[M]y childhood [F]riend helped me get over my ex

This one comes from a few years ago when I was nearing the end of my time in college. All through the end of high school and first few years of university, I had the same girlfriend. Ana and I were the super saccharine high-school sweethearts that you normally only see in movies. She was on the swim team, I was on the soccer team, and the two of us maintained genial relationships with almost everyone we interacted with in high school. “Popular” is a loaded term, so I won’t say that that’s what we were, but we were definitely well-liked. People were generally rooting for us to live happily-ever-after and we gave them every indication that we would.

That facade persisted through our first couple years in college. I can’t exactly explain why I fell for Ana so hard in high school, but there was something about her that just felt… intoxicating. Like, I was drawn to her in a way that I couldn’t articulate. It was probably her eyes. As much as I appreciate a well-developed physique, there’s something about *eyes* that enchants me, and Ana had these beautiful blue eyes that transfixed me whenever she looked my way.

But it became readily apparent as we continued dating through college (we both went to the same big university) that I was just way more into her than she was into me. I felt constantly inadequate in her presence; I had to engage in grand, romantic gestures to get even a modicum of affection in return.

Eventually, Ana let me know what I had already realized months prior: she just didn’t like me that much anymore. It crushed me to hear those words from someone that I thought I was going to spend the rest of my life with. I was a gracious dumpee, thanking her for our time together, but on the drive home I cried my eyes out.

The next day, my neighbor and childhood friend Emma came over to borrow some bar supplies. Part of the reason Ana and I had gone to the same college was that a lot of our mutual friends had also gone there, and Emma was one of them. I had known Emma for nearly twenty years at this point, so she was a close confidant and a dear friend. Because she felt almost like a sister to me, and because she was a certified 9/10, I had never considered her as a viable partner. She always felt way out of my league.

As I gathered the items that Emma needed (she was hosting a Gatsby party for her friends and needed my cocktail accoutrement), she asked me how things were going with Ana.

Have you ever had someone slap you on the back after you’ve been sunburnt? That’s sorta what it felt like to hear her ask that question.

Trying not to seem too devastated, I regaled her with a highly-sanitized version of our break-up. As I explained the situation, I could see an expression of concern growing on her face. Her lips pursed together and her brown eyes stared into mine. Even though I acted like I was okay, she was far too perceptive to believe me.

As I finished my story and handed over the supplies, she took my hand. My heart stopped. She placed her other hand on my shoulder and looked up at me.

“Greg,” she said firmly, in a tone that demanded my attention. “You’re a great guy. Any girl would be lucky to have you. I’m sorry that you’re going through this right now. If you want someone to talk to about… all of this, I’m available. You don’t have to go through this alone.”

She stood up on her tiptoes and gave me a quick peck on the cheek. She looked at me expectantly as I tried to process everything she was saying.

“Thanks, Emma,” I said, after mentally discarding half-a-dozen other responses. “I appreciate it.”

“You’re welcome,” she said matter-of-factly. She hesitated just a moment longer and then let go of my hand, released her grip on my shoulder and strode out of my apartment.

—

The next few weeks were… not great. I continued to project an air of contentment about my newfound singleness, but my grades began to slip and I started having trouble sleeping.

Eventually, Emma took me out for coffee to pick my brain about how exactly I was handling things. I tried obfuscating for a while, but with the precision of a patient boxer she broke down my defenses until I finally confessed how utterly shitty I was feeling. I could see the heartbreak in her eyes as her shoulders slumped. I bit back tears and gulped down way-too-much of my bitter espresso.

After a prolonged silence, she finally spoke up.

“Look, Greg,” she said, “I don’t… What I’m about to say might change our friendship… and I don’t want that… I value you as a friend and it’s *because* of our friendship that I’m even putting this out there.

Sometimes, when we go through these break-ups, it can be helpful to experience being with another person… a new person. That can help us see that the lies our ex told us aren’t actually true. We can get a second opinion, kinda. I know that, after I broke up with David, I actually benefited from hooking up with Alex a short while after.

But, I also know, for you… it might be complicated. You might have trouble trusting someone enough to try again. And I don’t blame you. Ana was a jerk. I’m sorry, I know you still care about her but it’s the truth. She did *not* treat you well and you deserve better. But I’m sure the trauma from that experience is going to be a lot to unpack before you have another serious relationship…”

I wondered where she was going with all of this.

