Playing pretend with an old friend [MF] – phone sex, J(ill)OI, not-quite-cheating [LONG]

**Disclaimer:** As you’ll soon learn, the circumstances of this story make some level of speculation unavoidable. Any fudging of actions or dialogue has been made in good faith. I hope you’ll accept, though, that the important bits – and there are many of them – have remained as clear and sharp as the night they took place.

Impatient and/or horny people can skip to the **[***]**.

**Fall of 1998. Nowhere, the Midwest, USA**

Me: A standard-issue small-town white nerd, aged 21. 5’7″ on my best day, not fat, but no muscle tone to speak of. Thick brown hair, dark green eyes, two godawful small-town tattoos, and, although it hadn’t been pointed out to me yet, a rather attractive, well-proportioned dick. At the time of this story, a bit inexperienced, but still a total pervert.

Allie: 5’4″, also 21, brunette with a wavy, shoulder-length cut that was doing its best to make people forget about the horrible 90s perm she and her peers rocked through four years of high school show choir. High cheekbones and narrow eyes that squeezed into adorable elfin slits when she smiled, which was often. What had previously been a rather average build had, thanks to time and circumstances, just started down the path to the type that would later be known as ‘thicc’. Full, round breasts, usually hidden under at least two layers of loose flannel, and a nice plump ass that found itself in similar situations. Blame grunge. At the time of this story, living with her boyfriend and their young child, and feeling ambivalent about it. Also a pervert.

My county school district made an experiment out of the ‘gifted’ kids in my year, brought them together from schools across the county and built two classes’ worth of All-Star (by Nowhere’s standards, at least) geeks that stayed together from 3rd grade all the way through junior high. I can’t pretend to understand what the district was going for with this. A grant project maybe, or a favor to the teachers, to get all the precocious little shits in one place. Maybe a photo op that grew out of control, I don’t know. One consequence that was definitely unintended was that after six years, we knew each other inside and out. Knew what buttons to push, just what to say to make it hurt, and when someone was certainly, definitely, not OK. Friendships in that group were ironclad. Enmities even more so. And by the end of 8th grade, we were all convinced of one thing: we were going to get out of Nowhere by any means necessary.

High school had other plans for us, though. A hundred different ways to fuck up your life before it even really gets started. For many of us, the fuckup of choice was drugs. The geeks of my vintage seemed to take to weed like they did to breathing. For others, booze. For others, Jesus. Or traffic accidents. Or a freshly-dead parent. Or jail. Or, as in Allie’s case, getting knocked up by your stoner boyfriend in the middle of your senior year.

Congratulations, Allie. You fucked up. Go directly to Nowhere. Do not go to college. Do not collect $200.

I, having only fucked up a little in comparison, ended up in a cheap state school an hour from home. In the fall of my junior year, a mutual friend from high school moved to town, and at her housewarming party, I ran into Allie again. Talk was easy, even after three years. We knew each other well, after all. Booze filled in the gaps.

The kid, she loved. The boyfriend, she did not. And the future, she did her best not to think about. “I,” she declared, “am well and truly stuck. Nowhere was bound to get a few of us, and it sure as shit got me.”

This would normally be the part of the story where we revealed the mutual crush we had failed to act on back then, but life is rarely that cliched or convenient. By the time we got to high school, with a few exceptions, the Geek Gang was generally quite sick of each other. Allie and I moved in different circles, first within the band and drama cliques, then within the stoners. Attraction had not blossomed. Not then.

“You can change things, though. You can always change things.” Buzzed as I was, I knew this was bullshit before the words were even out of my mouth. She shot me a withering look.

“I don’t think so.”

“Why not?”

“For starters, because I don’t cheat. Never have.” This was not where I expected the talk to go. I realized with more than a bit of fear that she might have assumed I was hitting on her, and was politely telling me to back off. I needed to correct this if it was the case, but also to be careful not to shut things down if it turned out she had raised the topic as a backhanded method of hitting on me. I tend to overthink these things even when drunk. Anyway, there was no point in getting defensive.

“Same here.” This was technically true – my relationships to this point had been either too abbreviated or too casual to allow for the possibility.

She locked eyes with me and took a sip of her drink as she chose her words. “But talking isn’t cheating.”

I let that slide. She didn’t.

“Isn’t it?”

“No.”

She didn’t look away. “And I’ll bet you can talk.”

I swallowed hard. “So…”

“So… let’s talk.”

“Don’t say that unless you’re serious.”

She dropped her eyes and took another sip. “I’m serious. Give me your number. You got a roommate?”

“No.”

