MILFception Ch. 02

"Johnny, hey. Hold up a sec." It was my neighbor, Ms. Richards. She was parking in her driveway just as I walked by and I hadn't really expected any acknowledgement from her. I was friends with her son David all through school, and never understood why she had a progression of shittier and shittier boyfriends the entire time I had known her. She was sweet as hell, and conventionally beautiful, and should have been pulling catches by the netful. Short, but classically proportioned, with perfect legs even if they weren't long. I had always harbored a crush on her, and as far as physical beauty went, she stayed a benchmark I kept for other women for years.

When I was a teen, she had mostly been stand-offish with me and back then I tended to take it as a rejection. I was invisible to this beautiful woman, and honestly it fed into some insecurity about interacting with women in general. In hindsight, and measured on my own experiences, I get it. When you're 40, and a significantly younger person has an obvious crush on you, the normal response is to not do anything to encourage it.

In the simulation though, she called out to me as soon as she got the car door open.

She was wearing a tight, sleeveless, purple velour dress, with sheer black stockings and black pumps. One leg swung out of the car, and the dress rode up enough to expose some bare flesh at the top of her thigh highs. My mouth went dry. I would have written this off as another place the simulation was airbrushing my memory, but that really was how she dressed every day. There were times I had seen thigh highs on their bathroom floor as a teen, and I had never seen her in pants or flats once.

As soon as her car drove past me on the walk to my mom's house I knew what the simulation was doing. It found an experience I had used to fuel some insecurity and was giving me a better version of it. There was a tinge of guilt about playing along given how the better version of the situation with my girlfriend's mom went, but in the end, none of this was real. This wasn't any worse than thinking of her while masturbating, and I had already done that countless times in my life.

"Hey, Ms. Richards. What's up?"

After taking a moment to pull the hem of her dress back where it was supposed to be she walked toward me, heels clicking off the pavement. "Hey, uh. Linda, please." She smiled at me, and remembering how much my teenaged self wanted that smile, my heart melted. She pushed her shoulder length hair behind an ear and said, "I have a couple things I need moved around and can't get them myself. I'd ask David, but he's already back at college. You think you could give me a hand this week? I can pay you a little."

"Sure. I uh. I don't know what I'm working this week yet, can I check and let you know?"

"Of course. Number's the same as before. I'm home around now every day."

"Okay, I'll let you know."

"Thanks, Johnny." She turned to walk back toward the house, and I shamelessly stared at her ass while she walked away. Her stockings had seams up the back, and her pantylines and garter clips were visible under her dress.

"You're welcome, Ms.... Linda." Her first name felt weird in my mouth.

At the top of the driveway, she bent over to get her purse out of the car, her dress riding up just enough to expose the top of a stocking and the clip of a garter. She looked back over her shoulder and caught me staring but gave no reaction.

When I left the Carter's, I didn't really know what to do. The normal level of blissed out after the sex was layered in confusion and panic. I had the smallest grasp on what the simulation was doing, taking memories I was insecure about as a teen and making them, "better," but I also knew it was malfunctioning somehow and I was stuck in it. It was only supposed to be 10 minutes in the simulation, and it had already been several hours.

I had wandered in the general direction of my mom's house until I ran into Ms. Richards, taking in the details of the simulation. It was pulling the neighborhood entirely from my memory, but at the same time it got details right that I don't think I could have remembered on my own. The right cars in the right driveways, phone booths in the right places. It was a perfect recreation. And if it wasn't, I didn't remember well enough to tell.

My mother's house was dim and grey inside. Nobody was home, and probably wouldn't be. My mom took a job at a hospital in the next town over my last year in school, and it was too far to commute daily. A couple of years after I finished school I was there alone except for every other weekend. She took the job in desperation more than anything, but it worked out for us. I got to have some real-world experience before moving out, and my mom got to ease into the empty nest.

I got in the fridge and drank some orange juice from the carton while I read my work schedule. My watch said it was Sunday, January 8^th, 1992. I worked tonight in about an hour, then off tomorrow. Did the simulation really need to make me go to work? I picked up the cordless, and dialed The Richards' house from memory even though there's no way I could have remembered what it was.

As it rang I walked to my room to look for a work polo. Linda answered, sounding as if she had run for it. "Hello?"

