My First Time: Someone Watching Me Fuck [MF]

*I’ve started writing a series of posts about my first times. E.g. my first blowjob, first time having sex, first threesome, etc. A lot of things I’m not allowed to post to reddit, so I’ll post them here to Patreon as exclusives for my Patrons.*

*And you know me. My name is Riley. I’m 26 years old, and a bit of a girl-next-door type. Specifically, I’m a 5’4” brunette with brown eyes, I wear my hair long, a bit past shoulder length, and I stay pretty toned with cycling classes. I’m no supermodel, but I’ve never had trouble attracting a guy (or even a girl).*

​

College continued to be an adventure for me. Intellectually, socially, and (yes) definitely sexually. After my first time with a girl (during my freshman year), I was hunting almost non-stop for new and exciting experiences.

Most of the time though, I didn’t seek them out. They just happened, and I could only look back on them and think, “wow that was hot.”

This is one of those times.

​

I met Mason during a group project in an economics class during second semester freshman year. He was an academic type, glasses, modestly tall (maybe 5’10”), white, brown hair, strong chin but quiet and reserved. Definitely a strong silent type.

There was an instant attraction, and pretty soon we were sitting next to each other in class, grabbing coffee afterwards, and generally hanging out.

Although there was a lot of sexual tension building, it took a few weeks for us to act on it, given that we were working together in class, and it felt like it would be crossing some line. Obviously this wasn’t a real issue, but whatever, we were young.

​

One night, in the middle of the week, he texted me to come over to his place and watch The Office, a series we had both been bingeing on at various points that year.

I got some work done, and headed over around 10pm. (It was college, so 10pm didn’t actually seem so late.)

​

He was staying in a smallish dorm with a roommate, who he said was going to be gone for the rest of the evening. The roommate was apparently pledging a frat and tended to be out all night for that.

When I got there, I noticed the two beds across the room from each other, with Mason’s neatly made. I came into the room and he gave me a hug.

He also showed me a bottle of whiskey he had gotten (which he was very proud of given that we were both 18), and I promptly grabbed it from him, winked, and took a sip from the bottle.

We both laughed hard and he said, “I knew you were fun, Riley.”

​

We propped open Mason’s laptop, and sat next to each other at the head of the bed, leaning against the pillow.

As we watched an episode, we kept sipping the whiskey, and I gradually leaned in closer to Mason, letting him feel my body more, and also huddling with him for warmth. It was winter in NYC, and even inside it felt cold.

​

I should also mention, he was wearing a t-shirt and sweatpants, which were a questionable choice given the clear outline of his erection that he was trying to hide with his arm.

I was wearing jeans, a long-sleeve shirt, and socks, having taken my shoes off at his door.

​

By the second episode, things were heating up between us.

Soon Mason asked, “are you cold, Riley? We can always get under the covers…”

I readily agreed, and was happy to pretend like we were doing it because I was cold, and not because he was trying to hide his boner.

We left the bottle of whisky on the floor, and slipped under the covers with the laptop sitting on top of Mason’s legs.

​

I was lying on my side, head against Mason’s shoulder, watching the show.

It didn’t take me long to move my hand closer and closer to his dick, which I could occasionally feel twitching even without touching it.

Our breathing become short, and were were both pretending to watch the show, but definitely weren’t.

​

I touched his cock, over his sweatpants and boxers, and it twitched hard.

I mean, I was afraid he was going to cum right away, given how strong a reaction he had.

Mason clearly was excited for this.

And yeah, I was too, but I knew I could contain myself.

Mostly.

​

I slowly started rubbing it up and down, and then moved my (now warm) hand to his stomach, slowly slipping it down into his pants and underneath his boxers.

He moaned, and his body arced when I grabbed his bare cock, which felt strong and warm in my hands.

He was average sized, uncircumcised, trimmed neatly, and absolutely throbbing in my hands.

“Oh my gawd Riley…”

​

At that point we stopped watching. He grabbed the laptop and set it on the floor, and I pulled off his sweatpants and boxers, with him following quickly by taking off his shirt.

​

Now, interestingly, he was totally naked, and I was totally clothed. I think maybe he just expected a hand job, but regardless, I wanted much more.

Sitting up on my knees, I gave him a full view of my body as I pulled my shirt off over my head, and then started unzipping my jeans.

I looked down at his cock, literally throbbing up and down, and I smiled coyly at him.

I pushed my pants down and then leaned over to push them to my ankles, and then pulled them off entirely.

He reached up to unclasp my bra, and did a pretty good job dispensing with it.

​

With us both completely naked, I felt the rush of weeks of built-up sexual tension.

I lowered myself down so I was laying on top of him, pulled the covers back over us, and started kissing him while letting him rub his cock against my body.

​

He was rock hard, and with every push of my body, I let his bare cock closer to my pussy.

“Do you have a condom?” I asked.

He reached over to a pile of stuff next to his bed, and fished out a condom from underneath a book.

I took it from him, and ripped it open with my teeth, grabbing the condom and reaching down to put it on him with one hand (a little trick I’d learned in high school).

​

Finally ready, I held his cock right at my pussy, looking straight at him…

​

…when we heard a key in the door, and the door opened to his roommate standing there.

