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 12 -- The Conclusion

It turns out that Jimmy told Tammy that, as Captain of the football team, he was expected to "share" his girlfriend with some of the other seniors who were on the team.  This is what I overheard Tammy talking about on the phone.  Well, I couldn't believe what I was hearing, but it seems like my sweet, innocent Tammy was going to listen to whatever Jimmy said -- and do whatever Jimmy asked.

The very next day, I heard that Jimmy and Tammy went to the beach -- along with Jimmy's teammate Marcus.  Tammy didn't share any of the details of what happened at the beach but he seemed completely fine with whatever did happen.  I guess Tammy enjoyed the extra attention of two boys instead of just one.  

I soon had the impression that Tammy's dates with Jimmy usually included one -- or more! -- of Jimmy's football buddies.  I began to become concerned that Tammy was letting himself get caught up in something that wasn't very healthy for a young lady like Tammy.  But as unhappy as I was that Tammy was being "shared" among the players on the football team, I soon learned that the situation was perhaps even much more worrisome than I knew.

Tammy had been very open with me about his early experiences with Jimmy, but as the summer wore on, Tammy became much less willing to fill me in on the details of what he was doing.  I started checking his phone when I could just to get an idea of what he was up to.  So you can imagine my shock when I found these photos on his phone.  Because that's not Jimmy that Tammy is kissing.  That's Jimmy's Uncle Mike who owns the garage where Jimmy works!  Mike is in his mid-40's and shouldn't be romancing an innocent teenager like my Tammy!

And not only was Jimmy "sharing" Tammy with his Uncle Mike -- but apparently, Uncle Mike was "sharing" Tammy with his friends too!  The photos on Tammy's phone weren't very clear so maybe I'm not exactly sure what I'm looking at. Maybe you can figure out what's really happening here...

Oh dear! Perhaps this is all my fault!  It was just so much fun when we started wearing cute pajamas and nightgowns together  I could never have imagined that it would lead to this.

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 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 8

When Tammy and Steve arrived at Steve's parents' home, Steve quickly poured himself a stiff drink.  They had already started having a conversation about exactly who Tammy was and Steve was beginning to come to terms with the fact that the beautiful girl he had been French kissing on the dance floor wasn't really a girl at all.

But Steve wasn't angry or upset.  He really mostly seemed confused and conflicted.  He had fallen very hard for Tammy and it was a struggle to incorporate this new, shocking information with what his eyes and emotions were saying.

"Do you want me to go?" Tammy asked at one point when Steve seemed to be out of questions and the silence hung heavily in the room.

"I don't know.  I don't think so. Maybe if we just spend a little time here together we can figure out what exactly we are feeling and what we should do next," Steve suggested.

So they sat quietly together on the couch for a few minutes.  Steve broke the silence saying, "God, you even smell fantastic."  That comment broke the tension and Tammy giggled a little.

"Steve," Tammy started, "I think you like me as a girl. And I know I like you. So maybe, just for the rest of the evening, we could both go on pretending that I'm really a girl."

"But what would your mother say? Do you think she wants this to be happening?  Do you think she wants you, her son, hanging out alone with an older man who, just a few minutes ago, was kissing you on the dance floor?!?"

"I think my mother has the hots for you just as much as I do. If I wasn't here, I bet she would want to be! But I'm guessing you have that effect on girls' mothers," Tammy offered. "So no. I don't think my mother would have any problem with me being here with you tonight. I think she would be happy that I've having this sort of experience with such a nice and handsome man."

Steve didn't have an answer to that. So Tammy continued, "So, if I really was your girlfriend, what would we be doing right now?"

"Making out, I guess. Is that what you want to do?" Steve asked.

"Yes!" Tammy breathed as he wrapped his arms around Steve's strong neck and kissed him hard.  And Steve kissed him back. Steve pushed Tammy down onto the couch and climbed on top of him.  Their kissing and their breathing became harder.  As did something in Steve's pants.

"If I was really your girlfriend, what would you want me to do now?" Tammy whispered.

"I'd want you to pull down my zipper and take out my dick and start to stroke it," Steve replied. And that's what Tammy did.  Tammy was amazed by how huge Steve's cock was -- many times bigger than his own little one.  And it seemed to grow bigger with each gentle stroke.

"May I put it in my mouth?" Tammy asked.  Steve could only nod.  Tammy kissed the end of Steve's rock hard dick, and then licked it, and then pulled it into his mouth.  Steve's eyes were closed and he was making quiet moaning sounds so Tammy figured he was doing it right.  "Oh that feels so good," Steve moaned.  "So good."

