A Reluctant Sissy -- Part 6 - Sissies for Hire

About a month had passed before I received another letter from Mrs. Trainer.

"Dear Mrs. ____,

Sorry for the delay in writing but things here at the school are very busy indeed.  This is a crucial time in our training process where we expect to see our sissies display the attitude and actions that are expected of them without any reminders, prodding or punishment.  We are still enjoying our trips into London and our Thursday night officers' parties.  And I am delighted to report that your son is by far the best behaved, hardest working, most delightful little sissy in the entire class.  We are absolutely thrilled with how far he has come in just five short months here.

There is a special privilege (well, I 'm not sure the sissies see it as a privilege) that we reserve for our most accomplished, most feminized, most obedient sissies.  On occasion, if one (or more) of our handsome, older Air Force officers wants to "borrow" a sissy, that is something we can sometimes arrange.  Well, I can assure you that ALL of the gentlemen are asking for time with your beautiful son.

Sometimes an officer will request a sissy to be their date for an evening of dining and clubbing in London.  Your Kimberly  went on such a date two weeks ago wearing that adorable black minidress.  Doesn't he look divine.  Our officer was so proud having this lovely sissy hanging on his arm all evening, showing him off to all his friends."                                                                                                               I stopped reading long enough to look at the first photo.  I nearly fainted at the sight of my son wearing a very sexy minidress -- and looking amazing in it.  He looked so delicate, so feminine.  The short dress made his legs look so long and slender, the high heels he wore added to the effect.   I took a breath and returned to the letter.

"Then last week, another officer borrowed Kimberly for an entire weekend, jetting him off to some swanky island resort.  We assembled some fabulous outfits for your son for this little adventure.  I simply love the very revealing black top combined with the wide leg trousers.  Your son looks like he stepped out of a fashion magazine!  And the fun part of wearing that top - it makes our sissies wish that their boobs were actually larger than they are (but the hormones only work so fast -- don't worry, you can expect a lot more progress in this department over the months ahead).  We also sent your son off with a sexy swimsuit for his resort getaway."

I stopped again to look at these two photos.....

"And please don't be concerned by the expression on Kimberly's face.  I'm happy to report that he is not sneering or frowning for the camera.  Rather, he is genuinely frightened of being sent away for time alone with these men.  As awful as life is for our sissies in the school, they become familiar with their surroundings and the routine and they take comfort in that.  But when they are sent off into the world on their own, with no chaperone, that can be very unsettling.  Your lovely Kimberly was absolutely trembling with fear before being sent off on these two "assignments."                                                                                                                But I'm happy to tell you that in both instances our officer friends were absolutely delighted with Kimberly's company!  

There is a group of three officers who have inquired as to whether they could take Kimberly away for a weekend at a country estate they are renting.  I think that sounds like a marvelous idea.  I'm sure they will find all sorts of ways to keep your darling son busy!  

I expect that there will be some sad faces over at the base when it's time for your Kimberly to be sent home to you.

That's all for now.  We are in the final stages of preparing your son to go home to you!

Sincerely, Mrs. Trainer"

Sissy Roommate Part 8 -- Spring Break Sissy

The rest of the fall and the winter went by quickly.

Of course, Tank set several new school football records -- and the team did make it to a Bowl Game for the first time in decades.  Even though football season ended, Tank continued to train hard all year round.

I continued to put all my effort into serving Tank and making him happy.  My own school work suffered badly -- I did terribly on two of my fall semester finals. But I realize I can't do everything and I have decided that caring for Tank is my top -- and sometimes only -- priority.

You may remember that last fall, Tank had me start taking birth control pills -- female hormones.  I didn't want to at first but Tank insisted.  Well they have had a powerful effect on me!  Almost immediately, I could feel swelling and intense sensitivity in my nipples and breasts.  My butt and thighs have gotten a lot fuller while the rest of me has gotten even skinnier. My complexion became clearer and my skin softer. And my hair started growing much faster and thicker.  There is no doubt that the birth control pills are starting to make me much more like a real girl!

