My First Time

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This story is based on my experiences, but I do not think I would ever go as far as the second part of the story, though it is my unalloyed fantasy !


My first time happened when I was 20 and it shaped the way that I have interacted with others ever since…
I was always sexually naïve and quite scrawny as a young man and all my mates used to tease me about my slightly feminine looks and long hair.
I liked girls but I always thought that I had a thing about men as well. Especially older men. I don’t know why. Maybe because I was only five foot six and nine stone dripping wet.
I remember this as if it was yesterday. 
I’d kind of heard of cruising sites (we didn’t have the net in those days: just graffiti on toilet walls) and I really wanted to just see what they were like. So I got on my bike one day and headed out to one of the local ones where I thought that there may be some action.
Not that I was going to take part in this action you understand – oh no I just wanted some titillation, something to wank about that night.
So with this in mind, I arrived, padlocked my bike and walked into the network of paths that were part of this densely wooded area. Bear in mind this was high summer – 23 degrees and the vegetation was all at it’s most abundant. Just as we like it eh?
I was only wearing tight shorts, a T shirt and sandals and just being here had made my cock tent in my shorts and when I looked down I saw a damp stain where precum was leaking.
Walking through the paths, I imagined all sorts of scenarios in my head and my cock was at a permanent state of attention.
Please note that up to this point my only experience was a rushed confrontation in a public toilet where I had wanked a man off through a glory hole. I can still remember it now, the cum covering the palm of my hand and me reaching for my cock and wanking with his cum dripping from my glans and mixing with my own…
Anyway, so bound up in my fantasies was I that I had not noticed an older man following me. He looked to my admittedly inexperienced eye to be in his sixties. Well built with salt an pepper hair and a slight tummy, he was my ideal man.
Stomach churning, I walked on, deeper into the woods, wondering what I should do. I realised I had gone off the beaten path and was now in a quieter part where there were lots of little caves made by the rhododendrons that seemed to abound her. 
I glanced back. He was only about twenty yards behind me. What was I going to do?
With trembling hands, I stopped and pulled my shorts down, stepped out of them and bent over as if to check my sandal.
My heart was racing  by now. What was I doing ? What would he do ? Did I really want to do this?
And all these thoughts went out of my mind as he came up behind me and caressed my bottom. He let his hand wander over all of my cheeks and then ran his finger up my crack.
I clearly remember that I whimpered at that moment. I was so turned on. I could not remember ever being so turned on.
“Oh, you like that, don’t you?” he said in a deep but quiet voice.
“Mmm” was all I could manage.
He looked at me and smiled. His hand went down to my crotch and took my cock into his hand. Then he started to walk away, pulling me with him.
I had no choice but to follow. This wonderful man was leading me by my cock and I had absolutely no choice but to follow him.
“First time?” he asked 
“Yes Sir” I replied
“No need for the Sir. I’m Brian”
“Chris” I managed to reply
“Do you want some fun Chris?”
“Yes please” There it was out of my lips before I could stop myself. I could run away of course. I could easily outdistance him, be back on my bike and gone in the wink of an eye. But…
I didn’t. I allowed myself to be tugged along by my small penis. I was embarrassed because I was leaking precum into his hand, but he didn’t seem to mind.
He pulled me through some bushes and into a little quiet sort of place surrounded by Rhody bushes. I realised it was very discreet and very quiet.
He stopped, let go of my cock. I wished he hadn’t. I wanted him to touch me again.
Instead he turned to me and lifted my T shirt up and over my head. I just stood there as he removed it.
Then he slowly and methodically stripped his own clothes off. 
I watched as first his hairy chest and then his gorgeous member hove into view.
I could not take my eyes off of it. It must have been eight inches long and nearly fully erect. It was uncut, but he put his hand down to it and pulled back his foreskin to reveal the loveliest glans I had ever seen.
Or to put it another way, the third one I had ever seen. That included my own and the other heavy cummer in the toilet.
