Eric - Down the Research Rabbit Hole

In 2002 I was straight, 100% heterosexual. So much so I never had a thought about gay sex, it never crossed my mind.

I grew up in a large family, with 6 kids, only one girl and she was the second child so there was a lot of masculine energy around the home. Especially when my sister moved out. I was child number 5, so you can imagine by the time I was in high school my parent's rules were pretty relaxed. To the point where I had girlfriends in my room and my parents didn’t care they just made me promise to use a condom if something happened. When my oldest brother had girls over they were not allowed in the bedroom and never home alone.

I’m no fool, my older brother got his girl pregnant their senior year of high school and now he works at the garage with my old man and my momma nearly beat his ass for making her a grandma at her age. I was not going to take part in that.

I had heard all the excuses from my homies when it came to condoms. “My dick is too big,” “I can’t stay hard,” whatever the excuse was had me nervous at a young age. Puberty hit me kinda young I guess so by the time I was 16 I was going crazy. I never had privacy in the house to beat off because I shared a room with two of my siblings. Couldn’t do it in the shower because we only had one bathroom and had to leave the door unlocked in case one of the other 7 people in the house needed to use the toilet.

I was scared to have sex but man I wanted it.

After my brother got his girl pregnant my mom put a huge jar of condoms on a table by the door and told us she wouldn’t ask questions just take a couple when you leave the house no matter what and she would keep refilling it.

It’s important to know that I’m not the athletic brother or the best-looking brother, but I am the smart brother. I planned things, I was organized, I studied, and I was always prepared. So when my homie Jacques was telling me how he and his girl were fucking and he couldn’t stay hard because of the condom and so they fucked raw, I told him he was insane. He told me since I was a virgin I couldn’t understand.

The conversation got me hard though, which was difficult to hide because I am blessed with an 8” cut thick piece of meat. Thankfully Jacques didn’t notice it.

Later that day I did what I normally do and went to the public library to get online. I live in a decent neighborhood, and we have a nice library just off the main road. It has 8 computers that are free for public use. I usually am here for homework since they require essays and stuff to be typed up. I also do a good amount of my research online.

This particular day I purposefully picked the computer in the back corner where people have to go out of their way to stand behind you and read what you’re looking at. I hopped on AOL and searched a bunch of different articles about condoms being a boner killer. One link brought me to a forum where some guy asked for advice on how he could stay hard using a condom. The responses were a huge mix of people giving suggestions and other people telling him you can’t and just not to use them. One response seemed like a good suggestion though, they said to masturbate while wearing a condom and you can trick your brain into liking the feeling. That was interesting, there was a jar of condoms at home I could practice with if I could find some privacy.

I noticed a link for a chat room, the room was labeled, “Men Seeking Men” and me being straight and naive I thought it was going to be a room for guys to get advice from other guys. So I clicked and went through the process to get a name and get into the chat. I noticed in the feed most guys were just posting their age, that they were male, and the state they lived in. So I posted, 16/M/NY to see what happened next.

“Troublemaker1 Sent you a private message” started blinking in the corner. So I clicked.

TROUBLEMAKER1: 19/M/NY here

Eric2002: cool

TROUBLEMAKER1: what are you up to?

Eric2002: I’m just doing some research.

TROUBLEMAKER1: on what subject?

I looked around to see if anyone was near me, there was only one other person in the computer section and it was an older white guy at the opposite end.

I nervously responded.

Eric2002: condoms and sex.

TROUBLEMAKER1: I’m an expert hahaha

Eric2002: really?

TROUBLEMAKER1: I’ve been using them since I was 15.

Eric2002: really?

Eric2002: 15?

TROUBLEMAKER1: Yes, but I can’t say I always use them all the time.

Eric2002: what do you mean?

TROUBLEMAKER1: You know how it is in the heat of the moment. Sometimes you don’t have one or don’t need one so you fuck raw.

Eric2002: Oh shit, for real?

TROUBLEMAKER1: My dick has needs hahaha.

Eric2002: isn’t that unsafe? What about pregnancy?

TROUBLEMAKER1: Pregnancy?

Eric2002: Yeah?

There was a pause. I thought maybe I lost connection, but then I noticed the larger chat window was still running.

TROUBLEMAKER1: I think it’s a risk we all run in the heat of the moment.

I thought about that for a bit.

Eric2002: I’m not trying to get into that kind of situation.

TROUBLEMAKER1: I get it, safety is important, that’s why you gotta get tested regularly even if you’re using condoms religiously. Have you been tested recently?

I felt myself blush as I started typing and retyping my response.

Eric2002: I am a virgin.

TROUBLEMAKER1: Oh shit, ok. So what are you looking for?

I thought about this for a bit.

Eric2002: just advice I guess. I really want to have sex but I’m nervous.

TROUBLEMAKER1: about what?

Eric2002: staying hard in the condom I guess. My friend was telling me he can’t stay hard wearing condoms.

TROUBLEMAKER1: yeah, that happens to some guys, it really depends on the situation I guess. Were you talking about using condoms or was this in the heat of the moment?

I didn’t quite understand what he meant.

Eric2002: we were just talking about it, he was telling me about the sex he had recently where he couldn’t stay hard and had to take it off and fuck raw.

