tagTranssexuals & CrossdressersWorking for a Living Ch. 02

Working for a Living Ch. 02


The Four Seasons

Pulling into the driveway, I saw Jaime's old pickup truck parked in the garage. I was a few minutes early as I got out of my truck and walked to the door. I knocked and stood on the porch, my jacket pulled up around my neck to keep the cold spring wind off my skin. The door soon opened and I was greeted but a smiling brunette. "You must be Chris, come in before you catch cold."

Jaime had described her roommate to me, but I think her smile was even sexier than I pictured. "And you must be Laura. Pleased to meet you," as I extended my hand. My eyes trying to steal a glance at her, but feeling she was doing the same to me.

"Jaime's almost ready but you know us girls and how long we take to get ready for a party! Can I get you something to drink?"

"Just a glass of water would be great. The road's a little slick and guessing it will be fun going over the pass to Jackson."

Laura returned from the kitchen with water for me in her left hand and a glass of wine in her right hand. She was wearing sweat pants and a long-sleeved t-shirt but I could still tell she had all the right curves. "This sounds like quite the party you're taking Jamie to this evening. You go to Jackson often?"

"I have some business in town, but don't get down there too often. This is a fundraiser for the Elk Refuge. It raises quite a bit of money every year but it's also the first spring social event every year so it's usually quite a party." We were heading to a party at the Four Season's in Jackson, Wyoming. It's a town with a lot of money and this really is the first party of the spring so it brings out the crowd. It's not really my crowd but business obligations make it a must for me to attend.

"How do I look," Jamie asked as she walked out of the hallway. I looked her way and I'm sure I grinned from ear-to-ear at her appearance. She entered the room and twirled around for both of us to see her from all angles.

"Damn girl, you look mighty sexy. We might not make it to the party tonight!"

"What kind of girl do you think I am? You promised me a party with the rich and famous!" Jamie was wearing a red gown that stopped just below her knees and snuggly hugged her 36C-cup breasts that left little to the imagination. As she turned, I got quite a view of her toned back, given the dress was backless. It came back together at her lower back and slid down over her sexy ass. She was wearing four-inch heels. A bit risky given the chilly conditions, but they did wonders for accentuating her shapely calves.

"Jamie, you look even better in that dress than you did in the store. You look beautiful." Jamie let her shoulder-length blonde hair spill onto her shoulders.

Checking my watch, "We should get going. Ready?" Jamie slipped on a heavy jacket for the ride to Jackson and grabbed her wrap for the party.

"Laura, can you get my overnight bag for me?"

I moved to Jamie and our lips met for the first time this evening as I hugged her tightly against my body. "You look amazing."


I'd met Jaime four months earlier. She was working on the crew building my house in Idaho. Later that evening, I'd found her stuck at the job site so I took her to dinner. Offering a place to sleep in a spare bedroom as a snowstorm had blown in, she ultimately shared my bed for the weekend. I hadn't realized when I picked her up that she had a surprise for me later that night. Jaime, this sexy lady construction worker, is a transsexual. Of course, I didn't realize until after she had given me the greatest blow I'd ever received.

We've gotten together a few times since that weekend, keeping things light but also very sexual. When I mentioned this party, I could see the excitement in her eyes. She was also very nervous about fitting in with a 'moneyed' crowd. She was used to working on their houses, not mingling with them. I convinced her it would be fun and she agreed.


We hadn't been on the road ten minutes when her cell beeped with a text message. Pulling it out of her purse, she read the text from Laura and it had just one word. "HOT!" She laughed and showed it to me as I drove, apparently you have another admirer.

We rolled into the Four Season's a little after six on Friday evening. The valet held Jaime's door open while the bellman slipped our bags out of the backseat of my Ram 2500. I hustled her into the lobby. Though it was late May, it still felt like winter. And having seen her dress, I knew that jacket wouldn't keep her that warm!

"Good evening Shelley," as we walked to the front desk. I could feel Jaime giving me a look of surprise that I knew the young lady's name.

"Good evening Mr. Shaw. You ready for the big party?"

"Ready or not, we're here! I'm sure Dolores will make it quite the evening." Dolores Thompson has lived in Jackson for years and she annually hosts the party. She plans it all year. "This is my date for the evening, Jaime Harrington."

