A Reluctant Sissy -- Part 6 - Sissies for Hire

About a month had passed before I received another letter from Mrs. Trainer.

"Dear Mrs. ____,

Sorry for the delay in writing but things here at the school are very busy indeed.  This is a crucial time in our training process where we expect to see our sissies display the attitude and actions that are expected of them without any reminders, prodding or punishment.  We are still enjoying our trips into London and our Thursday night officers' parties.  And I am delighted to report that your son is by far the best behaved, hardest working, most delightful little sissy in the entire class.  We are absolutely thrilled with how far he has come in just five short months here.

There is a special privilege (well, I 'm not sure the sissies see it as a privilege) that we reserve for our most accomplished, most feminized, most obedient sissies.  On occasion, if one (or more) of our handsome, older Air Force officers wants to "borrow" a sissy, that is something we can sometimes arrange.  Well, I can assure you that ALL of the gentlemen are asking for time with your beautiful son.

Sometimes an officer will request a sissy to be their date for an evening of dining and clubbing in London.  Your Kimberly  went on such a date two weeks ago wearing that adorable black minidress.  Doesn't he look divine.  Our officer was so proud having this lovely sissy hanging on his arm all evening, showing him off to all his friends."                                                                                                               I stopped reading long enough to look at the first photo.  I nearly fainted at the sight of my son wearing a very sexy minidress -- and looking amazing in it.  He looked so delicate, so feminine.  The short dress made his legs look so long and slender, the high heels he wore added to the effect.   I took a breath and returned to the letter.

"Then last week, another officer borrowed Kimberly for an entire weekend, jetting him off to some swanky island resort.  We assembled some fabulous outfits for your son for this little adventure.  I simply love the very revealing black top combined with the wide leg trousers.  Your son looks like he stepped out of a fashion magazine!  And the fun part of wearing that top - it makes our sissies wish that their boobs were actually larger than they are (but the hormones only work so fast -- don't worry, you can expect a lot more progress in this department over the months ahead).  We also sent your son off with a sexy swimsuit for his resort getaway."

I stopped again to look at these two photos.....

"And please don't be concerned by the expression on Kimberly's face.  I'm happy to report that he is not sneering or frowning for the camera.  Rather, he is genuinely frightened of being sent away for time alone with these men.  As awful as life is for our sissies in the school, they become familiar with their surroundings and the routine and they take comfort in that.  But when they are sent off into the world on their own, with no chaperone, that can be very unsettling.  Your lovely Kimberly was absolutely trembling with fear before being sent off on these two "assignments."                                                                                                                But I'm happy to tell you that in both instances our officer friends were absolutely delighted with Kimberly's company!  

There is a group of three officers who have inquired as to whether they could take Kimberly away for a weekend at a country estate they are renting.  I think that sounds like a marvelous idea.  I'm sure they will find all sorts of ways to keep your darling son busy!  

I expect that there will be some sad faces over at the base when it's time for your Kimberly to be sent home to you.

That's all for now.  We are in the final stages of preparing your son to go home to you!

Sincerely, Mrs. Trainer"

Sissy Roommate -- Part 9 -- Sissy on Display

It was the last week of Spring semester.  Again, I was doing very poorly in my classes because I was spending so much time and energy in performing my sissy duties for Tank.  I was pretty sure that I hadn't done well on my finals.  Regardless, Tank and I would be leaving our dorm room tomorrow.  Tank would be heading home; I would stay in the area and get a job for the summer.

It was Thursday afternoon and Tank had finished his last final exam that morning.  He seemed pretty happy that finals were done and so he spent most of the afternoon fucking me.  He was just starting in on me for the third time when his cell phone rang.  It was Jefferson, one of his buddies from the football team.  Tank put it on speaker, "Yeah, what's up?" Tank asked.

"Did you forget about this afternoon?" asked the voice on the phone.  "We were all supposed to be at the President's house for the awards ceremony at 4:00. I bet you forgot, didn't you?  Everyone is asking where you are.  You gotta get your ass over here."

