[M]y Best [F]riend Part 1: First time [Long]

This ended up longer than I intended, but it should be worth it. If you want to skip ahead, go to the *******
Also, on mobile.

Emily and I have been best friends since birth. Born just a day apart, our parents met in the maternity ward and quickly became friends. Shortly after our births, her parents moved into the 1920s bungalow next to and identical to ours but with a mirrored layout.

We both ended up with the small attic bedrooms, shared birthday parties and family vacations, and went to church and school together. Basically, we were inseparable. In any other world, we probably wouldn’t have been friends. Yet Emmy (my nickname for her as I couldn’t say Emily when I started talking) and I have always had a unique, unbreakable bond. We shared secrets and she was my biggest support through my bipolar diagnosis. Our parents even built us a tree house on the tree that sits between our yards.

Despite my self-esteem issues, I wouldn’t say I’m unattractive. 5’10 with curly brown hair and a dad bod, partially thanks to medicine that makes it hard to lose weight. Emmy, however, has a body that garners more attention than she wants. She stands 5’2 with brown hair, dark green eyes, and an hour glass figure. Think Rilee Marks with a more defined hour glass figure. They look surprisingly, albeit disturbingly, a bit alike. She always hated the attention her body garnered for guys as she was always fairly reserved.

Five years ago we were eighteen and seniors in high school. We both grew into introverts but were still as close as ever. We had a shared friends group and friends outside of that group. While we both dated throughout high school, the thought of dating each other never crossed our minds.

It was on prom night, however, that our friendship would change. Emmy and I were both single at the time, but we had dates for prom. I took Christine, a mutual friend, and she went with our classmate, Tom. While I chose to drive Christine and I in my WRX, Emmy rode in a limo with a group of her friends. The plan was for them to all go back to one girls’ house for an after party.

Prom was a blast, though, even as an introvert. I felt great in my tux. But by the end of the night, I was exhausted and ready to go home and decompress. As the night came to a close, Emmy approached me and said she was tired of socializing, too, and wanted to go home. Somehow, she orchestrated Christine taking her place.

Emmy was unusually quiet on the way home. She spent the trip across town from our high school staring out the window. When we got home, Emmy broke her silence. “Will you meet me in the tree house after I change? I need to talk.”

“Sure. See you in 5?”

“Thanks.” There was a bit of relief in her voice.

A few minutes later I was changed into my gym shorts and favorite shirt. I checked in with my parents and headed to the tree house, browsing Reddit on my phone while I waited. A few minutes later I heard Emmy’s back door and saw her shadow crossing the yard.

She sat down across from me, her legs crossed in front of her.

“What’s up?”

“Steven…I…do…” she stammered and then dropped her head, fidgeting with the cross necklace I gave her for her 16th birthday. “Sorry, this is hard.”

“It’s ok. You know you can tell me anything.”

After a moment of silence, she took a deep breath, lifted her head and asked “does the thought of going off to college a virgin bother you?”

“Well…I mean…believe it or not I do have…urges. And I’d hate for my first time to be with just anyone. Especially with the attention my stupid body gets me. I want my fist time to be with someone I trust and there’s no one I trust more than you. I mean, you’re my best friend and I can’t see there ever being an us, but we can learn together.”

I was speechless and just ended up staring into her deep green eyes, unable to comprehend what was happening.

“Shit. I’m sorry. I knew I shouldn’t have asked you and risked our friendship. Fuck.”

“No. It’s not that. A.) nothing will EVER affect our friendship. No matter what that will ALWAYS come first. B.) it’s a lot to take in. Having said that, yes. You’re right. Let’s do it. No pun intended.”

“Not now though. Next weekend when our parents are at their marriage retreat.”

“Ok”

And with that, we went into our respective houses, texted a bit, then went to sleep.

*****************

The whole week following was filled with anxiety. We talked a little about our coming rendezvous, but not much. On Friday, our parents left and we went to grab pizza before heading home. As we got in my car, I mustered up the courage to ask about stopping for condoms.

“No, I know we should be extra safe, but I want the full experience. I only get one first time. We can get the morning after pill but it’s also what should be a safe time in my cycle.”

“Or…I could…uhhhh…pull out.”

“What’s that?”

“Basically, when I’m ready to cum I pull my…uhhhh…dick out…and one of us strokes it until I cum.”

“C…could I do it?”