“Well, you know I have two, so – it might be awhile. Don’t you dare miss it, though.”

My blush was so intense at this point I couldn’t even play it off as drunkenness. Nevertheless, I gave it my best smirk. “Gonna give me a hint at least?”

She thought about it for a good five seconds, then smirked back and shook her head. “No. Just don’t miss it.”

She was as good as her word, or lack thereof – a month passed, and a second one was well on its way out. Enough time, in other words, for nervous anticipation to have stopped fucking up my sleep pattern. Not enough time that hearing the phone ring after 9 pm wouldn’t still cause an immediate adrenaline surge. The call came a bit before midnight on a Sunday. Being a fundamentally boring person, I was both in and asleep, but a single dorm room ensured that I could both hear and reach the phone without undue pressure. I even allowed myself a third ring to get my bearings.

“Hello?”

“Hey.”

“Allie?”

“Yeah. Sorry it took so long to get back to you, but y’know, life and everything.”

“I know.”

“But tonight, I’m alone. You?”

“All alone.”

A pause. “That’s good, right?”

I was already begin to tremble a little. “Yeah.”

“I mean, if you still-”

No hesitation. “I do.”

Another pause. “Me too.”

And there it was. No backing out now.

She led off. “So, you think you can talk.”

“*You* said you thought I could talk.”

An annoying and unavoidable aspect of late-stage flirting – both parties perfectly aware of where the conversation is headed, and would honestly just as soon get there already, but neither wants to appear pushy or creepy, or they just don’t want to blink first. If not handled properly, too much back-and-forth at this stage can put a damper on the whole proceedings.

I bit the bullet. “I guess there’s two ways we can do this. One, we can talk about what we *would* do to each other. And unless I’ve badly missed my guess, that’s going to involve fucking.”

“Yeah.”

“More potential that way, maybe. Less limits. More imagination required. Easier to lose track of things. Two, we can talk about what we *are* doing. And that’s going to involve touching, and describing what’s being touched, and telling each other what to touch, and when, and how.”

“Hmm.”

“Easier to focus. Just talk about what’s happening. Keeps things moving. It’s… real-er, maybe.”

“You’re not speaking from experience.” It wasn’t a question.

“No.”

“You got a preference?”

First gamble of the night. “I want to tell you what to do, Allie.”

“Do you now?”

“I do.”

She had bet that I could talk. But I *knew* I could.

“Kissing is important. Making out is important. More than that, it is fun. I don’t think either of us are the type to jump right into things without any buildup.”

“Unless I’m drunk. I don’t know about you. Where are you going with this?”

“Trouble is, unlike fucking, kissing is not nearly as much fun to talk about as it is to do. The kissing equivalent of jacking off has yet to be invented.”

She chuckled. “If I hadn’t been in the Geek Gang, I would’ve hung up on you by now. Twice if you count that ‘two ways to do this’ shit.”

“If you hadn’t been, I wouldn’t have said it. Give me some credit.”

“Anyway.”

“Anyway, let’s assume that we are both nice, charming people who know what they are doing. Let’s assume that we’ve started things properly with a few probing kisses, and when those went well, let’s assume we got comfortable, wrapped our arms around each other, and had a lovely long makeout session there on your couch. Let’s assume fingers intertwined, necks gently bitten, tongues sucked, and sore lips. Let’s assume hands under shirts and on top of crotches. Let’s assume we just *shocked* each other with how good we were at this.”

“I like these assumptions.”

“Let’s assume that all that excitement has left you on my lap, stripped to the waist. You’re facing away from me, leaning your back into my chest. You’re squeezing my thigh as I play with your tits, and I’m leaning over your shoulder as you tilt your head back to kiss me.”

“Very nice.”

“And here, let’s stop assuming, and start *doing.*”

“I’m ready.”

**[***]**

“Take your shirt off, and your bra.”

“Yes.” A rustle of movement confirmed it. “They’re off.”

“Sit down on the couch, lean back, and think of being in my lap. Think of me caressing you. I’m going to tell you what I’m doing to you, and I want you to do it to yourself if you can. Okay?”

“Mmm-hm.”

“I’m playing with your nipples. Brushing my fingertips lightly across them, tugging them gently, licking my finger and drawing little wet circles around them.”

“Mmmm”

“You have nice round tits, Allie, but you know I haven’t seen your nipples. Describe them for me.”

“They’re pink, and kinda big. Soft, most of the time.”

“Not now?”

“Not now.”

“Good. Now, one hand slowly travels down your stomach, stopping to trace a lazy circle around your navel, which I’ve also never seen. Tell me about it?”

“Innie. Sorta deep, I guess? I never really thought about it.”