"Shit," muttered Tank.  "I'll be there in ten minutes."

"And you're supposed to bring a date," reminded Davis. "Everyone is supposed to bring a date."

"Fuck fuck fuck.  Alright. Later." Tank hung up then barked at me.  "Hurry up and get dressed into something nice. You're coming with me to this awards thing."

"What?"  I asked.

"Just shut up and put on the nicest dress you got.  We have to hurry up."

I did as I was instructed and went to my closet.  I pulled out a cute polka dot dress that I had bought for our Florida vacation.  When Tank emerged from the bedroom, he was wearing a suit and tie.  I was breathless -- I had never seen him wearing a suit.  He looked so, so, so handsome.  My tummy did a somersault just from looking at him.  

"Are we really going to the University President's house?  For an event?  With other people?"  I was in shock.

"That's about right.  I'll explain more on the walk over there."

I quickly put on dress from vacation.  The dress was sleeveless so I added a little white sweater.  I freshened my lipstick and ran a brush through my hair.  I grabbed a purse before Tank pushed me out the door.                                                                                                                As we raced across campus Tank explained that at the end of the year, the new inductees to the school's Athletic Hall of Fame were invited to an event at the President's house.  A bunch of deans and other important people would be there.  And the press.  Tank explained that he was being inducted along with his buddies Jefferson and Jackson, both offensive linemen, both co-captains of the football team, and identical twin brothers!  He said there would be star athletes from other teams but he didn't know who.                                                                               He warned me that I better not to screw up and that everybody had to be totally convinced that I was really a girl -- or he would kill me (I don't think he meant that literally -- but he made his point.)

He told me to tell people that I was a friend of his from his hometown and that we had gone to high school together.  He said that I should say my name is Mary Ellen Molloy.  I agreed to do as he said.                                                                                  I struggled to keep up with him as we made our way across campus as my platform sandals were not made for walking fast.  And as we quickly walked my head was spinning -- first from the thrill and terror of being out on display like this.  Of course I had been out with Tank in Florida but that was different.  We didn't know people in Florida.  But this was campus!  The stakes were completely different.                                                                                                                       But my head was also spinning with the question of what Tank was thinking -- and feeling.  Tank was taking me out, in public, right here on campus.  People would see us together.  People might think we were an item. Should I interpret this as a new step in our relationship?  Was Tank ready for me to be something more than his little sissy sex toy?

I didn't have time to wrestle any further with these questions because we had arrived.  We walked into the President's mansion and there were like 70 people there.  I think I counted about 15 athletes receiving the Hall of Fame award, plus each of them had a date.  There were the senior university officials, including the president and his wife.  Then there were about 20 reporters and photographers there.  I had never been to an event like this -- either as a boy or as a girl.  Everything was so fancy.  Waiters brought around trays of champagne and hors d'oeuvres.  I could hear a pianist playing in another room.  It was like being in a movie.                                                                                                                             Immediately, Tank and I went over to his buddies, Jefferson and Jackson. "Glad you could make it," Jackson joked.  Then the two of them noticed me.                                                                                        "Oh shit!" said Jefferson. Then in a low voice, "Is that your fucking sissy?"                                                                            "Oh my God!" I screamed to myself.  I didn't know that Tank had told anyone about me. I started shaking.

"Keep your pants on.  And keep your voices down," Tank growled at them.                                                               Tank was then called away by a photographer leaving me with his two buddies.  "You are so fine," Jackson said as he looked me up and down.                                                             I gulped and managed to squeak out, "Would you excuse me please," and I walked over to the buffet table downing another glass of champagne on the way to calm my nerves.                                                                                                             I barely spent any time with Tank for the next hour and a half; the athletes were mostly talking among themselves, posing for photographs or being cornered by the university bigwigs.  The other male athletes' dates were really nice and we mostly talked among ourselves while our boys were busy.  The President's wife was also very nice and I talked with her for a bit.  I felt like I was pulling it off pretty well and the champagne was helping to give me a little extra courage.

