Mommy's Pajama Sissy -- Part 11

After the success of PJ Day -- and Tammy's "coming out" -- Tammy was on his way to having a very exciting summer.  In fact, I don't think I can remember seeing "Tommy" all summer long.

As the summer began, Tammy took a lot of interest in how he looked, asking me to take him to my salon every week so he could have his hair styled and colored in different ways. One week he'd ask for his hair to be straight and sleek and lightened; the next he'd want some curls back and a different shade of blonde. By now, Tammy's hair had really grown quite long so the stylist was able to make it look really great.  And Tammy started wearing more make-up -- which he had really never done before. 

And then there were the clothes!  I spent a fortune during the weeks after school ended to get Tammy all the different outfits he said he needed. Here are a couple of photos I took of Tammy after one of our trips to the mall.  Doesn't he look adorable.  You can see how he had his hair lightened.  And look at his eye make-up.  So pretty!  And check out those sexy sandals -- I wouldn't even be able to walk in those!

Right from the start, Tammy's schedule that summer was busy! The girls from his class started including him in their trips to the mall and hanging out at each other's homes.  Tammy would come home after spending time with the girls and tell me all about what they did -- and what they talked about -- which seemed to only BOYS, BOYS, BOYS!  And Tammy got his share of teasing from the girls because of Jimmy.  More on that in a minute!

One of the girls even got Tammy a job waitressing during the busy lunch time shift at the local diner.  I know this was hard work, but Tammy seemed to really enjoy it.  And I was glad that he was working during the summer -- even if just for a few hours a day.  Tammy looked so cute in the apron he wore when he was working. And every time I stopped by, Tammy was always getting a lot of extra attention (and some very good tips!) from the male customers.  

Well, back to Jimmy.  I had never dreamed that PJ Day would lead to Tammy catching the eye of the captain of the football team!  It was clear from the beginning that Jimmy was completely smitten with my little Tammy!  Some days, Tammy would get off work in the afternoon and go straight over to Jimmy's uncle's body shop and hang out there until Jimmy finished work.  And Jimmy was always asking Tammy to go out with him in the evenings and on weekends.  It all seemed innocent enough -- at least at first.  Tammy was thrilled with all the attention he was getting from Jimmy and how all the other girls from school were amazed that Jimmy and Tammy were "an item."  I had never seem Tammy so excited and happy as the times I saw him getting ready for a date with Jimmy.  He would spend hours getting himself all dolled up to look his nicest for his new boyfriend.  Sometimes he would try on dozens of outfits before settling on the one he would wear out with his new beau.

And Jimmy and Tammy did seem to have fun together.  Here are a few photos Tammy showed me of their time at the fair.  Just look how happy my little Tammy is.  And doesn't he look sweet in that little sundress he's wearing?  Jimmy certain seems to like what he sees!

 

The two of them spent a LOT of time together as the summer began.  There were dates to the movies and concerts, and trips into the city and lots of time on the beach. They really seemed to enjoy each other's company and seemed to be growing very close.

I know that the two of them would sneak off to be...romantic...together every chance they got.  My Tammy didn't even try very hard to hide it from me.  In fact, he loved talking about how being with Jimmy made him feel, how he loved being held tightly in Jimmy's strong arms, how he loved it when Jimmy would kiss him really hard.  But even if things seemed to be getting a little hot and heavy between them, I figured that they were just kids being kids and the experience of being together and exploring these romantic feelings wouldn't cause any harm.  And Jimmy seemed like a nice enough boy.  So I basically stayed out of it and let Tammy find his own way through this new terrain.

I was fine with all of it, really, until I overheard Tammy talking to one of his new girlfriends from school about something Jimmy called "sharing."

Mommy's Pajama Sissy -- Part 9

Tammy never shared with me all the details of his date with Steve. But it was very clear to me that Tammy had had an amazingly romantic and passionate evening.

But now Steve was gone, having moved to New York, and I could tell My Little Princess missed him, even though they had only been together on one exciting date.  But the last day of school was fast approaching and that was something good to look forward to.

At Tommy's high school, they have a fun tradition where the graduating seniors -- of which Tommy was one -- come to school in their pajamas on the last day of school.  Of course Tommy had never been one to get very involved in school activities.  He never went to football games or pep rallies or things like that. So I wasn't sure if he would even want to participate in Senior PJ Day, as they call it.

