Contents

1. The Frat Party Dare

2. The Rebound

3. The Wedding

4. The Frat Party Dare (Part 2)

5. The Legacy

6. The Honeymoon (The Wedding Part 2)

1

The Frat Party Dare

We all sat down in a circle, away from the madness of the rest of the party. We’d stumbled into somebody’s bedroom and figured it was the perfect spot to play a card game. I was with my friend, Jen, and a few other girls- along with a group of my frat brothers. I was still pretty new to the fraternity, although I’d completed pledging.

Sitting directly across from me was Jimmy- the hottest guy in our fraternity. He was an athlete, lean and muscular, and had a smile to die for. I’d had my eyes on him since day one, and I have to figure he’d caught me checking him out a couple of times. He was a party animal, though, and had a reputation for the quantity of ladies he took to bed with him. I knew I had no chance. Or at least that’s what I thought. 

“Truth or dare,” one of the girls said as she took out a deck of cards. “Except you don’t get to choose. Draw a black card, truth. Draw a red card, dare.” Everyone agreed to the rules. 

The first couple draws were tame. Someone mentioned the wildest place they’d ever had sex, which was on a beach. One of the girls was dared to flash the rest of the group and did. Next, the deck of cards landed on Jimmy. He drew a red. The rules stipulated that the members in the circle of the opposite gender got to pose the question or the dare. The women deliberated and came to a decision. 

“Make out with one of the other guys,” they said. 

Suddenly, my stomach was in a knot. I looked at Jimmy, wondering what choice he’d make. Part of me hoped it was me, of course- I’d have done anything to kiss a guy like him. Part of me hoped it wasn’t though. The potential for embarrassment was high. My heart started beating faster, with my nerves increasing. His eyes looked back at mine, and locked with the other guys in the room too. The few seconds it took for him to make his choice felt like minutes. 

“Adrian, come here,” he said. 

Fuck. That was me. Everyone hollered and cheered, knowing they were about to get a show. Jimmy stood up, and I stood up slowly and nervously. I walked over to him, our faces coming closer together. 

“Come on, man,” he said. “Let’s get it over with.” 

“Okay,” I said. I smiled and pretended to be just having fun- like him- and took a deep breath. 

Jimmy pulled me into him and our lips touched. I felt his athletic body press against my own less athletic but still proportionate frame. I felt a spark travel from my lips, down my spine, and into my groin, where my dick began to fill with blood. Fuck. I was getting hard. 

The dare was to make out- so the kiss lasted for several seconds. I even got a little taste of Jimmy’s tongue. I felt his strong arms holding my body, and I wanted the moment to both end and never end at the same time. If only he were kissing me because he actually wanted to, and not because of a dare. 

By the time he let go of me, my knees were quivering. I rushed back to my spot in the circle, trying to hide the tent that was obviously protruding in my shorts. I was pretty sure everyone saw, including Jimmy. Nobody made a comment though. Thankfully, the rest of the game was pretty tame, and a few minutes later we all decided to go back out and join the rest of the party. Jimmy and I were set to be the last ones out the door. Suddenly, though, I felt a hand on my shoulder. 

“Hey, Adrian,” Jimmy whispered. As everyone else exited the room, the two of us stayed back. 

“What’s up?” I asked, pretending like nothing was wrong or strange. 

“I, uh, I chose you to kiss on purpose, you know,” he said. 

“Huh?” I replied, still playing stupid. I could feel all the nerves and other feelings from earlier re-entering my body. What exactly was he getting at? 

“Don’t think I haven’t noticed the way you look at me,” he said. Oh shit. 

“I- Jimmy- I’m sorry,” I started. 

“Sssh,” he said, holding his finger to my lips. “Don’t be.” 

Instead of saying anything more, Jimmy took my hand in his and held it to his chest. My heart was beating out of my own like a drum. Slowly and methodically, he slid my hand down lower, over his stomach, abs, waistline- and eventually down to his groin, and his cock, which was bulging. I felt a warmth creep up inside my stomach. Suddenly, Jimmy kissed me again. This time he held on for much longer than he had in front of the group. 

I couldn’t believe this was actually happening. Jimmy began to pull off his shirt, exposing his naked chest. His skin was tan and glistening. He kissed me again. My hand was still on his bulge. 

“I always thought you were into chicks,” I said. 

“I am,” he replied in a whisper. “But I’ve heard dudes give better blow jobs. I guess I can be equal opportunity.”

“Oh,” I said, not sure of what else to say. We continued kissing.

“You are into this, right? We don’t have to…” he started. 

“Oh no, I’m definitely into this,” I said, pulling him toward me. He laughed, and I chuckled myself. This was indeed happening, and I was here for it. 

“Good. Get on your knees,” he commanded. 

I eagerly did as he asked. My face was now eye level with his crotch. He grabbed my head and pushed it into his shorts, where my face came into contact with his bulge. He breathed out a heavy sigh as I started to unzip them. When everything was undone, I took his boxers with his shorts and pulled everything down. His juicy cock awaited my mouth. I paused a moment, almost mesmerized by the sight I was seeing. 

“Well, what are you waiting for?” he asked. 

“Just savoring the moment.” That was the truth. Although I’d fantasized about it, I never thought this would happen with any of my frat brothers. Much less with Jimmy. 

Finally, I took Jimmy’s cock into my mouth. An excitement I couldn’t quite describe filled my body as the length of its shaft moved all the way across my lips and as far down my throat as I could take it. I nearly gagged. 

“That’s it,” Jimmy said. “Fuck, you’re better than anything I’ve had already.” 

That comment only made me want to work harder. I released it and took it right back, deep-throating it again, before moving into a steady blowjob. His cock tasted as sweet as I imagined. I lathered it with my saliva and caressed it with my tongue. I played with the tip, getting a hint of his salty precum. I started going up and down with a steady rhythm, using my hand for added sensation, doing the best job I knew how. Jimmy started to moan and thrust himself gently, adding to the rhythm I’d already created. 

“You’re fucking good,” he gasped. “That’s it. Take my cock.” 

