A Reluctant Sissy -- Part 5 -- Elegant Nights

When I opened my most recent update letter from Mrs. Trainer, these two photos fell out of the envelope.  I must have stared at them for five whole minutes before I could tear myself away from them to read her letter to me.

"Dear Mrs. ____, 

I am very pleased to report that our progress with your son is proceeding very, very well.  An entirely new personality is being revealed; One that is demure, gentle and obedient.  I am sure you will be delighted when you see the finished product in just a few short months from now.

Now that our sissy students have been with us for 16 weeks, the intensity of the training and our expectations of our "ladies" increases quite dramatically.  Days are longer, infractions are dealt with more severely and our behavior and personality manipulation (some might call it brainwashing) is taken to a new level.

We are very fortunate that our school is located just a few miles from a Royal Air Force base.  Over time, we have developed a relationship with a select group of senior officers from the base that we can trust.  Every Thursday night, we invite our officer friends over for a very swanky party with our darling sissies.  The officers tell their wives that they are working late (seems to happen every Thursday!) and our sissies entertain these handsome gentlemen from early in the evening until well past midnight.

We dress our sissies up in their finest outfits to show the officers how much we appreciate their company.  And it should be no surprise that your little Kimberly is one of the officers' favorites!  The gentlemen arrive -- in full dress uniform, of course -- around 6:00pm.  It's cocktails and flirting with the sissies.  Then dinner at 8:00 followed by more cocktails, dancing and...well, whatever the officers want to do.  We have plenty of space here at the school for the officers to take a sissy somewhere private for some one-on-one time.  This goes on for a few more hours until our gentlemen guests are exhausted and need to head home to their families.

You may be curious as to why we incorporate some much interaction with men into our training program.  Let me explain.  First, when our sissies are in the presence of alpha males, like our wonderful RAF officers, they are shocked into realizing just how little they have in common with such real men.  Being surrounded by strong, masculine, muscular men, our sissies feel small and delicate and weak.  They recognize nothing of themselves in our handsome guests.

Second, it is understood by all that the sissies are to cooperate with and please our guests at all times.  Our officers are accustomed to having their instruction followed and their needs met.  It is wonderful practice for our sissies to understand that their role is only to please and to serve.  At this point in their training, they are beginning to feel a sense of fulfillment, and even pride, in their submissiveness and servitude to these strong, dominant men.

I will write again with more photos as soon as I can.

Sincerely, Mrs. Trainer"

I put away Mrs. Trainer's letter and again marveled at the photos of my beautiful, elegant, ladylike son.  I could just imagine how these older gentlemen would absolutely drool at the site of such a lovely young "girl."  And while at first I was shocked by the thought of him being forced to endure...encounters...with men, I could see Mrs. Trainer's point that it was probably a very powerful indoctrination and re-education tool.  I reminded myself of just how bad his behavior was before I sent him away and how I was in favor of whatever Mrs. Trainer felt she needed to do to fix his awful behavior and attitude. 

 

Taking my Sissy Husband on Vacation

My husband and I are having the most wonderful vacation together.  That's me in the photo on the left, the brunette in the black dress.  But that's not my husband in the photo! That's my new vacation boyfriend, Jerry.  I met Jerry earlier this week at the resort bar.  You see my husband is not a real man like Jerry.  My husband is a feminine, submissive sissy. 

That's my sissy husband in this photo -- the pretty blonde "lady" in the sexy gold dress.  His real name is Martin, but he is living only as "Tina" this week while we are on vacation.  And as you can see, Tina landed a handsome new vacation boyfriend too! His name is Darren.

My Tina is very, very good at passing as a woman.  He works hard at keeping his body slender through a strict diet and body-sculpting exercises.  He keeps his hair long all the time, but dyed it and had it styled especially for this trip.

Don't you think they make a cute couple?  Darren is everything that my Martin/Tina isn't. He's strong, confident and decisive.  A real Alpha male! I love seeing Tina with Darren. It seems like Tina doesn't have a single idea of his own when he's with his hunky new boyfriend -- Tina seems only capable of agreeing with whatever Darren says and whatever Darren wants to do.

I love seeing how Tina behaves when he's with a real man!  That's why I planned this vacation to a singles resort.  Although we have been out together as two women many times before -- to restaurants and bars and so on -- we had never taken a week-long vacation like this before.  For Tina -- and for me -- it is a wild, new experience!

I know my sissy husband enjoys his time as Tina.  I know that his need to express him feminine side is far too powerful for him to resist.  And being in the arms of a strong, masculine man is so exciting for him, throwing his feminine feelings into overdrive. But tricking a man to believe that you are a real woman when you are not is playing with fire!  And Tina knows this. Each moment he spends with an unsuspecting man fills Tina with equal parts excitement -- and fear that his secret will be revealed.

