Ollie the Virgin Femboy

This one was written for a friend. He knows who he is. 

I sat with a black Americano and my iPad in my usual seat by the window. The girl behind the counter was warming a croissant for me and would bring it over in a few minutes. This was my favourite coffee shop. My little secret, hidden away on a side street in London.

It was never very busy here and I liked that. Today for example, there was an older guy sitting by himself in the middle of the room with a newspaper and at a table in the furthest corner from the door was a group of three boys, probably around seventeen or eighteen, who were engaged in whispering and giggling. It was empty but for us.

The boys were all pretty cute from what I could see at this angle. One of them seemed quite beautiful and I couldn’t help but keep my eye on him. He had a fantastic shy smile and long dark wavy hair. He managed to pull off feminine and handsome at the same time. His eyes shone even at this distance.

The pretty girl brought my croissant over and as she set it down on the table, a skinhead came into the cafe. He was loud and obnoxious from the start. The archetypal bully boy, I knew the type. The girl went to serve him. He messed her around with his order and then again when he paid. He took an interest in the three boys in the corner and went over to them, leaning over the table and clearly intimidating them. He flicked the older guy’s newspaper as he crossed to where the boys were sated.

The older guy got up and hurriedly left, clearly wanting to avoid any drama. The serving girl was trying hard to look busy so she didn’t have to engage with this asshole.

Suddenly the skinhead had one of the boys by his neck, pushing him back and up against the wall. There was a screech of chair legs on the tiles floor and a clatter as a couple of spoons were swiped off the table and hit the floor.

I jerked my head up. It was the pretty boy. I couldn’t hear what was being said as the skinhead was speaking quietly to him. The other two had gone silent and pale, sitting back in their chairs and clearly petrified.

I rolled my eyes. So much for a quiet Saturday. Unfortunately I wasn’t the sort of person who could just sit there and watch these cute boys get bullied. I just didn’t have it in me to do that. Besides…… it was the really beautiful boy, so I had to do something.

I stood and took my plate over to the counter and handed it to the girl. I winked at her, sat myself at one of the barstools at the end of the counter nearest the three boys, and spun around to face the group.

“Hey guys!” I said loudly, as cheerfully as I possibly could. “You guys look like you’re getting close!” I smiled and gave a little chuckle. The two boys who were still seated glanced at me, then back to their friend.

The skinhead turned his head to me, one hand firmly around the beautiful boy’s neck. “Look at this little cunt!” He said. He pulled at the boy’s trousers, which came down just far enough to reveal he top of some pink and cream striped panties that were tied at the hip.

“Oh wow, they’re nice!” I said. Suddenly these three made sense. A trio of femboys, I guessed. The skinhead must have seen a flash of pink or something and gone straight down the road of some homophobic bullshit bullying. Typical.

“What’s that?” The skinhead said with a sneer, taken aback at my comment. I noticed the two seated boys look at each other in surprise. Their expressions screamed “what the fuck is going on now?”

“They’re femboys?” I said. “I assume you like femboys, right? You trying to get a kiss or something. This boy playing hard to get?” I smiled broadly and shot a wink at the the other two.

The skinhead let go of the boy, his masculinity offended. “You fucking what?” He said, now turning his attention to me and glaring.

I’d had enough already and couldn’t be bothered to finish the game that I had started. I stood up off the barstool and took a half step closer, close enough to show I wasn’t afraid and could even be a little intimidating myself. I was taller, and while this guy looked stockier than me I could see it was mostly fat.

“Listen, dickhead. I’m not impressed by your homophobic bullshit and nor is anyone else. I think it’s time you left.” I said softly.

“Or you’ll do what?” He sneered.

I smiled at him. “Or I’ll knock you so flat you’ll have to roll down your socks to shit?” I replied. One of the two boys, the little blonde, sniggered at that.

The bully took a lazy, badly timed and poorly aimed swing at me. It was easy enough to step aside and catch his arm on the follow-through. I allowed his own weight to spin him around so that he was up against the counter. I pushed his arm far up behind his back, twisting it and bending it the wrong way. He cried out in pain.