“Do you like what you see?” he asked
I didn’t reply. I could not take my eyes of his wonderful appendage. I wanted to… I don’t know what I wanted to do, but I wanted him to show me.
I was still nervous, but I was so turned on that it overtook my skittishness.
“Chris?” He took my chin in his hand and pulled my face up so I looked at him. He was smiling.
“I don’t normally get this amount of admiration” He smiled. “It’s very flattering”
And with that, he bent forward and planted a kiss on my lips. 
Now I’m a pretty good kisser nowadays and my oral is well up to scratch, but that first kiss from a man just blew my mind.
He had total control of me. As he kissed me, he took my right hand and guided it to his cock. I tried to pull my hand away, but it was just a reflex and he knew that. He held firm and guided me to his warm flesh.
My hand took hold of his cock and it felt hot and stiff and I couldn’t get enough of feeling it. He kept on kissing me and I kept on playing with him.
Finally we came up for air.
“Would you like to suck me?” he whispered
“I’m not sure” I replied
“You don’t have to. Go down on your knees, have a look. Don’t worry I won’t press you. Take your time.”
I sank to my knees and his cock came level with my face. I still had hold of it and I gently wanked him as I stared at his genitals, licking my lips, wondering if I could…
Could what. Suck this total stranger’s cock? Make him cum?
He didn’t give me a lot of choice. That isn’t to say he made me. 
No, he just took a step forward until his hot, throbbing, warm cock was about half an inch from my lips. Then he just pushed forward until his lovely glans was brushing my lips.
My mouth just opened and I felt my first cock enter my mouth. It would be the first of many, but this was my first and I wanted to savour it.
I let him push it in as far as he wanted and waited for him to stop pushing.
With it about half in, he stopped. I felt his hands either side of my head.
“Look up at me Chris” With his cock firmly lodge in my mouth I gazed up at him.
“Just be gentle and suck me lightly, tenderly. Like it was your own.”
I pushed forward a little and felt him hit my throat. I gagged a little and pulled back, afraid he would push it right down.
Then I gently sucked him, pushing my mouth further onto him and then pulling out a little.
“Aaah that’s good.” He whispered. “Well done, you’re a natural. I’m going to cum soon. Do you want to have it in your mouth ?”
Well, I really wanted to please this wonderful man who was giving me this experience. I wanted him to  know that I was very grateful for his gentleness with me and I wanted to repay him.
What happened was I said “Yef” around a mouthful of his gorgeous member.
“I’ll take that as a yes then Chrissy” he said, his breath coming quicker. His hands tightened on my head as he started to pump his beautiful weapon in and out of my eager mouth.
I didn’t do much to be honest, just let him use me.
Then he was cumming. He was a heavy cummer and I have to admit I spluttered a bit as he filled my mouth.
But it was exciting. I had never felt so sexy and wanted by another person in a sexual way.
“Oh Chrissy, Chrissy look at you with my cum leaking out of your mouth. You look so goddamn sensual. Wank yourself now. Cum with me Chrissy.
My hand strayed to my cock and before I knew it I was splattering the ground with my seed as his deflating weapon slid out of my mouth.
He looked down at me and his thumb caught some stray cum and pushed it into my mouth. Eagerly I lapped it up and then swallowed all that was in my mouth.
I was eager to thank him but I was lost for words. I didn’t know if I wanted to run away or ask him to do it again. I was totally out of my depth.
“Sweetie” he said “Do you think you could be back here tomorrow ? I have so much to show you”
And I said yes
But that’s another story.

And here is the next part of the story.
We had agreed to meet at two in the same place. But  I was back there at half one, naked waiting for him. I kept touching myself and then stopping , sure I would cum if I did.
Then I thought I would go. This was all too much… but I didn’t.
I worried about other men coming in and forcing themselves on me. Could I stop them? Would I stop them?
Then Brian was there, walking into the clearing and everything became alright. My heart slowed and my cock rose as I saw him walk towards me.
