Crossdressing

1ball

Mistress Hannah's Pathetic Husband Part 3

I learn how manly my mistress wife can be

The first week of having a useful cock went well. For the first time since we got married, we had sex every night. After strapping my extension on, I would lick Hannah's pussy enough to get her turned on and then she'd choose a position. If I got physically worn out, she would choose another position. Because I was having sex so often and doing some research on the Internet, I was able to...Read On

Added: 20 Oct 2011 | Category: Crossdressing | Avg Score: 4.94 | Tags: humiliation  feminization  strapon anal   | 3 Comments

DrBill

Glimpses of Consequences

Davey's mother tries to teach him a lesson.

GLIMPSES OF CONSEQUENCES By DrBill "HOWA we going to start?" The ritual joke having been followed by the ritual groans, the Housewives of Worthington Acres came to order. The group had evolved from informal visits for coffee and complaining to a neighborhood organization of sorts. While the meetings still tended to be primarily boast and bitch sessions, they also traded useful...Read On

Added: 12 Mar 2007 | Category: Crossdressing | Avg Score: 4.57 | Tags: petticoat punishment  voyeur   | 6 Comments

summer1979

Summer in the fields

A one nooner stand

Steve is an average 19 year old on the outside. He has a full time job, a live in girlfriend (Amanda), divorced parents, and 2 cats. On the inside he's about to erupt. Summer is the eruption. Summer is Steve's "alter ego" who comes around every now and then. Steve used to let Summer drive around on the many less traveled roads in the area. Summer has never been with a guy, and she only...Read On

Added: 20 May 2009 | Category: Crossdressing | Avg Score: 4.63 | Tags: oral  anal  crossdressing  rimming  roleplaying   | 1 Comment

irishfella

Ten minutes in heaven

A story about a 16 year old caught in his mom's panties and then pays with it with his virginty

My name is Sam. I have been a cross dresser just recently. I am currently 16. I have short blond hair,dark brown eyes and I am very slim. I have a older sister who emigrated but I visit her once or twice a year with my mom. My dad passed away a few years ago. Considering my mom had financial problems she works a lot so that gives me time to cross dress. My mom is very sexy and has great...Read On

Added: 08 Apr 2012 | Category: Crossdressing | Avg Score: 4.33 | Tags: crossdressing  anal  ora lsex   | 3 Comments

davmay

The Day I Became a Girl

My wife was out of town and I started crossdressing.

(Minor details were changed for privacy reasons. More chapters to come..) Until recently I did not think of myself as a crossdresser. I separated my sexual desires and secret habits from who I was. Yes, I had been privately dressing in women's clothes but it was a temporary fetish that didn't reflect on me as a person. On multiple occasions I even threw away my girly clothes as if to prove...Read On

Added: 06 Sep 2012 | Category: Crossdressing | Avg Score: 4.45 | Tags: crossdressing  crossdresser  masturbation  panties  shaving     | 10 Comments

cdbottom2

Mom made me a Fluffer

another story between Missy adventures. Enjoy and please rate and comment all stories. :)

For most of my life I never knew exactly what my mom had done for work, neither did I know who my dad was. As such I just continued with life and thought to myself that I would find out what she did in time. My curiosity first peaked when I was 16, I was looking for my moms purse so I could exchange some of the money I got mowing lawns for people around my neighborhood for different bills....Read On

Added: 27 Aug 2012 | Category: Crossdressing | Avg Score: 4.91 | Tags: crossdressing  oral sex  masturbation  quickie sex  bisexual  porn star  milf   | 7 Comments

trinitytowers

The Feminisation of Michael - Chapter 3

The Feminisation of Michael. Chapter 3 I endured the rest of the afternoon with continued suppressed sniggers and laughter. I was glad when 5.00pm came and I buttoned up my jacket and put my handbag over my shoulder and left with a big sigh of relief. Sue was waiting outside in the car. “Hi Michaela,” she greeted me. “How did it go honey?” she beamed. “Fucking awful!” I blurted out....Read On

Added: 17 Feb 2010 | Category: Crossdressing | Avg Score: 4.85 | Tags: | 3 Comments

sissyslut_trish

Humiliated by my best friends

I had recently met a kinky lady online who agreed to be my mistress on a frequent basis. Tasks she set me included wearing panties to sleep in, leaving a butt plug in me, while we chatted and other kinky things. Last night, while we were chatting, I told her I was going to a friend's house with a few of the guys, to play cards and have a few drinks. Her dominant side took over and she told me...Read On

