Sissy Roommate - Part 10 - The Conclusion

 I know it's been a long story, but now you are up to date.  It's the start of Tank's Junior year.  I dropped out because I knew I couldn't care for Tank and take classes at the same time.  But Tank and I will be living together this year in a beautiful condo that a rich alumnus has provided for Tank.  I've been working hard to make sure it is clean and all ready for Tank when he arrives, which should be any minute now.

I bought some new clothes over the summer, including the outfit you see me wearing here.  I sure hope Tank likes it when he sees me.  And I curled my hair which got longer over the summer.   I'm making an extra effort to look nice since I haven't even seen Tank all summer long!

And best of all, the hormones really kicked in over the summer and my breasts grew a lot! 

Excuse me, my phone is ringing.  Oh great, it's Tank!

"Hi Tank! Are you almost here?  The condo is all clean and I...."

"Stop talking!" Tank barked through the phone. "Jesus Christ! Just shut up and listen!"

"OK  Sorry," I replied softly.

"Look, a lot of stuff happened over the summer. I'm engaged," Tank explained flatly.

"What? I don't understand. Are you joking? What are you saying?" I babbled.

"If you would shut the fuck up, I would tell you, you stupid sissy bitch.  You remember Amber Destry, the swimmer from the Hall of Fame event last Spring?"

"Yes," I answered softly. My tummy started doing backflips. Remember Amber?  How could I forget. She was like a living Barbie doll.

"Well we got engaged this summer. And her dad, who's loaded, has bought us a house off campus to live in together."

"But what about our condo? What does..."

"For the last time, shut the fuck up!  The good news for you is that the alum that owns the condo has agreed to let Jefferson and Jackson live there.  And they seemed pretty interested in you when they met you last year, so I decided that you can just start being their sissy from now on."

I couldn't even make sense of what I was hearing. Tank was engaged to a real girl.  I wasn't going to be living with him.  And Tank had just decided that I would now be...given?...to Jefferson and Jackson.  I started to feel faint.

"Got to go," Tank said and he hung up.

I put down my phone and grabbed hold of the kitchen counter to steady myself.  What was happening?  What was I going to do?  I didn't have a penny to my name and I had no where to go.  My head was spinning.

But not for long.  Because just then I heard the front door being unlocked and in walked Jefferson and Jackson.

"Hello sissy!  We're home!" shouted one of them in a loud sing-song voice.  The other one broke out laughing.

"Damn!  Look how he's dressed!  Did you get all dolled up because you knew we were coming?  You are one sexy sissy!" the first one said. 

The other one grabbed me by the throat with one hand and roughly grabbed one of my soft new breasts with the other. "It's true, Jack! The sissy really does have titties like Tank said!"  He kept squeezing my breast and my neck really hard -- and then he licked my face, from my chin up to my forehead.

Then Jack laughed and said, "You know how I love titties!" Then he said, "Keep holding him like that, Jeff.  I'm gonna get this party started!" as he unzipped his pants.

THE END

Sissy Roommate -- Part 9 -- Sissy on Display

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

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

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

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

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

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

"What?"  I asked.

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

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

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

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

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

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

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

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

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

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

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

A Sissy Refresher -- Part 10

Sissy Erica returned to the living room wearing the sweetest little ensemble; a strapless lace and satin dress with a matching little bolero jacket.

"What a perfect little outfit for the trip home!" I said.

"Oh, yes," Ms. Trainer agreed.  "Doesn't he look lovely!  My assistants have been loading all of Erica's new outfits into your car.  The cargo area of your Escalade is completely full."

"That's fine," I replied. "We'll let Sissy Erica sit in the back seat instead of the cargo area, as usual."

"You drive," Roberto said to me. "I'm going to sit in back with Erica.  I need to have my dick sucked on the drive home.  I might want to fuck him too."

"That's fine dear," I replied.










"You will find everything you need has been loaded into your car," Ms. Trainer said. "All his pretty new dresses as well as his extra corsets.  In about four weeks he should be ready to squeeze into the next smaller size."  I could see Erica's face turn pale when Ms. Trainer said he would be wearing an even tighter corset soon!


"Well, Erica," Ms. Trainer said, "I hope you are going to be a good little sissy for your wife/mistress and her lover.  I expect you to apply everything you learned here this summer to being the best little sissy you can be."

