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He knew he was late, or close to it, but should’ve been on time to catch the subway to make up for lost time since his bicycle had gotten a flat tire—his precious fixed gear. The bike slung over his shoulder, he dashed up to the elevated platform. There was one right there! He didn’t need to go far, just far enough, there was a bike shop somewhere, a quick fix and he wouldn’t be too late. The fare paid, a sigh of relief quickly turned to disappointment when the train pulled away. A thought ran across his mind to fling his bike at the passing cars out of protest for its audacity to pull away on time. Quickly dismissed under pretense that an additional something to fix on the bike wasn’t worth the risk. …

Subway Ride Read More »

I steered into the driveway that I had pulled into hundreds of times. This was the first time dressed as a woman. I knew I couldn’t stop what I started. I wasn’t controlling the overwhelming desire to be feminine. It seemed to control me. As a couple walked by, I pressed the remote and pulled into the garage. I watched TV for a while. Though it was late, I decided to try on the lingerie and heels I purchased. After dawning the bra, panties, garter belt, and stockings, I sat to put on the stilettos. Although the sales lady said they were four inches, they were probably more like four-and-a-half-inch heels. I stood up unsteadily. I carefully walked to our full-length mirror. My legs did look great. I walked around. I needed practice. I put …

Bob Returns To Crossdressing With Unexpected Results – Chapter Three Read More »

Amy had left me stunned.  I had left myself half dressed!  As quickly as I regained my wits I ran to my pants and threw them on.  Racing to the stairs, I ran down them two at a time, across the lobby, and out the front door.  I retraced the path to the Wildwood hoping to catch up to her and convince her to come back to my room, or at least get her number, but by the time I reached the bar, it was closed. My disappointment was palatable, and soon the cold, damp air of Seattle took away my adrenaline-filled rush.  My bare feet on the wet pavement turned back to the hotel.  I didn’t want to go back, I wanted to find Amy!  Reality had set in, and I knew that all …

Mia Found! Read More »

I left Jane’s house feeling exhilarated. I was fairly confident that I passed as a woman, but I only had Jane and Jim telling me that. Maybe they told every client that. As I drove, I thought about what I had done. I not only dressed fully as a woman, and received lengthy instructions on how to act like one, but I had made out with a man and sucked his cock until he came in my mouth. I felt guilty. But not for the reason one might think. It was not because of what I had done. I felt good about my feminization. It was because I was doing it without Joann’s knowledge. I knew if this was to continue, I had an obligation to tell her. I hoped she would have some level …

Bob Returns To Crossdressing With Unexpected Results – Chapter Two Read More »

Lee visiting Darla’s trailer after his workout soon became a regular event. He would shower and then dress in a robe he started carrying in his gym bag as the one she provided was a little small on him. He would then sit and have coffee with her as they talked about their training. Eventually, Darla’s looks, the scent of her perfume, and the feel of her silky clothing against his hand would get Lee excited and he would wrap her in his muscular arms and plant soft kisses on her pretty face as they slid off the couch. Once on the carpet his powerful arms placed her on her hands and knees and he made ready to penetrate her. It took Lee a while to get over the fact that Darla was not born …

A New Partner, Part 2 Read More »

“Mmm…mmm…mmmph!!!” Kneeling on the bathroom tile, hot water spurting out from the showerhead, a big juicy cock rammed its way inside Violet’s mouth. Its owner moved their hips back and forth, the phallus’ head tickling her soft palate. With a final thrust, the cock shoved itself deep in her throat. Gagging, she pulled her face back. A glistening spit-strand lewdly stretched out, connecting the throbbing member to her glistening lips. Deep-throating was never her forte. “God, Vivi, I’m gonna cum!” With a few jerks, ropes of jizz spurted onto her face before slowly trickling down her full cheeks and dribbling over her chin. “That was amazing.” Her partner, Alice, panted while reaching out to stroke Violet’s hair. Her gentle contours glistened under the faucet. Still on her knees, Violet stared up at her from the …

Violet Gathers Research Material Read More »

I continued chatting with Mia every chance I got. She seemed like she was interested in meeting, but like most intelligent people she was reluctant to share personal information that would allow us to meet. Her profile said she was in Seattle, almost 850 miles away, so I couldn’t very well take off and look for her every weekend! One day, while we were chatting, she mentioned that she had gone out the night before to one of her favorite places. “Oh, where’s that?” I asked, as nonchalantly as I could. “It’s called the Wildrose,” She replied. “I like it because it’s not too far away, and they cater to people with an alternative lifestyle.” We chatted for a while longer, and I asked her again if I could come see her. She was apologetic …

