A Reluctant Sissy -- Part 2 -- Dinner

About two weeks after I received my first report on my son's progress at Ms. Trainer's London facility for enforced feminization and obedience training, I received another update -- with more photos.  Let me share this latest update with you:

"Dear Mrs. ____,                                                                                                                               We wanted to let you know that we are continuing to make good progress with your son's transformation.  As you know, he is rather strong-willed and stubborn - but our staff loves a challenge!  And we have the tools and the experience to break down even the most reluctant sissy.                                                                                                                                                             The enclosed photos show your son dressed for dinner.  Dinner is a rather formal affair here at the facility and we insist that our sissies dress up nightly in an appropriately fancy and feminine manner.  We think your son looks absolutely divine in his dinner dresses.  As you can see, his still refuses to smile for the camera.  He is very unhappy with what we are forcing him to do and he is probably terrified of what the future holds for him.  Regardless, I think he looks simply divine in the nude colored dress and absolutely charming in the green dress"                                                                                                                                               I took a moment to study these latest photos.  I could hardly believe that this lovely creature in the long sleeveless dresses was really my son!  He looked so ladylike, so elegant.  But I certainly did recognize his scowl -- just about the only expression I ever saw him make.  Well, pout as much as you like, sissy boy.  I know you will be no match for Ms. Trainer's staff and their techniques! 

The letter continued:

"I understand that you never received much background on our process here at the facility as I know you deposited your son with us with some urgency.  I thought you would enjoy a quick overview of our process. Every day begins at 5:00AM sharp and our sissies make themselves pretty for the day.  Then for the next 12 hours, it is non-stop chores and training. We are proud of what wonderful domestic workers our sissy graduates are after hundreds of hours of cleaning and cooking and serving -- all under our most strict supervision, of course. There is intense training on etiquette, deportment, speaking, beauty and other skills expected of sissies (did anyone say massage?)  Training here includes classes led by my wonderful staff, supplemented with subliminal messaging and hypnosis.  We have also begun your son on medically supervised hormone treatment (you will recall signing a release for that.)                                                                                                 I did not share it with you in my prior letter, but we did have to use some rather extreme measures on your son during his first weeks with us.  But we know what we are doing in this area and we were able to get him to understand that he is to be obedient and submissive and cooperative -- or risk a repeat of the punishments he received when he first arrived.                                                                                                    Anyway, those days are behind us now and your lovely sissy son is making wonderful progress.    I will write again soon.  Sincerely, Mrs. Trainer."

 

A Reluctant Sissy -- Part 1 -- Arrival

It was just about two years ago that I finally decided that I had had enough!  I am a single mother and my son was completely out of control.  I didn't really care that he was a crossdressing sissy.  I didn't like him getting into my lingerie and make-up and dresses and shoes every time my back was turned.  But I could have lived with that.  There were other problems -- real problems.  He was close to failing out of school, he was getting into all sorts of drugs, and I was spending a fortune getting him out of trouble with the police for his non-stop shoplifting.

There were endless meetings with his teachers and counselors at school.  But they had no answers.  I tried family therapists, but they were useless.  I tried grounding him and every other form of punishment I could think of.  Nothing worked.

And then he stole several pieces of my jewelry and tried to pawn them. That was the last straw!

I remember reading somewhere that there was a Ms. Trainer who ran a service where she could improve the behavior of boys through feminization.  It wasn't easy to track her down, but I did.  I discussed my situation with her and she was very reassuring.  She explained that since my son was already a crossdressing sissy, her techniques should work very effectively on him.  She suggested that I send him to her new facility in London, where the staff and the process were extremely strict and effective.  A new semesters was just about to start and there was one opening (they handle up to six sissies at a time).  I considered this to be a real opportunity so I wasted no time at all in doing what she suggested.

Imagine my son's surprise when we arrived at Ms. Trainer's estate outside of London.  My son thought I had taken him to London so he could go pubbing and what not. You should have seen the look on his face when we pulled up the driveway and two enormous orderlies roughly grabbed him and dragged him out of the car and into the house!

After an initial period a six weeks, during which I had heard nothing about my son's progress, I received my first report from school -- complete with lots of photos!  Let me share their letter with you:

"Dear Mrs. ___, 

We are happy to report that your son has made good progress during his first six weeks with us.  We have decided to call him "Kimberly" -- we hope that name is satisfactory to you. He is settling into our routine of continuous training, behavior modification, and positive and negative reinforcement. There is evidence that we are starting to strip away his awful self-destructive behavior and replace it with a gentler, more compliant, feminized version of himself.  Enclosed please find several photos of how your son is dressed everyday here at the facility.  He really makes an adorable sissy!"

