A Reluctant Sissy -- Part 4 - Going into London

I was now getting updates from Mrs. Trainer every couple of weeks regarding my son's feminization transformation.  The latest letter read as follows:

"Dear Mrs. _____, 

Now that our most recent crop of sissy students has been with us for a couple of months, we have added a fun new activity to their schedules.  Every two weeks we get our little sissies all dolled up to spend a fun day in London!  It is so much fun dressing our sissy boys up in the cutest little outfits and to spend an entire day putting them on full display in the busy city.

There is so much to do in London; we usually start our day at a chic salon where the sissies can get their hair and nails done.  The ladies at the salon really enjoy working on our naughty boys and ensure that they all look their very prettiest for the rest of their big day out.  We usually do some shopping for dresses and pretty things at a few boutiques or one of the wonderful London department stores.  Then it's off to downtown (we call it "The City") where we go for lunch at some restaurant crowded with handsome young businessmen.  There is a lot of ogling and leering going on as our sissies try their hardest to ignore all the attention they are getting.  Sometimes a brave young banker will approach one of our tables and try to flirt with one of our boys.  It's very upsetting for our sissies to realize that they have been so feminized that they have become the objects of desire for real men!"

I stopped reading for a moment to take a look at the photos that Mrs. Trainer had included.  My heart nearly stopped when I saw the first photo --  my son in a pretty yellow cardigan, chicly belted around his skinny waist. And this was over a blue polka dot pleated skirt that fell just below his knees.  This was finished with towering pair of open-toe pumps and the same oversized pearl jewelry I had seen in earlier photos.  He looked simply amazing.  So stylish.  Simply gorgeous.  But as always, that naughty boy refuses to smile for the camera!  

I continued reading:

"Our day might include a ballet matinee or high tea at a fancy hotel.  You know -- all the things real ladies love to do.  And our sissies are expected to demonstrate their best behavior and participate enthusiastically in whatever activity we dream up for them.

Of course, your darling Kimberly is so very pretty that he attracts a lot of attention where ever we go.  Doesn't he look so sweet in the little pink and blue sweater and skirt ensemble he's wearing!?!  He wears this outfit so well that I promise that we will send it home with him when his training and transformation here are over."

I looked at the second photo that Mrs. Trainer had enclosed.  It was shocking to see how feminine -- how absolutely lovely -- my rotten son looked.  My mind went into overdrive in that moment, beginning to imagine the new life the two of us would be living when he returned home.  

Mrs. Trainer's letter concluded:

"You may have total confidence that we will complete your son's transformation to our very high standards.  You will be delighted with the lovely and feminine and compliant sissy that you will see in just a few short months.

Sincerely, Mrs. Trainer." 

Mommy's Pajama Sissy -- Part 6

When Steve returned from the rest room, I made an excuse that I saw friends across the room that I wanted to talk to.  That gave Steve and Tammy some alone time.  When I returned about 15 minutes later, Steve said that he needed to leave so we said our good-byes and he left.                                                                                                                 "Well?" I said to My Little Princess.                                                                                                              "He asked me out for tomorrow.  And I said yes." Tammy replied with a bit of embarrassment in his voice.  I squealed with delight at the news and gave Tammy a bit hug.  Tammy gave me the details.  Steve's family belongs to a fancy country club just outside of town. There was a "tea dance" scheduled for Sunday -- tomorrow -- afternoon.  Steve would pick up Tammy at 2:00 and head over to the club.                                                                                    "Oh what fun! I think the little black dress we bought yesterday would be perfect.  Don't you agree?" I said.                                                                                                                                                                 "I guess so," Tammy replied uncertainly. "I don't really know about any of this..."                                                                                                                "Oh, don't be nervous. We'll make you the prettiest girl at the dance and you will be full of confidence. But for now, we should get home so you can get a good night's sleep before your big date tomorrow!"  And so we left. 

