Kitten Ch. 04: My First Stranger Sex

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Sir takes me to a friend to be fucked by a stranger.
5k words
4.47
37.2k
8

Part 4 of the 8 part series

Updated 06/08/2023
Created 06/14/2016
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After having flashed truckers and others in restaurants, I was craving attention even more. I wanted to be seen, touched, fingered and fucked by strangers.

This is my burden to bear. I know it's not normal, but I crave attention from strangers.

Sir says I am the biggest tease he has ever known. I am only allowed to tease strangers when he says I can.

He only allows me to fuck people he knows...strangers to me, but not to him.

I am totally subservient to my Sir. He is my Dominant, and I submit to him totally, willingly, and without reservation.

I await his direction.

I must dress as he directs, never wear panties or a bra. When we go out, I must pull up my dress in back and sit on my bare ass. This often gets my juices flowing, knowing someone else, hopefully a man will be sitting in my juices a few minutes after I get up and leave.

Sir only allows me to refer to myself as "Girl" when I am talking to him, or in play situations.

He occasionally has me stand in front of him with feet apart at shoulder width, and he will slide his hand under my skirt or dress and finger me. This is called a "Wet Check".

This is usually performed in a public place, a restaurant or a pool hall, or one time on a fishing pier full of men.

If he "Wet Checks" me for more than a few seconds, or does it vigorously, it is difficult for me to hide the fact that I have just cum... especially if I squirt.

But letting the people around me know what is happening is not allowed. He likes to let their imagination run wild.

I am never allowed to say "no" to any kind of sex - as if I would anyway.

A friend of his apparently saw us together and thought I was his daughter or his granddaughter.

He explained to me that his friend was shocked to find out that I was his girlfriend, his lover and his sub, and that I loved to be seen nude by strangers.

The friend said he would kill to get a look at me nude sometime.

This was done by texting as his friend saw us while he was driving by us while we were shopping.

We hadn't done anything with anyone since he had allowed a trucker to finger me at a truck stop three months earlier.

I was suffering from withdrawal, and Sir knew it.

He knows how susceptible to teasing I am, and that it's difficult for me to come down after being turned on and not sexually satisfied.

I sometimes feel like my skin is crawling off me if I don't get fucked to orgasm regularly. Sir usually fucks me two or three times a day just to keep me from exploding, he says. He likes it as much as I do.

Sir bought me a dress to wear whenever I am going to be played with or fucked, or he has something sexual planed. He calls it my "Traveling Dress".

Often, when we are going on a road trip, and he is going to allow me to flash truckers, he will have me put on my traveling dress. Just hearing him say that gets me excited and wet in anticipation.

My dress is very lightweight white cotton, practically transparent if one looks closely enough or if I am standing with a light behind me. With an elastic bandeau top and no shoulder straps, it comes down to about 4 inches above my knees, and is full.

Also, when he has something planned, he will withhold sex, and will not fuck me for a couple of days. This makes me crazy and sometimes a little bitchy.

I love sleeping nude next to his nude body, and the feeling as he is spooning me is heavenly.

He is a sound sleeper, and sometimes I will reach back and squeeze his cock until it is hard. He has awakened several times as I was doing this, and punishes me, by adding on a day or two with no sex.

This is terrible punishment for me, as two more days without feeling his loving hands on me, and his hard cock in me is torture.

Sir had been withholding sex for several days. I knew something was up, but not what or when..

The worst part is not knowing. It gets me going, and I can't stop the wetness between my legs.

He doesn't allow me to touch myself, or masturbate during the withholding period. Usually, by the time we are doing something, I am aching down below, and am jumpy as a cat!

This time, he withheld for ten days!

I was in a constant state of agitation, couldn't sit on the furniture without leaving a wet spot, and sleep was fitful.

I wanted to at least fuck myself with a bottle, but it wasn't allowed. I cried a lot when Sir wasn't watching.

One day around noon, Sir said we were going out to lunch and I was to put on my traveling dress! "OH SHIT! OH HELL YES!" was my reaction! I could see the light at the end of the tunnel. "I'M GONNA GET FUCKED!!"

We went to lunch, I sat on my bare ass, I had a bowl of "She Crab Soup" and a salad. My favorite lunch of all time.

We finished lunch and nothing happened!

