The night I discovered my true self

This all happened three years ago.  I’m a 30-something accountant from Scotland.  I'm 5' 6" which isn't the tallest and I get called cute due to my babyface.  I have short brown hair and blue eyes and, for those who are lucky enough to find out, I have a decent 7" cut cock, which looks slightly bigger on me given my short height.  Being a longtime athlete, I keep myself in top shape and go to the gym or run at least four times per week.  I’ve never had trouble hooking up with beautiful women.  More than a few men have hit on me, too—unsuccessfully until three years ago.

After finishing at the office one Friday night, my fellow worker Sharon and I decided to head out for drinks.  Sharon is in her mid 30s with long dark hair, a pretty face with perky lips and a huge set of cans.  I’d hazard a guess at 32/34 DD, which is rather big for her small slight frame.  I’ve always had a thing for Sharon, but we had quickly ended up in the friend zone, which never allowed me to do anything or really broach the subject.

This evening, we decided to head to a lane in Glasgow relatively close to where we work.  It has a number of gay bars on each side and quite often we'd head to one that was known more as a lesbian bar.  I’ve always considered myself straight but didn’t mind going to gay bars as the drinks were cheaper and the atmosphere was always better.

After getting a couple of drinks, we headed to a nearby table. The inside of the bar is quite unique, you head underground to it where there are nice stone arches all round. It also has a number of areas split up and you can sit in different sections. This night we just sat in the main area as it was quiet especially for a Friday night.  There were maybe only five or six other customers plus a few bar staff.

Once we were seated, Sharon and I talked and laughed through the first drink before I headed to the toilet and back to the bar.  On returning to the table with a couple more drinks I noticed someone had sat down next to Sharon.  It was another guy who looked in great shape.  It never came as a surprise anytime we'd go out.  Sharon would attract other guys and often girls although 99 times out of 100 her would-be suitors were unsuccessful. 

The new person at the table wore a tight white t-shirt that showed off a swimmer's body. As I got closer, I could see he had wavy black hair, a cut jaw and piercing green eyes.  Even as a straight male, I could appreciate he was a good looking guy.  He quickly stood up upon my arrival.  He was slightly taller than myself—maybe 5’9”.  He shook my hand and introduced himself as Ross.  I noticed he, like many swimmers, had a v-shape body tapering down from broad shoulders to a narrow waist.  His quads were bulging at the seams of his jeans.  I worked out but this guy, I immediately thought, must live in the gym.

He said “Sorry, I didn’t realise I was gatecrashing your drinks.  I just came in and didn’t want to sit alone.”  I quickly said it wasn’t an issue.  I explained that Sharon and I worked together and only came out to celebrate being out of the office for another two days.

The night went on and as we three got tipsy we learned a little more about each other.  Ross was in Glasgow for the first time. He had come for work from London and was due back a few days later. He said he was gay but didn’t often go to gay bars due to sometimes unwanted attention and he’d rather be able to pick the right guy than have others throw themselves at him. 

I’ll admit it was good having him there.  He steered the conversation away from our work and into interests and hobbies.  He got quite interested when I said I used to play professional football (that’s soccer for Americans) for a short while.  He quizzed me on everything from lifestyle to the dressing room to trying to find out if any of the football players were secretly in the closet. I had to be honest and say I didn’t know. Out of the players with whom I’d played, no one was officially out, and most people liked to keep their personal life quiet. I didn’t really care about people’s relationships and concentrated on trying to win and be as good as I could for both myself and the team.

After probably too many drinks plus the odd shot here and there, Sharon asked if we wanted to head back to her flat to keep the party going.  Ross and I had no problem with her invitation.  The flat was a short walk from the bar and on route we spoke mostly about the bad weather.  The middle of January in Scotland isn’t warm at the best of times.  But this night was windy, cold and wet--the perfect trifecta for hypothermia.  We walked quickly not really saying much and were happy finally being able to enter Sharon’s flat.

