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."

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. 

My Sissy Neighbor -- Part 11: Some BIG Changes

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Sissy Attitude Adjustment

Poor Sissy Millie just couldn't seem to accept what was happening to him. 

Physically, Sissy Millie was a huge success -- his forced transformation from occasional crossdresser to chemically and surgically feminized sissy was nearly perfect.  His face was smooth and beautiful, his body was soft and slender.  His hair was long and full.  And his boobs were...well...incredible.  Just look at them!  I can't resist squeezing them and playing with them!

Everything was perfect except for his attitude.

You see, Sissy Millie continued to insist that he was "a man."  He kept shouting that his name was Simon and he would never be another man's full-time, live-in sissy slave.

This was a real problem for me.  Sissy Millie's new owner was scheduled to take possession of his sissy in just three weeks.  But Sissy Millie's attitude -- his entire mental state -- needed a major adjustment.  And quickly!

I've been through this many times before and I have never failed to break a sissy. Sissy Millie is going to wish he had cooperated with his transformation and succumbed to his new life before it came to this.  He is going to endure punishment beyond his wildest imagination.  Once it begins, he is going to start begging me to stop the torture -- begging to be allowed to embrace his new life as a sissy maid and sex slave.  But I am not going to stop until I know that Simon is gone and only Sissy Millie remains. And if that takes three weeks, well that's OK with me. 

Sissy Millie has been tightly corseted, bound and perched on that little stool all night long, a 12 inch dildo vibrating and pulsing wildly in his sissy pussy.  Morning has finally arrived after a long, painful and sleepless night.  He is terrified and exhausted. But his worst fears about what are about to happen to him are nothing -- NOTHING -- compared to what this final stage of his transformation will be like. We will completely break his will and his soul.

I feel no guilt about the suffering Sissy Millie will soon endure.  This is all his own damn fault.

A Sissy Nanny -- Part 3

The first time I realized that the lactation hormones I was feeding my Sissy Susie were working was when he started leaking milk!  One night Greg was screaming at Susie for something that he had done wrong, which Greg does very often.  While Susie was standing there, eyes lowered, accepting Greg's abuse, wet stains started to appear on the front of his maid's uniform.  "What the fuck is happening?" Greg yelled at Susie.  "Are you cumming out your tits?"  I thought that was really funny.  Poor Susie was so confused.  He had no idea that I had added the lactation drug to his daily diet of hormones.

We love making Susie leak - it has become a new hobby for Greg and me.  We learned we could make Susie leak just by yelling at him -- or by making him watch while Greg and I get romantic.   

Because we got so much enjoyment from making him leak, I threw out all of Susie's old bras and now only allow him to wear half cup bras that expose his nipples.  I also added a few satin blouses to his wardrobe.  Because of the lactation meds, Sissy Susie's nipples have grown really big and pointy.  And when he wears his new bras and blouses, his nipple are very prominent, sticking out beneath his blouse for for all to see.  And when he leaks, the satin blouses really show off the dark, wet stains.

Like I said, Greg and I have learned to make Susie leak whenever we want.  All Greg has to do is to start shouting at Susie and, voila, the milk starts flowing.  We can be out shopping and Greg will get into Susie's face and start shouting at him about how pathetic and stupid he is.  Then the dark, wet stains start to form on his blouse.  He usually starts crying at the embarrassment of leaking in public as well as the reminder that he even lacks control over his own sissified body.

Susie's boobs also start squirting every time he watches us get romantic.  We have always made Susie be our "attendant' while we make love.  He stands silently in the corner of our room while Greg and I get it on.  That way Susie is always ready to do whatever we need -- fetching us a drink or cleaning up our wet messes.   But nowadays while watching Greg fuck me, we get the added fun of watching Susie's boobs start squirting uncontrollably.  It must be humiliating beyond all imagination for Sissy Susie, his own body betraying him while watching his own wife get wildly fucked by a real man.

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.  

Completing my Husband's Sissy Journey -- Part 2

I enjoy having my husband, Colette, as my own, private lesbian lover and slave during the week.  But when the weekend comes, I'm ready to get out and really have some fun.  You see, I now have a boyfriend.  And so does my husband!  

