Diary of a Horny Student Ch. 22

22

"No, nope, nuh-uh, NO WAY," I said, pacing back and forth across the living room. I was in shock.

My upstairs neighbors and long time family friends Sandy and Don had asked me to house sit for them. I had planned on a pretty quiet night until my best friend Tara had joined me. This led to us accidentally discovering a treasure trove of Sandy and Don's personal, explicit, home sex videos. This wasn't entirely surprising, given what I knew about Sandy and Don's rather adventurous sex life, and the first half of the video we chose to explore lived up to that expectation as it featured Sandy both sucking and cumming on a cock that didn't belong to her husband. It was the second half, however, that caught me so off guard; the part of the video we currently had paused; the part where Sandy took the camera into the bedroom and revealed her best friend bouncing enthusiastically on Don's dick.

Her best friend who also just so happened to be my step mother Kelly.

"No, I don't...how is this possible? How could she..." I couldn't form a coherent thought. Kelly hadn't been on even a single date since my father died, and was a devout, church-going Christian, to boot. I could not reconcile that the sweaty, smiling woman with Don's thick cock up inside her was Kelly. I just couldn't.

"I mean, she's still a woman," Tara said, "everybody's got needs, right?"

"This isn't NEEDS, Tara, this is...GROUP SEX!" I practically shouted.

"I don't know, Miller," she said, a lusty smile on her face, "I think it's pretty cool, actually. Girl knows what she wants and goes out and gets it."

I just stood there, aghast and livid, hands on my hips, shaking my head. Tara began to giggle.

"This isn't funny!" I croaked, but all she did was laugh harder.

"Trust me," she said, gesturing to my whole situation, "THIS is very funny!"

The fog momentarily lifted from my brain and I was able to take stock of how ridiculous I looked: I was standing there, fuming, in only socks and a jizz-splattered t-shirt, my soft, spent dick flapping in the wind with every shift or angry outburst I let out. I couldn't help but join Tara's laughter.

And then there was Tara.

Tara was just as indisposed as I was: hard nipples pressing through her t-shirt, she was bottomless, legs crossed, hiding her pussy from sight. I looked ridiculous, but Tara...she looked hot as hell.

It was then that I remembered what had just happened. While watching the first half of the video, my best friend and I had crossed a line. We had shared sexual situations before, even masturbated in front of each other, but there was never any touching. Tonight was different. Tonight she stroked my cock and I fingered her pussy until we both had explosive orgasms.

It was all so hot, and so sudden, that I hadn't even considered what this meant for Tara's relationship with Sarah. She had effectively just cheated on her, with me, and despite how amazing the experience had been, to feel her on my fingers, and to feel her fingers on me, the idea that I was part of even more deception just made me feel awful.

"This is nuts...this is all so nuts" I said, in reference to everything. I needed to remove myself from the situation. Fast. "I'm gonna...I'm gonna go clean up. Maybe take a shower."

"You don't wanna know what happens next?" Tara said in a syrupy tone, her thick, pale thighs sliding along each other in a suggestive way.

"I...just can't deal with this right now" I said, playing dumb to her clear double meaning.

"You're telling me you DON'T want to see how this ends?" She said, sitting up in disbelief.

"Not right now...it's just all too much." It definitely was not a lie.

There was a moment of silence between us. We were both clearly running over events in our minds, each trying to figure out where to go next.

"Ok, sure," Tara finally said, "you go clean up."

Her tone was hard to read, and my stupid teenage brain told me it was better not to try, so I acted as though the matter was settled, and made my way toward the bathroom.

The minute I left the room, I heard voices and sounds coming from the tv. Tara was watching the rest of the video. Slipping into the bathroom, I paused just inside the doorway, held my breath, and listened. I could hear giggles, gasps, and long moans coming from multiple people. The loudest and most feminine of them I recognized as coming from my step mother Kelly. I still couldn't believe it.

I peeked my head out from the bathroom door, which had a straight line of sight to the living room. Flickering digital light cast shadows throughout the room and highlighted my best friend Tara, entranced by the visuals. Her legs were spread wide, one hand lost between them while the other caressed her own breast.

Somehow I pulled myself away and back into the bathroom. I could not wrap my mind around the events of this evening. Part of me did want to see the rest of the video. Part of me wanted to go back and fuck my best friend right there on my neighbor's couch. But right now I just wanted to eject from this entire situation. I needed this shower badly.

