tagTransgender & CrossdressersJacki's Journey into Sissyhood

Jacki's Journey into Sissyhood


I thought to myself could I really go through with it this time? I had to at least try it, didn't I? I took another swig of wine and then brushed the blonde strands of hair out of my face again as and I read through the message one more time. "Jacki, Id love to get together and treat you like the beautiful gurl that you are. Look over my pics and if you like what you see, send me your number and we can set up something, Steve." I sat there in a matching red lace bra and panties and black patent high heels, with my makeup, and my favorite blonde wig on, examining Steve's photos and offer. He certainly had a great body, for a man in his 50's he had a nice flat stomach, with broad shoulders and powerful arms, and just a dusting of dark hair across his chiseled chest. He was quite handsome in an all American guy sort of way, his short cropped hair was peppered with gray hair that continued to his well-manicured goatee. He was differently my type, the daddy/older guy type. I took one last drink of wine and thought to myself it's now or never, and entered in my number and hit send.

I guess I should explain how I got to this point. I had always considered myself a pretty normal guy, but I had a secret. When I had some time alone I loved to cross-dress. I started cross-dressing in college, primarily out of curiosity. I had become a fan of transsexual porn, so for me that kind of morphed into dressing myself. For me, cross-dressing was a sexual experience, I loved to post pictures of me en femme and have men salivate over my feminized body. I felt good to be viewed as a sexual object and be pursued as such. Not to mention how dressing in sexy, and sultry lingerie and women's clothes made me feel about my body. I considered myself straight, and I had many relationships with women, but when I was en femme I fantasized about being with a man. I was always was presented with offers by men to "make a woman out of me" but being too much of a chicken shit I never followed through with them.

Eventually I met a girl, who I thought was the love of my life, graduated, got married, bought a house with a two car garage, you know the American dream so to speak. I hid my fetish away, and really never thought about it anymore. Then one day I came home early to find my wife of 2 years in bed with both of her business partners. Turns out her little three-way was just one of many the group had been having over the past month, and only one of the 4 affairs she had in the past year. I thought I'd married the perfect girl, only to find out Id married the perfect slut. Oh well, water under the bridge.

After my divorce was final, I decided a new start was in order. I quit my job and headed for the west coast.

So there I was in my mid 20's, in a one bedroom apartment, in a new city where I knew virtually no one. It didn't take to long for me to fall back in love with my old perversion. Thanks to my new job and the boatload of money I was bringing home, in about two months I had a girly wardrobe that would rival my ex-wife's. I had procured makeup, several wigs, and even purchased a set of silicone breast forms to complete my look. To help fulfill my sexual desires, I had even begun experimenting with anal play, and had even started a sex toy collection.

I was always a smaller guy, and was fond of running, and yoga so I kept my body slim and in shape. I was short in stature, about 5'6" in shoes, 5'8-9" in heels. I now kept my body completely shaven except for the hair on my head.

The only hurdle I hadn't cleared was fulfilling my fantasies. That brings me to the present. I had made a promise to myself to ring in the New Year this year in style and explore my desires. So a couple of days before the New Year's Eve I posted an ad.

"26 year old crossdresser looking to ring in the New Year in style: My name is Jacki, and I looking for some manly company for New Year's Eve. I'd like to take my fantasies to the next level and want to be taken like a woman for the first time. "

I posted the ad with several pictures of myself in my lingerie and heels, and waited to see what turned up. As you might expect by the next day my mailbox was chock full of responses from men of all types and shapes. I set to work weeding through the numerous dick pics and childish one liners until I had about 5 men's messages singled out and replied to each. Steve was one of those guys. As it turned out Steve was the only of the 5 that lived in a reasonably close proximity, and was quiet attractive so he made the cut.

After hitting send on my computer, I let of a sigh of relief and finished my glass. I then got up and walked myself into the kitchen to pour me another glass. My cellphone lay on the counter as I began to fill it, when all of a sudden my phone began to vibrate.

As I looked down at the display, it was an unknown number, which I figured must be Steve. I swiped to answer then help the phone up to my ear and in my most seductive voice I said, "Hello."

"Hi, is this Jacki," a deep manly voice on the other end of the phone replied.

I answered back, "Yes this is, is this Steve."

"Yes it is darling," he stated.

"Wow, you work quick Steve. You must have been sitting by the computer waiting for my reply."

