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My growing curiosity was really starting to take control. I've spent so many years married, hiding my true thoughts and fantasies about sex.
My wife and k**s were going out of town a couple of weeks ago and I was going to explore more of what I wanted. As the day they were going to leave got closer, my pulse would race and my palms would sweat.
I just hoped I wouldn't chicken out.
Finally, I dropped them off at the airport and as soon as I did, I was freaking out. Just thinking about visiting my first gay bar made me have an erection so hard, I unzipped and released the pressure in the car on the way home.
As soon as I got to the house, I ran inside and started getting ready.
I shaved, had my shirt and pants picked out and with a splash of cologne, I waited for the bar to open.
I knew it opened at 7pm, so I waited until 8 to finally get in the car. I was so nervous driving there!!
As I pulled up, I noticed a couple of pretty young guys walk in.
I started to doubt whether I should go in. Should I just leave this as a fantasy? I'm a middle aged guy with a slight ponch and thinning hair. What if no one was even interested in me. That would be devastating.
But I gathered up my thoughts and figured, "If nothing happened, at least I would know."
As I walked in, I showed the doorman my ID and noticed my hand was shaking.
I went straight to the bar and ordered a beer to calm my nerves.
About a half hour went by as I sat watching people dance, talk, laugh and have fun. I stared at my drink occasionally and tried to figure out whether I should go.
Suddenly a guy about my age walked over to me and introduced himself. He said his name was Fred and he noticed me when I walked in.
He wasn't bad looking. A little chubby with a goatee.
We talked a while about jobs, etc. and then suddenly he put his hand on my knee, looked me in the eye and said, "How about we get out of here?"
I bolt of lightening ran through my body as I shakily said , "OK."
He said he didn't live to far from there and would I like to follow him home? I agreed and we both went to our cars.
I followed his car to an apartment complex about a mile away.
As I got to the door, he put his key in and as he opening the door, he looked over and said, "I'm glad you came. I was worried you would say no to me."
I walked in and noticed how nice the place was. Very neat and tidy.
I turned to see him shut the door when he walked right up to me quickly, placed his hand on the back of my neck and pulled me in for a kiss.
It was long and deep. The deepest kiss I'd ever been given. Our tongues wiggled in each others mouths for what seemed like an eternity. He grabbed my butt and pulled it in close. I could feel his throbbing cock through his pants as it touched my stomach.
He slowly pushed me against the wall and kissed me more, pushing his body more against me.
He finally stopped and said, "Sorry. I just....I just couldn't help myself."
I licked my lips and told him it was fine. I liked it.
"Are you ok if I sort of take over?"
I told him I was very new to this and yes, I wanted to learn whatever he needed to make him happy.
He looked at me and said, "Anything?"
I started to get a little worried and whispered, "Well...no Anything."
He smirked and said, "No, nothing bad, just...would you mind if I gave you something to wear?"
"No, not at all. ", I said.
He disappeared for a about 3 or 4 minutes and then came out with something blue and silky. "What size shoe do you wear?"
"Um....11."
"ok,", he said. "I think these will fit."
He then gave me what appeared to be a dress and shoes.
"I used to play dress up and well, It'd be great if you would wear these."
I'd only dressed as a woman once before and that was just trying on a girls bathing suit during a sleepover. This was way, above and beyond, but as I saw the huge bulge in his pants, I really wanted my lips around his cock, and now, I was willing to do anything.
