Big Bobby and Sweet Sally

He pushed a couple items through the crack which turned out to be a red wig in a bob cut and a red thong.

"Wait, Big Bobby..."

I began to protest but then he stuck another crumpled hundred dollar bill through the crack of the door.

"For your troubles. Please."

I said as sheepishly as I could, "Um, okay. I guess."

"Great. Now hurry up in there."

He closed the door hard and I was left standing there with stockings on and wig and thong in hand. Well I guess there goes the boxers. I could understand the wig, but the thong? I wouldn't even have the dress off in front of him for him to see it. But he did hand me an extra hundred, and I guess it really would complete the ensemble. I dropped my boxers to the floor and slowly slid the dark red thong up my legs. Once I had it all the way on it fit tight and snug against me, and the string really rode up the crack of my ass. Strangely, it started to make me get hard a little bit, but it could have just been the new and unusual sensation.

I then finally got to the dress. I had never put one on before, so figuring that out was a challenge in and of itself, but eventually I figured it out. I pulled it up past the thong and over my belly and most of my chest. When I first saw it I was correct, it was a tube top dress. It came up to just about cover my nipples and the bottom was well above my knees. A tiny tube top dress if I'd ever seen one. To finish it all off I placed the red-haired wig on my head and looked in the bathroom mirror to adjust it and put it right in place. Once I had done all that I noticed I looked quite feminine indeed. With just a little bit of makeup I would about pass for the real deal.

After a little bit of adjusting and pulling I was ready to finally present myself. I mustered up what little courage and confidence I had left and stepped back out into the room. Big Bobby looked up at me and a long grin spread across his face. I stood before him a girl, or at least, some kind of girl. I didn't know what he wanted me to do so I just stood there, in all my girl-like glory. But then I saw it, the look, the look in his eyes I knew Mary had seen a hundred times over.

"Oh my. Now that's my girl."

"How, how do I look?"

"You look like the real deal, baby. Like more than the real deal."

I giggled a little and Big Bobby slammed back the rest of the bourbon in his cup. He stood up and walked a few steps closer to me.

"Could I, could I maybe hug you?"

"Um..."

"Just for a second. I promise."

Before I could answer he had already moved in and taken me into a strong embrace. My lack of refusal after that was what kept me in that embrace. He was so big, and so were his arms. Even though this was the first time I had met him, I felt a certain amount of safety while in those arms. It felt comforting, in a way.

"You look amazing in that dress, you know that?"

"Thank you. Big Bobby."

"I love hearing you call me that."

I felt his arms slide down a bit. Then his hands suddenly went under my dress and pulled my ass cheeks apart. I gasped, but it was a good gasp. I opened my mouth in possible protest, but before a word came out, he covered my lips with his and kissed me deeply. His hands then began to open and explore my ass and I felt the string of the thong ride up my ass even further. Then he pushed me up against the wall as his kisses became more intense. That's when the moans began, from the both of us.

I don't know how it all happened, how I found myself in this position. All I know was that whatever was happening, I was enjoying it. As he pressed me up against the wall, I felt a couple of his fingers begin to slide their way deep inside my ass. I had never felt like this before, it was so amazing and sensual.

"God you are so damn tight Sally. Am I your first?"

"Ye, Yes. Big Bobby."

He let out a deep grunt of approval and started sucking on my neck. As he did, I felt my cock grow so hard that it was peeking out of the top of the little red thong. I felt his hard cock too as he pressed his heavy body into mine. With his one hand feverishly working further up my ass, his other hand unzipped his jeans and pulled out his monster-sized cock. Then he took one of my hands and placed it on the shaft, showing me how to stroke it just right. He met each of my strokes with groans and grunts of heated pleasure. I couldn't believe I was doing this, that this is what my evening would lead to. But I'll admit, it was turning me on as much as it was Big Bobby.

Then he flung me across the room and I landed on my chest on the bedspread, my legs bent and dangling off the end of the bed. I was nearly breathless after his savage toss of me as I heard him step slowly up behind. I pictured him admiring my now feminized body as he looked down on me in my tight dress, and how it made my ass look so perfectly round. He leaned down on his knees and I felt his hands feel up along both of my legs, rubbing and caressing. Then his fingers slid up under my dress and slowly rolled it upwards as he exposed my ass in the barely there thong. I heard a smacking sound and looked back to see him licking his lips. He made eye contact with me, and then he buried his face between my ass cheeks.