Well, he DID want to participate. And he wanted to participate in a very special way.

"Mother," he said to me. "I've been hiding all my girlish feelings from everyone for so long, always pretending to be someone that I'm not.  Well, tomorrow is PJ Day -- and it's the last day of school forever. So I want to go to PJ Day as Tammy.  The real me.  In a nightgown.  And if people don't like it, well fuck 'em!"

Tammy had never used language like that in front of me before.  It showed how strongly he felt about what he wanted to do.  So I gave him my full support.

Senior PJ Day arrived and we both got up extra early.  We took extra time getting Tammy ready for "her" very first appearance at Tommy's high school.  I warned Tammy that people would be shocked and that he would probably get some pretty strong reactions from people.  But Tammy was determined.

We hadn't discussed it before, so I asked Tammy, "So what exactly are you going to wear today.  Which nightgown have you chosen?"

Tammy replied.  "I have a favor to ask. Can I borrow your white night gown and robe set?"                                                                                  "You mean the one with the eyelet and lace trim? And the buttons down the front?  I haven't worn that one in years.  Well, I guess you can borrow it.  But, it's a bit...grown up and...romantic to wear to school."                                                                                                    "I understand. But it's what I want to do." And with that, I dug out the nightgown set from deep in my lingerie drawer.                                                                                           Tammy put it on and he looked absolutely stunning.                                                                               Ten minutes later I was driving him to school.  His hair and make-up were perfect. He wore just a bit of perfume.  As we pulled up to the front of the school, I asked one more time, "Are you sure you want to do this?"                                                                                             

 "I've never been more sure of anything." And off he went to the entrance of the school.

All morning I worried about My Little Princess being at school looking like a bride on her wedding night.  I kept me cell phone with me in case I got a call and needed to rush to school.  But no call ever came.  At 1:00, I drove back to the school to pick up Tammy, as the last day always ended early.

"How did it go?!?!" I asked excitedly as Tammy climbed into the car.

"It was great!" Tammy said with a smile.  And he proceeded to tell me all about his day. 

Mommy's Pajama Sissy - Part 2

When Tommy returned home from school the next afternoon, the first words out of his mouth were, "Mommy, can I dress up in your pretty pajamas?"

I will admit that I was surprised by how anxious and excited Tommy appeared to be to repeat last night's experience.

I told Tommy I would let him wear my pretty pjs as soon as he was done with his homework. Well, Tommy tore into his homework with a vigor I had never seen before.  After about an hour and a half, he announced that he was done.  I took him up to my bedroom where we picked out a light blue floral print set for him to wear.  I again sat him down at my vanity and fixed his hair and put a little make-up and perfume on him.  "There," I announced when I was done.  "Now you look and smell pretty."  He beamed when I said that.

He moved from the vanity to my full-length mirror, where for stood for nearly ten minutes, as he turned and struck various poses, mesmerized by his own girlish reflection.

I changed into my pajamas and we ate dinner together.  He chatted happily about his day -- something that he hadn't done with me for ages. Afterwards he helped me do the dishes without even being asked.  We watched tv together and generally had a wonderful time.

Our pajama fun continued every night. Each evening I would pick out a set of my pretty pajamas for Tommy and each evening he would race through his homework so that he change out of his boy clothes and into my ladies pajamas.  Over the course of that first week, I let him wear a pretty white set with red flowers, a black set with pick flowers, and a very sweet powder blue set.

Of course I knew this was a bit unusual, but it seemed to make him so happy.  And it also brought us much closer together.  He was so engaged and affectionate when he was wearing my pretty pajamas. I soon realized I was enjoying Tommy's unusual fixation with looking and feeling feminine as much as he was.

Mommy's Pajama Sissy -- Part 1

Last fall, shortly before Halloween, the weather turned suddenly very cold.  Our house is rather drafty so I wanted to be sure that my teenage son Tommy stayed warm.  But I then discovered that, over the summer, he had outgrown all of his winter pajamas.  Since Tommy and I were about the same size, I suggested to Tommy that he borrow a pair of my flannel pjs.  I handed Tommy a set that was white with a pale blue floral print.  I thought he might protest, but he didn't.

When Tommy emerged from his room wearing my pajamas, I could tell that his mood had brightened.  He went into my bedroom and stood in front of the big mirror, admiring his reflection. "Do you like those pjs, Tommy?"  I asked.

