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My First Time

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By *ville_guy OP   Man
4 days ago

Waterlooville

This is the story of my first time having sex with another man

So I knew from quite early on that I was bi-sexual, although I never admitted it out loud. I spent most of my teenage years sitting shoulder to shoulder with my best friend of 6 years wanking, whilst watching or looking at any porn we could get our hands on but mainly the 10 minute freeview you used to get on the TV at midnight before the pay-per-view stuff came on. Unfortunately I was too much of a chicken to act on it, although we both knew we wanted to as we ended up just watching each other wank in the end. The only time we ever took it slightly further was when we kissed in a bush and rubbed our cocks together, I would always think about that moment everytime I wanked or we wanked together and it would later be the reason I finally indulge in the greater side of sex.

Most nights I’d be up until stupid hours on the computer, starting with porn and eventually drifting into erotic stories. The ones that really got to me were always the “based on a true story” ones, which would always lead me back to those bushes and started sending my fantasies wild. This finally led me to roaming through local chat rooms talking to other people and exploring my bi-sexual fantasies.

It would probably be about 8 months after my first visit to the chat rooms that I would finally pluck up the courage to meet someone. Colin would usually be waiting in the chat room for me and we spent probably 4 months chatting, and wanking to each other on webcams, we tried numerous car meets and he was very patient with me after numerous last minute cancellations from myself due to my nervousness. Colin was early 50's, average build but probably had one of the nicest cocks I had ever seen, it was about 6 inches, quite thick with a perfect foreskin which didn't quite fully cover the end of his bellend but when you pulled it back it revealed a huge bellend that had an extra large slit.

This paticular evening was in the middle of summer after my 18th birthday, nice and warm and I was in luck my mum was away and my older brother was staying at his gf's for the night so I had the house to myself. Knowing this I decided this would be the night I would finally go through with it and I would get to hold another mans cock, and being at my own home I felt somewhat safer. As usual I went into the chat room and a private message instantly popped up, it was Colin, butterflies filled my stomach and I started to type, we started with all the usual "how are yous?" "Good thanks, but Very horny" etc. Then I explained the situation and asked if he wanted to come over for a few beers and some fun, his reply, a swift "yes", which instantly made my cock start to grow. He asked a time and I said whenever he was ready, he asked for my address and once again the butterflies returned as I started to type my address. This was it, I was finally going to kiss a man and feel another mans cock in my hand, and then I hit send, his reply was see you in 30 minutes sexy. The nerves instantly kicked in and I felt myself wanting to cancel, but I grabbed a beer and necked it to calm my nerves. It somewhat worked but I thought putting on some gay porn would make me horny subsiding the nerves as I imaged it was me and Colin. I put on my favourite video 'Chad Douglas fucks twink' as I watched, my nerves started to dissapear, I lowered my shorts down struggling to get them over my now erect cock and then out sprung my pre-cum soaked cock. I took the empty beer bottle that I had just finished and slowly lowered myself onto it imagining it was Colin's cock, about 15 minutes had passed and the nerves had almost dissapeared I decided to open another beer and then clock watched. 35 minutes had passed and I thought he wasn't going to show and then I saw his Silver Pegeout 305 pull into the end of the cul-de-sac. I watched from the window as he got out his car, he was wearing shorts, a slighlty baggy T-shirt and a baseball cap, my heart started to beat out of its chest as I proceeded downstairs to meet him at the door.

I opened it before he got to the door and invited him in with an almost whispered hello. He walked straight into the lounge which was just off of the porch separated by a door. He asked if he could use the toilet as he was "dying for a piss", I showed him to the downstairs toilet which was directly next to the front door. I think he sensed I was really nervous as he started saying how good it was to finally meet and we could take it as slow as I wanted, as he was saying this stuff I couldn't help myself and I walked back into the porch so I could see him taking a piss and I finally got my first view of an older mans cock in the flesh, he looked at me, smiled and then made a comment about the bulge which was growing in my shorts. I am not sure how long I had been staring at his cock for but he put it away swiftly and said "how about this beer then?"

Let me know if you would like me to continue, this is also my first ever story I have written, so apologies if it isn't great.

