My Online Friend Dave Pt. 03

"No," I responded harshly.

Alana looked confused to say the least.

"You're going to do it," I said forcefully, hoping she would be less resistant if she felt threatened.

"What the fuck are you talking about?" she asked

"I want you to fuck my ass. It is a huge fantasy of mine."

"I don't know, I've never done anything like that."

"Exactly! That is why you should do it. Relax and have some fun with it."

"What if I hurt you?" she asked.

"You won't, I promise," I responded. "I told you already that I want you to peg me. This is the first step. If you don't like it then we can stop and I won't mention it again.

"Okay, but you can't be mad if I stop."

"Absolutely not," I said as I scooted down the bed and laid on my back.

"Give me your hand," I said.

""Why?"

"You're going to lube me up,"

"What, no way,"

"C'mon, just roll with this. Again, you can stop when you want."

"Fine," she said as she stuck out her hand.

I grabbed the lube and squeezed a generous amount onto her fingers. I then reapplied it to the vibrator and handed it to her. I grabbed my legs behind my knees and lifted them towards my chest totally exposing my recently fingered asshole to her.

"Just rub the lube on my hole," I told her.

Alana reached over and gently touched my asshole for the first time with her slick fingers. I moaned, still not believing she was actually doing it. I've blown so many loads jerking off thinking about this exact scenario and I was actually living it out. She was watching as she began to rub back and forth slowly over my hole. She was tentative, not really knowing what she should do. It still felt amazing as I moaned some more.

"Don't worry, you can be more aggressive," I told her.

"Okay, do you want me to put a finger in," she asked.

I was totally taken back by this question. I thought she was going to rub around the outside and then go to the vibrator.

"If you want to, it would be great," I responded.

"I don't want to hurt you."

"Your fingernails are short, right?"

"Yes, you know I hate long nails," she responded.

"Then you won't hurt me. I've had two fingers in there before."

"I'm learning a lot about you today," she said while laughing

Alana continued rubbing as I watched her face to see if I could discern if she was okay with what was happening. She looked like she was especially pleased when she pushed down with her middle finger and penetrated me. It wasn't just the tip she went right to the second knuckle

"Oh, fuck," I moaned.

"Are you okay? Did I hurt you?" she asked.

"God no, that feels amazing!"

"Good, because I think I really like this," she said as she pulled her finger out and drove it back in.

"Look how hard your cock is? Why don't you stroke it for me? I want to see you jerk off with my finger in your ass."

I reached down and wrapped my hand around my cock and began to slowly stroke it. I didn't want to go too fast for fear of cumming too soon. This all felt so incredible.

Alana picked up the pace as her finger would disappear and then reappear in my ass. I was moaning as she fingered me.

"Yes, Alana fuck my ass. I've fantasized about this forever. Please fuck me," I said.

Alana began massaging my balls with her other hand. I could tell something was up by the look on her face.

"Your balls are so full, they are huge. I can't wait to see you cum,"

I knew that if I didn't slow this train down I was going to cum soon. I stopped jerking and tried to relax as Alana continued to assault my ass with her finger. She was inserting her entire finger in my ass and twisting it every so often. She had lost any inhibitions she had to start and was fully enjoying herself.

"Let's get the vibrator," I said, partly because I want it, but mostly to get a break so I wouldn't blow my load and be done.

"You're enjoying this, aren't you?" I asked.

"This is fantastic, I loved the look of pure pleasure on your face when my whole finger went in. You really do enjoy assplay don' you?"

"I do, Alana, I really do."

"Let me ask you something and be honest. If he asked, would you let Dave fuck you?" she asked.

"It's definitely a fantasy of mine and I like to think I would, but his cock is so big that I'd be afraid of what it would feel like. I think I would be more likely to let him if you were there with me."

"That's so sweet, my husband wants me to be there when another man stuffs his dick in his ass. I'm tearing up at how romantic that is," Alana said jokingly.

We both burst out laughing at the thought. I reached for the vibrator and gave it to Alana. She took it from me and walked to the nightstand. She opened the drawer and put it away. She then returned to the bed, reached over and picked up the black dildo I stuffed in my mouth earlier.

"Let's consider this the start of training for Dave's dick in your ass. This is long, but it's not too thick. In fact, it looks like the same thickness as Dave's cock pics. Perfect, I'm excited for this."

"Hold on, you're excited?"

"Yeah, I'm feeling excited that I can be part of hopefully making my husband's fantasy come true."

"You're assuming Dave wants to fuck me. Remember, he and Beth aren't into assplay."

