Tag: losing his virginity

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by ccallenreese ♥ 0 Leave a Comment

I never show this photo to anyone. I quietly transfer it from computer to computer, phone to phone, but never show it to a soul. I think my face looks ridiculous but that is exactly how I felt that morning. I woke up and there was a cute, naked boy spread over my legs. It was that moment I remembered I was not a virgin anymore. I had slept with my boyfriend on prom night. I remember it being strange, and not what we expected it to be like, because we were so horny we couldn’t think straight. James seemed to know his way around his hole better than me, and he gave me great tips on how to stretch him. I think he was really really eager to be fucked by a real cock for the first time. I later found out James had quite a collection of dildos. 

But wow. Sex! I couldn’t believe I had done it. It was an amazing, visceral thing. And to top it off, I woke up with this adorable creature snuggling me like a koala. Even though I was 18 and my world was very small, I still think that was one of the best things to ever happen to me though. So hot, so torrid. Just how it’s supposed to be – a fumbling, sweaty fuck between lovey-dovey teenagers. 

I was awake before James was though and found myself pretty stuck. I didn’t want to get up. So, I did what I could do – take a photo. That was the first photo of me as a man. I was a boy no more. 

I wonder what James would think of this photo. Maybe I can find him on Facebook. He has a pretty distinct last name. Aaand there it is. Damn, he got even hotter in college. Oh hey, it says he’s single. Well that doesn’t have mean anything. I’ll just…send him a message here. He probably won’t – oh wow he responded right away. Hey James, how have you been?

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Text is fictional.

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by ccallenreese ♥ 0 Leave a Comment

pussyboytoy:

I checked my phone for the fiftieth time, already knowing that the room number was 1403. I was nervous as I crossed the hotel lobby, butterflies roiling in my stomach. The concierge smiled at me but, thankfully, didn’t ask me any questions. 

I pressed up on the elevator, fixing my hair in the mirror one final time, giving my lips a final swipe with my cherry chapstick, hoping that I’d live up to his expectations. That I wasn’t about to get turned away at the door.

I saw the room number on my first pass, but I kept walking deliberately down the silent, carpeted hallway, trying to pluck up my courage to knock. Standing in front of the door, I took a deep breath and knocked timidly. There was a pause that felt like forever, that made me want to turn around and speed back down the elevator. 

Then I heard footsteps and before I could run the door opened. Bald and muscly, just like his pictures. He was wearing black slacks and a white tanktop that hugged his pecs. “Hi,” I murmured breathlessly.

“You’re even cuter in person,” he said with a smile. “Why don’t you come inside?” He beckoned me in to the spacious hotel room, seating himself on one of the two armchairs. I moved to take the other one, but he shook his head, patting his lap instead. 

“So, you said you’re a virgin?” he said as I nestled myself, somewhat awkwardly, on his lap, not looking at him. I nodded, blushing. “That doesn’t make any sense,” he laughed. He wrapped an arm around my waist. 

“Ever kissed anyone before?" 

I shook my head, and he chuckled, wrapping his fingers through my hair, steering me to his mouth. It was warm. His lips slid over mine, engulfing them. I moaned softly. He broke off. “You’re a good kisser,” he smirked.

I nodded, averting my eyes once more. He felt him frown, running his hand through my hair. “You okay?” he asked in his deep voice.

"I… I’m not sure. I – I just, I never thought it would be like this.”

He looked at me sympathetically, tilting my chin up so that our eyes met. “If you want to go, that’s okay. Look, I don’t know you, but that doesn’t mean I wouldn’t like to.” He hugged me tight. “How about this: I’ll pour us some wine and I’ll let you pick a movie to watch. Then we can take a shower together so that you can explore. And then, if you want, I’ll carry you back to the bed, naked, and I’ll take your virgin pussy.”

I shivered and then slowly nodded.

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by ccallenreese ♥ 0 Leave a Comment

The first time we had sex, it was after 13 long, slow months of dating. Julian wanted to go further, but was petrified stiff. No pun intended. He wanted to set a date to lose his virginity. At his request, I loosened him up with craft beer and Jack Daniels, and also at his request, put a little GHB in his drink. Just a little. He also took poppers. To say Julian relaxed instantly was an understatement – he was on me, crazy horny, and dragging me to bed.

We got naked and he wanted me to take him – was begging me to take him, to fuck him hard – but I couldn’t. I just couldn’t. He wasn’t sober, and even though he’d consented, I wanted our first time together be real. He wasn’t going to remember this. He was never going to know how much of it was the drugs and alcohol and how much was love and passion. I was never going to know either.

So, I edged him and capped it off with an intense handjob. Julian exploded all over my chest, then promptly passed out.

The next morning, he was gone before I woke up. I couldn’t get a hold of him until 9 pm that night. I had texted him stating if he didn’t respond to me right goddamn now I was filing a missing persons report. Julian replied and asked to meet me at a coffee shop.

He picked an isolated table in the back. Before I could get a word out, he  begins to blather about how gross and disgusting he felt. He was headachey; he couldn’t remember most of the previous night and was regretting having ruined his first time. I kept trying to interrupt him but he just kept talking, so eventually I just put my hand over his mouth and said firmly. “If you just shut up a moment, I’d inform you that we didn’t have sex.”
“….What?” Julian’s face furrows. “I don’t understand – I remember being naked, cumming…”
“You were on aphrodisiacs, horned out of your mind. I gave you a handjob because you said you’d only not like them if you were dead. I had to get you off the edge. You passed out like, right after.”
He blushes. “But we didn’t…fuck? You didn’t penetrate me with your cock?”
“No. For the exact reasons you described above. Handjobs were always something you were fine with, but penetrative sex was another matter. Just because you consented before the booze and GHB doesn’t mean you still do after you’ve taken them. I felt like such a creep. I felt like I was going to rape you, the way you just were grinding on me like crazy. You wanted my dick, but I didn’t know if you really did, you know? I just couldn’t do it. I didn’t want to "do the deed”, I wanted to make love with you. You were fucking hot, but it was not what I wanted.“
Julian sits in silence, blinking like an owl at me. "But… how can I be sure?”
“No open condom wrappers. No sore ass. You’ve never taken my cock before, I would have stretched you first. You would have remembered that.”

