Shemales Porn Stories
Page 14

First time glory hole part2

...... I woke up and the lights were now on so I was guessing it was night and they close this place at 12 so was hoping that the man who closes it down let's me go so I looked at my watch it was 11 so was hoping someone would come soon.

Someone came in I guessed it was the cleaner cos he went into the other stall and sounded like he was cleaning so I was hoping he will let me go he had finished cleaning the other stall and then open the door to the stall I was in he looked in shock to see me sat there with no trousers on after being shocked he looked round went to the main door and shut it... Continue»
Posted by briggs123 4 months ago  |  Categories: First Time, Gay Male, Shemales  |  Views: 3592  |  
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My first time

I sat in the car outside the address and to say I was nervous is a understatement. This was the first time I had ever done anything like this and I was half thinking of just driving away.

I had got messaging to Sara a month ago after liking the pictures they had posted. I was really in to clothed sex and the pictures showing Sara in a selection of boots whether they be leather or pvc, knee high or thigh high I didn't care as long as they have a stiletto heel l love them.

As for clothes I get hard for the slutty secretary look, a nice tight pencil skirt with some stockings and high heel... Continue»
Posted by big_rob49 1 year ago  |  Categories: Anal, First Time, Shemales  |  Views: 3584  |  
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Caught by my wife

I was stuck, I couldn't move, literally in headlights... I dress up okay? you caught me, I guess your the master now... I used to control my wives life and for good reason I pleased her, and she pleased me the best she could... well now that's changed.. she came home from work early last Tuesday and came in the side door of the garage, I use the garage to film my escapades. And all this time I've never been caught, now I'm caught and can not go back... I am passable. I'm always dieting, I work out but I work out to slim and femme myself.. My wife has the most beautiful body ever, and thats why... Continue»
Posted by reefermcrevolver 2 years ago  |  Categories: First Time, Group Sex, Shemales  |  Views: 3585  |  
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Little MIss Sissywhore




Little Miss Sissy Whore


Chapter 1 -- The Pick-up

Every year I waited eagerly for the three days when PC-Expo was back in town. In the past, I was always able to find some willing and naive out-of-town female to pick up, "do the nasty," and say my hasty good-byes. Most of them were from some small hick town and were entranced with the Big Apple. In fact, that was both the nickname for the city, and for me. Most women just couldn't wait to sink their teeth into me. So there I was, looking for some love, on the last day of the three-day convention. I walked up and down the ... Continue»
Posted by klammer 7 months ago  |  Categories: Anal, BDSM, Shemales  |  Views: 3576  |  
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An Unexpected Adventure

I had been thinking about getting laid all day. I had placed a personal ad online a few days before, and had decided on a man to meet. I spent the day making my body smooth and fresh, and preparing myself for a night of hot sex. The guy I was going to meet was 40-ish, black, and judging by his pic, quite handsome. He didn't send a cock pic, but said I would not be disappointed. He was staying in a hotel out by the airport, so I packed my car for the drive there (I usually dress at my destination). I left a little early so I could stop off at a bar for a few drinks to steady my nerves. I was fe... Continue»
Posted by cdncleggs 2 months ago  |  Categories: Hardcore, Interracial Sex, Shemales  |  Views: 3574  |  
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TV CD Sissy Slut Fucked hard at the Adult Video Bo

Put up a local CraigsLList ad saying "TV taking on all cummers
at a local Adult Shop", gave the date and time. Which was
last night.

I enema'd and bought some new black thigh highs to go
with my shoes. Legs looked hot if I do say so myself.

I got there early and was the belle of the ball. As soon as I walked in
several guys loitering in the arcade hallway, approached me. We got
into the largest booth and they put me on my knees. Unbuckled and
plop, 3 cocks in my face. Score Bitch! I went from cock to cock to cock.

Heavenly, the cocks were 5, 6 and 8 inches erect. Of course the ... Continue»
Posted by CrimsonQueen17 27 days ago  |  Categories: Gay Male, Group Sex, Shemales  |  Views: 3585  |  
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Sissy Serving Poker Night

I was terrified when I was actually invited to serve at the usual Friday night poker game with 5 guys I had been talking with online. Three of them are black and 2 are white. I arrived at the house to find a nice setup in a basement rec room with a card table and a pool table.

