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.

Sexy Beach Sissy

Sam is a total sissy.  He loves dressing up in his sister's clothes and pretending that he's a girl. He used to do it only around the house when his parents were out.  But now that he has his driver's license, he likes to go out in public as "Samantha."  Sometimes he goes to bars and clubs. Sometimes he'll walk around the mall or the park.  But his favorite thing to do is to hang out at the beach.

He saved enough money working part-time jobs to buy an old VW van.  This is both his car and his dressing room.  Every day during the summer, he leaves the house early in the morning as Sam. He drives to a quiet place to park and climbs in the back of the van and transforms into Samantha.  He fixes his shaggy black hair in a way that looks cute and feminine.  He does his make-up -- he loves wearing lots of bright red lipstick!   He puts on a bikini with just enough fabric to hide his fake boobs. And he wears a super tight panty under his bikini bottoms so that he is perfectly flat and smooth in front. Lastly, he puts on some dangly earrings and sprays himself with a flowery perfume. Once he is satisfied with his look, Samantha continues the drive to the beach.

On most days, Samantha arrives at the beach before there is any real action there so he hangs in the van and listens to the radio. There are a bunch of regulars that are also around early in the morning -- maintenance workers, cops, vendors, lifeguards -- heading into work. Samantha knows a lot of these men by name and a bunch of them go out of their way to swing by the van and flirt with the pretty brunette girl for a little while.  Samantha's favorites are the cops and the lifeguards.

Sometimes if the cop or the lifeguard is especially cute, Samantha will invite him into the van to make-out. The really lucky ones get to go into the back of the van where Samantha will wrap those pouty, red, slick lips around their cocks and suck them off.

But that's just the start of Samantha's day.

By now the beach is starting to fill up. Samantha grabs his towel and sunglasses and heads out across the quickly warming sand. The trick for Samantha is to find the right spot on the beach where he will attract a lot of attraction from the boys hanging out there.  He knows that sometimes big groups of older boys hang out on the stretch of beach just past the pier. There are fewer people out there and it's a perfect place to throw a football around.  Samantha will find a promising group of boys and place his towel just near enough that the boys will definitely notice him.  It never takes long before one or two brave boys will venture over a strike up a conversation with the cute brunette laying on her towel.  A little flirting, a little giggling and Samantha will easily hook one unsuspecting boy.

"Would you please put some sunscreen on my back?" Samantha will ask a guy he is interested in.  No boy has ever answered "no." Samantha gets a rush of sensual pleasure feeling a boy's strong, rough hands spreading lotion on his soft shoulders and back.

Some of the boys get the chance to go for a walk down the beach with Samantha.  Samantha likes how it feels when a big strong boy wraps his arm around his skinny, exposed shoulders. His pulse quickens when a boy pulls him close as they walk side-by-side. It makes Samantha feel so feminine. The walk along the beach often leads to some making out under the pier.  Samantha likes pressing up against a strong young man while they make out.  He especially likes feeling his admirer's dick get hard as they kiss.














And the luckiest boys -- the most handsome, most muscular, most studly ones -- get invited back to the van for a special treat. He starts off by getting these boys aroused with his mouth, licking and sucking their dicks until they are nearly ready to cum, But before they do, Samatha quickly repositions himself so that the boy is on top of him. With his soft hands he finishes the job so that that boy shoots his hot cum all over Samantha's flat, exposed, lotion covered belly.  

The boys at the beach don't know Samantha's secret. But now you do. So would you go into the back of the his van with him if he invited you? Of course you would.

Never too Late for Sissies

I often hear wives say, "I wish I had feminized my husband years ago. Now it's too late."  That is nonsense! It is never too late to feminize your husband. Just look how lovely Sissy Jessica is in his bikini!

