Sissy has a flat tire, will she be rescued?

I was on my way to meet Kyle at our usual rendezvous point on a deserted road off ironically-named Highway 69, when I suddenly heard a rumbling noise and found it difficult to steer. “Shit”, I thought as I pulled off to the shoulder, “not a flat tire.” I was not dressed for such a misfortune with my fuck-me boots, fish-net nylons, black mini-skirt, pink slutty top, and blond wig. My first concern was about breaking a nail before I realized that I have never changed a tire and would have no idea how to go about doing so.

Darkness enveloped the car and I wasn’t sure where I was on the highway as there were no visible markers. Complicating matters further was a light rain which I listened to while staring at my reflection in the wind shield. I took a deep breath to calm the anxiety gripping me as I desperately thought of a solution. First I would have a look to see what I was dealing with. It might not be so bad, I thought. I grabbed my purse which contain a small flashlight and stepped out cautiously.

Unsteady in my high heel boots, I took small sissy steps to the back of the car. The clacking of my boots on the pavement pieced the silence of the night. I sighed when I saw that indeed the tire was totally flat. Unsure what to do next, I returned to the car, but the door was locked. All the doors were locked. Somehow I had locked the door by accident and now, looking like a lost hooker in the rain, I raged against myself. “You stupid bimbo, you’re such ridiculous slut. Always cock on the brain. What a fucking loser you are.”

Not able to think of an alternative, I searched for a rock on the side of the road to break a window so I could at least get out of the rain. So focus I was I didn’t hear the pickup approach until I stood up. “Oh gawd, now what?” I thought. Not able to hide at this point, I simply looked away as if I’d disappear from view. The vehicle stopped, however, and I heard a window roll down. A man voice asked if I needed help. I hid my face as best I could with the bangs of my wig. “No it’s ok. I’ll be fine,” I replied in a soft, feminine voice, but he didn’t move.

“Looks like you have a flat. You’re not dressed to replace a tire, miss. I can help you. It’s no problem,” he assured me. But I thought that once he realizes that I’m no miss, he’ll disappear in a flash. After he parked and he approached to assessed the situation, he told me to warm up in his truck as he could see I was trembling from the cold and wet. I hesitated for a moment, not sure if I should trust this stranger, but I so needed to dry up that I walked to the truck in wobbly sissy steps. Inside I found to heat so soothing I began to relax and think about Kyle.

We had been meeting in this secluded area every few weeks for about a year after we met online. He was married and I was his steady “girl” on the side, though I’m sure there were many others. I would suck his beautiful large uncut cock in his car until he would explode in my mouth. He always insisted I swallow every drop which I was so happy to do. Sometimes we would talk a bit before I blew him. I loved our chats as it made me feel like a normal girlfriend, but usually he would pull out his penis and impatiently tell me to suck it. Lately he had been pressuring me to fuck. I was reluctant because I feared it would hurt terribly, given his size. Still, I did want to please him and feel him inside me. It was all I could think about and had been practicing stretching my hole in anticipation, so tonight I was going to give in. But now I was stuck in a stranger’s truck and I was worried, on top of everything else, that Kyle would be angry that I wasn’t there to service him.

Suddenly the door opened and my rescuer jumped in the truck. I held my breath as his eyes slowly scrutinized my body. After a pause he told me his name was Bobbi. “Nice to meet you Bobbi, I’m...ah... Amy” I replied hesitantly, not wanting to give my real name. Without any judgement or disrespectful tone he told me that he reached the same conclusion about my car and offered to take me back to town. I was relieved he was overlooking the fact that he had a weirdo sissy cross-dresser in his truck. “I would so appreciate that, but I don’t want to inconvenience you...” I said with my eyes lowered.

He assured me he’d be happy to give me a ride, but he didn’t move. He simply smiled gently and asked “so Amy, what are you doing out here? Sorry, I don’t mean to pry, but it’s a pretty dreadful night to be out... You don’t seem dressed for the country.” The question caught me off guard. “Well, I... I um... was meeting a friend” I replied. “Oh I see”, said Bobbi, “Well I can drive you there if you like. Were you going to a party?” Again I was off balance “No, no not a party. No, he’s probably gone now. It would be better to go back to town” Still Bobbi didn’t move. Instead he continued casually “So you were suppose to meet a guy friend. I’m sure he’ll be disappointed that you’re not there, I would be.”

