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My Sister's Boyfriend, Part 4

"A summer of sexual exploration"

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Author's Notes

"Again, takes up right where the last one (Part 3) leaves off."

Three weeks later I graduated. I didn’t see Matt again that summer, and to tell the truth I didn’t think a lot about him, either. My mind was far more occupied with Shana.

Although we hadn’t exchanged numbers or emails over Memorial weekend, I’d eventually asked Kelly for Shana’s contact info. But once I had it, I hesitated to use it, because I remembered her saying that night on the beach, “This is it.”

What did she mean by that? Did she mean for that weekend only, that she was open to seeing me again? Or did she mean it for good? Was I just a one-time fling? 

I finally worked up the nerve to send her a text, though I agonized for hours over what to say. How could I convey in a few words how much that night meant to me without sounding like a dumb kid? 

In the end, I decided on the simple approach.

Hi, Shana, it’s Andy, I wrote. I hope you don’t mind my texting you. There is a lot I want to say about the time we spent together, if you would like to hear it.

A couple of hours later she texted back.

Hi, Andy. Can you give me a sample?

I tried to picture her expression as she wrote this. It could have been said with a trace of irony or skepticism, or it could have been with the same come-hither look she gave me that night on the beach.

I decided to hold nothing back.

It was the best night of my life.

Ten minutes went by.

I think I would like to hear more. Skype me tomorrow night?

Absolutely!

So began a summer-long series of conversations with the woman who became my first and only real love.

We texted and Skyped several times a week, and I found I could really talk to her. She was smart and funny and affectionate, and she said she looked forward to seeing me at school in the fall. 

And while I couldn’t bring myself to suggest cybersex, Shana did flash her tits a couple of times, providing me several evenings of jackoff material. 

Meanwhile, I heard nothing from Matt, which was probably just as well. My growing feelings for Shana assured me that I was mostly straight, and I began to hope that what happened with him and Stan over Memorial weekend was an aberration. 

But there were times when images of my experiences with them would come crowding into my head, and I would get big hardons that wouldn’t go away without exhaustive masturbation.

Worse, as the summer wore on, I also found myself looking at some guys in a way I used to look only at girls -- that is, as potential sex partners. I had a summer job working in a neighbor’s construction business, and there was a co-worker I found myself attracted to, despite my resolve not to think about other men in a sexual way. 

Jason was a tall, rangy sort with close-cropped brown hair and brilliant blue eyes. He had been working construction for several years, leaving him with a permanent tan and a taut physique, and he was friendlier to me than most of the other guys, who tended to look down on the summer temporaries. I guessed he might be twenty-five.

One hot afternoon we got to talking while framing a garage behind someone’s house. It turned out he had grown up in a large working-class family that couldn’t afford to send him to college, so he was working and going to school part-time. He’d been married right out of high school, but split with his wife two years later when he caught her cheating with her boss. Since then he’d dated other women now and then, but none of them seriously.

When we were done for the day, he asked if I’d like to go out for a beer.

“I’m only eighteen, remember?” I said. 

“Oh, yeah, I forgot,” he said. “Why don’t you come over to my place, then? I’ve got a twelve-pack cooling in the fridge.”

“I’m kind of skanky,” I said, sniffing at the armpits of my sweaty T-shirt. 

I might have imagined it, but I thought his nostrils flared a bit.

“You got any clean clothes in your car?” he asked.

“I have my workout stuff,” I said. “There might be a clean shirt in there.”

“You can get a quick shower and change at my place,” he said. “I’ll lend you a pair of shorts.”

“Okay, then,” I said. “Sounds great.”

A couple of hours later we knocked off. I followed him home in his truck, got my gym bag out of my car and climbed the stairs to his apartment. He was waiting at the open door. 

“No more than two beers for me,” I said. “I gotta drive home.”

Jason’s two-bedroom was small and sparsely furnished but clean and sunny. I sat down on a stool near the kitchen counter and he fetched two beers from the fridge.

“You have a roommate?”

“Yes, but he’s on a business trip. He travels a lot.” 

He sat down on the other stool, clinked his bottle against mine and smiled. We both took big swallows of beer. 

“You hungry?” 

“Starving.”

“Let’s get a pizza,” he said. “My treat.”

“Sounds good,” I said.

“Pepperoni okay?”

“Love it.”

He picked up his phone, tapped it a few times and put it down.

“You got them on speed-dial or something?” 

“Yeah,” he said. “I order two or three times a week. I don’t even have to tell them what I want, they just send it, charge my card.”