The afternoon was nice but a couple of things made me...uneasy.  First off, Jefferson and Jackson were spending a lot of time looking at me from across the room and whispering to each other when they weren't being hounded by reporters.  That made me really uncomfortable.  The other things was that Tank was spending a lot of time talking to a girl athlete, Amber Destry, a champion swimmer.  Everyone knew who she was because she had been on the Olympic team!  Not only was she an incredible athlete, but she was super gorgeous -- over six feel tall and looked like a real life Barbie -- if Barbie as a champion swimmer.  I will admit to feeling pretty jealous when I saw this.

By 6:00, the event started winding down.  Tank told me to go back to our room on my own because he was going to go have dinner with Jefferson and Jackson.  I wasn't too happy about that but of course I didn't say anything.  I said my good-byes to some of the other girls that were still there and started the walk back to my dorm, alone, a little tipsy from all the champagne, with my head full of questions.

Tank didn't come back to the dorm at all that night. I had to vacate the dorm and turn in my keys by 10:00 the next morning, so I finished packing up my things and left for the summer, never having the chance to say good bye to Tank.

Sissy Roommate Part 8 -- Spring Break Sissy

The rest of the fall and the winter went by quickly.

Of course, Tank set several new school football records -- and the team did make it to a Bowl Game for the first time in decades.  Even though football season ended, Tank continued to train hard all year round.

I continued to put all my effort into serving Tank and making him happy.  My own school work suffered badly -- I did terribly on two of my fall semester finals. But I realize I can't do everything and I have decided that caring for Tank is my top -- and sometimes only -- priority.

You may remember that last fall, Tank had me start taking birth control pills -- female hormones.  I didn't want to at first but Tank insisted.  Well they have had a powerful effect on me!  Almost immediately, I could feel swelling and intense sensitivity in my nipples and breasts.  My butt and thighs have gotten a lot fuller while the rest of me has gotten even skinnier. My complexion became clearer and my skin softer. And my hair started growing much faster and thicker.  There is no doubt that the birth control pills are starting to make me much more like a real girl!

As spring break approached, Tank told me that he was going to Florida.  Some wealthy alumnus was letting Tank use his beachfront condo for the week.  And do you want to know the best part?  Tank asked me to go with him!!!  I leapt into his arms and kissed him so hard when he asked me!  I was over the moon!                                                                         Of course, I didn't own anything I could wear on a vacation in Florida so I had to ask Tank for some extra money to buy some new things, including the super cute bikini I'm wearing in the photo.  What do you think?                                                                                                 When I go to the beach or to the pool, I wear a pair of extremely tight panties so that I'm totally flat in the front.  And I added some special padding to the bra top that helps push my teeny breasts up so that I look like I have boobs like a real girl.

We had  really great time in Florida -- and I had Tank all to myself.   Well, mostly.  He still went to a local gym every day.  But sometimes I went with him.  I was able to take a Zumba dance/exercise class with a bunch of other ladies which was really fun.  

The whole week was a dream.  I would get up extra early to take my shower and to make myself look pretty before Tank even woke up.  Then I would make him breakfast and then Tank would have sex with me.  I think we did it in every room and on every piece of furniture in the condo!  After that would would go out to the beach or to the condo's pool.  I think it really turned Tank on seeing me out in public in my bikinis!  And even though the beach was public, Tank still made me give him secret hand jobs -- right there on the beach!

And in the evenings, Tank would take me out to restaurants and night clubs.  It was like we were really boyfriend and girlfriend!

I was so proud to be seen with Tank.  First of all, he looked so handsome when he put on a nice shirt and pants to go out. And of course, a lot of people would recognize him when we were out and would ask for autographs and selfies.  I felt like I was being escorted by a Hollywood celebrity!  It was so exciting and dreamy!

Tank was so nice to me the whole time we were away.  He even bought me a little gold necklace -- it's a pretty mermaid pendant on a thin gold chain -- for me as a souvenir of our trip.