"Yes, Ms. Trainer," Erica managed to reply.

"That's good, Erica.  I would expect nothing less from you.












"Now take off your little jacket," Ms. Trainer instructed. " I don't think you will be needing that for your ride home in the backseat with Roberto."  Erica took off the jacket as we once again gazed with amazement at how feminine and delicate Erica now appeared. Turning to Roberto, Ms. Trainer said, "Erica's tight little sissy-pussy has lubed up so he is ready to be fucked whenever you want."

Turning her attention back to Sissy Erica, Ms. Training said, "We will all miss you, Erica. You are a darling little sissy.  You are wonderfully obedient and pathetic." And with that Ms. Training gave Erica and deep, hard kiss on the lips.  Erica staggered from the experience of being kissed by Ms. Trainer, revealing just how extensively Sissy Erica had been broken, being erotically aroused by his tormentor.

Ms. Trainer continued. "Erica, I have been speaking with your owners and we've agreed that we will have you come back here for another 12 week Sissy Refresher course next summer!  Isn't that wonderful news!  We are already working on the new curriculum -- all sorts of new advanced sissy skills to teach you.  Isn't that exciting?"

I thought Erica was going to die when he heard this.  I added to the fun, "That's right, Erica.  Roberto and I are planning a long trip to Australia and New Zealand next summer so we decided that it would be best to bring you back here while we're gone.  Now answer Ms. Trainer, Erica.  She asked you if you were excited about coming back here for another 12 weeks of sissy training."

"Yes, Ms. Trainer.  I'm very excited about coming back for more sissy training," he barely managed to say.

"We are excited knowing that you will be back with us.  But for now, it is time for you to go and resume your duties caring for your wife/mistress and her lover."

"So hurry up and get in the car, sissy bitch," Roberto snarled.

And with that, Sissy Erica minced his way back to the car, returning to his life as a helpless, pathetic, feminized sissy toy for his wife and her lover.

A Sissy Refresher -- Part 7

"Now I don't know if you ever take Sissy Erica out with you in the evenings, but I think this dress would be perfect for a sissy night on the town," Ms. Trainer began as Erica re-entered the room, this time wearing a little black dress embellished with rhinestone around the neckline.  The dress was simple, classic -- but Erica still looked so damn sexy!

"Yes, sometimes we take Erica out with us, often when we have a male friend of Roberto's visiting from out of town.  It's fun for us to make it a double date, letting Erica be a real man's pretty date for the evening.  And yes, this dress would be perfect!  What man wouldn't love having a sexy escort like that!" Roberto heartily agreed.

Changing the subject, I asked, "So tell me, what is the diet you put the sissies on to get them so...svelte?"

"Erica, tell your wife/mistress what you ate while you were here."

Erica mumbled a response that I couldn't understand.

"Oh speak up, Erica, for God's sake! Nobody likes a mumbling sissy!"

"Baby food," Erica managed to say.

"What?" I exclaimed.  Barely able to contain my surprise and laughter.

"Oh, yes," Ms. Trainer explained.  "It's a wonderful way to control and minimize portions and calories and dignity.  One small jar, three times a day, will guarantee rapid weight and self-respect loss."

"No wonder he looks so slim and dainty," I remarked.

"Erica, sweetie," Ms. Trainer asked. "What else did you eat while you were here?"

Erica looked terrified.  "Nothing, Ms. Trainer.  I ate nothing else.  Only the food that I was given.  Honest."  Erica looked panicked, believing that he was being accused of an infraction of the rules.

"Don't get your panties in a twist, sweetie.  You're not in trouble.  I was just pointing out that you ate something besides baby food all summer."

Erica still looked confused and frightened.  "I was just pointing out, Erica," Ms. Trainer explained a bit impatiently, "that you also ate a lot of semen over the past twelve weeks.  And I mean a lot!  Isn't that true, Erica?"

Erica's fear instantly turned to intense shame.  "Yes, Ms. Trainer," came the pitiful response.  "I did eat a lot of semen."

"You see?" Ms. Trainer added.  "Our sissies get a perfectly balanced diet here!"  I almost fell on the floor laughing when she said that.

"Let's see another dress!" Ms. Trainer chirped.

