Sissy Madison's Vacation -- Part 1

Every schoolboy loves summer vacation.  But nobody looks forward to summer vacation as much as Matthew. That is because Matthew is a Sissy. And Matthew's Mother lets him be "Madison" all summer long!

In the past, Matthew mostly stayed at home during the summer, enjoying his free time wearing pretty dresses, high heels, jewelry and purfume around the house. Mother was always delighted to spend time with her sissy son, and encouraged him to be as feminine as he wanted to be.

Last summer, Matthew and his Mother did something new. They went on vacation to southern California together as mother and daughter for two weeks! As two ladies they did everything that tourists do in and around LA. Matthew even visited Disneyland as Madison which was great fun.

During their last few days in California, Mother suggested that Madison try wearing a ladies swimsuit and go to the hotel pool. Madison didn't have any swimsuits of his own, so Mother let him borrow one of hers. Madison squeezed himself into Mother's blue and white sheath suit. Mother carefully positioned Madison's breast forms into the cups and used a little make-up to give the appearance of some cleavage.

At first, Madison was nervous about going down to the pool in nothing but a skintight swimsuit. He felt so exposed -- practically naked. And yet he was thrilled by his own reflection in the mirror. After another hour of ensuring that his lipstick, his hair, his nails were all perfect, he worked up the courage to head down to the pool. He slipped on a pair of Mother's high heeled sandals, grabbed a towel and together they rode the elevator down to the pool level.

They found two lounge chairs near the deep end of the pool. Poor Madison was still so anxious about being in public in a ladies swimsuit that Mother ordered him a pina colada, which seemed to help. After some time -- and a second pina colada -- Madison started to relax. He began to see that his secret was safe even wearing nothing but a ladies swimsuit.  

And the more Madison could relax, the more he enjoyed the experience of being one of the pretty girls lounging around the pool, his soft pale skin exposed to the sun and to the breeze and to the eyes of all the other hotel guests. Madison wasn't aware of it, but Mother noticed that some of the men around the pool were staring -- or maybe leering -- at her sissy son.


Since that first experiment was so successful, the next day Mother suggested that they do it again. This time Madison  would wear Mother's black sheath suit. Together they worked to ensure that everything was prefect and that Madison looked like just another pretty girl going for a swim before they left their hotel room.   

This time Madison was much more confident. He knew he looked pretty and feminine in Mother's swimsuit. 

After lounging by the pool for an hour, Mother suggested that they walk to the cafe by the marina for lunch. Madison slipped on Mother's sandals and off they went. As they walked, this time both Mother and Madison became very aware of the stares he was getting, especially from the men they passed. This attention from strange men made Madison a bit uncomfortable and nervous -- but it also felt flattering and a bit exciting...

As they ate lunch, Mother announced that she had already been thinking about next summer.  Since this two week "Mother-Daughter" vacation had been so much fun, Mother said that she thought the two of them should do it again next summer.  But instead of just going away for two short weeks, she thought next year they should go away, to Florida, for six whole weeks.

Madison, of course, was delighted by this idea. He leapt from his chair and gave his Mother a sweet sissy hug! 

Dr.Thompson's Sissy

I do not like being owned by Dr. Thompson. But I am trapped. I am now Dr. Thompson's Sissy Tabitha.

It started last October, about eight months ago, when I visited Dr. Thompson, the school counselor. I was confused and worried about my urge to crossdress. I felt that I needed to talk to somebody and Dr. Thompson seemed kind and willing to talk to me. When I started talking, Dr. Thompson appeared very interested in hearing about my problem. He asked me dozens of questions and gently urged me to describe all of my crossdressing experiences and my sissy feelings in great detail. At first it was embarrassing to reveal my secrets, but Dr. Thompson was persistent and eventually I opened up and shared everything -- absolutely everything.

What I didn't know then was that Dr. Thompson was recording the interview with a hidden camera and microphone.

