Diary of a Horny Student Ch. 30

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Kerri's birthday party brings a number of surprises for Tim.
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Part 30 of the 33 part series

Updated 12/29/2023
Created 04/01/2022
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30

"Saturday night, 8 pm--be there!" Kerri's email said. This wasn't one from Just4theWatcherxoxo, the secret account she used to send me adulterous hook up messages, this was from her every day account. It was an invitation to the 19th birthday party she was throwing herself at her house, and I was one of about fifty who received it.

I hadn't seen her since our tryst in her garage, and I was conflicted about what spending more time with her might mean.

Our sex was electric, but it was starting to take its toll on me mentally. The last time we were together wasn't all that unique--it included me slamming my cock into Kerri's pussy while she was bent over the hood of her father's expensive car which, aside from the inclusion of the car, was pretty much par for the course with us--but while she was taking my dick deep inside her, my friend, Mike, Kerri's boyfriend, showed up. There I was, fucking my friend's girlfriend while he waited outside, totally unaware of what we were doing, or the fact that I could see him while we were doing it.

Suddenly there was a real face to the betrayal.

Add on top of that the fact that after I came deep inside her, Kerri left quickly to head off with Mike, where she had apparently gotten a load from him inside her on top of mine. I knew as much because of the picture of her well-fucked pussy, creamy and white, she sent me.

It turned her on. It made me Jealous.

It was a polarizing moment for both of us. It seemed to me that Kerri was starting to become less interested in sex with me, and more interested in the secrecy and danger of it all, whereas for me those same factors were too much--what we were doing was wrong. As far as I was concerned our affair had run its course, lest things get far more complicated than either of us wanted.

No one had gotten hurt yet, and I wanted to keep it that way, so I ended it. I just...hadn't gotten around to telling Kerri that.

"You're coming to my party, right?" the next email read, this time from Just4theWatcherxoxo.

I knew I was going to, it would be too weird if I didn't, but part of me wanted to bail. I'd gained some newfound confidence recently, but confidence or not, I wasn't sure if I'd be able to share space with Mike, knowing what I had been doing with his girlfriend. But it would definitely be suspicious if I didn't show.

I clicked on the grouping of email names in Kerri's party announcement. I scanned the invited, not sure what I was looking for, until one name stopped me--Tara's.

Tara and I hadn't seen much of each other lately, not since our blow up at lunch after that night watching Sandy and Don's videos. The fact that we had gotten so close, crossed the line, sent us careening away from each other at hyperspeed. She and I had experienced something special, and if anything else was going to happen between us it needed to be honest. As it stood at that moment, she had just come off of a bad break up, and I knew the timing wasn't right.

But ever since then I'd wondered if I had in fact blown the only chance we'd ever have.

I missed her. I missed my best friend.

My eyes then caught another name in the list: AmandsB121.

I felt the hair stand up on my arms--there was no doubt this was Mandy, Kerri's cute, bubbly cousin, the gymnast with the fake breasts, who I had met at the party at The Spot. We had had a great time talking, and I was thrilled to know we were headed to the same college in the fall, but our time was unceremoniously cut short by Steph, stealing me away in one of her meaner expressions of dominance.

I liked Mandy. I wanted to get to know her more.

Between the chance to reconcile with Tara and the chance to spend more time with Mandy, suddenly this party was starting to get more attractive. Surely those two alone would be enough to keep my mind off Kerri, and more specifically off Mike.

"Of course!" I finally wrote back.

****

Work the following week was slow, and it gave me time to think.

Up until now I was being a pussy, too afraid to pull the plug with Kerri for real, resorting to avoidance and ghosting as my tactic of choice. Despite all the sex I was having, I had no real confidence regarding women, at least not until the night I spent with my boss Letty.

Letty had spent the summer inflicting sweet torture on me, demanding I stay after work, where she turned me into her literal sex slave, taking all agency away and demanding I serve nothing but her sexual pleasure. I was happy to do it, too.

The final time we were together, however, the last time I had been in this building. the tables turned. Literally. She handed control back to me, and I used her body for nothing but my own enjoyment. I treated her like a common slut and made her scream. She gave me power, and along with it came a strange sense of confidence I'd never felt before, confidence I was determined to hang on to from here on out. I just didn't know how to implement it yet.