I walked past my mother's room, and saw that the blinds were open, there was a clear view of the Richards' house from there. I approached the window instead of going to my room and said, "Hey, Linda." Sometimes when David and I talked I would stand there so we could see each other. Linda wasn't standing in a window waving like David would, but I did catch her walking through their kitchen.

"Oh, Johnny. That was fast." She appeared in the living room window, where she lingered, taking off her shoes.

"Yeah, I just had to check my schedule on the fridge." She turned to face away from me and cradling the phone against her shoulder reached behind herself with both hands, unzipping the dress. I swallowed hard and said, "I work tonight but can come help tomorrow whenever you're home." She dropped the dress to the floor and stepped out of it. Her panties were bright red with lacy trim at the waist, and on over a black garter. She wasn't wearing a bra. The massive cock the simulation had given me was back at full mast in my pants, I thought it might rip its way out.

"Oh, that should work great." Her hands grabbed at the band of her panties and pushed them down off her hips. They slid all the way down her perfect legs to the floor leaving her just in her garter and stockings. She had the tiniest triangle of a tanline just below the dimples on her back, faint lines over her hips and no evidence on her back that she had been wearing a top when she got that tan. "Should I call when I get home, or will you be watching me?" She bent over at the waist to pick up her dress. It was only 20 or 30 feet away, and I could clearly see every detail of her pussy. "I mean, watching FOR me. Watching me? Jeez, not like you're some creep staring in my window or something."

"Uhm." I took a deep breath. "I'll just come over around 5."

"Sounds good. See you then." She hung up and abruptly turned around, making no effort to cover up. There was no acknowledgement on her face that I was there, but she was looking right at me. Her pubic hair was trimmed into an inch wide strip, with a similarly tiny tanline to the back framing it. Her stomach was flat, showing no signs of a pregnancy 20 years earlier, and her breasts stood firm and round in defiance of her age. Her body was the result of the simulation airbrushing again, but I had to admit, it was basically how imagined she looked when I was a teen.

"Fuck." I just stood there with the phone to my ear well after she walked out of the window.

I hurried out of the house to work, a video store connected to a small grocer's and gas station. The town had a bigger grocery store, and a better gas station, but no other place to rent movies that weren't porn. The day shift had left me an inventory list, and I set to getting on it as soon as I could. Navigating the POS menus came right back to me just like Ms. Richards' phone number had, a trick of the simulation for sure. I looked up at the movie playing on thew wall of TVs for a moment, and back down at the green and black of the POS monitor.

My inventory list was gone, replaced with flashing text, "JOHN PLEASE SEE THIS. We're working on a fix but keep running into a problem. Whatever you do make sure you don't..."

"Hey, Johnny," someone nearby said my name with a smile in their voice.

I looked up, and smiled back, suddenly knowing why the simulation wanted me to go to work. "Hey, Pam. How are you?" My eyes snapped right back to the POS and my inventory sheet was back. The note from the lab had disappeared again the second I was distracted. I almost shouted, "DON'T WHAT??" but kept it under my breath.

Pam, like Ms. Richards, was one of the many older women I had a crush on as a teen, but unlike the others, Pam and I had what I saw as a decent rapport. She came in to rent movies several times a week, and picked mostly horror and martial arts, both things I could have talked about endlessly back then. A few years later though, I came to understand it was flirting and I was just too dense or insecure to pick it up at the time. Pam was in her mid to late 30's and had a typical 90's rocker-chick aesthetic. Her hair was dyed black with a red streak and Bettie Paige bangs. She wore glasses with thick black frames, low-rise jeans and chunky boots, a skintight strappy tank top that didn't even come close to covering her bra, and a red and black plaid flannel shirt tied around her waist. There was also something about her I didn't really think of as weird at the time, but once I was out in the world, I learned it was a pretty uncommon sight. Pam had a slight frame, and huge, probably fake breasts. I was never really a boob guy in the way most guys seem to be, but I had a hard time not staring at Pam's with how much they stood out, and how little she covered them.

Looking at the tv wall, she said, "You got the good Indy on, I see." And gestured at me like she was going to tear my heart out. "Kali MA..."

Still irritated about the note disappearing, I halfheartedly said, "Most gore I can play here without getting fired."