He stopped in front of me and pulled my face to his and kissed me. A long, passionate kiss, me feeling his tongue around my teeth and almost fainting with the experience of it all.
Then he stopped and I felt… bereft. I wanted his sweet mouth, tasting of Wrigley’s gum back on mine, kissing me, treating me like I was his.
And, truth be told, I was. If he had told me to walk naked back to my bike and cycle home starkers I would have done.
“Hello Chris. Ready for some more fun?
I nodded.
“Kiss me again please Brian. It’s such a turn on.”
“In a little while Poppet” he replied. “Today I want you to go down on me then I’m going to introduce you to the delights of being fucked.”
He must have seen the concern on my face because he came close to me and kissed me again then broke off and whispered in my ear.
“Don’t worry sweetie, I’ll take it slow and we’ll have a good time. OK?”
I could only nod.
“You trust me don’t you?”
Another nod.
“Then get down on your knees and get ready whilst I strip.”
I sank to my knees on the loamy earth, aware of everything around me. The birds singing, the feel of the ground on my knees. And my cock vibrating like a tuning fork as I envisioned what would happen to me in the coming minutes.
Now you have to remember, when I was this age there was no worries about STD’s or anything like that and bareback was common.
He was naked now and he moved towards me, his cock waving at me as he strolled over.
He didn’t wait, just pushed it into my mouth and whispered “suck me sweetie.”
And I did. Gently, like he had taught me. I sucked gently on his glans, drawing groans from him as I drew his gorgeous member further into my willing hole.
Soon he took over and I felt his hands on my head as he fucked my mouth for about two minutes. I just held still, holding my hands on my heels like a good little boy, soaking up the sensations as he reamed me.
Then it was gone and I bleated as he took it out. I looked up beseeching to him, but he shook his head.
“It’s time sweetie. Get on to all fours and push your bum up in the air for me, there’s a good boy.
I turned over and did as he said. I felt really exposed with my bottom pushed up in the air and my face flat on the ground. The only thing stopping me running was the fact that this lovely man wanted to teach what this kind of making love was.

I felt something cold run down the crack in my bottom and looked back.  Brian was putting down a tube of lube. Then he pushed his finger into my virgin hole. Just his middle finger, slowly, so slowly, forcing its way into me.
“Ooh you’re nice and tight now aren’t you ? I like that in a man. Lovely little virgin cunt for me to break in.”
I heard the ‘C’  word and started. Then I thought. ‘Well that’s what it is to him. I’m a girl for him to use.’
I felt seriously sexed up now, knowing that he was going to use me for his pleasure. I had a strange sense of pride that I was pleasing him and pushed back on his finger.
“Mmm that’s it, just rock back and forth on my finger Chrissy, just let it work its way in.”
And I did, pushing back until he was fully in me and then pulling it out until he was almost out and then pushing back in again.
As I did this, I was moaning a little and making little remarks.
“Oh Brian, your finger feels wonderful. I am so turned on by what we’re doing. I can’t wait for your cock inside me.”
Then his finger was out of me.  Almost desperately I pushed my bottom further into the air looking to get his gorgeous digit back in me.
I needn’t have worried. He pushed his finger back in, but this time with his index finger as well. And now he took control, fucking me firmly with both fingers, twisting them as he did, making my little hole more elastic for what was to come.
Then again his fingers were gone and he grabbed me and turned me over, laying me on my back.
“I want to see your face as I fuck you for the first time. I want to see the ecstasy on your face as I enter you and ream your little cunt.”
There was the ‘C’ word again and it had the desired effect on me. He hadn’t talked dirty at all apart from that one word and that one word was setting my world on fire.
Then he pushed my legs in to the air so they were doubled back on me and I felt his cock lay against my balls.
I whimpered again as I felt it slide up and down my thighs and rub against my own penis, almost making me cum.
Then he grabbed it and pushed it to the entrance of my bud. 
