Shemales Porn Stories
Page 10

Milwaukee Cuckold was watched

Judy hadn’t done much lately due to some health issues. She used to jerk me off once every couple of weeks telling me what she had done and that had been less lately. One morning she walked into the f****y room and told me to be ready tomorrow morning as it was her turn to watch me. I laughed and said, “doing what?” She just smile back.

The next morning she told me we needed to run some errands. We stopped at the craft store and the pharmacy and then se said let’s stop at the office so I can pick something up. We went to my office and when we got back to my private office she said, “go jump... Continue»
Posted by toothmedic 3 months ago  |  Categories: Fetish, Shemales, Voyeur  |  
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Good Girl stay limp for Daddy!

Good Girl stay limp for Daddy!

Are you a Total Top, a real Daddy? Do you want your faggot to become a fully passive pussyboi, completely dependent on his fagcunt for all orgasms and sexual pleasure? You need to train him to think of his ass as a fully functional pussy, a full-time cunt. The advice below does not apply to versatile couples, only to those interested in a total-top–total-pussyboi type arrangement.

Tips for training a pussyboi –

1. Discourage the use of his cock. It is too small, anyway, to be of any use. Every time he uses his boiclit he is experiencing pleasure as a T... Continue»
Posted by StarScreamUSA 3 months ago  |  Categories: First Time, Gay Male, Shemales  |  
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The First 150 Rules for sissys

Rule#1: A sissy does not have a cock. A sissy has a clitty
Rule#2: A sissy wears a bra and panties
Rule#3: A sissy loves cock
Rule#4: A sissy loves cum
Rule#5: A sissy takes it in the ass
Rule#6: A sissy loves pink
Rule#7: A sissy loves her toys
Rule#8: A sissy dresses like a slut
Rule#9: A sissy shares
Rule#10: Sissies love facials
Rule#11: A sissy must have a tight ass
Rule#12: A sissy must have perfect bimbo makeup
Rule#13: A sissy grows big fake tits
Rule#14: A sissy is a pro cock sucker
Rule#15: One is not enough
Rule#16: A sissy belongs on her knees
Rule#17: A sissy doesn... Continue»
Posted by Sinderellla 3 months ago  |  Categories: Fetish, Hardcore, Shemales  |  
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Me and a daddy

This is a story about my meeting with a daddy. It was going to be two of them but sadly one didn't turn up and his cock looked so sexy.

I knocked on the door and waited for him to answer. He opened the door and ordered me in quickly, feeling my arse when I walked past him into the bedroom. He told me to get on my knees straight away and sniff his crotch, forcing my face into his hardening cock. The masculine Snell of his cock and balls already getting me horny. He then ordered me to strip whilst still smelling his crotch. Then he told me to get on the bed on my stomach in just my underwear... Continue»
Posted by sissyexeter21 3 months ago  |  Categories: Anal, Gay Male, Shemales  |  
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Mrs Officer (fantasy story)

After a good workout at my gym I get in the car to head home. I notice a police car follows me out of the parking lot. Thinking nothing of it, yet making sure I do the right speed, I keep rolling. I get about a half mile down the road and the cop hits the lights on me. Im looking, searching, trying to see if I failed to signal or what. I pull over on a side street and put it in park. The officer gets out and makes her way to my side of the car.
I can't help but notice how thick and powerful her thighs were in that uniform. She yells out "Driver get out and put your hands against the car NOW !... Continue»
Posted by Champdick 3 months ago  |  Categories: Anal, Hardcore, Shemales  |  
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First time with a transvestite

I have always enjoyed cross dressing, and in the few years I have been divorced, I have been lucky enough to dress whenever I pleased, but at 6, 2" and 15 1/2 stone, I'm never going to pass as a girl.

If you see my favourite videos on my profile, you'll notice that quite a few are transvestites fucking guys, and this is something I have always wanted to do, but the opportunity has never arisen....until last week

I was in Amsterdam on a business trip, and was supposed to fly in and back in a day. However, the meeting dragged on, and by the time we were finished, there was only one flight... Continue»
Posted by funwatford 3 months ago  |  Categories: Shemales  |  
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Indian CD Manusha Crossie got fucked in train

Though I am very active in having sex with men as a closet CD, I never tried anything in public and wanted to try at least once. So, I decided to grab the opportunity on my train trip to Delhi. Though I was not fully dressed up like a CD, with my attire, tattoos, and glossy lipstick, anyone on the platform or train could easily make out that I am a gay or a transgender and that thought gave me an instant kick.