I swallowed hard; “Was this a trap?” I wondered. I looked up and saw him smiling at me warmly. He was handsome and had kind eyes. I blushed. I didn’t know what to say and we were silent for a moment. Finally I thanked for his help “I don’t know what I would have done if you hadn’t come along.” He reached out to me and put his hand on my knee “Don’t worry about it Amy. You can relax. I’m happy to help.” His touch felt so good and reassuring. We started talking about the weather and other mundane things, but soon the conversation turned more intimate. “Do you always dress like this, Amy? I mean, it’s very sexy.” I laughed “no, only for special occasions.” Bobbi moved his hand up my leg, rubbing it gently. “What kind of special occasions?” he asked. I smiled coyly and said nothing. Enjoying the sensation of his warm hand, I opened my legs slightly to encourage his fingers.

“That feels nice Bobbi,” I said, unable to resist his advance. I closed my eyes and let out a deep breath. He moved up my tight skirt, but suddenly recoiled when he touched the hard plastic. “Oh no, It’s ok” I quickly assured him. He looked at me confused. “Don’t worry... I know it’s weird... it’s just a little cage for my clitty.” I lifted my skirt to show him. “I’m a sissy as you can tell. My boyfriend wants me locked up. He knows I’m a perverted slut. Sorry, I don’t mean to turn you off” I said, eyes lowered.

“No, no... It’s kinda hot. It’s just I wasn’t expecting that.” Bobbi words were comforting. I look at him and felt hungry for his affection. I moved closer and place my hand on his crotch. I suddenly wanted him badly, not only because he rescued me, but it was so long since I’d been with Kyle or anyone else and I was missing cock so much. As I rubbed his jeans and felt the contour of his manhood, I was overtaken with desire. I took a deep breath and undid his pants. I pulled out his beautiful semi-hard cock, leaned in to kiss the head and then slowly slid my lips down the shaft. The taste of his delicious warm flesh in my mouth was intoxicating and I felt my clitty swell in its cage. I delighted in feeling Bobbi’s excitement grow as I continued to suck his cock and lick his balls. I felt his hand on my head gently at first, then pressing down more firmly, making me gag which I loved and made me suck harder.

I pulled up, gasping for air and was about to resume sucking, but stop as I was gripped by another urge. Noticing the rain had stopped, I reached for my purse and took out a condom and lube. “Bobbi,” I said as I bit my lip “please take me. Please fuck me.” Without hesitating, he got out of the truck, came to the other side and prepared himself. I was out too with my elbow resting on the seat, legs apart, ready to be taken from behind. I felt him pull my thong to the side and then massage my hole with lube. He penetrated me with a finger getting me to relax. Soon he pressed in slowly. It was tight and I flinched, but on the third try my ass accepted him and he started pumping me slowly and gently. It felt amazing! I moaned in pleasure. I wanted the soothing rhythmic fuck to last forever. I felt dizzy with pleasure as he lustfully reached climax. When his cum exploded inside me, his pulsations gave me an amazing warm sensation. Before pulling out he held me in a tight embrace. When he backed away, I turn around quickly to pull off the condom and lick the remaining cum from his shaft. As I savored his delicious white cream, I didn’t notice the car slowly approaching.

When I stood up, I heard a door close and saw a man standing looking at us next to his car. At first I didn’t understand, and then I realized it was Kyle who I never expected to see. I never would have thought he’d come searching for me. I pointlessly straightened my wig and my skirt as he approached. It was obvious what Bobbi and I had been up to. I glanced in the trucks mirror and saw my smeared makeup, but I acted as though nothing inappropriate had transpired. “Hi Kyle, I’m I glad to see you! This is Bobbi. He was helping me... with my car. I have a flat...” I said, my voice trailing off. He stared at the discarded condom on the ground and responded wryly “Looks like he was helping you with more than just a flat.”

