Shemales Porn Stories
Page 79

A cum slut is born

There's little doubt about what turns me on most -- just check out my favorite videos and photos. Cum, Cum, and more cum. I'm a late bloomer as far as discovering my kinky side. After a long, dull marriage consisting of vanilla sex, I got divorced a few years back and decided to explore some fantasies. I love porn, and I've always been somewhat envious of the chicks in the xxx vids, they always seemed like they were having tons of fun getting their cunts, mouths and asses filled with hot cum. Multiple cum shots really turned me on. But I'd always identified as heterosexual -- so how could it b... Continue»
Posted by jizzlover123 2 years ago  |  Categories: Fetish, Group Sex, Shemales  |  Views: 3530  |  
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she had a COCK bigger than mine ..oh my !

this is no B.S ,no fantasy, no make belief, no fairy tale,.. this is a TRUE STORY and an ACTUAL EVENT.

iv always been a very observant k** growing up always trying to find the unseen and overlooked things in life i guess you can say curious....how curious ??:] well...

there was this older lady who il call Ms.Auburn who lived in the neighborhood that everybody knew,especially the men because she was a tall long legged brazilian chick with a pair of double D's that you couldnt possibly overlook and she would always come out on her steps with a short tight satin auburn coloured housecoat a... Continue»
Posted by jerkme 2 years ago  |  Categories: Fetish, First Time, Shemales  |  Views: 1734  |  
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Turning my neighbour on in pantyhose part 2

So.....there I was. Lucy...dressed up to the nines, crossed legged on the window sill. The guy next door, rock hard, almost licking his lips! I was sooooo turned on. I knew I looked fab today! Big headed? Sometimes you just know dont you? You are about to get to know me better....

Was it wrong to be turning this guy on so much? His cock sure wasnt bothered! He wanted to Fuck me because he fancied me...because I looked like a sexy, hot maid! I would imagine this is one of his fantasy's...I'm just happy I'm succeeding in making it a reality.

So did I stop? Quit while I was ahead? What... Continue»
Posted by lucyslegs 2 years ago  |  Categories: Fetish, Gay Male, Shemales  |  Views: 581  |  
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Shemale fun

Recently I've been chatting with a very feminine and beautiful shemale named Lisa.

We've been trading photos and dirty talk over chat lines and emails. I've always fanatsized about a cick with a dick and unexpectedly the opportunity came that we could potentially meet. Being married I had to concoct and excuse as to why I had to go to (city name withheld) and my wife didn't see any reason not to bnelieve me. My wife knows that I love porn, but I've never expressed to her that cock also turns me on - especially shemale cock. Somethings are better left secret.

I arrived at the hotel th... Continue»
Posted by seizetheday 2 years ago  |  Categories: First Time, Shemales  |  Views: 1469  |  
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my first tranny (pt. 1)

you always remember your first time.


I remember my first blow job from an ex. (believe me, thats another story.) the first time I touched a pair of tits. the first time I ever ate pussy. the first time I fucked a woman in the ass. & I'll always remember the first time I was with a tranny.

her name was brooke. I always wanted to be with a tranny because I was always curious. I mean, shes a chick right. but then she has a dick. you all know some trannies are drop dead beautiful. this one was. I was looking in the e****t section of one of those paper you get at a porn shop. I always want... Continue»
Posted by radec_24 2 years ago  |  Categories: First Time, Shemales, Taboo  |  Views: 2661  |  
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My Frist time with a tranny

My Frist time it was back when AOL frist came out. I was in a miami chatroom and I met a tranylicous. We Started to chat. I remember going to the profile on the side of the message window and I found out throu pics what a tranny was. I must of been 13 at the time or so. She gave me her address. it was not to far from Downtown so I head over to meet her as I smoked a joint. She had a nice apt, pretty empty She had just moved from Ny. After a little chat we had that helped me relax She came closer to me and we started to Kiss. I felt my bl**d rush threw my body I could feel my ear tingle. She w... Continue»
Posted by lucifer696 2 years ago  |  Categories: First Time, Shemales  |  Views: 1172  |  
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Where it all started

