Losing my cherry to Kai

This story is vaguely based on a true story, although I have taken license to embellish some parts. I look forward to your feedback. 

I also want to apologise to anyone who was waiting for my other stories to continue. I will try and set time aside to deal with them as soon as I can.

Kai and I had known each other for a few years, having done swimming practice together when we were pre-teens, and then having gone to the same school for the past two years. Whilst we were on friendly terms, I could not say that we were necessarily friends. He graduated early, meaning that we were no longer in the same classes. I honestly cannot remember how we started hanging out. I was just happy that I finally had a friend my own age. I had been plagued with rumours of sexual exploits of a homosexual variety in a boarding school that I had gone to. Given that this was a backwater of a town in bible-country, very few people wanted anything to do with me, especially guys my own age who were sensitive to being “tarred with the same brush” as me. Whilst I tried to strenuously deny the allegations, it was no use. Kai was one of the first people that I felt that I could tell and not be judged. He was, of course, understanding, and it felt good to tell the truth to someone and let my defences down.

Over time we started hanging out more and more. Then one evening, he came over, it was a little warm, so I suggested that we go down to the pool that was at the bottom of the garden. I lent him some swimming trunks, as he hadn’t been expecting to swim. I decided to skinny-dip, hoping that he would do the same and hopefully I could make a move. We were chatting about random things, but I had one thing on my mind. Eventually, I decided to broach the question,

“Have you ever had a BJ from another guy?”

“I’ve had a few gay guys giving me head, yeah.”

“Do you want a BJ now?”

“Yeah, sure, but are you sure that your dad won’t bust us?”

“There’s a place you can sit there, under the rocks, which should shield us.”

He swam over and removed the swimming trunks.  He was sitting on the edge of the pool, with his legs dangling in the water.  It was shallow enough that I was able to kneel in front of him, with my waist and below still in the water. It was not the first time that I would give a BJ (obviously), but his dick was HUGE. I barely managed to fit the head in my mouth. I was so happy being able to give my friend some pleasure. I just loved the feel of this mass of flesh completely taking over my mouth. I was sucking for all I was worth. At some point, I realised that he was trying to pleasure me, as he reached down and grabbed at my cock. Despite the cold water surrounding my member, it was rock hard, I was that turned on by having this moment with my best friend. The next thing, our bliss was shattered when my father came out onto the balcony to say that he was going to pick up my sister. As he wanted a response, I needed to evacuate the cock from my mouth, without it making a slurping sound, so that he wouldn’t be suspicious. I was still delayed in answering, which probably generated its own suspicions, but it was the best that I could do. When the doors shut, indicating that my father had left us alone. I tried to go back to Kai’s manhood, but either the interaction had been a buzzkill, or I was not as proficient in protecting his cock from my teeth (a possibility that I would only learn much later. He was/is such a gentleman).

We left the pool, dried off and made our way back to my bedroom.

“I feel bad that you weren’t able to cum.”

“It is what it is.”

“You have a beautiful cock.”

“So I have been told.”

“I’m still horney, and you know that I am a virgin?”

“I had my suspicions. I’m guessing that you would like to change that?” He said, raising his eyebrows.

“I’m game, if you are?” I couldn’t believe my luck, I might be losing my virginity to one of the largest cocks I had ever seen, and not only that, I was about to come a lot closer to my friend.

“Ok, but we’d better be quick, as your dad could be coming back soon.”

Fuck, I’d forgotten about that, but hey, I didn’t need to be told twice. I was naked and on my bed, with my legs spread open.

“Dude, an arse doesn’t have natural lubrication. Do you have some baby oil or cream? Also, a shirt that you don’t mind throwing if it gets messy?”

I was a little nervous when he said the part about getting messy, but I didn’t want to lose this opportunity. I jumped out of bed, and grabbed a running shirt from the closet and the baby oil that I had used to lube my carnal ministrations. I gave both to him and lay back down on the bed. He tucked the shirt under my arse, and then squirted some oil on his hand. He massaged some onto his cock, and after squirting some more on his hand, he started rubbing into my arse crack. His finger connected with my hole, and I gasped in a mix of pleasure and discomfort. The oil was cold, but the finger was giving me pleasure that I had never known before. He looked at me, and was very factual,

“This is going to hurt, probably a lot. I don’t want it to hurt more than necessary, so relax, and don’t fight my penetration. Also, don’t forget to breathe. I wish I had more time to make this even more special for you, but I’ve already been caught by my parents when I was fucking a girl. That was uncomfortable enough. I don’t feel like doing round two with your father and it being you that I’m fucking.”

I nodded my assent, even though inside, I was shitting myself. My lizard brain, and the desire to get fucked won out, and I lay there as Kai swung his legs onto the bed and manoeuvred my legs back towards my body so that my arse was at a good angle for the coming invasion.

“Hold your legs behind the knees. Yeah, like that. Just remember to relax and breathe.”

One of his huge hands came up and grabbed behind my neck and he gently rubbed my face. It did help me to relax for a brief moment. I turned into the thumb that was gently rubbing my cheek. The next moment, I felt the pressure at the entrance to my anal cavity. The pain became excruciating. I gulped in air and shut my eyes, involuntarily trying to move my arse away from the source of the pain. Kai’s second hand clamped onto the other side of my head, and my face was violently brought forward. I opened my eyes, to see Kai looking somewhere between concerned and pissed.

