Truckstop Tess (18+ XXX)

The afternoon sun filtered through the sheer curtains of Tess’s bedroom, casting a warm glow on her vanity table where an array of makeup and lingerie lay scattered. At 25, Tess had perfected the art of transformation, and today was no different. She began with her hair, long red tresses cascading down her back as she brushed it until it shimmered. Her hands then moved to her makeup, expertly applying dark eyeliner and ruby red lipstick that made her lips look impossibly full. She was petite at 5’8″, but with curves that defied her height—an athletic hourglass figure that was the envy of many women.

Tess reached for the skimpy red bodycon minidress that barely covered her ass, slipping it on and adjusting it so that it clung to her every curve. She then added the Sexy Mesh white Corset Ruffle Lace Up babydoll lingerie, the plunge underwire bra holding her 36 DD breasts in place, creating an even more pronounced hourglass shape. Sheer Garter Belt Babydoll Lingerie was clipped to white thigh high silk pantyhose, and finally, she put on the red panties gaff, hiding her cock completely. The 5 inch red stilettos completed her look, making her feel powerful and sexy.

She took one last look in the mirror, admiring the expertly crafted makeup and the way the lingerie peeked out from under her dress. Tess loved dressing slutty and sensually sexy, and today she was on a mission to find adventure at the truck stop.

As she walked out of her house, Tess kept her head down, avoiding any eye contact with her neighbors. She didn’t want to draw attention to herself before she was ready. Once in her car, she drove to the large truck stop, her heart pounding with excitement.

The truck stop was bustling with activity when she arrived. Tess walked around, feeling the eyes of every trucker on her. Whistles followed her as she strolled by, and she reveled in the attention. She was the hottest woman at the truck stop, and she knew it. Her long red hair swayed with each step, and her curves were impossible to ignore in her skimpy outfit.

It wasn’t long before she caught the eye of a man who stood out from the rest. He was about 6’5″, with muscular arms and washboard abs that were visible even through his tight shirt. His dark hair was slightly tousled, and he had an air of rugged confidence about him. Tess started lusting for this hunk of a man, and she slowly made her way over to his semi truck.

“Hey miss,” he said, panting slightly from chasing her. “Can I, uh, buy you a drink?”

“We’re not at a bar,” said Tess with a smile, “but I’ve got some stuff back in my truck if you’d like to come.”

Tess wiggled her way back to his truck, shaking her ass as best she could without falling out of her heels. All the other jealous truckers whistled and honked their truck horns as she passed. Once she reached the truck, she saw the sexy man with the largest arms like tree trunks in tight shirt and jeans. Tess started lusting for this hunk of guy slowly walk to Bryan tuck with him to really lust for her, slowly getting aroused.

“I’m Tess,” she introduced herself, and the trucker said his name was Bryan.

For about twelve minutes, the two talked, with Bryan getting so aroused with his back leaning against the truck as Tess flirted, knowing she would be Bryan’s bitch soon. Bryan suddenly grabbed Tess, kissing her softly at first, then intensely, while holding her gradually and then tightly. He rubbed her all over her body, eventually lifting her dress and feeling her panties. At the same time, Tess started feeling Bryan’s growing cock bulge in his jeans.

As Bryan continued feeling Tess’s ass and kissing her, he found a big surprise hidden under her panties. Tess was a little scared that something might happen and whispered in Bryan’s ear, “I’m one of those special girls.”

Bryan said, “I don’t care. You are one of the hottest pieces of ass here. Almost all the other women walking around the truck stop are not especially natural women. In fact, you are the most beautiful woman I’ve ever seen. Trannies are always the sexiest women ever, knowing how to satisfy men crazily.”

Bryan guided Tess to a darker part between the truck cab and hitch, hidden from all eyes to see. With a long kiss, Tess felt Bryan’s humongest bulge with her own cunt straining her panties and dress between them. She got down to her knees, unzipped Bryan’s pants, and his largest cock fell out. Tess had never seen a cock so big in her life—it must have been at least 11 inches long and as large as a rolled-up newspaper. Tess grabbed hold of Bryan’s cock with her small hands, licking and kissing the tip before licking up and down his shaft. She eventually sucked on his golf-ball-sized balls, driving Bryan crazy, and then she swallowed the tip of his cock, eventually taking in all 10 inches with her lips touching his balls. Tess started sucking Bryan’s cock slowly, then faster, swallowing all of it like a lollipop. At the same time, she was rubbing her own cocklet in her panties. Bryan grabbed her head to help her swallow his cock, eventually holding it all the way in. Bryan said, “I’m going to cum. You want it inside?” Tess nodded. Bryan was breathing heavily, easing up his cock until it was only a quarter of the way inside Tess’s mouth, and then he came, shooting globs and globs of cum with some leaking out of Tess’s mouth as she swallowed most of it. At the same time, Tess’s cock strained and released her cum all over her panties, with some leaking down her leg. Bryan lifted Tess up to kiss her passionately, sharing his cum in Tess’s mouth. At the same time, Bryan stroked Tess’s cock, catching what was left of her cum into the cup of his hand and then placing it into Tess’s mouth, kissing her and tasting the comingling of their cum. Bryan said, “This is one of the best blowjobs ever. This is why us truckers love you crossdressing trannies.”

Now Tess, it’s time for a drink as we rest,” Bryan said, picking up Tess in his arms and kissing her before opening the truck cab door and bringing her into the truck. They sat in the back of the cab, and Bryan grabbed two glasses, pouring 18-year-old scotch. Both clinked glasses and drank the scotch. Tess and Bryan proceeded to have small talk about Bryan’s life as a trucker and Tess’s love for being a woman and satisfying men. Tess loved dressing up as a woman and being serviced by several men at the truck stop for a few years, including being a regular lover for the owner of the truck stop, Bruce.