I was jumpy, waiting for something to start. Nothing!

After lunch, we went to the City Marina, and walked the docks and looked at boats. I was about to jump out of my skin!

Then, Sir stepped onto this really big boat with windows all around. It was tied across the pier from another big boat. He had me step aboard, and we went into the "Saloon" as he calls it.

There was a couch and some very plush chairs ... the deck was carpeted, it looked like a living room with windows on three sides.

The view of the marina was glorious!

Sir then took me by the shoulders and looked into my eyes and said a very good friend of his was going to visit me today, here on the boat.

He said the man would take my dress off so he could see my nude body. I was getting excited!

He said the man was going to have his way with me, and I was to allow him to do whatever he wanted. I was to be respectful, compliant, and willing with his friend.

There were just two things I needed to know before his friend got there.

The first was that his friend was not a good looking man. He was short, fat, bald, and not good looking in the face.

Repulsion must have showed on my face. Sir smiled and said his friend was a wonderful person, and a dear friend of Sir's. I relaxed...a little!

Then I asked what the second thing was.

Sir said His friend had the biggest cock he had ever seen on a man! Sir has played in groups for years, and has probably seen a lot of big hard cocks, and I was impressed, but didn't have a frame of reference for a cock bigger than Sir's.

Then Sir told me that If his friend's cock was too big for me, that I could speak freely and say I didn't want him to fuck me.

Ok, this got my attention! HOW FUCKING BIG WAS THIS MAN'S COCK?

Sir had never stipulated that I could deny sex because a cock was so huge! I was a little taken aback, when I saw the shadow of someone walking down the dock toward the boat.

Sir had me sit on the couch to await the man's arrival.

Just as I sat down on the couch, I felt the boat move and saw a very large man come into the saloon and greet Sir with a big smile and a handshake.

All I could think of was, "Come over here and let's get started!"

Then the man turned around and looked at me. I was shocked!

The man was a bit shorter than Sir, about 5'9" tall, and massive in size!

He was bald and his face was scary looking, almost malformed with big lips. I remember thinking how good those lips must feel on a pussy.

I was so put off by his looks, the thought entered my mind to run out of the boat and off the pier to Sir's truck to await my punishment.

Then the man turned and looked at me and smiled. His teeth were crooked. I was panicking at the thought of him touching me.

I looked at his hand when he and Sir shook hands. His hands were massive! Fingers the size of sausages.

Looking at me, he said to Sir, "Is this beautiful creature the one I'm going to get to touch?" He had the most beautiful voice...like a radio announcer. I relaxed and smiled a nervous smile at him.

He and Sir sat on chairs opposite the couch I was sitting on and began TALKING! OMFG!

Didn't Sir realize I hadn't been touched in ten days? Didn't he realize I wasn't allowed to touch myself in any sexual way...FOR TEN FUCKING DAYS!

Didn't he realize My body was shaking from anticipation, my pussy was on fire, and my juices were literally running down my ass cheeks to the couch I was sitting on?

I pulled my dress up and opened and closed my legs (a technique I use to masturbate when I can't be too obvious), my body was tense, and my hips ached from the constant tension.

My head was screaming,"I NEED TO BE TOUCHED, KISSED, AND FUCKED NOW!"

I gave Sir my "Needy" look and he laughed under his breath. Sir said to the stranger, "Go touch that woman. She's yours for the taking, but be gentle...you know why."

I heard myself squeal as the man approached and knelt down in front of me. Up close he was even scarier than from a distance.

I felt nauseated!

His fat face was unshaven. Then he smiled a very loving smile at me, his large lips opening and showing off his crooked teeth.

I was repulsed!

My Kegel muscles were exercising themselves... I was on the verge of a huge orgasm!

I thought to myself, "This isn't happening! This man is physically the ugliest human I have ever seen in my life, and I want him to fuck me like a stallion!" Yet, he was so nice. I felt guilty about what I had though about his looks.

He then reached over and took down the top of my dress, exposing my breasts. His eyes lit up and I instantly liked him.

He reached over and gently touched my breasts with his fingertips, feeling all around my nipples. I love the gentle touch. I began shaking visibly.

I took a deep breath to try to control my shaking. He gently squeezed my breasts and then moved his fingers across my nipples.

I gasped! Tweaking my nipples goes right to my pussy! I heard myself groaning.

