A Reluctant Sissy -- Part 1 -- Arrival

It was just about two years ago that I finally decided that I had had enough!  I am a single mother and my son was completely out of control.  I didn't really care that he was a crossdressing sissy.  I didn't like him getting into my lingerie and make-up and dresses and shoes every time my back was turned.  But I could have lived with that.  There were other problems -- real problems.  He was close to failing out of school, he was getting into all sorts of drugs, and I was spending a fortune getting him out of trouble with the police for his non-stop shoplifting.

There were endless meetings with his teachers and counselors at school.  But they had no answers.  I tried family therapists, but they were useless.  I tried grounding him and every other form of punishment I could think of.  Nothing worked.

And then he stole several pieces of my jewelry and tried to pawn them. That was the last straw!

I remember reading somewhere that there was a Ms. Trainer who ran a service where she could improve the behavior of boys through feminization.  It wasn't easy to track her down, but I did.  I discussed my situation with her and she was very reassuring.  She explained that since my son was already a crossdressing sissy, her techniques should work very effectively on him.  She suggested that I send him to her new facility in London, where the staff and the process were extremely strict and effective.  A new semesters was just about to start and there was one opening (they handle up to six sissies at a time).  I considered this to be a real opportunity so I wasted no time at all in doing what she suggested.

Imagine my son's surprise when we arrived at Ms. Trainer's estate outside of London.  My son thought I had taken him to London so he could go pubbing and what not. You should have seen the look on his face when we pulled up the driveway and two enormous orderlies roughly grabbed him and dragged him out of the car and into the house!

After an initial period a six weeks, during which I had heard nothing about my son's progress, I received my first report from school -- complete with lots of photos!  Let me share their letter with you:

"Dear Mrs. ___, 

We are happy to report that your son has made good progress during his first six weeks with us.  We have decided to call him "Kimberly" -- we hope that name is satisfactory to you. He is settling into our routine of continuous training, behavior modification, and positive and negative reinforcement. There is evidence that we are starting to strip away his awful self-destructive behavior and replace it with a gentler, more compliant, feminized version of himself.  Enclosed please find several photos of how your son is dressed everyday here at the facility.  He really makes an adorable sissy!"

I stopped reading to marvel at the enclosed photos.  I was stunned by just how lovely my son looked in his pretty new dresses.  He had become so skinny in just a few weeks.  And his hair was dyed such a pretty shade of blonde.  His make-up, his jewelry, his sky-high heels -- everything was just so perfect and dainty and feminine.  I could barely believe my eyes.

The letter continued:

"Of course, even though we know he is a sissy at heart, he is resisting the feminization process.  This is normal and not a cause for concern at this early stage.  As you can see, he refuses to smile for our photos. As we remind him daily, we don't care if he is happy or not; he is only succeeding in making his transformation more difficult and more miserable for himself.

We will keep you posted as our time with your son proceeds.

Sincerely, Mrs. Trainer"

Sissy Roommate Part 3 -- I Chose a Path

After Tank forced me to give him a blow job, I raced out of our room and cleaned myself up in the public bathroom down the hall. I decided that in the morning that I would go first to the Dean's office to report Tank and then go to the Housing office to demand a new room. I was going to tell them everything that happened to me last night.  I would probably get Tank expelled.  Or arrested. But for now, it was late at night and there was no way I was going to go back to my room.  I went down to the TV lounge on the first floor of the dorm.  I tried to fall asleep on the couch but I had no luck.  I was still awake at 4:30 in the morning when a special edition of the university newspaper was delivered to the dorm. 

I picked up a copy of the paper and couldn't believe my eyes. The front page -- I mean the entire front page -- was a photo of Tank!  A one word headline splashed across the top of the page, "Savior!"  I proceeded to read the story about Tank -- 3 whole pages and about 10 more photos!  Tank was one of the most highly recruited high school athletes in the entire country having set about a million high school records in football and track.  After an impressive performance as a Freshman at a powerhouse SEC school, he had, at the last minute, decided to transfer  to State U.  It was highly unusual and top NCAA officials had to approve the transfer.  The article eventually got around to some interesting stuff; at his prior university, there had been accusations of sexual assault and other things. There was even a rumor that he had broken the jaw of a teammate for blowing a coverage assignment -- during practice! But no actual charges were ever filed against him.  I got the feeling that people had been covering-up for this guy for years! And now, here he was.  At State U and in my room!