"OK", I said. I'll be right back.
I walked into his bathroom as he told me where the bedroom was and that he'd be waiting.
I walked in, shut the door and looked at the dress. It was pretty. Low cut and silky smooth.
I slipped off my clothes and put it on. I then put the shoes on and yes, they did fit. They were high and I'd never walked in high heels before, but got the hang of it pretty quick.
I walked out and shut the light off. I noticed a dim light coming from where he said the bedroom was and started towards it.
There he was, laying under the covers, a tent from the bedsheet where his penis was.
I walked to the end of the bed, put my hands on the sheet and slowly crawled towards him.
I ran my hands over the sheet to his manhood and slowly played with it, letting the sheet smoothly rub on it.
He threw his head back and moaned a little, "yes".
I crawled up further until my ass was over his bulge. I moved the dress to flow around me and laid my cheeks over his cock, letting it slip between them.
I rocked slowly back and forth as a pinned his arms down.
I could feel him pushing up against me with his hips.
After a while, I let his hands go and pulled the sheet down over his cock.
There it was, throbbing and ready.
I slid my lips over the sides of it for a couple of minutes and then finally, quickly put the whole thing in my mouth.
"GOD, YES!" he said.
I cupped his balls and moved up and down with my mouth. He grabbed my hair with both hands and started fucking my face. Harder and harder, moaning louder and louder.
"Wait, wait, wait!", he said. "I'm gonna cum too fast."
He then grabbed my leg and pulled me over his face, putting my cock into his mouth.
I was sixty nine-ing!
It felt so good to finally let go. To be myself. To have this man sucking my cock as I sucked his. Not a care in the world.
"Cum in my mouth!", I said as I grabbed the bottom of his shaft, putting his head in my mouth.
"Oh, thank you!", he screamed.
It only took a couple of jerks for him to explode his warm cum in my mouth. I didn't think twice. I just quickly swallowed what I could and let the rest run down my face.
The thought of him cumming made me cum and he had me shoot it on the pillow.
We laid there for a while, tired and sweaty.
As I got up, he also got up, came around to my backside and wrapped his arms around my belly.
He kissed my neck and whispered "thank you" in my ear.
I reached back and held his member, which was already hard again.
I slowly rubbed it as he held me.
It felt so strange wearing a dress and heels as a man held me close, but it also felt so good. In that moment, I was his. I was his love doll and I told him if there was anything else he wanted, I'd do it.
He told me to bend over the bed and I did.
I knew what he wanted and I wanted it bad.
He went to retrieve something from the desk by the bed and then came back.
I felt the dress lift up over my ass. A slow, slightly cold liquid ran down my ass crack as he messaged it in.
Then I felt it.
The tip of his cock was in my hole. Not a lot, but enough to feel it.
He slowly started pushing it in and I twisted and turned to make it happen.
He was finally in about halfway.
It hurt, but it felt so good.
I looked down and saw my feet in those high heels and was more turned on than ever.
I was his woman and he was fucking me.
"Grab my ass", I told him.
He grabbed both sides and began pumping harder and harder.
"I'm gonna come again.", he said.
"Good. Make me yours!" I yelled. I didn't care if anyone heard me. I wanted his cum inside me.
Then I felt it. It's warm ooze filling in my hole. He grunted and groaned behind me until it was finished.
My legs were jelly and I had to lay down on the bed, but it was the best I'd felt after sex in a long, long time.
I filled with his cum, laying on his bed in a dress and heels.
I laughed a little, wondering what my wife was doing right now and if she had a dress like this.