I was nervous as I approached the front door and knocked having never done this before. The party host answered and immediately I was told to get dressed in something sexy and start serving drinks. Well since the only thing I brought with me was my thong and high heels, I put those on and came out, trembling with nerv... Continue»
Posted by johndavies4321817 1 year ago  |  Categories: First Time, Group Sex, Shemales  |  Views: 3563  |  
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married my young son

Hi, am Zizi, am 35, am not what you'd call a natural woman, am quite fake, by that I mean am a very fake bimbo, blonde, blue eyes, high cheekbones, incredibly busty "fake 38DDD" and I always wear ultra padded bra, unless am fucking someone.

I always wear shiny or glittery short dresses and super shiny pantyhose, I never wear heels less than 6"...and nothing of this is painful as I take steroids and had this lifestyle since I can remember along with my friends; we used to compete who can get the most boys, I used to come either second or third because of that bitch Marissa...oh look at me, I... Continue»
Posted by starlight8998 8 months ago  |  Categories: Fetish, Mature, Shemales  |  Views: 3556  |  
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Flying High



The plane landed as scheduled. Luckily it had been a very smooth flight. I made my way through the busy airport. While I was waiting for my luggage my eyes went everywhere looking for beautiful girls. I saw my luggage come around and went for it. At the same time a voluptuous brunette reached for the same bag.

“Excuse me,” I said. “I’m pretty sure this one is mine.”

“Oh I’m so sorry, the look like mines.” Her voice was soft and sounds a little hoarsed. I looked her up and down. She had a very latin style, which my cock i... Continue»
Posted by Pedeco 2 years ago  |  Categories: Shemales  |  Views: 3553  |  
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turned into a slut by my dad

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 crossD93 2 years ago  |  Categories: Anal, Shemales, Taboo  |  Views: 3552  |  
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Black Mamba - pt 2

As I entered the bedroom, Jennifer indicated that I should stand and
approach her. I rose to my feet and stood before her feeling intimidated by
her size and demeanor. Jen reached out and yanked my precum soaked panties
down to mid thigh, roughly f***ed my now withered member between my legs
toward my ass, then pushed my aching balls up into my body cavity. She then
drew up my panties tightly so that my cock was effectively trapped.
"When you are in my presence, your worthless clit is to remain tucked away
as it is now, unless I order you to do otherwise. Do I make myself perfectly
... Continue»
Posted by germanboi4bbc 1 year ago  |  Categories: Fetish, Gay Male, Shemales  |  Views: 3551  |  
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His sissy sex slave

I started jerking off to ejaculation when I was around 18. Once I started doing it, it was all I thought about, 27/7 it seemed like. I collected fuck mags and porno tapes wherever I could find them, to use as visual aids. Just looking at those sexy nude women being loved up by their hot men made my dick so fuckin' HARD! Because of that I was able to convince myself that I was normal, of course, in retrospect it is obvious that I was identifying with the women.

One day when my mom was at work, I was laying in her bed, masturbating. I got up and rummaged through her underwear drawer. The draw... Continue»
Posted by nicoleinberlin 1 year ago  |  Categories: BDSM, Interracial Sex, Shemales  |  Views: 3539  |  
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My first time with a shemale (true story)

My girlfriend had been out of town for a couple of weeks and i was so horny and wanted to get upto something kinky.
I called a shemale site from la costa del sol called taiakshemales and arrange to meet one of the beauties.
I was very nervous as i drove to her house as i never touched a dick before.
Once i was in her room waiting for her to come out she was wearing this sexy lingerie very slutty and a bead panties that just went around her tool.
She asked me if i had any experience and what i liked most, i told her i had never touched a dick and was very passive and shy.
The next thing sh... Continue»
Posted by allurs85 3 years ago  |  Categories: Anal, Fetish, Shemales  |  Views: 3529  |  
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The first encounter

I remember my first relationship with another man. Sixteen, still in high school in a small town and ready to go to anywhere but where i was. John was 30 and a high school teacher. We met at a summer camp. A group of us became friends and would meet on week-ends to party and generally hang out.
The first time that John and I were alone came that first fall; following the end of summer camp with both of us back to school. John called me and asked if I wanted to get together with some friends. So he picked me up and off we went on a Saturday morning adventure. We started the party fairl... Continue»
Posted by christoboy30 1 year ago  |  Categories: First Time, Gay Male, Shemales  |  Views: 3523  |  
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Slutty Sissy Used in a Cheap Motel Part 2