I thought about how I planned to complain to the Dean and realized that maybe this wasn't such a great idea.  Getting Tank to come to State U was probably the administration's greatest accomplishment.  Nobody was going to listen to my complaints.  I sat there on couch in the TV lounge  struggling to make sense of my predicament. And eventually I drifted off to sleep. 

As I slept, I had the strangest dreams. I dreamt about Tank.  I dreamt that I really was a woman.  I dreamt about being called "girl" and "bitch" and "slut," like Tank had called me.  And scariest of all, I dreamt about performing oral sex on Tank, his enormous hard dick sliding in and out of my mouth while I eagerly sucked on it.  Oh God! What was happening to me?

The dream continued.  Now a soft voice was calling to me saying over and over, "We're here for whatever you need. We're here for whatever you need. Just ask. Just ask." That's what the little man had said before he left our room.  And in the dream I looked in a mirror and my reflection was a beautiful girl! I had breasts and wore a pretty dress and make-up. "Whatever you need...whatever you need..."  And again, Tank's massive dick was in my mouth, my head vigorously bobbing up until he came.

I woke with a start, my head pounding.  I got up off the couch and wandered around campus as the sun was just starting to rise.  I walked down to the Athletic Center which was open but practically empty.  I found myself walking past the girls' locker room.  There was a huge bin by the door labeled, "Lost and Found."  I stopped in front of the bin and looked in it.  There were dozens of pieces of clothing and underwear in a jumble.  No one was around so I reached in and pulled out a pretty, lacy pink bra.  I shuddered as I held it.

There was a large plastic shopping bag on the floor near the bin.  Without thinking, I grabbed the bag and starting cramming handfuls of clothing from the bin into the bag.  When it was full, I found a paper grocery bag and filled it too.  As I started lifting clothes out of the bin, I noticed that there were some lipsticks and other make-up items rolling around the bottom of the bin.  I grabbed those as well.  I even found a necklace and a bracelet and those also went into my bag.  With my two bags of girls' things I made my way out of the back of the Athletic Center and walked back to my dorm.

When I entered, Tank was just getting up.  I noticed that he had thrown his dirty socks and underwear on my bed.  Tank said to me, "Well, did you do what I told you to do?  Did you get some girly stuff to wear?"

I looked at the floor.  I was so ashamed to be pushed around like this.  It was so humiliating.  And yet I felt so powerless to resist.  "Yes," I said softly.  

"Good. Put it on and then get over here.  And hurry up."

I took my two bags of clothes into the bathroom.  I dumped out my random clothes onto the floor, having no idea what I had gathered or what size everything was.  I stripped down and slipped on the pretty pick lacy bra and some panties that were really tight. I rolled up two pairs of panty hose and used them to fill out the bra cups. Then I put on very short black denim skirt and a pink and black paisley top that didn't even cover my tummy.  I slipped on the necklace and the bracelet.  I was about to go back into the room when I remembered that I should put on make-up.  I chose one of the lipsticks and quickly put some on, although I don't think I did a very good job with it.

I was checking myself in the bathroom mirror and was getting dizzy seeing this very feminine reflection in the mirror when Tank bellowed from the other room, "Hurry up!"  I snapped out of my reverie and returned to the bedroom where Tank was waiting for me, completely naked.

"Let me see you," Tank said.  I stood in front of Tank, my eyes lowered, too ashamed to look at Tank.  "Yeah, that's a lot better.  You know you should have been born a girl.  I mean just look at you."  I felt like crying from the shame of my situation -- and yet I was strangely excited by what was happening.

"Well don't just stand there.  Get busy."  Tank plopped down on his bed.  I sat down on the edge of the bed and started rubbing his cock which got hard almost instantly.  "Mmmm, yeah baby, I like that.  You are a good little whore."  And after a few minutes he said, "Now suck me off, slut."  I obeyed.  I slid his giant cock into my mouth and licked and sucked and did everything I could think of to it.  Tank didn't have to force me this time.  I submitted to Tank's superiority and assumed my new position as his sissy.

