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Dressing Stories

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Stage six of my journey to becoming Joann

A defining year in becoming a complete cross-dresser.

As I awoke on Christmas morning I found three presents on the end of my bed. There were handwritten tags on each with the message: open in private. There was no doubt in my mind as I opened them that they were from Sis. The first was a body shirt that pulled down and snapped in the crotch. It was white with a v-neck trimmed with lace around the neck and sleeves. The second was a set of breast forms slightly bigger than my...

Stage five of my journey to becoming Joann

Enjoying myself feeling like a women

As I opened my eyes it was quite light. I sensed it was late morning. Bob was still spooning me, but his dick was soft and must have pulled out of my ass sometime through the night. I quietly rolled out of the bed and walked to the bathroom. Before sitting to pee, I reached around and pulled another condom from my ass. I guess when he lets his dick soften inside me it shrinks from the condom leaving it in my tight ass. I’...

Stage Four Of My Journey To Becoming Joann

Continuing journey into the world of cross-dressing...

The next morning I told Sis that I spoke with Bob on the phone, as she suggested, and he invited me over to his apartment on Friday night. I think she was as excited as I was. She said we would have to pick out an outfit tonight when we both got home for the big event.   The next day all I could think about at work was Friday night. Toward the end of my shift, my phone buzzed that I had a text message. It was from Bob. My...

Stage Three Of My Journey To Becoming Joann

Continuing journey into the world of cross-dressing...

As we drove home from the Halloween party Sis asked me if I enjoyed my first time out as Joann. I replied, “It was great. How did you come up with the name Joann?” “Well, I really didn’t think about it until I introduced you to Michelle. I actually started to say Joseph when I realized I needed to correct myself. I guess Joann was the only logical name at that point. Do you like it?” “Yeah, it’s nice,” I replied. “Thank y...

Stage Two Of My Journey To Becoming Joann

Falling further into the journey of cross-dressing

Life was becoming a little confusing. I was out of high school and attending the local community college part-time at night while I worked at the machine shop during the day. I played soccer on the college team in the inter-county conference. Mom helped me buy a nice used car. Still, I wore panties, a bra, and nightshirt to bed every night. Sis was working part-time at a hairdresser while taking cosmetology courses in the...

For just a moment after opening her eyes Julie didn't know where she was. As her eyes became accustomed to the darkened room she was able to pick out the shape of the furniture, thanks to the sliver of light coming through the blackout curtain. That's when she remembered that she was in a suite at a local four-star hotel. The clock on the nightstand told her that she had been asleep for only ten minutes. 'It wasn't suppos...

The postman

Lucy gets a delivery from the postman that was a bit more than she expected.

Lucy was in her man mode at home when she heard a knock at the door. She answered it and it was the postman delivering a couple of packages for her. They were full of sexy lingerie and three sexy dresses. The postman came inside her hall to talk. The postman had obviously found out what was inside the bag. “I’m sorry, but one of the bags broke so we had to repack it for you.” “Thanks. Everything Okay, nothing damaged?” “W...

Taking That First Step Part 3

Lance's transformation continues

Lance had arrived at the specialty shop as himself, a young man wearing women's lingerie under his jeans. He was met by the stunning Cassandra, the shop owner and his confidant. She treated him to a wig, lipstick, eye shadow and then directed to one of the changing rooms. Waiting inside was one of the sexiest lingerie combinations that he had ever seen.  Upon exiting Cassandra reappeared clad in black leather, she looked...

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Taking That First Step Part 2

Lance returns to the specialty shop

Lance's family was surprised to hear him up and moving at 6:00 AM. Saturday was his day to sleep in now that school was out for the summer and he didn't work on the weekends. They didn't question it and soon fell back to sleep as Lance headed to the master bathroom. He showered and then toweled off before heading back to his room. Once in his room with the door locked behind him, he removed the sexy lingerie that the stun...

Jessie's Path

A true story of the Path that Jessie took.

One’s path in life has three primary sections. The first one is what made a person who they are. Everything from their parent’s genetics, to how they were raised, the environment they grew up in, and any uncontrollable outside influences causing a life changing event. The second section of the path is what we see, feel, hear, taste, and touch at this very moment in time. It is a collection of fleeting moments that may or...

The Three-Man Weave

A girl proves her skills as a baller, in more ways than one.

I took the outlet pass from Darrel just before mid-court on the right side. Johnson slid over to try to make me give the ball up, but I crossed him over and cut back towards the center of the court. I spotted Malcolm running the wing on the other side of the court quickly, then drew the defense away from him by turning my gaze back to the right side of the court at D.J who is getting ready to spot up at the three-point li...

Jamie's Gradual Grooming, Part 3a

Jamie's transformation picks up pace.

I gradually woke up from a deep and warm sleep. My slow awakening became very sudden as I came to two realisations. One, I was wearing underwear from the night before and two, they were wet! I quickly pulled the duvet up and over my head, as if lots of people were watching. I slowly put my hands into my panties and felt a warm liquid all over them, I'd had a wet dream. Straight away I tried to think about what I had dream...

Beautiful Sins

I am your most beautiful sins.

They call me Bella Sinns and of course, it's not my real name. I am not complex. In fact, I'm pretty fucking simple. I will tell you what I want and either you do it or you don't. I work by a simple formula. I reward those obedient and punish those who can't fucking listen. Such simple rules. My body is built for your pleasure. Pure and simple. I am tall, a few inches under six feet with long legs. My toes treated with te...

People always react in different ways when they find out about my cross dressing. Girls are usually more accepting than guys but everyone is different. I was twenty-two when I went to university and decided I would be completely open about it with everyone I met there. I found that most people were pretty cool with it, although some took some time to get used to it. I spent the first year living in halls with three girls...

More about Lillian

How I spent my time with Lillian

I took my time getting settled in before phoning Mr. Gordon, I knew he would just bitch and bellyache about my being late for work. He would remind me time and again about how generous he was in letting me have some time off, but that he expected an extra effort from me for doing so. After I slammed the phone down and felt bitter about it, after all I had improved his business in the short time I'd been his manager, he wo...