Tiffany The Cross Dressing Slut free porn video

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I was at the swimming pool with a couple of friends and my cousin. I was 15 at the time, My Cousin, Mark, being 13 and my friends John, 14, Steve, 14, and Henry, 16. We were all drinking beers we asked a guy to buy us at a local grocery store, and were relaxing.
We were all chilling in our shorts, with all our upper halves revealed, with John and Mark were the only ones to have six packs. Everyone was drinking, we were having a blast!
20 Min Later, we walk over to the Jacuzzi, and sit down all calm...in serenity..
We started talking a bit, asking each other what would we do for a million dollars, or what is your craziest sex fantasy with a girl, would you ever do your mother, sister, or dog? From then on the questions got nastier and crazier till were we found ourselves at the point arguing which of our cocks are bigger.
John claimed he was 8 inches, which I though was bogus. Henry said he was a good 7 inches but pretty thick. Steve justs sits there and saids hes 6 inches and my cousin, Mark, stands tall with a smile and saids "Im 8 inches too!"
I was being quiet the whole time..until every one looked at me..
Well Jack? How about you?
I was only 5 inches then and pretty embarrassed of it..I said, " Im 8 inches too!"
"Well", said John, "Looks like I am the biggest here!"
"Prove it" said Mark,
At that instant, John gets up and pulls down his pants revealing a gleaming 8 inch cock
Everyone just sits there amazed...
"Well how about you guys?" said Mark,
Everyone gets up pulls down their pants, each revealing to the exact measure they said, Meaning everyone was bigger than me..
Well I stood there with my 5 in cock feeling pretty embarrassed..
What else could I do?
Then we realized Steve was attempting something..
He turned off the Jacuzzi, and was trying to stick his cock into the holes..
"Hey guys! This feels mad good! Try it!"
And all of us, kinda drunk, started trying to fuck the Jacuzzi holes around the perimeter of the Jacuzzi.
Henry was having a hard time doing so...but all of us succeeded in the task..
So all of us were having "fun" trying to fuck the holes..
10 Min later all of us finished trying to do so and turned on the jacuzzi back on, leaving everyone insatiably horny and nothing to fuck... or thats what I thought..
Now before I let you venture on and read the next part of the story..let me give you a brief but excellent description of myself..
I was about 5"8 and weighed around 175, had somewhat little fat, since most of my weight was in my big ass.. I would say it can compete with a black ass due to its big size. I had black hair, brown eyes, and lovely lips!
Now back to it!
"Im kinda hungry" I said, "Im'a go get something.. Ill be right back!"
Right before I left the pool I saw everyone lean in and talk, most of em pointing to my ass, which left me somewhat puzzled as I left to go bring something to eat..
I come back 5 min later to see everyone settle down and become quiet as I sat back down in the pool. Everyone was holding another beer, drinking it till the last drop.
"Anyone want some M&Ms?"
"Ya sure pass some here" Mark said..
As I get up to give him, John, Steve, and Henry all get up and grab me!
"Oh yeah! I was planning for this to happen" Mark said, as he pulled down his pants..
They pulled down mines too.. only to slip on a pink thong..
So now I was naked with a thong, Held back against my will against Mark's throbbing cock. I was a virgin then..
"Open wide" he saids as he shoves his large and hot cock down my throat..
I was gagging, choking on a 8 inch cock down my throat, and could not emit any sound..
I tried fighting so hard, I was writhing and fighting amazed no one was looking at us..
Then the fighting got calmer, and calmer..till the point where I could not hold my sexual hunger and craving anymore..
I pulled my head off Marks dick and turned around to John, Steve and Henry..
"You guys are looking pretty lonely back there, you naughty fucks, just spanking my ass.. how about letting me go so I can really show you what a good time is.."
All of them looked at me amazed.. I was getting "raped" and I wanted it!
Henry, Steve, and John all let go of me, and Mark got pissed!
"You stupid idiots now h-"
I cut him off at mid sentence as a grabbed both is butt cheeks and deep throated his 8 inch monster..
I grabbed Steve's, John's, and Henry's pants and pulled em off..leaving them all hanging with their cocks out. I grabbed Steve's along with Mark's cock,
"I want you guys to fuck my mouth...just shove your dicks in and out"
I spit in both my hands and grabbed Henry's and John's cocks and started jerking them..
"The harder you guys spank me the better Ill jerk" I said with a wink..
I returned to Mark and Steve and opened my mouth wide as both of them threw their cocks down my mouth!
As their dicks rubbed against one another, and both my friends spanking me hard in the ass.. I began moaning, harder and harder with each spank, both my butt cheeks a bright red color, both cocks in my mouth, rubbing against on another..
Until I could not take it anymore, and ripped off my thong..