“If that’s what you want…”

As we arrived home, Emmy led me into her house, up the stairs, and to the familiar bedroom. We stood awkwardly for a moment, but before I knew it we were leaning in to kiss. A brief peck at first, but then we began making out. A feeling washed over me like never before when kissing my girlfriends. Things quickly became automatic. I could feel myself growing hard in my shorts as we pulled closer to each other.

My hands slid down her sides and to the edge of her burgundy t-shirt, lifting it while touching as much skin as possible. Emmy raised her hands over her head for me to remove it. I had seen her in a bathing suit plenty of times, but she always wore a one piece. Seeing her in her bra and blue jeans had me throbbing. She soon removed my shirt, then we removed each other’s pants. We stood there facing each other in our underwear. Soon, there would be no turning back.

“You first” Emmy commanded.

“No, you!” I teased. Until I saw the nervousness in her eyes.

“Ok. Together. Eyes closed on the count of three. We both open together on the second ready. One…two…three.”

I dropped my boxers, exposing my r/realitydick. “Ready.”

Meekly, I heard her respond and opened my eyes. I couldn’t have imagined the beauty before me. Her perky, but large breasts (34D I’d soon learn), tiny Areolas, flat stomach, and full bush with no sign of thigh gap. Seriously, ridiculously similar to Rilee Marks but hairy and wider hips. We stared at each other for what felt like an eternity.

Finally, Emmy walked up and kissed me deeply. She gently grabbed my cock and started stroking.

“Sorry it’s not bigger.”

“Dude, the only time I’ve seen a penis is a graphic in health class. I have nothing to compare it to and it looks fine to me.”

With that she led me to the bed and laid down with her knees up. I climbed on top of her and we made out some more. Our bodies pressed tightly to each other.

“Are you sure, Emmy? Once we start we can’t turn back.”

“Very sure.”

“If you want me to stop, just tell me. Promise?”

“Promise.”

I was determined to make my best friend’s first time as special as possible. I rolled over onto my side and began running my hands across her body as we kissed deeply. My hands paused to caress her breasts before sliding down and her stomach and through her thick bush.

I’ve always enjoyed seeing girls get off. I much prefer solo porn for that reason. Inexperienced though I was, I was determined to find her clit. And as my finger entered her slit, I heard her jump a little and moan. I began rubbing the sensitive spot and as she moaned she adjusted my hand to the perfect spot. I kissed down to her chest and took a nipple in my mouth and began to suck and lick as my fingers rubbed her clit in circles.

Emmy’s moan began to get louder and I began to run faster. Her hips began to thrust, she began to pant. Suddenly, she shouted my name as she had her first ever orgasm.

“Holy…shit” she said between pants. “Is that what an orgasm is?! That was amazing. I’m ready, Steven. Make me a woman.”

She didn’t have to tell me twice. I climbed over her and positioned my dick at her wet entrance. I hesitated, overcome with nerves and anxiety. She gave me a smile and pushed her hips up a little to encourage me. Slowly, I entered her. I was completely unprepared for the warmth that gripped me.

“Ow!”

I stopped. “Are you ok?”

“I’m fine. It just hurts for a girl the first time. It’ll get better.”

I slowly began thrusting into her. Her loans of pain gave way to moans of pleasure. We kissed as I thrust into her. I was trying desperately to focus on other things so I wouldn’t cum too fast. Judging by the clock on her table, I made it 5 minutes before I could feel the orgasm building in me. I pulled completely out of her, and Emmy looked at me confused. I kissed her lips then down her body to her clit.

Determined to make it last, I took her clit in my mouth. I remembered reading to do the alphabet with your tongue so I tried it.

“Oh!” Emmy exclaimed. “Mmmmmm.”

I licked and sucked her her clit until she came again. As I picked my head up, she guided me to her and surprised me by kissing me.

“It’s your turn.”

I grabbed a pillow and set it under her ass. As I entered her deeper, she gasped and began to moan again. She started to match my thrusts. I was again overwhelmed by the tight warmth around me. But I kept it up as long as I could. She got tighter around me as she had her third orgasm.

That was it for me. When I pulled out this time, Emmy could tell I was ready. She sat up and began to stroke my dick hard and fast.

“Careful! You’re not trying to pull it off me!” I chuckled.

She got the picture and stroked me until I let out a grunt and shot my seed all over her perky breasts.

“Whoa! That would have been in me?!”

“If we were bigger risk takers.”

“Wow.”

I laid down and we cuddled for about 10 minutes. I got up to use the bathroom, then came back to her bed. We resumed cuddling and she fell asleep in my arms.

Source: reddit.com/r/gonewildstories/comments/gms9mf/my_best_friend_part_1_first_time_long