It was a cold one.

After my shower, I put on some clean clothes and rejoined Tara in the living room. The pants she borrowed from Steph were back on, and she was curled up watching some non-pornographic tv, a very contented glow about her person. She was satisfied. I'd be lying to say I wasn't sad I missed it.

"How was your shower?" She said casually, not looking at me.

"It was...good." I had no idea what else to say. I had no idea what I COULD say. I knew what I wanted to know, though. Despite my better judgment, despite my tantrum and my rush out of the room, my curiosity got the better of me. "...How was the rest of the video?"

Tara's gaze turned to me. She smiled a devilish smile, and rolled her eyes at me.

Tara got up with a sigh. Her thighs jiggled deliciously as she sauntered over to me. Steph's shorts clung to her ass tightly, and I could see the slight sway of her perfect breasts beneath the large t-shirt.

She stopped in front of me, taking a moment to look me over. I had no idea what she was thinking, or where this was going, but before I had time to guess, she leaned over, and gathered up her discarded work clothes.

"Oh boy, Miller...You're gonna have to see for yourself." She said with another smile, and kissed me on the forehead.

A pat on the side of the cheek followed, and then Tara made her way out of the room, toward the front door.

I was completely flabbergasted, but I got the immediate feeling as though I had fucked up. And maybe I had; my best friend and I had been extremely intimate, in a way I think we had both wanted for a long time, and my response was to panic and eject. But I mean, who could blame me? I had just discovered a sex tape featuring my step mom and three other people--it was kind of a lot. And what about Sarah? I hadn't done anything wrong, had I?

As if sensing my panic and confusion, Tara stopped at the front door and called back to me.

"Let's get lunch this weekend, huh? I think we have a lot to talk about." The low light cast on her from the kitchen threw a deep shadow below the swell of her breast.

"Yeah. Sounds good."

Tara disappeared into the shadow of the night, and I was left alone with my thoughts as the light of the tv lulled me to an exhausted sleep.

The next two days at work, my mind was on anything but my job. I made sure to miss Kelly when I went downstairs to get ready in the morning. I don't know what I would have said to her if anything; the image of her riding Don's cock was still fresh in my mind. Everything I thought I knew about her was false, and I was still processing.

I thought about the state of my own love life--between what had happened with Tara, my cum-soaked rendezvous with Christine, and whatever it was that was happening with Kerri, it was anything but normal.

Hanging out with my best friend should mean going to the movies and listening to music, not jerking each other off watching stolen homemade porno, shouldn't it?

Spending time with the pastor's daughter should mean milkshakes and fun, chaste conversation, not cumming on her face while she masturbated and told me stories about fucking her ex-boyfriend, shouldn't it?

Helping my friend's girlfriend with their relationship should mean giving advice and talking, not receiving photos of her cum-splattered body and watching them fuck so she can get off, shouldn't it?

I had conflicting feelings about all of it, but the truth was, it was not because of the acts themselves, but because I was really enjoying myself. I was having the time of my life doing these lewd, taboo things, and a part of me felt bad about that.

Lewd, taboo things like group sex with your friend and her husband. The disc was still in the player, just waiting for me to watch the rest. I had two more nights to myself in that apartment, and I wasn't sure my curiosity would leave me alone.

"Tim, could I have a moment," my boss Letty said from behind, snapping me out of my daydream. I nodded, and followed her into her office.

Office was probably too generous a term for the tight corner room she worked out of, but there was a desk and a lamp, and she made it work. It was also spotless. Perfectly neat, with every element in its exact perfect place.

"Sit down," she said, leaning slightly on her desk. It was the most relaxed I had ever seen her. I plopped down in the chair in front of her.

For the first time ever, I looked at Letty and realized how attractive she was. Behind her big glasses and buttoned up exterior was a good looking girl, and if her body was anything like her office, everything was tight, tidy, and firm.

I wondered if she ever had an orgasm.

"Tim, I think we're going to have to let you go." Letty said the words with little emotion, but they hit me like a hammer.

"What? Why? I mean, have I--" I scrambled for anything to grasp on to, but she cut me off.

