I’ve received a lot of DMs asking for more stories with me and best friend so I thought the next logical step was for me to write about the time we finally got to have sex. Hope you enjoy it as much as the last one!
After the night described in my last story, mine and Emily’s friendship changed. We were still inseperable and best friends, but also sexted a lot and we found as many excuses to be naked in front of each other as possible. We decided to set some ground rules mainly so that we didn’t ruin our friendship. We loved the sexual chemistry we had, but we both knew that we didn’t have a romantic future together. We also understood that our friendship was one of the best things to ever happen to the both of us and we didn’t want anything to even risk getting in the way of that.
The ground rules were pretty simple. No sex ever, kissing was allowed but only a peck on the lips. If we got really worked up and we were sharing a room we could masturbate together but we could only watch eachother with no touching (the previous story was a one off).
We compensated with those limitations as much as we could by doing other things. For example, we made sure that there was full eye contact whenever we told each other we loved each other. When we were masturbating together we usually said each other’s names as we came. Also nothing was off limits when it came to dirty talk, be if face to face (as long as there was no touching) or sexting.
This worked for us perfectly. We graduated from college and went on to get jobs in different cities, but not too far away that we didn’t see each other pretty much all the time. She broke up with James and got into a proper long term relationship and I met the woman of my dreams (obviously neither of our partners know the extent of our friendship because they wouldn’t want us anywhere near each other and in fairness who could blame them).
Our friendship didn’t waver, we didn’t drift apart, and we continued to be 100% in each others lives right up until I asked her to be Best Man at my wedding, which is where our story starts.
I was in the hotel room that the groom got free with the wedding package. I had showered and got ready so the only thing left to do was to put on my suit, but I still had a few hours left until I had to be downstairs so I was lying on my bed in my boxers scrolling through my phone when I heard a knock at the door.
I looked through the viewing hole and saw Emily stood there
“Open up choad!”
I opened the door and pulled her inside before the hotel’s other patrons came out of their rooms to see what was going on. I closed the door and turned back into the room to find Emily sat on the bed. She was wearing her best man’s dress which hugged her figure and showed her huge tits. We had tried to go for the sluttiest dress possible without pissing off our respective other halves.
“What are you doing here? And if you say something cliché like ‘making sure you don’t get cold feet’ I’ll slap you”
“As if! She’s way out of your league, you can’t afford to get cold feet. You’re lucky she lets you breathe the same air as her let alone fuck that riduculous porn star pussy”
Over the years we had shared pics of people who we had slept with and, ever since she had first seen my wife to be’s pussy, it was a running joke that Emily was insanely jealous that she had a full bush and huge inner labia that hung far down from her pussy and my wife had been blessed with society’s interpretation of the perfect vulva where it was totally shaved and nothing was on show save two perfect lips that met precisely in the middle.
“Well what do you want flappy bird?”
“HA! HA! I have come to give you your wedding present!” she stood up and twirled around the room “unzip me, please”
I stood up and walked over to her perplexed. The only thing I could think of this being was a matching tattoo she wanted us both to have. I unzipped her dress and helped her step out of it. After she hung it up to stop it from getting creased so turned around to face me with her arms spread as if to say “Ta Da!”
Underneath her dress she had tied red ribbon around herself. It crossed over her nipples, although they were so big and hard I could still see them poking through, and ran across her pussy. Over her pussy she had placed a large bow and as she turned I saw she had a smaller one between her butt cheeks.
“Well?” She asked
“Well what?” I was none the wiser as to what was going on
“Ergh!” She reached across to her handbag and took out another bow which she put in her mouth “what about now?” She said her voice muffled by the bow
“I have no idea what’s going on, Em”
“My holes! That’s my gift, I’m gonna let you fuck all of my holes before you get married”
“Are you serious?!”
“Yep!” She said as she walked over to where I was sat on the bed. She bent down and kissed me on the lips “it was the best thing I could think of to show you how much I love you. And that’s not all, unwrap me I have another surprise”
I reached up and started to unravel her. She spun with the ribbon and as if fell she faced me with her hands on her hips. Where I had expected to see her normal untrimmed hairy bush I was now met with a completely shaved pussy. This must have taken a lot of courage as if was sort of an unspoken fact that she had never shaved her pussy because she wanted to cover her dangling lips as much as possible.
“What do you think?”
“It looks amazing! I didn’t really realise how huge your lips were and how far they hang down from your pussy. Your clit is huge!” Without the hair her clit was clearly visible between her pink lips
“Yeah I know I had to get a bigger bow to cover them up. I’m not really embarrassed about you seeing them like this, but do you think Craig will like it? I’m gonna let him fuck me tonight and pretend it’s a present for him and not you obviously.”
“Of course he will. He’s eaten that pussy before he knows how big your lips are anyway.”
“Good. Well, now you know too and” she said as she straddled me rubbing her pussy lips against my dick which was hard inside my boxers “you get to watch them flap about as you pound the shit out of me” she kissed me deeply and pushed me back on the bed as she reached down and pulled my boxers off me. My dick sprang free and she sat in the cow girl position on top me rubbing my swollen head against her lips making them flap left and right.
“I’ve masturbated over something like this happening at least once a day, ever since the night I let you slap your purple head on my gaping asshole.” She said as she held my dick in line to her pussy and slowly impaled herself on it. We both groaned as she slowly worked at it until it was all the way in. She started to rise off of it and I watched as her huge lips gripped my dick on the way back out.
“How does that feel, is it tighter than Sarah’s?”
