Just This Once Ch. 01

Story Info
A troubled student gives into his gay desires and fantasies.
3.6k words
4.45
30.7k
45

Part 1 of the 3 part series

Updated 06/09/2023
Created 07/24/2018
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Jake was the star forward on the school soccer team. And I have been sucking his cock for several months now.

In the midst of senior year at Harboro County High School, with finals, graduation and college on the horizon, you'd think the salutatorian wouldn't find the time to obsess over a guy like some horny fan-girl. But then again, you'd think a lot of things.

My name is Matt. I'm a quiet, shy, 18 year old academic with practically zero friends. Despite my thin, "twink-ish" (one might even say girl-like) features, I did have a girlfriend up until recently, but like most things in my life, that didn't last long. And as I'd mentioned before, I'm in an intimate oral relationship with the star athlete and student-body president Jake Caldwell.

The Caldwells are a rich family from the north side of Harboro, and probably the sole reason our division taxes are through the roof. Jake Caldwell has money, looks, and charisma to spare. If you'd split any of those attributes in half to make two people they'd both still be moderately wealthy, attractive, well-spoken gentleman. Every girl in the school wanted Jake and I can see why. I didn't even think I was gay until I met him.

My debacle began 4 months ago. Back then seemed like an eternity ago, considering the things I'd learned about myself in such a short time. What I do remember is the old me. The me that wanted to please his parents, the me that wanted to surpass the valedictorian, the me that wanted to attend an ivy league college. The reserved version of myself that seemed to understand where I was heading. Some nights I lay awake thinking about what I'd give up to go back. And other nights...

What I can't remember is how I got here. I remember the events, but I can't remember the reasons...my headspace. There are several things to consider, none more important than the other. First, my parents divorced. This was 5 months ago. During winter break. It didn't really surprise me considering how much they've hated each other for years. But then my perspective changed when my girlfriend, Kaitlyn, asked me to have sex with her. And I refused. I'm a virgin still (all things considered), but the timing didn't seem right. I was nervous, and my mind was elsewhere. She didn't talk to me until a week later when she broke up with me. And all those thoughts I had of being better at love than my parents dissolved.

The Monday after she dumped me (after spending all weekend looking at her social profile pictures of her partying and kissing other guys) I got a B on a test. Not enough to lose my rank but enough to guarantee I'd never be valedictorian. I remember a lot of sadness and anger. And then emptiness. My entire world crashed.

And then I remember Jake.

It was a sunny afternoon, great for sitting on the bleachers at the soccer field until I was sure my mother had fallen asleep at home. I did what I usually do. Listened to music, did homework, stared off into the clouds etc. The only thing different today was that soccer practice had been cancelled. I saw the sign on the door as I had passed. "Great, then I should have the field to myself," I remembered thinking. That was when I heard a voice. "Did my practice get cancelled?"

I had seen Jake in the hallways before. I had noted that he was handsome, but we never really crossed paths and I didn't put too much thought into him. But somehow this was different. He stood there, his back to the sun with a radiant warm glow in the afternoon heat. His face was perfectly symmetrical, and his chin was gorgeously chiseled. His green eyes had a stern but soft expression. His nose was sculpted like a Greek statue and his lips were widely pillowed...kissable even. His brown hair fell messily, but stylishly, down to his brows and stuck to the sweat on his forehead. His neck was narrow and had a distinct Adam's apple that bounced up and down when he spoke. His broad shoulders made a divot at the neckline and proceeded down to his defined musculature. His forearms bulged with veins and his large, slender but strong hands were rough and much bigger than mine. He wasn't overtly buff or beefy, but he had achieved this equality in his fitness. Almost like seeing him run a marathon or benching 200 lbs would not be out of place. His defined washboard abs were rigidly visible under his practice jersey, and his thighs bulged out under his soccer shorts. As did something else. Even his calves were noticeably toned in his long socks. If I had to describe the perfect male body, I'd use Jake as a reference. That's how handsome he was. I felt like a tiny frog in the shadow of this harmonious god. And I was unbelievably jealous of him.

After staring at him for way too long I managed to mutter, "Yeah, there was a sign on the door."

He blinked at me for a moment. "Damn, that's what I get for leaving my stuff in my car. I was running late this morning" he admitted, making him seem pleasantly more human.

"You sit out here a lot. I noticed last time during my water break. Are you on the second string?" he asked.

"N-no, I don't play sports. I just like how quiet it is out here." I knew my point was easily debatable but it was too late to change it and I was too tired to care.

