The Ad


I never thought I would find myself in a situation quite like this, yet here I am. On my hands and knees on a bed, ass sticking straight out, as a hot "girl" stood behind me slamming her huge cock in and out of me like no tomorrow. To you it probably seems like I'm not the type of guy who is into that sort of stuff, well you're right, I'm not like that at all, I am not gay in the least bit. Never even had a single thought in all twenty' four years of my life of being with another man, let alone a shemale. So you may be asking yourself, why then am I with a shemale right now in the first place, right? put it simply, I was curious...and I originally had no intentions of having her fuck me.

Really though, everything had been going according to plan, at first...I guess really, it was my own foolish fault. Let me start at the beginning just to make it so everyone understands the story better... sound good?

My name is Tyler White, I'm twenty four years old, I live in Philadelphia and I work as a kitchen assistant at a local bakery. My job is pretty simple, just cleaning dishes, crushing up boxes in a really cool machine, general cleaning and mopping the floors at night.

I've lived a relatively normal life. I was your typical "player" sort of guy, always with a new girl ever since my early teen years. I never, ever, had any trouble finding a girl or getting laid, but what I did have trouble doing was keeping the girls I would hook up with. I had never been in a serious long term relationship.

In fact I think the longest relationship I've ever had was about six months or so, before we broke up after she found out I slept with her best friend. Yeah, that was me, I had been that way for as long as I could remember. Hey though, it wasn't like I was proud of being that kind of person, really I was far from proud of it, at least anymore I was.

I had been seeing a girl named Sara for about eight months now; the six months relationship I mentioned was my longest relationship, before the one I just ended. In truth, I had been falling for Sara, slowly but surely without even realizing until things went a little sour. I got a little taste of my own medicine so to speak, when I caught her fucking a friend of mine in her bed.

That was two days ago, and to my own surprise I had actually been really depressed since it happened. She'd offered no excuse, not that any excuse she could offer would justify her actions, but it still made it hurt worse to know that she did not even feel any remorse. Now I guess I understood how all the girls I had done that to in the past had always felt.

It was a bit of an eye opener and had left me feeling ashamed of who I was and the things I had been doing since I was in freshmen year of high school; no more, I told myself. I was going to change, I was going to be a good man, find a beautiful woman and treat her right, marry her and have a family.

Maybe, not just yet though...

I woke up on a Thursday morning and had to get ready for work. I drug my feet the whole time that I was getting ready, taking a shower and putting on my uniform. I was still feeling pretty down and not looking forward to an eight hour shift at what I considered to be hell, but what could I do? So, I put on my fake smile, got ready and made my way to the bakery where I worked.

Even there though, I just kept dragging my feet, thinking about Sara, that mental image of her fucking my friend burned into my head. When my break rolled around at about 12:30, I stepped outside and lit up a cigarette, taking a deep drag off of it and blowing the smoke out. The door to the shop opened behind me and one of my co-workers, Larry stepped outside.

"What's up Tyler," he said. "Got a light dude," he asked, flashing a cigarette for me to see. I fished through my pockets and pulled out my Zippo lighter, flicking it open and lighting his smoke for him.

"What's up with you Tyler? You seem so bummed out; it's not like you."

I didn't exactly want to talk, but Larry was a cool dude and I wasn't about to be disrespectful to him or push him away. Plus, I couldn't act that way at work anyway, it would only make me look bad in the end."I caught my girl fucking some dude the other night,"

"Damn bro," he replied. "That really sucks."

"'s what I deserved I guess. I've done the same shit to so many girls over the years it's ridiculous. I guess you could just call it karma."

He gave me a pat on the back, taking a drag of his cigarette as I threw mine to the ground and stomped it out. "Well, cheer up buddy," he said trying to bring a smile to my face.

"Plenty of ladies out there on the fields...I'm sure you know that yourself though, since you were such a player before this girl."

"Yeah, but I don't know Larry. I mean, maybe I'm not meant to date."

"Nah, don't say that, everyone is meant for someone."

I wasn't so sure, I thought, as I leaned back against the wall behind me and looked up at the grey sky above, it looked like it was going to rain any second. I sighed, pushing away from the wall, and checking the time on my cell phone getting ready to head back into the bakery and end my break.

