Bad News for My Sissy Husband

"Sweetie, do you have a minute to talk?" I called up the stairs.  My darling sissy husband, Lily, came down right away.

"Yes, Martha. Is there something that you need?" he asked.

"My, don't you look extra pretty today!  That pink top is super cute on you and really shows off how you are...developing.  And I love that necklace on you!" I cooed.

"Thank you, Martha," he replied softly. I could tell he was both thrilled and a bit embarrassed with my compliments.

"Sweetie, we need to talk. Now I know you have really been looking forward to our vacation to the Bahamas tomorrow," I started.

"Oh yes, Martha.  I'm very excited about our trip!" he replied breathlessly.

"Yes, well," I started. "There's been a change of plans.  You're not going," I stated matter-of-factly.

Completely blindsided by my announcement he responded, "What? No! We've been planning this trip for months!"  His eyes were starting to tear.  This announcement was getting him rather upset.

"Now Lily, really!  Think about it.  I mean, just look at you.  Look how much you've changed!  Your hair, your breasts, your hips.  You have become so feminine!  How can I be expected to go on a romantic Caribbean vacation with you?  You can barely even pass as a man anymore!  Needless to say, you can't take your shirt off on the beach now that your boobs have grown so much," I explained.

"But I did all of this for YOU!  YOU wanted me to become more feminine, more ladylike.  I made all of these changes because YOU wanted it!" He was starting to cry as he spoke.  Goodness, the hormones make him so emotional!

I put my hand on his shoulder, "Oh, Lily, of course I know that. This is how I want you. Soft and feminine and gentle.  I love having you as my sweet little sissy housewife.  You look and smell so pretty and you take such wonderful care of me.  You are exactly the way I want you. At home, that is.  But on a romantic vacation?  Well, that obviously is not going to work."

"So you cancelled all of our vacation plans?" he asked stupidly.

"Oh, good heavens no, silly girl.  The trip is all paid for.  I'm going with Ben."

"Ben? Who's Ben?" Lily asked.

"Ben Martins, silly. My editor," I said. Then the wailing really began.  

"You're going on vacation with Ben?!?  Why? How? What's going on?" Lily was starting to get a bit hysterical by this point.

"Well, Lily, Ben and I have been spending a lot of time together finalizing my latest book. And he is going through a difficult time since he is getting divorced.  Anyway, over the past couple of months, he and I have gotten rather...close.  He really is a very nice man.  And so tall and handsome!"  The crying got much worse when I said that.

By now I was growing tired of Lily's sobbing. "Now calm yourself. You know this is for the best. Look, I am a woman and I have needs -- and believe me, he really knows how to fill my needs!  Ben and I will be able to have a wonderful, romantic vacation together in a way you and I simply can't anymore. Besides, you have fallen way behind on your chores and this will give you a whole week to get caught up."

Lily had no words in response to that.

"And since I'll be spending more time with Ben at his apartment when we get back from the Bahamas, I thought it would be nice if you would go over there while we're away and get it all tidied it up.  It really is a mess and you wouldn't want me having sex in an apartment that wasn't properly cleaned, now would you?"

"Well, would you?" I repeated a bit more sternly, in case Lily thought it was a rhetorical question.

"No, I guess not," he answered softly.

"No, of course not," I agreed.  "Now pull yourself together. I know, let's go to the mall and I'll buy you something pretty to cheer you up.  And while we're there, you can help me pick out a new bikini and maybe a sexy nightie to take on my trip.  OK?  Now dry those eyes and grab your purse."

Sissy Roommate -- Part 6 -- Sissy Doubts

Tank has been giving me money almost every week to buy more outfits.  I think it gets him very excited to send me off to the mall with the assignment of buying clothes to wear that will make me look pretty for him.                                                                                    Here's a cute little outfit I bought on my shopping trip last week.  I love this little denim top.  I think it really shows off how skinny I've become since I started dieting extra hard.  I think my arms look so pretty and feminine in this photo.  And of course I bought another short skirt.  I love how this one is just a little bit flouncy and how it moves and swings as I walk.  But it is so short! If I sit or bend over, my lacy panties are on full display for all to see.   

Tank has been sending me out in public dressed as a girl more frequently.  Tank took these pictures of me outside our dorm building before telling me to go to the Student Union to buy some snacks for him.  At first I was super nervous about walking around campus looking this way. But I was really surprised to discover that nobody recognized me.  I guess that's partly because I was always sort of a loner and didn't have any real friends on campus when I was living as a boy.  But I also like to think it's because I look really cute as a girl.  I certainly get some admiring looks and sometimes comments from the boys I pass as I walk around campus.

