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.