Thursday, February 27, 2014

A Sissy's Dinner Date Fantasy - Part 1

My name is Sean and I have been a sissy crossdresser all my life.  I have always kept it a secret, dressing up like a girl alone in my little apartment.  I only ventured outside "en femme" occassionally and only if I was pretty certain I wouldn't run into other people.

Night after night, I would come home to my apartment and transform myself into the lady of my dreams.  I had become very talented with my make-up, my mannerisms and my voice.  I knew that I looked very attractive and convincing when dressed.  Alone in my apartment at night, I would read romance novels and fashion magazines and watch chick-flicks on TV.  But the more time I spent pretending to be a girl, the stronger my fantasies became to actually experience life as a girl.  I became obsessed with the idea of being desired and romanced by a real man -- just like in my novels and in the movies.

About six weeks ago, when my obsession became too much for me to control, I went into action.  I created a profile of my femme self on  It took me several hours to get it just right.  First, I picked out a few of my best girlie photos, including these two below.  I like the one on the left because it shows off my legs.  And I like the one of the right because it makes me look more sophisticated and mysterious.

And finally, just to make sure I got everyone's attention, a photo of me in a bikini!

I came up with a back-story that sounded believable and would be appealing to men browsing through the website. I was, according to my profile, Sheila Landers, a 26 year-old junior high school teacher who had recently moved to the area.  I said I was looking for a "successful, older gentleman who was interested in a long-term relationship."  I described my interests in all sorts of girly things, like ballet and cooking.  I described in detail my idea of a perfect first date -- a candlelit dinner at a French restaurant followed perhaps by a romantic walk...I got myself excited just thinking about it!

What my profile didn't include was anything that was actually true. It didn't say that I was a 20 year-old sissy and college drop out who worked for minimum wage in a corporate mail room. It didn't say how the idea of being romanced by a man excited me and terrified me -- all at the same time!

When I was finally satisfied with my profile, I pressed Enter and posted it on Match. I didn't really know if anyone would write back to me or even notice my profile.

I needn't have worried about that. About two hours after I uploaded my profile, I had about twenty requests from men wanting to meet me. Within a week, I had over two hundred offers for dates!

Tuesday, February 18, 2014

Uncle Jim Gets a Sissy

After my parents died in a car accident, I was sent to live with my Uncle Jim.  I had never really liked Uncle Jim.  I had always thought that he was sort of rough and maybe a little strange. I was about to discover how right I was.

Uncle Jim lived alone in a big, old farmhouse far out in the country.  His wife, Darla, had walked out on him many years ago.

No sooner had I brought my suitcase into the house the Uncle Jim announced, "You won't be needing your old clothes.  I got plenty of better clothes for you to wear.  You see, when Darla ran out on me, she left all her old things.  And so now you can take Darla's place.  So why don't you go upstairs and put on one of Darla's pretty dresses while I go out back and burn your old clothes."

I began to protest but Uncle Jim started beating me.  Hard.  I was no match for him; I was small and weak and he was huge and strong.  It didn't take long for him to wrestle my suitcase away from me and to drag me up the stairs to Darla's old closet. He picked out a dress and threw it on the bed.  "Now get changed like I told you to!" he shouted.  "There's underwear and make-up in those drawers and there are pretty shoes in the closet.  Now hurry up, get dressed and get your ass downstairs."  He hit me again before he slammed the door behind him and stomped down the stairs.

I was paralyzed.  I started crying as I sat on the bed, looking at the flowery dress that was lying there. Then I smelled smoke.  I looked out the window and true to his threat, Uncle Jim was burning my clothes in the back yard.  I knew I was in big trouble and that I had better start cooperating or something really bad would happen to me.  I put on one of Darla's bras, a pair of her panties, the dress and some shoes.  I put on some red, red lipstick and some rouge on my cheeks.  I took a deep breath and headed down the stairs to where Uncle Jim would be waiting.

That was nearly a year ago.  I have been living and dressing as Darla all day, everyday, since I arrived.  My hair has grown longer and I am now better at doing my make-up and walking in high heels. Uncle Jim calls me Darla and expects me to do everything a good housewife does. I cook and serve three meals a day for him. I scrub the floors and wash the windows. I vacuum and I dust. I do Uncle Jim's laundry. My chores are endless. I hate my life. As I do my chores, hour after hour, day after day, all I can think about is how wonderful and free my life used to be, when I was a normal boy. But that life is behind me now. I am the Sissy housewife/slave of a demented monster.

Uncle Jim gets very mad at me if he catches me daydreaming or not doing my chores vigorously enough.  And he gets furious if he thinks I don't look pretty enough or if I don't sound and walk and laugh enough like Darla did. And when I disappoint him he throws me over his knee and spanks me brutally.

And after I have cleaned the the house from top to bottom and after I have put away the dinner dishes, I have to put on one of Darla's nightgowns and take care of my "husband's" sexual needs.   No matter how awful my household chores are, nothing is as awful as having Uncle Jim's giant naked body on top of me, kissing me and feeling me up all over. But worst of all is when I have to do the things that he says Darla refused to do. I have to put Uncle Jim's cock in my mouth until he gets ready to cum. Sometimes he likes to cum in my mouth and make me swallow it.  But mostly, he likes to pull It out just before he cums and shoots it all over my face. After I clean us both up, Uncle Jim usually climbs on top of me again and falls asleep. That's when I usually start crying until I fall asleep, getting a little rest until my life as a sissy housewife/slave starts again in the morning.  

Saturday, February 8, 2014

Sissy Training -- the Final Lesson

Unless a client specifically requests that his new sissy be delivered as a virgin, I always arrange for my sissy creations to have one final important "lesson" before I consider my transformation work to be complete.

My sissies have to submit to a "lesson" in sissy lovemaking given by my good friend, Mr. Rhino.  Mr. Rhino is an enormous and strong black man with the biggest cock I've ever seen.  Seriously,  it's like a baseball bat!

The sissies know what is expected of them, even though they are scared half to death. They are to submissively lie on their backs and allow -- no, invite -- Mr. Rhino to fuck their tight little sissy pussies.  And despite the agonizing pain they experience, they are expected to pant and moan like the little sissy whores their new Masters will want them to be.

Here Mr. Rhino is giving Sissy Sally his final lesson.  Poor Sissy Sally was close to tears as he lay on the bed watching Mr. Rhino undress, exposing his monster dick.

But here's the best part.  When I have other sissies-in-training in my house, I make the more junior sissies sit on chairs next to the bed, watching their more senior sissy sister get his fucking lesson.  It's great fun to watch the junior sissies as they sit and watch in horror. Some burst into tears watching the fucking show as they all know that within a few short months, they will be receiving the same special lesson from Mr. Rhino and that giant black battering ram he has between his legs.