I took [m]y [f]iancé’s little sister’s virginity [fM] [Str8] [x-post from gonewildstories]

My fiancè Jamie and her little sister Madeline have the same Jewish genes and good girl charm, but they certainly have different body types. Madeline is a taller 19 year old with DDs and a voluptuous figure. Jamie has been training for the Chicago Marathon, so her ass keeps getting smaller and more firm. Her medium perky Cs compliment the small ass quite nicely.

This past weekend the family gathered at their parent's house in Maine for some birthday celebrations. Dinner followed by board games led to a very PG-13 version of 'Never Have I Ever.' As the parents and older folks made their way home and to bed the game continued with more raunchy questions.

Maddie was wearing blue and white checkered pajama bottoms and I noticed about halfway through the game that her teal thong with pink ribbons on it was hanging out. She must have caught me looking because she pulled it out of sight and looked right at me with a wink. Holy shit.

As if to play off of my perverted peeking, she started asking about the fact that I must not have been with any girls other than Jamie. Slightly inappropriate considering the younger cousins were still sitting within earshot. The math was easy in her mind, as Jamie and I had come to age together for over 10 years and were indeed exclusive partners.

My awkward way of answering the question must have sent the wrong (or right) message because Jamie ended the game and announced that she was going to bed. Madeline and I both agreed that we weren't tired and she suggested that we grab a beer and get in the hot tub. I had no idea where this was going. I changed and met her out back in the tub with a few Lagunitas IPAs.

To my surprise she emerged from the house and into the gazebo/tub wearing nothing but a sports bra and the the same teal thong.

"I saw you peeking at my ass so hopefully you can handle yourself, I left my bikinis at the Cape Cod house last weekend."

Maddie must have found the water too hot because she couldn't seem to submerge her whole body gracefully. Watching her attempt to lower and re-lower her bottom half in the hot water was way too sexy. I was already hard as diamonds from seeing her cute little ass bounce in and out of the water as she struggled to adjust.

Hoping that everything was back to normal, I sipped my beer and tried to make small talk about Lagunitas opening up a brewery in Chicago. She bitched about the strong flavor and asked if I had anything else. I was staring at her wet, now see through white sports bra and completely tuned out.

Here I am caught red handed for the second time gawking at my future sister in law. She jumped across the 8 person tub onto my lap and said I needed to keep my eyes off her body while laughing and putting her hand on my chest. There was a silent pause when I felt her run her hand from my collar to my waistline.

Maddie looked me in the eye and said I must be lying about only fucking one girl. Insisting that I have been loyal to Jamie must have turned her on even more.

Maddie lifted her ass out of the water again, turned around and grabbed a beer. Confused, I asked why she wanted another, seeing as she just finished complaining about the flavor. "It's not for me, I have to get you drunk so we can keep having fun out here." Madeline bent over the tub to grab my beer key, while "accidentally" putting her beautiful curvy backside right in my direction. I could see the side of her pussy was coming out of the little teal number and I audibly let out a little wimper. I. could. not. take. it.

"Madeline you know I'll never cheat on Jamie right?" I could see the now-obvious sexual energy radiating from her.

She turned around and looked at me confused. Returning to my corner, this time she sat on my lap facing toward me with both legs spread on each side of my now throbbing crotch.

"Um, what is happening?" I poorly faked innocence.

With that she reached behind her back and pulled the bra half off letting her nipples show, which broke the camel's back. I grabbed the bra and ripped it over her head, not wanting to wait another second.

"I can't fuck you Maddie." "Shut up," she whispered.

We made out with our bodies half in the water for the next few minutes, she was grinding on my now untied trunks under the water. I could see the thong beginning to slip off and reveal her shaved cunt.

With her tits exposed she hopped out of the water unexpectedly and suddenly. Grabbing my hand the whole time, she whispered "I wanna take you to my bedroom." We ran through the patio doors, across the living room and up to her bedroom with her ass and tits completely exposed. Thank god no one was awake.

On the way upstairs I could not help but look at all of the photos and decorations that reminded me of Jamie. Here I was hooking up with her little sister just 20 feet down the hall from where she is sleeping in her room.

Maddie pushed me into her desk chair so I sat down unsure what to expect. She bent over in front of me, shaking her perfect ass and pussy at my face. She was obviously freshly shaven and still dripping water from the hot tub. I decided to fingered her while she bent over and buried her face into the floor, her soft moans and heavy breathing were risky and made me nervous. Jamie or their parents could easily hear if awake.

Without warning her I took my dick out and pressed it against her little slit. She turned around and scolded me. "Were taking this slow! Does Jamie even know how to edge you?"

Maddie stood up, grabbed her pink Victorias Secret bathrobe off the back of her door to cover up and motioned toward the bed. She laid down next to me, but not before grabbing a jar of Coconut Oil from her nighstand.

"I'm going to make you squirm and beg to cum, lie back." Maddie was stroking my cock slowly with just two fingers for at least 5 minutes. The melting oil on her hands made for the silkiest skin on skin contact you can imagine. I felt like I was going to cum, but that's when she stopped in her tracks, slipped the robe off to reveal her nipples.

"I need to cum all over you." I begged. "Not until I let you, I'm going to make you scream."

