Dorm Room Exploration

August 19

Dear Diary,

I'm so nervous about tomorrow. It's my first day of college! I'm not worried so much about the classwork, but the social aspect makes me anxious. I've grown up with the same friends my whole life and I'm finally breaking free from the people that have defined my identity so far. I hope I'll find some friends easily. Maybe I should join a club or a sorority? Who knows. I also wonder if I'll find a boyfriend. I never dated anyone seriously in high school, but hopefully that will change now that I'm older and away from home. Everything seems so overwhelming right now. I guess I'll just wear a cute outfit, try to appear confident and intelligent in all my classes, and see how it goes.

Luckily, I do have one comforting figure from my pre-college life. I get to share a dorm room with my twin brother! Normally, the people who assign students to their dorms would not assign a boy and a girl to share a room, but they make exceptions for family members. I think the administration realizes that being a freshman can be stressful, and that it helps to have someone familiar close by.

I haven't shared a room with Brandon since we were really little, but I have good memories of that time. As a kid, I always loved pretending to be asleep until we heard our parents snoring. Then I'd crawl down to his bunk, hide under the covers with a flashlight, and stay up all night with him whispering and playing games and just having fun. It was like a sleepover every night with your best friend. Who wouldn't want that as a kid? Once we hit puberty, our parents moved us to separate rooms, but we never lost that closeness. Throughout middle and high school, we definitely had our own friend groups and interests, but at the end of the day, we were still each other's best and closest friend. I hope we can still stay that way during college. Right now, I can see him sleeping on the other side of the room while I'm at my desk, and I already feel comforted. No matter what happens tomorrow, I'm glad that I can come home to someone I love.

August 20, afternoon

I made it through my first day of freshman year! The first day of class was exactly what I expected: mainly just going over the syllabus, learning names, and setting expectations. The real learning would happen later. When I went to the cafeteria for lunch, I saw a few girls who also looked nervous and friendly and asked if I could sit at their table. They were so friendly and readily welcomed me in their group! I felt so relieved. Even if these girls didn't end up being my best friends, at least I didn't have to endure the embarrassment of sitting alone in the dining hall.

I couldn't help but notice that Brandon was sitting at another table, eagerly talking to this beautiful girl and blushing the whole time. I quieted the strange pang of jealousy in my stomach that unexpectedly occurred when I witnessed this. What was that all about? We've always had separate friend groups before, and I've seen him with girls in the past. I couldn't quite place the source of my jealousy, so I decided to ignore it. It was probably just first day jitters. I'm sure as soon as Brandon comes home tonight, he will tell me all about this new girl he's chasing and I'll feel better about the whole thing.

August 20, evening

Just as I expected, Brandon started gushing about this Kelly girl as soon as he walked in the door. He couldn't stop talking about how she was planning to be a doctor and how she was so smart and funny and beautiful. The whole time he was going on and on about her, I felt a mix of emotions. I was grateful that he felt close enough to me to tell me all the little details about his first day of class and his new crush. But that pesky jealous feeling kept returning every time he said Kelly's name. What exactly do I feel jealous about anyway? Is it the fact that he seemed to find a romantic partner right away, as usual, while I'm still a virgin who hasn't ever gotten laid? Perhaps I'm projecting my own sexual frustration on him. I'll get to the bottom of this eventually.

August 21, morning

The weirdest thing happened last night. I fell asleep pretty early since I was exhausted from all the first day excitement. However, at about 1 in the morning, I woke up to a distracting rustling sound from the bed next to me. I kept my eyes mostly closed and turned to the side to face my brother, the whole time acting like I was still asleep. The street lamp outside our window made it so that there was a faint light in our room every night. When I opened my eyes ever so slightly to see what was happening, I noticed an up and down movement happening right in the middle of my brother's sheets. Oh my god, I've caught my brother masturbating! Still pretending I was asleep, I decided to watch my brother touch himself. I watched as he jerked himself off harder and faster until he let out a little whimper. He immediately covered his mouth with his hand and looked over at my bed to see that I was still sleeping. I gave no indication that I was awake and he visibly relaxed. After he rolled over with his face turned toward the wall, I turned to lie on my back, eyes wide open, trying to ignore how wet I was from watching my brother cum. I told myself that it was just a normal reaction to watching anyone be sexual, and it didn't mean I was into my own brother in that way. Regardless, my fingers still found their way to my pussy, where I rubbed my clit in quick, urgent circles until I let out a whimper of my own.

