Losing my Bisexual Virginity [MM]

It all happened when I was 21 and stuck in my hometown. I had just been brutally broken up with a few months earlier and was still devastated by it. Out of nowhere a good friend of mine pulls me aside and, out of character for him, asks if he can ask me a question and keep it between us. Not having a reason to distrust him I tell him sure. He then asks if he can fuck me.

I was blindsided. I had no idea how to respond. I stood there for a moment and tried to pick out words, any words, of “No… Maybe…I’m not sure?” which surprised me as I was 100% straight! He realized I needed some time to think about it and told me to just let him know and his next Saturday was free. For that or just to hang out.

My friend named “F” was 32 at the time. A Staff Sergeant in the Marine Corp., married, and was into a lot of the same stuff I was. He was taller than me by a few inches (6’1″), had tan skin (Italian), brown eyes, and high and tight cropped dark brown hair. As you can imagine he was fit. This made my 21 year old pale skin, blond hair, blue eyed scrawny frame look even more so next to his. So you can imagine how this proposal intimidated me a bit. I drove home and couldn’t stop thinking that a MAN was interested in me sexually! It really rocked my world. After a few days and still not being able to stop thinking about it I reached out to a mutual friend. She was older and had experience in this and after realizing I wasn’t getting her hints just laid it on me. “Dude, if you can’t stop thinking about it and it’s driving you this crazy just try it. Try the dick. If you don’t like it you’ll know.”

Later that night my friend “F” texted me wondering if I had made up my mind. This wasn’t his first text to me about it either, yet this was the one I was able to respond to with some confidence. I told him I’ll meet him at his place at 7pm on Saturday. Yet I’m not sure how much I’m willing to experience and I reserve the right to back out if I don’t like it. Obviously he agreed.

Saturday at 7pm I was knocking on his door. My heart was pounding so fast, and I had so much adrenaline running through me it felt time was going slower. As I knocked and waiting for him to open the door a million thoughts went through my head. What he would do to me, want me to do to him, and I just couldn’t keep track of it all.

He opened the door with, “Hey dude. Come on in” as he had before in the past. He was acting as if nothing had changed between us, and that I was just there to hang out. When we both knew that wasn’t the case. He was wearing just basketball shorts and a t-shirt. Whatever conversation we did have didn’t last long. Soon I was following him down the hall to his bedroom to get fucked. My heart was racing again and as I closed the door behind me F asked me what I wanted to do with a smirk.

I told him bumbling to find words that I didn’t know, and I wasn’t sure how to go about this. He caught on after a bit and took control. His first command to me was to get naked with him. He was naked first, and watched me as I stripped off my jeans and boxers from the other side of the room. It was the first time I’d been naked with another man. And F was looking at me with lust. I could tell because I’d given women that look before. And his cock was growing a bit. I asked him, “What now?” blushing and bashful as I stood naked in the bedroom he shared with his wife.

Looking at me knowing he can get more out of this situation than just fucking my ass he took control. F’s next command to me was to get on my knees in front of him. Hesitantly I did as I was told, and was glad he had carpet in his bedroom. This was a 180 for me as when I am with a woman I am the one in control and telling them what to do. Being on the opposite end of this I knew things could get crazy fast. As I looked forward I was perfect height to see his slowly growing cock and massive balls. I looked up at him for reassurance and direction.

“Go on. Play with it. Stroke me hard.” F told me gently but firmly. I swallowed hard, swallowing nothing as my mouth was dry, and looked back at his cock and balls. I slowly reached out my right hand and grabbed his cock. With my left I grabbed his balls. F just stood there looking down at me as I got him hard.

It was odd holding another man’s junk for the first time. It was familiar, but backwards. As I stroked him hard I realized he was quite thick. Also his balls filled my palm and were nice and heavy. I kept rolling his balls in my palm and stroking his cock. Soon F was fully hard and I realized that I was giving another man a hand job in his bedroom.

I look down embarrassed by this clarity of thought. What I saw made me question on my sexuality more and more. I was rock hard. Something I was doing with F I was enjoying. How much I wasn’t sure. I was a bit disgusted yet turned on more than I thought possible. I couldn’t keep my thoughts together and had trouble reminding myself I wasn’t gay or bi. Even though testing it was why I was there.

F was getting satisfied with the hand job but wanted more. He told me to look up at him. I did and wondered what he would have me do next.

I looked up and didn’t need to say anything. He smiled at me and said, “How about you suck my cock.” It wasn’t a question. He was telling me to. I look back to his thick cock in my hand and back up at him. Then back at his cock. As I stared as his cock in this moment I reassured myself that coming here and trying cock was what I was there to do. I wanted, no NEEDED, to find out if I was gay, or bi, or whatever. I purse my lips and using my tongue I mustered up as much saliva as I could. I took a breath and moved closer to his cock. I paused as the moment of truth hit me. It was now or never. I took the leap of faith and took F’s thick hard cock into my mouth and began to suck.