“I’ll give you two choices” I said as calmly as I could. “You either fuck off or I’ll break your arm so badly you’ll remember me every time it gets cold or rains. You get me?”

“You wouldn’t fucking da.....”

I applied a little more pressure, shutting him up immediately. He was desperate to shout out in pain but he dare not. I pushed a bit more. I needed him to know I would, and I could.

“Okay....okay.....alright I’ m going” he cried out.

I ushered him toward the door, one hand on his shoulder and the other still grabbing his arm. As we got closer I gave it one final twist, just enough to ensure it stayed sore for a day or two. “This is where I drink coffee. If you come back, you’ll really piss me off.” I growled. I let go and watched with glee as he ran the rest of the way to the door and got the hell out of there. I noticed he was halfway down the street before he even tried to straighten his arm out.

I turned my attention back to the boys. I was greeting with a cacophony of “thanks mister” and similar from the boys and the girl behind the counter.

I handed the girl my card with my number on it. “If he comes back, just message me.” I said. She blushed and nodded.

“Let’s refresh their drinks” I said, gesturing over to the boys “What was it, hot chocolate? I reckon they could do with the sugar after that. I’ll have an espresso, please.” The girl got busy with the order. I helped the beautiful boy to sort his chair out and get seated. He was trembling and he had a red mark on his neck. The blonde boy was smiling now, his adreneline having kicked in, but the third boy seemed terrified still and he was as pale as a sheet.

“Don’t worry boys. He’s gone. And he’s not coming back. You ok?” I said to the prettiest of them.

“I think so” he said a little shakily. “I…… I wasn’t expecting something like that……”

“You really fuckin’ showed him!” The blonde lad blurted out. He had an American accent. It just made him all the cuter.

“So what do we have here?” I asked as I pulled up a chair and sat. “You’re clearly British, you’re American….. and you…..?” I looked at the third boy, with the darkest hair and palest skin. His eyes were still wide and he looked really worried. I figured he was in shock.

“American” he said, but he didn’t elaborate.

“These are friends of mine” the beautiful boy said. “We met online. You know….. gaming?” I nodded. “We all like….er….. you know……” he trailed off.

“Dressing up?” I offered. The boy nodded, blushing and going shy on me. It was adorable.

“I live in London. These two flew over to spend some time here during the holidays. I thought we’d be okay in London of all places……”

I nodded. I was sympathetic. “I understand. But don’t let one arsehole spoil your fun. He’s gone. Not coming back. What do I call you guys?” I asked, trying to keep things light and just wanting to make sure they were all okay.

“I’m Ollie,” the boy said. It suited him. God, he was attractive. “And this is Mitch and Dale” and he gestured to the blonde and the dark haired boy respectively.

“Now what do we do?” Asked Mitch. “He won’t go out now. Look at him…” he tipped his head to Dale and rolled his eyes.

Ollie frowned and looked sad. “I don’t know. Maybe go find somewhere to hang out on our own?” He suggested. Mitch looked underwhelmed at the suggestion.

I suddenly wanted to intervene. I had the urge to make the day better for these boys. I must admit I had an ulterior motive in that I was not averse to spending more time with young Ollie, but my intentions were true.

“Hey, my apartment is literally around the corner, opposite the park. If you want, you guys can come to mine for a while. I can look at that mark on your neck, Ollie. Maybe Dale here just needs a little while to get over our meeting with the local caveman and when you’re feeling better you can all go do whatever…..maybe spend some time in the park? We can maybe play some board games or something……. Unless that’s too boring for you three……?”

Ollie and Mitch exchanged glances. Mitch slowly started to grin, but Ollie seemed unsure.

“I know, I know…. Don’t talk to strangers….” I said with a grin. “I promise I’m not an axe murderer. If you like you can have my card? That way you know who I am and maybe you can tell someone where you’re going for a few hours?”

