My Orange-Haired Barista by Yossarian66

Rating: 85%, Read 11084 times, Posted May 11, 2017

Fiction | Anal, First Time, Gay, Oral Sex, Virginity

Being a professional writer I spend a lot of time at my local coffee shop. When the words don’t flow at home I pack up my computer and notebooks and head down the block for a latte and a change of scenery.

The local crew know me and knows my drinks and, as a result, I have gotten to know them pretty well. I hear all about their school schedules, their love lives, even their hopes and dreams. I felt very at home there, which is good since my average visit is three to four hours.

One afternoon I went in as usual and spotted him immediately. He was a new boy and, as the low man on the totem pole, was assigned to garbage and bussing, the lowest job in the place. I am normally only attracted to dark-haired boys, but there was something about this one that gave me pause. I shared a smile with him as I passed on my way to order.

Once settled out on the patio I got out my idea book and got to work. I had a great idea for a horror novel, somewhere between Koontz and King, but with a lot more sex. As I finished up a character sketch of my protagonist, I saw my orange-haired beauty come out, in search of more trash to collect and tables to clean. When I smiled at him this time, he gleamed back the brightest set of teeth and sexiest smile I had had in a long time. My loins stirred at the thought of those lips planted around my cock. He finished his run and disappeared back inside and I returned to my work.

An hour later he came back out, without the apron, so I figured he was on a break. I waved him over and he nodded and sat down with my. I got out my kit and started rolling a cigarette.

“I’m Joe,” I said. “I haven’t seen you here before.”

“I’m Derek. I just started.” He eyed the cigarette I had just made and I offered it to him and proceeded to roll another. His lips held it in such a sexy way it took me a minute to pick up my lighter and light them.

“Tell me about yourself, Derek.”

“Nothing much to tell. Just started college, working here to earn a little coin. They tell me in there you’re a writer.”

“Yup, I am.”

“Published much?”

I listed a few of my books and his face lit up. “Wow, man! I’ve read all of those. You’re great!”

I chuckled. “I’m okay. I’m no Hemingway but it pays the bills.”

“Man, that’s what I want to do, be a writer.”

“Just stick with it. It takes some time, but it’s a mostly great life. What do you write?”

“Right now, just some stories and shit, you know.”

“That’s a start. If you like, I’ll read some of it and give you some pointers.”

“Really? That would be great!”

“Tell you what.” I looked at my watch. “What time do you get off?”


“Okay, why don’t you run home and get your stories and come over to my place around six. Will that give you enough time?”


I gave him my address and he thanked me for the smoke. As soon as he was back inside I packed up my stuff. A quick trip to the market and I was all set.

He arrived exactly on time. I had changed into a pair of running shorts and a t-shirt, something comfortable just in case. Derek carried a folder with his stories and I handed him a beer as we sat down. I picked up the first story and dug in.

It was utter crap, full of cheap symbolism and no passion. He didn’t even type well. I reread it, hoping I had missed something, but the second time around it was even worse.

“How about dinner?” I said.

The food was simple, just pasta and a salad. Derek dug into it with relish and it brought back memories of me when I was in college and had a chance to eat away from the horrible fare in the school cafeteria. I evaded his questions about the story as best I could, finally calming him with a few vague comments.

We sat and had another beer and cigarette on the couch. I looked at his blue eyes and pale, freckled skin and resisted the temptation to just rape him. As we sat and talked my hand found his shoulder. He looked at it but didn’t shrink away or anything. My eyes shifted down to Derek’s crotch, and I could see a bump starting to develop.

I looked up at him, trying to find an invitation to move forward. I brought my hand up to caress his smooth cheek, and our eyes locked. My breathing picked up in anticipation.

“Um, Joe. I’ve never…”

“Shhh. Just go with it. Everything’s alright.” I went for broke and brought my lips to his. We shared a warm kiss as I took him in my arms. I took his hand in mine and guided it down until it rested on the front of my shorts. My cock jumped to his touch and he started rubbing it briskly. I reached inside his shorts and found his tool past the bristly growth of his pubic hair. Any inhibition Derek may have had was long gone, judging by the tight grip he had on my cock.

I broke away from him and motioned for him to follow me to the bedroom. Once we were there I took off his clothes and looked him over. Never have I seen skin so white. He was mostly hairless, except for the carrot-colored thatch between his legs. His cock had risen, all seven inches. It was just about the skinniest cock I had ever seen but it would do.

“What do I do now?” he asked.

“Sit down on the bed. Have you ever gotten a blowjob?”

“Naw. I’m a total virgin.”

I knelt in front on my barista and took him in hand. Gently I licked at his balls and stroked his pole. Derek let out little mews and moans of pleasure as I sucking his young, stiff prick. I was so hot with the knowledge I was giving Derek his first sexual experiences. All too soon he exploded in my mouth, and I swallowed every drop of his teenage spunk.

