The First Time

"Hey, you okay if I stay over?" Jake said. My heart leapt as I looked up, I hoped my face didn't betray me. It was late and it made sense. We both had a uni paper to get in and we had been at it a while.

"Yeah sure," I said, trying to act cool. "Not sure where you're going to sleep though." I only had one room. I shared a house with some other uni students. They were all out drinking, doing what students like to do. We were stuck in trying to finish our work. I didn't mind though, I was with Jake.

"I'm pretty sure we're adult enough to share the same bed," Jake said. "Or is it too gay?"

I laughed. "Yeah I imagine we'll be fine," I replied. "As long as no one finds out."

"I'll try and keep my hands to myself," Jake added. "No promises though." He winked at me and I felt my cock stir.

I couldn't take my eyes off him at that point. His hand went through his short blonde hair, his t-shirt was tight on his slim muscular body. He was openly gay, and very confident. The complete opposite of me. We were both 19, had met in our first year at university and had been best friends since.

I was still working out my sexuality and hadn't shared my thoughts with anyone. I knew I fancied Jake, that was one definite, but I was too scared to tell him. If he didn't like me back it would make things awkward between us.

"Yeah, you keep those wandering hands to yourself," I said, laughing weakly. "Come on we need to finish this work."

We got our heads down and cracked on. I wanted to get it finished, the thought of sharing a bed with Jake had given me some motivation. I knew nothing would happen, and I knew I would be disappointed, but a guy can dream, right?

Jake seemed highly motivated too, occasionally glancing up at me whilst working, and we soon finished.

"Well that was incredibly boring," Jake said. "I need a piss." He jumped up and headed to the shared bathroom.

I watched him go, his fine ass squeezed into his jeans. I felt myself harden at the thought of sleeping in the same bed as him. I was desperate for something to happen between us. I touched myself through the fabric of my tracksuit bottoms, a soft moan escaping my lips. I shook my head and got up to tidy. Jake soon returned.

"Just going to get ready for bed," I said.

"Okay," Jake replied.

It was my turn to use the bathroom. My cock annoyingly semi hard as I pissed. I straightened my dark hair in the mirror and put it back into a ponytail. I finished up and headed back to my room.

Jake was standing looking through my books and turned when I came in.

"All set?" he asked.

"Yeah think so," I said casually.

He took his t-shirt off and I inwardly groaned. I had seen it before but it always made me feel funny. He was slight, but toned and muscular, his visible six pack looked good enough to eat. He was shaved all over, smooth and hairless. A thing I had copied on my body. I hated myself for not being able to make a move on him.

"Fuck," I cursed, under my breath. I had just realised my mistake. I was so used to it I had forgotten. I walked over and picked up my pyjama bottoms and another t-shirt. I went to head back out the door.

"I thought you just got ready for bed?" Jake asked

"Just putting these on," I said casually.

"You're not normally so shy," he said. "What's wrong with here?"

"I just feel a bit inadequate next to that body," I said, trying to make it sound jokey.

"Don't be daft," he replied. "You've got a great body."

Not great like his great, I thought. I was too thin, but I did like the feminine quality to it, made me look better in the clothes I really liked to wear.

"I'll be back in a sec," I said, moving towards the door. He moved and cut me off. I could see the look in his eye.

"Don't make me undress you," he said, laughing. He had a habit of play wrestling with me, jokingly pinning me down. I can't say I normally complained. If I really told him not to, I knew he wouldn't, and I knew I should now, but still couldn't bring myself to say no. I wanted it.

"Don't you dare," I laughed nervously. The thought of him undressing me made me nearly groan.

"Then get changed," he said, a mischievous look on his face as he advanced towards me.

I couldn't let him see what I had on underneath, why was I such an idiot. "I can't," I mumbled.

He jumped me, tickling me as he pushed me back onto the bed. I couldn't help but laugh as he pinned me down

"Get off!" I squealed.

"No chance," he laughed. He straddled my legs, pinning me down. I felt him ground down on my upper thighs, I desperately willed my cock to not get any harder, but it was betraying me. Luckily he moved, flipping me over on to my stomach. I half heartedly resisted.

"Let's get these off then," he said laughing. He pulled my tracksuit bottoms down hard and stopped laughing. I flushed red.

"What are these then?" he said. I didn't sense disgust in his voice at the sight of my pert bottom in my lace panties. I moaned as he touched them, squeezing my bum cheek. "They look nice."

"I like wearing them," I mumbled. He ran his hand up my back under my t-shirt feeling a bra strap.

"Good. You're wearing the set then," he said. I sensed no shock in his voice. My cock pressing into the bed got harder as his hand returned back to my pert bottom. He squeezed again.