A Sissy Refresher -- Part 4

Erica re-entered the room where Roberto, Ms. Trainer and I were sitting.  This time he was wearing an elegant gold cocktail dress, sleeveless with a deep vee back.  The bodice of the dress was decorated with little pearls, while a wide sash of gathered fabric wrapped around him, just below the bust.  He looked so elegant and beautiful.  Simply stunning!                                                                          I was still astonished by how skinny and delicate he looked, his pretty new dress draped over his slender shoulders.  Ever since I feminized him five years ago, I have been able to easily dominate Erica -- mentally and physically -- but in his current emaciated state, I'm was pretty sure I would be able to do anything I could imagine to him physically.  Pick him up.  Throw him down.  Slap him around.  Anything.  The thought got me excited.

I looked again at Erica's face.  The fear and sadness were so visible, his eyes barely holding back back tears of shame and anxiety.                                                                                         "What's with this crazy fashion show?" Roberto asked. "Why can't we just throw Erica into the trunk of the car and take him home already?"                                                                                         "Roberto, I already explained this to you about a dozen times," I said with some exasperation.  "Part of the training Erica received was in becoming a 'decorative sissy.'  Ms. Trainer is letting us see some of Erica's new outfits that he'll be wearing at home."

"What's wrong with his maid's uniforms?" Roberto asked.                                                                                                                                                Ms. Trainer jumped in to help me out.  "Roberto, 'decorative sissies' are all the latest rage.  Of course it only really works if you have an exceptionally pretty sissy like Erica.  But let me explain.  Of course there is nothing wrong with him wearing a maid's uniform.  When Erica is doing his chores -- cooking, cleaning, etc. -- he will continue to dress as a maid.  But at other times he can serve you in a more 'decorative' manner.  Like when he is bringing you coffee in bed or greeting you when you return home in the evening, Erica will change into one of his pretty new dresses and high strappy shoes so he can look his very best while he's serving you.  And think how elegant it will be when Erica greets your guests at the front door dressed like this, to take their coats and to show them in.  And say you and your wife are relaxing in den or entertaining another couple, Erica can be posed where ever you want him, silently and motionlessly adding some beauty to your home.  As a 'decorative sissy,' think of him more like a pretty vase or painting on the wall than as a person."

"Or a Barbie doll," Roberto responded.

 "Yes. Very much like a Barbie doll," Ms. Trainer replied.  "But you can't gang fuck a Barbie doll in the ass, now can you?"  We all had a huge laugh at Ms. Trainer's joke.  Well, all except Erica.                                                                                          "But won't that be a lot of extra work, changing in and out of his maid's dress and these fancy dresses, re-doing his hair and make-up, several times a day?" Roberto asked.                                                                                                               "Of course it will be a lot of extra time and effort for Erica, but he doesn't mind.  Do you, sweetie?  You will be honored to work hard to be extra pretty around the house. Right?"

"Yes, Ms. Trainer.  I will be honored to make myself extra pretty around the house," Erica replied softly, staring down at the floor, unable to meet our eyes as his future as a Barbie-like fuck toy was joked about right in front of him.                                                                                               "Such a sweet sissy," Ms. Trainer cooed.  "Time for another dress!"

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.

Taking Delivery of My New Sissy -- Part 2

I kept my spent dick in my sissy's mouth until it started to go limp.  Sissy Gwendolyn expertly and eagerly cleaned every drop of cum off of it with his well trained tongue.

"Take off your top," I directed.  "I want to see your titties."  My new sissy obediently did as his master instructed.  

"Now I 'm going to fuck your pretty little sissy ass-pussy.  How do you feel about that?" I asked.

"Oh, please, please, please ram your enormous cock up my sissy-pussy," my new sissy pleaded desperately.  My dick sprang to attention once again.  I was going to fuck the shit out on this sexy sissy plaything.

As my new Sissy wiggled out of his sheer black lacy top, I was able to admire just how perfect and feminine his little sissy body was.  I took a moment to drink in his long skinny legs, his pale, soft skin and those incredible titties.  The room had mirrors everywhere -- even on the floor -- so I could enjoy the sight of my new plaything from several angles at once.  This was the best moment of my life.

