The Truckers Wife (Sissy, Crossdressing, Gay)

I stood behind the register, watching as Bryson grabbed his energy drink and pack of cigarettes. He was the only one in the store, but it was almost 3 am at a truck stop in the middle of nowhere — so that was to be expected. “Another long haul?” I asked him as he placed his things on the counter. The man nodded, adjusting his hat. “Yup. I’ll be away for almost an entire month.” I pursed my lips together as I rang up his total. “Sorry to hear. I bet your wife hates that.” The man chuckled, “I suppose — but she loves my paychecks, I can tell you that much.” I laughed. Working at such a remote truck stop — I pretty much only serviced regulars like Bryson. It was an easy job — even if the pay was next to nothing. “That’s a shame — I hope she takes care of you when you’re home,” I added, placing his things into a bag as he paid. Bryson smirked, glancing up from the card reader. “She sure does, besides, when I leave she makes sure to send me off with some things to… keep me occupied.” His smirk grew devilishly. My curiosity was piqued. “How so?” He chuckled darkly, looking around to make sure no one was within earshot. In truth, there likely wasn’t anybody around for miles. “Well…” The man began, lust in his voice. “My wife likes to wear my favorite pair of lingerie for days up until I leave. Then I take the clothes with me, her naughty, womanly scent lingers on the fabric for days and days.” He winked as the blush filled my cheeks. “Perfect for those lonely nights.” I swallowed hard, my pupils dilating. “Damn… Lucky guy” was all I could muster. The mere thought of Bryson snuggling up in the back of his truck with his wife’s dirty panties up to his face was exhilarating, to say the least. Bryson noticed my reaction, a knowing smirk spreading across his face. "You seem mighty interested there, boy. Want a peek?" I whimpered softly, my face burning hot. "I-I couldn't. That would be wrong..." “Not at all. In fact… I think she would love knowing that another man is enjoying her sexy lingerie.” His smirk grew. I bit my lip. Sure, it was dirty, but it had been so long since I’d been with a woman — a whiff of Bryson’s wife's worn lingerie would make my knees turn to jelly. “P-perhaps a quick peek won’t hurt?” Bryson smirked, “Good boy. I’ll be back.” He rushed out of the store, leaving me with my dirty thoughts. Thankfully, he returned quickly, a plastic bag in hand. Bryson placed the bag on the counter with a knowing grin. I peered inside, my heart racing. A delicate black lace bra, stockings, and matching panties lay crumpled at the bottom. Even from here, an intoxicating scent wafted up –- a heady mix of floral perfume and something more primal. My mouth went dry as I leaned in closer, inhaling deeply. The musky aroma of a woman's intimate areas filled my nostrils. I could almost taste her on my tongue. Heat rushed to my groin as vivid images flashed through my mind –- Bryson's wife writhing in pleasure, her juices soaking into the lacy fabric. "Go on, take a closer look," Bryson urged. With trembling fingers, I reached into the bag. The silky material slid across my skin as I lifted out the panties. They were still slightly damp. I brought them to my face, breathing in her scent. My cock strained against my jeans. "She wore those for three days straight," Bryson said gruffly. "Can you smell how wet she got thinking about me?" “Mmh~” I nodded weakly, unable to form words. My entire body tingled with arousal. I wanted nothing more than to bury my face in those panties and pleasure myself right there behind the counter. I held the panties out, the threads were so thin that the fluorescent light shone right through them, the wet spots were clear as day as my mouth watered. “Fuck…” I moaned, unable to hold back. Under his shorts, I noticed Bryson’s cock bulging and tenting. That made my mouth water even more. “You know…” The man began, his devilish smile growing. “You look kinda like my wife.” “Wh-what?” I whimpered, pupils dilating. He nodded, his eyes scanning me up and down. “Petite, delicate, dirty blonde hair.” He laughed, “Even your ass looks just like hers.” The blush in my cheeks seared hot enough to put the sun to shame. Bryson leaned in closer, his eyes gleaming with mischief. "I bet her lingerie would fit you perfectly. Why don't you try it on?" My jaw dropped open in shock. "I-I couldn't possibly! That's your wife's dirty lingerie..." "Aw come on, where's your sense of adventure?" He teased, his voice low and gravelly. "No one else is around. It'll be our little secret… Besides, I can see how fucking hard you are getting." I swallowed hard, my mind racing. The thought of slipping into those delicate lacy garments, feeling