Mary had been married to Jeff for over 20 years. Mary knew Jeff was a crossdressing sissy, but she didn't mind. She enjoyed having a husband with a feminine side who listened to her, doted on her, enjoyed shopping with her. But as Jeff experienced some set-backs at work and was starting to consider early retirement, Mary decided it was time for some changes in their lives. Mary decided that they would both be happier if Jeff took his sissy-ness to the next level and became a woman full-time -- or at least a sissy version of a woman.

Jeff resisted at first.  But that's the good thing about sissies; they have no spine and no ability to push back. So in the end, Jeff did exactly as Mary ordered and became Jessica.  And weren't the results fabulous!  Jessica looks ten -- maybe fifteen -- years younger than Jeff did when his transition began.  And look at him now!  He looks totally hot as a woman, even in a skimpy bikini.

But Mary wasn't done yet. She also decided that both she and Jessica needed to have real men in their lives. Jessica was horrified -- distraught -- by Mary's suggestion.  Jessica cried and protested but to no avail.  Mary got her way as always.  

It was easy for Mary to find countless older men online who wanted to have a sissy of their own. She eventually selected Terrence, a wealthy divorced businessman, for Jessica.  Mary arrange all the details for their first meeting and subsequent dates.  It worked out perfectly. Once in the presence of a real man, Jessica easily and naturaly slid into the role of the woman in the relationship.  That was eighteen months ago. Now Jessica is embarking on the next exciting chapter of his life -- as Terrance's wife. That's right! Jessica and Terrance got married last month and those bikini shots were taken on their honeymoon!

Jessica is in heaven being the pretty, obedient and subservient housewife for his husband.  You can see how happy he is being feminine and domesticated and servile to a real man.  He spends hours every day making himself pretty. He derives total fulfillment by being the object of his man's desire -- and by satisfying that desire with every part of his feminized body.

Tonight, Jessica and Terrance are having a double date tonight with me an my new boyfriend.  Jessica is making dinner for all of us -- for his husband, for his ex-wife that feminized him and for his ex-wife's lover!  Could there possibly be a greater expression of what it means to be a total sissy?

So my friends, as you see, it is never to late to help your sissy fulfill his destiny!

My Sissy Neighbor -- The Conclusion: Honeymoon

A lot of time has passed since my last post.  And a lot has happened for my sissy sister, Anita.  The biggest news is that Anita got married!                                                                                                                                                     A very handsome, divorced lawyer (his name is Jackson) was looking to buy a home and Anita became his realtor.  One thing led to another, and before long, they were dating.  Six months ago,  Jackson proposed to Anita, giving her the biggest, most beautiful diamond ring I have ever seen!  Of course Anita said yes!  Here are some lovely photos from their "Engagement Shoot."  Isn't Anita exquisite?

 The wedding was intimate and lovely. I was the Maid of Honor and of course mom was the Mother of the Bride!  And, as you would expect, Anita was the most beautiful bride ever!!!





Here are some photos from their honeymoon in Hawaii that Anita posted.  Here she is in a lovely black and white print dress that I helped her pick out.  Anita loves how this dress shows off her every curve.  Of course, she isn't wearing a bra underneath a dress like this.  I'm sure that Jackson is so pleased to have snagged the gorgeous Anita to be his bride and to have this lovely creature hanging on his big strong arm as they stroll around this tropical paradise. And Anita told me all about the hot sex they had during their honeymoon.  Apparently, Jackson has quite the sexual appetite -- and the equipment to go with it!  Anita said their honeymoon was a continuous round of eating, drinking, dancing, swimming and fucking!   

And here's Anita lounging by the pool. She loves putting her crazy curves on display in her sexy swimsuits. She knows that every guy around the pool can't take their eyes off of her -- even when their wives and girlfriends are right there!  Just check out Anita in her blue one-piece.  It can barely contain her giant boobs!  I love it! 

I am so happy that my sissy neighbor has found her new life as a successful business woman, a beautiful, voluptuous lady, and a devoted and loving wife of a handsome man. It has been a wonderful experience for me watching this amazing transformation and journey. And through it all I guess I lost a sissy neighbor and gained a sister. 