Just typing the words made my dick get hard in my boxers.

TROUBLEMAKER1: well it’s good that you had that conversation and know each others history. Do you trust him?

Eric2002: Of course, we been homies since we were 5 years old.

TROUBLEMAKER1: oh, wow, that’s lucky. But you’re still a virgin? You didn’t let him go raw?

Eric2002: I’m still a virgin, I told him it was dangerous and he was stupid for fucking raw. He told me I wouldn’t understand until I lost my virginity.

TROUBLEMAKER1: he sounds a bit pushy, do you like that?

I had to think about this.

Me: I guess, he’s my boy hahaha.

TROUBLEMAKER1: I see, what have you done together?

I thought that was a weird question.

Eric2002: well we been homies since we were little, so we’ve done just about everything together.

TROUBLEMAKER1: oh really?

Eric2002: of course.

TROUBLEMAKER1: so you trust him?

Eric2002: of curse.

TROUBLEMAKER1: but you’re not letting him hit it raw?

Eric2002: I mean, I don’t have much of a choice in it.

TROUBLEMAKER1: well, you do, but I like that attitude.

Eric2002: what do you mean?

TROUBLEMAKER1: you let your homie have what he wants.

Eric2002: well, he’s my boy hahaha

TROUBLEMAKER1: I get that. I had a boy like that back in High School, we were real tight and he let me give it to him any way I wanted and he just took it, it was great.

I wasn’t really following what he meant, but I thought he was trying to relate.

Eric2002: that’s cool.

TROUBLEMAKER1: yeah, but he went away for college and I stayed home and go to community college.

Eric2002: which one?

TROUBLEMAKER1: CUNY Albany

Eric2002: no shit, I’m not far, my house is near that new Walmart

TROUBLEMAKER1: really?

Eric2002: yeah, I walk to that plaza all the time. Gotta cut through the back though, I’m not walking all the way around hahaha.

TROUBLEMAKER1: damn, that’s close to me, I got a house with some homies over by the Olive Garden.

Eric2002: oh wow, it’s a small world, my sister hosts at that Olive Garden hahaha.

TROUBLEMAKER1: I’m Tucker, my friends call me Tuck.

Eric2002: I’m Eric

TROUBLEMAKER1: what do you look like?

Eric2002: black, skinny, 5’9”, but I guess that’s half the guys around here hahaha

TROUBLEMAKER1: yeah, I’m black/200lb/6’1”

Eric2002: oh so you’re a big dude

TROUBLEMAKER1: I’m in good shape, I play ball with my homies all the time.

TROUBLEMAKER1: Unless you’re talking about my dick, then I’m certain I’m bigger than your boy Jacques hahaha

That was a weird thing to say, but that’s just how guys talk.

Eric2002: well I don’t know about that, I’ve seen Jacques and my boy is packing hahaha

TROUBLEMAKER1: why don’t you come find out?

Another weird thing to say. I didn’t know how to respond to this. I also didn’t understand why my dick was so hard just talking about this stuff with a guy I don’t know.

TROUBLEMAKER1: unless you want to save it for your boy?

Eric2002: what do you mean? You want me to come over and look at your dick?

TROUBLEMAKER1: I was hoping for more than a peep show.

What was this guy talking about? This was getting weird.

Eric2002: I’m not sure what you’re getting at.

There was a pause.

TROUBLEMAKER1: if all you want to do is watch, that’s cool, but I’m horny as hell and was kinda hoping to fuck.

What the fuck? He wants me to watch him fuck? I admit the idea of watching people fuck in front of me made my dick leak a little precum. My heart started racing a bit and I nervously typed out a response.

Eric2002: you want me to watch you fuck?

TROUBLEMAKER1: that would be hot, but I try to stay low-key and prefer one on one stuff.

My dumb ass still hadn’t caught on to what was happening, and my dick had already started taking over my brain with thoughts of watching this dude fuck his chick and all the potential scenarios where I could drain my balls with his girl.

Eric2002: oh, so what were you saying?

Another long pause.

TROUBLEMAKER1: you could come over and we can just see what happens. You seem cool, sound like a good lookin dude, I’m horny, you’re horny right?

Eric2002: I’m always horny hahaha

TROUBLEMAKER1: then come over and lets see what we can get going.

I liked how easy he was to talk to about this stuff, but I must have been frustrating him.

TROUBLEMAKER1: I get you’re a virgin and holding out for your boy Jacques, but you gotta get your nut right?

Those words melted my brain. Was he talking about us fucking around together? I had a little bit of panic when I realized we were having two different conversations this entire time. I scrolled up in our chat and realized he thought me and Jacques were butt buddies. I looked around the room again to make sure no one else saw. I don’t know why I felt like everyone could tell what I was chatting about through some sort of 6th sense or something, but I shyly typed my next message.

Eric2002: Dude, I’m not gay.

I should’ve just ended the conversation there and closed it out, my moushe hovered over the “X” about to close it, but a part of me needed to see his next message, which came at a delay.

TROUBLEMAKER1: I aint gay, just horny.

The five words that changed everything for me. I reread that sentence a dozen times. I’m also not gay, and I’m also really horny.

TROUBLEMAKER1: you gonna swing through?

I typed and retyped variations of “no,” but couldn’t bring myself to hit enter.