the silky fabric caress my skin where it had caressed hers... It sent a forbidden thrill through my body. "I… Fuck" I whimpered, even as my fingers itched to reach for the lingerie. Bryson's gaze raked over me appraisingly. "You've got the perfect figure for it. Slender, smooth, just the right curves in all the right places. I bet you'll look absolutely stunning." His words sent a shiver down my spine. No one had ever spoken about my body that way before. I felt simultaneously embarrassed and oddly flattered. "Why don't you start with the bra?" Bryson suggested. "Test the waters?" I reached into the bag with trembling fingers. The bra was even softer than I imagined, delicate lace and satin sliding across my fingertips. I couldn't resist rubbing the fabric between my fingers, marveling at its silky texture. "O-okay," I whispered, heart pounding. "I'll try it on." “Good boy.” Bryson's eyes lit up. He circled around the counter, coming to stand behind me. "Here, let me help you with that," he murmured. His large, rough hands grasped the hem of my shirt. I shivered as his knuckles grazed my bare skin. Slowly, he lifted my top, exposing my slim torso. I raised my arms, allowing him to pull it over my head. I whimpered, my heart racing and my mind turning to mush. I knew this was wrong… but then why did it feel so right? Cool air hit my bare chest. I crossed my arms instinctively, suddenly feeling very exposed. Bryson's hungry gaze roamed over my body. My nipples hardened immediately, pressing against my forearm. "Beautiful," he breathed. "You're even prettier than I imagined." His compliment made me blush furiously. No one had ever looked at me like that before - like I was desirable, sexy even. It was intoxicating. Bryson unhooked the bra, holding it out for me. "Arms through the straps," he instructed gently. “O-okay~” I obeyed, slipping my arms into the delicate straps. The cups settled against my chest as Bryson fastened the hooks behind my back. The lace felt incredible against my sensitive skin. "There," Bryson said, his voice husky. "Take a look." I turned to face the mirror behind the counter. My breath caught in my throat. The black lace contrasted beautifully with my pale skin. The bra fit perfectly, as if it had been made for me. For the first time in my life, I felt truly pretty. My hard nipples brushed against the lace -– poking through the threads Bryson’s hand slipped around my waist, pulling me into his body. I whimpered, the scent of his wife’s perfume on the bra and his own manly scent created a dangerous cocktail in my head. His fingers stroked my exposed hip, circling around to my slender stomach. “You look even hotter in the bra than she does.” He laughed darkly. “Now… Ready to move onto the panties?” I bit my lip, my mind racing. Could I do it? Could I take that next step? Normally, I couldn’t imagine it — but the bra seemed to have awoken something in me… and I needed more. I looked up to the man, the corners of my lips curling into a smirk. “Yes, sir~” “Good boy,” He praised, “Now take those pants off for me.” I paused for a moment, then slowly unbuckled my belt. My hands trembled as I unzipped my jeans. I hooked my thumbs in the waistband and pushed them down over my hips. They fell to my ankles with a soft thud. I stood there in just my boxers, feeling incredibly exposed. My cheeks burned with embarrassment as Bryson's eyes roamed over my body. But there was also a thrill of excitement coursing through me. "Those too," Bryson said, nodding at my underwear. Taking a deep breath, I slid my boxers down. My semi-hard cock sprang free, bobbing slightly. As the cool air hit it, it began to stiffen further. Bryson chuckled. "Look at you, getting all worked up. You're loving this, aren't you?" I whimpered softly, unable to deny it. My cock was now fully erect, pointing straight out from my body. A bead of precum glistened at the tip. "Let's get those panties on you," Bryson said, handing them to me. With shaking hands, I took the delicate lace garment. I stepped into them, sliding them up my legs. The silky fabric felt incredible against my skin. As I pulled them into place, my hard cock strained against the flimsy material. The wet spot of his wife’s juices pressed up against my shaft, making me shiver. I turned to look in the mirror again. The sight of myself in the bra and panties made me gasp. I looked so feminine, so pretty. It was humiliating to see myself this way - but also incredibly arousing. My cock twitched, a damp spot forming where the head pressed against the lace. "You look perfect," Bryson growled. "Such a pretty little thing." I spun around, admiring the black lace as the pantie string buried between my bubbly cheeks. “How