First Post Here https://www.reddit.com/r/gonewildstories/comments/3qt16b/i_took_my_fianc%C3%A9s_little_sisters_virginity_first/
A week and a half had passed since we returned from the Maine house. A week and a half since Madeline, my fiancé’ Jamie’s younger sister, lost her virginity to me. 10 days after I had sex with a girl other than Jamie for the first time.
It all started with Jamie’s suggestion that we each try sex with one new person before our wedding. The “hall pass” made sense because we had both been exclusive for 10 years (since we were 14 and 16).
Madeline waited almost 11 days after she seduced me to talk about meeting up again. “I was really hoping you would fix the glass on my busted iPhone.” She was cashing in on the favor I drunkenly promised her months ago. Maddie made her visit to Chicago possible by suggesting to Jamie that they dress up as Victoria’s Secret Angels for Halloween. Home run idea.
I was picturing the PG-13 rated costumes that you on TV. Madeline had apparently taken the intensity up a notch. She ordered wings, corsets, thigh highs and (my favorite) cheeky panties with big bows on them. She also added some knock off kimono robes to cover up their asses just enough to get away with the ridiculous getup.
After hours of driving for Maddie, and an hour of getting ready in the bathroom together, finally I got to see these costumes. “We need your help with the wings” Madeline ran over to me as she was holding up both sets of wings. I had to cut small slits in the back of the cheapo robes so they could clip the wings to the corset underneath.
Jamie was first, so I positioned myself behind her and performed the job. Jokingly, Jamie grinded her nearly bare ass on my crotch. She giggled, “Do you like my hair? It’s a mess.” Madeline was looking at us the whole time, “You guys are so cute.” Next, I was cutting Madeline’s robe. Surprisingly, she did the same grinding motion as her sister. Jamie was in the other room, “Should I wear my hair up” she yelled from the bathroom. Madeline was continuing to grind on my quickly growing dick. She kissed me on the cheek, turned around and bent forward to grab her phone. Maddie finally replied to Jamie, “Sure, do whatever you want. Lets take some pictures.” Meanwhile, her reach was giving me a full view of her mostly-exposed ass and the perfect outline of her covered pussy. Maddie ran into the bathroom with her phone and shut the door.
In no time we were at Lucky Strike in downtown Chicago, 4-5 of Jamies friends in tow. With so many of Jamie’s friends around, I had to play good-future-husband and bullshit with them. At several points in the conversation, I noticed Maddie looking at me and smiling for no apparent reason.
Before too long, Halloween Saturday came to an end. Madeline was wasted, but on the other hand Jamie was stone-cold sober. Good girl, she was planning a long run by the river in the morning with her trainer.
The Uber ride back was quiet, but Maddie was tapping me on the leg. She motioned to her phone and unlocked it to reveal a picture of her and Jamie in the mirror. A picture from earlier in the bathroom. A perfect view of them facing away from the mirror in their new cheeky panties, pretending to grab eachother’s ass (Hoverhand?). She must have snapped it when they were changing. I joked with one word “Instagram?” Jamie looked back at us and Maddie put her phone away, we were pulling up to the apartment.
The next morning Jamie went out for a run, while Maddie and I stayed back so I could “fix her iPhone finally.” With a 10 mile route in mind, we knew Jamie would be at least a couple hours. I still had it in my head that I would somehow finally reject Maddie at the last moment. Still feeling a little guilty about our first hookup.
As soon as Jamie walked out of the door, Madeline stepped into the bathroom and told me to wait on the couch. Madeline walked out of the bathroom wearing last night’s costume without the robe. “You’re going to make me cum this time right?” I laughed, but quickly realized she wasn’t kidding. The last time we fucked, her first time being penetrated, she cried and bled. “Maybe we should work on the iPhone,” I halfheartedly suggested.
My phone can wait, the crack is small. She grabbed her boobs and pulled them up and out, over the tightly fitting corset. I couldn’t stand it anymore, this fantasy was getting too real. I stood up and she leaned forward to kiss me eagerly.
Maddie turned around and started grinding on me, she reached back and unbuttoned my jeans. As she was undoing my pants, she revealed a bottle of coconut oil and squeezed most of it on my mostly-hard cock. “I asked Jamie to borrow some of your coconut oil for my hair” This was the same bottle of oil that Jamie and I had used to fuck a few days prior.