Finding Mia Read More »

The snow squalls were relentless, the wind howling around the old light post where we had parked. Cassidy smiled and looked up at the stars, despite the winter cold, and with a coy glint in her eye said, ‘You sure you want to do this here?’ I grinned back, unbuckled my seat belt, and leaned into Cassidy, pushing her back so she was reclining her seat. I then reached down, surgery-gloved, and emerged her thick one-eyed member from inside her warm track pants. Already glistening with precum, I then went in for it. Cassidy stroked my hair as I expertly worked her bulbous head with my tongue, flicking and caressing, savoring the taste of her sweetness. I was in heaven, and my enthusiasm was palpable, pushing Cassidy deeper and deeper into a trance of pleasure. …

Jizz for Java Read More »

“I felt guilty about being responsible for ruining your first pair, and when I couldn’t decide which one looked the best on you, I knew you had to have them all. You looked so damn sexy, and I’m feeling very turned on right now.”  Sophie beamed at me when we were outside the shop. To thank her, I invited her back to mine where I could change into the panties and we could have a pizza a little later if she fancied. To my delight, she agreed. As soon as I arrived with Sophie back at my parent’s house, she insisted that I modelled some of the panties for her properly. I stripped down, fully comfortable with letting Sophie see me this way, even though I wasn’t comfortable with my own body. There was no …

Down The Rabbit Hole – Part Two Read More »

“Are you who I talk to about the interview?” I whispered, looking down the long hallway. “Stephanie, right?” he said, standing from the desk. “It can get a little confusing with all the rooms. Please, have a seat on the couch.” I walked into the cramped office. It was little more than an angled desk, a chair, and a couch next to the door. I sat down, sinking into the cushions more than I expected. “I really like that blazer,” the guy said, “unique pattern.” “Thank you! It was a gift, wasn’t quite sure how to wear it in an outfit to be completely honest.” I pulled at the blazer’s sleeve. I wore a simple top beneath it, tucked into waist-high skinny jeans, and ankle boots. “Well business casual will fit right in here,” he …

A Job Interview Gets Intimate Read More »

I figured it was worth the risk. I fashioned my hoodie into a workable dress, then headed down to the hot tub. I spied Rick next to a grill, jamming to some music I couldn’t quite hear. “Rick,” I waved. “Tara, right?” he asked, pointing with his tongs. “Stephanie,” I corrected. “Right, right,” he said, “Tara is the blonde.” “No,” said a woman at Rick’s side, “Tara is the redhead. Hi, I am Penny, Rick’s wife. You moved in just down the hall, yeah?” “Yup,” I said, “nice to meet you.” A guy a little younger than me hopped out of the tub, dripping as he stood by Rick’s side. He had a shy smile and a cute little pudge to his stomach. He stood next to Rick as if waiting to be introduced. “Stephanie, …

A Birthday Surprise For My Neighbor Read More »

It’s been said that there are no better cocksuckers than men, and when you consider that men should know best how to work their own equipment, the reasoning is quite simple. I was once a professional cocksucker myself, so from my own experience, I know this to be true. If you met me for the first time, you’d never guess that I was born in a male body. I’ve already written a lengthy series about my transition nearly fifty years ago, so I won’t go into much of that here. I’ll just say that I know what I’m talking about when it comes to men being the better cocksuckers. I’ll admit that percentage-wise, most of the men I’ve been with were bisexual cocksuckers like me. Then after I transitioned, I attracted heterosexual men looking for …

TransTales – Million Dollar Blow Job Read More »

On the night of our “wedding”, my stepmother had my grandmother take me to the new villa that I was going to call home. Everything that I saw was just the same overtly feminine thing possible. The floor was pink and white marble, the walls were covered in pink floral wallpaper. The couch was also covered by white leather with pink silk pillows. We walked through the house to what I was told was my new bedroom. The room was an exact replica of the one that was in the old house. However, there was a new piece of furniture under a cover. I was curious what it was, but my grandmother told me that I was not able to see it yet. “Grandmother, what is the big secret that I have to wait for …

From Eighteen Years Old Boy to Lesbian Secretary Part 7 Read More »