"Oh yes, Mommy.  I do.  I think they are very pretty," he said.  "Mommy," he continued hesitantly, "Do you think I'm pretty?"

"Pretty?" I responded with surprise.  "Well, I never thought about it, but yes, I suppose you are pretty."

He smiled.  "I want to be pretty.  Pretty like you," he said, still gazing at his reflection.

I was puzzled but also very touched by what he said.  "Well, maybe I can help you to be even prettier," I suggested.  I sat Tommy down at my vanity and started to brush out his hair.  His curly, dirty blonde hair hung down nearly to his shoulders.  As a boy, his long hair gave him a wild, surfer dude look.  But as I brushed it I realized just how pretty his hair was.  I gathered up some of his hair and pinned it up in back.  I brushed out a few tendrils and let them fall to the sides of his face.  I dabbed some pink gloss on his lips and brushed a little blush on his cheeks.  When I asked him if he wanted me to spritz him with a little cologne, he said, "Yes please, Mommy."

Tommy and I proceeded to spend a delightful evening together, both of us wearing pretty flannel pjs.  We snuggled up together under a blanket on the couch and watched tv together, something we hadn't done since Tommy was just a little boy.

That night, I even tucked Tommy into his bed.  He did indeed look very pretty, with his lips and cheeks pinked with my make-up and his brushed out hair falling across the pillows.  I kissed him good night on the forehead and he said, "Thank you Mommy."

As I turned off his light and closed the door to his bedroom, I wondered if this was going to prove to be a one-time event.  I suspected it would not be.

My Sissy Neighbor -- Part 9: The Real Anita

Over the next several months, Anita became more than just a pretty and competent assistant to my mom in her real estate business.  Anita was proving to be a valued partner to my mom.  Together they increased mom's book of business by 100%!                                                                                             Anita was living and working full-time now as Anita, a very attractive, young professional woman.  Here are some photos of Anita in full realtor-mode.  Look how poised and confident and relaxed he looks.  He was meant for this life and this career!

As for the matter of his real estate license, well obviously he aced the exam with no issue.  But there was still the matter of his name.  His realtor's license had to be in his legal name.  So mom took Anita down to the court house and helped him with the paper work necessary to officially change his name from Andrew to Anita.  While they were at the court house, Anita asked mom, "Is it OK if I change my last name too?"  Mom replied that he could do that if he wanted to.  "I want to have the last name 'Campbell'", Anita said.  Mom was shocked.  Campbell was our last name.  "You are my real family," Anita explained to mom.  "And besides, since I'm supposed to be your niece, wouldn't it make sense that we might have the same last name?"  Mom was so happy and so proud, that she started crying in the court house.                                                                                                                                                      "I'm so happy," mom said.  "And I don't think of you as my niece.  I think of you as my second daughter."  That made Anita cry when she said that.

Of course, by now I was away at college, so I missed mom and Anita a lot.  But I was able to come home every few weeks.  They were both always happy to see me.  When I would come home, Anita and I would typically sleep together in my bedroom -- slumber party!  I don't know if mom knew we were having sex, but I didn't care.  I needed to spend every possible minute with my beautiful Anita.

Anita was also getting a lot of romantic attention when I was away.  As I said, male -- and sometimes female -- clients were always hitting on him at work.  Mom had a strict rule about not socializing with "active clients."  But after a deal was done, mom said that Anita could socialize or date anybody he wanted.  Well I know Anita went on a lot of first and second dates.  But he had to avoid letting anything get to serious because...well it's obvious why.

My Sissy Neighbor -- Part 7: Sissy Anita's Date

The week seemed to go by very quickly and suddenly it was Sunday -- and time for Anita's date with the manager of Club Satin.  This guy obviously enjoyed using his position of authority to take advantage of the women who worked at the club.  And now the creepy manager had turned his attention to our Anita. And poor Anita was too frightened to turn him down.

Anita came over to our house around 5:00 to get ready as he usually does.  He had agreed to meet the manager at a trendy bar downtown for a drink at 6:30 and then they would go down the block for dinner.

Even though Anita didn't really want to go out on this date, he sure dolled himself in a way that any man would certainly find irresistible. Just take a look at the photo I took before Anita headed out for the evening.  He is so gorgeous!