He started pushing more aggressively, holding my head in place. I rested my hands on his ass, which was smooth, muscular, yet surprisingly soft. I looked up at him and made eye contact before re-focusing. He moved faster, fully fucking my throat, occasionally forcing me to take his cock as deep as I could. I almost gagged a couple of times, but I would have let him do it as much as he wanted. I reached inside my own shorts for my cock, which was itself throbbing at this point. Jimmy continued going at an intense pace. My jaws were getting sore, but I didn’t care. 

“Adrian, you’re gonna make me cum,” he gasped. My dick leaked at just the thought. “Take it in your mouth?” he said as if he was posing a question. 

“Mmmhmm,” I moaned with his dick still in my mouth. I couldn’t wait to taste his load. 

“Oh shit, here it comes,” he said in a moaning, high-pitched voice. 

Jimmy’s load busted out of his cock and into my mouth. As soon as I tasted its savory sweetness, I blew my own load in my shorts, the situation being so intense I couldn’t stop myself. I didn’t let a single drop of his cum escape my mouth. It was delicious and heavenly. 

“Well, what was the verdict?” I asked as he pulled his shorts back up. 

“Huh?” he said, looking confused- clearly with no idea what I was referring to. 

“Dudes or chicks?” 

“If they’re all good as you, dudes, hands down,” he said. “You, uh, might have to do that again sometime. If you want, that is,” he said, trying not to make any assumptions. 

“You know exactly where to find me,” I said. 

We cleaned up and went back out to the party. Our friends and the rest of our frat brothers were none the wiser. 

2

The Rebound

I couldn’t wait to see my buddy, Matt. I anxiously waited for him at baggage claim, waiting for him to walk out after his flight had just landed. He was coming to New York to visit me for the weekend. We hadn’t seen each other in months, but he’d insisted when he found out my wife, Hannah, and I were separating.

“Hey bro,” I said with a huge smile when I saw him come through.

“Hey Andy, good to see you man,” he replied as we shook hands and gave each other a pat-on-the-back style bro hug.

“What have you been up to, man?” I asked once we were in the car, driving to my apartment.

“Nothing too crazy. Just working and the same old stuff, you know,” he said.

“How is the dude hunt going?” I asked. Matt was gay- he’d come out to me many years earlier, when we were in college. I was fully supportive of him, and knew he was always on the hunt.

“It’s going,” he said with a laugh. “It’s a wide net without much depth, if you get me.”

“Oh I get you man.”

“What about you? How are things?” he asked.

“You know, they’ve been better. But I’m glad you’re here. Thanks for coming,” I said.

“No problem dude.”

Once we got settled in my apartment, we went out for dinner and drinks. It was nice to spend time with someone- anyone. I’d moved to New York a couple years before to be with Hannah, and most of the friends I’d made had been her friends. Since we’d separated a few months before, I hadn’t been out much. I was so happy to have Matt here with me.

When we returned to my apartment late that night, I crashed on the bed and turned on the tv. Being New York, the apartment was tiny, and although I did have a small couch, I hadn’t thought much about its size and where exactly Matt was going to sleep. The bed was also about the only piece of furniture in the apartment well-positioned to view the television, also.

“Where am I crashing?” Matt asked.

I looked around, scrambling in my head trying to figure out a solution. I couldn’t believe I hadn’t thought about this before. But there was really only one option that made sense. I had a double-bed that I used to share with Hannah.

“I guess you can crash in the bed with me, if that’s not too weird for you man. I’m sorry, I didn’t really think about it. I’m a bad friend.”

“Not at all,” he said, jumping on the bed and lying down without hesitation.

We lay there and watch tv for a while before we drifted off to sleep. I didn’t think much else of the whole thing- that was, until the next morning.

The sun peeked through the one tiny window I had and I opened my eyes. It took me a second to realize Matt was still next to me. And a few seconds later, as was typical after a night of drinking, I realized I’d woken up horny as fuck. I had a severe case of morning wood. I looked over at Matt, who was still apparently asleep. I couldn’t help but notice the massive bulge in his boxer briefs.

I didn’t know what to do. I desperately wanted to jerk off, but I felt trapped. I knew if I shuffled around, it would probably wake Matt. I decided to try to get up to go to the bathroom as quietly as I could. Sure enough, though, as soon as I moved Matt opened his eyes.

“Damn,” he said. He was looking at his bulge, and then his eyes quickly drifted over to mine.

“Morning,” I said, laughing, the only way to deal with the awkward situation we found ourselves in.

“I guess this happens when you sleep in the same bed,” he said.

I was shirtless, and I noticed Matt glancing at my body, which was nothing new. I knew he was attracted to me, but I also didn’t care. I trusted him not to damage our friendship. In that moment, though, I wasn’t sure if I trusted myself. An idea formed in my mind.

“Dude, I have a strange suggestion,” I said.

“Shoot,” he said. “Can’t be weirder than having morning wood in bed next to your best friend, who you’re not sleeping with.”

I laughed nervously. “Would it, uh, be weird if we, maybe, jerked off together?” I asked. Matt’s eyes opened widely.

“You, uh, really want to?” he asked. He seemed to be on the same level I was- both uncomfortable and intrigued at the same time. At the very least, he didn’t say no.

“Why not?” I said casually, trying to lighten the mood.

Matt’s eyes blew up and he took a deep breath. Then he smiled.

“Alright man, let’s do it,” he said.

“Cool.”

Since it was my suggestion, I pulled down my boxers first, letting my cock free. Matt smiled and pulled his off next, tossing them to the side. We both began stroking. I grabbed my remote and set up the television to play some porn. Matt kept glancing back and forth between me and the tv.

“You can look at me, dude, it’s alright,” I said.

I had to admit that part of me was turned on by the fact that I turned him on- that he wanted to look at me while he was touching his cock. It was nice to feel wanted, even if it was a dude who was attracted to me. Matt’s eyes came to rest on me, and he seemed to be getting more into it. I found myself paying more attention to him than the porn myself.

“Dude, I’ve always thought this, but never really told you…you’re fucking sexy,” he said. It caught me off guard that he was being this bold, but I couldn’t blame him.

“Thanks,” I said. “You look like you’ve been in the gym yourself.” Matt blushed.