Sunday morning was very busy with getting Tammy ready for his big date with Steve. After breakfast, we spent all morning making Tammy look his prettiest.  We did his hair and his make-up.  He wore some of the new underwear we had bought at the mall just two days ago.  He slipped on his pretty new black dress, its straps accentuating Tammy's delicate shoulders, its neckline plunging intriguingly low.  I lent Tammy a chucky necklace and some strappy black sandals that went well with his outfit.                                                                                     "Mother," Tammy asked as he was admiring his own reflection in the mirror, "Don't you think I need to be honest with Steve about....everything? I mean, it doesn't seem very nice to be tricking him this way."                                                                                                                                               "Well," Mother replied, "I think you will need to figure out what needs to be said and when over time.  Don't worry about it too much right now.  Just try to have a good time and enjoy the experience. But if you decide at some point that you want to give Steve the truth, well that will be up to you.  But be thoughtful -- actions have consequences."                                                                                        Tammy was still thinking about his mother's advice when, at 2:00 sharp, Steve pulled up to the house in his BMW and off they went.                                                                                                                       Well, Tammy had never been to a fancy country club, let alone a tea dance, even as Tommy.  The experience was thrilling for him.  The valet parked Steve's car and Tammy entered on Steve's arm.  Waiters were passing trays of champagne and Tammy took one and drank it quickly.  Steven found a little table near the window where they sat and chatted. Older couples -- friends of Steve's parents, Tammy figured out -- would stop their to say hello to Steve. Each time Steve would proudly introduce Tammy as "his friend."  Everyone was friendly and polite.

When the jazz ensemble started playing again after a break, Steve asked Tammy to dance, and Tammy agreed. Tammy was really starting to relax, having had three glasses of champagne by this point in the afternoon.  "Why did they call it a tea dance if all they served was champagne?" he wondered to himself, as Steve led him to the dance floor and wrapped his arms around his pretty date.                                   

Mommy's Pajama Sissy -- Part 5

Well, I imagine you could already guess what might happen next. I couldn't stand having My Little Princess with me only when we were home alone and wearing our nightgowns. In early May I went out and bought Tammy some pretty dresses and shoes that he could wear out in public! 

There was a bit of nervousness at first, as you might expect. But the thrill of going out in public in a pretty dress was more than enough to motivate Tammy to summon enough courage to join me on some real-life adventures.                                                                                                                                           After several days of planning, we were all set for an exciting weekend together. Friday afternoon was very warm, so I dressed Tammy in a gauzy turquoise dress -- he looked simply lovely! Our Friday adventure started with a visit to the nail salon, where Tammy got his first mani-pedi. He was so nervous at first that his hands were shaking. But he settled down and his pretty soft pink nails looked divine. Then I took him to the mall where I let him pick out -- and try on -- several more new dresses and shoes and handbags. We went to three different department stores and must have been there for two hours! And of course I needed to buy him some bras and panties -- today he was borrowing my under garments but needed a collection of his own. Then we had dinner together at a restaurant where Tammy realized that he was getting some serious attention from our waiter!  Tammy handled it well and we had a simply wonderful time.

I had a busy Saturday planned for us. I dressed Tammy in an elegant royal blue silk dress. He looked stunning -- and so grown up! We had lunch together at an intimate cafe downtown that is very popular with ladies out for the day together. Then a matinee of a play at the Civic Auditorium. And finally, the highpoint of our day, we went to a fundraiser reception at the art museum.  Since alcohol would be served, the event was restricted to guests 21 and older -- which Tammy wasn't.  But I was so confident in his ability to appear like a grown-up lady and I knew this wouldn't be a problem. When the ticket taker asked the two of us for our IDs when we entered, I simply said to him "thanks for the compliment" and the two of us walked right on in to the event.  It was magical.  The museum was beautiful, the guests were all dressed up, there was a string quartet playing -- it was heaven! And I could see that My Little Princess was in heaven too.