Eric2002: I don’t know.

My heart was beating so hard I was sure it was echoing throughout the library.

TROUBLEMAKER1: we don’t have to fuck, just come suck my dick.

He wanted me to give him a blow job? That’s disgusting.

Eric2002: I don’t think I can do that.

TROUBLEMAKER1: well what do you do?

Eric2002: I don’t know.

TROUBLEMAKER1: what do you and Jacques do?

My mind flashed back to when we were 13 and a couple times we jerked off together. We were real horny at his place, I was sleeping over, we slept in the same bed and he said he needed to jerk off before going to sleep. I told him to go for it and watched. I pulled mine out and jerked next to him, I nut pretty quick though seeing him jerking, I didn’t even see him bust because I was in the process of cleaning up my cum.

Eric2002: we jerked off together.

TROUBLEMAKER1: that’s it?

Eric2002: yeah.

There was a long pause.

TROUBLEMAKER1: I can beat off on my own homie, you gotta give me more than that.

I was so nervous, I don’t know why I kept participating in this conversation. My palms were getting sweaty.

Eric2002: like?

TROUBLEMAKER1: you got a nice ass?

I thought about it.

Eric2002: depends on what you like.

TROUBLEMAKER1: I like to slide my dick between some nice cheeks like they are titties, your ass big enough for that?

Eric2002: It’s not that big

Eric2002: but maybe, you could try.

What was I saying?

TROUBLEMAKER1: that’s a good attitude. What else can I try?

Eric2002: I don’t know.

TROUBLEMAKER1: if it feels good can I slide it in?

My heart was beating so fast I was feeling light-headed.

Eric2002: you mean fuck me?

I felt a drop of precum squeeze out of my dick into a wet spot in my boxers.

TROUBLEMAKER1: if you want me to.

Eric2002: I don’t think so.

TROUBLEMAKER1: Just the tip then?

I was practically shaking with nerves now. No way was I letting him do that.

Eric2002: thats kinda gay, isn’t it?

TROUBLEMAKER1: no, but it feels real good for both of us.

Eric2002: It does?

TROUBLEMAKER1: oh yeah, trust me, you will love it.

Eric2002: How is it not gay?

TROUBLEMAKER1: you’re not gay, I’m not gay, we’re just two guys helping each other bust a nut.

I was so horny and this guy was giving me all kinds of ideas that made it seem so casual for us to do, not the same pressure of having sex with a girl and having to be good at it and make her orgasm, just two guys having fun that’s not gay because we are both straight.

Eric2002: I guess we could try it.

I hit send, with hands that were shaking like I was out in the freezing cold.

TROUBLEMAKER1: hell yeah, can you come over now?

Eric2002: I can, but I have to be home by dinner.

TROUBLEMAKER1: where you at?

Eric2002: the library

He gave me step-by-step instructions on how to get to his house, and even gave me his number in case I got lost.

I closed out the window and quickly searched “condoms + butt sex” and got a lot of hits for porn and I got scared and logged off. I don’t know if the librarian can see my search history so I closed out of everything quickly. I reached into my pants and tucked my dick up into the waistband of my boxers, sticking out the top, thankfully my baggy t-shirt covered it up.

Fifteen minutes later I found myself walking up on a house that looked like the one he had described. I stood there staring like a fool and the door opened and a big black dude with tight braids walked out in a beater and some basketball shorts riding low, his boxers sticking out the top. His muscular arms and shoulders on display, a couple tattoos on one of his arms. He smiled at me and waved me over.

I walked up the steps quickly and into his house before I could change my mind and run. He closed the door and locked it, saying nothing. He walked me through a kinda messy house that smelled like weed and into a bedroom near the back of the house. He closed the door behind us and pushed the little button lock on the handle.

“My roommates tend to walk in without knocking,” he smiled.

I hadn’t given much thought to any of this and felt even more nervous no knowing there was a possibility that someone could find out about this.

“Are…are they here?” I asked.

“Nah, they are in classes and working, we should be good to fuck around for a while.” He unconsciously grabbed his crotch at the word “fuck.”

I nodded my head.

“You smoke?” he asked. “You seem jittery, it’ll help,” he held out a joint.

I had smoked a few times with Jacques, so this wasn’t new to me. We sat on Tucker’s bed and lit up. His weed was strong and did get me relaxed fast. We smoked the entire thing, not saying much.

“You want the last hit?” he asked, holding it out for me.

“Nah, I’m good,” I smiled, eyes glossy and I leaned back.

“Good,” he lit it one last time and took a long drag, held it, and then blew out the smoke. “Take your shit off, get comfortable.”

Instinctively I obeyed and without getting off the bed slipped my jeans and shorts off, casually folding them and setting them neatly on my shoes at the foot of the bed. He watched closely at my every awkward move.

“Beater and drawers too,” he grinned, putting the ashtray on his nightstand.

I nervously slipped my boxers off and pulled my tank over my head, bunching the two up and dropping them over the edge of the bed hoping they land on my other clothes.

He looked me up and down and smiled. “Damn bro, you got a good body.”

I felt heat rise in me from his approval.

“Don’t hide that dick, lets see it,” he said, pulling his beater off and revealing his toned torso.

I moved my hands from my dick which was now getting hard fast.

