The Web Ch. 03

"So sorry to disappoint," Cathy said lightly. "Maybe I can make up for it this morning?"

"Maybe," I answered. "What do you have in mind?"

"First, I thought we ought to make sure our chaperon is on duty. Kelly, are you over there?"

"On duty, Ma'am," Kelly chirped. "How can I serve?"

Cathy sat up, pulling at my arm to get me up as well. "Why don't you join us while I tell Brad my request?" She patted a spot beside her.

A very naked Kelly sat down on the bed beside us. I had seen her naked several times before, of course, but it was different to see her this way before Cathy and I had gotten aroused. I tore my eyes back to Cathy, not wanting to break the mood.

"Brad, remember what we did yesterday afternoon, after coming back from the pool?"

I nodded.

"I, um, really liked it."

"I could tell," I said, grinning.

"Well, anyway," she said, hesitating a bit, "I would like to do the exact same thing again. That is," and she looked deep into me as she took hold of my cock, "if you would like to."

"I'd love to, Cathy." My cock started stiffening in her hand.

"I guess there is only one small thing I'd like to change," she continued a little more confidently now, still looking into my eyes. "I'd, um, like to trade places with Kelly."

Time stopped...and didn't restart.

I tried to figure out what she had just said, but her penetrating eyes made it hard to think. Trade places with Kelly. What the hell did that mean? Damn, I can't think! All I can see are those eyes, boring into mine!

Slowly, I put the words together and thought about what it meant. The blood rushed to my cock before I fully worked it out. No, it couldn't be. If Cathy traded places with Kelly, then Cathy would be sitting on the chair, and Kelly would be...

"I think you like the idea," Cathy said softly, tracing her fingertips over my rigid cock. She must have sensed my bewilderment, because she smiled at me, and then leaned close to brush her lips against mine. After the lightest of kisses, she continued leaning until her lips were next to my ear.

"Yes," she breathed. "I want to watch you and Kelly play with each other's...bottom. Don't worry, it's alright. That's what she and I were talking about in the bar when you walked up, remember? I can feel that at least one part of you likes the idea," she giggled as she squeezed my cock, "but does all of you like it?" Cathy leaned back.

"I know it bends the rules a little," she continued, looking into my eyes again, "but I think we can all maintain our relationships. Kelly and I are very good friends, and I would like her to experience a little of the pleasure I have found."

"You're sure that you're OK with this?" I said, my brain finally able to produce language. "No regrets afterward?"

"More than sure." Cathy gazed confidently at me. I looked over at Kelly.

"And you, Kelly. This is what you want?"

Kelly winked. "Shocked I'd settle for you?" She smiled. "Yes, Brad, I'd love to."

I leaned in and gave Cathy a kiss. "Better get comfortable over in your chair."

Both ladies laughed. I got up and went to the bathroom for a couple of towels. When I returned, Kelly was patting the bed beside her, the bottle of lubricant in her hand and a wicked grin on her face. Cathy had pulled her chair close to the bed, and she giggled when I tossed her one of the towels.

"What I do to please my friends," I said as I stretched out beside Kelly.

"It's hard to be a true friend, isn't it?" Kelly said, kneading her hands into my back. "Thank you for giving sooooo much."

"Whatever," I countered. "Actually, maybe it won't be that bad."

"Oh, it will be real bad, Brad." I jumped when I felt the swat strike my ass. "I'm a bad girl, remember?"

"I do now." I looked over at Cathy. She smiled back at me, but I could also tell she was hot and excited. She shifted her eyes and watched intently as the second swat struck the other half of my ass.

"OK, I think I taught you your lesson," Kelly cooed. "Let's rub the pain away, shall we?" Kelly shifted to a very light touch and started tracing her fingertips over my ass.

"Ummmm," I groaned as her touch lit my fires. "That feels great."

"Good," Kelly said, her voice more serious now. She continued the massage, increasing the pressure and backing it off. I let myself respond to her fingers, grinding my hips into the bed. As I warmed up, I pulled one leg forward and arched my back slightly, inviting her to go further.

Kelly responded to the invitation, plunging her fingers deeper between my cheeks. I pushed back against her hands, enjoying the feel of Kelly's touch. I looked over at Cathy. She was still staring intently at Kelly's hands, and I saw her swallow involuntarily. Her fingers traced a pattern around her own pussy lips.

