tagTranssexuals & CrossdressersWorking for a Living Ch. 04

Working for a Living Ch. 04


The buzzing of her cellphone on vibrate was barely noticeable over the hum of the vibrator between her thighs. Normally Jamie would have just ignored it but Chris had told her he might call if his meeting finished early. Her hand felt for the phone on the nightstand beside the bed. She looked at the screen and saw Chris' name so she flipped it open to answer. "Hello," she said nearly breathlessly as the tip of the vibrator probed her asshole.

"Jamie?" was the quizzical response as he thought she sounded a bit different. "I'm about 5 minutes from your place. Do you want me to get some wine and stop by?"

"Forget the wine. Key's in the usual place." Jamie's breathing was erratic as she hung up the phone. She looked down over her breasts to see her roommate Laura's mouth sliding up and down her fully erect cock. She could feel the first six inches of the thick vibrator sliding in and out of her asshole. Jamie's fingers pinched her ample nipples. Her knees bent with Laura between her thighs, her cock was filling Laura's warm mouth. Laura bobbed her head quickly up and down, taking Jamie's full seven inches into her mouth. Jamie began to cry out as the cum shot from her cock and filled Laura's mouth. Jamie thrust her hips upward, her cum spilling from Laura's lips. After the second stream of her warm cum filled Laura's mouth, Jamie turned her head to the doorway and saw Chris leaning against the doorjam with a large smile on his face.

Chris eye'd the scene before him. His sometime girlfriend Jamie was lying on her back with her long blonde hair on her shoulders. Her 36C medically-enhanced breasts rising and falling with her heavy breathing. Her body was muscled from the construction work she does for a living. And of course, her beautiful cock now only partially erect, lay on her smooth skin. Her roommate Laura was on her elbows and knees between Jamie's legs. She turned and smiled at Chris, dribbles of Jamie's cum running down her chin. Both girls were nude from head to toe. This is the first time Chris had seen Laura naked. He had imagined her body and Jamie had described it but nothing is like seeing the real thing with your own eyes. His first surprise was how big her breasts were when she raised up to look at him. His second surprise was how dark and how full her pubic mound was between her thighs. He knew she would be dripping wet as well.

"Well I see I'm a bit late to the party!" Chris walked over and gave Jamie a long, passionate kiss. He then moved a couple steps down the bed and brought his lips inches from Laura's. She leaned forward and pressed her moist lips to his. Chris could taste Jamie's cum on Laura's tongue as they kissed for the first time. As they broke their kiss, Chris straightened up, "I guess I have some catching up to do!" And he began to undress himself.

By the time Chris was as naked as the girls, Laura had moved aside of Jamie. Chris crawled onto the bed at their feet. His left hand reached for Jamie's cock but he slid between Laura's thighs. His tongue licked at her lips, finding his way past her thick pubes. Laura let out a quiet moan as she felt him beginning to attack her sex. His hand slowly stroked Jamie's cock coaxing it back to life. By now, Jamie was sucklling the thick nipples that capped Laura's breasts. Chris' right hand parted Laura's pubes and held her pussy lips wide open to his tongue. His tongue dove deeply between her swollen lips. He could taste her juices on his tongue, it was obvious she had been quite aroused from going down on Jaime before he arrived. Chris' tongue found her clit and he began to rub it furiously from side-to-side as three fingers began to fuck her.

Jaime could feel her cock grow hard from being stroked by Chris. Laura's body began to thrash as Chris brought her near her first orgasm. Jaime's lips covered Laura's. She forced her tongue inside, forcing her lust on Laura. Laura tried to cry out as her body was being ravaged by Chris' tongue. He roughly lapped her clitoris as his fingers pumped in and out with urgency. Her hips thrusting into his hand before shuddering into orgasm. Chris could feel his hand coated in her juices and Jaime broke their kiss. "Oh Fuck! Oh Fuck! I'm cummming!" she yelled out for all to hear. Without missing a beat, and catching Jaime by surprise, Chris quickly moved over and lowered his mouth onto Jaime's thick cock.

