24
Running used to clear my head. These days things were spinning so fast and hard that I couldn't focus on running; no matter how hard or far I ran, I only thought about the variety of confusing situations I had found myself in. Situations that left my mind reeling, and my cock painfully hard.
It had been a confusing week.
Four nights ago my best friend Tara and I jerked each other off while watching one of my upstairs neighbors' many sextapes.
I had no idea what was going on with Tara. We had shared sexual activities before, but as far as I knew she was in a relationship with my next door neighbor Sarah, and I couldn't imagine she would cheat on her. Plus, we had almost kissed afterward, which would have sent us barreling past a barrier that was still intact despite what our numerous recent shared sexual events would otherwise suggest, but we stopped dead in our tracks when we discovered that also featured on that sextape was my step-mom Kelly.
Two nights ago I watched the rest of that tape, and drained my balls while watching my step mom get double penetrated by her best friend's husband and some mystery man named John.
I had found the whole thing highly erotic, but strangely it didn't make me view my step mother in any troubling oedipal light. It actually made me feel closer to her, to understand her a bit better. I had no idea why.
Then last night I met my boss after closing time for "training," which was not a lie, except the training I received was as her submissive sex slave. She bossed me around, forced me to eat her pussy, and didn't let me cum. It was torture...but I think I loved it.
And now here, on Saturday, I was only twelve hours or so away from fulfilling my part of a deal with my friend's girlfriend, Kerri, to clandestinely watch them fuck via webcam so Kerri could get horny enough to cum. Not only that, but then I am supposed to send her a video of me cumming while watching them, and in return she will send me a picture of herself wearing a semen facial.
And that's not even to mention my Christly friend with benefits Christine, the pastor's daughter who I may or may not be developing feelings for outside of the way her hands and mouth make me feel when she milks my cum into her mouth or onto her face.
As an 18 year old, red-blooded male, I should have been ecstatic, but to be honest I was starting to forget which way was up.
Rounding the corner coming back up to my house I spotted my next door neighbor Sarah stretching and preparing for a run of her own. A pale-skinned, redheaded bombshell, she was Tara's girlfriend...and also my longest standing crush.
More recently, however, she had been a font of wisdom regarding my troubled love life, so the opportunity to pick her brain about some of my current problems seemed like a gift. A gift wrapped in tight athletic wear that showed off her amazing figure.
Tara was a lucky girl.
I was also lucky, as my bathroom window looked directly into her bedroom, which, until very recently, had no curtains to speak of. This was a voyeuristic boon for my young, hormonal self, and provided me with full, unencumbered views of her gorgeous, naked form.
My mind instantly jumped back to Tara and I masturbating together, watching Sarah get fucked by her then-boyfriend. It was the first time I had ever seen Tara cum, and it was still the hottest thing I'd ever witnessed.
I knew it was wrong to spy, but I couldn't help it. I was being driven by something other than common sense.
As I drew closer, I waited for Sarah to turn to see me, at which point I waved and smiled. Sarah was the nicest person I knew, and was always quick with a big, beaming smile, which is why it was very surprising when she took one look at me, scowled, and began her run off in the other direction.
I stopped, and immediately felt a knot start to form in my stomach. Had Tara told her what happened the other night?
I stumbled into my house, a new anxiety-inducing problem stacked on top of everything else, only to find my step mother Kelly and her boyfriend Brian in the middle of breakfast. Brian had begun staying over, yet another life change I had to get used to.
I made small talk, but quickly got a glass of water and made my way upstairs to shower, but not before catching a hand slide up Kelly's leg after a giggle shared between them. I began to think I was going to be seeing more of Brian in the mornings.
Thinking about the scowl I got from Sarah, I peered out the bathroom window as I got ready to shower. Her new curtains were still drawn tight.
My mind was still all over the place as I ran through my hired chores up in Sandy and Don's unit, and I came back to the public display of affection I saw downstairs. I was happy for Brian and Kelly, but having a new man in the house was still a feeling that required getting used to.
