Finding My Dream Wo(man)

I'm your run of the mill middle-aged white guy; divorced, decent job, plenty of hobbies, and your standard list of perversions. I love women. I love the way they smell, I love their bodies, I love their personalities, and I really love having sex with them. I've had a few bisexual encounters in my day, mostly back in college, and while I have no phobias about man-on-man action, I have never been attracted to the same sex. Although admittedly, the sight of a large, erect cock has always made my mouth water. I guess you could say I do have some bisexual tendencies.

I own a condo in a small complex just outside a large metropolitan city. My adventures into the world of chicks with dicks began when a new neighbor moved in across the hall from my unit. But I'm getting ahead of myself.

Getting home from work one night, I noticed the empty condo was no longer for sale; I'd soon have a new neighbor. I only hoped they would be less annoying than the family that moved out. Between the screaming kids and the arguing parents, I was hoping for a little peace and quiet.

Over the next few weeks, I caught sight of my new neighbor on occasion, but had yet to have the opportunity to introduce myself. My balcony overlooked the parking lot, and I'd seen her getting in and out of her SUV a few times. She was a strikingly cute redhead, tall, about 5'9" with long flowing hair, often pulled back in a ponytail. Her face was lightly freckled and she had the body of a tennis pro; long and lean, with pert little breasts, maybe B cups, well toned legs, and a perfect little round ass. I was guessing she was somewhere in her mid-thirties and looked to be doing well in life based on her nice car, expensive wardrobe, and ability to buy the large 3 bedroom condo in this upscale complex.

I'd only seen her either dressed for work in the morning or coming home after a workout. She usually wore a lycra sports bra that perfectly accentuated her fantastic figure, including a tight little tummy that had clearly been developed over years of ab exercises. She always wore a short tennis skirt that made her long legs look even longer, and oh so sexy.

I never saw anybody else go in or out of the condo, so I assumed she was single. As you can tell, I was in full stalk mode as I looked for the perfect opportunity to make my move.

On a Friday evening I was out on the balcony, enjoying a glass of wine after a long week at work when she pulled into the parking lot. She was dressed for a workout and I watched as she opened the tailgate of her SUV and struggled to extricate a large box, her little ass wiggling so invitingly. My cock stirred to life as nasty thoughts raged in my dirty mind.

Finally, my chance, "Excuse me Ms." I yelled down. "Do you need a hand with that?"

She straightened up and looked around, bewildered, as she blew a loose strand of hair from her adorable face. She bit her bottom lip and scrunched up her perfect little nose, trying to figure out where the offer was originating.

"Up here," I shouted. "Hi, I'm Scott, your neighbor. Can I help you with that big box?"

"Hi Scott," she replied. "I'm Carla. Thought you'd never introduce yourself. I don't mean to be a pain, but I'll never get this stuff upstairs without some help. Thanks for the offer."

"I'll be right down."

Channeling a world class sprinter, I made it to the parking lot in record time.

We shook hands and extended the normal courtesies before wrestling the big box out of the car. It appeared to be some workout equipment, the expensive kind you'd find in a nice gym. The close up view of her perfect little ass was almost too much to handle. This girl was indeed smoking hot.

"You starting a new gym?" I quipped.

"Not exactly," she giggled. I found her voice to be intoxicating, a deep husky tone that made my cock stir with anticipation.

"I love working out, but I hate the cheesey atmosphere at the local gym," she explained. "I've got the extra bedrooms here, so I thought I'd buy some equipment and setup my own home workout space."

"Great idea," I said. "Let's wrangle this bad boy upstairs. I'll even help you set it up if you like."

"Thanks Scott, you are quite the gentleman."

If she knew the dirty thoughts going through my mind, a gentleman is not the way she would have described me.

We spent the next hour putting the equipment together and getting to know each other a little better. She handled the tools like a pro and she was clearly in great physical shape as she had no problem lifting and holding the large steel tubing. I couldn't keep my eyes off her beautiful legs, only wishing her tennis skirt was a little more revealing. I got periodic shots of her tight little butt concealed in a pair of lycra boy shorts when the skirt got unintentionally hiked up, but only enough to peak my curiosity.

