raising my eyebrows. “Want some soup and a grilled cheese?

“Nope, just had a few drinks. I’m good,” he said grinning. “And yes, two for me please,”

We ate the sandwiches and soup on the couch, flipping through the channels, but nothing was really on TV.

“You shoot anything?” I asked.

“Nope, but my back is killing me.”

Apparently after a weekend on his back bird hunting, he had nothing to show for it but soreness. I can think of way more better things to do while laying on my back!

I flipped over to Die Hard 2.

He finally asked, “So what’s up with you? You’re acting all weird. I know something’s up…”

FUCK! Was I that obvious? I’ve dealt with Catholic guilt my whole life, even though I hadn’t gone to church in years. There was know way of getting out of this. He could smell bullshit a mile a way and I was a fucking horrible liar. There’s a reason I didn’t play poker.

“Umm. Yeah,” I stammered. “We need to talk. I found your fleshlight and I’ve been borrowing it…”

He looked at me and laughed. “OK dude. That’s kinda gross, but whatever.”

“I used it this weekend.”

His eyes got big and he smirked. “You know I shot a load in there before I left?!?”

“Yeah, I figured it out after it was too late. It was still wet.”

“Fucking gross, but I bet you liked it you fucking perv.”

I laughed. “I’m not going to lie, it was pretty hot.”

“Please tell me you cleaned it out.”

“Not yet, but I will. I just wanted to let you know.”

“Were you seriously going to let me fuck that thing with your dried cum in there?”

“Well, no...yes...maybe,” I laughed.

“Fuck! If I hadn’t said anything...you are a fucking perv!” He laughed and got up to go to his room. He came back and tossed the fleshlight to me.

“Dude, go clean it out.”

I washed it in the kitchen sink and tossed it back to him.

“Now please go in my nightstand and get me the bottle of lube.”

“I know where it is,” I said. “And only because you said please.”

“Fuckhead,” he laughed.

I brought him the lube. I had a hunch where this might be going…

“You remember when we used to jerk off together?” I asked.

“How could I forget. You couldn't keep you eyes off my dick.”

“And how we both fucked your girlfriend?”

“She wasn’t really my girlfriend…”

“Doesn’t matter. She was hot and I liked fucking her with you.”

“It was fun...” he admitted.

“I know it’s been awhile, but I wouldn’t mind doing it again,” I said.

“I know. I’m fucking hot and I turn you on.” He laughed. “Seriously bro, there’s just been a lot going on…”

He and his wife have been split up for a few months, and he’s been staying with me. It doesn’t look like things will change anytime soon.

“Oh shut up! You’re sooo full of yourself!” I said sarcastically, tossing a throw pillow at him.

“And that makes you want this even more” he said, pointing to his dick. He pulled down his basketball shorts, his beautiful cock sprung up.

He opened the lube and started rubbing it on the tip of the fleshlight, working it around the fake pussy and then into the toy.

“You know it’s not real,” I said. “You don’t have to buy it dinner and foreplay it to death.”

“Oh shut the fuck up. Bad habits.”

He looked at me and asked, “What are you waiting for?”

I dropped my shorts and my dick sprung to life too. What can I say, we both get hard fast! I took of my shirt and watched the show.

He lubed up his cock, and inserted it into the fake pussy. He thrusted slow at first, then started fucking it faster.

“I’m really fucking horny,” he admitted.

“I can see that. Me too. Give me a turn,” I said.

“Not yet, give me a minute.”

His body stiffened and he grunted. “Holy shit, I’m cumming!”

He slid his dick half way out. I could see it pulsating as it shot load after load into the sleeve.

“Fuck, I needed that!” he said. He pulled his cock out the rest of the way. It glistened with lube and cum. He wiped it off on his shorts.

“It’s always fun putting on a show for you.” He looked at me and winked, handing me the fleshlight. “It’s ready for you, should be nice and sloppy. Let’s see what you’ve got.”

He handed me the bottle of lube.

“No thanks, don’t think I need it,” I said, inserting my dick and feeling the inside coated with my brother’s cum. I fucked that fake pussy hard. I laid down on the couch, dick in the air, moving the fleshlight up and down.

“Want to give me a hand?” I asked.

“No man, that’s ok. I already brought you some pussy. That’s the only way you can get it!” We laughed.

I was getting close. “Wanna see me cum?” I asked.

“Not really, but ok, go for it!”

I fucked it harder, and started to feel my balls tense up. I thrusted my dick all the way in and cum shot out the end of the fleshlight all over the glass coffee table.

“Holy Fuck, that was hot!” I said.

“Look at the mess you made,” he said laughing. “That was a nice load, bro.

“Glad you’re here to teach me some stuff.” I said sarcastically. “But I really miss hanging out with you like this.”

“Hanging out with our cocks out?” he laughed.

“Yeah, I really do. I hope this isn’t too weird.” I said.

