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Book II

 

Jeremy

 

So Steve and I have moved into Dads and we share the Spare bedroom I guess you could call it our room, and although it is a bit cramped with Steve’s queen and my “daybed” which is really a twin we have always gotten along well and have been sort of sleeping together off and on since freshmen year so no big deal. Sam hung out with us a lot, when asked if he had any friends in high school he said he liked being with us better, although he did have a close friend he thought we’d enjoy meeting. Sam was totally infatuated with Steve and me, we made a great triad, and Sam was turning into a total cumdump, and he wanted Steve’s cum in his hole.

 

I couldn’t believe how my life had changed in such a short time, it had just been around Valentine’s day when I met up with Matt for the first time, now he was asking us Steve, Sam and I to make sure our schedules were clear on Monday he had something he wanted to do with us around 3, Steve went over to pick up Sam, and we all met at the clinic over on 21st. Matt was having us tested for HIV and STI’s to play it safe, we all knew what Steve’s test would prove, but Matt needed to confirm his progression, and told us we would most likely all go on Meds, PrEP for Sam and I , and the HIV cocktail for Steve. We each had the more expensive test to detect the actual virus along with the Swab test that took about 20 minutes to complete along with some blood was taken and we all had to piss in some cups. The results were not surprising, preliminary test had us as negative and we would have to wait on the STI test but we knew they would come back most likely as negative too since it has only been us fooling around since we all met.

 

Matt paid for all of us to get our meds and we all started on Travada as our treatment. And on the way home he had a serious talk to myself and Sam about being true to our PrEP regimen or it wouldn’t work. Matt cooked dinner for us when we got home and texted Sam’s dad about him spending the night, Steve would take him to school in the morning and Matt would make sure he got his homework done.

 

It was beginning to look like a family, even Uncle Tony agreed that we were slowly becoming like a close knit group. Spring break was coming up and once again Matt asked us to get the time off as he wanted us to enjoy or break from school, and he had some special plans for us.

 

Thursday finally arrived and as we all prepared for school Matt came in to make sure we would be ready to go by 4 that afternoon. Classes dragged on but Steve picked me up at 3 from my last class, we arrived back at the apartment at around 3:30 Dad was waiting and already had loaded his luggage in the car, he was waiting on us to finish our packing based on what information he had provided us on our destination.

Sam was excited, to see us, after his dad had dropped him off after school, we finished loading our suitcases with Dad’s help. Just before 4 we loaded into the car and Matt drove us to the airport, we parked in long term parking and caught a shuttle to the terminal, we checked in the followed dad through security to the boarding gate, it appears we were headed for Chicago We boarded the plane and were soon up in the air, about a hour in Sam got up to use the rest room, Steve suddenly had to go too. Ten minutes later he came back and whispered that

Sam needed help if I could go check on him. I shuffled out of my seat and headed back towards the rest room where Sam was in need of help, I knocked lightly on the door that Steve had said contained the boy. Sam Opened the door and pulled me in quickly so as not to attract attention. Once the door was closed and locked Sam planted a hot passionate kiss on me while undoing the buckle of my belt and the buttons on my pants, before I knew it he had my pants around my ankles and had turned pressing his ass up to my now hard cock rubbing his cheeks up and down my shaft, soon my cock found his wet pucker and slid into his cum filled hole

 

“Oh my god did you and Steve just have sex in here?”

 

“Oh yeah, we both joined the mile high club, just like you are doing now”

 

“And you let him fuck you bare”

 

“What a better way to join the club, and I’m on PrEP”

 

I just shrugged, all the time he was riding my cock and getting me close to shooting my load deep in his hole to join Steve’s, I grunted and blasted away filling Sam with my load. I reached around to find Sam’s cock drizzling precum on the floor, I pulled out of his ass and turned around towards the door, as Sam reached into his pocket and pulled out a small butt plug, he turned around and shoved his cock up my hole, I hurt like hell going in with just his precum to lube the way but I knew Sam would not last after getting fucked by Steve and my cocks, he started slow and easy giving me a chance to get used to the intrusion, but soon all the precum had me lubed up well as I relaxed he was pounding into me pushing against my second ring then he growled a bit and shot his load into my guts, planting it as deep as he could get. He grabbed a towel and wiped us both off pulled up my pants and unlocked the door.

 

“I’ll be right out, go back to our seats, don’t want anyone getting suspicious”

 

I returned to my seat and Steve gave me that all knowing look and I just had to smile, as did my dad. About five minutes later Sam returned, grinning ear to ear.

 

“What took you so long dude”

 

“let’s just say the steward came to check up on me and I treated him to some special sauce”

 

Steve and I kept asking him questions, as we got the story out of him we both got boned up, the cute steward who helped us board came to check up on Sam shortly after I left the restroom and Sam told him everything was ok, but the steward asked Sam to open the door so he could see for himself. Well Sam opened the door and let the steward in his hard cock hitting the steward in the thigh, the steward then dropped down in the cramped space and started sucking Sam’s cock, then Sam turned around and as the steward started rimming Sam the cum began to drip out and the attendant became quite attentive feltching out the two loads of spooge from Sam’s hole, before standing up and shoving his cock in and breeding my sweet friend with the third load of the flight at 30,000 feet. We all sort of drifted off to sleep after all our activities.

 

The plane touched down shortly after midnight our time, 2am Chicago time. Dad went to the Rental counter as we all collected our luggage from the carousal, we double checked on the number of bags to make sure we weren’t forgetting something, we took the rental shuttle to the car and as soon as Dad loaded everything into the ford escape we piled into the vehicle. Dad started the car and programed our destination in the GPS navigation system. And we were off, arriving at our hotel around three in the morning. Dad checked us in and the bell hops took our luggage to our suite. It was two bedrooms, a living area and a small kitchen/bar area, for me the lap of luxury.

