Roommate [F] caught me [M] masturbating [college] [inexperienced] – Part 2

Link to Original Post here: https://www.reddit.com/r/gonewildstories/comments/59t4ga/roommate_f_caught_me_m_masturbating_college/

Holy crap Reddit. Sorry for not posting for so long – some big things happened in my life just a week after my original post, and I completely slipped on updating this story. Things are still settling, so I’m not sure when I can post again, but I had a free night and wanted to post part 2 of my previous account of my sophomore year of college.

Once again, same warning: not the kinkiest story around, just the classic story of a boy jerking it to a girl. And be prepared for a lot of jerking (seriously, a ton). Also, Part 2 is LONG AS HELL. A lot of setup took place before the next big thing happened between us.

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At the end of my last post, I said the embarrassment was gone once I had caught Vanessa masturbating after she caught ME dick-handed in the bathroom. Well, I was wrong. By morning, I was so completely ashamed and embarrassed that I didn’t even come out of my room. I had absolutely no idea what to say, and even less idea of what to do. But all I know is that I was completely blindsided – Vanessa was SMOKING HOT and I couldn’t believe that I hadn’t seen it before. My Sunday morning was filled with two cycles of embarrassment followed by replaying the events of the previous night followed by jacking off followed by deep shame. Rinse, repeat.

We crossed paths in our living room that evening. She was fortunately already out when I eventually emerged from my room to run errands, but was right in the living room when I got back from the grocery store. We froze when we saw each other, and both let out a clipped “Hey…”, and nothing. Just the awkwardest few seconds of my life.

Then, all at once, we were stumbling over each other with apologies.

“I am so sorry you had to see that…”
“Sorry I barged in!”
“I can’t believe I didn’t close -”
“It was stupid! It’s your BATHROOM and-”
“No, seriously, that was my bad”

We stopped, still looking at each other across the living room. And, without anything else to do, we both just started snickering with hands on our faces at the ridiculous situation. In seconds, it turned into full-on helpless laughter. Thank God, after that moment, most of the tension was broken, and I knew we were just friends again.

Vanessa finally made eye contact, and said in her much-closer-to-normal-chipper voice, “Look, it’s nothing either of us hasn’t seen before. We’re adults, and we can just forget this happened!”
I let out a sigh of just plain old relief. “Thanks, I’d really like that.” And I meant it! As incredibly hot as the experience had been (the part she didn’t know about), at that moment, I was just grateful that it looked like our friendship wasn’t destroyed. In fact, maybe no one else had to know about my crazy embarrassment!

Wrong. So wrong. Completely, totally wrong – it remained private about 3 days.

The school week started again, and we went back to the usual routine in college. That group of 8-10 friends hung out most days of the week, and often came back to our place after dinner to drink and hang out. After Vanessa and I had talked, it had cut most of the awkward tension, but not all of it – we were still putting a little distance between each other. Apparently, there was enough weirdness in the air for one of our chattier, and more social friends, Maddie, to pick up on almost immediately.

When we were hanging out at our place that Tuesday or Wednesday, maybe six of us were sitting on the couch watching some show together when Maddie and Vanessa, who had both been in Vanessa’s room, burst into our living room. Maddie is holding a beet-red Vanessa by the hand, and immediately proclaims to the group, “GUYS, Vanessa found HIS porn stash!” Her other hand was pointing an accusing finger right at me.

I was stunned and completely confused. She had??? Even without understanding, I felt a guilty, incriminating flush creep up my neck and onto my face. Oh God, this group was mixed company, like 50-50 guys and girls! Every group in college makes sex jokes, but we hadn’t reached the level of comfort yet of joking about individual porn or masturbation habits, so this was like the group hitting new levels of camaraderie at my expense. The room immediately erupted into laughter and predictable, but damned hilarious heckling.

“Ohhhhhh!”
“Dude, Vanessa is nice girl, don’t be showing her that shit!”
“Vanessa, was it weird? Was it like weird stuff?”
“I bet it was like, German dungeon porn-”
“No no, gotta be like GILFs”

This continued for a long, long ass time. Even as I was laughing so hard I could barely breathe, my ears were absolutely burning with embarrassment. It wasn’t even true!! The only person as red as me was Vanessa, who, as outgoing as she was, looked completely ashamed. Eventually…

“Oh God, what if it’s really messed up? Just all these pictures of normally dressed Martha Stewart”
Todd, bless him, followed up with, “No no, something just truly disgusting. Shit that no one could be into. Just hundreds and hundreds of the nastiest pictures… of James’ mom.” Popcorn went flying at him, and with that, he helped spread the targets to other people. He’s a good guy.

