Simon and Me In The Hotel

We entered the hotel room, a knot of nerves in my stomach as I had never done anything like this before or since, he was a head taller than me, I felt so small next to Simon and I could feel his eyes on me as we entered the sterile looking Holiday Inn room. I knew he wanted me from the moment he looked at me and now he had dragged me to this hotel room, whispering to me in the five minute taxi ride here of how he would take me. The door closed behind us and now I was his, the only thing I hoped was that he would take me gently for my first time.
I felt Simon’s hand on my shoulder as he turned me around to face him, he must have noticed my shyness and shaking as he leaned down and pressed his lips to mine, I shared my first kiss with another man, although superficial there would be more to come. A strong arm wrapped around my waist and pulled me in as he deepened the kiss, pulling me into his embrace and pressing our bodies together, it feels so silly now that I never reacted as his hand slid down my back and rested on my butt, giving it a light squeeze as I tried my best to kiss him back. Simon was a lot older and more experienced than me – that is to say he had some experience – and I was just trying to keep up with his advances.

Finally we broke the kiss and he stared down at me and I up at him, I was trying to speak as he looked at me, my nerves making me shake as I swallowed deeply.
“Shall we do it?” I said, I look back and think how embarrassed I was at that moment I am pretty sure I blushed like a beacon.

My hand clumsily groped at his crotch, I tried to stroke his cock and balls but ended up grabbing them and squeezing a little roughly, I can barely remember how he undressed me, the next thing I remember I was wearing only my boxers and his hands roamed over my naked skin, his hands groping my cock through my underwear as he stole another hungry kiss from me. I felt how hard I was and could see how hard he was inside his jeans, I would have tried to undo his belt but did not dare try to show him how much I was shaking.

I felt so numb as he pushed my boxers down, slipping them down over my hips and letting them drop, I felt myself naked in front of him and wanted nothing more than to turn away as the million thoughts of how good an idea this was. Was I gay? If I was gay did I want to lose my virginity to a stranger like this? If I didn’t lose it to him nobody would accept it...
“Turn around.” He said and there was no turning back as I knelt on the edge of the bed, submitting myself to him, he would take me however he wanted tonight.

I heard him taking off his clothes behind me as I looked at the wall, I reached behind me and started to try and finger my ass, my nerves again taking the better of me as I assumed he would not do it himself.
I felt him move my hand to the side and his own finger press against my anus, I have to say now that aside from a tongue this was the first time anybody had been inside me and I let out what I thought was a sultry moan that came out more like a parrot squawking as his finger pushed inside, it was so unusual feeling his knuckles push against my muscle, I tightened up so much he placed his hand on my back and began to whisper to me to relax and that he would take it slowly.

Simon did not withdraw his finger at all for almost a full minute, when he did there was the unusual movement once again as it slipped out, he must have put a lot of lube on his finger as it seemed to slide out so quickly only to be pushed straight back in, slowly and carefully he slid his finger in and out of me again and again until pulling it all the way out. At this time I did not want him to put it back in for some reason I could never explain for the moment I felt that finger pressing against my ass again I wanted it to push back inside, this time with a second pressing in with it, my anus pressing in before the lube let it slide inside, the two fingers popping inside and curling around, parting slightly and trying to pry my ass open, I could already feel it was slackened from the movements and stretching, my anus clenched almost involuntarily as Simons skilled fingers prepared me and opened me up, the feeling that he had done this many times before just seemed to make me harder as both fingers slid out of me finally.

There was a long moment of awkwardness as I heard a tearing sound of a condom wrapper being opened and a quiet snap as he rolled it over his cock, another moment passed as he lubed his cock, he was very thorough. My nerves began to come again and for some reason I felt my feet were cold and it was uncomfortable, my arms hurt from being on all fours, maybe someone was watching from the tower block across the road, maybe the maid would come.... I felt the head of his cock against my asshole, the head of the condom crumpled against the quivering muscle and his hands holding onto my hips, holding me in place in case I tried to get away, I had given myself to him in the bar as soon as he had grabbed my butt, I had been his since I got into the taxi with him and now was the inevitable moment as we were naked and entwined in the hotel room with his cock slowly pressing into me.

