tagTranssexuals & CrossdressersWorking for a Living Ch. 05

Working for a Living Ch. 05

bycall_me_dana©

I pulled out of Chris' cabin just after six in the morning on a sunny July day headed for the beaches of Southern California. Chris had left two days earlier to visit an old neighbor from years ago but I knew what he was really doing. He had had a visit from Kelly, an 18-year old from Washington a couple months earlier. She spent the weekend with him I was certain they had fucked each other the entire time, but he never said a word. When I saw him later, Chris explained that he used to be close with her parents but had lost touch when they moved to Eastern Washington and split up. When he told me he was going to visit for a few days, I decided I needed to get away myself. I called up a friend from high school, actually an old girl friend from high school, and she told me to come for a stay.

I had gone to his cabin and spent the night in his bed. I fingered myself to orgasm two times between his sheets last night. I wanted him to smell my scent when he returned from his trip. With that in mind, I made the drive down the mountain to Idaho Falls on a crisp July morning. I pulled off the highway to get a venti coffee at Starbucks and my favorite apple fritter. It was still in the upper-40's when I crossed the road and pulled into the station to fill up the tank in my old Ford pick-up truck. I noticed her when I pulled into the station but didn't really give her a second thought. I slid out of the cab and once again felt the chilled air on my bare legs. I knew it would be blazing as I drove south through Utah so I dressed for the day, not the morning.

I stood, in skirt and jacket and hiking boots, shifting from one leg to the other as I pumped regular gas into my truck. I saw her moving from car to car, asking something and moving on to the next. I heard someone say something about Salt Lake City and she just moved on to the next car. She finally got to me and smiled while asking "Can I get a lift to Vegas?" She had slept-on blonde hair, a Levi jacket and jeans and she was pulling a large suitcase.

I turned away from the truck and smiled back at her. I'm not sure how I'd missed her large breasts previously but as she stood in front of me. They looked huge against her jacket. I quickly sized her up and didn't read 'psycho killer' in her appearance. I'm not big on giving strangers a ride, but I knew I would be on the road for eight hours or so with only my iPod for company. Besides, she had a really cute smile even if it looked like she had slept on a park bench.

I told her I wouldn't make Vegas until tomorrow and she gladly accepted. I think I was the only promising offer she'd had that morning. I helped her throw her suitcase into the bed of my pick-up and finished filling my truck. I told her I didn't have a/c in my truck so it would get pretty warm in a couple hours and she'd have to listen to the country music on my iPod being played through the truck speakers. None of this seemed to matter. I pulled my jacket off and pushed it behind the bench seat as I slid back into the truck. I was wearing a tank-top with a long-sleeve shirt over it. Out of the corner of my eye, I could see her sizing me up as she fiddled with the lap belt.

When she wiggled out of her jacket as the heat from the motor kicked into the cab, it became very obvious how well-endowed she really was. Her breasts strained against the t-shirt she was wearing. I told her I was Jaime and heading to see some friends in Southern California. She told me her name was Debbie and she was from a small town in Montana. A friend from home told her she could get a job dancing in Vegas and make big money. I quickly surmised the type of dancing.

We headed south on Interstate 15 through the potato farm country of Southeast Idaho with Debbie chattering away at everything and anything. It was like she had been bottled up and suddenly found an ear. Whenever I wondered why I had offered her a ride, I'd sneak a glance across the bench seat at her shapely legs and huge breasts. It was coming up on 11a and half-way to Salt Lake City when the sunshine really started getting warm. We had long since turned off the heater and opened the windows for an attempt at cool air. There is plenty of wide-open spaces on this part of the road with not many stops. "Hey Jaime? Do you think you could pull over so I could put some shorts on?" I knew she had to be getting hot wearing those jeans and I knew I'd be able to check out her legs.

I found a spot that had a bit of a shoulder and I eased the truck off the highway. Debbie hopped out of the cab and I could see her standing on the bumper and reaching into the bed to get at her suitcase. My eyes bugged out as her huge breasts hung down with gravity. I pulled off my long-sleeve shirt while I waited for her. She jumped down and opened the door. She was gonna change on the side of the road! "Don't peek and watch for cars, k?" Debbie turned away and leaned against the seat as she unzipped her jeans. She pulled them down, bending over enough for me to see she was just wearing a thong! For having such large breasts, she really was quite thin and shapely. I stared at her lower back and cheeks until she pulled the shorts over her hips. She just rolled up her jeans and stuffed them on the floorboard. As she climbed back in the cab, I had to admire her tanned legs. Her shorts really were short!

