Stepdad Ch. 03

Before getting back in bed, I took off my panties, leaving my night shirt on. Once the flash drive was in place and I started the video again. I watched it from the beginning because I loved watching Mom suck my favorite thing as well as the tit-fuck session. I was extremely turned on and wet by the time the video got to the point where Derick inserted the toy into Mom's ass. I watched that part in slow motion. I noticed how slow he went and how wet Mom was. I paused it and reached down between my legs, fingering my wet pussy with two fingers, moving them deep and covering them with my super slippery juices. Once covered, I moved my fingers lower and smeared my juices around my tight little bum hole.

It felt good, highly sensitive. With my other hand I played with my clit. I learned on the web that playing with it helped with anal sex. With one finger, I probed my tight hole, gently starting to press firmer on the center. The sensation was nice and my finger went in a little, causing me to hear my blood pounding in my ears from excitement. My heart was frantic in my chest. It frightened me a little how worked up I was.

My anal muscle acted on its own. Pinching my finger as it slipped in further. I pulled it out more from surprise than pain. It seemed like it was telling me I wasn't meant to put things in, it was made for exits only. Mom had somehow learned to control that instinct and let the toy inside with what looked like ease. I took the time to watch Derick put the toy into Mom again a few times. It almost looked like she was pushing out as he was sliding it in. I put my finger back down there and felt my tight hole move as I pushed out. Then, as I pushed, I moved my finger in and the result shocked me because suddenly my finger was inside my body up to the second knuckle. It had gone in really easy!

I thought my heart was racing before, but now it was practically jumping out of my chest as I held my finger inside my ass. My muscles had latched onto the middle when I stopped pushing out and I felt how tight I was. It was a strong muscle, but one I learned I could control if I practiced and concentrated. Without moving my finger, I explored what my sphincter could do. My heart didn't settle down and I found myself really aroused. My nipples were rock hard as was my clitoris, but not only that, my pussy was practically dripping down toward my finger inside my ass.

It felt strange and tight and I wondered how in the world Mom could open herself up enough to take something three times the size of my finger. I looked at the toy lying on the bed next to me and shook my head in disbelief. The laptop was paused on the toy pushed into my mother up to the first rib. It fit in her, so I had to believe it could fit inside me too.

The more I explored and played with my muscles and started moving my finger the more I got accustomed to the sensations. I quickly realized the tightness could be controlled and the longer my finger was inside me the less tight it became. I was soon sliding my finger in and out all the way as deep as it would go. I kind of liked it. Especially when I played with my clit and pussy with my other hand.

After about ten minutes I got even more adventurous and added another finger into my ass. With what I had learned, rather quickly I might add, I adjusted to this new width and found the new fuller sensation pleasant as well. I knew I was over halfway to taking the toy. Not bad for a beginner. I was impressed with how much the anal play added to masturbation, finding myself very close to cumming with less effort than had I not had my fingers in my ass. I'm sure the excitement and newness of what I was doing helped.

As I played I started watching the video again, since I had yet to finish it. I fingered my ass and played with my clit as I watched Derick fuck Mom with his awesome dick. He soon started moving the toy in her ass as well, alternating the shafts. When he pulled out he shoved the toy deep and vice versa. It was unbelievably hot. Mom was loving it and taking it like a champ. The amount of cock in her was seriously crazy but she seemed to love every second like a true 'porn queen'. The more I watched and the further and harder Derick fucked Mom, my arousal skyrocketed. Juices from my pussy ran to my moving fingers and added lubrication for my ass, only increasing my pleasure. Then when Derick finally pulled out and practically drenched Mom with the biggest load I'd ever seen, I knew I had to go through with what he wanted.

I was so close, I never got a chance to try the toy or add anymore width because my climax took over. The pleasure was incredible and what my ass did during my contractions was even more so. It squeezed my fingers tightly, practically forcing them out as the orgasm flooded me with pleasure. I came and came as I watched Derick's cock spew his load onto Mom's back with the toy still stuck up her ass. I managed to keep my fingers deep and rode the wave of rapture until I fell limp, removing both hands from my trembling body. It was stunningly good.

