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I have been a closet cross dresser since my early teens seeking my mother’s panty hose and underwear I thought I had kept it well hidden when I turned twenty I got a place of my own I found it very hard to get my women’s clothing since I didn’t have the courage to go out in public which brings me to my story . a friend of moms named Sherri was bag ng problems with her old man and they had spot up she came to me and asked if she could move in and help with the rent I was all for it Sherri wes a tall red head very pretty and we’ll built a couple of weeks went by she was gone one evening a pair of her sandals was by the door so I tried them on this was the first par of ladies shoes that was even close to fitting me I had ever put on the Feeling was overwhelming I walked around the house n her sandals and made my way to her bathroom once inside I locked the door and started looking around she had everything razors makeup there was panties everything a young crssdresser could hope for I ran me a hot bath in her tub and climbed in after adding some oils I lathered my legs up and shaved them for the file time in my life I will never forget that feeling I than shaved my armpits and got out of the tub and tried to drain it but my hair kept plugging the drain finally I got the water out and looked at my body in the mirror I couldn’t believe it was me next I put on a pair of her panties and bra the bra was tight but I got it on anyway than I put the sandals back on and opened the door to go into the kitchen and there stood sherri I didn’t know what to do or expect from her she smiled and said I finalize fought you I said what it turns out that she knew all along womanI was a crssdresser.I tried to get my clothes and she said no we are going to discuss this right now in the kitchen we sat at the table and talked for hours about my desires to dress as a woman so that eventful night started my life as a woman she told me that I wasmto spend the next three months totally as a woman except when I was at work then I would just wear woman’s undergarments so my transformation started Sherri helped me become a woman I was to keep my body totally shaved nails panted while in the house wear makeup everything a woman does I was in heaven until one day when Sherri told me its time we tàke another step tonight you will go out as a woman I bathed shaved and put on a pair of Sherri’s panties andpantyhose and her bra since I still didn’t have anything of my own then makeup and lipstick coupon ear rings all with Sherri’s help she than went to her room and returned with a pair of capri’s and a black sleeveless top and black sandals when I got it all put on I looked amazing all but my has but Sherri fixed that she found me a long black wig i couldn’t believe it I was finally a woman and I was scared to death about going out our first stop was a gas stop I pumped the gas then went inside to pay I dropped the money and a man bent down picked it up and handed it to me I thanked him and paid and went back to the safety of our coutthen we went out to a different town for the night out we got to the town 65 miles away Sherri sent me in to a motel to rent a room and the lady working there didn’t say anything other then enjoy your stay to be continued

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Beginnings

Looking back on my life, I realize that we are all products of our experiences, but certain events are more pivotal than others. When questioned, most people would say the most important things were things planned, like college, marriage, and children. Whereas those are indeed important, I think the course of my life has been defined more by the little things, like a chance meeting, or unexpected event. I guess I should start my story from the beginning. My name is Carol. I was the only...

Beginnings

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This is a true story it happens over 50 years ago before all the news an information regarding sexual predators, gays and bisexuality. I am now 65 years old still horny but much wiser about various facts of life. Here is my story about my first sexual experiences, good or bad I let you decideA Friend and I were hitching home from school in those days it was fairly common practice then, often it would take a couple of different rides before we reached our respective homes. This day we hadn’t...

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Beginnings

I was six years old, and “the woods” was actually nothing more than an empty lot behind my family’s home, with a stand of trees and a lot of brush. In the center of it, trampled down by years of kids using it as a hideout, was a small clearing that could not be seen from outside, and anyone coming towards it made so much noise that you always had plenty of warning… and the night before, I had almost had Christy talked into pulling her pants down for me when her mom started calling for her to...

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Introduction: How I learned what a naughty boy I really am:) Bye, Mom, I yelled as I ran out our back door. I knew that Christy would be waiting for me, and I was in a hurry&hellip, she had promised the night before that she would meet me in the woods, at our secret spot, and continue what we had talked about then. I was six years old, and the woods was actually nothing more than an empty lot behind my familys home, with a stand of trees and a lot of brush. In the center of it, trampled down...

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Beginnings

back when I was much younger I was introduced to my first cock. It started like many others I guess, a friend (Rick)and I finding a mutual enjoyment of the playboy, penthouse, hustler , etc magazines. Of course that led to us first showing each other which pics we liked the most, and since we both knew what we were doing, we then moved on to masturbating in the same room. That eventually led to one of us touching the other,since everything we did felt better than the last, of course it...

Beginnings

The arrangements were simple.She loved her husband. She had an open relationship with him. But she had an itch that needed to be scratched. The itch was S&M. She spent hours at a time discussing her desires, her interests, in chat rooms, on messenger with strangers and with friends.I was one of them. Just another bloke who sat in chat rooms and made no secret of what he likes. It was easier that way. Sit around and wait for people who'd read my profile and understood my tastes to happen...

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As I sit here as a middle aged and jaded man, with the glass definitely half empty, I look back on my early sexual awakenings and experiences. During my lifetime I have had sex with both men and women, and got very different rewards with the encounters I had. Sex with men took place in public toilets, and was taboo and thrilling; sex with women was emotionally rewarding, but lacked the thrill of my gay encounters! But going back further, shortly after discovering my ability to orgasm through...

Beginnings

I never realized the pleasure that could be derived from anal stimulation until an old girlfriend slipped a finger up my ass while working on my cock one time.She had my cock pretty well lubed up, with the excess finding its way down the crack of my ass as she worked my shaft with one hand and my balls with the other. She eventually moved from massaging my balls to running her finger down the crack of my ass spreading the oil and teasing my tight puckered hole with each pass.I was surprised at...

Beginnings

The heat behind the heavy leather hood was unnerving, almost unbearable. She could feel trickles of her sweat mixed with her tears run down her flesh. Her cheeks muscles ached from the penis shaped gag that had been forced between her teeth. Muting her screams and groans of fear and ecstasy. She was captured in the darkness. The silver ring on her collar had been fastened with heavy chains to the padded floor. The platform she knelt upon was tilted, her body inclined so that her ass was raised...

Beginning

A summer a few years my mum was offered use of a friends beach up the coast. It fronted onto a small secluded beachwith only a few neighbours and a small shopping centre.My friend Mickey went with us so I'd have some companionship for the few days we were to be there and mum couldjust relax and enjoy the solitude.Well anyway it was a nice place a bedroom each big lounge kitchen spacious bathroom and its own pool too.After we arrived Mickey and I headed sown to beach with nothing more than our...

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