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Got the best head of my life and my first prostate massage from my Fiancé's little sister. [MF] [Oral] [Chapter 3] | 2016

Here's the first 2 chapters of my fiancé's little sister and I. This is all very real. In a way I wish none of this was real.

Chapter 1

https://www.reddit.com/r/gonewildstories/comments/3qt16b/i_took_my_fianc%C3%A9s_little_sisters_virginity_first/

Chapter 2

https://www.reddit.com/r/gonewildstories/comments/3v7bsx/did_it_with_my_fianc%C3%A9s_little_sister_again_we_had/

Chapter 3

Maddie and I hadn't seen each other in weeks. I had been making it a point to ignore her Snapchats which were fewer and farther between. More than 2 months passed since our last iMessage, things had most certainly dried up. Until the seemingly world crushing breakup with her new boyfriend.

"Jamie you don't understand, he called me a slut!" I heard Maddie complaining to her sister on speakerphone. "We were making out in his room, and he freaked on me after I tried to unzip his...." Jamie disengaged speakerphone before I could hear the details. She walked into our bedroom with the phone calmly talking her little sister off the ledge.

I took the opportunity to have a nice little 420 sesh while waiting out the phone conversation. Jamie walked out of the bedroom and laughed at me, I must have looked really stoned. "She's really bent up a about him. Apparently he was saving himself for marriage and she thought it would be easy to break his willpower. Not so much." Pretending to not be intrigued I asked "What was his name again?" I added, "They were only together for a few weeks right?"

Jamie went on to explain that she wanted to use some frequent flyer miles to visit her devastated sister. We had yet to visit Maddie at her new (first ever) apartment.

Two days until departure, I get a call from Jamie and Maddie's father. He wanted to chat about some simple wedding planning items, which we sorted quickly. "Listen, Maddie was lamenting about you not being able to join them in Michigan this weekend." I tried to interrupt. "I am going to book you a flight to meet them, we don't want money getting in the way of some family bonding." I was shocked, confused and a bit nervous. Thinking of course, there was only one reason Maddie would want me in Michigan.

I flew out to Ann Arbor (via Detroit) about 6 hours after Jamie, landing at nearly 1 AM. Figured I would grab an Uber and find the two girls either A: Wasted or B: Asleep. Turns out both A and B aren't mutually exclusive.

Upon arriving Maddie opened the door with her hand covering her mouth, laughing into her hand and trying to be quiet. "I'm so stoned, and I cant stop laughing at your shoes." I was wearing my light pink sailing shoes, they had become sort of an inside joke over the years. Walking me into the apartment she informed me, "Your fiancé passed out on me a couple hours ago." Abruptly adding, "I'm so glad you're here!!"

I parked myself on the couch next to Jamie, who was curled up and passed out. I was gently rubbing her head but she did not wake up at all. Maddie tapped my shoulder from behind, "Hey let's toke, I've got a piece in my room." I tried to wave her off, but she insisted by locking her elbow with mine and pulling me up off the couch.

Maddie sat down on her bed and reached under it with both hands. As she bent over to reach, her cleavage was totally visible and I clearly saw one of her little pink nipples. However, they were clearly now pierced. Without thinking I said, "So they're pierced now?"

A long silence came and she seemed to ignore what I said. She was grinding weed and carefully emptying out the bowl for her cute little RooR bubbler. Finally she replied, "I thought that book was shut?" I looked at the floor and laughed, thinking my best bet was to change the subject and get out of that bedroom ASAP. "Let me hit that, Jamie says you're getting medical weed now? Impressive."

Maddie slowly let out a big hit, and quickly motioned toward the door. "Shit shit, close the door, our neighbor is a crazy old professor." I fell for her first trick. With the door closed, she could be more aggressive. When I turned around after shutting the door, she was 1.5 feet from me standing with the bubbler and offering it to me. I lit the bowl and began to take a long slow inhale.

"It is so cool that you still smoke weed, I wish Jamie didn't quit after college was over." She was moving closer slowly, and now had extended her hand to my chest. She had become an expert at bending my willpower. "So you're looking at my tits pretty intently." She giggled, "It's ok I'm used to it, they look badass now." I handed the bubbler back to her, trying to think of a way out of this. "I'm so tired from the flight, might need to pass out with Jamie."

"Yeah I'm going to put my PJs on." Maddie casually walked over to the closet and took her tank top off with no warning. I shielded my eyes and moved toward the door to excuse myself. "Wait wait, you can just use the air mattress, it's under my bed." Let me grab it. She reached for the air mattress before replacing her top. First she was covering her boobs with her arm, "Eh, it's nothing you haven't seen before." She was walking around her room topless hunting for the air mattress while I tried to distract myself with the weed.

"You know I could clean this for you, it looks pretty dirty." I pointed to the bubbler, trying to change the subject with my back to her. Suddenly I felt her hands on my back, "How do you clean something like that?" Her hands moved down to my shorts as she reached around and tried to fiddle with my belt. I knew what she wanted.