All the time he was looking at me. I thought it was with love, but more likely it was lust. After all, it’s not every day you get to deflower a naïve 20 year old and cum inside them is it?
He pushed and I felt his glans push into my anal bud. A harder push and I felt myself begin to open under the assault of his cock.
All the time he was watching my face, concern laced with lust. I suspect if I had a mirror the only look on my face would have been adoration as I was already in love with this man.
Then he pushed harder and I felt him pop inside me.
I won’t lie, that hurt. But not for long and his ministrations with his finger had helped as he pushed more of his turgid length inside of me.
“Are you Ok sweetie ? Because I’m not going to last long in your warm, tight bottom.”
I nodded. I remembered what I had read in the graffiti on a wall in a toilet.
“Fuck me please Sir. Please. Breed me.”
That did it I think. I didn’t know what the words meant, but he obviously did as he pushed himself in to the hilt, pulled back until he was almost out and then literally slammed it back in.
There wasn’t any more as I saw the look of pleasure on his face and felt his member pumping his seed into me. 
Reaching down, he grabbed my cock and rubbed me several times before I too had a shattering orgasm, shedding cum all over my tummy and chest.
We lay there for I don’t know how long, with his cock inside of me, warm and wet. When he eventually pulled out of me, I felt his cum run down my bottom. I thought it was the sexiest feeling ever.
We lay said by side and discussed what had gone well. I, of course, said everything. And he agreed that it was the same for him.
Now he wanted more and wanted me to meet his friends.
But as they say that’s another story.
I had arranged to meet Brian the next week. He had promised he would be bringing his friend George with him and maybe Frank as well, if he could get the time off work.
I shared my concerns about me and three older men and he told me not to worry as they would treat me with respect and not to be afraid.
Well the next week, I arrived early in the spot and stripped naked, wondering whether I should actually be doing this. I was sure I was a bit in love with Brian, but I didn’t know his two friends and could I stand to be fucked three times ?
I didn’t know, but my average sized cock did as it stood out from my body, giving me the seal of approval. There was no doubt that I was sexually aroused and that I was being  trained to be a slut for older men. I didn’t care though as my excitement grew as the time came near for them to arrive.
And then they were there. Three of them. My Brian and Frank and George.
Frank was well into his sixties, tall with a beer belly and a leering look to him. I didn’t take to him, but wondered if my burgeoning submissive nature would allow me to be turned on enough to be excited by him.
George was an unassuming man of average height with sparse salt and pepper hair, also in his sixties. He seemed a bit ill at ease, but looked at my naked body hungrily, like he wanted to ravage me there and then.
I sensed that this was not going to be the gentle sex that I had with Brian and that these two wanted a bit more of the rough side of gay sex with me.
Again, my cock told me that I wanted this as I made no move either to cover myself up or get dressed. I just remained on my knees and let them examine me.
I began to realise that this excited me. A lot. And that I was excited at my submissive thoughts of what they would do to me. I watched George massage his cock through his corduroy trousers and wondered what it would feel like in me.
“So this is the slut you’ve been hiding away then” said George “I hope he’s as tight as you say he is. I like a nice tight cunt.”
“Personally, I hope that he’s as good a cocksucker as you say Brian” Frank said “I want to stretch his throat with my cock”
“Oh he is” Brian said “I promised you a new slut and here he is”
I was distressed at Brian’s change in attitude towards me.
“Brian, I thought that you liked me and that you cared for me. But it doesn’t seem like that now”
“That’s because I don’t” he replied. “I realised from the start that you are a submissive slut and that you would turn up this week. You would have turned up if I said I had half a dozen friends coming, wouldn’t you ?”
I said nothing, looked down at the floor. His words shamed me, but this just made me more excited. I was embarrassed and humiliated by their attitude towards me, but the overwhelming sentiment was one of raw sensuality.
His boot came up and nudged my cock. I flinched from it. 
“Look, that wouldn’t be stiff if you didn’t want to be used would it ?” 
