The Web Ch. 03


With a final kiss to the head, Cathy let my cock drop to my leg and climbed back up beside me, a satisfied grin on her face. I pulled her lips to mine and kissed her deep, tasting the salty tang in her mouth. For some reason, I always enjoyed kissing a woman who recently swallowed my load, probably because I was using another sense to remember a great orgasm.

Cathy lowered herself to the bed beside me and draped on leg over mine. I wrapped one arm around her, pillowing her head, and lazily caressed her lower back and ass with the other.

We looked into each other's eyes, kissed, and just relaxed. I think I may have dozed—I looked over to see Cathy smiling at me.

"Worn out, sleepyhead?"

"Hey, when you're a sex god, there's a price to pay," I replied.

"I'll gladly pay with you," she whispered and reached down to pull the covers over us. I heard Kelly stirring, turning the lights off and getting into the other bed. I lied there in satisfaction and peace until sleep took me deep.

I woke to find sunlight peaking from behind the shades. Cathy was facing me—I hadn't seen her face asleep before. She looked peaceful and beautiful. I lowered my head slightly and let my eyes wander down to her breasts, rising and falling slowly. For the first time, I saw her nipples when she wasn't aroused. I smiled when I saw her necklace still draped against her chest.

"Enjoying the view?" an arch voice whispered in my ear.

"I'm admiring your necklace. It looks wonderful on you."

"I trust it doesn't hurt that it's on a naked woman in bed with you?"

"That probably adds a little to the allure, I'll have to admit."

"How about if it was swinging above your face, when that naked woman was riding you?"

"I'm sure that would add immensely to its beauty. We should try and see."

Cathy chuckled softly and then leaned in for a kiss. We made relaxed love, letting ourselves slowly wake up and heat up. When Cathy climbed over me, we both looked over and saw Kelly face down, her hand underneath herself and her raised hips moving in slow circles.

"Lovely morning, isn't it?" Kelly giggled.

Cathy rolled her eyes as she rocked over me. I came first in a satisfying blast, Cathy intently watching my face. After recovering, I sat up and scooted back against the headboard. Cathy smiled when I invited her to sit back against me, and she squirmed against my probing fingers until she too shuddered in a satisfying climax.

"Join me for a quick shower? We can all get cleaned up a little faster," I asked Cathy after she stirred.

"Love to!" she answered.

"Aren't you going to ask me, too?" Kelly pouted. "I'm feeling left out."

"Cat got your tongue?" Cathy whispered as she felt a hint of an erection behind her.

"I'll be merciful and save you the agony of answering," Kelly chirped. "You two go ahead, but move out! I'll be starving soon."

Cathy and I had fun soaping and rinsing each other. Once, after she cleaned my back, I got a playful swat on my butt.

"That's for what you were thinking when Kelly asked to join us," Cathy purred into my ear. "You men are all alike."

"Yeah, you're probably right," I laughed. "It's hard to keep my imagination in control when I'm in a room with two beautiful women."

"Keep up the compliments."

"I intend to."

After Cathy and I dried off, we hung our towels and stepped back into the room to let Kelly have her turn.

"Well don't you two look quite the couple, stepping casually into the room naked?"

I took Cathy's arm in mine in an exaggerated flourish. "Madam, may I conduct you to your lingerie drawer?"

Cathy laughed. "Thank you, sir!"

As Kelly showered, Cathy and I dressed and went out on the balcony to enjoy the morning. As we stood against the railing, Cathy looked over to me.

"Brad, I really a really good time last night. I was interested to try, but I didn't know it could be that good."

"Watching you immerse yourself in the moment was very intense for me," I said. "I think that anything you want to do in bed, you will enjoy it immensely."

"Maybe it's the partner I'm with," Cathy said. "Thanks for taking that small step."

We both laughed, knowing that the big step was really Cathy acknowledging her desires and going with them.

"Cathy, we'll continue the 'small steps' as you are ready. There's a lot of pleasure to explore, and I think that you'll love it."

"That sounds great," she replied.

We enjoyed a nice breakfast on the patio. I choose good food, knowing that I had stamina to maintain. We went down to the pool, and the ladies' bikinis turned a few heads when they took off their cover-ups. I put them beside each other and lied back as they chatted, enjoying the morning sun. We dangled our legs in the pool and generally relaxed. As the morning wore on and I enjoyed the company of two ladies, I started to get horny. An idea formed in my head.

"How are you doing, Brad?" Cathy asked. "Kelly and I are thinking about going up."

