Shemales Porn Stories
Page 72


while in our early teens my cousin nicolas and
i used to look at porno mags and videos up in my
tree-house which was quite a ways from any other
structure. during these sessions nic and i would
whip out our young hard-ons and whack off to the
images of naked women and men of all ages. we got
together to do this about once a week and discuss
the sexual escapades we may or may not have had
with girls we went out with during the week. a week
after nic had graduated (i was still a junior) he
came over to the tree-house and said
he was leaving for the city "to find himself."
when i... Continue»
Posted by qrystofer 2 years ago  |  Categories: First Time, Gay Male, Shemales  |  
  |  9

For Hentai/ futanari lovers only

First it starts off with Jay and Hex spending time together for the first time since Jay came home from the military. After a day of hanging out at the lake the two decide to head back to Hex's place for jay to see where he lived since he moved out from home. Upon arriving at his new home they decide to order some pizza and watch a new movie that hex ordered on cable after they eat they continue to watch the movie. An hour into the movie everything goes black the two think the power went out but little did they know that no power was the least of their problems as the room slowly began to ligh... Continue»
Posted by HERCK 2 years ago  |  Categories: Anal, Masturbation, Shemales  |  
  |  3

my week away with my Dom. BF

So, I am a cross dresser, a submissive cross dresser, and my BF knows how to really use me! We had talked about how I got turned on when he was rough with me, when he took me anyway he wanted to during the weekends we spent together. How I fantasized about being a slut for one or two more of his friends at the same time. How just talking about being the group slut, being at their mercy was such a HUGH turn on for me!

I knew he was going on vacation in a couple weeks, and would be gone for about 10 days or so. What I did not know was that he had set me up to be able to come along with him... Continue»
Posted by subrhia 2 years ago  |  Categories: Anal, Group Sex, Shemales  |  
  |  5

The first night

We finally meet in a bar after exchanging messages. Admittedly I’ve been turned on by the thought of where the night could lead but you can tell I’m slightly nervous. As we enjoy our first drinks together we chat about nothing in particular but I notice a cute smile you have as we talk.

You can see that I’m becoming more comfortable and open with you so you decide to ask

‘hunni, what do think will happen tonight?’

I lean in close and whisper

‘I want you to be my first’ before kissing you softly on your lips.

We start to kiss passionately and then decide to leave the bar.

As ... Continue»
Posted by kinkymister 2 years ago  |  Categories: Anal, Hardcore, Shemales  |  
  |  4

Fucking my friend's little sibling

After a night out I stayed over at my friends sl**ping in the spare room. In the morning my friend had work and left without waking me but she told me the night before she had work and I could stay until she got home again.

Waking up in the morning I felt groggy and tired but one thing I did notice was I woke up with morning glory, I was rock solid and made a huge tent of the quilt. I needed to sort this out. I slid my hand down into my panties where it was stretching them and slid them off allowing my cock to grow to it's full size, I was so horny and instantly began wanking to hard and f... Continue»
Posted by shemalecharlotte 2 years ago  |  Categories: Masturbation, Shemales, Taboo  |  
  |  12

My b*****r caught me crossdressing

It all happened 3and a half years ago.I started secretly crossdressing about an half a year before.One day my parents went out and told me that they will be late,and my b*****r was staying at his friends house (he was 17 back there and i was 14).As soon as they left the house i ran down to my mom's closet and starting picking some thing sexy from her varedrobe and i was putting it on. In that time i had my own thongs that i secretly bought,i put them on,my mom's push up bra,and her sexy red dress that has a big cleavage,and i put on her tights too.I was looking like a real whore.I went to the ... Continue»
Posted by sissygirl1988 2 years ago  |  Categories: First Time, Shemales  |  
  |  9

Sweet Charity

You may have heard of the phrase sweet charity, well in my case it was certainly sweet to me. I have built up a large part of my CD wardrobe through judicious visits to charity shops wherever I may be in the country. In one of my local charity shops there's an assistant called Wendy who I would judge is in her mid fifties but looking well on it. She's always well turned out in neat blouses, always a just above the knee skirt, never bare legs and 3 to 4 inch heels of various kinds. I must admit that my fairly frequent visits to this particular shop engender a feeling of hornyness on two counts.... Continue»
Posted by SiobhanSeeDee 2 years ago  |  Categories: Shemales  |  
  |  5