He nudged my cock with his boot again when he didn’t get a reply. 
“Would it ?”
“No” I replied in a quiet voice
“No Sir” he said. From now on you call us Sir. Do you understand ?”
“Yes Sir” I replied still looking at the ground
“Are we done fucking about here ?” said Frank. I want some of this bitch. She looks like she needs breeding.”
I looked up and saw he had taken his shirt off and was busily divesting himself of his trousers and pants.
As his pants came down, I saw his cock. I couldn’t take my eyes off it. It was about seven inches and quite fat and rigid. He was obviously well excited by the thought of taking this naïve slut.
As soon as he was naked, he walked over to me and grabbed my head, pushing my face up and pushing his Manhood towards my mouth.
“Do you want my cock then ? Because you’ll have to ask for it if you do.”
I did want his cock. I wanted it more than anything. I wanted it in my mouth, so I could suck it and then feel it pumping in and out of me.
“Please can I suck your cock ?” I asked in a timid voice
I didn’t see the slap coming, but he planted his open hand on my cheek, rocking my head back. It wasn’t a hard slap, but nonetheless shocking for me.
“Please can I suck your cock SIR” he said. Get it into your head that you are owned this afternoon and you will do as we say”
“Yes Sir, sorry Sir” I gabbled “Please Sir, I so want to suck your cock Sir, please would you let me ?”
He pushed his cock towards my mouth and I had the scent of it in my nose. It smelt of urine and stale cum. When he pulled his foreskin back, there was a rind of smegma there.
“That’s it. Clean me before we start. That’s what you’re good for. A little cleaning bitch. What are you ?”
“A little cleaning bitch Sir”
I took his cock in my hands and licked around his glans, dislodging the stale smegma. It tasted sour and wrong in my mouth, but I had no choice but to continue.
I had no choice because he would have slapped me again if I had not. But I also had no choice because I found that I wanted to. I wanted to serve this gross, bully and please him. Please him by cleaning his filthy Manhood.
When I was done, he grabbed my head with both hands and plunged his cock into my mouth, sawing it an and out with no thought of what it was doing to me.
I coughed and spluttered as his Manhood pushed its way down my throat and then back out again. When I put my hands on his legs to stop the assault, he slapped them away. George came up behind me and grabbed my arms, holding them back behind me.
Now I was on my knees, with my hands being pulled out straight behind me, my body being pulled upright as Frank continued the assault on my mouth.
“I’m not going to fuck you at the moment” he said, panting. “I’m going to cum soon and you’re going to get it all.”
With that, he pulled his cock out of my mouth and wanked it furiously, his breath coming in short gasps as he came nearer his climax.
Then it was on him and he shoved his fat cock back in my mouth and I could taste his cum spewing into me.
“That’s it bitch don’t waste it. Make sure you drink it all. That’s first rate jizz that is. You don’t really deserve it, so make the most of it.”
Gradually, his flow slowed down  and stopped. As his Manhood came out of my mouth, he pushed it forward to be cleaned. Much to my humiliation, I eagerly leant forward to lick the little streamers and blobs of cum from him, before he took it away.
“And now it’s George’s turn. And he is going to fuck you” Brian said.
I had not realised that Brian and George had stripped off and I turned to look at George. He was not a particularly big man (though bigger than me), but what caught my attention was his cock.
It must have been ten inches long and quite thick as well. I couldn’t take my eyes off of it as it swayed in front of him. I quailed at the thought of it piercing my poor little bud, knowing I had no choice.
But still… part of me wanted it, to be pushed to take it, to be made to have that enormous weapon inside me.
I was pushed down onto my knees and then my bottom pulled up into the air. My head  was on the ground and my anus (my cunt, they called it a cunt) was poking up in the air as if I was a willing participant here. And I suppose I was.
A finger entered me, thick with lube and went in right up to the knuckle. I realised it was Frank and he was enthusiastic about the way he went about it.