“Ah fuck! No sorry your pussy is nowhere near as tight as hers. I can’t fit in all the way straight away like we just did”
“Oh my god! Fuck! I love that you know exactly what I want to hear! Even though you tell me my pussy looks fine are you secretly glad you ended up with a perfect little innie to fuck instead of having to look at this mess every night like Craig?”
“Ergh I know you want me to say yes, but I can’t, you know how much I love your huge lips. When I’m fucking Sarah I imagine your huge lips on her pussy and it makes me come so hard. I just wish your pussy was tighter than this!”
“Fuuuuuuck! Is it okay if I make it up to you with my ass hole? That’ll be nice and tight for your monster won’t it?”
“Yeah baby I can’t wait to ruin that hole. I hope you’ve kept it hairy for me”
“Yeah it’s as hairy as when you saw me gape it for you at college. I’ve never let anyone in there it’s just gonna be your hole forever!”
Suddenly I lifted her off my dick and laid her down on the bed on her back
“Sorry I was gonna come and I want to try all your holes first”
“Eat my pussy before you fuck my other holes, I wanna watch you suck on my lips”
I grabbed around the hips and dragged her towards the edge of the bed so I would be able to kneel down, but before I could she stopped me and said “Oh wait hang on I’ve got another surprise!” With that she got on all fours and spread her butt cheeks to show me that a sparkling butt plug was wedged in her tight hole.
“To be honest, I had to wear it because I’ve never done anal and there’s no way I could take your dick without training it up; I’ve been wearing one for like two months. But! It also means I can show you this” and as I watched she slowly pushed the butt plug out of her hole until it shot out on to the bed. Emily let out a relieved noise as her hole adjusted to no longer having the plug in “Seriously, I would never do that for anyone else, it’s so embarrassing. I’ve been thinking about you watching me do that for the past month and it makes me come in like 30 seconds. Okay eat my pussy baby, make me come nice and hard”
I dragged her towards the edge of the bed and lifted her feet above her head. I didn’t bother with teasing and sucked her lips straight into my mouth, alternating between doing that and tonguing her huge clit.
“Oh fuck fuck! Slow down! Do it in little circles around my clit!”
I did what she said and every now and then sucked her clit into my mouth, it was big enough that I could have it in my mouth and use my tongue to roll it around.
As I continued to lap at her pussy, I saw her hands start to clench on the bed sheets and her chest starting to flush a reddish colour so I stopped suddenly.
“Ergh! What are you doing I was about to come!”
“I know I’m just edging you a bit I’ll let you come soon don’t worry”
With that I lifted her legs higher and rimmed her hairy butthole. I had never done this with anyone before but it felt right with Emily
“Oh fuck! Yeah tongue fuck my brown hole! It’s yours! I wanna taste my bum hole on your lips when you fuck my asshole.”
I kept going taking huge licks of her hole and putting my tongue as far in as I could, feeling her clench it around my tongue. I moved back to her clit and continued to alternate between them, edging her until she cried out and came as she shouted my name.
“Holy shit I thought I was gonna pass out! I just came so hard.” She turned around on all fours presenting her butt to me again. Her hole was still gaped from the butt plug surrounded by hair that was wet from where I had rimmed her
“Turn back over, I wanna see the face you make when you get your asshole fucked.”
“Ergh how do you know exactly what to say to make me feel so degraded. I love it when you humiliate me like this, I just wanna be your little fuck toy”
She turned over and held her legs as far as back as possible. I used some lube on my dick and lined it up to her hairy hole. She gritted her teeth and nodded and I slowly pushed myself inside her.
Her anal plug had worked. Although it was ridiculously tight I didn’t have much bother getting it all the way in. We both groaned in pain and pleasure as I bottomed out inside her.
“Okay take it all the way out and shove it all the way back in. When I fuck Craig later I’m gonna show him my asshole and pretend it’s just my resting gape. I want you to see me stood with you at the altar knowing you’ve completely wrecked my hole and that under my dress it’s just there wide open waiting for you if you wanna use it again.” She kept up this dirty talk as I did what she said. Soon her hole was letting out loud squelching noises as I entered it again and again “Kiss me so I can taste my asshole” we kissed passionately as I continued to batter her brown hole “In a bit I’ll suck you clean and then you can fuck my face. I would let you come inside me but Craig will probably be suspicious enough when he sees the damage you’ve done to my hole without your come dripping out of it too”
We continued to fuck her tight little hole for a few more minutes and when I felt I was getting close I pulled out of her, put her on her knees, and let her suck my swollen dick clean.
I held out for a minute or two before grabbing her hair and forcing myself down her throat. She took it like a champ, with tears running down her face, making huge gagging noises as I hit the back of her throat again and again.
Finally, I couldn’t take it anymore and I aimed my cock at her face as I came harder than I ever had. She opened her mouth and swallowed as much as she could but most of it landed on her face gluing her eyes shut.
“Fuck that was amazing!”
“Yeah I take my best man duties seriously, Choady”
Source: reddit.com/r/gonewildstories/comments/hvv9in/best_friend_lets_me_fuck_her_on_the_day_of_my
One of the hottest stories ive ever read on here
These are great stories but I’m curious, if you are inseparable friends and have great sexual chemistry, why exactly don’t you just marry each other?
Hella fuckin hot. I’d love to know your dynamic. It might sound kinda cheesy, but do you think you’re eachother’s soulmate but not eachother’s love if your lives? Which is funny that I ask bc I’m not sure how much I believe in soulmates ? but it kinda makes sense tho?
So was this the only time it happened? Or did it happen again?
I want you to do anal with Sarah just to make her mad lol
Great story liked it a lot !
Does your wife know
I hope for more stories like this between you two
Really hot