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Mac And Duri's First Time

After spending a wonderful Christmas in Nags Head, Mac and I returned to John Adams and the final semester of our senior year.

The amount of work both Mac and I put in during our that time kept us apart a lot, and, when we did meet friends and attend fraternity functions, I was shy about showing our relationship to everyone. Our friends didn’t seem surprised at all, but other people were obviously shocked. It didn’t help that I kept catching wind of snide remarks from girls that Mac had dated.

“No wonder he couldn’t hold onto a relationship for long. He’s gay!”

“This explains so much.”

And my favorite: “I knew he always had a thing for that guy!”

Mac had to have been aware of the gossip, but it seemed to roll off his back. I would have been more worried about it, but between my workload and trying to catch some sleep, I didn’t have the time. What did it matter, anyway? We were leaving in a matter of months and would probably never see most of these people again.

Mac and I had agreed we would both live in Boston after graduation, but there was the question of what Mac would do there. After a session with his advisor at the school, he settled on applying for an internship with a local TV station. Because it was late in the game, we were afraid he wouldn’t get in. The night he got the call that he got the summer internship, he was over then moon. I’d never seen him so happy.

Before we knew it, graduation day was upon us. It rained, which meant the ceremony had to be held in the university gym and invitations would be limited. The restriction didn’t matter to me since, unsurprisingly, my father and stepmother couldn’t make it. I was hurt, but with Mac’s family all over me, I didn’t have a chance to feel alone for long. When his parents gifted me with a university ring just like the one they got for Mac, I burst into an embarrassing torrent of tears.

That weekend, Mac’s parents helped us settle in Boston. I had secured a job with the Chamber of Commerce weeks before as the Assistant of Events and Program Coordinator. I was scared shitless.
It had been Mom Murdock’s idea that Mac and I live separately for a while, so we could both get a feeling of standing on our own. Mac was against it, but I really wanted to prove to myself that I could do it. Privately, I was also worried about taking our new relationship to the next level. So, Mac agreed to stay the summer in a tiny studio apartment near the TV station while he was doing his internship there, and I got a place on the other side of town closer to my job. The situation wasn’t ideal. Traffic in Boston was awful. But we could make it work for one summer, right?

On a Thursday evening in late June, Peyton called me. He’d secured a position as a personal assistant on a ranch in East Texas, of all places, and was loving it. Or maybe he was loving Texan men in cowboy hats.

“I swoon on a daily basis,” he told me, sounding happy. “They don’t seem to know what to make of me, but my boss is a big LGBTQ advocate, so I don’t get any hate.”

“That’s good, but be careful. I worry about you. Your hair’s not pink, is it?”

“Sending you a pic.”

A few seconds later, I received a picture of Peyton lying on a bed, smiling sexily for the camera, his hair a bright platinum blond.

“It looks great!” I told him truthfully.

“Thanks! Now, let’s get to the important stuff. I’ve barely been able to talk to you since graduation. How’s sex with Mac?”

“We aren’t living together,” I reminded him.

“Oh, sorry, I forgot cohabiting was essential for having sex. Come on, Dur!” Peyton groaned.

“I want to hear more about your job and the cowboys," I said.

“Don’t change the subject." Suddenly, he gasped. "Oh my God! Duri, don’t tell me you haven’t done it yet! You’ve been together for six months!”

“Six months of homework, exams, job interviews, and…and…” I left off, feeling defensive but unable to successfully build my case when we both knew the truth: I was chicken.

“Just admit you’re scared,” Peyton said.

“I’m not,” I said in a small voice. “I’m...I'm terrified.”

Peyton made a sound with his tongue and teeth. “Haven’t you done anything?”

“Yes, of course! But not…you know. Penetrative.” I whispered the last word.

Peyton laughed. “What, are you afraid the cat will hear you?”

I’d adopted a cat—or, rather, a cat had adopted me. His name was Rex, and currently he was sitting behind me on the back of the couch.

“Hate to break it to you, Duri, if you’ve done stuff, you have had sex. Not everyone gets into penetration.”

“But I want to,” I said, pouting. I really did, but the thought paralyzed me with fear. What if it was too painful and I couldn't go through with it? What if Mac was sorry he was dating me?

