Diary of a Horny Student Ch. 33

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Tim's summer comes to a climax.
11.8k words
4.9
25.4k
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Part 33 of the 33 part series

Updated 12/29/2023
Created 04/01/2022
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33

I had the windows down and the volume up on my drive home from Alex's college. The wind felt good whipping over me. I had gone there only with the intention of helping Alex move back in, and maybe to experience my first college party--I had never expected to leave there with some much needed closure.

Alex's roommate came back early--a roommate that left me blindsided when she turned out to be my ex Steph. I had no idea if or how we would reconnect while I was there, but we did (boy did we ever), and I left for my drive back home with empty balls and a clear head.

The only thing on my mind now was my best friend Tara. I needed to tell her how I felt, how I REALLY felt, before it was too late.

Rolling up to the house, I parked the car and pulled out my phone. I typed "Hey" into the message box, hit send, and waited.

And waited.

And waited.

Cold sweat began to form on my back.

Then finally, three bubbles, and "Hey yourself" in the reply box.

I let out a breath I didn't know I was holding.

"Do you think we could talk? The three of us, I mean." I typed back.

A shorter wait this time, then the three bubbles.

Then the bubbles disappeared.

Then returned.

Then disappeared.

I couldn't tell if she was writing something extra long, or if she wasn't sure what to say at all.

Then a single word reply: "sure."

Ok. Good. Progress. I was drafting my next message when my phone buzzed with another one from her.

"How about tomorrow night, after I get back?"

My stomach dropped. Got back from where? I couldn't see the spot where Don and Sandy usually parked, so I couldn't tell if one of their cars was gone. Could Tara be off on some weekend getaway with them?

What if there was a fourth person there with them?

My mind immediately jumped back to the dvd we each had seen, the one where my step mother Kelly got double penetrated by Don and a nameless friend of theirs.

My cock twitched at the thought.

But that was none of my business. That didn't matter. What mattered was talking to Tara. So I shook off the thoughts, and wrote back that the time sounded great.

Taking a breath, I put my phone away and headed inside to freshen up before going next door to tell Sarah the plan.

****

My house was eerily quiet when I entered, and surprisingly a mess. Kelly usually kept a pretty tidy household, and required Alex and I to do the same, but not today, and as I made my way around I began to realize why: Kelly and her boyfriend Brian had had the house all to themselves...and they made the most of it.

There were plates and glasses piled up on the kitchen counter, and two empty bottles of wine nearby, indicators of a romantic dinner well-enjoyed.

Moving toward the living room told even more of the story. A man's shirt dropped in the middle of the hallway. A thin red cloth draped over one of the living room lamps, no doubt to create mood lighting. Dress pants and shoes in a pile by the couch. Nothing too interesting, considering what two adults spending an evening together might get up to, but it was what I saw on the floor next to the pants that caught my attention: black high heels, black lace panties, and a sexy black corset with a delicate black eye mask next to it.

It was here that the lines began to blur - the lines between the Kelly I knew, and the intense sexual being I saw on those videos. This sexy lingerie, the mask, was something much more erotic than I would ever have expected in real life from Kelly. I imagined the show she must have put on for Brian, sexy and mysterious, the corset pulling her waist tight, holding her breasts up deliciously high for him. I imagined her on her knees between his legs, lavishing passion onto his big cock with her mouth before climbing onto his lap and slowly slipping him inside her.

Or maybe he'd take control of his masked vixen, and bend her over the arm of the couch, grip the stringed back of the corset tight, and fuck her hard from behind.

The possibilities were sending my mind in a million different directions. The mental walls between the step mother I knew and the sex goddess I saw on video began to break down even further when I took a closer look at the mask and corset.

I saw it on the mask first: a dry, translucent streak on the left side, just outside of the eyehole. I felt a tingle run up my back. I looked down at the corset--streaks and splotches of the same dried translucence covered the front of it, localized on the cups of the bra.

I knew at once what this meant.

I didn't know how they got there, or in what position, but these soiled garments told me one thing: that whatever activities the two lovers got up to last night, they ended with Brian spurting his cum all over my step mother's body, and probably her face as well, based on the mask. I wondered if he had been fucking her and pulled out just in time to cover her with his nut, or if maybe she was on her knees, head back, mouth open, waiting to take all of his sticky reward.

