Diary of a Cross-dresser Ch. 01

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The yearnings of a sissy and his fantasy come true.
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Adikon79
Adikon79
11 Followers

This story is based on my own personal experiences and any comparison or similarity to anyone else's story, experiences, or copyrighted material is purely coincidental. This story contains adult material and language and should only be read by those legally permitted to do so. The story within is the copyrighted material of the author and should not be redistributed, sold, or copied without the permission of the author. All names have been changed to protect those involved. Enjoy!

*****

~ Preface ~

Before reading my diary you should know a little about me. I am a middle aged adult male, kinda tall, and rather manly looking. For the majority of my life I have lived what most would consider a straight life. Sure I had the occasional gay experience when I was younger. I have gotten another guy off, sucked a few cocks and had my own sucked by another guy. Nothing major really just the curious mind of a young male exploring his sexuality.

A few years ago though by chance viewing the varied porn sites most males visit, I came across the world of sissies and cross-dressers. Now before this I had had the occasional fantasy of being physically transformed by a lover, the most extreme of which involved being transformed into a female by a strong male type person.

What follows is one of the most successful encounters I have had the pleasure to enjoy, and with any luck will continue to enjoy.

*****

~ Chapter 1: The Beginning ~

It was the beginning of fall, the leaves were turning, the air was becoming crisp, and I was feeling a bit randy. I have tried a few times before to find just the right guy, but always seemed to come up short. Sure finding a guy who wants his cock sucked by a cross-dresser is not hard, plenty of men out there needed a good bj, and making them moan with my mouth and hands and having their cock explode between my lips is fun and all, but it is far from the experience I was looking for, craving. I really wanted to find a guy who really wanted me, who I turned on dressed as a woman, and who would really make me feel like a girl. Sadly, these men are few and far between it seems.

Knowing of the disappointment I was likely setting myself up for I went ahead on the my favorite site for fishing and posted an ad to see what turned up. You can't find what you are looking for unless you try, right? Sure enough within minutes of my ad going live on the web, the replies came in. I sorted through the usual replies, some pic fishing, some just curious, and some just looking for a quick blow and go. I wanted something more though, and soon sifted through the refuse to come up with a few possibilities. "Now to see who is who," I thought to myself as I began to reply to them. Now in my ad, I had asked for people to include a pic or so, as I had posted a few in my own ad. Quickly one didn't reply at all, so he was out. Then I was down to two. One older professional type replied early promising a mind blowing sexual experience, and the other lived near by and seemed genuinely interested in giving me what I was looking for. After a few more sorted emails the professional man dropped out due to a sudden personal engagement, and thus made my choice easy with the closer guy.

He was a cute one, and called himself, Jim. We shot back and forth a few more emails discussing the details of our meeting. When he could be here, what he liked, what his expectations were, the usual fair. His pics, mmmmm, his pics made my inner girl squeal and blush. He was reasonably tall, short hair, fairly fit, and with such a nice cock. He was a dream come true at least in pictures, though the emails we were exchanging made him more desirable by the letter.

We agreed to meet later that afternoon. I put on my favorite attire, a red bra and panties, a white blouse/tank (which with the bra showed off my cleavage nicely, with my inserts ), a long dark skirt, and my red and white striped knee high stockings. I brushed my long dark hair, and tied it back in a nice ribbon and waited for him to arrive.

I was nervous, as I always was with such meetings. You never know what to expect sometimes. Is he what he said he was? Will he be as he said he would? Would he like what he saw when he got there? All these thoughts and more ran through my mind. The tense few minutes before his arrival seemed to drag on for hours. Then he arrived. I swallowed hard and got up straightening my blouse and skirt and prepared to meet him.

I stood at the top of the stairs, as I head the front door open, and heard his voice call out, "Hello?"

"Hi, Jim" I called back out to him "I'm upstairs."

He closed the door and looked up the stairs. I was so relived to see the smile on his handsome face as he looped up the stairs at me. "Why hello there, Lacy," he said as he came up the stairs. Lacy was the name I often used when cross-dressing for my feminine identity.

He got to the top of the stairs and wrapped his arms around me in a hug. I smiled, and we took a moment to look each other over. He ran his hands over me, giving my tits and ass a squeeze as he gave a pleasant 'murr' in response to what he felt.

"Would you like to come into the bedroom?" I asked. He nodded and I took his hand and led him into the bedroom. He continued rubbing my round ass as I led him there, making me shiver a bit.

When we got into the room, I turned to see him slipping his shirt off, then soon followed by his belt, pants, and boxers. As his boxers slid down I came to see the most beautiful hard cock, I think I had seen. I moved up wrapping my hand around the shaft and giving it a small stroke, to which he let out a soft groan. I smiled.

He continued to feel me up rubbing my tits and ass. Then he grabbed me by the waist and moved me over to the edge of the bed. "Bend over," he whispered into my ear as he pushed me. Now I should note, I love masculine dominant men, so him taking charge as not a turn off, but a turn on. I bent over, obediently, pushing my ass out a bit. I was caught a little bit by surprise, pleasant as it was, by his straight forwardness. He felt up my ass a bit more then pulled my skirt up and pulled my panties down, leaving me exposed to him. He then moved up and ground his hard cock into the cleft of my round ass, making me groan in pleasure. Then he bent over my still grinding, "get up on the bed" as he grabbed my hanging tits, rubbing them.