Chris raked the underside of her cock with his teeth as he slid up and down the length. His hand began to rub and pull on her scrotum as he ran his tongue around the crown. Laura lay beside them and watched. Though she had been with Jaime many times, she had never seen anyone else going down on her roommate. Laura's hands roamed over Jaime's nipples, teasing and toying wth them, heightening her arousal. Chris took Jaime deep and inhaled, creating a vacuum in his mouth. Her cock cumming in his mouth. He gagged at first, still new to the sensation, but doing his best to take all of her cum. As he felt her cock begin to shrink in his mouth, he lifted his head to look at the two girls lying side-by-side.

"Well we've both cum. You can leave now." Jaime was laughing as she said it, barely able to get the words out of her mouth. Chris bulled his body up the bed between them. Rolling over onto his back, each girl wrapped one of their thighs over his as they moved close together.

Chris kissed Jamie but then did the same with Laura. "I've never been with roommates ... until tonight."

"Does Laura look like you'd imagined? Or should I say fantasized?"

Chris thought for a moment before speaking, "Actually her breasts are much larger than I had thought and I never pictured such a hairy bush."

Both girls giggled at his comments. "I used to keep it shaved smooth. Jaime bet me $100 I couldn't go six months without shaving. I win the bet tomorrow!"

"Then I better fuck you tonight so I'll know what it feels like," as Chris rolled her on top of his body. Her thighs instinctively moved apart and his rock hard cock pressed to her wet pussy.

She adjusted slightly and lowered herself onto him. Laura began to ride his cock in a smooth, fluid motion. Chris smiled into her eyes. He knew that Jaime and her had shared much small talk in the months he'd known them and they both had wondered about this moment. Laura had control of her body and she clenched her pussy around his cock as she lifted herself off his body before slamming her hips back down to him. Chris met her body with thrusts of his own, his cock ramming deep into her moist sex. Laura's large, full breasts danced above him as her body pulsed from their fuck. After ten minutes of this foreplay, Chris grabbed her upper body and rolled her away from Jaime. He was now on top of her and looking down into her eyes. His cock throbbed in her pussy, seemingly growing in length, as he took control. He began to thrust hard and fast into expanding pussy. Suddenly Laura could feel Jaime's index and middle fingers rubbing her aroused clit. Chris' hard cock furiously pumped in and out of her pussy. "Oh Fuck! Oh Fuck!" she cried over and over as her body began to tremble deep inside her sex. Chris pinned her arms to the bed as he pistoned his cock in and out of her. Jaime's fingers on her clit put her over the top. Laura's pussy exploded with her orgasm coating Chris' cock. And then he too shot a thick, warm stream of his cum. They continued to thrust at each other, their bodies cumming over and over until finally she was overflowing. Her dark pubes were totally covered in a mixture of their cum. And Chris fell on top of her. Their hearts pounding in rhythm as they both tried to catch their breaths.


The next morning found me and Jaime driving up the hill to my place for the weekend. We hadn't seen much of each other lately and with the warm summer days, we thought it would be a great time. Not much had been said about the night before until we were almost to the dirt road turn-off to my cabin. "You really liked fucking Laura, didn't you?"

I couldn't tell if it was mere curiousity or jealousy so I tried the middle of the road response, "No more than it appeared you liked being fucked by her." I responded with reference to seeing them for the first time.

The road is pretty bumpy but when I looked sideways, I was sure I could see a devilish grin on her face. Apparently that was the right answer.

I brought in her overnight bag and by the time I had taken a leak, Jaime had already opened us two Moose Drool's and had lost her t-shirt leaving her in a bikini top. Again those 36C's just cried out for me. I could feel my cock wiggle to life in my jeans. She handed me a beer and wrapped her arms around my neck. Our lips pressed firmly together, as did the rest of our bodies. Her body is so firm, I always love the way she feels against me. We went outside and sat on the rocker on the deck. The view was toward the lake and watched the jet skiers and water skiers as we drank our Drool, but we both knew this was just a subtle form of foreplay. When I finished my beer, I reached over and began to stroke the crotch of her shorts. Jaime was already aroused and waiting for me. "I thought you'd never finish that beer cowboy." She took a long swig on her beer, draining the remaining fluid in a sexy sorta way.