As Tank came in my mouth, he growled, "That's right, swallow it all, bitch. You like that, don't you, you little whore."  I did my best to swallow it all down but there was just so much.  Some escaped my lips and dribbled down my chin.  Having no more use for me, Tank roughly shoved me away, saying, "Clean yourself up, you filthy cunt.  You're a disgrace.  And do my laundry."

Sissy Roommate -- Part 2 -- The First Time

As I said, I am Tank's full-time sissy girlfriend now.  I wear only girl clothes and make-up and I keep my hair long and in a very feminine style. I diet to stay super skinny.  I slather my body with creams and lotions to keep my skin soft.  I do this all to please Tank.  I haven't seen Tank all summer and he should be arriving any minute. Here are some photos Tank took of me last spring. He likes it when I wear really short skirts.

But I wasn't always a girlish sissy living only to serve a demanding, strong alpha-male. My life changed completely that first day that I met him.

"Come over here," Tank said, without even bothering to ask my name.  "I have a cramp in my leg.  I need you to massage it for me."  Tank pulled off the sweat pants he had been wearing, revealing a thin pair of nylon gym shorts.

I did not want to do what Tank was asking.  "I don't know anything about massages or..." I started to explain.

"Just do it now!" he demanded, pointing to his thigh.


I don't know why, but I complied with his order.  I figured he was an important athlete and that I should try to help him out if I could.  I knelt by his bed and started rubbing his thigh.

"Mmm.  Yeah.  That's good.  Rub harder.  Yeah," he said.  I was pleased that I was doing it right.  "You're hands are so soft.  Like a girl's."  I felt embarrassed when he said that but I kept on rubbing his thigh.

"Now jerk me off," Tank said as if it were the most natural request in the world. I was completely shocked when he said that.  I pulled away from him and said I wouldn't do that.  "Yes you will," he insisted.  With one hand he yanked down his shorts and with the other he grabbed my wrist and forced my hand on his enormous dick.  "Do it," he commanded, keeping his hand firmly wrapped around my wrist.  I was really scared and no match for this mountain of a man.  I wrapped my fingers around his huge cock and started stroking him, pumping him.  "Yeah, bitch! That's it!"  His breathing got more rapid and his dick started swelling.

"You know," he said, "You sort of look like a girl.  You got long hair and no muscles.  Yeah, I think we're going to pretend that you really are a girl."  He was really panting now.

"Use your mouth, bitch" he ordered.  No way I was going to that, but Tank grabbed hold of my hair and forced my head to his crotch.  I sealed my lips tightly closed, but with his other hand, Tank pinched my nose so I couldn't breathe. "Open wide, slut," he said with a laugh. As I opened my mouth to gasp for air, Tank jammed his dick into my mouth.  With both of his hands now tightly holding my head in place, I had no ability to move or fight back.  And in an instant, Tank's cock exploded, filling my mouth with spurt after spurt of his hot, sticky cum.

When he was done with me, he roughly shoved me away.  "Next time, wear a dress and some make-up or something so it won't feel so gay."

"What the fuck," was all I could think, as I pulled myself up from the floor and ran out of the room. 

Sissy Roommate -- Part 1 -- What I Look Like Now

It's the start of the college year.  I would be a junior now except that I dropped out after the end of last year.  But my boyfriend, Tank, is starting his junior year. I didn't think I would be able to take care of him properly and go to classes at the same time so I dropped out. 

I have been working for days getting our off-campus apartment ready before Tank arrives later this afternoon.  I bought new sheets and towels for him, new pots and pans for our kitchen, even some nice pictures to hang on the walls.  And I scrubbed every inch of the place so it would be sparkling clean when Tank arrives.  Of course I had to spend most of the money I earned waiting tables this summer, but it will all be worth it if Tank is happy with how our apartment looks -- and if he is happy with me.  And I spent the rest of my money on some pretty new clothes and shoes.  I don't have a single dollar left -- but that's OK because Tank has tons of money.