Bryan began to kiss Tess, his tongue deeply entering her mouth. His hands caressed her boobs but quickly moved to her ass. His hands lifted up her minidress and searched underneath as they kissed, rubbing her ass and reaching for her panties and caressing Tess’s cock. Tess started rubbing Bryan’s jeans, feeling the growing bulge again, driving her own arousal. Bryan then quickly and crudely stripped his clothes off.

Thrust before Tess in all of its glory was a fully engorged 11-inch cock that turned Tess into a hungry bitch. Tess jumped onto Bryan, kissing him so passionately, working her slut mouth up with Bryan’s mouth. Bryan pulled down her panties and slid them to her ankles. Tess then stepped out of the silken material and let Bryan push her gently but forcefully onto all fours on the bed. Behind her, with his raging hard-on, Bryan then bent over a bit and began to kiss Tess’s ass, kissing her cheeks hard before beginning to tease her hot asspussy hole with his tongue.

Tess got on all fours on the bed in the truck cab, awaiting the ride of her life, spreading her ass cheeks. Bryan slowly entered Tess, giving her time to adjust to the pressure of his huge cock. Tess began to flutter in pleasure, with her own cock (about six inches) fluttering engorged but helpless as Bryan penetrated her. Then Bryan began to fuck her. He fucked Tess good, plowing her ass from side to side, in and out deeply. Bryan had the crossdresser begging for more. “Bryan, give me more, I love your big cock,” Tess urged Bryan on and on. Suddenly, Tess felt Bryan begin a violent shuddering, rocking the truck cab like an earthquake, and his tempo increased and decreased. He fucked in and out of Tess like a jackhammer relentlessly with anal penetration. As Bryan fucked Tess in the doggy position with Tess’s own cock getting very aroused, Tess stroked it constantly to keep it just hard enough and erect. Bryan slowed down as he neared climax and then sped up again and again, from doggy style to face down with her ass up for 30 minutes, driving Tess to lunacy, making her scream like a banshee so loud that people outside could hear her scream and moan with her constant erections.

Bryan suddenly grabbed Tess, turning her gently onto her back and kissing her. He lifted Tess’s legs over his shoulders with Tess reaching for Bryan’s cock, guiding it to her tight, battered ass as Bryan pushed his rock-hard cock into her wetness. He thrust forward, and Tess felt the head of his cock hit her ass cervix as he groaned. Then he pulled back, and Tess got this desperate, frantic little feeling as he rammed it back in, then slowly building up speed. Bryan kept pounding Tess’s ass nonstop as she screamed so passionately, loud enough to wake the dead for 45 minutes, slowing down and speeding up while alternating her right leg and left leg on his shoulder. As Bryan thrust his manhood into her, occasionally lifting her body, arching it into the air with each pounding thrust relentlessly, Tess wondered how much more she could take of Bryan fucking her boi pussy.

As Bryan continued fucking Tess on her back, Tess started grabbing Bryan’s body, pulling herself up to kiss him, wrapping her legs around Bryan’s body, facing him, kissing him passionately. While in the Lotus position, Tess started riding Bryan’s cock up and down, with her hands and legs wrapped around him, kissing him constantly. Bryan was grabbing Tess’s petite ass, guiding Tess as she rode his cock fully inside her ass with extra deep penetration. Tess loved every minute of riding her stud.

After riding Bryan’s cock and kissing him passionately for 15 minutes face to face, Tess pushed Bryan onto his back. Tess continued riding Bryan’s cock in cowgirl style. As Tess rode Bryan up and down, she occasionally leaned forward to kiss him with her hard cock between them, and then Bryan would grab Tess’s ass, helping with the riding of his cock. Sometimes Tess would place her hands on Bryan’s washboard abs, riding up and down, then arch her back, continuing to ride the cock with her cock springing up full mast and then returning from leaning forward to kissing Bryan, then arching her back over and over. Tess rode Bryan for a long time like a woman possessed, screaming in pure ecstasy for 30 minutes with her 36DD breasts bouncing up and down constantly.

Tess switched to reverse cowgirl, riding Bryan’s cock like rocking a horse, eventually with Tess’s cock springing straight up. Tess continuously rode Bryan’s cock up and down, leaning forward and back, occasionally with Bryan moving up to kiss Tess on the back of her neck with Tess’s breasts constantly bouncing. After a while of riding Bryan’s cock, Bryan said, “I can’t hold on anymore. I’m ready to cum.”

Bryan almost yelling, announced, “I’m cumming…” Then with one last great thrust, Bryan slammed his cum into the deep of Tess’s ass. Tess reached down and just grabbed her own cock, and it erupted into a powerful orgasm, spraying cum all over her and leaking into the bed. Exhausted, Tess collapsed with Bryan still on top of her, with his cock buried inside her, shrinking. Tess felt globs and globs of cum leaking out of her ass. Bryan said, “Wow, I’ve never had a woman like you.”

Tess swung around and started kissing Bryan passionately. She collapsed onto Bryan, both tired from hours of intense lovemaking. They kissed with Bryan cuddling Tess until they both fell asleep into the morning. Tess kissed Bryan one last time. Bryan said to Tess, “I’m here twice a month, love to see you again.” Tess smiled at Bryan, “Of course.” She walked out of the truck cab, walking off into the sunrise.