Derek collapsed back on the bed, sated with pleasure. As he recovered I shucked my clothes and joined him, rubbing my naked flesh against his.

“Liked that?”

“Geez, that was awesome.”

“Ready to return the favor?”

“Oh yeah!”

Derek sat up and grabbed my cock, stroking it up and down, fascinated with his new toy. He tried to imitate what I had done to him, licking around the head of my penis, gently rubbing my sperm-filled balls. Finally he took my engorged shaft in his mouth, struggling with my girth as I rested my hand on his back. I knew I wasn’t going to cum from his first attempts at fellatio, but I was enjoying it nonetheless.

I moved up on the bed and Derek followed. I slipped my hand between his legs and Derek shifted his weight to allow my access. After rubbing his balls for a bit I moved at finger to his tight, virgin boy pussy. He moaned as I worked first one, then a second finger into his young ass. Derek’s hand found my cock and he proceeded to jerk me off as I finger-fucked him hard and fast. His thumb worked on the head, his other fingers squeezing my shaft.

The time had come for Derek to lose his cherry. I reached over and grabbed the tube of lube I kept by the bed for just such an occasion. I greased up my cock and gently parted his ass cheeks. “Relax.”

I moved behind him and rubbed my slippery, purple cockhead against his tight pink hole. I applied pressure pushing the tip inside him. I pulled it out and pushed it back in several times, each thrust gaining a little more ground. Derek clutched a pillow as I worked all nine inches into him. I began pushing harder, deeper, until his ass adjusted to me cock plowing into it.

Finally, I just grabbed his hips and fucking him hard and fast. My balls slapped against his, the pressure building as I fucked my little boy toy. I couldn’t hold it any longer; his tight ass milked the sperm out of me. With a loud grunt I pushed my cock all the way in him and held it there as I spewed my cream deep into his body. I collapsed onto him and held him tight, totally spent. I kissed him on the ear and hugged him close. Derek was silent, overwhelmed at this new experience.

He rolled over to face me and I gave him a sweet kiss on the lips. “How was it, sport?”

“It hurt at first, but then it was great! Kind of weird, though.”


“I always thought my first time would be with a girl.”

I lit two cigarettes, handing him one. “Girls can be fun too.”

“You mean you fuck girls?”

“I have, but I like fucking little boys like you better.”

We lay there until our hands found each other’s cock. With our eyes locked we stroked each other back to erection. Derek was fascinated with my penis, commenting on its size and girth. I loved his equally. His bright orange pubic hair was so unusual, such a novelty.

“Derek, would you like to fuck me?”

“Yeah, Joe. Can I?”

“You’d better!” I punched him on the shoulder, playfully, and handed him the lube. “How would you like to do it?”

“Doggie style?”

“Woof, woof!” I got up on my hands and knees, offering my ass to my new lover. He squirted lube on his prick and moved it to me. Being more experienced at this, I was able to take his skinning cock with the first thrust.

He grabbed my hips and fucked away, lost in these new sensations. It took quite an effort to stay upright against his powerful motions. I squeezed at his invading cock as best I could, but Derek was in his own little world, centered on his young prick. All too fast he cried out as his shot my ass full of his sperm.

“Sorry, I came too quickly.”

“Not a problem, sport. You did fine.”

I suggested a shower and soon we were both soaping and rubbing ach others wet bodies. We kissed long and hard under the water, glorying in the feel of each other’s flesh. He was so skinny, just like his prick, with hard muscles underneath his pale skin. I have never seen anyone who was so white.

We toweled off and I threw him a clean pair of shorts. We went back to the living room and had another glass of wine.

“Derek, I’m sure glad I found you at the coffee shop.”

“I’m glad you found me too. This was great.”

“Glad you enjoyed yourself.”

We sat on the couch, his back to me. I held him in my arms and just kind of rocked him. He fell asleep that way and I just stayed with him until I fell asleep as well.

I woke up at 1 AM, and Derek looked up at me.

“Want to spend the night?” I asked.

“I don’t have any things with me.” He replied.

“All you’re gonna need is a toothbrush and a lot of stamina. And I have a spare toothbrush.”

Our relationship started out casually enough, with us getting together a couple of times a month. We always started out with me evaluating some piece of his writing. Over the next several months his work began to improve. His characters began to show signs of life, going from flat and wooden caricatures to living, breathing beings with minds and motivations all their own.

I decided I needed a vacation and invited Derek to join me. We drove up the coast to a little hideaway I visited a couple of times a year. It had been quite a while since I had brought anyone with me, as these trips were meant to be therapeutic rather than sexual.

It had been a couple of weeks since we had done anything sexual, as Derek was going through finals. The tension in the car was palpable. I wanted to ravish him as soon as possible. Once we got settled we got naked and worked up an appetite for dinner.

