My entry into a bi life

by Free Spirit

2 Oct 2020 3669 readers Score 9.3 (39 votes) PDF Mobi ePub Txt


Before I start I have to state that I did willingly consent to everything that happened throughout this encounter and I was never physically harmed in any way. It was just rough roll play.

Let's begin......


The situation I found myself in all began as I approached my mid 20s and my relationship with my then girlfriend began to fall apart.

We both enjoyed going out with our mates and having a good time but for whatever reason our two groups of friends just didn't get along.

At first her friends seemed to like me but as time went on I would come to find out some of them would actively try to steer her away from me and encourage her to leave me. Around a year and a half into our relationship she confessed to me that on a night out with her friends something happened with another guy. We tried for another six months to make it work but I guess there were just too many hurdles in the way for that to happen. Then something happened that turned my whole world upside down and made me really look at my life in a way I never really had before which in turn prompted me to do something about being in a miserable relationship and move on.

Down at the local pub where we used to regularly go drinking, this new guy (Callum) started to work there behind the bar. He was a really good looking, 6ft, mixed race lad in his late 20s. He was really funny and always had a smile on his face. All the girls would fawn over him even though he told them from the beginning he was gay.

All the guys liked him because he was really into football and the usual lad things we all got up to. He also helped a few of them get dates with women that probably wouldn't have given them a second glance normally.

He'd been working there for a couple of months by now when one night during the week, me and my girlfriend had a bit of a row so I ended up staying down the pub. Last orders had been and gone and everyone else had left. Callum and the landlady had finished cleaning up. All that needed to be done was for her to cash up before we all went our separate ways and headed off home.

While she did that, me and Callum went out the back to smoke a "cigarette". He knew me and my girlfriend had a bit of bust up and offered me to come round to his so we can both have a bit of time apart and calm down. By now it wasn't unusual for a few of us to end up back at his after closing hours as he became good friends with us all.

Once there we sat on his two seater sofa, had a few drinks and talked about the usual lad stuff while we played fifa on his playstation. After a couple more we ended up talking about my relationship and how it wasn't really working out. At one point he jokingly said "Maybe you should consider moving on" while giving me a cheeky wink. 

Callum would often lightly flirt with the lads but we all knew it was just a little light hearted fun.

I joked back saying "Maybe it is. This obviously isn't making me happy". I don't think he was expecting that answer to be honest. 

"Why are you bi?" He asked, looking shocked. "No" I replied. "I'm just fed up". He then asked if I had ever thought about other guys in that way to which I told him I hadn't given it any thought. He left it at that and we carried on drinking and having a laugh.

Ofcourse I have but I never had anyone I felt comfortable enough with or had the trust in to be able to confide in them.

As the night went on and I got a little more drunk I began to think about it a lot more. A while later, Callum noticed I had gone a little quiet. He asked me if I was alright to which I replied "Yeh I'm good. I was just thinking about what you said earlier". He asked "Which bit?". I blurted out, "The bit about me moving on" while winking at him.

My secret was out. His jaw dropped and he said "You would have been the last guy I thought would have admitted that".

I could feel the blood rush to my head as I realised the gravity of what I had just admitted to. Callum noticed I had gone bright red. "There's no need to be shy" he said while grinning at me.

"What have I done?" I said as I hurriedly jumped to my feet and tried make my way into the kitchen to get another beer and I guess to try get away from the conversation I started, thinking it was a mistake.

As I began to scurry into the kitchen Callum grabbed my wrist and stopped me. He looked me right in the eye and told me "It's alright". It's alright mate, honestly. I won't tell anybody I promise". 

I made him promise again like you do when your unsure. "Thank you" I replied. I shouldn't have said anything. He asked me "why not?". 

I broke my hand away from his and asked if he wanted another beer. He said yes and left me to go ahead and have a minute to myself in the kitchen.

