Grant - The Night of Seven Dildos

From the first inklings of attraction as a kid all the way through high school, I was 110% straight. It was the mid to late 80s when I went through puberty, and I never once had an attraction to other guys, barely any fascination. It was no secret that homosexuals existed; you couldn’t turn on the news without hearing about the gay pandemic. It never really registered for me, though; as a heterosexual guy, you didn’t worry about such things. Sure, I had jerked off with my closest friends, but all guys do that; that’s not gay. It was never sexual, always just about getting off, and if you were lucky, the other guy would jerk you off so you could feel another hand on your dick. We liked to use the phrase “helping each other out.”

As a legacy, I was expected to join my father's fraternity. I was excited about it. My father wasn’t very happy as a person, but he would light up when telling stories of his fraternity days, so I knew it had to be great. He did warn me that being a pledge was hard and that you would be tasked to do stupid and odd things, a lot of it involving nudity or some kind of embarrassing act, but he also said it was how they would weed out the weak. Once you make it through, they are your brothers for life, and you live like a king on fraternity row. He warned me about having safe sex, giving me the speech about how he knows what young men get up to and that I don’t want to get anyone pregnant before I’m married, and he bought me a box of condoms to hammer his point home. Starting my freshmen year of college in the fall of 1991 as a virgin, I was looking forward to the frat parties and the sex I was promised.

Being a pledge was mostly spent doing degrading things, and some of the pledges couldn’t handle it and dropped out. The last night of challenges was the one that really changed my life. Thankfully, my Big Brother gave me the heads up that I wanted to be showered and have taken a “good” shit beforehand. I didn’t know what was happening, but I wasn’t all too surprised when the challenge was an obstacle course the brothers had set up.

It was called “the Night of 7 Dildos,” which, clearly, none of my frat brothers were going into advertising. The pledges had to strip down to their underwear and do the obstacle course; the catch was, at the end of the course, your last challenge was to pick from the bin of dildos, all of them different sizes from five inches up to ten inches in varying girths. Then your big brother had to fuck you with the dildo while you jerked off. The real winner was the guy who cums first. The real loser was the guy who cums last because, to become a brother, you had to complete the challenge no matter how long it took you to cum.

We all groaned as the rules were set out for us, but I didn’t really care; I was determined to win, I get oddly competitive. I played soccer in high school and had skills out on the field. The dildo stuff sounded weird, but I had been warned that pledging, and certainly Hell Week would be degrading and this seems to check that box, besides, how bad could it be?

I managed to be third through the obstacle course because I couldn’t do a ten-second keg stand, and it took me two tries to get it. When I made my way to the dildo bin, the two smallest ones were already taken and being inserted into my fellow pledges asses, so I grabbed the next smallest, which was 7” with an average thickness, and handed it to my Big Brother who grinned ear to ear at me and said, “ok.”

I stood on the circle, which was just a hula hoop on the ground, facing my fellow pledges, dropped my briefs, and quickly stroked my dick to get hard. This certainly wasn’t the first time in the hazing that we had all been nude together, not even the first time that involved jerking off, but the dildos were a new addition.

“Lube or no lube?” my Big Brother asked.

“What’s the difference?” I asked.

He chuckled, “Lube is better,” he said confidently and started lubing it up for me.

He put his left hand on my bare shoulder, standing close enough behind me I could feel his body heat, and whispered, “Spread your legs and your cheeks,” as the cold dildo started rubbing its way between my cheeks. I did as I was told. He found my hole. “Just try to relax, push out like you’re taking a shit,” he said in a whisper, hoping the other pledges didn’t hear. Then I felt an excruciating pain as the tip breached my sphincter, but I couldn’t scream because the other two pledges didn’t.

“Just breathe,” I felt his hand massaging my shoulder and the warmth of his breath on my ear. I clenched my fists and tried to breathe as he continued to push all seven inches of rubber dick into my ass. It was painful and weird at the same time. As the rubber balls pressed against my ass, he whispered, “There, now quick, start jerking.”

