Stuc in the Middle

Hello everyone. This is a continuation of a story that I started quite a long time ago. If you haven't read that one yet, I would suggest you do so (just realize that it was an earlier story so I was very inexperienced in writing erotica), however, not reading it won't take away from this one. This one starts where the other one left off but some of the dialogue has been changed. While the first one was very oral centric, this one is very anal centric, specifically about taking a guy's anal virginity. There is a lot of anal sex, a little bit of humiliation and degradation and involves potentially unsafe sex practices. This is a work of fiction. Please be safe out there.

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I was still sitting on the ground, my legs folded under me and my back resting against the seat cushions of the couch. I was breathing heavy and glistening from a mixture of sweat and the remaining remnants of cum that I had not managed to scoop off of my body and into my mouth. Sitting properly on the couch, on either side of my splayed body, were Chris and Steve, two of my bookstore regulars although today was the first time that they had shared me. Hell, to my knowledge, it was the first time they had even met. I'm definitely not complaining though. They had fed me their cocks and cum and it was marvelous.

My eyes were closed and I was lost in my post-orgasmic state when I faintly heard them talking to each other.

"That's why I love this fucker," Chris said. "He never disappoints. Some of the best head you can get."

I heard the couch crinkle, like he was moving his head and then he said. "We really should hook up outside of this place, like a hotel or something and really put him through the paces without worrying about a time limit."

"Sounds good to me," replied Steve. "But I would guess we still have maybe 20 minutes left here on the timer. What do you think we should do?" If I had been able to see his face, I would have seen a shit-eating grin spread across his face as he looked at Chris.

"Well," said Chris as he pondered over his answer. "I've never had a chance to fuck this little slut's pussy. You?"

"Nope," replied Steve, "head only."

I felt Chris readjust himself on the couch, like he was sitting up and turning slightly towards Steve. "I say we take this bitch's virginity. You KNOW he wants to get fucked, most likely by a daddy type, but instead of giving in to his true nature, he's been teasing us by not giving that shit up."

Steve readjusted too. "I mean, that's just not right. Teasing us like that."

Their tone was mock serious, but playful at the same time.

Chris said, "We would really be doing him a favor, you know. He doesn't know the pleasure he can get by giving up his cunt to us."

Steve replied, "Yeah, I mean, we really would be providing a public service."

Chris then tapped me on my arm, "You hear that boy? We're going to be nice to you and fuck that tight little ass of yours.

Steve added, "Yep, we are going to turn you into a nice little ass whore."

My eyes flew open and I looked up at them as my head rested back on the couch cushions where they sat. I had heard what they were saying in the sense that I knew they were talking, but none of it had REALLY registered with me. I was lost in my own world, but Chris had brought me back to reality with the quick tap on my arm and the string of words that followed.

Before I had time to really process the ramifications, they were both standing and grabbing my arms to lift me to my feet. I've always wanted to try anal, I'll be honest there, but the idea has always scared me. My visits to the bookstore to give head to strangers was a way for me to deal with my bi-sexual feelings, but I still considered myself straight. I know, it is weird, but I know I am not alone in this. This justification is used by a lot of men who are not ready to out themselves to the world. It is like someone who smokes, but never buys a pack of cigarettes. They only bum ones. They rationalize it to themselves that they are not a smoker because they never buy any. Giving head was like bumming a smoke. It didn't make me gay, it made me curious.

So there was that, but there was also the pain portion. To say that I've never TRIED anal would be a lie. The idea has always intrigued me, as I've already said, because of the stories I have read about how good it feels. So because of that, I've tried it a few times here in this very bookstore but each time I had tried it, the guy must have thought I was walking around with a warmed up, lubed ass because they just tried to jab their cocks into me without taking their time. The pain would be immense and the mood would quickly be killed.

"I don't know guys," I pleaded, "I don't think I'm ready for that. It always hurts way too much."

I was now standing and they had their hands on me in various places on my body, roaming over me like they were inspecting me. Steve looked at me and said, "Just relax boy. We are going to take our time, go slow and get you nice and opened up. You will love the way it feels to get fucked, but you have to just relax and give your body to us."