I think Tank really likes me and that makes me very happy.  He certainly gets excited and wants to have sex with me a lot. But I guess I should tell you that Tank sometimes brings girls -- especially cheerleaders -- back to our room. He says he needs to keep up his image and that people would think it was really strange if he wasn't sleeping with a bunch of girls.  Anyway, the hardest part is when he texts me that he's bringing a girl over and I have to clear out of the dorm room immediately.  And sometimes I'm all dolled up because I was expecting to spend the evening with Tank.  So I have to quickly clean off my make-up and change back into my boy clothes and plan on spending the night sleeping on the couch in the TV room downstairs.  I guess I get a little jealous when Tank is sleeping with girls and sometimes it's hard for me to fall asleep on the couch thinking about him being in bed with them.  But I believe that Tank really loves me -- in his own way -- and that this is just one more way I need to be a good sissy and to be supportive of my man.

As much as I enjoy making Tank happy -- and as natural as it has become for me to dress and act like a girlish sissy -- sometimes I wonder if I am doing the right thing.  Each day I feel a little part of the person I was before I met Tank disappear.  Sometimes I even get confused if I'm even really a boy any more.  Where will all this lead?                                                                      Anyway, tomorrow I'm going ride the bus back to the mall to buy some more clothes. And this time I am going to go dressed as a girl. That way I can try on things in the ladies dressing room and people won't look at me funny when I'm shopping for bras and underwear. I don't think anyone will guess that I'm not really a girl.  Do you?

Sissy Roommate - part 5 -- Some New Clothes

Well, my trip to the mall was quite an adventure.  I had made a list of the things I thought I would need.  More sexy underwear, some sexy tops and some short short skirts were definitely on the list.  I also planned to buy some more make-up and some brushes and sprays to make my hair look nicer.  And I hoped I would have enough money left over for some perfume -- I thought that Tank would really enjoy that.                                                                             But one thing made me extra nervous about my shopping adventure: Tank had also told me to get some clothes to wear outside.  He was going to make me go outside fully dressed as a girl! So I needed to be smart about what I bought since this wasn't just for sissy dress-up games in our dorm room.

Here's one of the outfits I bought for myself on that first trip to the mall.  Don't you like this cute little top?  I didn't realize when I bought it that it wouldn't even cover my tummy!  But I think it looks super cute.  And I think it looks nice with the short plaid skirt I bought.  I also bought some shoes and a bag that I could take outside with me.

Here's a close-up of my face.  I think you can see that I've gotten a lot better with my make-up.  I think I look very pretty in this photo.                                                                                         Maybe you can tell that I have plucked my eyebrows into a pretty arch shape.  That, along with some eyeliner and mascara, helps make my eyes look extra big and pretty.                                                                                             And Tank really likes it when I wear lipstick.  With some practice, I've gotten really good at putting it on. I spent a little more to get extra long wearing lipstick because regular lipstick doesn't stay on for very long since Tank likes kissing me so much.

And as you can see, Tank was true to his word.  He made me go outside behind our dorm to take these photos.  I was so scared that someone would see me as we went out the back stairs.  But the sensation of being outside dressed as a girl was so exciting!  I loved the feeling of the cool fall air on my exposed skin.  I loved posing for my man as he took dozens of photos of me.                                                                                                And I could tell that Tank was getting excited by taking me outside and making pose for photos.  Because when he was done taking pictures, he grabbed me by the wrist and rushed me back upstairs to our dorm room.  "All fours!  Now!" he growled. I quickly did as I was ordered and positioned myself on my hands and knees on the floor.  Tank pulled down his pants and approached me from behind, lifting up my skirt and pulling down my lacy panties.  Tank loves to fuck me in all sorts of different positions -- but I think he likes it best when I'm on my hands and knees.  I love it when he spanks my bottom while his dick is pumping in and out of me.  It gets me so excited when Tank says how tight my "pussy" is while he's fucking me.  I have to admit that it's pretty painful when Tank fucks me because his cock is so enormous. Sometimes it hurts so much that I cry while Tank is pounding away at me.  But it also makes me feel so happy and fulfilled to be pleasing Tank and to submit to him so completely.