Sissy Madison's Vacation -- Part 4

Madison had spent the last few hours in the company of a handsome lifeguard who had taken a lot of interest in Madison after seeing him lounging around the pool in his new blue bikini.

Madison had just returned to the hotel room, and was telling Mother about his evening.

"And what about your new lifeguard friend?" Mother probed.

"Well," Madison began tentatively. "He was really funny and really nice to me at the bar. He paid for my drinks. Then when I told him I had to leave, he insisted on walking me back here from the pub. So..."

"Yes?" Mother prompted.

"So, we walked back along the beach together. He put his arm around me while we walked. At first I was surprised and I almost pulled away. But then I decided that it felt sort of nice. It made me feel safe and protected. And then he kissed me. It made me feel dizzy when he did that."

"And then?" Mother asked, barely able to believe what she was hearing.

"Then he started kissing more. A lot more. It felt so good. Oh Mother, I'm so confused. I know I'm not really a girl, but something happens when I'm with him."

"It's OK, darling," Mother comforted. "I think it's lovely that you're experiencing feelings that women have. He's very handsome and strong and masculine...It's only natural that he would make you feel some girlish, romantic emotions."

After a moment Madison continued, "He wants to see me again. Tomorrow is his day off and he wants to take me out on his friend's boat for the day. I already said yes. Is that OK?"

"Of course, darling. That sounds lovely. Now get some sleep so you will look your best for your big date tomorrow.  I think you should wear your leopard print bikini. I think you will look nice in that."

In the morning, Madison put on his new bikini and slipped on a lacy cover-up and his high heeled sandals. He packed a small bag with his lipstick, his sunglasses, his sunscreen and his hair brush. Mother walked him down to the marina where the lifeguard was waiting on his friend's boat.

"Welcome aboard!" he said as he took Madison's hand and helped him step onto the boat. Madison waved good-bye to Mother as the lifeguard maneuvered the boat out of the marina.  As they got into open water, the lifeguard stripped off his tee shirt and Madison slipped out of his cover-up. Madison tried not to stare at the handsome lifeguard's tan and muscular body but he couldn't help himself. 

The lifeguard offered to let Madison steer the boat for a while.  Madison stepped up to the steering wheel and the lifeguard moved in close behind him.  As Madison held the wheel, the lifeguard wrapped his strong arms around Madison's little waist.  Madison shuddered when the lifeguard began kissing his neck. As the lifeguard pressed himself tighter against Madison's back, Madison could feel the lifeguard's dick stiffening. Madison moaned softly with excitement. 

Once they were out in open water, barely in sight of land, Madison and the lifeguard moved to the cushioned benches in the back of the boat and resumed the passionate hugging and kissing that had begun last night.  Madison became feverish feeling the lifeguard's strong, hard body pressed hard against his own soft, skinny body. The lifeguard's enormous erection was not well concealed by the nylon swim trunks he was wearing. Completely swept up by the romantic feelings he was having, Madison pulled down the lifeguard's swim trunks, freeing his massive cock.  Madison wrapped his delicate, manicured fingers around it and began pumping gently. He then lowered his head into the lifeguard's lap and put the now rock-hard dick in his mouth.

After fifteen minutes of stroking, kissing, licking and sucking, the lifeguard could resist no more and exploded in Madison's mouth, blasting his hot semen down Madison's throat.  As the lifeguard came in his mouth, Madison also shuddered with an orgasm, even though his little penis was tightly tucked between his legs. 

Before their day at sea was over, Madison would make his lifeguard cum again two more times.  Madison felt so fulfilled pleasuring this strong masculine man.

As they returned to shore, Madison could see his Mother waiting on  the dock. "Oh dear," thought Madison. "Whatever will I tell Mother about what I did today?"