In five minutes, we were in our suite with a view of the ski lifts. Jaime walked around the suite, seemingly in a trance. "I can't believe how big this place is! And it's so beautiful."

"No, this is just a room. You are beautiful!" She blushed as I handed her a flute of champagne. "To a fun evening," the line was corny and we both knew it, but I just had to say it, as it was so true. I pulled her close to me and we kissed with passion. My hands wrapped around her and squeezed her sexy ass. She pressed her thigh to my crotch and she soon had my cock growing uncomfortably in my slacks. Jaime broke our kiss and took a long drink from her glass then handed it to me to hold.

Before I realized, Jaime already had my belt unfastened and my zipper pulled down. I looked down as she took my nearly erect cock into her wet mouth. I could feel the freshness from the champagne on my skin. I've come to greatly desire her cocksucking abilities in these few months I've known her. Jaime's lips slid over and around my crown as her tongue licked the underside of my now erect cock. I could feel her strong fingers massaging and squeezing my balls. Jaime's mouth opened wider as she took all of my cock. I watched her, mesmerized by this beautiful lady as she began to pump up and down my erection. Her fingers tugging my balls, increasing my urgency.

I knew she wanted me to cum quickly now and she would make me wait later. I swallowed the last of my champagne as she buried my cock in her mouth. Her index finger lightly raked my asshole and my body shuddered from the sensation. My cock erupted in her mouth, shooting a warm stream of cum down her throat. Jaime continued to massage my balls as she drained me, her mouth still wrapped tightly around my cock.

Finally, to my body's relief, Jaime stood up and took her champagne glass from my hand. She took a long swallow before returning her lips to mine. I looked into her eyes and I could sense the smile on her face.


Finally around seven, Jaime disappeared for a few minutes to touch up her make-up before the party. "Nervous?" Jaime just nodded and smiled.

We made our way to the Grand Ballroom, Jaime tightly holding my arm as we walked. We could hear the music as we approached. Walking inside the Ballroom, I could sense Jaime hesitating as she took in the setting. I quickly grabbed us two flutes of champagne as we strolled around the room. I shook hands as we made our way to old friends. Dolores found us and greeted me with the hug of an old friend. I've known Dolores for years. I could see her looking over my date like an old mother hen. Introducing Jaime to her, Dolores swept her away from my arm. "Come with me girl and I'll introduce you to a few of the other ladies and we can give Chris some time with the guys." I should have told Jaime to expect this but figured it would just make her nervous.

Dolores brought her back to me twenty minutes later, "She's a wonderful girl Chris. Do save me a dance later."

"You know I will Dolores. And yes she is."

Just before dinner, I spotted an old friend across the room. "I see someone I want you to meet." "Harrison, how are you old friend?" We shook hands and he gave that trademark Harrison Ford smile.

"Doing well, though apparently not as well as you tonight," as he extended his hand to Jaime. I introduced them, but I'm honestly not sure Jaime even heard me.

As we walked to our table, "that's really Harrison Ford, isn't it?"

"Yes. He has a ranch up here. We've done some business together over the years."


After dinner, the band began to play a mixture of jazz and country and pop. I grabbed Jaime's hand and led her to the dance floor. As we danced close, I whispered into her ear all the sexual things we were going to do together when the party was over. She definitely garnished many looks as we danced, both for her appearance and for the mere fact that she was an unknown to the crowd.

As we stood chatting, I felt Harrison's hand on my shoulder. "As I'm here tonight alone, would you mind if I danced with your gorgeous lady?" I looked at Jaime but knew the answer without asking. She smiled and took his lead to the dance floor.

I watched them dance, one up-tempo and a pair of slow songs, before they returned. "Thanks Chris and thank you Jaime."

After he left, "I can't believe I just danced with Harrison Ford. Laura will never believe me!"

"Don't worry, I'll back you up with her. Now that I got the movie star to turn you on, how about we slip out of here for the evening?"

Jaime blushed at my comment, "Let's go quickly and I'll show you how turned on my date has me!"


As soon as the door was closed behind us, I had Jaime pinned against it. My lips pressing firmly on hers as my tongue pushed hard and fast past her lips. My body pressing hers as my left thigh slipped between her legs. The four-inch heels made us nearly the same height. At first, my hands held her wrists tightly as I gained control but then I released them so I could caress her magnificent breasts. We kissed for minutes, my cock growing harder as I humped her thigh. She had me so aroused I thought I would cum by just pressing her against the wall.