Tina and Darren have been an item for three days now -- and we have three days left in our vacation.  Can Tina keep up the act for the rest of our vacation without letting Darren find out the truth?  I certainly hope so.  I expect that Darren would be furious beyond belief if he learned that the woman he was falling for was really a man.

So how does Tina manage to keep his secret? Well, the first night was easy --  just some flirting and a little pawing at the resort bar, with a brief good night kiss at the end of the evening.  By day 2, things were heating up, with some heavy making out during the day and a hand job in Darren's room at the end of the evening.  (His cock is enormous, Tina reports!) 

Today is day 3 of their steamy relationship.  I caught Tina and Darren making out like crazy earlier today -- including in the swimming pool!  Now we are all dressed up for a double date together.  First we'll have some Happy Hour cocktails, then a romantic, candlelit dinner together, followed by dancing at the outdoor bar until late. It's what happens after that that has Tina very nervous.

"You better hope he likes blow jobs!" I told Tina. "And I hope you are really good at giving them.  Because he is going to expect to get some serious action from you. And since he can't fuck you, you better find some other way to keep him interested." Tina has practiced giving blow jobs on the strap-on dildo I sometimes use on Tina's backside.  But Tina has never had a real cock in his mouth -- or down his throat.

 

Of course, I've been fucking my new vacation boyfriend every chance I get this week.  We run off to his room a couple of times during the day and of course in the evening. He is amazing in bed! And I always give Tina a detailed report on my sexual encounters with Jerry.

I really hope that Tina -- and his pretty mouth -- can keep Darren satisfied and unaware of the truth. They make such a cute couple and Darren really seems rather smitten by Tina. And I can tell Tina is really falling for Darren.

Keep your fingers crossed that Tina can really pull it off. With a little luck -- and a lot of sucking -- Tina just might come home with wonderful memories of his romantic vacation with Darren -- and a tummy full of Darren's hot, sticky cum!

 

Mommy's Pajama Sissy -- Part 12 -- The Conclusion

It turns out that Jimmy told Tammy that, as Captain of the football team, he was expected to "share" his girlfriend with some of the other seniors who were on the team.  This is what I overheard Tammy talking about on the phone.  Well, I couldn't believe what I was hearing, but it seems like my sweet, innocent Tammy was going to listen to whatever Jimmy said -- and do whatever Jimmy asked.

The very next day, I heard that Jimmy and Tammy went to the beach -- along with Jimmy's teammate Marcus.  Tammy didn't share any of the details of what happened at the beach but he seemed completely fine with whatever did happen.  I guess Tammy enjoyed the extra attention of two boys instead of just one.  

I soon had the impression that Tammy's dates with Jimmy usually included one -- or more! -- of Jimmy's football buddies.  I began to become concerned that Tammy was letting himself get caught up in something that wasn't very healthy for a young lady like Tammy.  But as unhappy as I was that Tammy was being "shared" among the players on the football team, I soon learned that the situation was perhaps even much more worrisome than I knew.

Tammy had been very open with me about his early experiences with Jimmy, but as the summer wore on, Tammy became much less willing to fill me in on the details of what he was doing.  I started checking his phone when I could just to get an idea of what he was up to.  So you can imagine my shock when I found these photos on his phone.  Because that's not Jimmy that Tammy is kissing.  That's Jimmy's Uncle Mike who owns the garage where Jimmy works!  Mike is in his mid-40's and shouldn't be romancing an innocent teenager like my Tammy!

And not only was Jimmy "sharing" Tammy with his Uncle Mike -- but apparently, Uncle Mike was "sharing" Tammy with his friends too!  The photos on Tammy's phone weren't very clear so maybe I'm not exactly sure what I'm looking at. Maybe you can figure out what's really happening here...

Oh dear! Perhaps this is all my fault!  It was just so much fun when we started wearing cute pajamas and nightgowns together  I could never have imagined that it would lead to this.

Mommy's Pajama Sissy -- Part 8

When Tammy and Steve arrived at Steve's parents' home, Steve quickly poured himself a stiff drink.  They had already started having a conversation about exactly who Tammy was and Steve was beginning to come to terms with the fact that the beautiful girl he had been French kissing on the dance floor wasn't really a girl at all.

But Steve wasn't angry or upset.  He really mostly seemed confused and conflicted.  He had fallen very hard for Tammy and it was a struggle to incorporate this new, shocking information with what his eyes and emotions were saying.

