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 Sissy and his Mother have a Weekend Adventure -- part 3

Janey had a little headache when he woke up the next morning.  But we weren't going to let a little hangover spoil out last "mother-daughter" day in the city.  Janey wore a pretty black and white sleeveless dress, which was perfect because the day was warm.  Our plan was to have breakfast and then head to church -- going to church gives Janey the perfect excuse to get all dressed up on a Sunday morning. Then some more shopping, a light lunch and then back to the hotel for Janey to put his dresses away before heading home.

But just as we were leaving the hotel to walk over to the cathedral we ran into Janey's young banker friend from last night. 

"Janey!" he exclaimed when he spotted us.  He gave Janey a quick kiss on the cheek.  "I'm so glad I saw you.  I was going to call you later, but now I can ask in person."   The young banker looked my son up and down, his gaze lingering on Janey's sexy legs. "Wow! You look...amazing," he panted.

The young banker seemed to have lost his train of thought staring at Janey -- and Janey was so mesmerized by his romantic young banker that he had no idea what was going on.  I helped everyone out.  "Was there something you wanted to ask Janey?" I prodded.

"Oh, yes, right," he managed to stammer as he collected his thoughts.  "I have these tickets to a big charity fund-raiser on Friday night at the Downtown Yatch Club. It's one of the big social events of the year.  It is going to very nice party and I was wondering if, well, if you would be my date for the evening."  

Immediately, and without consulting me, Janey replied, "Oh yes!  I would love to go!"  And with that Janey gave his new boyfriend a big hug.

I, of course, was terrified.  Janey was quickly getting into very deep waters here and I was not at all certain that he would be able to pull this off.

Thinkly quickly, I explained to both of them that Janey and I would again get a hotel room for Friday night and that Janey could go to the party provided that "she" was back to the hotel by 1:00AM.  The banker gave Janey some more details and promised to be in touch soon.  We said our good-byes --  including a big, long kiss for Janey -- and Janey and I continued on with our ladies day out.

The days that followed that magical weekend were very difficult for Janey.  Not only did he have to change back into his boy clothes for the week, but poor Janey was experiencing his first schoolgirl crush. The emotions were so powerful.  He was simultaneously mopey and sad because he missed his young banker boyfriend and wildly excited about seeing him again at a fancy, very adult, cocktail party on Friday.

The school days passed very slowly for Janey that week.  When Friday did finally come, I let him miss school so that I could take him back in to the city to shop for a new dress to wear to the party.   We checked back into our hotel and hit the designer boutiques.  And we found the perfect dress!  It was a black, sleeveless dress with little white polka dots.  It was a faux wrap style that had a bow on one side and was cut tantalizingly low in front. The full skirt came right to his knee, a layer of chiffon gave the whole dress a romantic, elegant effect.  Janey looked stunning in his new cocktail dress.

We spent most of the afternoon getting him ready.  I took Janey to a salon near the hotel to get a mani-pedi (I knew he wanted to wear his favorite open toed shoes with the ankle strap) and to get his make-up done.  

Janey's banker met us in the hotel lobby. I thought the young man was going to die from excitement when he saw how pretty Janey looked. The banker had arranged a limo to take them to the party.  I said goodnight to the young couple and whispered to Janey to be careful.  As the limo pulled away from the curve, I gave a little wave as I watched Janey head off for his first date as a young lady.  

Of course I stayed up waiting for Janey to come back to the hotel that night. When he did get home, he was wide awake and bubbling over with excitement.  Janey had to tell me about every detail of his dreamy, romantic evening:  the music, the celebrities he saw, the food, the drinks, the pretty dresses the "other" ladies wore -- everything.  He even had to describe the fancy ladies rest room at the yatch club.  But mostly he wanted to describe how charming and romantic his date was.  How they danced together and how they made out on the balcony overlooking the harbor.  

Then Janey said, "He wants to take me out on another date -- alone -- tomorrow night."  

I knew that this charade must not continue. Someone was going to get very hurt when the truth came out -- probably Janey.  "No Janey, that is not a good idea.  I can't allow you to do that.  This is all getting very...complicated.  Just what do you think is going to happen when he finds out you aren't really a girl?"

"I already told him and he doesn't care!" Janey replied.  My mouth dropped open and I almost fell over with surprise.  "It's true," Janey continued.  "I told him that am a Sissy during the limo ride after the party.  At first he didn't believe me until pulled down my panties and showed him."

"WHAT?!?"  I exclaimed.  "What did he do then?"