Just look at my perfect Gwendolyn in the picture to the right.  I did fuck him right there.  As I fucked him he started crying, either from the pain of my giant cock up his tight little ass or from the humiliation of being another man's sex toy.  I smiled at the thought that both were true. I must have dumped a gallon of my hot sticky cum in his ass!

And then it was time to take my sissy home. While Sissy Gwendolyn and I were getting acquainted, Ms. Trainer's staff had move Gwendolyn's few possessions into my car.

"Would you like us to dress him before you take him to your car?" one of Ms. Trainer's assistants helpfully offered.

I thought for a moment.  I knew there was a heavy snow falling outside and a bitter cold wind.  "No thank you," I replied.  "He can walk out to my car dressed exactly as he is."

Taking Delivery of My New Sissy -- Part 1

Yesterday was the happiest day of my life. You see, I took possession of the new Sissy I had ordered from Ms. Trainer's Feminization Service. When I set eyes on my new Sissy boy, well my heart nearly stopped beating -- and my great big dick got instantly hard! 


When I arrived at Ms. Trainer's I was led into a private reception room where my sissy was waiting for me.  He was patiently kneeling on the floor, his skinny, frail little body barely concealed by a flimsy, sheer black lingerie set.  I thought he looked like a little angel.  His skin was pale and soft, his face was made-up perfectly, and his perfect titties were visible through his sheer lacy blouse.

I had gotten addicted to sissies about 5 years ago after my second wife left me.  I never had much luck with women.  They won't tolerate my abusive behavior and my insatiable need for sex. That's when I started hanging out at tranny bars and picking up sissies for one-night stands.  It was easy and I could treat them like shit -- and they seemed to enjoy it.  But I grew tired of the bar scene and the drag queens that I was having sex with weren't doing it for me any more.  

That's when I learned about Ms. Trainer's Service.  For an enormous sum of cash (don't worry, I'm rich) Ms. Trainer said she could provide me with a trained, transformed sissy that would meet my every requirement.  Well that's what she did and she exceeded my expectations.

My new sissy is simply gorgeous.  At first I couldn't take my eyes off his perfect little sissy body.  But then I noticed his big, beautiful hazel eyes.  I was entranced.  I knew I had found the sissy of my dreams!

"Your new name is 'Gwendolyn'," I announced.  "And you shall call me 'Daddy'.  Or 'Sir'  Any Questions?" 

"No questions, Daddy...Sir," my new sissy answered immediately and meekly.

"Good," I responded.  "Now, tell me about yourself.  Tell me where you come from and how you came to be here," I asked.

Sissy Gwedolyn seemed surprised by the question at first but after a moment started to answer.  "Well, Daddy, Sir," he started.  "I was born in a town outside of C..."

Before Sissy Gwendolyn could even start his first sentence, I slapped him hard across his pretty sissy face. "Nobody cares about who you were or where you came from," I snarled.  "As far as we are concerned, your entire life started today, right here, when you met me. I am your life.  I am everything.  Beyond me there is nothing.  And without me, you are nothing.  Do you understand?"

"Yes, Daddy Sir.  Yes, yes, I understand.  Please forgive me.  I am so sorry.  That will never happen again," Sissy Gwendolyn managed to blurt out knowing that he had badly transgressed.



"Now suck my dick," I commanded.  Sissy Gwendolyn did exactly as directed. As he unzipped my pants and pulled down my briefs, he gasped -- either in admiration or more likely terror -- at the size of my monstrous cock.  He quickly regained his composure and focus. He pulled his pretty shoulder length hair back away from his lovely face and went to town on my cock.  My new little sissy knew exactly what he was doing in the cock sucking department!  He kissed, licked and sucked my rock hard dick until it exploded in his pretty little mouth.  He eagerly swallowed every single drop of my cum as if it were the most expensive and delicious champagne in the world!

A Sissy's Mother Has a Plan -- Part 2

Mr. Robbins had never experienced a blow job like this before -- not from any of his girlfriends or from his ex-wives or even from any of the hookers who worked for him. As he looked down at the reluctant sissy he was face fucking, he felt a sense of power and excitement he had never felt before. It was electrifying to have his dick sucked by a boy that was transformed into a girly love toy just for his pleasure.