"Yes, I am assuming he wants to fuck you, but so what if he doesn't? Did you ever think I would offer to fuck your ass with a dildo so that you are ready do take it in the ass from another guy? How fucked up is that? You have a lot of fantasies, is that one?"

"That's actually a few wrapped into one. I like your combined version, though," I said while laughing. "Okay, let's do it! You've inserted more large objects in your pussy than I have in my ass so you run the training,"

"What does that mean?" Alana asked.

"Have you forgotten our vegetable phase in college?"

"Shit, I did. That was fun though. I wish I knew then what I know now. You definitely would have taken one in the ass!"

"I would have let you do anything you wanted to me then and still will now," I said.

"I never in a million years thought I would say this, but I really want to fuck your ass with this dildo."

"Where do you want me?" I asked fully submitting to what was about to happen.

"Get on all fours," she instructed.

I did as I was told and got on all fours with my ass fully exposed to Alana. I was nervous, but so incredibly excited that this was happening. Just the fact that Alana was willing to do this sparked a flame in me for her that had long been out. My thoughts were interrupted when Alana began to rub my asshole again.

"Oh Tim, this is going to be fun. I really think I'm going to enjoy this. You know, I'm sensing that I have some power over you when it comes to your ass. Do you agree?"

This was strange. I've always wanted to be dominated sexually. But, I never thought Alana would want to play. Was I wrong? Apparently I was.

"Answer me!" Alana said as she slapped my ass.

"Yes, I agree," I responded.

"See Tim, you're not the only one who watches porn. I've recently been watching alot of porn about husbands submitting to their wives. And I have to say, it really turns me on. I usually finger myself thinking about you submitting to me, but never really thought I would have the guts to follow through with it. I also didn't think you would be into it, but I'm starting to think otherwise now that I know how serious your ass fetish is. So now, I was thinking we may actually share in this fantasy. Am I right?"

"Yes, ma'am," I said softly.

"Say it loud and clear," Alana said as she plunged her finger in my ass.

"Ohhhh, yes ma'am. You own my ass," I grunted feeling the full length of her finger.

"Don't worry, just because I own you doesn't mean I won't take good care of you. We'll get your ass in shape to take Dave's cock in no time. Would you like that?"

"Yes, ma'am."

Alana was sliding her finger in and out of my ass with ease. She slowed her pace and I felt her squeeze more lube on my ass.

"We need to make sure you are loosened up enough to take Dave, don't we?" she asked

Before I could answer, Alana slipped a second finger in me causing me to moan loudly. I didn't have time to answer before I felt the sting of her slapping my ass.

"Answer me!"

"Yes, I need you to loosen my ass so Dave can fuck me," I stated.

While she continued to finger me from behind, Alana began rubbing my balls and jerking my cock. I was in heaven to say the least. I wish I could have seen from afar what I looked like on my hands and knees with my wife's two fingers buried in my ass. Regardless of what I looked like, the feeling was amazing. Alana was going slow because I think she could sense that I would cum quickly if she quickened the pace.

"How does it feel to have my fingers in your ass?"

"Amazing, I can't believe this is happening. It's so fucking hot that you are dong this to me," I said.

Alana pulled her fingers out of my ass and slapped it hard twice.

"Good, go get a towel to put on the bed. We are going to need it for what is next and don't touch your cock. This is a little break so you can calm down. I can't have you cumming too quickly if I'm going to get you ready for Dave's cock" she said.

"Yes ma'am," I said as I got off the bed and went to retrieve a towel. I could feel the slickness of the lube between my ass cheeks. I also felt the emptiness in my asshole with Alana's fingers. I didn't realize how long she was in me, but I was ready for more.

"So how do you want him to fuck you," she asked when I returned with the towel.

"However he wants I suppose,"

"Right, but if you could choose, what position would you choose?" she asked.

"I suppose missionary so I could see what is happening and watch his reaction," I responded

"Tim, that is fucking hot. I thought you would say doggie so you wouldn't have to look at him. Do you want him to cum in you?"

"Absolutely, he's come on me plenty of times. I want him to fill me."

Suddenly Alana's demeanor changed back to her stern domineering ways.

"Get on the bed and lie on your back. Pull your legs up so I have clear access to your ass. Your first real dildo session is starting now."

I did as I was told and got into position. My nerves were causing me to shake a little as I watched Alana cover the dildo in plenty of lube. I had never had something that size in my ass before. I have a high tolerance for pain, but I wasn't sure about how high it was for my asshole. I was excited though. Just sharing this intimacy with Alana was amazing.

"Spread your ass cheeks, cock sucker."

Alana was certainly enjoying her newly found role in dominating me. I have to say that I was too. I liked that she was in control and I was subservient to her. This whole thing was so polar opposite from our past. It was exciting and new and by the sound of it, it was our future.