It was odd to have another man’s cock in my mouth. Knowing what it was like having your cock sucked, yet being on the other side of things was a unique thing. As I sucked him I took my hands off his shaft and balls and placed them on my thighs. My head bobbing up and down on his now glistening shaft. At first it just tasted like skin, as if I were licking my arm or something. Yet soon after it began to have a unique taste to it. As I sucked him I could feel ever ridge, muscle, and throbbing vein in his shaft. I could tell when something I did with my lips or tongue gave him pleasure. I realized 5 minutes into sucking him that I was taking him to the back of my throat and he still wasn’t fully in my mouth. I could also smell his musk. That unique smell men have down there. It was intoxicating! I had no idea men could smell that “good” down there. Even though the view wasn’t great the smell and taste were wonderful.

F took his hands and put them on the sides of my head near the back, just past my ears. He started to move my head how he wanted me to move. After a couple of minutes of moving my head he started to move his hips. I could feel my mouth getting “fucked”. The only thing I could do other than continue to suck him off, was to think “So, this is what getting face fucked feels like” as I gagged every few thrusts as his cock hit the back of my throat. The face fucking didn’t last long. and soon he let go of my head. “Hey, guess what I can call you now?” F asked knowing full well I couldn’t answer him with a mouthful of cock. “A cocksucker” F tells me playfully. I don’t think I’d ever felt humiliation I enjoyed until that moment. It made me feel so dirty, so wrong, as if this was a title you didn’t want but still earned.

I kept sucking his cock. Twirling my tongue around his head, pushing it up curved like a U along his shaft as I bobbed my head. I was doing everything every girl had done to me to him. “Damn are you sure you’ve never done this before?” F asked me. Again I couldn’t answer him because his cock was in my mouth. Spit was dripping off of it, down my chin, and a bit on my chest and thighs. I noticed I was swallowing more. Either I was producing a lot of spit, or something else was happening. Hearing F moan from my sucking I put the thought aside and just kept doing what felt right. (I learned later I was swallowing his precum).

“I’m close” F warned me. My mind went into a warning overdrive. “WHAT!?! CLOSE!?!” In all honestly I didn’t think this far ahead. I knew sucking him off would get him to cum. I just didn’t think about what to do when he got there. I was too busy enraptured by stroking his cock and feeling his balls. F put his hands back where they were before. I kept sucking, not wanting to stop and blue ball him, but also because I wanted to finish the task I was told to do. F’s moans got louder and more guttural. I was swallowing at lot of spit at this point and enjoying every moment of it. Then he tensed and it happened.

I felt his cock thicken and pulse in my mouth as he pulled out all but the head. I felt his cock pump and was rewarded with my first taste of another man’s cum. With just one spurt his cum halfway filled my mouth. Then there was a second. And a third. I could barely keep it all contained in my mouth as he pulled his cock out. I looked up at him in those seconds. I watched as his cock spurt cum right at my eyes. I closed them as the warm sticky thick cum hit my left eye covering it. The next one my nose, then my right cheek, then my forehead, then my left cheek… He came so much he completely covered my face.

I stayed there on my knees, head back so it didn’t drip all over me and the carpet, covered in F’s thick sticky cum. I felt him flick the last few drops of it onto my face. “Don’t move. I’ll get you a towel” and I heard him shuffle off deeper into his bedroom. As what felt like minutes to my blind and mute self I had to decide what to do with him cum in my mouth. It was beginning to liquefy, had lost none of its potency in flavor or smell, and felt like it coated everything. Even the spaced between my teeth. I realized I was left with two options. Wait for the towel and spit it up into that, or swallow. With no way to gauge time I felt like I had been there for 5 minutes. So I did the only rational thing. I swallowed his load. I could feel it coat my throat, and on an empty stomach I felt it pool inside me.

A moment later a towel was draped over my shoulder. “Here you go man” F said. I clumsily picked up the towel and started to clean my face off. His cum felt like it had gotten into my pores, if there were even possible. I handed him the towel back and said, “Thanks”. F realized this and teased me for swallowing his cum. He relished being able to call me a “cumslut” now. I shuddered again with the delightful humiliation. Standing up I noticed something on the bed was different. There was a long towel draped over it with a bottle of KY jelly. I looked at F and he told me “If you want to get fucked, get on your hands and knees with your head facing the end of the bed.” I looked down and he was rock hard again.

I gulped and made my way to the bed. I had enjoyed everything so far. Let’s see if I enjoy getting fucked.

With F’s cum still feeling like it was coating my face I got onto the bed on my hands and knees with my head facing the end of the bed. Just as he commanded me to. I could still taste and smell his cum, yet that was dissipating a bit now. At this point in my life I had never had anyone do anything with my ass. I’ve had girls jerk me off from behind and stuff. Yet never anything touching, playing, or being inserted into my ass. F aimed to change that. In fact that was why I was there, so he could fuck me. That was the original reason I was there.

