Fun with Chrissy

Story Info
A young man explores his fantasies.
2.9k words
4.58
58.7k
56
7
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

I know this is a bit short, compared to some of my other stories. There will definitely be more to it later on though, I assure you. I apologize for my lack of posts lately. I've just started a new job and it's been keeping me busy. I don't intend to stop writing anytime soon though.

*****

I can remember the first time that I stumbled upon trans porn. I was young and had found my fathers magazine collection, while he and my mother were out one night. After shifting through the pages for a few minutes, I came across an ad for a phone sex line in the back of the magazine. The woman in the advertisement, was absolutely beautiful, with short red hair and green eyes. Her breasts were not too big but her nipples were nice and perky and she had both of them pierced. As my eyes traveled further down though, I was surprised to find that this sexy red head happened to have a very big cock between her legs...I'm sure you can imagine how confused I was.

I wasn't just confused as to how a beautiful girl like her could have a penis; I was also stunned, at how turned on I was, just looking at the picture. I wound up putting the magazine away and trying to forget all about that sex ad on the last page. It's not like I could have called the number anyway, I was obviously too young at that point and I didn't know anything about using credit cards or stuff like that. It didn't stop me from exploring through the internet though.

All it took was a few minutes of searching Google, which was still quite young at that point. After typing in a few things in the search bar, I finally came across a site that catered specifically to beautiful girls that came with something a little extra; "shemales" as they liked to call them. I would later learn that the correct term however, was transsexual.

I can't tell you exactly how much time I spent as a teenager, looking at porn videos and pictures of these sexy women and their extra equipment; especially the videos. There were videos of girls with big dicks and girls with smaller dicks. Girls who liked to be fucked, and girls who liked to do the fucking...even those who loved doing it both ways. I found myself specifically attracted to the material with the more dominant ones. I found myself watching clips of guys getting rammed in the ass, by some of the most gorgeous girls that I had ever seen.

Throughout high school, I found that I wasn't really too interested in dating. It's not that I couldn't find a girl, believe me I could. The majority of my friends were actually girls and I'd had a few of them, try to flirt with me and even ask me out. I had only gone out on two dates, one with a friend of mine named Heather and the other girl was Erin. They were both very nice but obviously, it just didn't work out with either one of them.

Erin was a bit more pushy then Heather, and on our first and only date, I actually managed to get laid. It was a moment that should have been a very big deal for me, since I had just lost my virginity to one of the hottest chicks at school. For some reason though, I just really didn't get much out of the experience.

We broke up a couple of days later. I think Erin knew, that it wasn't going to work. She knew that it hadn't felt right that night that we'd slept together and I was quite thankful, that she didn't make a huge deal out of it, or hold it over my head. Instead, she ended up one of my best friends.

Deep down, I knew why I was struggling with girls. I was struggling with girls,

because none of them had that something extra, that I had grown to crave from all the porn I had been watching. There was no shame in what I felt, I would have gladly hooked up with a beautiful red head or brunette if they told me they were packing a bigger cock than me. There just wasn't anyone like that at my school, and so I was forced to push those feelings down deep and rely on the internet for relief.

It wouldn't stay that way forever, though.

When I finally got my chance, I was nineteen years old. I had been out of high school for a year at that point, and was working as a dishwasher at a restaurant in the City. The day of my 19th birthday, I decided to take that huge step and do what I had always wanted to do...meet an actual trans girl in person.

I found a girl on Craigslist...not the most reliable source, by the way. I spoke to a few different people, just to find that they seemed rather shady and I ended up cutting ties with them rather quickly. It took a few attempts, before I found

Chrissy.

Chrissy was a tall, beautiful blonde, standing at about 6'1" to be exact. Her long blonde hair stretched down to the middle of her back and those deep blue eyes, were absolutely mesmerizing.

Chrissy was an escort, who lived in Center City...not very far from where I was working. She advertised herself as being a very open minded person, who loved to help fulfill people's fantasies. She was versatile, meaning that she could be top or bottom but, she actually preferred to top. That was okay with me since it's honestly what I was looking for, mostly. I sent her a text message at the number she provided, and we started talking for a few minutes.

The conversation wasn't overly long, as I didn't want to annoy her and cause her to lose interest. I just told her what I was looking for and that I was a first timer...she had mentioned in the ad, that she was very good with first timers.

We set up a time and date to meet up; that exact day, actually. She didn't do outcalls, so I had to meet her at her apartment, if I wanted to go through with this.

I left work that night around 8:30 and sent Chrissy another text message, to let her know that I was on my way. She texted me back with her apartment number and told me to come right inside, when I arrived. When I got there, I stood outside of her apartment door for what felt like an eternity, trying desperately to work up the courage to walk inside. When I finally convinced myself to go through with it, I grabbed the door knob and pushed the door open before stepping into her apartment.