"I want all of you to start licking my hole!! NOW!"
Henry and Steve hesitated but Mark and John got down and started to teach my asshole what a good licking feels like..
Both Mark and John now swirling their tongues around my tight hole, and I started moaning as Henry decided to be romantic..
He came over to me and started kissing me..and I would moan and kiss him back..
His tongue was swirling in my mouth, licking it all inside, as I felt Steve's finger inside my hole along with the rimming motion of Mark and John..
Oh I was so hot...I felt so wet in my hole, I felt so sexy with my tongue meeting Henry's, I felt so gay with four men doing my every desire,
I got up and walked to the edge of the jacuzzi, pointing my finger at Henry and fingering my ass..
I wanted to give him a prize for his romantic move
He got up and walked toward me all excited, but I stopped him 2 inches away and made him sit on one of the benches.. then pointed at Mark and John and Steve to sit at the other edge of the pool.
I smiled and started teasing Henry while on all fours, poking my hole, moaning loudly, teasing him to the verge of explosion.
I forbade him to jerk and just let him sit there with a THICK 7 inch cock about to explode..
For my first time, I knew what I was doing as doing it good..
I wanted Henry to be so hard, So horny, that he would become a sex beast..
I wanted Henry to fuck me with his all.. I wanted him to fuck me till I cry..
The second I pointed backwards, Henry jumped up, but was disappointed once I pointed at the other 3 and called them over..
I started sucking John off and jerking the other two while I started shaking my ass to tease Henry.. I was moaning loud on Johns cock...sucking it with pleasure,
Then I pointed at Henry..
He came up from the pool and reached for a bottle of lube he got from the house..
I took it out of his hand and threw it into the pool.. "No need for that babe", I said.
And then he shoved it in..
Yes, the first cock in my ass..
And the loudest I ever moaned!
I was moaning and panting hard, amazed he didn't rip my ass apart. I let go of all their dicks and started focusing on the one currently up my asshole..
Henry was fucking my like a beast, as his dick pushed up the walls of my ass, as I felt it go in and out, I was going nuts! He was fucking me with full force, I was being fucked so hard, I was moaning, crying, holding on to John ...
I started licking Johns balls, as I felt Henry's balls slap mine..
He was fucking me so hard, taking revenge for the way I teased him, screwing me with all his might. I felt like my eyes were rolling in my head, I was in heaven...
Then Henry stopped, and called over Steve..
Then he pulled out and whispered in my ear,
"Ever heard of double penetration?"
My dick got hard as a rock and so the same with my nipples..
I got so excited..
Henry and Steve lied down and intertwined themselves with their balls and dick meeting one another..Two cocks standing in somewhat of a perfect unison.
I was standing on top of em, about to sit on two hot throbbing penises..
I slowly lowered myself...first feeling Henry's cock, then drooping down onto Steve's..
I was in so much pleasure...I didn't even mind the pain..
I was jumping up in down in joy, moaning sounds emitting from my neck, and 2 penises throbbing in and out of a tight hole.. Mark and John sitting watching with envy..
Looking at them.. I thought about Mark and John.. and looked at my two lovers below me with a lustful smile..
How about we try 3 guys?
Both looking up and liking the idea.. I called Mark and John over..
"Measure your cocks up against the other and make out.."
John and Mark looked at me in amazement..
"Cmon, for me? It really turns me on!"
John shrugged and leaned in and started to French kiss Mark as I measured their cocks.
To my amazement, John wasn't lying , his cock was the biggest...
And he was my third candidate..
He lied down spread his legs and lined up his dick with Steve and Henry's..
"Oooh, this is interesting" and once again lowered myself onto their cocks..
3 cocks in one hole, one slutty gay bitch on top of em, moaning his lungs out, as the cocks were moving in and out.
3 cocks in one hole, and I was LOVING it!
I was going crazy, moaning, and jumping, and cursing... I was so horny!!!
Then Henry saids along with Steve " Im cumming! I need to pull out!!"
I looked at Henry and said "In here babe!" and pounded all their cocks with my huge ass...
John, Steve, and Henry all came inside of my ass..It was dripping cum!!! It was all over as I fell off.
I looked at Mark and told him..."I want you to finish in me babe.."
Mark stuck his dick in my cum filled ass without any questions..I was fucked by three cocks but it was still tight!!! And I mean TIGHT!
And He fucked me, harder, and harder, and harder,
and I was moaning louder and louder and louder....
I couldn't take it anymore and I said "IM CUMMING, OH MY GOD IM CUMMING!!! CUM WITH ME MARK!!!"
And then I let out my cum and so did he all in my asshole...
I felt so good after that..I wanted to stay thier bitch forever,
As Mark fell on top of me..
And I said, " As your new bitch, what should be my name?"
Tiffany, Yes Tiffany.. the cross dressing slut with a big ass...

