tagTransgender & CrossdressersDaddy at the Truckstop Pt. 01

Daddy at the Truckstop Pt. 01


This was an encounter that almost happened with a Daddy a while back. We talked about doing this for a first meet to make up for other times that didn't work out, and while talking about it with him was undeniably hot, it ended up not happening for a few reasons, chief among them safety. I think about how hot it would have been to smash a lot of my boundaries this way, though. Enjoy, and comments wel-cum :)



I couldn't believe I agreed to this, but here I was. The truck stop is maybe an hour from my house, and I was pulling into it from the highway now, dressed in stockings, panties, and my schoolgirl skirt stuffed underneath the pants I was wearing. Right next to me was my sissy bag, with everything else I'd need today - however it turned out. This would be my first time meeting 'Daddy' as I've been calling him, and the first time I'd be dressed in public. We'd been chatting for so long, and it was finally time for me to meet him. Coming here is what he required of me, with everything to dress up.

I pulled into a space, and began the rest of my transformation. I was a little early, I thought, so I had time. I took my pants and shoes off, stowing them in the back, and brought out my 6 inch heels with ankle straps, blond wig, what little makeup I had, and the mesh arm gloves. There wasn't a lot of room in my little car, but I managed to strap the heels on over my fishnet stockings, and set the wig in place with some adhesive, apparently very strong, and did my best with some eyeshadow, fake lashes, and slutty red lipstick. Up close, you could tell I was a stocky sissy, but from far away I thought I'd be passable enough. Just as I finished, I was about to text him that I was ready, but I heard a tapping on my window. Startled, I rolled down my window a bit, and said "'Hi Stacey". I had told him what my car looked like, he had been watching me for at least a little while. Then he said 'Bowling Ball', the safe-phrase we had agreed on before, and I knew it was Daddy.

I nodded "Hi Daddy, it's nice to meet you." And I got out of the car with my bag to go with him. I tottered on my heels, so nervous, as he led me, his hand starting on my ass, and moving up to the back of my neck and squeezing just a little, directing me towards his white van parked about 50 ft away. He opened the side and got a small backpack of his own, and said "Give me your bag, Stacey."

Setting it into the van and reaching in, he pulled out the leather cuffs and collar I brought, and a coil of rope. "Turn around." he said, and I did slowly. Knowing what was next, he placed the cuffs on my wrists, strapping them securely in place, pulled them behind me, and with a 'click' he used something to fasten them together. "That lock should keep you secured just fine, Stacey." I tested my bonds, and I had almost no slack. I was trapped. Next came the collar, sliding around my neck, and this time he showed me the lock as he secured the strap of leather around my throat, not tightly, but not loosely either. Clipping the chain leash to my collar, and placing the rope into his pack, he shut the van and started to lead me away from it, out into the parking lot. "Ready, Slut?"

"Yes Daddy." I meekly said, my cheeks burning.

There were more than a half dozen trucks in the parking lot, and Daddy slowly led me around near most of them. I could see some of the truckers looking at us, and I felt so exposed in his hands like that, under strangers' eyes. We had talked about my fantasies, and what he liked to do with sissies, and my horniness finally got the better of me, knowing that I needed to be taken under his control. After a few minutes of showing me off, he led me towards the back of the lot where the woods started. Past the edge of the trees, not doing all that much to hide us, was a fallen tree trunk, a gnarled stump, and several smaller trees surrounding us. Daddy stopped here, took a towel from his pack, laying down underneath us, and turned to me.

"Well, wasn't that fun, Stacey? Now I think it's time to break you in a bit, I've waited long enough to use you". He groped at my ass, the back of my neck again, and brought his thumb to my lips, pushing it in as I swirled my tongue around it. "On your knees, it's time for you to be my slut." Restrained and unsure of my footing, I did my best to drop to my knees, with Daddy helping me down a little.

Once I was there, he grabbed my chin, making me look up into his eyes, and he said "One last chance, Stacey. I just use you here, take your mouth and pussy, and then stop there.. or, I make those fantasies come true that we talked about. Remember, if it's the second choice, you only get to use the safe phrase twice, and then only to take a break. Otherwise, there's no backing out." The choice raced through my mind as he unzipped his pants, pulling out his hard cock, it must have been 8 inches, and tracing my lips with the tip of it. "What's it going to be, slut? If you don't give me an answer at the count of 3, I'll chose the second option for you."

My eyes widened as I considered this one last time. "ONE..." He poked the head of his cock past my lips for a second, hitting the tip of my tongue and pulling out again. "TWO..." as he wrapped the leash tight around his fist. After a longer pause, he stared at me, his cock poised at my mouth, waiting an extra moment for me to speak up, and I couldn't bring myself the choose the first option, so turned on, so horny that he'd made me. "THREE." I closed my eyes, opened my mouth wider for him, as he pulled on the leash, forcing my head onto his throbbing cock. "Good Girl. We're gonna have so much fun today, slut."


Daddy guided my head with the leash as I sucked him. It had been a while since I had a cock in my mouth, so he only gagged me occasionally to get me used to it. "Good, Stacey, mmm. You need more practice, but that's why you came today, right?" I could only nod and moan into his cock as he thrust it in again, gagging me. With my hands cuffed and locked behind me, I was helpless to his whims, just as we talked about. It was scary to be tied and exposed like this - dressed like a schoolgirl slut- in the woods next to the truck stop, but it was turning me on so much, too.

I closed my eyes, lost in the sensations of his cock between my lips, and after a minute he let some slack into the leash. "Keep sucking, Look up, slut." I opened my eyes, bobbing on his cock, and he was holding a camera. He took shot after shot of his cock stuffed in my face, and my eyes went wide. I knew it was going to happen, but they were now the first pics of me sucking cock, dressed like a schoolgirl... "These are a good start, slut. We'll make you into a little porn star, yet." laughing to himself slightly as he pulled the leash, and my mouth, back onto him.

