Thursday, May 26, 2016

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. 

Wednesday, May 18, 2016

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.

Thursday, May 12, 2016

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.








Thursday, May 5, 2016

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! 






Saturday, April 23, 2016

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. 

Sunday, April 10, 2016

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!