First Time

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First Time with a Sissy


“Well hello,” I said, as she strolled into my office & sat down, “I was starting to wonder if you were going to show or not.”

“You know I’d never pass up an opportunity with you honey,” she replied, coyly flashing that coquettish smile at me that I loved so much.

“Did you lock the door behind you??” I asked.

“Sure did, & yours is the only car left in the parking lot.”

“Good, well let’s get down to business then,” I said, rising from my chair.

******************

I had done well for myself over the course of my life, graduated valedictorian in high school, was a two time All American in football, graduated Suma Cum Laude from college, built a successful finance company from the ground up, but something was always missing. I had always been pretty good with the ladies too, having had my share of girlfriends & casual hookups along the way, but had never felt like I was in love. I threw myself head first into my career & that kept me occupied most of the time, but I still had all of this money & success & no one to share it with.

That was until I found Juliana & my entire life changed.

I was at the office one night, late, & I decided to take a break & surf around on the internet a little. I was browsing through some singles ads & I saw a banner for a TS dating website. I didn’t know much about transsexuals, but the woman on the banner was gorgeous so I clicked away. Her name was Juliana & she was drop dead gorgeous. She was 22, 5’7″ tall, 130lbs, & absolutely beautiful. She was totally shredded & the sight of her ripped, washboard abs instantly got me hard in my pants. She had long, shoulder length blonde hair, perfect D cup sized tits, & several sexy tattoos that made her jump right off the page.

But when I saw her rock-hard dick, it was then that I fell in love.

The first picture in her profile was at an angle from below, she was wearing a black, lace bra that was pulled down revealing her beautiful tits & a matching lace garter belt with no panties. Her cock was standing proudly out, erect, & ready for action. At that moment, I had no idea what came over me, but I wanted her cock in my mouth so bad that it started to water. I unzipped my pants, fished out my own hard cock, & started masturbating, right there in my office (good thing no one else was there).

I continued scrolling through her pictures, finding one of her holding her erect cock toward the camera, almost like she was offering it to me to suck, her lips pursed & waiting for contact from my tongue to make her feel good. Yet another had her in a white, camisole type teddy, her cock hard & throbbing beneath, waiting to escape from its prison. Yet another had her lying on her back, completely naked, legs spread, her hard prick standing at full mast, just waiting for me to come ride it.

I was furiously wanking my cock now, practically drooling on my keyboard as I felt my orgasm approach, when suddenly my cock erupted, spraying the contents of my balls all over the front of my pants & desk, covering everything in front of me as I shot, rope after rope of hot cum all over the place, making a complete mess. I fell back in my chair, panting & out of breath from my orgasm, cum everywhere, & my goddess, fully erect, displayed in front of me on my computer screen.

As I exited back to the main page of her profile, I noticed a green light indicator pop up that said “available”. Almost falling over myself to get to my phone, I called the number, hoping she would answer.

“Hello,” a sexy voice answered.

“Is this Juliana??” I stammered, both excited & nervous at the same time.

“Yes,” she replied, “Who is this??”

“My name is Max,” I said, struggling to find some additional words. “Are you available right now??”

“I am,” she replied, “My rate is $400/hr. If you are interested, I will Face Time you.”

My phone buzzed in with a Face Time request from Juliana’s number, I took a second to compose myself, fix my hair, & then answered.

“Well,” she said, “Aren’t you a cutie.”

“Thank you,” I replied, “You are absolutely gorgeous.”

“So, what do you have in mind honey??” she asked.

“I don’t really know,” I answered, slightly befuddled, “I saw your profile & I was scrolling through your pics & I…, uh,”

“Did you cum??” she asked, matter of factly.

I don’t know if it was from embarrassment or what but I didn’t really know what to say at that point. Forgetting that we were on a Face Time call, I assume that my flushed face or the cum on the front of my pants is what gave me away.

“It’s OK honey,” she said, reassuringly, “You’d be surprised how many times I get that same reaction. I’m at the Hilton on Parkway, room 412 if you want to come by.”

“I’ll be there in 10 minutes, “I said, hanging up & dashing out the door.

*****************

As I started to walk around to the front of my desk, Juliana rose to meet me. She was wearing a long, black, leather trench coat with matching leather, high heeled boots. She grabbed me, pulled me close to her as we embraced, and began kissing me, probing her tongue deep into my mouth. He hands were already busy, pulling on the buttons of my shirt & tugging on my belt, frantically trying to get my clothes off of me.

“I’ve been thinking about this all day,” she panted, breaking our kiss & ripping my shirt open, “I can’t wait to pound that tight little ass of yours!!”

Just hearing her talk like that always made my cock jump. I never would have guessed that I would love being topped by a gorgeous transsexual; however, two years after first stumbling across her profile online & then meeting her, that’s exactly what’s happened.

“Get on your knees,” she instructed me, taking a step back so she could unbutton her coat, “Now!!”