Eventually the night ended after about two or three thousand more me-watching-porn jokes took place. It became a running joke that I was some porn-obsessed horndog. After James went to bed, Vanessa immediately came to my room and knocked on my door. She was biting her lip nervously as she quickly told me what had happened. Maddie had felt like things were off, had grabbed Vanessa, pulled her into her room, and asked point blank if something had happened between us. I imagine Vanessa was like a deer in the headlights, but eventually, in her panic, she said that she had seen something… Apparently, Maddie excitedly jumped straight to “Oh shit, did you find his porn stash or something?” Vanessa hadn’t given an answer, which Maddie THANKFULLY took to be confirmation and immediately came out to tell the group. (Sounds bitchy, I know, but she’s actually a good person, very much the life of the party. And I indirectly owe her for what happened with Vanessa later.)

“I’m so sorry. I’m so embarrassed.” Vanessa looked very upset with herself, clearly guilty over the roasting I had just gotten.

I took a breath, and realized that I really wasn’t mad. As embarrassing as it had been, it was a lot less embarrassing than if the truth had come out. And these guys were good friends – even if it was something they ribbed me with, these weren’t the types of people to judge me as a person, or whisper behind my back. It would become one more thing that we gave each other shit with.

“It’s OK, really. Thanks for not spilling the beans about… you know.”
“Still… sorry.” She didn’t look convinced.

As weeks wore on, though, she realized that all the joking wasn’t malicious and she soon started joining in. Over the next couple months, being comfortable with joking around about porn and masturbation actually opened up a lot of new conversations for us that had previously been off limits. She would often come to my room just to chat after she got back from class, and we’d normally spend 10 minutes talking about our days (she honestly did this with everyone before you read too much into it). But now, our conversations would occasionally slip into our sexual history. I knew that I was horny 24/7 and intensely curious, but I realized that she was pretty damn curious as well, and had become a lot more open and even a little flirtatious with me.

Before we started talking more about this stuff, I had heard a little about her time with her ex, but this is where I really learned more about her sex life. Over those months, I learned that her ex had gotten really angry at her when she suggested other positions than missionary. I learned that she used to feel a little proud when she finished him off and saw him cum, but he was really ashamed of it and thought cum was dirty, sinful, and gross. She learned that I hadn’t had sex yet, only some trips to second and third base. I learned that she masturbated about once every couple of weeks. She learned that I masturbated every couple of days, if not more. I learned that she had tried to use a hairbrush handle once before but it had felt weird so she only used her hands. She heard the shameful and exciting story of how I had once heard about putting ice on my balls while whacking off – it was mediocre and shrink-y by the way.

These talks taught me a lot, made us a lot closer, and were a totally unexpected hot new experience for me. In short, this was my masturbation fuel for that whole semester. My dick would have been begging for mercy if I hadn’t been training it almost daily since I was 13 – that’s just good planning and consistency, every body. And, in case anyone is wondering, I hadn’t heard her masturbate since that first time. I’d often walk quietly and keep an ear out when walking by her closed door, but I never heard a damn thing. I’m pretty sure she found our talks exciting too, but she was clearly either stealthier or more careful than I was.

Fast forward to the fall, just a few weeks before Thanksgiving break. It was my birthday, and we have this awesome tradition that this group of friends started.

One of our friends was a student worker in the package room for some office at the university, so he got access to a giant 3 foot wide by 3 foot long, 4 foot deep cardboard box filled to the brim with packing peanuts. Everyone else in the group would pool money for a birthday gift, and we would put it at the bottom of the box under all the peanuts. On top of that gift, we would always hide in there some different gag gifts that were specific to that person. Previous gag gifts had included a really shitty street magic DVD to one of our friends who did card tricks, a 100-pack of scrunchies to one girl with very long hair who had a really awesomely awkward middle-school photo of her wearing like 5 different scrunchies, and so on. You probably see where this is going for me after the events earlier in the year.

We had come back from dinner to our apartment to drink and party, and eventually they brought out the giant cardboard box, which was now covered with markers and stickers after having been used for a year. I start awkwardly leaning into the pit of packing peanuts, digging around for my gift as everyone is standing around me, watching with anticipation. I pull out a couple of small funny objects, but then feel… some kind of thick paper?

I pull out, to the hoots and hollers of my drunk friends, a copy of Hustler magazine. Hah! Laughing, I ask, “OK, OK, who’s idea was it to get this one?”

Without hesitation, Vanessa puts her hand up with a big smile, “Me!”
James followed up with, “Yeah, we figured she would know what you liked!”