"That's much better! I think it's gonna get real hot today!" I was thinking the same thing when I realized my cock was getting stiff in the boyshorts I had on under my skirt. I hadn't really 'tucked' myself away in the morning as I hadn't expected any excitement on the drive. I was beginning to feel a bit uncomfortable as my thoughts lingered on Debbie and her body. "You okay?" Her question snapped me out of it for the moment as I put the truck in drive and accelerated back on the highway.

A few minutes down the road, Debbie asked "So tell me about this guy you're all pissed off at?" I thought about it a minute then launched into how we met on that cold winter day while I was working on his cabin. As I told the story, I could feel myself becoming aroused thinking about Chris and the wild sex we had shared. I tried to casually smooth my skirt and shift on the seat but I could do nothing about my nipples hardening and pressing through my bra. As I spoke, Debbie had turned her body slightly towards me and lifting her left thigh onto the seat. Her short shorts were barely covering her sex. Sneaking a peek in her direction as I talked, I could see her nipples were also pressing through her t-shirt.

I was totally unprepared when she unhooked her seat belt and slid into the center seat. She put her hand on my bare thigh as I gripped the wheel with both hands and tried to focus on the road. "It sounds like Chris is a great fuck!" as her hand slid to the inside of my thigh. My cock was fully erect now and straining against my shorts. I couldn't even look into my lap but could only imagine it tenting my skirt. Debbie leaned over and tongued my ear. As she did, I felt her hand cup my balls. She jerked her hand free and screamed "Are you a guy? I've heard about drag queens ... are you one of them?"

I didn't know whether to pull over or keep driving, so I just kept driving. "Debbie ... listen to me. I'm not a guy." I looked at her and her face was kind of blank. "I'm a woman but I still have a cock." She didn't move away but she didn't put her hand back on me either. "And I've got to tell you that you are making me crazy with your body!"

Debbie finally focused enough to say, "I've never seen anyone like you before. I'm shocked." Before I could say anything else, she asked "Does it work?"

I smiled for the first time in 15 minutes. "Oh yes, it works very well!"

Debbie put her hand back on my inner thigh and moved it tentatively back up to my cock. I'd gone a bit soft in the interim but I jumped when she touched me. Her hand caressed my cock under my skirt. She rubbed me through my boyshorts creating quite the sensation for my body. She had me hard again in just a few moments. Again, I struggled to concentrate on the road. My heart skipped when she pulled her hand free and I saw her sliding across the seat towards the door. "My last boyfriend always said I was great a giving head!" And with that she lay down on the seat and put her head in my lap. I looked down and only could see her dirty-blonde hair lying all around my crotch. She had lifted my skirt and pulled down my shorts to allow access to my cock.

Her lips slipped around the head. I was already leaking like a crazy woman just thinking about her. Her lips opened wide and she quickly slid down my shaft. I was taking deep breaths as I did my best to maintain composure for driving. I have gone down on a couple guys while they were driving and it never occurred to me how hard it was for them to keep us safe. We were doing 65 on the highway. I could feel Debbie inhale as she deep-throated my cock. The added suction seemed to press on my cock from all sides. She would slide up my cock with her teeth stopping under my rim. I could feel her tongue probing my peehole before she would slide back down my cock. My breathing was getting ragged as she was getting me close. I looked down a couple times and realized I had slowed to 55 as my foot would lift off the accelerator.

Debbie made a few fast strokes up and down my cock and the change in rhythm did it for me. I held her head with one hand as my cock shot a stream of cum down her throat. I could hear her gagging to swallow as a second stream followed. Finally I released her and she pulled her mouth free of my cock. Just ahead was a Ranch exit and I took it. Ranch exits are just what they sound like - no real roads, just access to a faraway ranch. At the bottom of the ramp, I slammed on the brakes to get my breathing back in sync. Debbie sat up and smiled at me as she pressed her lips to mine. I could taste the residuals of my semen on her tongue. "Your last boyfriend was right!"