I moaned out in ecstasy as his tongue slid past the tiny string of the thong and licked and entered my hole.

"Oh Big Bobby!"

My toes curled and my eyes rolled back as I basked in this new experience. His face stuffed all the way up my ass was an awakening, pure and simple. I couldn't help but crave more as I stuck my ass out and pushed myself further into his face and tangy tongue. It was bliss, and I was succumbing to every second of it.

As he slid his tongue out of me he also slid the thong off and left it a tangle around my thighs. I looked back again and saw him bending back up and reaching for the belt around his jeans. He eyed me with eager abandon as his belt became undone and he undid his jeans. I looked forward, now realizing that I was about to truly experience the ecstasy Mary had felt countless times in this very room. As I heard his jeans hit the floor, I raised my ass even further in the air, letting him know I was ready to be taken, ready to experience the fullness of the Sweet Mary experience. But now it was me, Sweet Sally, who would experience it all.

I felt the strength of his hands grasp onto my hips, and then I felt his true strength begin to press against my craving hole. His head was pushing further and further inside me as he held tight onto my hips and skinny frame. I gasped loudly at the purposeful intrusion, and at the feeling I had never felt before. It was a feeling of intense fullness and of my final surrender to this man.

My gasps didn't stop him or slow him down, they only made him take me further. I could feel every inch of him inside me now, and I began to push back against him to allow even more of his manhood his prize. After a few minutes, Big Bobby slowly slid out of me and by then we were both breathing heavily.

"God you're tight. Tight as all get out."

"Tighter than Mary?" I cooed.

"Mary was never this tight, baby."

I stuck my ass out a little more after his compliment and he didn't hesitate to go right back inside me. His full weight fell into me, and as I moaned his name loudly, he began to increase his pace and his vigor. I grasped onto the bedsheets as he started quickly thrusting in and out of me. With each thrust my stiff cock was squeezed between my body and the bed and was rubbed and milked to my undying pleasure.

"Oh, Big Bobby. I've never felt anything like this."

"Just you wait, darling."

I never imagined I'd take a cock up my ass. And, of course, I never imagined I'd like it so much. But here I was, all dolled up and dressed in feminine best, as my ass was probed and plundered by the cock of Big Bobby. I also never could have imagined this night would lead to me being opened in so many different ways. All I could do was moan louder and louder as he held me in place and had me take all of him.

One of his hands let loose from the meat of one of my hips and I felt it slide beneath me to the meat between my legs. He began to rapidly stroke and tug on my hard little cock which caused my eyes to roll like crazy.

"You're practically as hard as I am, Sally."

"Uh huh," is all I could get out between the pace of his strokes and his pounding of my ass.

"Can you feel how hard I am inside you?"

He slowed his thrusts and I thought he might be close to finishing, but then he intentionally pulled all the way out and then slammed himself all the way back in with an even more aggressive thrust.

"Uh, yes..."

"Yes what?"

"Yes, yes sir?"

"That's right, baby. You're taking all of that cock, aren't you?"

"Yes, sir," I said even more exuberantly.

My yells and moans of yes sir seemed to finally push him over the edge as I felt his heated sperm spill into me. He pulled out and had enough seed left to coat my ass with his sticky spray. Only a few more yanks and the thought of him marking my ass with his juices was enough to get me to cum and empty my cock as well. Then Big Bobby collapsed on top of me and we lied there together still merged into one.

I didn't want to say anything. I didn't want to break the tranquil moment we were now sharing together. He eventually rose up and I could feel his eyes burning into my backside and the prize he had just laid claim to. There were a few moments of silence before he pulled the red delicious thong all the way down my legs and off of me, and then used it to wipe and clean my wet ass and hole.

We got into bed together just a little bit after that and he had me remove the dress completely and he removed what little clothing he had on left as well. We lied there together naked as the whirlwind of a night hung in the air and in our minds. He spooned up behind me and I stuck out my body to press closely into his.

He whispered in my ear, "Can I ask you something?"

"Yes, Big Bobby?"

"Would you like to come with me on the road tomorrow? I will show you so much of this world."

"I'd like that very much Big Bobby."

He pulled me in close and I cuddled up next to him, and I was content.

"My sweet, Sweet Sally."