Saturday, December 31, 2016

Never too Late for Sissies

I often hear wives say, "I wish I had feminized my husband years ago. Now it's too late."  That is nonsense! It is never too late to feminize your husband. Just look how lovely Sissy Jessica is in his bikini!



Mary had been married to Jeff for over 20 years. Mary knew Jeff was a crossdressing sissy, but she didn't mind. She enjoyed having a husband with a feminine side who listened to her, doted on her, enjoyed shopping with her. But as Jeff experienced some set-backs at work and was starting to consider early retirement, Mary decided it was time for some changes in their lives. Mary decided that they would both be happier if Jeff took his sissy-ness to the next level and became a woman full-time -- or at least a sissy version of a woman.











Jeff resisted at first.  But that's the good thing about sissies; they have no spine and no ability to push back. So in the end, Jeff did exactly as Mary ordered and became Jessica.  And weren't the results fabulous!  Jessica looks ten -- maybe fifteen -- years younger than Jeff did when his transition began.  And look at him now!  He looks totally hot as a woman, even in a skimpy bikini.

















But Mary wasn't done yet. She also decided that both she and Jessica needed to have real men in their lives. Jessica was horrified -- distraught -- by Mary's suggestion.  Jessica cried and protested but to no avail.  Mary got her way as always.  



It was easy for Mary to find countless older men online who wanted to have a sissy of their own. She eventually selected Terrence, a wealthy divorced businessman, for Jessica.  Mary arrange all the details for their first meeting and subsequent dates.  It worked out perfectly. Once in the presence of a real man, Jessica easily and naturaly slid into the role of the woman in the relationship.  That was eighteen months ago. Now Jessica is embarking on the next exciting chapter of his life -- as Terrance's wife. That's right! Jessica and Terrance got married last month and those bikini shots were taken on their honeymoon!



















Jessica is in heaven being the pretty, obedient and subservient housewife for his husband.  You can see how happy he is being feminine and domesticated and servile to a real man.  He spends hours every day making himself pretty. He derives total fulfillment by being the object of his man's desire -- and by satisfying that desire with every part of his feminized body.















Tonight, Jessica and Terrance are having a double date tonight with me an my new boyfriend.  Jessica is making dinner for all of us -- for his husband, for his ex-wife that feminized him and for his ex-wife's lover!  Could there possibly be a greater expression of what it means to be a total sissy?

So my friends, as you see, it is never to late to help your sissy fulfill his destiny!






Saturday, December 17, 2016

Taking Delivery of My New Sissy -- Part 2



I kept my spent dick in my sissy's mouth until it started to go limp.  Sissy Gwendolyn expertly and eagerly cleaned every drop of cum off of it with his well trained tongue.

"Take off your top," I directed.  "I want to see your titties."  My new sissy obediently did as his master instructed.  

"Now I 'm going to fuck your pretty little sissy ass-pussy.  How do you feel about that?" I asked.

"Oh, please, please, please ram your enormous cock up my sissy-pussy," my new sissy pleaded desperately.  My dick sprang to attention once again.  I was going to fuck the shit out on this sexy sissy plaything.

As my new Sissy wiggled out of his sheer black lacy top, I was able to admire just how perfect and feminine his little sissy body was.  I took a moment to drink in his long skinny legs, his pale, soft skin and those incredible titties.  The room had mirrors everywhere -- even on the floor -- so I could enjoy the sight of my new plaything from several angles at once.  This was the best moment of my life.
















Just look at my perfect Gwendolyn in the picture to the right.  I did fuck him right there.  As I fucked him he started crying, either from the pain of my giant cock up his tight little ass or from the humiliation of being another man's sex toy.  I smiled at the thought that both were true. I must have dumped a gallon of my hot sticky cum in his ass!


And then it was time to take my sissy home. While Sissy Gwendolyn and I were getting acquainted, Ms. Trainer's staff had move Gwendolyn's few possessions into my car.

"Would you like us to dress him before you take him to your car?" one of Ms. Trainer's assistants helpfully offered.

I thought for a moment.  I knew there was a heavy snow falling outside and a bitter cold wind.  "No thank you," I replied.  "He can walk out to my car dressed exactly as he is."


Saturday, December 10, 2016

Taking Delivery of My New Sissy -- Part 1



Yesterday was the happiest day of my life. You see, I took possession of the new Sissy I had ordered from Ms. Trainer's Feminization Service. When I set eyes on my new Sissy boy, well my heart nearly stopped beating -- and my great big dick got instantly hard! 


When I arrived at Ms. Trainer's I was led into a private reception room where my sissy was waiting for me.  He was patiently kneeling on the floor, his skinny, frail little body barely concealed by a flimsy, sheer black lingerie set.  I thought he looked like a little angel.  His skin was pale and soft, his face was made-up perfectly, and his perfect titties were visible through his sheer lacy blouse.
I had gotten addicted to sissies about 5 years ago after my second wife left me.  I never had much luck with women.  They won't tolerate my abusive behavior and my insatiable need for sex. That's when I started hanging out at tranny bars and picking up sissies for one-night stands.  It was easy and I could treat them like shit -- and they seemed to enjoy it.  But I grew tired of the bar scene and the drag queens that I was having sex with weren't doing it for me any more.  

That's when I learned about Ms. Trainer's Service.  For an enormous sum of cash (don't worry, I'm rich) Ms. Trainer said she could provide me with a trained, transformed sissy that would meet my every requirement.  Well that's what she did and she exceeded my expectations.