"Do you want me to go?" Tammy asked at one point when Steve seemed to be out of questions and the silence hung heavily in the room.

"I don't know.  I don't think so. Maybe if we just spend a little time here together we can figure out what exactly we are feeling and what we should do next," Steve suggested.

So they sat quietly together on the couch for a few minutes.  Steve broke the silence saying, "God, you even smell fantastic."  That comment broke the tension and Tammy giggled a little.

"Steve," Tammy started, "I think you like me as a girl. And I know I like you. So maybe, just for the rest of the evening, we could both go on pretending that I'm really a girl."

"But what would your mother say? Do you think she wants this to be happening?  Do you think she wants you, her son, hanging out alone with an older man who, just a few minutes ago, was kissing you on the dance floor?!?"

"I think my mother has the hots for you just as much as I do. If I wasn't here, I bet she would want to be! But I'm guessing you have that effect on girls' mothers," Tammy offered. "So no. I don't think my mother would have any problem with me being here with you tonight. I think she would be happy that I've having this sort of experience with such a nice and handsome man."

Steve didn't have an answer to that. So Tammy continued, "So, if I really was your girlfriend, what would we be doing right now?"

"Making out, I guess. Is that what you want to do?" Steve asked.

"Yes!" Tammy breathed as he wrapped his arms around Steve's strong neck and kissed him hard.  And Steve kissed him back. Steve pushed Tammy down onto the couch and climbed on top of him.  Their kissing and their breathing became harder.  As did something in Steve's pants.

"If I was really your girlfriend, what would you want me to do now?" Tammy whispered.

"I'd want you to pull down my zipper and take out my dick and start to stroke it," Steve replied. And that's what Tammy did.  Tammy was amazed by how huge Steve's cock was -- many times bigger than his own little one.  And it seemed to grow bigger with each gentle stroke.

"May I put it in my mouth?" Tammy asked.  Steve could only nod.  Tammy kissed the end of Steve's rock hard dick, and then licked it, and then pulled it into his mouth.  Steve's eyes were closed and he was making quiet moaning sounds so Tammy figured he was doing it right.  "Oh that feels so good," Steve moaned.  "So good."

After playing with Steve's dick in his mouth for about 10 minutes, Tammy said, "I want you to make love to me. Treat me like a real girl and fuck me.  Please."

"Let's go upstairs to my bedroom," Steve replied.

When they got there, Steve stripped naked. "Are you going to get undressed?" Steve asked.

"Oh, no. I don't want to be naked. I need to be wearing girl's clothes to feel like a girl," Tammy explained. "Give me a minute." And Tammy exited Steve's bedroom.  A moment later, Tammy returned wearing a black satin and lace nightgown. "How's this?" Tammy asked with a smile as he twirled in front of Steve.

""Did you take that from my mother's lingerie drawer?!" Steve asked with some distress.  Tammy nodded yes with an enormous smile on his face. "Oh, God, I'm going to be in therapy for years because of you." Under the silky nightgown, Tammy was still wearing his bra and padding, so he had the shape of  a woman and Steve couldn't help but be excited by the image of a sexy woman standing before him. 

"Wow," said Steve, "You look amazing. I am so turned on right now." And with that, the two lovers climbed into bed.  Steve positioned Tammy on his side, with his bottom facing Steve.  Steve lifted the hem of Tammy's nightgown, exposing his soft little bottom.  Steve applied some lubricant and warned Tammy that it might hurts a little since it was his first time. Steve began to gently work his giant, rock hard dick into Tammy's virgin sissy pussy.  With each stroke, Steve's cock penetrated deeper and deeper into Tammy. Soon, Steve's thrusts became harder and quicker, his moaning louder, his grip on his feminine lover tighter. And as Steve came inside of him, Tammy's own little penis also exploded into the soft, silky fabric of the nightgown that was rubbing against him.  

For Tammy, the experience was quite painful -- but also exquisite. Allowing his body to be given over for the pleasure of a real man. To feel a real man plant his hot sticky seed deep inside his body. To surrender completely to the needs of the woman that lived inside of him.  It filled him with a sense of happiness and fulfillment unlike anything he had ever experienced.

As Steve's dick began to soften, he started to withdraw from Tammy's backside. Tammy reached around and grabbed Steve's ass. "No," he said. "Please leave it inside of me for just a bit longer."

As they lay there, still wrapped tightly together, they both fell asleep for a few minutes, both feeling exhausted and content.

When they awoke, Steve kissed Tammy again and said, "I think I need to drive you home now, darling."

Don't look so sad, little Sissy!