"I wish I had the extra space to setup some equipment like this," I commented. "I spend most of my workout time either running or swimming. I'm not a big fan of the gyms around here either. A bunch of roid heads hopped up on adrenaline as they try and grunt ridiculously heavy weights over their heads in some kind of tribal macho bullshit ritual."

"Exactly," Carla laughed. "But you look like you stay in pretty good shape," she quipped as she gave my bicep a squeeze; her touch sent a jolt of electricity straight to my groin. "Maybe you can use my home gym sometime...once I get it all outfitted?"

Bingo...just the invite I had hoped for. "That would be great." Although the kind of workout with Carla that I was envisioning had nothing to do with exercise equipment.

We were hitting it off really well, so I decided to keep the ball rolling.

"I've got an open bottle of wine next door, if you want to come over and join me for a drink?" I offered.

"Why don't you go grab it while I jump in the shower?" she replied. "I'll give you the full tour of my new place."

Damn, my fantasy of her asking me to join her in the shower was a no-go. Maybe I'd been watching too much porn lately.

As I grabbed the wine, I couldn't help wondering, how such a beautiful young woman could be single and available; I'd hit the lottery with her moving in right across the hall from me. It was like a dream come true. I couldn't afford to screw this up, so I decided to play it cool and let this opportunity play out slow; well, relatively slow. My cock was aching with excitement and I had to mentally check my libido as I headed back to Carla's.

I looked around Carla's place, sipping my wine, as she finished in the shower. She had some amazing art work, really expensive furnishings, and stunning style. This girl was sophisticated, cute, and friendly...the triple crown of hot chicks in my book.

"Where's my wine? I need a stiff drink," she giggled as she emerged from her bedroom, her hair still wet, wrapped in a big terry cloth robe.

I was ready to give her something stiff, but I bit my tongue and played it cool.

We sat on her couch and finished off the bottle of wine as the sun set outdoors. We had several things in common, both enjoying mountain biking, tennis, and going to sporting events. She was a foody and loved to cook (another perfect fit as I love to eat). Carla was a consultant for a prestigious firm in town, having just moved here from the Midwest to take a new promotion.

With a loud yawn, Carla announced, "Scott, thanks for all your help today. I think we can become really good friends. I don't have many close friends, partly because I have a bit of a secret. But I think if we are going to be friends, I need to be honest with you."

She stood up and walked over to one of her still packed moving boxes. She pulled a dvd from the box and gave it to me.

"I'll tell you my story, but first, I want you to watch this movie," she sighed. "I think I can trust you and we'll see if you can deal with my secret. Now skeedaddle you big sexy man, I've had a rough week and need to get some sleep."

She bent down and gave me a kiss on the cheek, pulling me up from the sofa and showing me to the door.

"If after watching the video, you want to know more, you're invited to dinner tomorrow night," she said. "And I'll answer all your questions then. And promise me, you'll keep my little secret. Goodnight."

"I promise," I replied. I mean, how bad could it be, right?

She gave me a big hug, her pert breasts feeling so good against my chest. As she pulled back, she looked me straight in the eyes and dove back in, grabbing the back of my head and pulling my face to hers. "Enjoy the film" she whispered before she gave me the sexiest, deepest, most unexpected kiss I've ever received. Her tongue was soft as velvet as she gently explored my mouth, holding the kiss for what seemed to be 30 seconds, although I wanted it to last much longer.

With a cute little bye-bye waive and a wink, she turned on her heels and disappeared behind her front door, leaving me dazed and confused, and wanting more.

As I walked across the hall, I wondered what had just happened. What secret could she have? Is she a convicted murderer? Did she have some mental disorder? Would any of that matter as I had already fallen head over heels for this beautiful woman.

I undressed, popped the dvd into the player, and settled into bed to see what this was all about.

The title popped up on the flatscreen, "Transvestite Surprises." Holy crap, it was a porno. Did Carla accidentily give me the wrong dvd? And why would she have a porn movie about trannies? And why was my cock starting to rise to attention?

I got my answers almost immediately. The credits were rolling, and up popped a picture of Carla, dressed like a dominatrix, in high heeled leather boots and a form fitting latex outfit, swinging a riding crop with a look of pure evil in her eyes. She looked younger, but there was no mistaking that it was her. The name under her picture read "Carlita Long" and there was no missing the huge bulge running down her inner thigh under the tight fitting black suit.

