Big Bobby and Sweet Sally Ch. 02

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The road calls and Sweet Sally follows.
3.2k words
4.55
13.3k
10

Part 2 of the 3 part series

Updated 06/08/2023
Created 09/16/2017
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I woke up the next morning in the motel bed, naked and alone. My first thought was that Big Bobby had left me, that he had left and moved on to his next conquest. I let out a sad sigh, then my ears picked up the distinct sound of a shower head pumping out water, and a smile quickly crept across my face. After a yawn and a quick stretch of my arms, I sat up and saw Big Bobby's belongings still scattered around the room, as well as the dress I had worn the night before. Then I noticed the red thong lying beside it, still sticky with Big Bobby's cum.

I started to get hard thinking about the night before as my eyes were drawn to the bathroom door. I was just about to get up and see if he needed some company in the shower when I heard the water quickly cut off. A few minutes later, Big Bobby stepped out of the bathroom in all his glory with nothing but a towel wrapped around his body.

He eyed my slim little body and said, "Morning."

"Good morning."

"Glad to see you stuck around."

"You too. I, I had fun last night."

He moved in with a smile and a quick kiss on my forehead.

"As did I."

He dropped his towel and walked over to one of his bags, his large back and body on display before my very eyes. I started to get harder as I assumed he was ready for some more play, but then he pulled out a pair of boxers that he quickly threw on, as well as some jeans and his hat.

"I have to get moving."

"Really? So soon?"

"The roads a callin', babe."

He looked at me and saw my eyes go glum. Then he walked back over to me, still shirtless, and caressed my cheek.

"Were you serious about last night? About going on the road with me?", he said with hope in his eyes.

I returned his look with my own set of hope-filled eyes and said, "Of course I was serious."

He took his hand from my cheek and went and grabbed another one of his bags and tossed it on the bed.

"Then that's yours. Open it."

He threw on a shirt as I unzipped the bag. My eyes widened as I saw the contents. It was full of girlie clothes: dresses and shorts and panties and bras.

I was speechless, so he spoke for me.

"From here on out, as long as you're with me, you'll only wear what's in that bag. You're my girl now, and you're gonna look like my girl."

"But I..."

"I know, I know. It'll be an adjustment. But we'll work on it, okay?"

"I don't know what to say."

"Say yes."

I sat there still naked, thinking about the brilliant night of passion I had just experienced, and I wanted to experience so much more.

"Yes."

"Good. Now let's get to work on you."

Get to work on me? I didn't know what he exactly had planned, I mean I had a pretty good guess, but this was all so new and unknown to me. I pushed the thought out of my mind and started to look through the bag. First I picked out my undergarments, a pair of light pink panties and a matching bra that I lied on the bed next to me. Before I could pick out an outfit to go with the bra and panties, Big Bobby walked up to me with something in hand from another one of his bags, a razor and some shaving cream.

"Before you get all dolled up we need to take care of some things."

"Uh, okay."

"Take this razor and shaving cream, along with your bra and panties, and go into the bathroom. I want you to shave off all that body hair of yours, from your chest to your legs. Let me know if you need any help."

He pushed the razor and shaving cream into my hands.

"Um..."

"Like I said, if you're gonna be my girl, you gotta look like my girl. Do girls have hairy chests and legs?

"Uh...No."

"No, Sweet Sally. No they do not. Now like I said, I need to get moving. With or without you."

He reached for the bra and panties and put them in my free hand. Then he crossed his arms and looked down at me, and I knew what I had to do. I stood up, my girl-making items in hand, and walked into the bathroom and closed the door.

I now stood in the bathroom yet again, unsure of what I was doing or what had gotten into me. This whole thing was becoming a whirlwind of an experience that had maybe gone too far. I had quickly agreed to Big Bobby's proposal, but was it just because I was still held captive by the ecstasy of our previous night's passions? Was being Big Bobby's girl something I was really ready for? I wasn't so sure one night of feminized fun was enough to erase all the years of supposed heterosexuality I'd been living under.

That's when I looked in the mirror and scanned down my naked body, and at all the hair that would need removing. My hair was light, like I'd said before, and there really wasn't all that much of it to begin with. It wouldn't take that long at all to remove, actually. I placed the bra and panties on the sink and looked at the shaving cream and razor. What the hell, I thought. Not like you get this kind of offer every day. And its just hair, it'll grow back.

I made a quick effort of coating my body hair with the cream and then doing my best with the razor. Having never shaved my legs, or any other part of my body but my face, was a bit of a challenge at first. I did my best though and when it looked like the job was done I looked to the bra and panties.

"Here goes nothing."