"It's good shit." She was carrying a basket from the grocery with a frozen pizza and a cheap magnum of red wine while she browsed the aisles. After a couple minutes of looking, she said the thing I remembered most about our interactions. It was a frequent visitor on late nights when my brain wanted to reflect on regrets without my consent, and something I remembered every detail of how she said it. "My roommate is out of town tonight, so I get to watch whatever I want for the first time in forever."

She didn't have a roommate, she had a husband. The second part was coming though. After setting a copy of Burnt Offerings on the counter, she asked, "You work pretty late?"

I knew this didn't happen the same day as the talk with girlfriend's mom. The simulation was playing fast and loose with chronology, tossing everything it could at me regardless of when it happened.

"10." That was the exact same thing I had said in real life. Then I left it there and rang her up, she went home to an empty house after a breakup, and I went to read the new issue of Fangoria. This was not real life. "You want some company?" It came out smooth, like I'd been practicing saying it in this exact situation for two decades.

"Honestly, I'm not used to being home alone. I would really like that."

"I'm not going to pass up Karen Black and frozen pizza."

She laughed a single loud laugh that was more teeth than anything. "I'll save Karen for you but I'm eating the pizza now." I bagged her things for her and she said, "see you in a bit. You know where, yeah?"

"Yeah."

"Cool." She stood there awkwardly for a second and asked, "Hey, how old are you?"

"18."

She flashed a thumbs up, "Got it. See you after 10."

I kept watch for more notes from the lab, but didn't notice any, then a couple hours later I was knocking on her door.

"Hey Johhny!" I had half expected the simulation to have her answer the door naked, but she was dressed the same, just without her boots or flannel. "Come on in." Her house was a 70's style open floorplan, the living room sunken to the right side of the kitchen, and the bedrooms and bathrooms down a hall to the other side. She had a fire going in the living room fireplace, and the bottle of wine was open on the coffee table next to a mostly empty glass.

We made our typical banter for a few minutes and went to start the movie. I sat down on the sofa while she put the tape on. Tracking lines streaked on the TV and she sat next to me, taking a sip of her wine. "I haven't seen this in years. I'm stoked." Video started playing, but instead of trailers and titles, it was an ad for a 1-900 sex line. She fidgeted with her drink and looked over at me.

After the add ended and it cut to a shot-on-tape video of Jenna Fine In a black body suit walking through a sparsely decorated house. Completely flat in tone, Pam said, "huh." I looked over at her, and instead of watching the tv, she was intently watching my reaction. "Guess I switched up the tapes." She took a sip of her wine again and asked, "Do you want to watch this for a bit first?"

I grinned a little shyly back, "Yeah, I guess we can do that." Jenna walked into a room with a naked man, and without pretense dropped to her knees and started blowing him.

After a brief moment my cock was straining against my jeans. Pam had been watching it grow instead of the movie and tapped a finger on the taught fabric around it. "That looks uncomfortable. If you need to let that out it's okay. Nothing I haven't seen." A smile was cocked on her face. "Tell you what." She stood up, "I'll take mine out too."

We both raced to undo our pants. She was wearing a pair of black boyshorts with purple trim. I took my boxers down, "Jesus. You were hiding that thing in there this whole time?" She followed, getting bottomless except her socks, throwing her panties on the sofa. Her pussy was shaved completely clean, and she had a tattoo of a heart with some tribal flare at the sides on her pubic bone. We both just stared at the other's genitals for a minute, and she said, "I'm not going to fuck a teenager, but if you need to take care of that, I'd love to watch." I slowly started stroking, and her hand dropped to her pussy. She sat back down, facing me with her legs apart, masturbating. "Jesus H Christ, look at that thing."

We watched each other masturbate for several minutes, and she said, "Okay, really, not going to fuck a teenager, I'm just," she reached a hand toward my cock, "going to help." Her hand gripped it, not even making it all the way around, and she laughed, reaching out with her other hand. She stroked me while Jenna started taking anal, precum started to drip off my head, and she absently brought her hand to her mouth to lick some off that had collected there. "Fuck, I'm going to need more of that."

