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!

 

Mommy's Pajama Sissy -- Part 10

When I picked Tammy up from school, he was all smiles.  "Well, how did it go at school?  How did people react to seeing you as Tammy -- and in a nightgown?"

"It went great!" Tammy practically shouted.  "Of course, when I first arrived, I got a lot of stares walking down the hall to homeroom. But mostly I think people were staring because they didn't know who I was -- or why someone was wearing such a fancy nightgown to PJ Day!"

Tammy continued. "When I first got to homeroom, people were shocked.  I mean speechless. I thought it was hysterical!  But after just a few minutes, a bunch of the girls -- the cool girls, the ones that never talk to me -- came over and started fussing all over me. They were saying how pretty I was, how jealous they were, and so on.  It was totally fun!"

"It was sort of funny," Tammy continued, "That I was the one wearing the prettiest nightgown! Most of the other girls were wearing pajamas or flannel nightgowns -- like the ones we wear together in the winter. Nobody was wearing a fancy, pretty nightgown like me."  I was relieved to hear this as I thought Tammy's selection of nightgown wasn't exactly appropriate and I thought it might cause a problem -- but apparently not.

Tammy continued, talking a mile a minute. "But of course, the boys noticed me too.  A bunch of them just couldn't stop staring at me while I was chatting with the cool girls.  And then a couple of brave ones came up to me.  At first I was worried that they were going to give me a hard time or start calling me names.  But that didn't happen. Instead Jimmy Michaels came up to me a said 'Wow, you really look amazing. I barely recognized you.'"

I was shocked to hear this because I was aware that Jimmy Michaels (who was captain of the football team, by the way) had never been nice to Tommy over the years, calling him names like "sissy" and "faggot" just because he didn't like to play sports and because he mostly kept to himself.

"Well, after homeroom, we all went to the auditorium for the end of year presentation. The girls from my homeroom asked me to sit with them, and we were joined by the cool girls from the other homerooms.  And everybody was super nice to me and made a big deal about how pretty I looked." Tammy was practically breathless from talking so fast.

"Then after the presentations, we all went to the gym where they handed out yearbooks.  And they had pizza and soda and everybody spent the rest of the day signing each others' yearbooks and chatting and eating.  This time Jimmy Michaels came up and talked to me, even offering to get me some pizza and soda. He told me that he would working all summer at his uncle's car shop on North Street and he said that he hoped that we would get to hang out together over the summer..."

"The whole day went by in a flash. Before I knew it, it was time to go home."

"Well, young lady, you certainly had an exciting day!" I said. "You must be exhausted."

"Oh, I guess. But I'm supposed to meet some of the other girls at the mall at 3:00.  Can you drive me?  And tonight, Jimmy invited me to go with him to end of year bonfire down by the lake -- can I go to that too?"

"Well, I don't see why not. If it's what you want to do," I said.

Tammy's life experienced a big change as a result of his wearing a pretty nightgown to PJ Day.  That whole summer was a whirlwind of parties and days at the lake and afternoons at the mall and nights at the movies. Needless to say, I had to spend quite a bit of money on getting Tammy all the clothes that he needed now -- casual outfits and jeans and tank tops; swimsuits and cover-ups; party dresses; the works!

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. 

Mommy's Pajama Sissy -- Part 3

By the time Christmas arrived, Tommy and I had been sharing my collection of pretty ladies pajamas for several weeks.  He had wore every set I own at least a few times.  I thought Tommy would enjoy something new.

On Christmas Eve, it is our tradition to open one gift each, saving the rest for Christmas morning.  This year, I had picked out a very special Christmas Eve gift for Tommy to open.

When Tommy opened his gift, he was almost overcome with joy.  Inside was a pretty blue flannel nightgown of his very own.  "Oh Mommy!  I love it!  Can I put it on now?"

"Of course sweetheart," I replied.  And when Tommy returned downstairs in his pretty new nightie, he had a second surprise.  I was wearing the exact same nightie.  "Surprise, sweetheart!  Now we're twins!"  Tommy ran up and hugged me.  He told me he loved me.

I fixed his hair and put a little lipstick and blush on him.  I added just a spritz of the flowery perfume he liked so much.  He was simply lovely in his pretty new nightgown.