While we chatted and drank our beers, I began to wonder if he was being more than just friendly: inviting me for a drink, then to stay for dinner, then offering a shower. Didn’t seem likely, but as I was now aware, you never know.

I became conscious of my sweaty smell.

“Maybe I should get that shower before the pizza gets here.”

He pointed down the hall. 

“First door on the left. I’ll bring a fresh towel and a pair of shorts and put them next to the sink.”

I grabbed my spare T-shirt and headed for the bathroom, which lacked a tub but had a good-sized shower with a frosted glass door. I undressed and dropped my sweaty clothes on the floor.

I was leaning into the shower to turn the water on when the door opened behind me. I looked over my shoulder, and Jason was standing there, shirtless, holding a towel and a pair of basketball shorts.

“Oh, sorry,” he said. 

“No worries,” I said, standing up. 

Our eyes met briefly, then Jason’s glance flicked down at my crotch. When he looked back up and realized I had seen him, he looked away, embarrassed.

I turned back to the shower and got in. Closing my eyes, I let the water wash over my head and shoulders and began to soap up. I felt my cock stiffening. I asked myself, What is going on here?

A noise made me look up. It was hard to see through the frosted glass, but it seemed Jason was still standing in the doorway.

I opened the door part-way and stuck my head out. He was still holding the towel and extra shorts.

“There’s a back brush here if you want it,” he said.

We looked at each other again. 

“Bring it in,” I said, and ducked back into the shower.

Well, that was gutsy, I thought. Maybe he’ll come in here and kick my ass.

I turned enough to see his shape through the frosted glass. It looked like he had dropped the things on the sink. Then he bent slightly and something dark fell to the floor. His shorts.

I turned back into the stream of water, facing away from the open shower door. I heard him step in and close it behind him.

“I swear I wasn’t planning this when I asked you over,” he said. 

“And I swear I wasn’t expecting this when I accepted.”

“Hand me the soap?” he asked.

I passed it back to him without turning

He worked up a lather and started washing my back, tentatively at first, then with more assurance. His hands, hardened by years of manual work, felt rough on my skin. But they felt good, too, and as he worked his way down, massaging my aching muscles, I began to relax. 

“I completely forgot the brush,” he said.

I laughed and said, “No problem, that feels awesome.”

“Ever do this before?” he asked. 

“Yes,” I said. “You?”

“No.”

I briefly wondered if “this” meant to him: just taking a shower, or something more?

I turned around. We looked at each other, then down at our cocks. His was a big one, bigger than either Matt’s or Stan’s, with a thick shaft that curved slightly upward and ended in a  perfectly shaped corona, now almost purple with excitement. The swollen head was no more than two inches from the tip of my own, equally swollen cock.

“Your turn,” I said. “Turn around.”

I lathered up and began spreading suds on his neck and shoulders. I washed them thoroughly, massaging the muscles as I went. His muscles were tense at first -- from work or sexual excitement, I couldn’t be sure -- but I felt him relax in my hands.

I worked my way down his back. When I was done with the lower part I squatted. 

“Lift your foot.”

He shifted his weight to his left foot and lifted the right an inch or two. I lathered up again and washed it, working the soap between the toes and massaging the sole vigorously. 

“Oh my God that feels good,” he said.

“Other one,” I said.

He shifted his weight and I washed the left foot the same way. Placing it back on the floor, I lathered up again and began working my way back upward, washing and massaging his calves and the backs of his thighs. 

When I came to his buttocks I said, “Spread your legs a bit.”

He hesitated a second before complying. Still squatting, I went to work on the left cheek, kneading it vigorously with both hands, then switched to the right. I made a point of slipping a finger into the cleft now and then. 

When the outside of his cheeks was done, I put a finger into the cleft and drew it steadily downward. When I got close to his puckered hole I felt him tense up, but I kept going, pressing a fingertip into it, enough to make him gasp.

I withdrew the finger and stood up.

“Tilt your head back,” I said.

When he did I angled the nozzle to wet his hair. I picked up a bottle of shampoo, squeezed some into my hand and lathered him up. As I leaned toward him the tip of my cock bumped his ass. He drew another sharp breath. 

After a thorough wash and scalp massage I had him lean back again for a rinse.

“Turn around,” I said.

He faced me, our cocks as rigid as before but still not touching. I lathered up his chest, gave it a good massage, enjoying the feel of the muscles in his pecs. I rubbed the flat of my thumb across his nipples, which made his cock give a little jump. I lifted one arm, washed the armpit, then worked my way from the shoulder to the fingertips. I did the other arm, then began washing his six-pack. 

As I did so I bumped his cock two or three times with the back of my hand. I pretended not to have noticed. 

