Posts Tagged ‘Crossdressing Sex With Women’

Sissy Caught Wearing His Aunties Pantys Is Punished L1 Part 1

Friday, December 17th, 2010 by admin

Sissy Lauren is caught wearing and masturbating in his Auntie’s Panties.  She found him in front of her bedroom mirror wearing her favorite pair of pink satin panties.  His was rubbing his cock through the panties while looking at himself in her mirror.  Auntie told her sister who told her to do what she wanted with him.  Auntie thought that he could benefit from feminization training so she sends him to Mrs Loving for serious training.  This clip starts off with Sissy Lauren being punished and spanked as Mrs Loving embarrasses him by making him tell her what he had done.

Sissy punished for being caught in his Aunties panties

Sissy punished for being caught in his Aunties panties

Sissy Learns to Service His Mistress With His Tongue

Friday, December 10th, 2010 by admin

Ms Simone is training her sissy to service her orally.  He’s been taught to lick her clitoris gently until she tells him she’s ready for more of his tongue.  Her pussy is wet because it makes her hot to tease and humiliate her crossdressing sissies.  Sissy glides his tongue over her pussy lips and clit until she is ready to come.

Sissy Learing How To please his mistress

Sissy Learning How To please his mistress

Standing Naked In Front Of Mistress

Tuesday, November 16th, 2010 by admin

Imagine how humiliating it would be to stand in front of your mistress naked, while she just sits there and stares at you.  Would your sissy cock start to grow?  Would you be embarrassed and shy?  Mistress doesn’t care because you’re there for her entertainment and pleasure.  In fact she enjoys seeing you squirm not knowing what she is going to do to you.  Would she punish you?  Well, of course she will.  Rather you deserve to be punished or not she’s going to paddle you.  Do you know why?  Because she likes it.  It brings her pleasure as you’ll soon find out.

Standing Naked In Front Of Mistress

Standing Naked In Front Of Mistress

Sissy Monikas First Feminization Session With Mrs Loving

Saturday, October 16th, 2010 by admin

Mrs Loving Greet A New Sissy Trainee Sent By His Mother

Mrs Loving Greet A New Sissy Trainee Sent By His Mother

Telling Her Sissy Her Training Rules

Telling Her Sissy Her Training Rules

Mrs Loving Helping Her Sissy To Relax

Mrs Loving Helping Her Sissy To Relax

Lets Get Those Ugly Boys Clothes Off You

Lets Get Those Ugly Boys Clothes Off You

Does Your Mother Know You're Wearing Girls Panties

Does Your Mother Know You're Wearing Girls Panties

What A Cute Sissy Ass You Have

What A Cute Sissy Ass You Have

Mrs Loving's First Look At His Sissy Clitty

Mrs Loving's First Look At His Sissy Clitty

She Puts Him In His Very First Girls Brassiere

She Puts Him In His Very First Girls Brassiere

How To Find A Crossdressing Play Partner

Friday, October 8th, 2010 by admin

Follow along with me as I find another crossdresser to play with.  Before I was married I did this several times and now my wife thinks, that for several loving reason, It would be nice if I could find a tg lover.  I’m going to write about my experiences success and failures along the way.  Oh, and a few pictures too!.  But first, it might be helpful to know a little about us and how this came about.

Donna is my second wife.  I divorced her after 27 years of marriage.  We didn’t have children which made everything easier.  Our sex life had never been good and it actually got worse over the years. In our 23 year I told her that I had been women’s underwear since I was a boy.  She accepted that very well but it didn’t change any thing in the bedroom.  Eventually I came to realize that I wanted a relationship that would support and encourage my crossdressing and my fetish. That was not going to be possible.  I didn’t know, when I left her, if I would ever find what I was looking for but I’m enough of an optimist to take the chance, take the risk.  Even though sex was terrible We were very good companions and friends.
I moved to San Francisco and lived of my savings for awhile.  I found a cheap large furnish hotel room with a a very tiny kitchen.  It was in the tenderloin district so not the best neighbor hood, to say the least.  Once I got settled in a began to cruised the internet trying to hook up with play partners.  I was looking for straight women and crossdressers and found both in short order.  Thank you, Craigslist!  After 4 months of really fun playing with several crossdresser I answered an ad from a woman who I later turned out to marry.  She was a professor of gender studies at the university, erotic artist and had just left her female partner of 12 years.  She identifies as a bisexual dyke.  She’s also 15 years younger than me.  Since we meet, 9 years ago, I’ve transitioned to living full time as a woman.  I’ve done without therapy, doctors and hormones.  I did get breast implants though.
We both wore dresses when we we married.  Her Catholic family was in full attendance.  they are loving and excepting.  All her nieces and nephews, and there are many, call me Auntie.  Her dad now opens doors for me.  I shop and cook  for the family at holidays and my mother in law loves and buys me something very girly for Christmas.  Like beautiful hair clips or silk lounging robes.
Donna and I have the most amazing sex life.  With her encouragement and support I not only came out as being transexual but I came out as a sissy.  I know that in our community sissy came mean a wide range of things.  Sissy is the world I use that encompasses my erotic desires.  Little pink satin dress trimmed with lace, frills and rosebuds.  Sissy panties with rows of lace across the bottom.   Stockings and garter belts next and finished off with pink hair bows and ribbons.   Donna loves to dress me and play with me all along the way.  She’s learned that I love her to do it in front of a mirror so I can see us and especially me!   I love women in old fashion underwear.  Full cut panties, girdles, stockings, petticoats, slips and nightgowns.  I but all her play clothes so she’s wearing what excites me the most.  I love the time when we dress each other.  Everything I’ve ever wanted to do with a woman sexually we’ve done.
Donna cares so much that I’m erotically fulfilled that she asked if there was anything missing for me.  She asked “I know you really like sex with other crossdresser.  Do you miss that?”  I told her I did and she asked if I’d like to find a crossdresser to play with from time to time.  I said that only if she was there.  At first she was interested and we talked about it for many hours until she came to realize that it might be best if I play without her but she wants me to tell her all about what we did with and to each other.  I’m guessing we’ll both masturbate while I tell her.
I’m writing all this to give you some background. I’m going to start a group called How To Find A Crossdressing Play Partner.  I’ll write frequently about my search for a play partner.   I’ll post the ads I place and the sites I place them on.  I’ll write about the responses I get.  You’ll be able to follow all along and even into the bedroom once I find and meet my soon to be crossdressing lover.

