Megan and I have been best friends for about a decade now. Growing up, she lived in a neighboring town and our paths didn't cross until high school when we met through some mutual friends. She and I immediately hit it off, bonding over great conversations filled with banter, mutual interests, and some light flirtation. We felt free to talk to each other about whatever crossed our minds, including anything and everything sex related. When she lost her virginity, I took her out for ice cream to celebrate. If one of us had the hots for someone, we'd wingman each other without a second though. Most if not all of the stories I've written here she's heard and knows the details as well as I do. When she had her first threesome, she called me immediately after to give me a play-by-play, resulting in us talking about what she enjoyed and what she would change if there was another opportunity. She's texted me an album of nudes, asking which ones would be best for her "tasteful portfolio." We've even sent each other links to porn we think the other would like if they were in a dry spell and needing a good release. With all that being said, we've never made a move on each other. We definitely find each other attractive and know that about each other, but the risk of hooking up or dating and it ending poorly is a risk neither of us were willing to take.
Megan is about 5'2" with very long blonde hair, a great ass, B/C cup tits that don't drop an inch when her top comes off, and one of the more fun personalities I've met. She's quick to laugh, gives shit as good as she can take it, and can fit in with any group of people. She's a world traveler with great stories and moved to a big city to live out her dreams. She's the first to suggest exploring a new dive bar but doesn't mind staying in for a movie marathon. Despite all the great qualities she has, one thing she really struggles with is making a move on someone she's interested in. I've offered tips before, even going as far to roleplay, but that usually wouldn't go very far as my acting is shit and it ended up not being very helpful.
We were both home from school on break and she called me one night on her way home from picking up a bartending shift. She was talking before I could even say hello.
"Wanna come over tonight? Long day at work and need a relaxing evening to take my mind off things."
"I've got a couple errands to run, but I could be over in about an hour or so. Everything good?"
"I'll tell you when you get here. An hour works great, I need some time to decompress. Bring a swimsuit and a bottle of wine."
I pulled into her family's driveway with a bottle of red wine, a chocolate frosty from Wendy's, and a swimsuit. Megan was waiting for me by the front door and gave me a huge hug when I walked in. I awkwardly set the goods down on the table behind her before returning the embrace, picking her up off the ground slightly as I did so. As we broke apart, her mom came around the corner to say hi, give me a hug, and ask if I was staying the night because I arrived so late. I had stayed over a couple times in the past so it wouldn't have been uncommon, but I told her I honestly wasn't sure yet, I'd see where the night takes me. She laughed and said "that's the beautiful thing about being young, you can get into some pretty serious trouble doing that when you get older."
Megan and I broke away from her family to change into swimsuits to hot tub. We hadn't seen each other yet in the couple days we had been home, so we were eager to catch up (even though we kept each other up to date on pretty much everything in our lives anyway). As I opened the hot tub, she was already telling me about her shift and some guy that sat at the bar all night. I heard the very beginning of the story, but my mind tuned out audio processing when she dropped her towel, showing off her black bikini. The top was strapless, emphasizing her impressive cleavage and revealing a touch of underboob. Her bottoms were modest but had a tough time containing her ass. Her long blonde hair was tied up in a messy bun on top of her head. I must have zoned out for a minute, because the next thing I remember was her laughing, snapping at me, and saying, "I know they look awesome, but you've seen them before and I'm trying to tell you a story here." I smiled, apologized, and gestured for her to continue.
We sat next to each other in the water, jets whirling around us, as she caught me up on her night. Megan talked for nearly a half hour straight, but the short of the story is as follows. Apparently there was an extremely attractive guy sitting at the bar that chatted her up all shift. She was feeling really good about her prospects and towards the end of her shift, asked him if he had plans that night or if he was free to grab a bite to eat. He had an early morning and declined, but asked if she was free the next weekend. She had plans with friends and told him so, which flipped a switch in him. He became moody and slightly aggressive, before closing his tab and stiffing her on the tip.
"Men," she muttered under her breath. "I don't fucking understand. I looked hot tonight, I know I did. It was a slow night so he had excellent service. More than all of that, we actually talked. Like real, interesting conversations. Where did I go wrong?"
I knew it was a rhetorical question, but I gave her a sarcastic response. "Seriously? I mean, you could've dropped your cabin trip this weekend for a guy you just met, that's not unreasonable. Or you could've just said 'If you have an early morning, I'll just come over tonight.'"
"Just because I would've fucked him tonight doesn't mean I want everyone to know I would've fucked him tonight. There needs to be a little bit of mystique going into it, a little bit of the chase." She sighed, "I mean Jesus, the chase is damn near the best part. I could almost get off on the chase itself."
I agreed and put my hands up in a "what are ya gonna do?" type of way and she made a little pouty face before downing the rest of her wine glass. "Speaking of chases, how's it going with (girl x)?"
I started to tell her how we had kinda lost interest in each other but it wasn't really a big deal, I wasn't sure there was anything there anyway. We talked for about another hour about school, sex, and gossip before she suggested we go inside and watch something. By this point, we'd finished the bottle of wine and started on another, so I was resigned to spending the night. We changed out of out wet clothes after she let me get one last good look at her bikini and met in the basement. The house was dark at this point as everyone had gone to bed, but we figured we had no responsibilities, might as well see how late we can stay up.
"What are you thinking, movie or TV show? We could watch New Girl, new season came out a couple months ago."
"Megan, we watched the new season the last time I was over here."
"Ah. Well... what time is it? Wanna see how many Harry Potter movies we can get through?"
I checked my watch and saw 10:30. "Sounds good to me. My bet is we're asleep before the first one is over."