After being fucked and bred by the first 2 strangers and watching my sissy hypnosis videos I was definitely ready for at least one more deep fucking. It was around 10 p.m. when the next guy knocked on my door. I opened the door to find a very large black man about 6'8" and a smaller black man who was about 6 feet even. I invited them both in and was very excited that I was going to be tag teamed by 2 black cocks. These two guys were very demanding and knew exactly what they wanted. I knew that I would do whatever they told me to do, because every ounce of my male thought process was gone and m... Continue»
Posted by cumslutchloe 11 months ago  |  Categories: Anal, Hardcore, Shemales  |  Views: 3517  |  
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I gave a blowjob to the taxi driver -TRUE STORY-

It's a 100% true story like the rest of my stories (Although it took 2-3 hours to seduce the young repairman *see: Airconditioner repairman laid some pipe*)

I never really liked clubbing unlike my best friend B. but she was really into that and therefore, i did accompany her several times despite enjoying the scene myself.

I went to clubbing on a Saturday night as usual with my best mate B., it was almost 23.30 when we arrived due to heavy rain that hit the region. Although it was rainy, the club was very crowded and packed with every kind of people - drags, lesbians,gay couples and e
... Continue»
Posted by Slave4str8twinks 11 months ago  |  Categories: First Time, Hardcore, Shemales  |  Views: 3511  |  
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Poker Night Part 1

It was another Friday night. My roommate was having another poker game with his buddies and I wasn't allowed to join in. I spent so much time preparing snacks for everybody, but when I was all done, my roommate Craig told me to go in my room while his friends came over for a few hours. I dunno why he wouldn't let me play, I was actually quite good at poker. I sobbed and went into my room, not even allowed to take a single bite of the delicious snacks I slaved over.

I moved in with Craig a year ago. Every Friday he and his buddies would have a poker night. Sometimes at our place, sometimes ... Continue»
Posted by ConvertedGirl914 2 months ago  |  Categories: Gay Male, Shemales  |  Views: 3506  |  
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A Threesome to Remember - 2 CD's


Since I was a young man I was always curious to find out what it would feel like to get fucked by a hard cock while sucking on a cock. It wasn't until I was 20 that I really started to take the steps to make that fantasy a reality. At 20 I had my first gay experience, I got my cock sucked by one of my gay friends from school, but that still didn't satisfy my kinky fantasy, not even close.

After being referred to craigslist - casual encounters, I figured it was worth a try to post my fantasy up
to see if anybody might be interested. I received countless of men interested in helping me ful... Continue»
Posted by cd_player 1 year ago  |  Categories: Gay Male, Shemales  |  Views: 3505  |  
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steam room sex



Steven rode into the parking lot for the 24-hour gym just as the sun was beginning to rise. The brisk air kept Steven awake during his travels as he rode to the gym around 5 am. Steven's first class was at 7 am and he loved to get in the gym early mainly because no one else was around.

Locking up his bike Steven walked through the double glass doors and into the lobby. He waved pleasantly at the woman watching the counter who smiled politely back to him. Making his way to the locker room Steven changed into a pair of shorts and a white T-Shirt then locked away his duffel bag.

Casuall... Continue»
Posted by tombret123 2 months ago  |  Categories: Masturbation, Shemales  |  Views: 3498  |  
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Sissy gurl meets Daddy

The doorbell rang, and Samantha's heart fluttered. She raced down the stairs and opened the door. She answered the door and managed to open her lipstick lips and say "hello sir". She stood in front of him with her Plaid skirt and white blouse, thigh highs with red bows, red mary janes and otherwise dolled up. Her hair in pigtails, he enters and follows Samantha up the stairs.

he sat right down in the leather chair, asking for Sissy to pose. Samantha did exactly that, prancing around in front of him in her school girl outfit. she looked right in his eyes, posed seductively and said "does dad... Continue»
Posted by SissyXtina 1 year ago  |  Categories: BDSM, Fetish, Shemales  |  Views: 3492  |  
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