Don't look so sad, my little Sissy Princess!  After taking a long break, I have decided to come back and add some more delicious Sissy fantasy stories!  Isn't that wonderful news?                                                          There are a few stories that I started writing down a few years ago that I will finish up and get posted.  Some are sweet and soft and romantic stories that will make all you little Sissies swoon with pleasure.  Some are a little bit rougher and scarier.  These stories will make you little Sissies squirm with fear -- and envy.                                                                                      So turn that frown upside down, little Sissy!  Mistress Trainer is back with more stories for you.                                                                                Now get on your knees and open that mouth nice and wide because I have some gentlemen friends in the next room that are dying to meet you!

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 6

Erica re-emerged from the other room, this time wearing a lovely silver dress with a matching chiffon bolero.  It accented his fabulous new figure superbly.  He looked so elegant and dainty.

"Ms. Trainer, please tell me more about the training Erica has received since he's been here," I inquired.

"Of course," Ms. Trainer replied.  "This is a brand new program for us and I am very pleased with how well it went in its first year."

She continued, "I developed a curriculum that would help advanced sissies, like Erica here, develop the skills they need to take their service and submission to you to the next level.  The course work covered three main areas: service skills, beauty and comportment, and sex techniques."  Roberto was suddenly interested in hearing more when the third item was mentioned.


"In the area of service, Erica has been learning wonderful new skills.  He can now perform a Swedish Massage on the two of you.  He has learned some interesting new breakfast in bed recipes and serving ideas.  And he has learned important new skills to help you plan and hostess and serve when you are entertaining.  Isn't that all correct, Erica?"

"Yes, Ms. Trainer," came the soft reply. "That is all correct."

"Erica, take off the little jacket while I continue," Ms. Trainer instructed.

"Yes, Ms Trainer," Erica said as he complied.

"Where was I?  Oh yes, beauty and comportment.  Well this whole decorative sissy thing requires some new skills for our sissies, like making themselves as pretty as possible and posing for hours like a mannequin..."

"Or a Barbie," Roberto interjected.  We all laughed.

"And he can do his own hair.  Isn't it lovely?  It's very difficult to make it look so nice, but Erica has been a very good sissy student.  Of course he has to sleep in his curlers, which is very uncomfortable, but it's all worth it."

Ms. Trainer continued.  "In the sex department, well that's where things got the most interesting.  Wouldn't you agree, Erica?"

"Yes, Ms. Trainer," came the timid and shameful reply.



"Our little Erica here has developed some impressive new skills.  We did lots of fellatio practice over the past twelve weeks. Erica can now accept the biggest imaginable cock down his throat.  We also had a pussy worship course -- I taught that one myself.  And I'm pleased to report that Erica has a very, very talented tongue.  You will be very pleased.  We also practiced some group sex.  Erica learned to take two dicks up his ass and two more in his mouth, all at the same time!  Erica, how much is two dicks plus two dicks?" Ms. Trainer asked in her speaking-to-a-child voice.

"Four dicks, Ms. Trainer," came the pitiful reply.

"Oh my, Erica!  Did you pleasure four men at once?  Why what a little whore you are!"

We burst into laughter once again.

"Go change, Erica," Ms. Trainer instructed.

A Sissy Refresher -- Part 5

When Erica reappeared, Ms. Trainer excitedly said, "Oh, Roberto, this one is for you!  Now I know you like to have the boys over every Wednesday for poker.  And I know you like to have Erica serve them drinks and food and so on.  Now, what do your buddies think about being served by a sissy?"

"Some of them are really freaked out by it," replied Roberto. "But most are into it, since he is so pretty and will do whatever they tell him to do."

"Well, imagine this, Roberto.  Instead of greeting your friends in a maid's uniform, picture Erica appearing dressed like this!  He looks like the hostess at a fancy club or casino, don't you think?  I think it will really add some elegance to your poker parties.  Now are you getting the idea of what a 'decorative sissy' can be?"

"Yes, I think so.  I mean, he looks fantastic in that dress.  It's SO short!" he said with a giant smile.

"Now wait until you see this," added Ms. Trainer.

And with that she instructed Erica to remove the little chiffon bolero jacket that he had been wearing over his dress. Two skinny straps held up Erica's sparkly blue dress.  The spaghetti straps seemed to accentuate how skinny and delicate his shoulders now were.

"Oh, yeah," said Roberto. "That is so fuckin' hot!"

"I knew you'd like this," said Ms. Trainer.  "And I know your friends will as well.  I think they will really enjoy ogling your sissy while he is dressed like this.  I bet a lot of hands will find their way up that short skirt for a grab of his cute little ass, don't you think?"

"I know it!" said Roberto.  "Turn around, bitch," Roberto ordered.