It was a small apartment, with just enough room for a couch and a recliner in the living room. I found Chrissy sitting in the recliner, wearing a bathrobe and smoking a cigarette. She looked up at me as I opened the door and smiled, flicking some of the ash from her cigarette, into the ashtray on her lamp table.

"You must be Ryan, right?"

Her voice was soft and soothing, a bit deep but quite alluring. I nodded my head in response, and Chrissy sat forward in her recliner. She took one final drag of her cigarette, blew the smoke out and crushed the cigarette in her ashtray.

Chrissy stood and crossed the threshold in my direction, stopping directly in front of me. Shaking, I reached for my wallet and pulled out the exact amount of money, that Chrissy had asked me for. She accepted it and counted it out, just to be sure it was the right amount. When she seemed satisfied, she looked back at me and smiled.

"So Ryan, now that you're here...what do you want?"

"I-I um..."

"You seem so nervous," she smiled. "Are you?"

I didn't have to answer that question. Chrissy knew, just by the look in my eyes, that I was beyond nervous; I was completely terrified. If anything though, that seemed to be a turn on for my beautiful blonde mistress. "There's nothing to be scared of Ryan, I told you I'm good with first timers...I won't bite you...unless you want me to, anyway."

I blushed and laughed a little, though it was an uneasy laugh. Chrissy moved closer to me now and I could smell the intense mixture of perfume and tobacco. She reached out and took my left hand in hers, pulling it into her shower robe and placing it over one of her breasts. "Don't you want me, baby?"

"God...y-yes," I stammered.

Her breasts were so soft and my cock immediately sprang to attention, as I started gently rubbing her nipples until they were nice and perky. She grabbed my hand again and moved it lower and I knew exactly where she was going to put it next. Within seconds, I was holding her cock in my hand; HER cock, not my own. This was the first time that I had ever touched another dick, besides my own and I had waited for a very long time to do so.

Chrissy then reached out and started trying to undo my belt, sliding her hand into my pants and wrapping her fingers around my hard dick. She stroked it for a few moments, before pulling my pants down to my ankles and releasing my seven inch cock from its prison. She stepped back then and removed her shower robe, allowing me to see her cock for the first time.

It wasn't actually the very first time. I had of course, seen a picture of it on her Craigslist ad but, seeing it in person was completely different.

She was clean shaven and circumcised, just as she stated in the ad. She looked to be about eight or nine inches and pretty thick. As Chrissy stepped towards me again, she grabbed my hand once more and returned it to her now fully erect cock, before taking hold of my own again. Now we were stroking each other and I was slowly starting to get a feel for the situation, although my anxieties had not completely disappeared just yet.

As we rubbed our cocks together, I could feel mine becoming slick with pre-cum. I looked down between us and saw that Chrissy was also dripping with pre-cum. It was such an arousing thing to see, I felt my heart starting to beat faster in my chest. I was starting to sweat and my breathing was becoming heavier. Chrissy smiled at me and that's when she leaned in, pressing her soft warm lips to mine, and slid her tongue into my mouth.

I groaned, kissing her back, still stroking each other as we kissed. We made out for nearly a whole minute before parting, and she smiled at me again. "Do you want to take this a little further? Or do you just want to keep jerking each other off?"

I cleared my throat, proud of myself for having gotten this far. Now it was time to push even further past my fears, and take this to another level. "C-Can I suck it?"

Chrissy gave me a sly grin, letting go of my cock and stepping back. She reached down and started stroking herself, with lust burning in her eyes. "Get down on your knees," she demanded.

I kicked my jeans off the rest of the way, then sank straight to my knees in front of Chrissy. She ran her soft hands through my hair and pressed the tip of her cock to my lips, just probing them for a few moments and rubbing against them.

She started rubbing her cock against my cheeks, slapping me in the face with it a couple of times; she was teasing me. I felt like such a slut at that moment, like one of the guys that I had watched in the hundreds of videos that I had seen on the internet. Eventually though, I decided that I'd had enough of the teasing.

I opened my mouth and swallowed all eight inches of her cock at once.

"Mmm, such an eager little boy," Chrissy groaned.

She was clearly impressed by my desire to suck her cock, and she watched as I bobbed my head. My lips slid up and down over her cock, my tongue flicking and licking the head of her shaft, before sliding all the way back down again. She would slip right into my throat and I would choke. My eyes filled with tears brought on by my gag reflex but, I pushed past it and continued trying to deep throat to the best of my ability.

I must have been doing a good job, because Chrissy was moaning and panting, pushing my head all the way down with both hands.

She kept pushing my head all the way down, lodging her cock deep in my throat, her heavy balls pressing against my chin. I groaned, reaching around and grabbing her ass with both hands. I gave each of her cheeks a nice squeeze, resulting in a few giggles and laughs from Chrissy.

"You're such a naughty boy," she said, seductively. "Do you want me to cum in your mouth, or on your face?"

