Is your wife cheating on you? - by Blair

Do you have a tiny dick?

Is your wife going on a business trip with her boss, who happens to be an ex and happens to be really hung?

Is your wife not answering today?

hmmm..... I think I can tell you what she's doing!!  want to hear more?

Youtube Sissy Commercial - by Blair

How about this for a fun activity: making a sissy commercial on youtube where you wear something sexy and show off on camera and tell everyone they should go to www.SissyPlayground.com to be humiliated by our mistresses?

Jaimie wants to do that for us!  He wants to dress up in his pink petticoat and make a commercial about how much he loves me and the other girls at Pleasure Playpen!  Maybe some guys will see it and want to call all your favorite mistresses!

Plus we all get to see it and will have a great laugh!!

"Queer" Boy Steve - by Stacey

Steve is a VERY long time client of mine who loves sucking cock, and since he hasn't sucked cock in quite a while, his punishment is to have his pictures posted today.  Here are some of his tiny... puny.. little dicklet and some of him balls deep on a cock.

Have you been a bad boy and need your pictures posted to motivate you?  Send them my way!!
pleasureplaypen@yahoo.com

or call us at 1-877-SISSY-CHAT

Erotic threesome - by Paige

You're dating my best friend and we are at our house drinking (your gf and me live together). I keep flirting with you very subtly by putting the conversation on you and laughing and touching your leg.

I am wearing something sexy and provacative and notice you staring at me through dinner.   When your girlfriend leaves to go to the bathroom, I make my move.  I slide over on the couch, slide my hand up your leg and lean in and whisper what I'd like to do to you (to find out what I said you'll have to call me 😉🤐)

Your cock is instantly hard and you lift me up and push me against the wall, kissing me, lifting up my skirt and dropping your pants.  And thrusting that hard cock inside of me.  Your hand over my mouth to muffle my screams.

When you hear your girlfriend you quickly pull out and start to pull up your pants, jetting to the kitchen to put yourself back together.  I tell you to wait there and to just look in at the two of us

Your girlfriend comes back in and sits down, asking where you are.  I tell her you'll be back in a few more minutes and pour her a glass of wine.  Then I start to flirt with her.  Before long she's shirtless and we are making out.   You can't take it any longer and come in

What would you do next?

Jackie my sissy client - by Melanie

I have TONS of sissy clients. And although I do not have a picture to share of Jackie, I thought some of my sissy clients might like to hear what he's done.

Jackie (formally Edward) decided he wanted to live his life as a tranny. He started taking hormones so he could enjoy his womanly features and voice.   He quit his job and became a hair stylist at a salon as his new self Jackie

His next big accomplishment will be to get a boob job

I'm so proud of Jackie for going out and living his life just how he always wanted to be!

Adult Baby Pictures - by Amber

Here are some pictures from my play time in my nursery with my adult babies

Paying online

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Racial roleplay - by Daphne

Into some racial play and role playing?

how about I am your spoiled white sugar baby and you're my black or Asian sugar daddy (depending on what you are).

I like to tease you in my bratty way and beg you to take me on shopping trips and pay for my pedicures, phone bill, etc.  I do so love showing off my sexy feet after a nice pedicure and massage.  You enjoy listening to me tell you what i'd buy with your money and how i'd tease you with my beautiful white body.

I can also do degradation of you or other women of other races.  Telling you that I am the best and the only one for you.

When we are done shopping we go home and you fuck the shit out of your sugar baby!  And while I ride that cock I continue to talk about how this white pussy is the only one you need.  And your pathetic cock should be worshiping this white goddess!

What do you think?

Strong athletic women - by Vicki

I have had some callers lately who love a strong, athletic woman who can just completely over power them.

Their fantasies are either wrestling or boxing related typically

This last fantasy went like this:

I took a guy in a boxing ring, wearing a sexy black and red pair of tight little short shorts with matching halter top that showed off my stomach and my tits.

He thought he could take me until he took the first swing, when he missed, he fell into the ropes and I hit him in his side lightly.  Just toying with him a little, punching and hitting lightly, thinking that I am weaker

Once he was tired from bouncing around the ring I went for it and took the first swing.  Hitting him in the jaw and dropping him to his knees.  I pushed his head down and said "eat the mat!"

He had precum stains in his speedos after that!

If you want to know where else this fantasy went... give me a call!

Pictures of our favorite Adult Baby Boy!

This is one of the girl's favorite adult baby boy!  If you want to see if you are a better one, you can email pictures to: pleasureplaypen@yahoo.com

Here are some new pictures of Eric D

Hardcore chastity - by Reagan

This is exactly what I want you to have prepared when you call:

 

List of items needed:

• chastity cage
• lock
• pink lipstick
• pink nail polish on fake nails (you should have them on your nails already)
• razor (to shave some fun parts)
• dildo AND vibrator to suck or maybe fuck yourself with
• handcuffs 
• tape

 

There are some variations of what we can do depending no how hardcore you can really handle.  But if you're interested in seeing what each item will be used for, then call me!