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By *Jexpert555Man
4 days ago

Southend

Great start, would like to hear more

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By *on779Man
4 days ago

colchester mersea

I’d like you to continue think it’s great!!

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By *ich65Man
4 days ago

Chorley

Great start, look forward to more 🔥🔥😈

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By *eadar123Man
4 days ago

dublin

More please

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By *i Biker60Man
4 days ago

bitown

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By *reenland1Man
4 days ago

Paisley

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By *ef123Man
4 days ago

Felixstowe

😈😈😈👍

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By *harliesfunMan
4 days ago

North Tyneside

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By *nts hornyMan
4 days ago

Derby

Very nice pleasure tell us more

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By *rjizzMan
4 days ago

nearby

Yes pls!!!

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By *esley 60TV/TS
4 days ago

PERTH

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By *igh_22Man
4 days ago

glasgow

Very well written. Looking forward to then rest

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By *ingbongMan
4 days ago

hull

Great start, please carry on xx

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By *asher72Man
4 days ago

Newton Abbot

Nicely written and going in the right direction. Please let us have more

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By *yrman57Man
4 days ago

Ayr

Looking forward to the continuation.

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By *ville_guy OP   Man
4 days ago

Waterlooville

I came out of my cock staring daze and had Colin follow me back into the lounge and then into the kitchen. As we walked through Colin gave my arse a firm squeeze and commented on how firm and pert it was and that he couldn't wait to see it in the flesh. A whole new sensation rushed over me, my arse had been squeezed before but that was by girls at teen discos. This however, was a hand which covered my entire cheek and belonged to a man who was older than my dad, and was now standing inside my kitchen, my cock twitched like it had never done before and I felt a whole new wave of horny rush over my body as the surreal feeling hit me that there was 100% no going back now.

I grabbed a beer for Colin and myself, opened them and asked if he wanted to go sit in the garden as it was a warm evening. He accepted and we walked through the kitchen out onto the decking and I grabbed some cushions from the shed for the seats, I sat down and was hoping Colin would sit opposite me as I had invisiged rubbing his crotch with my foot would be hot and ease me in slowly, but he decided next to me would be the spot. Which I am sure will be agreed was indeed the correct spot. My house was in the corner of the cul-de-sac, so we had the largest garden in the street, behind us was a large mechanics garage which had no view into our garden, as did my neighbour to the left and the neighbour to the right wasn't in so I knew we were safe from peeping eyes and ears.

Colin sensed I was still nervous as he sat next to me, but I think he soon realised that the horniness eased my nerves very quickly. As Although we had gone through the same conversations online before, he asked me them again and what I was into and wanted to do this evening, maybe it was to test me to see if I was a keyboard fantasist. The instant I started to explain my cock grew and that new sensation returned and the nerves went, I explained I would like to try kissing, sucking and to be fucked for the first time. I asked him if he had anything he wanted to try and he just replied with you and everything you've just mentioned. That comment definitely made my cock twitched and I could now feel a moist patch growing in my shorts from the pre-cum. We continued with small talk and I explained how I became to realise I was interested in guys, and as I was speaking I looked down and could see a pretty hefty bulge in Colin's shorts. I got the feeling I used to get when me and my friend would sit next to each other wanking, the feeling that I was always so scared to give in to. My heart started beating ten fold again and I just reached over and placed my hand on his bulge, I couldn't beleive it, I had done it, I was touching another mans cock albeit outside his shorts, but it was now filling the void of my hand and I loved it. It felt very surreal and an annoyance crept into my head that I hadn't done this years ago with my best friend. That annoyance quickly vanished when Colin reached over and placed his hand on my inner thigh, I thought this was going to be an American Pie moment where I would explode just by a simple touch.

Colin took a swig of his beer, as did I and then he lent in, with his hand still on my thigh and with this new found feeling of an almighty horn, I met his lips with mine pretty quickly and forced my tongue into his mouth. I don't think he was expecting me to be so eager because he placed his beer down so he could re-adjust himself a bit better.

Now the next few minutes were kind of a blur but I remember the kissing was great and very passionate and I moaned A LOT. Colin would later tell me that the moaning whilst kissing was the biggest turn on that evening and instantly made his cock rock hard. I felt his cock growing as I was still rubbing it outside his shorts, his hand was still slowly rubbing up and down my inner thigh until it happened. He took his hand of my thigh and grabbed my rock hard throbbing cock from outside my shorts, again, another new wave of feelings rushed over me as I pushed my lips and tongue into his even harder and making a involuntarily moan which he seemed to enjoy as he grabbed my cock even harder and adjusted his crotch so I could now get my hand around his cock too, his cock felt huge as I slowly wanked his cock over his shorts and boxers and I had to push his hand off of mine as I was ready to explode. After about 5 minutes of kissing I was quite aware I was being loud and suggested we should probably go inside just to be safe, Colin agreed and we both got up, left our beers on the table and proceeded to the lounge.

Thanks for all the messages, I am thoroughly enjoying writing this from memory. I will add that although this is a true story some minor details have been added to make it a better read and length.

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By *on_canberleyMan
4 days ago

Frimley

Please keep going with the story

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By *ernne67Man
4 days ago

Shoeburyness

Keep going

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By *hrisukbishareMan
4 days ago

Edinburgh

Wonderful

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By *endeepMan
4 days ago

Gt Yarmouth

Very nice, just wiping my helmet with the leaking precum...cheers

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By *orfolklad90Man
4 days ago

Great Yarmouth

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By *nts hornyMan
4 days ago

Derby

Mmmmmm

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By *atcher23Man
4 days ago

Loughborough

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By *aypee46Man
4 days ago

Nuneaton

A great story so far

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By *kyluke69Man
4 days ago

Gravesend

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By *ravelguyMan
4 days ago

Ipswich

Loving this,please continue

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By *ature boyMan
4 days ago

Erdington

Lovely cant wait too hear more

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By *illmecreviceMan
4 days ago

Reading

I’m really enjoying this

What happened next?

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By *ab-biguyMan
4 days ago

;-) Pembs ;-)

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By *ville_guy OP   Man
4 days ago

Waterlooville

As we walked through the kitchen I looked down and saw a huge wet patch on the front of my shorts created from the copious amounts of pre-cum I had leaked, this made me smile and every ounce of nerves I once had were now gone and replaced with excitement. As we walked into the lounge, I walked over to close the curtains just so no neighbours could see in from the street side, although I am sure most would have loved the show. I turned round and Colin was stood in the middle of the lounge between the two sofas, I walked over with excitement and again our lips met, tongues were intertwined and my moans became evidently louder knowing no one would be able to hear.

As we continued kissing with immense passion, Colin reached down and placed both hands inside my shorts and firmly grasped each cheek pulling my groin into his, so our cocks pressed against each other through our shorts. Colin then proceeded to slowly grind our cocks together and then using his index fingers he reached inside my crack and parted my cheeks ever so slightly, with my hole slightly spread and his fingers millimetre’s away from my virgin hole I couldn’t take it anymore and needed to feel his bare cock in my hand.

I pulled my cock away from his and began to undo his zip so I could reach inside the front of his shorts, I still have a very vivid image and feeling of that first time holding another mans cock in my hand. It’s massive I thought to myself as I now had my hand wrapped around Colin’s bare cock which led him to pull away from our kiss and moan but to make sure this is what I wanted.

I will say that I couldn’t have asked for a better first-time experience, Colin was gentle (when needed 😉) and always checking I was okay.

Colin soon realised that I was perfectly fine with how this was going as I proceeded to slowly wank his cock whilst kissing him again. Colin then proceeded to tug at both sides of my waistband so my shorts came down enough to free my cock, Colin grabbed my cock and I remember the warm yet cooling feeling of his hands against my foreskin and the sudden fear that I might be about to cum, and that would be it over with. I pulled away sharply with his cock still in my hand and asked him if we could wait a while for me as I didn’t want to cum instantly and then not want to continue. He agreed, and with a firm hand grabbed my shoulder and guided me onto my knees making the remark that he would love for me to suck his cock. I slowly went down and got to my knees, whilst Colin removed his shirt prompting me to remove mine too, Colin’s bulge was now at eye level, and another wave of feelings came over me.

I had watched numerous porn videos of this moment when a guy pulls down the shorts and the cock springs out and fantasised about being in that position and now here, I was. I eagerly tried to unbutton Colins shorts but had a little trouble so he helped, and as I slowly pulled at each leg of his shorts, the moment I had fantasised about, finally happened. Colin’s cock sprang out and I was now inches away from it. I remember looking at it for a few seconds and just admiring it, especially the huge slit and leaking pre cum. I got closer to it as I wrapped my hand around it to admire its beauty and lapped up the precum oozing out of the end. Colin let out a little moan, and I began to slowly put my lips around the end of his cock, it felt strange but a good strange and I slowly worked my way down it trying to think what I would want from a blowjob to feel good. Colin’s moans were a clear indication that I was doing something right, occasionally I would go too far, and it would cause me to gag, this made my cock twitch and made me think that maybe this is a good thing. Occasionally I would pull off Colin’s cock and then would stroke it looking at how his big helmet would burst out when I pulled the foreskin back.

Colin suggested that he moved to the sofa for comfort which I agreed to, I remained on my knees as he moved over to the larger sofa of the 2 and took a seat. I quickly crawled over and assumed position between his legs and in front of his cock, making me look like a right cock hungry twink. I began to work at his cock again and tried to slowly get it further down my throat each time, knowing that every time I gagged my cock would twitch, causing it to bounce and leak more pre-cum. Colin’s moans continued and after about 3 minutes he adjusted himself so he could reach over and grab my arse again. Then I heard a sucking noise and that’s when it happened Colin reached over and rubbed his wet finger over my hole and applied a tiny amount of pressure, my whole body shuddered and the feeling of another person touching my hole made me turn into a sex crazed animal.

I took hold of Colin’s other hand and placed it on top of my head guiding him to start forcing my head onto his cock. This made me gag and tears started streaming down my face, but I loved it, all the while Colin was still probing at my virgin hole. Colin took my eagerness as a sign to get things moving forward, so he slowly inserted a finger into my hole, it slipped in with ease as I had previously used the bottle to pleasure myself before he arrived. Colin was surprised as he slipped two fingers in and remarked how easily they had entered my twink hole, I told him what I had done whilst he was en-route here. His eyes lit up and he asked me to get on all fours on the sofa, this is it I said to myself I am finally going to feel an actual cock inside me instead of all the implements I had been using for the past 3 years or so.

Thanks again for the private messages, apologies for not responding, there have been quite a view. The next part will be the final part and what I presume you have all been waiting for

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By *ature boyMan
4 days ago

Erdington

This is great

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By *ustcuriousgeorgeMan
4 days ago

Shropshire

Brilliant story and great writing

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By *erricMan
4 days ago

home

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By *asher72Man
4 days ago

Newton Abbot

I’m leaking 🍆💦

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By *illitMan
4 days ago

Knaresborough

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By *imassagesharerMan
4 days ago

Northampton-East

Colin is a very lucky guy having such an eager lover, you sound gorgeous

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By *illmecreviceMan
4 days ago

Reading

Lovin it

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By *urgye2001Man
4 days ago

southampton/ealing

Question is first time for what? Playing with another man's cock, me too young to mention, getting my cock sucked, again too young to mention, sucking another cock, can't really remember, getting fucked, attempt early twenties, and fully fucked, early 30's by working guy in his early forties when we were the only ones in a public toilet. He stood behind me, yanked my jeans and u/pants down , made me bend over toilet bow when me 32, I felt spittled fingers at my hole, so I realised what was about to happen, thought at long last, let it and sure enough felt his knob probing my hole, it was pushed in, and the full length followed, asked him to stay still for a while, he said not and proceeded to hump me for 5 mins till he stopped, asked him if he had climaxed, yes and his cock was withdrawn. THAT was my first time but next 6 weekly fuckings I got from him. So he broke me in initially and got 6 more fucks in me.

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By *urgye2001Man
4 days ago

southampton/ealing

next was a guy called Frank, met in the Biograph, took me back to his flat in Chelsea, stripped my trousers etc down, bent me over the bath and fucked me till he climaxed. Before Aids days.