Even in spite of our conversations about masturbation and sex, I was still a bit surprised that Vanessa had had the idea. She was clearly no longer embarrassed or guilty about her part, and was actually egging me on. Interesting.

A couple days later, Vanessa dropped by my room as she often does and we start catching up about our days as usual. She was wearing her usual, skin-tight yoga pants that showed off her perky round ass and a simple shirt. I was wearing soft grey sweatpants. After a couple minutes of chatting, she sees the Hustler on my desk and picks it up and starts reading the cover.

“Oh, I kind of thought this would be more explicit.” She said, as she flipped open the first page.
“Uhh… you should just keep going.”
“Wait… is this even safe to touch?” She stuck her tongue out at me.
Wow, I did not expect that. “Of course it is! God, what kind of question is that?”
She laughed and flipped another page, “It’s just boobs, nothing crazy. I mean- Oh. Wow, you can see right inside her.”

She turned the page around to show me and it was a model spreading her pussy lips. I was instantly hard as a rock. I’d already looked through the magazine (obviously), but it was pretty tame compared to any video you could find online. But as extroverted as Vanessa was, this was still real forward for her, and looking through it together with me was incredibly hot, and still so strange for this semi-innocent girl.
I struggled to think of something to say. “Yeah, they like to pose like that a lot.”
She laughed – she seemed comfortable, but her voice sounded just a little strange and her cheeks were a little more pink than usual. “God, some of these look so uncomfortable.” She turned the magazine around again, it was the centerfold. There was a woman with her knees on the chair, turned around 180 degrees, and somehow sticking her butt out in a way that let you see her pussy, also spread with her hands.

“Well, being a model is probably hard.” I said, cleverly. God, I’m witty.
“I mean, it’s probably not that hard.” She immediately climbed onto my spare chair and took up the same position, without holding her crotch. “Hurts my knees though.”

My eyes were glued to her ass, which looked perfectly round and squeezable in that position. I felt my dick throb, and it was one of those rare occasions where I could actually feel pre-cum coming out the tip. She got down from the chair and I quickly looked back up at her face as I said, “Darn, not the career for you then?”

She laughed and looked down my body, then immediately back up at me as she got off the chair. I registered there was an awkward half-beat before she cleared her throat and then said, “No, as glamorous as that must be. Anyway, I gotta do some homework, talk to you later!” And left.

I blinked at her sudden departure and looked down at what she had looked at – I was pitching a serious tent in these sweatpants and there was a small, very obvious wet spot in the grey fabric at the peak where my head was. I slapped a hand to my face, embarrassed all over again, though it didn’t stop me from closing my door and immediately jerking off. As soon as I finished, I had this feeling of cold sweat – did I just ruin something great by showing too much excitement there?

I didn’t have to worry for long. She continued coming to my room over the next couple of weeks, and perusing that Hustler magazine became a part of our daily catch-up time. She’d often have comments in the first few times that still stick out in my memory – freshman me would never have believed that Vanessa could say these things:

“Wow, this guy’s penis is huge!” (Oh, my ego…)
“Her boobs are huge, but they look super fake”
“Oh my God, she’s got two fingers in her vagina but her nails are 3 inches long!”

We talked about how she had looked up some porn before but found it really fake. We talked about my own porn preferences – big mainstream porn stars were sometimes hot, but amateur stuff was way better in my opinion, especially in video form. She didn’t even know amateur porn was a thing!

These conversations kept going for a couple of weeks, but weren’t really escalating into anything more. Our talks about this stuff started to get shorter, and I could kind of feel her interest going down. I loved these times we had, and obviously wanted them to continue – on top of being really hot, they were also a big part of how I got more comfortable around women and gained confidence in general. But I had no idea what to do to keep her interest in it.

Then Thanksgiving time hit, and with it, a number of school projects due in the same week before break. We both got busy, and started spending more time in the library and in labs. With the help of caffeine and a lot of sleepless nights, I finished everything in the end, but had barely talked to Vanessa in a long while before she went home for the holiday.

I was staying at this apartment over break as my parents were traveling to visit more distant relatives, so I had a few quiet days to myself. Now that the craziness of school was gone until finals, I had some time to think about what to do about Vanessa – how the hell was I going to keep her interest alive?

Then a spark came to me – an inspired plan. It was sheer genius. I knew EXACTLY how I could escalate the situation. Without wasting a second, I pulled up some porn and started beating it, edging several times for good measure. Then, as I got close to orgasm, I grabbed the magazine – I flipped it open to the centerfold that Vanessa had mimicked in my room, and blew a huge, huge load all over the page. There was so much that the model was barely visible underneath, almost as much cum as when I had heard Vanessa in her room.