I stopped reading to marvel at the enclosed photos.  I was stunned by just how lovely my son looked in his pretty new dresses.  He had become so skinny in just a few weeks.  And his hair was dyed such a pretty shade of blonde.  His make-up, his jewelry, his sky-high heels -- everything was just so perfect and dainty and feminine.  I could barely believe my eyes.

The letter continued:

"Of course, even though we know he is a sissy at heart, he is resisting the feminization process.  This is normal and not a cause for concern at this early stage.  As you can see, he refuses to smile for our photos. As we remind him daily, we don't care if he is happy or not; he is only succeeding in making his transformation more difficult and more miserable for himself.

We will keep you posted as our time with your son proceeds.

Sincerely, Mrs. Trainer"

Bad News for My Sissy Husband

"Sweetie, do you have a minute to talk?" I called up the stairs.  My darling sissy husband, Lily, came down right away.

"Yes, Martha. Is there something that you need?" he asked.

"My, don't you look extra pretty today!  That pink top is super cute on you and really shows off how you are...developing.  And I love that necklace on you!" I cooed.

"Thank you, Martha," he replied softly. I could tell he was both thrilled and a bit embarrassed with my compliments.

"Sweetie, we need to talk. Now I know you have really been looking forward to our vacation to the Bahamas tomorrow," I started.

"Oh yes, Martha.  I'm very excited about our trip!" he replied breathlessly.

"Yes, well," I started. "There's been a change of plans.  You're not going," I stated matter-of-factly.

Completely blindsided by my announcement he responded, "What? No! We've been planning this trip for months!"  His eyes were starting to tear.  This announcement was getting him rather upset.

"Now Lily, really!  Think about it.  I mean, just look at you.  Look how much you've changed!  Your hair, your breasts, your hips.  You have become so feminine!  How can I be expected to go on a romantic Caribbean vacation with you?  You can barely even pass as a man anymore!  Needless to say, you can't take your shirt off on the beach now that your boobs have grown so much," I explained.

"But I did all of this for YOU!  YOU wanted me to become more feminine, more ladylike.  I made all of these changes because YOU wanted it!" He was starting to cry as he spoke.  Goodness, the hormones make him so emotional!

I put my hand on his shoulder, "Oh, Lily, of course I know that. This is how I want you. Soft and feminine and gentle.  I love having you as my sweet little sissy housewife.  You look and smell so pretty and you take such wonderful care of me.  You are exactly the way I want you. At home, that is.  But on a romantic vacation?  Well, that obviously is not going to work."

"So you cancelled all of our vacation plans?" he asked stupidly.

"Oh, good heavens no, silly girl.  The trip is all paid for.  I'm going with Ben."

"Ben? Who's Ben?" Lily asked.

"Ben Martins, silly. My editor," I said. Then the wailing really began.  

"You're going on vacation with Ben?!?  Why? How? What's going on?" Lily was starting to get a bit hysterical by this point.

"Well, Lily, Ben and I have been spending a lot of time together finalizing my latest book. And he is going through a difficult time since he is getting divorced.  Anyway, over the past couple of months, he and I have gotten rather...close.  He really is a very nice man.  And so tall and handsome!"  The crying got much worse when I said that.

By now I was growing tired of Lily's sobbing. "Now calm yourself. You know this is for the best. Look, I am a woman and I have needs -- and believe me, he really knows how to fill my needs!  Ben and I will be able to have a wonderful, romantic vacation together in a way you and I simply can't anymore. Besides, you have fallen way behind on your chores and this will give you a whole week to get caught up."

Lily had no words in response to that.

"And since I'll be spending more time with Ben at his apartment when we get back from the Bahamas, I thought it would be nice if you would go over there while we're away and get it all tidied it up.  It really is a mess and you wouldn't want me having sex in an apartment that wasn't properly cleaned, now would you?"

"Well, would you?" I repeated a bit more sternly, in case Lily thought it was a rhetorical question.

"No, I guess not," he answered softly.

"No, of course not," I agreed.  "Now pull yourself together. I know, let's go to the mall and I'll buy you something pretty to cheer you up.  And while we're there, you can help me pick out a new bikini and maybe a sexy nightie to take on my trip.  OK?  Now dry those eyes and grab your purse."