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My bride to be cheated on me as a girlfriend, again when she was my fiancé, and thereafter as my hot wife for 23 years. I guess the stars aligned for us.Me-For some reason I turned to slutty, tight black satin gloves in bed, without ejaculation, a year before I accidently discovered masturbation and gushing in the bathtub. I was 12 the first time I ejaculated, rubbing my cock with slippery shampoo. An overwhelming surge of floating and pleasure washed through my virgin boner as my sudsy palms...

1 year ago
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Cross Dressing Lover

The weekend started off the same as any other for Dhiren. He threw off his drab male work clothes with alacrity and stepped into the shower. He shaved his face, legs and pubic area as was his custom, then, after turning off the tap, moisturized his legs, stepped into a pair of lacy pink panties and hooked on a matching bra. The feel of the light, soft, feminine fabric had always been a thrill to Dhiren, ever since that fateful day when, aged fourteen, he found himself alone in the house all...

Gay Male
3 years ago
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My Road to Crossdressing part 2

I had dressed up since I was a teenager but it was only occasionally. Usually, it was just lingerie and it was always for me and just for masturbation. It was about ten years ago that I decided I wanted to go further and start using makeup and breast forms and wigs etcetera.Quite by chance one day, I rang an old friend just for a chat. I found out that he had rented his house out while he was travelling. The person on the other end of the line was a woman, or so I thought. We got talking and I...

Crossdressing
3 years ago
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A Cross Dressing Fantasy ndash Chapter 5

A Cross Dressing Fantasy – Chapter 5In the low light of our bedroom, late on that Friday night after Beth had transformed me from a former cross dresser into her new girlfriend she had asked if I liked being her girlfriend. I did not hesitate for one second, “Yes Beth,” I said lying naked against her naked body, “I love being your girlfriend, something inside of me seems to have changed and this seems so natural and I feel complete.”My crotch was wet with my cum and her creamy arousal but I was...

3 years ago
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True tales of submission and crossdressing Chapter Two William

Introduction ------------ Following on from my first instalment, here is another true story. As before, I have tried to remember events as accurately as I can, but of course all speech is paraphrased. I hope there are people out there who enjoy reading this, and perhaps it will inspire people to go ahead and indulge their fantasies. Whatever your kink, there's probably someone out there who will be into it too, and it's not a crime to enjoy life! Curiosity... ------------ So...