“I’d like to kiss it.”

A pause. Here, I think, is the moment when Allie realized that she had been right about me and talking.

“I’d make you kiss it.”

“Thank you. Now my hand continues down your stomach, to the fly of your jeans, and very carefully undoes your top button. After that is the zipper?”

“Yes.”

“I leave that alone. For now.”

She sighed, but without disappointment. “Tease.”

“Now I want you to move. I want you on the couch, on your knees, facing off to one side. Lean forward and put your hands on the armrest.”

“That’s… gonna make it hard to hold the phone.”

“Speakerphone? I think you can get away with making some noise tonight, and we’re both gonna need our hands, too”

“Hang on.” A little movement, a faint electric downshift, and then Allie’s voice, sounding a little further away, a little fuzzy, but somehow more forceful. More raw. “Okay.”

“We’re both on our knees now, you leaning over the armrest, me right behind you. I cup your breasts from behind, lift them, stroke them, gently pinch your nipples and hold them in place.”

“In place?”

“Yes. You’re going to do it this time. I hold, you pull. Lean back and pull them.”

“Ohh-hh… that’s hot.”

“It is. Do it again.”

“Oh, baby-”

“Now think of my hands sliding down your sides, back to the front of your jeans. My thumbs slip under the waistband. I slide them apart, one towards each hip, and back. Your hands need to be my hands, Allie. I want you to do this for me.”

“Yes.”

“Back and forth. A little further each time. Over your hips and back across your stomach.”

“Mmmm-”

“And now they meet again at your fly. One hand grips your waistband, the other finds your zipper. And I slowly, deliberately, unzip your pants. Pulling them open, exposing your panties. Tell me what I see.”

“Black. Cotton. Strappy Jockey bikinis. Kinda boring, sorry.”

“Not boring. Cute. Now my thumbs slip under the strap of your panties and start to slide back and forth. Just like before, just one step hotter. Over your hips and back. Is that nice?”

“Yes.”

“I’ll bet you’re moving your hips under my hands, moving along with them, aren’t you?”

“Mmm-hm.”

“Good. One hand rests on your hip now. The other starts to slide forward again,my fingers in your waistband this time instead of my thumb. Tracing the crease where your thigh and stomach meet. A little further, inside your panties now. Slowly, further, deeper, and now I can just barely touch the hair of your pussy-”

She inhaled deeply.

“A little more, a little further, slow, slow, slow… and… stop.”

“No.”

“My palm is gently pressing against your lower belly. My fingertip is right above your slit.”

“Don’t stop.”

“You want me to stroke you.”

“Yes.”

“Stroke your pussy.”

“Yes.”

“You want my fingers to start working your hot, wet little clit.”

“*Fuck* yes.”

“You want me to make you cum.”

“Yes, baby-”

“And I will.”

“Ohhh-”

“And it’ll be lovely, and I’m going to cum hard for you, too. But not just yet.”

“Please, baby-”

“Uh-uh. You’re gonna do something for me first. And it’s gonna be hot, and nasty, and you’re gonna love it. Promise.”

Another deep breath. “You’re a goddamn tease. I never thought *you* of all people would be a tease.”

“But I am, and here we are. And you’re getting teased, and you’re liking it. My hand moves away again, over your hip and up your spine, stopping, palm flat between your shoulder blades, bracing you. Other hand moves to the back of your panties. The hand on your back tenses, fingertips digging into your skin just a little bit as the other hand starts to grip, and tug, and work those black cotton panties up between your cheeks.”

My second gamble. I didn’t really think she’d freak out and, as butt stuff goes, the request was almost comically innocent. Still, comedy was definitely not the note to strike at this point in the conversation. The last thing I wanted was for her to bust out laughing. Worse still would be a flat ‘um, yeah, okay’ type of response- a clear signal that her train of thought had been knocked completely off the rails.

I held my breath as the seconds passed.

Allie, her voice equal parts whisper and hiss, broke the silence. “*Nasty.* I didn’t know you were kinky at all.”

“I knew you were.”

“Yeah, how?”

A pause. “Well… you did it, didn’t you?”

The whisper-hiss again, this time much, much closer to the phone. “*Yessss.”*

The mother of all shudders passed through me, and all I could come back with after composing myself was, “See?”

“Fucking. Little. Tease. I gave myself a wedgie, smartass. Now what?”

Unexpectedly, it was me who had to hold back a laugh. “You are *so* cute, Allie, but you’re talking too much. Remember I’m right behind you on that couch, and you’ve been feeling my hardon pretty much since we started. You’re going to show me how bad you want it now.”

