I'm 41 and have a more than active sex life. My Girlfriend and I have been together for over ten years. We are both sexually adventurous and started to do role playing games about two years ago. It turned out to be alot of fun. It was like putting on a small play. We would get costumes, work out a basic scenario and improvise from there.
For the last six months we've been hooked on cross gender games. I would dress like a woman and she as a man. I am amazed at what a turn on it is for me to dress and act like a girl.
It started with one of my old French maid fantasies. She had done it for me several times and had all of the stuff already. So, she asked if I would be the maid and she would be the guy. We talked about it for a while and I finally agreed.
She had a realistic looking strap on and we both got dressed. It turned out to be one of the best things we had done. It was such a turn on for me to dress up and suck her 'cock' that I was immediately hooked. I insisted on doing it every chance we got.
As time went on I got better and better at dressing like a girl. I already had long hair that I kept in a pony tail, so it was no problem to cut and style my hair. I had gotten a rather slutty wardrobe. D-cup silicone breast forms. My own makeup kit. A corset like waist cinch and had been practicing my female voice around the house non stop.
Sandy and I even dressed up and hung out around the house in our spare time. She would call me Susan and I called her Andy. We had a three day weekend coming up and I was dead set on spending every minute being Susan.
After work Thursday, I rushed home to get dressed and ready for the weekend. I quickly showered and shaved. We had agreed to do some things that were much more daring than we had done before and I was really looking forward to it.
We were going to do things that were a little more public. Giving me an extra thrill knowing that guys would see me dressed as a girl. I thought I was a pretty ugly girl but Sandy assured me I was quite pretty and that guys would definitely think I was sexy.
I hurriedly collected the things I wanted to wear and stood naked in front of the mirror. I enjoyed watching myself transform from my male self to my female self.
Today I was so turned on that the first thing I needed to do was satisfy my boner. I began to play with myself and think of the activities we had planned. I came almost immediately and greedily licked up my own cum.
Next I took a small butt plug and lightly taped it to the end of my cock. I lubed the plug, pulled it between my legs and stuffed it into my ass. I rearranged my balls and stood up to examine my handy work. I smiled broadly. With my cock pinned back like this, there was no chance of it getting loose and it looked almost exactly like a bald pussy with big puffy pussy lips.
I put on the waist cinch and smoothed it out. I smiled at my hourglass figure as I modeled in front of the mirror again. I put on a see thru white bra and inserted the breast forms. They looked and felt so real it was amazing. They had big erect nipples and large brown areolas. I wiggled my ass and watched as my tits bounced.
I was so turned on, I had to pull my cock loose and jerk off again.
When I finished, I pinned my cock back again and put on a see thru white thong. I smiled as I examined myself in the mirror again. My 'pussy' was clearly visible and it looked so real, even I would have sworn it was real. I bent over to inspect my smooth round ass and was as happy with the way my ass looked as I was with the way my 'pussy' and tits looked. I just couldn't have been happier.
I sat at the makeup table and curled my hair. Since we planned on going out, I spent extra time putting on my makeup, nails, eye shadow, eye liner and polish.
When I finished, I examined myself in the mirror. With every step, I got happier and happier. Things were really shaping up. I looked more like a girl than I ever had before. The see thru bra and panties were what really did it for me. It was almost as good as being nude with a real pussy and tits.
I heard Sandy come in the door and went to meet her. When she saw me she stopped dead in her tracks.
"In a hurry to go out?" she said with a laugh.
I blushed and smiled. "Yeah, I've been thinking about it all day. I can hardly wait."
She smiled "Well, you finish getting dressed and I'll get a shower."
I gave her a quick kiss and headed back to the bedroom. I smiled at myself in the mirror as I put on a loose white button down blouse with big lacy lapels. I still wasn't used to the buttons being on the wrong side, so it seemed like it took forever to button it up. Once it was buttoned it looked great.
It was fairly sheer and lightweight. So it moved and billowed quite easily. I could see my erect nipples sticking out a mile away, and I could even make out their color. Plus with the deep low cut front, I could look right down it and see my tits when I bent over. This was great!
I pulled my black stockings as high up my thighs as I could get them. I put on a mid thigh pleated black skirt and a pair of black boots with 4" heels.
My transformation complete, I modeled for myself in front of the mirror again. As I did this, a big smile crept across my face. I did a quick spin and watched as my skirt twirled out high enough to expose my panties and ass.
I just loved high heels! They made my ass stick out and gave me the cutest little bubble butt. I was so happy with the way I looked I was thrilled I still thought I was kind of homely, but at least I was hot.
I walked to the kitchen and made myself a drink as I waited for Sandy to get dressed. When she came out, she was dressed in some pretty conservative clothes. A simple pull over dress that came to mid calf and some brown pumps. She looked like a school teacher.
"I thought we were going out." I said shocked.
"We are." she said "but you like being a girl and you look so hot, I thought you should be the attraction."
I smiled "Cool"
"Now get over there so I can take a picture." she said pointing.