Ollie seemed to quickly make up his mind. “No, that’s okay. You don’t seem like a murderer!” And he grinned. It was the most beautiful, shy grin in the world. “But are you sure you don’t mind? I mean, we’ve already ruined your Saturday……..” He added.

I laughed. “I’d love the company, I promise.” I said. “But It’s either TV or board games because my console is broken.”

Ollie smiled warmly. “That’s ok. We like board games.” He said.

The rest of the morning was great fun. We played a variety of board games before settling into a mammoth game of monopoly at Mitch’s insistence. I applied a little cream to Ollie’s neck and by the time we ordered lunch to be delivered, the mark had all but faded away. We carried on until late afternoon. I could barely take my eyes off of Ollie, who seemed to go coy and shy whenever he caught me looking. Mitch was a terrible flirt with everyone and spent the entire time making innuendo about anything and everything, but he was a lot of fun and if Ollie hadn’t been in my eye line I’d have fancied the pants off him. Dale became less withdrawn too, but it was clear that he was the nervous one of the three and the least comfortable. Still, he made a good attempt to join in the fun.

When the game finished and Mitch was crowned winner, I went to fetch everyone more hot chocolate. Mitch offered to help and trailed behind me. As we were heating milk and getting mugs ready, I decided to ask some more personal questions.

“You mind if I ask.....” I started, but he interrupted me.

“The femboy thing?” He asked with a huge grin, somehow guessing what had made me curious. “Sure, ask!”

I laughed. “Okay, yeah..... the femboy thing. All three of you?”

“Sure” he said. “Ollie is pretty cutsie, Dale is like a doomer goth femboy.”

“And you?” I asked with a grin.

“I’m the real cutie. I do fem real well.” He batted his eyelashes at me before throwing a question back at me. “You gay then?”

“Well..... sometimes. I’m bi or maybe pan I guess.”

“I figured. Don’t worry, I’ll stop flashing my eyes at you. I know you only have eyes for someone else....” and he grinned again.

“Oh?” I asked, but I blushed and gave the game away.

“You fancy Ollie. It’s as plain as the nose on your face. It’s okay. Shame, you’re kinda hot. And I’m way more experienced than he is”

I really laughed at that. “Well, you’re kinda hot too” I said, mimicking his accent. “And i do kinda fancy you too.”

Mitch grinned, poured the milk and picked up the tray. “Nice of you to say so. Hey, you know Ollie has nowhere to sleep tonight.....?” He winked at me, turned his back on me, and walked back to the living room where the others were waiting.

I raised my eyebrows at that. Was Mitch trying to set me up with his friend? I wandered back to the living room where the three of them were whispering and giggling like they had been back in the cafe.

“Do you guys want some time to...... talk or whatever?” I asked.

“Oh, no, sorry!” Said Ollie. “It’s your apartment! That was rude, sorry!”

“We were just talking about what we do next” said Mitch. “Dinner and sleeping arrangements.”

“You have plans for dinner?” I asked. “You really are welcome to stick around and I’ll order. There’s a pretty good Five Guys near here that delivers.....?”

“You’ve already done way too much!” Said Ollie and Dale nodded.

“It’s entirely up to you, but it’s really no problem. I’d only be here, alone, if you didn’t stay. And I had great fun today, so I owe you.”

Mitch piped up. “Well I’m up for staying if you guys are. But we did say we’d show each other our gear…..” Ollie went red again as did Dale, but Mitch ploughed on with that sloppy grin on is face. “So maybe our new friend here won’t mind if we get changed into our femboy gear. Maybe he can rate us or something….”

I jumped right in. “That’d be cool by me…… if you want to, that is?”

They all exchanged glances. Eventually Ollie said “Hey, I’m up for it if you are. Dale…..?” The dark haired boy finally rolled his eyes and agreed, but he was smiling so I assumed he was cool with it.

And so the evening continued. The boys used my spare room to get changed into their femboy outfits and we had a weird but entirely brilliant dinner of Five Guys, ice cream, and the most incredibly sexy costumes I’d ever seen. I was practically nursing a hardon all night.