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When I was 12, I went to shop for shoes with my mother. I would walk around the store, making my mother laugh out loud. The onlookers at the store, would often look at me in astonishment and wonder, â€œHow is this little boy handling pencil heels so wellâ€?.Â My mama knew it back then that I was born different and she fought the world to make me who I am today, a proud cross dressing gay male. It was my first prom and I was nervous. I was worried that I will be made fun of at school, but my mama...

Confessions of a Sex Crazy Cross Dresser Part 8

Chapter 15: Dangerous Duo I woke up the following morning to an empty bed. I went to the bathroom and when I came out there was a knock on the door. I looked out and saw Peggy with a bag and two cups in her hands. Upon opening the door, Peggy came inside and placed the drinks and bag on the table and gave me a kiss. “I thought you might want some breakfast,” she said. She had on a pair of white shorts, a light blue tank top and her sneakers. “I brought coffee and donuts.” This girl might be a...

BiSexual Cross Dressing Cuckold

My bride to be cheated on me as a girlfriend, again when she was my fiancé, and thereafter as my hot wife for 23 years. I guess the stars aligned for us.Me-For some reason I turned to slutty, tight black satin gloves in bed, without ejaculation, a year before I accidently discovered masturbation and gushing in the bathtub. I was 12 the first time I ejaculated, rubbing my cock with slippery shampoo. An overwhelming surge of floating and pleasure washed through my virgin boner as my sudsy palms...

First time dressing

I do not claim to be a grammar expert and as such you will find some grammatical errors in this story. The errors can be the switching of tense, spelling errors, or typos. I ask if you find an error please send me an email so I can correct and make the story enjoyable for others.WARNING! This text file contains sexually explicit material. If you do not wish to read this type of literature, or you are u******e Eighteen, PLEASE DELETE THIS FILE NOW!!!!II did not know I had a disorder did...

My Road to Crossdressing part 2

I had dressed up since I was a teenager but it was only occasionally. Usually, it was just lingerie and it was always for me and just for masturbation. It was about ten years ago that I decided I wanted to go further and start using makeup and breast forms and wigs etcetera.Quite by chance one day, I rang an old friend just for a chat. I found out that he had rented his house out while he was travelling. The person on the other end of the line was a woman, or so I thought. We got talking and I...

The twin sisters of the cross dresser policewoman

（This post is a fictional story on a bondage forum in China, and I am the prototype of the story. I just translated it into English. The copyright belongs to the original author, and the portrait right of the photos in the original link belongs to the original author and me）In the middle of a gloomy and horrible room stood a woman with a shawl. She was wearing a sexy red cheongsam, a pair of sparkling flesh-colored stockings like cicada wings wrapped around the beautiful woman's slender legs....

AutoRide Made Me A Cross Dresser Whore 8211 Part 1

I’m a male, and cross-dresses occasionally in private. After cross dressing I get hard and then get off rubbing my dick against bed. Sometimes I post my cross-dressing photos online and get excited by comments and chats. I fantasizes about being seduced/forced to cross-dress and made to serve like a whore by dominant stranger(s). I’m darkish brown, lean. Has little hair on my upper body. Thin. Have slender arms. Soft face. And thick lips. And finger thick but long. My butt is rather fine and...

Highlights of the Day A Jo Cross Story

A LITTLE PSA FROM JO: Kirsten has finished writing her update on the day for you all, but I've just taken the netbook from her to add a little something of my own. I want to thank you all for taking an active part in her adventures. The truth and the fantasy. If I sometimes seem a little pushy in the feedback comments about the targets I set....That is because I can only have Kirsten at certain times and days because of work, personal lives, etc. And as I read your amazing suggestions, I...

Wartime

Elizabeth Fleming told me some of this story in the years before she died, aged eighty, in 2010. The more graphic scenes are mine but the emotions and surrounding history are hers. She was my Great Aunt, great in so many ways for she was the third family member I ever revealed my sexuality to, the first two being my parents. I had known since girlhood that she shared a cottage in Hampshire with her friend, Portia, but had never known their relationship was more than sisterly. When I told her...

firsts time Im seen as cd crossdresser

From a young age I liked dressing up in womens lingerie and clothing.... as I got older I grew up over weight a little and more so the older I got..... by the time I was I was in my late teens I had nice size breasts....nice enough to fill a bra. So worked up the courage to buy some lingerie online and when I received it in the mail I was so excited. I couldn't wait to try everything on.... I had brought a white lace bra, matching panties and white suspenders and stockings.....I tried them...

My First Time with a cross dresser

Growing up, like many children I went through phases. I would climb trees and play football, then as I reached my mid-teens I continued these phases but also became a lot more sexually aware, thanks to the porn magazines and porn films usually belonging to my mates dads or older brothers.Now I am in my late teens and at college.One day my Dad made a pot of tea and breakfast.“Did you sleep well, son?” he asked as I entered the kitchen.“Not bad thanks, Dad, how about you?” I replied.“Pretty good...

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