Can I Be This Lucky?

Story Info
Guy comes across hot TS hooker in parking lot.
3.6k words
4.56
99.7k
42

Part 1 of the 2 part series

Updated 10/31/2022
Created 10/06/2009
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 had just broken up with my wife of 4 years. So I was definitely not feeling good about myself. My time in the Navy was just about up, & not a second too soon. Now that I was done with my wife, I had no reason to stick around here anyway. I decided to go check out a movie to get my mind off things. I had been mindlessly walking for the past 2 hours, so I wasn't really sure where I was at the moment. Taking a few minutes to get my bearings, I realized I was about 3 blocks from the movie theater on the base. I had no idea what was playing, I just needed to do something to get my mind off my soon to be ex wife.

I had to cross the parking lot of a large factory to head towards the movie theater. The lot & it's accompanying building looked like they hadn't been used in years. Ah well, this area is full of old abandoned factories anyway. As I made my way across the lot, I heard a honk behind me, & then a female voice. I turned around to see a very pretty girl in a black Eclipse, motioning for me to come over to her. She had long brown hair that came down around her face, big pretty brown eyes, full lips that were begging to be kissed, and her breasts were poking out of the low cut shirt she was wearing. She had on a lot of make up, but didn't look like she really needed. I assumed immediately she was a prostitute, thou I couldn't remember ever seeing one around here before. She was extremely hot for a prostitute, unless you assume they all look like Vivian from Pretty Woman. Where I grew up, there were plenty... & NONE looked remotely like Julia Roberts. This girl didn't look like Julia, but she definitely looked like she could be in movies. I walked slowly towards the car to find out what she wanted.

As I got closer, I could see she was a bit intimidated now. Being a 6'2 230lb black male, in very good shape, & generally wearing a scowl, I was used to this reaction from white girls around here. But she had called me over, so I wasn't sure if she had lost her nerve, or my facial expression had scared her. Being as pretty as she was, I figured I better brighten up my face before she took off. I at least needed to find out what she wanted. So I threw on a smile as best I could & then, while walking closer.

"Can I help you with something Miss?" I asked.

She smiled, licked her lips, & responded in a very sultry, sexy voice. "You look like you could probably help me with a lot!"

I had a smile from ear to ear at that point. I was very flattered, thou I knew for certain at that point she was a pro. No woman this hot would come on that strong, at least not in the middle of no where. Maybe at a bar, I suppose.

"Ok." I laughed. "What is it you'd like me to help you with?"

"Well," She stated. "I'm looking to make some money, & you look like you could use someone to put a smile on your face. I saw you walking along looking either mad or depressed. I couldn't tell which. Either way. I think I can help you." She winked.

Thinking about it, she was right, I could use some cheering up. Even if from a pro. Hell, why not. At least I know she wont come looking for me in a week wondering why I never called her after we fucked.

"You're probably right pretty lady. So, what are you offering, & how much?" Might as well get right to the gist of it. LOL.

"You like head?" She asked.

Dumb question. "Um, yea. I'd say so." I smirked.

"Yea, stupid question. Honestly, I'm new at this, but that's not the point. How about $40. And I leave you with a big smile on your face!" She winked again & licked her lips again.

I bet she could. "$40..." I thought about it. Not expensive, & I can definitely spare it. "Sounds like a good deal to me."

"I don't suppose you have a place we can go, do you?" She asked.

"Nope, sorry babe." I had to say. "I'm not from around here. I'm not stationed on this base. I had to come here for personal reasons, so no private place to take you."

I was staying in the room of an old friend for the weekend. Bringing some strange hooker back to his room to get head on his couch & then kick her out just didn't seem like a fun experience.

"I suppose I can take care of you here, in my car. Though it wont be very comfortable." She responded.

"That works for me." I lied. I'd much rather have had a comfortable spot, but who am I to bitch about the particulars of a cheap blow job from a smoking hot hooker.

I walked around the front of her car. It was a very nice car. Probably no more than a year or 2 old, shinning brightly, fresh, clean leather interior. I instantly figured it wasn't her car. It probably belonged to a guy she was sleeping with from one of the ships. Probably a dancer or a waitress at one of the local joints... Short on funds, needs money for gas, or something, & figured she'd give this a shot. At least, that's what is going through my mind. She could be a psycho killer about to drug me, cut me up into little pieces, & feed me to her dog or some crap. Ah well, the chances you take when you're young. LOL. As I got in, I saw she was wearing a very short skirt. Probably didn't cover much more than her asscheeks when she was standing. As I got in I must have looked apprehensive. She leaned over & touched my leg.