#

By the time we reached central Utah, the mid-afternoon temperature was nearing 100 and it was boiling in the cab of my truck. We had pulled through a drive-thru for lunch and were each finishing the last of our two Cokes. "My plan had been to drive to Cedar City tonight but how about we stop early and find a room with air for the night?"

Debbie spread her legs a little bit and I could see her fingers dancing on her sweaty, bare skin. "That's okay with me if you don't mind me getting out of these sweaty clothes!" It was obvious we were both wanting more than that fantastic blow job in the cab.

I pulled off and found a small chain hotel that looked clean and had a pool outside. I went into the office and got us a room for the night. The smooth-faced kid at the desk kept staring at my breasts through my sweaty tank. I teased him a little as he fumbled to give me the room key. I swayed my ass I left the desk as I knew he'd be staring and probably go jerk off after I'd left. I knew he was no more than 18 or 19 and mine were probably the best tits he'd seen in his life, or at least in the last month!

It was an average sized room with a king-sized bed and the a/c was already set to medium. Debbie walked straight over to it and turned it to high. The cold air blasted out of it. I checked to make sure the curtains were closed tightly and when I turned around, Debbie had already pulling off her t-shirt and was unfastening her bra. She turned around and I had my first vision of 40DD breasts. They sat high on her chest with just a hint of sag. Her nipples were the size of nickels and I couldn't wait to touch them. We were both sweaty and I'm sure just a little smelly but neither of us cared at that moment. When I got close enough, Debbie pulled my tank over my head and quickly removed my bra. My 36C's with their perfect shape looked small as I stood next to her. I could tell she was admiring my well-toned, muscled body - the result of long hours of construction work. I bent down and pressed my lips to her left nipple as my hands felt her up. They felt even bigger than I had imagined all day in the truck.

I lifted my face and pressed my lips to hers. We embraced tightly, our sweaty bodies now chilled by the cold air blasting on us and kissed each other hard. We worked our way to the bed and pulled the covers down to the foot. I fell backwards onto the cool sheets. Debbie slipped out of the short shorts and crawled on top of me wearing only her thong. My cock was once again rock hard and I felt her press her sex over me as we kissed. She began to slide down my body and stopped at my tits. Her mouth sucked first the left, then the right nipple deeply past her lips. Once again, the suction she created was electric on my body. Her body kissed down the center of my belly and she was soon to my skirt. I lifted my hips and Debbie slid my skirt down my thighs. My cock was dripping precum inside my boyshorts.

Debbie kissed my cock through the sheer material causing me to jump as she did. She lifted the waistband and slid them over my cock. When I lifted my hips, she took them down my thighs as well. Debbie moved just long enough to push my skirt and shorts off my legs. I was now nude and lying under this sexy woman I'd picked up at a gas station mere hours before. She smiled at the small triangular-shaped patch of pubes just above the base of my cock. Debbie crawled between my legs and grabbed my cock by the base. Her tongue swizzled around the tip as her eyes looked up at me. The sexuality and the cold had my nipples so hard it was almost painful. My fingers pulled and pinched them in anticipation of her taking my cock in her mouth once again. Debbie's tongue coated my crown as her hand stroked my shaft. Her left hand began to playfully tug at my sac. Her lips opened and slid around the crown of my cock. I felt her warm mouth cover my cock and I sighed at the way my body would soon feel.

Debbie's mouth took my entire cock into her mouth and she again inhaled. It was like all the air left her mouth and their was pressure on my cock. It felt like nothing I had ever felt. Her mouth began to fuck up and down on my cock. Her saliva coated my cock as she rode me with her mouth. I was beginning to feel my orgasm rise but when she popped a finger inside my asshole, I creamed like I had never cum before! I shot a thick, warm stream into her mouth as she finger-fucked my asshole and sucked on my cock. She continued to ride my cock and soon my cum was spilling out of her lips and running down my cock. She had me a fucking mess, both with cum all over me and my head reeling from the sensation. Finally I had to shove her away as my cock was so sensitive to any more of her touch.