 

We were all too tired to enjoy much and we all just stripped down and crashed on the king size bed. A tangle of teen and tween flesh, a horny sight for dad as he retired to his room, stripped naked and laid down on his king-sized bed, and was soon asleep

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Book II

 

Steven

 

I guess you could call me a wild kid since I was the dare devil of the family, skateboarding, motocross, skydiving, if it was slightly dangerous

I was there to do it, I had to prove I was tough to my older brothers, although I was the baby of the family I had to prove myself to my three older brothers who were much older than me, I was an oops as my mother was preparing for menopause, at 42 she wasn’t expecting to be pregnant again her last child being born 10 years ago, but then I popped into the world and my brothers never let me forget that I took quality time away from them. They had all been born in moms late twenties and early thirties and there was just less than four years between all of them. Being 10, 11, and 13 when I was born. I was loved by all of them but I was at the same time treated as an inconvenience until I reached about 10, then it was let’s see what we can make Stevie do. I was a tough little kid who really was only trying to find acceptance from my older brothers most of my life. I thought I had just about done that when I announced to them I think I like boys, I think I was about 14 or 15 at the time, they told me it was just a phase that all the sports and hijinks had clouded my judgment to give it time and I’d get a girlfriend. Well time went by and I got to the point I was masturbating over a shirtless picture of my best buddy, I knew for certain on my 18th birthday after my bro’s threw a party for me and my best bud, Brad and I grabbed the birthday money after the party. We hopped in his car and took off for Berkeley just up the way. We were standing outside a place called the Steamworks. As Brad opened the glass door, he turned to me

 

“Steve hand me your wallet, I need your ID “

 

I handed him my wallet and he walked up to the window and got me a locker and a membership, then paid for himself as well, we were buzzed in and he lead me to the lockers. I had the inclination to kiss my buddy for a long time but when we entered the baths and got our lockers, he got put on a room waiting list, I found my locker and Brad went to his, I was still clothed when he came up to me and planted a deep wet one on me, he was naked wrapped in a towel around his waist.

 

“Take your clothes off, silly”

 

He lifted my tee shirt over my head and unbuttoned my jeans then slide down the zipper, i had gone commando so as he slide my pants down I was now naked, standing in front of a locker with my best bud, kissing me and holding my clothes, he shoved my clothes in the locker and wrapped the towel around my waist then closed the locker and slid the band holding the key up my arm. He hugged me then took my hand and led me down a darkened hallway.

 

Most of the room doors lining the hall were closed a few were opened and upon looking in I saw naked men laying there either playing with themselves or with their ass up, most were a lot older then us, a couple of the guys wandering around were within a year or two of our age. Men would reach out and touch me as I passed, many eyes were upon us, we came upon one door and a twenty something Latin guy was laying there playing with his hot Latin cock, Brad stopped our progress and stood and watched the guy, then he motioned for us to enter his room, Brad guided me in and the guy reached out and rubbed me through my towel, my cock which was already tenting the towel went rock hard he tugged at my towel and it dropped to the floor my cock disappeared into his throat, he fondled Brad while he sucked on me, brad rubbed the guy and I continued feeding him my cock. The night was early and I didn’t want to cum yet so I pulled out and the guy turned around and offered up his ass, Brad slipped a condom over my cock and I slid into the Latin’s ass, god it felt good his muscles gripped my cock and as I pumped into him he purred and cooed like a cat in heat. I still didn’t want to cum yet so I pulled out as Brad slid in he’d pound the guy till he was really close then he’d pull out and I would slid into the hot Latin ass, we tag teamed that guy for about half an hour then he said he was getting sore and we left his room promising to return and finish the job, we wandered back to the play area and I soon found myself in a cubicle with Brad in the next one, Hot daddies and guys were wandering around on a raised platform and a daddy approached my enlarged glory hole and presented his cock, I tentatively put my hand on it then placed it to my lips, taking the head into my mouth, tasting for the first time precum, I was hooked, Brad next to me was deep throating a hot twink like us and sucking him. The daddy I was sucking grunted the blasted his load into my mouth and throat, lavishing his seed on me. Brad and I wandered the halls and the maze taking in as many loads of cream as the participants would allow, retiring occasionally to the steam room and the Sauna to take breaks from the sex, each time ending up putting on a show of making out and fondling. I became a safe top that night, finally realizing my lustful fantasy with Brad.

 

Graduation came shortly after our night of debauchery, and summer was upon us Brad got me to log into various gay websites and applications for my phone, I went a couple hours to the east to a good university and was paired up with a hot athlete named Jeremy who I at first thought was Straight because he never seemed interested in the frat boys I would bring back to the dorm room to corrupt by spring break though I realized he was jerking off to all the hot guys I was sucking and fucking across the room. Our realization of each other turned a sexually tense situation into a close relationship that made us best buds, almost brothers I knew Jeremy was virtually a virgin and didn’t want to rush him into anything sexual, I was falling for his innocent charm, though I found out he was using my stories of my exploits as good jack off material. We survived our freshman year and ended up spending the summer together, his Uncle Tony helped us find housing for our sophomore year as his mom was getting very sick and was in and out of the hospital. Jeremy was brought up in the east bay but when his mom got sick in his early high school years they moved to be closer to tony and his family. Soon Jeremy was spending his weekends with his mom or Tony. I was left free to explore my sexuality and my fascination with Daddies. That’s when I met Pete at a sex party I was invited to, I started hanging with Pete who was about 15 years older than me, he had some really hot daddy friends and a little of a wild kinky streak. We saw each other for about 6 months when he said he knew of this really hot sex party the last weekend of February, I was excited to go at the time, Pete was beginning to get really dominate with me and I guess in a sense was making me more kinky and perverted, getting closer and closer to abandoning my safe sex stance and making me less of a dominate top, Edging me closer to bottoming. The weekend was upon me and Pete picked me up and in no time we were up in the foothills at a really nice mansion the host no doubt was well off. I entered and Pete instructed me to strip, towels were provided and I walked around the party like it was a bathhouse. It seemed like I always had a cup of beer or other lavation and soon I was buzzed and my head was foggy. One of Pete’s friends asked me if I wanted to see what it felt like to be in the sling, I being a little wobbly and having difficulty in standing agreed and was soon laying back in the leather apparatuses I felt hands on my naked skin and probing my ass, someone dropped down and began rimming my ass, tonguing me deep, as I relaxed I suddenly realized that his tongue had been replaced with a log thin cock, I looked up into the mirror over the sling and did not notice a condom and began to freak, asking if he was fucking me raw and he nodded and told me it was too late as I already had two of his loads in my gut, my hole felt sloshy as a longer thicker cock was shoved in using his cum for lube. By the end of the night and two of the other guess who had been led to a sling had been bred by at least two third of the tops there. Pete took me home and had Jeremy help me into the house and to bed. If felt used the next morning and considered breaking it off with Pete, then he called and talked me into another few weekends of parties, all bareback and convinced me to bring some of my hot friends, I sort of felt like bait for these guys luring hot twink’s to the bb parties.

