Sunday, April 13, 2014

Sissy Madison's Vacation -- Part 3

Madison was having the most wonderful summer of his life. Spending all day, everyday, lounging and sunning himself beside a crowded resort pool wearing a pretty ladies swimsuit was like a dream come true.  And the more time he spent pretending to be a pretty girl in a swimsuit, the more his confidence grew.

On the evening that they arrived at their hotel in Miami, Mother suggested to Madison that he might like to try a different style of swimsuit. Mother was going to take Madison to a local mall to go shopping, but as they walked through the resort, they noticed some very cute swimsuits in the window of one of the boutiques off the hotel lobby. In particular, the boutique's window displayed several high waisted bikinis that Mother thought might look wonderful on her sissy son.


Madison was very excited by the idea of wearing a two-piece swimsuit. The helpful saleslady found the bikini in Madison's size in several colors and patterns and Madison picked the three he liked best. In the fitting room, Mother helped him try on the bikinis. Mother made Madison go out into the store wearing the bikini to see himself in the big mirror. The saleslady said that he looked "very chic."  Some other customers stopped what they were doing and looked approvingly at the lovely young lady in the cute two-piece who emerged from the fitting room.


In the end, Madison picked out three suits that he liked the best and Mother bought them. Madison was thrilled with his new bikinis. That night he had trouble sleeping because he was so excited that tomorrow he would be wearing one of his new two-piece suits around the hotel pool.  He decided that he would wear the black one first.

When tomorrow came and Madison arrived poolside in his new bikini, he started getting a lot of attention almost immediately. Maybe it was the swimsuit or maybe it was just that the men in Miami were more assertive, but Madison was attracting men like moths to a flame!


As soon as Mother and Madison sat down, one of the pool boys started trying to flirt with Matilda. And during lunch, the waiter tried to get Madison's phone number. And later that afternoon, a young businessman brazenly walked up to Madison's lounge chair and started talking with him. At first all this masculine attention made Madison uncomfortable, but after a while he started enjoying it. It made him feel extra feminine and beautiful.


The next day was more of the same. This time Madison wore his new blue bikini. And again, the men seemed to emerge from everywhere trying to get his attention. At one point, a photographer working for the hotel asked to take Madison's picture and asked him to strike a few fun poses while he took pictures. 

Towel boys, waiters, other guests -- men of all ages -- were flirting with Madison. It was all just a harmless game and Madison played along. But that was about to change.


After Madison and Mother returned from lunch, one of the lifeguards came over to where they were lounging. The lifeguard was tall, blonde and very handsome. Wearing only his tight red swim trucks, his perfectly muscular physique was on full display. When he started flirting with Madison, Madison turned bright red and was barely able to stammer a reply of any kind. Mother watched all of this with great interest and a little bit of worry. After a few moments, the lifeguard moved on, leaving a confused and embarrassed Madison to sort out what had just happened.


"Well, he seemed nice," Mother innocently observed as they both watched the hunky lifeguard walk away.


"Huh? Oh, yes, I guess," Madison answered distractedly.


For the rest of the afternoon, Madison couldn't stop thinking about the lifeguard. He couldn't even concentrate enough the read his Cosmopolitan magazine.


As Mother and Madison were preparing to head back to the room to get ready for dinner, the lifeguard reappeared. This time he was wearing a tee shirt and baggy shorts, which was somewhat disappointing to a very bewildered Madison. The lifeguard explained that he had just gotten off work and that a few lifeguards and some other off-duty hotel staff were going out to a pub just a short walk from the resort. He asked if Madison would like to join them. Madison began to blush uncontrollably.

Madison couldn't speak. So Mother jumped in. "Well, Madison, I think that could be fun for you. I'm sure you would enjoy spending some time with people more your age. You do want to go, don't you?"


Struggling to make sense of his emotions, Madison replied, "Umm, yes. I do think that sounds like fun."