It was time for the lower half of his body. I squatted again, my face just inches from his straining cock. I washed his shins, knees and the fronts of his thighs. As I worked his cock bumped against my forehead two of three times, and once hit me in the cheek. Again I pretended that nothing had happened.

I looked up at Jason. He had a pleading look on his face.

I soaped up again and put both hands on his balls. He drew another sharp breath as I began rolling them in my palms, gently kneading and squeezing them.

Still looking into his eyes, the way Stan had looked at me, I soaped up once more and moved my hands to his cock. He whimpered. Grasping the head carefully with the left hand, I spread soap on the shaft with the right. I let go with the left hand and gave his cock several firm strokes. He moaned.

I let the water rinse the suds away. His cock was barely two inches in front of my face. 

I was just about to open my lips when I heard a noise and Jason gave a start.

“Fuck, it’s the doorbell,” he said. “Pizza’s here. Fuck fuck fuck fuck.”

With obvious reluctance, he opened the shower door and stepped out. As I stood up I saw him through the frosted glass, grabbing the towel from the sink and disappearing.

I finished washing myself. My cock was rigidly erect. I thought, boy, my sex life sure has been interesting lately. 

I stepped out of the shower. There was no other clean towel in the bathroom, so I walked down the hallway and into the kitchen, naked and dripping wet, my swollen dick leading the way.

Jason stood there, wrapped in “my” towel, holding a pizza box. I hooked a finger in the cloth and yanked it free.

“You took my towel,” I said matter-of-factly.

I dried myself off and tossed the towel back his way. It landed on his head.

I went into the living room and sat on the couch. I heard Jason put the pizza in the oven.

He came in and stood on the rug in front of me. His cock was still diamond-hard. 

“Where were we?” he asked.

“Here,” I said, and took his cock in my hand. 

I said earlier than when Matt had not just sucked my cock that night weeks earlier; he had worshipped it. Now it was my turn to show reverence for the male member.

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Jason’s member was certainly worthy of it. It was eight inches long, easy, and as big around as a beer can. A blue vein ran along the top of the shaft, and the ridge along the bottom was as prominent as a range of mountains. The head was perfectly shaped, as I said, flaring smoothly outward from the slit, with a long string of precum dangling from it.

I pulled him closer to me and for the next ten minutes did everything I could to pleasure him the way Matt had pleasured me. I massaged and sucked his balls. I licked the underside of the shaft, giving special attention to the super-sensitive skin near the tip. I tongued the slit, tasting the precum that was flowing freely now. I covered it with kisses. 

I looked up at him and locked eyes the way Stan had with me. I opened my mouth and let him slide it in, pressing against the underside with my tongue. I took in four inches, then five, then six, and felt the head pressing against the back of my throat. I fought the gagging feeling, breathing through my nose and consciously relaxing my throat.

He pressed a little further, and my nose touched his public hair. My eyes began to water.

“Oh, my God,” he said. “No one has ever come close to doing that.” 

I backed off a little, caught my breath, and pressed forward again. This time I took him more easily. I repeated the move and began to feel more comfortable with my throat totally filled with cock. 

Jason was so keyed up that barely two minutes passed before I felt his cock swelling and his balls contracting. He made a gurgling noise deep in his throat, gripped my head with both hands and thrust deep into me.

“Ohhhh,” he moaned. “Oh my fucking God.”

A flood of cum shot into my throat. His cock was so deep in me that I couldn’t really swallow, so I just let him fill my mouth with his seed. I opened my lips and let it flow out of my lips and down my chin. 

I still had not taken my eyes off him. He must have seen the tears leaking from my eyes, because he backed off enough to let me get my breath. When I did I closed my lips around his throbbing cock and swallowed. It was a huge load.

My lips were still clamped tightly around the base of his cock. He backed out slowly, wincing as the suddenly sensitive skin slipped along my tongue and through my lips. The head came out with a pop. 

Jason’s legs wobbled, and he sat down hard on the rug. He looked at me briefly, and then lay down on the rug and closed his eyes. For a second I thought he had passed out.

My cock was painfully hard, and I was desperate to get off. I kneeled next to him and started jacking furiously.

“No, wait,” he said. “I want to suck you.”

I lay down on the rug next to him. He rolled partway up and took my cock in hand. 

“Um, I’ve never done this,” he said. 

“It’s okay,” I said. “Guys know what guys like.”

He was a little clumsy, and at one point I had to tell him to watch his teeth, but in the end he did a damn good job, bobbing up and down, taking in all but the last inch of my shaft. 