 

Spring break rolled around and I started feeling like shit, I though good thing it was during my time off from school. Jeremy nursed me back to health from my bout with the flu. A few weeks later Pete showed up and offered to take me to the clinic and have me tested for STI’s, of course they ran a HIV test and it came back positive. Pete said he would take care of me, he moved me into his inner circle of friends and I helped him and his friends pick up younger guys and invite them to their parties. After 8 Months of that I couldn’t take it anymore, but Pete convinced me to keep going that he’d help me make it better, I put up with his bullshit for two more months before he called me a ungrateful asshole and I was getting too old for him anyway, about that time he found a cute 18 year old Twinkie boy who he used just like me, I knew the kid and tried to warn him of the dangers, but he pulled me aside and told me it was ok he liked being dominated, and Pete Had No idea he was already on PrEP, behind his back. I wished him good luck and drove away promising myself never to be taken in by anyone like Pete.

 

About the time I was breaking it off with Pete and company, Jeremy had found a really nice guy, who I originally thought was taking advantage of my best friend and was about to tell him so when, Jeremy told me it was actually his biological dad, so he doubted he would screw us over like Pete did.

 

I really got to know Matt and I never seen Jeremy so happy, then Matt asked us if we would like to move into his spare room to save us on expenses, I was interning at an architecture office and though the pay was ok it barely was paying the bills alongside my stipend from my grandparents estate which I couldn’t really touch much of until I was 25, getting full control of the trust when I reached my 30th birthday.

 

It had been a year since I had the Fuck Flu as Pete explained it to me and a lot had changed I was closer to Jeremy, who not only introduced me to his dad, Matt, but a hot little Jock boy Named Sam was infatuated with me and I started thinking of him as the little brother I never had and he loved having sex with me, safe of course but Matt arranged for me to go on meds and for Steven and Sam to go on PrEP to keep them safer. Then he asked us if we would like to have a really fun Spring Break, We all of course said yes so here I was at 30,000 feet squished in a airplane bathroom with my raw cock up Sam’s rear blasting my Toxic cum into the hot little jock, I went back to my seat and Sent Jeremy over to help Sam take care of his itch for cum and when he returned without Sam I just looked puzzled. Sam returned about ten to fifteen minutes later explaining, the cute attendant that assisted us on boarding had used him as well as a cumdump.

We arrived in Chicago and Matt whisked us to a Really nice Hotel where he had a suite reserved, and we all collapsed on the bed together after stripping off our sticky sweaty clothes, falling asleep in each other’s arms, Matt had gone into his Room and most likely collapsed after disrobing himself.

 

Later that morning I was the first to wake and untangle myself from the others I walked naked into the living area of the suite, made two cups of coffee and carried them into Matts room, he was sprawled naked on top of the bed and after taking a sip of coffee climbed on next to him and cuddled my hot little benefactor, e wiggled his ass against my boner and soon my precum had lubricated his hole and I slipped In bare into his hole, giving him a slow passionate fuck enjoying the feel of this mature man, the daddy of my dreams. It took me about 20 minutes of slow fucking him before I reached the point of no return shooting my Poz cum into his rectum. He opened his eyes as I pulled out and I handed him the second coffee

 

“thank you for your gentle fuck to wake me, and thanks for the coffee, did you just fuck me bare?

 

“yeah I figured you have been on PrEP for a week it would be alright”

 

“I didn’t go on PrEP, I gave my pills to Sam, I’m still chasing”

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Book II

 

Sam

 

Wow, It had been a emotional roller coaster ride over the last month and a half, Not only did I get to fulfill a fantasy of mine since I was a freshmen in high school, but that fantasy was now my possibly my boyfriend, yes he was four years older than me and he was seriously involved with his roommate and Dad, but I liked both of them too. As a matter of fact I  wanted his roommate Steve to want me too, I think he liked me as his kinky little brother type relationship. We were quickly becoming the three amigos as we were always together when we weren’t in school or at work, and his Dad Matt made things easier for us to be together, encouraging us to hang out and facilitating hot make out sessions.

 

Speaking of Matt, I suspected that he was having meetings with my Dad, John, not sure if they realized I knew but I did and I was happy that my dad slowly was warming up to me, and we were finally getting closer. My dad did a lot of traveling with work and until I was a little past 14 I spent a lot of time with a nanny to watch over me, although I don’t think it had a lot to do with him dismissing the nanny when I was almost 15, I had come out to him just before my 13th birthday, and he decided I could take care of myself, we had a house keeper who kept the house clean and did the laundry, and I was quickly becoming a pretty good cook, hence I could feed myself. He even liked my best friend Darren who would spend a lot of time doing guy stuff together, we played on the same sports teams and had almost the same classes so we helped each other a lot with our homework. I was a pretty dependable and responsible kid.