Waiters passed glasses of champagne and little hors d'oeurves. About 45 minutes into the event we found ourselves near one of the bars where a young gentleman was chatting with a bartender.  I struck up a conversation with the handsome young man whose name was Steve. Steve looked very dapper in an expensive suit and tie. He seemed happy to have someone to talk to. He told us that he had recently finished business school and was home visiting his parent before starting a new job in New York with a big bank. He explained that his parents had bought tickets to the event, but were suddenly called out of town for the next few days. He was attending the event alone and didn't know anyone else there. Of course I introduced my lovely young Tammy to the handsome young Steve. Tammy had had several glasses of champagne by this time and was starting to loosen up a bit. It didn't take long for Steve to start flirting with his pretty new acquaintance. And it didn't take long for Tammy to play along and join in!

At one point Steve excused himself to use the restroom. "What a catch!" I said to Tammy. "Oh stop, Mother!" he replied. ""Don't be silly."

"I'm not being silly," I answered. "He's obviously smitten with you and I can tell you like him too." Tammy turned bright red when I said this. "Why not see where this goes. He's only in town for another two days. Then he's off to New York. Why not see what can happen before he leaves town..."

Tammy was initially dumbstruck by my suggestion.  But his internal feminine needs -- and the champagne -- pushed him to be bold enough to surrender to his urges.

"Alright, mother," Tammy said. "Let's see where this goes."

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."

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 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 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 4

Martin had ordered some champagne from room service which was a very good idea because even though Danielle was excited by everything that was happening to him, he was also very frightened.  The champagne helped to settle his nerves.

"Martin," Danielle said softly, "I need you to know that I've never done this before."

"That's OK," Martin replied coolly, "I've done it lots."

Danielle wasn't exactly sure how this was going to work. If he took off all his clothes, he wouldn't look like a girl anymore and that would spoil the effect for Danielle -- and maybe for Martin too. So while Martin was in the bathroom, Danielle pulled out a sexy nightgown that he managed to stuff in his purse before leaving.  He slipped his nightgown on over his well-padded bra and panties. Danielle freshened his lipstick, put on a bit more perfume and checked himself out in the mirror.  He was very satisfied that he looked pretty and sexy in his nightgown. And with his bra and pads in place, he had all the right curves.  His fantasy was intact; he was a beautiful woman about to have sex with a handsome man.  He slipped on the hotel robe and waited.

Martin emerged from the bathroom looking very sexy. He was also wearing a hotel robe. They made out for a few heavenly minutes. Then Danielle dropped his robe to the floor, revealing his sexy nightgown. Martin looked admiringly at Danielle and gave him a little wolf whistle. "Let's get under the covers," he said.  And so they did. And then the action began.

Martin took control and directed Danielle every step of the way.  And Danielle did everything -- everything -- Martin told him to do.  It started with Danielle stroking and massaging Martin's cock, which made it get stiff.  Danielle was amazed by how big Martin's cock was! It seemed to keep growing and growing the more Danielle played with it. It was at least ten times as big as Danielle's tiny penis.

Then Danielle was instructed to kiss and suck on Martin's cock.  Martin started pumping slowly back and forth in Danielle's mouth. Danielle struggled to fit much of Martin's giant dick in his mouth but he tried his best.  Then Martin's rocking started to get faster and stronger.  After a few minutes, Martin was forcing powerful, deep thrusts into Danielle's mouth, forcefully holding Danielle's head in place so his cock was snaking into Danielle's virgin throat.  And that is when Martin started cumming for the first time.  It seemed to Danielle that a gallon of hot semen was flooding into his mouth.  "Swallow it!  Swallow, bitch!" Martin growled.  Danielle never heard him talk like that but figured it was what real men say when they're excited.