He pulled his finger out and put two in and sawed them in and out.
Then he stopped with his fingers deep inside me.
“Hey bitch, fuck yourself on my fingers. Go on, you know you want to”
I pulled my self forward and felt his fingers come away from me. Then I pushed back and felt him enter me again. I started a rhythm, feeling his fingers loosening my… cunt as I pushed and pulled him in and out of me.
Then he took them out. Just left them tickling the periphery of my cunt. 
I couldn’t help myself as I desperately pushed back to get his fingers back inside of me. Every time I thought I  was near, so he would pull away.
In the end, I gave up, actually whimpering with frustration.
Frank roared with laughter
“Look at you, you slut. You just love being fingered don’t you ?”
When he didn’t get an answer, he slapped my bottom. 
“Don’t you ?”
“Yes Sir. Please Sir, I want your fingers in me again” The words tumbled out of me. I didn’t want to say them, but… I did.
I felt his fingers come back into me, the index and middle as before. But then I felt him worm his third finger into me as well. And I groaned as he opened me up more.
“Don’t moan bitch. You’ll thank me when George takes in a minute”
Then he added his thumb as well and I felt my cunt begin to gape open.
“You’ve got a nice gape there” Brian said
Then his fingers were gone and I felt George settle down behind me, pushing his monster up against my pert little bottom, sliding it in the crack of my buttocks.
“Hold your arse crack open” he ordered
Obediently, my hands went to my bottom and pulled my cheeks apart, revealing my abused cunt to him.
The next thing I felt was his mushroom head pushing against my little bud. He pushed and then shoved it and I felt it pop into me.
It was a relief of sorts as his monster head was inside me now. 
I got my hands underneath me and pushed myself up.
Frank came down to my level and put his face in mine.
“Bet you’re glad I wore you in now aren’t you ? Say thank you”
“Thank you Sir for fisting me and preparing me for Sir’s monster”
And then George was pushing his whole ten inches inside of me. It felt like he was going to go on forever. I gritted my teeth and waited for him to all be in me.
Eventually, I felt his large balls bang against my bottom.
“Nice and tight” he said. “ I won’t be able to hold off long fucking this one”
Then he pulled back and I could feel him almost leave me, then he pushed it all the way back in again.
“Like that do you ?” asked Brian
And I did. I wanted him in me so much that when he pulled back I was whimpering for him to push it back into me again. I could barely speak.
“Yes… Sir… I love his cock deep in me. I want to be bred. I deserve to be used like this.”
George had now got a rhythm and was sawing his monster cock in and out of me, getting faster and faster as he reached towards his climax.
I was making inarticulate noises as he fucked me, my head coming up, mouth open… which gave Brian the perfect opportunity to fill my mouth with his eight inches.
Now I had George reaming my virgin cunt, banging away harder and harder and Brian in my mouth pushing his cock into my throat and pulling out again.
Something had to give and George gave one last huge shove and I felt him explode inside of me, his cum coating my insides and dripping out around his cock.
Soon after, Brian shot his load, half over my face and then the rest in my mouth, me eagerly lapping up the rest.
Slowly, we all came down from the high and I felt George slip out of me. I rolled onto my back exhausted. 
But they hadn’t quite finished with me. Frank came and squatted over me, wanking himself again, and then cumming all over my cock and balls.
“Go on slut, rub it in and bring yourself off. You know you want to”
And I did, feeling his cum over my cock as I massaged it into my skin and then my glans, letting it lubricate my hand.
I could feel my orgasm building and then Frank put his hand over my mouth, spreading cum over my face. Eagerly, I  lapped it off his hand.
That was too much for me and I had the most enormous orgasm shooting my cum all over my tummy and chest.
As I lay there panting, feeling cum truckling into my mouth and out of my cunt, the others were getting dressed.
Brian came over to me.
“You don’t have to be here next week. But I bet you will be. I have another two men lined up so there will be five of us. See you then”
And do you know what ? I was.
But that’s another story.