As Anita was trying to get out the door to get downtown on time, mom was nervously giving him all the advice a mom could give a daughter going out on her first date -- "don't drink too much," "do you have some emergency money?" "call me immediately if you need me," and on and on.  It was very cute, but I think it was making Anita even more nervous.  Eventually, mom let Anita go and he grabbed his purse and car keys and headed out for the evening.

Mom and I waited up for Anita to get back home -- it was almost midnight when he got back.  Mom, of course, had been worrying herself sick. But we both sighed in relief when we heard Anita's car pull into the driveway.  But our fears returned when he walked in.  His hair and make-up were rather a mess.  I had never seen him looking so forlorn, so weary. Obviously something awful had happened on Anita's date.

"You poor, poor thing," mom cooed.  "Sit down here, dear, and I will bring you some tea. Now tell us what happened to you."

Anita described his evening. "It started out fine. The cocktail before dinner was fun and the restaurant was nice.  The manager was an OK date -- he talked a lot about himself which I guess all guys do.  He was pretty funny.  After a couple of drinks he got very, very flirty and...hands-y, but that wasn't so bad -- I get that at the club all the time. It was after dinner that things turned awful." Anita took a sip of his tea.

The manager, Anita explained, wanted them both to go back to his place.  Anita had tried to get out of it.  "I told him that it was late and that going back to his apartment wasn't a very good idea.  And besides, I told him, I'm having my period."

"Good girl!" mom exclaimed.

"But that didn't slow him down at all," Anita said.  "He claimed that he only wanted to go back to his place for one final drink and to talk a bit more. So I agreed. Stupidly." Tears started to well up in Anita's eyes. We waited silently for an eternity for Anita to go on.  Finally he exclaimed, "He forced me to give him a blow job!"

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 5: A Sissy Happy Ending

So that became our routine each night. Anita and I would make out for a little while after he came back from the club. And then I would help him change back into Andy before he went home. And when we were done kissing and cuddling, and while Anita/Andy was changing, we would chat.  I wanted to learn more about Andy's feelings about being Anita so we talked a lot about that. One night I asked, "I've read that some crossdressers get really...aroused by dressing up like women.  Does that happen to you?"

Anita answered a bit reluctantly, "Yes. And I don't mean just a little. The idea of dressing up and being Anita is very...exciting.  I'm sure this sounds weird but I get turned on just my seeing my reflection in the mirror. And I like it when men flirt with me and treat me like a pretty girl."  He paused for a moment. "And I really get excited when you kiss me while I'm still dressed as a girl."  That made me happy when he said that.

"How do you deal with getting so turned on?"

His face turned red. "I usually jerk off as soon as I get home at night."

"Oh, I see," I replied. I thought for minute. "Wouldn't it be much more fun if you did that here, while you're still dressed up and can see your reflection in the mirror?" He couldn't believe what he was hearing.  Then I really blew his mind.  "I could help."

"Get undressed from the waist down," I instructed. I went into the bathroom and brought back a bottle of hand lotion and a towel. "Scoot over," I said and sat down next to Anita on the little vanity bench. 

I could tell he was frightened. "I've never done this before," he whispered.

"Don't worry," I said, "I've done it lots.  Now just look at yourself in the mirror and try to relax." Anita took a deep breath and stared at his gorgeous, sexy reflection in the mirror.

I put some lotion on my hand and wrapped my fingers around Anita's penis.  It was much smaller than other guys' dicks (I guess I get around a bit -- don't tell mom!). It sprang to rock hard attention with just a couple of strokes.  Then I whispered into Anita's ear, "You are a very beautiful woman."

And when I said that, his cock completely exploded!  It was like a semen fire hose! And it happened so fast I didn't have time to get the towel out.  Anita's cum went flying everywhere -- all over the vanity, the mirror -- it was crazy! I had never seen anything like that before.

Anita started apologizing almost immediately about the mess he had made. I just laughed and kissed him and told him it was alright. "My, my," I said. "It looks like you really needed that." We both had a good laugh.

It was late so I mopped up Anita's cum from the vanity and the mirror, then helped him get changed back into Andy as quickly as he could.

And this became another part of our nightly routine -- a little kissing and cuddling -- and a very happy ending for Anita. 

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.

My Sissy Neighbor -- Part 3: Sissy Works Hard for the Money

Anita makes a lot of money working at Club Satin.  He works there during their peak hours 7:00 to 11:00pm, Tuesdays through Saturdays.  And nobody -- nobody -- knows Anita's secret.