Danielle's ass was next and Martin was ready to do again after just a few minutes rest.  Martin smeared lube on his dick and on Danielle's ass. He positioned Danielle on all fours and then he went to town.  For Danielle, it was very painful at first, having a giant cock rammed up his butt for the very first time. But after a few minutes it started to feel good and Danielle enjoyed the feeling of giving his man such pleasure. Just like before the thrusting start slowly but picked up speed and power as Martin's excitement built. He fucked Danielle hard.  With one arm wrapped around Danielle's waist, he used his free arm to spank Danielle's ass -- hard -- in time with his thrusts. "Say you love me, bitch!  Say it!  Say it now and say it loud!" he yelled at Danielle. Danielle didn't like being called "bitch" but he did as he was told.  "I love you, Martin.  I love you!" he said as loud as he could. As Martin came inside Danielle's ass, Danielle's little dick exploded too, spilling his cum all over the sheets.

Martin wasn't done.  He had taken three Viagra pills as soon as they had checked in.  He shoved his filthy dick back into Danielle's mouth and Danielle didn't protest. After several minutes of more rough thrusting, Danielle could tell Martin was about ready to cum again. Danielle prepared himself to swallow another flood of semen.  But Martin didn't cum in Danielle's mouth. Instead, Martin pulled out of his mouth just before cumming, shooting wads of hot cum into Danielle's face and hair.

Martin climbed out of bed and let out a little chuckle as he looked at the cum soaked sissy mess lying there. "Here," Martin said, handing Danielle his champagne glass, "have a drink."

 "Are you coming back to bed?" Danielle purred.  "I want to snuggle."

"Sure, I'll be there in just a minute," Martin said.  Danielle pulled the sheets up to his chin and promptly fell asleep.

A Boyfriend for my Sissy Husband -- part 3

Saturday arrived and Danielle was sticking to his pile of lies, claiming the he and Martin would be spending a day downtown doing all sorts of cultural things.  In reality, I knew the two of them were going to check into The Inn at the Pier for a romantic rendezvous.  I was so disgusted with Danielle for his lies and for being so easy to manipulate.  Letting a man he had just met convince him to spend the day in bed together having sex!  I could barely believe this was happening, even though it was all happening according to plan. 

Danielle dressed the part for his date of museums and lunch and theater.  He wore a very pretty cream colored skirt and a fitted white jacket. Danielle had asked my to buy him some new bone colored high heels to complete his look. Danielle looked wonderful. His outfit was conservative and stylish at the same time. There was a slight chill in the air, so he also wore a lightweight black coat.

Off they went, not to downtown like Danielle said, but to the lake where Martin had made a reservation for a room for the day at "The Inn" which is a really exclusive and expensive hotel. When they arrived at the front desk, Danielle started to get nervous and have second thoughts. But when the receptionist greeted them as "Mr. and Mrs. Rittenhouse," Danielle felt yet a new surge of excitement and feminine delight that the receptionist really believed that he was Martin's wife!

They went up to their room.  They had very little with them; Martin had brought only a small bag and Danielle only had his purse, although he managed to stuff a few extra essentials in it without me noticing -- or so he thought. The first thing Danielle did was to go into the bathroom and put on the diamond heart necklace that Martin had given him; he had been afraid to put on before leaving home.

Martin wasted no time.  He took Danielle in his arms and started hugging and kissing him, saying all sorts of things to him about what a beautiful 'woman' he is and how he wished Danielle could really be his 'wife.' The experience was overwhelming to poor naive Danielle - the fancy room, the view of the lake, and most of all, the strong, confident gentleman who was seducing him.

"Danielle," Martin whispered in his ear, "Let's go to bed."  Danielle nodded and giggled enthusiastically in response.

A Boyfriend for my Sissy Husband -- part 2

A week passed and it was time for Danielle's second date with his new "boyfriend," Martin.  Of course, Martin wasn't really Danielle's boyfriend - he was a man I picked to construct a wild psycho-drama for my sissy.

Danielle was all giggly and nervous before Martin arrived to pick him up.  Unlike last week when Danielle was terrified of being out with a man, tonight I could tell he was excited and looking forward to it.  Something deeply feminine and girly had been awakened by his first date.  It was as if Danielle was being flooded all at once by the emotions of a 15 year old girl!

