Shemales Porn Stories
Page 6

Becoming Kitty

I guess I should start with that I've loved to wear panties. In school, I would sneak into my mom's room and put on her panties. While I was straight, at least so I thought, my fascination with panties never stopped.

In college, after my parents died in a car accident. I had my first gay experiences, including my first crossdressing experience for Halloween my high school. After my parents passed away and since I was an only c***d, I basically came out and began to openly experiment with my sexuality with both men and women.

However, my true passion was dressing as a woman and having se... Continue»
Posted by CumLovingKitty 2 months ago  |  Categories: First Time, Gay Male, Shemales  |  
  |  6

She knew what she was doing

Oh god she knew what she was doing...

The latex gloves fondling my aching balls, fingers squuezing and tugging as he hungry, made up lips worked my shaft.

Her moans were driving me crazy and it was everything I could do not to empty in her throat right there.

I remember trembling when I walked up the stone path to the front door. 29 and married for 6 years, but here I was about to knock on the door of a man dressed in womens under wear. A year of shameful and guilt wracked wanks to sissy and tranny porn, watching those soft cute trannys sucking and taking cock like real women.

Af... Continue»
Posted by DaRoyale 2 months ago  |  Categories: Shemales  |  

The College Fantasy Part 2 (Futanari)

I was still in shock. The taste of her cum pervaded my mouth and there was some running down my chin. I couldn't believe what had happened and I could believe even less how much she had cum. Her newly grown cock had continued growing from when I had first noticed it. Even though she had just blasted me with her load she was straddling me while rubbing her massive footlong cock, almost double the size of my own. I had yet to cum and was still feeling a bit horny although the situation had caught me off guard and I was softening up a bit. She just looked and giggled. Her expanded tits boun... Continue»
Posted by fictiong 2 months ago  |  Categories: Fetish, Hardcore, Shemales  |  
  |  2

P and I spend an amazing night with Ivy!

P and I have been buddies and fuckbuddies for a little while. We're both bi and we hooked up through my fiancee (she loves to watch us play together) and we found that beyond playing with her, we had a bit in common. We're the same age, but where I'm kind of bearish, he's smooth. My cock is thick with a big mushroom head and his is longer and thinner. We both love to suck and stroke together, although that's as far as we had gone until that night.

P called me one night, wanting to have a guys' night out. Drinking, gambling and hitting strip clubs and sex stores. My fiancee said to have fun... Continue»
Posted by Mrtommyboy 2 months ago  |  Categories: Gay Male, Group Sex, Shemales  |  
  |  2


“So, Ronnie, how about another drink?” George asked me.

“Oh, George, I’m so d***k, but what the hell, sure, I’ll have another.”

“Thassa boy,” said George.

“Let me hit the head, George,” I said and slid out of the tavern booth, then staggered to the bathroom.
Once inside, I locked the door long enough to take off my pants, then my jockey briefs. and stuff them in my pants pocket after I’d put my pants back on. I looked at my swaying image in the old mirror over the sink. I smirked and pulled down my fly, and pulled out my hard cock. Then I almost fell over, and decided to stick my co... Continue»
Posted by ssup28 2 months ago  |  Categories: Shemales  |  
  |  1

late night sissy turns into live in

Short story my first one! I ran to the store to get some smokes and a few beers and found a new friend.I saw what I thought was a girl riding a scooter stop so I said hello then I realized it was a very sexy dressed guy.He says hello and goes inside I wait for him to exit. He comes out and I just smile and make small talk.I see he is very feminine and that gets me hot.We talk for a bit then he asked me if he can have a beer I said sure,we drink a beer and I then ask if he would like to come over he says sure.
We get to my place he gets in my van and says lets just sit and drink a few beers,he... Continue»
Posted by lookdowner 2 months ago  |  Categories: Gay Male, Shemales  |  
  |  5

First night out as a sissy

Nervously, I came out of the restroom. I had never come out side fully dressed in my girly outfits. Rickey was about meet me in 15 minutes so I hurried. I found out what cross-dressing is when I was in high school and that was the time when I, with a slim and little frame started doing it. Inside house and at various encounters I had brought the dresses with me in bags. But outside among people dressed as a girl?! Now way, never…till now! I could not believe that I was outside wearing a tank top and hot pants! Every step I took gave me goosebumps. Every time Ilifted my head and saw any one loo... Continue»
Posted by CumLovingKitty 2 months ago  |  Categories: First Time, Gay Male, Shemales  |  
  |  4

Becoming the neighbourhood slut - Part 3

Read Part 1 and 2:


"Hello guys" I said quietly as I finally reached the living room and entered it. I stopped at the entrance, my gloved hands were on my tiny leathered waist to model my body for the men and to show them exactly how slim and vulnerable I am.