As spring break approached, Tank told me that he was going to Florida.  Some wealthy alumnus was letting Tank use his beachfront condo for the week.  And do you want to know the best part?  Tank asked me to go with him!!!  I leapt into his arms and kissed him so hard when he asked me!  I was over the moon!                                                                         Of course, I didn't own anything I could wear on a vacation in Florida so I had to ask Tank for some extra money to buy some new things, including the super cute bikini I'm wearing in the photo.  What do you think?                                                                                                 When I go to the beach or to the pool, I wear a pair of extremely tight panties so that I'm totally flat in the front.  And I added some special padding to the bra top that helps push my teeny breasts up so that I look like I have boobs like a real girl.

We had  really great time in Florida -- and I had Tank all to myself.   Well, mostly.  He still went to a local gym every day.  But sometimes I went with him.  I was able to take a Zumba dance/exercise class with a bunch of other ladies which was really fun.  

The whole week was a dream.  I would get up extra early to take my shower and to make myself look pretty before Tank even woke up.  Then I would make him breakfast and then Tank would have sex with me.  I think we did it in every room and on every piece of furniture in the condo!  After that would would go out to the beach or to the condo's pool.  I think it really turned Tank on seeing me out in public in my bikinis!  And even though the beach was public, Tank still made me give him secret hand jobs -- right there on the beach!

And in the evenings, Tank would take me out to restaurants and night clubs.  It was like we were really boyfriend and girlfriend!

I was so proud to be seen with Tank.  First of all, he looked so handsome when he put on a nice shirt and pants to go out. And of course, a lot of people would recognize him when we were out and would ask for autographs and selfies.  I felt like I was being escorted by a Hollywood celebrity!  It was so exciting and dreamy!

Tank was so nice to me the whole time we were away.  He even bought me a little gold necklace -- it's a pretty mermaid pendant on a thin gold chain -- for me as a souvenir of our trip.

I was so happy while we were in Florida.  I felt like the time there -- parading around in my bikinis, being on the arm of a handsome man, receiving a lovely piece of jewelry -- was making more feminine, more girlish, every day.  I think the experience was changing how I thought and how I felt about myself -- and how I felt about Tank. One night, as I was sleeping tightly wrapped in Tank's arms, I even dreamed that I was Tank's wife.  Isn't that incredible?  

I'm really in love with Tank.

Sexy Beach Sissy

Sam is a total sissy.  He loves dressing up in his sister's clothes and pretending that he's a girl. He used to do it only around the house when his parents were out.  But now that he has his driver's license, he likes to go out in public as "Samantha."  Sometimes he goes to bars and clubs. Sometimes he'll walk around the mall or the park.  But his favorite thing to do is to hang out at the beach.

He saved enough money working part-time jobs to buy an old VW van.  This is both his car and his dressing room.  Every day during the summer, he leaves the house early in the morning as Sam. He drives to a quiet place to park and climbs in the back of the van and transforms into Samantha.  He fixes his shaggy black hair in a way that looks cute and feminine.  He does his make-up -- he loves wearing lots of bright red lipstick!   He puts on a bikini with just enough fabric to hide his fake boobs. And he wears a super tight panty under his bikini bottoms so that he is perfectly flat and smooth in front. Lastly, he puts on some dangly earrings and sprays himself with a flowery perfume. Once he is satisfied with his look, Samantha continues the drive to the beach.

On most days, Samantha arrives at the beach before there is any real action there so he hangs in the van and listens to the radio. There are a bunch of regulars that are also around early in the morning -- maintenance workers, cops, vendors, lifeguards -- heading into work. Samantha knows a lot of these men by name and a bunch of them go out of their way to swing by the van and flirt with the pretty brunette girl for a little while.  Samantha's favorites are the cops and the lifeguards.

Sometimes if the cop or the lifeguard is especially cute, Samantha will invite him into the van to make-out. The really lucky ones get to go into the back of the van where Samantha will wrap those pouty, red, slick lips around their cocks and suck them off.

But that's just the start of Samantha's day.