Sissy Roommate -- Part 4 -- My Purple Dress

So from that day forward, I have been Tank's sissy.  He has a tremendous sexual appetite, needing to cum two or three -- and sometimes more -- times every day.  He also expects me to do other stuff for him, like his laundry, which I do every day without being asked.  I know he expects it so I just do it.

At first, I would go through bouts a doubt and self-loathing.  What was I becoming?  Why was I doing this?  I would think about performing oral sex on Tank and get sick to my stomach.  But then these feelings would subside and be replaced by feelings of warmth and happiness and satisfaction unlike any I had ever experienced before, as I assumed the role of the subservient, obedient woman serving her superior, masculine male. 

About half of the things I took from the lost and found bin at the gym turned out to fit me pretty well and it seemed to please Tank when I would get dressed up.  I also got much better at doing my make-up and making my hair look prettier. I also bought a ladies razor at the drug store and started shaving my body. I really like it when Tank runs his big rough hands up and down my soft, smooth legs. 

The best item that I took from the lost and found was a really pretty purple dress.  It had a lovely floral print and a fancy lace inset around the neck line.  I felt so pretty when I wore this -- just like a princess!  

Sometimes, when I would emerge from the bathroom after putting on my dress and my make-up, Tank would have me stand in the middle of the room with my gaze directed downward -- a position of total submission.  He would say something like, "Who do you belong to, sissy bitch?" and I would reply, "I belong to you, Sir." This little ritual would continue for several minutes until Tank was worked up into a frenzy.  Then he would grab me and roughly shove his enormous dick into my mouth.  

Other times, when he saw me wearing this dress, Tank would sit naked on the edge of his bed and he would tell me to climb on his lap and we would make out for a while before he decided it was time for me to suck him off.

Even though I looked pretty in the clothes I had taken from the lost and found, after a while, Tank got tired of seeing me wearing the same things all the time.  He told me to get some more clothes. He peeled off four $100 bills from a fat roll of money he had in his sock drawer and threw them at me. "Go buy some new clothes. Get some sexy stuff."

I had never bought girls clothes before but at least I knew something about my size based on the things I took from the gym.  I decided that the next day I would take the bus to the mall.

Mommy's Pajama Sissy -- Part 10

When I picked Tammy up from school, he was all smiles.  "Well, how did it go at school?  How did people react to seeing you as Tammy -- and in a nightgown?"

"It went great!" Tammy practically shouted.  "Of course, when I first arrived, I got a lot of stares walking down the hall to homeroom. But mostly I think people were staring because they didn't know who I was -- or why someone was wearing such a fancy nightgown to PJ Day!"

Tammy continued. "When I first got to homeroom, people were shocked.  I mean speechless. I thought it was hysterical!  But after just a few minutes, a bunch of the girls -- the cool girls, the ones that never talk to me -- came over and started fussing all over me. They were saying how pretty I was, how jealous they were, and so on.  It was totally fun!"

"It was sort of funny," Tammy continued, "That I was the one wearing the prettiest nightgown! Most of the other girls were wearing pajamas or flannel nightgowns -- like the ones we wear together in the winter. Nobody was wearing a fancy, pretty nightgown like me."  I was relieved to hear this as I thought Tammy's selection of nightgown wasn't exactly appropriate and I thought it might cause a problem -- but apparently not.

Tammy continued, talking a mile a minute. "But of course, the boys noticed me too.  A bunch of them just couldn't stop staring at me while I was chatting with the cool girls.  And then a couple of brave ones came up to me.  At first I was worried that they were going to give me a hard time or start calling me names.  But that didn't happen. Instead Jimmy Michaels came up to me a said 'Wow, you really look amazing. I barely recognized you.'"

I was shocked to hear this because I was aware that Jimmy Michaels (who was captain of the football team, by the way) had never been nice to Tommy over the years, calling him names like "sissy" and "faggot" just because he didn't like to play sports and because he mostly kept to himself.

"Well, after homeroom, we all went to the auditorium for the end of year presentation. The girls from my homeroom asked me to sit with them, and we were joined by the cool girls from the other homerooms.  And everybody was super nice to me and made a big deal about how pretty I looked." Tammy was practically breathless from talking so fast.

"Then after the presentations, we all went to the gym where they handed out yearbooks.  And they had pizza and soda and everybody spent the rest of the day signing each others' yearbooks and chatting and eating.  This time Jimmy Michaels came up and talked to me, even offering to get me some pizza and soda. He told me that he would working all summer at his uncle's car shop on North Street and he said that he hoped that we would get to hang out together over the summer..."