It happened on my train journey to Delhi a month back. I was wearing a lady v-neck slim fit t-shirt a thigh-sized shorts and slippers with my sexy lady specs on. I also had tattoos on... Continue»
Posted by manushacrossie 3 months ago  |  Categories: Anal, Gay Male, Shemales  |  
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My dream to be a d**g house whore

Who I want to be
Look I am not like your typical gurl. I am well educated from a good home and I have a great practice. I am clean disease free and always smell nice. I have always been a sex addict since I was little. As I got older my tastes got kinkier and kinkier. I have now been a submissive since my teen years and I just came to the extreme side of that. It all started a year ago when I started seeing a new mistress. She was into feminization so she started dressing me. I liked it ok as she would use dildos on me but what I really liked was being called names and made to go out in publi... Continue»
Posted by dncn31 3 months ago  |  Categories: Group Sex, Hardcore, Shemales  |  
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Choosing An Outfit.

Tammy was my next door neighbour when I grew up. We went to school together and were very good friends. She was beautiful, athletic and great natured, and would have been the perfect girl for me or indeed any guy. Alan was the son of my mums best friend, six months older than me so like Tammy we were at school together and because of our mums, we saw a lot of each other out of school too. Alan's parents had split up so he spent some weekends with his dad who was a big fan of the outdoors, so we often were out with him, camping, fishing and boating when Alan was at his dad's.

As we went into... Continue»
Posted by JemC 3 months ago  |  Categories: Gay Male, Shemales  |  
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Meeting Tara again

For a few weeks i replayed the night i had spend with Tara over and over in my head, each time i would get a hard and get super horny, to the point that i would jerk off 3 maybe 4 times a day. I practically lost interest in all porn other than shemale sections. My knowledge grew as did my interest. Tara the sexy trans woman of my dreams has sent me down the rabit hole. I am waiting to find out how deep it will go.
As i mentioned previously i am a tall guy 32years old with 240 pounds to my frame. I have an 8 inch cock and i am in love with trans women. I had been txting Tara and flirting with ... Continue»
Posted by b84bomber 3 months ago  |  Categories: First Time, Shemales  |  
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My first time with a shemale

OK, I was wasting my time on shamble videos and pictures on the web for about 8 years! When I first entered a porn site I almost got sick, but soon I got really curious about it but didn't dare to click that button; couldn't explain why I wanted it so much though. Eventually I pressed it. I started with shambles alone, then shambles fucking girls, then shambles fucking shemales and end up with shemales fucking guys... I started loving it, watching it on a daily basis. My fetish for thong tanlines was covered also, so I became addicted to shamble porn.

Eventually I watched so much shemale po... Continue»
Posted by lokojoro 3 months ago  |  Categories: Shemales  |  
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White Sissy, Chocolate City

This northeastern city was a world away from the two stoplight Oklahoma town where Bon-bon had grown up. The population in this metro area was a little over four million while his hometown could boast no more than three thousand residents. Back in the O.K. state, there were no Black residents, here almost half of the folks were Black. It would have been a culture shock for most people, but the O.S.U. Cowboys fan embraced it.

Bon-bon’s government name was Andrew Conway. He had recently celebrated his twentieth birthday after having moved to the city just eight months ago. He had attended cl... Continue»
Posted by faggyboi 3 months ago  |  Categories: Gay Male, Interracial Sex, Shemales  |  
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The return of Sir Roger


** This was written as a follow-up to another story – which was a memory of some of my time living on St. Croix. I was in my mid-twenties then, lived there for five years and, mostly slutted around or, made money by being a TS prostitute.


A few weeks later, on a beautiful Sunday morning, the girls and I were having a late breakfast on the veranda of the good old King Christian. Molly was sitting directly opposite me at the table. Suddenly, she looked up, directly behind me, gave a twisted little smile and said, “Ut oh s*s…here comes your boss man!” before I could react to her rem... Continue»
Posted by swat412 3 months ago  |  Categories: Anal, BDSM, Shemales  |  
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Double teamed and a ‘noon delight’


This one had my cleaning woman [at the hostel] rolling her eyes again.