He let out a small growl, “mmm, that’s real good, you want to see mine?”

I nodded like I was just asked if I want free money.

He stood to the side of the bed, slowly pulling his shorts off, his boxers were clean an new looking, a massive dick swinging inside them. He put his shorts on a pile of clothes on his dresser, then reached inside his boxers and stroked himself for a second before dropping his boxers too. I stared in awe at his dick. The only dick besides mine I had seen hard was Jacques and mine was bigger than his, but this guy had me matched inch for inch but his dick looked harder and thicker, possibly angry if that’s a thing. I could tell from the way his skin was pulled back and the shine of precum on the head that he was uncut, just like a bunch of guys in the locker room.

He stared at me, slowly stroking as he knelt back on the mattress. “Let me see that ass,” he said in a low voice that matched his muscular body.

I was sitting with my back to the wall and didn’t know how I was expected to present myself. I hadn’t seen much porn so I just slowly lay flat on his mattress so my hard dick was rubbing his sheets and he could get a good look at my ass.

He leaned forward and I felt his big hand gently rub my left ass cheek. I let out a sigh, no one had ever touched me like this, I never even had a girl grab my ass during makeout sessions. The closest thing I had was getting my ass smacked while playing ball, but this was sensual, this was erotic, and he wanted this more than I needed it. I didn’t realize how horny I was until I noticed even the heat from his body was turning me.

“Scoot this way,” he pats the mattress towards the center of the bed.

I shimmied over, closer to him. He immediately straddled my ass. I felt his weight on my upper thighs, the hair from his legs and ass rubbing my skin. It was so weird, but so hot at the same time. Then I felt it, his dick, the heat of it, the weight of it, the thickness of it, along with his big balls suddenly resting on my ass. He palmed my ass cheeks like basketballs and gently massaged them, then pulled them apart so his semi hard dick could rest in the crack and it sent my hormones into overdrive and I felt my brain leaving my body as the blood drained into my rock hard dick.

I sat up on my elbows, looking back at him, I had to see what he was doing, I had never felt pleasure like this before. I couldn’t crane my neck enough to see clearly, but what I could see was this good-looking dude, naked sitting on me. I saw his arms flex as he worked my ass cheeks with his hands. I saw his abs flex as he rocked his dick between my cheeks, his eyes glued on either his dick or my ass, but the smile on his face said he was really enjoying it.

I felt the tip of his dick slide across my hole and it shot a bolt of pleasure up my spine, it felt so good I felt my hole clench and a drop of precum dripped out of my dick onto his sheets.

He grabbed my narrow 28” waist, putting the weight of his upper body on my lower back and he gently started to run his dick up and down between my ass cheeks, his heavy balls slapping at the bottom of my ass with every stroke. The pressure of his weight felt good, but the dick sliding across my hole was invigorating, a soft moan escaped my lips as he used my ass as his own play toy.

“Damn Eric, you have a nicer ass than you let on,” he stopped and tapped his tool on my hole.

I let out a soft groan, I didn’t know how to respond. Should I compliment his dick? That would be kind of gay right?

“Can I put some lube on you so my dick slides easier?” He asked with an excitement in his voice.

“I guess,” I popped up on my elbows again, looking back at him the best I could.

He pulled out a little box from under his bed, flipped open the lid and pulled out some lube, then put the box on the nightstand. He squirt a generous amount on my ass and then stroked some onto his dick. I had never had my ass played with, or any other intimate sexual experience other than my hand on my dick so I was blindly going along, just enjoying one new feeling after the next. His confidence in everything he was doing was intoxicating. As he slowly stroked his dick with his right hand he was using his fingers on his left hand to smear the lube up and down my crack, it dripped down onto my balls and between my legs a little, but he rubbed it in like it was a lotion and my ass and upper thighs were coated in it.

He tapped his cock on my crack, and the thump of his meat resonated through my body sending waves of excitement to every nerve ending I had, another drop of precum squeezed out of my dick and onto his bed.

“Damn that ass looks good bro,” he palmed both globes again, squeezing them together and then pulling them apart. He shift his weight so his dick could rest in my crack like a hot dog in a bun, his balls dangling down onto mine. He squeezed my cheeks together and let out a soft moan as he gently slid his dick back and forth between the cheeks. The feeling his dick gave me as it slid across my hole was something else. I didn’t know your ass hole could give off pleasure like this and I let out a soft moan with him as another drop of precum squeezed from my cock onto the mattress.

He slowly humped me like this for a few minutes, it was like an amazing free massage and I was getting so turned on by it. I told myself I was turned on by the feelings and not the guy, but I knew a little bit of it was Tuck getting off on my body, using my body for his pleasure. I let out another soft moan when he lay flat on my back and his weight pushed his dick into my crack with more pressure, rubbing more ridges across my hole.

“Feels good huh?” he whispered into my ear, his breath warm on my skin.

His nude, muscular body completely coverd mine, the heat was intense, but the skin on skin contact was blowing my mind as he continued to hump my ass gently.

“Uhhuh,” I managed to groan out.

My arms folded under my head as a pillow, I just lay there, enjoying him enjoying me.

A few more thrusts and his dick dropped between my balls and my thigh, he pushed and moaned in my ear, the lube letting him slide easily, his precum adding more wetness as his dick pushed down and back up.