"He said that if I wanted to be his Sissy that I needed to suck his cock.  So I did.  Right there in the limo.  And after he came in my mouth he told me that I suck cock better than any real girl that he's been with.  And that he wants me to be his Sissy! Isn't that wonderful, Mother?  I am so happy!  I am in love with him, Mother."   

Before I fainted, the last thought that passed through my mind was that my sweet little Sissy daughter was now a complete Sissy slut!

Sissy Goes Outside Part 5

For the last few weeks, I've been with Dick every possible minute.  We spend hours in his apartment where he lets me suck on his cock and please him in other ways.  I love making him cum!  It makes me feel alive and valuable to know that I'm giving my Man the pleasure he deserves.

And now we go out together at night too, several times a week.  We go to the movies and bars and restaurants.  It is so exciting to be the feminized Sissy possession of a big strong man.  I love spending my afternoons making myself pretty for Master Dick.  And I love spending my nights being kissed and fucked by him.

I am working so hard to make myself more feminine and sexy for Dick.  I've been dieting and lost seven pounds.  And I've started taking my sister's birth control pills.  The pills have already started making my skin softer and prettier and my nipples have become very swollen and sensitive.

Dick is nice to me almost all the time.  But sometimes I disappoint him and he has to punish me.  I understand.  It is important that I learn to be a perfect Sissy and to always please my Master.  Sometimes Master Dick has to spank me if I have failed him in some way.  He seems to like spanking me, especially if we are out in public.  I am very grateful to my Master for helping me to become a better Sissy.

Master Dick had told me that he had "special plans" for tonight. So I stole this elegant outfit and strappy I I wanted to look my best for my big night with Master Dick, so I borrowed and pretty lacy outfit and sexy strappy shoes from my mother's closet. Then I spent most of the afternoon at the beauty salon and had the girls give me "the works". They even gave my hair some pretty highlights.   I feel so beautiful and feminine!  Dick almost fainted when he saw me!

Dick had made reservation at the fancy French restaurant overlooking the river.  It was all so romantic!  And then, as we were waiting for dessert, Dick got down on one knee.  The whole restaurant went silent and everyone was watching us.  Then, Dick pulled a ring from his pocket and said loudly enough for all to hear, "Will you marry me?  Would you be my Sissy Wife?"

"Oh yes!  Yes!" I exclaimed.  "Of course I'll be your Sissy Wife!"

The people in the restaurant clapped, although they seemed a bit confused by what they just saw and heard.

So now I am going to be married to my Master Dick, who I adore and worship.  I will be able to dedicate the rest of my life to pleasing and serving my Master/Husband.  I am so happy!

And it is all because my sister and her friends caught me dressing in her clothes just a few months ago.  What a lucky Sissy I am!

Sissy Weddings!!! A Sissy Prepares to Walk Down the Aisle

Oh, I do enjoy a Sissy wedding!

It is such fun preparing a reluctant Sissy for his big day.  Ideally, a Sissy doesn't even get to meet his new Master/Husband until he is standing on the alter, repeating the vows that I've written for him.

Sissy Bethany's wedding was such a special day.  Over the past two years, relentless training, surgery and hormones had transformed an ordinary young man into an exquisite feminized Sissy.  The tranformation was difficult, but Sissy Bethany was beginning to understand that he had no hope of ever regaining either his freedom or his masculinity.  And physically, Sissy Bethany's transformation was nearly perfect.  His facial features were delicate and beautiful, his breasts were full and luscious, and his skin was silky and smooth.

It was only two weeks ago that I informed Sissy Bethany that I had arranged for him to be married.  I told him in lurid detail how he was soon to become the property of a real man.  He sobbed when I told him this.  He was terrified by the idea of becoming the Sissy Wife and Slave to a superior male that he had never met.  How he begged me not to make him marry another man!

But of course, nobody cares what a Sissy wants.  And I warned him sternly that I would tolerate no complaints or misbehavior on his wedding day.

When the big day came, I had the girls from the salon meet at us the church where there is a small room near the back where brides can get ready.  The salon girls did a lovely job -- both with his make-up and with tormenting him.  Then I dressed him in the most adorable bridal lingerie set I had ever seen.  The corset-like top showed off his big soft boobs so nicely.  He wore 4 inch white satin pumps on his stockinged feet.  I pinned the lace-trimmed veil to his hair.  He eyed with fear and curiousity the enormous white garment bag hanging in the corner, holding the gown he had never seen.

