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chapter one of my up coming book  

jessicareign 40T
3 posts
8/8/2019 9:49 am
chapter one of my up coming book


I was excited, really excited, and if I was being honest a bit scared. It was a huge life altering decision, one I’d been saving for since I was old enough to work. And I was so ready to get started. I’d packed my bags and left my foster home morning, my eighteenth birthday. I was staying the night in a hotel after which I would board a train for the west coast. was where It began, where I’d become Jessica, start my transformation. But in truth my transformation began now. It started with the clothes and makeup I bout morning and with the reflection I saw in the mire. I’ve never been vain; I’ve never had cause but looking at myself all I could think was “Damn!”
I wore the classic schoolgirl uniform, not the costume you find in lingerie stores but something more like the real thing. A blue and grey plaid skirt hung halfway to my knees. A black corset with breast forms under a white short sleeved blouse. And black knee- socks with a pair of open toed flats. My hair was a dark red just long enough to be styled, I wore it down, so my bangs hung across one eye brushing down my cheek. My nails were a dark blue matched my skirt. The finished product was edgy and sexy without quite crossing the line into slutty.
The hardest part had been my makeup. There was no shortage of tutorial videos online, but they were only of so much . I supposed it was one of those skills took time and practice. It took me nearly three hours to get it right, I’d had to wash my face and start over several times before I was happy. And even then, I felt like I was settling for less.
But sill, looking at myself I couldn’t but think I was meant for this. I never made a good boy. I was too short, to skinny, my frame to small. My foster parents claimed puberty skipped me. It didn’t of course, It just wasn’t much of one.
The only thing marred the picture was the telling lump in my skirt, my erection. It wasn’t much, barely noticeable. I had a small dick, easy to hide when soft. But hard it was just over four inches, enough to stick out the top of my panties and form a vertical lump in my skirt. It was do to the thrill of it all, the smell of my perfume, the feel of my panties, my skirt against my thighs, it all served to excite. But it also felt right, true as if I were finally myself. I knew in time it would all be ordinary. Skirts and cute tops, dresses and sexy underwear, these things would simply be my clothes. But right then they were something else, something more, a forbidden fruit.
Closing my eye’s, I tried to push my thoughts away from my reflection. Not the truth of it, the girl in the mire was me and I her. It was the excitement I tried to push away. I wanted this to be normal, I didn’t want the fact of my clothes alone to make me hard.
Just breath, I told myself, breath and relax, but was easier said than done. I was too excited, too thrilled, I was finally becoming Jessica. I’d spent most of my life dreaming about this day. No small conservative town, no religious foster home. It was just me now, a boy who always wanted to be a girl, and was finally able to fallow his dream. No, I told myself, not his dreams but her. Never his or him again.
You need to get out, I told myself, out of the closet, out of this hotel room. So, taking a deep breath to calm my nerves I grabbed my room key and purse and headed out the door, it was time for Jessica to show her true face to the world.
The walk was exhilarating. My whole life I’ve had to watch how I walked, sat, moved, always careful not to be too feminine. It’s hard to go so completely against one’s nature but It was simple survival growing up with conservative foster parents. But now I was free, I could just be.
I made my way to a strip mall I’d seen on the bus ride in, just a couple blocks walk from my hotel. As it turned out the place had a pretty cool thrift shop. I bout myself a black sundress, two skirts and a couple cute tops. I also found a kickass pair of boots, black leather with straps up the backs buckled to the sides. I couldn’t believe my luck when they fit. I was only a size five and a half in men’s, small for a guy but still a little big for a girl.
But the best part of the place had been the cute guy at the register, I caught him checking me out. felt incredible, it was one thing to dress up but quite another to feel desired. I couldn’t myself, I smiled and gave him a little wink. The smile I got in return… well let’s just say weak knees. While I browsed, I spun a little fantasy wherein I took him back to my hotel and… and line of thought was making me hard again. I closed my eyes and took a deep breath. It was still tucked but it would pop out if I didn’t get my mind out of the gutter. For good measure I slung my purse in fount of me before checking out.
“Did you find everything ok” he’d asked.
“Yes” I said using my best girly voice, which was beyond passable. As I said before, I drew the short stick at puberty and my voice never really dropped, plus I’d been training my voice in secret for years.
“I like your outfit” he said.
“Tanks” I said blushing, my stomach suddenly fluttering with butterflies. Was he flirting?
“You make a hot girl, do you dress full time, take hormones?” he asked.
I froze, butterflies died, and my blush turned to one of embracement. Fuck, I thought, he knew, he’s probably been laughing behind his hands since I walked in.
“Because I wouldn’t have known” he said contradicting my thoughts, “I didn’t know until you came up to the register. If you’d been wearing a choker” he gestured toward my collar, “I’d have gone on thinking you were just some cute girl.”
My Addams apple, I thought touching my neck. “No” I said, “but I plan on starting soon. Hormones and dressing I mean. I’m leaving for California tomorrow, it’s a whole thing, becoming Jessica…” I trailed off realizing I was rambling.
“’s too bad” he said. “ your leaving I mean. We just met.”
Fuck he was flirting with me.
“You’re going to be hot you know. I mean you are hot but after a year or so of hormones, WoW”
“Thanks” I said grinning. Fuck I was blushing so hard, I had to of been beat red.
“So, Jessica” he said leaning in, his elbows on the counter, his grin turning sly, “Can I ask you a personal question?”
“Ok” I said a bit hesitantly.
“Sex” he said, “are you all girl? Or do you expect reciprocation?” he gestured down towards…
“No” I said quickly, “I prefer the guy ignore it, just pretend it’s not there.” And then for some unknown reason I added, “I actually prefer to from anal it’s just a better orgasm.”
He laughed, “So, you hands free?”
“Yes” I said, “but I still need a dick to ride.” I don’t know why I said it, the realization I did mortified me, it wasn’t even true, I was a virgin. I almost turned and ran from the store right then. But it was a good thing I didn’t because his next words…
“Is an invitation? Because I’m free after five.”
Was it? Holly shit things just got real. “Yes” I said before I had a chance to talk myself out of it, “if you’re really interested.”
“Yah, I’m interested” he said, “do you have a place?”
I gave him my hotel and room . Then after an awkward moment added “So, I’ll see you?”
“No later than five thirty” he said
“Ok, I’ll see you then.” I was grinning ear to ear; I could hardly believe it a cute guy just hit on me. I all most tripped leaving the store when he called after me, “did you know you have a great ass?”