Added: 02 Aug 2012 | Category: Crossdressing | Avg Score: 4.55 | Tags: crossdressing anal humiliation   | 5 Comments

Chrissy_CD_slut

Chrissy Gets Bolder Meeting Todd Again

Chrissy gets a good hard fucking by her new friend

I really hadn't expected Todd to call me after that night. I know how guys are when the night is getting short and you need someone to satisfy your needs. I did think about him a few times and wanted to see him again. I had enjoyed my first experience with a man so much it seemed that's all I could think about was my next cock. When I went to class I would catch myself looking at guys as...Read On

Added: 21 Oct 2011 | Category: Crossdressing | Avg Score: 4.85 | Tags: anal  reluctance  creampie  crossdresser  gay  bisexual   | 7 Comments

summer1979

The Afterparty

Steve awoke dizzy and confused. His head was spinning from all the alcohol he consumed from the party last night. As he tried to focus his eyes in the pitch black bedroom he realized he was bound to each corner of the bed. He struggled to free himself but the straps were to tight. It wasn't his bedroom; the sheets didn't feel the same and the bed was much bigger than his. Perhaps someone...Read On

Added: 31 May 2009 | Category: Crossdressing | Avg Score: 4.43 | Tags: crossdressing  bdsm  voyeur  

trinitytowers

The Feminization of Michael - 2

The Feminization of Michael. Chapter 2 I continued with the “weekend” clothes for another few weeks and consistently had people commenting, laughing and making things difficult when I was out shopping. I continued at work in the more feminine suits and blouses too.  The rumours increased and somehow word had got around that at the weekend I wore dresses and full make up! This couldn’t...Read On

Added: 11 Feb 2010 | Category: Crossdressing | Avg Score: 4.77 | Tags: | 3 Comments

libertina

A Whole New Me - Part 1

Borrowed panties and a day with my friend reveal a whole new side to me!

“Honey! Are you around?” I shouted from my room, rummaging through my drawers and naked from the shower. “What’s up, sweetie?” My girlfriend, Lisa, popped her head around the bedroom door. Her eyes taking in my body and a cheeky smile forming on her pretty face “Oh, looking good.” I wasn’t the most muscular guy but I wasn’t fat at all and Lisa always claimed she liked my body not being...Read On

Added: 26 May 2012 | Category: Crossdressing | Avg Score: 4.65 | Tags: panties  bi  bisexual  first time  thong  crossdressing   | 8 Comments

jimymac

Date with my wife - her story

Today started like any other day, except for one thing. My husband informed me as he brought me morning coffee, "Sweetheart, tonight when you come home, go straight upstairs, cleanup and put on the outfit I have laid out on the bed." He said this with a grin on his face. You know that grin like the one you see on a child's face as you enter the candy store. "But what if I need something?"...Read On

Added: 03 Jul 2012 | Category: Crossdressing | Avg Score: 4.9 | Tags: lingerie  strap on   | 2 Comments

LilPandaKisses

Surprise

Aubrey greets his boyfriend home from work in a new way. Slight BDSM ahead.

Aubrey swallowed the lump in his throat as his wrists grew sore from his restraints-being handcuffed to the headboard of the bed, naturally he grew stiff. Speaking of stiff... he peered down, under the frilly black miniskirt of his maid outfit was a visible bump, straining against the panties that constricted it, said lingerie was clinging to his soft pale skin. He bit a plump bottom lip...Read On

Added: 24 Dec 2011 | Category: Crossdressing | Avg Score: 4.69 | Tags: anal  oral  crossdressing  bdsm  femboy  gay  lingerie   | 7 Comments

cassandrababy

Adventure in St. Louis

Cassie's adventures on a night in St. Louis

A NIGHT IN ST. LOUIS Work can really suck. At this moment I am sitting on an airplane wrapping up a three day business trip. Thank goodness I know how to make work fun. If someone gives you lemons, I say make lemon meringue pie, because lemonade is not good enough. What I am getting at is you have to make the most fun in your life, because life is too short. If you have a passion, make...Read On

Added: 18 Jan 2011 | Category: Crossdressing | Avg Score: 4.88 | Tags: crossdressing  anal  oral  quickies   | 9 Comments