I guess it all got started when I was a teenager and joined a swim team with Brian, who was my best friend and whose parents also happened to be my parents closest friends. We had to swim in skimpy little speedos which didn't conceal much from the imagination and hugged your every curve very tight when they got wet. One day after practice Brian and I were alone in the locker room when he looked at me in my suit and told me how sexy I looked. I was suprised by the comment, but even more surprised at how it turned me on. "You really think so?" I asked him, shocked at the excitement I felt a... Continue»
Posted by cdmelissaluv 2 years ago  |  Categories: Anal, First Time, Shemales  |  Views: 1699  |  
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PantyBoy Gets A Reaming

I love to get really in touch with my feminine side. I get so turned on when I watch a man look my body up and down while I'm wearing some really sexy lingerie. I feel so naughty and slutty, knowing that I am going to let him do anything and everything he wants to me!! I was chatting in a room on one of the big websites when an IM from a guy in my area came across my screen. He wasted no time telling me how he liked my pictures that I had posted and how horny they had made him. I told him that flattery would get him everything, and he immediately invited me to his place. I don't usually meet i... Continue»
Posted by LRock4fun 2 years ago  |  Categories: Gay Male, Interracial Sex, Shemales  |  Views: 1180  |  
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My dream encounter with a tranny

There is nothing more hot than to have a slim, pretty body on my hands to fondle. To feel their erections starting to grow and to taste their cocks in my mouth. I lose control when I'm around a shemale.

I have fantasized a lot about getting fucked for long periods of time and in a lot of different positions. Unfortunately, all my shemale hookups have been with e****ts that do the deeds rather quickly and then leave. I still have to find a shemale friend to spend long long hours either fucking, fondling or sucking.

I dream about a hot, slim, tender shemale arriving at my doorstep. She beg... Continue»
Posted by feinor11 2 years ago  |  Categories: Anal, Hardcore, Shemales  |  Views: 1055  |  
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Sissy Training

This is a true story, looking back it is hard to believe it actually happened, but it did.

I was working for the government in DC and living in Maryland and my fiancé was up near Cape Cod. Just about every weekend she’d fly down or I’d fly up to spend the weekend together. We’d been doing this for about a year since I took the job in DC. Our sex life was fantastic. We’d role play, put each other in light bondage… all sorts of fun things. I knew she was bi and we occasionally would invite another woman to join us. She also knew I liked to dress up. We’d often go to the local thrift sto... Continue»
Posted by MichelleSEmass 2 years ago  |  Categories: Fetish, Interracial Sex, Shemales  |  Views: 2695  |  
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first time cumming

When I was 12 I began secretly stealing my s****rs pills and clothing and make up, I was dressed up as a girl when I was younger and enjoyed the feeling so growing up I have always had a time to connect with my femme side, when I started stealing her clothes and make up I would look up videos online to see where all the make up went and what was good colors for my complexion, I've always been pretty skinny but the last year I let myself go and put on a few extra pounds and began to fill in the bras and panties a lot better than usual. After noticing how great it felt I began to diet again but ... Continue»
Posted by reefermcrevolver 2 years ago  |  Categories: Anal, First Time, Shemales  |  Views: 599  |  
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My first time with a tranny

I always had a strong sex drive, and since I had been around 16 I had been turned on by gay porn. I must say that I am straight, well on second thought, better say that I am bisexual. And I always have and will like girls. But there is something about a cock that turns me on and I then discovered shemale porn. I think that a hot sexy shemale and a cock is the best combination there could be. I have a strange fascination with cocks and a hot sexy girly body tops it off.

In August 2007 I was 24 years old and was constantly masturbating to shemale porn. My best friend was getting married and ... Continue»
Posted by feinor11 2 years ago  |  Categories: Anal, First Time, Shemales  |  Views: 6206  |  
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Night out

My wife knew that I liked to dress and would often help me. Usually it just consisted of dressing up and watching TV or maybe having hot sex. Once she had me dress and took me for a drive to the park where she made me walk around and pose for pictures. She’d also take me to the local thrift stores where we’d buy new things for Michelle. In bed we’d often talk about me dressing up and going someplace in public like a club or show. It seemed to make us both hot and the sex we had afterwards was fantastic.
One weekend we had to go to Providence for a friends wedding. My wife told me she w... Continue»
Posted by MichelleSEmass 2 years ago  |  Categories: Anal, Group Sex, Shemales  |  Views: 1174  |  
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Sissy Training

This is a true story, looking back it is hard to believe it actually happened, but it did.