& i WAS thinking of you after all:)


warning: this is a longish message. i'm not expecting a response & i know you're busy, but i need someone to talk to.

so... i increased my workouts & my body rubbing & lotion-ing & i ate better & TRIED to get more sl**p & by the end of my week, i'd put a 1/4" on my tits, 3/4" on my ass & took another 1/2" off my waist to put me at a solid 38-29-38 (34 ribs/31 low waist... suck in the waist to 27&1/2... arch it all for dramatic effect...) as well, i lost 2.5 lbs to weigh my 5'11" in @ 147.5.

i knew there was no fukin' way i was going to see you but why not try to look good anyways... Continue»
Posted by roxxanna 2 years ago  |  Categories: Shemales  |  
  |  2

Charlie s****r-Boy seduced by Old Fisherman

Hi, Dee. We have similar turn-ons.

I was very young, when I opened up a dresser drawer and saw a small pair of white panties laying on top of everything!

My Dads work friend and His daughter had just stayed the night. She was My age. It was Her panties! Daddy, His friend and the girl slept in one bed and Sharlee and Me slept together, in another room. The Men tried to keep the girl quiet, but She was Young and Willing to be taught 'special' things when Her Daddy shared Her with each of His friends on the weekends. She liked to giggle, I know that!

Anyway, I looked up and down the hal... Continue»
Posted by sharleesisterboy 2 years ago  |  Categories: First Time, Gay Male, Shemales  |  
  |  2

How i became a sissy/my first blowjob

I'm a 17 year old sissy now but i started crossdressing 4 years ago when i was 13 :).This is the story. One day my parents went to our lake house for the weekend with my s****r but i was feeling sick so they left me with my grandparents. They were taking care of me for a day or two and i got better so they left and i was home alone.I had 5 more days until my parents were back.One day i was feeling very bored so i opened my s****rs closet and looked at her stuff. I noticed thongs,i never knew she wore them (she was 17 back then). I wondered how they would feel so i put them on. I never felt sex... Continue»
Posted by sissygirl1988 2 years ago  |  Categories: Fetish, Shemales  |  
  |  12

trannie's beach photographer

I was looking to tranny photos on the beach so I started to think what if I was that photographer
Who shoot those photos .... and wrote this. ...

Nice ass and cute dick ... mmm if I was the one who's take that shoot ... I will slapping your ass and squeezing your dick and balls hard while I do that I would kiss deeply and suck your tuong ..mmmm yummy and bit your lips nicely mmm.. in turned you around and start massaging your asshole mmm what a tight asshole mmmm and so sweaty ass mmm.. you're wet !!! Mmm -funk me now - you say it ... and I'm so hard and big mmm .. I tried to put it but i... Continue»
Posted by 4dragonkiller 2 years ago  |  Categories: Anal, Gay Male, Shemales  |  
  |  2

Sissy adventure No. 2

I have always loved meeting guys in adult cinemas. You can get up to allsorts, its easy to arrange and most importantly it feels well dirty! That's why i was really excited to chat to an asian guy who wanted to take me to an adult cinema in Brum. I am ok going on my own, but SO much better to have a date!

So we organised it for Saturday night - much better than Strictly. He was there as i tottered round from the car park to the entrance in my ridiculous heels. This did create a bit of a stir amongst some passers by, but I didnt pay any attention as I was 100% focused on not falling over!

... Continue»
Posted by hannah_maid 2 years ago  |  Categories: Anal, Shemales, Taboo  |  
  |  4

A Love Letter From My pet ^^

I assign my pet nightly homework. This normally involves some self training through sissy videos as well as the occasional wind warping task. As she is not allowed to touch her sex, all of this is a wonderful tease for her. Making her sissy eggs swell and ache in beautiful need.

I awoke one morning to find this love letter in my email.

Enjoy :)


Dear Mistress's huge, yummy, wonderful, thick, delicious shemeat,

No matter how hard I try, I cannot stop. I cannot stop thinking of how wonderful you are. How wonderful it i... Continue»
Posted by dwadd73 2 years ago  |  Categories: BDSM, Masturbation, Shemales  |  

Sissy Captions Transcribed

Pet had a new assignment last night. Certainly video reinf***ement of her slutty sissy desires was on the agenda. But this time, she used multiple neural pathways for her reinf***ement.

