Diary of a Horny Student Ch. 32

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Tim gets a spicy introduction to the college experience.
11.9k words
4.83
11.5k
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Part 32 of the 33 part series

Updated 12/29/2023
Created 04/01/2022
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32

The sharp pain in my head woke me up. My brain felt like there was a six foot spike splitting it right down the center. The pain woke me up, but the dryness of my mouth kept me awake.

My eyes were blurry, overwhelmed by sunlight bombarding them. One blink, no good. Two blinks, no good. Finally I rubbed them, and my surroundings started to come into focus: I was on a couch...in a room with...only three walls?

No, I was outside. Sort of. Outside AND inside. I was...on a balcony. It was a gorgeous morning, aside from the splitting headache, and I shut my eyes trying to remember where I was, and how I got there.

****

"Don't you have any like...friends or something who could help you with this?"

I stumbled my way toward Alex's car, carrying one of many cardboard boxes that we jammed into the small vehicle, each one seemingly heavier than the last. She was heading back to college this weekend, and for some reason her mom, my step mother Kelly, thought it would be a good idea not only for me to help her pack, but to accompany her to campus for the night.

Neither one of us was particularly thrilled with the idea.

It's not that I didn't like Alex, we were...perfectly cordial with each other...and I was always happy to help when needed, but the timing was inconvenient.

Timing, and time itself, was the only thing I had on my mind recently. The summer was quickly coming to an end, and soon the people I'd known my whole life would be dispersing into the world for the first time, starting new lives and meeting new people. Pretty soon the longest relationships of my life would ostensibly be over. Pretty soon Tara would be gone.

She was my best friend, and lately we had both discovered that there might be something more than just friendship, and time was quickly running out to determine whether that was true, or whether we were just young.

Time wasn't the only thing standing in the way, however.

Tara and I shared practically everything as friends, and one of the most electric revelations we shared was the discovery that Sandy and Don, my step mom's best friends (and not to mention my ex-girlfriend Steph's parents...), our upstairs neighbors, were secretly kinky swingers with a penchant for filming their exploits. This was quite exciting, so much so that Tara and I both shared explosive orgasms when we viewed one of the tapes, but apparently videos weren't enough for Tara. She wanted to experience it for real, which brings me to the next explosive revelation we shared: that for the last who knows how long, Tara had been joining Sandy and Don in their bedroom. That's right, my ex-girlfriend's parents were fucking my best friend.

My feelings on this were complicated to say the least. I was angry: angry that she didn't tell me right away, angry that she was doing it at all, angry that she might be doing it to get back at me, angry that maybe she didn't consider me at all. I was Jealous: jealous that it wasn't me getting to experience Tara's body, jealous that I might never be what she'd want now. And of course, I was horny: I mean I had seen Tara's body, I had seen Sandy and Don, I knew what they were capable of--let's face it, I had jerked off to a video of them fucking my step mother, you think I DIDN'T want to see what it was like when they fucked Tara?

I thought about it constantly. How they might do it, who would get the most attention. I wondered if Sandy held Tara's hair while Don fed his large cock down her throat, or maybe the two girls sucked him at the same time. I wondered if Tara ate Sandy's pussy while Don fucked her, or vice versa. I wondered if he fucked her in the ass. I wondered if Sandy and Tara waited patiently on their knees, kissing, while Don worked himself to the edge. I wondered if they'd present their bodies to him, heads back, mouths open, while he finished himself all over their faces.

I couldn't stop thinking about it, all the possibilities, to the point that I needed to distract myself by getting lost in the body of another girl, a voluptuous Korean Christian girl named Talia. She was excellent. I got to introduce her to a world of sex, and we had fun, but it quickly ran its course and I was back to square one, realizing that I could sleep with all the women in the world and I'd only just be running from the conversation I knew I needed to have.

Tara and I needed to put all our cards on the table, and we were running out of time to do it.

But there was another variable involved as well: Sarah. She was my next door neighbor and longest crush, but she was also Tara's ex-girlfriend. There was definitely unfinished business between them, and the shared knowledge between her and I about how Tara was spending her nights had me spending more time with Sarah than I ever had in my life. This was something I would have relished a lot more if there wasn't a central issue monopolizing the focus for both of us.