As I dropped to my knees in front of her, she peeled off her overcoat, revealing that gorgeous, toned body of hers. She had on a black lace bra & matching garter belt (just like the picture I fell in love with) with no panties on underneath. Her cock, which she must have been hiding tucked between her legs, was rock hard & sprang out to greet me.

God it was beautiful.

When fully erect it was about 8.5″ to 9″ long, about 2″ thick, uncircumcised, & completely shaved. She had large veins that throbbed when her blood was pumping & her big, hairless balls hung below like nectarines. She had a tattoo of Tinkerbelle on her left hip & one of a dream catcher on her inner left thigh, which was apropos, I thought, as that gorgeous piece of she-meat hanging between her legs was just like my dreams coming true. She peeled back her foreskin, revealing her pink glans, & stroked her length a few times, prompting it to reach its full size, before rubbing it against my lips, teasing me.

“You want this cock, don’t you??” she asked, looking down at me kneeling before her.

Yes, yes I did, more than anything I wanted Juliana’s cock in my mouth.

“Tell me,” she said, imploring me with her eyes, “Tell me you are my little cock slut.”

“I am your cock slut,” I replied, “Please let me suck your dick.”

With that, Juliana pushed the head of her cock past my lips & into my mouth, eliciting a moan from both of us as she did so. I began to service her, bobbing up & down on her length, sliding my tongue along the base of her engorged prick, sucking on her tip, & probing my tongue inside her cock slit searching for a taste of her juice.

“Oh God, yes,” she moaned, her cock buried in my mouth, “Take it all!!”

I felt her hands reach around to the back of my head & pull me forward, burying her root to the hilt in my throat, her balls coming to rest against my chin as I deepthroated her. After years of practice, I knew she loved this, holding my head in place, her erect penis sliding down my throat as she face fucked me. I could feel her veins start to throb as she pounded her rigid tool down my windpipe, & I knew she was close, about to reward me with her sticky goodness.

“Fuuuuuuccccccckkkkkk!!” she cried out as her cock exploded, blasting her load deep into my gullet & down into my stomach. She eased her cock back so that just the head was in my mouth as she continued to pump her hips & ejaculate, filling my mouth with her seed, feeding me her sperm that I needed & wanted so badly. She must have been really backed up because try as I might, I couldn’t swallow fast enough to keep up with her, causing some of her jizz to leak out the sides of my mouth. Noticing this, Juliana pulled her cock from my mouth with an audible “pop” & proceeded to paint my face with the sticky remnants of her load. Once she was spent, & I was completely coated, she fell back into the chair behind her, her cum dripping from my face.

“I never get tired of that,” she said, gasping for breath & stroking her semi erect cock, “Now, bend your ass over your desk so I can fuck you!!”

I did as I was told, dropped my pants around my ankles, & bent over for my goddess, ready for her to mount me & pound me with her gorgeous lady cock. I could feel her stalking up behind me, her eyes soaking up the sight of my naked ass bent over & ready for her.

“So nice,” she purred, as she began rubbing her cock in the crack of my ass, obviously enjoying seeing me like this, ready for her to breed me, to make me hers. I could feel her hard prick sliding between my cheeks, teasing me, as she grew back to full length.

“You want this, don’t you??” she asked, knowing full well the answer to her question as she continued to rub her hardening dick against me. “Tell me you want my cock in your ass, tell me you want me to fuck you.”

“Oh God yes,” I replied, “Please fuck me Juliana!!”

I was startled by a heavy handed “smack” on my ass, followed by Juliana chuckling, as she continued to slide her cock against my ass, teasing my hole.

“You’re such a little whore,” she teased, as she began to press her cockhead against my asshole, probing, seeking entrance. I relaxed my muscles, trying to accept her rock hard erection inside of me, wanting her to top me, to fuck me, to make me hers.

“Good boy,” she said, feeling me loosen to accept her as she continued to probe, sliding her tip just past my sphincter & popping into my ass. She slowly inched inside of me & held me there, my ass stretching to accommodate her girth, as my body accepted her cock & her dominance over me.

“I want to hear you,” she said, “Since no one is here, I want to hear you moan while I fuck you, understand??”

I knew one of Juliana’s biggest turn ons was hearing my moaning & me calling out her name while she fucked me. Truth be told, it really turned me on too, bottoming for her, having her be the dominant top while she fucked me.

With her right hand on my shoulder & her left hand on my waist, she slowly fed the rest of her cock into my ass, inch by inch, until she was hilted, buried balls deep inside of me. I never grew tired of this feeling, being so filled by her, about to be fucked, as she leaned against me, her breasts against my back, her breath, hot against my neck.

“You ready baby??” she asked, her voice husky with lust, “Are you ready for me to fuck you??”

I could feel every vein in her dick throbbing, blood pumping into her erection with anticipation, just waiting for me to say yes, to beg her to fuck me, so she could go to work, so she could fuck me like a wild animal.

