It was a different world when I was young. You were either a male or a female and if you attempted to cross the line between them you faced ridicule, social rejection, and even physical violence. However, there were still some who dared the journey and blazed a path for us gurls to follow to where we are today. I’m so glad to have met two of them.
I guess I started dressing when I was in college. One of the girls I went out with for a short while left some of her clothes in my apartment when she left. I couldn’t resist trying them on and found myself infatuated with wearing women’s intimates. This became compounded by my obsession with pornography on the internet. Given my lack of endowment, it seemed that women were enjoying sex more than myself.
I fell into a routine where I would put on a pair of panties, a bra, and a nightie, which made me hard, and then jerk off until I came all over myself. My desire to continue would subside immediately after shooting my load, ending any further sexual activity. Again, women seemed to continue to enjoy sex when it was over for men. My curiosity about being a woman grew deeper.
Most of the time I was home, I wore panties and a bra. Sometimes, nothing else, sometimes with a long shirt, sometimes in a sweatsuit. When I watched porn, I began to play the part of the woman. I would use a piece of kielbasa and pretend it was a man’s cock. First, I would put it in my mouth, eventually learning to take it in my throat. Then, I would put a condom on it and take it anally. This made my orgasm unbelievably intense. I started to wipe the cum from my skin and lick it off my fingers. Still, I felt I needed to go further.
One day, I decided to go food shopping wearing a pair of panties and a bra under my winter clothing. It was such a thrill. The whole time I felt like someone was going to discover what I was doing. However, I began going out more and more. I even bought a pair of pantyhose to wear out, but I restricted it to undergarments only. I didn’t have the nerve to dress like a woman on the outside.
Watching some porn one night, there was a girl sucking a dick through a “glory hole.” As the video went on I realized she was at a so-called adult bookstore. I immediately surfed the net to see if there was such a thing in the vicinity of my home. Sure enough, there was one about ten miles away. I had to go check it out.
The first time I went I dressed in normal men’s clothes and undergarments since I didn’t know what to expect. It was a Saturday night and it was amazing. There were private booths, small theaters, and large cubicles with a round padded table in the middle. A woman was laying on one of the tables with a man fucking her pussy while sucking another. There was a small group of men around the table watching, including me. Watching porn in person is so much more intense than watching it on the internet.
At one point, I could feel a hand rubbing my leg. It took me by surprise at first. Before I knew it the hand was probing my cock. Then there was a whisper in my ear, “Do you want to feel mine?”
I was mortified and couldn’t move or answer. My lack of response must have presented an opportunity. He opened his zipper, pulled out his cock, and too took my hand, placing it on his cock. A hundred feelings went through me instantly, but the thrill was the strongest. His cock was warm, almost hot. Hard, yet the skin was soft. I slowly began to move my hand up and down his shaft using my sense of feel to become acquainted with it. As the crowd began to respond to something going on with the woman, the cock was pulled from my hand as its owner turned and moved in closer to the action.
The crowd broke up about fifteen minutes later when the woman put her clothes back on and left with one of the men. I started walking around when I noticed another woman standing with two men. There was something strange about her. When I overheard her talking, I realized she was not really a woman, but rather a man dressed as a woman. I think I was more excited at her than I was with the real woman a few minutes ago.
I went home, changed into a bra and panties, and almost swallowed a whole kielbasa deep throating it while jerking off to an amazing orgasm. Then, I wiped my cum with the kielbasa and put it back in my mouth.
After that, I began to visit the adult bookstore wearing a bra and panties under my clothing. I was determined to experience oral and anal sex with a man while feeling like a woman. Unfortunately, I didn’t seem to be getting much interest the first three times I went. That was about to change.
On my fourth visit, I was sitting on a padded bench in one of the small theaters watching a video of a woman sucking an enormous cock, wishing I was her when two women came in and sat on either side of me. The one on the right softly said, “Hi, I’m Jenn. How are you tonight?”
I stammered a little before answering, “I’m okay,” in a quiet almost whisper.
While she seemed to have a strange voice, she was quite stunning. The one on the left leaned into me pushing her breast firmly against my arm, “My name is Brittany. It’s kind of quiet in here tonight. Do you come here often?”
Although I was still nervous, I began to loosen up a little as I fumbled for an answer. “This is only my third or fourth time. I guess I’m new to this.”
The one on the right, Jenn, asked, “Do you like CDs, dear?”
That’s an interesting question I thought to myself. Here I am, a wannabe CD, being asked if I like CDs. The answer would have to be yes, so I naturally said out loud, “Yes.”
This prompted Jenn to put her hand on my shoulder. One of her fingers started to follow the contour of my bra strap. She expressed her surprise by putting her other hand in front of her mouth with a slight giggle. Brittany leaned forward, looking at both of us, with an inquisitive look and a questioning, “What?”