As the cockhead slowly pushed inside me I tried to clench my anus but he had prepared me well, I could not tighten up enough to push him out and I felt his warm head slip inside me, the head felt wrinkly and it was a curious sensation trying to guess which part of his cock was inside me. Slowly, inch by inch he slipped inside me and it felt like my stomach was moving as he kept pushing in, his cock feeling endless and a sigh of relief leaving me as his hips finally touched my bum cheeks, the feeling was not painful, just one of quite extreme discomfort as his cock was lodged inside me, the first time I had ever had a cock inside me and he held it there, his hips pressed against my bum and looming over me as I glanced over my shoulder, my mind was playing out a battle of sensations as I almost willed this thing to hurt, there was no pain. The jibes from my school friends years ago about being ‘bummed’ and the shame I should have felt as I was being taken by another man, There was no shame.

As I glanced over my shoulder he leaned over me and kissed me once more, his tongue curling around mine as he slipped his hips back barely half an inch before pressing in again, as we broke the kiss I asked another question that seems stupid now.
“Do I feel good inside?” I said, I don’t even remember his response.

I turned my head away and nodded, not even sure what I was nodding at as his cock began to slide out of my ass, it felt a lot shorter this time as he slid out and pushed back in, his groping hand slipping over my nipple and urging me up off my arms, one hand on my shoulder and one wrapping around my cock, pumping it a few times as he slipped in and out of me slowly, I was groaning and biting my lip as I was taken slowly. Eventually he slid completely out of me, standing me up and turning me around, pushing me down on the bed on my back and it felt like he was trying to push my knees past my head, it must only have been at my stomach and once more I felt his cock pressing against my anus, slipping inside me easily, his body kept my legs spread and I looked up at him as I felt his penis slide in and out of me, quicker and quicker until he was fucking me, I seem to remember myself crying out and moaning as Simon studied my face, after what seemed like two minutes I felt a gush of warmth like liquid being poured inside me as Simon let out a loud, brute groan.

I opened my arms and he lay on top of me, his cock still inside me as my hands wandered over his back, I had not cum or even felt a lot of pleasure from being fucked like that, but he had taken me and made me his, he had used me to cum. It was a strange feeling being fucked by someone who was such a stranger and pure lust had fuelled us. I felt his cock slipping out of me, the condom he was wearing had a wad of cum inside it and all I wanted now was to go to the bathroom as I felt the lube leaking out of my slackened asshole.

*

It was midnight by the time we got into the bed together, I half expected him to leave once he had had sex with me but together we cuddled, not often I had slept naked but tonight it seemed appropriate. As we entwined I felt Simon’s hand grasp me and play with my cock, he gave me a slow hand job and it felt for a long while like I would never cum but as he held me cradled in his arm with my head resting on his chest, his hand slowly tugging at my cock as he kissed at my forehead I felt myself shudder and cum on his hand and I felt then like I was his little plaything, putty in his hand for him to manipulate.

*

We drifted off into sleep, he held me in his heavy arms and I simply lay and thought about things, for a long time I just wanted to get my clothes and leave but was too scared to move, some of the time I thought about my ass and how it still felt a little raw and sore. I snuggled up to him completely and smelled him, the smell of his sweat was very pungent and I felt like his ‘girl’ for that night.

We woke at about 5am it felt like, the dawn light was coming through the window but the sun was not even up yet, when I say ‘we’ woke, he shook me awake gently, he must have woken up first, maybe he was shaking me awake to tell me to leave? I felt his groping hand at my cock again, tugging me awake although I needed no help being 17 and forever horny, before I knew it I was lying with my head on the pillows and him lying on top of me again, I could feel his condom covered cock running over my soft butt as I shook my hands in front of my face asking him to stop, I felt like telling him it was a good idea last night but was it a good idea in the morning? I felt a slug trail of lube running down my bum, I guess I was still coming to my waking senses, it is not every day you wake up and moments later are on the verge of being fucked, he pressed the head of his cock against my asshole and looked me in the eye, daring me to say no.