“God yes,” I cried out, “Take me now, please fuck me baby!!”

I felt her hips recoil & her cock slide out of my ass all the way to the tip, just like a knight unsheathing his sword from its scabbard, before she thrust forward & buried it right back inside of me, her full length impaling me, gored on her massive erection.

“Arghhhhhh,” I moaned as she started to fuck me, her hips thrusting like a well-oiled piston, hammering her throbbing prick deeper & deeper into my insides.

“So good,” she panted, as she continued fucking me, driving her cock into my bowels, over & over, working herself into a frenzy. She reached her hand underneath me, finding my rigid cock, & started stroking me, pumping her hand up & down in rhythm with her thrusts.

“You like that, don’t you??” she asked, as she continued fucking me & stroking my cock, using it like a fuck handle to get deeper inside of me.

“God yes, I love it,” I cried out, my brain a mush of lust as Juliana continued reaming me, “I love you fucking me!!”

Suddenly she buried herself balls deep inside of me & held me there, stopping thrusting for a minute while she caught her breath.

“Turn over,” she barked, her cock hilted inside of me, “I want you to watch me fuck you.”

Making sure not to let her fat cock slip out of me for even a second, I threw my right leg up & over the side of my desk, Juliana guiding me past & supporting me so I didn’t fall, until I was flat on my back, my legs up in the air, Juliana’s cock still inside of me.

“Very good,” she mused, smiling down at me as she slid her hips forward, making sure she was sheathed fully in my ass, “you are becoming such a little bottom for my cock that you can’t even bear to have it out of you for one minute, can you??”

Truth be told, no. I wanted her cock in my mouth or in my ass at all times, it was almost all I thought about every waking moment.

“I can’t think of anything better than having you inside of me,” I replied, as Juliana started pumping me again, her balls slapping against my ass as she resumed fucking me.

She lifted my legs up onto her shoulders & pulled my hips toward her, burying her dick as far into my ass as it would reach. Without withdrawing, she began gyrating her hips, grinding her erection against my prostate & causing my own cock to begin leaking pre-cum all over my stomach.

“That’s so fucking hot,” she said, noticing the effect she was having on me, “There is nothing sexier than being able to make you cum without even touching your cock!!”

I was in heaven. I was flat on my back, my legs spread wide open, & my ass being filled with a gorgeous shemale cock. At that moment, I couldn’t think of any other place on Earth I’d rather be.

“Slide up,” Juliana commanded, breaking my moment of bliss, “I want to really mount you.”

I did as I was told & scooted up further on my desk. Juliana followed, climbing up on top of the desk onto her knees as she spread me open, leaning her weight against me. She leaned all the way forward, into a full missionary position, my legs spread around her waist, her gorgeous tits pressing against my chest, as she began kissing me, her tongue invading my mouth much like her cock was doing to my ass. As we passionately kissed, she began thrusting her hips again, sawing her massive tool in & out of my ass, fucking me harder & harder.

“God your ass is so good,” she panted into my mouth, “I could fuck you like this forever.”

“Please fuck me Juliana,” I replied, as I moaned out like a whore.

And fuck me she did.

With her full weight pressed against me, she began pumping for me for all she was worth. I could feel every inch of her rock-hard prick stretching my walls, bottoming out inside of me. With each thrust her cock probed & massaged against my prostate, causing my cock to twitch each time, rubbing back and forth as it was trapped between our bodies, grinding against Juliana’s washboard abs.

I felt my body relax & surrender completely to her as my legs collapsed, falling to my sides, out flat from my body. My head fell back against the desk & my eyes rolled back in my head, completely lost in pleasure as Juliana continued to breed me, pumping her erection into my ass over & over again. I could feel her heartbeat pulsing through the veins in her cock as she fucked me, edging closer & closer to her climax.

“You’re gonna make me cum,” she panted as she continued to thrust, “Where do you want my load??”

“Inside of me,” I replied, my brain a mush of lust, “Please cum inside of me.”

She continued pumping, pushing her throbbing cock as far into my ass as it would go, when I felt her erupt like a massive geyser inside of me, coating my bowels with her seed, painting my insides white with her warm, sticky nut.

“Fuuuuuuucccccccckkkkkkkkkk!!” she cried out, filling me with her semen, as she continued thrusting & ejaculating her sperm into my ass, breeding me like the little cum slut I was.

The friction from her firm, toned abs rubbing against my own dick as she fucked me caused me to blow my wad too, my cock popping off & shooting a load between our bodies, covering both of our stomachs in cum.

As Juliana’s orgasm subsided & her cock started to soften, she withdrew from my ass, & slowly slid off of me, leaving me lying on my desk with her cum still on my face, her load leaking from my ass, & my cum covering my stomach. I can only imagine what a well fucked mess I looked like.

“Same time next week honey??” she asked, putting her coat back on over her naked body.

“Absolutely,” I replied, “I can’t wait!!”

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