Two foreigners showed up at the hostel about four in the afternoon, this week. They were the typical travelers on bikes; the one bike was in need of some major repairs. After registering them I pointed them in the direction of the local mechanic. They were clean looking guys, in their early thirties, attractive and from Spain. Half an hour later they were back. As I had suspected, the one bike was in bad enough shape that it would be noon or later the next day before it was repaired.

I told them where they could get... Continue»
Posted by swat412 3 months ago  |  Categories: Anal, Gay Male, Shemales  |  
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Dinner time, Cum, from My Man

Ohhhh, Daddy! You are my Man!

You Use me like I'm Your Submissive Bitch, when You show me off, at dinner, with all Your Man Friends!

We arrived at the party and You whispered to me, in my ear, to wait for You, here, outside the Men's bathroom, with my bare arms folded behind my lower back, looking down at the carpet, with my legs close together, just like Your Friends Submissive Girlfriends have to do, till You got done in there. That, I'm to call out for You, if a Man approaches me and touches me.

Some of Your Friends noticed Us arriving and waited for You to go into the bathroom and... Continue»
Posted by SissyCharlie 3 months ago  |  Categories: Anal, Interracial Sex, Shemales  |  
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Donna! You wait for me, here, outside the Men'

Ohhhh, Daddy! You are my Man!

You Use me like I'm Your Submissive Bitch, when You show me off, at dinner, with all Your Man Friends!

We arrived at the party and You whispered to me, in my ear, to wait for You, here, outside the Men's bathroom, with my bare arms folded behind my lower back, looking down at the carpet, with my legs close together, just like Your Friends Submissive Girlfriends have to do, till You got done in there. That, I'm to call out for You, if a Man approaches me and touches me.

Some of Your Friends noticed Us arriving and waited for You to go into the bathroom and... Continue»
Posted by SissyCharlie 3 months ago  |  Categories: Anal, Interracial Sex, Shemales  |  
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My new assistant - her story, part 3

The next week, Mr. Anderson told me to come to work early on Wednesday. We usually arrive at 8:30 but Mr. Anderson had a meeting at 8:30 and wanted me to help him get ready. I did not realize how heavy traffic is at that time in the morning and I arrived at 7:15. As I entered the office, my boss stood up and walked towards me.

As I rushed in I started my explanation, “I'm sorry I'm late....”

Mr. Anderson put his finger to my lips and quieted my breathless rambling. “One is either on time, or one is late. You are late.” he said sternly.

He took my purse and bag from my hands and set... Continue»
Posted by MassMan669 3 months ago  |  Categories: BDSM, Fetish, Shemales  |  
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Looking a Little Knocked-Up


My one disappointment in life was/is not being able to get pregnant, especially with a few of my black lovers.
As I said in another story and, shared with a few in chat, is that my mother told me (later in life) that she was glad I wasn’t born a girl, ‘You would have been pregnant by the time you were 11 or 12.’ She was right…

We both remembered, when I was eleven years old, me asking her if I could get pregnant. I didn’t ask specifically about ‘me’ but if a guy could get pregnant. I asked her because, I’d recently lost my virginity and Ron was fucking me every chance we had. I was just ... Continue»
Posted by swat412 3 months ago  |  Categories: Anal, Interracial Sex, Shemales  |  
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Bookstore pickup

I'm a regular customer of a local sex store. They sell clothes, toys, etc. They also have a large video rental business. I'm there all the time.

About a year ago, I was in there looking at the transexual and bi videos when I noticed a larger woman standing near me. I took a closer look and realized it she was not a genetic female. She was wearing a red silk blouse, black skirt, stockings and 3" heels. Damn she looked sexy.

I stepped closer and and knelt down to look at the lower racks, but I really wanted a closer look at this sexy lady. She was about my age and clearly comforta... Continue»
Posted by RichVaman 3 months ago  |  Categories: First Time, Shemales  |  
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High School Sissy

Even when growing up I always seem to be on the fem side, my shape
was more of a girls shape then a boys. As I was growing up my parents would
always dress me clothes that were stuff that a boy would wear, because if
they dressed me in something that was sex neutral I be mistaken as a little
girl. As I got a little older I liked being a boy since jerking off was
always fun. But when I was alone I find a way to get into my older s****rs
room and try on here clothes. By the time I was 16 I have to say that there
were times I be able to get dressed in one of her outfits and almost pass
fo... Continue»
Posted by hottniklez 3 months ago  |  Categories: First Time, Group Sex, Shemales  |  
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