**

For the next couple of days I experimented further. I did it in the shower, in my bedroom and once on the couch when nobody was around. It was exciting and I found playing with my anus very enjoyable and fun. I never let on to Derick that I was preparing to give him what he wanted. For all he knew I was still resisting him and not caving in. I had yet to try the toy but I was pretty sure I had learned enough and played enough that I would be able to handle it.

The mention of a third video from Derick was the last straw.

"You play a hard bargain. So I'll up the ante... three videos now," he said at breakfast one morning.

"Three, huh? Wow... how can I pass that up? Three videos for you watching me fuck my ass with the toy. Man that's a good deal," I said.

"The sarcasm is oozing from your mouth, but you know it really is a good deal. One for three. That's way better, considering our original bargain."

I stood up from the table and took my dishes past him to the sink. I set them down and as I walked out of the kitchen I turned back and looked at him for a few seconds before I spoke.

"You're absolutely right, Derick. It's a great deal. Send them all and I'll be waiting for you in my room," I said before turning and walking away.

The look on his face before I turned was priceless.

My heart was racing again as my walk turned to a run to my room. I sat on my bed and kept refreshing my email to see if he'd send them. The chime on my phone gave me chills as his email came through. He had attached all three videos. About a minute later as they were downloading on my laptop, he knocked on my door.

"Come in," I said.

He opened the door and let himself in.

"You sent them," I said, looking at my computer.

"Yep, now it's payback time," he said.

"But I haven't watched them yet," I said.

He kind of looked stunned and didn't know what to say.

"Just because you sent them doesn't mean you deserve your fair share. I get to watch them first then you get your payback," I said.

"Right... damn," he said, turning to leave.

"Unless you want to watch me watch them," I said, stopping him.

"Only if it leads to the agreed upon deal," he responded as he turned around.

"You mean me fucking my ass with this," I said, picking up the toy from off my bed.

"Exactly."

"Are they worth it?" I teased him further.

"All three of them are for sure," he said without hesitation.

"You better be right, this thing is pretty big," I said stroking the toy with my hand.

I could tell it turned him on to watch me play with the toy. I sat down on my bed and moved my computer next to me. The videos were almost done downloading. He had labeled them with the date they were made already for me. I knew he expected me to watch the oldest one first. The one I'd already seen.

"Which one is the best," I asked him as they finished downloading.

"Actually, probably the oldest. If you remember, that one was made after those four days of no sex you so forcefully reminded me of."

"Oh, so it probably has some crazy hot stuff on it."

"And a massive cumshot," he added.

He was right. I had watched that cumshot several times since the first time and was still amazed by how much this older man had inside him after four days.

"Oh, I'll bet. What about the other two?" I asked.

"Well, it's a tossup between the first and last. You'll just have to watch them and see."

"Well, do I want to save the best for last then?" I asked.

"Oh, well I guess you can."

It was what I wanted him to say. I now had free rein to watch a new video I hadn't seen.

"Good, then I think I'll start with the second one," I said.

As he watched, I pulled my nightshirt off the cross-armed way and tossed it on the floor. He grinned as my breasts were out in the open for him to see. I liked the way he looked at me, I especially like the large bulge in his pajama bottom that got larger the more he watched me. I picked the second video and double clicked it.

I wasn't prepared for what I saw when the video began. Derick's naked body filled the screen. It took me a second to realize that Mom had the camera this time.

"Oh this is new, Mom's filming this time," I said.

"Yeah, I convinced her to direct and film that one," he answered.

I was thrilled because it was more of what I wanted to see. I could tell my mother was just like me and loved his cock. She kept the camera focused on it most of the time. I could hear her voice tell him what to do. His long cock hung between his legs only slightly aroused at the beginning of the video. Mom made sure that didn't last long.

"Grab that cock and stroke it," she said on the video.

He obeyed and I watched the cock of my dreams grow in his hand until it was hard and throbbing. I was so engrossed I almost forgot he was standing in the room watching me watch him. I was already touching my sex through my panties, rubbing my growing clit as Mom moved closer to him until his cock was the only thing I could see on my screen.