"Maybe you need to try something new," Larry suggested.

"New? Like new what? Not much of anything new about pussy to me Larry,"

He laughed, and for the first time I even cracked a slight smile, even though it was brought on by my own attempt at making a joke.

"Like, take a break from women."

"Larry...I don't know if you know this, but I'm not gay dude."

"Who says you have to be gay man? It's just for fun right? Listen, if you don't dig dudes, that's fine. But sometimes it's cool to step outside the boundaries and try new things, you know? Why not try with a tranny?"

"A tranny," I laughed. "Like chicks with dicks?"

"That's another word for them," he chuckled, putting out his cigarette on the wall.

"Check out Craigslist man, under the casual encounters ads give it a try. You'd be shocked to see some of them aren't half bad looking, I've seen a few who could really fool a guy until they drop their panties. And no one says you got to take it in the ass or anything, you'd be the one dishing out the fucking if you know what I mean."

I spent the rest of my shift considering what Larry had suggested maybe it was a good idea to try something new. At the same time though, the idea of hooking up with another man made me sick to the stomach. I was like I said earlier, far from gay. I had never entertained a single thought of homosexuality in my life, so how would I 'step outside the boundaries' if I wasn't interested in anything but women?

Being an eight hour shift, I got two breaks, so at 3:00 I went outside again and went onto the internet through my cell phone. I went straight to Craigslist and started scanning through the casual encounters section under "T4M" meaning transsexual for male.

Most of the ads on there had pictures, and though some of them did not show faces, the ones that did actually didn't look to bad. If you looked close enough at most of them you could tell they were not born women, but they still did look feminine enough for my eyes. I was having trouble getting past the idea of having sex with someone who had a dick like me, but I took into account what Larry had said; no one said anything about me sucking cock or getting fucked in the ass.

So what was the harm in any of it really, right?

I could find a "girl" set the meeting up, get my dick sucked and fuck them in the ass, and that would be that. Plus, I loved anal sex; so hooking up with a transsexual was the perfect excuse to have anal sex. I continued scanning the ads and finally found one that I liked, the description identifying them as a passable Cross dresser or Transsexual. I opened the ad, and was surprised to see a pretty attractive looking "girl" picture staring back at me on my screen.

Her name was apparently Lacey, she had blue eyes and red hair.

Twenty four year old passable cross dresser looking for someone to spend the night with. I am versatile, so I can fuck or be fucked or both, whatever you prefer. Give me a call if you think you're the one for me. Lacey,

The phone number was listed down below and I selected it and opened the options menu, clicking the "call" selection. I put the phone up to my ear and listened as it rang once...twice...three times, and then finally half-way through the fourth ring, I heard a soft click followed by a sweet and gentle voice coming from the other end.


I froze...was I really going through with this? Did I have the balls to do this...I knew she definitely had the balls.

"Hello," she repeated and I broke out of my trance, answering quickly before she would hang up thinking no one was on the other end.

"H-Hi," I stammered. " this Lacey?"

"Yes it is; whose calling?"

" name is Tyler, I'm responding to your Craigslist ad?"

"Oh, hey," she replied her voice changing to one of excitement.

"I'm really glad you called me; I'm really horny baby. You want to come over?"

It was now or never, I thought, pushing myself to give her the answer she was waiting for.

"I would love to," I answered. "I'm at work right now though...I get done at 5:00, so any time after that is good for me, how about you?"

I could not help the sudden feeling of anxiety and fear that I must sound like a total fucking douche bag or something...I shrugged it off, trying to keep my calm and continue this conversation to the end.

"Sure that's fine with me; what time can you be here?"

" about 6:30?"

"Sounds good," she said happily. "I'll text you my address, okay?"

We hung up and about a minute or two later I received a text message from her cell phone number with the address and a brief list of directions to get there. I sighed, my stomach in knots, stood up and went back inside the bakery to finish up my shift. 5:00 could not get here fast enough, When my day was finally over with, I made my way straight home in quite a rush to get cleaned up and get to Lacey's.