The man then laid me back on the couch, placing my hands above my head and pulled me by my hips to the edge of the couch.

I couldn't believe how strong he was! I opened my legs wide to him, hoping he would eat and finger me!

My dress was up around my waist, completely exposing my lower half to him. He lifted the bottom of my dress over my face, and I thought, "Here it comes!" I couldn't see what was happening!

He blew his hot breath on my clit, and I squirted a bit. I could feel my juices running down my ass crack.

I was about to jump out of my skin!

I could hear myself making noises in anticipation of being entered by a cock. The feel of his hot breath on my pussy was such a tease! My brain and cunt were screaming for any kind of relied! Anything!

Then, came the delicious feeling of his tongue on my clit! OMFG! He lapped at me for a few seconds. He licked from my asshole all the way up across my clit! I was about to scream!

I jumped, as he introduced two very big fingers into the opening of my pussy, parting my inner lips, spreading my juices along my labia.

My legs opened wider by themselves, and as he slid his VERY BIG! fingers into me, I had a huge orgasm and sprayed all over him!

I hadn't been touched in ten days, and this orgasm and squirt were huge! Such a relief! But I wanted, no, NEEDED! much more!!

I could hear a woman somewhere squealing and saying, "I'm, I'm, I'm..." then he started sliding his big fingers slowly in and out of me, crossing my G spot with every stroke!

I started cuming and couldn't stop until he very gently slid his fingers out of me, causing me to jump.

He moved the hem of my dress down, uncovering my face. I saw his face again and realized just how unattractive he was. I was repulsed by him, and I wanted so badly for him to fuck me!

My emotions were running wild!

He smiled at me and kissed my clit gently. He stood up in front of me and It was then that I saw the bulge in his trousers. It was massive!

I thought surely he had stuffed his trousers with socks or a giant double ended dildo, just to impress me.

I laughed a little and looked over at Sir. He just smiled.

The man then unfastened his belt and his trousers, and pulled his zipper down. He opened and dropped his trousers.

I was astonished at the massive size of the cock that fell out!

I had never seen an uncircumcised cock before, and never a cock of this size. It was enormous, and my first thought was that it looked like Sir's forearm!

I looked at Sir and said, "Girl doesn't know if she can take that cock...it's HUGE! Sir, what do I do?"

Sir looked at me and shrugged his shoulders. It was up to me. The man then kneeled in front of me, leaned up over me. I thought he was going to fuck me right then and there!

He lowered his face to mine, kissed me on the forehead and whispered to me, "I am going to fuck you with the biggest cock you have ever seen. I am going to be very gentle...at first...then I am going to slide every inch of this cock deep into you, and after I finish, you are going to beg your Sir to invite me back to fuck you over and over. I'm going to own your cunt!."

With that, he gently bit my neck, something that drives me wild! He said to me, "Are you ready?" I whispered, "Yes Sir. Please be gentle."

As I lay there on my back, completely exposed with legs spread as wide as I could open them, on the couch in the saloon of the boat, staring in disbelief, my wetness running down my ass crack.

Sir's less than attractive friend with the great "Fuck Me" voice and the biggest cock I had ever seen just inches from my opening, was kneeling over me as he told me he was going to fuck me with that monster!

I started shaking with excitement and a great deal of fear at what was about to happen to me. I looked into his eyes, and saw the most kindness I have ever seen in a man's face.

I wanted to feel his massive body on me, crushing me with his weight, and pressing that giant uncut cock deep in me, opening my body to a whole new world of possibilities! I shuddered at the mental picture of it opening me up.

I asked him if I could see his cock up close before he fucked me with it.

He stood in front of me, his cock just inches from my face. I sat up. I was astounded at the size of it!

The sight of the foreskin covering the head gave me goosebumps! I touched it with my finger. It was soft to the touch even though his cock was hard and getting harder.

I asked if I could pull the foreskin back. He said, "Yes, gently please."

I wrapped my hand around the end of his cock, my fingers unable to reach all the way around. My first thought was that I had never seen a cock this big on a human, either in person or on the internet!

I gently pulled the skin back, and revealed his cock head. It was massive! It was about the size of a very large plum, and nearly the same color, with a very prominent ridge around the head.