“What does Mac say about it?” Peyton asked.

Fiddling with the corner of the sofa pillow, I said, “He hasn’t said anything about it. But he has to want to do it, right? He’s been with a lot of girls.”

“Yeah, he was a  real man-whore," Peyton said.

"He was not," I defended. "He was never in a relationship with more than one girl at at time."

"You need to sit down with him and talk about the next step in your relationship, Duri.”

I groaned, throwing my head back against the couch and causing Rex to jump down onto the floor and walk away, miffed.

“What are you afraid of, exactly? And stop biting your fingernails. I know that’s what you’re doing,” Peyton said.

Jerking my hand away from my mouth, I clenched it in my lap and thought about his question. What am I afraid of?

“I guess I’m most afraid of being bad at it.”

“You can’t be bad at it. Be glad your a bottom.”

“But what if I don’t enjoy it? Even worse, what if he doesn’t? What if it hurts so bad I cry?”


"Duri, you'll be fine."


"Tell me how. You’ve done it before.”

“Just casual sex. You and Mac are in love.”

“What about David?” I asked, referring to his douchebag ex that Peyton had finally dumped for good our junior year of college.

“He wasn’t want I’d call a considerate lover; let’s just leave it at that," Peyton said.

“Big surprise there," I mumbled. "So…you’ve never had good sex with anyone?” I was starting to panic. If Peyton, who wasn’t afraid of his own shadow the way I was, had never enjoyed sex, there wasn't much hope for me.

“Sure,” Peyton said, "I've had great sex."

“And? What made it so good?”

The silence was total and spread for so long, I looked at my phone screen to see if the call had dropped.


“Pey? You there?”

He cleared his throat. "The attraction was strong. At least on my side. That should make you feel better. I know you’re physically attracted to Mac. Anyway, Duri, talk to him. Tell him what you’ve told me—that you want him to fuck you but that you’re scared. He’s a good guy. He’ll go slow. But keep in mind that things won’t be perfect. But it’ll be special because you guys love each other, and hopefully it will feel good in the end. Just know the first time is never easy for anyone.”

“Okay.” Feeling a little better about my situation, my mind began to backtrack. “Who was your special person that you had great sex with?”

“Hey, listen, I have to go,” Peyton said abruptly. “My boss is calling.” He hung up before I could finish saying goodbye.

For the rest of the afternoon, I continued thinking about everything Peyton had said. I'd been telling the truth when I said Mac hadn't said anything about having sex. But I knew he thought about it, just like I did. We'd both gotten pretty worked up while kissing lately, but Mac was too nice of a guy to push things when I shied away from going any further.

Peyton was right: we needed to have a conversation.


The following day was Friday, and Mac and I were meeting after work. I told myself I would talk to him then.  


Maybe I shouldn’t have picked a moment when Mac had just taken a big bite of pasta to tell him I wanted us to have penetrative sex. As he coughed into his napkin, eyes watering as he stared across the table at me, I handed him a glass of water.

After several long swallows, he rasped, “God, Squish. Give me some warning next time.”

I smiled. “I hope there isn’t going to have to be a next time.”

He eyed me warily before wiping at his eyes. “How long have you had this on your mind?”

“A while,” I said sheepishly, hiding my face behind my water glass as I took a long drink.

“Why haven’t you mentioned it before?”

Rubbing my thumb over the smooth handle of my fork, I said, “Peyton said I should tell you.”

“You’ve been talking to Peyton about our sex life?”

He didn’t seem mad, just surprised.

“I don’t have anyone else to talk to about it,” I said.

“Uh, what about me? Aren’t I the obvious person?”

“I didn’t want to admit I’m scared,” I muttered.

Leaning forward, Mac covered my hand with his. “Don’t you think I’m scared, too?”

I looked at him in astonishment. “Why would you be afraid? You’ve done it lots of times!”

“Not with a guy.”


“See—we’re both new at this. But if we talk to each other and take things slow, everything will be fine.”


Mac squeezed my hand before going back to eating his ziti marinara. When I didn’t pick up my fork, he said, “Finish eating, and tell me about your day. How did the project go?”

We tabled the conversation, but it remained at the back of my mind. I hadn’t thought about the fact that Mac had never slept with a guy before. It made sense that he would be nervous, too, and that made me feel a little better about it.

