I fucked [M]y best friends G[F], Sister [F] and Mum [F] within 2 weeks and i don’t what to do

I need more tags confession/cheatings/advice

“You know when shit happens and you don’t know how said shit happened and how to deal with the aftermath of said shit” – Anonymous

Hi Everyone, I suppose you can say this is a story but also me asking for advice. This all happened rather recently and I’ve been torturing myself inside for the past weeks and i just don’t know how to proceed. But first I’ll give you all a lovely story of how it happened then we can go from there. Buckle in it’s a long one.

Before i begin I’ll give you some backstory/context/descriptions of all involved. I’m changing our names but thats about it.

I (Ben), stand around 6ft 1 tall, with light brown hair and brown eyes. I have an athletic build from playing rugby for years. (Second row). I haven’t struggled in the ladies dept ever and very much live a nomadic lifestyle when it comes to relationships. *wink*

My best friend (James), is taller than me around 6ft3 but we share the same features. Hair/eyes etc. But he’s a big built motherfucker. Like me he played rugby, but was a tighthead. We have been friends since Primary. People would often joke that we were brothers, I would often spend a lot of time around his house, so I was rather comfortable around his family.

I suppose i should mention one thing now. James saved my life when we were 15 in a sense. We went on a holiday to Australia, i had the unfortunate experience being bit by a snake. But James being the hero he is, chased and caught the snake so it could be correctly identified so i got the correct anti venom. This is one reason why i feel like utter shit right now. He’s my Brother and he saved my life and i go and fuck everyone close to him.

Anyways, moving onwards. Next up is Jess.

Jess is James’s long-time GF. She went to our school and they have been together since like 6th form. Over 6 years now i think. Oh i forgot to mention. I’m 22, James and Jess are 21 soon to be 22. Jess is a cute blonde girl, with brown eyes and a bubbly face. She stands around 5ft 8 but has soft features. She has around a B cup bust, and a small but toned arse. She honestly is very pretty and a great laugh, I’ve always treated her like Sister in a sense.

Moving on is Becky. James’s older sister (23). Gonna be brutally honest. I’ve wanted to go balls deep in Becks since I’ve known her, I’m pretty sure she is where i get my taste/type of women from. She dark brunette, with brown eyes that are truly amazing. Soft facial features, that just make fall in love at first sight. Her body just seemed to get better as she got older, she has a generous C cup, she hits the gym hard and I’m pretty sure you can bounce anything off her arse. She is around 5ft 5. We are and always have been florty and teasy with eachother.

That finally brings me to Sue (48) . James’s Mum, who i often regarded as an Auntie. I didn’t really pay much attention to her looks but looking now, i just realised she’s a mature version of Becky. Brunette hair, brown eyes. She is slightly taller than Beck around 5ft 6/7, she has a great body for pushing 50. Hardly any stretching or sagging. Very much a 30 year old body on a 48 year old. She has generous D cups and a really big arse.

With that out the way lets begin shall we

Tbh it was just a normal day in covid life, i was going about my business (I’m a plumber by trade) and i received a text from Jess on the 5th Feb

“Hey Ben, Our bathroom sink isn’t working can you pop round and look please”

“Yeah no worries ill be there in 30”

I made my way round to Jess’s. Her and James recently bought a house back in July (was kind of ran down but they are slowly doing it up). I go upstairs and start looking at her sink, she comes and joins me to have a chit chat whilst i figured out the problem. Didn’t take her long to ask about my tinder antics (this was a common occurrence, Kind of a running joke that our friendship group regards me as a slut. I don’t deny it. My recent conquest was a big tit blonde called Lucie. Jess is one of those who loves details and i don’t hold back.

“So how was she” – she asked as i was fidgeting under the sink

“Probably had the best tits I’ve ever seen”

“Hmm ok, How was she in bed though”

“She was loud asf to be honest. Felt sorry from John (My neighbour)”

“I swear you say every girl you’re with is loud” Jess chuckles back at me

“I think they just all are. Guess i treat them right”

then all of sudden she blurts out

“Me and James haven’t had sex in weeks”

I rarely got an insight into their sex life, James was very crude when it came to it. I came from under the sink

“what why? Is everything ok?”

she just sighed

“I feel like we are drifting apart Ben.”