He laughed, "I was afraid if I didn't act quickly, some other lucky guy might get you first."

I giggled back, "No, Steve, you got dibbs."

We made small talk back in forth for a while, before I asked, "So, would you like to come over and spend New Year's Eve with me tomorrow night?"

"Absolutely, I'd love to," he asserted. "What time should I come by?"

"How about 10 or so, that will give us time to get acquainted before, we RING in the New Year," I giggled.

"You got it, I can't wait. Just text me your address later."

We said our goodbyes and I collapsed into my sofa in lustful excitement. I let my hands rub up my silky legs and then pat my ass. "Here, that ass. Tomorrow night you get your cherry popped."

I tried to fall asleep around 11, but couldn't sleep and I tossed and turned all night as images danced in my head.

The next day flew by, as I need to clean up the house, for company. Before I knew better it was 5 in the afternoon which signified the time for me to start my process. I had been periodically cleaning myself with enemas throughout the day, but I decided on one more before my bath. I filled the bag with lukewarm water and inserted the hose into anus and allowed the water to flow. I held a whole bag and half of another, before having to let it go. The water ran crystal clear signifying my rear was completely clean.

I had filled the tub with warm water and my favorite bubble bath, and set my radio to Katy Perry new cd and relaxed. As the music played and the warm water relaxed me I used my razor to clean up all the 2 day stubble from my body. When I was convinced I was clean and smooth, I exited the tub and toweled dry. Next came the application of the vanilla scented body lotion which I applied liberally to my skin. The lotion had a little glitter to it giving my smooth skin a girlish luster.

Setting down at my makeup table, I began sorting through brushes and powders and creams. Starting with primer, then foundation, and followed by blush. Next I curled my lashes, followed by eye shadow and mascara. Lastly came my candy pink lip gloss, I coated my lips and pouted them. I sat back to observe my work. Not bad I thought to myself, somewhere between slut and drag queen, just the look I wanted. I then opened my bottom drawer and retrieved my breast forms and body glue. I carefully applied glue to the back of the forms before slowly placing them on my chest. Once done a little concealer helped blend the edges in. The forms gave me a small D cup chest and really looked great, not to mention had a great feel and weight to them.

I then went to the closet and began sitting out my outfit. First came my black lace bustier. It was accented with small pink bows and the back featured pink satin ribbon enclosure. The bustier also had garters and a matching lace thong. The thong came first, then I shimmied the bustier up my torso putting my arms through the shoulder straps then tightening the satin ribbons to achieve the desired look. I then retrieved a pair of black sheer stockings from my hosiery drawer. Sliding the first silky stocking up my leg and fastening it caused my clitty to leak precum, causing my to have to stop and clean it up with tissue before it made a mess. Eventually I got the other stocking in place and the lace top attached to the garters of my bustier. For my shoes for the evening I selected my sparkly pink platform pumps from closet and slipped my feet into them. Lastly my blonde shoulder length wig, was settled into place and I brushed and teased the wig to life.

I stepped in front of my full length mirror to observe my work. Wow Jacki, you really outdid yourself tonight, I thought, as I stared back a young blonde bimbo. My false tits were pressed up nearly to my neck by the bustier and my bubble but look delicious in these heels. "Steve, is a lucky man tonight," I said to myself as I tossed my hair behind my shoulder with my hand. I the put on my black lace robe that covered my ass barely and tied the satin tie around my waste. I sat down at the makeup counter and affixed two gold hoops to my ears, buckled a rhinestone choker around my neck and added a couple of bracelets to each wrist.

I looked at the clock to check the time, it was 9:15. I checked my phone to see a new text. I opened it: "On the way sexy gurl, be there about 9:50." I smiled, and laughed. I loved being called sexy. I hopped up to leave my room before catching myself. "I almost forgot my most important piece of Jewelry."

I walked to my night stand where I kept my toy collection and fished out a bottle of lubricant and my glass butt plug with a pink crystal in the base. I crouched down on my heels and pulled my thong to the side exposing my hole. I then dabbed some lube on my fingers before massaging the liquid into my sissy pussy. Grabbing the plug by the base with the other hand I added another drizzle of lube to the tip of the plug. I placed the toy at my entrance and cooed as the cool glass touched my love canal entrance. I slowly applied pressure and the tip began to slide home. I gasped as the 1.5 in toy passed through my inner sphincter and set in place. I rearranged my thong and stood up. The cold glass created quite the sensation against my prostate, causing my clitty to throb and give off juice. I looked down and decided that I'd just place some tissue in my panties to minimize the mess until Steve got here.