It was a typical old Scottish flat. Red sandstone and high ceilings in every room. It was a fairly standard size—maybe smaller than normal with one kitchen/dining room, a nice toilet and a couple of average sized rooms.  On entering the flat, we all headed to the kitchen/dining room for some warmth and a few more drinks.

 

We sat round a small table at the far side of the room away from the kitchen and continued to talk.  Sharon provided a bottle of Prosecco wine, which isn’t my go-to drink but after a few hours of drinking it didn’t really matter.  We continued to talk, delving into our past relationships and breakups and describing people to whom we were attracted.

Around an hour later, Sharon decided it was time to spice things up.  She asked if we wanted to play a game of truth and dare or cards against humanity. We quickly settled on truth or dare and Sharon offered to go first.  As we all probably cautiously do, she decided to pick "truth" and Ross set the tone by asking “what’s the biggest dick you’ve ever taken?” Sharon went bright red and said “about 7 inches” whilst holding her hands apart to give a visual estimate. I thought to myself if that was 7” I’m actually verging on 9” but kept quiet.

We each took a turn answering embarrassing questions and as the new bottle of Prosecco was opened, Sharon made a new rule that only "dares" were allowed.  She said the game was too vanilla and cautious and we should lighten it up.  

I was first up and dared Sharon to remove her top and bra for the rest of the night.  I don’t think this is how Sharon thought the game would go.  She looked a little annoyed.  As I said, I’d always had a thing for her and really wanted her to see me not as a “friend” but as someone with whom she might end up.  But “friend” was where we had landed from the initial time we met each other.

With a look of peevishness, she slowly started to take off her bra and these massive melons appeared with nipples so pointy they looked like they could cut glass.  My cock began to harden.

Next was Ross who thought it was appropriate to dare me to motorboat Sharon’s breasts.  I had no trouble with that request!  In my head, I hoped she was as happy.  It turned out she might have been.  After I’d been in between her breasts, she pulled my head up and gave me a deep French kiss.

Next was Sharon’s turn.  With a slight smirk on her face she just said “ for 30 seconds I think you two should French kiss.”  Wow, that was payback, I thought.  It was my turn to look a little shocked and pissy.  Before I could say anything, however, I felt Ross right beside me.  He held the back of my head and leaned in to kiss me.  It was a strange feeling having the initial kiss. I felt the unusual feeling of a little stubble but it wasn’t unpleasant. 

Ross quickly started moving his hands to other places even touching my groin and then onto my cock which was already hard and twitching.  The kiss wasn’t broken until Sharon laughed and said “I think that’s enough you’ve been at it for 45 seconds.”  She looked at me and said “I think you enjoyed that more than you wanted to” with a little wink and a stare down at my jeans—with an obvious outline of my hard cock.  I was a little embarrassed but I couldn’t say I didn’t like it.

After sitting down and trying to get my head straight, I heard Sharon say, “Ross, I dare you to try and keep John as hard as possible for two minutes.  If you make him cum, I’ll give you a treat.”  This was a double dare.  But I couldn’t really complain.  Ross pulled me back up and began kissing me again while rubbing my cock through my jeans. I was still rock hard and undeniably getting more and more into it.  As he kissed, Ross unbuttoned my trousers, pulled them down, fished out my tool, fell to his knees and began sucking it.

This wasn’t quite what I had imagined going out for drinks but I had to admit it felt good.  Ross expertly licked around my mushroom head and took my balls in his mouth one by one before engulfing my full cock.  I’d never had anyone quite go straight down the full 7” and he did it with ease. He sucked my cock like a Dyson and it felt amazing.  When I looked over at Sharon, I got more turned on as she had started rubbing herself. She had her dress lifted up and one hand down her pants. She stared right at me and then at my cock getting expertly sucked and couldn’t hide the smile from her face.