We curled up on the couch and threw a blanket over us. Megan rested her head on my shoulder and I could tell she was fighting drifting off before too long. I put my arm around her before I noticed her stirring. Out of nowhere, she sat up with a sigh of frustration.
"Ugh, fuck that guy."
"Who, Harry? I mean the kid is 11."
She laughed a little, saying "no, not Harry. The guy from the bar. I'm trying to not let him get to me but he got me so worked up and now I can't stop thinking about how the night could've gone." A slight pause followed by, "maybe you should leave, I need to get myself off."
I laughed and pointed out that I'd had at least a bottle of wine at that point, no chance I was going anywhere.
"Well, maybe you go sit in the bathroom for a while. Scroll Twitter or something and just stay in there until I tell you to come out."
I looked at her, waiting for her expression to change indicating she was joking. When I didn't move, she laid down on the other end of the couch and began to move her hand down her shorts and said, "well, are you gonna give me a little privacy?"
"Megan, how the fuck am I supposed to just sit in there when I know you're out here getting yourself off? That's an impossible task for anyone, much less a 21 year old."
I began to realize she wasn't joking when she closed her eyes and let out a little sigh as her entire hand disappeared into her shorts. Her words were starting to come a little more breathless now. "I don't care what you do, jerk off to it for all I care."
A slight moment of hesitation hung in the air, interrupted by a couple of nearly inaudible gasps coming from Megan. She paused slightly, opening her eyes to look at me, then closing her eyes again and getting back to work. I couldn't believe what was happening, sure that she was playing me somehow. But when she let out a little moan and started to rock her hips back and forth I realized that this was actually happening. I slowly untied my sweatpants and reached inside, grabbing my cock and began to stroke. I stroked long and slow, incredibly turned on but mostly confused by the situation. Megan's eyes fluttered open to look at me again, and when she saw my hand in my pants, she let out a louder moan and a little smile. This erased all confusion on my end, I was fully in the moment.
Megan slid her free hand up her shirt and started squeezing her tits. I took that as a cue to slide off my sweatpants and underwear so they hung around my knees. Megan watched, her hand still going in circles in her shorts, trying to get words out smoothly but too worked up to do so.
"Holy shit... I'm just realizing that... that I've never seen your cock beforeeeee. Not bad at all." She sat up to get a better look, taking off her shorts and underwear in the process. She now was positioned on all fours, her head a foot or two away from my cock, shirt up over her tits, and her ass in the air as she began to plunge a finger in and out of her pussy. I took my free hand and reached over to grab her tits, causing her to take her eyes of my dick and look up at me.
"u/RoyFookingKent... should we do this? I mean, this is a big move, I don't know if I want to date right now, and I don't want this to ruin anything between us. Friends with benefits gets messy every single time." The entire time she said that, she was furiously fucking herself with her fingers.
"What if... ok hear me out... we're this far already. Let's do exactly what we're doing now and when we finish, if we want to fuck we'll have an actually conversation about it."
"That sounds.... good to me... fuuuuuck pinch my nipple. Mmmmm ok you can touch my tits all you want but no pussy."
"Fine, no touching pussy and no touching dick, good line to set."
"No kissing either, I think kissing is really intimate."
I laughed again. "And you fucking yourself a foot away from my cock while biting your lip isn't?"
She didn't answer that, instead switching to rubbing her clit as she stared at my cock. She let out a high-pitch whimper, and moved to lay down on the couch. She rolled over so she was on her back with her head resting on my thigh, head turned to watch me stroke myself. I leaned my head back and let out a groan, beginning to pick up the pace a little. I turned to look at her body in the darkness, watching her tits heave with her breathing, shaking every time her body did. I grabbed a handful of them as I listened to her moans mix with the sounds of her wet cunt. I could see the wetness on her hand.
"Fuck Megan, you sound so wet right now. This is so fucking hot, I can't believe it."
She moaned her agreement as she looked up at me. "I know we set ground rules, but this isn't breaking one. Can you wrap your hand around my neck? I think.... I think I'll cum immediately if you do."
I looked into her eyes and slowly grabbed her throat. She kept her face towards me as her breath caught, eyes rolled back, and body violently shook as she came hard. Watching her body move and listening to her sounds, it was becoming too much for me to bear.
"Fuck, you're so god damn hot. You're gonna make me cum Megan."
Trying to catch her breath, she rolled off the couch and knelt between my knees. "You couldn't take your eyes off them earlier, cum on my tits" she said, pulling up her shirt.
I couldn't get words out, so I looked at her to make sure she was ok with it. She nodded and I immediately erupted, shooting ropes of warm cum all over her tits. We held eye contact the entire time and she placed her hands on my upper thighs, as close as she could get without crossing the lines we had set.
We were quiet for a second before she giggled and said she was going to clean up quick. She disappeared into the bathroom as I sat there in disbelief. When she came out of the bathroom, she put her shorts back on and curled up next to me. "Well... That was fucking hot."
"I can't believe it, that was one of the hottest things I've ever done."
"We're good, right? No weirdness?"
I thought for a second, thinking about how to go forward. "I actually think you're right... no weirdness. If we had fucked then maybe, but I actually think we're good." Then, with a wink I added, "If we can do this without it being weird, we should definitely do it again soon."
"Eh, we'll see. You'll just have to guess when I'm horny and come over."
I smiled saying I'd keep that in mind. We cuddled for a minute before she said, "I tasted a little bit of your cum in the bathroom."
My head snapped towards her. "Really? And...?"
"Tasted like cum. You've got a good diet though." She smiled and laid her head against me before we fell asleep on the couch.
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