I finished all the apartment chores about an hour ago. That left me time to get cleaned up, do my make-up and put on one of my pretty new outfits before Tank is scheduled to arrive.  Do you like how I look?  I bought this dress over the summer and I think it is sweet and sexy at the same time.  And I think Tank will go crazy when he sees my over-the-knee socks and platform sandals.  What do you think?  After being apart all summer, I really hope Tank likes what he sees when he arrives.  I don't like to disappoint him.                                                                     Maybe I have gotten ahead of myself. Let me fill you in on some things.  First of all, Tank and I have been roommates since the beginning of last year. Tank is a superstar football player - that's where his nickname comes from.  Oh, and one more thing.  I'm not really a girl.  I'm Tank's sissy. 

It all started last September, at the beginning of my Sophomore year.  I had a really great dorm room -- a double room with its own bathroom -- but I had no roommate.  The Housing Office warned me that at some point I would be assigned a roommate and that my "single" was not a permanent thing.  Well, about one week into the semester, I came back to my room after dinner and there was this enormous guy in my room -- 6' 8" at least.  Everything about him was huge -- his shoulders, his neck, his biceps.  With him was a little man in a suit who was talking a mile a minute. "Well, Tank," the man said to him, "Since your decision to come to State U was so sudden, this is the best room we have for you. Of course, we'd rather have you down in the Athletes' Village by the gym, but that's all full right now.  But on behalf of the administration, the university is DELIGHTED to have you join us! I hope you can make do with this housing...situation until we can get you a more appropriate room." The little man seemed to be referring to me as part of the lousy rooming situation that Tank was going to have to tolerate.

"I'll make it work," Tank replied, his voice, a deep, rumbling baritone that sounded like distant thunder.

"That's swell, Tank!  Just swell! Let me know if there is anything we can do for you," the little man said as he handed Tank his card -- and an envelope that I would later learn was stuffed with cash.  "And good luck with the season. We hear that you just might break a lot of school records and even take us to a Bowl Game this year!  And let me know if you need anything. We're here for whatever you need. Just ask." With that the little man excused himself.  

The two of us were now alone in our room.  Tank plopped down on his bed and looked over to me.  I thought he was going to start a conversation, but instead just said, "Come over here."

A Pretty Little Sissy for Ms. Jones -- Part 2

"Good," said Ms. Jones with a satisfied smile. "Because I want us to become very special friends." And with that she took of the blouse and skirt she had been wearing and stood in front of Veronica in just her bra and panties. Sissy Veronica's eyes nearly popped out of his head having never seen a woman undressed in real life, let alone a sexy, curvy goddess like Ms. Jones.

"Now tell me, Veronica, tell me that you want to be a beautiful woman like me.  Say it!"

"Oh, yes, Ms. Jones, I want to be a beautiful woman just like you!"  Ms. Jones smiled with great satisfaction.

"Now come here, Veronica," Ms. Jones instructed.  She wrapped her arms around the sissy's narrow shoulders and pulled him close to her enormous breasts.  She kissed him hard on the lips and let her hands start to explore Veronica's skinny, smooth body.

"Now, Veronica, I want you to start kissing me all over my body," Ms. Jones instructed and sissy Veronica did as he was told, starting at Ms. Jones' neck and working his way down to her breasts, her belly and beyond.

As Ms. Jones looked into her new sissy plaything's eyes, she thought about all the fun they would have together.  She thought about how exciting it will be to attack her sweet young thing with an enormous strap-on dildo, taking Veronica's sissy virginity away from him.  She thought about how much fun it will be to invite her friends over -- men and women -- and to share her sissy plaything with them.  She started thinking about having a couple of giant studs spit-roast the little sissy -- one dick in his mouth, the other up his sissy pussy -- while she filmed it for the internet.  That thought made her pussy very wet!

"Now, Veronica, you have to understand that your are a sissy and that you now belong to me.  That means you have to do everything I tell you to do, without question or hesitation.  Do you understand me?"

"Yes, Ms. Jones, I understand," Sissy Veronica softly replied.