He and another hostess are responsible for greeting guests -- 99% of whom are men -- and showing them to their tables.  Whenever there is a lull at the front door, the hostesses take turns walking around the club, checking on all the tables.  It starts with a simple "How is everything here?  Do you have enough drinks?  Is there anything else I can get for you?"  But Anita and the other hostess are well practiced in the art of moving from there to more chatting and flirting with the male guests.  The hostesses are often invited to join the men at their table and to have a drink.  This is strongly encouraged by the manager as it makes a lot of money for the club -- and it earns Anita and the other hostess extra tips for the evening.  


Sometimes the men get drunk and little frisky.  Anita's butt gets grabbed probably a hundred times per night.  And when a drunk asks Anita to sit on his lap or to kiss, Anita has a standard answer ready, "Sure, for $100!"  You'd be surprised how many men, having had too much to drink and wanting to show off in front of their friends, are willing to pull out a $100 bill.  Anita doesn't disappoint -- a deal is a deal.  He jams the bill into his bra and climbs onto his customer's lap.  He wraps his arms around the stranger's neck and gives him a deep, long, French kiss.  









Just imagine this luscious creature climbing onto your lap, looking deep into your eyes, and pulling you close to them.  Just imagine feeling her soft round bottom on you lap, smelling her perfume, touching her silky hair.  Just imagine how you would feel when this gorgeous woman closed her eyes and parted her lips to give you an amazing, deep, wet kiss!  Anita must drive the men crazy!

And just imagine how you would feel if you then found out that this angelic creature was really a boy!  Wow! Well, no need to worry about that because no one knows Anita's secret.

My Sissy Neighbor -- Part 2: Seeing is Believing

After seeing Anita's photo, I'm sure most of you don't believe that Anita is really Andy.  But it's true.  I swear.

I told you that Andy comes over to our house around 5:00 in the evening.  Mom has turned the spare bedroom into "Anita's Dressing Room."  Anita's clothes and shoes and stuff -- and there is a lot of it -- fill the dresser and the closet. Mom found an old vanity table and a cute upholstered bench at a tag sale. She also bought a really good lighted make-up mirror for Anita.










When Andy arrives, my mom always greets him with a big hug, knowing that his own parents are such losers that he gets no affection from them. She then brings him a cup of tea to the dressing room and Andy begins to transform. Sometimes I like to sit in the room with him while he does his make-up and gets dressed.  It's amazing what he can do.  Here are some photos I've taken of Andy changing from boy to girl.

Here you can see how he's already done his eyes and eyebrows and is starting to do his contouring. You can see his hair is still pulled back the way he wears it to school.  Without his make-up on you can see how young he really is.  But with his make-up on he looks so much older and more sophisticated.  Andy told me that the manager at Club Satin believes that Anita is 26 years old.  But as you can plainly see, he is much younger than that.












The contouring he does is super complicated but it is really effective.  I've been trying to learn to do this myself, but I'm not nearly as good at is as he is.  And his finished look -- dramatic, sultry, glamorous -- is perfect for working as a hostess in a dark night club. 




And then his is nearly done.  He uses some light powder to achieve the finishing highlights.  Then he brushes out his hair and -- finally -- puts on his lipstick.  When he's done there is absolutely no sign of Andy -- only Anita.  He puts on his bra and padding, his jewelry, his outfit for the night and his 5 inch high heels.  And then he heads out into the night to his life as a night club hostess. 


He is so beautiful! 

My Sissy Neighbor -- Part 1

Andy has lived next door to me ever since I can remember.  We've been in the same grade and attended the same schools since kindergarten.  Andy has some big secrets that only my mom and I know.

Andy has always been...different.  I have known that he is a sissy for many years.  When we were little, he used to come over to my house almost every day after school.  He never wanted to play boy games or run around outside. Instead he loved staying inside with me, playing with my Barbies together, having tea parties with me and my stuffed animals, playing dress up in my mother's closet -- that sort of stuff. To me he was just like a sister and best girlfriend all in one. My mother saw all of this.  She was concerned about Andy and his sissy tendencies. But she was more concerned about his home life.  Andy's parents were a mess -- his father unemployed and abusive and his mother a big drinker.  There was always a lot of yelling going on in their house. Mom was happier when Andy was at our house.  At least she knew he was safe and felt cared for here.