When I first told Colette that I had taken a new male lover, he was very upset.  I let him cry for a few minutes but then ordered him to stop his blubbering.  Having a lover is what I wanted and Colette would just have to deal with it.  When he wouldn't quit sobbing I slapped him a few times until he stopped.

The very next night I invited Marcus, my lover, over to our house to spend  the evening with Colette and me.  I made Colette dress up and look his best before meeting Marcus. Here's a picture of Colette putting on his bra as we both got dressed for the evening.  Colette served us drinks and hors d'oeuvres that he had prepared.  He looked so pretty!  I know he was upset watching Marcus and me making out on the couch right in front of him.  But Colette behaved himself and worked hard to make me proud.


But that was just the beginning.  What Colette didn't know then was that I wanted Colette to share Marcus with me!  Marcus would become Colette's handsome lover too!



When I explained all this to poor little Colette, I thought he was going to explode!  He cried and cried.  He begged me not to do this.  But I had made up my mind.

So now, every Friday and Saturday night, Marcus takes his two beautiful "girlfriends" out on the town.  We go to bars, restaurants, dancing.  We even go on vacation together.  I bought Colette lots of pretty new clothes so he can look his best when we are out on our date nights with Marcus.  Here's a pretty pink dress that I think looks very nice on him.

At first it was very difficult for Colette to participate in our special "double dates."  But he cooperates because it is what I want.  

Tonight, Marcus is going to take us to dinner at the fanciest French restaurant in town.  We are celebrating our one year anniversary as a couple (plus one!)  And then after dinner we are going to go to the nightclub at the Hilton where we can dance and drink until very late.  I bought Colette a special new dress for tonight and we spent the afternoon at the beauty salon having our hair and make up done for our big night out.  Doesn't he look beautiful!  I made Colette pose for photos when we left the salon.  I think he looks pretty happy in these picture.  I think Colette enjoys being the object of Marcus's attention and desire a lot more than he admits!  What do you think?

I'm sure Marcus will be pleased that our sissy lover looks so pretty tonight.

A Sissy Gets Married Off

I had known about my husband's feminine urges since before we were married.  I didn't mind his cross dressing or his need to be submissive to me.

At first this was exciting for me too.  I had always had a dominant streak and my husband's Sissy submission to me fulfilled certain needs I had as well.  But eventually, I tired of the game.  In my strict hands, my husband had progressed from a weak-willed, cross-dressing male to a beautiful, fully feminized submissive Sissy.

I needed to make some changes in my life.  Most importantly, I needed to kick my Sissy husband out of the house so my new lover could move in with me full-time.

My Sissy husband was very upset when I explained that I had arranged to marry him off to a man I had found who was looking for a Sissy wife.  There were lots of tears and he begged for me not to go through with this, but I had made up my mind.  Anyway, who cares what a Sissy wants?

That was six months ago.  I am now very happily living with my handsome lover and my Sissy ex is living with his new Husband and Master.  My Sissy ex's entire life now revolves around pleasing his Husband and Master.  He spends hours each day ensuring that his hair and make-up are perfect as his Husband requires.  He toils around the clock to ensure that the house is spotless, clothes are washed and ironed, and that meals are on the table when his Husband returns home from work.  And of course, my Sissy ex has to satisfy his Husband and Master's endless sexual needs as well.

From the photos I've seen, it looks like my ex is starting to embrace his new life as the Sissy wife to a real man.   He certainly seems to enjoy being treated as a "lady" by his strong and dominant Husband.  Look at how he smiles as his Husband and Master touches him with his rough, strong hands.  Look at how he moans with pleasure when being kissed and having his Husband fondle his big boobs.

I guess it was always his destiny to be the submissive Sissy wife of a real man.


 

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."

Reluctant Sissy Bride

  

The Colombian drug lord had waited a long time and paid a quarter million dollars to have this Sissy made for him. His heart raced and his cock swelled the instant he laid eyes on the equisite Sissy bride sitting before him.

Two years ago, the drug lord had been betrayed by a former business partner. He thought long and hard about how he would get his revenge. And so he arranged for the kidnapping of deceitful partner's only teenage son and to transform the spoiled brat into his very own Sissy wife.