"Your work just isn't getting any better, and your attention is constantly drifting. I've got two other people on your shift working extra hard to pick up your slack, and that's not fair to them, to me, or to this company."

I hung my head. I knew she was right; my mind had been on pretty much everything BUT work, and I finally hit the wall. "I'm sorry, I'm sorry, you're right. I've got...a lot going on at the moment, and I've been letting it distract me."

"I know you've got a lot on your mind," she said, softening only just, "I remember what it was like being your age." Letty was only in her mid-twenties, but I couldn't for a second imagine this woman as a hormone-fueled teen. I bet while the other teens were out partying, Letty was home tucking in bedsheets and making sure all the pencils were equally sharp. "But part of getting older is learning control, and how to handle all the things life throws at you."

"I know," I said softly, "You're right, you're right...I just...I can't lose this job. If you could give me a second chance, I could..." I trailed off, not knowing the answer.

"I've given you a lot of chances, Tim," she said, crossing her arms.

"I know, I know, but I promise, this time I'll be better. Seriously." I pleaded.

There was silence as Letty considered my groveling.

"Ok, listen," she began, taking in a deep breath, "I'm gonna give you another chance, but you need to prove to me you can do what I need you to do, ok?"

"Yes, definitely, anything!" I practically shouted.

"I know you're off tomorrow, but what I need you to do is come by after closing so we can go over some things, ok?" She looked sternly at me over the tops of her glasses.

"But it's Friday ni--" I began before being cut off

"Sacrifices have to be made, Tim. Priorities. Now are you going to take this job seriously or not?"

I deflated, defeated. "Yeah, I am. Tomorrow, after closing. Got it."

"Good," she said, moving past me to the other side of her desk, "now go finish your shift."

She didn't look at me again as I got up and slowly exited the office. I took a moment outside the doorway, and lamented the loss of my Friday night.

"That didn't sound great," I heard Gina say from beside me. I turned to see her grinning a sly, shit eating grin.

"Nope, it wasn't," I said flatly. "She was going to fire me."

"Was?" Gina purred.

"I got a second chance. I'm coming in tomorrow after closing for some sort of retraining."

"I see," Gina said, her lips pulling into a smile once again, "well good luck, Tim...I hear she's pretty...strict. I hope I see you Monday!" She winked at me and walked off. "If you're still in one piece, that is."

One piece? What was she getting at?

I couldn't worry about it right then, I had to put in actual effort for the rest of my shift. I focused on work, which was actually a nice distraction from everything else, and rounded out my time. As I was leaving I saw Gina waiting by the door again, but once again I couldn't see who she was waiting for. She had changed her pants before leaving though, and was now sporting some short shorts and fine fishnet tights.

Wherever she was going, I don't think it was home.

Back at Sandy and Don's I had dinner, a much needed shower, and plopped down on the couch to watch some tv. The same couch I had been on the night before when Tara and I had watched the video.

The video that was still in the player.

I thought about the basket we found the disc in. It was one of many. It seemed like group sex, or at least videoed sex, was a past time Sandy and Don engaged in quite frequently. I wondered who else was on the videos. I wondered how many Kelly was in. How long had she been doing it? Did she do it when dad was alive? Did he know? Did he ever...

My phone buzzed. It was an email alert.

It was from "Just4theWatcherxoxo".

My cock started to swell as I opened it.

I hadn't heard from Kerri in a few days, not since I had boldly asked her what I could do for her in return for the hot, dirty photos she had been sending me. Photos of her body splattered in her boyfriend's cum. I worried I had pushed it too far, and maybe she was backing off a bit. She was sending lewd photos to her boyfriend's friend, after all, which is generally a huge no no. She didn't seem to feel bad about it, though...and neither did I. I didn't quite know why. I felt bad about Tara cheating on Sarah, but not about Kerri and I doing...whatever it was we were doing. Maybe this was it, maybe this was her coming to her senses and breaking the whole thing off.

I tentatively opened the email.

"Hey there," it began, innocently enough, "I'm sorry I haven't been in contact in a bit. I've been thinking a lot about what you asked last time."

Here it was, I thought, this was it.

"And I think I know what I want in return."

My cock surged. I wasn't expecting that.

"I've never cum as hard as I have when you watched us fuck, and I want that again. I want you to watch us fuck."