He massaged my thighs and ass, caressing and stroking. My cock raged underneath my body. He stroked the small of my back, pushing my T-shirt up. I moaned.

"You like that?" he asked.

"I do," I said. "It feels so nice."

I felt kisses on my back as he moved up towards my neck. His body lying over mine. I felt his own hardness press into me as he lay down on top of me, his kisses reaching my neck. I moaned again.

"Do you want this?" Jake asked.

"Oh god yes!" I said. Moaning as he pushed down into me, leaning over and kissing me. The angle awkward, my head stretching back, but it was still hot.

"Turn over," he said, into my ear. I shivered at the breath on my neck.

He lifted himself up and I turned over. My cock strained to escape the panties I was wearing, and as he pressed back down into me there was no doubt how much I wanted it.

"Mmm. That feels good," Jake said, slowly moving his hips on my pelvis, grinding me against him. We kissed passionately. We got lost in the kiss, our bodies moving and rubbing together. He pulled away and I groaned. He moved down my body, more kisses and licking. I pulled my t-shirt over my head, my bra and panties now plain to see.

Jake straddled my thighs again. My cock was so hard now it threatened to rip through my delicate underwear. He touched me through the lace and I groaned, how I didn't cum just then I'll never know.

"Can I see it?" he asked. Such a gentleman, I thought. I nodded.

"Please touch it," I moaned. He smiled and watched my face as he took it out, his eyes went to it and he moaned softly. My cock stood tall, 6 inches and thick.

"It's gorgeous," he said. He bent down and kissed the end. Please, I begged in my head, desperate for him to take it in his mouth. And when he did I moaned loudly.

He pushed his head down, taking me in deep. He came back up, he kissed and licked my shaft. I had no hope. I was so excited now, I knew it would be quick and embarrassing.

He slowly sucked me off whilst I desperately tried to hold on. He forced me down his throat and I felt the end squeeze down past his tonsils.

"Oh fuck," I groaned. "I can't hold on!" Jake looked up at me and came up for air.

"Cum for me," he said seductively, and took me back in his mouth. He moved his mouth up and down my shaft and I exploded with a loud groan. My cock pumped my load into his mouth and I felt him drink it down, sucking me dry. My body shook as I moaned. It was the best feeling I had ever had.

Jake finished getting every last drop out of me and crawled up my body. He kissed me, and I tasted the familiar taste of my cum.

"Sorry. I couldn't hold on," I said, my face felt on fire as he stared deep into my eyes. "It was too intense."

"Don't apologise," he said. "It's fucking hot that you lost control. Hope there's more."

"There is. My turn," I said. Jake smiled down at me. He got up and stood by the side of the bed and dropped his boxer shorts, a cock slightly bigger than mine sprang free. I sat up, pulling up my panties, desperate to touch him. I had only ever touched mine before.

I took it in my hand and stroked it, my other hand caressing his irresistible abs. I smiled up at him as I bent forward and took him in my mouth. He moaned and his hands gripped my head. I felt excitement coursing through my body.

The throbbing shaft slid past my lips, I felt the veins against my tongue. It was so amazing. I pushed him as far back my throat as I could manage before gagging.

"That's good," Jake moaned. "So deep." I guessed all that training taking my dildo down my throat had paid off. I just hoped my asshole would be tested the same.

I sucked Jake off for a bit, my head bobbing back and forth. Then he did what I wanted, he gripped my pony tail, his fingers woven in my hair, and he started fucking my mouth. He started moving his hips, the head of his member banging against the back of my throat. I gagged and spit ran out of my mouth and over my chin. I loved the abuse on my throat, but now I wanted it somewhere else.

I pulled off his cock. "I want you in me," I said looking up at him.

"Are you sure?" he asked. I nodded and turned around, getting on all fours on the edge of the bed, sticking out my bum.

"Have you got other clothes you want to wear?" he asked. "Is there more?"

I couldn't believe what he was asking. I thought about saying no but I couldn't resist. I had fantasised so many times about being fucked in certain outfits. I got up and went to my drawers. He watched me.

I opened a drawer and pulled out a short black pleated skirt, I put it on. I flushed red imagining Jake looking at me, the skirt high on my thin thighs. I found a cropped t-shirt and pulled that on top. I turned and let my hair down.

"Stunning," Jake said. "I like it."

"Thank you," I said quietly.

"Have you got any lube?" he asked.

"In there," I replied, pointing to the bedside table. My cock was hard again. I went to the bed, sat, and waited.

Jake rummaged around and found it, along with something else.

"Hello!" he said. Waving around my toy.