"The whole day went by in a flash. Before I knew it, it was time to go home."

"Well, young lady, you certainly had an exciting day!" I said. "You must be exhausted."

"Oh, I guess. But I'm supposed to meet some of the other girls at the mall at 3:00.  Can you drive me?  And tonight, Jimmy invited me to go with him to end of year bonfire down by the lake -- can I go to that too?"

"Well, I don't see why not. If it's what you want to do," I said.

Tammy's life experienced a big change as a result of his wearing a pretty nightgown to PJ Day.  That whole summer was a whirlwind of parties and days at the lake and afternoons at the mall and nights at the movies. Needless to say, I had to spend quite a bit of money on getting Tammy all the clothes that he needed now -- casual outfits and jeans and tank tops; swimsuits and cover-ups; party dresses; the works!

Mommy's Pajama Sissy -- Part 5

Well, I imagine you could already guess what might happen next. I couldn't stand having My Little Princess with me only when we were home alone and wearing our nightgowns. In early May I went out and bought Tammy some pretty dresses and shoes that he could wear out in public! 

There was a bit of nervousness at first, as you might expect. But the thrill of going out in public in a pretty dress was more than enough to motivate Tammy to summon enough courage to join me on some real-life adventures.                                                                                                                                           After several days of planning, we were all set for an exciting weekend together. Friday afternoon was very warm, so I dressed Tammy in a gauzy turquoise dress -- he looked simply lovely! Our Friday adventure started with a visit to the nail salon, where Tammy got his first mani-pedi. He was so nervous at first that his hands were shaking. But he settled down and his pretty soft pink nails looked divine. Then I took him to the mall where I let him pick out -- and try on -- several more new dresses and shoes and handbags. We went to three different department stores and must have been there for two hours! And of course I needed to buy him some bras and panties -- today he was borrowing my under garments but needed a collection of his own. Then we had dinner together at a restaurant where Tammy realized that he was getting some serious attention from our waiter!  Tammy handled it well and we had a simply wonderful time.

I had a busy Saturday planned for us. I dressed Tammy in an elegant royal blue silk dress. He looked stunning -- and so grown up! We had lunch together at an intimate cafe downtown that is very popular with ladies out for the day together. Then a matinee of a play at the Civic Auditorium. And finally, the highpoint of our day, we went to a fundraiser reception at the art museum.  Since alcohol would be served, the event was restricted to guests 21 and older -- which Tammy wasn't.  But I was so confident in his ability to appear like a grown-up lady and I knew this wouldn't be a problem. When the ticket taker asked the two of us for our IDs when we entered, I simply said to him "thanks for the compliment" and the two of us walked right on in to the event.  It was magical.  The museum was beautiful, the guests were all dressed up, there was a string quartet playing -- it was heaven! And I could see that My Little Princess was in heaven too.

Waiters passed glasses of champagne and little hors d'oeurves. About 45 minutes into the event we found ourselves near one of the bars where a young gentleman was chatting with a bartender.  I struck up a conversation with the handsome young man whose name was Steve. Steve looked very dapper in an expensive suit and tie. He seemed happy to have someone to talk to. He told us that he had recently finished business school and was home visiting his parent before starting a new job in New York with a big bank. He explained that his parents had bought tickets to the event, but were suddenly called out of town for the next few days. He was attending the event alone and didn't know anyone else there. Of course I introduced my lovely young Tammy to the handsome young Steve. Tammy had had several glasses of champagne by this time and was starting to loosen up a bit. It didn't take long for Steve to start flirting with his pretty new acquaintance. And it didn't take long for Tammy to play along and join in!

At one point Steve excused himself to use the restroom. "What a catch!" I said to Tammy. "Oh stop, Mother!" he replied. ""Don't be silly."

"I'm not being silly," I answered. "He's obviously smitten with you and I can tell you like him too." Tammy turned bright red when I said this. "Why not see where this goes. He's only in town for another two days. Then he's off to New York. Why not see what can happen before he leaves town..."

Tammy was initially dumbstruck by my suggestion.  But his internal feminine needs -- and the champagne -- pushed him to be bold enough to surrender to his urges.

"Alright, mother," Tammy said. "Let's see where this goes."