Being at work, I also didn't know how I managed to keep my mind on anything other than that last night with Letty. It helped that she hadn't been in at all that week, though, which was very unlike her. Even still, there seemed to be a sense of closure with her that kept my thoughts on what was to come that weekend, and not where I had cum last weekend.

Still there were some unanswered questions about that night, about the whole summer, really, and as I sat in the breakroom nursing a soda, the biggest question of them all sauntered in for her break: Gina.

This whole week, Gina acted nothing but normal around me, almost as though she HADN'T been there with Letty and I last weekend, hadn't forced our boss to eat her out while I watched, hadn't sucked my cock, hadn't been painted with my cum as our boss jerked me off into her face, using my dick as though it was her own.

Like I said, many questions.

She sat down across from me and casually started flipping through her phone as she sipped her soda.

I looked around. There was one other employee in the breakroom. I couldn't start asking real questions with someone else there, that much I knew for sure.

"So...no Letty this week, huh?" I asked casually.

"Nah, she's on her end of summer vacation." Gina said casually back.

"So that's something she does pretty regularly?"

"Yeah."

"I can understand that," I began, continuing in weak code as not to tip off the other person in the room with us, "especially after how intense the end of last week was."

Gina's eyes flicked up to mine. She put down her phone.

"Yeah," she said, turning her full attention to me, "she likes to create some space for herself...after a week like that."

"So she's had weeks like that before?"

"She has one every year."

"There seemed to be a pretty big lead up, over the summer...is it always the same?"

"Yes. She always picks someone new to assist her though."

"You seemed to be pretty used to the pressure--how many times has she picked you?"

"I've been helping her out pretty regularly ever since I first started working here. Letty found out quick that she and I work pretty well together."

"I'll say." I paused, thinking about how long Letty and Gina had been "working together." Then about how long Letty had been running this game. I wondered with how many different lovers. "Does she...does take this week of because she knows that the 'pressure' will be gone soon? So she doesn't have to deal with it anymore?"

"Bingo," Gina said with a slight sadness.

I felt a little hurt. Gina could tell.

"Why does she pick them?"

"To make them better workers."

"I see."

"You should know...not everyone she picks gets put in charge the way you were. You have to earn it. You handled yourself really well, Tim, I will say," She said with a smirk, "maybe the best I've ever seen. You're pretty...talented."

"Thanks," I said, meeting her gaze, feeling some of that newfound confidence making its presence known. She was leaving me an opening. An opportunity to explore it. "You know...I know we didn't get to do much, but...I got the sense you and I would work pretty well together too."

"Oh yeah?"

"Yeah..." I pushed further. "Tell me, do you still need assistance with that thing we talked about last week?"

Gina's smile got bigger as we both remembered our encounter days before our session with Letty. Gina had asked if I'd help her fulfill a promise to the fans who subscribed to her online cam show--the promise of sucking a cock on camera and taking a big thick load.

"Actually no," she said, pressing my buttons back, "I got someone else to help with that."

"That's too bad." My mind raced, and my pants tightened as I wondered who the lucky guy was.

"It is," she said, shifting a bit in her chair, "he wasn't anywhere near as suited for the job as you were." Her tongue quickly moistened her lips and she bounced an eyebrow at me.

"You're on inventory in the stockroom today, right?" I said, giving my own lips a quick once over

"I am."

"That's pretty solitary work."

"It is."

"How about I give you some help right now...help you get off...early?"

Gina's eyebrows raised at my choice of words, and at my forwardness. Our eyes remained locked, each of us testing the resolve of the other.

Gina smiled and bit her lip seductively.

I barely remember leaving the break room. What I do remember is Gina's hands gripping the stock room shelves tightly, little moans and coos escaping from her excitedly. I remember her wet, velvety pussy wrapped around my cock, and the slap of my hips against her beautiful ass as I fucked her from behind.

I remember that we probably should have been trying to keep it down, but honestly neither of us cared. We were in a secluded corner of the stock room, and weren't expecting any company.

I remember Gina's shirt pushed up over her voluptuous tits, and holding on to them for dear life as I rocked into her. Despite splashing my cum on them that previous night I hadn't gotten to touch them, so I made sure to take them in as much as I could. They were exquisite.

I remember Gina beginging to chant in pleasure, her head hung down between her outstretched arms, "I'm gonna cum...fuck, I'm gonna CUM!"