Honestly i was bit shocked at what she was saying.

“Don’t be stupid Jess. James loves you. Honestly, if something was wrong you know he would tell me. Think we both know he’s probably shattered from work that’s all”

She let out a deep sigh and lowered her head and mumbled

“I don’t think he’s the problem…It’s me”

Obviously all my attention was diverted from the sink to Jess at this point

She continued

“We’ve been together over 6 years now, and i hate to say it but … I’m losing interest. I feel like over the past year I’ve noticed a change in me and James isn’t fulfilling me enough”

I chimed in

“What does that even mean Jess”

“Sex Ben, Sex…” she looked as if she was about to cry

“Have you tried to speak to him about this? Does he even know what you are feeling like now?”

“I tried but he just comes home and goes to sleep. We barely speak at the moment” as she starts to cry

I stand up and walk towards her (she was sat on the bath) and wrapped my arms around her to hug her. She graciously accepted burying her head into my chest.

“I don’t know what to say Jess… I can try talk to him if you want”

She slightly nods

“Thank you Ben” she muttered as she pushed her head back from my chest. We both met with our eyes.

She leant in and kissed me on the lips.

I should’ve stopped it. I should’ve fucking stopped i, God I’m so fucking dumb. but i didn’t, I allowed it and accelerated it. I introduced our tongues and my hands began frantically exploring her body. She let out soft moans that just turn me on even more. I hook my arms back around her and pickup her up, she wraps her legs around my waist. We attack each others mouth still as i carried her to bedroom. At any point I could’ve stopped but i didn’t. I dropped her on the bed gently, Undid my buckle and drop my trousers and boxers revealing to her my dick. She rushed back up and took me into her mouth. She tongued the underside of my shaft whilst taking inches of me deep into her mouth. She took a brief pause to take off her top and bra, and pull down her yoga pants. (No panties underneath) I latched onto her breast as she took me back into her mouth. I ran her perfect pert nipples through my fingers, Her moans were amazing and just kept spurring me on. I had enough, i wanted to be deep in her. I nudge her shoulder with my hand and she laid back down the bed. I dropped to my knees and begin licking her pink pussy. Didn’t take me long to find her clit which i gently circled with my tongue. I felt her breathing become slower and deeper, a few more seconds of licking her clit she froze and gasped. Shortly a vibration ran through he body as her pussy leaked its juices.

Completely in the zone, i grabbed my dick and thrusted it deep into her. She was tight, it was a struggle not to bust my load on impact. I gave her 10seconds to adjust to my girth before turning into my normal self as pummelling her with a steady hard tempo. All she could do was murmur my name along with several fucks and i within deep into her. I felt her walls contract around my dick, her body froze again and she let out an almighty moan gripping onto the bedsheets. I felt all her juices run down my shaft. I was getting close. I exit out of her, and pick her up and spin her round to doggy. I entered with haste and kept the same pace as before. Her head just buried into the bed.

“Jess, i’m gonna cum”

“Yes Yes Ben, Cum in me ” “Please mhmm Cum in meeee” as i pummelled her even harder, shortly after with one deep thrust i exploded, blasting deep inside of her. i let out a long “aghhhhh” as i normally do when i bust. After i finish pulsating i gently spank her ass and pull out and collapse on the bed.

Didn’t take long for the instant guilt to me and her as just laid there on the bed

She was the first to speak

“Think its best we don’t mention this too anyone”

I just laughed “Yeah i think thats best”

I sat and grabbed my clothes and got dressed and just stared at her and smiled

“I’m sorry Jess” I couldn’t pinpoint to you what i was sorry but it just felt right to say.

I swiftly went back to the sink. one the pipes was loose so easy fix. I shortly go to leave afterwards. Jess just remained in the bedroom in the same position (flat out naked on the bed) As i looked in i asked if she was ok?

“Never better Ben…Never better” she looked at me with a smile.

I waved and left as quickly as i could.

I couldn’t think straight the entire day after that. I was just plagued with guilt. I even had texts from James, completely normal texts but i struggled to reply. Didn’t take me long to think about random theories. The sink’s pipe was clearly just loosened. Did Jess do it? On purpose? you get the idea.