Mother's Pretty Little Sissy Daughter -- Part 2 -- Getting Ready for a Sissy Day

*** This is a continuation of a story from 2012.  To find Part 1, click on the "Sissy Jessica" Label in the right margin of the blog.  Enjoy! ***                                                                             As you already know, I have been pushing my son, Jesse, to embrace his feminine side.  In fact, I want him to become my daughter, Jessica, full-time.  Jesse is much too pretty to be a boy I think. And I tell him that almost every day.

I encourage my little Jesse to dress up as Jessica every chance he gets.  I do everything I can to get Jesse to think of himself as a girl.  I want him to let go of being a boy and to embrace a completely and permanent feminine existence.

Jesse still goes to school as a boy, but he spends all his time at home as a girl.  He has been living this way for almost six months.  He has become so naturally feminine that it has become unbearably painful for me when he reverts to being a boy.  And over that time, Jesse's hair has started to grow out long and beautiful and his body is slender and pretty as a result of the strict diet I keep him on.

As soon as he gets home from school and throughout the weekends, there is no sign of Jesse, only Jessica.

And because he spends so much time as Jessica, he has become very girlish and feminine. And he very talented at doing his hair and make-up.  Here are some photos I took of Jesse getting ready to spend a Saturday with me as mother and daughter.  He starts his day with a warm bubble bath, soaking in a tub where fragrant oils soften his skin. The experience relaxes and prepares his body and mind for a day of feminine fun.

After his bath he applies lotions to his skin before he begins to do his hair and make-up. Since he has been doing his own hair and make-up almost every day for several months, he has become a true expert at making himself look beautiful.   

I have a fun and exciting day planned for the two of us.  First, we will go to the big shopping mall that is about 20 minutes away.   We'll shop for dresses and lingerie at the big department stores.  Jessica always gets so nervous when I push him into a ladies dressing room to try on things.  Then we"ll head downtown for lunch at a restaurant we like. 

 I haven't told Jessica this yet, but there is a huge car show going on downtown.  The streets will be crowded with people and we'll probably have to park far away.  And of course the car show attracts men -- and teenage boys -- by the thousands.  So Jessica will get plenty of attention and admiring looks -- and comments, I expect -- from the men and boys we will be walking past.

Doesn't that sound like fun?

Now hurry along and finish getting ready, Jessica.  We have a busy day planned!

Sissy Priscilla Part 1 -- Mother's Sweet Sissy Daughter

I have always known that my sweet little boy was a sissy.  At first he tried to hide his interest in everything girlish from me.  But I could always tell that he was more interested in girly things than a little boy should be.  He so enjoyed sitting with me at my vanity as I did my make-up and standing next to me in my closet as I picked out what dress to wear.  He was fascinated with my lingerie, my perfume, my hair curlers -- really everything that was feminine.                                                                                                                                          I knew that he secretly tried on my clothes when he thought I didn't notice.  When I thought he was ready, I spoke to him about it.  I reassured him that I didn't mind if he wanted to play dress up at home.  I told him that I thought it was sweet that he had feminine feelings and interests.  I urged him not to keep this bottled up inside and to feel safe letting his girlish feelings out at home.  At first he tried to deny what I was saying, but it didn't take long for him to crack and to admit the longings that were deep in his young heart.

These are some photos of what my son looks like now when he is at home.  Isn't he adorable?  He is so naturally feminine and girlish I sometimes forget he isn't really a girl.  He spends his days at school as a boy but after school and on weekends, he is my daughter, Priscilla.  I let him borrow any my clothes if that's what he wants to wear -- but he has a closet full of pretty outfits and drawers of lingerie of his very own. Priscilla is simply the sweetest little girl any mother could dream of for a daughter.  I don't know who is happier that there is a young girl in the house -- Priscilla or me!

For the past few years, I have been encouraging his to let his hair grow out.  His hair is now long for a boy, but I don't think anybody notices or cares; these days it seems like anything goes.  What's important to us is that his hair is now long enough that he can style it to look pretty and feminine when he wants to be Priscilla. I even take him to my beauty salon when he needs a haircut.  My stylist does such a nice job with his hair.  

We have such fun together as mother and daughter.  Here is a photo I took when Priscilla and I spent a weekend in the country.  We stayed in a cute little bed and breakfast, went antiquing, shopped for crafts and clothes.  In the evening we went to a state fair that really fun.  I noticed that a lot of the teenage boys at the fair were "checking out" Priscilla as we walked around together.  Can you blame them?  Of course not! My Priscilla looks adorable!  No one had any idea that the pretty young girl in the beret was actually a boy.

