Spring Break Sissy

When I told my parents that I was going to Florida for spring break, they were really worried.  They pictured me hanging out at wild, drunken parties and stuff like that.

But actually, my spring break is very different -- but my parents don't need to know that. 

You see, I am spending the entire week as Professor Wilson's sissy!


Here's a photo of me in the hot tub with my Professor and Master.

It all started last fall when I was taking Professor Wilson's Human Sexuality class.  I went to see him during his office hours one afternoon because I needed help understanding an assignment.  He closed the door to his office after I sat down.  Before I could even ask a single question, Professor Wilson asked me, "You're a sissy, aren't you?"

I was shocked and scared by his question.  The truth is that I am a closeted cross-dresser, often having fantasies of submitting myself to be feminized and controled by a dominant man or woman.  But this was my secret.  I had never told anyone this.  How could Professor Wilson possibly know?

"I asked you a question, sissy!" he shouted.  "Don't deny it.  I know what you are.  I can tell.  It's my expertise, after all.  Now I am going to ask you again.  Are you a sissy?"

I lowered my eyes to the floor, and softly answered, "Yes," unable to resist the Professor's command.

"I knew it!" he exclaimed with a self-satisfied smile.  "Well from now on you are going to be MY sissy.  That means you will do whatever I tell you to do.  You will submit to me in all ways.  Do you understand?"

"Yes, Sir," I meekly responded.  Professor Wilson smiled again.

I now visit Professor Wilson at his home every evening and every weekend.   When we are together, he is not nice to me at all.  As I walk in the door, he instructs me on how I should dress for the evening.   I prepare myself as quickly as possible -- make-up, lingerie, a dress, stockings, heels -- the works.  He then proceeds to order me around for the next few hours.  This usually includes cleaning his house, doing his laundry and making his dinner.   If I do anything that displeases him, he throws me over his knee for a harsh spanking.  

When my chores are done and he has finished eating, he has sex with me.  He often orders me to bend over the back of the couch so he can take me from behind.  If there is a big game on TV, he makes me suck on his cock while he watches the game.  Then after he cums and I have cleaned up the mess, he orders me to get out.

My Professor/Master has helped me to understand that, as his sissy, I exist for only one reason -- to serve and please my Master -- and that my feelings have no importance.  I am just an object for him to use for his pleasure.   

Now it is Spring Break and Professor Wilson has arranged for a perfect Master/Sissy vacation.  All year I have growing my hair out and Master has kept me on a strict diet so that I would look extra girlie for our trip.  He rented a beautiful condo that has a view of the Intercoastal Waterway, a big deck and a hot tub.  He packed several pretty outfits for me to wear, lots of sexy lingerie and even two bikinis!

Master has been so nice to me since we arrived at the condo!  Of course I have to do all the chores and follow all of his orders and he has spanked me a few times.  But mostly we are passing our days and night in bed or in the hot tub.  It has been so romantic!  We have been spending hours and hours kissing and having sex.  And after he is done having sex with me, he has been letting me snuggle up against him.  I feel so safe and happy when Master wraps his big strong arms around me. 

Here we are in the tub again.  I am giving him a handjob.  His enormous, hard cock feels so good in my soft, manicured hand.  I am so content and fulfilled serving and pleasing my Master.  

I wish my Sissy Spring Break would never end.

New Sissies at the Beach

Last week I took my two newest Sissies for a day of fun at the beach.  It was a holiday weekend, so the beach was very crowded and my Sissies attracted a lot of attention!

These two fell into my clutches just a few weeks ago.  They are just at the very beginning of their transformations.  Their boyish haircuts are just starting to grow into more sissyish styles -- although I already dyed their hair to a prettier, more feminine color.  They are still very confused and frightened by their captivity and forced transformations.

My newest Sissies were horrified when they saw the outfits they would be wearing.  But their protests subsided after a few whacks with my hairbrush.

And aren't they absolutely darling!?!  I just loved dressing these two up in these identical sissy bathing suits -- with the matching sissy cover-up.  The high waisted panty (with an adorable little bow!) and the training bra tops are simply devine.  And the little pink heartsare just perfect for little Sissies.

I love this photo.  The Sissy in front is about to start crying as I just ordered him to take off his cover-up and let everyone see him in his pretty Sissy bikini!

Sissy Goes Outside Part 1

I liked dressing up in my older sister's clothes and I did it whenever I was home alone.    First, I would put on one of her bras and a pair of her panties.  Next I would go to the bathroom and do my make-up and fluff up my longish hair.  Then I would go through her closet, trying on her dresses, skirts, blouses and shoes.  I even dressed up in her nightgowns and bathing suits.  I would pose in front of her full length mirror, admiring my feminine reflection.

That's exactly what I was doing when disaster struck.