Later that evening i got a text from Jess

“You free to talk?”

i said yes and shortly she called me

Tl;dr of the phone call : We both agreed it was just an impulse mistake and it shouldn’t ever happen again and we will tell no one. Although she thanked me for the great time.

In hindsight that was a huge red flag after we literally just agreed it was a mistake but we’ll get to that later.

After the phone call i felt much better but still very guilty. I resigned myself to my house for a few days.

On Tuesday(9th) i was just at a clients house servicing their boiler when i get a text from…

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Sorry this was long one and took a while to write, I’ll next part as soon as so you guys can help me in the present before i fuck up (even more). But would love to hear your advice (obviously without all the details). As of writing this (14th Feb) James doesn’t know anything.

Source: reddit.com/r/gonewildstories/comments/lkdf25/i_fucked_my_best_friends_gf_sister_f_and_mum_f

72 comments

  2. Wow first off great story can’t wait for more.

    As for advice, i would feel like James probably has already expected you and his sister to have done something? Since you apparently flirt and tease all the time.
    As for his mum and you cheating with Jess i dont know. You fucked up ahaha

  3. What does the stand up, morally correct version of you think you should do? When you have that answer, then you will know.

  4. Great writing.

    Advice wise, nothing wrong with the exception of the GF. Sister and Mom are fair play unless the Mom is married.

  7. Great read!

    ​

    advice: note, I’ll be providing across the three different stories But for Jess’s sake, don’t feel guilty about it. If push comes to shove and the news comes out, you can say she‘s the one who started it, although it doesn’t sound great, you were previously talking about sex and her relationship with James and it just happened. You do have to think though how guilty Jess feels rn, so if I were you, just be prepared for them to have the talk, as all cheating stories come out…eventually (don’t believe me, look at the number of those from r/Infidelity and r/relationship_advice being unable to believe they’ve been caught or caught cheating a cheater.)

  10. You fucked up man it’s too bad but to me you have 2 choices come clean (which probably wont end well and end the friendship and jess and james relationship , which seems like its already in the gutter) or hold it in and keep lying to james which would save the relationships but I cant promise that your guilt will faid so you would have to live with that.

    I’m really sorry mate I know most guys would also fall into that trap from the first instinct

    This advice is just based on this part so I dont know how you would come out from the rest of your ‘adventures’

  11. Seem like you fuck big time with james gf but for sister and mum. It is fair play unless she is married. Love to hear the rest of story. How can you feel guilty and end up fucking the sister and mum after the gf?i dont think there was any guilt there mate.

    What is done is done. Just keep your mouth shut about james gf. Let her break up with him.

  14. I’d love to be your friend, dude. lol

    Jokes appart, keep fucking the girl is a mistake even bigger that starting it. I really thing this event should only be kept in your memories. BUT if you think their relationship will end, there is a possibility that she tells him, and that would be bad. Consider telling him if thats the case, cause there is the possibility that the damage is smaller.

  16. Great story. Well written. My guess is that your home country’s ‘plumbers’ are much more articulate than those in my country.

    If true you’re a complete sh*t. With ‘friends’ like you, who needs enemies?

  19. DON’T FUCK James!
    Censorship on reddit prevents me from reading about James’ mother and sister. But, I hope you “LEGGED THEM DOWN AND SMACKED THEM JACK’EM”!!!

  22. Incredibly hot! We need the stories with the sister and mom asap!

    I’d say to cool it with Jess until they sort things out. From my own experiences with women, she definitely planned the entire session down to a T. The fact she wanted your cum too is so hot, ngl

  23. Why is there always a hottie named Lucie in the stories from ‘Straya on this sub lol

  25. [F]ar away in the land of [F]almuth lived a [F]emale [F]abrege egg artist na[M]ed [F]elicity, she is known [F]or being a very [F]un person [F]requently [F]inding [F]antastical [F]eistas

  28. does he have any female gamily members you havent banged? you should make a list of his female family members and see how many you can cross off the list. maybe granny needs the cobwebs dusted off too.

  31. Go ask your mate how he feels about the relationship, depending on his response either tell him he needs to end it (if their feelings are mutual) or tell him she told you they are feeling distant. Don’t tell him about the sex, and if he asks why you are seeming off just tell him it’s because of this situation.

