Straight virgin gets his gay cherry popped



I had a little crush on an older boy in the cycling club. He liked me too.

I’d never had sex with anyone before meeting Lou.

I’d had girlfriends, but we were just fumbling around. I’d had my hand up a few skirts and fingered a couple of girls but we weren’t old enough to go further.

One girl had taken my cock in her hand and was close – oh so close – to giving me an orgasm when her parents came home unexpectedly and we had to dive for opposite ends of their living-room couch. I just managed to pull up my jeans before the front door opened. Had to put a magazine in my lap to cover my erection as her ma came in. And then I couldn’t be polite and stand up when she entered the room. Very embarrassing and frustrating and something must have been said, because that girl broke up with me a couple of days later.

I did get a hand-job to completion one afternoon in the woods behind our school. From the girl with the reputation. Every school has one. It was fast. I think she must have jerked off half the boys in our year. But that was it. I wanted to fuck her, but she only put out for seniors. Jerking off boys her age was like a hobby for her.

I masturbated a lot. Anything could get me going and I spent a lot of time in my room getting relief.

So anyway, like I said. Almost zero experience. And I’d just turned 16, which made me completely legal. I felt the pressure was on to get laid or I’d be a virgin forever.

And then Lou. He was a member of the cycling club I joined. He was 19. I looked up to him because he’d competed in local races …and done OK. And he was great with new members. Encouraging them, organizing training, helping to tune bikes, etc.

I suppose I started to hero-worship him. I’d hang around and watch whatever he did and try to copy him. I went out and got a proper cycling kit because of him. Tight spandex. It did nothing to disguise your junk, that’s for sure.

I’d noticed and maybe even admired how big a bulge there was in Lou’s shorts. I wasn’t packing like him, but was still self-conscious about my bulge. First time I showed up in the new shorts, Lou looked me up and down and told me I looked good. That was all I needed to hear.

One weekend there was a training ride scheduled and I signed up. But when I arrived at the meeting place there was nobody there. I was just about to leave when Lou showed up. He was driving, though. His bike was on the roof rack. He explained that only one other rider had signed up that weekend, so he’d called him and cancelled the training. But he thought I might enjoy a ride with just us two.

I was really pleased. Getting to be alone with my hero. I guess it was a crush, but I hadn’t given it much thought.

Lou said he had a particular loop planned but it was not nearby so we could drive there together. We got my bike next to his, up on his roof, and set off. It was a nice sunny day and we drove for about an hour out to the coast. Lou parked in a quite spot and we got our bikes down.

The ride was about ten miles. Not too far. And the views were great. We looped inland and up so that the last part, back to the car, was downhill and looking out to sea. We climbed off our saddles. It was a relief to stretch out and I kicked off my shoes. Cycling shoes can be quite uncomfortable when not clicked into the pedals. I peeled off my socks, too. Lou did the same.

Lou had a surprise. “I brought a lunch for us, if you want.”

“Oh yeah! I’m starving!”

He went to the trunk of his car and grabbed a day-pack and a blanket.

“I know a spot. It’s not far. You don’t need shoes, it’s nice to walk barefoot on the grass.”

He handed me the blanket to carry and I followed him across the grassy meadow towards the cliff top. As we approached I saw a small path, invisible until you were nearly on it. We went down and it led to a small shelf nestled under the cliff edge. Flat and grass-covered and secluded.

“This is my private place” Lou told me.

I was pleased that he would share it with me. He made me feel special. We spread the blanket out and sat down. He handed me a sandwich and a drink and we ate in silence, staring out at the ocean. There were some sailboats out on the water and, looking down, you could see people on the beach below us. But, unless we were standing, we were invisible to them.

After we’d eaten, I lay back and enjoyed the warmth of the sun. “Sometimes when the weather’s like this I sunbathe naked here” Lou told me.

“Really?” I was kind of shocked. I don’t think I’d ever been naked out of doors.

“Yeah, nobody can see and the sun feels nice.”

“Well I could see!”

“I didn’t think you would mind.”

“Why not?”

“Well, I’ve seen you… looking at me.”

I guess I had been. And maybe he thought I was interested in him, ‘that way’. I wasn’t sure myself. I wanted to be like him. Wanted him to think well of me.

“I like you Lou. You’re really nice.”

“And I like you too, Luke. That’s why I thought we’d both enjoy a little private ride.”

“I am enjoying it, Lou”

“So, would it be OK it I took off my clothes in front of you?”

What could I say. It was OK. I was curious.

“Yeah, OK…. “

He stripped off his top and then scooted his pants down without standing. I tried not to stare, but he looked over and saw me looking at him. I looked away, but he spoke up.

“It’s OK, you can look. I don’t mind.”

“No that’s OK” I said, feeling my cheeks redden, and looking out to sea again.

He reached over and touched my hand.

“No, Luke. I want you to look at me. Please.”

I turned to face him. Looked at his face. He had an expression of pleading, almost.

“Look at me, Luke.”