My new sissy is simply gorgeous.  At first I couldn't take my eyes off his perfect little sissy body.  But then I noticed his big, beautiful hazel eyes.  I was entranced.  I knew I had found the sissy of my dreams!




"Your new name is 'Gwendolyn'," I announced.  "And you shall call me 'Daddy'.  Or 'Sir'  Any Questions?" 

"No questions, Daddy...Sir," my new sissy answered immediately and meekly.

"Good," I responded.  "Now, tell me about yourself.  Tell me where you come from and how you came to be here," I asked.

Sissy Gwedolyn seemed surprised by the question at first but after a moment started to answer.  "Well, Daddy, Sir," he started.  "I was born in a town outside of C..."

Before Sissy Gwendolyn could even start his first sentence, I slapped him hard across his pretty sissy face. "Nobody cares about who you were or where you came from," I snarled.  "As far as we are concerned, your entire life started today, right here, when you met me. I am your life.  I am everything.  Beyond me there is nothing.  And without me, you are nothing.  Do you understand?"

"Yes, Daddy Sir.  Yes, yes, I understand.  Please forgive me.  I am so sorry.  That will never happen again," Sissy Gwendolyn managed to blurt out knowing that he had badly transgressed.



"Now suck my dick," I commanded.  Sissy Gwendolyn did exactly as directed. As he unzipped my pants and pulled down my briefs, he gasped -- either in admiration or more likely terror -- at the size of my monstrous cock.  He quickly regained his composure and focus. He pulled his pretty shoulder length hair back away from his lovely face and went to town on my cock.  My new little sissy knew exactly what he was doing in the cock sucking department!  He kissed, licked and sucked my rock hard dick until it exploded in his pretty little mouth.  He eagerly swallowed every single drop of my cum as if it were the most expensive and delicious champagne in the world!



Sunday, September 25, 2016

My Sissy Neighbor -- The Conclusion: Honeymoon

A lot of time has passed since my last post.  And a lot has happened for my sissy sister, Anita.  The biggest news is that Anita got married!                                                                                                                                                     A very handsome, divorced lawyer (his name is Jackson) was looking to buy a home and Anita became his realtor.  One thing led to another, and before long, they were dating.  Six months ago,  Jackson proposed to Anita, giving her the biggest, most beautiful diamond ring I have ever seen!  Of course Anita said yes!  Here are some lovely photos from their "Engagement Shoot."  Isn't Anita exquisite?
 The wedding was intimate and lovely. I was the Maid of Honor and of course mom was the Mother of the Bride!  And, as you would expect, Anita was the most beautiful bride ever!!!





Here are some photos from their honeymoon in Hawaii that Anita posted.  Here she is in a lovely black and white print dress that I helped her pick out.  Anita loves how this dress shows off her every curve.  Of course, she isn't wearing a bra underneath a dress like this.  I'm sure that Jackson is so pleased to have snagged the gorgeous Anita to be his bride and to have this lovely creature hanging on his big strong arm as they stroll around this tropical paradise. And Anita told me all about the hot sex they had during their honeymoon.  Apparently, Jackson has quite the sexual appetite -- and the equipment to go with it!  Anita said their honeymoon was a continuous round of eating, drinking, dancing, swimming and fucking!   



And here's Anita lounging by the pool. She loves putting her crazy curves on display in her sexy swimsuits. She knows that every guy around the pool can't take their eyes off of her -- even when their wives and girlfriends are right there!  Just check out Anita in her blue one-piece.  It can barely contain her giant boobs!  I love it! 

I am so happy that my sissy neighbor has found her new life as a successful business woman, a beautiful, voluptuous lady, and a devoted and loving wife of a handsome man. It has been a wonderful experience for me watching this amazing transformation and journey. And through it all I guess I lost a sissy neighbor and gained a sister. 





Monday, August 29, 2016

My Sissy Neighbor -- Part 11: Some BIG Changes

As you know, Anita decided that it was time to become a woman for real.  Anita had been living an working as a female for some time very successfully.  But he made up his mind; he wanted his body to finally match the woman he was inside.  One important motivator was his love life.  Anita was attracting the attention of lots of very desirable men -- but Anita could never let a relationship develop because "he" was not really a "she".  Yet.

The process took some time.  Anita had consultations with several doctors.  He started hormones.  And several months ago he took the plunge and had the complete operating -- top and bottom, if you know what I'm talking about.  There was a tiny amount of facial surgery, but since he was so pretty already, this part was very minor.



Anyway, I was somewhat surprised -- and delighted -- when I realized some of choices Anita made.  Most obvious was his chest!  He opted for really big boobs!  And they looked great on him.  And now that he has these killer tits, he just loves showing them off.  Just look at some of these photos!  These are just two of the dresses he bought recently that put his tits on full display for everyone to see.































I was so impressed with Anita's new boobs that I decided to have a boob job too!

And Anita's dick is long gone too.  No more late night hand jobs for my sissy neighbor.  But we still see each other a lot and usually sleep together in the same bed when we're together.  But now we're not secret lovers.  We're sisters.  Although I will admit that when we are alone together getting ready for bed, I can't take my eyes off of her amazing body as she gets undressed.  I think she knows I enjoy looking at her; she always takes her time and ensures that I have a good view as she gets dressed and undressed.







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. 

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!