My body was overheating, and my cock was hard in my pants. Luckily the sound of laughter shook me out of the trance I was in. It was coming from behind the closed door of Kelly's bedroom. They must still be in there. I wondered if they had been fucking when I got home.

I absolutely did not want to deal with what would happen if Kelly came out of her room to find her step son gawking at her cum-covered lingerie, so I quietly went into my room, put on some fresh clothes, and discreetly left to make my way over to Sarah's.

****

"They clearly didn't know what time you were coming home, huh?" Sarah said, pouring herself a glass of water. She had just gotten back from a run, and her skin was delightfully flushed. I did my best not to stare at her amazing body poured into stretchy workout gear.

"Guess not. I'm kinda surprised they just left their clothes lying all around, especially the lingerie."

"Well...good sex makes you do crazy things sometimes," she said with a chuckle into her next big sip.

"Ain't that the truth."

"I found my mom's sex toy once," Sarah began while giving her shoulders a long stretch.

"Like in a drawer or something?"

"No," she chuckled, "right here drying, actually" she said, pointing to the counter next to the sink. "I guess she just totally spaced and forgot to put it away."

"Oh wow--how'd that go?"

"I just played it off like I hadn't seen it, and the next time I went in there it was gone, but her face was SUPER red."

"That's hilarious."

"Yeah, it was pretty funny."

"Was it like a vibrator?" I said, probably prying too much.

"No, no fancy parts, just...a dick. One that was...kinda huge." She said with another chuckle.

"Damn," I said, my eyebrows going up, "go mom!"

"Yeah I was actually a little jealous," she said, followed by a nervous silence, "so the next time I had the house to myself for a weekend I might have..."

"You did NOT," I said, laughing. All she did was give an embarrassed smile and nod

"I was curious, what can I say!" We were both laughing hysterically now, though I was also feeling my cock twitch at the notion of Sarah, my longest standing crush, fucking herself with her mom's huge dildo.

"And?" I said, still laughing, curious myself.

"BUDDY," was all she said, putting her hand to the sky in praise.

We both burst out in laughter again at her confession.

"I can top that," I said, not even thinking.

"Give it to me," she responded excitedly.

"Well it's not me, it's actually my step-sister."

"Ooh interesting--let's hear it!"

"She..." I paused, second guessing what I was about to say, but unable to resist the sparkle of anticipation in Sarah's beautiful eyes. "...lost her virginity to her mom's boyfriend."

Beautiful eyes almost bugged out of her head. "Whoa, WHAT?"

"It's true."

"How...when...what..." Sarah was flummoxed.

"Before you start thinking anything, it was before he even met Kelly," I reassured her, "Alex met him at college at the bar he was working at, totally randomly, and went home with him and..."

"Got fucked by her mom's boyfriend." Sarah said again, matter of factly.

"He wasn't--they weren't--" I tried to wrangle the narrative, but gave up. "In so many words, yes," I finally conceded with a chuckle.

"Damn, dude, you're right--you win!" We laughed again, and then it faded down into a slightly awkward silence, until she finally said "Hey come with me--I'm gonna go take a shower, then we can talk about tomorrow, ok? We can do it in my room--we won't have to answer any questions if my mom comes home that way."

"I, uh..." I was suddenly lost for words. Sarah's bedroom. A space I had practically scanned every visible inch of while peeping on her through my bathroom window. A space that had been a dream, but was about to become very real. "Yeah, sure, that works."

****

Sitting on the edge of Sarah's bed, I could hardly believe where I was. I had fantasized about this moment a million times, albeit definitely not like this. It was interesting to see the rest of the space, outside the small rectangle I'd seen through the window. It seemed like the normal bedroom of a normal young woman--posters on the wall, tv at the foot of the bed, desk, piles of clothes strewn about--definitely not the sex chamber of the girl of my dreams. But then again this girl was no longer in my dreams. She was real. This was Sarah. This was my friend.

"So what's the plan?" She said, strolling back in wearing a loose t-shirt, short gym shorts, and a towel around her head. Her nipples pushed faintly through the fabric of the t-shirt--it was clear she wasn't wearing a bra.

"Well, I don't want to do it at my house," I said, trying to remain focused, despite my cock suddenly tightening my pants.

"That's no problem, let's do it here--Mom leaves tonight, and then I'll have the house to myself for the next two days." Sarah worked the towel through her wet hair, her tits jiggling deliciously beneath the jersey fabric with each shake.