On the screen, she reached down and ran her long, skinny fingers down the length of her bulge, her milky white skin creating a stunning contrast against the jet black of the latex pants, and hissed toward the camera, "Have I got a surprise for you, bitch!"

The screen faded and other actors were introduced. I looked down and realized my sheets were tenting obscenely, my cock now rock hard, a wet spot forming on the thin cotton material as I was already leaking precum.

Damn, Carla did have a secret. And while I probably should have been disgusted, I was anything but.

Could that bulge really belong to Carla, or was she wearing some kind of strap-on? Regardless, she'd been in porn for some period of time and she appeared to be the star of this movie as the first scene was of her, in a dungeon, dressed in the rubber dominatrix outfit and looming over a man restrained across a wooden bench.

I won't bore you with the play-by-play of the scene, but let it suffice that when the man finally relented and begged her to let him suck her cock, she unzipped and presented one of the biggest fucking boners I've ever seen. And unless the special effects were created by the team from Star Wars, the cock was very much real. I'm no slouch in the package department, but her cock was considerably bigger than mine. Long and thick, with huge veins running the length, and a massive sagging sack of balls that could likely produce a volcanic eruption of epic proportions. Maybe the camera added a few inches, but regardless, this was one very, very impressive package.

She proceeded to fuck the man's face like a devil possessed, ultimately forcing her entire length down his throat till her balls were literally bouncing off his chin. The guy was obviously a pro, as it was one of the most impressive acts of deepthroat I had ever seen.

When she finally tired of fucking his throat, she pulled her spit covered rod from his tortured jaws and said, "Now bitch, I'm gonna take that cherry ass of yours."

The guy had a look of terror in his eyes, "Please, Mistress, please don't. You'll rip me in two."

"I hope so," she cackled with an evil laugh as she positioned herself behind the restrained man and lined up her huge pole with his hairy ass.

With no hesitation, she buried her thick rod up the man's ass as he screamed and pleaded her to stop. In no time at all, she was ball deep (again, obviously the bottom man was a real pro) and she started fucking him like a wild animal.

"You love that don't you you sissy whore?" she screamed.

"You are my pathetic little fuck-toy, aren't you bitch?" she continued.

"This is exactly what you wanted all along, isn't it cunt-boy? You wanted a big dicked she-male to take your ass and fuck you like a bitch in heat." Between strokes, she whipped his back and ass with her riding crop.

I couldn't take my eyes off the screen. My hand found my rock hard cock and I stroked myself slowly, using the precum to lube my piston. I went slow knowing that any faster would cause me to lose my load.

I had watched tranny porn before, but I'd never seen a she-male as beautiful and in total control as Carla (Carlita?). She was amazing and her stamina unbelievable. She fucked the poor bastard for a good 20 minutes before pulling her throbbing member from his wrecked ass.

"Where do you want my sweet load, little piggy?"

Not waiting for his answer, she moved back in front of the man, lined up her rocket with his face and gave it a few long strokes.

"Arghhhhhhh, I'm cumming," she groaned as she erupted all over the man's upturned face, literally coating his mug in ropes of thick, white, spooge. "Open your mouth, slut," she commanded. The look of pure ecstasy on Carla's face told me she either really got off on this, or she was a world class actress.

She jerked several spurts on his tongue then buried the big mushroom head back into his mouth "Suck out every last drop you little whore."

I couldn't take it any longer and with one final jerk, exploded all over my chest and stomach. I'd never watched a porn scene any hotter in my whole life. And the star of the scene was my next door neighbor, the same neighbor that gave me this movie to watch.

I skipped forward several scenes and watched Carla perform twice more; once with a woman and another scene where she dominated another man. She was completely nude in the scene with the hot little porn starlet, and if it weren't for the big cock between Carla's legs, you'd have thought she was the most beautiful porn star you've ever seen. Her body was perfect, her tits clearly natural, and in the scene with the other woman, she revealed her perfect little ass as she was strap-on fucked doggy-style by the girl.