This was my master, diabolical, genius plan. Vanessa would come back from break, we’d chat, and she’d open up the Hustler and see my cum and… uhhhh…. what? What the fuck was supposed to happen after, exactly?

And there I was, struck with the age-old post-jack-off clarity that we all know. Maybe it was the three or four extra days of not masturbating because of how busy I was. Maybe it was some kind of pent up sexual frustration with the whole situation but, this… this idea was the dumbest fucking plan I had ever had. In fact, it was kind of desperate and definitely gross. What the hell had I been thinking?? I looked down at this sad, soggy Hustler, and the sad drowning porn star that must be judging me wherever she was in the world.

I left it there while I thought of what to do. I was just at a loss. Eventually, I closed it and threw it away in the trash in my room (it had dried a good amount). For the next couple days, I tried and failed to think of anything that would help my situation with Vanessa. I forgot all about that magazine.

Fast forward to Sunday after Thanksgiving. I had been on a big group text with my friends and four of us, including Vanessa, had decided to watch a movie and get dinner before class started again on Monday. I had just gotten back from the gym, was sitting in my room and was going to take a shower when Vanessa came back, a few hours before the movie time. She came in and we caught up about normal stuff. She told me how her time at home was and how different members of her family were doing. I told her about how crazy my crunch period right before break was, and that staying here had been quiet and relaxing, and a great chance to de-stress.

I was looking away when she spotted the Hustler in the trash and picked it up.

She started saying, “Aww, did you get tired of…” and trailed off. She flipped open a couple pages, but then the rest of the pages were stuck together in a huge block, crinkling with that dry cracking sound as she tried to turn them. She looked back at me curiously and innocently, and I was staring at her wild-eyed, mouth a little agape.
“Umm, what is this, water?”
I couldn’t say anything, I just had my mouth open in shock.
“What is this?” She repeated blankly, and she pulled the pages apart. It opened on the centerfold and I could see the big, whitish outlines of all of my cum stains on that page that had soaked into all the pages below.
I watched in horror as realization dawned on her face. Her eyes grew wide as she realized what it was, and she let out a tiny squeak as she dropped it onto my desk, still open to the centerfold, all my shame exposed to the world.

“Is that SEMEN? Is that yours?” She put her hands over her mouth in shock. Even in that moment, my mind blank, spinning in circles and going nowhere, I still thought… those hands were just touching my cum and now they’re on your face?

That thought jolted me out of my mental vacuum. I face palmed and winced into my hand. “Holy shit, I can’t believe you just saw that.”

And then I heard Vanessa laughing, a loud, uninhibited full laugh. Without realizing, I just started laughing too, and we were just both laughing until we couldn’t breathe and there were tears in our eyes. Months of talking, and we had somehow ended up in the exact same spot as that first day after she caught me in the bathroom.

Eventually we calmed down enough for her to rib me, as usual, “Wow, is this what you meant by ‘relaxing’?” She had a big smile on her face, clearly giving me shit.

We were a lot closer at this point so I comfortable enough to fire back through my laughing, “Well, that was part of it!”

“Wow, you must have been really stressed out. Look at this!” She started poking at the page and trying to bend it, showing how stiff the page was.

“Look, we all have our different ways of coping. Is mine so bad?”

She rolled her eyes, “I mean, everyone masturbates, but this is kind of overdoing it. Did you have something against the magazine or something?”

I cocked my head at her, a little confused. My adrenaline was running high, maybe I didn’t understand what she was saying. “..What do you mean?”

She laughed one more time, her face a little pink again. “I mean… I get that you use porn, but why did you…” She looked a little awkward as she picked how to phrase it, “Why did you finish on the magazine like… so many times?”

I furrowed my brow, my head still turned at her. “So many times? …huh?”

She picked up the magazine again and turned it at me, huge cum stains obvious over most of the page. “…all this?”

That’s what she meant! “Oh, that was just one time.” I said matter-of-factly.

She blinked a few times and there was an awkward silence. “You’re kidding.” She said at last.

“Uhh, nope. That was just once and then I threw the magazine away.”
“No way.” Her voice had changed… it’s hard to describe, but it was suddenly a little more serious.

“Seriously, just once.” I said. Her face was disbelieving. I was unsure, “Is that weird?”

“Uhh, definitely. At least I think so? My ex didn’t cum nearly as much as you.” She said it kind of fast, and I realized there was a tiny bit of shake in her voice all of a sudden. Her face was definitely rosier now.