“Mmm, hold your legs tight together, let me fuck between your legs,” he whispered in my ear.

I did as I was told, trying my best to press my thighs together as his hips bounced on my ass and his dick slid between my thighs, rubbing my balls, occasionally it would pop out and hit my grundle, and once it even slid back up across my hole and the pleasure that shot through me was so intense I let out a loud moan that sounded like a strangled cry.

“Fuck yeah, Eric, you like it?” He cooed.

“Yeah,” I struggled to say, his weight keeping pressure on my body.

He kept it up for a bit, and more frequently his dick would pop out and slide across my hole eliciting a moan from me. I felt like such a punk for enjoying it, but man it felt good.

After a few more minutes of frotting, another dozen strokes of his dick across my hole and he pushed himself back up, grabbed my waist, and went back to letting his dick exclusively slide across my hole, pressing my ass cheeks together for maximum pleasure for his dick, and it felt amazing for me too.

He leaned over and grabbed his little tube of lube, squirted a little more on my crack, and then used his dick to smear it directly on my hole. The sensation was intense, something about the gentle pressure, the localized attention being directly on my hole, his slick dick head slid around and circled my hole with such ease there was almost no friction.

“Mmm,” I moaned, my unbelievably hard dick squeezing out another drop of precum as I gently humped his mattress.

He kept circling my hole with his dick head and gently pressed harder, it felt so good, I humped the mattress a little more and squeezed my ass cheeks around his dick to maximize my pleasure and fuck I thought I might cum. He pushed a little harder and it started to become too much, I groaned when it went from pleasure to uncomfortable, but then he gave another gentle thrust and the head breached my outer ring of muscles. A sharp pain shot from the tip of his dick up my body and came out a sofucated, “ow, bro, what the fuck?”

“It’s just the tip man,” he said calmly.

I popped up on my elbows, “Nah dude, that fucking hurts,” I turned my head to look in his eyes.

“Just relax, push your ass out,” he told me.

I don’t know what the fuck that means, but this shit hurt. My dick immediately went limp. He pushed his dick head into me again, a little harder this time and I shot out from under him and off the bed, holding my ass hole and pacing the room.

“Fuck man, that hurt, fuck,” I glared at him and tried to catch my breath.

He chuckled, “You’re a virgin?”

A new pain shot through me, the word “virgin” cut like a knife. Like I’m suddenly not cool enough. I continued to rub my asshole, “I am,” I admitted, feeling far less confident than when I walked in here. The pain in my ass was becoming less as I paced. I saw my clothes neatly piled at the edge of the bed and debated getting dressed. Tucker was sitting back on his heels, legs spread so his balls dangled just above the mattress as he slowly stroked his dick while grinning at me.

“Come on man, come lay back down and let me get the tip in,” he cocked his head and his toothy smile was on full display.

“I don’t know, that fucking hurt bro,” I rubbed my hole and felt a wetness, “Am I bleeding?”

He laughed, “Nah bruh, that’s just some precum,” he shook his head.

Ew, he got his juice on me? What the fuck?

“Get that little ass back over here, you promised me I could get the tip in if I invited you over, don’t tell me I wasted my time,” his tone changed.

I felt bad, I did tell him that. I felt my heart start to race as I continued to rub my hole and watch him stroke himself.

“I didn’t think it would hurt that much,” I said with a timidness in my voice.

He rolled his eyes, “Bruh, it ain’t hurt that bad, I’ve taken way more than the tip and it stings at first but then it feels great if you don’t punk out,” he shook his head disappointed in me.

I felt a sudden rush of frustration, “I ain’t no punk,” I stoped rubbing myself, the pain had completely gone now.

He shot me a crooked, devilish smile, his eyebrows raised high up, “bro, it looks like you’re punking out on me, can’t even handle the tip, gonna leave me with blue balls.”

I rolled my eyes, huffed, “ugh, fine, I’ll try it again,” I hated being called a punk. Being a bit on the nerdy side at school and not the athletes my brothers are I have always been called a punk or a runt.

“I don’t know man, you’re just gonna bitch out if it stings again, certainly ain’t gonna let me get my nut,” he scoffed.

“No, I told you I would and I will,” I tried to regain my man-card.

He shifted his weight to lean back and make room for me on the bed, “Alright, we’ll see,” he said and gestured for me to climb back into place on the bed.

I quickly got back on the bed and lay flat, grabbing a pillow from the headboard edge and clutching it as I lay my head on it.

I heard him click the lube back open and pour a few heavy drops onto my crack, then he ran his fingers over my hole, that felt good, way better. He pushed the tip of his finger into my ring, and neither of us said anything, it didn’t hurt the way his dick did, just felt weird.

“You ok?” He asked.

I nodded yes.

He pushed his finger slowly deeper into me, very slowly and my hole clenched but the speed at which he pushed allowed him to get his full finger in me without any pain, just felt so weird to have something in my ass. He let it sit there for a minute, I could hear him stroking his dick with the other hand, the lube making a squishy sound with every slow stroke.

“Damn that’s tight,” he started to wiggle his finger.

This definitely felt weird, “what are you doing?”

“Just opening you up, your ass is hella tight and I don’t need you jumping out on me again because my dick is bigger than a finger,” he said.