I let out a contented sigh as Kelly's fingers found my anus. I brought the other leg forward a bit to open myself up. Kelly responded by probing deeply around my ass. Her touch was more confident than Cathy's had been, perhaps because she had seen my comfort with it yesterday.

Ready for more, I raised up onto both knees, arching my back to give Kelly total access. She hummed her approval and slid her entire hand over my anus, rubbing and prodding. I let her continue like this for a while, knowing the next stage would probably go quickly.

I felt Kelly twist and heard the snap of the lubricant bottle. Her hand left my ass for a short moment, then returned. I relaxed completely and let her slide inside.

"Ummmmm," I groaned as I felt Kelly's finger. She didn't pause, but just slowly pushed to the bottom. I reached back and encircled my cock while she started working her finger in and out. I twisted my head to look at her and she smiled back at me in genuine pleasure—she was enjoying this. I then looked over at Cathy, who noticed my head turning this time. She winked and then looked down, drawing my attention to where her fingers were sliding between her pussy lips.

"Looks like someone is enjoying the show," Kelly observed.

Cathy looked up. "It is pretty hot."

"I know how you feel. You two have giving me some great shows the past few weeks," Kelly answered.

Even in my aroused state, I couldn't help it. "Maybe I'll get to enjoy a show myself some day."

The ladies both busted up laughing.

"Brad, you are evil. If I didn't have my finger up your ass, I'd get you for that."

"Somehow I don't feel too safe, though," I answered.

"At least you're smart," Kelly answered. She drizzled the lube on another finger and slowly pushed it in.

"Ahhhhh," I moaned and pushed back into her hand. I began to pump my cock as she slid her two fingers in and out, going deeper each time. Finally, she was plunging all the way in. I collected the precum leaking out of my cock and slipped it over the shaft, enjoying the warm, slick feeling.

"This is hot, Brad," Kelly said. "I'm really enjoying this."

"Not half as much as I am," I groaned. "You're doing great...Keep it up."

I looked over at Cathy again, and her fingers were dancing over her pussy. I felt Kelly's other hand start rubbing over my ass while she continued to stroke in and out of my hole. The combination of watching Cathy, feeling Kelly's hands both on me and inside me, and sharing such intimacy with both of them, had me rushing toward a powerful orgasm.

I lightened the pressure on my slick cock to draw out the pleasure, but I kept the strokes fast. Heat radiated from my cock and ass, and spread through my entire body in waves. I was just barely touching the underside of my cock, riding the knife edge of release. When I couldn't hold back anymore, I squeezed down and pumped my cock hard. Kelly felt it and plunged her fingers in deep, spreading my ass with the pressure of her knuckles.

"Uhhhhh, ohhhh, ahhhhhhhhhh," I moaned as my orgasm overtook me. Ropes of cum shot out of my cock as spasm after spasm engulfed me. My toes clenched and I balled the sheets in my left hand, completely unable to control my body as I succumbed to the waves rolling through me.

Finally, the spasms settled down and I relaxed to enjoy the aftershocks. Kelly expertly worked both of her hands to prolong the sensations without being too intense. I slowly stroked and milked the last pleasure from my cock. I had lost track of Cathy in the throes of my orgasm, so I opened my eyes and looked over at her. She lay back in the same post-orgasmic glow I was feeling, slowly stroking her swollen pussy lips with one hand while the other cradled a breast. She smiled as she noticed my gaze, and I smiled back. Her eyes expressed contentment and acceptance, reassuring me that she was comfortable with the intimacy between Kelly and me.

"Whewwwww," I sighed, letting go of my cock and resting on my forearms.

"Just relax, Brad," Kelly said as she slowly worked her fingers out of my ass. She continued to slowly stroke back and forth, but brought them out a little more each time. With her other hand, she massaged around my opening, keeping me relaxed as her fingers worked themselves out. When they emerged, she continued to rub my butt.

"That was unbelievable, Brad," Kelly said. "Just like Cathy said, I could feel your contractions, both in your ass and in your cock. It was like I was riding the waves with you."

"They were really good waves, too. Thanks, Kelly. You were awesome."

"You're welcome. Now, I'm just a little horny myself, so when you think you've recovered, let's get cleaned up."

"Can't wait for me to get my hands on your ass, huh?" I laughed as I got up and started toward the bathroom. Kelly followed, shaking her head at me.