"Can't argue with that!" He smiled. "What's your name? I'm Jake."

"I know who you are," I replied in the friendliest tone possible. "My name's Matt."

"Oh, I think I know you. You're the valedictorian, right?"

The word made me cringe a little. "Salutatorian" I said, expressionless.

"Same difference. Way smarter than me," he said. It was hard not to like him. "Mind if I sit? I have an hour and a half to kill."

For anyone else I would've said no. But something about him made me want to be his friend. Which is strange because I purposely had no friends. "Sure," I said.

And we sat. And talked. For like an hour. It was easy to open up to him. And he was a good listener. I told him about my parents, and Kaitlyn, and my grades. He seemed genuinely sympathetic. He told me about his girl troubles (which weren't really troubles in my opinion), which included many sexual encounters but no love. He also opened up about feelings of being liked only because of his looks and money and position on the soccer team. While it was hard to sympathize with him, I guess it made sense from his perspective. Then he asked me something.

"Why didn't you want to sleep with your girlfriend?"

I thought for a moment. "I wasn't ready. It was all so sudden and my parents had just gotten divorced."

"Were you attracted to her?" he asked, raising an eyebrow.

"...yes"

"You hesitated," he said.

I thought for another moment. "No," I admitted.

"Are you gay?" he asked.

"I...I look at gay porn sometimes." I wasn't really sure why I was telling him these things.

"Me too," he said.

My face went blank. I was in awe. I feel like I had been told some forbidden knowledge. Here I was comparing him to a god and he was scared and unsure like me in many ways.

"I feel like a sexual deviant sometimes. My parents would disown me and coach would kick me off the team if they found out the things I've done," he said.

"What things have you done?" I asked, surprised to find myself intrigued.

"Sometimes I look at the other guys when they shower. And a few times I've stayed behind to sniff their jock straps," he admitted.

The conversation had turned flirty in the most awkward of ways, and I can see a weight being lifted off his shoulder for telling me that.

"What about you?" He asked.

I thought for a moment, unsure if I should say anything to him only to find out he'd hit record on his phone and planned to send the audio of me admitting perverted things to everyone. In a moment of "nothing-to-lose" mentality I answered.

"Sometimes, I watch straight porn, and imagine I'm the woman. I even put on my mom's lingerie and makeup while I do it and masturbate like a girl."

"Woah, really?" he exclaimed, excitement in his voice. "To be honest, that's kind of hot."

I could feel my cock grow a little bit in my pants. I was shocked when I recalled whom I was talking to. I could feel my face blushing beet red.

"You're really cool to talk to," he said.

The butterflies churned in my stomach. "T-thanks...you're really cool, too."

"Can I ask you something?" He spoke cautiously now.

"O-ok," I said nervously. I felt like a boy in a romantic movie asking a girl to prom.

"Do you want to fool around? Just this once? Like, get it out of our system?"

I stared at him. "I can't say that I don't want to, but I kind of wanted my first time to be with a girl," I said glumly.

"That's ok. We don't have to have sex. It doesn't count unless there's penetration." He sounded reassuring.

I thought long and hard. He seemed truly genuine. But this was risky. He could take pictures of me. He could lead me to a secret locker room where the entire soccer team was waiting to beat me up. I couldn't.

Before I spoke, he grabbed my hand. "Come on!" he whispered loudly, before hopping off the bench. He pulled me down the bleachers like a kid with a balloon. My heart began to race, and I couldn't stop smiling. I wasn't thinking, I was doing, and so was he. We didn't say anything, but we both were thinking the same thing: this was dirty, exciting and surprisingly fun.

We got to the bottom of the steps, and then Jake stopped and looked in every direction to make sure nobody saw. His grip was firm. My hand felt soft and tender like a girl's in his, which gave me goose bumps.

"Under here," he said, gesturing to the bleachers against the exterior wall. We snaked through metal bars, ducked under cobwebs, and stepped over cigarette butts and used condoms before we reached the center. Here, we would be completely secluded, so we would have plenty of time to hide if anyone came. Not that the thought of getting caught didn't turn me on.

After making sure we were completely alone, I spoke. "D-do we kiss?"

Jake pinned my chest against the wall, his forearm planted against my back almost like he was arresting me. He oozed authority and dominance, so it was easy to follow his lead. He ran his hands down my body and planted them on my ass for a full on, embarrassing grope. He leaned forward to whisper in my ear.