The throb in my shorts signaled my excitement, but I had no idea how we were going to pull that off again. The last time was a right place right time situation, and would be hard to recreate.

"I know it's asking a lot, and I know it'll be hard to pull off, but I've got an idea. If you're in, message me back and I'll tell you the plan...and the catch."

I was very intrigued, but the last line made sure the hook was in deep: "Meanwhile, enjoy these pictures ;)"

There were three files attached to the email, all numbered with the file heading "Just 4 you." I felt my throat get slightly dry, and my pants get tighter.

I opened the first one: It was a full body nude, shot in an artistically clever way to keep her face out of the image. On her knees on a bed she posed seductively in front of a bright backlight that threw her whole body into shadow. It might have obscured her face, but it accented the languid curves of her body perfectly. Her thick, beautiful breasts stuck out large and perky from her chest, nipples at full attention. Her arms plunged down between her legs, pushing those gorgeous globes together slightly, presenting them to the camera, and allowing a slight glimmer of highlight to catch the tops. The swoop of her back cascaded down into the lovely swell of her ass. I thought about touching it. About squeezing it. About bending her over.

Catching my breath, I opened picture two: A mirror shot, showing off that lovely curve of her back and rear, but this time in full light, and this time with a specific purpose. It wasn't just her curves she was showing off--this time there was a bright red patch on one cheek in the vague shape of a hand print. And on top of that mark, spreading over her ass and up her back, were four, distinct, thick splatters of cum.

My hand shot right down into my pants, fished out my cock and started stroking when I saw that photo. My mind ran wild with visions of Kerri on all fours, her boyfriend Mike slapping her ass while he fucked her. I thought about the sounds and moans she must have made as he sank into her over and over, accenting his thrusts with a firm swat of her cheeks. I thought about her tight pussy milking his cock so well until finally he pulled out of her and erupted all over her body in orgasm. I was jealous.

Quickly opening the third picture, my cock flexed between my fingers: this shot was a look between her spread legs, directly at her pussy. Her lips were wide and creamy, flushed red, above them, pooling on her lower belly and pubic bone was more fresh semen. This wasn't just Kerri's pussy, it was Kerri's pussy after it had been fucked.

Once again I pictured her, this time on her back, legs bent up, Mike's cock pistoning in and out of her until he had had enough and shot his load onto her smooth belly.

I was transfixed. There was no escaping now. I immediately wrote back "I'm in." and hit send.

I cycled through the pictures again as I massaged my dick, but Kerri wrote me a reply before I could even make it all the way through.

"Yay!" It said with a smiley face next to it. "So what we're going to do is, this Saturday, at 9 pm, you're going to click this link." There was a jumbled collection of numbers and letters that were highlighted as a web address. "That's going to take you to a place where you can watch the live feed of the webcam in my bedroom."

This just got interesting.

"Once you're set up, you'll text me a thumbs up, and shortly after that you'll get a little show put on by the two of us, and hopefully knowing that you're watching us, even over the internet, will be enough to get me off. Sound good?"

It sounded suspect, but I was too charged up by hormones to make a rational decision. "Sure, let's do it," I wrote, and then remembered the other part of Kerri's first email, adding "what's the catch?"

I sent it. Maybe a minute later her reply came through: "The catch is...I want you to cum this time...and I want to see it."

This was getting VERY interesting.

"I want you to take a video of the moment you shoot off while watching us fuck."

I was not expecting this. Kerri was blasting right through all sorts of boundaries now, and I wasn't sure I wanted to go there with her.

"Just in case you need some convincing, I've attached a sample of what you'll get as a thank you."

I saw the attachment. Another numbered photo with the "Just 4 you" title. I clicked it with bated breath.

Popping up on my phone was a cropped close up of Kerri's dark, almond-shaped eyes, painted with alluring makeup, staring directly into the camera. This wasn't a particularly scandalous photo, or at least it wouldn't have been, were it not for the viscous, white streak lashing the bridge of her nose, up between her eyes, and across her forehead.

I audibly groaned. She had only minutes before sent me a close up photo of her freshly stretched pussy frosted with jizz, yet it was this tease at the prospect of seeing her cum-covered face that sent me into overdrive. All thoughts of boundaries vanished, and I clumsily wrote back the reply of "You're so fucking dirty. Let's do it."