My [F] First Friend With Benefits [M] [Long]

So I was absolutely floored by the amazing response that I got from my first story earlier this year! I thought it would just kind of get swept under the rug, but you all seemed to really enjoy it, so I thought you might enjoy another! Unfortunately, due to life stuff, school, and a brief stay in the hospital, I got delayed in posting this story from when I wanted to. But here I am! So let’s get it underway! Like with the previous story, skip to the asterisks (***) to get to the fun stuff! If you haven’t read my first post about losing my virginity, you should! You can read it [here](https://www.reddit.com/r/gonewildstories/comments/d7iupp/losing_my_virginity_to_a_hung_friend_fm_long/)!

My summer after losing my virginity to Chris was full of fun, and not all of it sexual. I fucked Chris as often as I could, trying new things and exploring what I enjoyed, what positions I liked, etc. I also went on vacation with my parents and got to relax some before the intensity of college. When I got back from vacation, I packed up my things, said goodbye to my friends (fucked Chris one more time) and left for college 12 hours from home! Yeah, I wanted to go somewhere new.

When I arrived at college with all the other bright-eyed freshmen, I was excited, nervous, and rearing to go. I had brought whatever could fit in the trunk and back seat of my car, and I spent the next several hours checking into my dorm room, meeting my roommate, and moving everything in. My roommate was nice, sweet, and never ever home. I spend easily 75% of my nights in this room alone, which I’m not complaining about!

So here I am, alone and a little freaked out, but also excited. I’ve heard so many things about college, classes, the people, and of course, parties! Now I’ve never been much of a party girl though high school, but I also am the type of person that can happily reinvent myself if I’m in a new environment. As pleasantries were exchanged and everyone was meeting each other for the first time, I found a few sophomores and juniors who were more used to the area and how things worked. It took a couple of tries, but I found someone who knew that a fraternity on campus was going to be starting the new school year with a party at one of their member’s houses. With a little bit of begging, I got myself an invite.

Waiting for Friday night to roll around was agonizing when I wasn’t being kept busy with orientation and everything that comes with getting into college. Finally though, it arrived, and I dressed up in my most fashionable party-worthy outfit. Admittedly, that outfit was not what most people would call “sexy,” but it was stylish. I showed up and was blown away by the drinks flowing, the people talking and laughing, and in general the entire environment. It was awesome!

Like I said I have never been into the party scene at high school, so I was a little bit of a wallflower until the girls who invited me started introducing me to people. Once I got a little more comfortable, I started sneaking drinks away from the drink table when I thought people weren’t looking (not that any of them cared). I always poured my own drinks and made sure I didn’t leave my cup unattended, especially after a few guys started talking to me. They didn’t seem like bad guys, but safety first!

That night I flirted with a few guys, and eventually settled into an increasingly hot conversation with one cute guy. A few drinks, a bit of groping, and an invitation to one of the upstairs bedrooms later, and I was naked with my legs spread wide and this guy jackhammering into me.

Now I know what you’re thinking. “Hey Emily, you really went into detail last time why aren’t you doing it this time? Also where are those asterisks to tell me dirty stuff is happening?’ Well, chill out. This isn’t the story. This guy jackhammered, came on my chest and left me frustrated and still horny. It wasn’t that great. I got dressed quickly and snuck out of the room while he lied on what I assume was his own bed. I didn’t meet anyone else that night at the party, and eventually went home and masturbated while my roommate was off to who-knows-where.

The real story is when I showed up again for the party next Friday.

When I walked in again, I was pleased to find that my disappointing one-night stand was nowhere to be seen. There were a lot of familiar faces and a few new ones. From those new faces, there was one guy who I knew I wanted to fuck me from the moment I laid eyes on him.

Jake (as I’ve been calling him to my reddit friends) is an athlete, but not one of the major sports teams’ athletes. He’s tall (like 6 foot 3 or something), short brown hair, clean shaven, tanned skin and lean but strong muscles. I got myself a drink and made my way over to him while saying hello to people again. I think he saw me making my way over to him, and he greeted me very politely but also casually. We struck up a conversation and I found out that he’s in his third year and is studying to be a doctor. Our conversation seemed to stretch through the night, occasionally changing when other people joined the conversation. Drinks kept flowing, and conversation became flirting. Flirting became touching (mostly me touching him).

***Here are your damn asterisks! ;) ***

Somewhere around midnight Jake finally puts his mouth near my ear and asks me the question I have been begging to hear, “My roommates are all here, which means right now my apartment is empty. Want to come back to my place?”

I grin like a giddy schoolgirl (alright, fine I am one) and agree. I get a knowing and approving look from the girl who gave me a ride to the party as I said goodbye and slip out with Jake when his uber arrives. The ride back, we keep talking, trying to keep it PG rated for the poor uber driver.

When we get there and his door closed, it was game on. I’m not quite drunk but I’m tipsy at this point, and that gave me the courage to skip any awkward conversation and lock my lips on his. He steps toward me and I step backward, and we keep moving like that until he guides me to his bedroom. I part from him and unbutton and throw off my shirt, followed quickly by unclasping and tossing my bra away. As I undress, Jake is also taking his clothes off, and when he drops his shorts to the floor, I can see the tent in his boxers.