“Nah man, it was fun.” Anyway, that’s more pussy than you’ve had in awhile,” he said laughing.

“I can say the same for you,” I retorted.

“Ouch! Good night bro. Make sure you clean this mess up,” he said, walking to his bedroom.

He closed the door. I took took the fleshlight and let our cum drip out, watching it pool on the glass table. It was quite a mess.

I licked the table clean, his cum and my cum mingling on my tongue. It was the first time I’ve tasted my bro’s cum.

Hopefully this is the beginning of a new era of brotherly bonding. I’ll keep posting if more good shit happens.

 

[jamiejag88]

Brother In Laws's Bachelor Party

October 2016

I have two amazing brother in laws who are both fucking hot. Steve is a few years older than me and straight as an arrow. He's a CPA, pretty boring and vanilla, but I have lusted after him for a long time! He's fit as fuck, with furry pecs, abs and an amazing treasure trail. I've only seen him shirtless a few times, at the pool and beach, but have always wanted to see more and where that treasure trail leads to...

My bro in law AJ is a few years younger than me. He's quite the exhibitionist (lucky for me) as he walks around their apartment in nothing but his underwear showing off his package without a care in the world. Its no secret that I'm bi with a boyfriend and that I lust after him. He playfully flirts and messes with me all the time; its all in good fun. AJ has dark hair and manscapes a lot. Sometimes he has a hairy chest, sometimes he's smooth, but he always leaves his treasure trail and pits alone. He has the bushiest pits that I have ever seen. Its fucking amazing. I'm also pretty sure that he's bi or that he has fooled around with guys before. Just a hunch...

At AJ's bachelor party, his brother and best man hired two strippers and a party bus (with a pole) to take us out for a night in New Orleans. We hit up a few bars and clubs and had live entertainment in the bus. The strippers were actually pretty hot and great tour guides. They were really funny and even got AJ and my older brother to do a strip tease together, which was hysterical and hot at the same time! Anyways, at the end of the night, we ended up back at the suite properly inebriated.

My brother, Steve, and few of AJ's friends crashed. Me, AJ, his brother and another friend Rob continued the party on the balcony with some beers. It didn't take long for the convo to turn to sex. Rob was talking about how much pussy he was getting in college and then it lead to how hot the strippers were, etc. AJ is in his tighty whities and its obvious that he's turned on. It grows and grows, and his cock head starts to protrude from the pee slot.

"Shiiiiit dude, I got a boner!" he announces. We all laugh.

"Better do something about it," I say, half kiddingly. To my surprise and delight, he whips out his cock.

"Put that thing away. No one wants to see that," said Rob.

"I'm not going to lie, I do" I said smiling.

Drunken dares are issued and cock sizes and manliness and thrown about. Next thing you know, the four of us all have our dicks in our hand. I usually have whiskey dick, but I was on full display that night.

Turns out Rob had the biggest cock, at least 9 inches and thick as fuck. AJ and I are roughly the same, but since he was smooth that night he looked slightly bigger. His brother had some issues and couldn't get it up. But AJ did vouch for him. Apparently, they used to jerk off together when they were growing up, the same as me and my older brother.

It didn't take long for any of us to blow our loads. I was the first to come. As AJ announced he was about to nut, he got up and ejaculated over the balcony. I thought it was the funniest thing, laughing until I almost pissed myself. Rob was again the star that night. He fucking unloaded all over his chest, the cum soaking into his white undershirt. It was fucking hot.

"So guys, do you eat your cum?" I asked, as I raised my hand to my mouth and slurped some of the cum off my finger.

"Fucking gross" said Rob, as he retreated to the couch. We all ended up going to our beds.

I shared the room with my brother and Steve. My bro was already asleep on the floor and I got in bed with Steve. He was sound asleep in only his boxers. Boy did I have some good dreams!

I was the first to wake the next morning. I took advantage of the huge jacuzzi tub in our bathroom (it wasn't event the master bath). I hear a knock on the door. It's Steve telling me to hurry up, he had to piss. I tell him to come in. He sees me in the tub, with bubbles up to my chest and stares at me with a grin and laughs.

"I won't look" I say as I close my eyes. He must have really had to go, because my usually reserved brother in law pissed right in front of me for a good minute. I (mostly) kept my word, but I did sneak a glance and saw the top of his ass as he was pissing. God he's so fucking hot.

A few minutes later my brother comes in.

"Just a fair warning, I'm taking a shit" he says laughing. Thankfully he did the courtesy flush thing and I did keep my eyes closed for that. He then jumped in the shower. We have seen each other naked hundreds of times, jerked off together and even had a threesome with his girlfriend, so being naked was no big deal. But no matter how many times I see his cock, it still turns me on.

All in all, it was a great night. I saw strippers, awkward male stripteases, jerked off with my bro in law and his friend and saw Steve take a piss. What a night!

 

[MusicMan321]

That was a nice story to read I liked it man

 

[jamiejag88]

Thanks!