On the way home, Mac stopped at a drug store and went inside, coming out a few moments later with a bag. Stomach clenching, I couldn't ask him what was in it.

As soon as we got inside my apartment I asked Mac the question that had been burning in my mind since dinner. “What are you worried about when it comes to us having sex?”

Mac stopped petting Rex and turned to me, resting his hands on my shoulders. “I’m most afraid of hurting you. I never want to hurt you. Just knowing that you’re scared about it bothers me.”

“I’m not afraid of you. I’m afraid of the pain, or that I’ll do something wrong.”

“Okay, then it sounds like we have the same worries.”

Leaning in, he kissed me gently. I loved kissing Mac. I could get lost in it for hours. As I opened up for him, he drew me in closer, hands moving down my back and squeezing my ass. My breathing quickened. There was no question in my mind that I was ready to take the next step, if it wasn't for my fears. Mac and I had gone from kissing to hand jobs to blow jobs over the past six months, and every fiber of my being wanted more. I wanted to feel him inside me. I wanted it very much. Heart hammering, I stood on my toes and deepened the kiss, drawing a groan from Mac’s throat.

“Do you want to be inside me, Mac?” I asked, looking up into his eyes.

“Jesus. Of course I do, Duri.”

I pulled back to look at him. “It won’t be like it is with a girl.” That much I knew.

Tapping my nose with his finger, Mac said, “Our sex life is about us and no one else. I want to touch you. Be close to you. It doesn’t have anything to do with what body parts you have or don’t have.” He ran his fingers over my chest, making me tremble. “I love the way your nipples get hard when I touch them.” He stroked both of them with his thumbs, and, even with my shirt as a barrier, my knees went weak.

Taking his hand, I said, “Let’s go in the bedroom.”


My heart thumped wildly as we walked down the hall. As soon I was through the door of the little room that held my bed and dresser, I stripped off my shirt and stepped into Mac’s arms. This kiss was considerably more heated than the last, with Mac’s tongue possessively sweeping through my mouth until I felt light headed. His hands were warm on my bare back.

“You’re skin’s so soft,” Mac said, nuzzling my ear. Abruptly, he dropped to his knees. As he grappled with the button of my jeans, I watched, barely able to breathe. When he took my hard cock out of my underwear, I couldn’t help but gasp.

Raising his head, Mac latched onto one of my nipples with his mouth, making me jerk. He smiled against my chest. Releasing my nipple, he moved to the other side, teasing me with his lips. I jutted my hips forward, my needy cock seeking friction. Needing to feel his skin on mine, I tugged at his shirt until he yanked it over his head and tossed it onto the floor. His tongue trailed down my torso, lower, lower. I sucked in a breath he breathed over the head of my cock.


When I let out a needy little whine, he wrapped his lips around it and sucked.

“Mac,” His name came out on a sigh as I entwined my fingers in his thick, dark hair. If I was half as good at giving head as he was, I’d be happy. He was an absolute master at it.


Which made me wonder something.

Swallowing, I forced myself to take a step back, my cock falling from his mouth with a slurping noise. “Were you nervous the first time you did this to me?”

Lips red and slick, Mac gazed up at me.

“Hell, yeah. I had to watch a shitload of gay porn before I did it.”

“Really?” I asked, eyes widening. I never suspected that.

“It was Vlad’s idea.”

“You talked about it to Vlad?”

Mac looked sheepish. “I guess I can’t say anything about you talking to Peyton, can I? I just didn’t want to embarrass myself by doing everything wrong, and Vlad's had a lot of experience with guys."

I stroked his hair. “You did everything right. You always do. Your mouth feels so good on me.” I nudged his lips with the head of my dick.

With fire in his eyes, Mac licked the frenulum before taking my cock into his mouth again and sucking until I arched my back and moaned. With slow bobs of his head, Mac sucked me until I came into his mouth. He swallowed all of it, like he always did. I tended to spit out most of his spunk when I gave him head. Something about the consistency made me gag.

Breathing erratically, I loosened my hold on Mac’s hair, patting his head in apology.