    Chances are they will end up splitting anyway, these things just happen in life. He is still your best mate.

  32. Honesty. Maybe not abt the sister and mom. But tell him abt the gf. Talk it out. In the end she started it, so even tho it was ur fuck up to keep it going, she did initiate, and she was iffy abt their relationship. Honestly just go to him, talk it out, maybe take a punch or 2, but ull be ok.

    As for the sister and mom. Lmao no idea what to say here. Good job?… it shouldn’t really be something to be ashamed of with ur friend (compared to u sleeping with his gf). I wouldn’t mention it now. My logic is that u have information that he needs to know rn. Life altering stuff. Maybe leave the bro mentality out of it rn and just tell him what his gf is feeling abt him

  37. I am expecting james to kill you. Please keep us updated or we’ll assume you’re dead.

  40. Your situation is rough , but I been there I had a friend and apparently he was a bad lay, all his girlfriends eventually pushed me into a corner to hook up with me. Gotta say my friend wasnt into oral sex , giving or receiving and was a plain missionary type of a guy. That just leads to breakup no matter how much love is in equation. If your partner is not sexually compatible with you or viceversa save yourself years and just breakup early. Also dont feel guilty at all , chicks at 22 have an insane libido and will purposely hit or tease their bf buddies for attention, but then the fantasy goes out of control which leads to what happened. Forget about it most couples in their 20’s rarely stay together for more than 5 years.

  46. Wtf ben, this is James, you could have at least changed the names! Can’t believe you fucked Jess, my sis and my mom, you better hide your dog cuz I’m cummin bro.

  50. I hope that James isn’t a regular reader of posts in this sub. Or that you’re bullshitting with a lot of detail you provided, otherwise he’ll work it out pretty damn quick.

  51. If this is a story nice well put together and I like the premise.
    But if any of this is real then go away. Don’t explain don’t tell him just leave him and his family alone if at any point you considered him a friend then leave. Telling him will only make you feel less guilty it will do nothing to help him knowing about his gf is one thing but what advantage or even help would knowing about his family. Stop being selfish just do the honorable thing and leave him to live the rest of his life without such a toxic person.
    Also stop calling yourself his friend you were never that close if it was this simple to push you over.

  52. Sorry Dude, but you’re definitive POS.

    “Just because you could, doesn’t mean you should”
    -Dr: Ian Malcolm

  55. What a banger story.

    As for advice, Man, I think you need to tell James about Jess. But i think we all know if you do that you’re fucking up your chances with Becky and possible your friendship. But will be interesting to see how this progresses.

  56. Don’t tell anyone. She wanted it. She needed to compare to see if she was missing anything before being stuck with it for the rest of her life. Invite her over. See if she wants more. Hit it as often as you like. If she really liked it she’ll want more whether it’s from you or someone else.

  57. You don’t know what to do? Protect your shoulders from probable rotator cuff injuries caused from the endless high-fives you will be getting from your buddies.

  60. I’ve had a similar situation in regards to fucking my best friend’s sister. I kept it to myself for like two years and told him earlier this month. He took it well since she’s become a well established hoe since the first time we’ve hooked up. My best advice is to come clean about his girl and sister and take the ass kicking you deserve. But you need to speak with his mom and establish that you will both die before that info gets leaked

  61. Dude, assuming this is true, its not like anybody would lie on the internet, right? Assuming it is true, you obviously have to fuck James. There is no other way.

  62. Athletic, tall, good with the ladies AND on Reddit? Ha. Pretty sneaky, but you don’t trick me. We don’t do that here.

  64. Great story! I would fuck them all as long as you can get away with it. In the end it’s the things that you don’t do that you regret.

  65. Plot twist: he is going to ask her to marry him and he has been planning things out ?

  67. Well you pounded it out, you either tell him, or continue on guit free. Because honestly your 21/22 young and dumb and running on hormones

  68. I read the title and thought that was going to be far more fucked up than it was haha

  69. Aussie here, don’t chase snakes. Alot of them are angry fuckers, they’ll sooner kill you, your dog, then hunt down your parents. The anti vemons produced can be some what universal till you can give a better description

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