does it feel? Being turned into such a little slut?” I whimpered, biting my lips. It felt… So fucking dirty — yet so sexy at the same time. The scent of her perfume and womanly musk filled the air — melting away my rational thoughts. Bryson's hands slid down my sides, coming to rest on my hips. He spun me around to face the mirror again. I gasped as his rough palms cupped my ass cheeks, kneading the soft flesh. "Look at that perky little butt," he growled in my ear. "Just begging to be spanked." Without warning, he brought his hand down hard on my right cheek. I yelped at the sharp sting, my cock twitching in the panties. "You like that, don't you, you little sissy slut?" Bryson taunted, groping and squeezing my ass. "Look how hard you are, straining against those pretty panties." I whimpered, unable to tear my eyes away from our reflection. Bryson towered behind me, his large hands roaming possessively over my lace-clad body. I looked so small and delicate in comparison. He slapped my ass again, harder this time. I cried out, my hips jerking forward involuntarily. “Ohhh fuck~” "That's it," Bryson purred. "Moan for me like the sissy slut you are." His fingers dipped between my cheeks, rubbing teasingly over my hole through the thin fabric. I gasped and squirmed in his grasp — pushing my ass back as my tight hole puckered. "P-please," I whined — my voice breathless. "Please what?" Bryson asked, his voice husky with lust. "Please fuck your tight little sissy ass? Please make you my bitch?" I moaned wantonly, beyond shame now. "Yes, please," I begged. "Make me your sissy slut." His smirk grew as he pulled his hand back from my reddening ass. “Happily… Though, I think we can doll you up a little more.” Bryson’s gaze fell to the makeup tucked away at the corner of the store. It wasn’t a wide selection — but there was enough to doll me up like a little sissy whore. I watched with bated breath as he walked towards the small make-up section, picking out some bright red lipstick and eye shadow. My heart skipped a beat as he came back with the girlish make-up in hand. “Now, let’s get you nice and pretty.” Bryson approached with the makeup, his eyes gleaming. "Hold still, princess," he murmured. I trembled as he uncapped the lipstick. The waxy red tip glided across my lower lip, leaving a trail of vibrant crimson. He traced my upper lip carefully, filling in the curves. "Rub your lips together," he instructed. I obeyed, feeling the creamy texture spread. When I parted my lips, they felt fuller, more luscious. Bryson's thumb brushed the corner of my mouth, smearing a stray bit of red. Next came the eyeshadow. "Close your eyes, baby," he said. I felt the soft brush sweep across my lids. Back and forth it went, depositing shimmery powder. "Open." I blinked, unused to the weight on my lashes. In the mirror, my eyes looked bigger, more feminine. Bryson's fingers tangled in my hair, mussing it artfully. He stepped back to admire his handiwork. "God, you're gorgeous," he breathed. "A perfect little sissy doll." I gazed at my reflection in awe. Glossy red lips, smoky eyes, tousled hair. Combined with the lingerie, I looked like a completely different person. Like a girl. My cock throbbed against the lace panties. “Th-thank you… Sir.” I whimpered, my heart racing like a stallion. I always had a girlish figure — a delicate and feminine personality — and I just needed a real man to let that personality shine. I ran my hands down my sides, feeling the lacy panties and bra hugging my curves. My lips were red and plump — and my eyes popped with the shadow. I looked… So sexy. Bryson chuckled — eyeing me like a predator that had cornered its wounded prey. At this point, the bulge in his pants was a full tent — his cock straining to be let free. “Your lips look so plump and sexy…” He groaned. “Though, I think they would look even better around my cock.” I whimpered, staring up at him through fluttering eyelashes. I licked my lips, the delicate fabric against my hard nipples made my entire body shiver. My hands moved with a mind of their own as he continued to massage my perky ass. With trembling fingers, I began to unbuckle his shorts. The man groaned, his wife’s scent filling the air between us as my own pre-cum stained the fabric of her panties. “That’s it, whore.” He chuckled, fingers digging into my cheeks. “Be a good little sissy and pleasure my cock.” His words sent a forbidden thrill throughout my entire spine. I bit my lip as I slowly unzipped Bryson's fly. My heart raced as I reached inside, feeling the heat radiating from his groin. My fingers brushed against coarse hair, then wrapped around his thick shaft. I gently pulled it out, gasping softly as it sprang free. Bryson's cock