I was brought back to reality by the slight pressure of the dildo pressing against my anus. Alana was being gentle, having not done this before. She was still afraid of hurting me. She pushed a little harder and still no penetration.

"Just relax your muscles to allow it in. Actually put this pillow under your hips, it might help."

I put the pillow under my hips and waited for Alana to try again. She did, but with her finger instead. It slid in easily as did the second one. What a wonderful feeling. This lasted about twenty seconds until she withdrew them.

"Push harder," I instructed. "If it hurts too much I'll tell you. Don't worry about me.

I watched as Alana lined the dildo up and began to push. It was harder, but still not enough.

"Harder, fuck my ass. Push it harder," I yelled

And she did. When it entered me it was like the air was sucked from my body. It fucking hurt. It took everything not to whimper and cry. But, I knew I couldn't because she would stop.

"Don't move," I told her. "Give me a second to adjust."

"Are you okay?"

"It fucking hurts, but I'm okay. Use more lube and push a little."

Alana squirted more lube and then pushed a bit. I responded with a groan, and it wasn't from pleasure. I started thinking that this was a bad idea and I'll just stick to blowjobs. Then she pushed more and the pain continued. My eyes were closed and my hands clenched the towel that was under me.

"Should I stop? Alana asked.

"No, not yet. Just keep pushing slowly then pull back a little then push a little further."

This continued for a good 15 mins until she had about seven inches in. My ass was starting to relax and I was actually starting to feel pleasure. I think Alana was too as she was smiling and shaking her head.

"You're doing great, how does it feel?

"Really good," I said. "I can't believe I'm taking this in my ass or that you are the one doing it. So fucking hot"

"Well you are baby, and soon enough it will be a real dick as Dave is fucking you. Is that what you want?"

"God, yes. I want him to bury his cock in my ass,"

"Pick your head up, I want you to watch me fuck you now,"

Alana slowly pulled all but two inches or so from my ass. She then pushed it back in in one motion,

"Oh fuck yes, that feels amazing. Fill me up."

"That's it, take my dick in your tight ass. Dave's going to fill you up and I'm going to watch as you scream," she yelled. "You're just a dirty cock whore."

Alana continued to fuck me slowly for several minutes. I still hadn't touched my cock because she would let me. I tried several times, but she slapped my hand away. The pleasure of so much dildo in my ass was indescribable. I literally had never been happier sexually. Alana was really fucking me with it. It was beautiful.

"Tim, the entire ten inches is in your ass right now," she said in disbelief.

I looked down and it was true. Besides that handle in Alana's hand, the entire dildo was up my ass.

"Fuck me!" I said

"I know, right?" she said, shaking her head. "Unbelievable!"

"No, fuck me! I want you to fuck me faster, now!" I screamed

Alana looked a bit confused at first, but then caught on and started pistoning the dildo in and out of my ass. I grabbed hold of my cock and started to stroke it with abandon.

"Yes, that's it baby! Dave's big load is coming soon in your ass. You know how big it is. I want to see it dripping down your leg after he fucks you."

"Yes, yes, fuck me, faster. C'mon. Ohh, I'm going to cum. Harder, fuck my ass."

The first rope hit my cheek while the rest covered my chest and stomach. There was so much of it. I've never cum so hard. I was still stroking my dick when Alana leaned over and took it in her mouth. She had never taken my cum in her mouth and to see it shocked me. She then got up from the bed leaving the dildo in my ass and approached me.

"I love you," she said as she leaned in close to lick the cum off my cheek. Once it was in her mouth, she leaned in further and kissed me. I willingly accepted my cum from her.

"I know you like to taste your own cum. It looks like there is quite a bit to clean here. Hand me my phone.

I reached over to the other side of the and grabbed her phone. Alana was giggling when I handed it to her.

"What's so funny?" I asked

"I'm going to take some pictures of you cleaning all your cum off yourself with a dildo stuck up your ass. Then you are going to give me Dave and Beth's contact info so I can show them what a good little cum slut you are."

I did as I was told and began scooping the cum off my stomach and depositing it in my mouth. I was not humiliated. I was so turned on by the day's events that I didn't lose my hard on the entire time I was eating my cum. In fact, I left the dildo in for a while after I was done.

About ten minutes later Alana was typing on her phone.

"And done...," she said.

"Did you really just send them the pictures?"

"No, you and I can pick those out together. I just ordered a ten inch black strap on to use when I fuck your ass next. I want to know the feeling of grabbing your hips from behind while I bury my cock in you. This one has more girth than what you just took, but you did so well I figured you'll be fine." she said as she winked and left the room.