Maddie repositioned herself in the reverse cowgirl position with the robe still 2/3 on her. Her ass was peaking out of the short robe. She turned around and stroked me slowly with her, tiny wet hands. I didn't notice at first but she was fingering herself while touching me.

Maddie stood up and dropped the robe, now only donning the teal thong that was now visibly wet. I stood up to meet her but she shoved me back down on the bed.

Her next move was to bend over and touch her ankles. Her pussy was clearly visible through the thin teal satin, it was driving me mad. I began to stroke myself, which she could hear. This prompted her to bounce on top of me and stop my motion.

She reached to her nightstand and grabbed two items. One was a pink rabbit vibrator, which she placed in my hand. This was getting more insane by the minute. The other item was a lamb skin condom, (which is a bit of foreshadowing).

Assuming the reverse cowgirl position again, she dropped the thong below her pussy this time. I turned the vibrator on and to her surprise shoved it into her her tiny pink ass. "Aww, fuck that was not-" she barely managed to say before I began to aggressively finger bang her beautiful white, smooth and now oily slit.

Burying her face in the down comforter I could almost hear her screams of ecstasy. Thank god she knew how to mute herself. Maddie flipped around with the rabbit still vibrating in her ass, and kissed me with force equivalent to hurricane Katrina. She took the opportunity whisper something I'll never forget.

"I'm a virgin, please don't be mad." 10 or 15 seconds passed as I took this in.

"My sister said her first time with you was perfect, I can't trust anyone else to fuck me. I’m only 19, I don’t know any mature guys like you."

I sat in silence and dropped my hands to my side, all I could hear was the vibrator (still in her ass, comically). Rolling her over forcibly, I said “OK, but this is seriously unforgivable, one time only and we can’t tell anyone.” She grinned and reached under herself to pull the battery charged rabbit out of her ass.

I pulled my boxers off and reached for the jar of coconut oil to re-lube myself, albeit unnecessary, she was totally wet. I set my oily cock on her stomach as if to say ‘your move.’

Maddie rubbed my member on her cheek while looking up at me and laughing with excitement. “I remember the night Jamie lost it to you, I was only 15 but she told me the whole story when she got home.” Maddie had been jealous of her older sister for nearly 4 years, my mind was blown. I guess she idolized her sister to the point that she wanted to lose it to the same guy as her. I was taking advantage.

Maddie was lightly stroking my cock with her lips while I let my fingers graze the outside of her pussy. This went on for more than 10 minutes, driving me absolutely mad. I kept trying to reposition her for the final act, but she was resisting.

Finally we rolled over and I put my dick right in front of her slit and made eye contact, “This is it, are you sure?”

Fucking her was the greatest feeling since I took Jamie’s virginity nearly 5 years ago. I took it as deep as I could (bareback) without causing pain, because she was clearly wincing and trying to stay confident. I was too turned on by her painful gestures, so I kept fucking her harder. It looked like she was about to cry with ecstasy. Unfortunately I could not last much longer.

The teal thong was now around one of her ankles, so I grabbed it and held it to my face. The smell of her pussy was exactly the same as Jamie’s, how much different could it be? Although inexperienced, Maddie had clearly planned for this. She flipped over and laid on her stomach, while spreading her legs to reveal the most breathtaking angle I had seen of her young body. I reinserted myself and went at it even harder, now she was really in pain. This new angle gave me clearance to fuck her even deeper than before.

I reached around to grab her tits, and noticed that she was clearly crying. There was no question that she was serious about being a virgin. Although I felt somewhat empathetic, this turned me on way too much. Still fucking her unprotected, she suddenly realized the risk she was running.

“Shit I’m not on birth control, pull out! pull out!” Now the condom-grab made sense.

I was clearly about to come, pulsing and struggling to continue fucking her. I pulled out and shot several warm ropes all over her perfectly positioned ass. Now realizing what had happened, I backed off, still with the thong in my hand. She laid motionless still whimpering and catching her breath. I don't think she came all the way, honestly.

I stood up and took it all in, there she was, the teenage little sister of my fiancé. Having just taken her virginity, I felt a little remorse, especially after I noticed the small amount of blood dripping from her vagina. She was clearly embarrassed and somewhat delirious. Madeline immediately collected her robe and covered herself.

Looking at the floor at first, she looked up at me, moved toward me and kissed me again on the forehead. She bit my ear and said “Thank you times a million, I’ll never forget this, but you can’t tell ANYONE.” I looked down and saw more blood running down her leg.

I left the room, showered off and met Jamie in bed. She assumed that we had passed out on the couch downstairs, not suspecting a thing. I kept the teal thong as a souvenir, and being my perverted self I have vacu-sealed it for later enjoyment ;-)

Edit: Madeline is on her way to Chicago to visit us for Halloween. Those two planned it last-minute. Her and Jamie are dressing up as Victoria's Secret Angels and Maddie has texted me telling me she's wearing the same robe that I saw her in… Jesus Christ. Will be totally unable to resist banging her again, and we'll have the condo to ourselves while Jamie is out tomorrow morning.

Source: reddit.com/r/sexystories/comments/3qz2cw/i_took_my_fiancés_little_sisters_virginity_fm