I looked to my left and right and saw my fellow pledges already stroking their dicks as their big brothers pushed and pulled dildos from their asses. Their faces mixed with pleasure and pain. I nodded to my big brother and started stroking my dick. It didn’t take long for me to get hard since I hadn’t jerked off in three days. I’m surprisingly comfortable in this situation from years of jerking off in odd places as quickly as possible since I shared a room with my actual little brother.

The pain around the dildo started to settle the longer I stroked my dick, but it was when my big brother started pulling the dildo out and pushing it back in that I felt the real pleasure that people get from this. His grip on my shoulder tightened as his other hand pushed the dildo into the rubber balls and then back out until the tip almost fell out of my tight hole, then right back in until the balls rested on my ass cheeks. I jerked faster, looking over at the other pledges, which were now four guys, stroking while getting dildos shoved in and out of them.

On the next stroke, my big brother changed the angle ever so slightly and hit something inside me, which made me moan, and the other guys giggled hearing it. The hand on my shoulder tightened its grip and my big brother did it again, “that’s your pleasure spot, just keep jerking and I’ll keep doing it,” he whispered. He kept his word, and after a few strokes, I no longer felt any pain, only pleasure. I stroked faster, pounding my fist on my cock and clenching my ass on the dildo, but he forced it deeper, hitting my prostate even harder, and it was like that spot was a release button. My balls suddenly tightened, and I was instantly having the most amazing orgasm of my life. Shuttering as I shot rope after rope of cum into the hula hoop on the ground, the first rope almost hitting the pledge across from me on the hoop. I was getting cheers from the frat brothers as I continued to unload in front of everyone.

My big brother squeezed both of my shoulders, leaving the dildo buried in my ass, “Good work, pledge! Let’s hear it for Grant!” He shouted, and everyone cheered again as I reached back and slowly pulled it out of my ass. It looked a lot smaller than it felt, but I’ll admit that was the best orgasm I’ve ever had. I pulled up my underwear and walked awkwardly to the champion platform, where I was handed an ice-cold beer.

I watched silently as the rest of the pledges took their time getting off. I wondered if they were deliberately taking their time to enjoy this experience or if they just didn’t like it at all. I couldn’t ask that question, but their faces told me they hated it.

I paid close attention to their body language. None of the brothers seemed to be trying to help their pledge like my big brother helped me. They were basically stabbing their pledges with the dildos. I felt terrible for my buddy Thomas, he got stuck with the biggest dildo, and he was struggling to take it, yelping when his Big Brother shoved the dildo into his ass. He groaned with discomfort the entire time, and the brothers kept laughing at him for it. There was no way he was going to cum any time soon.

The next pledge shot his cum into the circle and got cheers from the brothers.

The only other pledge that seemed to enjoy it like I did was Adam. He almost looked like he was rocking his ass on the nine-inch dildo he got stuck with. Though his Big Brother wasn’t jabbing it into him, he was just slow fucking him with it, and the fake balls never seemed to be touching his skinny ass. He also seemed to be ignoring the other guys as he kept his eyes closed and stroked his hairy cock that looked a lot like the dildo I had just used. The size was about the same, though he looked a little thicker, which you wouldn’t expect from a tall, skinny guy like that.

Everyone was cheering on the remaining pledges and I was rooting for Adam to cum next, he did. I don’t know how, but I could tell by how much he savored the moment that he really enjoyed his orgasm as much as I did.

A few days later, after a few beers, I tried to talk with him about him enjoying the dildo. We were both pretty drunk, and he agreed that it was intense, but then, he dropped a bomb on me that I wasn’t expecting. “You think that’s good? You should try the real thing,” then he laughed almost like a Jack Nicholson in Batman. As the words bounced around in my head, one of the sorority girls who had been invited to the party interrupted our conversation and dragged him off. Those words stuck with me, though, at least until one of the girls took me upstairs, and I drunkenly lost my virginity to her. It was great, but the orgasm didn’t come close to being as good as with the dildo in my ass; I chalked it up to having been pretty drunk.