Jenn answered Brittany with a big smile, “She’s one of us, Brit.”
Brittany shot back, “Oh dear, she needs our help.” With that, they hugged me from both sides.
Jenn declared, “My poor baby. We’re here to help you. Do you have any clothes with you?”
Still somewhat in shock and a little confused, I answered her, “No.”
Jenn told Brittany, “Take her to the ladies' room, Hun. I’m going out to the car to get her some clothes. I’ll meet you there.”
Brittany took my hand and led me to the ladies' room. The bookstore appeared to be a converted old fast food building having both a men’s and ladies' room. Once in the bathroom, Brittany inquired for reassurance, “You do want to be a woman, don’t you?”
Feeling some embarrassment, but not wanting to pass up the opportunity, I had to answer, “Yes.”
She took my coat off and then my shirt leaving me with just my bra on my top half. “I love your bra honey,” distracting me a little from my now extreme embarrassment. Then she instructed me to kick my shoes off before she untied my sweat pants.
The door opened at the same time she was pulling down my pants. Jenn came in with a large carry bag. She looked me up and down. “Nice body babe. You look good in those panties. Let’s get you into some nice clothes to show off that body. Sit up on the counter.”
I sat up on the counter between the two sinks. Brittany and Jenn each took a black stocking and rolled them up my legs. Then, they told me to stand on the floor. Brittany wrapped a garter belt around my waist and hooked it in the front before attaching the garters under my panties to the top of the stockings. At the same time, Jenn inserted a pair of breast forms into my empty bra. I could feel my cock hardening. Brittany giggled and kissed it through my panties as she said, “Gurl, you have to learn to control that.”
Jenn stood in front of me with a black dress instructing me to step into it. Brittany zipped it up from behind me. “Time for the face and hair,” declared Jenn. She put make-up on my face, followed by an eyebrow pencil, eye shadow, and mascara. At the same time, Brittany was putting nail polish on my fingernails. While my nails were drying, Jenn put lip gloss on my lips.
They finished by putting a blond wig on me and brushing it. When they turned me around so I could look in the mirror, I couldn’t believe it. They transformed me into a passable-looking woman in about twenty minutes. Jenn took a pair of strappy high-heeled shoes out of the bag and helped me put them on. Brittany put a necklace and bracelet on me.
“Well, what do you think? How do you like it?”
I was in awe. “You two are incredible. I can’t believe this.” They both hugged me at the same time.
“It’s time to strut our stuff,” declared Brittany. They put my clothes in their bag and put it under the bathroom counter before the three of us walked back into the dark halls of the bookstore.
We walked back to the theater room where they first met me. This time we got quite a different response than I’ve gotten in the past. We were like celebrities. Within a few minutes, there was a small crowd of men around us. Brittany whispered in my ear, “Well Honey, what would you like from one of these men?”
I felt like Brittany was my fairy Godmother granting me one wish for anything I ever wanted. It only took me a moment to decide before I whispered back in her ear, “I’d like to suck one of their cocks.”
Brittany immediately announced, “My girlfriend would like to suck the best cock here. Who thinks they have the best?”
There was some quiet whispering amongst some of the men when one of them pushed his way into the front, pulling his pants down, and declaring, “Here you go, it’s the best and the biggest.”
I had to agree with him. It was probably bigger than the kielbasas I had been practicing on the past few months. It was erect, but not hard as a rock. I reached out with both of my hands to feel it. The skin was soft and warm. I cautiously leaned forward and licked the end of it. There was an almost sweet taste to the large drop of precum on my tongue. I had to have it in my mouth.
I pushed him back a step so I could get down on my knees in front of him. Brittany slid over on the bench directly behind me. She pulled the hair on my wig behind my head. I licked down his shaft and back up feeling his bulging vein with my sensitive tongue. Then, I put my lips around the tip using my tongue to feel the slit and taste more of his precum. I never realized how sensual a man’s cock was in a mouth. The lips and tongue are so much more sensitive than the hands.
I moved my hands from his cock to his ass cheeks to I could put more of him into my mouth.
Brittany was still holding my hair back. Using my hands, I pulled him towards me taking him to the entry of my throat before pulling back while my lips slid along his beautiful shaft. Again, I pulled him into my mouth and pulled back with my lips sealed on him. When he was almost out of my mouth I wagged my tongue on his slit along with a slight sucking action. I began repeating this routine over and over. He put his hands on top of my head urging me back and forth pulling a little harder each time as he approached the back of my mouth.
As I continued I could feel his cock becoming more slippery from my mouth. I had to have more of him and I knew what we both wanted next. I gripped his ass tighter and pulled him hard into my mouth. The first thrust pushed him into my throat a little. His cock was smoother and softer than the kielbasa being gentler to my throat. The second thrust I pulled him in further. My chin was buried in his balls on the third thrust as I took his entire cock. His grip began to tighten on my head.