She kept one hand clamped to my cock but maneuvered down between my legs. Both hands stroked me until a drip of precum showed. She watched it, half fascinated, then licked it off in a slow trail up my frenulum. It felt incredible. Slow and firm she kept stroking my cock, and each time it started to ooze she stopped stroking, squeezed it firm, and licked up the drips. She kept the base of my cock locked up in her grip, squeezing it tight, but only stroking it up and down a fraction of an inch. As the Jenna Fine scene ended, she started kissing the underside of my head, occasionally letting her tongue take another lick at precum that might have gathered there.

Her eyes were glazed with lust. The underside of my cock still pressed against her lips, she said, "I kinda want to make this take all night." Another scene started on the video. A woman in red lingerie walked through the same empty house from the first scene to the back yard. I thought I knew the actress, but her name was beyond me. "You okay with me teasing your cock all night?"

"No place I'd rather be."

She smiled and gave my dick a wet open mouth kiss on the underside of the head. "Good. Now watch your movie."

The woman in the video walked past a group of men and began a strip tease for them while they watched. She kicked off her lingerie and the camera panned down her body. On her pubic bone she had a tattoo, a tribal heart design. "Oh." The camera went back to her face and my brain finally made the connection. Even though she had a different hairstyle and wasn't wearing glasses, that was a younger Pam in the video. "I didn't recognize you."

Looking over her shoulder at the tv, she chuckled, "that was before I got married. I hope you like it." She spit on my cock and stroked the whole length, "my husband hates it."

In the video the guys had lined up with their dicks out, and Porn Pam was blowing them one by one, working her way down the line, effortlessly deepthroating the bigger ones. Between my legs she was completely making out with my throbbing cock, covering it with doting kisses, slow licks and drool. I tipped my head back and groaned and she slowed to a stop.

"Were you about to cum? You don't get to cum yet."

"No, just getting close."

Fingernail tips of one hand danced across the sensitive spots on my cock. "Okay good. I need way more time with this than that." She took the whole head in her mouth, and slowly sucked. As her video turned to a gangbang, she kept at it, licking, kissing, stroking, occasionally sucking the head, and backing off every time she thought I was close. In the scene she groaned and said, "more anal."

She smiled at me and said, "I love this part," and swallowed my dick all the way to the balls making the smallest of gagging sounds.

Porn Pam said, "Really guys, pussy is closed." She rolled on her back and made an X with her index fingers over her pussy. The first guy started fucking her ass right after.

My cock twitched deep in her throat, her eyes started to flutter, and she pulled off, stroking the full length slowly in a drool-soaked hand. "This was so much fun to shoot."

She swallowed me again but backed off this time and set into a slow deep rhythm, milking me with her throat. The first guy pulled out of her ass and came on her face and Porn Pam said, "fuck yeah." The second guy mounted her anally, her face still covered in cum.

She worked my cock slow and steady until the fourth guy was blowing a load on her face. Backing all the way off, she said with a mouth full of drool, "I cannot tell you how good it makes me feel to have a real dick in my mouth right now." She stroked the full length, and said, "do you want to cum for me?"

"Dying to."

She grabbed her panties off the sofa and said, "You want to cum in these?"

"I will cum wherever you want."

She smiled and wrapped the head of my dick in the crotch of her panties, kissing and stroking the entire length. The panties were soaked, she must have been dripping wet even before we started watching the porn tape. Just as the last guy in the video was cumming on her face all the endless teasing was too much. Pam, and Porn Pam said nearly in unison, "cum for me baby," and my mind flooded in pleasure. She squealed, adjusting the panties to catch as much of the cum as she could, giggling and stroking me, getting every drop of my load into her panties.

We made eye contact, and she was grinning, all teeth again. She set the panties on the coffee table, and asked, "Still want to watch Burnt Offerings?"

"Fuck yeah I do."

We fell asleep in a pile by the end of the second reel.

In the morning I woke up laying on my side with her hair in my mouth and her still naked ass pressed against me. My cock was between her thighs, and throbbing hard, in that way morning wood does. Her bare pussy was grinding against it in her sleep, leaving it soaked between her thighs. If she hadn't said the night before she wasn't going to fuck me, I would have been tempted to just slip it in. After a moment though she groaned to half awake, and one of her hands drifted down to her crotch, stroking at the head of my cock. She chuckled, clearly not all the way awake, and guided me into her pussy. The chuckle grew into a laugh, and she said in a throaty first-thing-in-the-morning voice, "I'm fucking a teenager."