"Well, Timmy," Dr. Thompson said as the two hour meeting concluded. "You really are quite the little sissy faggot aren't you?" Dr. Thompson's tone and words had suddenly turned harsh and mean. "Here's what we're going to do. You see, I recorded everything you just said -- sound and video -- and unless you want me to share this with everyone you know, you're going to do everything I say. Do you understand?"

I was so shocked that I couldn't even respond.  That's when Dr. Thompson slapped me hard across the face. "I asked you a question, sissy! DO...YOU...UNDERSTAND?"

I finally nodded and said that I understood.  And that's when Dr. Thompson started taking over my life.

Dr. Thompson convinced my parents that I had some kind of learning diability and that I needed to have "special tutoring" every weekend. In reality, Dr. Thompson was arranging to have me be his very own weekend sissy captive. Instead of attending the special classes he described to my parents, I have to go to Dr. Thompson's house every Saturday on Sunday morning and spend the entire day as Dr. Thompson's sissy plaything.



As soon as I arrive, Dr. Thompson orders me to strip out of my boy clothes and then he begins the process of dressing me up like a girl. Dr. Thompson has an enormous collection of girl's clothing -- I guess I am not his first sissy. He spends several hours supervising me as I transform into Tabitha, ensuring every detail conforms to his very perverted and very precise desires. He watches me as I slip on a bra and panties, as I do my make-up and make my hair look pretty. My outfit for the day depends on his mood. Sometimes he has me put on a frilly party dress. Other times he dresses me up in a sexy lady outfit. Some of the clothes are really uncomfortable, like this one. The stockings and panty are made of a really tight rubbery material and he laces the corset so tight that it is hard to breathe.

Once I am all dressed and my face covered with make-up, Dr. Thompson starts ordering me around. Usually it starts with me making his lunch.  Then I have to tidy up his home -- vacuuming, dusting, washing windows, doing his laundry. After he tires of watching me scurrying around like his private maid, he tells me to sit next to him on the couch.  Then he starts feeling me up and kissing me.  I have to sit on his lap, feeling his hard dick poking me through his trousers.  Eventually he takes me by the hand and leads me back into his bedroom where he does terrible things that I can't even talk about.  And all the while he takes photos and videos of me. Then, as evening approaches, he orders me to clean off my make-up and to change back into boy clothes so I can go home. 

This went on all fall and all winter.  I dreaded every weekend but at least the end of the school year was approaching. I figured I would be free from Dr. Thompson's clutches, at least during the summer until school started again.

But those dreams were crushed.  Dr. Thompson spoke to my parents and convinced them that there was a special summer camp for children with my "learning disability." He even managed to get them to pay him $3000 in "camp fees."  But of course, there was no summer camp. Dr. Thompson had just arranged to have me as his full-time sissy travelling companion for five weeks.

Here's a photo of me taken during our long summer vacation together.  I am kept dressed as a girl 24/7.  He makes me wear fancy, silky dresses and high heel shoes everywhere. He even took me to a beauty salon for have my hair and nails done. He enjoys taking me out in public -- restaurants, shopping malls, sightseeing, even on airplanes -- knowing how scared and uncomfortable I am being paraded around like this. If anyone ever asks, he says that I am his daughter. I have to call him Daddy when we're in public.

But when we're alone in our hotel room, we are no longer "father and daughter." He gets very excited by making me look and act like a girl in public. So when we're in the privacy of our hotel room, he becomes a crazed sex monster. He fucks me over and over and over, until he falls asleep. Then it starts all over again the next day.

I have no hope of escaping from this sissy nightmare!  

A Sissy's Dinner Date Fantasy -- Part 4

Two months have passed since that first weekend when I went out on dates with two different men. I found that experience so thrilling that I instantly became addicted to meeting new men on the internet and having them wine and dine me. Over the past two months, I have been out on dates with 23 different men!  I love how it feels to be the object of desire for these men, to be pursued, to be romanced. My heart races as I exchange emails with each new man. And the anticipation builds as we arrange for our first meeting. My excitement reaches a fever pitch as I prepare myself for each new date -- as I do my make-up and hair, as I put on my sexy lingerie and dress. It is electrifying! And then the date itself -- it is exquisite to be treated as a lady by a handsome gentleman. And almost every date ends the same way -- we go back to the guy's apartment where we make-out and before long my head is in his lap and his dick is in my mouth!

