Before I got to college, a few guys had tried to play with my ass, but I never let it go anywhere. One guy talked me into trying anal. He got the tip in, but I was so self conscious and anxious that I couldn’t relax. It hurt and I made him stop. So I guess technically that was my first time, but I don’t count it. This is the story of the first time I got fucked in the ass for real and the moment that made me love anal and ass play.

I was drinking vodka cranberries in my dorm freshman year with my roommate, Amber. We had gotten pretty tipsy,and I was getting hornier with every sip.I was seeing a guy pretty regularly, but he hadn’t called me back, so Amber suggested I go knock on the door of a guy that lived on the opposite end of our hall. (I don’t remember his name, but for storytelling purposes, we’re going to call him, “Seth”).

Seth was cute but seemed shy. I had drunkenly kissed him at a dorm party earlier in the year, but it was just a spontaneous thing and I ended up going back to my room with someone else.

I was already wearing skimpy gym shorts, but I changed out of a baggy sweatshirt and into one of the tight baby-doll t-shirts I liked to wear to raves back then. I played with my tits for a second to make sure my nipples were poking through my t-shirt (like Rachel from Friends had role-modeled for my generation), headed down the hall, and knocked on his door.

“Uh, hi,” he said, clearly not expecting to see me.

“Hi. I’m a little drunk and I just wanted to know what you’re doing right now,” I said, kind of pushing my way into his room.

“Umm, just watching TV,” he replied.

“Oh,” I said, trying to look cute and giving him an awkward pause so he could make a move. But it didn’t look like he was going to seize the moment.

So I just walked over, threw my arms around his neck, and kissed him. While clearly too shy to make the first move, he immediately welcomed my advance, his hands finding their way to my ass right away. We stood there making out for a minute before I led him over to this reclining chair he had awkwardly crammed into the corner of his tiny dorm. I pushed him down onto the chair and straddled him. As things progressed, I got more and more turned on, and started grinding into him. I could feel how hard his cock was through his sweatpants and I pressed and rubbed my clit on it while we made out. It was actually kind of cute. Dry humping and making out with a shy guy… it felt like a high school make out session…at first.

He kept rubbing his ass with my hands, over my skimpy shorts, but I noticed that more and more he was sliding them directly over my asshole, down onto my pussy, and back. I assumed he was building up to slipping his hand inside my shorts to finger me in the “traditional way”. But as we both got more turned on, he was increasingly rubbing and pressing on “the back door”.

I don’t know if it was just the way he was doing it—pressing just right and then rubbing his hand gently back and forth over the thin fabric that was covering my tightest hole—but for the first time, it felt really good. And each time he pressed on my asshole, I got wetter and wetter. As I got more and more turned on by it, I started pushing my ass back into his hand and he pressed and rubbed.

Seth was clearly getting more confident as he realized I was not pulling back. He sat me up a little, admired my tits for a second, and ran his fingers over my lips erotically, before sticking his middle finger into my mouth. I sucked on his finger and kept grinding my clit on him.

“Get it really wet,” he said, clearly starting to feel himself. I did as I was told, and eventually he took it out of my mouth, pulled my shorts to the side with his left hand and began rubbing my raw little asshole with his freshly lubed finger.

“Fuck!” I moaned as I got more and more turned on. I could feel the pressure increasing as he rubbed it in a circular motion and I braced myself knowing that any second he would break the surface.

“Relax, okay?” He gave me the warning just in time for me to take a breath and feel it dive in. I gasped a little and, reading my cue, he left his finger still for a second to let me adjust. But it didn’t take long before I was back to kissing and grinding into him. He started plunging his finger in and out of my tight little ass, slowly at first and then faster.

“You’re going to make me cum!” I cried out, grinding faster and harder while he fingered me. And just as soon as I could say it, I came hard, pressing my face into his neck and grinding my clit into his hard cock. He slowed the pace of his finger inside me and I enjoyed one of the most intense orgasms I ever had. I was almost in shock, shuddering, moaning, and practically gasping for air.

I laid on top of him for a minute trying to gather myself, still surprised that ass play had sent me spinning like that. But before too long, I started to feel his hips moving, pressing his still-hard cock into me, as if to remind me that he was still “unresolved”. So, dutifully, I started rubbing his cock through his sweatpants with my hand, slid off the chair onto my knees, pulled it out, and aggressively plunged it into my mouth. Initially, I just wanted to repay him, but having a hard cock in my mouth never fails to make me want more.