Reine Fucks Her Sissy Crossdresser With Her Strap On Cock

Monday, October 4th, 2010 by admin

Reine takes of the sissy panties and exposed his hard excited cock.  Being strap on fucked makes his sissy clit very hard and dripping.  Aren’t the sissy crossdresser black Mary Jane T straps just so cute?  Reine has lots of experience using her strap on and she knows to take her time in the beginning.  She squirts some nice thick lube on his ass and her dildo and very, very slowly begin to push her cock into his ass pussy.  Once she gets the tip in she add more lube and pushes into him just a little further.  She paused to give her crossdresser time to get to the feel of her cock in his ass.  Soon he got adjusted to her cock and slowy began to push his hips and ass onto her cock.

Once Reine felt him slide himself deeper on to her cock she knew he was ready for more.  She began to pump into him with more forcefully unto she was slamming into and his cock was hard and bouncing in front of her.

Reine Gets Ready To Fuck Her Sissy Crosdresser

Reine Gets Ready To Fuck Her Sissy Crosdresser

Sissy Crossdresser Is Fucked With Strap On Cock

Monday, October 4th, 2010 by admin

Reine loves to fuck pantyboys and sissy’s with her strap on dildoe while she teases and humiliates their little cocks.  She always begins by having her crossdressers kneel at her feet and kiss her high heel pumps and work their way up her thighs.  Here they learn to be obedient because the next thing she demands is that they suck her dildo as if it were a mans cock.  She likes threesome with another man and her crossdresser but first they must learn to suck cocks and take one in their pussy asses.

She dresses her crossdressing sissy in a little pink satin dress with lots of lace trim and pretty rosebuds and shiny pink ribbons.  She puts him into pink sissy rumba panties that have four rows of white lacy ruffles across the but.  She loves how they look on him when she pulls them down to get full access to hiss sissy clitty cock and his pussy asshole

Sissy Crossdresser Sucks a Strap On Cock

Sissy Crossdresser Sucks a Strap On Cock

He especially loves being dressed up and pantied by a woman

Thursday, September 30th, 2010 by admin

Mistress peeks inside her pantyboy’s nylon panties to see his sissy cock growing excited and hard.

What’s in these panties, Mistress Alice wants to know.   This is woman that loves crossdressers and gets excited when she gets the chance to play with one.  Her she is with Sharon, one of the members of pantyclub4men.com.   He sent me an email sometime ago and asked about being in movies.  He was able to sign a model release form and he was single and he didn’t think anyone would see him unless they too were a crossdresser.  He’s been in several movies and always has really powerful cums.

Sharon loves being seen by a woman when  he’s crossdressed.  He especially loves being dressed up and pantied by a woman.  He gets so excited, hard and swollen.  As soon as Mistress hold open he pair of panties and tells him to step into them his cock gets hard.

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She peeks into his panties

Some Crossdressers Love To Be Peed On By A Pretty Woman

Wednesday, September 29th, 2010 by admin

Watch this sissy crossdresser receiving his mistress pee. She spreads her pussy lips and pees in his sissy mouth.

In this movie Mistress Alice Culminate a long feminization training session with what her sissy needs and wants most.  She lays him on the floor and directs her urine stream right into his mouth.  His sweet little pink dress get all wet but he he loves it any way.

Mistress Alice Puts Her Crossdresser in Panties and Stockings and Makes Him Masturbate While She Watches

Tuesday, September 28th, 2010 by admin

She loves the look of that hard cock in panties.  She likes to make pantied cocks come into their panties.

Mistress Alice joined Pantyclub4Men sometime ago.  We’ve just completed shooting her fifth movie.  Mistress Alice can be very forceful as you see in her next movie.  She dresses a crossdresser in pink frilly satin rumba panties, a little pink satin lacy dress with satin ribbons and bows and then a blond curly hair wig.  When he misbehaves she gives him the ultimate punishment.  Golden showers is one of her specialties.