A very nice hypnotic trainer, with lots of flashers and captions. But... i wonder? What do ALL those captions really say?

Thanks to pet... we now know.


“Sissy gif Training 3, Sexy Time”

Put on a nice outfit and find the nearest coc... Continue»
Posted by dwadd73 2 years ago  |  Categories: BDSM, Fetish, Shemales  |  
  |  4

mom's sissy

You know those words that just have so much impact on you they just shut you up and keep you thinking for the rest of the day? There have been other instances in my life that have done this to me, all of them done by my mother. The first time when I was a c***d she asked me if I had tried on her pantyhose in the bathroom. This was true because after I had my fun with them I placed them in the hamper. That was one of the very first times I had ever worn female clothing. Naturally being a little k** I didn't know how to react to the situation so I got angry and basically over reacted saying thin... Continue»
Posted by nicoleinberlin 2 years ago  |  Categories: BDSM, Mature, Shemales  |  
  |  3

mom's sissy

You know those words that just have so much impact on you they just shut you up and keep you thinking for the rest of the day? There have been other instances in my life that have done this to me, all of them done by my mother. The first time when I was a c***d she asked me if I had tried on her pantyhose in the bathroom. This was true because after I had my fun with them I placed them in the hamper. That was one of the very first times I had ever worn female clothing. Naturally being a little k** I didn't know how to react to the situation so I got angry and basically over reacted saying thin... Continue»
Posted by momandboys 2 years ago  |  Categories: Fetish, Mature, Shemales  |  

The Seduction of Lynda - A work of fiction

I was still horny for Heather after our suckfest the previous night, when Lynda asked if I was free this week. She’s married, and doesn’t get the chance to meet very often and when she does it’s usually short notice. We had chatted a few times, and had agreed to meet up sometime, although she doesn’t meet for sex, just dressing and chatting. Lynda had booked a room at a hotel on the off chance that someone was available, and I agreed to meet her there.

We agreed to meet in male form, and then get dressed up, as it made her more at ease, and she didn’t want to go out dressed up. It didn’... Continue»
Posted by misssuzywhyte 2 years ago  |  Categories: Anal, Shemales  |  
  |  4

On an escapade.....Out an about . Page 2.....cont.

Istroked his thigh an slipped across his buldging crotch an before i saw what he intended he`d stuck a massive snoggin kiss full on my lips! oooow..a bit ov a shocka but i soon responded an enjoy`d a long sexy snog with him his hands were all over me,an the other guy was also feelin me up too,ooooowww my god ! i was luvin this now , with my ass against the table legs waist width apart a fella either side of me fondling an feelin me up as i wank both cocks , hmmm one starts kissin down my exposed front breast an stomach all the way to my wiggly little clitty , which he suk`d at a while as i sno... Continue»
Posted by saharasarah 2 years ago  |  Categories: Shemales  |  
  |  2

A NIght Out - A work of fiction

After the fun I had had with Jane, I decided it was time for me to get out and about and meet other transvestites. I had a taste for sucking tranny cock, and I wanted more. I couldn’t believe myself, after one evening of hot tranny sex I was a cock hungry slut, who couldn’t wait to get her red lips round another hard and sweet cock.

I decided that the best way to meet girls was to go on one of their nights out. I chatted To Jane online as usual, and she told me of a night out in Glasgow in a couple of weeks. Unfortunately she couldn’t go, which disappointed me as I wanted to play with h... Continue»
Posted by misssuzywhyte 2 years ago  |  Categories: Shemales  |  
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A Little Hard Work Never Hurt Anyone......Especially not Chrissie!

It's hot and humid today and I'm sitting here in my a****l print bikini bathing suit sipping on the first glass from a pitcher of margaritas.
I'm not really certain why but I started thinking about something that happened back in my second year of college. My BFF since grade school
and I decided that in order to create a little extra income during the summer break we'd set up a little free-lance house cleaning business. We
placed an ad in a couple of the local weekly papers, mostly because they charged markedl... Continue»
Posted by chrissieCD 2 years ago  |  Categories: Anal, First Time, Shemales  |  
  |  6