August 22, morning

Brandon didn't act weird or anything the past few days, so I'm assuming that he doesn't know I watched him masturbate. Thank goodness! We tell each other almost everything, but we've always steered clear from talking about sex stuff. I don't want him to feel weird about his decision to share a room with his sister. But, I found myself thinking about Brandon touching himself all day while I was in class. It was distracting for so many reasons! I secretly hope he does it again tonight so that I can watch. I think I'll pretend to be asleep until I hear that rustling sound again.

August 22, evening

Well, it looks like I won't get what I was hoping for tonight. Kelly has been in our room ever since dinner, and they have been flirting the whole time. They've been cuddled up on the bed, giggling with each other and occasionally making out. I've been trying not to interfere by just sitting at my desk pretending to do homework, but I still feel annoyed and jealous that she is in the room with us. I don't want to cockblock my own brother, so I stay quiet and ignore them. I'm still going to "go to sleep" early so I don't have to spend all this time actively avoiding eye contact with them.

August 23

Oh. My. God. Last night took a completely unexpected turn. As I planned, I "fell asleep" around 10pm,

hoping they would at least quiet down a bit. I lied down on my side so that I was facing my brother's bed, even though I knew I'd probably just see the two of them cuddling together. After an hour, nothing was happening so I started to drift off in to actual sleep. However, at about midnight, I woke up to them whispering to each other:

Kelly: Brandon, I really want you to fuck me tonight.

Brandon: Kelly, I really want to fuck you too, but I can't do it with my sister in the room! We're close and all, but that's just too weird.

They both look over at me to see me fast "asleep." I snore a bit for good measure.

Kelly: Is she a deep sleeper? We can just keep it quiet and she probably won't notice.

Brandon looks over at me one more time before saying, "Yeah, I used to share a room with my sister and she could sleep through anything: storms, sirens, you name it. I'd know if she was really awake."

Kelly: That's good enough for me. At this point, I want to fuck you so badly I don't even care that your sister is in the room.

I try not to gawk in disbelief as I see Kelly take off her clothes and Brandon rustle in his bedside table for a condom. They're actually going to have sex with each other while I'm in the room! I'm embarrassed to admit that the thought of watching my brother have sex was way too enticing for me to fall back asleep, but I still adjusted my body to get a better view of what was happening.

At first, they played it safe by doing stuff under the covers next to each other. But, as they felt more confident that I was asleep, they got a little more creative and risky with their positions. I watched with anticipation as Brandon threw the covers off, forced Kelly into a doggy style position, and started to pound her from behind. Kelly was trying to muffle her pleasure by moaning into the pillow.

This was just too much for me. I was so wet from watching my brother fuck this girl that I began to touch my clit while I watched the scene unfold in front of me. Just as I expected, I was dripping wet and yearning for release. I was hoping that Kelly's moans would drown out any sounds coming from my direction. I got so caught up in what was happening that I stopped worrying about pretending to be asleep, and soaked up the full picture with my wide open eyes.

At one point while Brandon was still fucking Kelly from behind, he looks over at me. My eyes grew wide with fear as I saw Brandon realize I was watching him. After he sees my eyes, his gaze travels down to my hand, where he can clearly see me touching myself. To my surprise he smiles and mouths, "Keep going" while never taking his eyes off of me. Because of Kelly's position, she thankfully has no clue about what is happening next to her. Watching my brother fuck while he watches me touch myself gets me so close to my climax. Brandon starts to cum, looking me straight in the eyes the entire time. The forbiddeness of the entire situation, from the voyeurism to the newfound sexual connection with my brother, sends me over the edge and a wave of intense pleasure washes over me. I have -never- cum like that before. The fear of being caught by Kelly set in and I immediately pretended to be asleep again.

I knew I'd have new experiences in college, but I never thought that masturbating to the sight of my brother fucking would be one of them! I wonder what tonight will bring?

August 24, morning

Diary, I am at a loss for words. Once Kelly left this morning, Brandon and I had a talk:

Brandon: So, about last night...

Me: Uh...yeah. Wanna talk about it, or just pretend it never happened? No one ever has to know. It wouldn't be the first twin secret we've had.

Brandon: I think it's best if we talk about it. Can we cuddle in your bed and chat? Like we used to?

Because it was a twin bed, I lied on my side, preparing to be Brandon's little spoon. We used to cuddle like this when one of us had a rough day, but the physical closeness was different now. I became acutely aware of how I could feel Brandon's cock pressed up against my ass. My mind immediately flashed to an image of Brandon fucking me from behind like he did with Kelly last night. I shifted a little bit, again trying to ignore how wet I was getting from this simple interaction with my brother.

Me: So, what do you want to talk about? You go first.

Brandon: I saw you looking at me last night, Amanda. And I know you liked what you saw. Have you always thought about me that way?

Me: Honestly, no. I mean, you're my brother. It didn't even occur to me before. What about you? You certainly didn't seem surprised that I was looking at you like that. Have you thought about me before in that way?