The excitement was too much for Mr. Robbins. As he started to cum, he roughly pulled Sissy Billy's head into his crotch, ramming the full length of his dick far down the sissy's throat. Mr. Robbin's orgasm was explosive. It felt as if he was pumping gallon after gallon of semen into the feminized plaything in front of him. It was the most powerful orgasm of his life!

But for poor Sissy Billy, it was not enjoyable at all.  He struggled to remain conscious throughout the ordeal as the giant cock was forced down his throat while Mr. Robbins roughly gripped the back of the sissy's pretty little head. 

As Mr. Robbins slowly removed his spent cock from Sissy Billy's mouth, he had a realization. Why should he put up Billy's mother -- that gold-digging bitch -- when he could just have her sissy son instead?  He sent a text to his "driver" who was waiting outside.  "Need U 2 take out trash."

Sissy Billy was collapsed on the floor after his brutal face fucking.  He was gagging, gasping for air and sobbing all at the same time.  Mr. Robbins kicked Sissy Billy.  "Go fix your make-up, Sissy," Mr. Robbins said. "I'm not done with you yet."

Billy had seated himself at the vanity when the "driver" -- one of Mr. Robbins' thugs -- burst into the room. Mother and Billy were shocked when this stranger, this mountain of a man, stormed into the bedroom.

"What's going on here?!  Who are you?!" Mother screeched, as she tried to cover her nearly naked body.  

"Which one?" the driver asked, ignoring Mother's question.  

"The old one," replied Mr. Robbins. And while Sissy Billy sat in open-mouthed shock, the driver overpowered Mother and held a drugged rag over her nose and mouth until she was unconconsious. The driver then threw Mother over his shoulder and carried her out to the car.   

"What's...what's happening?" Sissy Billy managed.  "What did you do to my Mother?"

"Don't worry about her.  She's just going away."  What he didn't say was that Mother would soon be lying in a New Jersey landfill.

"Well now, Billy," Mr. Robbins continued. "It looks like it's going to be just you and me from now on. You're going to move into my house and you're going to be my full time Sissy whore.  Doesn't that sound like fun?" he added with a snear. 

"Maybe I'll give you some great big boobs.  Yeah, I like that idea.  And maybe I'll cut off your dick."  Mr. Robbins' own dick was starting to get hard again.  Roughly, he grabbed the sissy and bent him over the back of a love seat, positioning the sissy's little bottom up in the air. "Time to lose your sissy cheery!" Mr. Robbins said as he drove his big dick into Billy's tight little bottom.

"On, yeah! That feels great!" Mr. Robbins exclaimed.  Mr. Robbins had another explosive orgasm while tears of pain, humiliation and fear poured down Sissy Billy's face.  

A Sissy's Mother Has a Plan -- Part 1

Billy had been seated at his mother's vanity for the past two hours while she did his hair and his make-up, ensuring that Billy looked like a sweet and sexy young lady.  Heavy gold earrings hung from his recently pierced ears.  His eyebrows had been plucked into gentle arches.  His recent strict dieting had succeeded in making him very skinny and delicate looking.

He wore nothing but a darling little bra and panty outfit in the softest pink. Mother had padded the bra cups to give the appearance that Billy had little breasts.  The bra was festooned with a a large bow and long ribbon. It was a very seductive outfit.

The doorbell rang and mother exclaimed, "Oh good!  He's here!  Now don't forget ANYTHING I told you about what you are going to do tonight. Do you understand?"

Billy turned on the little vanity stool on which he had been perched.  He looked at his mother who was wearing the identical pink bra and panty set.  His anxiety was mounting by the minute.  He pleaded, "But mother, do I really have to do this? Please don't make me. Please!"

Mother was not going to tolerate even a hint of insubordination.  She needed Billy's complete and enthusiastic cooperation.  Mother stormed over to where Billy sat on the vanity stool and pointed her long, manicured finger directly in his face.  "Do NOT let me down tonight or you will regret it! I think we should both consider ourselves very fortunate that Mr. Robbins has taken such a keen interest in us.  With just a little more effort, I think he might ask me to marry him and then all our problems will be solved.  We are completely broke and things have been very hard for me ever since your lousy father ran out on us."

"But mother, please!" Billy said as tears welled up in his eyes.  "I've been good.  I let you dress me up like a girl and go out with both of you on your dates.  I even let Mr. Robbins touch me and hug me. But this is completely different. Dressed like this he is going to expect only one thing.  Sex!"