"Oh yeah, does that feel good? Stroking that big cock for mommy. Mmmm, so tasty," Mom said.

I grinded on my clit as I watched him stroke the vein covered monster on the screen and saw movement across the room. The monster was out and hard in real life brilliance. Derick was stroking it just like on the laptop in front of me. I didn't know what to watch and found myself digging into my pussy, making a mess of my panties. I quickly pulled the material over to one side and shoved my fingers deep as I watched the twin cocks before me. It was like a dream come true.

"I've got to have you," Mom said, reading my mind and saying what I wished I could say.

The video was a little jumpy after that because Mom had climbed on the motel bed to lay on her back. The image stabilized and I could see her legs were spread and Derick was crawling on the bed toward her. I watched the video as he knelt in front of my mother and fed his cock into her pussy. From Mom's point of view, I was able to imagine Derick doing the same to me. I tore my wet panties off, grabbed the toy and shoved it in deep, looking up at him watching me. He wasn't stroking as fast anymore, more caressing his cock and holding it than actively stroking. The view on the screen was amazing. His body rocking back and forth as Mom filmed him working his cock in and out of her.

I fucked myself at the same speed as he fucked Mom and looked up at Derick and back at the screen.

"That's it, babe. Give it to me. Don't stop... just like that," Mom said on the video.

Derick was moving fast, pounding Mom hard and deep, making the video a little jumpy. A few times I caught glimpses of her breasts rolling in large circles as he thrusts into her. She mostly kept it up at him and on his cock moving rapidly in and out.

"I want you to cum... Keep going and cum," Mom said.

When she said this I looked at how much time was left on the video. To my surprise it wasn't much. This was going to be a quickie apparently. I watched and fucked myself just as fast as he was Mom and when I looked up at Derick he was grinning as he watched me. Less than a minute later I watched him pull out of Mom and cum on her stomach. A few bursts almost reached her boobs but it wasn't near the load I'd seen on the stolen video. After he finished, Mom stopped filming.

I eased my thrusts and looked up at him again. "That was a short one," I said.

"Yeah... she said she had to get back to work that day. We didn't have much time."

"Oh, well, the other's better be longer," I said.

"Don't worry, you won't be disappointed."

I was moving the toy in and out of my pussy nice and slow. I was wet and I'm sure the toy was lubricated enough to be inserted into my ass but I didn't make a move to do so. Before I started another of the videos, I admired Derick standing a few paces away. His cock was still fully erect and pre-cum was oozing from his slit, running down the V to meet his shaft. He had fished it out of his pajama pant slit so all I could see was his long cock extending through the material. With my other hand, not holding the toy, I reached under myself, inserting a finger below the toy and smeared some secretions around my little anus. This got his attention big time and I swear his cock lurched on its own. I circled my tight hole and pushed out as I inserted my index finger slightly while he watched. I was lying mostly on my side and with the long toy extending toward my chest, Derick could easily see me fingering my bum.

The look on his face could only be described as hungry lust. He hadn't ever looked at me like that before. Just my finger in my ass had him all sorts of worked up. I had a good feeling he'd not be able to resist once I inserted the toy. He'd have to fuck me then. He had to.

Pulling my finger out, I went back to my pussy and smeared more juice around my hot, tight hole, watching his expression. He had started stroking his cock again and the effluent of pre-cum had doubled since I started playing with my ass. To tease him further, I took the toy from my pussy and moved it back toward my anus, twisting and rubbing it around my tightly closed hole. His mouth was partially open and his cock was raging hard as he watched. Placing the toy's tip at the entrance to my anus, I pushed the toy slightly, getting a feel for its width. Not much went in but the reaction from him was perfect. Moving it back into my pussy, I watched the frustration wash over his face.

"Not yet, silly. I still have two videos left," I said as he looked at my face with almost kid-like disappointment.

I loved teasing him. One of these times he would have to act on it and finally take me just from sheer frustration. I half expected it this time but he gathered his composure.

"Sure, that's the deal," he said.