As Andy got older, to other kids at school he just seemed to get weirder. When we got to high school, he had let his hair grow long and even partially bleached it.  He was also incredibly skinny and his clothes were all black and goth. He usually kept the hood of his black sweatshirt pulled up over his head.  And even if you did see he long hair, he kept it pulled back in a sloppy pony tail in a way that made him look more like a rocker than a sissy. He really kept to himself; he didn't have any friends except for me. The other kids thought that he was so odd that they didn't even bother to tease him. But I knew he wasn't so strange. He just had a secret life that he wanted to protect and being a loner was the best way to do it.

You see, almost every night, Andy disappears and his alter ego, Anita, comes alive.

Andy has told his parents that he works as a dishwasher at a restaurant on the other side of town six nights a week -- Tuesday through Sunday.  They don't bother to check up on him and since he contributes the $300 every week to help pay for the family's rent money, no one complains.  But Andy doesn't wash dishes at a restaurant.  Andy, or rather Anita, is one of the hostesses at Club Satin, an expensive "gentlemen's club" downtown. And he doesn't earn $300 per week. He earns about $1,500 every week.  It's true.

And when he's all dolled up at Anita, no one would ever know that "she" is really a "he."  I mean, just look at this photo!  He's incredibly beautiful as a girl!

How does he do this with no one else knowing?  Because my mom and I help him.  He leaves his house around 5:00 in the afternoon and drives his beat-up used car over to my house where he pulls into our garage. He then takes the next hour or so changing from Andy to Anita.  And he is absolutely amazing with make-up and his hair. He keeps all his supplies at our house: his make-up, his dresses and shoes, his bras and panties, his jewelry, his padding for his hips and boobs, the works.

His ratty pony-tail gets combed out into a pretty style that just brushes his shoulders.  His lips are crazy full and sensual.  He eyes look huge and sexy underneath his heavy false eyelashes.  Then around 6:00, when he is ready to head to work, he lets mom and me admire the finished product.  We are always incredibly complimentary about how pretty he is.  I know he likes hearing the support especially from my mom.  She tells him to "be careful" every time before he gets back into his car and drives to the club. 

A Boyfriend for my Sissy Husband -- The Conclusion

By the time Danielle woke up, it was already dark out.  His eyes were blurry and his head -- and his ass -- hurt. A lot. He managed to read the clock on the end table and it said 9:25!  Danielle had told is wife that he would be home by 6:00! He had been asleep for several hours. What had happened?  Danielle fumbled for a light switch.

"Martin?  Martin?  Where are you?  Did you know it is after 9:00?  I really need to get home now.  My wife is going to kill me!  Martin?"  But Martin was nowhere to be found.  Martin was long gone Danielle had slept because Martin had crushed several Ambien tablets and put them in Danielle's champagne.

Danielle ran to the bathroom and looked in the mirror.  He looked awful.  His make-up and hair were a total mess.  And there was Martin's cum caked on his face and in his hair.  "Martin!  Where are you?" he wailed again.  He looked for his purse so he could at least comb his hair and fix his make-up but he couldn't find that either.

But he did find an envelope propped up against the champagne bottle with "Danielle" written on it. Danielle opened the envelope and pulled out the letter inside and started reading it:

Dear Stupid Sissy Slut --

By the time you read this I am long gone.  How does it feel to have my semen drying deep inside your sissy ass-pussy and in your throat and on your face?  Does it feel like you've been used as a worthless sissy cum bucket?  It should.  Because that's exactly what you are.

I made you tell me that you loved me. You shouted it while my dick was up your ass! But I want you to know that you meant nothing to me.  You are just a weak, worthless sissy bitch.  Your only value is as a place for real men like me to leave our sperm.

I can't believe how easy you were to manipulate.  You believed every word I said.  I have never met anyone more stupid or more gullible in my entire life.

By the way, I took you purse and your phone.  And I took back the diamond heart necklace.  I will give that to someone I actually care about.

Good luck checking out of the hotel -- the front desk is expecting you to pay.  The room cost $950. I'm not sure how you will handle that without your purse, but I don't really care.

I am sure that you will never forget me.  But I want you to know that I have already forgotten everything about you.

Martin

Danielle had to read the entire letter twice to begin to comprehend what it was saying. And when it sank it, he began to cry.  And cry. His feelings were crushed. He collapsed to the floor, sobbing so hard that he struggled to breathe. His heart was broken and he felt like such a fool and such a failure. Martin's letter was right -- he was just a worthless sissy bitch.