"Do you want to be my secret girlfriend?" he said in a sexy low tone that sent shivers through my body. My dick stood to attention. Not thinking, I nodded, finding myself intensely aroused by the objectifying character he was playing. I thought it best to comply and act submissively. "Get on your knees."

It became vividly clear Jake had done this sort of thing before... but probably not with a boy. I dropped to my knees, looking up expectantly at him, wondering if he knew what to do next. He pulled his soccer shorts down to his knees, exposing his grey tone sports boxer briefs. I could see the outline of his dick, and while I couldn't make out its length I was certain it was incredibly fat and thick. The smell of him was intoxicating. I remember thinking about a documentary about compatible pheromones in breeding animals, and concluded that must be the case here.

"Press your nose against it," he said in a commanding voice. His demeanor had changed, and I quickly realized this must be the way he acts during sex... confident, stern, in complete control. I would not be surprised if it made the girl's he's been with soaking wet. I inhaled his musk and my back shivered and my head became light, like smelling a permanent marker. "Take it out," he said, almost meanly.

My stomach turned in knots from the nerves. Up until this point, what I've done could be classified as strange. But we were rapidly approaching the point of no return, and I was keenly aware I'd live with it for the rest of my life. But I didn't want to stop. I pulled his waistband down, revealing a defined "V" connecting his abs to his pelvis, covered in small, masculine, well-groomed patch of pubic hair. My heart felt like it was going to beat out of my chest.

Jake grinned at me, running his fingers through my hair, and the longer this went on, the harder it became to consider pulling away. Then, his semi-hard cock bobbed out, nearly planting itself on my nose. I recoiled.

Jake's cock was big. At least 8 inches, and it made me feel very insecure about mine. It was thick too. About 5.5 inches in circumference, I would guess. The light pink tip was a perfect mix of round and angular, great for jabbing the hole AND caressing the insides. As far as penises go, I would say it was ideal. Clean, circumcised, appealing, not deformed or strange looking in any way. And it was veiny, too! The thing practically pulsed in tune with his heartbeat. I almost felt flattered I was considered worthy to see it. Why did I think that?

Beneath the cock swung two gigantic balls, and when I looked at them I felt strange. Like I was a girl who'd never seen them in real life, despite being attached to two of my own my whole life. The thought made me feel giddy and excited like a virgin girl in an 80's movie.

"Go on, don't be shy. Touch it," Jake said. My own cock was rock hard listening to his dominant voice. This was hot.

I bit my lower lip and raised my dainty hand (which was about ¾ the size of his dick) to it. The heat from it radiated off warming my hand, like a pot of boiling water on the stove. I wrapped my fingers around the shaft.

~That's it. I'm bi now~ I thought to myself. ~I can never take this back. I'm touching another man's penis ~

"Good girl," Jake praised. "Why don't you stroke it a bit?"

I did as he said, stroking the shaft up and down slowly. His sheath felt like warm silk in my girly hands. Sweat dripped off his balls as they bounced and shook. I became aware of the afternoon's heat once again and felt the sweat in my armpits. The only sound was the shaking of the trees in the spring wind and the low hum of summertime insects in the surrounding woods. We were completely alone.

After awhile, the cock started to sound wet, and began making a squishing sound. The tip began to leak a clear liquid: pre-cum as Jake explained. I knew I had made it before but I don't remember paying much attention to it. Usually it just pooled in the pair of my step-mom's panties I was wearing. Now I had an up close and personal view, taking in every detail of Jake's cock so that I could apply it to my jack-off sessions later.

I instinctively leaned forward and pressed my lips to the tip of his cock, like trying to prevent a soda from fizzing out of the can. That was obviously the correct next step because Jake let out a low-toned moan in response. I kissed his tip, tasting the salty pre-cum for a moment before I felt Jake's hand on the back of my head, urging me to put more in my mouth. By now, the pressure in my pants had become unbearable, and as I held on to his cock slowly lowering my lips onto the upper shaft, effectively sucking my first cock, I took my free hand to unzip my jeans and let my oppressed cock out of my pants. Seeing me begin to take my pants off, Jake moaned in approval.

"Take your pants off, I want to see your ass."

I obliged, taking a brief moment to completely remove my pants and my shirt leaving me in my boxers. Unsatisfied by the view, Jake bent over me and grabbed me by the fabric of my boxers and stuck his finger in an old hole on the back leg (I always get cheap clothes and my underwear is no exception). He began to tear the fabric around my thigh until half of my ass cheek was visible. He did the same to the other side, effectively making a makeshift pair of booty shorts that clung to the crease of my ass allowing my cheeks to stick out.