My Sissy Neighbor -- Part 6: Worried Little Sissy

Anita works at Club Satin five nights a week - and he makes a lot of money working there.  He gets paid well -- all in cash -- plus he makes even more money by having customers buy him drinks or paying for a little bit of making out.  But I told you that his parents think he works six nights a week as a dishwasher.  That's because on Sunday nights, when Club Satin is closed, Andy comes over to my house and becomes Anita -- and just hangs out with mom and me.  

Sometimes we'll stay in and watch a movie on TV.  But usually we go out as as three ladies.  We often start by going to the mall.  Anita always needs to buy more clothes and shoes and make-up.  It's really fun to shop with him. He's really good at suggesting clothes and make-up that mom and I should try. And mom really enjoys watching him shop for sexy, glamorous clothes and ridiculously high heels for himself -- things she would never, ever buy for herself.  I think it's exciting to go into the dressing rooms with Anita to help him try on things. Here's a picture I took last week of Anita trying on some bright pink lipstick at Macy's.  What do you think?







After a bit of shopping, we then go out to dinner somewhere.  Anita always insists on paying.  He does make a lot of money working at the club and he likes to show his appreciation to my mom for all she's done for him.  My mom puts up a bit a fight every time, but Anita always wins and pays our bill.

It's really fun to be out with a girl as glamorous as Anita.  I'm not bad looking at all, but I don't have have the style that Anita has.  Men will literally stop talking or walking -- or even breathing, I think -- when they see Anita. Sometimes you can overhear people trying to figure out if Anita is a model or a celebrity that they've seen on TV.  And men are ALWAYS hitting on him!  Guys will often send drinks over to our table -- and it's not because they are so turned on by mom or me! And some men will barge over and try to start flirting with Anita -- right while we're having dinner.  Mom is really good at shoo-ing these annoying guys away.  But it does give the three of us a big laugh every time.  

But the most fun situations are when we run into some boys that I know from school.  These guys start totally drooling over Anita!  They have absolutely no idea that the hot girl they are getting boners for is really that boy in the black hoodie that they pass everyday in the hall at school! I can tell Anita gets a bit nervous during these encounters -- but I know there is absolutely no way that the dumb boys from school will figure out who this crazy hot chick really is.

Anyway, we were out with Anita tonight, doing our usual shopping and dinner thing.  Anita looked glamorous as always but he tones it down a bit when he's not going to the club. Doesn't he look absolutely adorable with his hair pulled back like this? You'd swear he was a super hot sorority girl, wouldn't you?  At the end of the meal, Anita told us something worrisome -- you can even see the worry on his face in the photo. "I can't go out with you next Sunday," he said. "I have another...commitment."

Mom could sense that Anita was uneasy so she pressed for more information and this is what Anita said.  "Next Sunday night I'm going out -- on a date, I guess -- with the manager of the club.  You see he likes to go out with all the girls, especially the dancers. And last night he asked me.  I think I sort of have to go out with him.  None of the girls turn him down -- ever.  I think it would be a big mistake if I said no. So I agreed to out with him next Sunday night when the club is closed."

"I don't like the sound of this at all!" mom said. "And besides, he probably doesn't want to go out with you to talk about current events, if you know what I mean." Anita and I both giggled.  Mom is so funny. She can't even say "He obviously wants to have sex with you -- and that would obviously be a huge problem for you!"  But we understood exactly what she was saying.  Mom tried to convince Anita to cancel his date but he was too scared to do that.

"Well, I guess you'll just have to do what the rest of us girls do in that situation," mom advised. "You'll just have to tell him you're having your period!"

My Sissy Neighbor -- Part 4: Sweet Sissy Kisses

After working until 11:00, Anita comes back to my house to change back into Andy before heading home.  Mom always greets Anita at the door with a big hug.  She's usually in her big fluffy bathrobe because it is late, but she is too worried to go to bed until she knows Anita is home safe.

Andy's home life is more than just terrible. Andy is deathly afraid of what his father would do to him if he ever found out about Anita.  As it is, Andy's father is abusive towards him in many ways.  Andy is right to be scared, if you ask me.

Anyway, I usually hang out with Anita and chat while he changes.  I'm usually in my bathrobe too. I usually hang up his things while he gets undressed and washes off his make-up. He puts anything that needs washing, like his bras and panties and stocking, in a hamper and my mom will put them in the laundry with our stuff during the week.  (No chance of mixing up Anita's underwear with mine -- his bras are 34DD and mine are 36A!)