"Great!" the lifeguard answered enthusiastically. "Are you ready to go now?"


"Here, Madison," Mother said as she handing her son a beach cover-up to wear over his bikini. 


"Are you sure you don't mind, Mother?" Madison asked, searching as much for guidance as for permission.


"Of course not dear. Now you have fun. I'm sure it will be just fine." And with that, Madison slipped on his high heeled sandals and off he went with the lifeguard.


When Madison arrived back at the hotel room a few hours later, he was a little drunk and very, very excited. He started telling Mother about his evening -- about the other people he met at the pub, how nice the lifeguard's friends were, the music that was playing, what he drank. Mother was happy that her darling sissy son had enjoyed himself. But she expected she wasn't hearing the whole story. 


"And what about your new lifeguard friend?" Mother probed.


"Well..." Madison began tentatively, nervous about telling Mother everything that happened that evening. 

Sunday, April 6, 2014

Sissy Madison's Vacation -- Part 2

Summer was here again.  The winter had seemed to last forever for poor Matthew/Madison because he was so excited about the summer vacation he was going to take with his Mother.

This summer they were going to visit Florida for six weeks!  Mother had made arrangements for them to stay at several resorts along the Atlantic coast.  They would fly into Jacksonville, then work their way slowly down the coast ending in Miami.  And Matthew would get to be Madison the whole time!


Mother had started planning months in advance, organizing their activities and outfits for the trip.  Their first stop would be at a beauty salon in Jacksonville where Matthew could get hair extensions and long, pretty nails applied.


They would stay at five different resorts along the coast as they headed south.  Mother had researched all sorts of things to do -- sightseeing, activities, restaurants -- to fill their time.

But once they got to Florida and Madison got his hair and nail extensions, all he wanted to do was wear his pretty new swimsuits and hang out by the pool.  Last summer, Madison wore his mother's swimsuits. This year, he would wear his very own pretty swimsuits that mother had bought for him. Mother had picked out two swimsuits for her sissy son. Madison had tried them on at home and they fit him well and they securely held his breast forms. One of the suits was a pink and white striped sheath suit and the other was a blue and white polka dot suit.  Both helped to give Madison the appearance of sexy feminine curves.


Every morning, Madison and his mother would order breakfast from room service.  After eating, Madison would spend the next two hours getting ready.  He refused to go down to the resort pool until his hair, his make-up, nails -- everything was perfect. Then, by mid-morning, Madison would be down at the pool, sunbathing on a lounge chair, reading a fashion magazine and experiencing the nervous thrill of being stared at by other hotel guests -- especially all the men! He loved showing off his long, smooth legs and feeling the cool breeze and the warm sun on his exposed shoulders.  It felt so sensual to rub suntan lotion onto his soft, exposed skin.



And while Mother might have wanted to do other things, she indulged her sissy son's desire  to spend all day beside the pool showing off how pretty he looked and felt. Together they would eat lunch beside the pool.  They would go for brief dips in the pool or the hot tub.  There was nothing else Madison wanted to do.


During their stay at the first resort, Madison wore both of his new swimsuits, alternating the pink one and blue one each day. But since he was wearing his swimsuits all day, every day, Mother suggested that they take a break from the pool and go shopping for some more swimsuits for her sissy son.

They drove to a fancy mall where Mother found a style of swimsuit that she thought would look nice on Madison. It was a tank suit with thin straps and covered with cute ruffles. She found the suit in the right size in three different colors -- one in black, one in a pink check and one in blue with polka dots. 





Madison tried them all on in the fitting room. When Mother asked Madison which one he wanted, he said, "Can I have all three?" Mother simply could resist anything her darling sissy son asked for and so Madison had three new cute swimsuits to show off in.









Monday, March 31, 2014

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! 


Sunday, March 23, 2014

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!  

Sunday, March 16, 2014

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.

Tuesday, March 11, 2014

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?