We continued stroking for a few minutes. My cock was beginning to leak. I was more turned on by the situation and the novelty of it than anything playing on the tv. I decided I would see how far I could take this and how far Matt wanted to go.

“You can touch me, too…if you want,” I said.

Matt looked at me and then hesitantly reached out his hand. He slowly moved it toward my body. I nodded, sensing he was seeking permission one more time. Finally, his hand came to rest on my chest, and slowly started moving around as he got more comfortable. I scooted closer to him on the bed- close enough that our bodies were touching.

My cock was hard as a rock at this point. I got a surprising jolt when Matt touched me. I didn’t care that it was a dude, or that it was my best friend. I realized I hadn’t been intimate with someone in months, and that this was an opportunity we both wanted to flesh out. I got goosebumps as he ran his hands and fingers all over me, playing with my muscles, running in the cuts in between them.

“You have a good touch,” I told him.

“Yeah?” he said.

Our faces were now closer together. I was looking him directly in the eyes. I knew what direction it was headed and I didn’t stop it.

“Can I…” Matt started again. I knew what he was going to ask.

“Yes,” I said before he could finish.

I put my hand on the back of Matt’s head and pulled it toward me. Our lips met in an explosion of intensity. I was surprised at how much I was enjoying this, completely wrapped up in the moment. I knew he was, too. It was the first time I had kissed a man, and the ruggedness of his scruff against my face definitely reminded me of that fact. There was something masculine about it though that gave mea rush. I couldn’t put my finger on exactly what it was, but it was keeping my dick hard. And it was time to take care of that.

“You wanna suck my dick?” I asked after we’d been kissing for a while. Hearing myself say it, it didn’t sound as eloquent as it had in my head- but Matt jumped at the request.

“Fuck yes,” he said immediately.

“Get on down there, then,” I said, cracking up at how much he was enjoying it.

Within seconds, things were serious. Matt’s lips were wrapped around my shaft and going up and down with purpose. It felt fucking amazing- better than any blow job I’d gotten from my wife or anyone else, for that matter. I moaned with pleasure while he went at it.

“Dude that feels fucking amazing,” I said.

“Does it?”

“Fuck yes man. Keep doing exactly that,” I told him.

It felt so good I began to arch my back; pulses were running throughout my body that I couldn’t control. The work Matt was doing on my cock had me in pure ecstasy. I couldn’t believe how fast it happened, but I felt that familiar feeling come on quickly. He was talented for sure.

“You’re gonna make me cum,” I warned him. He kept doing what he was doing. “I’m coming,” I said, giving him one last chance.

Before I was done talking, my cock had released. I couldn’t hold it or keep it in. My load spilled over into Matt’s mouth as he kept sucking my dick; some of it drizzled down the length of my shaft.

“Well,” I said when Matt had swallowed my load and lay down next to me. I didn’t know what to say. He resumed stroking himself.

“Well,” he said with a huge smile. A few seconds later, he blew his load on his own body. It was an impressive one. “What’s for breakfast?” he asked, winking. We went about the rest of our morning as planned, like nothing had happened. But the whole experience only left me wanting more.

That night, I brought up the topic again- carefully, though. As carefully as I could.

“Hey, bro, what happened this morning didn’t make things weird, did it?” I asked.

“Not weird for me if it’s not weird for you. I just sucked your dick, man. I’ve….sucked dick without drama a lot.”

“Oh,” I said. “That’s cool.” I felt incredibly awkward. Thankfully, Matt took over from there.

“Why do you ask? Do you want me to do it again?”

“I wouldn’t stop you,” I said.

We were standing next to the bed. Matt pushed me down and kissed me before getting on his knees and pulling down my shorts. He wasted no time getting my cock in his mouth and getting it fully hard. His mouth felt so good- the perfect amount of warmth, moisture, and suction.

“You really do that well,” I admitted.

“I know,” he said. We both cracked up.

As he sucked my dick, I became more and more curious. Matt’s attraction to me had turned me on, and I wondered how far I could take that. I wanted more. I wanted to know more. I figured he already had my cock in his mouth…what boundary was left?

“Are you a top or bottom?” I blurted out. He stopped sucking my dick and looked at me intently.

“Versatile,” He said. “Why do you ask?”

“I’m curious.”

“Dude, if you want to fuck me, all you have to do is say the word,” he said.

“I…I want to fuck you.” I couldn’t believe the words came out of my mouth so easily. What was happening? Was I maybe into dudes as much as chicks? Did it really matter?

“You have lube?” he asked.

“Of course.”

We both prepped ourselves. I lay back on the bed, stroking my lubed up cock. It felt almost as good as having it in his mouth. Once he was ready, he sat over my hips, and lowered himself onto my cock as I held it straight up in the air. As he lowered, his eyes rolled back into his head and he took several deep breaths.

“Everything okay?” I asked.

“Yeah. You kinda have to warm up. It doesn’t work so easily right away,” he said.

“I gotcha. Do whatever you need.”

Matt didn’t take long to work himself up the way he needed. Within a couple minutes, my cock was entirely inside him, and he had the biggest smile on his face that I’d ever seen. He started rolling himself back and forth, massaging his hole with my cock.

At first, the weight of his body and the tightness of his hole struck me as a pretty stark contrast from having sex with a woman. I quickly grew into it, though. The same masculine feeling of kissing a man with stubble came over me as his muscular body did its work. And his hole was warm, tight, and provided a sensation on my dick unlike anything I’d ever experienced. Matt was already gasping, breathing heavily, and I soon followed suit.

“How does it feel compared to a pussy?” he asked.

“It’s different,” I said at first. We both had a little chuckle.

“Yeah?”

“But it feels fucking incredible.”

With that, things heated up. Matt rode me more aggressively and started moaning louder. I started pushing inside him myself, taking control of the action. We eventually flipped over and I took complete control, thrusting inside him in missionary with his back on the bed.

“You feel so fucking good inside me,” he said with a moan and heavy breath.

“My cock feels good inside your hole,” I told him.

My body tensed up as I slipped in and out of him, the stimulation on my dick like nothing I’d ever experienced before, not even his mouth that morning. It was incredible; it was electrifying. I loved how much Matt was apparently enjoying it, too.