 

As I was saying, I think he was having meetings with Matt and they were discussing me and my friendship with Jeremy and Steven, maybe even Darren. I was happy to see my dad making a friend as with taking care of me and traveling, he really hadn’t made many friends male or female since my Mom left us. I also rally liked Matt and sort of thought of him as a second Dad, I was even thinking of introducing the trio to Darren, but that would have to wait as my dad had told Matt he could take me away on Spring Break.

 

Evidently Matt had told Dad where we were headed, but wouldn’t tell us boys, it wasn’t till we arrived at the airport that we discovered we were headed to the windy city, Chicago. We boarded the plane and took our seats with the assistance of the attendant Will, He was late twenties and very thin but muscular. After the plane had been in the air for about forty minutes, I whispered to Steve I needed to use the facilities, and hinted he should follow me in a couple minutes. I walked back to the laboratory and noticed it was just off of the galley of the plain where Will was prepping the in-flight service, I smiled at him before entering the toilet, I did not lock the door and a couple minutes later Steve was entering into the cramped space. I was seated on the potty when he entered and locked the door behind him. I unzipped his pants and pulled out his growing piece of meat, sucking on it to get it hard and wet then carefully stood up and turned to the mirror and lt him slide his meat between my cheeks, I was prepared and handed him a small tube of lube and he slicked up my hole, he squeezed some out on his spit slicked cock and proceeded to slide his monster back and forth between my ass and my thighs

 

“Fuck me with that monster, give me your bare meat, isn’t this why I went on PrEP”

 

I whispered back to him as his head caught on my pucker then began to slide into my hole. He slowly worked his cock in and out of my hole then after about five minutes he whispered back at me

 

“I’ve been wanting to do this with you for about a month now, breed your ass with my Poz cum, ahhhhhghhh , here it comes, oh fuck, welcome to the mile high club stud”

 

He pulled out and I sat back down on the toilet and cleaned off my ass juices and his blood streaked cum from his dick, zipped him back up and told him I still wanted Jeremy to join me in the club.

 

A couple minutes later I repeated the sequence of events and took Jeremy’s hard cock into my hole now slicked up with Steve’s cum. Jeremy fucked me and joined the mile high club having two massive loads in my hole I pulled out a medium Butt plug I somehow got through security in my carry on, then transferred to my baggy cargo shorts when in the restroom at the airport. After Jeremy exited the restroom I was getting myself cleaned up when Will came to the door knocked lightly then opened the door to find me with a raging hard on and a plug up my hole, He stepped inside and began to feed me his drooling cock, he too soon had me pressed up against the sink and mirror and was plugging my creamy ass using my boys cum for lube.

 

“You’re awfully cute to be such a cumdump, boy you want my cum in there to”

 

“Oh yes sir please add to my load count”

 

“Oh yeah, you take all loads boy, even my highly charged Poz one”

 

“Oh yes sir Poz me up, Breed me with your toxic load”

 

With that he grunted and shot what must have been a weeks’ worth of cum up my ass deep into my gut, he grabbed the plug from the sink and shoved it back in my hole then proceeded to lick the cum that had escaped around the plug then kissed me with the combined mixture of jizz still in his mouth, giving me a taste of the cram that was in my colon.

 

I returned to my seat, walking gingerly so as not to dislodge the plug and sat back down. Resting my head on Jeremy’s shoulder I soon drifted off to sleep, awaking to the sensation of the plane touching down, still groggy, as where my Buddies we made it through the terminal and to baggage claim then out to the shuttle that took us to the rental car, Then Matt drove us to our hotel.

 

The hotel was a lavish one in downtown Chicago, we turned the car over to the hotel staff and valets who unloaded our luggage and escorted us to the desk where Matt checked us in then the bell hop showed us to our suite. It was a elegant suite with two bedrooms off of a living room, complete with mini kitchen/bar. Jeremy, Steve and myself were still pretty tired so Matt let us strip down and retire to the bedroom where we fell asleep in each other’s arms, the butt plug still firmly now being held in place.

 

I awoke the next morning to find Jeremy snuggled behind me pressing his engorged cock into my plugged hole, his precum lubing the way as it slide alongside the plug and he was double penetrating me with the plug in place it was a little painful being stretched so much, I pulled away and removed the plug then sank balls deep onto Jeremy’s hard tool. It felt so good to have him buried inside me, slowly gyrating his hips in his sleep, or at least I thought he was sleep, I matched him with pushing back on his cock then he grunted and made another deposit.

 

I got up and looked for Steve, only to find him fucking Matt, the only cock I hadn’t received a donation in my rear from on this trip so far.

 

They were fucking on their side spooning each other so I crawled up and slid in front of Matt and slide his cock into my creamy hole so now he was giving and taking.

 

Steve shot a load into Matt as Matt Blasted a load into me, then Jeremy came in and began fucking Steve, the Sex train started gathering speed again and we all blew another load just a half hour later. Matt directed us into the large Shower and we all washed the travel grim and the sex off ourselves and each other then he had us get dressed. He opened the drapes to allow in the mid-day sun

 

“Wow, what a view, and wish my dad could be here to see this”

 

I exclaimed, knowing my dad had conducted business in Chicago before but doubted he ever got a chance to s this vista. Matt smirked then asked if we were hungry. Being tweens, of course our answer was yes so he arraigned with the concierge for an authentic Chicago style hotdog and pizza lunch, he got directions from the hotel to the best hotdog stand within walking distance than we were off to a pizzeria dogs in hand. As we entered the pizzeria the last of the hotdogs were consumed, Matt polled us on our favorite toppings and went to the counter to order a couple large pizzas and to procure a soda for me and a beer for Jeremy, Steve and himself. We went and found a table that was close to the arcade and still within good view of the large screen television, which was playing the Final four tourney. Matt came and sat down with us then stacked tokens in front of each of us, enough to play some games. Jeremy and I went into the arcade and started playing some of the one shooters and Steve went for a high tech pinball machine. We finished a couple of games and returned to the table, where Matt was seated with a young man seated close to him, wearing a hoody so I couldn’t tell who it was from the back, I came around to the table and the boy took off the hood, I was in shock, it was Darren

 

“Dude what are you doing here?”