Danielle had begged me to take him shopping for a new dress to wear.  This was going even better than I could have dreamed!  Danielle explained that Martin wanted to take him to The Windsor for their second date.  The Windsor is a very exclusive and very expensive restaurant and after hours club with wonderful food and live music and dancing.  Danielle was all aflutter with the idea of being asked out on a date there.  I agreed to take Danielle shopping and we bought a very elegant purple dress for him to wear.

When the big day arrive, once again Danielle spent most of the afternoon at the beauty parlor getting all prettied for his date.  The girls at the salon made him describe every minute of his prior date.  They told Danielle how lucky he was to have such a handsome and charming man pursuing him and taking him out to really fancy places. Instead of becoming anxious by their chatter like he was last week, this time Danielle was flattered and encouraged by it.

Martin picked up Danielle and took him away for the evening. Here are some photos of the two of them on the grand staircase heading downstairs to the club after they finished with their dinner. It was another dreamy dinner date for Danielle -- his girly feelings completely overwhelming his natural heterosexual tendencies. 

Danielle was much more relaxed than he was on their first date.  And Martin was much more flirtatious.  After the wining and dining, the lovebirds moved to the dance floor, where Martin expertly led Danielle as the combo played a variety of slow, romantic songs.  Danielle felt so safe in Martin's strong arms.  Danielle felt like he was floating on air, twirling and swaying in his lovely purple dress and 4 inch sandals.

When they couldn't dance anymore, Martin navigated them both to a sofa where they sat.  Martin said, "Danielle, I know I only just met you, but I want you to know that I already have very strong feelings for you.  Danielle, I'm falling in love with you."

Danielle's heart must have almost stopped beating when he heard this. Before Danielle could open his mouth, Martin took out a small wrapped gift from his pocket.  "Here, Danielle, this is for you."  Danielle nervously accepted the small box from Martin and opened it. Inside was a beautiful heart-shaped pendant covered with about a dozen diamonds.

"Oh my!  It's lovely!  I...I don't know what to say.  This is all so unexpected!" Danielle managed to sputter.

"I'm sure it is," Martin said calmly as he helped Danielle put the necklace on.  "You don't have to say anything.  But I do want to see you again.  And soon.  And for longer. And for more."  Danielle looked confused so Martin elaborated. "Next Saturday, let's spend the whole day together. Here's my idea.  We can drive over to the lake and get room for the day at the Inn on the Pier.  We can get to know each other better, if you know what I mean."  Now Danielle knew exactly what Martin meant.  Danielle knew this was not something that he should agree to but he couldn't help himself.

"Okay," Danielle said.  "But I can't tell my...spouse.  I know that meeting you was all her idea but I don't think she would approve of me checking into a fancy hotel with you."

"Not a problem," Martin responded.  "All of this can be our little secret.  You can tell your...spouse...that I have planned a full day of activities together downtown, we'll go to the museum, then lunch, then a matinee...I will pick you up at 9:00 and have you home by 6:00.  And no one will ever suspect what we're up to."

"You are a devil, aren't you, Martin Rittenhouse?" Danielle replied with a wide grin, barely able to contain his delight that this handsome man was pursuing him as if he were the most beautiful woman on the planet.

There was more kissing and groping in the car before returning Danielle home.  I again was waiting in the living room.  Danielle gave me a report on his evening, delighted in sharing details of the dinner, the dancing, the music.  But he did exclude a number of details.  He said nothing about the necklace he received (he must of taken it off just before coming inside), nothing about Martin's profession of love for him, and nothing about their sneaky plan to screw around in a hotel next Saturday.

Of course, Martin kept no secrets from me.  And I fully expected my pathetic sissy husband to mislead me about what was really going on between him and Martin. Danielle didn't know it, but he was quickly digging himself into a hole from which he might never emerge. 

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."