The guests were arriving.  From the room in the back, I had Sissy Bethany peak out into the church.  There were over 200 guests (all friends of the Groom, of course)  seated in the pews, all happily chatting with one another, waiting for the ceremony to begin.   That's when his fear blossomed into a full panic.  "Please Mistress, PLEASE!" the pathetic thing begged.  "Please don't make me do this!"

Well that did it.  I slapped him hard across the face and screamed at him, "Now listen here, Missy!  Stop your whining right this minute.  You are going to march up that aisle like a good sissy and surrender yourself to your new Husband and Master!  Or do I have to give you a spanking?"  My voice was loud enough to be heard by the guests in the church, who all started laughing at Sissy Bethany's humiliation.

Just then the organ started playing the Wedding March.  "Time to go, Sissy," I said.

"Alright, Mistress," Sissy managed to say through his tears.  "I'll be good.  Will you help me with my gown?" he asked, pointing to the garment bag.

"Oh no, Sissy.  No gown for you.  Because you misbehaved, you can be married dressed just as you are.  I'm sure your Husband/Master will enjoy seeing you wearing your sissy lingerie as you recite your vows to him.  And I'll bet some guests won't be able resist giving you a feel as you walk pass."

Sissy Bethany went pale with shock.  I handed the Sissy his bouquet and literally shoved him out the door.  "Start walking," I said pointing down the aisle.  And that's what Sissy Bethany did, slowly and shamefully walking down the aisle, wearing only his exquisite lingerie and veil, towards his future as a Sissy Slave Wife.  The guests hooted and laughed as the humiliated and half-naked Sissy walked by.

A Sissy Gets Ready to Go Home

Charlie had been nothing but trouble for his poor Stepmother.  He had gotten involved with drugs and shoplifting and had gotten expelled from high school just too many times.  And around the house he was rude and obnoxious. 

Fed up with this nonsense, Charlie's Stepmother did the right thing and delivered her rotten stepson to me for some...improvements.

It wasn't easy and it wasn't quick.  But in a little more than two years, Charlie was gone forever and in his place was -- TA DA -- Sissy Charleen!  All it took was some hard work -- and some hormones, some surgery, some sleep and food deprivation, and lots and lots of beatings.  Sissy Charleen was now a quivering, submissive and totally obedient feminized girly-boy.

I enjoyed preparing Sissy Charleen on the day his Stepmother was coming to retrieve him.  Starting very early in the morning, I had the girls from the beauty parlor come over to give Sissy Charleen "the works".  First, a total (and I mean total) body waxing -- ouchy!  Then his hair was shampooed and put up in rollers.  While he sat under the hair dryer, the girls did his make-up and gave him a mani-pedi.  His hair was then brushed out and styled, soft curls pinned back with a pretty bow.  Adorable!

Now, up until this point, little Sissy Charleen had no idea why he was being all gussied up.  As I zipped him into the cutest little pink dress, I explained that his Stepmother had come to take him home and that she was waiting right outside.  Well the little Sissy nearly passed out when I said that!  Sissy Charleen was terrified of being under the control of his Stepmother in his new feminized condition.  Sissy Charleen started to cry and begged me not to return him to his Stepmother.  I sternly instructed him to stop crying, lest he spoil his lovely make-up.  I then reminded him that no one cares what a Sissy wants and that he had best work hard to obey and to please his Stepmother-- or there would be trouble. 

I stepped back to look Sissy Charleen over one last time and to admire my work.  His arms and legs looked so delicate and feminine.  His hair and make-up were perfect.  And the dress I had chosen was simply lovely -- so sweet and innocent.  I gave his hair a final fluffing out and made sure his sparkly heart shaped earrings weren't hidden. He stood there, so prim, so feminine, so terrified, as I invited his Stepmother to enter.  The poor little defeated Sissy's chin quivered as he fought so hard to hold back his tears. 

As she walked into the room and saw her transformed Sissy stepson for the first time, she screamed. "OH MY GOD!"  She nearly collapsed with laughter as she drank in her little Sissy.  Of course Sissy Charleen was dying of humiliation, but he stood there, eyes lowered, as he had been trained.  The Stepmother eyed Sissy Charleen's bust and asked aloud, "Are they real?"  She brazenly walked up to Sissy Charleen and gave his boobs a rough squeeze.  "OH MY GOD!" she screamed again.  "They are real!"  Her riotous laughter resumed.

"Come along, Sissy Charleen.  Time for us to go home.  But first we're going to go downtown so all of your old friends can get to see the new you!"