Sissy Roommate - Part 10 - The Conclusion

 I know it's been a long story, but now you are up to date.  It's the start of Tank's Junior year.  I dropped out because I knew I couldn't care for Tank and take classes at the same time.  But Tank and I will be living together this year in a beautiful condo that a rich alumnus has provided for Tank.  I've been working hard to make sure it is clean and all ready for Tank when he arrives, which should be any minute now.

I bought some new clothes over the summer, including the outfit you see me wearing here.  I sure hope Tank likes it when he sees me.  And I curled my hair which got longer over the summer.   I'm making an extra effort to look nice since I haven't even seen Tank all summer long!

And best of all, the hormones really kicked in over the summer and my breasts grew a lot! 

Excuse me, my phone is ringing.  Oh great, it's Tank!

"Hi Tank! Are you almost here?  The condo is all clean and I...."

"Stop talking!" Tank barked through the phone. "Jesus Christ! Just shut up and listen!"

"OK  Sorry," I replied softly.

"Look, a lot of stuff happened over the summer. I'm engaged," Tank explained flatly.

"What? I don't understand. Are you joking? What are you saying?" I babbled.

"If you would shut the fuck up, I would tell you, you stupid sissy bitch.  You remember Amber Destry, the swimmer from the Hall of Fame event last Spring?"

"Yes," I answered softly. My tummy started doing backflips. Remember Amber?  How could I forget. She was like a living Barbie doll.

"Well we got engaged this summer. And her dad, who's loaded, has bought us a house off campus to live in together."

"But what about our condo? What does..."

"For the last time, shut the fuck up!  The good news for you is that the alum that owns the condo has agreed to let Jefferson and Jackson live there.  And they seemed pretty interested in you when they met you last year, so I decided that you can just start being their sissy from now on."

I couldn't even make sense of what I was hearing. Tank was engaged to a real girl.  I wasn't going to be living with him.  And Tank had just decided that I would now be...given?...to Jefferson and Jackson.  I started to feel faint.

"Got to go," Tank said and he hung up.

I put down my phone and grabbed hold of the kitchen counter to steady myself.  What was happening?  What was I going to do?  I didn't have a penny to my name and I had no where to go.  My head was spinning.

But not for long.  Because just then I heard the front door being unlocked and in walked Jefferson and Jackson.

"Hello sissy!  We're home!" shouted one of them in a loud sing-song voice.  The other one broke out laughing.

"Damn!  Look how he's dressed!  Did you get all dolled up because you knew we were coming?  You are one sexy sissy!" the first one said. 

The other one grabbed me by the throat with one hand and roughly grabbed one of my soft new breasts with the other. "It's true, Jack! The sissy really does have titties like Tank said!"  He kept squeezing my breast and my neck really hard -- and then he licked my face, from my chin up to my forehead.

Then Jack laughed and said, "You know how I love titties!" Then he said, "Keep holding him like that, Jeff.  I'm gonna get this party started!" as he unzipped his pants.

THE END

Sissy Roommate -- Part 2 -- The First Time

As I said, I am Tank's full-time sissy girlfriend now.  I wear only girl clothes and make-up and I keep my hair long and in a very feminine style. I diet to stay super skinny.  I slather my body with creams and lotions to keep my skin soft.  I do this all to please Tank.  I haven't seen Tank all summer and he should be arriving any minute. Here are some photos Tank took of me last spring. He likes it when I wear really short skirts.

But I wasn't always a girlish sissy living only to serve a demanding, strong alpha-male. My life changed completely that first day that I met him.

"Come over here," Tank said, without even bothering to ask my name.  "I have a cramp in my leg.  I need you to massage it for me."  Tank pulled off the sweat pants he had been wearing, revealing a thin pair of nylon gym shorts.

I did not want to do what Tank was asking.  "I don't know anything about massages or..." I started to explain.

"Just do it now!" he demanded, pointing to his thigh.


I don't know why, but I complied with his order.  I figured he was an important athlete and that I should try to help him out if I could.  I knelt by his bed and started rubbing his thigh.

"Mmm.  Yeah.  That's good.  Rub harder.  Yeah," he said.  I was pleased that I was doing it right.  "You're hands are so soft.  Like a girl's."  I felt embarrassed when he said that but I kept on rubbing his thigh.

"Now jerk me off," Tank said as if it were the most natural request in the world. I was completely shocked when he said that.  I pulled away from him and said I wouldn't do that.  "Yes you will," he insisted.  With one hand he yanked down his shorts and with the other he grabbed my wrist and forced my hand on his enormous dick.  "Do it," he commanded, keeping his hand firmly wrapped around my wrist.  I was really scared and no match for this mountain of a man.  I wrapped my fingers around his huge cock and started stroking him, pumping him.  "Yeah, bitch! That's it!"  His breathing got more rapid and his dick started swelling.