His young skin was like ivory and silky to my touch. His ass cheeks were small, round and smooth. The firm, tight nut-sack nestled between his upper thighs, bulged with two delicious orbs. His cock was hard between my lips as my tongue played with its spongy tip. He was standing as I knelt. Each of my hands held a warm, pert, protruding ass cheek as they pulled his hips against my face. I was sucking his flesh, biting it playfully with my teeth, stroking his skin with my tongue. Moving in and out, his stiff cock was caressing my lips, pushing against the roof of my mouth. I could feel his passion. I could feel him throbbing against the inner lining of my cheeks. Oh God, what a sensation! I wanted to eat him alive.

The index finger of my right hand found the texture of his tight, young anus and caressed its wrinkled surface. It too was warm and soft, yet spongy and tight. My fingertip lingered there and then, slowly, began to work its way in. His body responded with a spasm as his butt cheeks contracted around my finger. He arched his hips harder into my face and began fucking my mouth faster, with more urgency. I could hear his intense breathing as he suddenly clasped my head with his hands. He buried his fingers in my thick, grey hair as he pulled me inward to meet his thrusts. He was using my head to fuck his cock as the rapidity of his bucking increased. What an erotic sensation! What a divine feeling! I could feel his energy increase with each shove. He was groaning now, preparing himself to release his seed onto my tongue.

My own erection was getting harder as my hands squeezed his ass cheeks, holding his belly close to my face. Ohhh, I wanted to feel him explode in my mouth! I pushed my finger deeper into his asshole and began pumping him. First one finger, then two, then a third I was now giving him a deep ass-fuck with my right hand. I wrapped my left arm around his hips and continued to pull his loins toward me. We were in total unison. We were One in our hot, mutual lust.

My fingers were penetrating his love-hole ever deeper. With each thrust of my hand his sphincter opened wider. The natural resistance of his anal ring was now completely gone, as I felt the inner lining of this rectum along the full length of my fingers. I continued to push into his love-hole as he continued to pump my mouth. My own untouched cock was ready to explode and I was groaning. Our mutual energy was now beyond control and almost violent. We were consumed in utter lust.

Suddenly, I felt an explosion in my loins, as my sperm erupted in white, creamy spurts that landed on the blanketed floor and on his feet. Simultaneously I felt his body buckle and shake as his cum began spurting into my mouth, his ejaculate hitting my tongue, his balls bouncing against my chin. We collapsed onto the carpet and lay, exhausted, with arms and bodies intertwined.

He was so perfect, almost feminine, his smooth, supple legs wrapped around my own. His sweet cock, now soft, was caressing my larger, older manhood. Our breathing had become slow and even. I kissed the silky skin of his neck and kissed his lips, while he sighed as his left hand fondling my testicles. My right hand cupped his balls and penis, squeezing and massaging them, pulling on each testicle, pinching the spongy, moist tip of his velvety cock. Then, we fell asleep.

After about twenty minutes of delicious slumber I awoke. My

Derek was still sleeping in my arms. I wanted to fuck him now and I wanted to fuck him hard. I wanted to ravish his rectum.

I reached under his hips and took his hard young flesh into my right hand. I began to jerk him, slowly at first, then harder and faster. I worked on his asshole as I ground my hips, cock and balls against him. His pre-cum was making my right hand moist and he was close to ejaculating, but I wasn't ready for his release. I wanted him in full heat and lust when the moment arrived.

I turned my body around with my knees now between his legs and my face buried between his ass cheeks. He was groaning louder as my right hand squeezed and kneaded his balls and cock, my tongue firmly imbedded in his sphincter. I was fucking his asshole with my tongue, getting ready to ravish his luscious back entrance with my hard and meaty cock. I fell on him as my arms embraced his shoulders and my engorged cock fell into his crevice. My hips began to move rhythmically as my cock slid back and forth between his cheeks. He was meeting my movements with his own, alternately lifting his hips, and then dropping them. He was inviting me in. The tip of my penis found his rosebud, which was wet and ready for my assault.

The tip of my cock entered easily. His anal ring locked around the fleshy head of my manhood, inviting me to have my way with him. I did. I plunged the full length of my cock deep into his bowels and began thrusting with hard intensity. I was fucking him in total abandon. His body was pinned underneath mine, my hips bucking back and forth as my meat ravished his asshole. He was quivering all over, meeting my attack by pushing his ass against my stiff, swollen member.

I buried my face between his neck and right shoulder, my lips kissing his soft skin. He turned his face toward mine and our lips met. His tender mouth opened to receive my tongue, his own now pressing against my lips. My mouth opened and we began French-kissing passionately as my cock pumped his ass. He was groaning as we tongued each other, exchanging saliva, feeling each other's hot breath. I let go of his shoulders and took his head into my hands. My fingers were buried in his bright orange hair.