After a couple of minutes, Ross stopped and said "I think we have him nice and hard but it’d be such a waste to let him cum now.”  He chuckled and said “Sharon, you’re next.  I want to see your skills.”  Sharon got down on her knees and just took in my full cock to the base. Talk about hidden talents.  I’d sat next to Sharon for five years and even in my fantasies she didn’t do this well.  She let me face fuck her for a few minutes until her eyes were watering and her face was a slight mess.  Sharon and I both kissed until she broke it off, held my head and said “I want to see him fuck you.”  I thought this was maybe one step too far.  I began to protest but she looked me straight in the eye and pleaded. "Please let me see him fuck you.  I’ve always fantasised about watching two guys fuck in person.”

I didn't know what to say.  I had enjoyed everything so far and knew I couldn't really get out of it.  So I said to Sharon, "I’ll let this happen on one condition.  I get to fuck you first.”  Sharon didn’t say anything.  She just looked at Ross who had a massive grin on his face and held out her hands.  We each took a hand and went with her to her bedroom.

Once inside, we all stripped off our clothes.  Ross told me how gentle he’d be.  He said he only “topped” and knew how to break guys in, even the straight first timers.  Then he winked.

Sharon lay down on the bed. I got on top of her and slowly kissed her body, working down to her breasts to her belly to her clit.  She was incredible and within minutes she was moaning and writhing under me.  She held my brown hair, controlling where I could go and bringing herself closer to cumming.  As this was going on, I felt two hands spread my ass cheeks.  Ross was behind me diving his tongue into my hole. I’ve never been rimmed before but the way his tongue dived into my hole drove me crazy. I could feel it getting deeper and deeper and invading my bowls.  My hard cock was dripping pre-cum.

I couldn’t wait any longer.  I pulled myself up and inserted my hard dick in Sharon’s vagina. She moaned straight away and started almost immediately cumming. As I fucked her harder and harder, she became wetter and wetter and even squirted.  I watched as her eyes roll back into her head as she made some incoherent noises.  I’d never experienced such a lubricated hole before.

As I was pounding Sharon, I suddenly became aware of a new sensation.  A hand was on my ass and a finger was brushing against my hole. It was wet with lube and putting pressure on my ring.  As I continued to fuck Sharon, my hole gave way and the finger made its way inside.  I felt full.  My ass felt so weird until he moved around and started putting pressure in certain spots.  

I could feel my load rising and told Sharon I was close.  I withdrew and aimed my cock at her face. As I wanked off, the finger kept its rhythm and prodding until I shot a massive load.  About five or six ropes of cum splattered across Sharon’s face. She was well and truly coated in my seed, but it didn’t stop me from pulling her up and kissing her. I was so caught up in all of this I only remembered Ross was there when he took his finger out my hole.

As I turned around to see Ross for the first time completely naked, I noticed two things. He was much better looking than I’d ever thought and he was currently wanking the biggest cock I’d ever seen. It was about 9.5” with a huge head and curved almost like a banana.

 

Sharon saw this as well and smiled knowing I was in serious trouble. She slapped my ass and said “you're up big boy” whilst laughing and just lay back on the bed to watch the action.

I moved close to Ross and kissed him while touching his rock hard cock. My hand barely got round the girth of it.  I continued to kiss him. I kissed his neck and went down to his nipples, lightly biting them and the back up to nibble at his neck and ears.  It was then that I whispered into his ear “Have you ever fucked a women?"  He shook his head no and then looked at Sharon. I said “Why don't you try and then I'll give you my ass.” 

Ross again shook his head no.  I said “You can break me in afterwards and you can stop if you don’t enjoy it.”  He grinned slightly and slowly moved over to Sharon stalking his prey.  She hadn’t heard my suggestion and only realised what might happen when Ross moved her legs to separate them.  Her eyes widened in surprise and she said, “ I don't think that will fit" as the tip of his cock pushed into her flaps.  She said urgently, “Wait I need lube,” which surprised me given her lubricated hole.  