Maddie unlatched my belt and started kissing my neck. "Where's that air mattress?" I said looking for any escape possible. "What so you want to fuck me on the air mattress?" I laughed, and turned around only to find myself staring at her big tits. They were even better than I remember. She was wearing yellow and blue studs to represent Michigan. She pushed me onto her bed, sending her weed grinder and box of goodies flying onto the ground.

The grinder hitting the floor made a loud crashing sound, and we could both hear Jamie waking up and moving in the next room. She was walking toward the door and started knocking. "Maddie are you still smoking weed? Did he arrive yet?" I could see Maddie's heart beating practically out of her chest. "No he's not here yet, I'll wake you when he gets here." Jamie gave up and returned to the couch. This was good enough for her to go back to sleep.

I started replacing my belt, but Maddie stopped me by grabbing my arm and immediately getting on her knees in front of the bed. "I'm going to give you the best blowjob of your life, then we're going to bed." I stood up and motioned to the door, still trying to resist. She literally grabbed me by the ankle and completely tripped me. Now she was holding my pink shoe in her hand, laughing like a crazy person. How did Jamie not hear me fall over? "If you don't let me blow you I'm going to tell Jamie all about us." My heart sunk into my stomach, but my dick was diamonds. I rolled my eyes, "Look this is the last time we do anything." She sarcastically quoted Sean Connery (a family favorite), "Discipline 007, Discipline." She was really stoned.

I sat on the bed, as she crawled up and positioned her face in my lap. Before long, my dick was poking through my boxers and she was licking my shaft. "I want to edge you for an hour, I love seeing boys squirm." I nodded, "Keep it quiet. This is really stupid and risky." She took that as a challenge and laughed like a crazy girl again, loud enough to startle Jamie. "Madeline what are you doing in there?" I was sure we were about to get caught. "Relax I'm just watching Netflix!" Maddie responded instantly before taking my whole dick into her mouth. She was rubbing the tip with her tongue in a circular motion with delicate precision. Suddenly I didn't regret giving in.

Maddie suddenly stopped blowing me and reached for her iPhone, unlocked it and handed it to me. "If this is our last time together I want to remember it. Record me." I laughed and threw the phone aside. She grabbed it again and firmly insisted. I pointed the camera at her as she started sucking me again. She whispered into the camera, "This is so wrong but it makes me so wet!"

Madeline is significantly younger, more immature and less experienced than Jamie but my god she is way better at head. She was licking my shaft up and down slowly and would stop and smile at me every so often, winking at the camera. If I stopped recording, she stopped stimulating me.

"You know, my room mate is a nursing major and she taught me all about prostate stimulation." I was terrified. Maddie ran into the bathroom and came out with a latex glove on her hand. I didn't think much of it, thought she was just joking with me. She resumed licking my shaft slowly as she had been doing for nearly 30 minutes already. I forgot about the glove.

Maddie took off her yoga pants, now down to only her boy shorts underwear with lime green laces. Her ass is by far her best feature. She spit on her hand to moisten my dick, then bent over in front of me rubbing her ass on my crotch. It was as if she was practicing for porn. (I was still filming all of this with her iPhone keep in mind.)

I gave in to the blowjob and grinding, but there was no way I was going to give into fucking her again. This is why I tried to object when she pulled her panties off. She put her panties over my face and pushed me back onto the bed. This was quickly becoming the kinkiest, most elaborate blowjob of my life. Her panties were wet, but not soaked, and had the fresh odor of young clean pussy. I've got a serious panty fetish, and am imagining that Jamie drunkenly shared this with her little sister.

Maddie stopped blowing me suddenly, stood up and told me to turn around and bend over. She reached for a small bottle of liquified coconut oil. She whispered, "Stole this from Jamie and we used it for our first time together. Remember?" The memory was turning me on like crazy so I did as she said. "I want you to cum all over these panties." She grabbed the underwear, threw them on the bed and turned me around to face the bed. Maddie, with her small frame, managed to push me down and bend me over.

Before I knew it, her fingers were completely in my ass. "Let me know if it hurts." She was fiddling around trying to stimulate my prostate, but I was uncomfortable and unsure. Maddie whispered, "Here it is." Suddenly I felt a wave of pleasure come over me. I was practically convulsing with pleasure. Maddie whimpered, "Close your eyes and think of Jamie." What. The. Fuck. Could not believe she actually said that.

I exploded all over her sheets, on the panties and finally onto her hand as she tried to stop the overwhelming load from getting everywhere. "Holy shit, I guess that worked." I turned around to see Maddie with a shit-eating grin on her face. I felt weak in the knees, embarrassed and ashamed of our cheating ways.

I pulled myself together, started looking for the air mattress again and realized something horrifying. Maddie had filmed the whole prostate massage and subsequent eruption on her phone. I didn't even realize it until I saw her sitting and watching the clip. She laughed, "That is the most cum I have ever seen."

The next day, Maddie sent me all of our sexy videos while we were at brunch. She is highly amused by risky behavior, as I had to squirm and hide my phone while the barrage of incriminating videos started coming thorough. I was sitting right across from Jamie.

I'm now legitimately scared of Maddie's risky behavior. Thoughts? Am I screwed? I'm supposed to marry Jamie next week and Maddie is the maid of honor.