"No shit, genius," Mother harshly replied.

"And besides," Billy said through his tears. "Mr. Robbins is a bad man.  Everyone knows he's part of the mob."

That comment enraged Mother.  She slapped her sissy son hard across the face. "You take that back! Mr. Robbins is rich because of his perfectly legimate waste disposal business. Now wipe those tears away and pull yourself together." 

Mother went downstairs and let Mr. Robbins.  When she led him into the bedroom, he saw that both Mother and her sissy son were dressed in the exact same sexy outfit.  A big smile crossed his face.  "Well," Mr. Robbins said. "This is going to be an interesting evening.  Let's see what this sissy can do.  Get over here and get on your knees, sissy."

Sissy Billy did as he was ordered.  He unzipped Mr. Robbins pants and outsprang an enormous cock.  "Don't just stare at it, sissy!  Suck it!  NOW!"

Reluctantly, Billy did what Mr. Robbins wanted.  He closed his eyes and put the stiffening dick in his mouth.  Mr. Robbins firmly held the back of Sissy Billy's head as he began pumping in and out of Billy's virgin mouth.

Completing My Husband's Sissy Journey - Part 3

Tonight, Marcus, Colette and I are "staying in" for the evening.  Colette prepared a lovely dinner for the three of us.  After he had finished clearing the dishes, Colette and I went up to our bedroom to get ready for the rest of the evening.

Colette took off the pretty little black dress he had been wearing and changed into a sexy outfit I had bought for him -- a silk brochade corset in the deepest green, sheer black opera gloves, and black seamed stockings. I had him slip on his sexiest shoes -- black platforms with a 6 inch heel.  He looked so beautiful as he stood in front of the mirror to brush his hair and to freshen his red red lipstick.  I noticed with great pleasure how his diet of female hormones combined with the corset was making his bottom look so soft and round.

I could see that Colette was getting nervous about what was about to happen so I gave him a Valium to settle him down a bit.  

I changed into a lacy black negilgee.  Almost as sexy as Colette's outfit but much more comfortable.

I posed Colette on the edge of a chair and invited Marcus into the bedroom.  When he saw the two of us in our sexy black outfits I thought his eyes were going to pop out of his head.  Marcus told Colette to stand and to turn around so he could enjoy the view of sexy Colette from every angle.  "That is one fine looking sissy!" Marcus said appreciatively.




























I wrapped my arms around our handsome lover.  "Well, Marcus, where do you want to begin.  Would you like us to suck your dick together?" I asked.  "Or maybe you'd like to fuck me while Colette tongues you asshole?"

"Nah," he replied.  "The sissy can wait.  I just want to have sex with you for a while."

"OK, darling.  Whatever you want.  Colette, sweetie, please go wait in ths closet until Marcus and I are done," I instructed. The combination of the wine from dinner and the Valium were having an effect on Colette. Obediently, he walked into the closet as he had done on other occassions when Marcus and I needed some alone time.  I closed the closet door and Marcus and I made passionate (and very loud!) love while Colette listened and waited in the closet. 

After Marcus had fully satisfied -- and exhausted -- me, he called out, "Sissy!  Get in here!"  Colette emerged from the closet.  "Get on the bed," Marcus instructed.



"Oh!" I exclaimed.  "He looks so pretty.  Let me take some photos before you two have sex!" I said.  I grabbed my camera and had Colette assume a variety of sexy photos on the bed.  Marcus was clearly getting turned on watching this, his huge cock already starting to get hard again.

I kept taking photos as Marcus used poor little Colette for his enjoyment, first with Colette's mouth and then with his "sissy pussy."  I have a whole collection of Colette's "action photos" posted on the web.

When Marcus was finally done cumming in my sweet little Colette, he told Colette to go sleep in the guest room so he could spend the rest of the night with me alone.  As Colette was about to leave the bedroom I said, "Colette, aren't you forgetting something?"

"Oh yes, of course," he replied. "Thank you for fucking me Mr. Marcus.  And thank you for fucking and pleasuring my wife in ways I never could."

"You're welcome, sissy," Marcus replied.  "Now get out."  And with that, Colette retreated to the little guest room for the night, a little unsteady in his high heels on account of the wine, the Valium and the serious fucking he had just had endured.