 

“Your Dad and Matt here made arrangements for me to surprise you, on my birthday”

 

“Oh god, with everything that has happened lately I totally forgot your birthday, I’m so sorry”

 

“It’s ok, your dad talked my parents into letting me come surprise you on spring break, and I’ll be staying with you if it’s no trouble”

 

“Fuck no, I’ve been wanting you to meet Jeremy and Steve”

 

Darren has been my best friend from school since like third grade, we hung out together and he was the first friend I ever told I thought I was gay. We did a lot together including cuddle and kiss and occasionally jack off, he was the one I told my secrets to including browsing on A4A, and manhunt, he was the guy who got me to sign onto BarebackRT and eventually Breeding Zone, we’d sit and cruise the net and read BB sex stories, we even shared Bug chasing fantasies but we never had real sex. And here he was with me and my little extended family who loved to get naughty, I was ecstatic and nervous for him all at the same time. I looked around the pizza parlor, and gave him a big hug then kiss.

 

I introduced him to Jeremy and Steve and we soon were munching down Chicago style Pizza and talking like we were all good friends and had known each other for years. Jeremy and Steve took an immediate comradery with Darren which made me very happy. After the five of us had scarfed down the two large Pizzas, Matt Suggested we head back to the hotel to take in the gym to work off the pizza and hotdogs then take a short nap before dinner.

 

We arrived at the Hotel and discovered Darren’s stuff had already been delivered to our room. We changed into Workout gear and headed to the gym in the hotel, a group of hot personal trainers were assigned to us and put us through some rigorous paces before allowing us to retreat to the sauna and steam room to relax

 

I went into the steam room with Jeremy and Darren, Steve and Matt hit the Jacuzzi sauna. As I kicked back in the steam room sandwiched between my two best friends we were all naked save for our towels and we were soon playing with each other’s penis’s stroking them and offering some nice hand jobs. Not wanting to get caught and thrown out of the hotel we kept it low key. After about 15 minutes in the steam room we all wrapped our towels around ourselves and headed out to the Jacuzzi where Matt and Steve were relaxing, they were a hot sight, they looked like dad and son enjoying a casual dip. About 15 minutes later we all got out and donned our workout clothes once again and returned to the room.

 

When we were back in the room Matt had us strip and head off to the bedroom

 

“it’s going to be a long night, with what I have planned for you four so get some rest, catch up on your sleep from last night and see you in a couple of hours"

 

the four of us laid on the bed naked and hard but we wanted to be fresh for the nights activities whatever they may be.

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Book II

 

 

Matt

 

I Woke up to Steve sliding in my ass his hot cock about to explode. I soon felt his tool swell and pulsate as he delivered his load unencumbered by any barriers, He wished me good morning and said that he figured it would be safe t fuck me, as I was on PrEP, I told him I was not and I was still chasing his toxic load, this made him even more horny as he began to massage the cum into the walls of my colon with his hard cock, before long he was going for round two, when Sam entered the room followed shortly be Jeremy. Sam squirmed in front of me taking my cock into his cummy hole and soon after Jeremy scooted behind Steve and began humping his cock into his former roommate’s hole, we were a sex train about to derail as our boiling balls churned up fountains of spooge. Not sure who fired first but it set off a chain reaction and soon we were releasing cum into the ass of the boy/dad in front of us, Sam shooting across the comforter and onto the floor. After we were all spent, I led them to the large communal sized shower off my bedroom and we all soaped and played with each other, finally when everyone was rinsed and free of the grunge of traveling for five hours, and countless loads of semen spilled into hot receptive holes, we all stood drying ourselves, clean at last. I sent the boys into their room to get dressed once dressed we headed out to eat, first stop was to get a good old Chicago style dog, not sure if the boys would like it, but I got one for each with the fixings, then as we continued walking and they devoured the treat we finally came across one of the famous Chicago style pizza parlors and I guided them in.

 

After quizzing them on their taste in toppings I went to order along with beverages. I returned to the table with tokens so they could play the arcade games and off they went just like little boys with a new present. I knew they would be occupied for a while. Just before the Beverages and pizzas arrived I looked over to see John standing in the door way with an adorable blonde boy of 18 about 5’7 and maybe 140 pounds muscled yet petite. He sent the boy over wearing his hoody pulled over his head, signaled he’d see me later and was gone. The boy’s name was Darren and he was Sam’s good friend from school who wanted to spend Spring break with Sam and his new fiends, for his 18th birthday present.

 

The boys returned to the table just as the Pizzas arrived and picked up their beverages then Darren turned around to face Sam. Sam’s jaw hit the floor as he was in a state of surprise then he started rattling off questions n why, how, what Darren was doing here. Darren explained the situation to him and they hugged and after looking around Sam kissed him full on the lips. We settled down to eat the pizza and the boys chattered back and forth, by the time the pizzas were devoured they all seemed like old friends, by the time we got back to the Hotel they were punching and shoving each other like schoolboys.

 

I had the boys hit the gym with me, having arraigned with the concierge for personal trainers for each of us, to keep us on track and working out rather than slacking and watching the eye candy which the hotel gym was full of. After a nice soak in the spa we headed back to the room, I had them strip and deposit their sweat gym clothes in a basket, then sent them to their room. I too needed to lie down for a while, it was around 3 o’clock local time but only noon in my body’s time clock, having gotten up this morning around 9 I barely had 5 hours last night. I striped off my clothes depositing my sweat shorts and top in with the boys, none of us wore underwear to the gym so it was just basketball shorts and tees in the bin. I set the alarm on my phone for 6 and laid down and was soon drifting off to sleep and to dreams of what might be in the future for us.