Ross smirked and started to push his way inside.  Sharon's body tensed as she tried her best to accommodate Ross’s Anaconda.  Slowly, inch by inch, Ross stuffed his 9.5” deep into her vagina.  Then he started pumping in and out until he got into a good rhythm.  WHAP!  WHAP!  WHAP!  WHAP!  Sharon started moaning loudly—making slutty noises I'd never heard before. 

At this point, I took my chance.  I grabbed Ross’s hips and planted my face between his ass crack before beginning to eat out his hole. He slowed his thrusts to give me better access.  I tried to replicate what he had done earlier and noticed he didn't complain—so much so he reached behind himself to hold my head in place forcing my tongue deeper into his ass. 

After several seconds, I came up for air.  I noticed a lube bottle beside me and decided to lube a couple of fingers.  I started pushing them into Ross’s wet hole.  Soon I was fucking his ass with my fingers—letting his backward thrusts drive the fingers in and out.  My cock had fully recharged and was pointing upwards.  

Ross increased his tempo until he was fucking Sharon at full speed.  Her eyes glazed over as she moaned in pleasure.  As I watched this unfold, I lubed up my now hard cock and pointed it directly at Ross' hole.  It was only when I placed my hand on his back to bend  him slightly over that he started to work out what might be in the offing. 

Ross started to mumble "I don't bottom" and “You’ll regret trying to fuck me,” but Sharon wrapped her legs round Ross’s torso and held him in place with a devilish grin.  She looked me in the eye and nodded her approval.  I started to push my swollen head into Ross’s hole.  Initially, he tried to push out my cock.  But then he submitted, letting his hole relax.  Soon my cock head was past his outer ring. "Fuck, oh shit, wait” was all he said. 

Ross’s cock was still in Sharon’s vagina.  It hadn't softened but his movements had slowed to a halt. He stayed still and didn’t try to move as my cock went in deeper and deeper.  Finally, I pushed all the way in and felt my balls rest on his ass cheeks.  As I began my thrusts, “It hurts fuck” was on a loop from Ross for the next several minutes.  Then he stopped talking.  I noticed he was rocking and slowly fucking Sharon again.  As I picked up the pace, his moans changed, and he was clearly enjoying being fucked with my 7” dick.

 

I grabbed Ross’ curly black hair and held it in my hand as I thrust in deeper and harder.  I moved up till I could almost reach his ear and said “You’re enjoying this.  You might want to be my slut from now on.”  His ass was tight and on every stroke it felt like he clamped down on my cock.  I knew I couldn’t last long and upped my pace to full speed. Just before I unloaded though, his ass tightened even more and I knew he was cumming inside Sharon. That’s all it took for me to unload straight into Ross’ bowls.  “Ohhhh fuucckkkk!” I grunted as my climax made me shudder and spasm before I collapsed against his back. 

I was still on top of Ross when my cock softened and popped out.  Rolling off Ross and onto the bed I now lay as Sharon had once done.  In a sex fueled daze. Sharon rolled against my side and kissed me passionately.  She said “That’s the hottest thing I’ve ever seen and done.”  She then straddled my chest before moving up and positioning her vagina just above my face.  I didn't know what was happening until I saw white liquid leak from her pussy.  It dripped onto my face and into my mouth.  Sharon then sat on my face and made me eat the load Ross had just detonated in her hole.  It tasted slightly sweet and had a strange texture but was enjoyable.

I could feel the bed shaking and pulled back from Sharon’s clit to see Ross wanking his big dick.  It was back at full mast as he watched Sharon and me.  Heslowly got off the bed and lifted my legs which Sharon gladly held. I was still licking her pussy as Ross rimmed me once more.   Sharon was once again moaning loudly as I started to moan into her. 

I could feel fingers at my hole again but this felt like two digits and maybe more. I continued to get fingered for a few minutes.  The fingers were roaming around and spreading and I started to find it more and more pleasurable.  Then Ross spoke again “You took my anal virginity.  I think it’s only fair that I return the favour.” 