I was still a virgin, something that I was pretty desperate to remedy, but I knew I could take Jake, and I knew I wanted it badly. I had put things inside me plenty of times and loved the feeling of it when it entered me, and the feeling of when something was deep inside me. I had treated myself to the 8 inch dildo for quite a while and it had become a good companion since.

"Why did you never tell me?" Jake said.

"I couldn't," I said. I didn't want to go through it now. "Please don't stop."

Jake smiled. He came back over, the rubber cock still in his hand.

"Think we need a little warm up first," Jake said. "Let's see that sexy ass of yours again."

It was my turn to smile as I bent over, sticking my bum back in the air. I felt Jake move behind me. He lifted my skirt up over my hips and pulled my panties down my thighs. I gasped as I felt his kisses on my cheeks and then moaned as he licked my asshole, covering it in his saliva, his tongue pushing into me, opening me slightly.

I felt a finger enter me and then a wetness, the lube I guessed, as he pushed a finger deeper, and then added another. I groaned and writhed as he readied my asshole with his fingers and tongue, with lube and spit.

He squeezed two fingers into me and I moaned as he fucked me with them. I was so hard again it ached.

I gasped again as I felt something larger press into me, I looked back and Jake was standing there with the dildo, pressing against my tight bud.

"Oh fuck, this is so hot," Jake moaned. "I want to see you take it before I fuck you." I groaned at his words.

"Please hurry," I begged. I wanted him now, wanted him inside me.

Jake pushed the end of the toy into me, the bulbous head stretching me wider. I was well lubed now but it was still big. The knot struggled and I winced in pain, but I ignored it, knowing what was coming next. When it broke through my resistance I cried in pleasure, the feeling of it sliding into me always felt amazing.

"Good boy," Jake said, as he pushed it into my tight hole. I took about half and he pulled it out, before sliding it back in.

"Oh god," I cried. He started to slowly fuck me with it, pushing deeper each time. I hoped preparing me for the real thing.

"Do you want me to fuck you Sam?" he said into my ear.

"Yes please," I moaned. "I want it so bad."

"How much?" he asked, continuing to assault my hole with the toy.

"Don't make me beg Jake," I replied. I knew I would though.

He laughed, not unkindly, and pulled the dildo out. I suddenly felt empty, wanting more. Luckily I was going to get my wish.

I felt Jake move close in behind me, and groaned loudly as I felt the tip of his cock press against my well prepared anus.

He guided himself into me, his cock stretching my readied hole, he pushed in deep and I cried out.

He started slowly, his hands gripping my skirt and thin waist as he started to delicately fuck me. Sliding in and out of my asshole. It felt amazing, better than I could have ever hoped for.

It wasn't long before he was fucking me harder, his thrusts picking up the pace as I moaned and pushed back onto him with every forward movement.

I started playing with my hard cock, wanking myself off as I got fucked.

Jake suddenly pulled me up into him, my thin body stretching tight against him. He reached round and took my cock from my hand and started stroking me himself.

"You're my femboy now," he said into my ear. I moaned loudly.

He fucked me faster, his hand moving quickly. I could feel my orgasm building quickly again. I wasn't used to the sensory overload. I loved it.

"Harder," I groaned. He sped up and used more force, pounding into me as he stroked my cock. God, it was too much. I came hard, cum covering the inside of my skirt as I shook.

"Fuck," Jake moaned, pure lust in his voice.

I squealed again as he pulled out and shoved me down flat onto my stomach, on to the bed, my cum filled skirt pressing into me. I was still cumming as he climbed on top and entered me hard. I cried out in pleasure.

He started pounding down into me, pressing me into the bed. His cock so deep inside me. His thighs slapped against me, making a clapping sound.

"So deep," I groaned, burying my head in the sheets.

"Fuck, fuck, fuck," he grunted, slamming into me. His pelvis banging against my boney ass. He kept going, each time filling my ass.

"Cum in me!" I moaned. I could hear he was close, his fucking so frantic, his breathing heavy.

He sped up, faster and harder. I groaned loudly as he pounded my tight hole. His thrusts stopped, and he cried out as he pushed hard into me and ejaculated.

"Oh fuck," I groaned loudly, as he filled my asshole with cum. His cock throbbing and twitching deep inside me. Cum squirting hard from the end, covering my insides. He slowly ground into me as he milked every drop from himself with my tight hole.

He flattened himself against me and kissed me on the cheek. His cock still dribbling into me.

"That was amazing," he said. "I wish you had told me how you felt."

"I wish I had too," I said. Looking at him over my shoulder, he went to pull out. "Not yet." He stopped and pressed back into me. I wanted him inside me for a bit longer.

"Okay," he said. "Our study sessions are going to be a lot more interesting from now on."

"I hope so," I replied, smiling.

The End.