Dales wasn’t really my type in his black gear, with black leather garters and choker, but he was undeniably sexy. Mitch, on the other hand, was a stunner. He wore a soft shade of pink and was a girlie as it was possible to be. His pleated pink skirt was scandalously short and he took great pleasure in showing his very skimpy cotton panties at every opportunity.

Ollie, however, was where I focussed my attention. He was wearing a short light blue skirt, thigh-high cream-coloured stockings, a cream blouse, and every now and then I got a flash of soft cotton panties in pink and cream stripes. He looked totally adorable with his shining eyes, his soft shy smile, and that long, wavy brown hair.

Eventually Mitch called things to a close. “Guys” he said. “We gotta shoot. If me and Dale aren’t back at the hotel on time my father will hear about it and I’ll never hear the end of it.” He made a face. “But Ollie, I checked…. There’s no way you can stay in one of our rooms without paying cash. If we have another person to stay there’s a charge and you know my father checks every receipt.” He tried to look sorry, but there was a twinkle in his eyes.

“Now you tell me!” Said Ollie. He didn’t seem angry, more frustrated.

“What’s going on?” I asked.

Ollie looked over at me. “I was supposed to staying in one of their rooms tonight. Mitch’s dad is loaded, so he’s paying for the trip and rooms.”

Mitch chimed in. “Trouble is, there’s no way to stay in the hotel without another charge and I can’t explain to my father why I had someone with me. It’s….er….. well it’s not my first rodeo and I’m already on my last warning. I’m out of excuses. I’m really sorry!”

Ollie looked incredibly sad. “It’s not your fault. I guess I’ll have to try to find a train home tonight instead of tomorrow night. It’s going to cut out time short, that’s all. I guess it can’t be helped.”

“Hey, why don’t I get you two an uber back to your hotel, and Ollie can stay here overnight?” I suggested. Ollie flushed red again so I quickly added “I have a perfectly good spare room. No charge to stay if you make me a coffee in the morning! And then you guys can do whatever you want tomorrow as planned.” I smiled. It was a genuine offer, but I did like the sound of some alone time with Ollie. Not that I expected it to go anywhere, but a guy could flirt, right?

Ollie seemed unsure but once again Mitch jumped in. “I think that’s a really generous offer and a terrific idea! I mean, you don’t mind? You’ve already been so generous with your friendship!”

“Listen guys, I’ve had more fun today than I have in years. I really appreciate you hanging out with an old guy like me. It’s been great. Of course I don’t mind. What do you think Ollie? No pressure. I totally understand if you don’t want to.”

Ollie sheepishly looked up, met my gaze with his, and then smiled. He nodded. “Okay” he said. “If you really don’t mind, I’ll stay and then tomorrow we’ll find some some way to pay you back!”

Dale and Mitch got changed again and I ordered them an uber. Ollie showed them out. I noticed he had kept his girlie gear on, which pleased me greatly.

He turned back from the front door as I was stepping into the hallway from the kitchen. Our eyes met again and he blushed, went all shy. “Hey” I said. “You want me to show you where you can sleep and everything? Make yourself at home, okay?”

“um…..” Ollie started. “I’d really…… is there any chance…….You see, the thing is…….. I don’t really like sleeping in strange places and stuff on my own. Is there any chance I can…..”

“Sleep in my room? Sure!” I said. I don’t mind.

“Okay, great!” Ollie said. He was suddenly beaming. “Only thing is, I don’t have anything to wear in bed……”

“That’s okay, I can find you a t-shirt and if you don’t mind wearing them, I have a pair of boxers that I bought that were too small for me. They’d still be big on you, but better than nothing?”

Ollie smiled shyly at me. “Oh” he said. “Okay. Thanks”.

I suddenly kicked myself as I realised I had missed something there. That was either an opportunity or an opening and I really wasn’t sure which.

Later that evening I tossed one of my t-shirts over and Ollie caught it. “I’ll find those boxers….” I said, wondering where I had stashed them.