I stood in the center of the room and posed as she took several pictures to start our night. We lived on the NC/Ga border in Blairsville and were planning on going to Atlanta so we could get some pictures of me flashing on the street.
I had always admired how women can show off their pussy in public and I wanted to try it in the worst way. I thought it would be fun to have pictures of me as a girl, putting my goodies on a very public display.
The drive to Atlanta was pretty uneventful. Sandy drove and I sat in the passengers seat. I opened my blouse and flashed several cars and trucks on the way. They all cheered and honked. I giggled when it happened, but it gave me more confidence in the way I looked.
When we got to Atlanta, we headed into Peachtree and parked at a small strip mall just off the road. As I looked around, I suddenly got very nervous and began to squirm in my seat. Sandy noticed my discomfort immediately.
"You'll be fine" she assured me "It'll be just like flashing those guys on the highway."
I giggled and smiled real big as we both stepped out of the car. Sandy came around the car and snapped a picture of me standing next to the car taking in my surroundings. I looked at her quickly in shock.
She laughed "That was perfect! Let's see some snatch!"
I stood dumbfounded for a second, looked around quickly and made a small curtsy as I pulled up my skirt. She snapped another picture and examined it in the viewer with a big smile.
"This is great! Take a look." she said handing me the camera.
I looked at myself with my skirt up. I could see right through my panties! It was perfect! It looked like a real pussy! I couldn't tell the difference and I knew it wasn't real. As I zoomed in on my crotch, I could feel my cock getting hard. It was a real turn on knowing I could show off my 'pussy' just like any other girl.
With renewed confidence we strolled around the mall. Sandy took pictures of me standing around in front of different stores looking in. Most of the guys walking by smiled at me and some even said hi. I smiled and returned the greeting.
We ventured into a clothing store. While in there, We took pictures me pulling up my skirt or exposing my ass while people stood around unaware of what we were doing. While looking at some jackets I tried one on and unbuttoned my blouse. I opened the coat and blouse at the same time, openly displaying my tits as a guy in his 70s stood on the other side of the rack.
I buttoned my blouse again and returned the jacket to the rack. I then pulled my panties to my knees and casually looked at the the guy while lifting my skirt. Sandy was taking pictures constantly. Once we had snapped enough pics we decided to get some coffee at the other end of the mall.
We both got cappuccinos and sat at a table outside. As we sat and talked about how much fun we were having, I heard a familiar voice behind me.
"Hi Sandy! I thought that was you!" it said cheerfully.
I froze! It was my friend Gabe. We were both finishers on the same crew. We had been working together and hanging out for about five years now. We got together quite often and it hadn't even dawned on me that he only lived a block away.
"Hi Gabe! Why don't you join us?" Sandy replied with a smile. "This is Susan."
Gabe was a mountain of a man. He was 45, black, 6'6" tall and we talked about sex all the time at work. He would tell me about the neighborhood sluts he hooked up with and I had told him about some of the games Sandy and I played.
I was staring at Sandy in shock as Gabe took a seat. When I glanced over at him, he had a big smile and was staring at me.
"I was hoping to meet your friend Sandy, but I see we've already met." he laughed.
I blushed hotly at being discovered like this. Gabe just kept smiling at me.
"Well, aren't you pretty? Out playing games?" he asked.
I looked up and nodded "I was going to be a girl and flash on the street." I admitted.
Gabe got an astonished look "Really? How's it going?"
Sandy offered him the camera and he began to review the pictures. He laughed and thought they were great. He especially liked the one with my panties down while a guy stood two feet from me unaware. He asked how I managed to make such a nice pussy. I told him about the butt plug and how I had taped my cock to it so it wouldn't get away.
He was instantly curious and insisted on seeing for himself. I smiled and pulled up my skirt to show him. Sandy snapped a picture of him staring at my crotch.
He asked to see it without the panties. I looked around quickly and pulled down the front of my panties. Sandy of course got a picture of that too
When she sat back down, she whispered excitedly "That was fucking perfect! We should walk around the stores and I can take pictures of you flashing him like he's a stranger!"
We all smiled at the idea and spent the next hour doing exactly that. I would walk by Gabe and flash him while he stared in shock. I would bend over and show my ass while he just looked. In every scene there were people milling about around us.
We even got a picture of us at the meat counter. He stood next to me, pulled up the back of my skirt and showed my ass to the guys behind me. I just smiled.
We went back to the cafe and ordered more coffee. I was becoming quite comfortable with being a girl and we talked easily. We looked at the pictures and talked about them. We talked about things we could do.
We talked about the meat counter picture and how much we all liked that one. We took a few pictures of Gabe feeling me up or playing with my tits at the table. As we continued to talk, Sandy began to get an evil grin.
When I saw that look, I knew she was thinking of something and had to ask
"Uh Oh, now what?" I said with a sideways look.
"We could do the street walker bit! I could take pictures of him giving you money and you kneeling in front of him like you're going to suck his cock!" she whispered excitedly.