“…So, I guess, what I’m saying is…” her tone became more hesitant and her words became more carefully measured. “Maybe, you shouldn’t try another serious relationship yet. Maybe you should try something lower-stakes and more fun. And, if it would help you out, if it would help you move on more quickly…”

She took a deep breath, stared deep into my eyes, and uttered a series of words that nearly broke my brain.

“I could sleep with you. If you wanted, of course.”

I blinked. A deafening silence filled the room as she held my gaze. I half-expected Ashton Kutcher and a camera crew to bust into our apartment at any second. No such revelation was forthcoming.

“Are you… serious?”

She leaned forward. “Yeah… I mean, if that’s way too awkward I totally understand… but if you’re going to have a casual fling with someone it might be easier if it’s someone you trust.”

My tongue twisted itself up in knots trying to compose a myriad of eloquent responses. In the end, all that I could muster was a singular syllable that sent a smile streaking across her face.

“When?”

—

Over the next couple days we worked out the logistics, which was a weirdly thrilling experience. I started to see Emma in a far more sexual light as we discussed things like birth control, kinks, limits, venues, etc. Eventually, we settled on a Friday night at her place when she knew her roommates would be out of town.

Admittedly, I started jerking off a lot more in the lead-up to the night of, knowing that if I wanted to last more than 0.9 seconds I would have to start building up stamina. I was not necessarily a chump, but Emma was unlike any other sexual prospect I had ever had. She had long brown hair, deep brown eyes, perky B-cup breasts, an ass toned by regular squats, and legs for days. She looked good in just about every outfit I’d ever seen her in, from frumpy hoodies to formal, backless gowns.

When I got to her apartment I knocked on the door expectantly, only to receive a text in response.

“Come on in. Bedroom. I’m ready for you.”

—

I walked into the room and froze in my tracks. Standing in the middle of her bedroom, with a sly grin slowly spreading across her face, was Emma, completely nude, bearing the prettiest shaved pussy and perky breasts I’ve ever seen. The room was bathed in violet hues from fairy lights that ran across the walls. This light fell in enchanting cascades across Emma’s body, highlighting every contour, every curve. The ethereal visuals combined with the scents from her essential oils diffuser made the whole thing feel like a fey encounter.

But for all the intoxicating sensorial wonders I remember, the detail that stands out most clearly in my memory is her eyes. Deep, brown eyes, regarding me across the room with a sense of playfulness, giddiness, and excitement. I could have stared into her eyes for hours.

I opened my mouth to compliment her, but my voice stuck in my throat. My brain was still processing the kaleidoscopic display in front of me. Not missing a beat, Emma strode forward, her lithe footsteps and swaying hips displaying a cool confidence. She placed her right hand on the back of my neck and pulled me into a passionate kiss, pressing her body against me. My heart rate immediately quickened and a shiver of electric joy raced down my spine.

She pressed her lips into my neck as she unzipped my hoodie, not even needing to look. She pulled herself away from me briefly, allowing me to pull off my T-shirt as she unbuckled my belt and pulled down my pants, freeing my already-throbbing cock which sprung promptly to attention. She giggled as it trembled mere inches from her face. Leaning forward, she grabbed the base of it and ran her tongue along the underside, concluding with a soft kiss to the tip. I nearly came right there.

“I never knew you had such a pretty cock,” she said coyly. She pulled her hair back and stared up at me pleadingly with those puppy-dog eyes of hers. “How long have you wanted this?” she asked, her voice taking on an increasingly husky tone. She fell into an almost-metronomic pattern of sucking my cock and then pulling herself off to make another remark. The dirty words sounded so strange coming out of her normally innocent mouth, and the shattering of her girl-next-door persona was driving me wild.

After a couple minutes of this, I could feel myself about to explode. Sensing this, she pulled herself away and walked back towards her bed, giving me an unrestricted view of her statuesque ass and legs. My heart thudded in my chest as I felt my body screaming to bend her over and fuck her into oblivion. *Not yet,* I thought. *Be patient.*

She sat down on the bedside and spread her legs, exposing her perfect, pink pussy. She ran her left hand slowly down her smooth, supple stomach until her fingers rested on either side of her engorged pussy lips. She spread them slowly, allowing me to bask in the view of her god-tier, sopping wet cunt.