“Well…..” He said, that shyness coming through again. “Um, I might just wear my, you know….. these panties to bed?” He said. “I haven’t worn them all through the night before. Is that okay? You wouldn’t mind…..?” He blushed again. Christ, this boy melted me.

“Of course I don’t mind!” I said with a smile. “You wear what you want. But if I end up staring it’s you fault, okay?” I added, laughing. I was trying to make light, but if this boy was going to wear his pink and cream striped panties to bed with me, I was looking. No doubt about that!

Ollie smiled. It was captivating. “You’re so kind” he said. “We’ve got to find a way to pay you back.”

I shrugged, not really knowing what to say. To break the awkward silence I pointed to my bathroom. “Bathroom’s there. I’m all done. I’ll get into bed and you get ready, okay?”

Ollie closed the bathroom door behind him and I stripped off. I wondered whether I should try anything with him and decided against it. He was altogether too sweet and innocent. I decided that I’d look, but not touch. I also decided that I would carry on as normal. I always slept naked, and I decided it was a big enough bed - it was actually two doubles pushed together - that he wouldn’t see anything and that I’d be up and about before him anyway. I jumped under the covers and waited.

Eventually Ollie finished in the bathroom. He had spent a very long time in there. He literally scampered all the way to the bed, gripping the hem of his t-shirt the whole way. I chuckled as he flung himself under the covers next to me. I pushed the button on my nightstand and the lights dimmed to their lowest setting.

We both lay there in silence for a while, maybe fifteen or twenty minutes. Ollie was a fidget and he gradually got worse, shuffling around as if trying to get comfortable. I got the sense he was working his way up to ask something and eventually he turned onto his side, facing me in the dim light, and said “Um….. can we cuddle?”

My heart skipped about ten beats. “I’d like that, but are you sure?” I asked.

“Y….. yeah.” He said, sounding anything but sure. I didn’t speak. I wanted him to continue and eventually he did. “I…..er…..I kind of like you, but…… you know……”

I smiled. “What do I know Ollie?” I asked. I wasn’t trying to be difficult. I just didn’t want to make any assumptions here.

“Well….. I’m not very…..um….. experienced.” He said.

I propped myself up on my elbow, looking across at Ollie’s beautiful features. His hair had fallen across his face and over one eye lending him a sultry look. “Are you a virgin?” I asked.

Ollie’s eyes went wide and I guess I had hit the nail on the head. “It’s okay to be a virgin,” I quickly added. “There’s no shame in that!”

Ollie recovered, put a hand over his face as if trying to hide from me, and said “Yeah. Yeah I am”

There was a long silence. I decided to wait, to show patience. I didn’t want to scare this amazing boy away.

“The thing is, I’m ready. Or I think I am!” He said, his voice soft and thoughtful, almost mesmerising. “I’ve known I liked boys…. well….. men….. for ages. Since I was about ten actually.” There was another long pause as Ollie thought about that, reflecting. I could just make out a tiny frown creating a little v-shape above his nose. It was cute as anything.

“I always wanted someone to….. to treat me nicely. You know? To kind of sweep me off my feet and treat me like a princess and just be nice….. and then hold me and we’d cuddle…… and maybe other stuff after that. It’s sort of my dream. And then you came along today and you kind of rescued me, and you’ve been sweet and fun and you’re not bad looking for an older guy…….”

I burst out laughing at that. “Thanks!” I said. “Best compliment I’ve had in years”

“Awwww I didn’t mean it like that!” He said. He shuffled closer to me, moving the covers so he could get his body next to mine. He reached out to touch me and take the cuddle that he wanted, but he flinched back.

“Oh! You’re naked!” He exclaimed

I chuckled again. It had slipped my mind that I was here naked. I was always naked in bed. And genuinely, I wasn’t expecting cuddles. “Yeah, I sleep naked. Sorry….. maybe another time?” I said, resigning myself to the fact that cuddles weren’t happening tonight.

To my surprise Ollie rustled under the covers again. When he’d finished he had peeled the t-shirt off and threw it down to the foot of the bed. He shuffled closer to me again and pressed his warm, slight frame against mine, his arm snaking over my chest as I lay back into the bed. I could feel the little bulge in his panties pushed against me.