 

My alarm woke me at 6 and I dragged myself off the bed, I wandered into the boy’s room to find them in a tangle of legs and arms holding and snuggling each other, Darren was right there in between them, sandwiched between Jeremy and Sam Stevens feet thrown over all of them. I went around and shook each one awake fondling as I went, We had come directly from getting out of the spa without showering so I slowly guided the sleepy headed boys who insisted they didn’t need a nap to the shower, climbing in after them and turning on the spray, the cold water woke them up fast before the water became warm and soothing. The boys washed Darren, and me as I caressed our new comer to our soiree and soaped him up, his cock was just slightly larger than Sam’s which made me happy as he would end up getting the attention he deserved tonight with that piece of meat, hell they would all be getting a lot of attention tonight. Once again we were cleaned up with fresh clothes on the boys in tee shirts and jeans, I in a button down and jeans as well, the concierge had recommended a couple casual dining restaurants within walking distance of both the hotel and our destination for the evening activities, the boys chose a BBQ place and we headed over, each of the boys got the large platters and I got the medium one, nothing like a good BBQ brisket of beef, home style baked beans and cornbread. After downing our meals it was almost 9 o’clock as we walked to our next destination.

 

I handed each boy $20 told them to get a locker and make sure they told the clerk they were here for CumUnion, I opened the door to the Steamworks and followed my charges inside, they each followed my instructions and were buzzed in, I asked a large room with sling and was put on a waiting list, but I was near the top of the list, and to speed things up got the VIP membership. I got buzzed in and found my locker stripped down and wrapped the towel around my waist. Upon looking for the boys I found them huddled around Steve at his locker, I walked over and rubbed on each of them, Steve and I had been to the Berkeley Steamworks but we were all Chicago virgins. I put my arms across Sam and Darren’s shoulders and started guiding them into the recesses of the bath house. We passed through the halls lined with doors, a few ajar with guys playing with themselves and some entertaining others, playing together. I could see the boys getting majorly turned on with all the flesh that was available to them, tenting their towels. We continued the tour of the facilities finding the sauna and steam room as well as the showers, finally ending up in the darkened play space. I found an empty sling and helped Sam climb in, Darren began playing with his cock. Jeremy and Steve straddled his head, offering up their cocks for him to fill his mouth with, Darren reached back and began fingering his hole, as I dropped down and began eating that delicious ass. Sam was in ecstasy in sensual overdrive, alternating between sucking Steve and Jeremy’s thick cocks, Darren playing with his cock and balls, and I began sliding my cock in his boy cunt. I was leaking precum something fierce and soon Sam’s hole was wet and sloppy from all my pre jizz and Darren drooling down over his balls, running down his crack for my cock to push into his hole. I was getting close and we were beginning to gather a crowd, which only added to the sexual excitement, I took a step back and a hot guy stepped up, I turned my head and kissed John just as he slid his cock into his son, Darren recognizing John continued to suck Sam but then came to clean off my cock, I stood him up and had him slide his cock in Johns crack, which was moist with sweat and cum, soon Darren had slid inside his best friends dad and was fucking John as Sam was taking his dads big cock. John leaned over and started kissing Sam, the whispered in his ear

 

“I’ve wanted to fuck this hole for years, but now that you’re legal I can, whenever you want it”

 

I pulled Darren off of John and began kissing him then lifting his leg up slid my cock into his hole, I found a fuck bench and leaned Darren over it plowing into his virgin hole, someone came around and shoved a cock in Darren’s mouth and began feeding him his cock, I slid into his tight ass slowly at first, until he was taking my whole cock deep in his boy cunt, I began pounding Darren while looking over at Sam being pounded by his dad, while slurping down Steve’s cock. Jeremy was fucking some daddy bear in the shadows, while fingering Steve’s hot rectum. Soon I shot my load into Darren as Steve was about to shoot down Sam’s throat, pulled him over to the bench to dump his load deep in Darren’s boy cunt I could actually see his balls pulse as he shot a massive load into Sam’s best friend, while Sam cleaned off my cum coated tool, His dad unloading a huge blast of cum deep in his intestine working the spooge into the intestinal walls. It was an illustrious start to the evenings CumUnion event, by the end of the night, early morning festivities we all managed to blast our loads multiple times in as many holes that would take our cocks in Raw. And Sam officially became a cumdump taking at least 15to 20 loads and we each ended walking back to the hotel leaking spooge out of our cum filled holes.

John accompanied us back to the Hotel, Sam was still a little shocked and Darren was in Gay boy heaven being with his best friend the way he had dreamed he could be for the past few years after realizing he was lusting after his gay friend. We got into the hotel around 4am and I had the boys re-shower and told them to have fun while John and I retreated to my room. I hinted to maybe join us in our bed, making it three to a bed. I heard the shower stop and the boys giggling then the shadow of my Norse god filled the door way then crossed the room and snuggled between John and me.

 

We were worn out from the evenings fuck fest and all soon fell asleep in each other’s arms. I awoke around 9 to the sounds of fucking coming from the other room, I got up and went to go pee when Steve entered into the bath behind me as I desperately tried to piss with a raging hard on.

 

“Here let me help you with that”

 

He dropped to his knees taking my cock into his mouth, I moved us into the shower and concentrated on releasing my bladder, it started out as a trickle then soon it was a full flow of piss into Steve’s mouth. I was about halfway through my release pulsing the stream to help Steve

keep up when I heard a voice behind me

 

“Oh yeah this looks like fun”

 

Then John was beside Steve with his mouth open, I alternated between the two pissing on them and filling their mouths with my morning piss. After the flow ceased, John sucked me to full hardness, then Steve stood up and slid his cock into my ass, which was still oozing cum and ass juices he pumped me a half dozen times then pulled John up and used the cum and ass juice from my ass to slide into John pounding his hole while I turned around and guided his cock to my hole, soon we were fucking each other in the shower standing up, Steve blasted in John then John dropped his load deep in me and we all began kissing and making out as I blasted my nearly toxic cream over all of us. I reached over and turned on the water and washed us all off. After the three way shower we all dried off and headed into the other bed room to find the other boys in a three way suck/rim fest. John slid his cock back in his boy and I slid into Jeremy, and Steve into Darren as we fucked our boys to another climatic orgasm.