"What do you understand, sissy?"

"That I am your sissy and that I now belong to you.  And that I must do everything you tell me to do," the sissy repeated back.







"Good, sissy," Ms. Jones replied.  "Now take off your bra and panties and put on this condom.  I am going to let you fuck me with your itty-bitty sissy-dickie-wickie."  Ms. Jones laughed.

Sissy Veronica stripped as ordered and put on the condom.  Ms. Jones instructed him exactly what she wanted him to do to bring her pleasure.  And he did it.  She had the most explosive and satisfying orgasm she had had in years.  Sissy Veronica came as well, of course.  It was the most exciting moment of his life.





"Remove the condom very carefully, sissy, and hand it to me.  Now close your eyes, tilt your head back and open your mouth."  Sissy Veronica did as ordered without question.  And as he did, Ms. Jones emptied the contents of the condom into the sissy's open mouth, squeezing every last drop of sissy cum out onto Veronica's tongue.  "That's a good sissy," Ms. Jones breathed. "Swallow it all, every drop.  Sissies have to eat cum every day, so get used to it.  Some days it will be your cum, but many days it will be another man's cum."







Ms. Jones handed Sissy Veronica the white bra and panty he had been wearing earlier.  "Put these back on and wear them under your clothes tonight and at school tomorrow.  You better be wearing them when you come to my house immediately after school.   Do you understand?"

Sissy Veronica put on the bra and panties and got dressed to go home.  "Yes, Ms. Jones.  I understand completely."

A Pretty Little Sissy for Ms. Jones -- Part 1

This is Ms. Jones. She is a forty-ish divorcee with an incredible body and some pretty kinky ideas. While she dates a lot of men, she rarely feels satisfied with conventional relationships. She's tried being with other women and with groups -- but nothing has ever really felt completely fulfilling. That all changed when she got to know Vernon, the boy who lives next door.

Ms. Jones and Vernon have a secret that they share. Actually they have several secrets. One secret is that Vernon is a little sissy fairy who loves to dress up and act like a girl. The other secret is that Ms. Jones has turned sissy Vernon into her feminized love toy.

Ms. Jones had known for some time that Vernon was a little sissy. She had discovered that Vernon was accidentally using the Wi-Fi signal from her house to access the internet. With a little help she was able to monitor the internet sites Vernon visited and even read his emails and blog posts! Well, Ms. Jones learned that Vernon was into some wild stuff. Little Vernon was visiting a bunch of hardcore tranny sites -- including this blog! -- and was exchanging emails with some other sissies and admirers. Thinking that all his internet activity was anonymous, Vernon wrote long emails and posts about how he loved dressing up like a girl, how he longed for someone to turn him into a woman with large breasts, and on and on.

Ms. Jones found it very exciting to be the only person in the world who knew Vernon's secret. She would sometimes subconsciously touch herself as she spied on her little sissy neighbor's internet antics. Over time she found herself thinking about Vernon obsessively, finding the idea of a girly-sissy boy arousing. She decided to take action.

One day when Vernon was taking the garbage cans out and was all alone, Ms. Jones approached him. "Vernon, I have something very important to talk to you about. But I am only going to say this once so listen carefully. I know you are a little sissy crossdresser." Vernon was about to say something to try to deny it but Ms. Jones would have none of it. "Shut up!" she snarled sharply, causing Vernon to jump. "I told you to listen to me and I meant it!" she said in a growling, commanding way. "I know you are a sissy faggot and that's OK with me. I don't plan on telling your mother or anyone -- if you do what I ask of you. Do I have your attention?"

Vernon nodded meekly. Ms. Jones noted with satisfaction how easy it was to dominate him with just a few strong words. She also noted that even dressed as a boy he looked rather girlish, his long brown hair hanging over his rather delicate features.

"Now, I think you are going to like my proposal. Starting tomorrow, you are to come over to my house everyday after school as well as on weekends. I have plenty of girly clothes and make-up and everything you need to have your little sissy fun. I will even help you. How does that sound?"

She already knew the answer. Even though it was hard for him to admit it, the offer was like a dream come true.