Then I felt something else pressing against my hole. I knew what was going to happen.  The wheels were already in motion so I tried my best to relax but the pressure and pain were so intense. I thought my asshole was being ripped open. I hoped Sharon’s house was soundproofed.  I began to yell “FUCK, SLOWLY… AAAHHHH!!!”  I had tears coming down my face.  After a few minutes, it felt like a pop and I could feel it inch by inch pushing inside my hole. 

It was burning like hell.  Ross must’ve felt my discomfort as well as he momentarily took out his cock.  I murmured, “God, thank you, it’s too big.”  Sharon sat again on my face and spread my legs wider.  “Fucking take it!” she ordered me.  I never knew she had a Dom side.  Then I felt it again. The cock was going back towards my ass.  “NO…NO…AHHHH…PLEASE NO” was all I could holler into Sharon’s clit.  But this time Ross’s Anaconda went in more easily.  I still felt some pain as I was stuffed full with his sausage.  After a few minutes, the pain had slightly subsided.  It still didn’t feel wonderful but it also didn’t feel like my ass was being ripped in half. 

I felt Sharon move off my face. She turned and watched as my hole was fucked.  She flashed a massive smile down at me then began rubbing herself with her right hand.  Her left hand retrieved her mobile phone.  She began taking a video of Ross’s cock thrusting in and out of my no longer virgin hole.  I tried to tell her to stop but the words didn’t quite come out.  It sounded more like “ddddddnt sssssssoppppp” rather than “don’t stop.”

As he had promised, Ross was gentle considering the size. He managed to take his time and get me accustomed to the monster that inhabited my ass--so much so that the feeling became more and more pleasurable.  He began hitting spots I didn’t know existed.  I went to feel my cock and realised it was rock hard and oozing pre-cum. 

Ross started to pick up the pace.  Soon he was pummeling my stretched hole.  To my surprise, I moaned “Fuck me, fuck me, fuck me harder!”  I didn’t realise what I was saying until the words had all come out.  Ross said “I knew I could get you.  You looked too cute.  I needed to fuck you from the moment I met you tonight.”  Sharon had rolled off me while filming my bottoming initiation.  Ross now held my legs upwards.  With every thrust inward, his balls slapped my ass cheeks.

Ross suddenly pulled out of me.  He quickly rolled me onto all fours and climbed onto the bed.  Fisting my brown hair he pulled up my face and positioned his massive cock at my hole once more.  Pushing his way inside, Ross fucked me harder than ever and I felt my prostate getting tagged repeatedly.  When he dropped my hair, my face and upper torso collapsed on the bed.  He completely owned me—making me his bitch on the bed.

 

I was in heaven.  Ross then pulled out and rolled me onto my back once more.  He said, “I need your help Sharon. I want to pull his legs up over his head.”  Sharon held me as Ross rolled my legs up and over.  As he plunged all 9.5” back inside, pile-driving my hole, my hard cock hovered above my face dripping pre-cum on it.  As Ross fucked me in this position, my cock continued to leak.  Sharon sat on my legs holding them tighter together, which gave Ross more pleasure.  She used her spare hands to wank me.  

It didn’t take long until I was on edge. Sharon kept wanking me and said, “Open wide honey.”  As my lips parted, I exploded my load on my mouth.  I tried to swallow all of it but couldn’t keep up with the huge amount of cum.  It coated my nose, cheeks and mouth.  As this happened, I felt Ross’s cock pulse and cum inside me.  His body spasmed as he unloaded his release.  

Finally, he pulled out his cock for me to clean.  I didn’t hesitate taking his cock in my mouth for the first time, liking the velvety feeling of his big head.  Whilst I worked on polishing his cock, Sharon started licking the cum off my face. She stood up over the kneeling Ross and fed him my cum.

That night, we took turns exploring everything.  Sharon even had a strap on which she was dying to use and we got a go at spit roasting her as well as some double penetration.  We spent that night plus the Saturday and Sunday drinking plenty of water and fucking like horny rabbits.  

Three years later, I’m truly bi.  I live with Sharon, but we keep in touch with Ross and quite often get the gang together for more fun