I said I wasn't sure I could take this in my vagina. He said, "I will be gentle ...at first... and you will ask me for more. I will stop if you say to. "

With that, I tried to put my lips over the head of his cock. Couldn't do it. My mouth wouldn't open far enough!

I did, however enjoy the musky smell of his cock, and I realized my body was screaming to be fucked!

He took me by the wrists and gently laid me back on the couch with my legs spread wide, my pussy open and fully exposed to the coming assault!

I was so scared, and so wanting to be fucked! I felt the tickling of my juices running down my ass cheeks.

I took a deep breath and nodded to him to proceed. He was looking into my eyes, and I was transfixed by his stare and the anticipation of what was about to happen!

He took his cock in his hand, leaned foreword a bit, touched it to my clitoris, slid it down and back up the lips at my opening, spreading my copies juices all over my bottom.

I could feel his strength, his size and his need as he massaged my opening with his giant cock head, pulling more of my lubricating juices out of my body.

The anticipation was killing me! I felt as if my skin was covered with crawling ants, and the only cure was...then he slowly opened me and slid just the head into my waiting cunt.

The pain was nearly unbearable, and I winced and cried out and sucked in a deep breath!

He asked if I wanted more.

I asked him to give me a second to adjust.

But for the pain, I wanted him deep in me right then!

I felt like he had shoved a hot poker into me. I panted for a few seconds.

Then as suddenly as the pain had hit me, I felt an intense pleasure spread from my stretched cunt up to all my girly parts. My nipples were so sensitive, they felt as though if anyone touched them, my pussy would explode with pleasure!

I took another deep breath and nodded to him.

He paused for what seemed like forever, and pushed some more into me.

I could feel that giant ridge around his cock head sliding into me, stretching the walls of my vagina. The sensation of stretching was excruciating, but the feeling of fullness was amazing!

I was having, for the first time in my life, an intense pain/pleasure experience!

I felt like a virgin again, and I guess in this case, I was.

As my breathing slowed, he looked at me and I nodded. Sir asked if I was ok. I told him I was, but had never felt this feeling before even when he had first penetrated me.

Sir was, as I have said before, a bit larger than average, but I was used to his size after about a week of him fucking me regularly.

I couldn't see how I would ever be able to adjust to this cock!

The man fucking me, slid his cock out to my opening again, and the emptiness was almost unbearable!

Then he pushed back into me, deeper than before!

I was cumming and crying at the same time, not sobbing, but had tears running down my cheeks.

The man looked at my face and asked if I was ok.

I nodded to the affirmative, and smiled through my tears.

He again pulled his cock out to my opening. I could feel the walls of my vagina being pulled out with it!

I gasped, and he pushed it all the way in!

I felt it hit my cervix, and the pain was too much!

The fullness was the most satisfying feeling I had ever experienced! He leaned down and said I was a good girl, and I had done very well, but that he had more for me.

I asked him to stop, that I was in too much pain. I didn't say anything about the pleasure I was feeling.

He pulled out of me, and I felt such an emptiness, and at the same time such a relief from the massive cock that had just opened me more than I thought possible.

I sat up and wrapped both my hands around his cock, as best I could, opened my mouth and tried to wrap my lips around the head.

Again, I was astounded by the size of this massive piece of man meat!

I cleaned his cock off with my tongue. I loved the taste of the juices from deep in my cunt with the muskiness of his cock mixed in.

I started Jacking him off with both my hands, and sucking on the head as hard as I could.

He lasted just a few minutes, and as he shot a massive amount of his semen into my mouth, I felt my vagina tighten in orgasm!

It hurt, and it felt so empty, and I so wanted him to fuck me to his completion, and to mine.

I savored the feeling of his incredibly thick semen filling my mouth. It didn't taste particularly good, but it was his, and I loved that he had told me what a good girl I was.

He spurted about five or six times. I lost count as I was just trying to contain it all in my mouth and attempting to swallow it, as if it were life itself!

I was still cumming, in pain and pleasure. As I was swallowing his ejaculate, I was holding onto his cock and cleaning the oozing aftermath of his ejaculation from the tip.

I took a deep breath. He backed away from me, leaned over, kissed me on the forehead and said, "I want some more of you." My heart pounded in my chest, my Vagina was sore and at the same time screaming for more of that beautiful huge cock!

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