I was all dolled up in my sister's make-up, underwear and a party dress.  The dress was my sister's favorite.  It had a feminine, white ruffled top, a black skirt and a wide belt that gave me a sexy shape.  I was also wearing her sexy new peep-toed pumps with really high heels.  I felt so girlish and sexy.  I was posing and admiring my reflection in her big mirror when I heard a girl's voice scream, "Oh My God!"   I spun around and saw my sister and two of her friends standing behind me. My sister's friends started laughing uncontrollably.  My sister shouted, "What the fuck are you doing in my clothes?!?"

I was too shocked to speak so one of her friends answered for me. "Your brother is a total sissy faggot!"

My sister glared at me for a minute and then said, "Don't move."  She went downstairs followed by her friends. I was so afraid and confused and ashamed that I that just stood there as she ordered.

A few minutes later the three of them returned.  "Well Sissy," she said, "I'll make you a deal.  I won't tell Mom and Dad about this -- but you have to do something for me."

"Sure," I said eagerly.  I would do anything to keep my parents from learning about this.  "What do I have to do?"

"It will be easy," my sister replied.  "All you have to do is to walk down Walnut Avenue, from Church Street to Parker Street." 

"You want me to go outside?  Dressed like this?" I exclaimed.  I had never even thought about going outside before.

"No!  Not in my favorite party dress.  We'll pick out something cute and appropriate for you to wear.  Now don't be such a Sissy," my sister said while her friends giggled.  "Walnut is a quiet street.  Now get into the bathroom so we can fix you up."

I really had no choice so I complied.  And my sister was right -- Walnut was a quiet street.  I should be able to do this.

Well, the girls teased me mercilessly as they made me  strip down to my sister's bra and panties.  They  went to work on my hair and make-up and made me look really pretty -- much better than I had ever done myself.  Then they picked an outfit for me to wear.  The girls helped me dress and then ordered me into the car.  Now I stated to get nervous and I said that I had changed my mind.

"Too late, Sissy!" my sister snarled.  "Shut up and get in the car."

I started to cry as the girls shoved me into the back seat of the car.

Scared Swimsuit Sissy

"Don't look so sad and worried, Sissy!" my Mistress said to me.  "You look lovely!"

I tentatively emerged from the bedroom wearing the tight and sexy swimsuit my Mistress had purchased for me.  I had never been outside in public in anything so skimpy and revealing.  I was scared to death to leave the safety of our hotel room.

"All those hunky men sitting around the pool will go absolutely crazy when they see you parading around the pool area looking like that!" Mistress said with delight. 

I was horrified by the image Mistress painted.  Mistress had chosen a hotel that was packed with men attending the big convention in town this week.  The pool would undoubtably be crowded with rowdy, horny men, just like Mistress said.

"Maybe if you're lucky, some beefy stud will offer to rub sun tan lotion on you.  Now hurry up and grab your towel and put on your sandals.  I don't want to keep all those hot men waiting!"

A Sissy's Education

"Quit your pouting and change your attitude right this second, missy," scolded my stepmother.  "Look at the time and you're not even dressed yet!"

"But you promised!" I cried.  "We had a deal.  You said I could go to college in the fall if I let you treat me like a daughter all summer.  Well, I did everything you asked.   I travelled all over Europe with you pretending to be mother and daughter.  I let you dress me up like a girl every day.  I even learned how to do my hair and make-up like a real girl."

"Wasn't that just delightful," she replied.  "And you looked so cute in your swimsuit on the beach in Capri..."   

"And," I continued, "I think you've been putting female hormones in my food."

"You figured that out, did you Einstein?" my Stepmother sneered.  "What gave it away?  Was it those B-cup boobs or the fact that your little 'thingie' doesn't get hard any more?  Now hurry up and put one your dress.  The car will be here soon to take us to the airport."

"But I'm not going!" I screamed.  "You can't make be go to a girls' finishing school!"

"Oh, I can and I will!" my stepmother shot back.  "Now you listen to me you little faggot sissy.  I know you like to dress up like a girl.  I know you've been trying on my things when I'm not home.  Don't try to deny it."

I hung my head in shame.  "We've already discussed this a hundred times," I said, defeated.  "Yes, I like to wear girl things occasionally.  I like to pretend I'm a girl once in a while." 

"Well, then, what's the problem?  I'm letting you live out your dream and pretend to be a girl all the time.  I'm even willing to spend a lot of money to send you to school to be the very best girl you can be!  Now one more word out of you and I will tell your father that you're a little sissy that likes to dress up like a pretty girl!"

Oh no!  Anything but that.  My stepmother held the trump card and she knew it.

"Oh my," my stepmother said, " the limo is already here.  Get your dress on and let's get you to school."

Swimsuit Sissies

The poor little sissies had never been displayed before in swimsuits. But here they were, nervously descending the stairs to the crowded pool area of the fancy resort.

Their Masters looked on approvingly at the sweet
sissies in their skin tight swimsuits and high heeled sandals.

In a few minutes, the sissies will be rubbing suntan lotion onto their Masters' muscular shoulders, fetching them drinks, and doing all the things that a pair of totally feminized boys should do for their owners.