“I want it.”

“Show me. I’ve got you on your knees facing out over the arm of the couch. one hand on your back, leaning you forward just a little. The other still has the back of your panties twisted up like a handle. Reach back and hold your panties just like that.”

“Yes.”

“Good girl. I’m pressing my crotch against your ass now. My hard cock against the denim, the denim against your soft pink skin, and a little strip of black cotton between your cheeks. Can you see that?”

“Oh, yes.”

“I want you to grind on me, Allie. I want you to work your hips like you were riding my dick. And I want you to pull your panties tighter up your ass with every stroke. Understand?”

“Yes.”

“Then get to work.”

“Oh, oh, *fuck*.”

“Spread your legs. You can rub yourself while you do it.”

“You too, baby. Stroke your dick for me, please.”

“Yes, baby.” Another gamble. I’d have to be very careful indeed. At this point, a stray gust of wind might’ve sent me over the edge, and despite a proven track record of multi-shot jerkoff performances, I didn’t trust my ability to recover in time for finishing Allie off. Still, as accommodating as she’d proved to be so far, she could’ve asked me to try to fuck a pot of boiling water and I’d have given it my best shot. “Now grind.”

A delicious static-y silence followed as Allie put on a show, in the dark, for an audience of one who wasn’t really there. My ‘view’ was a thin white noise of creaking furniture, a young woman’s heavy breathing, and the occasional whispered obscenity. It was more than enough.

“I — wish — you could see this. This is so — *fucking* hot.”

“I can see it, Allie. I can see the sweat on your forehead. I can see the panel of your panties stretching tighter and tighter against your pussy. I can see that thin black strip of fabric rubbing against your hot little butthole-” Fourth gamble.

“*FUCK”*

Jackpot.

“And I can see how you twitched when I said that just now, you nasty girl.”

“Fuu-uck…”

“You’re doing *great*. And you can do even better. Take your pants down.”

A few seconds of rustling. “You really like my ass, don’t you baby?”

“I *adore* it, Allie. Now get your hand back on your clit and fucking *pump* that ass.”

“Nggh-”

“Faster.”

“*Shit,* baby-”

“Faster.”

“Baby, I’m close, I’m close, please-”

“Me too, baby. You wanna cum?”

“God, yes-”

“Take your panties down.”

Another quick rustle.

“Get your fingers wet.”

“They’re *soaked* already-”

“Other hand.”

It took a second for her overstimulated mind to catch the implication. The last gamble of the night.

“*^(oh fuck me-“)*

“You want to.” It wasn’t a question.

“I *do.”*

“Go on.”

After a few urgent, sloppy licks to her fingers (sound likely exaggerated for my benefit), Allie reached back and with the same short, sharp inhalation she might make stepping into a too-hot bathtub, began to rub her anus, matching the ministrations of her other hand to her clit.

God bless the speakerphone. Glory, hallelujah.

Her little gasp did me in instantly – before I could say anything I was in the throes of a brain-melting, knee-buckling orgasm that had been building since the first words we spoke. Further speech, though, was beyond my capabilities for the time being. Allie’s orgasm followed right behind mine, her rising moan suddenly muffled as she clamped her mouth against her shoulder or, as I prefer to believe, on the arm of the couch. Our worlds were washed away in a flood of dopamine, and it was exquisite.

Silence settled in as we both caught our breath over the next few minutes. This was awkward. I wanted to hold her, to pet her, to push her hair out of her eyes and just look at her, but none of those options were on the table. I wanted more, and I believed she wanted more, too, and it wasn’t going to happen. I was in college where we were all supposed to be, she was stuck in Nowhere with the stoner boyfriend and the kid, and we hadn’t known how hot we ended up being for each other, and *it wasn’t fair.*

She spoke first. “That… was **fun**.” It sounded as though she was saying it for her own benefit. “So fun.”

There’s not much room to linger after phone sex, you don’t slowly wind down or change the subject. Post-orgasmic brain chemistry makes sure of that, along with a nagging need to wash your hands that certainly wasn’t there five minutes ago. More than a little anticlimactic, given the intensity of the climax. More than a little sad.

We exchanged grateful goodbyes, and, I’m sure, both bit our tongues to keep from letting the words “next time” slip out. Even in the moment, I was aware that the night was already shifting into the stuff of dreams, where it’s remained these many years since. I’ve revisited it, often, and intend to do so as long as life and memory allow.

I hope Allie does, too. I’ll never know, but I hope.

Source: reddit.com/r/gonewildstories/comments/bytkiq/playing_pretend_with_an_old_friend_mf_phone_sex

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