I was working for the government in DC and living in Maryland and my fiancé was up near Cape Cod. Just about every weekend she’d fly down or I’d fly up to spend the weekend together. We’d been doing this for about a year since I took the job in DC. Our sex life was fantastic. We’d role play, put each other in light bondage… all sorts of fun things. I knew she was bi and we occasionally would invite another woman to join us. She also knew I liked to dress up. We’d often go to the local thrift sto... Continue»
Posted by MichelleSEmass 2 years ago  |  Categories: BDSM, Group Sex, Shemales  |  Views: 2373  |  
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Panties For ME

Ok, here's a quick story and true at that. I was away on business one night and surfing for sex on Craigslist. The title of my post was "If I'm so strait then why do I want to get fucked like a girl?" It was a popular post and I got a bunch of replies, and a bunch of men wanted to fuck me. I'd just broken up with a girlfriend and I'd decided I'd finally give in to my urges and try the sissy thing for a few months.

After many advances, I ended up going with someone a little older and little less hot than the others because he had the ingenuity to ask what my fantasy was and actually asked m... Continue»
Posted by rikkk72 2 years ago  |  Categories: Fetish, First Time, Shemales  |  Views: 764  |  
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Abigail's First Time

This is the story of the first time I dressed for a man. I had been with men before, but had never been with one as a girl. I would say 95% of it is true. I tried to keep it as close to the truth as possible. I will say that the acts described actually happened, and we really did go four times. I leave you to decide which parts you think are the false ones.

I checked my hair and makeup in the mirror for what seemed like the millionth time. Nerves I guess. Tonight was the first time I was going to meet a man while dressed and acting as a girl.

I adjusted my dress, a dark blue bodyc... Continue»
Posted by cdboy22 2 years ago  |  Categories: Shemales  |  Views: 496  |  
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good fucking

thank god 3 months at sea not had rest or sex havin men around 24/7 can do things to a man,singapore been here few times wid times and some fucked up shit wow,
left for land 3 days leave was gonna make the most of it.
went in couple bars checking things out see what was happening,
found out there was a lady boy competition on thought what the hell always good for a laugh, never thought anything about it, as in men being women,
got in the club it was packed with sailors all with the same idea spose,
any way the guy in charge started to speak to the crowd asking if there was anyone
who w... Continue»
Posted by peternorth111 2 years ago  |  Categories: Group Sex, Hardcore, Shemales  |  Views: 1106  |  
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My sexual fantasies



Well, I've always had sexual fantasies, since I was very young, I discovered the joys of masturbation around the age of 8, I remember playing in my bedroom with my pillow, I imagined it as a woman, or something like that, and so I took the pillow and I put it between my legs, rubbing my little cock against the pillow in a sensual movement, thinking about dirty things, until I reached the orgasm and jizzed over the pillow, it was so exciting for me and I enjoyed very much those situations. I remember several afternoons playing with one friend of mine in the staircases of my condominium, we ... Continue»
Posted by Porcellone 2 years ago  |  Categories: Masturbation, Shemales, Taboo  |  Views: 1250  |  
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Turning my neighbour on in pantyhose

One of my neighbours whos in his early 50's and clearly a man of taste;) asked me recently had we got a cleaner in?! I said yes a couple of times a week. He seemed happy!
I know why..... My name is Lucy and I love strutting around in front of the window with sexy outfits on. I'm meant to be our new cleaner but I have to be honest, I don't do much, just a lot of bending over and stretching up high!
Yesterday I was dressed as 'Lucy the maid', shall we call her? I had 4 inch black leather heels on, which make my calves look fab!My favourite stocking patterned tights which are as equally shin... Continue»
Posted by lucyslegs 2 years ago  |  Categories: Gay Male, Shemales, Voyeur  |  Views: 1709  |  
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Why did I settle for that?

Just made it back from Miami, was a great visit, but it could have ended after the first night, and that would have been alright. Hated the dirnking and the smoke, but did meet another lovely tranny who did give me the tour and the break from this horrid northern weather.

Although the sex with her was good... Ok, average, I didn't think it was worth the money that spent getting there and back. Why did I let her shit on my chest while skull fucking me anyhow? Some things shall always be a mystery I suppose.

I did love what she wore, how she looked, and her long slender candy, it fe... Continue»
Posted by Stickpiggy 2 years ago  |  Categories: Masturbation, Shemales, Taboo  |  Views: 819  |  
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