The crying continued for some minutes but as his thoughts cleared, Danielle began to focus on some practical problems he had like getting home and paying for the hotel.  There was no choice but to call his wife and have her come rescue him. So that's what he did.

"Where the fuck are you?" I screamed into the phone when he called.  "You said you would be home at 6:00 and now it's nearly 10:00!  Where are you?"  I was really enjoying this.

Danielle confessed that he wasn't really downtown but instead at the Inn on the Pier and I responded with well rehearsed surprise.  Danielle had to spill everything -- his lying to me, the diamond necklace, having sex with Martin -- everything.  My anger in response was volcanic and Danielle had no defense.

I took my time driving down to the lake and picking him up.  He looked absolutely awful!  His hair was a tangled, gooey mess and his make-up was smeared. Mascara was running down his cheeks from all the crying. The girls at the reception desk couldn't help but giggle when they saw Danielle, a total train wreck, walk through the lobby. I paid the room charge which gave me yet one more stick to beat Danielle with. I had purposely parked my car several blocks away so Danielle could enjoy a nice long "walk of shame" down sidewalks crowded with people out for Saturday night.

Danielle cried and cried the whole way home.  The poor little sissy must have been near total emotional collapse with the combined effect of his extreme heartbreak and his total humiliation.  He repeatedly blubbered about how sorry he was. I remained shocked and furious -- even though he had done everything exactly the way I had hoped he would.

Danielle's waterworks had mostly subsided by the time I pulled the car in the garage.  I turned off the engine but before getting out of the car, I said to him, "You know, Danielle, you have truly disappointed me in so many ways.  Your little "affair" -- and especially your lies to me -- have changed everything. I have made a decision. From now on, you may continue to live here, serving as my maid, keeping the house spotless, making my meals, doing my laundry -- everything -- but I do not want to have to see or hear you.  Ever!  You will do your chores when I am asleep or out of the house or in our -- I mean, my -- room. Otherwise, when I am home, you are to become invisible. You will stay in the storage room in the basement, as quiet as a church mouse. That is where you will live starting immediately. And this is how things will be until -- and if -- I decide that things will change. Do you have any questions?"

The totally defeated little sissy just shook his head. "I can't hear your head shaking. I asked you if you have any questions?" I said with anger welling up in my voice.

"No, Ma'am.  No questions." my sissy whispered meekly.

Then I exploded on him, slapping him violently across the face until my hands hurt. "I told you that I don't want to hear you! What part of that didn't you understand!?!" I was screaming out loud but laughing inside.

The poor confused sissy just bowed his head in total subservience demonstrating that he understood.

"I'm going to bed now. After I'm upstairs you can get out of the car. In the morning after I leave for the day, you can move your things out of the master bedroom and into the basement."

And then for the coup de grace. "Since you were unfaithful to me, I have decided that I am going to have an affair of my own."  Whatever color was left in Danielle's face drained away immediately.  He was devastated. I had succeeded in completely breaking him!  I had restored the proper balance to our dominant wife/submissive sissy husband relationship.

I smiled as I thought about Danielle's diamond heart pendant, hidden from view, hanging between my breasts.  Just imagine how Danielle will feel when he learns that I am going out with Martin next Saturday night!

A Boyfriend for my Sissy Husband -- Part 1

There comes a point in the development of every sissy when you need to introduce men into the equation.  I realized this about a year ago regarding my own sissy husband. Danny -- or Danielle -- has always been a loving husband. But at home when we are alone together, he is also a totally submissive, feminine -- and very pretty -- sissy.  I don't mind.  If he wants to dress up in a frilly French maid outfit and wait on me hand and foot, why not? I learned to enjoy my role as a dominant -- a lot.  For him, the fantasy was complete; he was fulfilled by being my feminized servant, wearing high heels, make-up and dresses -- and enduring my abuse.

But I realized the fantasy wasn't complete for me.  I wasn't fulfilled.  My domination of him was beginning to feel tired and unoriginal.  What's the point of being a dom if your sub enjoys every minute of the experience? I needed to take this to another level.  And to do that, Danielle would need a man.

When I say "a man", I don't mean some casual grouping or kissing in a bar. Every dom makes her sissy do that stuff.  No, I'm talking about sending your little sissy on an emotional journey that will positively crush him.