We spent all Christmas Eve -- and most of Christmas Day together wearing our matching nightgowns.  And we had a wonderful on Christmas afternoon snuggled up together on the couch under a warm quilt watching chick flicks on TV.  My sweet Tommy cried during "The Notebook."

Over the next few weeks I bought Tommy -- or as I was now calling him -- Tammy -- and me several more pretty matching nightgowns to get us through the cold winter together. 

Mommy's Pajama Sissy -- Part 1

Last fall, shortly before Halloween, the weather turned suddenly very cold.  Our house is rather drafty so I wanted to be sure that my teenage son Tommy stayed warm.  But I then discovered that, over the summer, he had outgrown all of his winter pajamas.  Since Tommy and I were about the same size, I suggested to Tommy that he borrow a pair of my flannel pjs.  I handed Tommy a set that was white with a pale blue floral print.  I thought he might protest, but he didn't.

When Tommy emerged from his room wearing my pajamas, I could tell that his mood had brightened.  He went into my bedroom and stood in front of the big mirror, admiring his reflection. "Do you like those pjs, Tommy?"  I asked.

"Oh yes, Mommy.  I do.  I think they are very pretty," he said.  "Mommy," he continued hesitantly, "Do you think I'm pretty?"

"Pretty?" I responded with surprise.  "Well, I never thought about it, but yes, I suppose you are pretty."

He smiled.  "I want to be pretty.  Pretty like you," he said, still gazing at his reflection.

I was puzzled but also very touched by what he said.  "Well, maybe I can help you to be even prettier," I suggested.  I sat Tommy down at my vanity and started to brush out his hair.  His curly, dirty blonde hair hung down nearly to his shoulders.  As a boy, his long hair gave him a wild, surfer dude look.  But as I brushed it I realized just how pretty his hair was.  I gathered up some of his hair and pinned it up in back.  I brushed out a few tendrils and let them fall to the sides of his face.  I dabbed some pink gloss on his lips and brushed a little blush on his cheeks.  When I asked him if he wanted me to spritz him with a little cologne, he said, "Yes please, Mommy."

Tommy and I proceeded to spend a delightful evening together, both of us wearing pretty flannel pjs.  We snuggled up together under a blanket on the couch and watched tv together, something we hadn't done since Tommy was just a little boy.

That night, I even tucked Tommy into his bed.  He did indeed look very pretty, with his lips and cheeks pinked with my make-up and his brushed out hair falling across the pillows.  I kissed him good night on the forehead and he said, "Thank you Mommy."

As I turned off his light and closed the door to his bedroom, I wondered if this was going to prove to be a one-time event.  I suspected it would not be.

Sissy Priscilla Part 3 -- Mother's Wedding Surprise

After I had taken about a million photos of my beautiful sissy son bride, I told him that we should head back inside.  I could tell he was sad when I said that, sensing that our bridal fantasy day was wrapping up.  But I had other ideas.  In fact, the fun might be just beginning!

As I said earlier, sissies have such limited lives -- no friends, no romance.  But I knew I could change that.

You see, at the same time that I was making arrangements to rent the cottage and buy flowers for today, I had also gone online to see if I might be able to find a fantasy "groom" to make Priscilla's wedding fantasy complete.  There are plenty of websites out there for men looking to meet sissies. My challenge was to find the right one.  I posted some details of what I was planning for my little sissy and, needless to say, I got hundreds of responses from horny men wanting to have some dirty action with my sweet sissy son.  But one profile stood out from all the others -- a young, tall, handsome man, clearly well educated.  He seemed to understand what I was looking for in a "dream date" for Priscilla.  I arranged to meet him in person and I liked him immediately. His name was Kurt. 

So on the day of Priscilla's wedding, while Priscilla and I were taking photo's outside, Kurt arrived at the cottage and waited patiently for us inside. When he saw us starting to walk back toward the cottage, that was his signal to come out.  Little Priscilla was so frightened and worried when this tall man walked out of our cottage and started walking straight towards us.  "Now, now, Priscilla," I reassured. "Don't be frightened.  In fact I know this man.  His name is Kurt and I invited him."

Priscilla looked so confused and scared.  Kurt confidently strode up to Priscilla.  "Hello, Priscilla," he said.  "I am Kurt.  Your groom.  Your husband.  For today." 

