Thursday, August 18, 2016

My Sissy Neighbor -- part 10: Anita's Evolution

Anita was now living and working full-time as a woman.  His name was legally "Anita", and socially he was becoming more female every day.  Because he is so beautiful and charming, men are always asking him out for dates.  Anita sometimes accepts, but has to limit the intimacy because he is not at all what his suitors think he is.  But all of that is beginning to change!  Anita told my mom that he wants to become Anita permanently and physically, meaning that he decided to start hormone treatments and to start planning for surgery to become a real woman!  Isn't that exciting!
These are some photos mom took of Anita before going out on one of his recent dates.  In these photos, Anita has been on hormones for just a couple of months.  But doesn't he look different already?  I mean, he was already beautiful, but somehow the hormones are having some kind of effect on him in ways I can't explain.  I think he is incredibly beautiful.

Tonight, Anita is going to a charity ball on the arm of a handsome young (and successful!) banker who has taken quite an interest in our Anita.  Anita's gown is long and sparkly.  It clings to his every curve.  And soon enough, those curves are going to be Anita's own body, not carefully placed silicone pads.  Every eye at the ball will be on Anita, I'm sure.

Anita hasn't yet had surgery, but he has become a real woman as far as I'm concerned. "He" is really now a "she."

Wednesday, August 10, 2016

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.

Sunday, July 24, 2016

My Sissy Neighbor -- Part 8: Transition to New Life

Mom and I did our best to help Anita settle down after his horrible ordeal.  Mom wanted him to go to the police, but I knew he wouldn't agree to that.

"Well, at least you are NEVER going back to that awful club."

"But I have to!" Anita wailed.  "I need the job if I ever want to move out of my house!  I can't stay there anymore.  Things are so bad with all the yelling and drinking and..." Anita took a deep breath and continued.  "I think my dad is beginning to figure out that I'm not exactly the man he thinks I should be.  And if he ever figures out about Anita, hell kill me.  I mean it!"

He continued, "I've been saving up my money so I can move out of the house.  Maybe I will move to California."

Mom and I stared at each other for a moment and then said -- in unison, "Just move in with us!"

Anita looked confused for a moment and then said, "But I can't move in here.  I don't want my parents to know I live just next door.  That won't fix anything."

Mom spelled it out for him.  "Move in with us as Anita.  Let your parents think that Andy has gone to California or Timbuktu or where ever.  Graduation is in just a few weeks.  Stick it out until then.  Then say 'so long' to your folks, pack up your car and start the long drive -- to the house next door!"  Mom seemed very pleased with her solution.                                                                                                         "But, my parents will recognize my car," Anita protested."Sell it.  Get a new one with all the money you saved up." Mom replied.                                                                                                                                                      "But what would I do all day as Anita?  I've never lived full time as Anita before," he noted.
"Well..." mother replied, "I could use help with my real estate business,  Things are really booming.  And my own daughter has no interest in real estate." She was referring to me, of course -- and it was true. She continued, "Besides, she's heading off to college in just a couple of months."                                                                                            We talked about it for a long time into the evening and Anita finally gave in to mom's proposal.  A lot of things happened over the next few weeks. Let me fill you in:
Andy graduated and told his shitty parents that he was moving out.  He dropped his few belongings at our house and then traded in his awful car for a really nice used Audi A4 sedan.  It was definitely the car Anita belonged in.                                                                                                     Anita started helping mom out with her business, handling some simple phone calls, making appointments, sometimes signing-in people to open houses.  Here are some photos of Anita that mom took during Anita's first few days showing houses.  Mom noticed right away that Anita was a natural at this.  Anita can talk to anyone -- a skill he honed at the club, no doubt.  And of course, being gorgeous didn't hurt either -- especially with the male customers.  But mom noticed even the female clients seemed intrigued by and drawn to him.  Mom started giving Anita more and more responsibility.  And by the time I went off to college in late August, Anita was studying for his realtor's license.

And for me, the best part of the summer was having Anita living with us full-time!  We kept it quiet from mom, but we found lots of time for our little make-out and hand-job sessions. One day Anita asked me to show him how to eat pussy.  I was more than happy to let him practice on me!  And he was a natural!  I have never cum so hard or so many times in my life. It was such a turn on to see that beautiful blonde hair of his between my thighs; feeling those full, lip-stick coated lips and his very talented tongue go to town on my pussy.  It was the best summer of my life!                                                                                                                   "Anita," mom said one evening before they sat down to dinner.  "We need to talk."  Anita was concerned by mom's unusually serious tone.  "Anita, you are doing a great job helping me with the real estate business.  I am so impressed by how mature and professional you are.  And I know you are going to ace the real estate license exam."   Mom took a deep breath.  "But you can't be a realtor and sell real estate under a false name.  You have to use a real name -- on your license, on your business cards, everything."                                                                                                                           Anita turned pale.  His dreamy new life as beautiful Anita, as a young professional woman starting out on a real career, seemed to have crashed.  "But I can't live like this and call myself Andrew for goodness sake."                                                                                                          
"Of course not," replied mom. "So maybe this is the right time for you to say good-bye to Andrew and become Anita.  For real.  Legally, and if you want, surgically." Oddly, this suggestion came as a surprise to Anita.  Anita sat in silence as he thought about what mom had suggested.  And then mom added brightly, "And then you can be my niece for real!"

Monday, June 20, 2016

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!"

Sunday, June 12, 2016

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!"

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.