"That sounds great. I don't want to bake too much."

We walked back to the room. As we settled into the chairs to relax, I looked over at Cathy.

"Cathy, how would you like to take another 'small step,' but this time on me?" I asked.

"I'm sure I would," she replied, "but what do you mean?"

"Well, I would like to lie down and have you play with my backdoor, including slipping your fingers inside," I said. "It will be very pleasurable for me, and it will help you understand how to relax and enjoy it yourself."

"That sounds like fun," Cathy said.

"The only trouble is that we might have to find something to use for a lubricant," I said. "I'll have to see what will work in the bathroom."

"Oh, don't worry," Kelly piped up. "I'm packing."

I looked at her with narrowed eyes. "Somehow, I'm not surprised."

"Whatever do you mean?" Kelly asked, all innocent. "Let me get it while you get ready."

I draped a towel across the bed. "OK, Cathy, this will be a little more like a class, since I will describe what I'm doing. I'm going to start face down here and let you get me warmed up. You're a natural at massage, so you'll do great. As I get turned on, I'm going to get on my hands and knees. You can lubricate a finger then and work it in. The key to understand is that I'm going to completely relax my ass, so you'll slip in easily. Anal sex should never hurt if you do it right. You ready to try?"

"I think so."

"Don't worry, I'll talk you through it."

I pulled my shorts and shirt off, and I was happy to see Cathy slip out of her suit as well. She started with a general back massage, and then moved to my butt, kneading each cheek deeply before backing off the pressure and lightly tracing her fingertips across my flesh.

"Oh, god, that feels great," I said. "You know what you're doing."

Cathy alternated light and firmer touches, and she had me heating up fast. I spread my legs and she responded, working her hands deeper. I raised my hips slightly and arched my back, giving her unfettered access. Her probing fingers reached my ass, and I groaned.

"You're doing great, Cathy. Keep it up."

As Cathy continued her ministrations, I heard a noise and looked to see a very naked Kelly positioning a chair close to the side of the bed. "This is pretty hot," she said matter-of-factly. "I want to have a good view."

"Glad to provide the entertainment," I responded. "You got that lubricant handy?"

"At your service," Kelly said and placed it at my side.

I got up on my knees and spread my legs. Cathy followed me with her hands, rubbing and touching. It felt great.

"OK, Cathy, let's feel how I can relax or tense up back there. Place your finger over my ass and push gently." I tensed my sphincter. "Feel that? That's how it hurts. Now, feel as I relax. You just concentrate on releasing the tension." I felt her finger penetrate just a little. "See?"

"Yes, I do," Cathy said. "I can feel you relax and open up."

"Anal sex is about trust and about opening up to your partner. What happens in your mind happens back there as well. I trust you, and I want to give you the ability to pleasure me. In some ways, I will be giving you ownership of my ass. It's about the most intimate thing I can offer."

I let her continue to probe a little longer. "Why don't you get the lube," I said. "I'm good and ready."

Cathy squeezed some on her finger and set it at the opening of my ass. I relaxed completely.

"Now, just slowly push in and let my passage guide you."

Cathy pushed just her fingertip in, and I groaned. She twisted slightly and pushed in a little further. She naturally knew how to work her finger inside, sliding back a bit before pushing further in. She slid in easily and soon had worked her finger in to the base on her downstrokes.

Cathy's finger was working its magic, and I pushed back, enjoying the unique sensations as she slid in and out. I slid my hand under me and found my cock, starting a slow stroke.

"Feeling good?" Cathy asked.

"It feels great," I answered. "It will probably get harder for me to speak..."

I heard Kelly chuckle.

"so just put another finger in when you're ready. In fact, do anything you want. Rub your other fingers over my ass like it's yours. It feels really good to just let you take over."

I arched my back and ground back into Cathy's hand, really getting into it. In fact, I put on a little bit of a show for her benefit. I wanted her to see how much I enjoyed it so she could anticipate enjoying it herself. I looked over at Kelly and saw her eyes on mine, one hand pinching a nipple and the other busy between her legs. We looked at each other for a while, each enjoying our pleasure.

I groaned again as I felt Cathy's second finger slide in. She slowly worked them both in deep, squeezing the rest of my ass with her other fingers and rubbing with her other hand. I rocked back and forth, and stroked my cock more rapidly. My breathing became ragged as I reveled in the combined stimulation from my ass and cock. I let myself moan my approval as Cathy plunged into my depths.