Sissy Madison's Vacation -- Part 3

Madison was having the most wonderful summer of his life. Spending all day, everyday, lounging and sunning himself beside a crowded resort pool wearing a pretty ladies swimsuit was like a dream come true.  And the more time he spent pretending to be a pretty girl in a swimsuit, the more his confidence grew.

On the evening that they arrived at their hotel in Miami, Mother suggested to Madison that he might like to try a different style of swimsuit. Mother was going to take Madison to a local mall to go shopping, but as they walked through the resort, they noticed some very cute swimsuits in the window of one of the boutiques off the hotel lobby. In particular, the boutique's window displayed several high waisted bikinis that Mother thought might look wonderful on her sissy son.

Madison was very excited by the idea of wearing a two-piece swimsuit. The helpful saleslady found the bikini in Madison's size in several colors and patterns and Madison picked the three he liked best. In the fitting room, Mother helped him try on the bikinis. Mother made Madison go out into the store wearing the bikini to see himself in the big mirror. The saleslady said that he looked "very chic."  Some other customers stopped what they were doing and looked approvingly at the lovely young lady in the cute two-piece who emerged from the fitting room.

In the end, Madison picked out three suits that he liked the best and Mother bought them. Madison was thrilled with his new bikinis. That night he had trouble sleeping because he was so excited that tomorrow he would be wearing one of his new two-piece suits around the hotel pool.  He decided that he would wear the black one first.

When tomorrow came and Madison arrived poolside in his new bikini, he started getting a lot of attention almost immediately. Maybe it was the swimsuit or maybe it was just that the men in Miami were more assertive, but Madison was attracting men like moths to a flame!

As soon as Mother and Madison sat down, one of the pool boys started trying to flirt with Matilda. And during lunch, the waiter tried to get Madison's phone number. And later that afternoon, a young businessman brazenly walked up to Madison's lounge chair and started talking with him. At first all this masculine attention made Madison uncomfortable, but after a while he started enjoying it. It made him feel extra feminine and beautiful.

The next day was more of the same. This time Madison wore his new blue bikini. And again, the men seemed to emerge from everywhere trying to get his attention. At one point, a photographer working for the hotel asked to take Madison's picture and asked him to strike a few fun poses while he took pictures. 

Towel boys, waiters, other guests -- men of all ages -- were flirting with Madison. It was all just a harmless game and Madison played along. But that was about to change.

After Madison and Mother returned from lunch, one of the lifeguards came over to where they were lounging. The lifeguard was tall, blonde and very handsome. Wearing only his tight red swim trucks, his perfectly muscular physique was on full display. When he started flirting with Madison, Madison turned bright red and was barely able to stammer a reply of any kind. Mother watched all of this with great interest and a little bit of worry. After a few moments, the lifeguard moved on, leaving a confused and embarrassed Madison to sort out what had just happened.

"Well, he seemed nice," Mother innocently observed as they both watched the hunky lifeguard walk away.

"Huh? Oh, yes, I guess," Madison answered distractedly.

For the rest of the afternoon, Madison couldn't stop thinking about the lifeguard. He couldn't even concentrate enough the read his Cosmopolitan magazine.

As Mother and Madison were preparing to head back to the room to get ready for dinner, the lifeguard reappeared. This time he was wearing a tee shirt and baggy shorts, which was somewhat disappointing to a very bewildered Madison. The lifeguard explained that he had just gotten off work and that a few lifeguards and some other off-duty hotel staff were going out to a pub just a short walk from the resort. He asked if Madison would like to join them. Madison began to blush uncontrollably.

Madison couldn't speak. So Mother jumped in. "Well, Madison, I think that could be fun for you. I'm sure you would enjoy spending some time with people more your age. You do want to go, don't you?"

Struggling to make sense of his emotions, Madison replied, "Umm, yes. I do think that sounds like fun."

"Great!" the lifeguard answered enthusiastically. "Are you ready to go now?"