Well, it took some time for Priscilla to compose himself after much reassurance from me. "Come, come, Priscilla," I said.  "Play along.  This is all part of making today's fantasy complete."  After a while, Priscilla relaxed, mostly because Kurt was so charming and gentle with him.  Before too much longer, I was able to get Priscilla to smile and pose for some photos with Kurt.  Here's the first photo I took.


Well, after the first photo was done, I was able to take about two hundred more as I asked them to pose in various locations around the pond.  With each passing moment, Priscilla became more relaxed around Kurt and seemed to ease more naturally into his role as the petite bride to Kurt's manly groom.

"Now a kiss!" I shouted.  Priscilla was shocked when I said this.  Kurt wisely went in for a gentle peck on Priscilla's forehead.

"Oh that won't do at all!" I cried.  It's time for a real kiss."  And I guess Priscilla agreed.












Kurt pulled Priscilla hard against him as Priscilla closed his eyes and allowed Kurt to kiss him for a very, very long time. I was delighted to see my little sissy son experience romance for the first time in his life.  I took dozens of photos of this lovely embrace.



We went back inside the cottage where I insisted that Kurt and Priscilla act out a wedding ceremony while I took even more photos.  I had arranged for some wedding flowers for the living room to set the mood.  

"Do you, Kurt, take Priscilla to be your wife?" I intoned.  "I do!" said Kurt while Priscilla beamed.


"And do you, Priscilla, take Kurt to be your husband?"  "Oh yes, I do!" replied my eager and delighted sissy son.  "You may kiss the bride." I instructed Kurt.  And Kurt did as I told him, scooping Priscilla up in his arms and kissing his lovely bride.



















"And now for your first dance as husband and wife!" I shouted and pressed play on the CD player.  John Legend's "All of Me" began to play.  Kurt expertly led Priscilla around the living room in a gentle, slow, romantic dance.  As the song came to an end, I decided it was time for me to make my exit.  "Well, three's a crowd," I said.  There's a light dinner and a bottle of champagne for you two in the refrigerator.  I will be up in my room.  Have fun.  And congratulations!"  Priscilla giggled as I left.


At about 6:30 the next morning I heard Kurt leave the cottage and drive off in his car.  I came downstairs and found Priscilla, in his vintage peach peignoir set, sipping on a cup of coffee, looking rather disheveled -- and a bit embarrassed.

"Well, well, well," I said. "And how is the new bride this morning?"

Priscilla waited a moment, finally answering, "A bit sore, actually."  We both broke out in laughter when he said that.  I gave my sissy bride son a great big hug.  

"I hope you enjoyed your wedding fantasy, darling," I said.

"Oh yes mother.  That was the most wonderful day -- and night of my life."

Kurt continued to be a frequent visitor at our home after Priscilla's sissy wedding.  But those are stories for another time.

Sissy Priscilla Part 2 -- A Sissy Wedding Fantasy

For the past few weeks, I have been planning a very special weekend for my sissy daughter, Priscilla.  It all started when I was at a Thrift Shop and I happened to find a beautiful wedding gown in Priscilla's size for just $20.  Of course I bought it.  Here is the plan I came up with -- as soon as it was warm enough, we would rent a little cottage in the country for the weekend.  We would make the whole weekend about Priscilla's wedding fantasy!  Priscilla was so excited when I explained this to him and when I showed him the wedding dress.  I told him how we would do his hair and make up just so and then take a million photos of him as a blushing bride.  I had a few more surprises planned -- but that was all I wanted Priscilla to know about in advance.

We chose a weekend in late April and found the perfect little cottage to rent with a lovely property for taking wedding photos.  When the weekend finally arrived, I thought my darling little Priscilla was going to burst with excitement!

We drove out to the cottage on Friday afternoon, after Priscilla had come home from school and had a chance to change out of his boy clothes and into his girl clothes.  I already had everything we needed packed in the car so off we went.  We had a light dinner and afterwards I dressed Priscilla in a lovely vintage Vanity Fair peignoir set in the softest peach.  He looked so lovely as I tucked him into bed and kissed him tonight.  I wished him sweet dreams and urged him to get a good night's sleep before our exciting Saturday.