I remember kneading her breasts tightly, fucking her hard. I remember Gina exploding.

I remember her shivering, shaking, and then starting to giggle and laugh almost uncontrollably.

I remember her looking back over her shoulder at me seductively as I started to lose control. I remember her request:

"Cum in my mouth."

I remember slipping out of her, Gina quickly dropping to her knees in front of me. I remember feeding my riotous cock into her mouth, barely missing a stroke, and the feeling of her pillowy lips sliding over my shaft. The feeling of her hands steadying my erection and cupping my balls.

I remember bracing myself--one arm on the stock room shelves, one hand cupped around the back of Gina's coaxing, milking head. I remember grunting. Sighing. I remember filling her mouth with my cum.

I remember her encouraging moans; the pulse of her throat as she swallowed me down. I remember the kiss we shared after we put ourselves back together, her hand on my cheek. A smile.

I remember wanting more, that summer. I remember never getting it.

To this day every now and then when the memories come back I scour the internet, searching for Gina's cam feed, desperate for more of her. I've never found it.

****

Saturday morning rolled around and the house was as empty as it was the night before when I got home from work. Alex was gone, Kelly was gone. The previous night as I lay in bed I heard voices and laughter coming from Sandy and Don's unit upstairs, and I couldn't help but wonder if Kelly had been up there with Brian. If they were STILL up there.

I hadn't seen much of Alex lately. She'd been spending a lot of nights out, and any time I saw her leave she was definitely dressing to impress. I didn't know what she was up to...who she was up to...but she seemed to be enjoying her summer.

I hoped it was less complicated than mine had been.

I decided to go for a run.

I went on my usual route, and was thankfully occupied by the exertion, and not by the near constant confusion I seemed to be in. That all changed when I reached my turn around point, and was presented with a plump, athletic ass clad in tight workout gear, raised high into the air, its owner in mid stretch.

When she arched back up, I saw her hair first--her fire-red hair. I knew immediately it was Sarah.

She turned around to greet me as she heard my foot falls. Even though I knew I wasn't her favorite person in the world ever since she had heard the truth about my history of voyeurism involving her, I couldn't help but be taken by the split of her cleavage and the jiggle of her full breasts beneath her tight sports bra.

"Hey, Sarah," I said, "sorry to bother you, I didn't think you'd be here. I'll be on my way." I waved slightly, avoiding eye contact, and started to turn around.

"No, Tim, wait," I heard her call out. I stopped immediately.

I turned to face her, confused. She was already making her way toward me. Goddamn that jiggle.

"I uh, I have to tell you," she began almost nervously, "I've been running this route regularly on purpose. I've been wanting to talk to you, and I figured this was the only way I'd really be able to catch you."

"Oh?" I said, ready for a potential slap in the face that she'd never gotten close enough to deliver.

"Yeah, I..." I waited with bated breath as she crossed her arms and fidgetted. Woo boy, those breasts. "I'm sure Tara probably told you everything, right? That she knows everything, and that I know everything?"

"Yeah," I said timidly again.

"Well," she paused again, "I want you to know that what you did was wrong. It's a very intimate invasion of privacy and you shouldn't have done it."

"I know," I said, hanging my head. "I'm so sorry, Sarah."

"I know you are," she said, a pause coming again before she continued, "but I'm sorry too."

"What? Why?" I said, confused once more.

"Because I knew you were doing it. I knew you were watching me through my window."

"You WHAT?" I almost shouted. "You did?"

"Yes," she started, putting a hand to her temple as the truth started coming out, "It wasn't an accident that I didn't have blinds on my window, or that I was getting naked in front of it. I knew you could see right into my bedroom, and I could tell by the way your bathroom blinds shifted once or twice that you were probably watching me change."

"I...wow." was all I could muster.

"The truth is though," she continued," I wasn't doing it for you."

"Then who were..." I stopped. I thought. I knew. "...Steph."

Sarah nodded. "Your bathroom looks right into my bedroom...but so does hers. She and I dated for a while...if you could call what we were doing dating..."

"That sounds familiar" I said almost under my breath.

"...and when we broke up, I just...I couldn't get her out of my mind. We stayed friends...but she really has a way of sticking with you."

All I could do was nod.

"So after it was over, I started changing in front of my open window, hoping she'd see. Hoping she'd...want me again."