I looked up at him and said directly, “Do you want to fuck me?”

“Of course,” he replied like it was a stupid question.

He leaned over and grabbed some lube from under his bed and switched places with me, putting me onto the chair on my back. I started to slide my shorts off, but he stopped me. “Leave these on, they look hot.”

He pulled my shorts over with his left hand and slid his well-lubed dick inside soaking wet pussy. But after just a few seconds, he pulled it out and started teasing my little asshole with the tip of his hard cock.

“You’re really into that, huh?” I chuckled nervously.

“Of course,” he said, again like it was a stupid question. “Have you ever been fucked in the ass?”

“Not really.” I responded. “It hurt the one time I tried it.”

He leaned down and kissed me and said kind of softly, “Do you want to try it again? “I’ll help you.” I nodded nervously, aware of the irony that I was now the shy, nervous one and he was the one taking charge.

He grabbed more lube and started giving me pointers. “First, a lot of it is mental. Don’t be shy or self-conscious,” he said. “Just know that I think you’re incredibly sexy and your little asshole is so fucking hot. I love it.” Seth clearly considered himself an expert in both the psychology and the mechanics of ass-fucking.

He took some more lube on his thumb and started working my virgin fuckhole again. He slid it inside and I gasped a little. But this fingering wasn’t nearly as surprising as before and it was almost immediately pleasurable. I remember thinking simultaneously, “I’m actually getting into this anal thing” and “I don’t know how his cock is going to fit in there.” For his part, Seth continued to work his thumb around in a circular motion with a very serious, concentrated look on his face, like an artist preparing his canvass.

He pulled his thumb out, pressed the tip of his hard cock to the entrance, and said, “I’m going to go slow. Just relax.” I could feel the tip of his erection pressing harder and harder. He had a very nice looking cock—straight, clean cut, and hard as a rock. But it was average in size. That, however, was just fine, given the situation.

“Take a really deep breath, let it out, and relax your entire body,” he instructed. It started to turn me on even more that he was talking to me like a teacher and so I complied like an obedient little slut. As I exhaled, he pushed the head of his cock inside my tight little hole. I would describe it as incredibly intense, but it didn’t hurt like I thought it would, likely because of Seth’s various mental and physical preparations. He paused with his cock just inside my ass, waiting for me to acclimate. For a second, I tensed up around his shaft a bit and I think he could feel it. “Relax and breath,” he said. I followed orders, and when I exhaled again, he began to slide further in.

Once he was all the way in, he paused, leaving his hard cock docked inside me, reaching down to play with my clit. This felt amazing and my pussy was literally dripping all over what little bit of his shaft was still visible and onto his reclining chair. After a second, he started slowly pulling back and then pushed forward again. For a virtual stranger who was now fucking me in the ass, he was being quite the gentleman, reading my signals and taking it slow.

It didn’t take long for me to get over both my physical and mental hangups and once I did, I was completely in heaven. It wasn’t only the intensity of his cock being in the tightest of all places, but I felt like I had unlocked a new level of sluttiness. That turned me on more than anything. Even while it was happening I can remember thinking how much fun it was going to be now that I could let guys fuck me in all three holes. And I was already thinking about whether the guy I was seeing, who had a much larger cock, would fit.

I have no idea how long he pumped my ass, but it was probably only a minute or two. He pressed into me one final time and told me he was cumming. I think it’s universally true that guys like to be made to feel manly while they are cumming inside you. So, having regained full confidence in myself at this point, I encouraged him, saying, “Yes, babe! Cum in my ass, no one has ever been in there before.” This seemed to make him cum harder and he shuddered out the last drops into me.

When he pulled out a rush of cum immediately came with him, dripping down the front of the chair and onto the floor. He grabbed a t-shirt that was on the floor to mop it up and I moved my stretched out shorts back into place.

“Do you want to stay over?” he asked, resembling the shy, sheepish boy I had known him to be. I chuckled, which I think hurt his feelings a little. So I stood up with him, kissed him and said softly into his ear, “Thanks for teaching me how to do that. You’ll always be the first to fuck me there,” and I went back to my room. We exchanged a few awkward smiles in the hall after that, but he moved out about a month later and I never saw him again.

So “Seth,” if you read this: Know that you unlocked a new kind of sexual pleasure for me that I’ve loved ever since. I even masturbate anally sometimes. And perhaps most of all, there are a ton of guys who got to follow you that owe you big time!