That was actually, a very good question; I hadn't put a whole lot of thought into it until she had asked me. After contemplating my choices for a few moments, I decided that I wanted her to cum on my face. I freed her cock just long enough to give my response, before swallowing it whole once again.

Chrissy sighed, as she started to gyrate her hips, thrusting her dick in and out of my mouth. She was picking up the pace and thrusting harder and faster, becoming a bit more aggressive with me; I knew what that meant. I could tell by her heavy breathing and how much more aggressive she was becoming, that she was probably getting close now.

I wanted it so bad, that I reached up with one hand and started fondling her balls, gently massaging them in an attempt to bring on her orgasm faster.

I realized it had worked quite well, when Chrissy gave a sudden jerk of her body and a gasp. "F-Fuck," she groaned, as she pulled my head back and her cock slipped from between my lips. She reached down and grabbed her cock, slick with my saliva and started jerking furiously.

She threw her head back, gasping and panting, as she pumped her hand up and down her shaft. I closed my eyes, waiting for my reward. I jumped in surprise, when I felt the first shot of warm sperm, splash across my face. It covered my right eye; good thing I had closed both eyes, or I would have been temporarily blinded.

The second shot landed right on the bridge of my nose and ran down, into one of my nostrils. The next few ropes covered my whole face. I opened my mouth, a couple blasts landing right on my tongue and giving me a taste of her sweet cum. When it was over, I opened the one eye that I could and smiled up at her.

"You look like such a slut," Chrissy laughed.

"Did you enjoy it?"

I looked down at my hand at that moment, which had been stroking my own cock the whole time and it was drenched in my own cum. I had been so focused on sucking her dick that I hadn't even acknowledged my own orgasm until after it was over. It was crazy, that I could get myself off, just by sucking Chrissy's dick and having her cum all over my face.

"Yeah," I replied, happily. "It was...incredible."

"Let me go get you a towel."

After cleaning my face up, Chrissy invited me to sit down on the couch next to her and have a cigarette. I accepted the offer and we started talking a little. She had been living in Philly for two years now and moved here from New York City.

She had a very small group of clients but, she preferred to keep it that way...the less she had, the less drama was involved.

After talking for a few minutes, Chrissy asked if I wanted to try anything else; I did. I wanted her to bend me over and shove that beautiful cock, right into my virgin asshole. Unfortunately, she had failed to realize how low on time we actually were, until I told her what I wanted next. I couldn't believe that an entire hour had gone by, as quickly as it actually had. I had gotten so caught up in the moment that time had just slipped right by.

I cleaned up a bit more, and Chrissy walked me outside to the bus stop. It wasn't something that she did for most of her clients, unless they were in the middle of a good conversation. Apparently, she was enjoying our talk enough to walk me to the bus.

When the bus was about to pull up, Chrissy gave me a brief kiss on the cheek and smiled at me.

"Call me again, and we'll set up another date...next time, I'll gladly fuck that cute little butt of yours, if you're still feeling up for it."

I knew that I was definitely going to be up for it still. I promised to call Chrissy again, and got on the bus, looking out the window as she walked back to her apartment building. I smiled to myself, feeling satisfied with how things had turned out today. I already couldn't wait, to see Chrissy again.

Please rate this story
The author would appreciate your feedback.
Add Story To Favorites
Favorited by ajax_az, aaaaee, yosiq and 53 others
3.6k Followers
  • COMMENTS
7 Comments
AnonymousAnonymousover 4 years ago
dam

I wish I was you

Dar_JisboDar_Jisboabout 6 years ago
Another good Whiskey work

I like the fact that all your characters have a developed personality. (The sex is hot too, of course, but that's a secondary consideration.)

Looking forward to a part 2 of this story.

And congrats on your job.

FailedscoutFailedscoutabout 6 years ago
Well Done

Well done as usual. I almost always enjoy your work.

Thank you for writing and posting here.

CliterateDykeCliterateDykeabout 6 years ago

Hey Whiskey. I'm a femme domme dyke. Love your dtories, they're so damned sexy & sensual. You write well & have agood gift of capturing & expressing honest emotion via yoyr characters, who are so beautifully crafted & human. Thank you fir so many incredible hours of insight & pleasure.

Rwa4768Rwa4768about 6 years ago
More fun

This is something I have only fantasized about. I would love to read more about this topic.

Show More
Share this Story

Similar Stories

My New Trainer Workouts will never be quite the same.in Transgender & Crossdressers
"What Does She See in Him?" A high school boy finds the girl of his dreams is a bit more.in Transgender & Crossdressers
My Transgender Neighbor Mike falls for his blonde transgender neighbor, Caroline.in Transgender & Crossdressers
Shemale Step-Sister Teen boy spies on his shemale step-sister and gets a treat.in Transgender & Crossdressers
His Teacher, The Transsexual A young man ends up very close to a teacher with a secret.in Transgender & Crossdressers
More Stories