I was really enjoying meeting lots of different men and experiencing the thrill of many, many first dates. I meet a new man almost every Friday and Saturday night.  And then during the week, usually on Wednesday nights, I might let a man take me out on a second date. Some of my second dates have been really special and romantic, like being taken to the theater or a dinner cruise or a jazz club. And for treating me so nicely, I always give these men an extra special blow job at the end of the evening!

I had never been out with the same man more than twice until I met Chris Lewiston. Chris was some kind of investment specialist. He was very handsome and apparently quite wealthy. Of all the men I dated, he made me feel different. When we were together, I felt tingly all over. I would blush when he would compliment me. I would get all warm when he touched me. And when we were apart, I couldn't stop thinking about him. Maybe, I realized, I was falling in love with him!

So here I am on my fourth date with Chris. I bought another new dress just for tonight because I wanted to look extra pretty. We had a lovely dinner together. I was having a wonderful time.

"Tonight, I am going to make love to you all night long," he said as we finished our champagne.

Oh dear, I thought. Maybe going out on a fourth date was a bad idea. Of course he would expect that "things" would progress and that he would get to fuck me. But that could never happen because of my secret.

I started to make up an excuse as to why we couldn't make love tonight when he interrupted me.

"What's the matter, Sean?"

I nearly fainted when he said that.

"That's right, Sean," he continued. "I know everything about you. You see I arranged for a background check, an investigation into you. I was pretty furious when I discovered that you aren't really a girl. But the more I thought about, the more I realized that maybe it would be OK."

I started to relax when he said that. I started to breathe again. But my relief was premature.

"Yes, it would be OK because now you would be MY sissy. Here's what we're going to do. From now on, you will do everything I tell you to do. You are mine. I own you. Your only concern will be my pleasure. Do you understand, 'Sheila'?"

My mouth went dry. I was so shocked and confused by what was happening. But my inner sissy wouldn't allow me to fight back. I lowered my eyes and softly replied, "Yes, Sir. I understand."

"Good. Then get on your knees under the table and suck me off right now while I pay the check," he ordered.

I did exactly as he commanded. I slid beneath the table and crawled between Chris' legs. I unzipped his trousers and released his massive cock. It was already starting to stiffen as I started kissing and licking Chris' dick. And as I did so, I realized that this is exactly where I belonged. Chris would be the strict and demanding Master that I needed. As I stretched my lips around the enormous head, I thought about how Chris would be fucking me later. And when Chris' hot semen blasts into my sissy pussy, I will be forever branded as Chris's sissy.

A Sissy's Dinner Date Fantasy -- Part 3

I couldn't go out with Mark again on Saturday because I had already lined up a date with another man!  This guy's name was Jake Martin. He was in real estate and he wanted to take me to Le Maison too! I decided to wear my new dress and shoes again but I wanted to do something different with my hair. I called a salon that was willing to arrange my wig into a different style. They offered to do my make-up while they worked on my wig so that's what I did.

My second date with a man was even more exciting than the first. Jake was charming and funny. But he was also pretty aggressive. From our first few moments together in the restaurant, he had one hand on my stockinged thigh under the table, stroking and squeezing. At first it made me nervous, but after a glass of wine I decided I enjoyed it.  

The food and wine were just as wonderful as the night before and I was having a great time being an elegant lady in the company of a handsome man. 

At one point during the evening, I got up to use the ladies room, When I returned, Jake stood and pulled up my chair for me. How chivalrous, I thought. But as I sat and he pushed in my chair, he leaned in and started kissing my neck. I was so surprised, I almost fainted. And he wouldn't stop doing it until I insisted!  

By the time we were having our dessert and coffee, the restaurant was emptying out. That's when Jake really made his move. He pulled up his chair close to me and we just started making out -- right there in the restaurant!  I know that the waiters and the few remaining guests were staring at us, but I didn't care. 