Nervous, but getting use to the feeling, I feel F get on the bed behind me. Walking on his knees he gets between my legs, spreading them out with his so he can fit where he wants to. I feel vulnerable like I’ve never felt before, and for some reason it is hot as hell! I feel his hands caress and feel up my ass. Squeezing it, spreading my cheeks a bit, just playing with his new “toy”. I feel his left keeping my cheeks spread open exposing my asshole, and his right hand grabs the KY Jelly. I shudder waiting for him to begin lubing me up. Then I feel it. A cold dollop of lube squirted right on the top of my ass crack. F giggles as i react instinctively to the cold lube.

Holding me in place with his left hand on my hip he puts the lube down and uses he right hand to start lubing me up. I feel his rough manly fingers push the lube over my asshole, rim it to warm it up, and then with a bit of force his index finger gets into my asshole starting to spread lube. I gasp at the intrusion, but F keeps pushing and soon his finger is buried fully into my ass. Twisting his finger so my insides are fully lubed was an interesting sensation. Not pleasurable, yet not unpleasant either. I slowly finger fucks my ass with his index finger for a few minutes. Then he adds more lube and I feel a second finger force its way into my asshole. Just as before I gasped, yet not as much since I was expecting it. After a few minutes of lubing and stretching out my ass F was ready to replace his fingers with his cock.

Now I mentioned he is thick throughout this, and he is. How much he prepped me was only enough to get the very head of his cock into my asshole. I knew this and didn’t know if how much he prepped me would be enough. I was soon to find out as I hear him lube up his cock. I will never forget that sound, or what happened next. I feel F shuffle on the bed behind me. With his left hand on my hip he raises my ass up. I can feel him aligning his cock, and then his cock head in all its slick glory is pressing against my asshole. I take a breath and feel him push.

As he kept pushing I could feel the ring of my asshole open up more and more. It was an odd sensation being stretched open. I had felt it before doing something else, yet never like this. A few times I had to tell him to stop because it did hurt. Yet soon he was right back at it, gently forcing me open again with his battering ram of a cock. Soon I felt my asshole “open” and his cock was able to slide into my ass more freely. This was when I began to start to moan. I could feel his cock opening up my insides and filling me as it throbbed. After a few minutes (he was being gentle) I felt his hips touch my ass. Then he teased me, “Where is my cock?”. He made me say “In my ass”, only to be replied with, “What am I going to do with it?”. I put my head down, partially ashamed, partially aroused and admitted aloud for the first time “Fuck me with it”. F just grunted and began pulling his cock out of my ass. I felt the void his cock had made for itself in my ass, and my asshole grip his cock so tightly I could feel it pulling “out”. It felt amazing!

Soon F was pushing his cock right back inside me. The feelings I had before were still there, and he was hitting my prostate like a champ!, yet now all resistance was gone. I was his to fuck as he pleased and he knew it. Pumping slowly at first I felt his lubed right hand grab my hip and him slowly start to pump my ass full of his cock. Slowly he picked up the pace and started to fuck me like he wanted. I realized I was at his mercy and I was not getting away until he was done fucking what was his. I couldn’t contain myself anymore as his cock rubbed my prostate and I started to moan like a porn star. This only made him desire to fuck me more.

I could feel what felt like orgasms flowing through me every 5 or so minutes, yet I wasn’t pumping cum. Regardless they felt great. F slapped my ass as he fucked me every now and then and I yelped when he did. I looked down and saw his huge balls swaying as he fucked me, my view partially covered by my rock hard cock. I was dripping precum like a very leaky faucet. I was embarrassed and ashamed to see myself enjoying getting fucked so much that I looked up. When I did I saw something that broke me mentally (in a good way). I looked up into his full length closet mirrors and saw myself, ass arched, getting fucked like a bitch. I put my face down into the mattress and howled in pleasure.

F fucked me for a little over an hour. My asshole was already sore and bruised before he was done with it. Yet I heard the moans I heard before when I was sucking him off. F told me once again he was close, and told me to jerk myself off while he fucked me. He wanted me to cum. I steadied myself on my left arm and with my right grabbed my cock and started to stroke. It only took a few and I started to explode in one of the most intense orgasms I’ve ever had! My balls drained to the point where I kept cumming yet no more cum was able to come out. All the while my ass clenched around F’s cock as he fucked me. Soon after I had left my substantial mess of cum under me F came. He forced his cock as deep into my ass as it would go and filled me with another large load of his cum.

Then it was done. I felt F’s cock start to shrink as he pulled it out of my ass. My hole taking more than a few attempts to wink itself closed. That embarrassed me and I’m not sure why. F got off the bed and went to the bathroom to clean up. I lay there my ass still in the air, my asshole on fire, and tried to recover from the lengthy ass fucking I just received.

Source: reddit.com/r/gonewildstories/comments/au5vvn/losing_my_bisexual_virginity_mm