The Web Ch. 02


"OK, that's a pretty good story. Maybe you can just look down and guess the answer to your question." My cock was tenting my shorts. "I love anal sex. I once had a girlfriend who liked it, and we explored each other in several ways." Kelly raised an eyebrow. "Yes. I think I can handle any of Cathy's requests in that area. I might even enjoy them," I finished, smirking.

Kelly rolled her eyes. "Good answer. Now..."

"Look, Kelly, I'm pretty open-minded. I kind of doubt that Cathy will ask anything that I will balk at. I mean, I'm a horny guy."

"I appreciate your sincerity, but I've got to know. If there is anything that you won't do, I want Cathy to know beforehand so she won't offer it up in a moment of confession and then clam up as she sees the shock in your eyes. Since I'm such a wicked, kinky girl, I figure I can think of about anything she can. Now, how about spanking?"

"Which way?"

"Both. Does it matter?"

"No," I said laughing, "I'm just being a pain in the ass. No problem."

"You sure are. Bondage?"

"Check. Haven't done it, but I could enjoy tying her up. Since I know you're going to ask, yes, I could probably let her do it to me. The main thing is whether it's a positive experience for both of us. I guess I would draw the line at something degrading."

"That's a great answer, Brad. I don't think Cathy has degrading in her personality, either giving or getting, so I think we're all safe there. I'm hoping she does the tie-up thing to you, though—I would love to see that."

"No doubt, you kinky bitch. What other depraved things are you thinking about?"

"Domination and submission?"

"The light kind is fun. Serous stuff's not really my style, but I could probably learn. Maybe it would be a growth experience."

Kelly rolled her eyes. "Always a smart-ass. OK, let's move on to taking pictures or making movies."

"Sounds like a good time, as long as we're careful where they end up."


"Aren't we doing that already with you in the room?"

"I'm talking about with strangers," Kelly said.

"As long as we're careful, I could go there," I replied.

"Spraying her with cum?"

"I'd rather not have to pull out too often, but that's more because Cathy feels amazingly good when I come inside her. Yeah, I would do it if she enjoyed it."

"OK, we outlawed group sex in the ground rules. There are wilder things out there, but I figure she would ask me before bringing them up. I guess you pass this part of the test."

"Thanks for the vote of confidence. There's more?"

"Yeah, and this is even more personal."

"Oh, boy, I can't wait."

Kelly looked directly at me, and her eyes blazed intensity. I immediately lost the playful attitude and waited for her question. Time lingered as she burned into me.

"What do you think of Cathy herself?" she said softly.

My face flushed and I felt like a seventh-grader surrounded by a crowd of girls asking the same question. "I, uh, well..." I stammered. I looked down, gathering my thoughts. "Look, Kelly, I need you to be a friend to me, too."

She reached out, lifted my chin and looked into my eyes. I saw openness and honesty there. "I am, more than you know. I'll keep your confidence in this."

I took a breath. "OK, I thought about this a lot on my run. Cathy is beautiful and fantastic in bed. You can see that yourself—what's not to like? But the weird thing is that we're getting to know each other backwards in some ways. I'm sharing her mind and her body at a pretty deep level, but it's been pre-arranged. We didn't do the simple stuff, like go on a first date, like I've always done before. There's nothing wrong with that, but it makes it harder to separate lust from love."

"What does your heart say?"

I felt within myself. "Cathy is the best thing that's ever happened to me." I looked up, surprised to have revealed that much. "Wow, I didn't know that was there."

"You're starting to pass the second part of the test," Kelly replied, her eyes knowing. "Now, what do you think Cathy is feeling?"

"That's harder. She obviously likes me and trusts me with some of her most personal secrets. But that can happen to a good friend too. Also, I've got to factor in our arrangement. We have to eat together and sleep together as part of the sessions. Cathy is very kind and gracious, and she would treat me that way no matter what she ultimately wanted..."

"You're overanalyzing this. Again, what does you heart say?"

I stopped using words and just felt deep down as I looked into Kelly's eyes.

"Cathy's falling for me."

I sensed approval in Kelly's face. "My work today is almost done," she sighed. "Now, I'm a friend to Cathy, too. Of course, if I suspected that she was falling for you, I would want to check that out to make sure she didn't get hurt. As I said before, she's invested a lot of trust in you, so this wouldn't be some regular boyfriend breakup."

"It's funny that those two questions were a lot harder than all your 'Will I do this or that sex act' questions."

"You're a great guy, Brad. You know what the truly intimate questions really are." Kelly started for the door.

"So did I pass the test?" I asked as I held the door open for her.

Kelly blew me a kiss. "That part is self-graded, lover-boy."


This time, I sent the flowers first. The note read:

"Just wanted to express my thanks for your 'patronage.' I really appreciate your continued business. Please call anytime!"

--Dr. Brad Heller.

I could easily have said more, but I wanted to keep my feelings a bit indirect for now. Cathy was on a roll with her sexuality, and I didn't want to complicate that with too much romance for a few more weeks.

Cathy called that evening. "I loved the flowers, Brad. Thank you so much!" We talked about a few things and scheduled our next session for Friday. I went out that night with some friends to catch some dinner and a couple of beers. Their company helped keep me from obsessing over Cathy.

Kelly called the next evening. "I've got a plan."


"It involves us going to a resort for the weekend. I figure we can get more done than in one evening back here. Cathy is up for it. If you are, just leave it to me. I know a place about an hour away."

"Sounds great. I'm in. Is this just so you can see us the next morning?"

"Yeah, I was feeling left out. By the way, I gave the green light to Cathy to bring up whatever fantasies she wants."

"Thanks. We'll both appreciate it. I know I will."

"Sweat dreams, Brad. It's going to be a long week."

"You said it, Kelly. 'Night."

It was a long week, but I called Cathy a couple of times and enjoyed talking to her. We were both looking forward to the trip and planned some time around the pool as well as a hike in the mountains surrounding the resort. I figured we needed to do a few things other than just screw all weekend.

Thursday evening, Cathy called. We chatted about our week, and then she said, "Brad, I'm really looking forward to our trip this weekend."

"I am too. I've missed you." I decided to let that much out.

"Missed me, or some outstanding sex?"

"Boy, that's a tough question," I replied.

Cathy laughed good-naturedly. "See you tomorrow, Brad."


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by Anonymous

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by Anonymous03/20/18

Still loving it

I realized that this has been out for a while. I dont understand why people haven't left any comments.

I've mentioned on other posts,...I really enjoy reading you.


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by dante_1_2310/07/17


Thanks forma an amazing story

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