As Jake was paying the bill, he practically insisted that I go back to his house with him.  And I agreed!  We took our separate cars and I followed Jake to an elegant townhouse at the edge of downtown.  Once inside, Jake turned on some music and opened another bottle of wine.  We sat down on the couch and started making out again.  Wow!

Before long, I found my hand was on his lap, stroking his enormous, stiffening cock through his trousers.  He started breathing hard when I did that and he suggested that we go back to his bedroom.  Knowing that would lead to big trouble I suggested that we stay on the couch. I unzipped his pants and his huge dick sprang out.  Without even thinking, I put my head in his lap and wrapped my lips around his giant cock.  I licked and kissed and sucked on his cock for over twenty minutes until he finally had to cum.  And when he did, it was an explosion!  I swallowed every drop of his precious semen. 

It was almost 3:00AM by the time I finally got home. And even though it was very late, I couldn't go to sleep.  My mind raced with emotions from my exciting weekend with two different men. And the feeling of having a real man cum in my mouth while I hungerly sucked on his dick! For the next several hours all I could think about was how much I wanted to see both Mark and Jake again, to feel their lips on mine, to feel their desire for me, to excite them in the ways a real woman would.  I couldn't sleep at all that night wondering where this would take me next. Would I explore my girlish feelings with Jake or Mark -- or did I need the thrill of having many more men pursue me and desire me?   

A Sissy's Dinner Date Fantasy - Part 2

Within a week of posting my profile, over 200 men had written to me!  I read every single message that I received. Then I carefully studied each man's profile and photos and I wrote flirty notes back to several of them. It didn't take long before I had actually scheduled a date with one of them!

For my very first date I had selected a man that seemed particularly promising. He name is Mark Jensen and he was in his mid-40s, divorced and a bank executive. He described himself as being six-foot-two and in excellent shape. And best of all were his photos! He was very handsome, with strong, chiseled features. His dark hair had a bit a grey at the temples.  One of his photos was taken at the beach -- with his shirt off exposing his muscular chest and shoulders!

We exchanged several emails and then we talked on the phone. I had practiced my girly voice and he didn't suspect a thing. In fact, he said my voice was sexy. And at the end of our conversation we agreed to meet for a date on Friday night!

I couldn't stop thinking about my big date all week. Even though I owned two pretty dresses that I could have worn, I decided I needed something even more special. I went to Macy's and spent $400 on a gorgeous black dress and another $200 on some sexy sling-backs with 3 inch heels.

On the night of our first date, I met Mark at Le Maison, the fanciest French restaurant in town. He was already sitting at the bar when I walked in. He looked just like his photos -- tall, handsome, sophisticated. He seemed very happy when he saw me for the first time. He gave me a quick peck on the cheek as he greeted me and the Maitre d' walked us to our table.  

My dinner date was just heavenly. Mark was a perfect gentleman and I felt like a perfect lady. He ordered a very expensive bottle of wine which was wonderful. We chatted about this and that. Mark mentioned several times during dinner that I looked very pretty -- which made me blush each time. Being with Mark made me feel like I was one of the beautiful, enchanting women in the romance novels I had read. 

We had a second bottle of wine and our conversation became flirtier. I was having so much fun -- it was like a dream come true.  

As dessert was being served, Mark got out of his chair and gave me a big kiss -- right there in the restaurant! It was so spontaneous and so romantic!

After dinner, Mark walked me to my car in the parking lot. But the evening didn't end there. We made out in the parking lot for another twenty minutes. Mark pressed me up against my car while he frenched me hard. He was so strong and forceful. I could feel his dick getting hard as he rubbed against me. It was so exciting!!! His hands even drifted up to feel my breasts -- he had no idea he was squeezing silicone falsies. He practically begged to see me again on Saturday, but I said no -- not because I didn't like him, but because I already had other plans for tomorrow night!

You see, I had already arranged a date with another man for the very next night!

After I got home from my exciting first date as a girl, I put on a sexy nightgown, some soft music and made myself cum, looking at Mark's profile photos, imagining that our wonderful date hadn't ended in the parking lot.