"Here, Madison," Mother said as she handing her son a beach cover-up to wear over his bikini. 

"Are you sure you don't mind, Mother?" Madison asked, searching as much for guidance as for permission.

"Of course not dear. Now you have fun. I'm sure it will be just fine." And with that, Madison slipped on his high heeled sandals and off he went with the lifeguard.

When Madison arrived back at the hotel room a few hours later, he was a little drunk and very, very excited. He started telling Mother about his evening -- about the other people he met at the pub, how nice the lifeguard's friends were, the music that was playing, what he drank. Mother was happy that her darling sissy son had enjoyed himself. But she expected she wasn't hearing the whole story. 

"And what about your new lifeguard friend?" Mother probed.

"Well..." Madison began tentatively, nervous about telling Mother everything that happened that evening. 

A Sissy's Dinner Date Fantasy - Part 1

My name is Sean and I have been a sissy crossdresser all my life.  I have always kept it a secret, dressing up like a girl alone in my little apartment.  I only ventured outside "en femme" occassionally and only if I was pretty certain I wouldn't run into other people.

Night after night, I would come home to my apartment and transform myself into the lady of my dreams.  I had become very talented with my make-up, my mannerisms and my voice.  I knew that I looked very attractive and convincing when dressed.  Alone in my apartment at night, I would read romance novels and fashion magazines and watch chick-flicks on TV.  But the more time I spent pretending to be a girl, the stronger my fantasies became to actually experience life as a girl.  I became obsessed with the idea of being desired and romanced by a real man -- just like in my novels and in the movies.

About six weeks ago, when my obsession became too much for me to control, I went into action.  I created a profile of my femme self on Match.com.  It took me several hours to get it just right.  First, I picked out a few of my best girlie photos, including these two below.  I like the one on the left because it shows off my legs.  And I like the one of the right because it makes me look more sophisticated and mysterious.

And finally, just to make sure I got everyone's attention, a photo of me in a bikini!




















I came up with a back-story that sounded believable and would be appealing to men browsing through the website. I was, according to my profile, Sheila Landers, a 26 year-old junior high school teacher who had recently moved to the area.  I said I was looking for a "successful, older gentleman who was interested in a long-term relationship."  I described my interests in all sorts of girly things, like ballet and cooking.  I described in detail my idea of a perfect first date -- a candlelit dinner at a French restaurant followed perhaps by a romantic walk...I got myself excited just thinking about it!

What my profile didn't include was anything that was actually true. It didn't say that I was a 20 year-old sissy and college drop out who worked for minimum wage in a corporate mail room. It didn't say how the idea of being romanced by a man excited me and terrified me -- all at the same time!

When I was finally satisfied with my profile, I pressed Enter and posted it on Match. I didn't really know if anyone would write back to me or even notice my profile.

I needn't have worried about that. About two hours after I uploaded my profile, I had about twenty requests from men wanting to meet me. Within a week, I had over two hundred offers for dates!

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!

A Sissy Honeymoon

For the last two years, I have been under the strict and controlling hand of Master Roman.  He has trained and transformed me into an exquisitiely feminine, obedient and docile Sissy.

At first I resisted my captivity and transformation.  But Master Roman skillfully -- and often cruelly -- destroyed my will to resist as he forced my inner femininity to blossom.  Eventually I learned to embrace my new existance as Master Roman's obedient Sissy servant.  My life now revolves around pleasing and serving my Master -- and nothing else.

I must have succeeded in pleasing Master Roman because he asked me to marry him!  We had a lovely, private ceremony where I took my vow of obedience and servitude, and then Master Roman whisked me down to Jamaica for our Honeymoon. 

As we stood under the waterfall, I could feel Master Roman's cock getting hard as he pressed against me.  He held me tightly in his big strong arms, kissing me.  His hands moved up to my soft little breasts that had developed from the hormones Master Roman had been giving me.  He untied the little bikini top that I was wearing.  I moaned softly as his fingers played with my swollen, sensitive nipples.