We lay side-by-side panting from the oral fucking she had just given me for nearly fifteen minutes. Finally I felt Debbie moving around as she slid her thong over her hips. I moved down her body and got between her sexy thighs. She was smooth except for a couple days of stubble from the road. I extended my tongue and split her pussy lips open. I could taste the muskiness from sweating in the car and it turned me on further. I wanted to eat her and then I wanted to fuck her and I knew I had all night to do it! My tongue moved over her clit and I raked it back and forth. Debbie cried out when I touched it the first time and I was quickly hoping we didn't have anyone in the adjoining rooms! My tongue stroked back and forth as I brought three fingers to her pussy. I pressed them inside her as she opened to take me. I tasted her sex when I withdrew them - the pungent taste of sex. I pressed my face hard to her body as my tongue slashed back and forth across her clit. The three fingers plunged faster in and out of her juicy pussy. Debbie was crying out in whimpers and squeals as I ravished her sex. Finally her body could hold out no longer and she shook from side to side as her orgasm rocked her world. I continued to stroke her clit as her pussy flooded with her juices. "No more. No more. No MORE!" she screamed at me. "I can't take anymore of your tongue!"

I was only half-erect, I just hadn't had enough time to recover considering I'd cum four times in less than a day. But I pulled myself over her body, bringing the sheets with me as I did. My semi-erect cock pressed against her flooded pussy and we lay together. I delighted in feeling my firm breasts press against her much-larger, not so firm tits. I wanted to touch and to kiss and to suckle Debbie's magnificent tits for a while as I rebuilt my strength.

I rolled over so Debbie was on top of me. My cock was still just semi-erect but I wanted access to her tits - her incredible tits. I think she sensed this as she slipped her thighs around mine and moved to a sitting position on top of me. Her tits hung down in front of my face when she leaned forward with a hand on each side of my head. I reached up with my mouth and alternately sucked each hard nipple into my mouth. My hands began to play with each enormous mammary that hung down from her body. Debbie got into the action as she began to swing them back and forth - both teasing and taunting my lips as I tried to suckle them.

As she swung her tits in my face, her pussy began to grind on my cock. I could feel my cock stiffening but I really didn't know if I could cum again so soon. After a time, Debbie lifted her hips a bit and my cock slid between her awaiting pussy lips. All day long I had thought of fucking her pussy while sucking her enormous tits and the time had finally arrived. My seven-inch, thick cock was now sliding deeply inside Debbie's wet pussy. She smiled as she raised and lowered her body onto my hardness. I barely moved my hips as she reveled in fucking me. Debbie straightened up on top of me and I watched in great delight as her tits swayed and bounced on her chest as she fucked my cock. Her hand were now fondling my hard tits as she rode my cock.

We fucked for nearly an hour as my body regained it's sexual strength. After a spell of Debbie on top, we moved around so that we were both on our sides with me fucking her from behind. My hands moved over her body as my hips thrust into her. Finally I put Debbie on her back and pushed her knees up towards her tits. She was panting and moaning and begging me to cum inside of her. With her body fully exposed to me, I got up on my knees and drove my cock deep inside her pussy. I picked up my rhythm as I fucked in and out of her nearly bare pussy. Without warning to either of us, my cock spurted cum into her pussy and she cried out in joy as she felt my warm liquid fill her. I was totally spent and crashed down on top of her.

A little past eight, we stumbled out of the room and into the still hot Utah evening. A small restaurant was located across the parking lot and we had dinner before finding our way back to the room. We fucked two more times before sleep overtook our bodies. I'm not sure I really came either time but we had a great time and Debbie certainly did cum both times!

Morning seemed to come early and we awoke in one another's arms. We fucked one more time before helping each other shower in the small shower tub. Climbing into the truck, we both knew we had shared an amazing night of lust and sex and now we were driving back to the real world. A little after noon, I pulled off the freeway and Debbie gave me directions to her friends small house in Vegas. I waved good-bye as I pulled away from the house and headed towards Los Angeles.

#

Five hours later, I found myself winding through the streets of Malibu and staring at the Pacific Ocean out my window. It was hot, but after the oppressive heat of the California desert, the ocean air felt heavenly. I followed the directions that Rachel had e-mailed me and found myself in the gated driveway of a huge mansion that I knew had to overlook the ocean!

I pushed the intercom and gave my name when a female voice answered. The large wrought iron gates opened and I wheeled my old Ford pick-up into the drive and stopped in front of the house. A beautiful short-haired brunette opened the door and I knew it was Rachel as soon as I saw her smile. I almost felt like an eighteen-year old senior in high school all over again. Well, except I wasn't exactly Jaime back then.

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