“You just surprised me, that’s all” he said.

“How far do you want to go, Ollie?” I asked. I wouldn’t normally have said that, but Ollie was a lot younger than me, a lot less experienced, and I didn’t want him to feel forced into anything. That wasn’t my style.

“I….. I don’t know.” He said honestly. He pushed himself up, leaning on my chest so that he could look into my eyes. “Maybe we can stop if I get uncomfortable?” He said. It was the sweetest thing. Almost a plea for me fool around with him until he said stop. What he was really asking was, if I say stop, will you?

“Sure. I can do that.” I said. I was about to say something else but Ollie had plucked up the courage to press his lips to mine, so I shut up and we kissed.

Ollie’s lips were soft, warm, and electric. Whatever his experience level, he was a great kisser. I pulled him in close to me, running my fingers through his hair with one hand while I caressed his back with the other. He was a skinny little thing, pale and fragile and entirely beautiful. Our tongues danced together in a wet and passionate embrace. I was hard almost instantly, this boy imbuing me with an incredible sexual energy.

Ollie ran his hand all over my chest, gently playing my my nipple and my chest hair. His fingers were warm, soft, and his caress gentle. My skin was on fire wherever he touched and he was circling lower and lower.

I moved my own hand further down his back, my larger, rougher hands moving more deliberately than Ollie’s. I gently touched his side and he flinched and giggled, ticklish. I dropped even lower and he obliged me buy shifting his body just far enough up mine that I could reach his bottom. I took a handful of his bottom cheek and squeezed him through those delightful panties and he let out a little moan through our kissing. I touched his face with my other hand, my rough hand on his soft, flawless face, holding him as we kissed deeper and deeper.

In return Ollie snaked his hand down to my stomach. He ran his fingers through my hair until he was fully playing in my pubic region. Then that delicate little hand wrapped around my upright, hard cock. It felt incredible. Such softness, it felt like he was barely touching me. But it was enough to drive me crazy. I shuffled in the bed, spreading my legs apart. I dropped my hand below the waistband of his panties. His buttocks were hairless and as soft as the rest of him. He had the most peach-like bottom I had ever touched. I ran a finger a tiny way down into his crack starting from the base of his spine. He shivered and goosebumps flashed across his body.

Ollie broke our kiss and turned. He licked and sucked at my nipple, then traced his tongue all the way down to my navel. I giggled as he tickled me there before taking my cock in his mouth. That hot, wet tongue that had just been in my mouth was now teasing my penis, licking, sucking, engulfing. I shifted my weight again, holding myself back from thrusting my hips up and fucking his pretty mouth. He touched my scrotum with his hand, wrapped the other around the shaft of my cock, and fondled, jerked, and sucked me.

I felt precum leaking from me and he delved with the tip of his tongue into my pee hole, curious at the taste and wanting more.

I grabbed the boy and hoisted him over me, positioned him to straddle me while he continued to please my cock. I pulled the gusset of his underwear to one side and freed his own hard cock. It was perfectly formed, standing upright and strong like a young boy’s should. The head wasn’t big, but it was the perfect shape. He had shaved all over, so his scrotum was smooth and his balls were impressive. I took him in my mouth and formed a tight suction, pulling his cock inside and caressing it firmly with my tongue. He moaned loudly. He liked that.

We lay there for an eternity, our hands and mouths content to explore each other’s erection. As I lay there I had a wonderful view of the curve of his bottom. I reached up with my hands and caressed his cheeks, gently moving closer to the ring that I could not yet see.

Ollie reached back. He swiftly pulled at the knots on either side of his panties and they came free. I tugged at the material and let it slide noiselessly over his buttocks. And there it was, his pretty, pink entrance. I was struck with a flash of worry. His hole was tiny, unused. I wasn’t sure I could get a finger in there, let alone anything else.