Matt stroked his cock while I fucked him harder and harder. The harder I went, the louder his noises became, and the more intensely he stroked. Suddenly, his eyes went into the back of his head once more, his body tensed up, and an expression came over his face like nothing I’d ever seen.

“Oh shit,” he barely got out.

His hole tightened around my cock so much so that I was barely able to keep fucking him. Matt cried out- so loud that I was most confident my neighbors heard him, although that didn’t bother me. I’d heard them doing the same on numerous occasions. Matt’s cock exploded, and his load burst out all over his body.

“Damn dude, you had a lot in you,” I said.

“Thinking about sucking your dick again all day worked me up,” he replied.

I slipped out of him and stroked my own cock above him. His words in my mind made it so it took little effort for me to get off. A warmth filled me like a hot summer day and coalesced in my groin, ready to be released. I finally let go and blew my load all over him, adding to the mess that was already there.

“Looks like you enjoyed it too,” he laughed.

“Maybe just a little,” I said as I tossed him a towel.

Two mornings later, I sat in my car as I dropped Matt off at the airport. We’d had a great weekend as friends- and more.

“What now?” he asked.

“Come back as soon as you can,” I said. He nodded, got his suitcase out of the back, and walked inside.

Neither of us knew what was going to happen- or whether the weekend meant more than just a quick fling between friends. But the one thing I knew for sure was that I felt the best I’d felt since separating from my wife. That alone made me open to whatever may come.

3

The Wedding

I stood in the cool breeze from the patio, watching the moonlight glisten over the ocean. The weather was perfect. I was relaxing with my best friend, Brock, the night before his beachfront wedding.

“I can’t believe you’re getting married tomorrow, dude,” I said as we both sipped on a drink.

“Me either. It’s fucking crazy.”

“You ready to commit to having sex with just one person for the rest of your life?” I asked.

“You know, I’m not so sure I have to. Kayla, well, she’s pretty open minded.”

“Oh? Really? You’ve talked about this kind of stuff?” I asked.

I was shocked, both by the content of what he’d said and the fact that he felt open enough to say it. Even for us, these weren’t conversations that we were having every day.

“Yeah,” he said.

“That’s awesome, buddy. I’m happy you found your match.”

“Me too,” he said. He looked down, smiled, and took another sip of his drink. “Wanna take a walk?” he asked.

“Sure.”

Brock opened the gate that led directly to the beach. We walked for several minutes, going away from the resort and finding a secluded area before sitting down. He started unbuttoning his white button-down shirt.

“Why are you taking your shirt off?” I asked.

“Why not? We’re on a beach. When it’s an option, I choose less clothes,” he said. “You should do the same.” He squeezed my shoulder in a playful way.

“I guess I could,” I said hesitantly, but I ended up pulling my t-shirt off my back.

Brock tossed his shirt beside him. He was now shirtless, and his gym-built body glistened in the moonlight just like the ocean. It was a beautiful sight- one that I’d always thought was beautiful. I was pretty sure he knew I thought so, too. I’d come out to him a few years ago, and he’d been nothing but supportive. We even had detailed conversations about my sex life.

“I’m gonna miss hanging out with you, buddy,” he said, squeezing my shoulder in the same manner again.

“You think Kayla is gonna take more of your time than she does now?”

“I mean, naturally. We’ll still hang out. But she wants to have kids. A bunch of her friends are getting married soon. It’s gonna be a busy time in life, that’s for sure.”

“Ahh,” I said. I had a hard time hiding my disappointment. Was I going to lose my best friend?

Brock, moving a step farther than squeezing my shoulder, wrapped his arm fully around my neck and pulled me closer to him. I began to get nervous- I wasn’t sure what exactly was happening. He was a surprisingly touchy-feely guy for a straight guy, but this was a lot, even for him.

“Danny, buddy, I want to say thank you for being my friend.”

“No need to…”

Suddenly, before I could finish talking, Brock kissed me on the cheek. It was more than a peck- a lingering kiss. And despite its location, it took my breath away. His lips on my body were more than I could handle. A nervous warmth started creeping up inside my body, and my dick started to grow. My instincts told me to pull away- but I didn’t want to. I wanted to stay there with him, holding me.

Faster than I realized what was happening, Brock took things a step further and took my hand in his. He held it for a moment, and then put it on his leg.

“What are you doing?” I asked with a crack in my voice. I gulped.

“Just relax,” he said. “If you want me to stop I’ll stop, but I know you, Danny. I know you’ve wanted this for a long time.”

I gulped again. He was right. As he slid my hand ever closer to his groin, where I imagined a bulge awaited, there was no way in hell I was going to stop. My own cock had grown hard as a rock within seconds. But still…was this really happening?

“You don’t think this will make things weird?” I asked, my brain searching for one last excuse to hold out. “I don’t want to make things weird for you and Kayla, either.”

“Don’t worry about her. I said she’s open-minded. And as far as you and me- I won’t make it weird if you won’t,” he assured me.

“I won’t.”

“Good.”

My hand was now in the crease of his thigh. He stared at me in the darkness as our shirtless bodies touched each other closely. He put his hand on the back of my head and pulled me in for a kiss- this time on the lips. Brock started making out with me. It took me several seconds to recover my breath, but I found myself passionately swapping tongue with him in return.

“Are you into dudes?” I whispered. Brock was always the all-American, baseball player, straight guy’s guy talking about chicks at a party.

“I’m definitely into women, but I’ve been curious for a long time,” he said. “Kayla gave me the go-ahead to experiment.”

“Oh,” I said.

I wasn’t sure if that made me feel better or worse about the whole thing, or any different at all, but his lips returned to mine and any thoughts or reservations I had quickly dissolved. I was nearly naked, on a beach, making out with the hottest guy I knew.

“You can touch me,” Brock said as he pulled me closer.

With the green light, I pressed my palms up against his body. My free hand was suddenly squeezing his solid pecs and veiny biceps. He even flexed for me, which we both got a chuckle out of.

My other hand moved further inward, coming to rest on the bulge beneath his shorts, which was quite thick already. He was definitely excited. I massaged it, searching for the clear outline of his cock.