I thought about it for a while. "I guess we could? but where can we go?"
"That's easy" Gabe said with a smile "We can go out back behind the dumpsters."
"Really?" Sandy and I chimed in at the same time.
Gabe nodded, so we picked up our stuff and headed around the corner. Just like he said, there was a little alcove with 2 dumpsters and a small light. We went behind the dumpsters surveyed the area and made a short scenario.
We would stand close together. He would give me $20. I would kneel in front of him. Pull out his cock and hold it in front of my face. Maybe even stroke him a little bit to make sure he's hard for the picture. We all agreed and got ready to start.
Sandy stood back, Gabe and I smiled at each other as he handed me a $20 bill. I kneeled in front of him and smiled at the camera.
"Don't look at me!" Sandy snapped angrily.
I turned to face Gabe, and was suddenly shocked. I was about six inches from the huge bulge in his pants. I began to tremble as I stroked it through the fabric. I could feel his big meaty cock throbbing in anticipation. I stared at his bulge as I slowly pulled his zipper down.
Once I pulled his zipper down far enough, I was thrust into a new dimension. He wasn't wearing any underwear and his cock sprang free like a jack in the box. It smacked me in the face and scared the shit out of me.
I jumped and looked up at him as his half hard cock hung only and inch from my mouth. He had a big smile and was watching closely as I wrapped my fingers around the thick shaft. It was about nine inches long and two inches thick. I started breathing heavy and felt my cock getting hard.
I had sucked and been fucked by Sandy's strap on many times but that was nothing compared to this. I was on my knees and had a real cock in my hand. I was so turned on I could hardly stand it. It was hot, smooth and throbbing in my hand as I stroked it's length. I couldn't look away. I was fixated with his cock.
I watched in fascination as it got hard and a clear drop of cum formed at the tip. This was by far the most erotic thing I had ever seen or done. I was so carried away, I couldn't help myself. I licked up the drop of cum and greedily sucked the head of his cock into my mouth.
It was radically different than a strap on. It was warm, smooth and quite pliable. It had a thick musky taste and smelled of sperm. I went wild with lust. This was my first real cock and it was better than I had ever imagined. I grabbed his hips and sucked his cock hard and fast while listening with pride to Gabe's moans.
My cock was so hard that it was about to pull my butt plug out. When I squeezed my ass and rolled my hips forward. I felt the plug sliding in deep and my cock head drag across the soft fabric of my panties. I moaned as it sent a lighting bolt of pleasure through me.
I began to hump the air and moan loudly while I was sucking Gabe's big hard cock. After only a few seconds, I was bucking my hips and squealing like a stuck pig as cum shot out of my cock. Squishing between my ass cheeks.
I could feel Gabes cock throbbing in my mouth. I could feel my cock throbbing between my thighs and ass cheeks. I could feel my ass being covered with thick gobs of cum. I went into sensory overload and just about freaked out.
Once my orgasm subsided a bit, I could hear Gabe chuckling. I looked up at him, thoroughly disgraced as a man. I was dressed as a woman. I was sucking him off behind the dumpsters. And I had just cum hard.
I felt like such a dirty slut.
I would never be able to think of myself as a straight guy again.
Gabe was laughing at my humiliation while I looked up at him. He knew it was the ultimate blow to my manhood. The image of me dressed as a girl and getting off while sucking his cock for money, would be burned into both of our brains forever. Which made me even more aware of the cock in my mouth.
"Don't stop!" Gabe laughed "I was about to get mine too!"
I could hear Sandy giggling and snapping away in the background. I accepted my fate and sucked his cock like the sloppy whore we all knew I was.
Without a word, Gabe grabbed my head and began filling my mouth with thick streams of cum. It tasted so good, I didn't even think twice about swallowing. besides, if I was going to be a slut, it was only natural.
"YEAH! Now That's What I'm Talkin About! That's the way to blow Gabriel's horn baby!" Gabe exclaimed as he pulled his satisfied cock from my mouth
I looked at the ground and shook my head as I stood up. My shame was complete. I was a sperm burping gutter tramp.
Sandy and Gabe on the other hand were looking at the pictures in the viewer and seemed to find them quite amusing. They both agreed, as a girl, I was a good cock sucker. In fact, they had never seen a better one. They both thought that was quite funny.
Gabe looked at Sandy "He's pretty good. How much to make him my girl for the night?"
"For $150 she's yours for the weekend." she said seriously. "I'll bring her some more cloths in the morning."
"It's a deal" Gabe laughed and handed her the money.
Sandy stuffed the money in her purse "Have fun Susan, I'll see you in the morning." and headed home.
I stood dumbfounded as she drove off. Gabe smiled and waved at her.
"Well, let's get going." he said "You're gonna have to work that ass if I'm going to make my money back."
I gave him a big smile and we walked toward his apartment. In a strange way, I had gotten what I wanted. I was going to be Susan all weekend.