But I had to taste it. I shuffled again to get a better angle, let Ollie’s cock fall away, and I locked my mouth over his hole and I lapped. He wiggled and moaned loudly again and that spurred me on. I pulled his cheeks apart with my hands and pushed my tongue against his entrance. I wiggled and pushed and salivated, making him slick as he wiggled and pushed himself down on my face. Eventually the tip of my tongue started to break through and he moaned even more loudly. I tongued that hole like I have never eaten ass in my life. It was delicious, soft, and everything I had ever dreamed of. Olie’s reactions made everything so much better. I guessed he had never been eaten out before, because he was squirming and moaning and wriggling all over the place.

Suddenly I felt an incredible wave of sexual energy wash through me. I thought I was going to cum. I’d never had that before, like some kind of pre-orgasm. It sent me into a frenzy and I wanted so much more. I moved my hands to his hole and very gently started to slip the tip of my index finger inside him. He flinched, tightened up, but I held him tight, sucked his ring again, and then tried again. This time he remained relaxed and my finger slid inside. He was so tight! But he was youthful, too, and elastic. I was up to the first knuckle with ease, his passage lubricated by my saliva.

Now I fingered him. I used my mouth, my tongue and several fingers, each darting in and out in turn. It was driving him crazy and me too. Then I pressed down on that pretty pink hole with my thumb and the boy gave a low, deeply sensual moan as it slid inside. He stopped sucking me, leaned forward and arched his back. He wanted it.

I gently - ever so gently - pulled him open with my thumb. I continue to tongue him, and lubricate the way and to relax him by tracing the tip of my tongue around the edge of his hole. I gradually worked up to pressing my other thumb against him, remaining careful not to pinch his skin or force anything too far.

To my delight Ollie moaned loudly again, this time for even longer. He pushed his bottom back toward me and down, seeking more of my thumb. I pushed up to meet him and he exhaled deeply as the second digit penetrated him. I left them there together for a minute before I began to move them around, gently opening him up. The hole was incredibly tight, untouched by another’s hand, but he was becoming more and more relaxed, closer and closer to being ready for me.

Ollie started to suck me again, the shock of being penetrated by my two thumbs now passed. He was really going for it, bobbing his head up and down and moaning as he did so. I focused on the final action, of pulling my thumbs apart and applying more and more of my saliva into that space. A few minutes later I figured he was as ready as he was going to be without toys, and I was impatient to go to the next level.

I lifted Ollie off me and rolled him onto his back. I leaned forward and positioned myself over him, my feet now where my head had been.

Ollie’s face was flushed red and he had a crystal sheen over his eyes. He was breathing heavily. This was it.

He pulled me into another long, soft kiss. I toyed with asking permission but then I figured that moment had passed. I just prayed he didn’t call time and ask me to stop. Despite my promise, I was no longer certain I could have.

He pulled his legs right back for me, his wet and sticky hole glistening in the dim light. I took each ankle and pushed them further back and lined myself up. I placed his legs over my shoulders, rubbed the head of my cock around his anus and applied some pressure to keep it locked onto the target. He used his legs to bring me close and I bent low. Our tongues met from open mouths as we half-kissed, half-licked each others mouths. Then I pushed.

Ollie closed his eyes tight, but he continued to caress with his tongue. I flexed my hips, driving my erection forward against the boy’s virgin hole. I could feel his flesh moving against the pressure and then I felt his ring start to open. Ollie whimpered, squeezed his eyes closed, and I gave a quick, hard thrust. The head popped inside him and he let out a soft cry. I kissed him, remaining still and letting him get used to me, the worst of it over.

I had come this far, but I needed to be sure now. “Are you okay?” I asked, concern written all over my face.

Ollie opened his eyes and a small tear fell from the corner to run into the sheets. He met my gaze, his face a mask of lust, heat, and yes, uncertainty. He nodded, unable to speak. I could feel the tightness of his entrance pulsing with his heartbeat, but I could feel the tension begin to release as he relaxed. He was getting used to me. His facial expression changed. Uncertainty faded and curiosity at these new sensations took over. He reached an arm behind my head and pulled my down to kiss him again and I took that as I sign.