“I won’t, I’m not a punk,” I told him.

He slid his finger out gently, added a generous dollop of lube and then pushed two fingers into my hole.

“Oh shiiiit,” I groaned as he pushed them both in slowly until they were completely inside me.

“Ok, that’s it, maybe you won’t be a bitch after all,” his voice softened again, becoming more playful like it was before.

He wiggled his to fingers, fingering my hole like my boy Jacques says he fingers his girls pussy. I just hugged the pillow tighter and did my best not to groan or worse moan because it was uncomfortable but every now and again it would feel really good and I could feel my dick getting hard again just from all the touching and pressure inside me.

The sound of the cap on the lube snapped open again, another dollop dropped onto my hole and his two fingers more easily pushed it into me as the squishy sound of him stroking more lube on his dick could be heard in the quiet room.

He slowly pulled his fingers out and rubbed them on a hand towel he had with the lube. He repositioned himself on my legs again, spreading my ass cheeks apart so his big dick could lay between them.

“Mmmm, I think you’re ready,” he said softly, squeezing my cheeks against his dick as it slid between them and across my hole.

He tapped the head of his dick on my hole, the vibration felt good, real good, and I was ready to prove I wasn’t going to back out. He shift his weight on me again, the tip of his dick lined up with my tight hole and he wiggled it, it felt good, way better than the first time he put the tip in. Then, he pushed and the tip actually popped into my hole. While it wasn’t a shooting pain, it did surprise me, and felt very uncomfortable.

I sucked in my breath and groaned, burying my face into the pillow.

“You ok?” he asked.

“Yeah, fuck, ungh” I grumbled into the pillow.

He held it there for a minute, then let it pop out and gently pushed it back in, it stung less and less with each time he pulled out and popped the head back in. After a few minutes it actually slipped in withe ease and kinda felt good.

“Fuck you’re hole is tight dude, good thing I precum a lot,” He chuckled with a glee in his voice.

The thought of his juices in or even on my body kinda grossed me out, but I nodded my head agreeing with him.

“Feels fucking good,” he said, continuing his gentle assault on my hole.

I felt him push a little more in and I groaned, the pleasure draining from my body and the sting returned, I groaned. “Ah, fuck man, what are you doing?”

“Just relax, I’m trying to help you open up, you’re too tight, I want you to enjoy it too,” he told me, pushing a little deeper.

I started to squirm from the uncomfortable feeling inside as he stretched my hole to fit the girth of his dick. He held my waist with his hands, pressing down and holding me in place as I squirmed.

“Just relax bro, trust me, I know what I’m doing, don’t punk out on me before it feels good,” His voice dropped a bit.

I grit my teeth as his dick reached new depths inside me, “fuck man, ungh…it’s too much,” I told him.

“It’s just the tip bro, barely,” he rocked his hips, trying to get more into me.

“Ungh, fuck, it feels like way more than that,” I tried to keep my voice calm.

“You need me to pull out?” He asked, with a tone in his voice that triggered something in me, making me feel like I needed to prove to him I wasn’t the little bitch he thought I would be.

“No, it’s fine, just doesn’t feel good,” I hissed, hugging the pillow tighter.

“It will my guy, just gotta fuckin relax, your hole is enjoying it, and trying to pull my dick in already. If you keep sucking me in I’m going to nut pretty quick,” he told me.

I felt an odd sense of pride in giving him that kind of pleasure, but fuck I don’t think I can handle this for long. “Ahhh, shit,” I groaned feeling him push even deeper, “fuck man, that’s way more than the tip,” I groaned.

“Your ass was pulling me in bro, fuckin swallowed my entire dick, I’m balls deep in you,” he sounded so excited, gyrating his hips on my ass.

I don’t know how my ass pulled him in, but I was determined to push him out. I squeezed my cheeks the best I could and pushed my ass up to push him out but I felt his dick sink more into me. I felt him rock his hips and his balls were sliding on my taint.

“Yeah, that’s it Eric, fuck your ass feels good,” he moaned at my trying to push him out.

He started to slide his dick out, relief washed over me, but then he pushed back in until his balls dragged on me again and I groaned.

“Ungh, wait, wait, Tucker, unh… what are you doing?” I managed to meekly say as he slid his dick back out and back in again.

“Mmm…bruh, just let me fuck you for a minute,” he whispered.

“What? Nuh-uh, ungh, you can’t fuck me, that’s…that’s fucking gay dude,” I started to panic with his continued thrusts.

“It’s fine man, I’m just using your ass to bust a nut, you’re just helping me out,” he grunted as he started to pick up a haphazard rhythm.

“Ungh, wait, dude, hold on, I, ungh…this isn’t what we talked about,” I started to wriggle under him, twisting my torso to look back at him.

He didn’t slow down or speed up, “Bruh, you promised you’d let me use your ass to get my nut,” he had so much pleasure in his voice.

I hissed as he hit a new deeper spot in me, “fu-uck…I didn’t agree to you fucking me.”

“It’s even better,” he said, then rocked his dick deep into me and put his weight behind it.

“Ahh, fuck dude,” I groaned. The pain and pleasure mix was a weird sensation, I noticed my dick was semi-hard under me and I could feel myself leaking precum every time he thrust deep like that.