I was a nervous wreck, and a huge part of me could not even believe I was doing what I was about to do. I took a shot of Jack Daniels just to try and push down the worry; I convinced myself that this was no different than any of the other times I had fucked random people. Except this time, it was someone from Craigslist and it was a transsexual, this time, I'd be fucking someone with a dick, instead of a pussy.

A quick shower, something to eat, and then I was out the door again and making my way to Lacey's apartment. According to the directions in the text message, she lived somewhere on Cottman Ave., up closer to the Boulevard.

I knew there were shops up and down Cottman in the direction of the boulevard, and most of those shops all had apartments over top of them. So I assumed she probably lived in one of those studio apartments over top of some pizza shop, bar or any other place that I would drive past on the ave.

I followed the directions and within fifteen minutes I had arrived at the address, to find that I had been correct; Lacey lived over top of a pizza shop right by the Boulevard. I parked my car, walked up to the door and stood there for a few moments before getting the courage to continue.

There were two door bells, one for the top floor and one for the bottom...the text message said to ring the top bell. So I pushed it, and held it for a few seconds before letting go. A minute went by and nothing; than a few more seconds passed, and still nothing. I was beginning to feel anxious. Maybe I had held it too long and pissed her off. Maybe she got tired of waiting for me and went out.

Maybe she had been fucking with me, maybe it was a troll and she was just looking to lure horny men like me to her front door only to be met with no answers when they ring the door bell. Maybe, I should shut the hell up and stop worrying so damn much, I thought to myself.

Finally, I heard someone yelling from behind the door to hold on a second and a few moments later the lock clicked and the door swung open. There she was; the same face I had seen in the picture on the Craigslist add.


"Hey, you must be Tyler?"

"That's me," I laughed nervously.

"Well c'mon in cutie," she smiled pushing open the screen door for me. I stepped inside and she closed it behind us, before leading me up the wooden stairs to the top floor.

When we reached the top, I was surprised to find that she had a pretty nice apartment; like I figured, it was a studio apartment. The walls were painted a light blue, the floors were hardwood. There was a beautiful kitchen with a small card table sitting in the middle of it for eating. Down the hallway, I could see three doors; one probably for the bathroom, one probably a room-mates room, and the third I assumed was hers.

"So, make yourself at home," she spoke up breaking my train of thought. "You want a drink?"

"Uh...water is fine, thank you."

She filled up a glass and handed it to me. I took a sip and she motioned for me to sit down at the card table in the kitchen with her. We both took a seat across from one another and she smiled at me, noticing how nervous I looked.

"You're a first timer, aren't you," she asked.


"I can tell; you look absolutely terrified," she said, unable to help but laugh.

I chuckled, looking down at the glass of water and realizing how ridiculous I must look right now tapping my foot and drinking the water like I had never had a drink in my life.

"It's okay," she continued. "I'm good with first timers. So tell me Tyler, what is it that brought you to a girl like me? Are you an admirer?"


"You know; a guy' who takes interest strictly in transsexual women and cross dressers?"

", I uh, I'm totally new to all of this. Just sort of a spur of the moment,"

She seemed intrigued at that and she leaned back in her chair.

"So, how does a totally straight guy like yourself come about looking for a t-girl out of complete randomness if they're not an admirer?"

Here's where it got interesting; I decided to just be straight forward with her, since she looked like she would probably just laugh, and tell her it was my friend Larry's idea. I told her the whole thing, how depressed I was, how Larry suggested I try something new and how he had recommended hooking up with a shemale, and as I assumed Lacey found it funny and laughed.

"Okay then, you give a new definition to curiosity killed the cat,"

"Yeah? Yeah... I guess I do don't I? Sorry," I laughed.

"Don't be," Lacey said scooting forward in the chair.

"Your cute, and if you're the cat than I guess I'm a fan of cats. So what is it you want to do?"

I thought about that for a moment; I hoped that she wasn't going to be pissed off when I told her I was only interested in being a top, since her ad specified that she liked to do both. I was still turned off at the idea of sucking cock, or getting fucked in the ass, so there was no way any of that was going to happen.

"I'm just looking to be a top," I said as my nerves began to settle.