By now the beach is starting to fill up. Samantha grabs his towel and sunglasses and heads out across the quickly warming sand. The trick for Samantha is to find the right spot on the beach where he will attract a lot of attraction from the boys hanging out there.  He knows that sometimes big groups of older boys hang out on the stretch of beach just past the pier. There are fewer people out there and it's a perfect place to throw a football around.  Samantha will find a promising group of boys and place his towel just near enough that the boys will definitely notice him.  It never takes long before one or two brave boys will venture over a strike up a conversation with the cute brunette laying on her towel.  A little flirting, a little giggling and Samantha will easily hook one unsuspecting boy.

"Would you please put some sunscreen on my back?" Samantha will ask a guy he is interested in.  No boy has ever answered "no." Samantha gets a rush of sensual pleasure feeling a boy's strong, rough hands spreading lotion on his soft shoulders and back.

Some of the boys get the chance to go for a walk down the beach with Samantha.  Samantha likes how it feels when a big strong boy wraps his arm around his skinny, exposed shoulders. His pulse quickens when a boy pulls him close as they walk side-by-side. It makes Samantha feel so feminine. The walk along the beach often leads to some making out under the pier.  Samantha likes pressing up against a strong young man while they make out.  He especially likes feeling his admirer's dick get hard as they kiss.














And the luckiest boys -- the most handsome, most muscular, most studly ones -- get invited back to the van for a special treat. He starts off by getting these boys aroused with his mouth, licking and sucking their dicks until they are nearly ready to cum, But before they do, Samatha quickly repositions himself so that the boy is on top of him. With his soft hands he finishes the job so that that boy shoots his hot cum all over Samantha's flat, exposed, lotion covered belly.  

The boys at the beach don't know Samantha's secret. But now you do. So would you go into the back of the his van with him if he invited you? Of course you would.

Never too Late for Sissies

I often hear wives say, "I wish I had feminized my husband years ago. Now it's too late."  That is nonsense! It is never too late to feminize your husband. Just look how lovely Sissy Jessica is in his bikini!

Mary had been married to Jeff for over 20 years. Mary knew Jeff was a crossdressing sissy, but she didn't mind. She enjoyed having a husband with a feminine side who listened to her, doted on her, enjoyed shopping with her. But as Jeff experienced some set-backs at work and was starting to consider early retirement, Mary decided it was time for some changes in their lives. Mary decided that they would both be happier if Jeff took his sissy-ness to the next level and became a woman full-time -- or at least a sissy version of a woman.

Jeff resisted at first.  But that's the good thing about sissies; they have no spine and no ability to push back. So in the end, Jeff did exactly as Mary ordered and became Jessica.  And weren't the results fabulous!  Jessica looks ten -- maybe fifteen -- years younger than Jeff did when his transition began.  And look at him now!  He looks totally hot as a woman, even in a skimpy bikini.

But Mary wasn't done yet. She also decided that both she and Jessica needed to have real men in their lives. Jessica was horrified -- distraught -- by Mary's suggestion.  Jessica cried and protested but to no avail.  Mary got her way as always.  

It was easy for Mary to find countless older men online who wanted to have a sissy of their own. She eventually selected Terrence, a wealthy divorced businessman, for Jessica.  Mary arrange all the details for their first meeting and subsequent dates.  It worked out perfectly. Once in the presence of a real man, Jessica easily and naturaly slid into the role of the woman in the relationship.  That was eighteen months ago. Now Jessica is embarking on the next exciting chapter of his life -- as Terrance's wife. That's right! Jessica and Terrance got married last month and those bikini shots were taken on their honeymoon!

Jessica is in heaven being the pretty, obedient and subservient housewife for his husband.  You can see how happy he is being feminine and domesticated and servile to a real man.  He spends hours every day making himself pretty. He derives total fulfillment by being the object of his man's desire -- and by satisfying that desire with every part of his feminized body.

Tonight, Jessica and Terrance are having a double date tonight with me an my new boyfriend.  Jessica is making dinner for all of us -- for his husband, for his ex-wife that feminized him and for his ex-wife's lover!  Could there possibly be a greater expression of what it means to be a total sissy?

So my friends, as you see, it is never to late to help your sissy fulfill his destiny!

Sissy Madison's Vacation -- Part 4

Madison had spent the last few hours in the company of a handsome lifeguard who had taken a lot of interest in Madison after seeing him lounging around the pool in his new blue bikini.