“Shit bro, this is the best ass I’ve ever fucked, you’re gonna make me nut quick,” he told me, repositioning to get even better access to my hole.

I could feel every ridge of his cock sliding in and out of me. My heart was beating so fast. This was all happening so quickly I hadn’t thought about what was going on, I’m losing my virginity to a man. I’m having sex, with a man. Shit, he’s fucking me without a condom! I went into an instant panic and tried to push myself up from under him.

“Wait, no, you can’t fuck me without a condom,” I twisted myself up to look him in the eye. My waist still held in place from his strong hands and his dick buried deep inside me.

He stopped fucking, “Bro, I’m already fucking you,” he looked at me like I was being crazy.

“Yeah, but…I didn’t know you were going to fuck me and I can’t have sex without a condom,” I warned him.

“Ugh, fuck dude, ok, I’ll put on a condom, but you can’t bitch out on me,” he slowly pulled out of my ass.

“I won’t, I just can’t have unsafe sex,” I told him and rolled onto my back, feeling the new emptiness inside me as he hopped off the bed and started digging through his little box. The head of my dick was coated in precum, I started stroking it to full hardness, my legs spread on full display, no longer feeling shy about being naked with him.

“Shit,” he said, closing the little box and then opening the top drawer of his dresser, “hmmm,” he moved some things around and then closed it too. “Hold on,” he ran out of the room.

I slowly stroked my dick, I can’t believe I’m going to let him do this. I guess it’s not gay if we’re not gay right? I mean, I’m definitely not gay, I’m just helping my new friend have an orgasm…if anything I’m just being a good friend right?

He came back in the room with a packet that looked like it might have soy sauce in it, but he ripped it open and a condom popped out, “it’s gonna be tight on me, it’s my roommate’s, but it should work,” he said, struggling to stretch it over his long hard dick. Even rolled out it barely made it to the root of his shaft. He added lube and stroked himself back to a full erection.

“Ok, now are you gonna let me get my nut?” He asked, smiling at me, spreading my legs.

“Uh…ok, yeah,” he hitched up my legs under my knees and put them on his muscular shoulders, using one hand to guide his dick to find my hole and pushed. The head popped back in, “ow, shit,” I groaned.

He gave me a look when I groaned to make sure I wasn’t gonna punk out, and then he slowly continued to push it all the way back in. It felt even weirder now. Somehow I felt even more like a bitch in this position. He slowly pulled out and pushed back in, I groaned and he moaned in unison.

“Fuck yeah, Eric,” he pushed my legs closer to my chest, making it harder to breathe but he more easily was able to thrust his cock into me. It stretched my hole and hit a spot that was a new source of pleasure for me.

I couldn’t help but moan, “oh fuck.”

“Yeah, take my dick bro, open that hole for me,” he whispered, looking down at me with a lust I had never seen before.

This new pleasure was feeling good, really fucking good. “Oh fuck Tucker,” I started pulling on my dick and rocking my hips in the hopes his flared head would hit that spot in me some more.

“That’s it, stroke yourself off man, I told you it would feel good. You like that dick in you?” He asked.

“Unhg, yeah,” I admitted instinctively, my brain wanted me to lie, I didn’t want him to know I was enjoying him fucking me, but my body gave me up.

“Fuck yeah you do, get your nut and I’ma nut in you bro,” he started fucking me harder, not faster but hard enough that his hips slamming into me sent and extra vibration of pleasure to my dick and insides, and fuck it was going to make me cum.

“Mmmm, Tuck, I’m gonna cum,” I cried out, feeling that familiar tingle in my balls as my ass pulsed around his pistoning cock. The amount of pleasure sensors firing off in my body was overwhelming.

“Oh fuck yeah, get your nut bruh,” he didn’t skip a beat just slammed harder into my ass.

“Oh God, I’m about to bust,” I cried out and felt my balls tighten He slammed into my tightening hole with even more vigor, my toes curled and my leg muscles pushed him up as I felt my entire body tightening and relaxing at lightning speed. The orgasm started in my asshole and my body convulsed as I pound my dick and it erupt hot cum all over my chest and stomach, rope after rope shot out and I moaned so loud the neighbors probably thought he was killing me. “Oh fuck, ungh!” I twitched and jerked as my balls completely emptied themselves.

He pushed harder in as my ass clamped down and tried to push him out. “Ahh, shit,” I groaned and pushed on his chest to stop him, his dick sliding out with force. “Fuck, that hurts,” I told him.

He ripped the condom off and started jerking himself, “That was awesome, did you like it?”

It took me longer than usual to recover, my mind in a post-nut haze, “dude, I can’t…that was intense,” I was still catching my breath, squeezing the last few drops of cum out of my softening dick onto my purlicue.

“The best orgasm you’ve ever had?” He smiled, stroking himself faster.

I shook my head no, my body trying to deny it, but the truth came out my mouth, “yeah,” I chuckled, embarrassed.

“Good, now it’s my turn,” he said, pushing my legs off his shoulders and to one side.

“What do you mean?” I was confused as he manhandled my body and flipped me back onto my stomach, my cum now smearing onto his bed.

“Just let me fuck between your legs until I nut,” he straddled my legs again, pouring more lube onto my ass, his cock and letting it run down between my cheeks to my grundle.

