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My Roughest Adventure

"I bit off more than I could chew"

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I have been asked by some members of Lush, to write about the craziest thing I have done. I hope to complete it without getting as upset as I was for months after it occurred. Until now I have only related this story to one other person.

This event happened almost Two years ago.

My man and I are members of the swinging lifestyle. At the time of this event I was new to the lifestyle. I liked the new and exciting life changes, and I went a little overboard at first. I must admit, I am still little crazy when it comes to sex. But this was a new thing for me, and to be free to have sex for pure fun, with no commitment required, was very exciting.

My man and I are on a few websites for meeting people in the swing lifestyle. There is one, however, that is my favorite because my man doesn't check it very often, so I can chat away without his knowledge. I get to know others who love sex as much as I do, without his knowledge.

I began chatting with Paul on my favorite site, choosing him because his profile picture was a close up of his awesome cock. I love large cocks and his was as beautiful as any porn-star - big thick and gorgeous.

He lived in a suburb of Boston, not too far away from our home. He told me of his love of kinky sex and his life in general. This chatting went on for about three months or so. He told me he was forty-five, divorced, and worked in Medical technology. I began to trust him and pleasure myself to our shared porn and fantasies. He, like me, was into some crazy sex and his ex-wife had left him because of his kinky lifestyle.

He belonged to some strange groups and shared many pictures of his wild sex parties and fantasies with me. Some were even more extreme then anything I had tried and I didn't think he would actually do many of them.

It was winter and cabin fever had set in since there were few parties lately. I needed to get out and, in a lucky turn of events, my man decided to go to a Bruins game with his kid. After work, I could hardly wait to go online and see what I could get into. I arrived home unsure if it was to be an internet night or something better.

Paul came online and asked me to join him in a chat. He did this when ever he saw me online. I asked what he had planned for the evening and he said something hardcore. Paul asked me if would it be OK if he brought some friends for a get together. My first thoughts were no, but then he showed me picture of his friend Tommy. Paul told me Tommy belonged to a group with him and it would be a lot of fun. He asked to meet me at a Bar in Boston and I hesitantly agreed.

I was nervous but horny and the thought of feeling of Tommy's large penis inside me had me wet with anticipation. I jumped in the shower, shaved any hair from my head to my toes, covered myself in my favorite lotion and put on my one piece black dress with heels. Nothing underneath.

It was now five pm and I knew the game my man was going to started at seven pm, giving me five and a half hours of freedom.

I arrived at the agreed to restaurant and sat at the bar. I ordered a shot of Patron and Appletini and watched television. I think some of the people had the idea that I was a hooker, but I managed to ignore them until I heard Paul call out my name. He hugged me and kissed my cheek. He looked just like his pictures online. He was tall and kinda heavy, not a stud by a long shot, but behind him stood Tommy, roughly the same age, and a real dream. From a picture Paul had sent, Tommy was well endowed.

We moved to a Table and had a few more drinks and chatted about things. I could feel Paul's hands on my legs which drove me wild as the feeling of being wanted, as well as cheating, rushed over me. The tequila didn't even slow down my thoughts of heading to Paul's place. 

Paul asked if I was interested in having some fun with the two of them. I told them nervously, "I think so." He assured me that everything would be fine and we left.

I followed them in my car to a condo which overlooked the water and appeared very expensive. I parked my car where he indicated and we got on the elevator as he gave me a kiss.

When we were in the hall way of his apartment, his cell rang. He answered and his conversation was a little creepy since it was referring to me. It ended with him telling someone "yes you can" as he hung up, smiling. We entered his abode and he asked me if I wanted a drink. I told him yes please, but all he had to drink was some high end bourbon, which I had on the rocks. He took only a bottle of spring water.

He told me that before we went into the other room, he would like me to look at something first. I was curious but said yes. He asked me if my man had any idea where I was and I told him no, but if my man tried hard enough he could find out. He smiled and called me a good slut, kissing me again.

He handed me a piece of paper which read the following:

I am here on my own free will. I know my man has no idea I'm here. I want him to know, if he ever finds out, that it was my choice to be here. By signing this, I agree that I'm going to have sex and obey Paul in any way he instructs. I am allowed to have the following rules and a safety word.

I wrote down the words, thinking this was just silly. No poop or pee. No snuff and no marks. The the safety word that came to mind was "enough".

Paul told me to sign it and, as I did, he took a picture.

I said, "Hey, we agreed no face pictures!"

He told me he knew and asked me to hold up the paper as he took another picture with me holding it. Tommy was in the other room setting up. He told me that in that room there would be no pictures at all and put the camera down. That's when things began to change.

He took the paper, put it on a table and turned to me.

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He told me to take off my clothes, now! I pulled my dress off over my head and stood before him naked.

