[M]y (ex)girlfriend’s best [F]riend

“Hey can we meet up? I need to talk to you.”

It wasn’t unusual for Gracie to call me. We’d become friends in our freshman dorm, and even closer since I started dating her roommate and lifelong best friend, Cara, at the beginning of junior year. In fact, I dare say that she’d become my best friend with our shared loved of reading, The Simpsons, and oldies music. We even worked at the same bookstore part time.

“Yeah, what’s up?”

“Not on the phone, meet me at the swings.”

I put on a hoodie and walked to the center of camps on that usually warm February day, not knowing my life was about to change. I arrived to find her sitting on the swings holding some papers.

“I don’t know how to tell you, so read this.”

She handed me an email chain between her and Cara where Cara is asking her to go home for the weekend because her high school boyfriend is coming to visit and they need alone time. Despite Gracie’s protests, she outlines how she plans to cheat on me despite knowing I had plans for us, the excuse she plans to use, how he knew about me, and even that she kept me around for homework help and convenience. My heart sank.

“I’m sorry, Steven.” She said. “This is the first I’ve heard of it and you’re such an amazing guy. I wanted you to know.”

After a pause she continued. “I know you know I feel myself drifting from her. I don’t know if I’m seeing a different side of her now that I live with her, or her outgoingness versus my introversion. But I can’t stand the things she does, especially when she uses your ADHD and bipolar against you. Do you want to take a walk and talk? Or just walk in silence? I’m here for you.”

We walked and though I said little, she reassured me through it. I began to reflect on how during first semester Cara and were physical, but never farther than kissing and heavy petting. After Christmas break she was distant unless she needed something. Gracie was absolutely beautiful. 5’3, b cup breasts, and an hourglass figure. Cara was about the same height but curvy and a cute face. The more I thought, the more I realized there was nothing but physical attraction and attention.

This was Gracie came out with “especially with you saving and planning a romantic weekend for a Valentine’s present. I know it’s supposed to be a surprise to her, but I’d never ditch a guy who does the kind of things you do for her. I’ll love to find a guy like you. If it were me, I’d cherish every moment with you.”

“Wait.” I said. “Is the girl who has never had a boyfriend saying she’d date me?”

Gracie stopped for a minute and thought. “Well, I mean…I’ve never thought about it until you just said that, but yeah. You’re a great guy. Cute, funny, kind. I enjoy our time together. And you know the reason I haven’t dated is I want something real, not just some passing thing. My parents were so in love that mom’s death destroyed my dad. I want that kind of bond. Even if it made me, at 12 years old, be the carer for he and my brother.

The conversation changed from there. It became talking about a potential relationship between us. I admitted thinking she was out of my league. Eventually, we came up with a plan for me to catch Cara in the act, freeing us to be together.

“Well, would it be cheesy for my Valentine’s surprise for Cara to be our first date? Or is that too much for you?”

“Steven, you’ve become my best friend. I feel comfortable enough and, honestly, now that I’m admitting my feelings to myself, attracted enough that I think I can jump ahead a little. I feel safe around you. I know you’re not going to push any boundaries.”

That night Cara informed me she’d have to cancel our plans because she had a couple of papers to write. I feigned sadness, then at the time agreed upon with Gracie I met her at the dorm door. She let me in and took my keys to wait at my car, bag in hand. I showed up to surprise my “girlfriend” just in time to find her locking lips with another man. I ended it on the spot and walked away a free man.

Gracie and I checked into our room and dropped our bags. It was more amazing than the pictures. King bed, sitting area, shower AND soaking tub big enough for two with a window that opened into the room and an amazing view of the town. It was then that we shared our first kiss. I felt it through my whole body as we made our way to the bed.

We kissed more as my hands played with her tits. I was on autopilot now. This wasn’t the 19 year old libido I was used to, but a drive and passion. My hand unbuttoned her jeans and slid through her shaved pussy to find the wetness below. Gracie moaned as I rubbed her clit. My brain kept waiting for her to stop me but instead she encouraged me.

“Oh my God. Right there. Don’t stop.” She moaned and moved her hips into my hand. “Fuuuuuuuuucccckkkkkk.” Her whole body tensed.

“That. Was. Amazing. Is that what an orgasm feels like? Because if so, I definitely want more of those.” She laughed.

“Sorry. I should have asked. I never felt such a desire to touch someone, not even Cara.”

“Worth it!” She grinned.

We dressed in our nice clothes and headed to the restaurant. Gracie was stunning in a full length dress, her cleavage peaking out of the top. We talked in hushed tones through dinner, teasing each other. Gracie admitted to having fantasized about me before even though she’d never even masturbated, but couldn’t stop me because she, too, felt an electricity in my touch.

The clothes didn’t stay on long in the room. While Cara and I had played with each other, it was never fully nude. Outside of porn, when Gracie’s dress fell and she stood in front of me in cotton panties and a plain bra, it was the most nude I’d seen a girl in real life. We stripped each other to our skin.

“Can I touch it?” Gracie asked, staring at my hard cock. I laid on the bed and she gingerly stroked it.

My eyes were focused on her perky breasts and soon I was kissing them and licking her nipples. My hand found it’s way back to her pussy and teased it again. Her body was writhing under me as she came again.

“This will surprise you,” she panted. “But fuck, I need all of you now. I’m on the pill. Fuck me, please. Make me a woman.”

Being the awkward guy I am, all I could say as I crawled over her was “stupid, sexy Gracie.” A Simpsons reference that made us bust out laughing as she grabbed me and guided me to her entrance.

Gracie cried out as I pushed through her hymen. I stopped, worried about having hurt her so bad. But she quickly soothed me and I began to slowly thrust in and out of her. Soon, the tears dried and became moans. I rubbed her clit while I thrusted and she grabbed the sheets as she came on my cock.

“Let me ride you” she demanded.

I rolled over and she climbed over me. Her tight pussy soon engulfing me once again. I played with her tits and rubbed her clit as she set the pace. Rocking and thrusting her hips. When her muscles began to tighten again, I knew I couldn’t last.

“Gracie, I’m going to cum!”

This only encouraged her and she rode me faster. I felt her getting closer but her muscles gripped me harder and my hips thrusted into hers. Just as I began to shoot my load, she collapsed on top of me. My cum continued to shoot into her. When it all subsided and my dick grew soft, she climbed off me and my cum dripped out of her pussy onto me.

Gracie wiped a bit with her fingers and licked it off. “Mmmm. Semen” she said in her best Homer Simpson voice. “Looks like you uncovered a side of me I didn’t know existed.”

Source: reddit.com/r/gonewildstories/comments/sv7isa/my_exgirlfriends_best_friend