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Showing posts with label cross-dressing. Show all posts
Showing posts with label cross-dressing. Show all posts

A Talk About Seduction (Karen learns a lot from Lydia)

A Talk About Seduction
“I know you are nervous; it’s alright, honey.  My first time I went out in public dressed as Lydia, I thought everyone was going to see the bulge in the mini-skirt, and I would be outed,” the charming beauty in pink, who was born Lawrence Cooley reassured her child.

“That’s exactly how I feel now.  I mean, just walking in heels, wearing this frilly lingerie – and trust me, it’s rubbing up against my groin,” exhaled a very nervous Keith Cooley.

“Doesn’t that feel wonderful, the sensation of silkiness across your now softer body.  It gets better and better, Karen.  Tell me… have you thought about our double date tonight?”, said Lydia with a teasing but nurturing grin.

“Yes, Mom.  I think that we picked the right dress for my debut as your daughter.  I seem to have inherited your long, sexy legs.” Karen sighed.  “Mom?  Can I ask you something about umm… how do I say this…  sex?”

“Of course.  What piece of sage motherly advice can I give you about the birds and the bees?” Lydia replied quite eagerly.

“Well… I was in bed last night, and I dreamt of Allen and you excusing yourselves  (giggle) and leaving Oliver and me – alone.  He may want to seduce me.  Should… should I let him?” the young transvestite asked with eyes full of wonder – and lust. 

Lydia put her arm on Karen’s shoulder and cooed, “Let me tell you, my dear.  After 40 years of a blasé masculine life, I found the meaning of life in the throes of the most incredible orgasms  - in Al’s bedroom.  If you want to know if Oliver is the right guy,  MAKE him seduce you.  As  women, we can manipulate virile men into whatever we DESIRE!”

Out With The “Big Girls” (Shauna, watch, learn and "grow")

Out With The “Big Girls”
"So tell me, Shauna,” whispered Jerry Smith to his teenage son Sidney, at the busy restaurant, “Do you like the gift that your grandma and I gave you for your 16thbirthday a little or a lot?”

“I love them, Mom” chirped the blonde teen, “And it’s cool that you both got a pair for your own.  I guess this means we’re not going back to doing guy things, like going hunting?”

Jessica, Jerry’s alter-ego looked down at her sweet new assets, and then giggled as she saw that her new daughter was just as blessed, as she mulled the question.  She replied, “Well, I am looking forward to our next visit to Victoria’s Secret a lot, but I think we have a new hobby, thanks to our new weapons.  Say Mother, what do you think about us three going hunting?”

Paul Smith cooed, “Watch and learn girls.”  

 Phyllis then turned and smiled at her the middle aged waiter came to the table with the three blonde T-girls.  “A Coke for my granddaughter, and two Cosmos for my daughter and I.  By the way, I’m single – here’s my number.”

As Phyllis slipped the man her number, Jessica poked Shauna and whispered, “That’s how sexy girls like us to hunt.”

  Shauna smiled and nodded  She would soon be hunting alongside them both.
 

Prize Fulfillment (Sasha + Jane play to win!)

Prize Fulfillment
Jack Taylor entered every contest and promotion he could.  And when he and his son Steve went to claim their prize from Snapz Studio, they were shown the fine print: they had won a mother-daughter makeover and photo-shoot, along with the $10 grand prize.  Figuring they would walk away, the Snapz PR team was shocked – they accepted the prize!

“Looking pretty foxy over there, MOM!” giggled the now sweet and femmed SASHA.

 “Not bad yourself,” cooed the elegant and sexy JANE.   “I must say, I love how this feels – right down to the frilly lingerie!”   That got both of them giggling and blushing.

By the  way – LADIES,” the Snapz executive said while seething, “the contract requires you both to pose for advertising with the winners of our father-son contest, and they are dressed in three piece suits, while you both are in cocktail dresses.” 

“Yummy,” the new mother and  daughter sighed in perfect harmony.
 

Babes In Joyland (Dina's family have holiday bliss) MERRY CHRISTMAS/HAPPY HOLIDAYS!

Babes In Joyland
Darren Crawford  had to bribe his sons Chad and Scott to dress as girls to go along with his own drag disguise – they were posing as Dina, Caitlyn and Shay, the manufactured wife and daughters of Darren’s neighbor, Jeffrey Reed.

The Reed “girls” were being introduced to Jeff’s senile old grandma, who wanted to see the lifelong bachelor with family so that he wouldn’t be excluded from the will.  Jeff promised Darren that he would give help him pay off the mortgage, and then agreed to buy  both boys the new video game system.


TWO WEEKS LATER 
 
“Jeff, honey, the girls and I have a gift for you.  We love the way we look and feel.  Caitlyn and Shay have never been closer than as sisters, and Caitlyn actually has been asked out by a young man…”

“Mom!  It’s just to see a movie…”

“Sis, I can’t wait until I’m your age and Mom and Daddy let me date!”