“Look Kyle, I’m sorry, it’s not what you think. I locked myself out...” I said trying to defend myself. But Kyle interrupted “It’s exactly what I think. You fucking slut. You just can’t keep your panties on, can you? ”

“No Kyle, please don’t be upset with me... I... he was so kind... it meant nothing. I’m sorry...” I pleaded feebly. Kyle remained stoned-faced and replied “oh yes you will be sorry.” He swiftly reached for the lube on the seat of the truck, unzipped his pants, grabbed my arm and forced me to my knees. “Ouch Kyle, you’re hurting me” I complained, but he was unsympathetic. “Just suck it, you slut. It’s what you live for isn’t it? It’s all you think about, isn’t that right you pig, you fagot slut?” He was furious and though he frightened me, I was totally aroused. “Yes... It’s true... It’s all I want... Oh Kyle...” Faced with that beautiful cock I was overcome with desire. I trembled as I took it with one hand and began kissing it admiringly. I ran my fingers gently over the masculine veins that ran from the base to the foreskin which covered the thick head. I looked into his eyes as I slid its large head in my mouth.

I slowly rolled my tongue around and then under the loose foreskin as stroked the cock sensually. I sensed he was becoming impatient, so I sucked his firm shaft harder. I could not go much beyond the head as he was so thick and large, but still managed several inches, making loud slurping sounds as I did. “Oh that’s it... Keep sucking it slut,” Kyle moaned while pushing my head down. I was sucking wildly now and gagging, forcing me to pull out and gasp for air and then plunge back down. Kyle pulled my hair to direct me to his balls which I kissed, licked and sucked passionately.

Suddenly he lifted me up, turned me around, and forced me to bend down. He starting massaging my ass with lube and as he was preparing to penetrate me, I worried about the pain, but yearned to feel him inside me. He pressed in. I cried out, but he was indifferent. He pressed in again. It hurt terribly, but I focused on relaxing. Again he pushed, slowly stretching my rectum. Dizzy with pain, I thought I was going to faint as he inched deep inside me. As he continued his slow pumping motion, it started feeling more tolerable. With each thrust I moaned loudly. As Bobbi watched the scene unfold, his initial alarm gave way to arousal. I motioned to him to come closer when I saw him stroking himself over his pants. Now in front of me, he unzipped his pants exposing his erection. Immediately I grabbed his cute ass and started sucking him. It was so thrilling to be spit roasted, to know that soon I’d be filled with cum in my ass and mouth.

As Kyle kept fucking, now faster, the pain was replaces with a wonderful tingling, soothing sensation which made me moan loudly while Bobbi worked my mouth with his delicious cock. I was in cock heaven and the pleasure they provided transported me to ecstasy. I felt light and blissful as I experienced my first sissygasm. Little strands of cum oozed out of my limp clitty as I let a series of squeals and pleasurable moans. Kyle grunted and I knew he was close to orgasm as well. Grasping my hips tightly, he pushed in with a deep thrust. He let out a loud cry of pleasure and I felt his cock pulsate in my ass. He filled me with cum with a second and third thrust before pulling out. Then it was Bobbi’s turn to shoot his load of delicious warm cum, this time down my throat. I choked on it as he held my head tightly. Cum oozed from my nose and spilled from my mouth. I was surprised how much Bobbi had produced this second time. “Oh that was amazing,” I told him as I tried to straighten up. I grabbed his arms as my legs were weak at this point and I thought I’d collapse.

I was a mess. My wigs had fallen, my makeup was completely smeared, cum dripped down my legs from my aching ass over my torn nylons, my boobs were lopsided under my torn top and my boots were scratched and battered. Kyle laughed at me as he pulled up his pants. “Fucking whore” is all he said before leaving.
I looked at Bobbi who was still holding me up and I wondered what he thought of me now. I stumbled to the truck with wobbly sissy steps to retrieve my purse and when I did, a thought occurred to me. I unzipped a pouch inside the purse and found a spare key for the car I kept for emergencies. “I really am a bimbo slut” I thought to myself.