When I returned I handed him his beer and sat down beside him again. "I guess nobody else knows?" he asked. "Nobody" I told him. He said I don't need to worry and he was in exactly the same place a few years before. He put his arm around my shoulder and gave me a little hug and a nudge and told me everything will be alright.

Picking the playstation controls up he threw one in my lap and carried on as normal. We played for a while but knowing what I'd admitted to, I just couldn't concentrate and it must have showed. 

Callum put his controller down and said " So come on. Let's talk about what's going through your mind". He asked if I was okay to which I coyly told him I was. "So what is it then?". "Are you worried about me telling someone else still or are you just thinking about how big my dick is?" He laughed, making light of the situation and trying to bring a smile to my face. 

It worked. I laughed and told him "Both if I'm being honest". A wry smile washed over his face. "Oh really" he quipped while rubbing what I then noticed was a big bulge laid down his trouser leg. "I told you, your secret is safe with me". "Why don't you take it out and find out" he said while taking hold of my hand and guiding it towards his bulk. 

I pulled my hand back away. "You haven't done this before have you?" he asked. I shook my head as I felt myself go red once more. "I won't pressure you into doing anything you don't want to". 

There was a bit of an awkward pause before Callum asked me, "So what do you think about when you imagine yourself with another guy then?". "You don't want to know" I laughed out. He said "I'm sure it's nothing I haven't heard before". "I've probably had the same thoughts myself". I told him I was unsure if I should tell him because I wasn't sure if it's normal to think about thing's like that. "What do you mean?" Callum asked. After a long pause I told him "I don't I think I should tell you because I don't think it's something most people think about".

He quizzed me further, asking if it was all manner of normal things and worked his way up to some more hardcore things when he said "Alright, I think I've got it now". "It's pretty extreme isn't it and something you can't stop?". "I'm right aren't I?".

I told him it might be along them lines yes. He then said he assumed that I wasn't wanting to be a top. I wasn't aware of the lingo or terms used in the gay community at the time as I had convinced myself I was solely straight so I had to ask him what a top was. He explained and I said no I'm definitely not a top. 

"I am and I know exactly what you want" he said looking directly into my eyes while again rubbing his straining package. "Your right, not everyone will admit to wanting that but more people do than you would think I assure you" he replied. He then said most people will use a safe word when it gets too much to handle. 

I stupidly (or maybe not) said "But how would that be anywhere near authentic if you have a safe word?" to which he said "Ah ha, we're definitely talking about the same thing then". "It can be arranged someday if you really want to go down that road" he said while again guiding my hand onto his bulging crotch. This time I didn't pull away and I let him press my hand onto his warm, thick, long cock. He began to rub my hand up and down his shaft. Letting out a deep sigh he asked if I'd like him to fulfill my fantasy.

I realised the gravity of what he was asking and I said "Maybe another day" while smiling myself to try lighten the situation. 

He then raised my hand up his body with his while his other released his trouser button and undone his flies. He didn't give me chance to pull away this time and slid my hand down his boxer shorts onto his throbbing hard meat. It felt so big in comparison to mine. 

I'm an average 7 inch maybe slightly bigger if I use a ring but he is a good 8+ inch at a guess but it was his sheer girth that surprised me the most. I couldn't get my fingers all the way around it that's for sure.

Callum soon had his arm around me while I got to grips with stroking him gently and caressing his impressive manhood. In awe of his big cock and in slight disbelief of what was going on, he nudged me with his arm towards him.

Me, never being in this situation before and reading the signs wrong slightly, I slid off the sofa onto my knees and placed myself between his legs. "I only wanted a cuddle but don't let that stop you" he said while letting out a cheeky laugh and quickly jumping to his feet so his bulge was directly in line with my face.

He slowly pulled down his boxers and his dick sprang out in front of me like a NASA rocket about to take off. Callum assumingly taking onboard what I had admitted to earlier once again asked "Are you sure you don't want me to take control?".  I paused for a little while to think about what I wanted. In a haze of excitement and disbelief someone as hot as Callum was in front of me willing to oblige me my deepest darkest fantasy I blurted out "You know what, I think I do yeh".