We stopped kissing and gazed into each other's eyes. He was watching my face as I fucked his asshole with total abandon. He wanted to watch me as I released my load. He wanted to see the look in my eyes as the sperm erupted into his rectal canal. He wanted to watch my face as my body buckled and shook with the power of my orgasm. I started to come and with it came a roar. I was out of control. My body was shuddering with the release pulsing through me as I continued thrust. With each thrust his eyes would close slightly and he would utter a soft grunt. At last, when the final drop had been expelled my body relaxed and my breathing slowed.

As if to say 'thank you', he glued his lips once more to mine, his tongue gently probing and tonguing my own. I reached under his belly and felt his cock. It was still hard and inviting.

I rolled him over toward my face, took his young, stiff cock in my mouth and sucked him dry. After he came in my mouth, we fell asleep in each other's arms for the second time on that hot and sultry afternoon.

When we woke up we shared a shower, too spent to do anything but soap each other up. We dressed and held hands as we made our way to the lodge for dinner. People there thought Derek was my son, which gave me an erotic thrill. Most of the women and even some of the men looked Derek over with that unique blend of intrigue and desire. They could look all they wanted but he was mine, at least for now.

The next day after breakfast we went to the beach, clad only in t-shirts and speedos. Derek was a little shy about the tight swimwear I had bought for him, but I assured him he looked plenty hot. He said I looked good in mine, for a middle-aged man. I slapped his ass playfully at that remark.

We set up at the beach. I rubbed sun oil all over him, as I was sure his creamy white skin would burn easily. After he returned the favor we lay down on our blankets, enjoying the sun.

I awoke around noon and Derek was staring at me. I smiled before he pressed his lips to mine, a happy puppy-dog look on his face. We held each other and just kissed.

“Derek, how adventurous do you feel?”


I pointed to an outcropping of rocks. “On the other side of those rocks is a clothing-optional stretch of beach. Interested?”

“A nude beach?”

I nodded.

“I don’t know…”

I got up and grabbed our towel. “Come on. It’ll be fun!”

I lead him by the hand down the beach until we came to a path in the rocks. It was narrow and wet, so I told Derek to be careful. I recalled my first trip here when I was in college. The pledge class from my fraternity had been dared to go on the beach, strip naked, and stay for one hour.

When we got to the end of the tunnel I surveyed the secluded stretch of shore. There were only a few people there, mostly singles. I waved to a couple as we set up our own towel. I quickly shed my speedos and lay down in all my glory, daring my young lover to do the same.

Derek was obviously nervous. He hooked his fingers on the side of his suit and hesitated. He reminded me of the freshman boys back in high school taking their first gym shower, not sure how they would measure up to the upperclassmen.

“Just do it!” I said.

In one fluid motion he stripped off his speedos and lay down, ass in the air, on the blanket. I giggled at his embarrassment.

Before long we attracted attention. A huge hulk of a man walked towards us. He had to be six-foot five and at nearly three hundred pounds, all of it muscle. His body was covered by a thick mat of black hair, exceeded only by the biggest and thickest bush of pubic hair I had ever seen. I could barely make out that there was a cock and balls in there somewhere.

“Hey,” the man said. “I’m Tim.”

“I’m Joe, this is Derek.” Derek tried to sink into the earth so as not to be seen.

“Nice to meet you. You guys locals?”

“Nope,” I replied. “Just up for a couple of days.

“Sweet. There are a couple of us over there getting ready to make lunch. You guys want to join us?”

I looked at Derek, unable to detect what he was thinking. I always like to be sociable, so I agreed for both of us. We picked up our stuff and followed Tim back to his group. As we approached we saw three other men, all naked, sitting around a makeshift driftwood table.

After introductions we took the proffered food, which was delicious. I was glad to see Derek finally opening up a little, relaxing. We spent the afternoon with the men, casually eating and talking and sharing life stories. All their eyes were on Derek. I could see that every one of them wanted to fuck my little treasure. I’m not sure Derek noticed the lust in the air and I didn’t want to share.

When the meal and socializing were finished we said goodbye and walked back to our bungalow. Ever the ambitious writer Derek spent the rest of the time on his writing. I played around with my own work, not really into it.

The rest of the trip we only made love one more time and, as it turns out, it was the last time. Derek had tasted the forbidden fruit of gay sex and found it really wasn’t for him. We remained friends and I continued to help him with his writing. He managed to publish his first novel before he turned twenty-one, but it was roundly panned by critics and ignored by readers. After that we slowly lost touch, but I would always have the memories of my little orange-haired barista.

Rating: 85%, Read 11084 times, Posted May 11, 2017

Fiction | Anal, First Time, Gay, Oral Sex, Virginity


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