After a couple of minutes of getting lost in my sucking, he pulled me off of his cock. "Time to get you used to having a cock up your boipussy, bitch." he gruffly said as he pulled my leash and forced me to shuffle on my knees over to the gnarled stump nearby. He made sure I was bent over it, and tied my knees & ankles so that they were at either side of my perch, forcing my ass open for Daddy. I could hear him tearing the wrapper to a condom as he came into view, then sliding it over his now very hard cock. "I'm going to give a choice, Stacey, since you've been a good little slut so far. This is going up your ass one way or another, and to help keep your squeals down, I can give you this gag." as he pulled a bright red ball gag out of the pack now resting beside me. "Of course, if you have this in, you can't use the safe word, but a good little slut like you won't need it for a simple fucking, am I right?"

I thought about it for a moment before looking up at him, whimpering "Yes Daddy, you're right.. if you think your slut needs a gag, she should wear one.." Daddy gave me a crooked smile.

"Good gurl." he said as he pushed the ball between my teeth and painted lips, buckling the strap in the back. He stepped away for a moment, grabbing his camera before coming back into view, taking more photos of me helpless. He came back around behind me and started to feel my ass. "Keep your eyes front and down until I tell you, slut." I kept my gaze cast downward.

I felt a cold sensation on my boi hole, guessing that it must be lube. "We don't want you hurting too much, do we?' He chuckled again. He slid one finger in, probing me, followed by a second, and then a third. I winced at some pain, but I also started to moan into my gag. "I think you're just about ready." I saw his hand reach into the pack again out of the corner of my eye before he said "Look behind you, to your left, slut." I obeyed, looking back as far as my position would allow, and I gasped into my gag. I could see three truckers at the edge of the clearing, rubbing their tented pants as they watched the show we were putting on. My mind raced as I saw more movement behind them. One? Two more men walking this way? I wasn't able to tell fast enough as Daddy slid a thick black cloth over my eyes, and tied the ends of a blindfold behind my head tight as I whimpered into the gag.

"Now things are getting interesting, Stacey, wouldn't you agree?" Daddy growled as I felt what must have been his cock start pushing its way into my loosened hole, as I he pulled on my leash, choking me slightly as I moaned in pain. A few minutes passed as he teased it in and out, inch by inch, filling me up as I tried to adjust to the burning in my ass. Part of me wanted to use the safe word before remembering that I couldn't speak, but I knew that I needed this, to be treated like a cheap whore, fucked without any choice, giving myself to Daddy. Once he was buried all the way into me, he rested his cock in my stretched out boipussy until I quieted down some, and he began sawing his meat in and out of me, pulling on the leash, pulling on my hips, occasionally slapping my ass while muttering "Yeah, you're a tight fuck, Stacey. You're going to be a good whore for Daddy, I have plans for you. Mmm yeah bitch, moan for me."

In spite of myself I had already started to feel good from his fucking, his cock hitting that spot deep inside that was driving me wilder with lust, balancing out the discomfort, and I started moaning into the gag, beginning to meet his thrusts as best I could, tied and prone as I was. After a while of intensified fucking, Daddy pulled out and I heard him come over to my front, loosening my ball gag and letting it dangle around my neck. I heard him slip off the rubber of the condom before pushing his engorged member into my mouth. No sooner than had he entered my mouth, he started to cum hard. A couple of shots hit the back of my throat as I started to cough, and he pulled out, the next spurts landing on my face. "That's a good slut, swallow what you had left in your mouth, and leave the rest on your lips."

I gulped what remained and rested for a moment saying 'Yes Daddy' as I relaxed my jaw.

Still massively turned on from the intense fuck, I waited anxiously, trying to rub my hard cock against the tree stump for a little more stimulation. I heard some rustling for a couple of minutes before I felt a smack on my ass, startling me. "Now, now, slut. No getting off on a tree stump. You still have work to do." He spanked my ass a few more times, and I let out a little yelp for each one. "Who do you belong to, Stacey?" SMACK.

"You, Daddy!" -SMACK

"What are you, Stacey?" -SMACK.

"I'm Daddy's little whore!" -SMACK.

"Good gurl, you're coming along nicely." Daddy spoke off to the side.

I immediately felt another hard cock wrapped in a condom at the entrance of my pussy as two hands gripped my hips. It must have been one of the truckers! Daddy was already starting to share me with them, and not just putting on a show! In the chats, he said he'd turn me over to whatever truckers were there, wanting to use me, and pimping me out. He said it was the only way a bitch like me could learn to be a good whore, but I didn't really believe that he'd do it.. not at a first meeting like this! But there I was, tied and dressed in the woods about to be fucked by a man I couldn't see. I started to whimper as another cock pushed past my lips, this third man tugging at my leash, pulling my head onto his cock as the one behind me buried his cock up to the hilt. Was it too late to use my safe word? Would it matter, since I would only get a break, and they would all start using me again? I didn't have much time to think as I was lost in a haze of lust again, cocks stuffed in both ends.

"Don't worry, I'm making them all use protection. Are you surprised, Stacey? I hope you didn't think I was kidding about fulfilling those fantasies we've talked about for so long. Be a good whore for these men, and make them happy. There are more waiting..." I heard Daddy laugh to himself off to the side. My god.. he was turning me into a whore for these strangers in the middle of nowhere, and as scared as I was, I was lost deeper in the overwhelming lust I felt as the two men began using me harder.

-To be continued.

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