Over the next couple of weeks, I tried my best to quelch the desire to repeat that experience, to see if I could get as good of an orgasm in more traditional ways. I tried sober sex with that same sorority girl. It was great, but not as great. I tried waiting a few days with no jerking off, but that just made me frustrated. Eventually, I considered buying a dildo and trying it for real, as Adam suggested.

I took the bus into the shady part of the city and went into an adult bookstore for the first time. Walking around it, I was like a kid in a candy store. All kinds of toys and fetishes I didn’t know existed. I had only ever purchased porn magazines at the gas station, but this place had videos of all kinds and a much wider variety of magazines.

When I found the dildo aisle, I suddenly felt embarrassed. The clerk at the register was watching me as I picked out a dildo that looked similar to the one I used at the party. It was expensive but worth it. The clerk recommended a lubricant, and I took that too.

I hid it in my room for a while before trying it out. Finding private time in the frat house was hard because I had to share a room with another guy from my pledge class. Anthony was not the most fun roommate, but he was the cleanest, which was nice.

When I finally got the chance, I stripped naked, laying on my bed; I lubed that sucker up and pushed it into my pucker. This time, I was expecting the sting and knew what to do. I quickly was able to get comfortable with it and was able to jerk off with it in my ass.

I had a pretty great orgasm that night, but it was still missing something. It’s just not the same as when my Big Brother was using it to hit my pleasure spot. I could get pressure on it, but…It was not the same. Still, it was a great orgasm, but I was chasing the high of that orgasm from the party, and the perv in me wouldn't let it go.

Over the next couple of weeks, I tried a few different times to get it right. The closest I was able to get was spreading my legs like a frog, laying on my back, and using the heels of my feet to sort of jostle the dildo around in my ass while I jerked off. It was better yet, but still only a shadow of the real thing. That’s when it hit me: I needed the real thing. I needed one of my brothers to…help me out, use the dildo to help me get that orgasm, or hopefully better since I’ll be able to do it in my own bed. I knew just the frat brother to do it too.

“Adam,” I drunkenly flung an arm around him as I sat next to him on a beat-up lawn chair by the fire in our backyard. He was sipping a beer, staring at the fire. He looked at me and smiled the smile of a guy who’s had a few too many drinks and struggled to focus on me this close-up. He stands about a foot taller than me, so putting my arm around his shoulder was a stretch, and I released him. He has a long neck and a small head, short wavy hair, and looks pretty good in the light of the fire.

“Grant, cheers,” he said, holding up his beer, and I clinked mine against his.

I didn’t want to beat around the bush, so I looked around to make sure no one was in earshot before I lost my nerve, “Bro, I gotta ask you a favor,” I chuckled.

He looked around, his eyebrows knotted together, and he smiled curiously, “What?”

“You remember the dildo jerk-off contest from the…” I started to say.

He cut me off, “Yeah, I remember,” he sipped his beer, turning his gaze back to the fire.

“Well, you said something to me that has been bouncing around in my head ever since. Do you remember what you said?”

His eyebrows raised, and his forehead crinkled. “Umm…I drink a lot, but I’m sure it was stupid…whatever I said,” he chuckled and sipped his beer again.

“Well,” I looked around again and sipped my beer, “you said if I liked that, I should try the real thing, right?” I watched his prominent Adam's apple bounce in his throat as he swallowed his beer and then licked his lips.

“Yeah?” His eyes squinted as he tried to focus on mine.

I chuckled, “Well, this might sound crazy, but…I tried the real thing and…”

He nearly spit out his beer, “You did?”

“Yeah,” I grinned, “but I don’t think I did it right; it wasn’t quite as good as what we did in the competition.”

His grin widened so much I could see all his teeth, “Well,” he bit his lower lip, “maybe you did it wrong?” He sipped his beer.

“That’s what I was thinking,” I nearly shouted because I was so excited that he didn’t laugh at me and that he understood where I was coming from. “I was thinking it was because in the competition, my Big Bro knew what he was doing and…well, I can’t ask him, so I was thinking maybe…you would be interested?”

He laughed, “Me?”