"You know," he said, "You sort of look like a girl.  You got long hair and no muscles.  Yeah, I think we're going to pretend that you really are a girl."  He was really panting now.

"Use your mouth, bitch" he ordered.  No way I was going to that, but Tank grabbed hold of my hair and forced my head to his crotch.  I sealed my lips tightly closed, but with his other hand, Tank pinched my nose so I couldn't breathe. "Open wide, slut," he said with a laugh. As I opened my mouth to gasp for air, Tank jammed his dick into my mouth.  With both of his hands now tightly holding my head in place, I had no ability to move or fight back.  And in an instant, Tank's cock exploded, filling my mouth with spurt after spurt of his hot, sticky cum.

When he was done with me, he roughly shoved me away.  "Next time, wear a dress and some make-up or something so it won't feel so gay."

"What the fuck," was all I could think, as I pulled myself up from the floor and ran out of the room. 

Sissy Roommate -- Part 1 -- What I Look Like Now

It's the start of the college year.  I would be a junior now except that I dropped out after the end of last year.  But my boyfriend, Tank, is starting his junior year. I didn't think I would be able to take care of him properly and go to classes at the same time so I dropped out. 

I have been working for days getting our off-campus apartment ready before Tank arrives later this afternoon.  I bought new sheets and towels for him, new pots and pans for our kitchen, even some nice pictures to hang on the walls.  And I scrubbed every inch of the place so it would be sparkling clean when Tank arrives.  Of course I had to spend most of the money I earned waiting tables this summer, but it will all be worth it if Tank is happy with how our apartment looks -- and if he is happy with me.  And I spent the rest of my money on some pretty new clothes and shoes.  I don't have a single dollar left -- but that's OK because Tank has tons of money.

I finished all the apartment chores about an hour ago. That left me time to get cleaned up, do my make-up and put on one of my pretty new outfits before Tank is scheduled to arrive.  Do you like how I look?  I bought this dress over the summer and I think it is sweet and sexy at the same time.  And I think Tank will go crazy when he sees my over-the-knee socks and platform sandals.  What do you think?  After being apart all summer, I really hope Tank likes what he sees when he arrives.  I don't like to disappoint him.                                                                     Maybe I have gotten ahead of myself. Let me fill you in on some things.  First of all, Tank and I have been roommates since the beginning of last year. Tank is a superstar football player - that's where his nickname comes from.  Oh, and one more thing.  I'm not really a girl.  I'm Tank's sissy. 

It all started last September, at the beginning of my Sophomore year.  I had a really great dorm room -- a double room with its own bathroom -- but I had no roommate.  The Housing Office warned me that at some point I would be assigned a roommate and that my "single" was not a permanent thing.  Well, about one week into the semester, I came back to my room after dinner and there was this enormous guy in my room -- 6' 8" at least.  Everything about him was huge -- his shoulders, his neck, his biceps.  With him was a little man in a suit who was talking a mile a minute. "Well, Tank," the man said to him, "Since your decision to come to State U was so sudden, this is the best room we have for you. Of course, we'd rather have you down in the Athletes' Village by the gym, but that's all full right now.  But on behalf of the administration, the university is DELIGHTED to have you join us! I hope you can make do with this housing...situation until we can get you a more appropriate room." The little man seemed to be referring to me as part of the lousy rooming situation that Tank was going to have to tolerate.

"I'll make it work," Tank replied, his voice, a deep, rumbling baritone that sounded like distant thunder.

"That's swell, Tank!  Just swell! Let me know if there is anything we can do for you," the little man said as he handed Tank his card -- and an envelope that I would later learn was stuffed with cash.  "And good luck with the season. We hear that you just might break a lot of school records and even take us to a Bowl Game this year!  And let me know if you need anything. We're here for whatever you need. Just ask." With that the little man excused himself.  

The two of us were now alone in our room.  Tank plopped down on his bed and looked over to me.  I thought he was going to start a conversation, but instead just said, "Come over here."

A Christmastime Sissy - Part 2

As I explained in my previous post, my husband, "Suzanne," is a crossdressing sissy.  I love him very much and I decided to give him the greatest gift of all at Christmas -- the freedom to be exactly who he wanted to be.  Suzanne had a "hall pass" for the months of December and January to be the woman he always dreamed of being -- and to do it with his handsome boyfriend, Paul.