"Perfect. That'll be great." I said, trying not to stare.

"So like...what are we going to say to her?"

"Well," I began, realizing for the first time that I don't think I had ever considered it yet, "we definitely don't want to sound like we're shaming her for anything, but I think I speak for both of us in saying I'm pretty interested in exactly how and why this all started."

"Yeah, I definitely would like to know that," she said, finishing off her hair. She walked to her hamper, dumping the wet towel inside, and paused in thought. She wasn't doing anything special, but at that moment she looked like a Greek statue. "Tim," she said, breaking the thoughtful silence, "what exactly do you want out of this?"

"Huh? What do you mean?"

"Like, what do you want from her? Why are we doing this?"

"You don't want know what's going on with her?" I said, trying not to sound defensive.

"No, of course I do, but...that can't be it, can it?"

"What are you trying to say?"

Sarah moved over to the bed, sitting next to me. "What I'm trying to say is..." She paused, long enough for me to cut her off.

"I just need her to know that I care about her. And that I always will. No matter what."

Sarah smiled, and put her hand on mine. I returned the smile, but quickly popped up off the bed, face flushed with a heat of unknown origin. "I, uh, need to use the bathroom," I said, kind of scattered.

"Down the hall to the left," she responded.

****

It felt good to move around. After relieving myself, I stayed a moment in the bathroom, rubbing some cold water on my neck, thinking about the question Sarah asked. What DID I want from tomorrow? Was I expecting Tara and I to admit our love for each other and ride off into the sunset? Did I expect us to tear each other's clothes off and fuck right there? And what of Sarah? Was this going to be awkward with the three of us there, and not cathartic at all? Would Tara feel like we were ganging up on her? Would ALL THREE of us tear each other's clothes off and fuck right there on the floor? Is that what Tara and Sarah wanted? Is that what I wanted?

I loved her. I was sure of that. I just didn't know what that love really was. What it really meant, or looked like. I'd know when she was there though--I'd know when her gorgeous face was right in front of me.

I had no answers, and slowly made my way back toward Sarah's room no more enlightened. I glanced at the pictures on the wall, chuckling to myself at the funny faces and childhood hijinks captured there.

"These pictures are hilarious, Sarah," I called out.

No response.

"Sarah?" I said, with no response again. I moved back to Sarah's bedroom and stopped in the doorway. Sarah was sitting on her bed where I left her, but her focus was trained across the room.

More specifically, her focus was trained out the window.

"Hey, what's--" I began, and suddenly her head whipped over to me like she was broken out of a trance.

"I uh..." she started but couldn't find the words. Her cheeks flushed immediately red.

I crossed the room to where she was and turned to look at what had transfixed her. Now it was my turn to flush red. The tables had turned on my house-to-house peeping, and now I was inside Sarah's bedroom looking over into my own bathroom window.

"Is that, uh..." Sarah said, again not able to finish the words."

"Yeah," I practically whispered, sitting down on the bed next to her, "that's Kelly and Brian."

Kelly gripped the porcelain of the sink tightly, a look of ecstatic joy on her face. She shot out an arm to steady herself on the wall. My step mother's tits shook deliciously, rhythmically, as her lover Brian sent his cock deep into her, over and over from behind.

Brian had a strong grip on Kelly's hips, and the two gasped and groaned silently as he fed her body his cock. His thrusts weren't overly fast, but they were intense--determined and driving--and it was clear from the faraway-yet-focused looks on both their faces that they were deep into their pleasure.

Kelly suddenly spasmed and shook, the smile on her face replaced only for a moment with the unmistakable concentrated grimace of orgasm. Brian grasped at her, holding tight, shepherding her through her euphoria. Her breaths were deep and labored. Reaching around, his hands kneaded and massaged her breasts. Brian tucked his head deep into her neck, whispering something into her ear.

The grimace lifted and the smile returned. She nodded.

Brian backed off, slipping out of her. Sarah and I got our first look at his cock, standing hard, straining, and glistening with my step mother's cum.

I heard Sarah gasp slightly.

It was my turn to gasp, internally at least, as Kelly, smiling and excited, dropped to her knees in front of Brian. Grasping him by the root, she leaned in quickly and took him into her mouth. Her head bobbed deep and quick, sucking his hard cock, and sending him into overdrive. Now it was Brian's turn to breathe heavy and labored. His eyes closed tight. Kelly brought her other hand up and slipped it under his balls, massaging and rubbing rhythmically in time with her milking, sucking mouth.