"Oh? Well that's a rarity; most guys who come to me want me to shove my cock up their ass and treat them like my bitch. But' I have to say, it's been quite some time since I got a good pounding I don't mind,"

There was something about the look she was giving me now, sitting across the table from me, smiling seductively...she had a look that made it seem like she wanted to pounce over the table and tackle me to the floor. Somehow, that look gave me a sudden rush of blood to my groin and I felt my cock begin to stiffen in my pants.

I was surprised that I was already so aroused, and we weren't even doing anything sexual yet; it was just that look in her eyes, it was just driving me crazy. She stood up finally, and instead of pouncing over the table like I thought she was going to do, she walked around the side of it slowly. She placed a finger on the card table and drug her hand over the surface as she stepped ever so slowly towards me.

She stopped right in front of me, and sat down slowly on my lap, draping her arms over my shoulders and leaning in close. Her eyes were lined up perfectly with my own, as were her lips, I could smell her scent. She was wearing perfume of some sort, and I found myself getting even more aroused by her sitting on my lap and the smell of her perfume.

She was intoxicating,

And then, it happened... before I could speak, or do anything myself, Lacey moved in and kissed me right on the lips. It was soft and gentle at first, but within seconds it was as if a fire had been ignited. I felt her tongue rubbing at my lips, requesting permission to enter, and as soon as I opened my lips and welcomed it inside we broke out into the most intense make out session I had ever encountered.

I pulled her closer to me, kissing her passionately, with my cock throbbing in my boxers as we went at it together.

Our lips parted, but our bodies did not; her mouth went right for my neck, biting, sucking and licking, leaving a rather large hickey in the place of her lips when she was done. From there, she almost literally ripped my shirt off and threw it to the wooden floor before planting her mouth on my chest and leaving a trail of soft wet kisses from my collar bone to my left nipple. She traced a circle around my nipple with her tongue, and I moaned, leaning my head back and running my hand through her hair as she sucked my nipple.

From there, she went for the other one, licking and biting it gently, before moving back up to my neck and then licking my earlobe. This girl was crazy, she was making ME crazy; I had never felt so hot in my fucking life.

As quickly as it had begun, it had come to an end, as she slid off my lap and onto her knees; the beginning of something even better was right in front of me. She smiled innocently up at me, her red locks of hair covering her face as she reached up to undo my zipper and button. She unzipped me, grabbed hold of the pant legs and tugged. I lifted my ass up off the chair to allow her to tug again, and she pulled my jeans along with my boxers down to my ankles. My raging hard cock sprang free immediately, standing at full attention and a tiny bead of cum was visible leaking from the tip already.

"Mm," she said as she began to stroke it softly.

"You're big and hard; I love it baby. I can't wait to feel it inside of my tight, little asshole."

Just the thought of me fucking her ass made my dick throb even more, as she continued stroking it slowly at first. I groaned, leaning my head back and waiting for her to give me more....her hand felt great, but I wanted something else. I wanted to feel her warm wet lips, the same wet lips that had kissed me all over a few minutes ago, wrapped around my cock sucking me dry.

She must have read my mind, and it wasn't long before I had gotten exactly what I wanted. She started out by teasing me with her tongue, licking the tip for a few seconds and then moved down to my balls.

She licked and sucked each one, one at a time, and I groaned at the incredible sensation. From there, she ran her tongue up the length of my seven inch cock to the head, swirling it around the head before finally swallowing me whole. She took my entire length all the way to the back of her mouth and immediately began bobbing her head in a perfect rhythm. I was in heaven, as she sucked and stroked and I was also amazed at how well she could deep throat me.

It wasn't so much my size, I didn't think at least, but most of the girls I had been with over the years had never been able to deep throat me. Not all that well anyway, the few who could were only as good at it as they wanted to be.

Lacey though...she was an absolute fucking expert at deep throat. This girl seemed to absolutely love sucking cock, and that was another trait that I admired and never before had I seen in a real girl. I had never met a girl who actually LIKED to give head; they always wanted you to eat their pussy, but when it came time to suck your cock they would only do it because they felt obligated.

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byWhiskeyIsGood© 20 comments/ 91006 views/ 102 favorites

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