My eyes were tracing the room to see the guys. Everything was like it was happening in very slow motion. At first glance I was looking for Mark, but I couldn't see him. One guy, second, third, fourth... fifth... SIXTH... SEVENTH... EIGHTH... and finally Mark. Yes, a total o... Continue»
Posted by analhottie 2 months ago  |  Categories: Anal, Group Sex, Shemales  |  
  |  3

getting used by many

I had been talking with Kevin now for about a month online. We kept talking about getting together, and he wanted to know how far I would go. I had told him that I was a total slut and loved to be used, abused and humiliated. He said that I would be perfect pig for him, and if I was real and not just someone online looking to tease he would take care of all my desires. Kevin said that he would set the ground rules that I must follow for our upcoming encounter, and I said I would.

Kevin told me that I would be picking him at the el stop after he was done work which would be around midnigh... Continue»
Posted by slut2eatcum 2 months ago  |  Categories: Anal, Group Sex, Shemales  |  
  |  2

My Perfect Transsexual Bitch

My Perfect Trans Bitch

I met the proto-bitch in a nice little kratom bar I occasionally patronized
when I wanted to unwind. Clean, Old West style bar, dimly lit but not dark.
Christopher (later Chris or Chrissy) was sipping some green variety so
I ordered her a better, more expensive red vein Thai with pollen.
(I found out much later that she was paying the owner for food and kratom
with sex. (She had to wrestle with me until I listened to her good advice
to not rush back there and end up in prison.)
I never really got high from kratom, just relaxe
... Continue»
Posted by yutubeslut 2 months ago  |  Categories: Anal, Interracial Sex, Shemales  |  
  |  2

Trip to the mall

So here I was again on a trip the the local mall. My wife the finest shopper of them all was in need of some new makeup, so the good guy i am decided to open my wallet and take her. (NOW before we go any further, I am a closet shemale and now even crossdresser fan for years) So upon arriving at the mall weake our usual rounds and eventually stop at her favorite chain makeup store, yes I've been there before. Today though as my wife was doing her thing with a female sales person, I noticed a very interesting young lad working. Now there is always what considered the "gay guy" working in these ... Continue»
Posted by Fnumo38 2 months ago  |  Categories: First Time, Gay Male, Shemales  |  
  |  1

Becoming sissy Jenny Part one

Hi, my name is Jonas and I´m 25 years old. This is the Story of how I became a sissy. So actually my name is Jenny now. But lets not get ahead of ourselves. The story has a slow build up, I hope it´s interesting for someone. Thats part one, I will continue the story from time to time. Everything sexual in this story happens to people over the age of 18.

I guess it all started whit my mom being a gold digger. One of those women who have a pretty face and a nice body and try to make a living out of it. After a few years of being an e****t, getting to know people, sucking the right dicks, gett... Continue»
Posted by jenny42 2 months ago  |  Categories: First Time, Masturbation, Shemales  |  
  |  2

A tribute to Joy

I had always loved women’s clothing. Well truth be told, I had always wanted to wear women’s clothing. I envied women’s ability to change their look with just a little effort, a tight skirt; that was so sexy in one way to a pair of jeans that was sexy in an entirely different way. Then there was the hair thing. I thought that it was so cool the way that women could change their entire look, even their personality by just wearing their hair differently. I really like women. If it wasn’t for that monthly thing I would want to be a woman. I would be a lesbian if I had my final sexual preference. ... Continue»
Posted by justluvtrans 2 months ago  |  Categories: Anal, First Time, Shemales  |  
  |  13

Fantasy Mum and her bloke pt2

In the end i figured the situation was way too crazy. I got on with my day as usual and put the card in my pocket.