After stroking me to full length, she turned around and kept grinding on my slippery, wet, throbbing cock. I grabbed the bottle of oil and dumped the rest on her ass, so it would be shiny and slippery. This is where I reached into her tiny pussy with one finger. Even one finger was enough to make her moan. I could see her whole body react as I fingered her very slowly and carefully.
Maddie fell on top of me and began unbuttoning her corset with one motion. Her whole top half was exposed, and I could see thick tan lines. She had spent the last week in Cancun with her Sorority. I yanked on her panties to pull them half off and asked how she wanted to do it. Instantly Maddie turned around to the reverse cowgirl position and put her warm pussy right in front of me. Her ass was still shiny and covered in lube, I could see her pussy was ready for me.
I could see her perfect pink slit and tiny tight asshole right in front of my dick. She put her labia right up against me and I held it there. This is when I realized she had no idea how to insert me without help. I still can’t believe how inexperienced she is. Once I was inside of her, we held still and she started audibly wincing. I barely went in and quickly noticed she was way too tight for this position to work without pain. This is when she took the lead and inserted me all the way by sitting all the way up on top of my dick. She winced even louder, and I was worried she was in serious pain.
“No pain no gain” she said as she laughed and half-moaned. Maddie was now slowly bouncing up and down, but soon flipped around so she could kiss me while on top. I hugged her tight to slow her down, and felt her hard nipples press against my chest. She was getting more wet by the minute. Soon Maddie was moaning louder, but I could tell she was trying to repress the involuntary noises. Jamie always tried to mute herself too, embarrassed to moan too loud.
As she was riding me, I started to think about how many times Jamie had ridden me in the exact same spot. Honestly, Jamie is better at sex, but Maddie’s younger and tighter pussy make up for her lack of experience. I was starting to feel the climax coming on too early.
“Lets slow it down, take a break, let me touch you for a minute.” I begged. “This is my first orgasm from sex.. My rules.” She took this as a challenge, looked at me in the eye and clenched her pussy as tight as she could. I whimpered and tried to pull her off of me. She started to ride me faster until I warned her one final time “I’m going to blow inside of you.” Maddie started kissing me, taking deep breaths, she wanted my cum inside her.
I started to release, while trying to hold it back. This is never an awesome feeling, but the sight of her shiny ass was worth it. She screamed and panted loudly, twitching her pussy up and down lightly to finish me off.
“Thank god we used a condom,” she sad jokingly. “Uhh I think CVS downstairs has Plan B?” The cheeky panties were still around her ankle, so she pulled them back on. As soon as she had the underwear on, she exclaimed “Oh my gosh, its leaking out of me.” Maddie embarrassingly put her hand over her crotch and retreated to the bathroom.
We got plan B and chatted for about an hour before Jamie got home. I ended up fixing the iPhone just as Jamie got back. This will be our last time having sex, but we’re going to remember it forever and keep it sealed in the vault.
I think Maddie and I will have a strange, ongoing bond for a long time. I still have the panties from the first time we fucked in the N64 box and I also have the picture of her and Jamie in the mirror as a memory.
Source: reddit.com/r/gonewildstories/comments/3v7bsx/did_it_with_my_fiancés_little_sister_again_we_had
Is there anyway we can get some pics.
Sorry but no chance.
Geeze if u guys REALY want fotos tell me what to post, I could b convinced
fun story, good thing plan b is so easy to get now
Anything "wrong" is typically hotter/sexier, so kudos for the hot story. I’m going to pretend this is fan fiction…. this stuff can fuck people up years…
Her left thumb please.
What can fuck who up? Confused.
we actually had to go to 3 stores, all in downtown chicago, the first two stores were sold out LOL
If you’re genuinely confused as to how this situation can "fuck people up" for years then you’re either the biggest moron in the history of the world or this is just fan fiction. I sincerely hope it’s the latter as well, for the sake of your fiance. If this is true, the truth *will* get out eventually. Keep that in mind. If this is true then you also need to tell your fiance and end the relationship as soon as possible.
This whole thing is so fucking hot. I’ve always had relationships where they were "wrong" and this is my type of boat! Great story!
legs
Maddie’s ass would be nice
What’s your plan B when your wife finds this out years down the line?
how about sharing the pic off the 2 girls doing the selfie in the mirror, with their Halloween get up?
Man her little sister has got you blackmailed like a motherfucker man. Don’t piss her off.
I’m thinking like blocking out her face and jst like a body shot. Even one of your wife to. Now that would give everyone on here reading your great story a visual of what your dealing with.