“Oh, ah…ok,” I was still reeling from everything that happened in the last hour.

He slid his dick across my hole, it puckered from the attention, I let out a soft moan. He humped my ass like this for a minute until his dick slipped down between my legs and he lay on my back, treating my legs like a fuck toy. The weight of his bigger, more muscular body on mine was comforting, I could feel his breathing, his moans tingled through my naked body like a warm hug. His chin dropped down over my shoulder as his dick popped back up between my cheeks and across my hole. “Mmm,” we both moaned gently.

He pushed himself up into a plank so he could fuck across my hole but his dick head caught on my hole and the head popped in, it stung and I yelped.

“Ahh, fuck man,” I groaned, my post-nut hole was not as willing as my horny hole was ten minutes ago.

“It’s ok,” he whispered in my ear, his dick fell out on his next thrust and slid across my hole again, and again we moaned together.

A few more thrusts and his hips shifted and his dick caught on my hole again, this time the head and a little more pushed in.

“Oh fuck,” I popped up on my elbows, my back meeting his chest.

His chin on my shoulder, “Just let me get a few strokes in.”

The warmth of his face against mine, the feeling of his heart beating against my back, I couldn’t think and said nothing. He pushed deeper, slowly, my hole adjusting back to the size of his hot rod.

“Mmm fuck yeah, open that ass for me, help me get my nut man,” he kept pushing until I felt his pubes brushing my ass cheeks and we both moaned.

He held it there for a second, grinding against me. Then one slow stroke, then another, he kept a very slow pace being as gentle as possible but after a dozen strokes, it hit me that he was no longer wearing a condom.

“Ngh…the condom?” I asked, my heart pounding in my chest.

He bottomed out, “It was too tight, I was never gonna bust with that thing on. Besides I don’t have another one,” he kept stroking his dick in me.

“Are you going to pull out?” I whispered.

“You’re ok, it’s ok bro, just help me bust real quick,” he whispered in my ear.

I huffed, resigning, “Are you close?”

“Yeah bro, real close, just enjoy this dick in you for a minute,” he groaned, thrusting a little faster, holding me tightly.

The increased power of his thrusting was hitting me raw, part of me was enjoying it but another part was in pain, “fuck man, pull out and I’ll suck you,” I offered.

He kept thrusting, “Nah, your ass feels too good, I’m getting real close,” he was hitting it faster and harder, with shorter strokes but really digging into me.

“Ungh, fuck,” I buried my face in the pillow and groaned.

His dick felt bigger than ever.

“That’s it, man, that’s it, I’m about to bust,” he warned, his thrusts getting shorter and shorter.

“Hurry up man,” I shouted into the pillow through clenched teeth.

He moaned, and thrust hard, “Oh fuck I’m gonna bust,” he grunted, “Ungh,” thrust, thrust, “ungh,” he moaned and spasmed and I felt his dick dig deep as his load shot into my ass, the heat and liquidity of it lubed up my insides and his dick smoothly stroked in and holy fuck did those last deep thrusts feel good as he twitched and pumped until he collapsed on top of me.

“Shit,” he said out of breath.

I lay there, feeling his sweaty body on my back, his dick softening inside my ass, my cum smearing between me and the sheets, completly fucked out.

“Tucker?” I whispered.

“Mm?” He moaned softly.

“Did you nut in me?” I asked.

“Mmhmm,” he groaned, pleased with himself.

“Is…is that ok?” I asked, genuinely unsure.

“Mmhmm, better than ok, the best,” he sounded half asleep as he slowly rolled off me, taking his softening dick with him as my hole clenched shut.

I rolled onto my back, catching my breath and trying to wrap my mind around everything that transpired.

“You gotta go homie,” Tucker said, his tone changed to concern.

“Huh?” I wasn’t sure if I did something wrong.

“Didn’t you say you had to be home for dinner?” He asked.

I jumped up, steadying myself on my new legs, my entire body felt weird and different. “Shit, I’m dead.” I quickly pulled on my boxers, grabbing the rag he wiped the lube on earlier, “Can I clean up with this?”

He nodded and shrugged his shoulders.

I wiped the last of my cum off my stomach and then quickly finished getting dressed. I thanked him, which was awkward, and ran home.

It was fifteen minutes back to the library plus another fifteen to get to my house from there. With my mody completely stretched out and trying to clench my asshole so Tucker’s cum didn’t leak out of my hole and make a wet spot on my pants, I struggled to get home. I managed to get there just in time though, I was able to wash my hands, but mostly had to sit through dinner with sex all over me.

I was nervous the entire meal, thinking everyone could tell I just lost my virginity and that I must look different to everyone but no one was saying anything because they all knew I lost it to another guy.

After dinner, I said I had a lot of homework to do, took a long hot shower, and got completely cleaned up.

I spent the next two weeks trying to tell myself that I was still a virgin, that this didn’t count because it was with a guy. Then I would get horny and jerk off thinking about Tucker and after I nut I would tell myself it was just two bros helping each other out, and it was fun, and that’s fine.

By the third week I was jonesing to get friendly with Tucker again, so I called him to see if he wanted to help each other out again. Thankfully, he invited me back over as long as I promised not to be a punk.