"Well done, Arturo, well done," the drug lord said to the Sissy's trainer and surgeon.

"Yes," Arturo replied. "He is stunning, isn't he. He makes such a lovely bride. It's such a shame that he has been so resistant to the transformation, to his new body and his new life. It has been necessary to either keep him drugged or in restraints at all times. He is horrified -- nearly to the point of insanity -- by what we've done to him. It's unfortunate."

"Quite the contrary, Arturo. I'm delighted that the forced sissification has been torture for him. This couldn't be better!" the drug lord said with glee, enjoying the sweetness of his revenge.

"The Sissy's drugs are wearing off," Arturo explained. "I knew you wanted him awake and lucid for your wedding ceremony. His hands are tightly bound behind him; I suggest you keep him in restraints when not drugged. After the ceremony, let me know if you want him drugged for your wedding night."

"Oh goodness no!" replied the drug lord. "I will just tie him to my bed. I want my little Sissy to be able to enjoy his first night in bed as my little Sissy wife."  

New Sissies for the Harem - Part 1

As one of the wealthiest oil barons in Saudi Arabia, the Prince had unlimited funds with which to build his Sissy Harem.  Frail and effeminate boys were lured from ghettos in Europe and Asia with promises of jobs in the Prince's palace.  What actually awaited these unsuspecting boys was a lifetime of captivity and a 24/7 program of feminization.  After a year of hormones, surgery and intensive training, the thoroughly feminized boys "graduate" to become part of the Prince's Sissy Harem where their lives are focused solely on attaining sissified perfection and pleasing their Prince and Master in every way.  Here we see two of the Prince's favorite Sissies about to engage in some hot Sissy passion for the Prince's entertainment.

Sissy Drugged for Party Night

Sissy Maria was just starting to regain consciousness, having been heavily drugged earlier in the day -- as always happened before the weekly "party nights" that the Master arranged.  As Sissy Maria re-awakened, he could see that he had been dressed in a very sexy and revealing belly dancer's outfit.  In the mirrored ceiling he could see that his hair and make-up had done -- he had been primped and painted and dressed as a super sexy harem girl.  The room was still spinning as he started to become aware that he was surrounded by a dozen men, all of whom were starting to remove their pants.  He tried to move but the drugs left her with no control of his body.  He couldn't even scream.  He was stuck, on display on the table in the middle of the room full of his Master's horny and perverted friends.  Poor Sissy Maria, the drugs had now worn off enough that he was fully aware of the gang rape he was about to endure -- but was unable to defend himself in any way.  He squeezed her eyes tightly shut and began to silently sob at his fate. 

Sexy Sissy Escort

Feminized to absolute perfection, Sissy Annette was ready for another night as a high-priced sissy escort for visiting businessmen.  It had been a very busy week as there was a convention in town.  Sissy Annette was going on 3 or 4 dates every day!

How did poor little Sissy Annette end up in this position?  Three years ago, as a young crossdresser, he responded to an ad on Craig's List offering "transformation" make-up services from a woman named Vanessa.  Vanessa was an expert and made Sissy Annette look and feel completely feminine -- for a heavy price.  Sissy Annette was soon having make-over sessions with Vanessa several times a week and was soon deeply in debt.  Sissy Annette was addicted to Vanessa's tranformations and was completely ensnared in Vanessa's web.  

Sissy Annette soon moved into a spare room in the basement in Vanessa's house and Vanessa began keeping Sissy Annette in dresses and make-up 24/7.  Heavy doses of hormones were slipped into Sissy's food and Vanessa used mind control techniques to strip away the Sissy's independence.  Vanessa became Sissy Annette's pimp and she was determined to make this a "profitable" relationship.

Starved and brutally corsetted, Sissy Annette's body became slender and sexy.  Her swelling breasts filled out her tight dresses.  Men were highly aroused by the sight of her and enjoyed running their rough hands all over her delicious curves.

Sissy Annette sees her next "date" from across the hotel bar.  It is time to be flirty and charming and docile.  She will soon find herself on her knees in a hotel room upstairs...