“It won't be that long, baby.  Jeff, our gift is that you don’t need to pay us.  You just need to love us and make us your family.  And I love being a mom of two girls.  Say, wanna go for a third, handsome? ;)

 

Head Start part 1 (Nora + Glenda are studying... hard *giggle*)

 
Head Start
Starring Glenda (Dad)  and Nora(Son)

 
Gordon Brown never would have believed that his own son, Neil, would love to dress in drag as much as he did.  The day that Glenda and Nora met, there was an immediate mother-daughter bond.  It empowered them both.

Which is why they found themselves here, at a rowdy bachelorette party.  A long time friend thought they would enjoy a hen party in femme roles.  After all, they looked so incredible with their bright red hair & sexy legs.  But there would be a catch:  the bridesmaids had arranged for strippers.
 
 
Male strippers, who were going to letting all of the girls – the Browns included – have their way with their enormous, bulbous man-roots.  Glenda and Nora were tucking their tiny penises under their silky panties.  But now they were going to be up close to all of those dicks.  They were somewhat nervous.

To make things worse,  Nora was feeling a bit tipsy from the wine and the shots that the other girls were cheering her and Glenda on to down – and she had made a mess of her cute frock.  It was drying on a line outside – leaving Nora in her Maidenform bra and panties.  Her dainty little dick was slightly more in danger of exposure than Glenda’s – that is until “Mom” spread her legs in a very unladylike manner.  Her flesh colored panties were looking a little damp.  All of this SEX was getting to her, and most of the guests knew there was not a real vagina underneath those panties.   
 


But no worries, as most of the girls here knew about the Browns’ disguises.  Turns out, so did the strippers.  As Manny fed his massive cock to the topless maid of honor, the tipsy ginger T-girls whooped & cheered like the other horny bitches at the party.  Then the stacked blonde to their right (the blonde slut’s mom) requested that Manny bring that thick COCK over to their couch…

Their Home Team Pride (3 gen of football stars become Southern Belles)

Their Home Team  Pride
In the Deep South, high school football rivalries can bring a team together, or pit families vs. families.  The Pruitts and the Samuels are two such families.  Patriarch Lewis played for West County Blue Raiders, as did his son Mike,  and grandson Colin was the WCHS quarterback last year. 
 
For 40 years, Roger J. Samuels was Lew Pruitt’s friendly rival, and a Samuels (son R.J. and grandson Tripper) always lined up on Homecoming Saturday against a Pruitt on the gridiron – often with a wacky bet at stake, designed to embarrass  the defeated family. 
 
This year, the Samuels thought they had the best prank; the losing Pruitts were to dress as a bridal party and pose for wedding photos.  Little did the Samuels know that their targets of scorned actually had a another cherished tradition: “Lana”, “Melody”, and “Candice” often got together to glam up.  

The beautiful bride, her glamorous mother, and elegant grandmother (dressed in WCHS blue, of course) smiled and posed fiercely as the Samuels’ boys gawked at the three shapely blondes.  The T-girl trio would relish going “1- 1” with their handsome dates – for these Blue Raider babes, victory was certain.
 

Mom and Daughters get a Fresh Start (An adorable quintet of cuteness!)

Mom and Daughters get a Fresh Start
Jim (40): Thanks so much for helping your step-brothers become your pretty little step-sisters, Alyssa.  I couldn’t have done it all by myself, you know.

Adam (16):  Awww, Dad, you’re the one who taught me how to make myself over into a sweet little thing.  Before Mom passed away, you used to take the six year old version of me out, and treated me to cute dresses and shoes!  Then “Mary” took over your life, told you to be a man and made us purge every single feminine thing we owned.  I’m so glad you and your lawyers sent her packing.
 
Judi: I know, I know, but without her, we’d never have Ryan, Nicholas, or Christopher in our lives.  But she was so controlling, and then she had an affair with her conniving boss!  She won’t be out of prison until my new daughters are out of prison.  By then, Regina, Natalie, and Camille will be in high school.

Alyssa:  Mom, they already confided in that they were scared of Mary, and they love having you as their new mommy.  I told them that as their big sister, I want to be there for them as they grow into beautiful young women.  You know, one day it will be these hotties going out on dates with cute guys from high school.
 
Judi: Just like someone else I know who’s grown up to be quite the looker.  I really like Brandon, sweetie; he’s handsome and polite.

Alyssa:  And a great kisser! (giggle)  Now Mom – you need to get out of the house and find a nice man to take you out on the town.  It’s time for you the be the happy housewife!  Hey girls – don’t you want see our Mommy as a beautiful bride, and us four as her bridesmaids?