“Let me help you,” he said, unzipping his shorts and pulling his cock out like it was nothing. I looked around, seeing if I noticed anyone else on the beach. There was nobody in sight. “Relax, there’s nobody out here,” he said. We were indeed secluded.

I took Brock’s cock in my hand, stroking it as we kissed. My breath was heavy, and I found myself trying to catch it a few times. My body couldn’t keep up with all the sensations that were coming to it.

“You should suck it,” Brock said.

“Not afraid to ask for what you want, are you?” I said sarcastically.

“Not at all.” He smiled and bit his lip.

Of course, there was no actual hesitation in me. After our exchange, I buried my face in his crotch and took his cock as far into my mouth as I was able. He gasped and moaned out loud, loud enough that I worried someone would hear- but then I remembered how excluded we were and tried to relax again. I focused on sucking his dick. And what a great dick it was.

I deep-throated Brock’s cock a couple of times. I licked it from bottom to top, running my tongue around it as much as I could. I explored it just as I had explored his body with my hands. He squirmed in his seat on the beach and eventually lay back entirely on the sand. This gave me more room to work with, and I started moving up and down his shaft with a more regular rhythm. His moans followed the same pattern.

Brock put his hand on the back of my head. He pushed gently, although not forcefully- I was already sucking his dick with enough enthusiasm that he didn’t have to encourage anything. His body writhed, tightened, and squirmed. My own insides had butterflies flying around amidst an electric storm. I knew my dick was leaking. Brock’s was leaking, too; I could taste the sweet saltiness of the drip that was coming out slowly.

“Dude, you’re fucking good at this, damn,” he said as he gasped again.

“Thanks,” I said, the compliment blowing up my electrified body even more.

“Don’t stop,” he said, this time more forcefully pulling my head back down to my cock.

I sucked him again, with him now thrusting gently into my mouth. I knew he had to be close and I knew he had his eyes on the finish. I felt his cock thicken in my mouth.

“I want you to take my load,” he said. “Take it in your mouth.”

I didn’t respond, wanting to keep his cock down my throat, but that had been my plan all along. It definitely wasn’t going to change now.

“Oh shit,” he gasped out loud. “Here I come. Fuck. Fuuuuckkk,” he moaned out loud. Anyone relatively close on the beach could have definitely heard, but I no longer cared.

I swallowed all of Brock’s load as he exploded inside me. I felt the pulses of his cock on my tongue and kept it in my mouth until they were over.

“Dude,” he said, laughing. “That was amazing.”

“You mind if I get off?” I asked. I fully expected that he was not going to suck my dick in return, but I was hard as a rock and needed to take care of it.

“Not at all,” he said.

Brock didn’t suck my dick, but he did touch it when I pulled it out, tugging it gently. I nearly came just from that. Within seconds I’d jerked my cock and my load blew out as I tilted my body to the side, letting it fall on the beach next to me. I fell back, laying down naked with him.

“Well, how’s that for your last night as a bachelor?” I asked him.

“Fucking amazing, dude. Fucking amazing,” he said. It was dark and I wasn’t looking at his face, but I could almost hear his smile.

A few minutes later we walked back to the resort, and he invited me into his room. We ended up cuddling in bed the rest of the night. The following day, I was the best man at his wedding- and genuinely happy for him. He was right- nothing between us had changed. He was my bro.

4

The Frat Party Dare (Part 2)

That night at the party wasn’t the last time I would hook up with Jimmy. In fact, far from it. Over the next few weeks he started texting me when he wanted to get off. Knowing fully what I was getting myself into, I happily obliged. After parties, after class, in his bedroom, in his car- I was Jimmy’s on-call cock sucker. I still watched him flirt with chicks on plenty of occasions, but felt a sort of pride inside knowing he’d turn to me in a pinch. I didn’t mind the arrangement one bit, and we’d even become closer as friends and fraternity brothers.

“What’s up, buddy?” he asked at the end of a frat chapter meeting one night. It had been a busy week and we hadn’t seen each other much.

“Hey man. Just trying to get through all these exams, you know,” I said. He squeezed my shoulder.

“I hear you. Me too. I could really use some stress relief,” he said with an expectant smile. He definitely wasn’t subtle.

“Your place?” I asked, confirming I was in.

“That’s my man,” he said. He gave me a bro hug, and we walked the couple blocks to his apartment together.

Once inside, we put our bags down, walked straight to his bedroom and started making out. For a straight guy, I was surprised at how much he actually liked to kiss. He was letting me get touchier with his body, too. Once his shirt came off, I thoroughly ran my hands all over his torso, and kissed his smooth skin from his neck down to his abs. He squirmed and moaned like he was enjoying every bit of it. Eventually, I got to the main event- on my knees and his cock in my mouth.

“Yessss,” Jimmy stated, first in a deep voice and then moving into a gasp. “I always get reminded why you’re the best at this when you start doing that.”

I smiled, as much as I could while I had a dick in my mouth, and kept going. I pulled my cock out and started jerking myself. I kept up the routine for several minutes, both of us thoroughly enjoying it all. I thought I nearly had Jimmy to completion when he suddenly stopped me.

“Bud, I have a question,” he said. I stopped what I was doing.

“Shoot,” I said.

“What does it feel like to fuck an ass?” he asked.

Damn. I’d never thought this day would come. His question caught me off guard, but I would have done anything to get him to fuck me, so I quickly collected myself.

“To be honest, I prefer to be on the receiving end,” I said.

“Really?” he asked with a slight, mischievous smile.

“Yes. But I’ve heard it feels good. Tight. But, you know, a hole is a hole, right?”

“I mean I used to think a mouth was a mouth, but yours is clearly better than the rest,” he said.

“Are you saying you want to fuck me?” I asked boldly.

“Kinda,” he admitted.

“Then let’s do it,” I said.

Jimmy grabbed a bottle of lube and a condom out of his nightstand. He lubricated his cock and was about to toss the bottle to me.

“More,” I insisted. “It doesn’t work like straight sex. You can’t put on enough.”

“Gotcha,” he said, doubling up.

I took my turn with the lube while Jimmy lay down on his back, stroking his cock.