This seemed to be all Brian could take. One hand shot out, gripping the wall for stability. HIs mouth hung wide open. HIs body tensed. His other hand cupped the back of Kelly's head gently, and he mouthed two words that even from this distance were unmistakable: "I'm cumming."

Kelly never missed a stroke, and there in the bedroom of my longest crush, I watched Brian spasm, throb, and fill my step mother's mouth with hot cum. Cum she swallowed down easily.

Even after Brian finished, Kelly's sucking continued, but it was slower, gentler, more therapeutic. She wasn't trying to make him cum anymore, I think she was doing it just because she liked sucking his cock. Because she liked HIM.

My step mother slipped Brian's spent, swollen member from her mouth and gave the tip a nice kiss. Her big smile returned, met with an identical one from Brian as he helped her to her feet. The two embraced. They kissed, deeply and sweetly. Kelly leaned over and turned the water on in the shower.

"Jesus Christ, that was hot," Sarah said, the first sound besides increasingly deep and labored breaths to come from either of us since we started watching. My iron-hard cock did not disagree, but I was still a little disoriented as to what just happened. "I get why you did this all the time...it's hard to look away." suddenly a hand went to her flushed, red face and she turned toward me, all at once becoming aware of what we were doing. She got up and rushed to the window, quickly closing the blinds. "Tim, I'm sorry, we shouldn't have--it was just so hard not to--"

"No, I get it, trust me," I said, shifting, trying to hide my intense erection. I thought back to the videos I had seen of Kelly, with Sandra and Don, with the mysterious Kenny and John, and realized there was something different this time. That smile. That smile said it all. "She really loves that guy, doesn't she?"

"Yeah, I think she might," Sarah said, a far away tone in her voice.

Silence returned. I thought about what we had just witnessed. I thought about Tara.

"How many people have you slept with?" I blurted out, my focus still far away.

"Men and women?" Sarah asked back, not even casually objecting to the intimacy of the question. I guess she and I were well past embarrassment at something like this.

"Yeah."

"Seven," she said after a short round of mental math, "four guys, three girls." I immediately wondered who the two unknown guys and one unknown girl were. "You?"

"Five." Unlike with Jane, I told Sarah the truth. This moment wasn't about being dishonest. "Do you think you ever loved any of them like that? Like REALLY loved them?" It was a question I had been asking myself ever since my encounter with Steph.

"I thought I did...I know I WANTED to," she said, a thoughtful look coming over her own face now, "but honestly I don't know. What about you?"

"I don't know either," I said, thinking. About Tara. About Steph. About...Christine. "I think I better get going," I said, finally breaking the weird mood in the room. "I'll see you tomorrow."

"Yeah, sounds good," She said with a smile.

Leaving her room I made a last minute decision to go back to the bathroom. When I came back down the hall, past Sarah's room, her door was shut, and I could have sworn I heard the faint sound of labored breath and a low buzzing coming from inside.

****

The next day I checked my phone probably twice an hour, waiting for a text from Tara with a suggestion of meeting time. I spent the whole day visibly distracted, something my step mother Kelly definitely took notice of.

"Hey Tim, you wanna give me a hand in the kitchen?" I mindlessly agreed, and started drying the dishes as she washed them.

"So are you excited for college to start?" Kelly said, handing me the next dish.

"Yeah, I think I am," I said, honestly. I had felt really weird about things lately, a feeling that something was ending, and something new starting soon.

"A lot of changes are gonna come at you really fast, Tim," she said with a softness to her voice, "and honestly, they're never going to stop, and you're never going to get used to it. But I...I just wanted you to know that I think you're gonna do great. I'm always going to be here for you when you need me, Tim. And I just want you to know that..." her voice cracked with emotion "...that even though your dad is gone...no matter what comes next I still love you very much, and I'm proud of you. He would be too."

I felt a lump form in my own throat. What a woman. "I love you too, Kelly," I managed to choke out in response, "and no matter what happens next...you'll always be my mom."

A stuttered sniffle, a smile, and a big, warm hug. I knew why we were having this conversation--it wasn't just because I was going to college, it was because she knew things were going to change in a lot of ways very soon. And when they did, I knew I'd be nothing but happy for her.