"Don't worry big boy. No funny business here. I'm just looking to make some quick cash." She winked again.

She pulled out of the parking lot & headed back towards a busy intersection. As we drove, she struck up short conversation. It was, in fact, her brother's car. He was in the Navy & deployed right now. She was home with her 2 kids, & was short on money. She wasn't a normal pro, thou she had done it on occasion to help ends meet. She knew guys found her attractive, so why beat around the bush. You want sex, I want money. Easy arrangement. She also admitted that she loved sex. So why not get paid for something she'd probably do for free. I couldn't argue with her logic, thou something was just fishy about the situation. I'm a firm believer that anything that seems to good to be true... IS! I told her about my situation with my soon to be ex-wife, & that I was here to handle a legal matter not involved with my wife. I was sueing a finance company & a car dealership, so I had to come up here to meet with my lawyer. I was staying the night in the room of a friend in the barracks, & had been on my way to the movie theater when she saw me. She seemed to pay attention to what I was saying. She was good at faking interest at least.

We pulled up behind a big apartment building, in the back near the dumpsters. She looked over at me with a smile & look that said she wasn't really sure of what the next move was. Maybe she was being straight up. I figured why not get the business portion out of the way, so I reached into my pocket & pulled out 2 $20 bills & handed them her. She took them, sort of reluctantly, thou it could totally have been an act. She then looked over at me with a wicked smile.

"Lay your seat back!"

"Ok." I did.

She reached over & grabbed my crotch. Oh yea, this chick has experience. She starts stroking my throbbing, stiff cock through my pants. She pulls my shirt up & starts tracing her tongue around my navel, as she begins undoing my pants. I lift my ass off the seat to let her pull my pants & boxers down. She pulls out a condom, opens it with her teeth, puts the tip in her mouth, & proceeds to fit the condom on my raging hard on with her hot mouth. I am a mix of nervous, scared, excited, & about has turned on as I had ever been in my life. This chick could have popped out fangs & tried to suck my blood & I wouldn't have been shocked at this point. She looked up at me a look so sultry & seductive, my heart skipped. Is this chick really trying to seduce me? She already has the money. What's the point? Maybe she was serious. She engulfed my full 7 inches in one motion. I could feel the head of my dick squeeze into her throat. She stayed there for min... Until I felt her tongue on my balls. Whoa... She can deep throat while licking balls. This girl has talent! She slowly starts pistoning her hand up & down on my throbbing cock as she sucked on the head & plays with my balls. This girl has extreme oral skills. I'm to the point of exploding in about 3 minutes. She then stops & looks up at me.

"You are really enjoying this aren't you!" She said, while smacking my cock against her face & lips.

"Hell yes! I can see how you can make money at this." I said nonchalantly.

The look on her face told me I kind of hurt her feelings, which was strange in a way, but it fit everything else about her. I'm starting to think this was more about her getting some dick than about the money. But why would a girl this hot be stressed over dick? She engulfs my cock again, snapping me back to the events at hand. I can feel her tongue on the underside of my cock as she is squeezing the base & cork-screwing her face up & down, fucking my dick with her mouth. Each time going all the way down till her chin is against my balls, then she goes back up. She takes my left hand & puts it on the back of her head. I hold her head & wrap my hand in her hair & start to lift my ass up off the seat, driving my dick into her mouth. I can hear a guttural groan, & then a choked moan of approval. So I continue fucking her face while holding the back of her head until I cant hold back anymore

"Ughhhahhhh... Oh.. Shit.. I'm cuuuuummmiiinnnnggggggg!!!!" as I explode inside the condom.

After I finshed convulsing.. She slowly licks my balls & looks up & me with a cat who just ate the canary smile. She pulls the condom off, rolls it up, opens the driver door, & then chucks it into the dumpster. After closing the door she immediately swallows my bare cock, covered in my lingering cum. She sucks it clean, & comes up licking her lips.

"Yummy!" she cooed. "I should have just sucked your bare cock. I knew your cum would taste good."

I am about as shocked as I think possible at this point. My dick, which has started to go limp inside the condom, was not stiffening up again, in her hand. She looks at it with a hungry smile.