I was finally ready and in just enough time to pregame a bit. I poured myself some wine as I danced in the kitchen to some music. Good thing I had remembered to close the blinds or the neighbors would have gotten a show. As I finished my first glass, I noticed lights outside. I peeked through the blinds to see a black SUV had pulled up outside. A large well-built man stepped out. I thought to myself, its show time. I turned off my music and waited for the knock.

Eventually there was a rap at the door. I shouted, "Just a minute," as I quickly straightened my outfit, and tossed my hair about. The clack of my heels on the hardwood followed me to the door. I reached to the door knob and opened it.

As the door swung opened it revealed a hunk of a man, in a grey suit jacket and pants, and navy blue dress shirt. He was extremely handsome, and the pictures didn't do him justice.

"Wow, you look incredible. Looks like I won the lottery," he said as he stood in the door way gawking.

"Oh stop," I retorted blushingly.

"You must be Steve, come in, ... come in, " I insisted motioning with my hand.

Steve stepped inside and wrapped his left arm around me in a hug, "Wow Jacki, I think you smell as lovely as you look darling."

He released me from his strong embrace and I shut the door, "Well I'm glad you're pleased with the product."

"You could easily pass for a woman, hell any guy would be lucky to be here."

I smiled back, "You are two kind."

Steve lifted his right arm displaying a bottle of wine and champagne. "I brought you a present," he said with a wolfish grin.

"Well you sure do know the way to a gurl's heart, or panties," I laughed.

We laughed and talked and drank like old friends. Steve was really easy to talk to. In fact his story was similar to mine, he was divorced 10 years, after he found his wife cheating on him as well. We talked about our lives and fantasies, and drank some more. Before long we had drained the bottle of wine he had brought and finished off one that I had as well. Any inhibitions that I had were now long gone.

We were having so much fun we almost missed the countdown. Steve quickly poured us a glass of champagne and handed me mine as the countdown started. We chanted in unison, "8, 7, 6, 5, 4, 3, 2, 1, Happy New Year."

I then felt Steve's hand on the small of my back and he quickly spun me around and planted a deep passionate kiss on my pink lips. I melted into his embrace and lustfully returned his kiss. We finally broke, "I'm sorry, I just couldn't take it anymore I had to kiss you," he apologized.

"No, No I'm glad you did," I assured him as I smiled back. I then initiated a kiss and this time it was quite a bit hotter. Our lips met and our tongues explored each other's mouths. Steve's hands began to explore my body and he began softly kneading my firm ass.

I finally pulled away and purred into Steve's ear, "I think I'm ready to take this to the bedroom, I'll go get it ready you stay here, I'll call you when I'm ready."

This time Steve didn't answer, he just nodded yes. I spun around and walked myself to the bedroom. I shut the door behind me, then lit the candles on my nightstands and my dresser. I then turned the radio over to some R&B music, or baby making music as I used to call it, and turned out the light. When I was satisfied I had set the mood, I opened the door and gave Steve my best "come here big boy", and watched him sprint to my door. I grabbed him by the hand and led him into my chambers. He then pulled me close as and kissed me again.

Our tongues pushed against each other's as Steve untied my robe and I lifted his shirt of his rock hard body. We broke our mouth to mouth lock long enough to release the garments and then we were back at it as Steve groped my now exposed butt flesh. I fondled the growing bulge in the front of Steve's pants before I finally couldn't take it anymore. I dropped to my knees in front of Steve, and seductively unbuckled his belt. I looked up into his eyes biting my lips as he stared down in lust. I buttoned his pants and let them fall to the floor, revealing a pair of black silk boxers. I then hooked my thumbs under the elastic of his waist band and forced them downwards. As the slid down his skin all of a sudden his hardening member sprung free nearly hitting me in the face. I gawked at it in all its manly glory. Steve's penis was at least 7 inches long at this point, and a good 2 inches thick with a perfectly shaped pink head. Accompanying the shaft might have been the biggest set of balls I'd ever seen, like golf ball big. This was the first time I'd seen a man's package up this close in all its glory, and it was beautiful. I glanced up at Steve in amazement. He laughed, "Go ahead baby he won't bite."