After playing with Steve's dick in his mouth for about 10 minutes, Tammy said, "I want you to make love to me. Treat me like a real girl and fuck me.  Please."

"Let's go upstairs to my bedroom," Steve replied.

When they got there, Steve stripped naked. "Are you going to get undressed?" Steve asked.

"Oh, no. I don't want to be naked. I need to be wearing girl's clothes to feel like a girl," Tammy explained. "Give me a minute." And Tammy exited Steve's bedroom.  A moment later, Tammy returned wearing a black satin and lace nightgown. "How's this?" Tammy asked with a smile as he twirled in front of Steve.

""Did you take that from my mother's lingerie drawer?!" Steve asked with some distress.  Tammy nodded yes with an enormous smile on his face. "Oh, God, I'm going to be in therapy for years because of you." Under the silky nightgown, Tammy was still wearing his bra and padding, so he had the shape of  a woman and Steve couldn't help but be excited by the image of a sexy woman standing before him. 

"Wow," said Steve, "You look amazing. I am so turned on right now." And with that, the two lovers climbed into bed.  Steve positioned Tammy on his side, with his bottom facing Steve.  Steve lifted the hem of Tammy's nightgown, exposing his soft little bottom.  Steve applied some lubricant and warned Tammy that it might hurts a little since it was his first time. Steve began to gently work his giant, rock hard dick into Tammy's virgin sissy pussy.  With each stroke, Steve's cock penetrated deeper and deeper into Tammy. Soon, Steve's thrusts became harder and quicker, his moaning louder, his grip on his feminine lover tighter. And as Steve came inside of him, Tammy's own little penis also exploded into the soft, silky fabric of the nightgown that was rubbing against him.  

For Tammy, the experience was quite painful -- but also exquisite. Allowing his body to be given over for the pleasure of a real man. To feel a real man plant his hot sticky seed deep inside his body. To surrender completely to the needs of the woman that lived inside of him.  It filled him with a sense of happiness and fulfillment unlike anything he had ever experienced.

As Steve's dick began to soften, he started to withdraw from Tammy's backside. Tammy reached around and grabbed Steve's ass. "No," he said. "Please leave it inside of me for just a bit longer."

As they lay there, still wrapped tightly together, they both fell asleep for a few minutes, both feeling exhausted and content.

When they awoke, Steve kissed Tammy again and said, "I think I need to drive you home now, darling."

Mommy's Pajama Sissy -- part 7

 

Tammy was having a magical time at the fancy tea dance, being led on the dance floor by his handsome date, Steve.  Tammy allowed himself to be carried away by the experience, resting his head on Steve's shoulder.  And when Steve leaned in to kiss Tammy, Tammy didn't resist at all.  Deep kisses continued on the dance floor as the band played a slow, romantic song.

"I'm going to miss you when I leave for New York on Monday. Do you think you will be able to visit me?" Steve said.

That question triggered something in Tammy's head that he decided to act on.  "Steve," Tammy whispered in his ear as they danced, "I haven't been completely honest with you."

"Oh, really?" Steve replied, having no idea what he was going to hear next. "Well, now might be a good time to set the record straight. I'm ready. Let me hear it."

"Well," Tammy said softly into his ear. "For one thing, I'm not really 22 years old like I said last night. I'm 18."

"Yikes!" Steve responded with real surprise. "That makes me much older than you. I really shouldn't be dating 18 year old girls. Well, at least you're...legal.  I'm going to need to think about this. But in the meantime, please lay off the champagne.  You shouldn't be drinking."  Tammy agreed.  "Was there something else? Steve asked.

"Well, yes," Tammy started. "This is a bit hard to explain, but I wasn't exactly born this way. I mean, gender-wise.  I haven't always been a girl like this."

"Are you saying that your trans?" Steve whispered back to Tammy. "Wow, that is a surprise. But you're so...feminine. I would never have thought. I suppose you transitioned when you were young.  Wow, there is a lot to learn about you!"

To Steve's credit, he seemed more concerned with Tammy being 18 than the fact that his date was a transwoman.

"It's not exactly like that," Tammy whispered back. "I...I...I," Tammy stammered.

"You what?" Steve prompted, struggling to keep his voice at a whisper.

"Steve, I'm a boy," Tammy explained simply.  Steve went a little pale. 

They retreated back to their table where Steve said, "Look, there is a lot we need to talk about but we can't talk here. I was planning to take you out to dinner later, but maybe we should just go back to my folk's place and talk in private there.  Is that OK with you? Tammy agreed and off they went.

Mommy's Pajama Sissy -- Part 6

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

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

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

Mommy's Pajama Sissy -- Part 5

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

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

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

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

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

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

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

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