1 year ago
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My neighbor blackmailed and fucked me for Cross dressing

I had recently moved in a townhouse unit in Oklahoma. Still trying to adjust to the new neighborhood, I was also doing my best to keep my hobbies a secret. You see, I am a cross-dresser by passion. But my new neighborhood is strictly catholic and I can imagine the uproar my fantasies might stir. My next-door neighbor was an old man in his 60’s. He looked younger and stronger than his age. But, my secret unfolded and the neighbor fucked me for cross dressing. Within a couple of days of...

Cross Dresser
1 year ago
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Consequences of Cross Dressing

Consequences of Cross Dressing by Cindy Johnson ([email protected]) My dilemma was that I masturbated all over mother's gown and nylons and I frantically tried to clean everything up as fast as possible. I was frightened that it would leave a stain and I didn't know what to do but after twenty minutes of cleaning everything with soap and water, I felt like I was in the clear. I put everything back where it I found them and ran to my room reflecting on what had just happened. I...

3 years ago
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intro to the world of cross dressing1

My family was middle class mutt of a family. My mom brought two daughters and one son, Tammy, Lilly, and Teddy, or “Tee” as we call him, into the marriage; she had with my dad, and they had two, my brother and me. My full brother’s name is Ken, and I’m Sam. My dad was an accountant and a part-time college professor at the local community college, and my mom stayed at home as a housewife. We were all dragged to church every Sunday and when we became of age we were allowed to choose whether or...

1 year ago
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A Proud Cross Dressing Gay Male Who Enjoys Sex Free Sex Stories and Adult Erotica Stories

When I was 12, I went to shop for shoes with my mother. I would walk around the store, making my mother laugh out loud. The onlookers at the store, would often look at me in astonishment and wonder, “How is this little boy handling pencil heels so well”?. My mama knew it back then that I was born different and she fought the world to make me who I am today, a proud cross dressing gay male. It was my first prom and I was nervous. I was worried that I will be made fun of at school, but my mama...

Cross Dresser
2 years ago
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Friends With Benefits 8211 CrossDressing

Hi sexy people. Hand shake to guys and boobs shake to girls. I appreciate your comments on my previous stories. I’m going to narrate one more story which could be few people’s fantasy – Cross dressing. So let’s get started. Well one day I was hanging out with my fellow colleague Sindhu. We were quite close, as in, we have had sex couple of times earlier. But we were not committed. In fact she had a boy friend who was still a virgin. That means Sindhu never had sex with anyone else. We were not...

1 year ago
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Caught Crossdressing by my wife

Caught Cross-dressing by my wifeCaught cross-dressing by my wifeI have always been a cross dresser and enjoyed it. When I got married I put all my special clothes in the basement and lived a normal life. One day I was home from a trip early and found my wife was doing the laundry. There on the top of the pile were her pink knickers. I remembered I loved the feel of silk on my body. She left the room and I picked them up and I was running my hand across them and soon I was feeling and rubbing my...

1 year ago
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Thangaiku Theriyaamal Amma Magalai Oothen

Indru tamil kama kathaiyil ilamaiyaana magalum pinbu vithavai ammavaiyum eppadi usar seithu matter poten endru ungaluku solugiren. Suvarasiyam athigam irukum kama kathaikul selalam vaarungal, en peyar karthik. En veethiiyil oru pen ilamaiyaaga sexiyaaga irupaal, avalai thinamum sight adithu kondu irupen. Thinamum aval kalluri sendru varum pozhuthu iru velaiyilum sight adika arambithu viduven. Aval peyar nandhini vayathu 21 irukum, avaluku veetil aan thunai kidaiyaathu. Veetil oru amma iru...

4 years ago
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Cross dressing journey

Hello everyone I wanna tell you all about my cross dressing fetish and how it all started. Before I begin let me start by telling you all a bit about my family and myself. We are a family of three, my mom, dad and myself. Both my parents worked which gave me a lot of time to be alone. Although both of them worked it was my Mom who was the main bread earner of the family. Her name is Shikha and she is the vice president of a private company and earning a good salary apart from amenities like...