I slide my jeans off and attack his face again, and he picked me up and laid me down on his bed. He stood up and positioned his beautiful bulge next to my face, and I knew it was my time to get to work. I sat up, shimmied his boxers down, and his gorgeous cock sprung free and slapped me in the face, making both of us pause to laugh for a moment. He was about 6.5 inches, and was plenty thick to make it fun, and totally clean shaven. Like there wasn’t a hair anywhere on his balls or around them. So I did exactly what any good girl would! I opened wide and slipped his cock into my mouth and started sucking. Now I was at this time still relatively new to blowjobs (I’ve gained a lot more experience since then), but I at least knew to avoid teeth, and to work his shaft with my tongue. And it appeared to be working. He stood there with his hands either on his hips or running through my hair as I sucked his cock and played with his balls. I probably sat there on his bed and sucked him off for 5 or so minutes before I could feel his cock starting to twitch in my mouth, and he hurriedly pulled it from my mouth and told me to give him a moment or he’d cum. I tried to get my lips back around his shaft but he told me to give him just a couple of seconds and we’d get back to it. So I laid back down on his bed and made a show of putting my legs in the air and made a show of slowly sliding my black panties of and throwing them at his face.

He laughed and seemed to relax a little. I slowly let my legs down and spread them wide. I gave him my best sexy grin (which probably looked awkward in retrospect) and began playing with my clit. He watched for a moment like he was in a trance before crawling across the bed to me and positioned himself between my legs. I made him pause for a moment so I could pull off his tshirt, the last article of clothing on either of us. When it came off, however wet I was before doubled, because this guy had rock hard abs, and just the slightest trace of a six pack. I didn’t get to take in the sight for long though, because he had slipped on a condom, and was poking at my entrance. I moaned desperately and began to beg him to get inside of me, telling him I couldn’t wait any longer and I needed his cock.

Finally, as if an eternity had passed, he slid his cock inside me, and I gasped sharply as I felt him fill the hole between my legs with his warm, hard dick. I groaned in release, that feeling of euphoria sweeping over me once again, and he in turn groaned quietly, which was a huge turn on. I love a vocal man. He began to pump in and out of me at a slow pace, not a jackhammer like the bastard from last week. He was patient, ramping up to a quicker pace with ease rather than jumping straight to it. I could tell I was in for a lot of fun, because he seemed to know every button to press to play my body like a musical instrument. At one point he reached down and began to rub my clit as he slowly fucked me, and it sent little electric waves of pleasure through my body.

Now, by this point I had learned something important about myself and sex. I have learned that I lose track of time really quickly the moment someone is inside me. Once you’re past the five minute mark, I honestly have a difficult time differentiating 10 minutes from 30. I just lose myself in the moment and give it my all.

This had already begun, and I was already grabbing at his back and leaving light scratch marks across it, groping his ass as he thrusted into me, and pulling his face in to kiss him again and again. My arms couldn’t stay still, and I could barely keep myself contained as I lost myself in the feeling of being fucked. I do remember at one point I shoved him hard off of me, and made him lay down so I could climb onto his cock and ride it while running my hands up and down his hard abs. I rode him like I hadn’t ridden a cock up to this point, with a sense of urgency that I needed to cum, and I wasn’t hopping off until I was satisfied. I know I’m a lucky girl to be able to cum from penetration alone, but Jake kept reaching down and playing with my clit when he could catch me still for a half second. It was in one of those moments that he rubbed my clit with him buried deep inside me that I felt the familiar sensation building between my legs, and I stopped riding him to let myself shudder with pleasure as I came on his cock. I let out a shrill shriek and laughed as I tightened my legs on either side of his body until my pussy stopped its contractions on his cock. I took a deep, deep breath after my pussy had stopped contracting, and let out of laugh that probably made me look a little crazy (cumming has always made me prone to giggling for some reason). I looked down at Jake and I could tell that he was doing everything in his power to not cum inside the condom.

He had given me a lovely orgasm, so I hurriedly jumped off of him and ripped the condom off of his cock. I took him in my mouth and began sucking with urgency, working his whole shaft with my tongue until his cock jerked and he began to pump a huge load into my mouth. I kept my lips sealed around his thick member like a good girl until I was sure that he had ejaculated every drop of his warm cum into my mouth. I got close to his face and opened my mouth so he could see his cum swimming around inside, closed my mouth, swallowed, and opened it again so he could see that every drop was gone. Before he could react, I leaned in and kissed him on the lips real quick and pulled back just in time to see him make a hilarious face as if me kissing him after swallowing made him gay somehow. It was a little cute actually. I laughed and allowed myself to collapse on his chest and rest for a moment.

After several moments of me laying on top of him, he rolled me off and told me that he was going to take a shower before he went to sleep, and wanted to know if I wanted to join him. And how could I turn down that offer? We showered together, hands still all over each other until he reached his fingers inside of me and fingered me until I fell to me knees in the shower from another orgasm. After the shower we laid down in bed and chatted for a while longer before drifting off to sleep.

The next morning I woke up before him and showered again using his shampoo, and then woke him up to awkwardly say goodbye. Though I found out later that he was just as awkward as me, he asked for my number and I hesitantly gave it to him. He texted me later offering to meet up again if I wanted to go for round 2.

Two nights later I was getting dicked down by him again, this time in my dorm room. Then again, and again, and again until we could very comfortably be labeled as fuckbuddies, or friends with benefits. Whichever you prefer. Even through to the end of the semester, Jake and I remain friends and fuck at least once a week. We’ve talked about the situation, and both agree that we’d kill each other if we tried to date, but that we both love the sex, and both have fun spending time together as friends but not lovers.

There are plenty more stories I have that involve Jake, and I plan on telling plenty more of them in the future (such as the first time I ever took it in the ass!), so stay tuned if you want to read about those times! Anyways, this is getting way long, so I’m going to wrap it up, but thanks for reading and I hope you enjoyed!

Source: reddit.com/r/gonewildstories/comments/ee15fr/my_f_first_friend_with_benefits_m_long