“If you don’t breathe and relax now, I am going to slap you hard. I don’t want to, but you are going to hurt a lot more if I tear your arse than if I slap your face.”

I saw that he meant it and I exhaled and inhaled, trying to release my sphincter whilst my nails dug into the flesh of my legs trying to send the pain elsewhere. There was so much lubrication that the moment I stopped fighting it, the cockhead started its slow and painful way into my body. I was breathing laboriously, feeling like I was being split in two. I was seriously considering why I wanted this when all of a sudden an electric jolt shot through my body. My cock was rigid and I relaxed even more. Kai’s cock had hit my prostate, and I was in ecstasy. It was still painful, but I was also loving the feel of this python grazing past my love-nut as it opened me up for the first time. After what felt like ages, but was less then a minute, Kai stopped moving his cock. I shot him a quizzical look. He smiled generously, and said that he’d given me all he’s got. I started giggling,

“I hope that the python is comfortable in his new home.”

“He does enjoy warm, dark places, it must be said.”, said Kai laughing at the situation. “But seriously, are you ok?”

“I’m getting used to it. I feel full, in a nice kind of way. I can also feel the pain subsiding.”

“Ok, that’s good. I’m going to start fucking you now.”

All of a sudden a look came over his face and he leaned forward and kissed me. I was hardly expecting that, but it caused me to relax a little more. It was then that I felt the awesome cock begin to withdraw. I let go of my legs and started feeling the muscles of this man who was now starting to slowly withdraw and press in his manhood. His arse muscles were gently undulating under my fingers. I tried to wrap my legs as best as I could around his waist, just loving this negation of myself, being nothing more than a vessel to pleasure another man.

I guess that he could feel that I was starting to loosen up as he raised himself up from the almost prone position that he had been, and he grabbed my waist and started pistoning his cock up and down my love chute. I ran my hand down his heaving chest as he did so, and felt the slickness of his sweat as he sought to fuck us both to ecstasy. Each time his dick maxed out in my hole, I moaned. It was involuntary, but it was turning me on even more. My dick was bouncing from side to side. Pre-cum dribbling out of it and smearing across my stomach. Neither of us paid it any attention, as the only cock that was of interest was the one currently turning my arse inside out. I felt the drip of Kai’s sweat as it fell onto my body, his body odour starting to permeate my skin, my nostrils, and my world. I reached up and dragged his face closer to mine to that I could give him a kiss, further signalling my submission to his manliness. Submitting to him. This was where I was meant to be. Almost without warning, I felt my body seize up. I let out an animalistic cry as my head was driven back into the pillow with a primal seizure. My hips bucked, my arse squeezed, but could not shut, and rope after rope of cum shot across my torso and even landed on my face. During my second or third wave of orgasm, Kai’s eyes crossed, and he drove his dick into my body with such a force that my whole body shook. He then fell on me and hooked his arms under my shoulders as his body deposited his spunk balls deep inside of me.

We were both panting and trying to recover. I felt very much at peace with a man inside of me and on top of me. Kai’s entire weight was resting on me. I found it very comforting. Slowly his dick started losing its potency and my arse started doing what it was supposed to do and ejected it.

“Thank-you, that was fantastic. You have a great and tight arse. It felt so good fucking you.”

“It’s me that should be thanking you. You were amazing and being ploughed by such a monster cock was an honour.”

He smiled, kissed me on my forehead and then started to get up. I looked at him a little bit hurt and a little expectantly. I knew that he was “straight”, and we weren’t going to live happily ever after, especially not in a place where what we had just done could land us in jail. He saw my look, and then said, “Hate to remind you, but your father could be back any moment.”

“Fuck,” I said, as I sprung out of bed, grabbing clothes and towels, whilst simultaneously throwing the shirt, which was covered in oil, into the washing basket and hiding the baby oil. “We’d better go get cleaned up. Do you want to go first, or should I?”

“I think we’d better go together, we might not have much time.”

I wiggled my eyebrows.

“No, not like that you doofus.  I haven’t had such an intense orgasm for a while. We just need to hurry.”

We ran to the shower, and both got in. We were a blur of soap, arms, legs, torsos and dicks as we sought to remove all remnants of our carnal coupling from our bodies. We had just gotten out of the shower and were towelling off when we heard the sound of my father’s car coming down the driveway. We threw our clothes on, hung up the towels and ran to the lounge to watch some crap on TV, as though we’d been there for a while. Of course, dad came to check up on us, only for whatever program had been on TV to go to credits. Kai got up, thanked us for having him, but said that he really needed to get going.

“I’ll see you out to your car.” I said

On our way to his car, when we were in a blind spot, where my father couldn’t see us, he reached over and grabbed my arse, “you look after that fine arse of yours, I want round two before I leave.”

I smiled, “I hope you are prepared to make good on your promise.”

After he left that evening, I lay in bed, feeling up my arse and its puffy lips. I tried to transcribe to memory the whole episode, enjoying the feeling of my arse being a whole lot looser, but also being filled with my friend’s cum. I lost consciousness in a haze of bliss.

Unfortunately, Kai and I would never have a round two, as we never found the privacy again. Who knows, maybe one day I will be able to have Kai’s mighty sword sheathed in between my legs again.