I took her hand and led her into the house and straight to my bed. She quickly pulled my shirt over my head. Her lips covered my nipples, alternating from one side to the other. As she did, her fingers deftly unbuttoned the fly of my jeans and she pushed them over my hips. My cock was already erect in anticipation of her. Jaime pushed me backward onto the bed and pulled off my boots then my jeans. I scooted backward on the bed, my eyes never leaving her body. She reached behind and untied her bikini top and let it fall to the floor. Her breasts hovered in the air, her nipples already erect. She then slid her shorts over her hips and down to the floor, leaving her sex covered by sexy white lace boyshorts. The shorts were being stretched in a futile attempt to contain her deliciously erect cock. Jaime crawled onto the bed, much like I had the night before, and got between my thighs. Her lips hovered inches above my cock as she seductively licked her lips in lust and anticipation. I could feel her nails raking the skin of my inner thighs as I propped my head on a pillow so I could watch. She lowered her head but she avoided my crown. Instead she took my left nut into her mouth and rolled it around with her tongue. And then the right nut she did the same.

Finally she lifted her lips and pressed them to the crown of my cock. She licked the precum from my tip as she slowly circled my cock. She teased and toyed with it, even avoiding my muted thrusts as I tried tofind her lips. After an agonizing ten minutes, she parted her lips and allowed my cock to slide between them. Her tongue worked my cock as she slowly took my entire eight inches into her mouth. Jaime began to fuck my cock with her mouth. Her lips would almost leave my cock before she would relax and slide all the way down my length so her nose rested in my pubes. Then she would make the round-trip all over again, sometimes quickly and sometimes agonizingly slow. I could feel my orgasm rising within my body and knew I was very close. Suddenly her right index finger pressed against and then inside my asshole. The surprise and the sensation took me entirely off guard and my cock shot a thick stream of cum into her waiting mouth. She wiggled her finger before removing it but not before a second stream had left my body. Jaime raked the underside of my now-sensitive cock as she pulled herself free. She crawled up my body, laying her warm sexy body on mine. Her face now over mine, inches above me. I looked into her eyes and knew what she wanted from me so I complied. I opened my mouth and extended my tongue. She parted her lips and I quickly felt the warm cum I had just shot into her mouth being drizzled into mine. Last night I had sucked her cock and now it was as if I was sucking my own. She gave me just enough to want more and I reached up and grabbed her behind the neck and pulled her to me. Our lips crushed together and I soon felt her tongue pushing my cum between us.

When we had both swallowed, Jaime smiled at me as the cat did to the canary. "Now what cowboy?"

I raised my lips to her left ear, "Now you fuck me."

Jaime jerked her head so she could look into my eyes to see if I was kidding. It has been less than a year since we first met and I had only been with genetic women before her. Jaime had been amazed when I had sucked her cock for the first time at The Four Seasons but I'm sure she had never expected this. The first time Kelly had stuck her finger inside my asshole it made me wonder about a real cock. She could see in my eyes that I was very serious and a tear began to run down her cheek. "I never," but I cut her off with a kiss.

A moment later she was kissing her way down my body. My heart was racing in fear and anticipation. She kissed my semi-erect cock then helped me to roll over on my belly. By the movements on the bed, I could tell she was taking off the boyshorts she still wore. I then felt her strong hands on my asscheeks and her soft lips kissing down the crack of my ass. I tensed when I felt her tongue on my asshole for the first time but I told myself to relax. She was gentle as she kissed around the rim, occasionally running her tongue across my bud. Jaime coaxed me onto my hands and knees so my ass was in better position for her. I felt her moving between my thighs and I knew the time was now. "I'll be gentle cowboy," the words hanging out there for both of us to hear. "The first time," her little joke breaking my concentration and then I felt her cockhead parting my asshole. My head pressed into the pillow raising my ass to her beautiful cock. Jaime began a slow rhythm of fucking going deeper every few strokes. I could feel her hands caressing my hips and back in a soothing way. Her cock was going deeper inside my asshole and I could feel my muscles tightening around her. It felt different than I had imagined. It was more natural that I could ever believe. I could feel Jaime's rhythm picking up speed as her hands steadied her by holding my hips. I tried to say something to her but no sound could part my lips. It felt like the most painful and the most pleasureable experiences of my life all at the same time. Jaime's cock was now thrusting into my asshole as she neared her orgasm. I felt her body shudder as she grabbed my hips and her body locked against mine. Her cock shot cum deep inside my bowels and she buried her cock without moving. I screamed into the pillow and then she was collapsing on top of me. Her full breasts pressing against my back as we pressed to the sheets. I could feel her cock still buried inside my asshole and I loved it.