I was so happy while we were in Florida.  I felt like the time there -- parading around in my bikinis, being on the arm of a handsome man, receiving a lovely piece of jewelry -- was making more feminine, more girlish, every day.  I think the experience was changing how I thought and how I felt about myself -- and how I felt about Tank. One night, as I was sleeping tightly wrapped in Tank's arms, I even dreamed that I was Tank's wife.  Isn't that incredible?  

I'm really in love with Tank.

Sissy Roommate Part 7 -- Romantic Autumn Afternoon

When Thanksgiving week came around, most students left to go home to spend the week with their families.  But Tank had a big game and practices over the Thanksgiving break, so I stayed to be with him.  And when Tank wasn't at his two-a-day practices or in the gym, he was spending his free time with me.  Here some photos that Tank took of me one afternoon.  He had me get all dressed up and we went into the woods.  He brought a bottle of wine and we found a secluded place where we drank it and then had sex -- right there in the woods!                                                                                                                                   As I've said, my life is getting a bit confusing and complicated since I'm spending so much time dressed up and acting as a sissy girl.  Tank is insisting that I should be dressed and made-up like a girl any time that he's in the dorm room!  I want to make Tank happy -- and I certainly don't want him to be angry with me -- but it's really hard for me to do what Tank is demanding.

To give you a sense of how complicated my life has become: I have to be all dressed and looking pretty for Tank when he returns to the dorm around 9:00 after his early morning work-outs.  He's already eaten breakfast with the team but I always have some eggs and toast ready for him when he comes in that I make on the little hot plate we have. While he eats, he likes to watch ESPN on the TV -- and get a blow job from me.  Tank finishes with his breakfast (and with my mouth) a few minutes before 10:00.  Then he goes off to take his shower and do whatever he does all morning (I don't think he goes to a lot of classes).                                                                                                                            But I have 10:00 lectures to get every day -- and no time to wash off my make up and change back into my boy clothes.  At first I was skipping a bunch of lectures but I was really falling behind.  I realized the only way I could keep up with my lessons was to rush over to the lecture halls still dressed as a girl. I keep to myself and try to sit in the back so that I don't attract too much attention.  But sometimes a boy will sit next to me and try to flirt with me.  I guess I find that sort of exciting, but I try not to encourage it too much.

After my morning lectures, I stop by the dining hall -- still dressed as a girl -- and quickly eat my lunch.  At first I thought everyone would notice me, but so far I haven't had any real issues. Then I rush back to the dorm because Tank usually shows up there around 12:30 after he's had lunch with his buddies.  When Tank arrives, we usually make-out for a little while and then he has sex with me.                                                                                                         I had to beg Tank to let me change back into my boy clothes in the afternoons because that's when I have my small classes.  I can get away with sitting in a big lecture hall pretending to be a girl -- but that doesn't work at all for the small classes.  But since I don't have any classes on Friday afternoons, I usually stay dressed as a girl all day long.

Something else happened on that trip to the woods over Thanksgiving.  After Tank had finished fucking me, he handed me a small bag.  "You have to start taking these," he said.  I looked inside and wasn't sure what I was looking at. "They're birth control pills," Tank explained. "You know, female hormones.  They will make you more like a real girl."  I asked him where he got them and he explained that he told the team doctor that he needed the pills for his girlfriend, and the doctor handed him a six-month supply, no questions asked.

"But I don't think boys are supposed to take those," I stammered. "I mean, those are only for real girls."

"Shut the fuck up, you stupid sissy bitch. I said you're going to take them and that's what you're going to do. In fact, take the first one right now!" 

I fumbled with the packaging and managed to pop out a single pill from it's container. I washed it down with the wine.

"Good," said Tank.  "Now suck me off quick before I have to go to practice."

A Christmastime Sissy - Part 1

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

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

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

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

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

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

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

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

 

Taking my Sissy Husband on Vacation

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

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

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

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

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

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

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

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

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

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

 

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

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

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

 

Mommy's Pajama Sissy -- Part 11

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

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

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

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

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

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

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

 

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

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

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

Mommy's Pajama Sissy -- Part 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 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."