At sunrise, I brought Priscilla some toast and tea in bed and we started our day. After Priscilla showered, we spent the next couple of hours getting him all prettied up for his wedding fantasy. He started with his hair which was now almost down to his shoulders.  I watched him as he brushed in hair out in the mirror.  He seemed so happy and so natural getting ready to be a bride for the day.

Next I helped him into the lovely vintage gown I had bought for him.  I buttoned up his dress in back.  I felt so happy having the opportunity to dress my lovely bride-daughter -- even though my only child was a boy!  Since I never had a real daughter of my own, I thought this day would never come for me.  Yet here I was -- the happiest mother-of-the-bride that ever was!

Then he finished doing his make-up and voila!  My little boy was now a lovely, blushing bride.  He looked so beautiful!  I felt so proud and so happy as I looked at my little boy-bride.  

We spent the next 20 minutes pinning a wreath of fresh pink and white roses on his head.  He insisted that it had to be perfect.  It took me about ten separate tries to get it positioned to his satisfaction.  I was astonished just how much my little boy was acting like a real bride on her real wedding day.  Finally his floral crown was just right and he was complete!!!!

I picked up my camera and started taking photos for the next two hours.  We took photos everywhere -- in the cottage and around the lovely grounds. I could tell that my sweet Priscilla was having the time of his life pretending to be a bride for a day. 

I was happy that my sissy son was having fun, but as his mother I also felt some sadness.  Of course I knew that as a sissy, my son had no real friends -- and had certainly never had a real romantic experience of his own.  Real boys shun sissies like my son.  They really have nothing in common after all and could never be friends.  And sissies are too weak and too fearful to develop meaningful relationships with girls.  So while I was delighted to bring joy into Sissy Priscilla's life for one afternoon, the fact that it was just a pretend fantasy made me a bit sad.



But I had more surprises in store for Priscilla this afternoon -- something that he would never have anticipated.  I was nervous that perhaps I had gone too far -- but I was also far too excited to stop.

 

"Priscilla, darling," I called after taking a few dozen photos by the pond.  "I think it is time for us to go back inside now."

I could see a hint of disappointment on Priscilla's face when I said that, assuming that his day as a bride was coming to close.  But of course, he had no idea what further surprises I had for him.

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 Sissy every Weekend -- Part 7. After the Dance

Caroline followed me back to the bedroom.  She sat down on the edge of the bed and gently placed a hand on my shoulder.

"I'm sorry I teased you like that," she said.  "I really do appreciate what you did for me tonight.  And I would like to show you how grateful I am."

I had no idea what she was suggesting.

"Now take off your dress and put on your nightie and I will be back in a minute."  Caroline disappeared into the bathroom.

I forced myself to stop crying and dried my eyes with a tissue.  I stripped off the pretty dress, the stockings and the bra and panties I had worn to the dance and slipped on my pink nightgown.  Caroline emerged from the bathroom wearing only her bra and panties and carrying a bottle of lotion and a small towel.  "Now I want you to just lie back and relax," she said as she sat on the edge of the bed.  She looked so beautiful wearing just her underwear.  I tried not to stare but I couldn't help it.

As I laid back, Caroline lifted the bottom of my nightgown.  She squeezed some lotion onto her palm and began to gently stroke my little penis.  I had never felt anything like this before.  Here was the girl I loved so much, wearing only her bra and panties, giving me a hand-job!  My little penis instantly became erect.  As Caroline stroked me I tried not to think about how much different I must be than her boyfriend Robert.  Robert was big and strong and masculine; I as dainty and feminine, my skin was soft and my cock was tiny.

I couldn't believe this was really happening.

Caroline stopped pumping for a moment.  "Now don't make any noise, Sweetie.  We can't let anyone know what we are doing.  Do you promise to be quiet?"  I quickly nodded in agreement.  Caroline resumed playing with my cock with her soft, lotion-covered hands.

"Does that feel good, Tiffany?" Caroline whispered into my ear as she continued to pump my little penis.  "Ohhhh, yes," was all I managed to reply.

And then I started cumming.  My little cock just exploded, spurting and spurting, over and over.  Caroline smiled down at me while I orgasmed.  "Well," Caroline said.  "It looks like someone really enjoyed that!"  She kissed me on the forehead and went into the bathroom to wash her hands.