I raised my hand and caressed his silky shaft before grasping the shaft and slowly stroking his manhood. I was amazed how silky and soft it was as my hand moved back and forth over the stiffening rod. My mouth was beginning to water as I anticipated the first taste of cock. I stuck my lounge out as my hand guided the shaft towards its target. I flicked the tip tasting his salty precum, and felt his cock jump in my hand. I then swirled my tongue around his massive head as I had girls do to me as I heard Steve let out a moan. Finally to widened my lips and began inserting his dick into my mouth, before closing my lips securely around the head to savor the taste. It's hard to describe the taste, but it was like the first time I had a really good steak, I knew it was delicious and it definitely wouldn't be my last.

Next I began working his penis in and out of my warm wet mouth, and using my tongue to bath the underside of the shaft. I worked his rod in and out a few times, as Steve rocked back and forth, before removing his cock and licking the shaft and the head liberally. I then returned his now swollen tool to my moist hole and allowed Steve to slowly move his cock in and out as he pleased, as my tongue probed his piss slit. I worked my hand furiously jacking his exposed shaft as he drove his cock deeper and deeper with each thrust. Steve then placed his hand on the back of my head and drove cock ever deeper. With each invasion I concentrated on swallowing as much as I could. Before long Steve pushed his entire cock down my throat and held it there as my nose was buried into his neatly trimmed pubic mound. The sensation wasn't unpleasant as I thought it might be, as I calmly breathed through my nose.

Steve finally let me go and I removed my mouth from his sword. "Did I do good, Daddy," I giggled.

"Yes baby gurl, that was amazing," he answered as he pulled me to my feet. He kissed me deeply and lifted me to my feet, before sweeping my up in the muscular arms and laying me down on the bed. He then climbed on top of me lording over me as we kissed. Steve's hands explored my body. He caressed the silicone orbs on my chest playing with them like a real pair of breasts, with one hand; the other caressed my stocking clad legs up to my ass. After a bit his hand began to touch my clitty, before I stopped him. "No daddy, please don't play with my clitty. Treat me just like a girl tonight."

"Of course baby, I'll make you into a real woman tonight."

He kissed me once more on the lips before moving to my neck with his kisses. I moaned as he kissed me, and I stroked his now rock hard cock with my free hand. Steve slowly slid down my body with his kisses, before stopping and lifting my legs, and exposing my nubile ass. He softly kissing my smooth bottom as I grabbed my legs and pulling them into my chest. Steve pushed my thong to the side saying, "What do we have here," as he rotated and tugged at my glass ass stopper.

"That's your present daddy, I hope you like it," I cooed.

He replied, "That's sexy as hell baby girl."

Steve then firmly began to tug on the plugs base, as I moaned, "Oh, Daddy!!"

My anus could no longer hold the plus in and the plug came free with a loud "pop." My ass jumped as the glass stopper came free. Steve the inserted the plug bulb into his mouth tasting my ass as he moaned, "Um, baby girls hole is nice and fresh for Daddy. It tastes so good."

Steve sat the plug aside as he then turned his attention to my virgin bud. His tongue flicked at my opening lightly as my hole pulsed. I cooed as his wet tongue began to lap at my sissy pussy. My eyes rolled back into my head as Steve put his ass licking skills to work.

"Oh, yes that's it. Lick that pussy Daddy," I whimpered as Steve's tongue danced at my love hole. This was obviously not the first ass he had licked. As his wet tool assaulted my pussy, my clitty now had a stream of continuous fluid leaking from the head onto my lace covered stomach. I began to breath heavy and was nearly at the edge of climax just from the Steve's tongue.

I finally couldn't take it anymore and shouted in lust, "Fuck me daddy, please, give me your cock. Take me now!!"

Steve looked up from his work, with lust in his eyes. He was quickly to his knees and grabbed a pillow from the other side of the bed and inserted it under my hips lifting and exposing my ass. I then handed him a bottle of lube that he squirted a generous amount into his hand then some more into my ass. The slicked up his man meat with one hand and spread the lube into my pussy with the other.

Report Story

byjacki697© 3 comments/ 80159 views/ 49 favorites

Share the love

Report a Bug

2 Pages:12

Forgot your password?

Please wait

Change picture

Your current user avatar, all sizes:

Default size User Picture  Medium size User Picture  Small size User Picture  Tiny size User Picture

You have a new user avatar waiting for moderation.

Select new user avatar: