Chronicles of James - My gay experiences to date

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I'd responded to a thread on here about first times, and it was quite therapeutic to write down my experience.

It got me thinking that it'd be good to start documenting my experiences to date - if anything, as a release on my side, but also it might be of interest to some others on the forum, I personally like to read true stories.

So on that note, I'll use this thread to tell my own story about my experiences with men. All stories here are true, and I'll write them as real to what I remember. I'll be honest too about the experiences - not all of them have been positive for various reasons! Also, I'm not the greatest writer in the world, but hopefully some people will engage with this.

For context, my first experience was circa 2009 when I was about 23/4, so this will follow from there to present day. Some views from those earlier days may be quite outdated, so bear that in mind - I don't aim to cause offence.

I'll call each entry a "chapter", but they won't necessarily be big reads...so chapter is stretching it a tad...!

Chapter 1 is effectively the first time story I had posted on the first times thread....I'll drop it here though to begin.

Thanks, J x
 
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Chapter 1: James, meet James

First time ever with another man was when I was about 23/4. I'd put a "personal ad" out online (this was circa 2009) and started exchanging messages with a guy called James (same name as I weirdly!). We agreed to meet in Liverpool, so I took the train and he picked me up in his car.

He was mid to late 30s and quite tall, average looking but not unattractive, with a soft Irish accent. We didn't say much in the car and all I remember was my heart practically inside my throat as I thought I was going to get murdered...!

Pulled up outside a block of flats and he led me upstairs to the second floor, opened his door and welcomed me in. As soon as he shut the door he grabbed me and put my back to the wall, kissing me very intensely in his hallway. The guy didn't give me a second to take anything in. I felt like I couldn't breathe - mind was racing "omg I'm kissing a man" to "fuck I can't catch my breath". He led me into his bedroom and we both got naked and straight onto the bed.

I couldn't believe the size of his dick - I thought it was massive! It was the first time I'd ever seen another man's erection - it was probably about 7 inches but quite thick. I just wanted to touch it tbh, but I had no idea what I was doing. He told me to suck it, and I remember getting near to it and almost gagging - it had a vague smell to it which put me straight off. I put it in my mouth (it repulsed me) and then backed away, giving it a courtesy lick for a second or two and went back to kissing him. Not satisfied with my paltry attempt he asked me to suck him again and I just said I wasn't comfortable with it and kept kissing.

After about five mins of that and exploring his body with my hands, he suddenly asked if he could fuck me.

I thought, "fuck me, with that massive slightly smelly dick? Fuck off more like."

I was a complete anal virgin at this point so I again said no, I wasn't comfortable and hadn't ever done anal so it wasn't happening.

At this point, I think he was bored so told me to lie down next to him whilst we both wanked to completion. I hurridly got changed and he dropped me back at the station. Oddly, he kept talking about how he's besotted with some woman he worked with, and that loads of women are grateful to sleep with him etc all the way back to the station.

I remember having a cigarette outside the station (I don't smoke now, haven't for years) and almost wretching at the thought of his dick in my mouth - like I couldn't get the taste to go away.

Not my finest hour, surprised it didn't put me off meeting blokes!
 
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Chapter 2 - Pete

The night I got back from the odd experience with James, I found myself strangely intrigued about being with a naked man again, only this time I wanted a more positive, laid-back experience. So, onto the site I went again and put out an ad. Within minutes, I had a message from Pete in Manchester.

The first thing that appealed to me about Pete was that he could write well, used grammar properly and could spell. I was never into blokes who write lyke dis.

We set up a meet for the following day. I'd suddenly gone from being completely inexperienced with men, to meeting two different blokes in as many days!

I made my way to Manchester's Northern Quarter to a block of apartments hidden along a backstreet. Pressed the intercom, heart in the my throat again, and a welcoming voice let me in.

When I got to the apartment, it was huge - set inside a refurbished warehouse, with high ceilings, beams and open planned.

Pete was about 38-42 I'd say, 5 ft 7/8, medium build with short brown hair and a clean shaven face. Dressed casually, he had an air of calm about him.

We found ourselves in his kitchen, space separated us as we tried to work one another out. He was a good conversationalist, it didn't feel totally awkward (just a little), but he was good as asking me about myself and helped me to open up. I could tell he was a professional man with a decent job. He asked why someone like me would "resort" to an ad putting myself out there. I told him I was partnered with a woman and not "out", so wanted complete discretion whilst I explored this other side of me. He then asked about my experience to date and I told him, no holds barred, what had happened the day before.

He was taken aback, and was totally assuring about how not all blokes are like that. In a way, it felt he kind of took pity on me. He went to the fridge and took out some vodka: "Jesus, I feel like I need a shot after hearing that and it wasn't even me!" he laughed.

"Do you feel comfortable going to the bedroom?" He asked. Naturally, I agreed.

I sat on the bed as he closed the door. With some hesitation, he said "This is new to me too, not sure how to go about it" meaning the whole answering an ad thing and now having a stranger in his room. "Just come here and kiss me?" I suggested, and with that I had Pete pushing his body against mine as we kissed. It was different than yesterday, I felt relaxed, comfortable and was really enjoying the feel of this mans stubble brush against my face. His body felt warm, muscular and his hands were working their way around my body. This is how it should've felt.

Pete started to undress me. I stood up as he took off my jeans and pulled down my boxers. "Oh wow, you're pretty big" I remember him saying with a wry smile. He got down on his knees and put his mouth around my throbbing cock head. It. Felt. Amazing.

The warmth of his mouth, the feel of his tongue working its way up and down my shaft. I'd never experienced this before, and I was almost instantly addicted.

I brought Pete back up to my level and we looked at each other intently, before breaking into a passionate kiss, my hands frantically unbuttoning his shirt. I wanted - no - I needed - to see this man naked. His body was well proportioned, hairless aside from a few stragglers near his nipples. I started to unbutton his jeans and he stepped back to take them off, emerging to present me with a nice view of his hard cock. It wasn't big at all in comparison to my own and the one I'd experienced yesterday, but it was a good handful - maybe 5.5" length. One thing I remember thinking was "where are his balls?". He was all dick, his balls were definitely there but certainly not hanging down. It didn't matter, it was different to what I was used to and what my preconceptions were, but here I had a kind, passionate and naked man in front of me - I wasn't complaining.

I brought him towards me again as we continued to kiss, and I placed my hand over my cock and his, frotting together - the first time I'd ever done so. It felt incredible.

As I continued to fondle, I felt a sudden urge to cum - oh shit, that's quick I thought. I pre warned Pete and he lay down on the bed "shoot on me mate" he said - so I climbed atop him wanking away and blew the most intense load all over his stomach. My legs were shaking, my eyes wide open - what had we just done?

He looked at me and smiled reassuringly, he knew I was spent and rose to go to the bathroom to clean up. As he did, I got changed, and when he came back in the room he got changed too.

Making my way back to the front door, I said very little other than thanks and made my way home, not knowing if I'd see Pete again.....
 
Chapter 3 - Pete Pt II

**Note: this one does take a bit of a turn, maybe not for the squeamish**

It was a couple of weeks later, and after a few more messages back and forth, I was keen to meet Pete again for another session - only this time, I wanted to experience what it was like to fuck him. I asked during our message exchange if he'd be up for it. Initially, Pete was hesitant exclaiming that he doesn't "really do" anal but was more than willing to let me have my wicked way with him.

I remember being on the train on the way there and my dick was rock hard all the way just thinking about what it'd feel like fucking another man, reaching around and stroking his cock as I thrust inside him. In my head, I was thinking I'd be Brock Masters and he'd be Brent Everett from "Deeper in the Brig", one of the only gay porn films I'd seen at this point in my life and my usual wanking material. We both certainly didn't look like either of those blokes though ha! I was convinced the oozing precum in my trousers was evident to everyone else on the train - thankfully, it wasn't.

When I got to his apartment, it was the usual smalltalk before we made our way to the bedroom. We kissed like we'd not seen one other for years, passionately, tongues dancing as we writhed our bodies up against one another. Hands frantically trying to get one another undressed, to see each of our pulsating cocks taunt one another. Ecstacy.

Pete beckoned me on the bed, and asked "you ready?". I nodded, nervously, still rock hard and he handed me a condom. It felt like an hour before I could open it, fiddly thing, and I hastily put it over my cock, ready to make a big entrance. He flipped over and got on all fours, his manly but smooth arse luring me in.

I wasn't experienced with arse play at this point, so didn't touch, tickle, lick or kiss his arse - I simply spread his cheeks and started to nudge my dick head in him. As someone who now prefers to bottom, it makes me cringe that I was so selfish then!

His hole was tight, very tight. As soon as I got near him, Pete jolted forwards "ouch" he cried. "Are you alright?" I asked, he laughs "yeah, just been a while". I tried again....slowly does it and suddenly I was in...it felt different to my usual sex with a woman.. it felt dry and almost forced. I persevered, eventually getting the full length of my throbbing cock inside him. He took a deep breath and arched his back as I kept my dick in there, consciously throbbing it to hear him moan each time. My eyes were on him watching how he reacted to me being inside him, his eyes closed, his face different to what I'd seen before, "he's in a trance" I thought.

I start to pull out and thrust again, working up my rhythm slowly, it started to feel good, I could feel his arse close tightly around my cock, gripping it as if to coax my load up my shaft. My hands move around his front, I hold his package in right hand, his dick limp but sizeable. I then look down at my cock as I start to withdraw....in the throes of this magnificent experience, I wasn't expecting to see what I saw.

Shit.

Literally.

My cock was covered in Pete's shit.

Immediately, I felt completely turned off.

I backed away, and removed the condom carefully to make sure none of the mess touched my fingers. "You ok mate?" he looks back at me concerned. I could see the mess all over his arse, no longer teasing me but telling me to go away and clean up immediately. "Erm, just a bit messy think we'd best stop" I said. "Ah, yeah it can be mate it's ok no worries". I remember the smell to this day. This was the kind of thing I'd never seen in porn.

When I think back to this, having now had many more gay experiences, I feel for Pete as he must've felt slightly embarrassed, but equally, the anal was no surprise, sonI ask myself why didn't he prepare better? Was it timing?

I cleaned up, and made my excuses before hastily walking to the door to leave. All I wanted to do was run a hot shower over my cock and get super clean. In that moment as I was leaving, my attraction to Pete had waned and the prospect of topping another man seemed offputting.

Well, for the time being anyway.....
 
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Chapter 4 - Anthony (Escort Diaries Vol. 1)

It had been a while since the "incident" with Pete, and I hadn't heard from him nor had I reached out to him myself. Despite the less than ideal experience, I still felt the need for some man on man action - but where would I get it? I was loathe to put another ad online as in my head, the positives so far didn't outweigh the negatives. This was before gay hookup apps.

So I start googling and stumble on a local gay male escort site. "Is this legit?", I thought as I scrolled through the profiles of some unbelievably hot blokes. All sorts were there; chiseled, hairy, younger, older...and they explicitly offered sex. That was wild to me. Obviously growing up you hear about prostituting, and the stigma attached to it when it's women walking the streets, trying to get into cars. I was never one to even think about that, sex wasn't something I'd ever pay a woman for. But this? This felt different - these men were handsome, they'd been vouched for by other people like me, and it wasn't prostitution - it was escorting. Was that different? Maybe there's a discussion about that to be had somewhere else.

I kept reading, analysing the "customer" reviews. The hot guys with no reviews I dismissed instantly - were they fake? What would happen if I met them and they beat me up, stole my stuff and publicly outed me? I couldn't risk it, despite how hot they were.

I kept going back to one profile in particular; "Anthony". A tall, rugby-built and straight looking bloke. His photos were of him in sports gear, football kits, builders wear. He didn't 'look gay' to my eyes, when at a time I naively thought gay people obviously did have a certain look. He had a shaved head, stubble and was suitably hairy with thick thighs and a delightful chest. I didn't see his cock, none of the guys had their cocks on display on the site - the mind wandered. He was incredibly well reviewed though, having been escorting for a couple of years it appeared, and his manhood commented on quite a few times.

In my head, I'd made the decision - I wanted to meet Anthony, to suck his cock and to fuck him. Surely this guy would be ideal, he'd be clean, well presented, experienced and prepared. Plus, he was literally the epitome of what turned me on at the time - straight-looking hairy blokes.

On my way to the station travelling to work, I plucked up the courage to call him from my phone. When he answered, he sounded...well, a bit uninterested to be honest. I remember him mumbling, quietly, one worded answers. He asked me to text him with what I was after and so I did: I said I'm inexperienced, wanted a one hour in call, and I was looking to top a bloke.

We arranged our meet for a few days later at his house just on the outskirts of the city centre, easily enough for me to catch a train to. I got to the door of this unassuming semi-detached, about five minutes early, and knocked on. I could see his shadow through the door glass walk over slowly before he opened it up and gave me a glare. "Hi, I'm James", I said. He didn't say anything, just beckoned me with his head to come in and closed the door, locking it behind me. He was about 6ft 2 and deliciously masculine.

"Don't worry, not locking you in, just for privacy" he laughed. It was the first time I'd heard any personality from him, and it was strangely reassuring.

"We're upstairs" he mumbled, and walked ahead of me. I remember hearing the TV in his front room, "was anyone else here?" I thought, worried.

We got to the top of the floor and there were two bedrooms, one straight ahead and the other to the right. Anthony went right and sighed. As I followed, he was picking up his cat who had decided to snuggle on the bed. "Oh he's gorgeous" I said as Anthony moved him to the other room and closed the door. "Yeah, he picks his moments".

I stood in the room next to a chest of draws opposite the bed. Anthony just casually jumps on the bed, dressed in his black trackies and top, and sprawls his leg out. "So do I pay you now or after? I've not done this before, sorry" I ask nervously. "Whenever, I've locked you in now so you have to pay at some point ha" he said with a somewhat menacing grin. I laughed back, and took out my wallet counting the notes and laying the on the drawers for him.

"So how do you want to go about this then? I won't rush you, don't do anything you don't want to" he said to me calmly. That was nice of him I thought. "Erm, I'm not sure. Could I get a drink though? My throat is really dry" I asked. And it was - the nerves had been kicking in moreso than any other time I was with a man, and I was finding it hard to swallow. "God you're hard work" he laughed and he went downstairs to get me the drink.

Again, naively my mind was racing when he was making it. "Oh god what if he drugs me?" I thought. I couldn't shake that thought. I needed a drink, but convinced myself not to drink it all when he returned just in case.

As expected, he came back in with a glass of orange cordial and sat it on the unit, returning to the bed. I took a very small sip - it was enough - and took my coat and trainers off. I climbed on the bed and sat up next to Anthony. I couldn't take my eyes off his body - rugged, large but not fat, though not muscular either. Just manly.

"Take your time" he said, his face close to mine. I leaned in and we started to kiss. His mouth felt huge, like he was engulfing my face with each kiss. No tongues with Anthony though, he didn't put his in and I didn't want to make that move in case he wasn't into it. My hand rested on his thigh as we kissed, I couldn't help but think about that thick, hairy thigh under his tracksuit bottoms. I was throbbing.

I climbed atop Anthony, and started to kiss him around his neckline, feeling his stubble and my hands wandered up his shirt. The softness of his body hair was unlike anything else I'd ever touched, my tiny little gay mind was starting to blow.

I tugged at his trousers, and he started to pull them down to uncover his tightly packed black briefs. I could see the shape of his cock, already hard and waiting to be unleashed. I groped it, moving my hand up and down his thick shaft. I knew I had to see it, to feel it...I pulled his briefs down and moved to the side as he arched his back to completely free himself of his bottom clothes.

He looked magnificent. A thick, 7-8" hard cock complimented by a large set of shaven balls, hanging beautifully underneath in the midst of his burly rugby built legs. Lust took over as I gripped his cock at the bottom and went down to put my mouth over it.

If you'd read my first, and only, experience of sucking cock at this point in my life, you'll understand the benchmark I had here which was pretty low. But Anthony smelt shower fresh, his cock tasted sweet. I could suck that for hours. I remember the only obstacle for me to give him a great blowjob was his size. My mouth wasn't used to having something so thick inside it. "am I doing this right?" I thought, as I hastily made the most of this beautiful thick shaft in my possession.

I come up for air, and Anthony's still wearing his top. I start to take it off, wanting to see him in all his glory. I climb off the bed, keeping my eyes locked on his body and remove my clothes until I'm stark bollock naked with a raging boner.

"Pretty big yourself" he says as he beckons me back to the bed. We embrace as we kiss, his hands grabbing my dick and his, jerking them together. He moves toward the side unit and gets out a condom and some lube - removing the condom from its wrapper in a flash and starts to roll it on my bouncing cock.

He gets on all fours and I move in to mount his hairy manhole. He writhers around, sliding his arse against my cock - I knew he wanted it. I wanted it. But thoughts turned to Pete in that moment - what if it's dirty again? I couldn't concentrate, and suddenly my dick started to lose momentum.

I tried to shove my softening head into Anthony's manhole but it was no good - it wasn't happening. "What are you doing?" he laughed as he looked back at me. "Sorry" I mustered as I retracted and took the condom off. He flips over and reassures me "it's alright, don't worry, here lay down" - I lie down, stroking my dick which is now a semi boner, and he climbs atop of me, towering over me stroking his massive thick cock which certainly isn't shy like mine. I start feeling myself again, instantly turned on by this beast of a man wanking over me. "I'm gonna shoot over your dick" he says as he vigorously jerks his cock faster and faster before exploding all over my now raging cock. I grabbed my dick, using his warm cum as lube and furiously wanked it until I too exploded, my cum shooting so far I swear it hit the pillow behind me.

I lay there, catching my breath as Anthony climbs off me and throws me a towel. As I clean myself up, he's getting changed into his clothes, checking his phone and seemingly uninterested. "Thanks for that" I say as I begin to do the same. "Yeah no worries" he says, still looking at his phone. I get my trainers on, and my coat and we both go downstairs to the door, he unlocks it and says "see you soon" and I make my way back to the train station, feeling elated - I wanted more. That was the first time a bloke came on my dick - it was hot. I knew I wanted that again.