Shemale, trans, crossdressing – Gay Sexual Stories

A crossdresser takes the next step

It was going to be just another fun night. I was finishing fitting my wig and started outlining my lips with lip liner, and followed up with some Revlon red lipstick. While not great looking, I had a great pair of lips when painted with lipstick. For the past few years, when going on business travel I always took the early flight and packed some of Brenda’s clothes so I could crossdress as soon as I got to the Hotel. I had been a closeted crossdresser for years. Tonight I was going to wear a very pretty red and black …

Taking the leap from gay role-playing online to the real thing

I met Mark online.

I’d joined a gay chat room. I had been fantasizing about being with a man for a while and this was a harmless, anonymous way to explore my interest.

To begin with, I was very shy and didn’t know how to respond to the occasional message that came my way. Then I got into a conversation with a guy who made all the running. I only had to go along with his messages.

I’ve discovered that the best cybersex is to be had by going along with the person you are playing with. Unless it takes …

Wearing my favorite lingerie while camping and I get some unexpected visitors

While In college I enjoyed visiting a small state park camp ground not far from campus. The sites were far apart from one another and the trees were thick, so I was pretty isolated and out of view of other campers. I had been cross-dressing for years and enjoyed being alone in the woods where I would wear what I wanted undisturbed. I still lived in the dorm on campus and didn’t have much privacy, so I treasured my weekend getaways. As I set up camp, I had a bra and pair of panties on under my shorts and t-shirt …

A true story about my first encounter with a tranny

It happened on a Monday morning. After waking up with a throbbing hard-on. I called up my regular booty call. But she couldn’t make it. Because her husband stayed home from work that day.

So I decided to browse Craigslist, looking for someone local. After posting my ad, looking for NSA sex. I sat back and waited.

Within minutes, I received over a dozen new messages. But none of them really appealed to me.

Then after a few hours of receiving numerous messages, from both women and some men. I finally got a hit.

She was an older white tranny …

Shemale Pussy Whipped

It was a shitty day in a shitty week. The kind that made me curse my
ex-husband. He was the one who insisted we buy a house out in the
suburbs. James was a suburban boy through and through and craved the
acceptance of being gay while living out the white picket fence
lifestyle. We didn’t literally have a picket fence, but we lived on a quiet
suburban street with colonial style homes, all a hellish commute from my
job in the city.

I was the one stuck with the house and the shitty commute after the
divorce. Turns out …

Patty and Susan teach me how to be a panty wearing sissy

Susan was visiting last week. She wanted to show us her
new HP computer. Just amazing what those things can do.
Patty spends very little time searching the web even
though she is very technically minded and able to fix
most computer problems.

Anyway, Susan wanted to show off the speed of her new
computer. She flipped open the screen and clicked on
Explorer. It was surprising how much faster her
computer was than mine. Susan was also here to convince
us to join her in a sky diving lesson. Seems jumping
out of an airplane has always been her …

Rice and Poopy – Friday WMN

Have you ever seen a dragon in a tuxedo. Don’t laugh.
Whatever you do, don’t laugh. I just finished putting
out some unfortunate soul with a fire extinguisher and
do not look forward to doing it again.

A regal looking female muse stood on the dias, wings
fluttering in annoyance as the crowd took its own
sweet time settling down. I put the fire extinguisher
away and headed for the bar, knowing that the ceremony
would start later rather than sooner. Friday was still
licking some residual chocolate off a well built
Adonis of a muse in the back corner …

Testing Women

As I have said before, I really don’t understand some women.

Seems that after neo-abolitionist made such a big deal about the sex
and meat testings that a lot of companies were offering, the ‘cool’
thing to do for a large group of women would be to have themselves sex
tested. I’m not complaining, a cash stream is a cash stream. I just
don’t follow why they would be doing this. Of course some are weirder
than others.

Case in point. A group of 5 women came in (2 blonds, a red head, one
with brown hair and a black …

All Tied Up

My husband called me from work and told me that
tonight he expected to find me blindfolded and tied to the
bed waiting for him when he got home and that I wasn’t to
say anything unless I was asked a question. We have been
experimenting with bondage and had each tied the other up
several times over the last few months. This was new and
different so about 3 o’clock, I went upstairs and got
undressed and proceeded to tie myself down. I used some
padded cuffs on my ankles and tied each one to a bottom
corner of …

KAYLA AND TRACY: GOOD MORNING

Yes, your favorite auteur of transsexual lesbian erotica is back.
Yeah, RIGHT!

“Thirteen…fourteen…fifteen, whew!”

The sound of the bench press bar slammed down on the frame as the
amazon finished her work out. Blindly, she reached down and
grabbed her towel, wiping the sweat off of her face before she
sat up. Weary from exhaustion of a good morning workout, her
eyes darted around the cavernous workout room. The morning sun
flooded the room through the 2 story floor to ceiling windows as
the city rose to life under her penthouse. She wiped down her
bare chest with her towel, …

TS Jillian tease my balls and my asshole

I’m certainly no angel, and working girls have been a guilty pleasure of
mine for all of my adult life. I also have a passion for TVs, CDs, and
shemales, but I’ve usually lived in places they’re not readily available.
My first TV hookup was many years ago in San Francisco. One night in St.
Louis I picked up a couple of streetwalkers, and I was overjoyed to find
that one of them was a TV. I fucked them both before the night was out.

For the past ten years I’ve been unable to hook up for one reason or…

Gurl Bunny Ranch

So, here I am in LA, lost my job, had my car repossessed and got dumped by
my girlfriend. I’m late on the rent so I don’t even have a car to sleep in.

Basically, I’m screwed. I take a look at my bank account and I realize I
have about $1000 so I’m not totally broke so what do I do with the money?
Pay the rent, try to get my car back, pay some bills? No , I decide to take
a bus to Las Vegas and blow it there.

I checked into a shit motel and headed …

Suck it and see!

It was just another day at school for Bobby Mcallister, at least it was
until he saw his former crush Dina wearing an incredibly short black
miniskirt, his attention was immediately drawn towards her tight ass, he
was starting to get turned on. And then it only got worse when Dina bent
over to pick up a bock she had dropped and Bobby caught a glimpse of her
sexy red panties. Bobby was getting painfully hard at this point so he
ran in the direction of the bathrooms but ended clumsily tripping and
falling right in front of Dina, Dina …

The T-Girl Sessions – Janet

Rob had worked hard to get a date with Janet. He thought she was
attractive the first time she flashed her bright smile at him at the
diner. He kept coming back, and worked up the nerve to ask her out.
She didn’t say no right away, and mentioned that she had to be
selective about who she dated. He persisted, and finally she said yes.

Janet liked Rob, though she figured after the first date he would not
ask her out any more. A ride through the countryside, and they ended
up at an upscale restaurant in the next …

After years in slavery to Mistress Jennifer, I am sold again

I have been the slave of mistress Jennifer for a little
over three years. I was purchased for one hundred
thousand dollars from mistress Morgan. I am now twenty
four years old and have been in slavery for almost five
years.

I am in my kennel. my mistress and her mother have gone
out for the afternoon and I am safely behind bars. My
wrists are chained to my collar and I am in my chastity
belt and anklets. For the first time in weeks, I am
shaved and my nails have been polished in a pinkish
red. My nipple …

Category: Shemale, trans, crossdressing