We talk about all sorts of stuff while he's undressing. One night, a while ago, after he had told mom and me about kissing some of the customers at the club, I asked him, "Do you like it when you have to make out with men?"

"I guess I don't mind it too much. I don't think I'm gay but I like the idea that men find me desirable and sexy. It's very exciting and..." Anita searched for a word.

"Validating?" I offered.

"Yes!" Anita exclaimed. "Validating."

Looking at Anita and talking about kissing was making me feel funny. He hadn't started taking off his make-up yet and he looked so beautiful. "Can I kiss you?" I asked.

"Sure, if you want to," Andy replied. We sat together on the edge of the twin bed that was in the dressing room. I put an arm around him and looked deeply into his pretty eyes. As I went in for my kiss, he delicately closed his eyes, just like I imagine he does with his customers at the club. I was seriously turned on!

I could smell his perfume and taste his lipstick as we kissed.  I wrapped my arms around his slender body, feeling the corset he wore beneath his dress to give him that sexy wasp-waist shape.

We made out for about 15 minutes before I broke it off; it was late and Andy still needed to change and get home. "That was amazing!" I panted. "You are so sexy! And you kiss like a girl!" We both giggled at that.

"And so do you," he replied.  "I assume."

I needed a moment to figure out what he meant by that.  Then I realized -- he had never kissed a girl before.  Poor Andy!

After that, making out became part of our routine every night before Anita changed back into Andy!  I just love kissing my sweet, beautiful Sissy Anita.

A Sissy Every Weekend -- Part 4. Going to the Mall

On Saturday afternoons, after the twins are done with their sports, we often go shopping. Sometimes we take taxis to the glitzy stores downtown.  Other times we all pile into Aunt Jenny's big SUV and drive to the malls just outside of town.

The girls and my aunts just love shopping! They can try on shoes and dresses for hours. I guess I don't mind going along with them too much. When we go to the fancy stores, they always insist that I try on lots and lots of dresses. Sometimes it seems like they think I am some kind of living Barbie doll to play dress-up with.

Someone will always find some pretty dresses in my size. Then two or three of my cousins will pile into the fitting room with me while I strip down to my bra and panties. Then the girls will help zip me into the dresses. There is a ton of giggling and they love to take photos of me as I model the outfits they found for me. 

This weekend we went to the Galleria Mall where there are several big department stores. Here's a photo of me wearing  a fancy designer dress that I tried on at Nordstrom's that I could never afford.








Here's another dress that the girls insisted that I try on. I struggled to squeeze into this tight, clingy red and orange mini-dress. 

They all said that this dress made me look "so hot!" and that "guys wouldn't be able to resist me wearing this dress."  I don't mind dressing up like a girl, but I don't like it when the girls start talking about how "sexy" I am or how I must "really turn men on" and things like that. That kind of talk always makes me very uncomfortable. But even when I tell them to stop teasing me that way, they often keep doing it anyway.


















Then Aunt Jenny found this sweater and skirt set and suggested I try it on. Everyone said I looked cute in it and I thought it looked nice on me. Aunt Jenny said it was on sale and she insisted on buying it for me.  

Our next stop was Neiman Marcus. All of us tried on the summer dresses that were on clearance. Here's me in a pretty striped dress that everyone thought looked cute on me. Mother said it was a very good deal so she bought it for me.

Our last stop was Saks. Everybody tried on a bunch of outfits there. Aunt Jenny tried on a pretty blue dress but didn't like how it looked on her. She said that it would probably look better on me. So she dragged me into a fitting room and stripped off the dress. Wearing just her bra and panties, she helped me put on the dress she had just been wearing. When I came out of the fitting room, Mother and all of the girls gushed over how pretty I looked. Aunt Jenny insisted on buying it for me. As the sales lady was wrapping it up, Aunt Jenny said, "It's the perfect dinner date dress, don't you think?" All the girls giggled when she said that and I turned bright red.

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. 

A Sissy and his Mother have a Weekend Adventure -- part 3

Janey had a little headache when he woke up the next morning.  But we weren't going to let a little hangover spoil out last "mother-daughter" day in the city.  Janey wore a pretty black and white sleeveless dress, which was perfect because the day was warm.  Our plan was to have breakfast and then head to church -- going to church gives Janey the perfect excuse to get all dressed up on a Sunday morning. Then some more shopping, a light lunch and then back to the hotel for Janey to put his dresses away before heading home.