Brandon: No, I've never thought about you like that either! I guess I was just so caught up in the moment with Kelly, I wasn't really thinking straight at the time. I've always fantasized about being watched while I was fucking someone, and I guess I was just so excited that this fantasy was finally happening. I didn't really think about what it all meant.

As Brandon was telling me this, I could feel the bulge in his pants becoming larger. Instinctively, I pushed my ass against him to meet his growing cock. He immediately pulled me closer to him, pressing up against me tightly. I let out a whimper and he gently covered my mouth with his hand. Keeping one hand over my mouth, he started grinding his hips against me while he caressed the curves of my body with his other hand. I started moving my hips to meet his, and let out another muffled moan of pleasure.

Brandon moved his hand away from my mouth and slowly brought it down to my chest, where he firmly pressed down on my sternum. I was expecting him to grope my breasts, but I realized all he wanted was to hold me closer to him so that I couldn't move. I loved how he was taking control and forcing me to submit to his will. I knew at that point I would let him do whatever he wanted to me.

He maintained his grip on my upper half while his other hand slipped into my jeans. I was surprised when he didn't immediately go for my pussy. Instead, he grazed his fingers over my panties, driving me crazy! He was such a tease. Brandon purred in my ear, "I can feel how wet I'm making you. Should I keep going?" Another whimper escaped from me as I whispered "Yes, Brandon. Please don't stop!"

Before I could even finish my sentence, Brandon grabbed both of my wrists, pulled them up over my head and twisted my body so that I was lying on my back beneath him straddling me. I never would have guessed that my brother would be the dominant one in bed, but I was enjoying every minute of it. I wanted him inside me so badly.

He looked straight in my eyes and said, "Amanda, you're not allowed to cum until I give you permission. Is that clear?" I felt like I was melting beneath him as I replied, "Yes, sir." I could tell he was so delighted that I called him sir. With that, he let go of my hands so that he could take off my jeans and my panties, revealing my throbbing pussy. Brandon took a few moments to admire me and how visibly wet I was. Now that he was distracted and my hands were free, I took off my shirt and bra and lay there completely naked in front of my brother. He looked me up and down, took a deep breath, and just said, "Wow. I have one gorgeous sister. I can't believe I'm about to make her cum." I shuddered with anticipation at what he was about to do to me. Was he really going to fuck me?

Brandon looked at me with a devilish expression and said, "From now on, you are going to do exactly as I say. Start touching yourself while I take off my clothing and get a condom from my drawer. I want to watch you masturbate like I did last night." I was happy to obey his command, as my pussy was practically begging to be touched. I let out a moan as my hand found my clit and I began to press hard into my self. Never losing eye contact with my brother, I bucked my hips as I played with my clit and then slipped my fingers into my wetness. After slipping the condom on, he stood next to the bed and started to jerk himself off too. We were both getting so turned on watching each other masturbate. Finally, he sat on the edge of the bed and asked me to stand in front of him. What did he have in mind?

"Amanda, I want to watch my sister ride my cock. I want you to straddle me and ride me until I say it's okay for you to cum. Do you understand?" "Yes sir!" I exclaimed breathily. I was nervous, but that didn't stop me from eagerly climbing onto my brother's lap. I closed my eyes as I slowly positioned myself onto him. We both moaned with pleasure. His huge cock made me feel so full! I thought I was about to cum right then and there but I remembered his rule. He gripped my ass to pull me in closer as I thrust up and down on his dick. I opened my eyes and gazed into his while I rode him harder and faster.

"Oh my god, Brandon, you feel so good! I exclaimed. "Amanda, you feel incredible. I love watching you fuck me like this."

Hearing him say that nearly put me over the edge.

"Brandon? I'm so close. Will you please let me cum?" That devilish smile returned to Brandon's face as he said, "You can cum after you count down from ten. I want to watch you fuck me just a little bit longer." I continued to ride him as I moaned out, "ten..nine...eight...sev-"

I couldn't help myself as a loud moan escaped from my mouth. I had reached the point of no return.

Holy shit, I was cumming all over my brother's cock.

I could feel Brandon's hands grip me tighter as he was doing the same. We opened our eyes to look at each other, with him still inside me, and just soaked in the intensity of what just happened. After cleaning up a bit, we returned to the bed to cuddle and just enjoy being next to each other. After a few minutes of quiet, Brandon looks over at me with that devilish smile of his and says, "I think we're adjusting pretty well to our new college lifestyle, don't you?" I gave him a playful slap on the chest and returned to my previous cuddle position. I could certainly get used to this. I wonder what other new experiences my freshman year will bring?