Crossdressing

jennaryder13

Prom Date- Part 1

Jody is forced to dress as a girl for prom.

Jody was pretty much a typical 18 year old boy. He liked sports, hanging out with his friends, and playing video games. However, Jody had one deep, dark secret. He was addicted to wearing his sister's clothes. Every time the house was empty and he had the chance, he would sneak into her room and try on something pretty. Jody was always mortified of getting caught so he was very careful....Read On

Added: 01 Dec 2011 | Category: Crossdressing | Avg Score: 4.48 | Tags: prom   | 3 Comments

SluttyTammyCD

Neighbor fun

Slutty fun with neighbors

It was a typical Friday night. I would hurry home from work to complete my ritual. Take all of the necessary steps for a lot of anal sex, shave all over and transition from a male to a female. I put on a typical “uniform” for the trip to his house. A lacy black top with a lacy black bra under (looked more like a teddy than a top), a short pleated black skirt, black stocking, garter, and...Read On

Added: 09 Nov 2011 | Category: Crossdressing | Avg Score: 4.90 | Tags: dressing  cum  slut  cd   | 6 Comments

SluttyTammyCD

Total Sub CD Slut

His total sub CD slut

I could not wait to get home from work on Friday. My routine was the same. It was total preperation for the weekend. I was a highly placed executive with the company I worked for at the time. Nobody knew that I lived as a total sissy slut cock worshipping whore on the weekends. I was seeing a guy who was very dominate. I met him online. The first night he took me home he dressed me...Read On

Added: 03 Nov 2011 | Category: Crossdressing | Avg Score: 4.64 | Tags: tranny  dressing  cum  slut   | 1 Comment

1ball

Mistress Hannah's Pathetic Husband Part 9

The final forbidden fantasy fulfilled

When we returned home, we had a big late lunch because Mistress informed me that we might want only a light dinner and then a late snack. I spent the afternoon preparing as best I could for an unknown special night. This meant hair removal, nails, wig, makeup, enemas, buttplug, lotions, powders, perfumes, the whole works. When I finished, she laid out the clothes and jewelry I would be...Read On

Added: 02 Nov 2011 | Category: Crossdressing | Avg Score: 4.78 | Tags: interracial  cuckold  creampie  anal  redemption   | 7 Comments

1ball

Mistress Hannah's Pathetic Husband Part 8

A return to the body art parlor

As we tried to sleep one Friday night after Mistress Hannah had used my ass with unusual vigor, she was tossing and turning and keeping me awake. I got the impression that she was struggling with some personal demon that was becoming an urgent threat. Something had changed around the time two months earlier when I had first achieved the goal of putting my puny pud up her ass. I don't think...Read On

Added: 01 Nov 2011 | Category: Crossdressing | Avg Score: 4.83 | Tags: humiliation  panties  tattoos  strapon   | 2 Comments

1ball

Mistress Hannah's Pathetic Husband Part 7

Mistress makes good on her promise

It was 8 months since the first time Mistress Hannah had ordered me to put on her panties. In that time I had become both more of a man and more of a sissy. When we went to the theater club on Sunday nights, I had a variety of dresses, wigs and shoes to choose from. My aerobic workouts had boosted my stamina and I had gotten good control over my premature ejaculations. I still occasionally...Read On

Added: 31 Oct 2011 | Category: Crossdressing | Avg Score: 4.67 | Tags: buttplug  anal  panties  humiliation   | 1 Comment

1ball

Mistress Hannah's Pathetic Husband Part 6

Mistress Leelee uses me hard.

Having accepted the riding crop, Mistress Leelee seemed to understand that she was being given the opportunity to do something to me, but she was clearly lost. "He's yours now Leelee. It starts with the first order. If you're going to turn your cheating husband, a little experience with Michelle here will give you confidence. I suggest you order him to stand in front of you and work from...Read On

Added: 29 Oct 2011 | Category: Crossdressing | Avg Score: 4.71 | Tags: humiliation  strapon  lesbian   | 2 Comments

1ball

Mistress Hannah's Pathetic Husband Part 5

I serve lunch to sorority sisters

I was making progress as a slave but unkown to me, one of my stories helped Mistress Hannah see an opportunity for a particularly fun afternoon and a chance to help an old friend through a rough spot in her marriage. Several months of aerobic classes and feminization had increased my stamina and made me more comfortable when we spent our Sunday evenings out for dinner and as member/patrons at...Read On

Added: 27 Oct 2011 | Category: Crossdressing | Avg Score: 4.82 | Tags: humiliation  strapon   | 4 Comments

1ball

Mistress Hannah's Pathetic Husband Part 4

Mistress takes the humiliation to a new level

The third and final day of my transformative weekend started poorly. I had aches and pains all over. My neck and back and thigh muscles were sore. I had a little irritation from body hair that was growing back. And of course, my asshole felt all stretched out and very tender. I wondered if it would ever feel tight again. I also wondered what the evening would hold. I couldn't imagine that...Read On

Added: 24 Oct 2011 | Category: Crossdressing | Avg Score: 4.82 | Tags: humiliation  feminization  humor  beads  strapon   | 2 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

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

anotherfeeling

Summer dressing

Long hot summer for crossdressing student doing vacation job

It was the mid 1980s, I was 20 years old and it was the summer holidays. For the long break from college I'd managed to find a vacation job in Kent in the south of England. It wasn't brilliant but I was going to get some experience of working with computers, and earn a bit of money to keep me going during term time. The company was based in a small town where I had found a room in a house with...Read On

Added: 19 Oct 2011 | Category: Crossdressing | Avg Score: 4.94 | Tags: older  male  anal  oral  stockings  heels   | 15 Comments

1ball

Mistress Hannah's Pathetic Husband Part 2

The transformation begins

During my first week as her new slave, Hannah decided that I was too hairy for a little sissy boy, so I had to begin removing hair from the tip of my nose down. The mustache went first. It really was kind of pathetic anyways. I actually got compliments from some of the women at work about how handsome I looked without it. I had grown it because I had a "baby face" and I wanted to seem...Read On

Added: 18 Oct 2011 | Category: Crossdressing | Avg Score: 4.73 | Tags: humiliation  sissyboy  panties   | 6 Comments

1ball

Mistress Hannah's Pathetic Husband

She found my porn stash and now I must pay

My life had become miserable. It had taken two years of marriage for it to happen, but it had become much worse in the past few months. The worst part about it was that it was clear that my sweet wife's life had also become miserable and that she thought it was my fault. And maybe it was, but I didn't know why. I suspected it was because I'm a miserable example of a man and she deserves...Read On

Added: 13 Oct 2011 | Category: Crossdressing | Avg Score: 4.93 | Tags: panties  sissyboy  humiliation   | 6 Comments

Jess_cd

Accepting an invitation

On the third day of house sitting, I awoke to a nice surprise. After my neighbour, Daniel, had unexpectedly visited, I had decided to work on my make up and mannerisms. After a day of walking in heels, I had perfected my sexy walk as well as getting my make up just right. I was feeling in the mood to show off my new found skills so was excited to see a note waiting by the front door. It was...Read On

Added: 09 Oct 2011 | Category: Crossdressing | Avg Score: 4.65 | Tags: neighbour  tease  seduction  domination   | 3 Comments