When he sensed I was about to come he backed off, watching with fascination as the first shot of cum flew out of the head. He opened his mouth again and caught the following shots on his tongue. When I finally stopped shooting he swallowed, then bent down to the lick the first puddle off my stomach.

He lay back down next to me. It was so quiet I could hear the clock ticking in the kitchen. He turned his head my way.

“I don’t have the words to say how wonderful that was,” he said.

“I’m glad you enjoyed it.”

“Enjoy it? I didn’t just enjoy it. That was the greatest sex of my entire life.”

“I’m glad I was here for it.”

He was quiet for a moment. I turned to look at him. He started to say something, then stopped. 

“Go ahead,” I said.

“Would it be okay if I kissed you?”

“Sure,” I said.

He closed the distance between us and briefly touched his lips to mine. He did it again -- longer this time -- and then a third time, longer still.

“Wow,” he said. “The idea of kissing a guy used to seem disgusting. But that was actually great.”

He propped himself on one elbow and kissed me once more, this time with real passion. I felt his still-swollen cock against my side.

“I want to do more,” he said. “But maybe we should have that pizza first.”

“Okay,” I said. “Where did you leave those shorts?”

“Don’t get dressed,” he said. “I want to keep looking at you.”

So we enjoyed our pizza naked.

While we ate and sipped our beers we talked. Jason said he had been attracted to guys since he was a teenager, but had never acted on his urges. His family was very religious and uptight  about sex, and he was brought up to consider homosexuality an affront to God. 

He liked women and enjoyed sex with them, he said, but fantasized about men all the time. And once he was on his own, he started watching a lot of gay porn. 

“I’ve got some pretty hot DVDs in my closet,” he said suggestively.

I told him about my short but intense experience of sex with men

“You mean that was only the second blow job you ever gave?” he said.

“Yep,” I said.

“Wow, I would have thought you’d been doing it for years.”

I wasn’t sure I liked hearing that, but what the hell.

“The thing is, I’m totally in love with this girl right now,” I said. “My sister’s boyfriend said I might be a mostly straight person who enjoys sex with men now and then, and I think he might be right. It’s hard to say, though; it’s still pretty new to me.”

Jason was quiet for a moment. 

“I want to suck you again before you go,” he said, a yearning look on his face.

My cock twitched.

“Okay, but I’m too full right now,” I said. “Let’s chill for a bit first.”

We moved to the couch, still naked. We had just sat down when Jason got up again, went into his room, and came out with a couple of DVDs.” 

“Dude, who still uses DVDs?” I said.

“I found them in an old house we were rehabbing,” he said. “Didn’t want them to go to waste.”

He selected one and popped it in the player. 
The title came on. “Cum To My Place.”

“These things are so cheesy,” he said.

Didn’t matter, though. Before five minutes were up, Jason and I were making out again on the couch, paying no attention to what was on the screen. We ended up on the floor again, this time in 69 position, suckling each other’s dicks, bringing each other to the brink of orgasm and then backing down, again and again, until we both hit a frenzied peak of excitement and blasted into each other’s faces. 

After another long session of kissing, I finally had to go. Pulling on my clean shirt and dirty shorts, I got ready to leave. I was looking for my discarded T-shirt when I saw Jason had it in his hand.

“Can I keep this?” he said, dipping his head to smell it. “I like your smell.” 

A few weeks ago, that gesture might have seemed weird. Now, pretty much nothing did.

“Sure,” I said.

As I was walking out the door he grabbed my arm, pulled me back in and gave me a long kiss.

“We should do this again sometime,” he said, a big smile creasing his face.

“We should.”

We did do it again, three or four times in the weeks remaining before I went off to college. I think Jason would have liked to get together more often, but that was of course difficult when his roommate wasn’t traveling.

By summer’s end, I had gotten used to Jason’s big cock and could deep-throat him with ease. He was absolutely obsessed with my dick, and would lick and suck it as long as I could stand it. 

The last time we got together, a few days before I left for college, we were in his bed having a particularly intense 69 session when I began exploring the area behind his balls with my tongue. I hadn’t done this before, but the sounds Jason made told me I was doing something right. 

I edged closer and closer to his hole, hoping he had washed himself thoroughly before I arrived. Thankfully I smelled soap, but also detected a slightly funky scent that was strangely erotic. I probed a little further, and when the tip of my tongue touched the puckered pink flesh Jason shuddered and said, “Oh my God.”

We rearranged ourselves on the bed, Jason on all fours with me behind him. I spread his cheeks and dipped my face between them.