By the time the movie ended, I'd cum twice more and my cock hurt from all the stroking. As I drifted off to sleep, I had no idea what my next move would be. I'd never imagined meeting, let alone thinking of getting romantically involved, with a transvestite. But I had some very vivid dreams that night, and all of them included Carla mounting me like a dog and fucking me into submission.

The next morning, I watched the dvd again (and again). The production date was ten years ago and I did some surfing on the internet to see how many other productions Carlita had starred in. It seemed she had been pretty active in the business for about four years and had made nearly 100 movies. Not all the movies were in the bdsm or dominatrix genre, but a huge majority were. I wondered if that was just type casting (a beautiful, innocent looking redhead with a big powerful weapon that could satisfy the guys that demanded this kind of porn) or whether Carla was really into this fetish. None of the porn industry sites knew what had happened to her in the last decade and it appeared she had simply retired and moved on.

As the appointed dinner date approached, I showered and headed to the store to buy a bottle of wine. I was going to need some booze in me to get through this night.

I knocked on Carla's door and she answered, dressed in a pretty blue summer dress, adorned with little yellow flowers. Her hair was down and she looked simply amazing. Her big green eyes sparkled with a sense of pure mystery. I could tell she was relieved that I had shown up for dinner.

"Glad you decided to keep our date," she giggled as she grabbed my hand and pulled me inside.

"I'm sure you've got a ton of questions, but let's open the wine and I'll finish preparing dinner. We can talk while I'm cooking."

As she calmly took the chicken out of the oven, she asked, "Well, what did you think of my little secret?"

"Definitely a secret, but it was anything but little," I tried to laugh. "So, Carlita is really you? Not just some doppleganger?"

"It's really me, baby," she replied. "Before I tell you my story, truthfully, did you watch the whole movie?"

"Yes."

"How many times did you jerk off?" she asked casually.

"I, uhhhh, I, well," I stuttered. "I honestly lost count."

"Good. Thanks for being honest. I saw the way you were checking me out yesterday, so I figured you'd either be disgusted beyond repair or would be curious as a cat."

"Definitely curious, Carla," I responded. "I've watched my share of porn, and that was some of the hottest stuff I've ever seen. You were beautiful, amazing, and more than a little shocking. I've never seen a porn star literally own scenes the way you do."

"Thanks sweetie. Trust me, I'm all woman, and I love getting compliments like any other girl. The only difference with me is I pack a punch between my legs."

"You can say that again," I chuckled. "So you are a transvestite?"

"I guess you can say that. I'm kinda an oddity in that department. My parents thought I was a boy and raised me like one. Can't blame them for thinking that given the plumbing I was born with."

"But I was always very feminine growing up. When I hit puberty, rather than growing hair on my chest, I started to grow boobies. My body took on the curves of a young woman. I was producing estrogen, so actually I'm more of a hermaphrodite. I always felt more like a woman, even if I did have a penis. So my family moved, I changed my name from Carl to Carla, and I started dressing like a girl. As long as folks didn't see the big swinging dick between my legs, I was accepted as a female."

"Wow, what a story," I exclaimed. "Must have been really hard."

"That is the toughest part, baby. It does get really hard," she giggled, pointing down towards her crotch. "I considered having surgery, but in the words of that beloved cartoon character, Popeye, I am what I am. Besides, my cock gives me great pleasure, as I'm sure you can understand."

"Totally," I blushed. "How did you get involved in the porn industry? And do you need a can of spinach to pop that incredible boner?"

"Very funny; glad to see you were a Popeye fan too," she replied. "My parents weren't rich, so I couldn't afford to go to college right away after graduating high school. I was still a virgin as I was scared to death of how to approach a boy, or girl, about my condition. I did some research, if you can call watching porn research, to see what other people like me did for sexual release. After watching some tranny porn, I contacted one of the producers, set up an interview, and the rest is, as they say, history."

"Wow, you became a real star in that genre, huh?"

"You could say I had all the right parts," Carla joked. "I had matured into a pretty good looking girl, and thanks to good genes, I was packing a substantial piece of meat. And I was always horny, so I had no problem "performing" as they say."

"Anyway, I made some good money for a few years, enough to pay for college and graduate school. I found a good job and have done a pretty decent job of assimilating back into normal society. Not that the porn world is necessarily abnormal, but fucking for a living is not the kind of thing you want to tell your kids."