A young Spanish guy I met in that cinema came back with me, stayed the night, fucked me when first in bed, and during the night and again when waking up. He came to stay Sat nights for next 12 months. He eventually got married.

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By *urgye2001Man
4 days ago

southampton/ealing

next was a guy called Frank, met in the Biograph, took me back to his flat in Chelsea, stripped my trousers etc down, bent me over the bath and fucked me till he climaxed. Before Aids days.

A young Spanish guy I met in that cinema came back with me, stayed the night, fucked me when first in bed, and during the night and again when waking up. He came to stay Sat nights for next 12 months. He eventually got married.

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By *xcuriousguyxxMan
4 days ago

mostly browsing just now

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By *unwithuMan
4 days ago

Manchester

Looking forward to the next chapter

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By *harliesfunMan
3 days ago

North Tyneside

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By *iffy1968Man
3 days ago

all over the UK

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By *iffy1968Man
3 days ago

all over the UK

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By *ab-biguyMan
3 days ago

;-) Pembs ;-)

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By *ich65Man
3 days ago

Chorley

Looking forward to the next chapter OP. 🔥🔥🔥🔥😈

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By *ravelguyMan
3 days ago

Ipswich

Me too

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By *ikki1970Man
3 days ago

leicester

Looking forward to hearing the further adventures with Colin.

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By *umlover71Man
3 days ago

Lowestoft

Loving this story. X

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By *evansmileMan
3 days ago

Macclesfield

Lovely story, very arousing, please go on!

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By *ature boyMan
3 days ago

Erdington

anymore please,,,,

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By *teveapriestMan
3 days ago

Kearsley

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By *ature loverMan
3 days ago

.

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By *arlislebbladMan
3 days ago

carlisle

Awesome. More please

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By *aveygMan
3 days ago

North West

Hell, rock hard reading this

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By *ickrandom1Man
2 days ago

here

More please x

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By *orth yorks guyMan
2 days ago

Castleford

More please

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By *eddyfMan
2 days ago

Rainham

Great

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By *asc.btm.Man
1 day ago

North east

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By *ville_guy OP   Man
13 hours ago

Waterlooville

Oh, how I was wrong, feeling like a complete slut being in the position I was in, I put my head down to prepare myself and that’s when I felt another new sensation which caused my cock to leak a huge stream of pre-cum. Colin had put both hands on each cheek spread me apart and started to rim my hole, the feeling was intense and a feeling I will never forget, I imagined it was similar to what women felt when they had their pussy licked. I unintentionally pushed back into Colin’s face, and he took this as a please proceed motion. Colin worked on my hole for about 3 minutes switching between his tongue, fingers and lightly slapping my arse, this made me very relaxed, horny and ready to take his cock.

Colin stood up and asked me if I was ready to take his cock, I agreed and he slowly started to guide his cock to my hole, I remember feeling a slight bit of pressure and then I tiny bit of pain. Colin told me to hold that position for a minute until my hole was stretched and willing. Well, I think the excitement got the better of me because after about 5 seconds I felt my hole loosen and I pushed back onto his cock to which he grabbed both my hips and let out a loud moan, holding me onto his cock. We proceeded in this position for a couple of minutes and then he asked if there were any positions I wanted to try, now I was a sexed crazed teenager but apart from women and the standard doggy or missionary position I wasn’t sure. Then I thought about my little nerve reducing exercise I had done prior and thought about the Chad Douglas porno and what position’s he fucked the twink in, so I said I wanted to go on top and bounce on his cock. He thought that maybe we would just try me on top without the bouncing, to which I agreed. So, Colin laid on the floor in the middle of the lounge and ushered me over to get on top of him. Now this made me feel even more like a slut, as I was now reaching behind and holding his daddy cock and guiding it into my hole. Colin pulled me in for a kiss as his cock slid back into my hole and I slowly started to ride him; I sensed that Colin liked this position more as his moans became quite loud and he would start whispering in my ear asking if I liked his cock being the first one inside my hole. Then he spanked my arse pretty hard which again brought me out like a wild animal, I moaned and asked him to fuck me hard like they do on the pornos. He had me lean slightly forward so he could get the movement he required, lifted his knees and he started to slowly increase his speed all whilst making sure my cheeks were spread and checking every 10 seconds or so if it was hurting. After the 4th time of asking me I greeted every cock thrust with a push back hoping he would get the hint, which he did as he skilfully pounded me for what seemed an age and at this point with my cock pressed against his stomach and the movements we were making I could feel myself ready to explode so I asked him to stop. He was concerned that he may have hurt me, but I explained I still wasn’t ready to cum, so Colin told me to lift up and lay on my back which I obliged to all the while his cock still inside me. As I lay on my back Colin reached over for a cushion from the smaller sofa and placed it under my back so he could get a better angle to fuck me. He told me to hold onto the back of my legs just under my knees, so he had view of his cock inside my twink hole and asked if I was ready. I replied with some slutty remark, and he then proceeded to pull all the way out and then slowly re-enter until my hole was fully stretched and open to receive him each time. He gradually increased his speed and depth each time until it was at a good constant speed that came out every time and then was balls deep when he put it back in. I remember this going on for quite some time and the pleasure was insatiable, it had me saying all kinds of things to Colin which seemed to make him more eager to get more out of me.