Sarah and I would run together occasionally, but I hadn't seen her since Tara's big revelation. I had been avoiding her, focusing all my time on Talia. After Talia and I went our separate ways, instead of hoping to get the timing right and "accidentally" run into her, I for once in my life took the initiative and did something I'd never done before: I went up to Sarah's house, and knocked on the door.

****

"I can't stop thinking about it either," Sarah said as we moved into her living room. I had the details of her bedroom almost memorized from the times I had peeked across into it from my bathroom window, but I had no concept of what the rest of her house might look like. It was...very normal. "Part of me is angry, part of me is insanely turned on..."

"Yeah...it's a strange combination," I said with a slight chuckle. "Where I'm at with it...is that I can't tell her how to live her life--neither of us can--but I know that our time is almost up, and I'd regret it forever if I didn't talk to her about it. About us. And I know you feel the same way, which is why we both need to do it. Together."

She didn't need to respond--Sarah's silence spoke volumes.

"When you say 'talk about us,' I know you don't mean me," she said softly after a moment. "Why would you want me there?"

"I've asked myself the same question, and the truth is...this isn't about you and me. It's about her. I love Tara, and you love Tara, and this is about letting her know that we both love her no matter what she does, no matter who she does it with."

Sarah gave me a warm smile. "You're a good egg, Tim."

I smiled back, mildly embarrassed. Even in my current state I wasn't so distracted that I didn't feel a tingle buzz through me. She was so gorgeous.

"Even so," she said, brushing a lock of red hair off from her eyes, "it is pretty wild, though isn't it?"

"Yes!" I practically burst out. "I mean at the very least, they're literally old enough to be her parents."

"Honestly, that's the least weird thing about it. That part I...get."

"Oh?" I countered, eyebrow cocked. "What makes you say that?"

"I just...get it." She said, a slight blush starting to form on her pale, freckled cheeks.

"Oh really?" I said with a laugh.

"Yeah..." she trailed off, taking a moment to consider whether to continue. "I may have...lost my virginity to an older guy."

"Like...college age older?"

"Like college...professor...age..."

"Oh my," I said, eyebrows practically to the ceiling. "Are we talking newly hired? Or...tenured?"

"Definitely tenured." she nodded emphatically.

"I see..."

"It was my 18th birthday, I was on vacation, he was charming, and I was mad at my parents and wanted to do something naughty."

"And?"

"And it was fucking phenomenal." she said in a burst of nervous laughter. "So I'm just saying I GET it."

"So do I!" I said through my own laughter.

"You don't think less of me now do you?" She nervously asked.

"Sarah, I've spent the summer as the sub in a BDSM hook up relationship with my boss where she would fuck me but never let me cum. So no, I'm not going to throw the first stone there!"

Now it was her turn to have sky-high eyebrows. "Holy shit."

"I, uh...wow..." I said, feeling the heat rush into my face, "you're actually...the first person I've told that to. Not even Tara."

"I never knew you had it in you, Miller!" The way she said my last name made me think of Tara.

"Trust me, neither did I."

"And she never let you cum? Not once?" Sarah said, leaning in with interest.

"Well, she did," I said, "but only once. It was the last time we were together--she switched the roles and--"

"And she let YOU dominate HER?"

"Yeah." I responded, making no attempt to include my coworker Gina's role in the events of that evening.

"Wow...how was it?"

I caught the smooth skin of her thighs rub together slightly.

"Definitely worth the wait."

We both laughed again. From then on it felt like something lifted off of both of us. It had been pretty awkward between Sarah and I lately, but there, in her living room, having shared some pretty intimate experiences with each other (consensually this time!), we finally became really comfortable with each other.

"So...what were those tapes like?" Sarah said, genuine interest in her eyes.

"Honestly?" I responded, pausing to replay the greatest hits in my mind's eye. "Fucking incredible," I said with a deep sigh.

"Damn." There was a sense of longing in her voice, and her gaze drifted far away. "See anyone you knew in there with them?" She joked, coming back to earth.

"Ha--No, I didn't," I lied.

We continued to talk together for a while more, really enjoying each other's company. Then, as time wound down, we made a decision--once I got back from helping Alex move into school, Sarah and I would finally talk to Tara.

***

"Did you see how excited your mom was to have us out of the house?" I said, merging onto the highway.

"It was hard not to." Alex flipped through her phone in the passenger seat, mindlessly.

"I bet she couldn't wait for us to leave for the weekend so she could have Brian over." I said, shaking my head

"I don't blame her."