I opened the bathroom door and stepped out as the new me, my body now smooth and hairless like the girl Big Bobby meant me to be. Now clad in the matching pink panties and bra, which fit snug against me and felt good, I leaned against the door jam to give him a good look and a little show.

"Well, what do you think?"

Big Bobby licked his lips and came straight up in front of me. He felt up the front of my panties and my growing erection.

"You look good enough to eat already."

"Thank you, Big Bobby."

He stroked me over the panties until I was good and hard. Then he walked over and reached into the bag of girlie clothes and pulled out what looked like two rounded mounds of skin.

"These are breast forms, my Sweet Sally. You're gonna put them in your bra you see. Make it look like your tits are the real deal."

He took me over to a full-length mirror hanging off one of the motel room walls and stepped behind me as he pressed himself up against my backside. I felt him hard against my panty clad ass and I nearly melted. Then I almost melted again as he put his hands into my bra and placed and secured the breast forms. He turned my head straight and had me look at myself in the mirror, my new self.

"Can you believe how beautiful you look now? How much like a girl you look now?"

It was true. Even without my wig on I could see how much the shaving of my body hair and the breast forms had started to transform me. And how my body reacted to the changes by putting a slight curve to my body, giving me a more feminine stance. With a bit of makeup and my wig on, I'd practically be the real deal.

I felt Big Bobby start to kiss his way up my back and then up my neck. His wet kisses and hot breath touched my skin and I couldn't help but moan. He squeezed me in a tight embrace as I heard the sound of his zipper being unzipped. I got so fucking hard as I felt him pull my panties to the side. Then his cock began to enter me as his hands moved to my hips and my hands moved to the wall on either side of the mirror. Yes, this was exactly where I wanted to be. How could I ever think otherwise?

I closed my eyes as he slid his stiff heat further up my ass. It was just like before, like last night, but in a way, it was better. He had loosened me up more than I expected, stretching and molding my hole to the specifications and contours of his cock. And after knowing what it felt like to take a cock, I now welcomed its entry inside me, rather than fearing it.

I craved his cock now. I pushed back on his cock now. As I spread my legs and my hole wider, he didn't hesitate to take more and more of me and make me his own. He was making me the girl I never knew I wanted to be. He was making me his Sally.

"Oh, Sweet Sally. God I love how tight your ass is."

"Tightest you've ever had?", I teased.

"Tightest damn thing my dick has ever touched."

"Oh, Big Bobby. Keep making me your girl. I want it so bad."

"As you should, Sweet Sally. As you should."

I opened my eyes and looked straight in the mirror, looked straight at myself and what I had become. My erection had grown so again my head was poking out from the top of the pink fabric of my panties, my new tits bounced in rhythm with Big Bobby's thrusts, and my mouth was filled with nothing but moans and ohhhs. I stared straight at myself, and then back at Big Bobby behind me, taking and using me as he pleased.

I couldn't stand it much longer, it was all so much to take in at once. And that's when I came, spaying all over the mirror right in front of me. My ass clenched on Big Bobby's cock and I saw him drop his head back and then release a guttural moan. Then I felt his seed released into my ass and tightest of tight holes.

He pulled out of me and wiped his cock clean on my panties, breathing heavy as he stepped back and sat on the bed. The panties were wet from the clean up of his cock, as well as his cum that now slowly seeped from my hole, but he didn't tell me to remove them. I was to revel in the wet panties and his cum, like a good little girl. As I straightened back up and turned to him, he ushered me over to the bed.

As I came closer I found he had already chosen an outfit for me, all lied out on the bed and everything. He had chosen a black tank top and denim short shorts for my first trip out into the world as his new girl. Right above the tank top was my red wig to complete the ensemble. I stared down at the outfit and wig and prepared myself for my transformation. I was excited, and by the look in his eyes, so was Big Bobby.

"Do you like it?"

"I love it. Thank you, Big Bobby."

"Anything for you my sweet."

He gave me a quick wink which caused me to blush. I couldn't believe the power this man already had over me.

"Now they may be a bit tight. But we'll fix that soon enough. But honestly..."

He ran his hand up my now smooth leg and gave one of my ass cheeks a sensual squeeze.

"...Tight fits you just right."

God he had a way with words.

"You're special to me, Sally. Something real special."

I blushed even more than before, and he seemed to really like that.

"Now get on and get dressed. I'm gonna load our stuff up in the truck. Then we're gone."

He stood himself up, and as he towered over me, he looked down and looked over my light and lean form. His eyes said they craved more, but his body knew the time had come to finally get moving. As he went to get to our things, he planted a solid smack across my ass that broke the stillness in the room.