“Is that your preferred position?” I asked. “You like girls to ride you?”

“Yeah. Is that okay?”

“It’s perfect,” I said excitedly. It was my favorite position too.

When I was ready, I positioned myself over Jimmy’s hips and began to lower myself down onto his cock. The initial pressure had me excited- I couldn’t believe Jimmy was inside me. It quickly turned to pain, though, which I expected and knew I’d have to work through.

“Everything okay?” he asked.

“Yeah. It just…takes a minute,” I said.

Sooner than I thought, probably because I was with him, I loosened up. The pain gave way to intense pleasure as I started riding him back and forth slowly, his cock swiveling around in my hole, massaging deep inside my body.

“Your cock feels incredible, dude,” I couldn’t help saying.

“Your ass feels great, too,” he said.

His strong arms pulled my upper body down to him, where we kissed as our chests came together. It felt amazing for my body to be close to his. The spark of the kiss while he was inside me was more intense than any kiss I’d ever experienced. I was in ecstasy.

“You like to kiss more than I’d expect from a straight guy,” I commented.

“What’s sex without kissing?” he said, as if it were nothing at all. That response actually put me at ease.

We made out in between spurts of me riding his cock with intensity.

“Let’s try something else,” he said after things were getting going pretty intensely.

We switched positions, and I got down on my stomach on the bed while he put himself behind me. He slipped his cock back inside my hole, going in much easier than it did the first time. I buried my face in a pillow and moaned as Jimmy fucked me from behind with force.

“Oh…fuck…shit,” I kept saying.

I heard his breath close to my ear and his body, becoming sweaty, close behind me. At one point he held me, his chest touching my back, while he pounded away at my ass. His hips slammed into my cheeks with force. This guy knew how to fuck.

“Your ass feels so fucking good,” he said, sounding exasperated. I could almost feel his cock thickening inside me.

“Are you close?” I asked.

“I’ve been close for a while,” he said. He only kept going.

My own cock was leaking in between my groin and the sheets. He felt so good fucking me that I wondered if I was going to cum without touching it at all. Soon, sooner than I expected, in fact- I had my answer.

My entire body tightened as a pulse traveled from my groin out to my extremities and back inward. I’d never experienced an orgasm in my entire body like that before. Jimmy’s muscular arms held me the entire time, and he continued thrusting away, pushing his cock deep inside me.

“Oh shit,” I screamed, biting the pillow beneath me.

“Did, you, uh…” Jimmy started to ask.

“Yes,” I said. He slowed down and pulled out of my hole.

“Can I cum on your face? I’ve always wanted to do that,” he said.

“Anywhere you want,” I told him.

He straddled my body and jerked his cock above me. It was a sight to behold. His entire body tightened, his muscles popping, revealing every cut and vein. His body was impressive to say the least. Within seconds, he cried out, and his cock exploded all over my face. I licked up some of his load that had landed near my lips.

He tossed me a towel and collapsed next to me on the bed. To my surprise, we fell asleep together that night. We continued a casual relationship throughout all of college, and to this day, Jimmy was the best sex I ever had.

5

The Legacy

It was Alumni weekend with my fraternity. A bunch of my fraternity brothers were legacies, meaning during Alumni weekend their dads were on campus because they had been members of the same fraternity years ago. I, on the other hand, stood in a corner of the frat house backyard watching everyone else socialize with their dads during the welcome evening party.

“Bryce, come here,” my friend Alan said from a spot across the yard. He was one of my favorite brothers in the fraternity.

“What’s up,” I said as I joined him and his dad.

“Ken,” Bryce’s dad introduced himself, extending his hand.

I was immediately struck by this man. He was mid-forties, about twice my age, but that didn’t really matter to me. I found it attractive. He was an older, sexier version of Alan (who I was also attracted to- but I never would have said that to his face).

Most of the dads here showed their age- they were balding and overweight. Not Ken. He still had a full head of beautiful brown hair with just the right amount of gray mixed in. His handshake was firm, showcasing his strength. A shock ran through me when our hands touched- one that I was surprised by.

“Bryce,” I replied, introducing myself.

“Nice to meet you, Bryce. Alan tells me you guys are pretty close,” he said.

“Yes sir.”

“No need to call me sir. Just Ken. Any friend of Alan’s is a friend of mine.”

“Well, it’s good to meet you, Ken.” And I meant it. It was almost in that moment that I began undressing him with my eyes, getting him out of the business-executive type clothes he was wearing.

The three of us hung out for a while, talking, before some others came over and we went our separate ways. I found out Ken was the CEO of some company that he’d grown from the ground up. The position- and not the details- were what interested me. This was a man of power.

The next day, we all attended the university’s football game together, sitting in the same section. As we tailgated and watched the game, I was near Alan, and by extension, Ken. Ken kept up with the college guys better than any of the other dads- playing beer pong, taking his shirt off, and revealing an impressively chiseled body for a man his age.

“You might have to give me your gym routine,” I blurted out at one point, and immediately regretted.

“Thank you,” he said. “I’d be happy to.” He took the compliment in stride.

I kept my mouth shut for the rest of the day, but we sat next to each other during the game. I couldn’t help but steal glances over the course of the few hours, every chance I got. His chest popped out and was rock solid, and his back was one of the most sculpted I’d ever seen. He had the perfect amount of chest hair, too. I nearly had to leave my spot in the stands and go jerk off in a bathroom stall. Somehow, by the skin on my teeth, I maintained control.

That night we had a party at the frat house, but I retired early. I was pretty exhausted from the day. I was getting ready for bed and walking from my shower in one of the common bathrooms to my bedroom. Just as soon as I’d shut the door and put my things down, there was a knock on the door.

“Yes?” I asked.

“It’s Ken. Can I come in?” the voice said.

Mildly irritated and still with only a towel wrapped around my waist, I opened the door.

“What’s up?” I asked, only cracking open the door rather than allowing space for him to walk in.

“Not joining the party out front?” he asked.

“I’m kinda tired. I think Im just gonna hang out back here. Tell Alan I’m sorry,” I said.

“I totally understand. I’m not really a party person myself. Mind if I come in?” he persisted again.