As my orgasm approached, I slowed down my stroking, feeling the hot tingling radiating out from my groin. The tension became almost unbearable as I rode the edge, lightening my pressure as the internal pressure mounted. Suddenly, I could feel the contractions starting deep inside. Cathy gasped—she was feeling them, too. As my orgasm welled up, I involuntarily clamped down, squeezing my ass around Cathy's fingers.

"Uhhhh, uhhhh, ahhhhhhhhhh," I moaned as ropes of jism erupted from my cock. I could feel each spasm ripple through me and around Cathy's fingers. It was like getting twice the effect. Cathy held her fingers deep, and I twisted around them, drawing every last bit of pleasure from them as I milked my cock with my other hand. The pleasure stretched out in a long tail. I remained in that position for a while, enjoying the afterglow from a tremendous release.

"Wow," I said, after recovering. Cathy slowly drew her fingers out of my ass but kept rubbing as I relaxed down onto the bed. I looked over and saw Kelly in her own afterglow, her eyes unfocused, slowly stroking her swollen pussy.

"That was amazing—I'm totally spent and satisfied. You are a really quick learner," I said.

When I didn't hear anything, I twisted around to look back at Cathy. She had an unsettled look on her face.

"Brad, I'm...I'm really turned on. Could that for me?"

Looking closer, I could see the need in her eyes. I smiled.

"Turned you on, huh? Yeah, I'd be happy to. Why don't we both go clean up and get back in here, so I can get my hands on that lovely ass of yours."

As Cathy was washing her hands, she looked at me in the mirror, still worked up. I moved my head beside hers and placed my hand possessively on her ass.

"You need it, don't you?" I whispered.

"God, yes," she sighed, pushing back into my hand.

"Come on," I said.

We returned to the room and I draped her over the bed, climbing beside her. Kelly just leaned back and spread her legs again, shaking her head with an "I can't believe you guys" look on her face.

I gave Cathy a shorter version of the back rub, to avoid her the agony of waiting in heat too long. As I slid down over her firm cheeks, she moaned loudly. She kept her eyes closed, just enjoying the sensations. I started with massage and then lightened the pressure until she was squirming under my hands.

"Ummmm, feels good," she breathed.

I started working my fingers deeper, and Cathy responded by spreading her legs. I noticed her hips lightly thrusting into the bed as I guided closer to my destination.

"Ohhh," Cathy gasped as I brushed her hole. Her hips climbed off the bed.

"Like that?"


I let my fingers roam freely around Cathy's back entrance, drinking in the sight of her twisting body responding to my hand. She radiated eroticism—just completely lost in the sensations. Her hips pushed deeper into the bed and then flexed to open her up as much as possible. I placed my finger directly over her hole and let her drive into it, feeling her ass relaxing as she tried to draw it in. Cathy pulled her knees up and raised her hips off of the bed.

Something cool touched my leg, and I looked down to see Cathy holding the tube of lubricant.

"I guess someone's ready," I whispered.

"Ummmmm, please," she sighed back.

I spread a dollop over my finger and placed it back at her entrance.

"Just open up and enjoy," I said as I pushed in slightly. Cathy moaned, relaxing her sphincter as my finger pushed slightly inside. I backed out again, twisted, and then slid in a little further, gaining a deep groan from Cathy. At each stage, I waited to feel a sense of total relaxation before I pushed any deeper. Cathy continually groaned and sighed as I penetrated her ass; my other fingers caressing her cheeks.

"Ahhhh," Cathy sighed as she felt my finger bottom out. I started a slow piston movement, watching her rock back and forth in response. As she pushed harder, I did as well, twisting deep within her. I looked up and saw her arms crossed under her breasts, fingers playing with her nipples.

"Oh, yeah," Cathy groaned as I reached under her with my other hand, finding her pussy soaking wet. I slid along her slit lightly, letting Cathy dictate the pace.

Looking back at Kelly, I saw her fingers sliding along her own slit. Her eyes met mine.

"This is hot," she mouthed at me. I nodded, turning back to Cathy.

Cathy rippled her torso into my fingers on her pussy, signaling to me to increase the stimulation. I hooked my finger and slid inside, dragging along her clit as I plunged in and out.

"Ohh, ohh, uhh," Cathy panted. I looked down and saw her eyes open, staring over at Kelly. Looking back, I saw Kelly's fingers now dancing over her clit, her eyes locked on Cathy's. The two women were sharing a bond, the eroticism of the moment burning into me.