Madison had just returned to the hotel room, and was telling Mother about his evening.

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

"Well," Madison began tentatively. "He was really funny and really nice to me at the bar. He paid for my drinks. Then when I told him I had to leave, he insisted on walking me back here from the pub. So..."

"Yes?" Mother prompted.

"So, we walked back along the beach together. He put his arm around me while we walked. At first I was surprised and I almost pulled away. But then I decided that it felt sort of nice. It made me feel safe and protected. And then he kissed me. It made me feel dizzy when he did that."

"And then?" Mother asked, barely able to believe what she was hearing.

"Then he started kissing more. A lot more. It felt so good. Oh Mother, I'm so confused. I know I'm not really a girl, but something happens when I'm with him."

"It's OK, darling," Mother comforted. "I think it's lovely that you're experiencing feelings that women have. He's very handsome and strong and masculine...It's only natural that he would make you feel some girlish, romantic emotions."

After a moment Madison continued, "He wants to see me again. Tomorrow is his day off and he wants to take me out on his friend's boat for the day. I already said yes. Is that OK?"

"Of course, darling. That sounds lovely. Now get some sleep so you will look your best for your big date tomorrow.  I think you should wear your leopard print bikini. I think you will look nice in that."

In the morning, Madison put on his new bikini and slipped on a lacy cover-up and his high heeled sandals. He packed a small bag with his lipstick, his sunglasses, his sunscreen and his hair brush. Mother walked him down to the marina where the lifeguard was waiting on his friend's boat.

"Welcome aboard!" he said as he took Madison's hand and helped him step onto the boat. Madison waved good-bye to Mother as the lifeguard maneuvered the boat out of the marina.  As they got into open water, the lifeguard stripped off his tee shirt and Madison slipped out of his cover-up. Madison tried not to stare at the handsome lifeguard's tan and muscular body but he couldn't help himself. 

The lifeguard offered to let Madison steer the boat for a while.  Madison stepped up to the steering wheel and the lifeguard moved in close behind him.  As Madison held the wheel, the lifeguard wrapped his strong arms around Madison's little waist.  Madison shuddered when the lifeguard began kissing his neck. As the lifeguard pressed himself tighter against Madison's back, Madison could feel the lifeguard's dick stiffening. Madison moaned softly with excitement. 

Once they were out in open water, barely in sight of land, Madison and the lifeguard moved to the cushioned benches in the back of the boat and resumed the passionate hugging and kissing that had begun last night.  Madison became feverish feeling the lifeguard's strong, hard body pressed hard against his own soft, skinny body. The lifeguard's enormous erection was not well concealed by the nylon swim trunks he was wearing. Completely swept up by the romantic feelings he was having, Madison pulled down the lifeguard's swim trunks, freeing his massive cock.  Madison wrapped his delicate, manicured fingers around it and began pumping gently. He then lowered his head into the lifeguard's lap and put the now rock-hard dick in his mouth.

After fifteen minutes of stroking, kissing, licking and sucking, the lifeguard could resist no more and exploded in Madison's mouth, blasting his hot semen down Madison's throat.  As the lifeguard came in his mouth, Madison also shuddered with an orgasm, even though his little penis was tightly tucked between his legs. 

Before their day at sea was over, Madison would make his lifeguard cum again two more times.  Madison felt so fulfilled pleasuring this strong masculine man.

As they returned to shore, Madison could see his Mother waiting on  the dock. "Oh dear," thought Madison. "Whatever will I tell Mother about what I did today?"

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. 

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.

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! 

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 Match.com.  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!

A Sissy Honeymoon

For the last two years, I have been under the strict and controlling hand of Master Roman.  He has trained and transformed me into an exquisitiely feminine, obedient and docile Sissy.

At first I resisted my captivity and transformation.  But Master Roman skillfully -- and often cruelly -- destroyed my will to resist as he forced my inner femininity to blossom.  Eventually I learned to embrace my new existance as Master Roman's obedient Sissy servant.  My life now revolves around pleasing and serving my Master -- and nothing else.