First, I needed to find a man for my sissy.  If you think it might be hard to find a boyfriend for your sissy, forget about it!  It took me about 15 minutes on the Internet to find about a dozen promising candidates for the job of Danielle's lover.  I interviewed several and selected one man that I thought would be perfect.   He was tall and masculine, very fit and muscular.  He was older and looked and acted like the rich and powerful executive that he is. His voice was deep and his eyes were dark and penetrating and he had an air of power and confidence that felt very manly.  I might have slept with myself but I reminded myself that this guy was for my sissy.  Most importantly, he was willing to follow my instructions and thought my little "game" would be fun.

When I told Danielle that I intended to introduce him to a man, Danielle nearly had a fit.  "I'm not gay!" He protested. I slapped him hard for raising his voice to me.  But then I regained my composure and answered, "Of course you're not, dear. But you are a pathetic, submissive, girly sissy. And little sissies like you need to have the experience of being with a real man, to help you fully realize how weak and pathetic and submissive you are. So you will go out with whoever I select for you and you will behave like the total sissy girl you are. And in the end you will better understand who you are and what your purpose in life is."

Danielle was close to tears but he knew he was powerless to fight back. "And the best news," I cheerfully announced, "is that you are going out on your first sissy date on Friday night!" Danielle had no idea that I had already made all the arrangements before I even mentioned the idea!

After he regained a bit of composure, Danielle asked me, "Does he know that I'm...I'm...I'm...not really a girl?"

"Of course he knows you're a sissy," I answered. "He's really into sissy girls like you so you have nothing to worry about." But of course, Danielle did worry -- he nearly worried himself to death. He was positively dreading being sent out on a date with a strange man!

Danielle was a nervous wreck all week. We spent hours going through his wardrobe and selecting his outfit for his first date. I talked endlessly about what to expect on his date, dos and don'ts, and on and on. The more I talked, the more anxious he became.

When the big day came, Danielle spent most of the afternoon at the beauty salon getting the works done -- hair, nails, make up, waxing -- everything.  The girls at the salon teased him mercilessly about going out on his first date. Poor Danielle was growing more terrified by the hour. But when 7:00 arrived, my Danielle looked so pretty.  His hair and make-up were perfect. He looked so elegant in a pale gold outfit I had bought for him. The top was gathered at the neck and showed off his pretty, delicate arms and shoulders. I even let him borrow some of my gold jewelry to complete his outfit.

Danielle's "date", Martin Rittenhouse, showed up right on time. I ushered him in to meet Danielle and Martin gallantly greeted Danielle with a little peck on the cheek. Even through his make-up I could see that Danielle was blushing. Martin was the perfect gentleman -- so charming and so handsome in a charcoal suit.  Martin told Danielle several times how pretty "she" looked and how delighted he was to be with "her."  I could tell the Martin was already having an effect on Danielle; he was weakening before my eyes by the attention and compliments of this very handsome and masculine suitor.

So off they went on their date!  Martin drove them to Chez Printemps, a very fancy restaurant downtown where he had made reservations.  Martin, of course, gave me a full report afterwards.  Martin treated Sissy Danielle like a perfect lady all night long -- pulling out his chair, ordering for him, the works.  He kept the conversation light and interesting.  Danielle was mesmerized by the entire experience -- just as I wanted him to be.  When the second bottle of wine arrived and Danielle had loosened up a bit, Martin started seriously flirting with Danielle. Martin even reached across the table to hold Danielle's hand.

On the walk back to the car after dinner, Martin kissed Danielle.  And once they were in the car they started making out like crazy. Apparently, Danielle really got into it! 

Before returning Danielle to our home, Martin asked him for a second date, just as we had planned.  Danielle said yes.

When Danielle walked inside, I was waiting for him in the living room.  I could see that Danielle was on Cloud 9 -- a bit tipsy from too much wine and overwhelmed by the wonderful experiences and feelings of the evening.  I made Danielle tell me every detail about his evening out.  He was very embarrassed talking about making out with Martin but I got the truth out of him.  He was even more embarrassed when he told me that he had agreed to go out on a second date with a man.  Most of all, he was embarrassed to describe the whirlwind of feelings that were coursing through him.  When I was satisfied that Danielle had verbalized everything he could about his evening, I summed it up for him. "Well I guess this really does prove what a total femme sissy you really are."