"Oh!", was the only thing I could utter.

"Always time for more later, my little temptress."

He went to the bags and started organizing them. I turned back to the bed and the wardrobe that would be my new self while with Big Bobby. My toes curled as I ran a hand from the top of the wig to the bottoms of the short shorts. It was finally time to take Sweet Sally out into the world.

First, I slipped on the tank top, which was tight. Then I slipped on the short shorts, which were even tighter. I positioned the wig square atop my already short hair and went to the full-length mirror to look myself over.

The tank top fit tight against my now hairless chest, but the tightness of it squeezed against my bra and the breast forms which made me look like I had an honest to God decent rack on me. I was definitely all girl from the belly up. The short shorts were a bit too tight though. My legs looked girly for sure with my legs now smooth and bare as can be, but if you looked close enough at the shorts you could just make out my limp little dick.

I did my best to tuck it back, but with these being the tiniest shorts imaginable, the slightest of bulges was still evident. I worked the wig a little more, turning and positioning it until it looked just right, like my own red bob of hair. Another quick look in the mirror and a quick spin to check out my ass confirmed it, I really did look like a real life genuine girl.

Big Bobby came back in from taking out a load of bags and stopped dead in his tracks. His eyes widened with stunned excitement as he took in his first sight of me all dolled up, all smooth and delicate. They stayed that way as he walked up to me, and they stayed that way as I felt his arms wrap around my waist and pull me in close.

"Hi", he breathed out.

That's all he said. That's all he wanted to say. He let his tongue do the rest of the talking as he kissed me deeply and I felt his power. He was such a strong man and I was succumbing to every move he made. After his tongue wrestled with mine for a bit, less time than I truly wanted, he pulled away and his eyes caught mine in a deep stare.

"Hi there", I said as sensually as I could.

He kissed me again as he tasted me down to my core.

"Come on now. The road don't wait forever."

Both his hands went down to my ass, squeezing each cheek hard and with a forceful man's vigor. It was a challenge to get hard in my short shorts, but damn if he wasn't getting me there.

"Oh God, Big Bobby!"

His eyes were saturated in lust, and he looked like he wanted nothing more than to strip me bare ass naked and fuck me wherever he so chose to. And he would have, I had no doubt, except check out time was in five minutes.

"We'll play later."

"Promise?"

"I promise."

He gave me another quick kiss, another quick slap on my little ass, and then had me grab whatever was left in the room. The room was left as we would soon leave many rooms, a hot and sticky mess that smelled of two bodies becoming one.

I slipped on some flip flops before stepping out into the sheen of the bright morning sun, as well into the new life that lied ahead of me. Big Bobby pointed out his semi-truck, as blood red as his hat, and told me the door was unlocked and to load up the last couple bags. He had to return the key, then he turned to head to the office, leaving me there to warily eye the other trucks scattered about the parking lot. I breathed in a courage-building breath, then I started to walk to his truck, walking my first steps in my new body.

There were some glances from open truck windows as hungry eyes fell upon me. I was a fresh lamb among wolves, but I now belonged to the biggest wolf on the block, and my steps became less shaky as that thought circled my mind. Even if they thought I was a girl, which most probably did, they would never dare touch Big Bobby's prime new prize.

They watched me all the way to Big Bobby's truck and not one had a word to say. Once I was at his passenger side door I decided to be bold and test their hunger. I dropped one of the bags to the ground and then I bent over, presenting my ass in my denim short shorts to the whole lot of them. That's when I heard a faint whistle, and I shot back up and glared down the truck it came from. There was not one peep from them after that.

I saw Big Bobby exit the motel office and head toward me. I turned and faced the diner where I work, or worked, I guess would be the better word. My shift started in a few hours, but I'd be long gone on the road by then. It was the last part of my old life, my less than perfect life. But now, standing here the way I was standing, standing here as Sweet Sally, things were perfect. Big Bobby came up beside me and wrapped an arm around my side.

"You gonna miss it?"

I didn't know if he met the diner, or who I once was. I thought about it for a second and then had my answer.

"Not a chance."

He smiled and pulled me in for a kiss, and made this one last, as he showed all the other drivers who was king. Then he opened the door for me and held my hand as I climbed up onto the seat. He got in on his side and got behind the wheel. As he turned the engine on I felt the vibrations throughout my whole body, stimulating me all over. I kicked my flip flops off and put my feet up on the dash.

"Hey."

I looked his way and he looked mine.

"You ready?"

"Ready if you are."

He blew me a kiss and then we were off.

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AnonymousAnonymousabout 6 years ago
Wanting more

Is Sweet Sally going even farther

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