“I’m not dressed at the moment,” I said.

“I don’t mind,” Ken replied.

Oh.

Suddenly the game had changed. I slowly opened the door and allowed Ken into my room. A wave of feeling- something I couldn’t quite put my finger on- came over me. It was sort of a mixture of nerves and excitement all at once.

“I’m sorry to barge in here like this. I saw you in the hall and figured maybe you’d want to hang out,” he said.

“What, uh, what would make you think that?”

“Well, for one, you’ve been looking at me non-stop all weekend,” he said.

“I…I’m sorry about that.” I gulped, now deeply embarrassed.

“Don’t be,” Ken said. He smiled. “Come here.” He motioned me over with his hand and shut the door behind him.

I cautiously walked over to him, and he encouraged me along the way. I stopped when I was just a foot or two away, close enough to be in his personal space. I wasn’t sure what to do next.

“You can touch me if you want,” he said.

I lifted my hand but couldn’t quite bring myself to place it on him. He took it and put it on his chest and maneuvered it slowly, all the way down his body, down to his crotch, where there was already a large bulge.

“I’m not out to anyone here,” I blurted out.

“Neither am I. Your secret is safe with me.”

“Okay.” I gulped again.

Ken pulled me to him so that our bodies were completely touching. He kissed me on the lips and started making out. His tongue massaged mine; his mature, masculine lips were slightly rough and just perfect for my taste. I’d hooked up with a few guys on campus before, but never a man like this. I was in heaven.

As we kissed, Ken untied the towel around my waist and let it drop to the ground. My cock was undeniably hard and he began to stroke it. I breathed heavily and moaned softly as he did, and he continued kissing me.

“You want to, uh, take your clothes off?” I asked.

“You want to see me naked?” he replied with an excited smile. I only nodded yes. I absolutely fucking wanted to see him naked.

I watched Ken as he undressed. I felt weird watching him, but he didn’t seem to mind the audience. He kicked off his dress shoes, then unbuttoned his white button-down shirt. He undid his belt and let his pants down, revealing boxer briefs with an outline of his bulging cock. He then took off his undershirt, and then off came his boxer briefs. Just like that, I had him naked in front of me. He was beautiful, so much so that I didn’t know what to do.

“You want to touch it?” he asked. I nodded yes. “Go ahead.”

I gave his cock a couple of strokes as we resumed kissing.

“You ever had your dick sucked by an experienced man?” he asked. This time, I nodded no. I’d gotten head from a few guys on campus but mostly just jerked off. None of it had been all that great, admittedly.

Instead of conversing further, Ken pushed me down onto my bed, got on his knees, and put my cock in his mouth. Immediately the warmth of his mouth and sensation of his tongue rolling up and down my shaft overtook me. I felt my body tense and my toes curled multiple times. I grabbed the sheets on the bed in a futile attempt for steadiness.

“Holy shit,” I said.

“Feel good?” he asked, smiling, fully knowing the answer.

“Yes. Better than I’ve ever had,” I said.

He chuckled and went back down. He deep-throated my cock several times, enveloping the whole thing. Then he started sucking me up and down. I could feel his tongue rolling all around. He massaged my entire shaft and swirled it around the head of my cock. That part, especially, drove me wild.

As I lay back, there was nothing I could do except lay there and let him do his work. It felt so good- so intense- there were multiple times I felt like I was about to cum. He always stopped just in time, knowing when I was on the edge.

“When are you gonna let me cum?” I asked.

“It’s no fun if it happens too fast,” he said.

After several minutes he added his hand to the mix, which was a whole new dimension I’d never experienced. The sensation covering my entire shaft had my insides pulsating and my body shaking. At this point, I wasn’t even sure if I was going to last over one of his edging attempts.

“That feels so fucking good,” I said. He just kept sucking my dick, pausing intermittently to let me recover. In those moments he’d kiss my stomach, groin, or thighs.

Eventually, and mercifully, he resumed for good, sucking my cock with ferocity. He had his hand and all of his technique going. There was no way I was going to last. I immediately felt my load waiting at its gates.

“I’m gonna cum,” I warned him. He kept going. “I’m gonna fucking cum,” I said again.

Nobody I’d been with yet had wanted to swallow my load, but I gave Ken adequate notice. Finally, I couldn’t hold on anymore. My load burst out into his mouth. He kept sucking my cock throughout my entire orgasm, which had me writhing in the sensitive pleasure of it all. When it came to an end, I felt almost as if I couldn’t move. I struggled for a heavy breath.

“You won’t get one like that from any of these inexperienced frat boys,” Ken said. He started to dress again, apparently not worried about getting off himself.

“I think you’re right,” I agreed. “Fuck that was good.” He smiled.

“You’ll have to come visit Alan at our lake house this summer,” he suggested with a wink.

“I think I will. I definitely think I will.”

Ken left my bedroom just as inconspicuously as he’d entered.

6

The Honeymoon (The Wedding Part 2)

After Brock’s wedding, it was a few weeks until I heard from him again. He had been right- maybe we wouldn’t be spending as much time together after all. One day, out of the blue, he called me. I eagerly picked up the phone when I saw his name on the caller ID.

“Hey man,” I answered the phone.

“Hey, Danny. How have you been buddy?” he said in a warm, friendly voice typical of his personality.

“Oh, you know, same old, same old. Work and the usual.”

“Working hard and playing hard,” he said. We both chuckled. “Well, man, I called you for a reason. I have a request,” he started.

“Sure, what’s going on?” I said, having no idea what he was about to get into.

“It’s a strange one, but hear me out. I’d like to invite you….”. There was a pause, as if he almost couldn’t believe what he was saying, or couldn’t get it out completely. But he eventually got on with it. “I want to invite you on our honeymoon trip,” he said.

“Huh?” I was utterly confused. “With you and Kayla?”

“Yeah,” he said, sighing.

“You’re, uh, you’re gonna have to explain, bud,” I said.

“I know, I know, it sounds crazy. But hear me out.”

“I’m listening.”

“You know how I told you Kayla was open-minded?” he started.

“Sure,” I agreed.

“Well, we tell each other everything. Meaning…” he trailed off, but I could see where he was going with this.