He took my dress, purse and keys and said, "You will get these back when I feel you deserve them."

He grabbed my arm and led me to the living room. The couch was the only thing in the room which hadn't been moved. Beside the couch was a queen size mattress which I was thrown on as I entered the room.

Tommy looked at me and said, "Wow, she's beautiful." He dropped his boxers to let his hard cock, which had a huge hook to the left, fall out.

I smiled and was happy to suck it, but as I exclaimed, "wow", Paul yelled at me.

"Don't talk you married, cheating whore!" He grabbed my hair and pulled me to Tommy, "Suck it, cunt," he ordered.

The rest is a little blurry, as it happened a while ago, but this is what I recall. Tommy began to throat fuck me harder and harder, moaning and saying "yea suck it good", in a bad porn stereotypical fashion.

Paul got behind me and began fingering and spitting on my pussy. "Oh yes, you're gonna get it good, your man doesn't fuck you like this."

He had four fingers in me and it really hurt as he began fingering me roughly and pouring lube on both of my holes. This is where it began really hurting and I felt like I shouldn't have been there. I later found out that both of them had taken Cialis, so I was in for a long night.

My eye was on the clock as I was entered by Paul. I didn't want to be late getting home. He was hard and thick and he held my head so Tommy could continue to face fuck me. I was gagging and drooling. I began to feel like some of my favorite porn-stars, ones that Paul and I shared in common. I rolled with it. Paul made me cum with his deep thrusts and verbal abuse. He spun me around and ordered me to lick his ass and balls while Tommy had his turn.

Tommy banged away with anger and determination till he came deep inside me. Tommy then fell down and smiled.

Paul then told me to sit on his cock and ride it. Like a good submissive girl, I did. This went on till he pushed me off as he was about to cum. He did not want to release just yet. He pulled me around and put a pillow under my stomach and, before I could brace myself, his cock was in my ass. It hurt. I cried as he showed my ass no mercy, slapping it as he drove his cock deep. Thank the gods that he didn't last much longer. He came inside me and fell on top of me kissing my face.

"You liked that didn't you? It's what you dreamed about isn't it?"

I said, "Yes sir," to appease him, and he rolled off.

I was hoping they were done but I turned over to see Tommy hard again. He slapped his cock on my face, asking, "Who's cock was bigger, his or my mans?"

I told him that his was. He had me lick his balls and ass as he flogged his cock all over my face. He pushed me down on my back and raised my legs, then slid into my ass which was already sore and hurting. He moved slowly in and out so he could see my hole gape open. He said he loved watching that.

Paul told Tommy that I had never done double penetration before and it was going to happen now. He slid behind me in the spoons position while Tommy was still inside me. After a few tries, got his cock inside me. Both men picked up the pace and gave me my first DP experience.

At this point, I was so tired and sore, I wanted to go home. I just let it happen and moaned. Tommy came on my chest and fell over laughing saying, I was a great fuck as he watched Paul begin to really take me hard.

Paul put my legs on his shoulders and pounded away, moaning and sweating for what seemed like forever. He released deep inside me then rolled off. I slowly stroked his cock, which was still hard from his medication, and kissed it to make him happy. I finally mustered up the courage to say "enough" and pointed to the clock, which read nine pm.

I drank an entire bottle of water and Paul offered me a shower but I declined. I felt semen dripping out of me and Paul told me that it was for my man. I told him I'd be asleep by the time he got home, hopefully. They laughed and Paul got my things.

I dressed and they hugged me, thanking me and asking if I was okay. I told them I was sore and tired, but played nice. Paul said he'd talk to me later.

I got to my car and drove home, sore and crying a little. I was only partially satisfied, cumming only once to my recollection. I pulled into my dark house and began running a bath. I went to my closet and found my emergency 'morning after' pill, swallowing it down along with two aspirin. I lay in the bath, sore and feeling a little ill.

I felt awful as I climbed into bed. I tried to forget everything. My man came home and tried to spoon and talk to me but I was dead to the world. I think he assumed I was drunk and left me alone.

I slept late the next day and woke up to the lawn mower outside my window. I felt ill from the pill and wanted to be alone. I told my man I didn't feel well and that I'd drunk too much. He kissed me, told me to relax and he'd bring me brunch in bed. He told me he loved me.

I felt better as the day went on, until I was asked, "Do you want to go to a swingers party that night?"

I told him I was too sick. I took the next day off from work as well. I saw a message from Paul asking me if we could do it again sometime? I replied that it was an experience I wouldn't forget but no, I wanted to give some other guy some luck. He was relentless in trying to get me to come out again and, eventually, I had to block him. When he threatened to find me and tell my man. That was not the right thing to say.

It took five days before I could have sex again and overall, I felt like that type of sex should be left to porn-stars, not me.

No regrets.

Published 
Written by allflavorsboston
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