Hot! I was wondering when you’d post this story… I live right across the river from Lucky Strike. Too bad I didn’t see a couple of hot chicks dressed as VS angels on Halloween
Pretty reasonable request.. hmm
I doubt it, she is very passive and was honestly looking for a non embarrassing way to lose her virginity. Maddie had several chances with other guys but was afraid she’d be bad at sex. She knew I could’t judge her performance or tell anyone about her. Honestly I think she seduced me because she knows I can’t talk about it.
Thx for the kind words!
I doubt the truth will get out. Maddie and I are equally nervous about the other telling Jamie. It is mutually assured destruction. Only problem is that Jamie is "worried about Madeline’s social life, she still hasn’t done the deed" her exact words. Maddie will have to make up a story about her first fuck boy at some point.
Honestly I think the controversy fades with time. Jamie used her hall pass last month in Israel. She fucked her second cousin. This isn’t as racy as me fucking Maddie, I know. What would you suggest as my next move?
We’ll see about that in 10 years
Well, in that case you both are even! Made for each other.
The controversy will never fade. This’ll destroy all three of your relationships if it ever gets out.
I’m thinking a hall pass is different than fucking her little sister. I’d be *enraged* to find out my partner slept with either of my sisters. I feel like that’s an unspoken line you don’t cross without explicit permission. But, I mean, if you’re confident that she’ll never find out, my best advice to you is not to have booze at your wedding. Because then it WILL come out.
It’s not gonna be the last time. Sry
I like the way you ended it, its like a happy ending.
post the picture you talked about in the story (with the faces covered if you want). pics or it didn’t happen…
dick says yes it will happen again, head and heart say it can’t happen again.
it is the truth!
Hmm, I don’t know if I should. Maybe will post nn pics?
Personally I’d luv to see a pic of this girl, but maybe u should try to get ur fiancé on board with this. Have the sister recommend a little three way party and see if u can get her interested.
There is a lot of truthes as other people have mentioned I like how this is the tone you ended with. It was fun but now I’m doing the whole relationship thing. In the side you should check out nonmonogamy, sounds like you guys might have fun with it
You have absolutely zero empathy for the person you’re about to marry
I deserve this and, yes you’re probably technically correct. Honestly Jamie and I have a great relationship. We both got some weird shit out of our system this year, so I decided to write about it. Honestly writing about it made me feel guilty but also glad that I had the balls to go through with it twice.
I doubt it will ever get out, honestly. Maddie was looking for a secret way to lose her virginity. She was embarrassed to be a virgin, and wanted a sure-secret way to get a little experience. She has more to lose than I do, Maddie knows her sister would HATE her forever if this got out.
When are you going to tell her you used your hall pass?
Lol wow bet you were worried for a second
Ugh, Jamie is trying to set me up with her friend, and I’ve been basically adamant against it for a month. The irony is that Jamie feels suuuper guilty about (supposedly) using her hall pass first.
Hah, Maddie was saying she would drive north to Milwaukee if need be. The girl is probably veryyy fertile so I’m basically an idiot for busting anywhere near her vagina.
No, you *think* you have a great relationship and you thrive off of the attention you’re getting here. What kind of "great relationship" involves one of the partners secretly sleeping with the other’s sibling? You’re delusional and every comment you’ve posted ends with something along the lines of you’re "glad" or "you know it will happen again". At the end of the day you don’t regret what you’ve done, you want to continue with the affair, and you *still* want to marry your fiance. How fucking insane are you? Honestly. How would you feel if your fiance had sex with your brother multiple times? What about your father? I’m done talking to you because I’d rather just sit in ignorance thinking everyone in this situation is just fucked up in the head and is okay with this. I think that’s the only way I can reconcile living in the same world as someone like you and the person you’re having the affair with. On one hand I feel bad for you because you seem to recognize you’ve made a mistake, but in the same breath of air you gloat about how much you enjoyed it. I’m all for a good story, but not when it becomes personal and you’re clearly going emotionally annihilate someone. I wish you zero luck in the future and I hope your fiance figures you and her sister out for the scum you both are. Peace.
Agreed!
Keep it up….maybe you can be the father of both their children. Ha
I deserve the burn that you are dishing out here. Please consider the context though. Although I do regret what I’ve done, it isn’t a crippling guilt. IMO it would be different if I seduced Maddie. This was her idea, and honestly it was her ideal choice for losing her V-card. As for Jamie fucking my brother or my father, I guess the thought doesn’t exactly turn me on. Honestly though, if I had a brother I wouldn’t be PISSED if they did it once. Bottom line is, you do not realize how sexually open Jamie, Maddie and myself are. My guess is you are a bit closed out from your sexuality so anything wrong or new freaks you out. AMIRIGHT?