“You told her about the night before the wedding, on the beach, didn’t you?” I said.

“Yeah. And you know what dude? She was turned on by it. She’s been pushing me to ask you this. She, uh, she wants you to join us. She wants us to have sex- and she wants to watch.”

“Oh,” I said. I really didn’t know what else to say.

“Yeah,” he agreed, acknowledging that he understood my reaction. “We’ll pay your way. You get your own room. It’s a cruise around the Mediterranean,” he pleaded.

“So let me get this straight,” I said. I was about to spell it out for him- as much for myself as it was to make him acknowledge how ridiculous this all was. “You want me to go on a free vacation with you and your new wife so that she can watch us have sex.”

“Yes,” he said succinctly.

“I’m in.”

“Really?” he asked.

“Hell yeah, dude,” I said.

“Good. She’ll be happy,” he said, almost with a hint of relief in his voice.

“Are you happy?” I asked him.

“Hell yeah, dude,” he repeated after me.

With that, a week later, I was boarding a cruise with Brock and Kayla. At first things were a little strange, all of us knowing the context of what was going to happen. But after our first round of dinner and drinks, we all began to settle in. Kayla was cool. Brock was still the same best friend I knew. And deep down, I couldn’t wait for him to fuck me.

Things came to fruition, for the first time, on our first evening on the boat. The three of us were hanging out together in the stateroom the two of them shared. We were all loosened up. Brock had his shirt off, and I couldn’t help but stare at his sculpted body.

“You have a beautiful husband,” I told Kayla, feeling bold.

“I know,” she agreed. Brock was grinning ear to ear off to the side. “You should kiss him,” she said.

“Should I?”

“Yeah, come here buddy,” Brock said. It was happening. Things were becoming real.

I made my way over to Brock, who was sitting against the wall on the bed. When I was close enough to him, he pulled my head to his aggressively, and our lips met swiftly. My body became heated as an intense pulse of pleasure- one that I was now familiar with- ran through me as we made out for the second time ever.

“He’s a good kisser, too,” I said. Kayla laughed in the background, but I got the sense she was intent on being an observer. I let her fade out of my cognition and focused only on Brock. He really was a fucking great kisser.

“Lay back dude,” Brock said after several minutes of making out and intense feeling up of each other’s bodies. He seemed almost as into it as I was. I did as he said.

Brock began to kiss up and down my body, driving me wild. I broke out into goosebumps. He kissed my nipples, licking them slowly, playing with them sensually. I recoiled in pleasure and sensitivity. He laughed, apparently amused he had so much control over my body’s reactions.

I took a deep breath as he kissed lower and lower on my body. My nerves stirred as he got closer and closer to my cock. Is he actually going to…? His voice interrupted my thoughts.

“Can I?” he asked. He had his eyes on my cock and one of his hands inching closer and closer.

“Of course,” I said. I didn’t know what he was going to do, but I trusted him, and at that point would have let him do whatever he wanted.

Brock put his lips around my cock. I recoiled in pleasure, my back arching and my toes curling. He deep-throated my entire shaft and then started sucking up and down, just as I had done to him a few weeks earlier.

“Damn,” I gasped.

“Good?” he asked.

“Yeah. Fuck yes.”

He was surprisingly good for someone who I assumed didn’t have a whole lot of experience sucking dick. His lips slid up and down as his mouth moistened me and his tongue did the work of pleasuring my most sensitive areas.

“Oh shit,” I told him.

“What?”

“I’m gonna cum if you keep doing that,” I said. I imagined I wasn’t too far away, based on how I was feeling.

“Well we can’t have that yet, can we?”

Before I knew what was happening, Brock used his impressive strength to flip me over onto my stomach. He reached for something beside the bed and straddled my hips.

“My first time fucking an ass, any pointers?” he asked.

“Be gentle at first. But you’re going to love it.”

“Okay,” he said laughing.

Brock lubed up his cock and then spread some lube on my hole. He loosened it up with a few fingers first, and at that point I was already moaning. I wanted his cock in me.

“I want you inside me,” I told him.

“Can’t argue with that,” he said.

Kayla had been relatively quiet to this point, but I saw her smile out of the corner of my eye and felt her enthusiasm as we moved forward.

With me lying face down on the bed, Brock slowly pressed his cock into my hole. It felt incredible at first- the pressure of his girth ever so slowly opening up my hole, spreading it apart. As he pressed further, though, it became uncomfortable- which was expected. I winced.

“You okay?” he asked.

“Yeah. Just keep going,” I said. I’d experienced worse, and was determined to push through it for him. Thankfully, a few minutes later, we were in business.

“Holy shit,” I said as his cock reached deep inside my ass, hitting the correct spot.

“Yeah?” Brock said, confirming what he was doing was working.

“Yes,” I said. “Yes, yes, yes.”

Brock began pounding away at my ass from behind me. I stayed lying down for some of it, and some of it was doggy style. We traded back and forth. My body pulsated as his cock reached deep inside my hole and massaged my prostate. It filled me with an energy I had a hard time controlling. The only thing I could do was breathe.

His hips made audible sounds as they smacked into my ass with force. Brock knew how to fuck and was thoroughly enjoying it. My insides almost couldn’t keep up with how good it felt, but I didn’t want him to stop. I was shaking and sweating and pulsating and determined to take it all.

Brock came down to kiss me on the neck and my body contracted. Goosebumps broke out. I needed a deep breath but couldn’t quite catch it all the way. A pleasure unlike any I’d ever felt ran through me.

“Oh fuck, I’m going to cum,” I gasped.

“Yeah?” Brock said, sounding surprised and intrigued at the same time.

Before I had a chance to respond in words, I cried out loud, I think even scaring Kayla a little bit. My load spilled onto the sheets beneath me. I hadn’t done so much as lay a finger on my cock. Brock was that good.

“That’s crazy,” Brock said. “I kinda want to know what that feels like.” He was amazed that it was even possible.

“I can make that happen. Or at least try,” I said as he jerked his cock above my face.

“We’ll see,” he said, not committing one way or another. He finished stroking and covered my face in his cum. “But I have a feeling we’re at the beginning of a wonderful arrangement.”