"Think you're up for a bit more? I'd love to get your cock inside me. Sucking you off got me so fucking hot, I need a release. No extra charge... You're doing ME a favor!" She giggled.

I'm waiting to wake up in my own bed at this point. Having just cum all over myself in a mind-blowing wet dream. I get snapped back to the fact this is reality when she squeezed my balls with her left hand. Her right hand on my chest.

"Well?" she asked. "What do you think? Or would you prefer I drop you off at the movies?"

Tough question. Fuck this smoking hot chick, or get dropped off at a movie theater. "Yea, I think I'm up for another go!" I say happily.

She smiles sexily & then scoots back onto the driver seat. She reaches under her skirt & pulls down her panties, black & lacy. Damn.. sexy has hell. After handing me another condom, & getting ready while I put it on, she says, "Get behind me." She straddled the small center console & bends over between the seats. Her skirt slides up a bit & I can see her bare pink ass. So sexy & inviting. I rub the head of my cock up & down the crack of her ass. She reaches between her legs & rubs my cock, then lines me up with her hole, & I start to slid in. She moans out loudly when my head pushes inside, then I slowly slide in further & further. I pull all the way out, leaving just the head in, & then thrust in hard & fast. She is almost screaming every time I go in deep. I reach around & start playing with her nipples through her shirt... She yanks the shirt up, freeing her breasts. I lick the pointer & thumb of my left hand, & then reach around & squeeze her left nipple. I can feel her clamp down even tighter on my cock inside her. I rest my body on my elbows & am able to reach around with both hands & play with her nipples while I fuck her. She is moaning so loud & bucking so hard... I'm know she is faking it, but it's still a turn on... I pull back & relax, not sliding in, taking a break. She almost instantly jams her ass back against me, sending me right back balls deep into her. Then she leans forward & slams back again. She's moaning even louder now. I figure, if she's moaning this loud, what happens if I'm flicking her clit. I slide my left hand down her body to her flat stomach... But she grabs my hand sharply.

"I don't like fingers down there." She barks.

Wait. Something is odd about that. A thought starts forming in my head. I think I may know what the fuck is going on here now. I lean back a bit. Being in the condom, it is hard to tell, so I hold her waist away long enough for me to see it for sure. Yep, I'm in her ass. Holy shit. She cant be a... WTF? No way. She is still bouncing wildly on my cock while I am holding my weight on the seats. I am in a state of utter shock. This extremely sexy girl cant possible be a... guy. OK. One way to know for sure. I grab her hips & start pounding away hard into her.

She screams out. "Oh Yesssssss! Fuck me!!! Yes.. Oh please fuck me harder! YES!!! YES!!! YES!!!! Fuck me!!!"

I let me left hand slip off the seatback, sending me smashing against her soft, creamy body. As I do, I quickly shove my hand down her front & reach her pubs. I get my fingers stop when I feel the base of her cock. She quickly pulled my hand away.. At this point I am beyond disgusted. WTF??? How did I get into this.

Something weird is going on thou. Her squeezing tight bung, & the way she is grinding her ass back against me has my cock still rock hard. Shouldn't it have fallen like a wet noodle already. Fuck it, I might as well get this nut off. I start pounding her even harder than before. I'm fucking her as hard as I can... & she is loving it.

"Oh my god!!!! Yes.. Oh! Oh!! OH!!! YES!!! You fuck me so good!!!! Oh God yes!!!"

Is all I hear. The windows of the sports car are all fogged up. Her sceaming is almost piercing inside the small confines, & it's turning me on, despite my disgust at knowing she's a tranny. I finally feel the rising in my balls & know I'm going to cum..

"Shit.. I'm gonna cum!"

I flood the inside of the condom with my hot jizz. I slide out of her & fall over into the passenger seat. She lays there a second, then slides from between the seats & gets to her knees in the driver seat. She leans over pulls the condom off my softening cock. She then takes my dick in her mouth & gives it a solid licking. Cleaning all the remnants of my semen from it. She slides back into the drivers seat, opens the door, & chucks the condom into the trash. We sit there silent a few mins.

"That was so fucking good! I wish I could get more of that!" She said shyly.

My mind had been wandering for the entire silence. This was the sexiest chick I had ever seen in person. There was nothing masculine about her at all. She had soft supple breasts & nipples that stiffened when they got tweaked. She had just sucked a cock & gotten fucked hard, but she still smell fresh & sweet, like she'd just gotten out of a cucumber bath, like most women I knew did. She looks at my face & it finally dawns on her.