He asked me if I was sure as he lorded over me. I nodded my head and told him nervously "Yeh" once again

He laughed, took hold of the back of my head and told me to open my mouth. He didn't mess around at all. I hadn't even opened my mouth at all before his shiny bulbous helmet was pressed firmly against my lips.

"Come on open that fucking mouth you little bitch" he growled. Not wanting to disappoint I did exactly as he asked and tentatively began to suck his helmet. I struggled to get my mouth that wide as it's too small to accommodate his big cock end with any kind of ease. He let me do my thing for a minute before telling me "Come on, put some effort into it for fucks sake" before getting a tighter hold of my head and pushing my head down onto his hard cock until it hit the back of my throat and made me gag. He held my head there for a while before letting me catch a breath again. A couple of seconds later he shoved his way inside my mouth once again and this time began to gyrate his hips. It wasn't long before he ramped up the tempo yet again.

He lowered his hips slightly and really got a grip of my head and shoved his massive member right to the back of my throat this time before pulling away. Not giving me chance to get a breather he pushed right back in again and again. Every time he seemed to try harder and harder to get me to take him in my throat. He carried on like this for a short while before he told me to relax my throat and let him in or he'll have to make it go down his way. I tried my best but I couldn't seem to relax. After another couple of minutes of trying he pulled out and pushed my head away so I fell back onto the floor. He told me to take my top off and be on my front by the time he came back. 

He went upstairs and I did as he told me while I could hear him rummaging around through draws and stuff for a while before he hurriedly ran back down the stairs. "Right, this should help sort your little problem" he said as I felt him sit on the tops of my legs. He leaned forward and whispered in my ear as he took hold of my wrists once again and pressed his toned body against my back, "You will take my cock in your throat boy won't you". 

Not realising it was a question with never being in this situation before, he shook my wrists and growled "Won't you?". I nodded and said "Yes" in shock that he could be so forceful as I had always known him as this cheeky but polite, light hearted guy.

He dragged my wrists behind my back and proceeded to shackle them into what I later learned were leather wrist straps.

Callum told me to roll over and get up. I did as I was told and he lead me over to the wall beside the door. He grabbed me by the throat and ran his thumbs over my adams apple while telling me "I don't know about you but I'm going to enjoy this". He slapped my face playfully and ordered me to my knees.

I did as I was told and he didn't waist any time in making me realise just how dominant he could be. He slapped my face with his big, hard, heavy cock and then slapped my face with his hand again before stuffing his rod into my mouth once again.

This time he didn't let me ease into it one bit. He pushed right into my mouth and took a tight hold of my head once again. This time more round the back of my head and neck. I tried to pull away and I soon realised why he positioned me against the wall.

I had nowhere to go. Callum laughed as he drove his thick dick into my mouth and began to force his way into my throat. I tried to wriggle my head free but his grip round my head was too tight. I tried to cough as he went in deeper but that only made it worse. I was seriously gagging. He urged me to relax or things are only about to get worse. I tried to do as he told me but as I looked down his shaft and realised I was barely a third of the way down his big dick. I began to panic a little.

I think he sensed this and he pulled out to let me get a breath for a few seconds before ploughing right back in. He carried on like this for a while. Shoving it in a bit then pulling right out then sinking it right back in again. This lasted a couple of minutes before he started to push me some more. He drove in deeper this time and held it there once again. Closing my eyes as I tried to relax and focus on what I was meant to do while choking on his cock. Coughing once again and nearly being sick Callum told me to look up at him while he held me tightly in that position. I couldn't bring myself to do it because I was struggling so much which only spurred Callum to be even crueler.

He sunk his manhood into my throat further and scathed "Fucking look at me you cunt". Panicking, I knew I had to do as he said or I feared he would just go harder.