In the spring of 1981, when I was nineteen, a woman named Miriam Roston moved into my building. At least I initially assumed that she was a woman. In New York, people generally were non-judgmental and left other people alone. But this was in the East Bronx, not Manhattan, and after about a month, my family started speculating about her. They used terms like “tranny” and “shemale” to describe her, although they didn’t exactly dislike her either. But neither did they go out of their way to socialize with her. She lived on the fourth floor and we were on the sixth, so I often met her in the elevator. For some reason, she seemed to like me, and we often chatted a bit, sometimes for a short while in the lobby or out in …

A Hot Evening With Miriam Read More »

London, when the sun was shining, was one of my favourite places in the world. The good weather changed the vibe of the city, and although people still kept to themselves, it was clear that everyone just seemed a little bit happier and walked with a little extra spring in their step. Wearing denim shorts sporting a few rips from the wear and tear over the years and a faded yet treasured Linkin Park tour tee shirt, I enjoyed the feel of the sun on my pale skin as I walked through Hyde Park on my way to meet my best and longest friend Steve. I know that Steve had opted to take the underground, but on a day like today, that seemed like madness. Why travel on a train crammed full of people on …

Down The Rabbit Hole – Part One Read More »

My life as Bianca was rapidly progressing to the point of my never being a man again. My stepmother had reported that I as a man was abducted by a few men. The Columbian police had searched for six months, and they had called off the search. It helped that the captain was a family member, who was clued to the fact that I was in the process of becoming a woman. He made sure he had the necessary paperwork to get a new identification and a new birth certificate for me. My stepmother and grandmother both made me into a beautiful young woman. They had arranged for a surgeon to give me a set of breast implants and hip implants to get a full-figure body shape. I now had the measurements of thirty-eight, Twenty-two, …

From Eighteen Years Old Boy to Lesbian Secretary Part 6 Read More »

Now I look back on it, my boss Megan was into me from the moment I joined. I remember her being so kind on my first day, constantly popping back to my desk to make sure everything was okay. At one point, as she was helping me get set up on my computer, she leaned in really close, her hand resting for what seemed like ages on my thigh. But I put it down to her being a really tactile person. Some people just are. Plus, I didn’t mind her getting up close and personal, as she was hot. I guessed she was around forty, which made her ten years my senior. She was a little taller than me at five foot eight, and with really sexy big breasts and an ass I just wanted …

A Night To Remember With My Boss Megan Read More »

I began to slowly step across the plush pink carpeted floor, and feel the most intense desire to be a girly girl that I had ever had. The slight tug of the silk stockings and garter belt against the silky touch of my chemise under the skirt on my legs and the bounce of the fake breasts were only adding to the way I was feeling. The pink satin blouse with its contrasting black mesh sleeves completed the sexy secretary look that my stepmother had dressed me up as. My long jet-black hair was tastefully in a curly mass piled on the top of my head, and my makeup was still flawless as if it was just done. The bedroom that I was in kept telling me that I was no longer a boy and …

From Eighteen Years Old Boy To Lesbian Secretary Part 4 Read More »

I was locked in the same corset for six hours, and the corset was really beginning to be unbearable. I was going to be in it for the foreseeable future and I was unable to do anything about it. I also realized that my stepmother had put a good pair of gaff panties on my body. I looked like a woman down there now. I slowly realized that I was no longer tied to the bed. I slowly got up as the corset was really hard to get into a sitting position in. My stepmother had to help me get dressed for the day. She chose a black lace bra that matched the gaff panties I was wearing. She proceeded to slip a camisole on over the whole set of my lingerie. Next, she had …

From Eighteen Years Old Boy to Lesbian Secretary Part 3 Read More »

I sat in the living room of my apartment, watching television. My phone rang, and I answered the call. “Hi, Mike, it’s Greg,” my friend said. “Hey, Greg. What’s up?” I replied. “Not much. What’s going on with you?” “I finished working, and I’m watching the news.” I worked from home as a help desk tech for an MSP. When I graduated college, I applied and was hired. After six months of training, I started taking calls and helping clients with computer problems. The work was easy, and I could choose my hours, provided I handled several tickets daily. “Do you have plans for tonight? A few friends are getting together at my place tonight. Are you up to a party?” “I don’t have plans. What time?” I said. “We’re getting together at seven. I …

Pranked Read More »