"And look, if things get too hard for you and you want us to slow down or take it easier on you, just say 'mercy'. If you absolutely want us to stop everything we are doing, just say 'red' and boom, we stop. We are not looking to hurt you boy, we just want to fuck you and not just once, but repeatedly so it is in our best interest to make sure you like it," said Chris.

"OK, I mean, if you promise you will stop if it hurts too much, then. . . I guess," I said.

"Of course we will boy," said Steve.

"Ok then," I said. God, I gave in WAY too easy on that, but truth be told, I really did want to try it. I was nervous though. It is one thing to suck a cock, but this is giving up my body, my ass to a man. Actually, two men.

My first time getting fucked was going to be with two guys. Holy shit, what did I just agree to?

"Fuck yeah," said Chris. "Get on the couch on your knees and lean across the back so we have good access to you."

I walked the few steps to the couch and did as he instructed. My knees and shins were on the seat cushions and my chest laid on the back of the couch with my hands on either side of me, ready to push myself up should the pain be too much. My knees were still rather close to each other and Steve said, "Spread your legs out, far as you can get them."

I've been like this before as I've let a few men play with my ass, but the intention of being fucked was not there, at least not in my mind. It was completely different knowing that I was spreading myself wide so that these two (am I really going to take two guys during my first time?) could fuck me. At that moment, as I spread my knees as far apart as I could, I felt more vulnerable than I could ever remember.

"That is one sweet looking ass," said Chris.

I felt their hands began to rub my ass and it made me jump. I was a ball of nerves. I think they could sense it.

"Just relax," said Chris. "I promise you will enjoy this."

I tried to will myself to relax, remembering everything that I had read about tension making it hurt more, but to be honest, it was hard. Very hard.

They continued to rub my ass, my lower back, my inner thighs and my legs. Four hands caressed my skin and I had to admit, it felt really good. They were slow and methodical, like a sensual massage. Their caressing become a little more needing, a little more forceful and their fingers began to compress the flesh of my ass, hips and legs. They were now groping me. I lowered my head down towards the back of the couch and closed by eyes, enjoying the feeling of their hands on me.

Their fondling of my body began to center on my ass. They continued to squeeze and caress my ass cheeks, occasionally pulling them apart. They finally pulled my ass completely apart and held me open, exposing my bud to them.

"Oh, that's very nice," said Steve. "So sweet and tight."

"For now," said Chris which he followed up with a laugh.

One of them, I'm not sure which as my eyes were still closed, ran a finger across my puckered hole. There was a nice surge of tingly pleasure that ran through my body and I moaned. The finger ran across my bud again and I responded vocally once more.

"I think he likes it," said Steve.

They laughed.

Fingers then began to run up and down my crack and over my hole, multiple fingers running in an un-orchestrated exploration of my ass. I found myself slightly pushing back towards them. I was relaxing and losing myself to the sensations. Nothing like a bit of pleasure to make your reservations slip away.

I felt the fingers move and two hands grasp and hold open the cheeks of my ass. I wasn't sure, but based on the placement of the hands, it felt like only one of them instead of both of them. Each hand was grasping a cheek separately with their fingers pointing up towards my body and their thumbs grabbing the bottom portion. I received confirmation shortly after as I felt a tongue run across my asshole. I whimpered.

Chris or Steve, whoever was holding my ass open, began to lick me vigorously. I pushed myself back against their mouth and lost myself in the pleasure. As they ate my ass, I felt my hair being pulled which I responded to by lifting my head. I opened my eyes to see Chris's cock staring right at me. He pushed forward, the spongy head sliding against my lips and I opened up to receive him into my mouth. He began to slowly slide his dick in and out of my mouth while Steve devoured my hole.

I was in heaven.

My cock, which had deflated out of nerves, was finding new life.

I now realized that as much as I have loved sucking dick in the past, I enjoyed it so much more while my ass was being eaten.

Steve licked and probed away for a good five minutes, his tongue tracing the wrinkled skin or pushing inside me, a little at first and then deeper as I opened up to him. My crack was now a wet and soaked with his spit which I guess he figured was enough to move on to the next phase. I felt him press the tip of his finger against my bud and push. There was a slight bit of discomfort, but the proverbial tossing of my salad had made this step much easier.