"You felt it didn't you?" she asked.

"Yes. I did." I answered quietly.

She got the same worried look on her face she did when I 1st walked up to her car. Now I got it. She didn't realize I was as big a guy as I was from a distance. She was worried what I might do to her if I found out the truth. For some reason, that was the final thing that put me at ease. She wasn't on some game to fuck over someone. She was horny & looking for some attention. It wasn't about the money at all. We sat silent for about 10 mins. She finally spoke up.

"You're not going to hit me are you?"

"Hit you? Of course not." I replied. The look of relief on her face actually made me smile. "I'm not that violent a guy. I was a bit weirded out at 1st. But, I'm thinking now, I agree with you... I wish I could have some more of that!"

The smile on her face was as bright as any I have ever seen. She spoke towards the steering wheel.

"Ok. Truth. I'm a pre-op transsexual. I've been on female hormones for years. I was home with my roommate & very horny, so decided to come out & try to get laid. I figured to come at someone as a hooker because then they wont try to get too intimate with me, just basically use me to get off. Which would at least get me off to."

I thought about what she said. It was basically what she told me at 1st, just changing the parts that would have made her suspicious.

"I can totally understand being horny. I actually wasn't. I was depressed when you picked me up. You definitely improved my mood." We laughed.

I pulled her over to me & hugged her. She wrapped her arms around my neck.

"So," she asked, "Want to come back to my place?"

"No kids there to get in the way?" I responded.

"No kids." she laughed. "Just my roommate. Though, she can act like a brat sometimes. Do you have anywhere you need to go tonight?"

"Nope, not at all." I shrugged. "As I said, I'm not from here. I was spending the night on my friends couch & going back to Florida in the morning."

"Well, I have a very comfy couch if you want. And an even more comfortable bed you are more than welcome to share with me. As long as you promise to let me take full advantage of your big cock while you're in it!" She stuck her tongue out at me when she said the last part.

"I suppose I can live with those terms. Your roommate isn't going to complain about your screaming is she? I asked. Figured it was a valid question.

"Complain?" She laughed. "Not hardly. She'll more than likely come & join us. We share everything we can. Most guys she meets are assholes about me, so she dumps them immediately. You being a straight guy willing to make love to me is going to turn her on insanely. I learned how to suck cock from her. She is a complete & utter freak. You are probably in for the night of your life!"

She smiled slyly after that last statement & then backed out of the parking spot. Apparently we were very close to her place. What the hell had I gotten myself into! I'm not sure but, but I cant wait to find out!

Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
5 Comments
Joscelyn2tgJoscelyn2tgalmost 10 years ago
Parts Of This Were Very Familiar...

...And the story was well written. I wish there was a little more background, actually where we come from is varied and all over the map, so to speak. A lot of us you would never know and work incredibly hard to hide in plain site... because we had to in order to stay alive, let alone safe. Of course she was scared, and written with just the right level of hidden paranoia that's always there. Thank you for a nice story, and you should write more... because you write well. Unfortunately Cheers! --- Josie.

Mr_OwlowMr_Owlowalmost 11 years ago
Good

This was hot! A few notes though; don't use texting language in flowing texts like this, write out first instead of 1st and so on. I would also reccomend using an editor from this site to give your story that final polish. Otherwise it was really good and hot!

LowendtheoryLowendtheoryover 14 years agoAuthor
Thanks

Thank for the comments & votes! Part 2 has been submitted, so should be up shortly. =)

AnonymousAnonymousover 14 years ago
So very sorry...

...I meant to give you 5 stars, but my my mouse has a mind of it's own sometimes. Hope to see part two soon.

AnonymousAnonymousover 14 years ago
HOT Trans sex

Great story... le tme know what happens at her place~~

Share this Story

READ MORE OF THIS SERIES

Similar Stories

Shemale Surprise A married man is seduced and taken by a friend of his wife's.in Transgender & Crossdressers
Shemale Sister-in-Law Man gets massage from sister-in-law with shocking results.in Transgender & Crossdressers
A Surprising Landlady A new tenant gets an unexpected but welcome surprise.in Transgender & Crossdressers
His Teacher, The Transsexual A young man ends up very close to a teacher with a secret.in Transgender & Crossdressers
My Ex Girlfriends Mom Randomly seeing an ex girlfriends mom can be a good thing!in Transgender & Crossdressers
More Stories