Regina (7):  Oh yes, Mommy!  That would be so, so AWESOME!!

Camille (5):  I want to be the flower girl, Mommy!  Or a mermaid!

Natalie (9):  Alyssa, Mom - can you show me how to walk in heels?

Judi:  Wow – looks like we’re all going to have the time of our lives! :)
 

This Is Not a Dream (Denise + Amanda have awoken to a new day)

This Is Not a Dream
So here I am – Darren Irwin, single dad, buttoned-down  bookkeeper, nothing happening fellow, with soft brown hair extensions, a delicate white dress, and a blissful smile on my face.  For the time being – you can call me Denise.

And in my arms – my son Adam.  He’s usually wearing a Transformers T-shirt, but today, she –Amanda that is – too cute for words in her own matching dress. 

“Mommy,” Amanda whispers to me, “I always dreamt about being a pretty girl, and Aunt Shelley told me that she dressed you up years before I was born.  She even said that there was this guy named Gary who you went to school with who she wanted to take us out for ice cream.  Can we Mommy, pleeeeeze?”

“Baby, looks like we both had the same dream.  I can’t wait to see Gary again.”

Just One More Selfie… (you have a text from Julia + Christina)

Just One More Selfie
“You’re sure that this won’t get out?  We’ll never live this done,” I muttered as my son John take a selfie picture of the two of us in drag.  

“No worries, Dad,” he replied.  “This won’t get on Instagram, obviously.  My buddy Eric and his dad  (my boss, BTW) would be unrelenting if they saw us like this.”  

So why did I, Calvin Marx, red blooded man, father, and businessman, get dressed up like a foxy blonde, alongside his pride and joy?  Well, my late wife liked to dress me up for some bedroom games, and I caught Johnny in his room with her panties on… he looked cute, and he really liked the idea of us bonding by spending a weekend as mother/daughter hotties.

A year later, and Christina and Julia have a full wardrobe, and the hormones, and our discussions have led us to decide to go full time.  Jules sent this picture to Eric and George, and they are taking us out Saturday.  My daughter and I can’t wait until we get our new boyfriends to fuck us like the sluts we want to be!
 

The Tradition Continues (A tri-gen tale of boys making pretty romantic girls)


The Tradition Continues

Andrew:  What a great way to celebrate little Rodney’s birthday, Dad.  I remember when I was his age and you and Mom dressed me up in a cute little smock like our “girl” here.  I loved that time of my life – innocence.

William:  Do you remember how we kept doing that – until Doris passed away – and then we took that trip en femme for your 13thbirthday?

Amy: I sure do.  Every girl remembers their first kiss – that Craig was so dreamy! (giggle)  That experience helped me when I later met Gretchen.

Wendy: Yes, just as my dating experiences before I met your mother were a big reason I learned how to treat a lady, just as you learned to, son.

Renee:  Mommy, Gramma – look at my beads.  They’re soooo pretty!

Amy: Not as pretty you, my precious baby!  I just knew you’d enjoy letting us dress you after you watched us put on our clothes and our makeup.

Wendy: She’s a natural, Amy.  I think when she’s old enough, she’ll entice some young man to ask her out to a movie… or maybe even the prom.

Amy:  Oh I loved it when I danced with Gretchen in my tux – and then we went to her school and I wore that gown, and danced with her big brother.

Wendy:  And that was after Doris and I showed you the picture of me, her, and our dates.  (pauses)  I’m sure Doris and Gretchen are enjoying seeing the three of us now.  And I hope they would approve of our dates tonight.

Amy:  I know they would Mom.  Our guys are handsome, well-mannered and they sure know how to romance  a couple of newly single mothers. I sure  can’t for them to see us in those sexy tight dresses we bought, Mom!
 

Sweet Tea for Three (Have you made your reservations yet?)

Sweet Tea  for Three
It’s not that Dustin Morgan didn’t think the food at Sweetie’s Kitchen was as advertised: real homemade comfort food, with that addictive Southern sweet tea – it was that he came to Sweetie’s dressed as an attractive woman –  that includes a wig, bra and panties, a pretty blouse, and cute Capris.  But at the recommendation of Dustin’s younger brother John and father Vincent, he had visited the salon they recommended across town.  Of course, it was also concerning to Dustin that his dad & bro that they were also femmed up – and not for the first time either.   

“I’m so glad to have both my daughters here with me,” sighed Vera.   

“Thanks for joining us , sis,” tittered Jayme.  I want for you, me, and Mom  to come back here on singles night.  See who can find Mr. Right first.”   

Dating guys??  
 
This all so new to Desiree.  Just then the waiter came over and asked the trio if they needed a refill of tea.   

“Yes please,” Desiree answered as she found herself getting lost in Brian’s deep brown eyes.  Vera and Jayme grinned…
 

 
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