Getting to his feet, Mac stripped off the rest of his clothes. He had such a nice body—toned with just the right amount of muscle mass. As he slipped off his boxer briefs, I watched his cock spring up in an arch toward his belly.  It was my turn to fall to my knees. 

Trailing a finger over the head and down the rippling vein, I admired him. Mac made a sound half-way between a growl and a whimper, then groaned when I opened my mouth and took him in, making sure I kept eye contact with him because I knew he liked that.

As I sucked him, Mac ran his fingers over my head, shoulders, and face as though I was something unimaginably perfect, his eyes deepening to a smoldering green. I did everything I’d learned he liked best over the past few months, pausing to run my tongue over his balls before taking him down again until I choked on his girth. The first time I'd done that, I was so worried about gagging and throwing up, I could barely enjoy myself. Now that I’d learned how much of him I could handle in my mouth, I was able to relax as I listened to Mac’s breathing accelerate. Leaning his head back, he moaned loudly into the quiet room. I still couldn’t believe I could affect him this way. I determined to make him come hard, but before I could do anything more, Mac pulled out of my mouth.

“Get up on the bed,” he said softly.


Stepping out of my pants, feeling soft and pliant from my orgasm, I crawled onto the mattress and stretched out on my back, watching as Mac took lube and condoms from the drug store bag that I hadn't even realized he'd carried with him into the bedroom.

“We have to get you nice and loose,” Mac told me. “That okay?”

“How do we do that?” I asked, anxiety crawling up my spine.

“I’ll use my fingers.” Kneeling on the bed, Mac poured lube into his palm.

Taking a deep breath and letting it out, I clenched my eyes shut. Mac's lips brushed gently against mine, and, after a moment, I relaxed and kissed him back. We lay there for a long time, exploring each other’s mouths, before I felt Mac nudge my legs open with his hand. By that time, I was lost in a haze of delicious need, so I eagerly complied, only to tense up when his fingers slipped down my taint to my hole. He massaged it, continuing to run his tongue through my mouth, and after a few seconds I got used to the sensation and melted back into the mattress. I was surprised that it felt good. There was a lot more sensation in that area than I would have thought.

But when Mac gently poked the tip of his finger inside me, I tensed.

“Hurt?” Mac asked against my mouth.

“No, it’s okay,” I said.

Rising onto his elbow, Mac looked down at me as he carefully rotated his fingertip inside me. I bit my lip, embarrassed and turned on at the same time.

“You’re blushing,” Mac said, studying my face intently, his voice a sexy rasp.

“You have your finger in my butt.”

Mac laughed, and so did I, and the tension broke.

“I guess that would be kind of weird. Is it okay? Or do you want to stop what we're doing?”

"Do you want to stop?" I asked.

"I asked you first."

Mac’s hard cock pressed against my leg, so I figured he liked what we were doing. Yet I knew he'd stop everything if that's what I wanted.

I was nervous, but I did want this. And more than that, I wanted to please Mac. What we were doing right now didn’t hurt, it was just awkward.

“Keep going,” I said, leaning up to kiss him. Our tongues dueled, and I clenched my hands on his shoulders when his finger slipped inside me a little more.

Now, that felt really weird. But not bad. Relaxed from my orgasm and more than a little turned on to be kissing him and having him naked beside me, the intrusion didn't hurt as much as it could have. Besides, Mac being the one doing it  made it okay. Letting my legs fall open to give him better access, I nipped at his bottom lip with my teeth.

“I’m hanging on by a thread, here, Squish,” he said hoarsely.

Emboldened, I thrust onto his finger so that it slid as far inside me as it could go. Wincing, I wondered if I could handle another finger, but I soon forgot my fear when Mac started moving in and out.

“Do you like that?” he asked.

I nodded. “Yeah.” Closing my eyes, I let out a breath while I adjusted to the feeling, when, suddenly, he hit something inside me that brought my ass off the bed and my eyes wide open. “Oh!”

Mac stilled, a question in his eyes.

“That felt good,” I said, my face heating.

Mac moved his finger again, and another luscious zip of pleasure ran from my balls to the top of my head.
Looking intrigued, Mac swiveled his finger inside me, feeling around, until my legs started to shake uncontrollably. Every time his finger hit whatever it was inside me that felt so good, fireworks went off in my head.