I did not dare, I remembered how I had said I was his for the night and I was his to do whatever he wanted, he slid his cock into my ass and again no pain came, my slackened asshole obviously not fully closed after my heavy fucking last night, I felt him moving in and out of me, moving my legs to new positions as he took me slow and hard, pumping himself inside as I quietly sighed and moaned as I felt his cock stretching me once again, this morning already he was taking me. Simon raised one of my legs and put it on his shoulder, I felt myself opening up to him fully and my ass gripped him more as I watched the cover slide off his back and the quick cooling of no longer being in the heat trap, all there was now was his benevolent stare as he took me in the ass for the second time.

Slipping out of me he shift me around and made me face the wall, my hands gripping the headboard as I felt his hips slapping against my butt, his hands gripping my hips again tightly, one hand moving to my shoulder now and then to hold me rock steady as he pounded his cock as hard as he could, so hard he was knocking the air out of my lungs and almost making me cough with the force of his thrusts, my body was sweaty but there seemed to be no stopping Simon rutting into me and taking me so hard it made my ass go numb. Once again he stopped and slid out of me, gently coaxing me over to the window, he made me stand at the window, I was bending at the waist and watching people walk by the hotel as again and again his cock pounded into me, as I looked at the people he sped up, the sound of his hips slapping against my ass audible as I groaned and moaned at him.

He lay me back on the bed which had gone cold and made me hold my legs up, presenting myself to him and he made me watch as he slid his cock into my slackened butt, sweat felt like it was pouring out of me, the only stops he made was to lube his cock again, I felt like my asshole was completely slack and I had no control over it, my head drifted to the side and I saw that it was 7am, the sun was beginning to rise and Simon must have been fucking me for almost an hour now, He had simply woken me up and began to fuck me and there was nothing I could do but take it. I was his little toy, a hole for him to fuck hard.

After a long set of grunts I thought he might cum inside me again, yet it was a false alarm and he simply got off and me shoved me to the window once again, he must have liked my reaction. There was a slurping noise of lube leaking from my anus as his cock slid in and out of me and I had had an erection for so long it had faded away as I had been fucked for so long, my knuckles were white as my hands pressed against the windowsill and we watched a larger group of people passing the Holiday Inn, I was watching the people as I felt the cock sliding into me, pounding into me and I heard them speaking. I rose up slightly, Simon rising with me and never once stopping his relentless thrusting into me, I felt lube leaking down my legs and I almost wished the people would see us, I had many thoughts that I wanted him to be my boyfriend now, but something told me that would never be and to simply enjoy being taken like this.

Eventually Simon stopped fucking me, I felt completely exhausted and lay on the bed smelling of sweat as he grinned at me, he said something about wanting to fuck me again all day and I grinned stupidly and nodded, I felt my ass almost gaping after my long and rough fucking, last night being only a warm up for what I had experienced this morning.

Simon grabbed me by the hand and lifted me off the bed, naked we went to the bathroom together and got under the warm shower together, my nerves had disappeared now he had taken me for so long, I wrapped my arms around his chest and held myself close as his fingers flicked over my slack asshole and he brought the showerhead to clean me, rubbing the lube away as his rough fingers slid between my bum cheeks, he cleaned me thoroughly and the feeling of not being the first he had done this to entered my mind once again.

I slid down to my knees to come face to face with his hard cock, not wanting to miss anything I took it in my mouth, I could barely get past the head and my gag reflex almost made me puke right away, I took it a little slower and used my mouth to suck him off, a hand playing with his balls and tugging gently at the base of his cock, I licked the head and suckled at the head, sucking it like it was a cut and hearing Simon groan, in hindsight it was in pain but I continued to suck it like that until he pushed my head away a little, tugging himself quickly as he held me firmly but not roughly by the hair, soft grunts came from him as the water showered over us and ran down his body, eventually he started to shudder and I clasped my lips around his cockhead, feeling the warm liquid splash into my mouth, little squirts of it completely filling my mouth, the taste was horrific, like the sourest, saltiest meat sauce (excuse that pun) I had ever tasted, I swallowed half and almost puked the other half out, it splattered onto the floor and was quickly washed away by the water.

Without really speaking we finished cleaning ourselves and dried ourselves with the same towel, a strange distance between us after he had cum in my mouth. We dressed in silence and had one final kiss, not even promising to meet again he left, asking me to leave ten minutes after him.

If the story is to end on an amusing note it would be that after he left I realised I had no idea where I was or how to get home!