I put my knees up onto the bed, bent over, ass out and exposed as he ground his hard cock on me. "Mmmm I love your ass, and these stockings..." He stopped grinding to rub his hands along my striped clad legs, soliciting another shiver from me.

"Mmmm, I am glad you like them." I replied. He felt them up a while longer, before stopping and asking me.

"Would you like to suck my cock?" he asked, though I think he knew the answer.

I eagerly nodded. Then he climbed onto the bed, on his knees next to my head. I smiled inwardly being face to face with that swollen member. I licked my lips, and leaned closer taking the base of his shaft into my hand, and sliding that swollen head between my lips as he groaned. I always loved sucking cock, the smell, the taste, the feel of it between my lips, as well as the moans I could get from my lover. I began sucking and stroking him happily, gradually working more and more of his stiff length down my throat. Soon I had him moaning in pleasure as his hips began to buck, and I felt his hand on the back of my head. My head bobbed up and down to the sounds of his moans as he fucked my soft lips. My hand cupping and rubbing his balls as his cock fully slid down my throat. His free hand rubbing my back and sliding under me, rubbing my tits and pulling on my nipples as we continued. Soon though he pulled my head off, his hard cock leaving my lips, I was a little disappointed, though a little excited thinking of what he was about to do next.

He got up, and moved around me rubbing my ass. I heard the 'click' of the bottle of lube being opened up. Next then I know he had one hand rubbing and spreading my ass as his lubed fingers began pumping in and out of my boi pussy as he fingered me, getting me ready. I moaned and squirmed feeling him working my tight hole open for him. "Do you like to be spanked?" he cooed, and I nodded to which he responded with a few quick spanks of my ass, which only heightened my pleasure.

After a few moments of him fingering me I was so ready for his cock, I wanted him to fuck me, I needed his cock in me. "Ooh yes, please fuck me, baby," I begged him. He must have agreed cause soon I felt his fingers leave my well lubed hole, and I heard him jerking the lube over his cock. Barely had I registered this than I felt that thick head pressing on my hole and in a moment it popped in. I moaned aloud as his thick hard cock filled me so deeply and perfectly. He grabbed mt his working his cock in and out of me at slow steady pace. I was in heaven. Here I was the man of my dreams balls deep in my boi pussy and giving me the fuck of my life. We grunted and moaned in unison as he thrust into me, and I wantonly pushed back into him. He would speed up, and slow down as he fucked me. I loved every second of it.

After several minutes of this, he pulled form me. His slick cock popping as it left me feeling an emptiness in me that begged to be filled. Then he grabbed, and flipped me onto my back. I looked up to him somewhat surprised, as he came over me lifting my legs up and back near my head as he once again sunk his cock into me. I moaned and panted in pleasure feeling him once again filling me and fucking me as his girl and lover. His hands soon pulled my bra down, discarding the inserts and leaving me with my natural B cup. His hot mouth descended on them sucking and pulling my hard nipples with his lips and teeth as his cock pounded me a bit harder and faster than before. I moaned, my body bouncing with his thrusts as he took me. His hands rubbed my stocking clad legs he loved so much as he pounded my boi pussy. In and out his hard rod pumped me. Our moans joined in unison as he claimed me as his own.

Just when I thought he was getting close, he once more withdrew from me, and flipped me back onto my knees. He grabbed my hips, pulling me back to the edge of the bed where we had begun. Once again his hot rod suck into me, filling me. Every hard thrust only making me want it more. He had me, I was his slut completely and totally. Harder and faster, he pounded me. The slap, slap, slap of our bodies filled the room. "Oh yes, fuck me baby, fuck me good." I moaned to him, face down in the sheets, and ass in the air being filled so well, so perfectly. I could hear his breath coming faster as we both panted. I could feel his cock swelling, his body bent over mine, hands grabbing and pulling my tits as he fucked me with such fervor. I moaned and panted, faster and harder. Then he pulled from me and moaned aloud as his cock erupted and spewed his seed into my gaping boi pussy and over my ass, covering me in his sweet, sticky goo.

I collapsed onto the sheets, ass thoroughly fucked and came on, catching my breath, His firm hands rubbing my back as I smiled in my stupor and bliss. All I could do was murr in contentment after having been so completely taken. He climbed up next to me, and held me a few moments, as I snuggled into him blissfully happy and content. His strong hands running through my hair as he kissed me softly. This was what I had wanted for so long.

After a little while though he had to go. He cleaned me off, and we got up, as I dressed lightly and showed him out. I waved as he drove off, and quietly and happily looked forward to our next meeting.

Adikon79
Adikon79
11 Followers
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AnonymousAnonymousover 1 year ago

Very nicely done... both the writing and the seduction. I jacked of to your story twice!

valuesvaluesover 9 years ago
hot! hot!hot!

you lucky boi, i,m hoping for a similar experience very soon!!

AnonymousAnonymousover 9 years ago
i can only hope i get that lucky

as a now 54 year closeted cross dresser , i would to meet a guy like jim .

RebeccaCherieRebeccaCherieover 9 years ago
OMG. MMMMmmmmm

Jim sounds so strong and masterful. :-)

I do like a' man that takes charge.

Rebecca

AnonymousAnonymousover 9 years ago
To die fire

Get a D-R-E-S-S

Get cock up your A-S-S!

Act all girly, try your luck!

Feel that rec-tum gettin' fucked!

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