The next afternoon Vernon came over to Ms. Jones house as she had instructed. She greeted him with a big hug and brought Vernon up to her bedroom where she had him undress completely, right in front of her. Ms. Jones laughed when she saw how tiny Vernon's little dickie was. Vernon was so embarrassed but completely powerless to do anything other than accept the humiliation he was experiencing.










Ms. Jones reached into a dresser and pulled out a a very pretty white bra and panty set. She explained to Vernon that this underwear belonged to one her girl lovers who was just about the same size as Vernon. She helped Vernon pull on the panties and to tuck his tiny dickie. She then fastened the bra behind his back. "Vernon," she explained, "you are going to have to learn to do this all by yourself." She then brushed out his hair and put some make-up on him. She slipped a pair of sexy, strappy black heels onto his feet. She told him to lie back on her bed as she started to take photos of him. "Do you like this, Ver..." she hesitated. "Do you like this, Veronica?" she asked. 

"Oh, yes, Ms. Jones. Very much," he replied breathlessly.

"Do you like dressing like a girl, Veronica? Are you a little fairy sissy? Well, are you?"

"Yes, Ms. Jones," he replied. "I am a little sissy fairy and I like dressing like a girl."

"Good girl, Veronica," Ms. Jones cooed. "We are going to have a wonderful time together."

As Ms. Jones continued to snap photos of sissy Veronica in his pretty white bra and panties, she asked, "Do you like me?"

"Um, yes. Of course I do," he replied.

"And do you think I'm pretty, Veronica?" she continued.

"Oh yes, Ms. Jones. I think you are beautiful. I think you are the most beautiful woman I have ever seen."

"And do you wish you could have great big, soft titties, and a pussy, like I have, Veronica?"









"Oh, yes, Ms. Jones. Yes," Vernon panted.

"Good," said Ms. Jones with a satisfied smile. "Because I want us to become very special friends." And with that she took of the blouse and skirt she had been wearing and stood in front of sissy Veronica in just her bra and panties.

Sissy Priscilla Part 3 -- Mother's Wedding Surprise

After I had taken about a million photos of my beautiful sissy son bride, I told him that we should head back inside.  I could tell he was sad when I said that, sensing that our bridal fantasy day was wrapping up.  But I had other ideas.  In fact, the fun might be just beginning!

As I said earlier, sissies have such limited lives -- no friends, no romance.  But I knew I could change that.

You see, at the same time that I was making arrangements to rent the cottage and buy flowers for today, I had also gone online to see if I might be able to find a fantasy "groom" to make Priscilla's wedding fantasy complete.  There are plenty of websites out there for men looking to meet sissies. My challenge was to find the right one.  I posted some details of what I was planning for my little sissy and, needless to say, I got hundreds of responses from horny men wanting to have some dirty action with my sweet sissy son.  But one profile stood out from all the others -- a young, tall, handsome man, clearly well educated.  He seemed to understand what I was looking for in a "dream date" for Priscilla.  I arranged to meet him in person and I liked him immediately. His name was Kurt. 

So on the day of Priscilla's wedding, while Priscilla and I were taking photo's outside, Kurt arrived at the cottage and waited patiently for us inside. When he saw us starting to walk back toward the cottage, that was his signal to come out.  Little Priscilla was so frightened and worried when this tall man walked out of our cottage and started walking straight towards us.  "Now, now, Priscilla," I reassured. "Don't be frightened.  In fact I know this man.  His name is Kurt and I invited him."

Priscilla looked so confused and scared.  Kurt confidently strode up to Priscilla.  "Hello, Priscilla," he said.  "I am Kurt.  Your groom.  Your husband.  For today." 

Well, it took some time for Priscilla to compose himself after much reassurance from me. "Come, come, Priscilla," I said.  "Play along.  This is all part of making today's fantasy complete."  After a while, Priscilla relaxed, mostly because Kurt was so charming and gentle with him.  Before too much longer, I was able to get Priscilla to smile and pose for some photos with Kurt.  Here's the first photo I took.