“I ‘m looking at you, Lou.”

“No. LOOK at me.”

He moved his hand down and grasped his penis. My eyes followed the movement and I saw that he was erect and he started stroking his cock.

“Do you like it?”

“It’s big, Lou.”

“I know. I’m lucky.”

He spread his legs, slightly so that he could make longer strokes up and down the entire length of his long cock. I was transfixed.

“You like watching me?”

I didn’t answer, but I kept looking.

“I can tell you do, Luke”.

With his other hand he reached over and touched my crotch. It was only then that I realized I had a hard-on. I looked down. A wet spot had appeared. Pre-cum was leaking out of my cock as I watched Lou stroke himself.

“Join me, Luke. Nobody can see us.”

I wanted to do the things he did. Emulate my hero. But I was reluctant. He stopped masturbating, moved in front of me and started tugging at my shirt.

“Come on. It’s OK”

I sat still, lifted my arms, and felt him stripping my shirt off my body and up over my head. I looked up at him and had an urge to cover my nipples like a girl. But I didn’t. I sat there looking up at him as he stared at me. His erect cock swayed gently. He knelt down in front of me, reached up and grasped the top of my shorts. “Lift up your hips so I can pull these down.”

He just murmured it. It should have been said with more authority. I think back to it and want a reason for why I complied. I have none. I just did as I was told, and felt this man take off my last piece of clothing. Exposing me to his eye. I put a hand over my lap. “You have a nice cock, Luke”

“Err…. thanks.”

“Don’t cover it. Lie back and feel the sun on your bare skin. You’ll like it.”

I did as I was told. And he was right. The sun on my cock and balls felt great. We lay there together for a while. Naked. I looked over and Lou was gently stroking his cock.

Even though I was still semi-hard, I was too inhibited to let him see me jerking off. I just lay there, immobile. But I was enjoying the sun on my naked body. After a while Lou made another suggestion: “Turn over and feel the sun on your ass.”

I did. And he was right. The sun on my ass felt fantastic. It was almost sexual. Lou told me I ought to have some sunscreen on. He reached into his pack and pulled out a tube. I reached for the cream, but he held on.

“Let me put it on you Luke.”

Again I obeyed. He smoothed some lotion on my shoulders and down my back. I liked his hands on my bare skin, feeling him massage the cream in. Then I felt his hand begin to caress the smooth cheeks of my ass.

Oh man. It was so wrong, but it felt so good. He spent a long time on my ass. I got hard as he continued and had to reach below myself to get my stiff cock into a more comfortable position. That made my ass wiggle and Lou leaned down to my ear.

“You like it, don’t you, Luke?”

I did. I liked having my ass touched. Feeling his palm rubbing me. “Yes, Lou. It feels really good.”

“I can make you feel even better, Luke, if you’ll let me. I’d really like to.”

I knew that I could say no, but I wanted to please Lou. And anyway…

“OK, Lou.”

I said it in a tiny voice. But the words were huge.

“Turn over for me.”

I turned over, exposing my hard cock. His hand gripped it immediately.

“I’m going to give you a nice hand-job, Luke. Just lie there and enjoy.”

I closed my eyes and felt him dribble some more cream onto my cock and then he started to jerk me off. He was very good at it. Held me tight and stroked firmly up and down.

“I like your cock, Luke.”

Stroking. I was pleased that my friend liked my cock. His other hand reached between my thighs and cupped my balls as he stroked me. This was unbelievable. The school slut hadn’t done me this well. I spread my legs so he could hold my balls more easily. This led him to move his hand down more and I felt his fingers slip between the cheeks of my ass while he continued stroking my cock up and down.

I didn’t stop him.

I wanted to let him do what he wanted. So I helped him by spreading my legs even wider. Which Lou took for an invitation. I felt a fingertip at the opening of my ass. The sensation was enough.

“I’m going to cum, Lou.”

“Good boy. I’m glad you like what I’m doing.”

“Oh yes, Lou.” I looked up at him. “You’re making me feel so good” He stopped stroking. What??!

“No! Don’t stop! Please!”

“Don’t worry, I just need to ask you something.”


“Do you want me to make your cum even better?”

“Better than this?”

“Yes, if you trust me.”

“Oh yes, Lou. Whatever you want.”

“OK, let me know when you’re close.”

He started stroking again. I’d come back a little from the edge of cumming. Just enjoyed his hand around my cock. Up and down. A minute, no more, and I was back to the brink.

“Now Lou, I’m going to cum now!”

He stroked me faster, gripped my cock harder and I felt the fingertip on my anus pressed into me. He slipped a finger into my ass just at the moment that I came. Pushed deep into me and my cum shot up like a fountain, splashing back down onto my bare chest and belly. Spurt after spurt of cum as his finger went in and out of my ass. I didn’t know it could be like that. So intense. His grip on my cock relaxed and he slowly pulled his finger out.

I groaned. My body shook. My hips bucked involuntarily as the last vestiges of cum came from my penis.