I did as I was told. My head shook and my eyes streamed with tears as my mouth engulfed around half of his pulsing penis. Not because I was crying, it was because my throat couldn't handle him and the straining was too much for me to handle comfortably. Callum laughed at me and pulled out.

"Awwwwwww, Do you want some more?" he asked. "No that's enough. I can't take any more" I said as I gasped for air. He let me take a few breaths before trying to shove his dick in my mouth again. "Open" he demanded. I managed to keep him from doing so for a little while longer.

"That's how you want to play is it" he said before slapping me once again. "I said open your fucking mouth" as he pinched my nose. There was only so long I could hold out before I had to open my mouth again to which he took full advantage of. I managed to take a good lung full of air before he slammed into my throat once again. He slid in and out harder and faster than before as his excitement grew.

Still struggling once more he ordered me to look at him. I knew I had to comply so I did. I saw him bite his lip before he took hold of my head really tightly. I knew then there was more to come but I wasn't at all prepared for what came next. Before I knew it he thrust his hips forward so forcefully my head hit the wall once more and he drove his meat all the way into my straining throat. It felt like he was fucking the top of my lungs. The blood rushed to my head so much more than before. It felt like it was going to explode. My eyes felt like they was going to pop out.

I couldn't help closing them. It was way too much and as I wretched and my body tried to regurgitate his manhood, my face involuntarily screwed itself up in the battle of wills. "Open up that fucking mouth and look at me you cum hungry slut" he roared. 

I tried to do as he said but it was too much. He took his cock from my mouth and slapped me once more. Callum put his fingers under my chin and said "If you don't look at me I'm going to fuck your ass do you understand?". I nodded my head and frantically blurted "Yes, please don't fuck me?" I begged.

Callum stuffed his rock hard dick in my mouth again and waited for me to look at him before delving balls deep back into my throat. He was so vigorous that it was impossible to not gag and screw my face up. He carried on regardless for what seemed like forever until he pulled out, stepped aside and pushed me onto my front on the floor. 

"Oh I see. I guess you wanted this all along. I can't wait to see you try to walk home" Callum said while he slapped my ass. Then I felt him reach around to unbutton my jeans and began to pull them down over my ass. He pulled them down to just below my knees. The cold air hit my ass and I was so afraid of what was about to come I nearly pissed myself. I begged him. "Please don't, please don't fuck me Callum, your too big, please" but he just laughed as I felt him climb on top of me and begin to rub his thick slimy cock between my cheeks. 

"It's too late to back out now slut" he growled. I felt his hot meat press up against my tight hole. Gently jabbing at first as he positioned the head of his dick against my entrance. Callum begun to try push his way inside my tender asshole but my muscles kept his slippery cock at bay. I could feel Callum's hand grab his cock behind me then without warning he forced the huge end of his manhood inside my tight hole.

I winced and let out cry of pleasure and immense pain when all of a sudden there was a knock at the door and my girlfriends voice began to call us. Callum jumped up so quickly and had the leather restraints off in a flash. I really don't know how we got dressed so quickly but we were soon looking as normal as we did when we started (well almost).

I sat back on the sofa and pretended like nothing had ever happened while Callum answered the door. She came in and instantly knew something was wrong. She asked if I was alright and I said "Yeh why?". She said you look like you've been crying to which I replied "Well, our argument earlier really got to me".

Callum chipped in "Yeh he's a bit upset. We've just been having a bit of a heart to heart, you know". 

"Aww, that's so sweet of you Callum. Most of his friends would probably say forget that bitch, get rid of her". She fell for it. She took the bait hook, line and sinker. We hugged and agreed we can sort it out back at our place. The relief was so immense you wouldn't believe.

After another beer each we left for home and things were left there for the night.

To say it was a night I'll never forget is one hell of an understatement but this wasn't to be the end of my sexual exploration with Callum 

TO BE CONTINUED...

Part two coming soon.....