When Caroline returned she again at on the edge of my bed.  "You really were wonderful to go to the dance with me tonight."  She stroked the my cheek with her soft fingers.  "Now get some sleep."

She moved to her bed. "Oh, by the way.  Robert's parents have invited you, me and Mark out for brunch tomorrow morning.  I already said that we are going. It will be fun and I know Mark will enjoy seeing you again.  And if it all goes well, who knows, maybe I'll be able to show you how grateful I am again."  With that Caroline turned off the light and climbed under her covers.

Caroline was completely manipulating me.  She knew she had me under her spell and I was powerless to resist.  Tomorrow I would be out again -- with a boy who thought I was really a girl.

I struggled to fall asleep, but when I did, I had dreams about Caroline -- and Mark.

A Sissy's Dinner Date Fantasy - Part 2

Within a week of posting my profile, over 200 men had written to me!  I read every single message that I received. Then I carefully studied each man's profile and photos and I wrote flirty notes back to several of them. It didn't take long before I had actually scheduled a date with one of them!

For my very first date I had selected a man that seemed particularly promising. He name is Mark Jensen and he was in his mid-40s, divorced and a bank executive. He described himself as being six-foot-two and in excellent shape. And best of all were his photos! He was very handsome, with strong, chiseled features. His dark hair had a bit a grey at the temples.  One of his photos was taken at the beach -- with his shirt off exposing his muscular chest and shoulders!

We exchanged several emails and then we talked on the phone. I had practiced my girly voice and he didn't suspect a thing. In fact, he said my voice was sexy. And at the end of our conversation we agreed to meet for a date on Friday night!

I couldn't stop thinking about my big date all week. Even though I owned two pretty dresses that I could have worn, I decided I needed something even more special. I went to Macy's and spent $400 on a gorgeous black dress and another $200 on some sexy sling-backs with 3 inch heels.

On the night of our first date, I met Mark at Le Maison, the fanciest French restaurant in town. He was already sitting at the bar when I walked in. He looked just like his photos -- tall, handsome, sophisticated. He seemed very happy when he saw me for the first time. He gave me a quick peck on the cheek as he greeted me and the Maitre d' walked us to our table.  

My dinner date was just heavenly. Mark was a perfect gentleman and I felt like a perfect lady. He ordered a very expensive bottle of wine which was wonderful. We chatted about this and that. Mark mentioned several times during dinner that I looked very pretty -- which made me blush each time. Being with Mark made me feel like I was one of the beautiful, enchanting women in the romance novels I had read. 

We had a second bottle of wine and our conversation became flirtier. I was having so much fun -- it was like a dream come true.  

As dessert was being served, Mark got out of his chair and gave me a big kiss -- right there in the restaurant! It was so spontaneous and so romantic!

After dinner, Mark walked me to my car in the parking lot. But the evening didn't end there. We made out in the parking lot for another twenty minutes. Mark pressed me up against my car while he frenched me hard. He was so strong and forceful. I could feel his dick getting hard as he rubbed against me. It was so exciting!!! His hands even drifted up to feel my breasts -- he had no idea he was squeezing silicone falsies. He practically begged to see me again on Saturday, but I said no -- not because I didn't like him, but because I already had other plans for tomorrow night!

You see, I had already arranged a date with another man for the very next night!

After I got home from my exciting first date as a girl, I put on a sexy nightgown, some soft music and made myself cum, looking at Mark's profile photos, imagining that our wonderful date hadn't ended in the parking lot.

Elegant Sissy at Bedtime

Knowing that his Master demanded absolute Sissy perfection, Sissy Lisa spent hours each evening preparing himself for bedtime to ensure that his Master was pleased.  Sissy Lisa made sure that his hair and make-up were sexy and elegant.  He donned the luxurious night gown and robe that had been an "anniversary" gift from his Master.  Tonight they were celebrating the 6 month anniversary of Sissy Lisa's enslavement to his Master.

 
"Oh baby, you are so hot!"said his Master as Sissy Lisa made his grand entrance into the Master bedroom.  "Now get over here and wrap those pretty Sissy lips around my big fat cock."