But the roommate was rather drunk, and just walked across to sit on his bed.

(And by the way, the look of disappointment and frustration on Mason’s face was immeasurable! I still laugh at that.)

​

Mason cleared his throat, and the roommate looked up, clearly surprised to see me there.

“Oh, damn, Mason my man! Good for you, didn’t know you were planning to get laid tonight!”

I rolled off to Mason’s side, making sure I was covered up, and let them laugh a bit and chat.

The roommate went on, “the pledge event was an early one, so I’m back here for the night. Sorry to fuck up your plans man,” said the roommate.

“Dude it’s fine, could you just give us a few minutes?”

“Hell no, I’m passing out. But I mean, don’t stop on my account.”

​

They kept talking a bit, mostly Mason trying to negotiate his talk his roommate into leaving the room.

I stopped paying attention, and my hand roamed around a bit, finding Mason’s cock under the sheets, and noticing it had gone a bit soft. It was still chubby and wrapped in a condom, but no longer rock hard and throbbing.

​

I started stroking it slightly, noticing Mason gulp and stammer for a moment, something completely lost on his roommate.

But his cock quickly regained full hardness, and I was rewarded by feeling it throb in my hand again.

The roommate was clearly there to stay, but I was increasingly determined to not let that stop Mason and I from getting it on.

​

Mason laid back down in the bed, against the pillow, exasperated by his roommate, who was still sitting on the bed opposite us, seeing everything. And he wasn’t able to keep ignoring my actions next to him.

I moved my naked body on top of Mason, and whispered, “it doesn’t matter, who care about him.”

I felt Masons’s cock between my legs, and I reached down to push it against my pussy lips, which were dripping wet with anticipation of this moment.

​

I further lowered my body, and he was inside me, his throbbing cock feeling incredible as he pushed it all the way with a thrust of his hips.

I felt my tight, 18-year-old pussy completely filled with his cock, and my pussy clenched and unclenched it with a deep sense of craving.

​

I looked over and saw the roommate, now suddenly very interested, and possibly hard, although it was difficult to tell.

​

As Mason and I started grinding against each other, lost in our own desperate fucking, the roommate clearly was touching himself over his pants.

My breath quickened, and I felt my nipples hard as Mason grabbed one of my breasts while he fucked me.

​

Mostly though, he had his hands on my hips, pulling me down into his beautiful, hard cock, while I simultaneously gyrated on top of him.

​

I was getting warm, actually hot, for the first time all night, and I wanted to throw the covers off, but they were the only refuge of privacy that we had.

I started sitting up more, working to use more of my weight to grind into Mason

Our gyrations were so intense, I was honestly surprised he hadn’t cum yet, although I supposed the condom helped with that.

​

As I sat up more, the covers fell off of my back and we were both completely exposed.

The roommate stared intently, and I saw his jeans were unzipped and he was reaching into his pants to stroke his cock.

I kept fucking Mason, and I was now straddling him in a full cowgirl position.

​

I loudly moaned his name, grabbing both his hands and pulling them up to hold my breasts.

I was gyrating up and down on him harder and harder, and I remember this was one of the first times I experienced a true rolling orgasm that lasted much longer than usual.

It felt amazing and it just kept coming…

“Oh fuck, Mason, oh fuck, yesssss, omygawd yes that feels sooo good…”

​

Another few seconds of that, and I saw his face scrunch up and his hips start thrusting hard as he came hard inside of me.

“Oh Riley, oooooh,” he moaned/grunted.

​

I let us both settle down, with my head bowed, panting heavily, and his cock still inside of me, still mostly hard. 

He roommate was stroking himself, inside his pants, and I sat up slightly. Weird to say, but I wanted to make sure he could get a nice view of my tits. Since he was going to masturbate anyway, might as well make it a good show.

Mason looked away, laughing a bit but shaking his head, as his roommate’s legs stretched out and he clearly came inside his own pants.

​

Overall, it was an interesting experience. The feeling of being watched heightened the experience immensely, and I also enjoyed the introduction to having more than one person in the room. Sex had always been such a private experience for me until that point.

It was also just the first time of many for Mason and I.

​

**The full list of my first experiences:**

[Someone Watching Me Fuck](https://www.reddit.com/r/gonewildstories/comments/a4xdp2/my_first_time_someone_watching_me_fuck_mf/) (this story)

[Group Sex (only on Patreon)](https://www.patreon.com/posts/my-first-time-23240144)

[With a Girl](https://www.reddit.com/r/gonewildstories/comments/a35d00/my_first_time_with_a_girl_ff/)

[Touching a Boy (only on Patreon due to Reddit content restrictions)](https://www.patreon.com/posts/my-first-time-23132832?utm_medium=social&utm_source=twitter&utm_campaign=postshare)

[Anal](https://www.reddit.com/r/gonewildstories/comments/a3s6tx/my_first_time_anal_mf/)

[Masturbating (only on Patreon due to Reddit content restrictions)](https://www.patreon.com/posts/my-first-time-f-23171332?utm_medium=social&utm_source=twitter&utm_campaign=postshare)

Source: reddit.com/r/gonewildstories/comments/a4xdp2/my_first_time_someone_watching_me_fuck_mf