Damn that’s hot, you lucky sob
> My guess is you are a bit closed out from your sexuality so anything wrong or new freaks you out. Because I disagree with having a *secret* affair with my fiance’s sister? That’s absurd to you? That makes me a prude? If you all are so open with your sexuality why is this such a safe guarded secret? Hmm, that’s right… You commented on how it would destroy the sisters relationship. If you’re so sure it’s going to destroy their relationship, why would it be any different between you and your fiance? Yep, sounds like you all are really "open" with your sexuality and your fiance would be just peachy knowing you’ve taken her sisters virginity, fucked her again, and hid her thong in your console. I say that with an assuming tone because I’m still hoping this is a joke.
Thanks for the kind words, I wouldn’t call me "lucky" so fast. There is a lot of stress that comes along with this predicament. I’m looking at the positive and am thankful for the chance to score an epic pair of pussys.
I feel bad for Maddie. Sex with you sounds very unsatisfying. You don’t even try to get her off at all. She’s obviously trying positions that she thinks a guy will like and that obviously aren’t going to get a virgin off. She may not know this but you should. You’re using her for sex right now, don’t convince yourself you’re a sex God who’s teaching her how to have sex in a fulfilling way. It sounds brutal for her actually.
Real talk now. I’m definitely not great at sex. I caused Maddie a lot if pain, didn’t even get her off the first time. She says she orgasmed the second time but I’m not sure. My dick is a bit on the small side honestly, which Jamie likes because she’s very small set.
Size of dick has nothing to do with it. The positions you’re describing would be basically impossible for most women to get off with, let alone a newbie. She’s lying when she said she got off. No offence. She also may think that was a great way to lose her virginity but in the end she’ll realize it was a horrible idea and horrible experience. She got no benefit out of it what-so-ever.
No benefit? I think it is easy to argue that Maddie loved the forbidden nature of it. Plus she is glad to feel a bit more experienced. You’re like 65% correct though.
Yeah, I enjoy the fucked up stories as much as the next guy, but: 1) there is zero chance this doesn’t come out years down the line and ruin everyone’s life. 2) You either need to hook Maddie up with someone or move overseas if you’re going through with the marriage. 3) If God forbid you and Maddie hook up again, *please* go down on the poor girl, or help her masturbate herself to orgasm, or *something.* She’s obviously pulling out all the stops for you for some fucking reason, and you’re just being a selfish bitch. Get the poor girl off if you’re going to continue this self destructive affair.
Tell Jamie’s story, about her using her hall pass!
1. This is certainly not going to ruin my life. As for Maddie, this was her idea so I don’t feel bad. Honestly I really doubt Jamie would believe Maddie if I denied the affair. 2. Maddie is away at school hundreds of miles away. Jamie and her don’t talk much, so why worry? 3. She would have been better off if I warmed her up more the second time. Honestly for her, I think this was all about finding a clandestine way to get a little experience.
I don’t know all the facts and honestly want to forget about her fucking her 2nd cousin.
> Jamie used her hall pass last month in Israel. Birthright? Cause seriously, Israel is where Americans go to get laid. It’s like the whole purpose of the country. Anyway, I really gotta stop reading the comments in posts like this because they’re annoying as all hell. "Hey, hot story, totally jerked off, but now let me get back on my high horse and tell you all these things you did wrong."
It wasn’t birthright actually, she went and stayed with her aunt and brother in law who is in the IDF. The second cousin she fucked lives with them until next year.
Plan B: DENY DENY
Ahhh…same difference anyway. Reminds me I should take a trip over there.
In ten years this will be way past the supposed, "Statute of limitations" I’ll deny deny deny to the grave.
Maybe not the best kind of sex, but I am sure she is doing a lot to make up for that guilt. Dude, this might be the WETTEST period of your life. So enjoy.
I say keeping it in the family is to your benefit. Did your wife tell you herself about who her hall pass was with? I say you tell her. Who better than her sister rather than some random stranger or someone who can give you a disease?
Honestly I do think Jamie would be PISSED and Madeline obviously wants to keep it a secret now. After the first hook up Maddie was initially wanting to confess so I wonder if her opinion will change. To answer your question, Jamie did tell me. Her plan was to fuck him all along, and she admitted to sending nudes to him weeks before the trip.