12

Part 11

Caitlin slept on my bed for 5 hours. I suppose that wasn't so long considering that she had just come off a night shift, but it was an unpleasant 5 hours for me. I tried to spend that time productively doing housework. Occasionally, I would peek in on her. She was just laying there, nearly naked, dead to the world. I immediately regretted it each time I looked in on her. I was more frustrated than I have ever been in my life and seeing her naked only made it worse.

When Caitlin finally woke, she called out from the bedroom for me. I went to the bedroom and she was still laying on the bed. She patted the bed and I sat down.

"I'm hungry. Do you have food here or will we have to go out?" She asked with a bit of yawn.

"My refrigerator is pretty empty, so I guess it would be better to go out." I answered.

"Okay, I know a nice spot that we can go to that isn't far from here. Please grab my bag from the other room so I can get dressed." She said.

"Ok." I said and went to fetch her bag. I brought it to her and she began dressing. She chatted away about all sorts of random things. I tried my best to keep up with the conversation, but my mind was elsewhere.

We left my place and headed to a little Mexican place not far from where I live. The walk to the restaurant and most of the meal was occupied with mundane chit-chat. I learned that Caitlin and Tiffany normally have lunch at least once a week. I learned that they met each other on-line. I found all of that a little strange since Tiffany never mentioned Caitlin to me before. Tiffany and I shared so much with each other. I was a little hurt that she never mentioned a friend she saw at least weekly. I wish Tiffany were here right now.

I picked up the tab for dinner.

"Thanks for dinner! That was sweet. Dessert is on me, let's go this way." She said walking off.

We walked for a few blocks before I figured out where we might be going. Two blocks ahead of us was a sex shop that I had been to once or twice before. We were still heading in that direction and I was getting more and more nervous as we got closer. Once we were on the same block as the shop I was sure that is where she was leading me.

"We are going to make sure that you are milked dry tonight!" she said with an enthusiasm that I found disconcerting.

I remained silent and just followed her in. She paused for a second and scanned the store and moved with determination to the wall where a number of dildos were hanging. I followed behind her.

As she stood there studying the dildos she mused "which would be best..."

"Can't we just use the one you brought today?" I asked as quietly as I could.

"It isn't doing the job. You need to have the right tool for the job." she paused "Which one do you like?"

I just stood there looking at them. They were all different sizes. Some were realistic and some not.

"I... don't..." I started.

"I'll help you out. Pick your favorite of these 5." She said as she identified 5 realistic dildos all larger than the one she used on me earlier.

I sighed.

Since two of the 5 were just enormous, they were out. The remaining three were all still big. They were bigger than me. I was hating this. I knew she wasn't going to let me walk away from this decision, so I just chose one at random. They pretty much all looked the same to me.

I pointed at it, "That one."

"Okay. Why that one?" She asked

"I don't know, they all seem the same to me." I answered. The wrong answer, apparently.

"The same? " She said in a surprised tone as she stepped toward the wall of dildos.

She then pointed to each of the 5 in turn and described what she saw as distinguishing characteristics of each. Regarding the last one, she remarked how it was "girthier" at the tip than the others and might best stimulate my prostate.

"So, which do you want?" She asked again.

I pointed to the one that she said might be better for stimulating my prostate.

"Good choice." She remarked as she handed it to me. Let's walk around a bit and see what other fun things they have here. I love sex shops."

I just quietly followed her around. Whenever she remarked on some sex toy I would just nod my head or quietly make a comment. I was very self conscious walking around the store carrying a large dildo. Fortunately, there weren't many other patrons and those that were there seem to be focused on what they were looking at.

Finally, we made our way to the register. I put the dildo on the counter and the cashier, who was in her early 20's and very cute, looked up at the two of us and smiled. "This is a very popular one" She said looking at Caitlin.

"Oh, it's not for me. I prefer the real thing." Caitlin responded.

At that, the cashier looked at me and gave me a wink. I could feel my face get hot and I knew that I must have been blushing.

I paid the cashier and we left to go back to my place. During the whole walk I carried the black plastic bag containing the new dildo. I knew Caitlin was talking, but I didn't hear anything she said. I was lost inside my head. I was embarrassed and I felt like my world wasn't making sense. What the hell was going on?

Part 12

When we got back to my place, Caitlin said that we would take a shower before getting to my "p-spot." I got into the shower just as I had the first time. I washed her down part by part. When she was done, she told me that it was time to make sure I was clean. I put my hands on the wall just as I had been directed to do the first time.

"Good boy. But this time you're going to check yourself." She said as she handed me the bottle of body wash. She continued, "Just do it like I did the first time."

I let out a little sigh and took the bottle from her and lathered some in my hands and washed my cheeks and crack. Then I reached back with one hand to my anus and pushed a finger in. Caitlin leaned down and watched what I was doing.

"Put it in as far as you can." She instructed.

I pushed more of my finger in. I did not like the sensation at all, but something about doing this under her instruction and with her watching, made my penis struggle against the device.

"Good. Now move it around in there. Make sure you're clean." She said.

After a few moments, she broke in again, "That's good enough. Watching you do that is turning me on and I want some of that ass. Go dry off."

I stepped out of the shower and dried. Then Caitlin stepped out and I dried her off.

"Go get into position and I'll be there in a second." She stated.

I did as she told and waited. She came in wearing the harness and the new dildo. It looked even bigger on her because of her small frame. She then got behind me and lubed me and the dildo up. She pressed it against my anus. Inserting it took much longer than the last one. By the time it was in, I was breathing very heavily and shaking. Once it was in, I lowered my hips and she laid on top of me and whispered in my ear, "You're doing great," as I adjusted to its size.

Though she started slow, she eventually was pounding me. I felt like each time she pulled out she was taking my insides with her. But every time she thrust, well, it was starting to feel good. Involuntarily I started to push back with my hips to meet her thrusts. And every time her hips would meet my ass I would let out a gasp.

"That's right, take it! Take it, take it" She grunted with a few thrusts.

I she began to pick up her pace. I could tell she was getting close. I felt like I was going to bust out of the device. And then I felt spasming in my ass and groin. She came just a few moments later and collapsed on my back. After a minute or so she pulled out and rolled over. I rolled to my side and we both looked at the towel that was soaked with my cum.

She smiled and looked at me, "You came! Looks like you're a bit of a size queen. You slut." And then she laughed.

I actually found it both embarrassing and funny. I let out a nervous laugh.

"Don't be embarrassed. I also appreciate a big cock. Come here." She said.

I moved closer and she gave me a hug and whispered in my ear, "You did great. You should be proud. Most guys wouldn't be nearly as good a fuck as you are."

"uh... thanks, I guess." I responded.

We laid on the bed for a while and chatted a bit. Although my ass was a bit sore, the ache in my balls and groin was gone. I still felt horny though.

After a while, she got up, took the harness off and dressed. I walked her to the door and we said our goodbyes. She said that I could call her any time while Tiffany was gone and the she might even stop by for another "ride" if the mood struck her. Then she left.