I grinned, “Yeah, why? It was kinda your idea, so…I was thinking you probably know what you’re doing?”

He finished his beer and licked his lips, “I…well…yeah, but are you sure?”

“Dude, I’ve been chasing that orgasm like a crackhead needs crack,” I chuckled, and he laughed.

He shook his empty bottle, holding it up to the firelight to see for sure that it was empty, “Well…fuck it, yeah, you want to do it right now?”

“Uh…yeah! I was hoping you’d be game, so I made sure I showered and stuff before the party started,” I laughed, then chugged my beer.

He grinned at me, “Tommy will be in our room already, banging some dumb blonde; what about your room?”

“Umm…yeah, Anthony went…Home, I think, something about his sister getting married, I don’t really remember,” I rambled.

He nodded, stood up, adjusted his dick in his pants, and started walking back towards the house. When he got about ten feet away, he glanced over his shoulder at me, and I realized I was supposed to follow him. I stumbled to my feet and hustled to catch up to him.

In my room you could hear the music thumping and distant chatter, Adam locked the door behind us which was good thinking. I was glad to have had a few beers because now that we were here, I realized how awkward this was.

“How do you want to do this?” he asked.

“I don’t know. I was thinking…well, you have more experience, but I thought, at the party, it worked really well when I was standing, and he was behind me…” my voice started drifting as I gestured poorly with one hand on a shoulder and the other down by where my ass would be.

“Yeah, ok,” he smiled, “don’t want to look at each other, huh?” He chuckled.

“I mean, I don’t care either way, but…I guess, however, you want to do it; you’re the expert,” I shrugged awkwardly, unsure how to start this.

He bobbed his head, nodding, “Ok. " He reached forward, grabbing my shirt. My heart started racing. I guess this was okay. I lifted my arms as he pulled it off. When he reached for my belt, I kind of thought that was a bridge too far and stopped him.

“You know what? I can do this part,” I pulled at my belt until it came undone, my slightly too-big jeans sagging instantly on my hips.

He snickered, “Ok, take off your clothes,” he said, then took off his shirt.

“Oh, are you going to…” I started to ask why he was getting undressed and then realized it was stupid to think he wouldn’t want to jerk off, too.

He slipped off his jeans, standing in just his white Hanes briefs, his dick already hard, which made me feel better about being hard and asking him to do this.

“Where’s…the stuff, lube, and stuff?” He asked, grabbing his package.

I slipped my thumbs into my underwear, pushing them down with my jeans together, “Um…in the top drawer, behind my underwear,” I said, my voice cracking.

He looked down at my cut 5” hard dick, then back up at me and grinned, “Turn around and bend over, put your hands on the bed. He went over to my dresser, and I took a deep breath, turned to face the bed, and bent over the mattress, which was just about waist high because I had it on bricks so I could store my stuff underneath it.

I heard Adam shifting things around in my drawer. I slowly started stroking my dick in anticipation. When I heard the wood squeak as he closed the drawer, I knew I was finally going to get the orgasm I’d been craving. I heard him open the lube, then the squishy sound of him lubing up the dildo. I felt his hand start lubing up my ass crack.

“Woah, what uh…what are you doing, man?” I hung my head down on the mattress; I couldn’t look him in the eye while he did this. Between my legs, I could see something I had never expected: someone elses ball sack and hairy legs.

He snickered again, “I’m lubing you up, you didn’t lube your ass the last time?”

“No, I…I didn’t realize,” I buried my face in my folded arms.

“You gotta lube the ass, man. The ass needs the lube way more than the cock,” he chuckled.

The phrasing made me chuckle. He’s right, a dildo doesn’t need lube, it kinda makes sense now. He slowly pushed a finger into my hungry hole.

“Mmm…damn, that feels weird,” I groaned.

He chuckled, “You didn’t loosen up with a finger either?”

I laughed, “Not really, no.” I tried to relax around his finger, but as soon as I was feeling relaxed, he added a second finger. I groaned, “Damn…so weird.”

He chuckled, “Weird because it’s me?”