We both stiffened up. In that moment of mindless sibling conversation, Alex dropped her guard long enough to remind both of us that she and her mom Kelly's current boyfriend Brian used to fuck. In fact, Alex had lost her virginity to Brian. It was long before he met her mom, but that didn't make it any less awkward.

"Anyway," I continued with a clearing of my throat, "tell me about your friends. What should I expect this weekend?"

"Well my roommate isn't getting back to campus until next weekend, which is the ONLY reason I agreed to let you stay over, so you won't be meeting her, but she's...nice. Then there's Jane, she's pretty stuck up, but she's a good hang. She'll probably give you a hard time, don't let it get to you, she's rich so she's a snob, that's all. And then there's Meera--she's great. A ton of fun, and will drink anyone under the table. Very competitive."

"Mmhmm," I said, trying to get past the details to the important stuff, "are they hot?"

"You don't need to worry about that. You are NOT sleeping with any MORE of my friends. Not that you have even have a chance with them, anyway." Alex chided.

I just smiled. It's true, I had slept with Alex's best friend Steph, but Alex had no idea the extent of what Steph and I had experienced together. I had lost my virginity to Steph, but what Alex didn't know was that Steph had lost her anal virginity to me. Or that Steph had been in a relationship with our nextdoor neighbor Sarah. Or that Steph's parents also happened to be Sandy and Don, the hot older couple currently fucking my best friend Tara. Or that they also happened to routinely have group sex sessions with Alex's mom (my step mom) Kelly. Or that Brian had also been involved. Or that they had taped it. Or that I had seen those tapes.

Yeah, it was safe to say there was a lot that Alex didn't know.

I discreetly shifted the slight chub I was developing, thinking about all this carnal knowledge, and focused back on the road.

"Have you...talked to Steph much at all?" I asked as nonchalantly as I could muster. Alex and Steph had been best friends, but had had some sort of a falling out, and I had no idea where they currently stood. Steph was attending the same college as Alex, and had left home early to play catch up so she could start this fall as a sophomore like Alex. They were bound to cross paths, and I had no idea if that would be a good thing or a bad thing.

"We've talked." she said in a low tone, "things are...better. Good. I think. I hope."

"What happened with you two?"

"It's all in the past now. Not even worth talking about." She turned away from me, gazing out the window.

I left it at that.

We discussed the plan a bit later--I'd help Alex move in, then that night we'd be going to a party at some guy named Ryan's place. I couldn't gauge by the way she talked about him whether Alex was sleeping with him, but there seemed to be a good chance she was.

That was fine with me, though, good for her--I was just excited to get out of town for a couple days, and more importantly to get out of the incestuous circle of erotic acquaintances I had and meet new people.

***

"Oh, goddamn it, I thought you weren't gonna be here till next week?" I heard Alex say in surprise as she pushed into her dorm room.

The sudden entry disturbed a couple who had clearly been making out on the bed at the far end of the room, and I heard a rustle of clothing as I made my way in behind her. Sounded like her roommate was back early.

"I decided to come straight back after vacation, so I could..." her voice trailed off as I entered the picture. It was a voice I knew very, very well.

"What's going on here?" I said, looking across the room. Our eyes locked. Her hands drew her cardigan closed over her tight t-shirt. Her long, volleyball player's legs twisted nervously.

"Hi, Timmy," she said.

I looked at Alex. I looked at her roommate.

"Hi, Steph."

Our eyes locked for a moment, and three of the four of us recognized the awkwardness of the situation.

"How you doin, pal?" a voice rang out, and I suddenly found a wide, flat hand stretched out in front of me. Reflexively I reached out and shook it.

"Tim, Alex, this is Jack," I heard Steph say. I followed the hand up the arm of its owner to see a big brute of a guy with a crew cut and a grin that told me this guy never had to really work for anything in his life and he knew it. "My boyfriend."

My stomach dropped again. Of course. I looked at Steph. She said nothing, but I could see the pained look in her eyes. Her beautiful, blue eyes. I missed those eyes.

"You must be the little brother." Jack boomed.

My attention all at once was back on this fuckin guy.

"Little brother?"

"Yeah, this is my step brother, Tim" Alex stepped in, "he's helping me move back in and is gonna stay over tonight. Or at least that was the plan--he was gonna crash here in your bed--I wasn't expecting you back so soon, Steph."