     

 

 

Human Ashtray Chrissy! - by Amber

Chrissy is a married sissy who normally doesnt smoke! I have turned her into a chain smoking ash tray! Chrissy calls  several times a week to put on her cocksucker red lipstick and fire up those cancer sticks! I make her ash her cigarette in several different places on her body! Sometimes her hand,mouth,even her little sissy clit! When its time to put the cigarette out she chews it up and swallows like every obedient cocksucker should! Chrissy loves to wash down all that tobacco by swallowing her golden showers! Such a naughty little bitch isnt she?

Do you have a smoking fetish? Want to become another human ashtray in my collection? If so call me and lets make all your smoking fantasies cum true! 💄🔥🚬🚿

 

 

Adult baby store in chicago

Check out this YouTube link to an adult baby shop that opened in Chicago

http://www.youtube.com/watch?v=_IPEpzdWv60&sns=em

Showing off on Skype or Yahoo

Some of our girls can watch you on Skype or Yahoo!

While you can't see them, they are happy to make you do all sorts of humiliating things for them!  Of If you just like having someone watch you masturbate, that's cool too!

Some things that the girls have seen:

• Jeff E is a sissy bambi who dances around in his lacy bra and panties 
• Adam B likes to show off his body and his cock and cum on himself (sometimes his face)
• Eric D would gladly show himself off in his diaper or onesy if he had a cam
• Ray likes you to have you get him hard in public places to embarrass him.
• Thomas likes to take a shit in his diaper at work, but he needs some encouragement from you!
• And those are just a few!

It does cost and extra $.50/minute for the girls to watch you.

Here are the girls who are available to watch

SKYPE
Blair
Vicki
Amber
Paige
Monika
Valerie

YAHOOBlair
Paige
Valerie
Allie

Getting summer body - by Blair

summer isn't over yet sissy girls!

You MUST get your summer body back so you can wear skin tight summer clothes to be sexy on the beach for your man. Here are some websites with excellent tips and here are some rules to help. 

1) attach your favorite plug or dildo to your exercycle and you may only watch gay porn while perched and cycling.

2) when giving blow jobs, get on your knees, tighten your stomach muscles, and do isometric crunches and you bob your head up and down.

3) play your Lady Gaga and Madonna music and do lunges while vacuuming, (great to lift those baggy buns back up)

4) stop eating dessert with your boyfriend! Tell him he has the only dessert for you and you want him to eat it all so he will taste even sweeter when you get home. 

Follow these rules for a few weeks and read the information on these sites and you will be trim and sexy for summer. It's for your own good.

Matt E

I wanted to share this picture of Matt E that he emailed to us.  Doesn't he look cute?  He's trying on an outfit at the store.  should he buy it? 

I think he may need some work on looking more feminine... any of our sissies have any suggestions and tips?

Gagging - by Casey

Have a big dick?  Or do you have a tiny dick and like to watch a girl suck a huge, monstrous cock?!

Either way, I love a big dick!  And my favorite thing is trying to take it down my throat as far as I can and have you listen to me gag.

Whether its your dick or someone else's, the longer and fatter it is, the better!

Tell me all about your gagging fantasy and I will be glad to fulfill it!

My Adult Babies - by Amber

My absolute favorite thing in the world is being a mommy to adult babies! I have my very own adult baby who lives with me 24/7. He was a former coworker of mine who got fired for throwing temper tantrums and wetting his pants in the office. Everyone at work would always laugh at him for being a grown man who goes pepe in his pants.

 

One day i told him I think he should wear diapers and stay home and be a baby because real men do not wet their pants! Thats when baby David asked me to be his mommy. He has a couple rental properties and some investments so he can afford to pay all my bills and stay at home being a full time adult baby! I said yes and I have been baby davids mommy for almost 6 months now. He has his own crib,high chair,car seat,stroller and tons of toys.

 

Baby david always wears diapers his favorites are bambinos choosies and snuggies! In the day time when im busy I send David to adult baby daycare where he can play with all the other babies! Baby david loves getting changed by all the hot mommys there and gets very excited telling me about all the fun he has each day! All my adult babies love hearing about all the naughty things baby david does each day especially baby Eric or should I say Erica. I let baby eric speak to david on the phone and eric told him how jealous he was that he gets to go to adult baby daycare and have such a hot mommy like me.

 

 Baby david told Erica that he didnt want a baby brother but he would accept a baby sister. Erica has a tiny little pepe anyway so hes fine with a being a little sister! Baby erica loves calling in every week to check on baby david to see what he did in daycare and to see what kind of yummy babyfood he ate! Here a few pictures of my sweet baby boy and my diaper collection! Are you a sweet baby boy or baby girl craving a loving mommy? Would you like to be baby davids baby sister? need your diaper changed? Call me and lets make all your abdl fantasies becum a reality! 👶🍼👶🍼