When my tongue touched the pucker he shuddered and moaned again. I began licking him vigorously, in long steady strokes, pressing my tongue firmly against his hole on each pass. When I poked my tongue in his hole and flicked it back and forth, he started whimpering.

“Oh, my GOD,” he said. “Jesus that feels good.” 

Emboldened, I started tongue-fucking him. He actually whimpered.

Then, he said, “Fuck me, Andy.”

I had known this moment would come, but even so, I was uncertain.

“Are you sure?” I said.

“Yes, I’m sure,” he said. “Put your cock in me and fuck me.”

“I should loosen you up first,” I said. 

“No, just put it in,” he said. “There’s lube in the drawer.”

I reached over to the nightstand, pulled open the drawer and fished out a tube of lube. Repositioning myself behind him, I slathered some lube on my cock and laid it into his crack.

“Go slow,” he said.

I centered the tip of my cock in the puckered ring and began to push. 

Jason groaned, but he didn’t try to stop me. I felt a pop as I slipped through the inner ring, and he groaned again. 

“Are you OK?”

“Yes,” he hissed. “Keep going.” 

So I did. I pushed again, watching as the entire length of my cock slowly disappeared into him. 

Soon I was fully inside. He was really tight, compared to the girls I’d fucked, and the heat was intense.

“Hold on a sec,” he said. “Let me get used to it.”

He breathed slowly and deeply several times, and I felt him slowly adjusting to me.

“Okay,” he finally said. “Let’s fuck.” 

I pulled back very slowly, till all but the head of my cock was visible, then pushed back in.

Jason groaned.

“Oh … God…oh, Jesus,” he said. 

I bottomed out, pulled back again, pushed in again. As I picked up the rhythm, Jason’s moaning turned into groans of pleasure. 

“Fuck me, Andy,” he said, grinding his face into the pillow. “Fuck me.” 

I reached around and felt for his cock. It was rock-hard and dripping precum.

I picked up the pace. His groans rose in pitch. It sounded like he was about to cry. I was groaning myself. 

“I’m…gonna…cum,” I said, my voice raspy.

“Cum in me,” he said. “Shoot inside me.”

I was pumping hard by now. I let go of his cock, gripped him by the hips and slammed into him over and over. I felt the muscles around my cock tighten, and it sent me soaring over the edge.

“Ohhhhh, “ I shouted, slamming into Jason final time. I drove forward, pushing him downward, jetting cum into the depths of his ass. “Oh, Jesus.”

My orgasm must have triggered Jason’s, because he clutched the sheets in his hands, ground his face into the pillow and made a roaring sound, followed by something that sounded like sobbing.

Exhausted, I collapsed on top of him. I was still but he was still spasming inside, and each twitch squeezed a little more seed out of my cock.

We lay still, breathing deeply, for several minutes. I lifted my head, kissed his shoulders and neck, and slowly pulled my cock out of his ass.

“Oh, ow, oh, oh,” he said.

I collapsed on the bed beside him. He rolled on his side to face me, but kept his eyes closed. 

The sheets between us were soaked with cum.

“Was that you?” I asked.

“The minute you started cumming, I did, too,” he said. “I never even touched myself.”

“Wow.”

“God, that was incredible,” he said. “The feeling of your mouth on me was so intense I thought I was going to come out of my skin. And then being fucked -- I couldn’t believe how good it felt once I got over the pain. I had no idea your ass could be so sexual.”

He pulled me close and kissed me passionately.

“Did it feel good to you?”

“Hell, yes,” I said, laughing. “You were much tighter than a vagina, and when you got close to cumming it was like your muscles just squeezed the cum out of me.”

We lay there talking quietly for some time before I got up and started searching for my clothes.

“Can’t you stay a bit longer?”

“No, it’s late already,” I said. “Gotta get an early start tomorrow.”

When I was ready he pulled on boxers and followed me to the door.

“It’s been a hell of a summer,” he said. “I’m going to miss you. Are we going to see each other again?”

“Sure, why not?” I said. 

I swung the door open. As I did he pulled me close again and kissed me hard.

Looking over his shoulder, I saw that someone was watching us: a muscular Hispanic guy who looked to be in his twenties. He must have come up the stairs on his way to another apartment.

Our eyes met for a second, him standing there with a bag of groceries, me looking over the shoulder of a guy wearing nothing but boxers. He looked away -- was he embarrassed, or just amused? -- and headed up the stairs. 

Well, that secret’s out, I thought.

For some reason, I didn’t tell Jason we’d been seen. I just gave him another kiss, stepped out the door, turned once more to look at him. He looked like he was about to cry.

I turned and went down the stairs, feeling pretty bad myself.

 

Published 
Written by dondave
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