"Who are you?" Master Roman whispered into my ear.

"I am your obedient and loving Sissy Wife," I replied as he had trained me.  He smiled.

"And who am I?" Master asked.

"You are my Husband and my Master who I will serve and obey and for the rest of my life.  My only purpose is to please you," I said, reciting the acceptable answer. 

Master nodded and replied, "That's right.  And now to please me I want you to suck my cock."

I instantly fell to my knees and quickly pulled Master's cock into my mouth.  The water where we were standing was fairly deep so I struggled to breathe as I pulled his enormous hard rod into my mouth. 

As he started to cum, Master Roman said, "Sissy Wives don't need to breathe.  They just need to suck cock."  He then pushed my head underwater and held it there.  Even though I was practically drowning, I felt so fulfilled knowing that I was performing a service that pleased my Husband/Master so greatly.  It felt wonderful to being a good Sissy Wife, on my knees, feeling my Master/Husband's hot cum blasting into my mouth and down my throat.  Even as I started to lose consciousness, I ensured that I had thoroughly drained my Master/Husband and had swallowed every drop.

When I regained consciousness, I was on the floor of our hotel room.  These was a note jammed in my bikini bottoms that said, "Get cleaned up and put on new bikini.  Meet me in hot tub next to the big pool.  Hurry.  I need another underwater blowjob right now."

A Sissy Wife's job is never done.

Sissy on the Beach

Master Rick brought his captive Sissy Shelley to the beach for the first time. Sissy Shelley rarely left the mansion; he had been Master Rick's captive and sissy love slave for three years.


Today, Master Rick wanted to show off his little sissy on the beach. Sissy Shelley's body was totally hot! The hormones and surgery he had forced on his sissy had transformed him from a skinny young man into the ultimate in sissified beauty and perfection.


Master Rick dressed poor little Sissy Shelley in a skimpy bikini. His big, soft boobs were shamelessly on display for everyone on the crowded beach to see. His tight bikini bottom barely hid his tiny useless sissy cocklet.


Master Rick walked down to the water and dove into the surf, leaving Sissy Shelley alone on the blanket. Sensing an opportunity to escape, Sissy Shelley leapt up from the blanket and started sprinting down the beach, his huge tits bouncing madly as he ran. Master Rick saw his prized sissy captive making a run for freedom. Master Rick raced after his sissy and tackled him to the sand.


Master Rick pinned his sissy to the sand. Sissy Shelley knew better than to try to fight his powerful, muscular Master. With his hard body on top of the little sissy's lithe little frame, Master Rick whispered into Sissy Shelley's ear, "That was a very very stupid thing to do. You should know better than to escape. You are my sissy sex doll, now and forever. Trying to escape was a very bad thing to do. Tonight you are going to be punished -- severely -- for your misbehavior.


Sissy Shelley felt Master Rick's cock getting hard in his swim trunks.


Oh look at that," said Master Rick with a smile. "Thinking about beating you tonight is making me hard. Tonight is going to be lots of fun -- for me."


Master Rick pressed his lips onto his sissy's pretty mouth and kissed him very very hard, plunging his tongue deep into the sissy's mouth.


"Time to go home, you bad little sissy."

Sissy in a Bikini Pleases his Master

Although Sissy Lydia fought against his captivity and forced femininity training at first, he had now embraced his new life and his new body.  The hormones, the beatings, the forced sex, the hours of beautification procedures had stripped him of his old male persona.  Instead, his Master and Trainer had created a sexy and beautiful love doll with beautiful, full breasts, a luscious round ass, long auburn hair and soft, silky skin.  Now, Sissy Lydia's entire sense of self and purpose was to serve and please his Master 24 hours a day.  Sissy Lydia was so happy to pose seductively in his skimpy bikini while his Master played with himself, enjoying Sissy Lydia's show.