"Oh, my God." I clenched the sheets with my hands.

Mac kissed my nose. “I love watching you like this.”

“Ma-ac,” I whined, sensation building inside me.

“What do you want, baby?” he asked softly. “Another finger?”

Torn between embarrassment and arousal, I nodded, biting my lip. He withdrew his hand and dribbled more lube into his palm. When he pressed two fingertips to my opening, my eyes widened.

“Oh..." The stretch was a little painful. "Wait. Stop.” I grabbed his forearm.

Mac stilled, watching my face.

“Just let me get used to that a minute,” I said, breathing hard.

“Okay. Let me know when you’re ready.”

Mac kissed my cheeks, my forehead, my chin, before his mouth took mine in a deep kiss.

“I love you, Duri,” he said.

I melted. “I love you, too.” Swallowing, I took a deep breath and let it out. “Okay. Go ahead. I’m ready.”

Carefully, Mac pushed his fingers deeoer inside me. It hurt a little, but the more I breathed and concentrated on relaxing, the less I felt the sting. And when he found that spot inside of me again, I shouted, hips jutting upward on their own accord. Mac’s kisses became frantic, his tongue taking over my mouth. My cock was so hard, it hurt.

“I’m going to try three fingers,” he said, pulling away from our kiss to stare down at me. His pupils covered most of his irises. I nodded. When he pushed his three middle fingers into me, I cried out.


“Sorry," he said, stilling. '"You okay? I’m sorry if I'm going too fast. I’m getting so excited watching you—”


He started to withdraw his hand, but I stopped him, hand on his arm.

“I like what you’re doing. Just go slow.”

Mac lowered his lips to mine, stroking my tongue with his while stroking me inside with his fingers at the same time. The stretch burned, but I was so turned on, I didn’t care anymore.

Heart pounding, I begged, “Now, Mac. I want your cock inside me now.”

Removing his hand, Mac wiped it on the sheet before taking one of my legs and placing it on his shoulder.

He did the same with the other leg, then met my gaze.

Heart pounding in my chest, I nodded, and waited as he rolled on a condom. Then he put the head of his cock to my opening. The push this time felt different. His cock was larger than his fingers, but it was also a lot smoother. He slid home in one slow stroke, and I sighed.

“Oh, my God.”

“Good or bad?” Mac asked tightly, sweat glistening on his temples, making his hair curl.

“G-good,” I answered, squeezing around his cock experimentally. I liked the way it felt to be so full of him.

Mac caught his breath. “Fuck, Duri, oh my God.”

“Good or bad?” I repeated his question.

Mac laughed shakily. “Are you kidding me? You feel fucking amazing.”

I couldn’t help grinning. Putting my hands on each side of his face, I looked into his eyes and said, “Fuck me, Mac.”

When Duri and I first started dating, I’d been afraid I might have some trouble doing sexual things with a guy. Sure, I loved kissing Duri, but could I really do more when all I’d ever been interested in before was women? But I’d quickly found that giving Duri pleasure gave me pleasure, and our sex life had been satisfying up to this point. If Duri wanted it, I would have gone without ever having penetrative sex again, but he’d surprised me by bringing it up tonight over dinner. And now…now he’d said three words that had me frozen above him.

“Fuck me, Mac.”

My head buzzed, and I had to take a couple of deep breaths, willing my dick not to explode inside the tight confines of Duri’s body. Not only would a premature orgasm the first time we had sex be embarrassing as fuck, but it would bring this glorious moment to a screeching halt, and I wanted to enjoy every minute of it.
Duri lay naked beneath me like the male version of a siren, his dark eyes heavy lidded. It was all I could do not to teeter over the edge then and there. Added to that, I was suddenly overflowing with feelings. Closing my eyes, I began to count backward from one hundred.


I opened my eyes. The uncertainty I saw in his squeezed my heart.

Trying to put my feelings into words, I failed miserably. “It’s just…a lot. You know?”

But he nodded slowly, as though he understood exactly what I meant.

“I just…I want to do this right, Duri,” I took a breath and rushed on, “But God, I’m so fucking turned on right now, I’m afraid if I move an inch everything will be over before it even starts.”