But just as we were leaving the hotel to walk over to the cathedral we ran into Janey's young banker friend from last night. 

"Janey!" he exclaimed when he spotted us.  He gave Janey a quick kiss on the cheek.  "I'm so glad I saw you.  I was going to call you later, but now I can ask in person."   The young banker looked my son up and down, his gaze lingering on Janey's sexy legs. "Wow! You look...amazing," he panted.

The young banker seemed to have lost his train of thought staring at Janey -- and Janey was so mesmerized by his romantic young banker that he had no idea what was going on.  I helped everyone out.  "Was there something you wanted to ask Janey?" I prodded.

"Oh, yes, right," he managed to stammer as he collected his thoughts.  "I have these tickets to a big charity fund-raiser on Friday night at the Downtown Yatch Club. It's one of the big social events of the year.  It is going to very nice party and I was wondering if, well, if you would be my date for the evening."  

Immediately, and without consulting me, Janey replied, "Oh yes!  I would love to go!"  And with that Janey gave his new boyfriend a big hug.

I, of course, was terrified.  Janey was quickly getting into very deep waters here and I was not at all certain that he would be able to pull this off.

Thinkly quickly, I explained to both of them that Janey and I would again get a hotel room for Friday night and that Janey could go to the party provided that "she" was back to the hotel by 1:00AM.  The banker gave Janey some more details and promised to be in touch soon.  We said our good-byes --  including a big, long kiss for Janey -- and Janey and I continued on with our ladies day out.

The days that followed that magical weekend were very difficult for Janey.  Not only did he have to change back into his boy clothes for the week, but poor Janey was experiencing his first schoolgirl crush. The emotions were so powerful.  He was simultaneously mopey and sad because he missed his young banker boyfriend and wildly excited about seeing him again at a fancy, very adult, cocktail party on Friday.

The school days passed very slowly for Janey that week.  When Friday did finally come, I let him miss school so that I could take him back in to the city to shop for a new dress to wear to the party.   We checked back into our hotel and hit the designer boutiques.  And we found the perfect dress!  It was a black, sleeveless dress with little white polka dots.  It was a faux wrap style that had a bow on one side and was cut tantalizingly low in front. The full skirt came right to his knee, a layer of chiffon gave the whole dress a romantic, elegant effect.  Janey looked stunning in his new cocktail dress.

We spent most of the afternoon getting him ready.  I took Janey to a salon near the hotel to get a mani-pedi (I knew he wanted to wear his favorite open toed shoes with the ankle strap) and to get his make-up done.  

Janey's banker met us in the hotel lobby. I thought the young man was going to die from excitement when he saw how pretty Janey looked. The banker had arranged a limo to take them to the party.  I said goodnight to the young couple and whispered to Janey to be careful.  As the limo pulled away from the curve, I gave a little wave as I watched Janey head off for his first date as a young lady.  

Of course I stayed up waiting for Janey to come back to the hotel that night. When he did get home, he was wide awake and bubbling over with excitement.  Janey had to tell me about every detail of his dreamy, romantic evening:  the music, the celebrities he saw, the food, the drinks, the pretty dresses the "other" ladies wore -- everything.  He even had to describe the fancy ladies rest room at the yatch club.  But mostly he wanted to describe how charming and romantic his date was.  How they danced together and how they made out on the balcony overlooking the harbor.  

Then Janey said, "He wants to take me out on another date -- alone -- tomorrow night."  

I knew that this charade must not continue. Someone was going to get very hurt when the truth came out -- probably Janey.  "No Janey, that is not a good idea.  I can't allow you to do that.  This is all getting very...complicated.  Just what do you think is going to happen when he finds out you aren't really a girl?"

"I already told him and he doesn't care!" Janey replied.  My mouth dropped open and I almost fell over with surprise.  "It's true," Janey continued.  "I told him that am a Sissy during the limo ride after the party.  At first he didn't believe me until pulled down my panties and showed him."

"WHAT?!?"  I exclaimed.  "What did he do then?"

"He said that if I wanted to be his Sissy that I needed to suck his cock.  So I did.  Right there in the limo.  And after he came in my mouth he told me that I suck cock better than any real girl that he's been with.  And that he wants me to be his Sissy! Isn't that wonderful, Mother?  I am so happy!  I am in love with him, Mother."   

Before I fainted, the last thought that passed through my mind was that my sweet little Sissy daughter was now a complete Sissy slut!