When January was halfway over, I was beginning to realize just how happy Suzanne had been living out his fantasy of being a woman.  I mean, just look at these photos.  Suzanne looks so at peace, so fulfilled.  And while I wanted to get my husband back, I also felt I had to duty to help Suzanne achieve his/her own destiny.

At the cafe where we were having lunch together, I was about to tell Suzanne that he could continue living as a woman with Paul, if that's what he really wanted.  Instead, Suzanne surprised me with an offer of his own.

"Honey," he said, "You know that I have been enjoying my time with Paul over the past six weeks.  And you know that I also love you so very much."  I nodded in agreement, a few tears started to well up in my eyes.

"Well, Paul came up with an interesting idea.  Why don't the three of us...get together.  You know, as a "Throuple" as the kids say.  He's a very nice man and I'm sure you find him attractive." I couldn't respond.  I was stunned by what I was hearing.

"But why not give it a try.  Who says we have to chose between being together and me living as Suzanne?  I know it might sound crazy at first, but please just think about it.  I think it could be wonderful.  I love being Suzanne.  And I love you.  And I love the experience of being romanced and cared for by a real man.  Paul would do the same for you.  If you let him."

I was speechless. But looking across the table at my beautiful Suzanne -- his hair and make-up just so perfect.  His lovely smile and his pretty eyes.  His feminine gestures and lilting, gentle voice.  I felt an odd desire for him that I hadn't ever felt before.  He was just so...ladylike and elegant.  And then add in all the talk of having me get romantically involved with that handsome man.  My pulse starting racing and my panties started to get damp.

"Please say you'll think about," Suzanne begged.  "I think the three of us could have a wonderful life together."

Well, dear reader, that all happened five years ago.  I did agree to Paul and Suzanne's offer.  And our lives have become an exciting, magical journey.  Over the course of those five years, so much has happened: Paul's divorce was finalized, I sold my house and we all moved in together in Paul's lovely home, Suzanne started hormones and has become more womanly and more beautiful each day.  And while Suzanne and I are still legally married to each other, we even had a commitment ceremony where the three of us effectively "married" each other.

Suzanne is delighted to take care of almost all the chores around the house.  She prepares lovely meals for us, does all the laundry and tidying.  She fusses over Paul and me like some idealized housewife from the past.

And of course, there is the sex.  I hadn't realized how much I missed being in the arms of a real man.  And believe me, Paul is quite the stud.  He is tall and strong and very muscular.  And his cock is massive!  My own husband couldn't ever give me that kind of experience -- even when he wasn't dressed up like a girl.

Most nights the three of us climb into our king size bed together.  Suzanne and I usually wear matching nightgowns and we lay on either side of Paul.  As we snuggle up against his naked body, he wraps his big arms around us and pulls us close, our heads laying on his strong chest.  Love comes in all combinations -- sometimes all three of us at once, often any combination of the two of us.  I never feel any jealousy; my needs are fully satisfied and I am delighted when Paul and Suzanne have their intimate moments together. (And sometimes I like to watch!)

Paul often travels for work. Sometimes, one or both of us will go with him.  But most often we both stay behind, making that a special time for just the two of us.  I don't look at Suzanne as my husband any more -- I look at him as my beautiful, feminine lover and best friend.  And with that perspective, I delight in our lovemaking when it is just the two of us.  I love Suzanne's soft and smooth skin, her skinny delicate frame, her tiny adorable dick, and her extremely talented tongue.

So that is my Christmastime sissy story.  Maybe I should say it was my own Christmas miracle.

I hope all of your sissy dreams come true this Christmastime!

 

A Christmastime Sissy - Part 1

Well, Christmastime is almost here.  And I thought you would enjoy hearing a Christmas story about my sissy husband.  I've included a few Christmas photos of my husband -- that's him with the long curly hair, the pretty blue dress and the beautiful smile.

My husband has been a crossdressing sissy throughout his entire life.  I knew he was into dressing up in ladies clothes before we were married -- and I didn't mind -- really.  But over the first few years of our marriage, I began to understand just how deep his feminine needs ran.                                                           I had no problem with him dressing up as "Suzanne" on the weekends.  I even went out to bars with him a couple of times when he was all dolled up.  And when he was dressed up as Suzanne, he really enjoyed acting like the housewife in our relationship.  And do you think I was going to complain that he did almost all of the cleaning and cooking just because he was wearing a dress, a frilly apron and heels?  No way!  I'm no fool.  I had a great thing going.

