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."