Well, after the first photo was done, I was able to take about two hundred more as I asked them to pose in various locations around the pond.  With each passing moment, Priscilla became more relaxed around Kurt and seemed to ease more naturally into his role as the petite bride to Kurt's manly groom.

"Now a kiss!" I shouted.  Priscilla was shocked when I said this.  Kurt wisely went in for a gentle peck on Priscilla's forehead.

"Oh that won't do at all!" I cried.  It's time for a real kiss."  And I guess Priscilla agreed.












Kurt pulled Priscilla hard against him as Priscilla closed his eyes and allowed Kurt to kiss him for a very, very long time. I was delighted to see my little sissy son experience romance for the first time in his life.  I took dozens of photos of this lovely embrace.



We went back inside the cottage where I insisted that Kurt and Priscilla act out a wedding ceremony while I took even more photos.  I had arranged for some wedding flowers for the living room to set the mood.  

"Do you, Kurt, take Priscilla to be your wife?" I intoned.  "I do!" said Kurt while Priscilla beamed.


"And do you, Priscilla, take Kurt to be your husband?"  "Oh yes, I do!" replied my eager and delighted sissy son.  "You may kiss the bride." I instructed Kurt.  And Kurt did as I told him, scooping Priscilla up in his arms and kissing his lovely bride.



















"And now for your first dance as husband and wife!" I shouted and pressed play on the CD player.  John Legend's "All of Me" began to play.  Kurt expertly led Priscilla around the living room in a gentle, slow, romantic dance.  As the song came to an end, I decided it was time for me to make my exit.  "Well, three's a crowd," I said.  There's a light dinner and a bottle of champagne for you two in the refrigerator.  I will be up in my room.  Have fun.  And congratulations!"  Priscilla giggled as I left.


At about 6:30 the next morning I heard Kurt leave the cottage and drive off in his car.  I came downstairs and found Priscilla, in his vintage peach peignoir set, sipping on a cup of coffee, looking rather disheveled -- and a bit embarrassed.

"Well, well, well," I said. "And how is the new bride this morning?"

Priscilla waited a moment, finally answering, "A bit sore, actually."  We both broke out in laughter when he said that.  I gave my sissy bride son a great big hug.  

"I hope you enjoyed your wedding fantasy, darling," I said.

"Oh yes mother.  That was the most wonderful day -- and night of my life."

Kurt continued to be a frequent visitor at our home after Priscilla's sissy wedding.  But those are stories for another time.

Sissy Priscilla Part 2 -- A Sissy Wedding Fantasy

For the past few weeks, I have been planning a very special weekend for my sissy daughter, Priscilla.  It all started when I was at a Thrift Shop and I happened to find a beautiful wedding gown in Priscilla's size for just $20.  Of course I bought it.  Here is the plan I came up with -- as soon as it was warm enough, we would rent a little cottage in the country for the weekend.  We would make the whole weekend about Priscilla's wedding fantasy!  Priscilla was so excited when I explained this to him and when I showed him the wedding dress.  I told him how we would do his hair and make up just so and then take a million photos of him as a blushing bride.  I had a few more surprises planned -- but that was all I wanted Priscilla to know about in advance.

We chose a weekend in late April and found the perfect little cottage to rent with a lovely property for taking wedding photos.  When the weekend finally arrived, I thought my darling little Priscilla was going to burst with excitement!

We drove out to the cottage on Friday afternoon, after Priscilla had come home from school and had a chance to change out of his boy clothes and into his girl clothes.  I already had everything we needed packed in the car so off we went.  We had a light dinner and afterwards I dressed Priscilla in a lovely vintage Vanity Fair peignoir set in the softest peach.  He looked so lovely as I tucked him into bed and kissed him tonight.  I wished him sweet dreams and urged him to get a good night's sleep before our exciting Saturday.

At sunrise, I brought Priscilla some toast and tea in bed and we started our day. After Priscilla showered, we spent the next couple of hours getting him all prettied up for his wedding fantasy. He started with his hair which was now almost down to his shoulders.  I watched him as he brushed in hair out in the mirror.  He seemed so happy and so natural getting ready to be a bride for the day.