Five minutes passed before either of us said a word. I'm not sure either of us even took a breath! "I don't know that I've ever cum that hard." And she hugged me even tighter. As we lay there together, I could feel her cock grow soft inside of me and my cock grow hard against my belly.


A little past six, Jaime found me on the side deck grilling some vegetables for dinner. She was wearing one of my oversized t-shirts and from the curves and points that were appearent, nothing else. She reached for my beer and took a drink. "That was some surprise Chris. Thank you, you don't know how good that makes me feel."

Rubbing my ass I smiled, "I think I have some idea." and then she slugged me in the arm. #

The small art gallery in the historic section of Idaho Falls was doing brisk business this evening. Once a month, the city art council hosts a showing from an out-of-town artist and tonight it was Clyde Robinson. He has a unique perspective on photography and a variety of his pieces were on display. The ones that caught Laura's eye appeared to utilize a kaleidoscope for affect. She often comes with Jaime to the monthly showings but with Jaime up the mountain, she decided to come alone tonight. She wandered the gallery, saying hello to a few acquaintances, but found herself back in front of a large photograph of brightly colored plumeria.

"What do you like about this one?" a deep male voice standing behind her asked.

"The flowers are so beautiful and then for the picture to make so many of them on the print ... they are very interesting," she responded without turning towards the voice.

"But do you like the print, or just find it interesting?"

Turning now, "Oh, I like it very much."

Extending his hand, "I'm glad to hear that. I'm Clyde Robinson."

Laura smiled, realizing she was talking to the photographer. She studied his face, taken by his warm features and his friendly smile. She was surprised to note that Clyde was African-American, primarily because Idaho is a very caucasian state. "How about I fill your wine glass and then you show me which other photos you find interesting."

Laura laughed as she handed over her glass. She followed Clyde to the corner bar as he filled her glass. They wandered about with Laura pointing out a couple photos she also enjoyed and even pointed out a couple she didn't particularly find 'interesting'.

Clyde worked the room and answered questions about his art effortlessly as Laura walked with him. As the end of the showing neared, Clyde asked Laura if she would like to join him for a late dinner. When she agreed, he told her he needed a few minutes with the head of the art council and then she could lead him to dinner. Laura filled her wine glass and took a seat as she waited for Clyde. He returned about tweny minutes later, "Ready?"

He suggested a steak house so Laura took them to a brew pub and steak house a couple miles from her house. The place brewed it's own beer and cooked the best steaks in the area. Being a Saturday night, it was bit loud but they talked over the roar of the crowd. Clyde was from Florida so Idaho was a world apart for him. He was traveling around the west displaying his photos in a variety of galleries. It was part to expose his art and part to see a section of the country he had never visited. By the time they had finished dinner, the band had started playing in the bar. Clyde paid the bill and they grabbed their glasses and headed towards the music. The band was playing a blend of country and rock and Laura soon found herself on the dance floor with Clyde.

Laura looked the part of country, wearing her cowboy boots, tight fitting jeans and a pull-over sweater. The sweater did nothing to conceal her very large and firm breasts. As she danced with Clyde, he had the occasion to hold her tightly against his body. She judged him in very good physical shape and wondered if the art gallery wine and the brew pub beer had impacted her senses. When Clyde held her close to his body, she was sure she could feel his cock erect against her thigh. And it seemed to be some cock.

After an hour of dancing, Clyde asked her if she'd like another beer. She leaned close and whispered in his ear, "How about we drink it at my place?" He merely smiled as he took her by the hand and let her to the parking lot. She handed him the keys, "I think you better drive us."

She gave him directions and they were back at her house in five minutes. She opened the door and led him inside. Laura turned on some music as she grabbed a couple beers from the fridge. When Clyde extended his arm to take the beer, Laura pulled it back. "You've got to kiss me first." Clyde pulled her close as she wrapped both arms around his neck, the bottles clinking behind him. His lips covered hers and his tongue slipped inside her warm mouth. He kissed her hard, his hands squeezing her asscheeks through her jeans.

Breaking their embrace, she handed him the beer bottle as she took a long pull on hers. Then she sat the bottle down and ran her hands over his chest. Laura quickly unbuttoned his shirt and slipped her hands inside the fabric. His body was as fit and muscled as she had imagined while they were dancing. She pushed the shirt off his shoulders and her fingers ran over his skin.

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