“Kinda, yeah,” I tried not to make this more awkward, as his second finger started to feel good inside me. I slowly slid my right hand down to my cock and started stroking myself as he continued to lube and stretch my hole with his two fingers. As I stroked my dick I felt less embarrased by asking him to do this because it was starting to feel really good, I uncontrollably let out a soft moan.

“I think you’re ready for the real thing,” he said in a soft voice, then slowly pulled his finger from my ass.

I was so turned on, so ready, and the best part was I already knew it was going to feel good; I just groaned out something that sounded like a breathy, “Yeah.” Then I felt it, the slick tip rubbing up and down my crack, feeling softer and better than when I did it myself until it caught on my hole and gently pushed in. “oh, ungh,” I hissed,” feeling the first inch, then the second, pushing into me. I tried to push out like I had been taught, tried to breathe through it, and tried desperately to relax. Somehow, it seemed thicker than when I did it by myself…and the texture was softer and warm. As he continued to push it in, inch by inch, I realized it was definitely bigger right before I felt Adam's pubes, immediately followed by his hips pushing into my ass and pushing me into the mattress.

“Ungh…wha…wait, is that your dick?” I groaned, trying to twist my head around to see his skinny bare chest and naked hips pressed into my ass.

He chuckled out a confused, “Yeah?”

“Adam, ungh, what the fuck?” I didn’t know what to do.

He slowly started to pull out a few inches, then pushed back in, pinning me into the mattress, “You said you wanted the real thing; this is the real thing,” Adam's hands held my hips as he ground into me, gyrating slightly as he let out a satisfied “mmm.” His dick felt so warm inside me, so much better and bigger than the lifeless dildo in my drawer.

I bit my lip, “I…mmm, I didn’t realize, ungh, this is what you meant,” I groaned as he pulled out a couple of inches and then pushed them back in. Fuck this feels so much better than the dildo.

“Do you want me to stop?”

“No, I just…mmm,” the last thing I wanted was for him to stop, but…wasn’t I supposed to? I was enjoying this way too much and couldn’t think clearly, “I need mmm…are you wearing a condom at least?” I felt him pull out about half of his cock and push it back in, eliciting another moan from me, and I buried my face in my arms, embarrassed I was getting so much pleasure from his cock.

He scoffed, “No, should I?” He thrust into me again.

“Ungh…umm, what about disease and stuff? I don’t want to catch…mmm, anything.” I tried to look back at him, but between the beer and the gallons of dopamine dumping into my brain, my dick was doing all the thinking at this point.

“The gay one?” He chuckled.

“Mmm, yeah…that one,” I couldn’t bring myself to mention it.

He laughed, “Man, I’m not gay,” he said with such certainty I didn’t know how to respond. After a pause, he added, “I’ll put one on if you want. I saw a box in your drawer next to your dildo,” He said in a way that made me feel embarrassed again, but when his dick hit my prostate, it melted the thought away, and I felt precum drip from my dick into the mattress.

“Maybe…just for safety, right?” I mumbled through waves of pleasure.

He quickly pulled out of my ass, and I was left feeling empty as I heard the wooden drawer creaking open. As he dug around in the drawer, I started to come to my senses a little. I was hearing the people laughing downstairs as I was bent over my bed, and my fraternity brother was digging through my underwear drawer for a condom so he could put his dick…in my ass. This is all kinds of wrong.

“This box is empty. Do you have any more?” he asked, tossing the little box on the bed. I had a quick memory flash of using the last one with the sorority girl and telling myself to pick up more…but I didn’t.

“Ummm…no, do you have one?” I looked over at him.

“I…in my room, I do,” he shrugged, “but I’d have to leave,” he gestured at his completely naked body, which I hadn’t really looked at until this moment. He was thin and tall, with long arms, neck, legs, torso, all thin and long, but his dick was thicker than you’d expect from such a thin guy and just as long, if not longer, than my dildo. “Let me just do it without; I have really good control if you're worried about getting cum in you.”

I hadn't even thought about that, but I definitely didn't want him to cum in me, that's too much. “Umm…ok, fine,” I tried to sound like I was doing him a favor, but I really needed to see this out. I was too worked up to stop now.