"I'm sorry, I should have let you know I was coming back. I didn't mean to make things...difficult."

I swallowed hard at the word.

"No problem at all," Jack boomed, "Steph can stay at the house with me tonight."

The house. A frat guy. Of course.

"Got a little unfinished business anyway, don't we babe?" Jack followed up with a chuckle and a playful swat of her perfect ass.

"Stop!" Steph chided with a playful, yet embarrassed tone. She didn't' immediately meet my gaze afterward.

"Gross," Alex said under her breath, rolling her eyes.

"Hey why don't we leave you guys to get settled in, and we'll catch up with you at the party later?" Steph volunteered.

"You guys are going to the party?" Jack said, lighting up. I nodded. "Nice, dude! Little brother's gonna get a little taste of what college is really like!" he slapped me hard on the shoulder.

I hate this guy.

We said our goodbyes and the two of them left. I stood quietly in the middle of the room for a moment.

"Hey," Alex said, touching my back, breaking my daydream, "I'm sorry. She wasn't supposed to be here." Alex may have referred to what Steph and I had as "fucking her friend" in the car, but there, in that moment, she recognized how hard this must have been for me. She was a good sister.

"It's ok," I said with a weak smile. We both knew it was a lie.

****

Nightfall came, and after dinner, and freshening up, Alex and I made our way to Ryan's place. It was a couple blocks off campus, and as we approached the building, I was instantly entranced by the idea of a cool off-campus apartment. A place to hang and have parties. Real college stuff.

I had hoped to focus on the moment, but I had other things on my mind. I was wondering what I was going to say to Steph, if I should even say anything. What she would say to me, if anything. I wasn't sure how to act cordially around her yet, even though it had been months since we last saw each other.

"Hey, I wanted to tell you, before we go in," Alex said as we waited for the door to buzz, "she's not coming tonight."

"Huh?"

"She texted me earlier--they're not coming, she said she had a long day and wants to call it an early night. So...try to enjoy yourself tonight, ok?"

Alex's words I'm sure were meant to comfort me, but the drop in my stomach told a different story.

Soon the door buzzed, we entered, and at the top of the third flight of stairs we entered an apartment at the end of the hall where music was bumping and the party was in full swing. I usually did ok at high school parties, but this was a room full of older people, all strangers, and I suddenly felt a slight panic at the prospect of getting lost among them.

"Alex!" a voice rang out, and we both turned to see the big, bubbly smile of a short, curvy Indian girl making her way toward us through the crowd, drink in her hand raised up high. Another girl followed behind, this one taller, perfectly tanned, with much sleeker angles to her body than her friend. "You made it!"

Alex shared a hug with the girl, a big smile on her face. "Of course! I wasn't gonna miss this!" Another hug with the tall girl, and the three began to laugh and chat.

"Did you see Ryan yet?" Meera inquired, her eyebrows bumping.

"No, not yet."

"He's in the kitchen."

"I'll have to get over there. I definitely want to...talk with him."

They all giggled. I quickly started to feel myself fading into the background. Quickly started to feel like the "little brother."

"And this must be...Tim?" The Indian girl with the big smile said, pulling me up out of the mental waters.

"Yeah, sorry, Meera, Jane, this is Tim, my step-brother."

"Hi," I said, shaking their hands. I'll tell you, even all these years later, there's nothing that will snap a man out of a melancholy state like attention from a beautiful girl, and Jane and Meera were two beautiful girls.

Meera, the Indian girl with the big smile, had long, flowing, black hair, full of crinkles that framed her head adventurously. A little on the shorter side, she had thick, bold hips that were poured into her tight jeans, accenting her ass, but it was her low-cut blouse that really caught my attention. Below her smiling face, down her smooth neck, were two big, luscious, brown breasts. On display through the plunge in her neckline, they offered up to the world cleavage so deep you could almost dive into it. I wasn't an expert, but I was almost certain she wasn't wearing a bra.

Jane was much more stylishly, if conservatively, dressed, long legs extending out of perfect shoes, up under a mid-thigh dress, topped off with a blazer. Meera looked comfortable, Jane looked fantastic. I couldn't get a great sense of the body beneath her dress, but could tell that it was the kind of body that clothes should be grateful to be worn atop of. Deep eyeshadow and a subtle lip color accented her face. She had an icy demeanor about her, but wasn't altogether unpleasant.