Ok, I'll admit it. My twenties were one long decade of trying to escape loneliness. After a pretty huge, life-altering breakup just after turning twenty, I found solace online as I licked my emotional wounds. Chat rooms were my escape. I'm sure if I counted up all of the hours I spent slumming around in chat rooms during my early twenties I'd probably have about five years tacked on to the end of my life. I'd frequent chat rooms that were local to where I lived. Thankfully, I managed to form some virtual friendships that would help keep the loneliness at bay for a while.
One night while jumping from room to room in a fit of boredom, I instant messaged a few random girls with only one reply back a girl named ILoveGreenEyes. With a hint of sarcasm but a generous helping of openness, my chat with ILoveGreenEyes was going pretty well, lasting much, much longer than the typical "hi a/s/l?"
We got passed the typical pleasantries, with me asking where ILoveGreenEyes lived. I was surprised to learn she lived in the same town as a friend I had a falling out with back in high school, even mentioning that fact to her.
"What was his name?" ILoveGreenEyes asked.
"Randall Williams. We had a falling out over a girl I set him up with. I heard Randall had feelings for a girl at his school named Sharon even thought he was dating my friend Wendy at the time. He admitted that he was just biding his time until Sharon gave him the time of day and I tried playing white knight to protect her. It ended in me being dragged through the mud figuratively and nearly literally by both of their friends."
"Yeah, I knew him. Actually, I am Sharon."
And that was the moment when the life of 15 year old me collided with 21 year old me. Staring at that monitor I was dumbfounded.
When I hung out with Randall he'd love to talk over and over and over again about how Sharon was the girl he wanted to date, if she'd give him the time of day. Apparently she didn't have a lot of interest in him and it just stayed that way.
There was an instant bond that Sharon and I shared from that day on. Each time we'd sign on and see each other we knew we'd be in for a talk one way or the other. When we eventually graduated from instant messages to phone calls. Our calls would be the last phone call of the night for both of us.
Sharon's calls were a comfort and constant in those days. Having that common bond of Randall Williams gave us a short hand for our past making it so easy to just jump into our friendship without the worry of feeling awkward. Our talks had the feel of two old friends reuniting after years apart with a dash of arguing from time to time like we were brother and sister. At some point or other during our talks I'd offer to play a few songs. The first time I offered a mini concert she thought I was joking. After one or two songs over the phone she started becoming a fan of sorts, requesting from the setlist of songs I could readily play at a moment's notice. During one of those nightly calls I was sitting on my bed with my acoustic guitar when I heard her make an odd noise of discomfort.
"What the heck was that?" I asked, laughing slightly.
"No, really. You can make noises like that and not expect questions to be asked!"
"I'm cold, ok?"
"What do you mean you're cold? What are you wearing?"
She was silent for a moment. My guess was she was weighing out the truth verses any other option for an answer.
"I'm wearing a silk robe," Sharon sighed.
"That's it. I actually sleep naked all the time."
"You're a brave one for doing that. No wonder you're cold. It's supposed to get into the teens tonight!"
"Don't worry," she said. "I'm getting lots of covers to solve that problem. Soon I will be nice and toasty!"
As plutonic as these calls were for both of us, hearing Sharon admit to what she was wearing while talking to me flipped a switch in my head that night. Honestly, I didn't look at her as a sexual person before that moment. Yet here I was with thoughts of Sharon laying in bed with her robe opened wide. Her long black hair falling all over the pillows. Her plump body exposed, showing off her bountiful breasts. Her soft tummy hanging out slightly just over her meaty thighs.
My mouth went dry. My heart sped up a bit. I was shaking slightly, possibly from the cold but probably from the adrenaline rush of seeing Sharon in a different light. Laying back on my bed, I couldn't help it, I had to press the subject of her nudity.
"So just a silk robe, huh?"
"What do you mean no?"
"I mean no in that I'm not wearing the robe anymore."
"Aha… so you're under the covers with no silk robe on?"
"Sharon, at this point I'd say it's a yes or no question."
"Fine. Yes, I am."
"Uh, what was that supposed to mean?"
My mouth dried up at that moment making my voice crack.
"It means that I like the idea of you laying in bed naked while we talk, that's all. Is that a problem?"
"No problem at all," Sharon said in a very matter of fact tone.
I slid my free hand into my hand into my boxer briefs, letting it run up and down the length of my shaft. Between the tone of Sharon's teasing tone of voice most nights, the naked under the robe visual truly opened my eyes to realizing something: that maybe we both were in need of more than just friendship.
There were moments of silence on the line. Neither of us sure what to do next since this was stepping through a new door in our friendship. It was like a phone sex game of chicken. My heart raced a bit more as I kept sliding my hand up and down my rapidly growing shaft, getting more turned on knowing she wasn't hanging up on me like I thought she might.
"You're too quiet," Sharon whined in a slightly annoyed tone.
As I talked my voice got deeper, softer. "I'm just here. Is that ok?"
"I guess so," she said softly with a sigh.
"Sorry," I admitted, "I've just got a bunch going through my mind. Taking it all in."
"Like the fact that you're laying there in bed naked with a bunch of blankets on."
"Is that so?"
"Yes," I sighed giving my cock a squeeze. "It's a nice thought on a cold night."
"I bet it is."
A few moments of silence pass us by again. I think Sharon could hear my breathing getting deeper. Neither of us were willing to break down that wall. But neither of us wanted to hang up, either, even with the night getting later and later.