Next I helped him into the lovely vintage gown I had bought for him.  I buttoned up his dress in back.  I felt so happy having the opportunity to dress my lovely bride-daughter -- even though my only child was a boy!  Since I never had a real daughter of my own, I thought this day would never come for me.  Yet here I was -- the happiest mother-of-the-bride that ever was!

Then he finished doing his make-up and voila!  My little boy was now a lovely, blushing bride.  He looked so beautiful!  I felt so proud and so happy as I looked at my little boy-bride.  

We spent the next 20 minutes pinning a wreath of fresh pink and white roses on his head.  He insisted that it had to be perfect.  It took me about ten separate tries to get it positioned to his satisfaction.  I was astonished just how much my little boy was acting like a real bride on her real wedding day.  Finally his floral crown was just right and he was complete!!!!

I picked up my camera and started taking photos for the next two hours.  We took photos everywhere -- in the cottage and around the lovely grounds. I could tell that my sweet Priscilla was having the time of his life pretending to be a bride for a day. 

I was happy that my sissy son was having fun, but as his mother I also felt some sadness.  Of course I knew that as a sissy, my son had no real friends -- and had certainly never had a real romantic experience of his own.  Real boys shun sissies like my son.  They really have nothing in common after all and could never be friends.  And sissies are too weak and too fearful to develop meaningful relationships with girls.  So while I was delighted to bring joy into Sissy Priscilla's life for one afternoon, the fact that it was just a pretend fantasy made me a bit sad.



But I had more surprises in store for Priscilla this afternoon -- something that he would never have anticipated.  I was nervous that perhaps I had gone too far -- but I was also far too excited to stop.

 

"Priscilla, darling," I called after taking a few dozen photos by the pond.  "I think it is time for us to go back inside now."

I could see a hint of disappointment on Priscilla's face when I said that, assuming that his day as a bride was coming to close.  But of course, he had no idea what further surprises I had for him.

Sissy Priscilla Part 1 -- Mother's Sweet Sissy Daughter

I have always known that my sweet little boy was a sissy.  At first he tried to hide his interest in everything girlish from me.  But I could always tell that he was more interested in girly things than a little boy should be.  He so enjoyed sitting with me at my vanity as I did my make-up and standing next to me in my closet as I picked out what dress to wear.  He was fascinated with my lingerie, my perfume, my hair curlers -- really everything that was feminine.                                                                                                                                          I knew that he secretly tried on my clothes when he thought I didn't notice.  When I thought he was ready, I spoke to him about it.  I reassured him that I didn't mind if he wanted to play dress up at home.  I told him that I thought it was sweet that he had feminine feelings and interests.  I urged him not to keep this bottled up inside and to feel safe letting his girlish feelings out at home.  At first he tried to deny what I was saying, but it didn't take long for him to crack and to admit the longings that were deep in his young heart.

These are some photos of what my son looks like now when he is at home.  Isn't he adorable?  He is so naturally feminine and girlish I sometimes forget he isn't really a girl.  He spends his days at school as a boy but after school and on weekends, he is my daughter, Priscilla.  I let him borrow any my clothes if that's what he wants to wear -- but he has a closet full of pretty outfits and drawers of lingerie of his very own. Priscilla is simply the sweetest little girl any mother could dream of for a daughter.  I don't know who is happier that there is a young girl in the house -- Priscilla or me!

For the past few years, I have been encouraging his to let his hair grow out.  His hair is now long for a boy, but I don't think anybody notices or cares; these days it seems like anything goes.  What's important to us is that his hair is now long enough that he can style it to look pretty and feminine when he wants to be Priscilla. I even take him to my beauty salon when he needs a haircut.  My stylist does such a nice job with his hair.  

We have such fun together as mother and daughter.  Here is a photo I took when Priscilla and I spent a weekend in the country.  We stayed in a cute little bed and breakfast, went antiquing, shopped for crafts and clothes.  In the evening we went to a state fair that really fun.  I noticed that a lot of the teenage boys at the fair were "checking out" Priscilla as we walked around together.  Can you blame them?  Of course not! My Priscilla looks adorable!  No one had any idea that the pretty young girl in the beret was actually a boy.

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.