Lou was by my side, leaning over me, when I opened my eyes.

“Did you like that?”

“Oh Lou. You made me cum more than I ever did before.”

“Do you want to help me cum now?”

I didn’t hesitate. To answer, I reached down and took his big, hard cock in my hand.

“Yes. I want you to cum, Lou.”

“Not like this, though, Luke. Did you like my finger?”

“Yes, it felt great.”

“Then I think you’ll like something else. You have such a sweet sexy ass. I want to fuck it.”

I wanted to make him pleased with me. Wanted to be like him. Wanted to repay him for the amazing sexual arousal he had just given me. I had to give him my ass. I said nothing and started to turn over so he could fuck me from behind. But he stopped me. “No Luke, stay on your back.”

He took the cream he’d been using before and covered his fingers. Kneeling between my spread legs, he started to really lubricate the insides of my ass cheeks and then began to push a finger into my ass.

I reached down and took my ass in both hands and spread my cheeks. My hole was open to him. Another finger went into me. He was looking into my eyes as his hand motion caused him to enter me deeper and deeper.


“Yes. I like it.”

I did. He was gentle and patient and I was going to let him fuck me. My older man crush. The more I looked up at him, the more I wanted him. After a few minutes, he had three fingers up my ass. In and out. Still checking on me. Was I ok? Still Yes.

“I think you’re ready for my cock, Luke”

“OH yessss. I want you to fuck me. I want your cock.”

I lay flat on my back and lifted my legs in the air. Looked down the length of my naked body to the naked man between my thighs. His huge cock in his fist as he leaned forward and aimed his meat at my slippery virgin hole.


“Do it! Put it in me.”

I stared down and watched. Felt the head of his penis touch the entrance to my ass. He pushed in a little. Felt him stretching my ass. Wider than the three fingers he had used earlier. So big. Fat cock in my ass. Penetrating me. A little further in and he took his hand away.

He was into me now and he kept up a steady pressure as more and more of his enormous meat impaled my ass. He took hold of my ankles and put them onto his shoulders. With my hands free I reached up and locked my fingers around the back of his neck. Pulling him down onto me and causing more of his cock to go up my bottom. He lowered himself further and further. Finally his whole cock was inside me and his face was touching mine. His cheek against my cheek.

He whispered. I felt his hot breath.

“You’re such a sexy boy. I wanted you since the day you joined the club.”

“Mmm Lou. I liked you right away. I want you to have me.”

He started to fuck me. Lifting his hips and withdrawing his big cock until only the head remained inside my body. Then down again. Thrusting into me.

“I want to kiss you while we fuck, Luke.”

I relaxed my hold on his neck so he could raise his head. His lips went to mine. I opened my mouth and felt his tongue enter it. His cock pumping into my ass seemed to take on additional urgency. His hands went around behind me. My legs were still on his shoulders, may arms around his neck. He lifted me up. Our lips never separated. And then he was standing. I was suspended in the air. His cock impaled in my ass and he bucked his hips over and over. Fucking into me. Holding me in his arms. If people on the beach had looked up they would have been able to see. Been able to see me getting fucked. See me with a big cock in my ass. I didn’t care.

He lay me back down. Started to really go at it. Pounding my ass. I rocked myself up to meet every stroke. I wanted my crush to have his pleasure. Wanted him to like me. We broke our kissing.

“Oh, Lou.”

“You like being fucked?”

I answered in time with his thrusts.

“Yes, yes, yes, yes, yes, yes.”

“You like my cock?”

“Yes, yes, yes, yes, yes, yes. You have a wonderful cock. I love it in my ass.”

“Do you want my cum in your ass?”

“Oh yessss.”

I bucked up harder and harder to help. Wanting him to shoot his cum into me.


He drove his cock hard into my ass. Grinding his hips around. Trying to get deeper. I felt him spasm and then his cum started to fill my ass. Gallons of cum. Like he had shoved a hose up my bum and turned on the spigot.

He grunted. Groaned. Twitched. Bucked. Bucked again. I rode it all out. Holding him tight and loving how it felt to have him cum in my ass.

At last, he calmed down. Let my ankles drop from his shoulders. He lay between my thighs. His cock still inside me. I didn’t want him to ever pull out of me. But he had to, eventually. I felt my stretched ass slowly close, some cum was trickling out. I knew I would never be the same again. We dressed and walked back to Lou’s car. I was bandy-legged. Thankfully I didn’t need to ride any more. Lou dropped me back at my house. I showered as soon as I got in. I couldn’t help myself – I had to masturbate in the shower. And I had to jam a couple of fingers up myself while I did so.

So I’d lost my virginity…. just not how I had expected. Lou and I go on rides together every weekend now. Sometimes we plan to but don’t get around to it. Why waste time? I just go to his place and he fucks the daylights out of me. He’s very considerate… he always makes sure I cum first. One day I will probably get to fuck a girl. But I’m not going to worry about it. For the time being I am going to enjoy taking cock from Lou.

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