 

I ordered room service Sausage, Ham and scrambled eggs with champagne and orange juice for all of us, we mixed the two beverages much to the delight of all the boys and sat down to a hearty breakfast. Along with toast and jelly the boys were ready for our next adventure.

Edited by Rawdad4sons
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Book II

 

 

Darren

 

My birthday was last week, well actually earlier this week, and I feel like I’m going to burst. John, Sam’s dad, arraigned for me to meet up with Sam on spring break, I really don’t think he told my mom every detail but that’s for the best.

Like Sam I was raised by a single parent since I was 9, mine due to a car accident and not a divorce/ abandonment, so when we met the first day of Junior high, we had a connection and have since become like inseparable buds ever since. I was the first person Sam came out to, even before his dad, and he was the second person I told I was gay, my mom being the first last year. I don’t know why I waited so long to tell Sam of my gayness, he most likely already knew, what’s it call gaydar, but when I told him he was like “so what, now we can get on with our lives”. As anyone with eyes and was paying attention could tell Sam was my one and only crush, I idolized the guy, sure we were both jocks at school and that kept most of the bullying down, but together nobody messed with us, I was also saving myself for him I guess.

So when I found out that he and his new boyfriends were going away for spring break just a couple days after my birthday I was a bit crushed, if not a little jealous,  I was hoping he would want to spend it with me. When John pulled me aside the day before my birthday and asked what I wanted for my birthday, I just blurted out “ I want to spend spring break with Sam”, John told me he’d talk to my mom. John then made arrangements with her telling her that a good friend and father of Sam’s boyfriend was taking the boys to Chicago for spring break, and since he had a business meeting in Chicago he could drop me off with them and surprise Sam in the process. He came back to me and told me I had to keep it hush, hush with Sam and that we’d be taking the red eye on Thursday night. I was elated and at the same time somewhat scared, as it would actually be the first time I had met the boyfriends.

 

Thursday came and I could tell Sam was excited about spring break and I so wanted to tell him I was joining him, but I couldn’t spoil the surprise, and just played the supportive best friend. John picked Sam up from school and as we hugged goodbye gave me a wink and whispered “be ready at 7:30”, he then whisked Sam away to drop him off at Matt’s

 

I was excited too, I finally was going to meet with Jeremy and Steve, it has all Sam has been talking about for the last month is how Jeremy and Steve did this or that, and he occasionally would mention Matt as well. And now I was about to meet this dynamic group of guys, I won’t say I wasn’t jealous at first when they met but now I was actually looking forward to it.

 

I had met Matt when I showed up early to pick up Sam, we were going to a movie or something, and Matt was just leaving, it was obvious that they had been up to something more than having casual drinks and discussing their sons. To tell the truth I was actually hot for both of them as I imagined what it would look like if they were having sex together, played out like some of the porn movies that Sam would show me.

 

Sam and I shared a lot together, good times, bad times, taste in men, fetishes he actually help me set up accounts on A4A, BBRT, and Breeding Zone, to name a few and we would jerk to the stories contained within BZ, guess it sort of made me want to not only take it raw, but to take all cum loads, and in return breed as many boys and men as I could, it made me darn horny just thinking about taking and giving seed. I knew Sam was a bit of a chaser and I wanted to chase as well.

 

At 7:30 on the dot John pulled up and I loaded my duffle bag into his car, we then headed to the airport, after getting through security he took me to one of the nicer restaurants and we had dessert together. I always felt that John had a thing for us but he confirmed it that night, as he held my hand under the table while we shared a cobbler bringing my hand to his throbbing piece of meat, I could feel its hot steel steaming wanting me. He smiled and leaned in and told me he wanted to plow my fields for a long time now but was allowing me to experience his son first. As the time of departure approached John got friendlier and soon I felt very close to him.

 

Both John and I fell asleep on the five hour flight, and were a little groggy when the plane rolled up to the gate at nearly seven in the morning Chicago time, we got our luggage and John hailed a cab to take him to the hotel his conference would be at. He instructed me to use the men’s room to freshen up and he would be in a conference until around 11, which was about three hours away. He somehow got permission for me to use an unoccupied meeting room to doze off or play video games on my phone, it had a nice couch off to one side which I curled up on and played on my phone, using the hotels guest Wi-Fi before I slipped into a sound sleep. About 11:15 he shook me awake and we caught a cab to a Pizza parlor where he said they had the best Chicago style pizza and where I would catch up with Sam and company.

 

The boys were off playing arcade games when we entered and John gave me a little shove in Matt’s direction, I walked up to Matt and he gave me an unexpected hug and invited me to sit down. The drinks arrived, three beers for Matt, Jeremy and Steve, and two sodas for Sam and myself. I had my hoodie on so the boys wouldn’t know who was sitting with Matt when they came back from the arcade. Matt and I chatted a bit as we discussed some of his plans for us during spring break, it all sounded like a lot of fun. He told me that John would drop my bag off at his hotel and he had already made arrangements with the front desk to have it put in his suite.

Sam, Jeremy and Steve arrived back at the table and Sam stood there in a state of disbelief for a second

 

“dude what are you doing here, how’d you get here, oh my god this trip just got even more perfect”

 

Without even waiting for my response he grabbed me in a big bear hug and just about knocked the wind out of me, then he turned around to the others

 

“Guys I want you to meet my dearest and oldest friend, Darren. Darren this is Jeremy and Steve”

 

As he pointed to each of the hottest guys I had ever been lucky to be introduced too. I explained about how Sam’s dad and John had convinced my Mom to let me come on spring break with them, leaving out the part of John bringing me here. We started all talking as the pizzas arrived and soon we were devouring the pies and talking up a storm about the video games and the game on the big screen television, who we thought would be in the final four NIT and all other kind of bullshit.