Later on in the evening my mum came home, she said something about going out and headed for the shower. I sat in the livingroom listening to the water running, i kept getting flashbacks. The moaning, watching her getting fucked, the screaming, and of both her wet holes on show for me to see. Interestingly i also found myself enjoying the thoughts of seeing Tony turned on and him touching me. My cock started to twitch and grow, again my cock thinking for me i found myself headed... Continue»
Posted by jessicacd1982 2 months ago  |  Categories: Shemales, Taboo  |  
  |  1

MY first time with a TS

Actually it was not intended that I should visit Fransheska.

I had in fact been looking at Iris Baby... her profile I had seen on e****t Guide a few weeks ago. When I finally decided me and got it all in place, it turned out that Iris was not in the country. But then (the other day) she showed up here on the wiki.

And THEN finally I got a dial tone! But after three calls without answer I stood there with my 1,500 burning in the pocket - and a bulge in my pants - and still no deal. Now what?

Got my mobile out of the pocket and then scrolled down... Fransheska... the two Tayras... Lore... Continue»
Posted by mazis2003 2 months ago  |  Categories: Anal, First Time, Shemales  |  
  |  1

TRUE First Time Story

This is a true story. read stories sometimes but never thought i would ever type one, but as i get older i think some of my experiences could make for decent stories. I don't have the best imagination, so i am writing (and will only write) true, actual stories. I understand my profile is blank with no original content, because I'm very discreet about it, but am loosening up, and am beginning to make content that protects anonymity, so bare with me.

to start, i am a masculine male. overtly straight, but with a hidden i layer of bi.i had girlfriends and got with girls, but always wanted to ... Continue»
Posted by eman22 2 months ago  |  Categories: First Time, Gay Male, Shemales  |  
  |  4

Feminized by My Father

I opened my eyes, blinked, yawned, closed them again.

I felt confused, disoriented in a way that was... strange. It wasn't like waking up was supposed to be, I wasn't half asl**p. I can't remember getting in the bed, in fact I can't remember the last thing I remember. Where did consciousness end last? I was clueless.

I tired to move my body and I found it difficult. I could move though, I rolled over onto my stomach and opened my eyes, I was on the guest bed in the basement. Blinking didn't clear the fuzz from the world, so I went ahead and tried to get out of bed. As I stood I felt an i... Continue»
Posted by AssLover1992 2 months ago  |  Categories: Shemales  |  

Scum part 2

“Look away” he whispered as his naked body laid on top of mine.
As i turned my head to the side and faced the wall, I could feel his hard cock pressing against me as he made me raise my legs to allow him entry into me.
With no foreplay or anything he spat on to his hand and rubbed his spit against my hole.
As he f***ed his way into me, his body pushing against mine, my head facing the wall and his hand holding it so I didnt turn back… I tried to catch my breath as i felt his cock tear through me, forcing me to take it, and his foreskin allowing him to get deeply inside.

Every thrust from... Continue»
Posted by tarasexytgirl 2 months ago  |  Categories: Fetish, Hardcore, Shemales  |  
  |  2

total sissy humiliation

my phone buzzed.

looking at the screen the name before me both puzzled and startled me.
I had posted an ad on craigslist 10 days ago, offering to suck cock. i was 32 and had been dressing as a girl and fantasizing about sucking cock since i was 13.....and now being single, I'd decided to act. within 12 hours of my ad going live I'd had 10 emails from guys...some of which i deemed timewasters. I'd quickly narrowed it down to a guy named least thats what he said his name was.

Lee lived locally, and worked as a bar manager for a local pub. I knew the pub, it was a normal quiet pu... Continue»
Posted by hornyTVluvr 2 months ago  |  Categories: BDSM, Fetish, Shemales  |  
  |  6

Fucked by a ladyboy

A couple of months a had sex with a ladyboy for the first time. I met her on the internet, after chatting for a couple of weeks she was visiting my country for vacation (she's from Thailand).

We met in Amsterdam on a sunny afternoom. After walking through the city and showing her the touristical highlights, I asked her if she would like to come to my house. She agreed. On the way to my house we were holding hands constantly, and in the bus she rested her head on my shoulder. At my house we started kissing en making out. Then she asked my if I wanted to go to the bedroom. I showed her the wa... Continue»
Posted by gogolo999 2 months ago  |  Categories: Anal, Shemales  |