"Well, say something!"
"I'm not sure what to say," I sighed.
"Tell me about what you're thinking."
"Don't know if I should."
"You'll hate me if I do."
"No I won't."
"I bet you will!"
"Nope. I promise. I'll be your best friend!"
"Somehow I doubt that."
"You really want to know?" I asked. My heart was racing at this point.
"Ok, fine," I sighed. "I like the image of you laying naked in bed so much that right I have my hand down my pants and I'm touching myself. Is that ok?"
There was a long pause. I didn't think she'd hang up now. Not after this long of a build up. But she has surprised me before. My heart was hammering in my ears. The shaking of my body got a bit worse from the adrenaline high of the moment. Still I laid there and waited.
"Yes," she said softly. "It's ok."
My cock grew to it's full height with those simple words. I was done teasing and playing with it. Now I wrapped my hand around it and started to rub up and down around it's mushroom head. The pure release of us breaking through that wall of 'what if' had me practically giddy. Sharon could hear the excitement in the way I was breathing.
"I'm glad you think it's ok."
"This is a big night for us. You have me admitting to more things that I expected."
"Are you implying there's more to admit?"
"Maybe," I said coyly. I lifted my hips and pulled down my boxer briefs and sweatpants. My cock was so hard it poked me in the belly button as I laid back down on the bed.
"Since you already told me a secret and I admitted one of mine to you, I don't know if it's fair for me to have to tell you yet another secret before you tell me one."
"Just tell me," Sharon sighed, "then I'll tell you another of mine."
"Ok, fine. I just took off my sweatpants and underwear so now I'm laying here just as naked as you are while we talk. And just for the record, yes I am still touching myself. Happy now?"
"Mmmmhmmm," Sharon moaned. She always did an "mmmmhmmm" anytime I said something that might make her get sarcastic (which was pretty much most nights we talked). This "mmmmhmmmm" though had a little breathy quality to it. It sounded like Sharon was finding this more delicious than not.
"So what should I know about what you're doing over there?"
Letting out a long sigh, Sharon's voice got softer as she spoke. It had a quietness to it that helped me feel like she was letting me in on a secret that she'd never confide in anyone. To put it bluntly, it was a very sexy tone of voice for this moment.
"I might just be checking to see how wet I am."
I tightened my grip around my cock.
"Care to share?" I teased.
"I'm very wet."
"Really? How wet is very wet, Sharon?"
Another moment of silence.
"I'm wet enough that I feel it dripping out of me. It's starting to cover my inner thighs."
I was grinning from ear to ear. There was something so liberating about us discovering this side of our friendship. From the way my hardness was to the point of being painful that night, I could tell this was a moment that I wanted to relive each night as long as Sharon wanted to.
"Is anything else happening while you check how wet you are?"
"Sharon, at this point I think we've danced the dance enough to know we can be honest with each other. Just tell me."
"Ok, fine. I have two fingers inside of me."
My hand moved faster on my cock.
"That's hot! I wish I could see that."
Sharon moaned louder, her voice breaking up a bit. She was falling off the edge with me and now we were too worked up to care. I just pictured her laying there in bed. Her legs bent, open wide enough that her outer thighs rested against her bed. Her fingers teasing, exploring and frantically rubbing her soaking wetness as she tried to find release in this surprise turn of events.
"Do you like this?" I asked, feeling like the devil on her shoulder.
"I do," she breathed.
"I want you to do me a favor right now."
"Anything," Sharon sighed.
"I want you to tell me that I need to slide my cock inside of you and take you the way Randall always wished he could have."
Sharon let out a wail that sounded like she was crying and moaning at the same time. Her breath was coming in gasps as I imagined her fingers working in and out of her swampy wetness at lightning speed.
"I do want it. I want you to push your cock inside of me and let you fuck me like Randall always wanted to. Take it!"
Pushing my hips up into the air as I kept stroking, my breathing was coming almost as fast. I could feel the wave of pleasure building in my groin as my lower stomach felt like butterflies were going to rip out of me. My damn was about to burst and I wanted Sharon to know.
"It's too much," I groaned. "I'm not going to be able to hold on anymore. Sharon, I'm going to cum!"
Sharon was catching her breath in gasps. I can picture her breasts heaving, sagging to either side of her tummy. Her nipples so hard they're standing out of her giant areola like huge eraser tips. I imagined her thighs trembling as she pushed her fingers deep inside of her, probing to find that sweet spot.
My cock grew as hard as a rock in my hand. The moment was here. The tingling of the adrenaline, the muscles tensing in my loins as the sensation of deep muscle spasms took over sending me on a free fall of ecstasy. Like a fountain, rope after rope of white, creamy cum began to arc out of me.
Absently I started to moan and that moan turned into a series of guttural grunts as the spasms continued. Sharon was just as deep as I was. Her quivering voice letting out squeals that made me wish I was really filling her with my orgasm. I never imagined her sounding so vulnerable yet so excited to shed her sarcasm for a moment that was real. Her breath was shaky and only made that image of her thighs shuddering as her orgasm crested on her burned into my mind's eye.
Finally my hardness was at rest, laying limply against my stomach as we both fought to catch our breath.
"Dammit," Sharon mumbled.
"What? Are you mad at me?"
"No! Well, sort of, yeah!"
"I won't ask what I did since I was a willing participant. And, no, I'm not saying I'm sorry."
"You should be! Now I have to change my sheets."
I couldn't help but smile, more than just slightly proud of myself.
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