 

With lunch over and all of us stuffed with pizza, Matt herded us back towards the hotel, explaining that after all those carbs we just ingested that he had arraigned for us to all have a personal trainer for gym time when we got back to the hotel, and to get in our gym clothes as soon as we got to the room.

 

Upon arrival at the suite I was surprised that my bag was indeed there and I dug in and pulled out my jock, basketball shorts and a muscle shirt and quickly changed, in front of the other boys, into workout gear, they were changing too as I glanced over at Sam, Jeremy and Steve, I started to get hard, but I willed my mind onto something else. I needn’t worry as they were already semi hard themselves, we all took the elevator down to the fitness facilities and met up with our trainers for the day, mine was a hot twenty something blonde guy who could easily pass for a younger Brad Pitt, Jeremy’s trainer looked like a twink porn star and Steve’s was a thirty something hunk as well. I thought my wrestling and La Crosse coaches’ were tough but these guys were brutal, they put us through our paces and flirted heavily with us while doing so, we were all drenched in sweat as the 1.5 hour session ended, Matt suggested a sauna visit to relax us before heading back to our suite.

 

I had never been in a gym where all the amenities were located in the locker room, I’d always have to deal with co-ed situations, so it felt wonderful to just strip out of my sweaty gym gear and just wrap a towel around my waist, we handed the attendant our sweaty clothes and

Matt told him the suite number, I was mystified, but went with the flow. Sam and Jeremy took my hands and lead me to the steam room, while Matt and Steve slipped into the Jacuzzi, buck ass naked, once in the steam room I had Jeremy on one side and Sam on the other they began to tenderly caress my hard pillar of flesh, reached over to each of theirs and stroked their cocks as well . Before we knew it we were all drooling precum, but didn’t dare take it to the next level in such a public place, Jeremy wrapped the towel around his waist and led Sam and I out to join Steve and Matt in the Jacuzzi.

 

After soaking with Steve and Matt for about 15 minutes, Matt suggested we head back to the suite

 

“But we don’t have our clothes? How do we get back?”

 

At that Matt raised his hand for the attendant and suddenly the young man appeared with a bath robe for each of us along with slippers.

We each wrapped a robe around our bodies and slipped into the slippers then proceeded to the elevator then to our suite. Upon arrival at the suite, a very luxurious one I might add, Matt told us to lay down and get some rest before dinner, Matt went to his room and we retired to ours, as we each dropped our robes and tossed them to the side, we were soon caressing each other, Sam paying a lot of attention to me whispered in my ear

 

“You still serious about chasing?”

 

I shook my head yes as my boner got even harder, Sam began fingering my hole, sometimes scraping with his fingernails, occasionally adding spit to slick his fingers and make penetration deeper. Soon Sam led me to the bed and made me lie down, lifted my legs and began kissing my ass cheeks before moving in and tonguing my hole. Jeremy and Steve were on the other side Kissing and fondling each other as I experienced the most awesome sensation of my life, Sam dug into my hole loosening it up with his tongue and fingers, When he was able to get three fingers in and twisting them around to where I was moaning in pleasure he pulled them out and slipped the head of his cock into my hole using just his spit for lubrication. He paused with just his mushroom cap buried in my sphincter leaned over and kissed me passionately gyrating his hips slightly. As we were kissing I could feel his tool slowly entering into my once virgin hole, inch after inch till I felt his pubes tickling my balls and his balls slapping against my cheeks.

 

“I’m all in you Babe”

 

“Oh yeah, fuck me Sam”

 

Sam withdrew his cock back to the head, then slammed it back in, no more Mr. Gentleness, he started fucking me hard pulling out and driving back in trying to gain new depths with each new thrust, pounding me into the mattress.

 

“Oh yeah Darren, Babe I’ve wanted to fuck you for a long time”

 

“Mmmm oh yeah, fuck me”

 

“you want my load, I’m fucking you Raw, you want me to cum in you”

 

“Fuck yeah, give me your seed, Fuck, fuck, oh, FFUUCCCCkkkkk”

 

“Oh YEEEaaahhh, Giving you my seed”

 

I could feel my insides getting wet and sticky, Sam’s cock pulsating in my rectum, he slid it out carefully then Jeremy slid his big piece of meat in my hole t fill the gap Sam left, Sam crawled around and fed me his slimy cock, telling me to clean it off, Jeremy pounded me for another 5 minutes, then unloaded his load deep in my guts to join Sam’s massive load, while Sam and Steve took turns kissing me

 

“You ready buddy, now for your deepest desire”

 

“Making you my first was my desire”

 

“No, your other desire, Steve here has a viral load in the upper six figures, and he wants a chance to make a deposit in your Negative Ass, Pop your Poz cherry”

 

My cock which had been drooling Pre-Jizz into a puddle in my belly button suddenly hardened more then shot out a large amount of precum to add to the pool of man juice. Steve came around as Jeremy slid up and feed me his cock, covered in their cum and my ass juices, Steve rammed his cock home in one push, then roughly fucked my no longer virgin hole pounding away at my tender insides ripping gashes in my colon walls to allow his venom to sink in directly to my bloodstream he pounded me for about 10 minutes then blasted his load inside me

 

“There’s two more to add to your total for the night”

 

“Two?”

 

“Yeah I came shortly after I rammed it home then just fucked it into you while building up my second load to drive my toxic seed into you”

 

I thought “Holy fuck” I just took a hot toxic load into my boycunt my dreams were coming true. We all climbed onto the bed and cuddled and soon were fast asleep 

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