I gave myself a little space between my cock and the mattress so I could start jerking off again. He quickly lined back up and slowly pushed back into me, moaning as soon as he bottomed out. This time his hands roamed my back as he let me adjust to his size again, then slowly, his hands worked down to my hips, where he gripped on and started fucking me.

I couldn’t believe it; I was actually getting fucked by Adam. I was moaning and jerking myself off, loving this feeling inside me but trying to focus on the pleasure instead of the fact that it was quite literally another guy fucking my ass.

He was thrusting into me the same way I fucked that sorority girl, and the moans coming out of my mouth sounded only slightly different than hers. He didn’t fuck me nearly as fast as I fucked her, though. He made sure I felt every inch push in and pull out, grunting every time he bottomed out.

The slow, hard strokes he was pounding into me were giving me so much pleasure I was feeling…some internal pleasure I never got from the dildo. His moaning was also doing something to me, and I couldn’t help but rock my ass to get his dick head to aim right at my prostate with every thrust. That spot inside me made it all worth it, and I could feel the orgasm boiling up inside me as my balls tightened. I started rocking my hips up and down, the way I had seen him do on the dildo at the party, to match his thrusting. I tried to hold out as long as I could to savor it, but he seemed to deliberately try to push me over the edge with his cock. Speeding up and plowing harder into me, telling me how good my tight ass felt on his dick, it was all too much.

“Oh shit,” I grunted and unleashed a torrent of cum into the side of the mattress, fisting out rope after rope as Adam’s cock continued driving into me. “Shit, ungh,” I grunted and moaned as the last few ropes drizzled out and Adam pounded me harder into the mattress.

The pleasure quickly turned on me, and it now felt like when the dildo first entered my ass, “Ahh, shit man, ungh…” I grunted and tried to lean further into the mattress, my cum smearing on my now soft cock and into my pubes, feeling slimy and warm.

He thrust harder, panting, “I’m getting close; want me to cum…”

I cut him off, “Yes, ugh, just hurry,” I groaned through clenched teeth.

He gripped my hips tight, his thrusts shorter in and out only a couple of inches, but the speed doubled, and then he moaned and slammed his hips into my ass, pulling my hips tight to his as his dick twitched inside me. “Oh God…mmmm,” he moaned, then slowly pulled most of the way out and just as slowly pushed all the way in. “That felt so good,” he whispered.

“Did you cum?” I popped my head up, knowing what those words meant.

He chuckled, “Yeah,” his hands massaged my ass cheeks as he slowly pulled his cock out of me.

“Wait, inside me?” I had a little bit of a panic.

“Oh, I thought you wanted me to?” His voice trailed off; he picked his underwear up off the ground and used it like a rag to wipe the extra lube and, I guess cum off his dick.

I was in shock; my head spun from all of it as I leaned against my bed. My brain was trying to wrap around what just happened. I looked down to see my cum smeared in my pubes and on my cock, the bulk of it on the side of my mattress, soaking a growing wet spot into the sheets, and felt the warmth in my guts as my stomach started to feel queasy.

“Don’t worry. It’s no big deal. I don’t have anything, and you can’t get pregnant,” he chuckled.

I pulled on my underwear clumsily, “I’m gonna be sick,” I said, running for the door. I unlocked it and ran into the hall in my underwear; the bathroom was locked, and I ran downstairs through the party to vomit in the kitchen sink. My frat bros all cheered for me.

My big brother came up behind me. As soon as I was done puking, he handed me a beer. " This will wash the taste down,” he chuckled. We’ve all been there,” he looked me up and down. But maybe put some pants on before you come back to the party,” he shook his head at me.

I chugged the beer, grabbed another, and headed back to my room. Adam was gone, but the cum was still wet on my mattress. I tore the sheets off and lay on my cool bare mattress, letting the spinning room lul me to sleep. Telling myself he’s not gay, so I’m not gay, so it doesn’t even count as sex.

I believed it, too, for a while—until it happened again with a complete stranger at the party after the midterm exams were over.