My ass slowly opened to him as he pushed a single digit into my virgin canal. It felt warm and intrusive, but there was still twinges of pleasure as he pried open the sensitive skin that involuntarily clamped down on his finger. He took his time, taking a little more of my ass at a time and I found myself concentrating on what he was doing rather than Chris's large cock in my mouth.

"Hey, hey, focus on my cock," Chris said. "Don't worry about what he is doing back there. Focus on my cock, focus on trying to feel every inch, every vein and every texture of it. You are used to quickly devouring my it so this time, explore it as it slides in and out of your hot little mouth boy."

He then held out a small brown bottle to my nose and with his cock still filling my mouth, he told me to inhale. I took a large inhale from the bottle and then he switched it to my other nostril and had me do the same thing. My whole body became warm and my head began to float. I felt like I was in a state of euphoria. I became even more excited and his dick felt even better in my mouth. I felt extremely relaxed and I began to produce more saliva.

He then started sliding excruciatingly slow in and out of my mouth, giving me maybe half of his cock with each leisurely stroke. I tried to do what he said. I put all my focus on his dick. I took in every single texture of his cock, running my tongue over the hard, warm shaft to the large, spongy head. I noticed the difference between the skin on the outer edges of the head and the soft tips around the piss hole. I let my tongue feel each vein individually, each change in shape and tried to make him feel good in the process. The poppers were making this experience feel like it was the first time I had ever given head. Everything was so surreal and erotic. I could feel everything, even my heartbeat.

I was in a state of total relaxation and I had let my mind go away from what Steve was doing and focused completely on Chris's cock. I felt almost like I was in a Zen like state. It sounds weird, but I just completely focused on exploring his dick and nothing else.

I was aware then that my ass felt hot and I was taken out of the moment when I heard Steve spit on my asshole. My focus expanded I became aware that Steve was now sliding his finger easily in and out of my ass and it felt so amazing.

"That really worked man," said Steve. "Once you gave him the hit of poppers and he started focusing on your cock, his ass just loosened up and I slid right in almost immediately."

I was now focusing on the delicious cock in my mouth AND the finger that was probing my ass. He was really fucking me with it now.

I was still in a state of euphoria from the poppers, but Chris had me take another two hits, one per nostril which elevated it even more. Steve spit on my hole and then began to slide a second finger in. I could feel the pressure in my ass, but the pain was almost non-existent. I closed my eyes and enjoyed the pleasurable feeling coming from my hole. Chris continued to slowly fuck my mouth as Steve slid in and out of me at the other end. I was really starting to understand why many people like being spit roasted. Cocks entering your body from both end, providing you with two different, yet complimentary types of excitement and pleasure. I really wanted to feel that now. My hesitation was gone.

Chris presented me with the poppers once again and I inhaled greedily this time. A renewed sensations of warmth coursed through my body and the nerve endings began to fire, my focus renewed on the cock in my mouth and the fingers in my ass.

Steve was spreading his fingers as he finger fucked me, opening me up and eliciting moans from me which was muffled around Chris's cock. I felt Steve insert a third finger and at the same time heard him say, "Oh yeah, he's opening up very nicely. His ass is hungry."

"Well, then give him the real thing," Chris said. "We are running out of time."

I felt a few more thrusts, twists and spreads of his fingers in my ass before Steve removed his fingers. I felt his left hand grab my waist and almost immediately, the tip of his cock was pressing against my hole. He was about to invade my body. I was going to be fucked for the very first time. I was still swimming in the haze of poppers which I guess is a good thing because instead of being nervous, I was excited. I was horny. I wanted this. Hell, at this point, I needed it. I needed to be taken by them and used. It is what I enjoyed as a cock-sucker, but I was turning a new page. I was becoming a true bottom, offering up either hole for a man to use.

He pressed forward, the loosened muscles of my ass still offering a small bit of resistance to his large cock. He applied pressure and pulled on my hips. Chris continued to thrust slowly in my mouth, which in retrospect, was actually good for me. Knowing that his cock was in my mouth, it forced me to ensure that I didn't clench up for fear of hurting him, so I remained relaxed as Steve's tip popped through the ring of my ass and entered my virgin territory. He pushed the entire head in and then rocked back and forth with the head surpassing and then retreating through the tight muscle. It was slow, tedious movements which served to open up my ass for him in the most painless way possible.

"Houston, we are a go," said Steve.

"Hahaha, that's funny," said Chris. "You are doing good boy. See, we told you we would do it right for you."

I made a sound, a mix of a mumble, a moan and an affirmative response.

Steve, seeing that I was doing good and not experiencing too much pain, began to push forward. Slowly, bit by bit and retreating each time. Slowly taking new ground inside of me with each thrust.

Chris gave me another hit of the poppers and, once done, moved away from his slow thrusts and starting fucking my mouth with his usual speed and force. I focused on his dick, but felt Steve place his right hand on my hip and now with both hands, began to push farther into me with each thrust.

I was being properly spit-roasted.

Fuck yeah!

Then I felt it. A new sensation. Deep in my ass. A place that Steve kept hitting. It was unlike anything I had felt before. It felt amazing. I would later learn that he was hitting my prostate, but this was all new to me at the time. All I knew was that he was hitting a place I liked to call "OH MY GOD".

Then I felt his hips pressing against my ass and he stopped. He just stood there.

"I'm all in," he announced.

"Hell yeah," said Chris and then I heard them high-five. If I wasn't in such a high state, I probably would have laughed. Each of them with a cock buried in one end of me and high-fiving over me was just a funny sight to think about.

Steve started to pull out and then thrust into me a good nine or ten times before saying, "You want to give him a shot? I think we are almost out of time."

"Sure, yeah," said Chris as he pulled his cock from my mouth. Steve pulled out of me and I suddenly felt very empty. It was a strange feeling. This was how I was normally, but now, it felt different. Nothing in my mouth and nothing in my ass. Chris walked behind me and I felt him line himself up with my hole. He grabbed my hips and pushed in with his cock. Chris's cock is a bit bigger, definitely wider and I felt a small rush of pain and discomfort, but it was nothing unbearable, especially knowing what he might hit once he buried himself in my ass. I wanted to feel that feeling again.

He didn't slam himself all the way in, but he took his time taking my ass, albeit a lot faster than Steve had since I had already been properly opened up. When he was finally all the way in, he began to fuck me slowly for maybe 30 seconds while Steve said, "That is so fucking hot man. Look at how his ass just grabs your cock, like it doesn't want to let it go."

"Holy shit, this feels so fucking good," said Chris. "His ass is so fucking tight."

Just then, the timer on the TV went off which meant that we were no longer guaranteed privacy. The management team was very strict and if they saw a closed door with the green light lit and not the red light, they would open the door and wait until you either put in more money or left. Yeah, they could be pricks sometime.

Chris pulled out of my ass and, again, I felt so empty.

"Get up boy, we need to go," said Chris.

"Please, no," I begged. "Oh my God, that felt so good."

"Oh don't worry, we aren't done. We just aren't staying here," he said.

"Oh, ok," I replied. "Uh, where are we going?"

"Well, we can't go back to my place," said Steve. "Married. Can't rightly bring home two dudes for a gay threesome."

"Haha, me either," said Chris. "That's why we are going to go to his place," he said as he looked at me. I don't think it was really a question or if he was asking if it was ok. I think he was just flatly telling me that they were coming back, whether I wanted that or not.

"Uh, my place?" I asked. "Uh, yeah, I guess that would be ok."

I had a rule that I was about to break. I never brought guys back to my place. NEVER. Girls? Sure. Guys? No. But I needed to finish what we had started. I needed to feel what it felt like to be properly fucked. I needed this.

They started quickly getting dressed but I found that I couldn't keep my eyes off of their cocks while they were still out. They were so large and powerful and I found myself looking at them in a whole new light. I wanted them back inside of me NOW. I was just standing there like an idiot, looking at their crotches.

They finished dressing before I had even started and I was quickly snapped out of my trance as there was a loud banging on the door to the room followed by a sudden click of the lock and the door being swung open.