I kept a steady motion going, knowing that Cathy would get there when she was ready. She had flattened her chest against the bed, pushing her ass even further into my hand. She was completing offering herself to me. I stroked her ass possessively.

I felt the tremors of impending orgasm begin in her legs. She had closed her eyes again and had buried her face into the sheets.

"Mmmgh, mmmgh, ummmgh," she groaned as spasms wracked her body. Hanging on, I felt the throbbing begin in her pussy and ass that signaled a powerful orgasm. Her pussy clamped around my hand, her body went rigid, and her ass pulsed around me finger as the contractions rippled through her. I marveled at the intensity of her pleasure. Behind me I heard Kelly's moans as she came herself.

Cathy continued to slowly twist beneath me, squeezing out several aftershocks. Finally, she came to rest, letting out a long sigh. I slowly withdrew my fingers from her ass and pussy, getting a whimper when I pulled out. I continued to massage with the rest of my fingers, letting Cathy come down slowly. She stretched out her legs and lowered herself to the bed, sighing and groaning contentedly.

I stretched out beside her, my hand now resting on her ass. As she looked at me, her eyes conveyed a sense of vulnerability. Cathy's body had admitted—more eloquently than any words—her powerful response to anal stimulation. Both Kelly and I had borne witness to that. Cathy had shared something deep and irreversible.

I let my eyes communicate warmth and acceptance as I leaned in for a kiss. Cathy grinned shyly and opened her mouth to me. I kissed languidly, letting her feel my affirmation and affection through my lips.

When I pulled back, she opened her eyes again. This time, they were clear and content.

I lied with Cathy a while and then got up to wash my hands. As I came back and sat on the bed, Cathy rolled over and stretched languorously.

"I guess you could tell that I liked that," she said shyly.

"Just a bit," I replied, smiling back at her. "I think Kelly liked the show as well."

"Unbelievably hot," Kelly said, "but please don't start again. I don't think I can take anymore right now."

"We wore out Kelly the sex goddess?" I asked in shock. "I didn't think that was possible."

"Listen, buster, your fingers can only do so much at a time," Kelly shot back. "I may have to go down to the pool and rape some unsuspecting guy this weekend."

"I better get down there so I have a chance," I replied, getting a scowl from Kelly and some shakes from Cathy as she laughed.

"How about we rest a few more minutes, then get dressed and take a short hike?" I asked.

"Yeah, we should probably see more of this resort than the kitchen, pool, and bedroom, although that isn't too bad either," Kelly replied. We all laughed.

After a bit we got up and dressed. Cathy and Kelly went to the sinks.

"Maybe if I pull my hair in a ponytail and put a hat on, I'll look like I've been working out instead of spending the day in the throes of passion," Cathy said.

"That might pass a casual glance, but if anyone looks in your eyes, they'll know the score," Kelly said knowingly.

"Oh, haven't I showed you my mirrored sport glasses?" Cathy said lightly. "You'll just love them—I definitely turn into a sport babe."

Kelly snorted.

Cathy was right, she did look like a runner in her outfit. We checked at the desk and found a loop hike that was about an hour long. We found the trailhead and started out, getting into a rhythm and enjoying stretching our legs.

After a few minutes of just walking along in silence, Kelly piped up.

"OK, Brad, what you did there was pretty hot. I haven't seen a guy do that before."

"Yeah, a lot of guys would think that's unmanly or something," I replied. "Seems pretty silly to me. It's a whole different set of sensations, and it feels great. It also allows you to connect with a woman in a different way."

"I'll say," Cathy added. We all laughed.

"So, given what happened afterward, I have to ask," Kelly said slyly. "Did you have an ulterior motive in mind when you asked Cathy to play with you?"

"Well, let's say that I did want Cathy to learn from watching and feeling me. Telling someone how to relax is not the same as showing them how. The same goes for letting go and enjoying the sensations. I figured she would get a taste for trying it herself. I didn't know it would be so soon."

Kelly and I both turned to Cathy, who blushed furiously.

"Those 'sport glasses' aren't helping now, are they?" Kelly asked knowingly. Cathy looked down and just shook her head.

I laughed and grabbed Cathy's hand. "It's fun to put you on the spot," I said, "but in truth I loved sharing such an intense experience with you. After that episode, I know you'll love the rest when we get there."

"I think you're right, Brad."

After a minute, Cathy looked up, a challenge in her face. "Now, can we switch attention from my sexual needs to one of you two?"

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