Steve to Stephanie Ch. 01


This is my first attempt at a longer story with deeper characters and a more evolved story line. Stay tuned for the next chapter. As always comments are welcome.


Steve was mild mannered guy with a big secret. Steve was an avid cross dresser, very bi actually leaning towards being gay. Steve did not consider himself gay because he really wanted to be female. While having sex, Steve fantasized about being the woman. Since he normally bottomed it was fairly easy for him to see himself as the woman.

Steve liked to spend his free time dressed. He often went to the Oregon Theater on cross dresser night. He sucked cock and was fucked there. Steve sometimes took on dozens of guys in a single night. Once in a while he would even get it on with a woman who came to watch the festivities at the Oregon. When not at the Oregon he would dress up in his favorite little black dress, wig makeup and nails and cruise the glory holes at the adult bookstores.

Steve worked in the Pearl district in downtown Portland. His was a boring job in a cubicle crunching numbers eight hours a day. He did not interact much with his co-workers; he quietly went about his job. The one exception was Mary. Mary thought of Steve as one of the girls even though he never cross dressed at work and they were friends. It was Steve’s mild manners and slightly effeminate demeanor that attracted Mary to Steve.

Mary and Steve went to lunch often and talked about fashion. Although Steve had never told Mary of his cross dressing or transgenderism, Mary thought that deep down Steve was transgendered. She often asked his advice on fashion and they window shopped on their way to and from work.

It was on one of their lunch expeditions that the moment that changed Steve’s life forever happened. They were waiting on a crosswalk when an old lady started crossing the street. She looked homeless and was moving slow. A Tri-met Ümraniye Olgun Escort bus was rounding the corner at a good clip. Steve saw that it would hit the old lady. He jumped out in front of the bus, grabbed her and pulled her from harm’s way. He walked her to the other side of the street.

She was obviously shaken up as she realized the speeding bus had almost run her down. Mary had just caught up with the pair, when the old lady reached up and touched Steve’s face. The old lady said “You will get your heart’s desire through what you enjoy doing the most”. With that, the old lady pulled herself together and with a surprising spryness she was gone.

Mary looked at Steve and said “that was strange. Shall we get back to work?” Mary and Steve walked back to the office and finished off their work day.

It was a Friday night and Steve was looking forward to getting dressed and going out. In the shower Steve shaved everything with a new sharp razor. He toweled off and sighed as he looked at himself in the mirror. He thought that about the old lady, and said to himself “My heart’s desire is to be a hot young female. I just wish the old lady had been real instead of real crazy”

Steve pulled on a hot little pink thong and a garter belt. The little pink thong was great if Steve found a hot guy that wanted to breed Stephanie. He rolled on hose and attached the garter belt carefully lining up the seam on the back of his legs. Steve thought his legs were his best feminine feature. He then picked up his bra and fastened it behind his back. It had taken months of practice to do that but Steve thought it was an important step to get dressed as a girl would. He slid silicone breast forms in the bra. Adjusted “the girls” so they looked natural.

Steve sat down at his makeup desk. Turned on the lights and applied foundation. He then shaped his eyebrows and applied mascara Ümraniye Sarışın Escort and eye shadow. A little blush and he pulled on his wig and pinned it in place. After carefully brushing and styling the wig he looked in the mirror and Stephanie looked back. He slid into his little black dress; Stephanie was ready to hit the town.

Stephanie headed out of her apartment and went directly to her car. She giggled when she thought of all the times doing this her neighbors had never caught on. Stephanie unlocked the door, sat down and pulled her heels off. She had never got used to driving in heels. Driving always made Stephanie nervous because Stephanie’s driver license said Steve on it. She was however a careful driver and had never been pulled over.

As Stephanie headed out to Fantasy Adult Superstore she was thinking of sucking some yummy cocks. She missed a light turning yellow. Immediately a police car did a U-turn and hit the lights. Stephanie was petrified. The cop walked up to passenger side and turned his flashlight on Stephanie. He said “license and registration please”. Stephanie handed them over with a lump in her throat. The cop looked them over and said “you have some explaining to do Steve”

Stephanie replied “cross dressing is not illegal, so write me a ticket and I will be on my way”

The cop looked back at Stephanie “I think what we have here, is a case of a fake ID. I think I will have to take you in, unless of course you can think of some other way to deal with this issue.”

Stephanie did not want to go to jail. She cleared her throat and said “perhaps we can go somewhere more private and discuss it”.

The cop looked at her one more time and said “go two blocks west take a right and there will be a dark park on your left. Don’t try anything, I will be following you.”

Stephanie pulled into the park with the cop right on her Ümraniye Şişman Escort ass. The cop got out of his car and Stephanie got out of hers. He walked up and said “On your knees”. Stephanie immediately complied. She reached out and rubbed his bulge. She pulled down his zipper and reached in and extracted his hard cock. The cop was hung and had a pretty cock. Stephanie loved this. She licked him from balls to head before taking him in her mouth. She ran her gloss pink lips over his cock and started moving up and down.

The cop was moaning and calling her a slut. Stephanie was in her element. She imagined herself a young woman pulled over and getting out of a ticket. She felt totally feminine and in her element. Unfortunately the cop did not last long and was soon blowing his thick salty load down Stephanie’s willing throat. When Stephanie had swallowed the whole load, the cop zipped up and looked down at her. “Now drive more carefully”

Stephanie looked up at him and said “would you like my number? Next time you get horny you could come by and I could relieve your pressure.”

The cop smiled back and handed her his notepad and pen. Stephanie wrote down her number in her best feminine script. The cop got in his car and she got in hers. Stephanie was giddy, this was what she lived for. As she drove to the book store, she noticed her scalp tingling.

Stephanie walked in and all the guys stared at her. She had a line following her as she sashayed back to her favorite booth with a glory hole. As she opened the door a man raced into the booth next to her. She got on her knees and put her manicured hand on the glory hole. She heard a zipper and a nice cock appeared in the hole.

She looked it over and sniffed it. The man smelled clean. She took it in her mouth and started sucking, it was not long until the man stiffened and spewed his load into Stephanie’s eager throat. This time her cheek bones tingled. The man zipped up and left. He was quickly replaced by another hard cock. This went on for the next two hours until Stephanie’s jaw ached and it was time for her to go home. Each load caused another part of her to tingle. The last tingle was in her nipples.

Part 2 coming soon.

Bir cevap yazın

E-posta hesabınız yayımlanmayacak.