Chapter 2

As good as his word he was at my door at a quarter after five and he didn’t waste any time. He grabbed me up into a kiss before I could even close the door, it was the first time I’d ever kissed a boy and I liked it. His lips were soft yet strong, commanding. His tongue reaching, hungry.
After swinging the door shut, he cupped my ass pulled me against him and picked me up. I wrapped my legs around him as he swung me around pushing me against the wall our lips never parting.
Time passed and he had me on the dresser kissing my neck, ear, lips, pulling off my panties. Our cocks hard, mine pushing up against my skirt, his pushing against me.
Then we were on the bed, my knees bent, legs spread open to him. His wait pressing down on me, our bodies grinding together.
He pulled back, standing so he could pull off his shirt. Fuck he had a great body. I sat up and undid his jeans belt, button, zipper. I pulled his pants and boxers down together. When his cock popped out it slapped against my cheek, I giggled. Then leaning forward and kiss it. It was beautiful, clean shaved, perhaps seven inches and thick. I’m going to have this inside of me, I thought, and goose bumps ran up my body making me quiver, I was so lucky.
I ran my tongue up and down his shaft, I pulled it back and bent my neck so I could kiss the tip, I kissed his balls opening my lips so I could pull them into my mouth. I ran my tongue back up and then finally I took him into my mouth. At first, I only wrapped my lips around the tip and caressed it with my tongue. But it didn’t take him long to push forward and slid deeper into my mouth. I started to bob my head with the motion of his hips as he pushed deeper and deeper until he was brushing the back of my throat. It was glorious!
He moaned looking down at me his fingers tangled in my hair, his trusts coming faster, pushing deeper. Until his hands were suddenly grasping the back of my head, his cock forcing its way down my thought. I was choking on it but didn’t care I could have died happy right then. I kept my tongue pressed against him and my lips tight while he throat fucked me. I took it until I couldn’t take it anymore, my motions almost involuntary when I push away from him letting his cock slide from my mouth. He only gave me time for a couple deep breaths before he was pulling me up, his mouth seeking mine.
He laid me back onto the bed, kicked his pants the rest of the way off and came down beside me. He pulled me into another kiss. His hand reaching between my legs. His fingers slick with saliva he slid them between my ass cheeks and ran them up and down then pressed against my hole. Slowly he pushed a finger inside of me. I whimpered; my cock somehow growing harder my ass pushing out wanting more. He moved his finger in small circles, my cock throbbed, my hips moving in time with his motions. Then he stuck in another finger starting to fuck me harder. And then a third.
“God your tight” he breathed his lips against my ear.
“I’m a virgin” I whispered back without thinking,
“I’ll be genital” he smiled
“No” I said, I wanted him to fuck me hard, I wanted all of him inside of me. But then again, “well, maybe at first”.
He laughed then kissed me fingers still inside of me.
I moaned pressing tighter against him my body moving with his. “Fuck, I want you inside of me” I breathed. “Pleases!”
I hadn’t realized I’d spoke aloud until he was repositioning. In fount of me he lifted my legs pushing my skirt up. I reached down with one hand guiding his cock as he pushed forward. The tip pressed against me, slowly entering me. My body wanted to pull a way, to close-up, but I wanted something else, I pushed against him, grabbed his hips and pulling him deeper. There was pain at first, but it was a good pain, one bordered on pleasure. Then the pain was gone, and pleasure was all, a complete feeling of fulfillment.
I moaned! He pulled back then pressed forward again and again the sway of his hips moving his cock in circles as he thrust it in and out of me. Each repetition took him a little deeper until finally he was all the way inside. His hips slammed against my ass as his cock filled me. I moaned begging for more, “Please harder, Fuck me, Harrrder!”