But over time I began to understand that I was seeing just the tip of the sissy iceberg.  The part that I couldn't see, that was lurking beneath the surface of the water, was an unstoppable need for my sissy husband to push the boundaries, to come as close to experiencing life as a real woman as he could.  And that of course led to...men!                                                                                   I knew that Suzanne was spending a lot of time each day on the internet -- but I didn't know what he/she was doing.  As it turned out, Suzanne was meeting men who were looking for "relationships" with feminine, pretty, submissive sissies, just like my husband.  It took some time, but eventually I got onto Suzanne's email and blogs -- and let me tell you -- I nearly fell down.  There were dozens of men -- literally dozens! -- flirting with my husband, sharing photos, and asking Suzanne for dates -- and more!

I was surprised to learn how many men out there are really into sissies.  But I wasn't really surprised that Suzanne had caught their eye.  As a man, my husband is rather unassuming.  But when all dolled up as Suzanne, he is very attractive, I have to admit.  The few times we went out together as girls, he always got a lot of attention, compliments and free drinks from the men floating around the bar.                                                                                                                                                               One of Suzanne's online suitors turned out to be a very successful lawyer named Paul who was separated from his wife.  Paul lived in a town about 20 minutes away from where we lived.  By scrolling through Suzanne's email, I realized that they had been seeing each other -- very carefully and infrequently -- for several months.  That sneaky Suzanne!  I had no idea until I read his/her email.

Anyway, around Thanksgiving, I confronted my husband with what I had found.  He tried to deny it at first but he quickly surrendered since there was just too much evidence against him.  But once he admitted to what he had been up to, I reassured him.  I told him I didn't like him being unfaithful.  But because I understood what a complete sissy he was, being unfaithful with another man wasn't as bad as being unfaithful with another woman.                                                                            I told him that I was going to give Suzanne a very special Christmas gift: a two-month "hall pass."  Suzanne could do whatever she wanted -- anything at all -- for the next two months, until the end of January.  But I wanted her to get it out of her system and then I expected my husband to come back to me.  My husband agreed to my proposal with tears of gratitude.  

"Well, girl," I said to him. "Get busy.  Because on February 1, your hall pass expires. So go be a woman, in whatever way you need to."                                                                                                                                                                                           I'm sure that Suzanne's boyfriend, Paul, wasn't going to believe his good luck.  Instead of stealthily seeing Suzanne on a few rare occasions, he was going to get to have as much of Suzanne as he could handle for two whole months.                                                            

And that brings us to Christmas.  As you can see in the photos, these two love birds thoroughly enjoyed their time together.  Just look how pretty and happy my Suzanne looks.  And her boyfriend is actually a very nice man, fairly wealthy and not bad looking at all.  Suzanne really scored a winner.                                                 But as the days in January flew by, I was left with so many doubts.  Looking at these Christmas photos showed me just how much Suzanne enjoyed acting as the wife/girlfriend to a real man.  He/she seemed freer and happier than I can remember him being for a long time. I didn't want to lose my husband that I love so much.  But I also didn't want to take away from him an experience and a lifestyle that was clearly so fulfilling for him. So around the middle of January, after having given it much thought, I decided to have a conversation with Suzanne.  We met for lunch at a local cafe -- something we had been doing once a week throughout December and January.  I decided that I was going to leave it up to Suzanne to chose to either come home to me or to stay with his boyfriend.  

Well, as we sat down for lunch, and as I was about to start my prepared speech, Suzanne surprised me and started speaking.  "Honey," she started, "I have something important to discuss with you..."

 

Taking my Sissy Husband on Vacation

My husband and I are having the most wonderful vacation together.  That's me in the photo on the left, the brunette in the black dress.  But that's not my husband in the photo! That's my new vacation boyfriend, Jerry.  I met Jerry earlier this week at the resort bar.  You see my husband is not a real man like Jerry.  My husband is a feminine, submissive sissy. 

That's my sissy husband in this photo -- the pretty blonde "lady" in the sexy gold dress.  His real name is Martin, but he is living only as "Tina" this week while we are on vacation.  And as you can see, Tina landed a handsome new vacation boyfriend too! His name is Darren.

My Tina is very, very good at passing as a woman.  He works hard at keeping his body slender through a strict diet and body-sculpting exercises.  He keeps his hair long all the time, but dyed it and had it styled especially for this trip.

Don't you think they make a cute couple?  Darren is everything that my Martin/Tina isn't. He's strong, confident and decisive.  A real Alpha male! I love seeing Tina with Darren. It seems like Tina doesn't have a single idea of his own when he's with his hunky new boyfriend -- Tina seems only capable of agreeing with whatever Darren says and whatever Darren wants to do.

I love seeing how Tina behaves when he's with a real man!  That's why I planned this vacation to a singles resort.  Although we have been out together as two women many times before -- to restaurants and bars and so on -- we had never taken a week-long vacation like this before.  For Tina -- and for me -- it is a wild, new experience!

I know my sissy husband enjoys his time as Tina.  I know that his need to express him feminine side is far too powerful for him to resist.  And being in the arms of a strong, masculine man is so exciting for him, throwing his feminine feelings into overdrive. But tricking a man to believe that you are a real woman when you are not is playing with fire!  And Tina knows this. Each moment he spends with an unsuspecting man fills Tina with equal parts excitement -- and fear that his secret will be revealed.

Tina and Darren have been an item for three days now -- and we have three days left in our vacation.  Can Tina keep up the act for the rest of our vacation without letting Darren find out the truth?  I certainly hope so.  I expect that Darren would be furious beyond belief if he learned that the woman he was falling for was really a man.

So how does Tina manage to keep his secret? Well, the first night was easy --  just some flirting and a little pawing at the resort bar, with a brief good night kiss at the end of the evening.  By day 2, things were heating up, with some heavy making out during the day and a hand job in Darren's room at the end of the evening.  (His cock is enormous, Tina reports!) 

Today is day 3 of their steamy relationship.  I caught Tina and Darren making out like crazy earlier today -- including in the swimming pool!  Now we are all dressed up for a double date together.  First we'll have some Happy Hour cocktails, then a romantic, candlelit dinner together, followed by dancing at the outdoor bar until late. It's what happens after that that has Tina very nervous.

"You better hope he likes blow jobs!" I told Tina. "And I hope you are really good at giving them.  Because he is going to expect to get some serious action from you. And since he can't fuck you, you better find some other way to keep him interested." Tina has practiced giving blow jobs on the strap-on dildo I sometimes use on Tina's backside.  But Tina has never had a real cock in his mouth -- or down his throat.

 

Of course, I've been fucking my new vacation boyfriend every chance I get this week.  We run off to his room a couple of times during the day and of course in the evening. He is amazing in bed! And I always give Tina a detailed report on my sexual encounters with Jerry.

I really hope that Tina -- and his pretty mouth -- can keep Darren satisfied and unaware of the truth. They make such a cute couple and Darren really seems rather smitten by Tina. And I can tell Tina is really falling for Darren.

Keep your fingers crossed that Tina can really pull it off. With a little luck -- and a lot of sucking -- Tina just might come home with wonderful memories of his romantic vacation with Darren -- and a tummy full of Darren's hot, sticky cum!

 

Mommy's Pajama Sissy -- Part 11

After the success of PJ Day -- and Tammy's "coming out" -- Tammy was on his way to having a very exciting summer.  In fact, I don't think I can remember seeing "Tommy" all summer long.

As the summer began, Tammy took a lot of interest in how he looked, asking me to take him to my salon every week so he could have his hair styled and colored in different ways. One week he'd ask for his hair to be straight and sleek and lightened; the next he'd want some curls back and a different shade of blonde. By now, Tammy's hair had really grown quite long so the stylist was able to make it look really great.  And Tammy started wearing more make-up -- which he had really never done before. 

And then there were the clothes!  I spent a fortune during the weeks after school ended to get Tammy all the different outfits he said he needed. Here are a couple of photos I took of Tammy after one of our trips to the mall.  Doesn't he look adorable.  You can see how he had his hair lightened.  And look at his eye make-up.  So pretty!  And check out those sexy sandals -- I wouldn't even be able to walk in those!

Right from the start, Tammy's schedule that summer was busy! The girls from his class started including him in their trips to the mall and hanging out at each other's homes.  Tammy would come home after spending time with the girls and tell me all about what they did -- and what they talked about -- which seemed to only BOYS, BOYS, BOYS!  And Tammy got his share of teasing from the girls because of Jimmy.  More on that in a minute!

One of the girls even got Tammy a job waitressing during the busy lunch time shift at the local diner.  I know this was hard work, but Tammy seemed to really enjoy it.  And I was glad that he was working during the summer -- even if just for a few hours a day.  Tammy looked so cute in the apron he wore when he was working. And every time I stopped by, Tammy was always getting a lot of extra attention (and some very good tips!) from the male customers.  

Well, back to Jimmy.  I had never dreamed that PJ Day would lead to Tammy catching the eye of the captain of the football team!  It was clear from the beginning that Jimmy was completely smitten with my little Tammy!  Some days, Tammy would get off work in the afternoon and go straight over to Jimmy's uncle's body shop and hang out there until Jimmy finished work.  And Jimmy was always asking Tammy to go out with him in the evenings and on weekends.  It all seemed innocent enough -- at least at first.  Tammy was thrilled with all the attention he was getting from Jimmy and how all the other girls from school were amazed that Jimmy and Tammy were "an item."  I had never seem Tammy so excited and happy as the times I saw him getting ready for a date with Jimmy.  He would spend hours getting himself all dolled up to look his nicest for his new boyfriend.  Sometimes he would try on dozens of outfits before settling on the one he would wear out with his new beau.

And Jimmy and Tammy did seem to have fun together.  Here are a few photos Tammy showed me of their time at the fair.  Just look how happy my little Tammy is.  And doesn't he look sweet in that little sundress he's wearing?  Jimmy certain seems to like what he sees!

 

The two of them spent a LOT of time together as the summer began.  There were dates to the movies and concerts, and trips into the city and lots of time on the beach. They really seemed to enjoy each other's company and seemed to be growing very close.

I know that the two of them would sneak off to be...romantic...together every chance they got.  My Tammy didn't even try very hard to hide it from me.  In fact, he loved talking about how being with Jimmy made him feel, how he loved being held tightly in Jimmy's strong arms, how he loved it when Jimmy would kiss him really hard.  But even if things seemed to be getting a little hot and heavy between them, I figured that they were just kids being kids and the experience of being together and exploring these romantic feelings wouldn't cause any harm.  And Jimmy seemed like a nice enough boy.  So I basically stayed out of it and let Tammy find his own way through this new terrain.

I was fine with all of it, really, until I overheard Tammy talking to one of his new girlfriends from school about something Jimmy called "sharing."

Mommy's Pajama Sissy -- Part 9

Tammy never shared with me all the details of his date with Steve. But it was very clear to me that Tammy had had an amazingly romantic and passionate evening.

But now Steve was gone, having moved to New York, and I could tell My Little Princess missed him, even though they had only been together on one exciting date.  But the last day of school was fast approaching and that was something good to look forward to.

At Tommy's high school, they have a fun tradition where the graduating seniors -- of which Tommy was one -- come to school in their pajamas on the last day of school.  Of course Tommy had never been one to get very involved in school activities.  He never went to football games or pep rallies or things like that. So I wasn't sure if he would even want to participate in Senior PJ Day, as they call it.

Well, he DID want to participate. And he wanted to participate in a very special way.

"Mother," he said to me. "I've been hiding all my girlish feelings from everyone for so long, always pretending to be someone that I'm not.  Well, tomorrow is PJ Day -- and it's the last day of school forever. So I want to go to PJ Day as Tammy.  The real me.  In a nightgown.  And if people don't like it, well fuck 'em!"

Tammy had never used language like that in front of me before.  It showed how strongly he felt about what he wanted to do.  So I gave him my full support.

Senior PJ Day arrived and we both got up extra early.  We took extra time getting Tammy ready for "her" very first appearance at Tommy's high school.  I warned Tammy that people would be shocked and that he would probably get some pretty strong reactions from people.  But Tammy was determined.

We hadn't discussed it before, so I asked Tammy, "So what exactly are you going to wear today.  Which nightgown have you chosen?"

Tammy replied.  "I have a favor to ask. Can I borrow your white night gown and robe set?"                                                                                  "You mean the one with the eyelet and lace trim? And the buttons down the front?  I haven't worn that one in years.  Well, I guess you can borrow it.  But, it's a bit...grown up and...romantic to wear to school."                                                                                                    "I understand. But it's what I want to do." And with that, I dug out the nightgown set from deep in my lingerie drawer.                                                                                           Tammy put it on and he looked absolutely stunning.                                                                               Ten minutes later I was driving him to school.  His hair and make-up were perfect. He wore just a bit of perfume.  As we pulled up to the front of the school, I asked one more time, "Are you sure you want to do this?"                                                                                             

 "I've never been more sure of anything." And off he went to the entrance of the school.

All morning I worried about My Little Princess being at school looking like a bride on her wedding night.  I kept me cell phone with me in case I got a call and needed to rush to school.  But no call ever came.  At 1:00, I drove back to the school to pick up Tammy, as the last day always ended early.

"How did it go?!?!" I asked excitedly as Tammy climbed into the car.

"It was great!" Tammy said with a smile.  And he proceeded to tell me all about his day.