was magnificent. It was long and thick, the veiny shaft leading to a swollen purple head. It wasn't fully hard yet, but it was already impressive. I could feel it pulsing in my hand as it continued to stiffen. "That's it, baby. Get a good feel," Bryson growled. I whimpered as I tentatively stroked him. His skin was so soft, yet the shaft was rock hard underneath. My small hand could barely wrap all the way around its girth. I marveled at how it grew even larger at my touch. Pre-cum ran down his shaft onto my finger. Bryson groaned in response. Encouraged, I began to stroke him more firmly. Up and down I moved my hand, feeling every ridge and vein. My own cock strained painfully against the lace panties. I was so turned on I could barely think straight. All I knew was that I needed more of Bryson's incredible cock. “Mmh, that’s it. Dirty whore.” The man sneered, “My cock is ready for your slutty, sissy mouth.” I bit my lip, my mouth watering as I slowly fell to my knees. I knelt before Bryson, his massive cock bobbing inches from my face. Up close, it was even more impressive. Thick veins snaked along the shaft, pulsing with blood as it grew fully erect. The head was an angry purple, glistening with pre-cum. I continued stroking him slowly, marveling at how my small hand barely fit around his girth. His musky scent filled my nostrils, making my head spin. It was intoxicating –- all man, earthy and primal. My mouth watered as I breathed him in. My eyes drifted lower to his heavy balls. They hung low and full, swaying gently as I pumped his shaft. I could almost feel how swollen they were with cum, aching for release. The coarse hair dusting them tickled my knuckles as I stroked. “Dirty slut. You were born to be on your knees, playing with a real man’s cock, weren’t you?” He groaned, thrusting into my hand. I whimpered, “Y-yes, sir. I was born to be a sissy slut.” The words were a sin on my lips — but they tasted so fucking good. Bryson's scent grew stronger as his arousal increased. Sweat beaded on his inner thighs, releasing more of his masculine musk. It mingled with the lingering perfume on the panties I wore, creating an intoxicating cocktail. "That's it, princess," Bryson growled. "Worship my cock like the little sissy slut you are." I leaned forward, my hand holding the base of his cock as my mouth opened. My tongue lashed against his tip — the salty precum burst with flavor on my tastebuds as I let out another moan. “Ohhh~” My tongue lashed against his wet tip like a whip — more pre=cum oozing out as I took his shaft deeper into my mouth. “Fuck!” The man groaned, gripping the roots of my tattered hair as he urged me to take him deeper. “That’s it, fucking filthy whore. Take my cock in your little sissy mouth.” My hands left his shaft as it disappeared into my mouth. I gripped his thighs, gagging as the taste of his dirty, salty shaft filled my mouth. It was delicious. My tongue lashed against the rod, his moans urging me forward. I bobbed my head eagerly, taking more of Bryson's thick cock into my mouth. The salty taste of his pre-cum coated my tongue as I sucked and licked. My lipstick left red smears along his shaft. "Mmph," I moaned around his girth, my eyes watering as I struggled to take him deeper. The head of his cock hit the back of my throat, making me gag slightly. But I didn't stop. I wanted more. My mind raced with a million thoughts — but I couldn’t focus on a single one. This felt so right — I belonged on my knees, wearing slutty lingerie and pleasuring a real man. Bryson's fingers tightened in my hair, guiding my movements. "That's it, baby. Take it all like a good little cocksucker," he growled. I hollowed my cheeks, sucking harder as I slid up and down his length. My tongue swirled around the sensitive head, teasing the slit. More pre-cum leaked out, and I eagerly lapped it up. Though it was my first time sucking cock, some primal instinct seemed to take over. I found myself moaning wantonly, drunk on the taste and smell of Bryson's manhood. My own cock throbbed painfully, trapped in the lacy panties. Bryson began to thrust his hips, fucking my mouth as I held onto his hairy thighs for dear life. I relaxed my throat, letting him use me. Tears streamed down my cheeks, smearing my makeup. But I loved every second of it. As I took his cock, I noticed headlights in the gas station windows. Another truck pulled in. I whimpered, Bryson’s cock down my throat as I latched around his shaft. The man groaned, looking over his shoulders. “Ahh… That must be Jackson.” He smirked down at me. “When I went out to get the panties and bra, I also called Jackson and told him to pull in. He loves little sissy girls just as much as I do. I hope you don’t mind.”