She told me about how her ex would only dribble a tiny bit of cum, a few drops. Even the couple guys she had given handjobs besides him had cum only a spurt or two at most, and she was “amazed” when she saw one of them actually spurt a few inches when he came. She was listening to me with totally rapt attention as I told her that I had always cum a ton, and that it always shot several feet and could generally be a huge mess. It finally came out that I had been in the bathroom when she caught me because I had run out of tissues and didn’t want to accidentally hose down my whole desk when I finished. Even as I was describing this about myself, I was completely hard in my gym shorts, and I thought I saw her returning from looking down at my crotch a couple times when I looked back at her.

This would have been inconceivable to me earlier, but looking at Vanessa, it’s like she was a totally different person at that point. Now that I’m older, I realized that Vanessa must have been dripping. Her face was glowing, and her breathing was fast and shallow, and as we started talking about all this, she had started touching her neck constantly – I don’t think she realized any of that at all. As dense as I typically am, even I realized that both of us were really, really turned on.

But she caught me off guard. She had taken a breath and was looking at the clock, “Oh, hey. We have to leave for the movie in a half hour. Are you ready to go?”

I tried to think of something to hold onto the moment but had nothing. “Oh… I just got back from the gym, I need to shower -”

She cut me off unexpectedly, “OK great, I’ll go change first!” She got up, and I noticed that she took one more look at the open magazine, and then she suddenly left my room. I had a strong, strong feeling that I knew what she was going to do.

My heart started thumping hard in my chest again, and I could feel my adrenaline pick up. Both James and Vanessa knew and occasionally made fun of me for taking longer showers, maybe 15-20 minutes. I was only getting harder at the thought of what might happen. I picked up my clothes and towel and went to the bathroom – I made sure to turn on the shower before I closed the door so that it would be very audible. I closed the door, and slid the shower door noisily so that it hit the shower wall, and then I pressed my ear against the door. I listened as hard as I could and I thought, THOUGHT, that I could barely hear some foot steps approach from the living room, and then go back from where they came. It was almost impossible to tell through the sound of the shower running.

I demonstrated the most incredible feat of patience as I waited in that shower for two minutes. Then, heart pounding in my ears, I carefully opened the door and poked my head out. The coast was clear. I started tip-toeing my way out of the bathroom, closing it behind me, and started moving past my own room, headed toward the living room. On an impulse, I looked back in my own room – the magazine was gone. My heart skipped a beat. Holy shit, the magazine was gone. There was only one explanation: Vanessa had taken it. Vanessa had taken the cum-soaked porno mag from my room. What the hell was happening?

It was a weird sensation – I could hear my pulse in my ears, but I could also feel my pulse in my chest, and my dick, making it throb. I entered the living room and saw Vanessa’s door closed. I was only halfway across when I heard her moaning. My head spun from the dangerous amounts of blood that had now moved to my nether regions.

She wasn’t trying to be as quiet as last time. Maybe it was lust, or maybe it was knowing that I was showering, but I heard breathy moan after breathy moan. I reached the door and put my ear close. I could immediately hear how wet she was in between her voice and it was building fast. I carefully took off my gym shorts and joined her. There was already enough precum to almost use like lube, I was so turned on.

“Oh fuck…” I heard from the door. I pictured this petite girl spread out on her bed, rubbing her clit and fingering herself, moaning. “God… mnnn”
I pictured her looking at the magazine covered in cum as she stroked herself, and thought about this innocent girl seemed so turned on by seeing my huge load. It was too much, I could already feel myself getting close, and her voice was getting higher and more frantic. Her voice was so clear through the door.

Then I heard the most incredible sound. She was groaning and then, “Ahh… ahh… so much cum… yes… YES” and then a sudden, clipped silence. That beautiful, full silence lasted two whole seconds before it was followed by a massive groan as she came. I had already been close, but the moment I heard her say that, I felt myself go over the edge. I barely had time to grab my boxers from the floor as I came spurt after spurt into them, my legs bucking as I clenched my jaw to stay quiet.

I took a few seconds to recover, listening to the soft moans still coming from the other side of the door as Vanessa cooled down, but I tip-toed with weak legs back to the shower. It was the most satisfied that I had felt in months. The orgasm had been amazing, but knowing that Vanessa was that turned on by something about me had put me on cloud nine. When I got out of the shower, the magazine was back in my room, like it had never been moved.

Things were only going to get more interesting from there…

—
Once again, I know this ended up being incredibly lengthy so thanks to everyone who stayed with it. I’m not sure when I’ll get to part 3, but I’ll do it eventually!

Source: reddit.com/r/gonewildstories/comments/5xzy76/roommate_f_caught_me_m_masturbating_college