My hands were inside her dress, caressing her breasts and rubbing her nipples. I could feel them growing hard with my touch. There was so much sexual energy built between us. Her tongue wrestled with mine inside the warmth of her mouth. I could now feel Jaime beginning to grind her pelvis into me, as we were both needing one another right now.

I growled into her ear, "I want to fuck you Jaime," as we continued to hump one another against the wall. She pushed me away just far enough so she could slide down the wall. In moments, her warm mouth had surrounded my lust-engorged cock. She was quickly taking my entire seven inches into her mouth. There was no tenderness or foreplay involved this time. Jaime opened her lips and swallowed my cock. I put my hands behind her head so I didn't bang her head against the door as I fucked her mouth, increasing the pace as she found her rhythm. Her left hand was pulling on my ball sack as her mouth quickly sucked my cock in and out. Nearly as soon as it started, I was ready to cum. I pressed my cock into her mouth, her tongue caressing it as I did. I pulled out, nearly to her lips and shot my first hot stream of cum into her mouth. Her fingers quickly moved to my cock, milking me for all that I had. Then she released my ball sack and a second shot of cum exploded from my cock that was buried between her lips.

Jaime slid up the wall and smiled at me. We put our lips together to kiss and to my surprise she had swallowed all that I had given her without a trace remaining. I pressed my lips to hers and we kissed deeply once again. I unfastened her dress from behind her neck and helped her slide it down over her hips. She stepped out of it, using my shoulder for support as I picked up her beautiful dress from the floor and lay it over a nearby chair. I stepped back and looked at her from head to toe. She was wearing sheer boy shorts, thigh-high stockings and her four-inch heels. "My God you are beautiful! And did I mention Sexy too!" I could see Jaime blushing at my compliments. "Just stand there for me." And I quickly stripped out of my clothes, tossing them with much less care on the chair. My cock was hanging down between my thighs but I knew that was only momentary. I dropped to my knees and put my lips inches from her boy shorts. My fingers moved lightly over her inner thighs. I could see the goose bumps rising even though it was warm and toasty inside the suite.

I leaned forward and lightly kissed a few different spots on her shorts as my fingers crept to the waistband. Jaime's body stiffened with the anticipation of the moment. I pulled the shorts over her hips and slid them down her legs. As she lifted her left foot so I could remove the shorts, her cock sprang forward coming untucked from it's hiding spot. I smiled at what I now saw before me. I kissed the crown lightly and allowed my tongue to slip past my lips and lick the underside of her ever-growing cock. Playing lightly with it for the very first time, Jaime put her hands on my head and ran them around my hair. "Oh Chris, you don't have to do this." After a pause, "But please do."

Even though we've spent a few weekends together, I had never really played with her cock much and definitely had not brought it to my lips. I have never been with a man and had never really considered it. All of our sexual encounters to this point had been much like any man and woman getting together. I had pretty much decided that would change this weekend before I picked her up. Once I saw her in that dress, my mind was made for me. I knew it was what I wanted to do for both of us.

I wrapped my fingers around her swelling cock and opened my lips wider, accepting more of her delicious charms. My tongue began to swirl around her crown as I tried to remember all the techniques I so love. I could literally feel her cock growing larger in my mouth as I began to slowly pump my face on her cock. I was taking her deeper into my mouth, my teeth lightly raking the underside as she slid in and out. I could now feel Jaime beginning to thrust her hips slightly as my mouth would go down on her cock. My left hand stroked her, as my mouth would follow. Jaime was moaning in pleasure, both from my sucking and I'm sure just from the fact I was going down on her at this moment. "Oh Chris, I'm gonna cum sweetie." She pulled me to my feet and we kissed deeply as she wrapped her hand around mine and we jerked her off together. I could feel her cum splashing on both our bellies before landing on our hands. She brought my hand to her lips and licked her cum from it. It was so arousing to watch her be so sexy.

We both smiled, "Thanks ... I don't think I'm ready for that step yet."

She raised an eyebrow, "Yet?"