“No condom wrappers…” He fights the indignancy he’d been building all day, then releases it all in an audible sigh. He collapses back into his chair, exhausted. “oh my god. I am so relieved. Just…Jesus fucking Christ, I was coming here to break up with you!”
“I know,” I say softly.
“God you are amazing. You’re the best boyfriend ever. I am so grateful for your thoughtfulness.”
I give him a warm smile. “It’s because of you. You’re the one I really want to keep and cherish. I’m… I’m really hoping we can try this again? I want to be your first, if you still want me…”

He sits up. “Yes! Yes I do. When it’s right.”
“When it’s right.” I put my hand on the table and Julian put his hand over mind. I told him I love him and he blushed again, before telling me he loves me too.

A week later, he was over for dinner-and-a-movie when a heavy storm knocked out the power. We had dessert and coffee in bed, surrounded by candles, and one thing lead to another… The next morning, the Earth was verdant from being washed clean and Julian woke up a man.

We’re still together. To this day, I still wrap an arm around him in bed. I’m not letting him run off on me again while I’m sleeping. I love when he spoons up against me and wiggles his butt into my crotch, accepting that he’s stuck and might as well get comfy before I wake up horny and come after his hot self.
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Text is fictional. Source unknown.

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by ccallenreese ♥ 0 Leave a Comment

“Ohhh fuck yeah, I’m in! – It’s in, it’s in, god baby you swallowed me right to the hilt,” I purr.
“Ah–ow ow! Nng!” he crunches his face up.
“Shit, that was a bit fast wasn’t it? Are you ok, babe?”
“Yeah just…nnng,,” he holds his breath for a long moment and releases it, panting softly. “Gimme a sec. You’re in. You’re actually in me. I ..can feel you, it feels huge.”
I smile. “You flatter me. Are you in pain?”
“No just…I need a moment to adjust. Feels good. Feels hot.” He pulls my face close and kisses me.
I return it slowly while watching his face contort. I can feel him clench and squeeze around me, making my dick swell even more. “Relax, just relax. You feel amazing, babe, like this thick velvety glove around me.” I nuzzle his face, nose to nose. “Can you feel it too?”
“Oh yeah…I can feel it throbbing, the pulse. I do that to you?”
“Yeah babe you do,” I chuckle. “I love you so much.”
“I love you too – there’s no one else I’d trust to do this with. God you feel so huge! Fuuu. There. It – …it doesn’t hurt so much anymore. Feels…kinda good, actually, to be full.”
“I can start moving?”
“Fuck yeah,” he replies, getting bold.
I capture his mouth in my own and pull out before pushing back into his body, pressing him against the cool glass of the window. A groan spills from his throat as his ass pulls me in. His swollen cock poking into my stomach dribbles pre-cum down the shaft with every thrust.

I waited two years for him to be ready for intercourse. I used to curse the days I was horny and had nothing to put my dick in, but I’d just tell myself it’d be worth it one day to wait for him. He had to be ready, he had to be horny, he had to offer himself to me; if I rushed it, I would spoil the moment and it’d be lost forever. I’m so glad I waited. My virgin lover has become a man today, not because I was horny, but because he asked me to make him one. He is spread open and hard for me, and taking him is as sweet as I always feverishly fantasized it would be.

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Text is fictional. Photo comes from Mr. Jones Films, and the men are Brandon Jones And Dominic Pacifico. More pictures and trailers at an unofficial link here. Original website is flash, so I can’t direct link, but it’s here.

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by ccallenreese ♥ 0 Leave a Comment

It’s 2 am and the party is winding down. I need to leave soon – 10 am classes and all –  but I can’t find my roomie anywhere. I’m a tad worried. I brought him here because I knew a lot of gay guys were gonna be here, and I wanted him to feel comfortable in his new-found sexuality. I’d never forgive myself if someone raped him, or worse, kidnapped him and then raped him. Gorram it, where is he?

I jog up the stairs to the second floor of this McMansion, cursing it’s unnecessary amount of rooms. Bathroom? Nope. Closet? Nope, just one pissed off cat. The first bedroom is emitting light from under the door. I open it and find a pile of girls asleep on the bed. Weird, but nope. I walk to the end of the hall and pause in front of the second bedroom door. Green light? Wait, that’s smell? Weed, oh that makes…sense.

I push the door open, bracing myself for the wave of skunky smoke and bewildered stares of stoned frat boys…. but what I see inside blows my mind. There was my roommate alright, and two other boys – one being my younger step-brother and the other I did not know – in the middle of an intense threeway orgy of frotting and fucking. My jaw drops. I can see someone’s dick but I can’t tell whose it is. Wow, they are really going at it. They didn’t even pause when I opened the door. Heat spreads across my cheeks and my cock twitches in my pants. Goodness gracious.

I pull out my wallet and remove the condoms I put in there earlier and set them on the nightstand. As I back out slowly. It feels like I’ve trespassed into the lair of some nocturnal animal and am trying to appease it with an offering while simultaneously not catching its attention. With great delicacy, I tip toe out of the room and coax the door shut, returning the doorknob to its resting position without a sound. For a moment, I just stand there absorbing it all.

“Congrats, buddy, what a way to lose your virginity,” I say under my breath, a little smirk on my face. I whistle as I trot down the stairs and head home alone.