I grinned at him mischievously and selected the next video I hadn't seen. The most recent. The date was just the day before. It opened up on Mom facing away from the camera on her hands and knees. She was on the bed looking over her shoulder, her large breast hanging from her chest, wobbling slightly as she shook her head at the camera.

"Seriously? Again with the camera. I don't get why you keep doing it if you just delete them. You are deleting them, right?" she asked.

"Absolutely," I heard Derick's voice.

"That's a lie," I said looking up at him and pausing the video.

"Not really. I delete them after I send them to you," he said.

"Wow... if Mom only knew," I said.

"What she doesn't know won't hurt her."

I shook my head and hit play again.

"Well, if it works for you then whatever," Mom said on video. "Now come get me."

Derick walked toward the bed and seemed to kneel down because the camera angle changed. Then he set the camera on the bed right under Mom's pussy and started eating her. It was a major close up shot of his face and tongue munching on my mother's sex. From what I could see, it looked like he really knew what he was doing and since I knew how good he was with his hands I could only surmise he was equally talented with his mouth. Mom's moans and trembling legs confirmed it as the video continued for a few minutes with his oral munching of Mom.

He finally stood up, but left the camera under Mom. This part, I have to say, really got me turned on. His cock came into view and rushed right into Mom's well eaten pussy all the way to his balls in one long thrust. It was so close up and hot, I let out a noise of lust, totally forgetting he was in the room again as I watched.

"You like that?" he asked, reminding me he was there.

"Yes, a lot," I said not looking up at him.

"Then you're going to love what comes next."

I started fucking myself with the toy again. Driving it deep with the close up thrusts on the screen. But something happened and the camera moved quickly and went dark with a loud noise.

"That's when the camera fell off the bed to the ground," Derick laughed.

The video resumed when he picked it up and started filming from above. Mom's ass and back could be seen as he drove his cock in deep from his point of view now. He started moving the camera to the side, in close and several different angles as he continued to drive his cock home over and over. Mom was moaning and panting from the barrage of his thrusts, occasionally he would film her heavy breasts swinging freely and grab one of them with his free hand. I was really going fast and deep with the toy as I watched and could tell without looking that it was covered in my juices because it was moving very easily and smoothly in and out. As I watched and fucked myself, I reached behind again and added more secretions to my ass and fingered my bum with one finger. I heard Derick react to this and glanced up at him quickly to find him stroking his cock again. He had that look on his face again and I don't know what kept him standing there and not moving to my bed and fucking me.

On the video, I watched Derick move his thumb to Mom's anus and start rubbing her juices from his cock to her tight hole. She cooed and moaned and really cried out when he eased his thumb in all the way while he was still fucking her pussy. That's when I added another finger to my own ass and pre-cum from Derick's cock, dripped to the floor. He was stroking his cock with purpose now, watching me finger my ass and fuck myself with the toy as the video played on.

A few minutes later I heard the words I'd never in a million years thought I'd hear from my mother.

"Put your cock in my ass," she said.

My mouth fell open, my heart jumped in my chest and I was fucking freaking out. I looked up at Derick after hearing Mom say that and he just grinned at me, stroking his cock fast.

"No fucking way!" I practically screamed but then glued my eyes to the laptop screen.

I watched in awe, totally mind-blowing astonishment, as Derick removed his thumb and his cock from Mom only to grab his thick dick high on the shaft and bend it down to her partially open anus. My mouth dropped fully open as I watched my mother take this massive cock into her ass, nice and slow. The skin around the tight opening actually turned stark white from the sheer width of his cock but she didn't complain. He went agonizingly slow but inch by inch the enormous, wonderful cock, disappeared inside my mom's ass. The toy was one thing but I never expected Mom to let him put his dick in her ass.

Without even thinking or turning from the screen, I pulled the toy from my pussy and slid it back to my tight hole. Pressing out as I had taught myself, I pushed the toy into my anus for the first time. In my mind it was Derick's cock and I was Mom. It went in pretty easy since I had my two fingers in for so long. I felt the first rib slide in and the second and then the third.