Slowly but deliberately I pushed forward, the shaft of my cock sliding into his guts. He was so hot down there, so tight. He gripped me so that pushing into him was a real effort. He wanted it tough. His hands were all over my head and face as we kissed and kissed and kissed. Finally I was all the way in. He held my face in his hands as I bottomed out. He flexed his body, accommodating my cock and getting used to that that full-up feeling he must have had.

“Oh……” he said, an involuntary release. “It’s…… fantastic!” He said and he grinned and breathed heavily and kissed me again.

I gradually pulled back just a short way, and then pushed back. He whimpered and I did it again. His whimper became a moan and I did it again, pulling further out now, pushing deeper in. His moans became loud exclamations. “Ah! Ah!” he cried and I built up a rhythm and increased the speed.

Ollie unhooked his legs from my shoulders and wrapped them around me, pulling me in. He was frenzied now and I was too, gripped by his hot hole and electric tongue. He writhed underneath me.

“Fuck me harder!” He instructed, his voice breathy and soft.

I obliged. I was ready. I fucked him hard and fast and I kissed and licked. I nibbled at his ear and sucked his neck. His “ah…ah….ah…ah” spurring me on and driving me to go harder.

Ollie squealed loudly. I felt his ring constrict a round the shaft of my cock almost painfully. I looked down. He was shooting cum over both of us. His body pulsed and flexed and writhed as I resumed my fucking action.

“How…..” He half asked, half moaned.

Ollie held my face and looked me in the eye. “Cum inside” he said. He wanted the full experience. I had already taken his virginity but he wanted everything. His pleading eyes, hot, red face full of passion, his cheeks and forehead shining with perspiration…. It was adorable, sexy, cute and everything all at once. I took his plea as a command and I thrust deeply a few times. I was so ready.

I felt my body tighten. That incredible sensation in my groin built and built and built. My scrotum tightened and my balls seemed to contract. Suddenly I was there. I could hold it no longer. With Ollie holding my face and our eyes locked, I let out a deep, guttural, sexual grunt and my cock engorged. His eyes went wide, his tight passage feeling everything as I pumped molten cum inside me.

I collapsed on top of him. We were both breathing heavily. Both hot, red faced. Both entirely spent. He grabbed my face one final time, one last deep and passionate kiss. Tears were streaming from his eyes now and he cried into my face. Before I could speak he uttered “thank you, thank you, thank you……. I’m so happy. I’m sorry”

I locked my lips to his, my mouth wide. In every action I told him, there there my precious boy, don’t cry. His emotion gradually subsided. He laughed. I laughed too and we kissed a little more.

“Are you okay?” I asked.

“God, yes!” He said, a broad sloppy grin on his face. “Oh, that was…. It was amazing…..thank you.”

I hugged him close, my cock still inside him, our bodies covered in his cum.

“I should be thanking you. You were wonderful.” I countered.

“I never knew it could be like that” he said. “When you first….. put it in….. it hurt, but it was kind of a good hurt. I didn’t want it to stop. And then it got much better.”

I smiled. I was glad I was able to give this young man the experience he truly wanted.

“I’m exhausted!” He exclaimed, like that was as much of a surprise as anything to him.

I very gently pulled myself from him. I gathered some pillows and turned the covers around so that we could sleep where we lay. I snuggled into him and he into me.

“Do you need to…… want to…. Get cleaned up…..?” I asked tentatively. In honesty I didn’t want him to move away from me. I wanted to maintain this position for as long as I possibly could.

He shook his head and draped an arm over my chest. Within a minute or two we had both drifted off, sleep flooding our systems and replacing the sexual energy that we had discharged tonight.

I had never slept so well as I did that night, Ollie’s arm across my chest and his warmth against mine. I could feel his heartbeat all night long, hear his breathing and feel as his chest rose and fell.

I’d never been happier.

Depending on how this one is received, I might add to it later. Please feel free to comment and if you liked it, please rate it below. Thanks :)