Especially one who was being so forward with my step-mother.
For some reason, maybe out of some weird subconscious feeling of being pushed away, after I finished my tasks I made my way back to the bin of homemade sex dvds, grabbed a few, and headed back to the tv room.
I popped the first one in and scrubbed through a few videos of Sandy in all sorts of eroticaly compromising situations (including one involving a French maid outfit that I wanted to revisit later), but I was looking for something else. This time I was actively looking for a video with Kelly in it.
I found one on the disc labeled "KENNY."
This one opened in a hot tub. The joyous, giggling faces of Sandy and Kelly, drinks in hand, each clad in a flattering bikini top, laughed and joked with the man behind the camera. I recognized the voice of the camera man as that of Sandy's husband Don, who joked and laughed along with his two beautiful companions. They were discussing the arrival of the titular Kenny, and the fun he would add to their trip.
They laughed, they joked, they drank, and then soon enough Sandy waded over to Don and he hoisted himself onto the lip of the tub. Both ladies squealed with laughter as he revealed he was already nude, hard, and ready to play. Sandy joined him, undoing her miniscule top and letting loose her impressive breasts, but Kelly (or "Kel" as she was known in these videos) didn't. She sat back and watched in rapt amusement as her best friend gave a few short priming strokes to her husband's cock, and then deftly took him into her mouth.
Don gave his wife's ministrations plenty of screen time, but the camera kept finding its way back to Kel. He'd ask her dirty questions about what she was watching, and Kel would respond with few words, or sometimes not at all, but always a sultry smile. Sure it was hot that Sandy was sucking his dick, but the real eroticism came from watching Kel get hotter and hotter as she took it all in. He never asked her to join them--he didn't need to--he knew she would, once the heat inside her reached a breaking point.
After Kel commented on the amazing view, Don quipped that she should add to it, and with a smile and a gulp of her drink, Kel reached up and undid her top, freeing her beautiful, full breasts. But still all she did was watch. Only then did I notice she only used one hand to loosen her top--her other hand was plunged beneath the water, clearly touching herself as she watched the erotic display before her.
Then, a shudder, a shake, an involuntary closing of her eyes and gasping for air--she was cumming.
Now a deep breath, a smile, a finishing of her drink, and slowly Kel waded over to join her friend at Don's cock. She and Sandy kissed, and began trading his hard, slick member back and forth between their mouths.
Kel was so loving and attentive when she sucked him; she knew how to make him gasp and throb in ways that made it clear she had done this many times before.
There was something so intimate about watching the three of them together. This wasn't just some weekend fuck tape, this was three people who deeply loved each other having fun pleasing each other.
It made me think of Tara; is this what was on the horizon for us? Love, connection, and passion on a level wholly different than with anyone else? And what if it wasn't? What if crossing that line sent our whole relationship into a tailspin?
Don groaned as the girls egged him on, their faces pressed together just above his cock as they stroked him, and they both cheered and laughed as the ropes of cum began to ping pong across their jubilant faces and over their knuckles--real joy expressed at Don's orgasm. These three were something else.
I was hard as a rock the whole time, but I wasn't stroking myself. I was just watching. There was something almost wholesome about this lewd act they were performing, and I was enthralled.
Kel took Don's cock in her mouth one more time, sucking long and hard before passing it back to Sandy to finish the clean up. Then with a single finger and a satisfied smile she directed the stray streaks of cum on her face into her mouth, sucking the finger clean.
My cock twitched hard.
The next video started up and had an altogether different feel. Empty bedroom, static camera pointed directly at the bed.
There was some low, inaudible dialogue, and then Kel strode into frame wearing a sheer, purple robe that stopped just past her hip...and nothing else. One hand trailed behind her, and it became quickly evident she was not alone. Her fingers were locked into those of a mystery man, one whose shirt was already off, but still had on his jeans.