"What about your boyfriend?" I thought back to the first time Tara and I had crossed a line, when we jerked off next to each other while we watched Sarah get fucked by her then-boyfriend.

"He sucked," she chuckled. "He was a pretty good lay, but a terrible person. It doesn't make me proud to admit I was using him, mostly to try and make Steph jealous. I wanted her to see me--to see us--and to get jealous."

"Did it work?" I asked, tactlessly.

"I wasn't the one cumming in her mouth at prom, now was i?"

"No," I eeked out, feeling my cheeks blush, "I guess not."

"Steph has a certain power over people who...fall for her. It's the only reason I went along with her plan for me to seduce Tara." She ran her hand through her sweaty hair. "You have to believe me when I say I never wanted to hurt her. I never intended to..."

Her words drifted off and she looked into the middle distance. I could tell she had real feelings for Tara.

"I'm sorry," I said, "this all got way out of hand. I know what it's like to be under Steph's spell."

"Yeah," she said with a chuckle, "I guess we have that in common, don't we?"

"But tell me," I inquired, "if you knew I was watching...why did you get so angry?"

"Tim," She said with a wry smile and a shake of her head, "there's a huge difference between watching me get dressed and watching me get fucked."

"Good point." I chuckled back.

"Race you home?"

She took off down the path. My cock twitched. I took off after her.

Sarah hadn't been on my mind for quite a while...but as I trailed behind that perfect butt of hers, and watched that red ponytail bob and weave, she definitely was back.

We pulled up in front of our houses, gassed and heaving. I couldn't help but steal glances at her pulsating cleavage glistening with sweat.

"You know, we actually are kind of almost even." she said through huffing breaths.

"What?" I said, once again completely confused.

"I was helping Steph move out, and I caught her..." her fingers interlaced as a slight embarrassment came through her words "...watching a video you two made."

There was only one video--the video I had on my phone. The video she asked me to send her. The video of our last night together.

"Oh...my."

"Yeeeeeeah," she drew out through playfully clenched teeth.

"Yikes." the thought of Sarah, my biggest crush, seeing that video washed over me. There was a cornucopia of conflicting feelings. "How much did you see?"

"Enough." Another cute chuckle.

"Yikes."

"I wouldn't worry though, Tim," she said, taking a couple steps ahead and turning back to look at me, "You don't have anything to be embarrassed about. Trust me." A deep, sultry smile pulled at her lips. She adjusted the strap of her sports bra, giving those glorious globes a nice jiggle. It was a compliment that even then, after all that I had experienced, sent my heart aflutter.

But it was the next thing she said that shook me to my core:

"Tara's a lucky girl."

"Huh?" I choked out.

"You guys are together now, right?"

I shook my head.

"No, we're actually...we haven't spoken in a little bit."

"Seriously?" Now it was her turn to be confused. "I could have sworn I've seen her coming and going from your house a bunch of times recently. Like...coming at night and leaving in the morning kind of coming and going."

"I have no idea what you're talking about." I wasn't lying. I tried to shrug it off, but something cold inside me sank into my stomach. There were things I needed to know.

"Huh..." Sarah said with a shrug, "maybe it wasn't her. Maybe it was...your step sister?"

"Yeah, maybe."

Neither of us believed it.

We said our goodbyes, made plans to run together again the following morning, and went our separate ways.

After my shower I paused and glanced out the window toward Sarah's room. The curtains were still up...but they weren't closed all the way.

I felt a grin tug at my lips and I went about my day. I was determined to think with my head, not my cock.

****

I pulled up to Kerri's house at 830 to find the party already in full swing. It wasn't a huge gathering, but it was enough to make the house feel rowdy. There was booze, there was music, and as I said my hellos and scanned the crowd, suddenly, across the room, there was Tara. I had questions for her, but at that moment all I could do was drink her in.

Knee-high boots and bare, pale thighs extended down from a thin dress that almost seemed like some sort of nightie or teddy, bound around her waist by a big belt. Her perfect tits were held up and pushed together in perfect cleavage fully on display, a series of necklaces dangling down to deliciously tease the tops of her globes. In addition, strapped around her long, pale neck, was a choker, a small jewel in its center. Black lipstick, deep eye make up, immaculately-spiked hair, this girl was a hot gothy knockout.