At some point he’d freed my legs and my feet were pressed into the bed, toes curled, knees bent I pressed against him my hips moving with his. My cock throbbed in time. I felt like I could at any moment. Then he slowed and rolled me over putting me on top. Magically his cock never left me, “fuck was he good.”
Stradling him I leaned back, hands on his knees, back arched I started working my hips riding his cock.
My cock was throbbing, so hard it was almost painful, the tip overflowing with precum so much it was dripping down the side. The slightest touch would be enough to make me explode.
He pulled me forward bent his knees up for leverage and pushed his cock deeper inside of me, his hips thrusting up me from below. He grabbed the back of my head and pulled me down into a deep kiss. My cock brushed his stomach, once, twice and then finally exploded spraying across his stomach and chest.
At the same moment he pressed forward, and his cock swelled deep inside of me and then released, It swelled again, released and then again.
I collapsed against his chest panting his cock still inside me. We lay there for several moments before he started to soften, and I couldn’t a small sigh of regret when his cock finally slipped out.
Afterwards I lay curled beside him my head on his stomach. He played with my hair while I traced my finger along his cock reaching forward to give it an occasional kiss.
“Were you really a virgin” he asked?
“Yes, I mean I have toys but you’re the first guy I’ve slept with.”
“No girls?”
“God no” I said! I’d kissed a girl once, but it felt weird and wrong. And I never had the erg to do it again.
“You know” I said, “I just realized I don’t know your name.”
“Tim” he said with a laugh.
“Tim” I whispered giving the name a caress, “do you think you’ll get hard again?”
“You need more’’ he asked his voice sly.
“Yes please” I said with mock shyness.
I kissed his stomach, then the inside of his thighs. I kissed the tip of his dick pulling it between my lips into my mouth, caressing it with my tongue. And…
And I always wanted to feel a cock get hard in my mouth, feel it respond to my touch.

…………………………………………………………………………………………………………………………………………….

It had been an incredible night; one I’d never forget. When Tim left morning, he’d kissed me and told me to come the store if I changed my mind and decided to stick around. He’d made several such comments night. things like, “it’s a shame your leaving I could get use to this.” I was tempted, he was hot, a great kisser and an incredible lover. But I had a plan and besides he probably wasn’t looking for anything serious just a booty call.
Though he had changed one part of my plan. I had intended to wear my boy close on the train. I didn’t even intend to start dressing full time once I got to California. I was going to start hormones right away but for the rest I’d planned to get settled first, a job and an apartment. But with Tim I had truly been myself and I couldn’t go back, couldn’t pretend to be a boy anymore. So morning I showered, did my makeup and my hair, I put on the black sun dress and leather boots I’d bought at the thrift store. And checked out of the hotel.
When I boarded the train afternoon I did so as Jessica, forever leaving Jessy behind. ’s not to say I wasn’t nerves; my gut was tied in knots. And on top of I was sore, my back, my ass, even my jaw ached. I hadn’t realized how much Tim had worn me out, not until he was gone, and the excitement of the night had started to fade. But the aches weren’t all bad, they brought back flashes of memory and gave me thoughts made me want to giggle. I was no longer a virgin, I kind of wanted to shout out. Sex with a man had been everything I’d imagined and more.

hungandoral2 65M/61F  
70 posts
8/8/2019 11:48 am

I would like to get to know this talented lady:Tom


jd428776 57M
67 posts
8/8/2019 11:52 am

LOVED reading this! Thank you for sharing! It was like I was there. What an experience! Can't wait to read the next story!


scott6250 62M

8/8/2019 12:10 pm

well done

"Sweet, steamy, sensuous kisses light the bright fires of passionate lust within us." scott6250


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