Stuck in the Middle Ch. 02

"Fuck," I exclaimed and quickly grabbed my clothes and began dressing.

"Put more money in or get out," said the attendant in a heavy Hispanic accent. I quickly pulled on my underwear, jeans and shirt as the attendant made no attempt to hide his sleazy leering. I heard him make an air-sucking sound when I bent over to pull my underwear on, clearly signifying he liked what he saw. Chris and Steve just stood around and watched me as I dressed. I have never realized how hard it is to put your shoes on when you are being rushed and watched.

I finally finished dressing and stood up. The three of us filed out of the room and as I passed by the attendant, he did the same air-sucking through his teeth. He was fat and greasy and not what I would ever consider attractive. Now I knew how girls feel when they are leered at by guys they find repulsive.

We all retreated outside together, the bright sun taking a bit of time to get used to, especially after the multiple rounds of poppers I had taken. I started to walk to my car and Chris said, "No boy, you can ride with me. I'll bring you back when we're done."

"Um, ok," I said, my loins speaking for me instead of rational thought.

I walked to his car with him and Steve and got in the backseat while they got in the front. "What's your address," Chris asked. I spit out my full address and he placed it into his car's GPS. I noticed he pressed the "save location" button as well. The large screen came to life and I saw the distance and time to destination.

12 minutes.

12 minutes till I was going to be fucked properly for the first time. I, of course, knew how long it took to get to my apartment, but there on the screen was a digital countdown to the end of my anal virginity. At least that's what I believed at that moment.

He pulled out of the parking lot on to the street and drove towards my fate. Very little was said in the car, but the sexual tension was there. We got within a half mile of my apartment and Chris said, "Perfect, just what I was looking for."

I was a bit confused at what he meant until he detoured and pulled into a corner drug store. He parked out front and then turned back to me. "Go inside and buy an enema kit and a large bottle of water-based lube."

I looked at him, half waiting for him to hand me money, but as soon as I realized he wasn't going to do that, I said, "Um, ok."

I got out of the car and walked into the store. I began to walk around aimlessly, unsure of where to find an enema kit. The lube was easy to find, but the kit, not so much and I definitely did NOT want to ask anyone for help. Luckily, the store seemed pretty sparse of employees and customers so I could hopefully get out with only one person, the cashier, aware of my purchases. These two items combined were just as telling as if I wore a sign around my neck that said, "I'm about to get fucked in the ass."

After what seemed like an eternity, I found the kit and then walked with my head down to the cashier, thankful that I was about to get out of there, sight unseen by almost everyone. I placed the items on the counter, but no associate was there. I stood motionless, waiting.

Then I heard, "Sorry for the wait, is this...," the female voice said before stopping. "Mike, is that you?"

I involuntarily looked up at the sound of my name and found myself looking into the eyes of Kari Butler, my best friend's kid sister. Well, kid sister was a little off. She was eighteen and finishing her senior year, but she was still 9 years his junior. She was the youngest of the four Butler siblings and the only girl.

"Oh, um, hey, yeah, uh...," I stuttered. I could feel my cheeks emblazon with heat. "I, uh, didn't know you worked here."

"I don't. I normally work at the one off Market, but they were short staffed today so I'm filling in," she said. She was stunning. Really. Short, petite, tight body, small breasts, great lips. I've kind of always wanted to fuck her since she started developing into a woman.

"Oh, that's cool," I said, nervous as fuck. She went to grab my stuff and said, "How ya been? I haven't seen you around much."

"I've been good, staying busy," I said, trying to appear calm.

She looked at the items I was buying and a smirk appeared across her face. "Looks like you are getting ready for a fun time. You got a chick you're going to be visiting through the, uh," she paused, then said quietly, "backdoor?" She smiled bigger, happy with her turn of phrase.

"Yeah, but let's keep it between you and I," I said, my mind reeling from the thought that she believed I was buying this so I could fuck a girl in the ass.

"Well, aren't you just all sorts of prepared," she said and then giggled. "I've never done the enema, but I absolutely insist on the lube."

Fuck, did my buddies little sister just tell me that she takes it up the ass??

Then the thought popped into my mind. "Well, now we have something in common besides Todd, her brother and my friend."

"Yeah, uh, figured I'd get that too. You can never be too prepared," I said. I was quickly calming down and starting our normal conversation banter.

"Well, she's a lucky girl. It's not often you have a good looking guy that will go through this much just to make sure the experience is good for them too. You guys don't know how scary it can be to, you know, allow deliveries in the rear." I chuckled to myself and thought, "I do now."

"Yeah, well, it is all about making sure the experience is the best so it can happen over and over and over," I said, loving how I was able to talk in double-speak too without her even having the slightest thought that these items were to prepare my ass to take two cocks, not some 'lucky' girl I was going to bang.

She told me the total and I pulled out my debit card and made the purchase. She bagged up my stuff and started to hand it to me when my world got shattered. From my side, at the exit door, I heard, "Hey boy, hurry up," said Steve. "Chris and I don't have all day."

Fuck.

I turned bright red. I knew I did.

"Wait, is this for you?" asked Kari, complete shock spreading across her beautiful face.

Steve walked up and, unaware of who she was to me, said, "Yep, me and my friend are breaking him in today." He was, I'm sure, trying to humiliate me in front of a complete stranger, but instead, he was humiliating me in front of the sister of my best friend. "He's got a talented little mouth but this little slut wants to be filled from both ends." I was frozen in devastation. I couldn't move.

"OH. MY. GOD!" exclaimed Kari. "You're GAY???"

"No, I, um, I mean, I, uh, please don't say anything," I said and grabbed my bag from her hand. Steve put his hand on my neck and started to walk me out of the store, red faced and all. I looked back, my eyes pleading with her, "Please don't say anything, please!??!"

She just stood there, frozen from shock as we walked out of the store. My last image of her was just that and my stomach was tied in knots. Was she going to tell her brother? Our mutual friends? Would everyone know about my secret life? I was fucked.

We got back to the car and I slumped into the back seat, devastated. I had no idea what was going to come about from this.

We pulled out of the parking lot and Steve recounted the event to Chris as we headed the short half-mile to my apartment. They had a good laugh about it and then Steve turned around and said, "Relax man, she's just some girl. You never have to see her again."

"Actually," I said, "that's my best friend's little sister.

"Oh fuck," said Steve who then started laughing along with Chris. "Sorry about that. Let me guess, they don't know you like cock so much, do they?"

I looked down. "No," I said meekly.

"Well, maybe she won't say anything," said Steve.

"Or maybe she will and all your buddies will want to use you to get off with," said Chris. His simple statement sent an involuntary image of four of my buddies, naked and surrounding me, fucking me relentlessly and calling me a fucking faggot whore.

I actually got hard at that thought.

Then my phone buzzed.

I pulled it out of my pocket and noticed I had a text message. It was from Kari.

----- Kari: I think you and I have something we need to talk about. I won't say anything....yet. Promise.

I just replied with a simple message:

------ Me: OK

I put the phone back in my pocket and, holding out on a small glimmer of hope that my secret would be safe with Kari, gave them instructions on how to navigate the complex to get to my apartment. We parked in one of the unassigned spots, got out and they followed me to my apartment on the second floor. As I was walking up in front of them, I heard Chris say, "God, I can't wait to get back in that tight ass."

"Me too," said Steve. "I hope the walls here aren't that thin because I want to make this slut scream today."

I shuddered at the thought. Was I ready to be fucked hard and fast? Would it hurt too much or would I be begging for them to fuck me hard? I always read about how when a guy starts to get fucked, or even a girl for that matter, they end up wanting it harder and faster. Would I be the same way? I liked getting face-fucked that way, but my ass was different. Only time will tell...

I open up the door to my apartment and we all filed in. They closed the door and now we were alone. Just the three of us. It is a weird feeling having them here, in my apartment. It would have been one thing to know that they were coming here for me to blow them, but no, they were here to fuck my ass. Both of them. God, I hope they weren't thinking about trying to fuck me at the same time. I don't see how anyone could take two dicks in their ass. That just blows my mind.

"So, uh, what do you all want to do now?" I said. It was a dumb question. Of course I knew what they wanted to do. They wanted to fuck my virgin ass. But I was still a ball of nerves and not sure what to say.

"Get naked slut," said Chris. God, there was just something that hit inside of me every time I was called a degrading name. It was humiliating, but more than that, it was a turn on.

"Yes sir," I said. I slipped my shirt off and then kicked off my shoes. I undid my jeans and slid them down followed by my underwear. I stood in front of them, naked and vulnerable.

"Good, now take this," said Chris as he handed me the enema kit, "and go use it, shower and then shave your body. I don't want to see any hair on your body below your face. Oh, and make your face baby-bottom smooth too."

"Be quick about it too, slut," said Steve. I don't want to waste too much time here waiting for you to get yourself ready for us. I want to spend time making you scream."

My mouth dropped open slightly and I just nodded, my mind imagining them fucking me hard and me screaming bloody murder.

I grabbed the kit and went to my bathroom. I turned the water on in my shower to let it warm up and then I looked at the box. I removed everything from the enema box, read the instructions and followed them, doing the process twice. I then stepped into the shower and let the hot water cascade across my body. I painstakingly removed all of the hair from my face and my body. It was very time-consuming and I went through two razors to do so. I'm not overly hairy, but to get your entire body baby-bottom smooth takes a while to do.

As I was washing the remaining hair from my body and lathering myself up with soap, Chris and Steve walked into the bathroom to see me wet, soapy and hairless. They were both naked and sporting hard-ons. I started to wonder if they had been playing while they were alone.

They stood there and leered at me, exchanging comments about my body and what they wanted to do to me. Now see, this is the kind of leering that I enjoy. They are attractive, have nice cocks and I want to be used by them. What a complete change from the leering of the fat, greasy attendant at the bookstore.

They walked over and ran their hands over my body, feeling the slickness of my skin. They grabbed my ass and roamed their hands over my chest and legs. They bent me over and told me to pull my ass apart so they could inspect my work. I did as I was told and they marveled at my hairless bud. The cascading water rinsed the remaining soap from my body leaving me squeaky clean.

"Fuck, that's it," said Steve. "I need to fuck that ass. I'm tired of waiting." He turned me around and pulled me from the shower, throwing me over his shoulder. He started to walk to my bedroom and Chris turned off the water.

Steve threw me on the bed and I bounced slightly and then rolled on my back, my legs still together at me knees.

"Oh no," said Steve, "roll your ass over and stick your butt in the air. Keep your face on the bed."

I rolled over and got on my knees, keeping my chest and face on the bed.

"Spread your legs, reach back and pull your cheeks apart for us," he said. "For us," I thought. God, I still couldn't believe my first time was going to be with two guys.

"Now beg us to take your virginity, you cock loving whore," said Chris, his tone was even and almost menacing.

"Please," I said. "Fuck me."

They laughed.

"Not even good enough," said Chris.

"Please," I tried again. "Fuck my virgin ass. It is so tight. It will feel so good for you. I want to feel each of your cocks inside me. I need it. Please."

"Well, I suppose," said Steve. I felt the bed move and knew I was about to get fucked. I heard the flipping of a cap and realized that they had the lube. I felt some being squirted on my ass and then more was being spread on Steve's cock.

"Here you go," he said to which Chris replied, "Thanks." I assumed he handed the bottle of lube to him. I felt Steve rest his heavy cock in the crack of my ass and begin to hump his tool between my cheeks. Chris came around and said, "Here, take a hit slut."

I looked up, my chest still on the bed, and saw him presenting the bottle of poppers to me. I took two hits, one per nostril and felt my body relax and warm over. With that, Steve lined his cock up with my hole, grabbed my hips and started to push in. I felt the pressure of my sphincter giving way and there was some slight pain and discomfort, but nothing unbearable. I moaned as he worked his dick into me, little by little. The lube was definitely helping his shaft slide into me. God damn this felt good.

Steve began to push farther into me and soon, he was bottoming out, burying his entire cock into my ass. His deep strokes felt so good but I wanted more. I knew what it meant now to want to be fucked harder and faster.

I was moaning as he filled me over and over. "Harder," I said, almost unintelligibly.

"What was that bitch," he said.

I spoke louder this time, his cock sliding in and out of me at a steady pace. "Please, fuck me harder sir. It feels so good." I wasn't lying either. It really did feel good. I couldn't believe how easily it had been to give my ass up to them. They had taken their time in the store and even now as he was leisurely sliding in and out of my body, but upon my pleading request to fuck me harder, he grabbed my hips and starting to slam into me with deep, full strokes. The sudden change in the speed and even the depth as his hard thrusts probed deeper into my ass caught me by surprise and I screamed out in a mix of pain and pleasure. This only spurred him on. He slammed into my lubed hole with strong, deep strokes of his cock as it slid easily in and out of my ass with the same speed I've used on a wet pussy in the past. I was grunting, moaning and occasionally screaming out as he hit different areas in my ass. I felt so delightfully naughty having my virgin ass pounded by this older man while being watched by another.

He pulled out of my ass and with almost no delay, Chris took his place and pushed his cock into me, going slowly for 4 or 5 thrusts before taking his chance to plow away at my hole. I screamed into the pillow as the pleasure ripped through my body while my sphincter screamed from the pain of being stretched.

"Oh fuck yeah slut, you are taking these cocks so nice," he said as he furiously plowed me. "Now that you are open up, let's have some fun."

He spanked my ass a few times as he slammed into me. He would switch from fast, hard plowing of my ass, to slow, methodical penetrations where I could feel every inch of him filling me and leaving me. Steve was at my head and pulled my hair. I moved into a doggy style position in my hands and knees and Steve drove his lubed cock into my mouth. The lube wasn't the best flavor in the world, but it wasn't bad either and I honestly didn't care. With his hand in my hair, he pushed in and began to fuck my face hard, his cock slipping easily into my throat because of the lube. They tag teamed me from each end and spit-roasted me hard and fast. I was in heaven as these men used me.

Chris pulled out and Steve did so as well. Chris pulled me by my hair till I was down on the ground. They stood around me again with their cocks and he said to Steve, "Grab the lube off of the table for me, will ya?"

Steve grabbed the lube and handed it to him. Chris looked down at me and spat on my face. He then slapped me a few times and said, "You like being our whore, slut?"

"Yes, yes," I moaned, wanting them back inside of me.

He slapped me a few more times, not too hard, but enough to excite me from the abuse. "Open your mouth, bitch," he said, "and keep it open."

I opened my mouth and he held the bottle of lube out and let a long stream pour into my mouth. The taste, again, was not what I would actively seek out, but I could easily deal with it. He stopped the stream and then quickly pushed his cock into my mouth and right down into my throat. The lube made it even easier for him to bury his dick fully in me. He stood above me, bent over slightly and held my head and fucked my face straight down, my head tilted back giving him a straight path down my throat. We were making a sloppy, wet gurgling sound as he violated my over-lubed throat.

Chris pulled out and Steve took his place. They were very forceful with their fucking of my face now that I was lubed up. I was spitting and coughing a mixture of lube and spit as they went at me without holding back. They each took another turn face banging me solo and then, when Steve pulled out, they let me hold my head up normal and they took to pushing their hard, angry cocks into my mouth together.

"Only fucking whore's take two cocks in one hole," said Chris.

"What a pathetic little slut. He just can't get enough dick in him," said Steve. Their cocks snaked across my face and slid into my open mouth, my tongue lapping away at their heads and shafts while my lips tried to hold on to both at the same time.

"Ok, get the fuck up," said Chris. They pulled me up and then moved me to the bed, putting me on my back with my head hanging off. Chris got on the bed and grabbed my legs, lifting them up and presenting my ass to him. He pushed into me with almost no resistance now and began to fuck me hard. Steve stood close to my head and poured more lube on his cock. He stroked it, his dick slick and dripping with excess lube before pushing it into my mouth and deep into my throat. They plowed me from both ends again, continually talking shit to me about how much of a slut I was to let two strangers into my home to fuck me. They slapped me and spit on me, all which turned me on even more.

They went to switch again, but had me move. Steve laid down on the bed and had me straddle him. I squatted down on his cock and began to bounce myself on him while Chris stood and fucked my face. I found my legs starting to burn and felt sympathy for every girl who had ever rode me and complained about her legs hurting. It was a challenge if you weren't used to it.

After a few minutes, they wanted to switch again so they had me climb off Steve's cock. Chris told Steve to stay how he was, but slide further up on the bed. Chris laid down with his legs straddling Steve's and moved himself so that the bottom ridge of his cock was against the bottom ridge of Steve's. He held them up and said, "Get down here and suck us both bitch."