Lesbian
1 year ago
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My Road to cross dressing

I was bought up in a time when taboos about something alternative like transgender people or cross dressing was still considered to be a no go area. Society made one feel that you were an out cast or mentally ill. Luckily times have changed and it has become much more acceptable, even though we still have a long way to go. I first started dressing when I was about eighteen. My sister had this old green dress that she had thrown away. I remember liking that dress and secretly retrieved it from...

Crossdressing
2 years ago
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Tiffanys Torment

I glanced at my watch. I noticed it was almost 4:30 in the afternoon. The underground parking garage was filled with cars, but as of now no one else was around. Most folks were still working inside the building. That was just the way I wanted it. I was leaning against the trunk of my rented car, which had the hood up. There was nothing wrong with the vehicle. It was just a good way to stake out the place. Anyone who happened to notice me would think I was just some unfortunate guy having car...

3 years ago
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True tales of submission and crossdressing Chapter One Meisterin

True tales of submission and cross-dressing : Chapter One - Meisterin It is my intention to write a series of true life stories, detaling various encounters and adventures I have had. I know the site's called "Fictionmania", so I hope my contributions are not unwelcome. The stories are not as racy as most of the fiction posted on here, but remember than these stories are real, and described to the best of my memory (of course all speech is paraphrased). Hopefully the fact that these...

3 years ago
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Athena Corp Chronicles Futa Gym Shower Slut

It had been an interesting six months that led Andrew here. While home for winter break, his parents announced he wouldn't be returning to college. His mother, in particular, had decided the investment was no longer worth it. His father supported her decision wholeheartedly. Andrew was told that new opportunities for young men with no degree were opening up in their area. He had no idea what kind of jobs his parents meant, but he took them at their word. Mother allocated him a weekly stipend...

2 years ago
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My Road to Crossdressing Part 3

From the first time I dressed, there was always a sexual element. I used to find the time to wear something feminine and wank myself. It went hand in hand, so to speak. One of the things I loved doing was getting dressed up and laying on my bed with my legs over my head and wanking.When it was time, I would cum in my own mouth. I did it so many times but it was always uncomfortable, but I used to cum anyway. I didn’t swallow but spat it out, every time. I also used to kneel in front of the...

Crossdressing
1 year ago
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Tiffany at the Glory hole

Well, It was a summer day and Tiffany was just looking at the movies and pictures I had on the computer and had something on her mind. We had her nephew over to spend the night and it was a good excuse to say we were going to go out for a while so he could babysit. She wanted to drive to surprise me as to where she was taking me. I kept asking and she kept saying, "You will see, Besides I was looking at some of the movies and pictures and I want to try some of them." My mind was racing as to...

1 year ago
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Tiffany the twisted sister

My wife had an opportunity to do a month long meditation retreat in Bali, she said she knew all of my worries and planned ahead to make things easier for me, her older sister by 2 years was going to come stay with me and help with the house and k**s. That when she returned she would be my sex toy o do with as i please for a month and has set it up so each night i would receive a personal video of her playing and talking sexual for me in my e-mail each day. she had been making them while i was...

4 years ago
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Tiffany Ch 2

------------------------------------------------------------------------------------------------- The next few days were agonizing for me. I was on pins and needles, waiting (and hoping) Chris would finally call me. I felt so stupid, checking my cell phone every chance I got, or keeping my cordless home phone with me at all times while I was at home. I didn't dare leave the house except if absolutely necessary (I realized that I REALLY needed to go grocery shopping), for fear of missing...

3 years ago
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Tiffany Ch 1

------------------------------------------------------------------------------------------------- Hi! My name is Tiffany, or "Tiff", for short. This is the story about meeting the man who changed my life, Chris, and how I was finally able to "let myself go", sexually. I guess Chris was the guy that allowed me to finally express my sexuality and got me to "cut loose my inner slut"! First, let me tell you a little about myself. I'm 28 years old and live by myself in Miami. ...

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