Duri pushed my chest, and the next thing I knew, I was on my back and he was sitting on top of me, my cock still inside him. Only much deeper. He looked shocked, like he hadn’t expected how different the new position would feel. Experimentally, he wiggled around, and I sucked in a breath as ripples of pleasure ran through me.

Grasping his hips with my hands, I stilled his movements.

“I’m on a hair trigger, remember?”

“Sorry,” Duri said. He didn’t look sorry, though. A mischievous glint in his eyes, Duri slowly lifted his body until only the tip of my cock remained inside him, and then he just as slowly eased back down until our groins met.

“Ohmygod!” I said on a rush of air.

Then he did it again. And again.

Not in a million years did I ever think this night would end with sweet little virgin Duri bottoming from the top.

Waves of euphoria ran through me, and pretty soon I was moving with him, carefully undulating my hips on his every downthrust. Duri’s lips, so pink and sensuous, parted on his quick breaths, and his head fell back as he braced his hands on my thighs and rode me.

“Is it…are you…okay?” I was still worried about hurting him.

In answer, Duri let out the sexiest moan I’d ever heard. With that, something snapped within me, and, tightening my hold on his waist, I planted my feet on the mattress and began to thrust into him until he was crying out in pleasure. I was losing control and beginning to think I’d have to finish him off with my hand, when Duri suddenly arched his back and came all over my stomach. It was absolutely porn-worthy and had me coming into the condom within seconds, grinding my hips into him.

“I’m sorry. You’re going to have bruises,” I said a few minutes later as we lay panting on the sheets and I stared at my fingerprints all over his hips.

“I don’t care,” he said, rolling to lay his head on my chest. “Your heart is beating so hard.”

I laughed. “I wonder why.”

Duri looked up at me. “So, it was good? I mean, you liked it?”

“Did you think I was faking? That condom's full of my cum.”

Duri blushed and hid his face under my arm. Chuckling, I patted his silky black hair. “It was phenomenal. Are you hurting anywhere?”

He shook his head.

“Are you sure? I could get you a wet rag or something.” Besides the porn, I’d also read up on gay sex, but at the moment I couldn’t remember anything about aftercare except needing a wet rag.

“I’m good, Mac.” He peered up at me shyly. “I loved having you inside me.”

“You did?” My chest constricted. “Because I was going to say, if you didn’t like it, we don’t have to ever do it again. I mean, I enjoyed it, of course, but I enjoy everything we do together.” God, now I was babbling. Clamping my mouth shut, I continued to stroke Duri’s head.

“I really liked it,” he said against my chest. “At first it hurt a little, especially when I got on top, but then it got better and better. There’s, uh, this place you kept hitting that felt amazing.”

“I read about that. It was your prostate. A lot of men get pleasure from that kind of stimulation.”

He was silent a while, probably thinking about it. But then he surprised me by asking, “Mac, do you think you’ll ever miss being with girls?”

“What?” I pushed myself up to a sitting position and took his hand.

“Why do you ask that? No, I’m not going to miss girls. I love you.”

He sighed. “It just seems like it’s all too much to ask. To have you after having a crush on you for so long. To be dating you, and what we just did together. I keep thinking I’m going to wake up and realize it’s all been a dream.”

Pulling him close, I kissed the top of his head. “It’s not a dream. It’s real. We’re going to be together forever, Squish."

He turned his dark gaze to me then. “Really? You really feel that way?”

“I really do,” I said emphatically. “Now, do you want to take a shower before we go to sleep?”

He scrunched up his face. “I am kind of sticky.”

Grinning, I got up from the bed and tugged him into the bathroom. I would soap him down, wash his hair, and then carry him back to our bed.

In a few months, when my internship ended, we would get a place together. No more living separately. I understood why Duri wanted to do it, but I was pretty sure that, by the time summer ended, he would be as ready as I was to be together all the time. Until then, we’d make the most of the weekends and the occasional weekday dinner, and I would sock away all the money I could from my paid internship. My supervisor had hinted it was likely they’d hire me full time afterward, and Duri seemed to be doing well in his job at the Chamber.

All in all, I thought as I tugged Duri into the shower after me, everything about the future looked bright. In the fall, I planned to propose to him, and we really would be together forever.


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