"Damn, you've got a nicer ass than most girls at this school!"

I felt a little proud and turned on for meeting Jake's expectations. I resumed sucking his cock, bobbing up and down on about half the shaft. About halfway through the blowjob, some thought occurred to me: Jake was playing up his role to satisfy my fantasy. I thought it only fair to return the favor. I began to emulate what slutty girls did in the porn I watch. I arched my back and sucked my improvised panties into my ass crack to give him a nice view of my girly butt. I felt extremely naughty.

I opened my mouth a little, sticking out my tongue and allowing his cock to rest on it as I smiled up at him, teasing him a little. He seemed to really like it.

"Oh, so you're a dirty slut, aren't you?"

Jake grabbed my hair and began fucking my face in earnest, his balls slapping my chin with each thrust. I relaxed my throat and breathed through my nose to avoid gagging, but once again proud of myself for taking all 8 inches on my first try. Jake's skull fuck began to speed up and so did his grunts.

"Oh fuck, oh fuck, oh fuck!" Jake screamed as I felt an extremely hot sensation at the back of my throat. It felt like hot yogurt. I guess that would classify as a deep throat cumshot if we had filmed it for porn. Jake held my head firmly in place until every last drop escaped the tip. The orgasm shot spurts at first, and then thick globs that rolled down the back of my throat like syrup, making my whole body feel warm. He stayed there a moment, breathing heavily.

"Fuck that was so hot," Jake finally said after a minute. "Sorry about the underwear, I just really went for it in the moment."

"It's ok, they're old anyway."

Jake laughed. "Still, I promise I won't do it next time."

He pulled up his shorts. ~Next time? I thought it was just this once? ~ I thought to myself. Before I could protest, Jake looked at his phone.

"Oh shit! I gotta go. Thanks for the good time I really needed it. Meet me here tomorrow so we can do it again!"

Jake ran off, weaving the metal poles of the bleachers towards the parking lot. A little flustered and confused at the situation I only managed to mutter "Sure."

And then I sat there. Practically naked. Another man's semen in my stomach. And I was still hard as a rock. He didn't touch me or reciprocate the blowjob at all. And that was probably the hottest part to me. I felt like a dirty whore. I leaned back and began masturbating feverishly to the thought of what had just occurred for at least fifteen minutes, erupting into a river of cum onto my bare stomach. When I came to my senses, I got dressed and grabbed my things to go home, trying to shake the thought.

'I'm not gay...it's just a fetish," I said to myself. "I'll come tomorrow not to hurt his feelings, and I'll tell him it was a one time deal." I hopped in my car and drove home. I ended up masturbating like seven times that night.

That was four months ago. I give Jake a blowjob about 4 times a week now. It's usually the same. The place and the time change. Sometimes he cums on my face instead of in my throat. Sometimes I bring a pair of panties in my backpack. Sometimes I wait for him after practice and he makes me clean his sweaty balls. But it's always a blowjob, and nothing else. He cums, he leaves, and then I stay behind to masturbate. It never goes any further.

"It's just a bit of roleplay fun," he tells me. "It's our dirty secret."

I don't really care. I've gotten used to it. It's like an itch. Once I scratch it, I feel so much better. We don't really talk anywhere else. If we make eye contact in the hall, he smiles but not much else. And no one suspects. Why would they?

Every once in awhile I hear girls gossip about how hot he is and how much they want to fuck him, and I just smile. Smile because the hottest guy in the school violates my mouth and not theirs. It fills me with filthy pride.

Prom is coming soon. I don't know who to ask. There's only one person I'd want to go with. But that won't happen. Am I gay?

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6 Comments
AnonymousAnonymous5 months ago

Very hot, would love to have Jake getting caught sniffing his soccer mates jockstraps and him being turned into the cock sucker.

AnonymousAnonymousover 4 years ago

sounds nice just once , but then it was such a nice experience, i could see myself wanting to continue sucking his nice cock and feeling like a naughty girl.sometimes it's nice to be naughty.

stacejostacejoabout 5 years ago
Hott....

Love it want more.....

AnonymousAnonymousalmost 6 years ago
Great story

Can’t wait to read more. Really hot. I also agree it’s in the right category. The best TS stories start off slow with the cross dressing themes.

GundamXDGundamXDalmost 6 years ago
Great start!

I disagree with the other comment, considering Matt talked about crossdressing and wanting to be like the girls in porn. I’m hoping Matt fully crossdresses for Jake later on and gets fucked. Looking forward to the next chapter!

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