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!