I must have succeeded in pleasing Master Roman because he asked me to marry him!  We had a lovely, private ceremony where I took my vow of obedience and servitude, and then Master Roman whisked me down to Jamaica for our Honeymoon. 

As we stood under the waterfall, I could feel Master Roman's cock getting hard as he pressed against me.  He held me tightly in his big strong arms, kissing me.  His hands moved up to my soft little breasts that had developed from the hormones Master Roman had been giving me.  He untied the little bikini top that I was wearing.  I moaned softly as his fingers played with my swollen, sensitive nipples.

"Who are you?" Master Roman whispered into my ear.

"I am your obedient and loving Sissy Wife," I replied as he had trained me.  He smiled.

"And who am I?" Master asked.

"You are my Husband and my Master who I will serve and obey and for the rest of my life.  My only purpose is to please you," I said, reciting the acceptable answer. 

Master nodded and replied, "That's right.  And now to please me I want you to suck my cock."

I instantly fell to my knees and quickly pulled Master's cock into my mouth.  The water where we were standing was fairly deep so I struggled to breathe as I pulled his enormous hard rod into my mouth. 

As he started to cum, Master Roman said, "Sissy Wives don't need to breathe.  They just need to suck cock."  He then pushed my head underwater and held it there.  Even though I was practically drowning, I felt so fulfilled knowing that I was performing a service that pleased my Husband/Master so greatly.  It felt wonderful to being a good Sissy Wife, on my knees, feeling my Master/Husband's hot cum blasting into my mouth and down my throat.  Even as I started to lose consciousness, I ensured that I had thoroughly drained my Master/Husband and had swallowed every drop.

When I regained consciousness, I was on the floor of our hotel room.  These was a note jammed in my bikini bottoms that said, "Get cleaned up and put on new bikini.  Meet me in hot tub next to the big pool.  Hurry.  I need another underwater blowjob right now."

A Sissy Wife's job is never done.

A Sissy's New Bra

Sissy Monica looked down sadly at his expanding breasts.

Mother had started her Sissy son on a rigorous feminization program ever since finding a collection of graphic forced feminization magazines under his bed.  "Is this what you want, you pathetic faggot!" she screamed when she found his secret stash.  "I can make this happen to you, you know.  You're not much of a man anyway are you?  You're a pathetic excuse of a male, just like your father was!"

And from that day day forward, Sissy Monica was forced to live his life as a girl.  Sissy Monica was so ashamed of Mother's discovery and so scared of her temper, that he didn't fight back. 

At first, he continued to go to high school as a boy, transforming back into a Sissy girl as soon as he got home.  Mother filled Sissy Monica's closet and drawers with pretty girl clothes and taught him how to put on make-up and fix his hair.  At first, to make Sissy Monica look really girlish, Mother filled the cups of his bra with realistic silicone breast forms.

But that was months ago.  But since then, after Mother's strict regiman of dieting, figure training and hormones, Sissy Monica's body had started to change. 

Recognizing these obvious changes in her son's body, Mother gave Sissy Monica a very exciting gift.  It was a padded bra.  Mother ordered him to put it on.

Sissy Monica slipped the straps on over his skinny shoulders while Mother watched.  He expertly fastened the clasp behind his back.  To his horror, Sissy Monica realized that his own boobs neatly filled the cups of his new bra.  You see, Sissy Monica no longer needed to wear the breast forms -- his own breasts had swollen quite dramatically in the last few weeks.  Sissy Monica now had a curvy, womanly bust with just his own boobs in his own padded bra.

"Ohhhhh!" Mother cooed, "Look at you!  My little Sissy Monica has blossomed into a real lady!  Tomorrow let's go shopping for a cute swimsuit for you!"  Sissy Monica started to cry, realizing that he would be stuck forever as a Sissy girl and never again be able to live his life as a boy.

Sissy Monica never returned to high school after that day.  But later that spring Mother and her "daughter" Sissy Monica went on a 10-day Carribean cruise during which Mother delighted parading her reluctant Sissy Monica in the prettiest and most revealing cocktail dresses and swimsuits, putting her Sissy's new cleavage on display for all to see and admire.