Colin then said he was ready to cum and asked me where I wanted it, as I had only tried my own cum before, I was very eager to have another person’s cum in my mouth so proclaimed “in my mouth”. I thought Colin was going to get me to wank or suck his cum out, but he asked me to get on all fours again which I probably did a bit too quick, as he jokingly said what an eager slut I was. Colin again spanked my arse and made a remark about the slut I was, and this time entered me pretty quickly which caused a huge spurt of cum to shoot from my cock, something I have never been able to do again ☹. This seemed to send him into a frenzy as he pounded me as hard as he could spanking my arse on nearly every thrust, at this point I am quite certain that my neighbours heard me moaning asking to be fucked harder. Then with one final thrust Colin said open your mouth as he pulled out of my now heavily pounded un-virgin arse and then unloaded spurt after spurt of cum into my willing open mouth, and you can probably guess that a drop wasn’t wasted as he shoved his cock to the back of my throat so every last drop was eaten up. The taste was slightly salty, but it was thick and creamy, and I knew from that point on the only place I ever wanted cum was in my mouth. As Colin pulled his cock out of my mouth, I made sure to savour the taste and smell and I proceeded to cleaned every inch of his cock, Colin called me a horny little slut as he pulled me up onto my feet. He leant in again and kissed me making sure his tongue swirled around my mouth so he could taste himself, and then he grabbed hold of what I can only describe as my now aching, pulsating and as hard as granite cock and said the words I never thought I would hear from a guy. “Now it’s your turn to cum in my mouth”, I am embarrassed to say, as I had never had anyone deepthroat my cock before but once Colin had wrapped his lips around my cock and within 9 or 10 deepthroat movements I probably erupted with one of the most satisfying orgasms I have ever had, to the point I think Colin was amazed at how much cum I produced. My cock became very sensitive as Colin continued sucking me for about 30 seconds after I came, so I had to pull him off, and to my surprise when he came up and kissed me again he still had quite a large amount of cum in his mouth and decided that I should share the load which turned me on immensely as I wasn’t even aware ‘cum swapping’ which I later found out that was what it was called, was even a thing.

After a little clean up I asked Colin if he would like to sit back outside and finish off our beers, to which he agreed, he went to put his clothes back on, but I proceeded to walk out naked and take a seat. Colin eagerly removed his T-shirt again and followed me outside and sat next to me taking a swig of his now warm beer. I went and got two fresh cold ones and we sat chatting for half hour or so and that’s when Colin introduced me to squirt, a much easier way to meet guys which sent me on my way to cruising in local wooded areas and then to meet another older guy who turned into a bit of a regular which a huge cock, which I have stories about if people would be interested.

Apologies for the delay in adding the final part but I wasn’t well yesterday so didn’t come on 😊 I hope you enjoyed my first experience, it sure got me going writing it.

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By *teveapriestMan
13 hours ago

Kearsley

:l

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By *ight n whiteMan
9 hours ago

Swindon

That's a great story. Really looking forward to hearing about other experiences you had

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