Roberto went over and did exactly what Ms. Trainer described.  He roughly reached up under Erica's short dress and gave his bottom a hard squeeze.  "You like that, don't you, you stupid sissy bitch?"

"Oh yes sir," Erica obediently replied. "Yes, I like it when you grab my ass.  Sir."

"I think your friends will never miss another poker night ever again," opined Ms. Trainer.  "Now, be a good little sissy and put on another of your pretty new dresses for us."

A Sissy Refresher -- Part 1

"Come out here now, Erica," Ms. Trainer called.  "Your wife and her lover are here and they are dying to see the new you."

Tentatively, timidly, Erica -- formerly my husband Eric -- entered the room.  I gasped.  My Erica was gorgeous.  He was wearing a lovely silk dress in the palest gold.  His hair was perfectly styled.  And he was so skinny!

"Don't be frightened, Erica," Ms. Trainer said gently.  "You look lovely.  There is nothing to be embarrassed about."  Despite Ms. Trainer's reassurances, Erica seemed terribly nervous.  I could tell that he was on the verge of tears.  "Come along now, Erica.  Be a good girl."   Erica walked across the room and stood in front of Roberto and me. He delicately held a cute clutch purse in his manicured fingers.

"Ms. Trainer," I said. "He's lovely.  I mean...fantastic."  Ms. Trainer smiled with satisfaction.

"I thought you would be impressed," she replied.







I had deposited Erica here just twelve weeks ago.  Of course he was already a fully feminized sissy, having gone through Ms. Trainer's transformation process some years ago.  But now he looked so beautiful, so elegant.  And so incredibly skinny.

"How did you get him to be so skinny?" I asked.  Erica was already very, very thin before.  But now -- wow!

"Well, it's not too complicated.  It's a combination of a severe -- and I mean severe -- diet, combined with a lipo/body sculpting procedure, combined with some amazing corsetry that he's wearing that I get from Japan.  It's terribly uncomfortable -- but the results are so worth it!  Erica, don't you just love wearing your corset?"

Erica spoke for the first time.  "Yes, Ms. Trainer, I love wearing my corset."  His words were barely a whisper.  He seemed so upset.  I could see tears welling up in the corners of his eyes.  And he was trembling very slightly, perched about his silver, strappy high heels.







"Ms. Trainer," I asked.  Why is he trembling like that?"

"Well," she replied, "It has been quite a difficult twelve weeks for our lovely Erica here.  He has really done his best to cooperate with our refresher program for advanced sissies.  But it hasn't been easy, has it Erica?"

"No, Ms. Trainer.  It has not been easy," came his breathy reply.

"There, there.  Try to relax, Erica.  We wouldn't want your tears to ruin your make-up now, would we?

"No, Ms. Trainer," he replied.

Ms. Trainer continued.  "Our little sissy Erica may also be nervous about what awaits him when he returns home with you and Roberto.  All of this extra training he has received is for a purpose.  And he is well aware of just how attractive -- enticing, really -- he has become.  And I think he is nervous about what you have in mind for him."

"Ah, I understand," I replied.  Of course the experience of the last twelve weeks would have been both punishingly cruel, as well as plant seeds of anxiety for what his life would be like when we returned home.

"Now come over here, Erica," Ms. Trainer ordered.  "Let me help you off with your jacket."  Erica obediently stood still while Ms. Trainer undid the buttons in the back and slid the jacket off of my sissy.

As the jacket came off, Roberto said, "Damn!"

"Damn is right!" agreed Ms. Trainer.  "That is one fantastic looking sissy!"

I couldn't believe my eyes. With the little jacket off, Erica posed there in front of us, in his strapless dress.  His shoulders were impossibly skinny and delicate.  He was obviously dying with shame as Roberto and I took in this sight.  Again, I thought Erica was about to start crying.


"Now turn around Erica.  Let's show your wife and Roberto how pretty you are from the back," Ms. Trainer instructed.  I loved how Ms. Trainer talked to Erica in a voice you would use speaking to a little child. But when speaking to Roberto and me, she would talk about Erica as if he wasn't even in the room.  There was a sly, cruel -- but also very humorous -- way to everything Ms. Trainer did with her sissies.




Erica turned around and Roberto let out an involuntary whistle.  "Oh my God!" I gasped.  "His ass...it's simply perfect."

Ms. Trainer smiled with satisfaction.  And even with his back to us I could sense Erica's deepening sense of shame as we all talked about his cute round ass.

"Erica, go back into the other room and put on one of your other dresses.  I know your wife and Roberto will enjoy seeing you model your cute new outfits."  And with that, poor Erica minced out of the room to change.

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.

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!

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.