I led her to the bedroom, the covers having already been pulled back by the hotel staff. She slipped off her heels and stockings and jumped into bed beside me. In moments, she had me hard again. "I believe you promised me a fucking, Chris." She smiled at her wickedness. I rolled Jamie onto her elbows and knees in the middle of the bed. Moving in between her legs, I kissed her smooth ass cheeks my hands moved around her skin. Jamie was already rocking slightly to my touch, her body ready for me. I squirted the lube liberally on her rosebud and covered my crown and lined myself up behind her. I pressed the head of my cock against her asshole and pushed myself forward. The sensation was amazing as I felt my cock entering her expanding hole. It was like the first time for us.

Putting my hands on her hips, I pressed my cock deeper into her hole. Jamie was already moaning as I began to fill her up. I quickly settled into a quick in and out rhythm, we were both so ready to fuck. I found my cock buried in her asshole with my sac slamming against her body, quickly backstroking until my crown would almost part her rim before slamming forward and repeating. Jamie's moaning turned to lust, "Fuck me Chris ... please Fuck me harder!"

Her body moved with mine, I was sure her beautiful tits were swaying under her body as she ground her hips back into my body with each thrust. "Oh Jamie ... aaaaaaahhhhhh!" I groaned as my cock spasmed in her asshole filling her with my warm cum. I continued to thrust into her before collapsing on top of her, my energy totally spent.

We rolled onto our left sides and my right hand moved to her nearly erect cock. I circled her cock and began to pump her with my fist, my cock still buried in her asshole. Long, quick strokes the full length of her cock had her soon moaning. And just as quickly, she was shooting her cum on her belly and the soft white sheets. She finally wrapped her hand around mine to prevent me from stroking her any longer. "Please stop ... I-I-I can't take anymore right now." And we snuggled together on the sheets, our lust totally spent for the evening.


I awoke the next morning to find myself alone in the big bed. Pulling on the white robe, I walked out to the living room and found Jaime sitting on the couch and reading the Jackson Hole magazine. She was drinking orange juice and sucking on a large strawberry. The heat from the fireplace felt great on my skin. I admired her exposed sexy leg, her robe parted between her thighs. I must have watched her for a couple minutes before she realized I was there.

Smiling up at me, "Coffee?"

I moved between her thighs, down on my knees, "Later." I pulled open her robe, exposing her warm nude skin to my sights. Her breasts sat firmly high on her chest, her nipples swelling from excitement and being exposed to the morning air. And immediately before me, her cock lay against her thigh. I bend down low and lightly kissed her left inner thigh moving from just above her knee to just below her crotch. Her cock stirred at my attentions to her skin. I looked up as I crossed over to her right thigh. Jamie was lightly raking her nipples with her nails, her eyes watching my every move. My kisses, a bit firmer now, moved again from above her knee to her crotch. This time I had to kiss around her swelling cock.

My hands massaged her strong calves, feeling her soft skin and tight muscles. My tongue didn't stop at her crotch this time. I continued to her sack and lightly suckled the skin. My mouth opened and took her scrotum between my lips. This caused Jaime's cock to stiffen and slide over her skin. My right hand was now sliding up her inner thigh. My lips moved to the underside of her cock, my tongue tracing lightly. Soon my lips moved around her crown and my tongue licked across her tip. I opened my mouth and let her crown slip between my lips.

Jaime was now pinching and twisting her nipples, her moaning growing more intense. I began to slide up and down her cock, doing my best to bring her as much pleasure as she brings to me. My mouth felt so full, her cock going deeper into me. My right hand was now sliding under her butt, my index finger searching for her rosebud. Feeling my fingers, Jaime shifted slightly on the couch and planted her asshole on my finger. I began to pump my mouth up and down her cock. I was taking the first five inches of her beautiful seven inch cock.

Jaime was sucking on two fingers from her left hand as her right hand twisted and pulled at nipples and squeezed her tits. I knew I was getting her close. My mouth, sliding down her cock then sucking on her as I rode her back up to the crown. "Chr-i-s, I'm cum ..."

My index finger pushed inside her rim to the first knuckle as my mouth slid down her cock. Jaime creamed in my mouth causing me to gag but I took her cum in my mouth. I hesitated before swallowing as she pumped her cock in my mouth. The finger in her asshole was driving her crazy. I lifted my lips from her cock and she dribbled down her cock and onto her belly.

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