A Stepmother's Sissy

After my father's death, my evil stepmother sent me away to feminization clinic in Brazil.  There, over the course of 18 months, I was forced to undergo a total transformation from a normal teenage boy to sexy submissive sissy.  The feminization clinic was part hospital, part bizarre finishing school and part hellish concentration camp.


I was awakened extra early today and taken to the salon, where over the course of several hours my hair and make-up were done in a very glamorous style.  Then I was brought back to the Administration building where my trainers dressed me in this very fancy lingreie. 

As several bracelets were slipped on my wrist, I heard my stepmother's voice coming from the next room.  I had not seen her since she had imprisoned me in the clinic a year and a half ago.

"That's right, Sissy, your Stepmommy is here.  She can't wait to see what we've done to you!  Time for your big debut," one of my trainers said with a cruel smile.

"Well hurry up and get out here!" my stepmother commanded from the next room.  "Don't be shy -- no reason for my new stepdaughter to be bashful in front of her stepmother," she cackled.

I was frozen with fear, horrified by the idea of parading aroung in front of her in my bra and panties, my complete sissification on full display.

"Get out there and behave yourself -- or else," the trainer threatened, brandishing the cattle prod he always carried. 

I swallowed hard and braced myself for the humiliation that awaited me.  I nervously parted the beaded curtain that hung in the doorway and made my entrance to the other room.  There was my horrible stepmother, seated on a sofa snuggled up close to a man I had never seen before.

My stepmother squealed with delight when she saw me.  "Oh my Gawd!" she exclaimed.  "It's even better than I could have dreamed.  Look at you, you pathetic sissy faggot.  What a little sissy slut you must be, prancing around in your girly undies for everyone to see."

"Isn't this wonderful, Roberto," my stepmother said to the man next to her,  "Now that my loser stepson is gone forever, I will inherit all of his father's millions.  We are rich, Roberto!" she said giving him a big hug.

"Well, time to go home Sissy.  Today you start you new life as my personal handmaiden, my own fulltime servant tending to my every need.  Won't that be wonderful?" she teased.

"We will dress her and bring her to your limo," the trainer helpfully offered.

"Oh heavens no," my stepmother replied.  "She doesn't need clothes.  She looks so lovely just the way she is.  Come along Sissy, get in the car.  A new life awaits!"

Sissy Goes Downtown

The poor little sissy was shaking with nervousness. "Oh settle down now," the Mistress/Wife ordered. Sissy Tina was fully made-up and his hair was done perfectly and dressed in an elegant, impractical, and attention-getting pink suit. Best of all -- at least for the Mistress/Wife -- was the matching pink hat, purse and shoes.  Sissy Tina had burnt the breakfast toast last Wednesday and had to be punished.

"I have such a fun day planned for you," the Mistress/Wife said with a cruel smile on her face. "First, I am going to drive you into town, and drop you off at the corner of Market and High Street at 10:00. And from there you can begin your exciting day downtown." Sissy Tina started to feel dizzy knowing that a major humiliation had been planned for him. "From there you can walk to Kim's Salon where "Sissy Tina" has an appointment for a manicure at 10:30. Then at 11:15, "Sissy Tina"is expected at the Lancome make-up counter at Macy's where the girls there will fuss over you and help you look your prettiest. Oh, while you're at Macy's, be a dear and pick up some sexy boxer briefs for my hunky boyfriend Mark. At 12:30, they are expecting "Sissy Tina" at Victoria's Secret for a bra fitting." Sissy Tina thought he was going to die -- but the Mistress/Wife wasn't finished yet.

"Then I need you to stop at the photographer's studio and pick-up the photos from my vacation with Mark in Bermuda. Go through all the photos very carefully and pick out the three most romantic photos of Mark and me together and have them framed while you wait. Don't worry, I'll let you have one of the framed photos for your room."

"Then you'll have to hurry, because I've reserved a table for "Sissy Tina" at Cafe Moulin at 2:00. You'll be sitting alone at the table by the big window in the front where you'll be on display for all the passers-by to see. Mark and I will be sitting at another table enjoying watching you."

"But Mistress," Sissy Tina pleaded, "please don't make me walk all the way across town dressed like this. Everyone will stare at me -- nobody dresses like this. And please don't make me go into all those shops telling everyone that I'm a Sissy." Sissy Tina was near tears.

"Well," said the Mistress/Wife, "perhaps this will teach you to be more careful when you make breakfast for Mark and me in the future. Now stand up straight, put a smile on your face and get in the car."