“Thirsty?” she asked, raising an eyebrow.

I’ve never moved so quickly in my life.

My knees hit the floor as I raced forward, burying my face between her thighs. Her musk filled my nostrils and her moans filled my ears. Her pussy was a complex menagerie of tastes, and my tongue wanted to experience every single one. My technique was amateurish at best, but she didn’t seem to mind. My boyish exuberance made up for it as she flooded my mouth with her unique flavor.

My hands reached around to where her firm buttocks were perched on her luxurious bed sheets. I grabbed them, allowing my fingers to knead her ass cheeks as my tongue explored her warm pussy.

“Oh, fuck,” Emma rasped, “oh, fucking *fuck*. Yeah, that’s a good boy. That’s a good, good boy.”

*Hot damn,* I thought, realizing how much it thrilled me to hear those words. I hadn’t realized how much I had missed such simple affirmation.

After a few minutes of this she flexed her thighs against my skull, holding my mouth firmly in place as her body undulated hypnotically. I felt a warm wetness seeping down my chin as her breathing quickened.

“Fuck, almost there,” she said. To my surprise, she pulled herself away and stood up woozily, looking at me with a wild hunger in her eyes. I got to my feet, too, only to be knocked backwards onto the bed by a firm push. Before I could say anything she was on top of me, straddling me, her pussy poised mere inches from the twitching tip of my cock. Her normally perfectly arranged hair fell in messy strands around her face and she pushed herself downward, her dripping-wet entrance greedily swallowing my cock. I gasped and felt my whole body tense up in delight.

Gone was any pretense of patient foreplay. Pure, lustful hunger consumed both of us. I reached up and grabbed her breasts, my thumbs playing with her nipples as my fingers massaged her supple flesh. She arched her back and began methodically swaying her hips, bouncing her plump ass up and down the length of my shaft. Looking down, I could already see my cock and balls glistening with her pussy juices.
I wish I could say that we carried on for hours, switching positions and experimenting with every sexual activity known to man. Alas, I am merely a mortal man, and I’m pretty sure that no mortal man could last more than a few minutes with Emma fucking them like that. Her speed quickened into a rhythmic ride as the wet *clap* of our colliding bodies and the musky scent of our sex permeated the room.

A broad smile broke out across her face as we fucked, and it struck me just how *happy* she was. With Ana, I was always so keenly aware of my own inadequacy when we fucked. It always felt like a privilege to be able to fuck her, a privilege that she could revoke at any time if the whim took her. But here, with Emma, I could see just how much she *enjoyed* this. For the first time in a long time, sex felt *fun* again.

As this thought took hold in my brain, I realized that our fun was rapidly coming to an end. I could feel my muscles tensing up, in anticipation of an almost-volcanic release.

“Emma,” I gasped, breathless. “Emma… I’m going to…”

As if reading my mind, she pressed her hands into my chest and lifted herself off of me. I felt initially disappointed at the loss of sensation until she scurried down and plunged my cock down her throat, engulfing my shaft in the warmth of her waiting mouth. This one-two punch was the knockout strike, and I erupted down her throat. I heard her gag as she struggled to swallow what felt to me like a geyser of cum, but after a few seconds of throbbing and pulsing my cock softened and she tilted her head back, audibly gulping down the last drops of my seed. She opened her mouth and greedily sucked in air, her face flushed red. My limp cock slapped back against my crotch and oozed cum onto my belly, which she dutifully lapped up with a few deft strokes of her tongue.

“Wow,” I said. It was all I could say.

She crawled up on top of me, intertwining her body with me in a soft cuddle.

“Wow,” she repeated, looking into my eyes with a smile on her face and a glimmer in her eyes.

“Thanks for this,” I said, a quasi-clarity starting to return to my delirious body. “This was great. I think… this was what I needed…”

She kissed me on the cheek and nuzzled her head into my neck.

“You’re welcome,” she whispered as she closed her eyes and held me tight.

We fell asleep shortly thereafter in that same position, arms wrapped around each other, bodies pressed close. Normally I have trouble sleeping comfortably in a bed with another person, but I had no trouble that night.

Source: reddit.com/r/gonewildstories/comments/xt0yk9/my_childhood_friend_helped_me_get_over_my_ex