After we cleaned up, I got back on the bed and motioned Kelly to lie down. Cathy settled back into her chair and gave me a wink, mouthing "You're welcome" to me. I shook my head, not believing that I would be putting my hands on another beautiful woman this weekend.

"Ummmmm," Kelly purred as I started with a light rub around her shoulders and spine. I moved down to her lower back, getting another sigh of approval. I took the opportunity to study Kelly's body. I could see the swell of her breasts flattened against the bed, the taper of her waist, and then the flair of her hips leading to toned legs. Her ass slowly shifted as she ground herself into the bed. Sensing her need, I slid my hands onto her firm cheeks.

"Yes....that feels good," Kelly whispered. I traced my fingertips over her ass, watching Kelly arch her back to push into my hands. Kelly sighed, and her breathing deepened. I glanced over at Cathy and saw her attention focused on Kelly while her fingers traced between her legs.

Kelly spread her legs slightly, inviting me further. When I held back, she pulled a leg forward, arching her back further.

"Brad....please?" she begged. I relented and slid my fingers down around her puckered hole. Kelly had arched her ass enough that I had a good view as I circled, watching her twist to get my fingers on her sensitive spot. I committed the show to memory, knowing that it was a one-time experience.

"Ohhh....yes," Kelly sighed as I let my little finger trace directly on her anus. I started lightly and let her build the pressure as she continued to push her ass up into my fingers. With my other hand, I massaged her firm cheeks, giving her stimulation all over. Kelly enjoyed this position for several minutes, then she pulled her elbows and knees under herself and raised her hips from the bed. In this position, I reached under her and cupped a hanging breast, getting another sigh of approval.

Seeing Kelly push and writhe against my finger probing her ass, I decided to see if she really wanted to push against me as much as possible. I brought my thumb down to her sphincter, letting my other fingers spread possessively over the rest of her ass, hinting at what was to come.

Kelly immediately groaned and arched her back hard, bringing her pussy into my view. I let my fore and index fingers drift down along either side of her pussy, framing the puffy lips as she squirmed back against me. I realized I was hard again as I enjoyed the view of her ass and pussy just inches from my eyes. Looking up, I saw that Kelly had her eyes tightly shut, a look of concentration on her face. I turned my head to check on Cathy again. She turned up to me, and let out a long breath through pursed lips. Her eyes shone with excitement. She was definitely OK with this.

I found the bottle of lube on the bed and flipped it open with my left hand. Keeping my right hand brushing Kelly's ass, I drizzled a good amount on my thumb and replaced it at her sphincter. She pushed back and relaxed, opening up to me. I pushed in just a bit, getting a whimper of assent. As Kelly repeatedly pushed back into my hand, I worked my thumb in a little more each time, sinking easily into her inviting ass. With her moans of pleasure encouraging me on, I sunk my thumb completely into her. With a final push back, she spread her asshole around the thick part of my lower thumb, my hand jammed tightly against her.

"Oh, fuck, that feels good!" she panted. I started a twisting motion as I matched her thrusts. Her sphincter spread open on each push inward, and then pulled at my thumb as I stroked back. I drank in the sight of my hand plundering Kelly's gorgeous ass. I reached back down to her breast and twisted her nipple in my fingers, getting more sighs and whimpers of pleasure.

After letting Kelly revel in these sensations, I shifted back and moved my fingers to frame her pussy. She groaned and twisted back into my hand. I took a good look at her engorged pussy, the wet inner lips prominently leading down to the hood of her clit. I let my hands move inward, now sliding along her outer lips. Kelly quickened her thrusts to openly rut against my hand, my thumb plunging into her ass. Finally, I slid my fingers into her inner lips, working to drive Kelly white hot without pushing her over the edge.

"Ugghh, ugghh, ugghh," Kelly grunted in time to her thrusts. She had given herself over to the sensations, and I felt her raw need and her dependence on me. It was time to take her to climax.

I moved my hand from her breast and brought it under Kelly until I was touching her clit, both my arms now wrapped around her. Keeping the pressure on her ass and pussy from behind, I now gently teased her clit from the front, drawing her closer to the edge. As she ascended, I increased the pace but lightened the pressure until she was squirming in my hands.

"Oh, oh, oh." Kelly's whimpers increased in pitch. She had stopped thrusting, her muscles taut as she hunkered down on my hands. I kept her on the edge until she trembled, her back dotted with the sweat popping out of her pores. Then I felt it deep in her ass, the involuntarily quivering of her inner muscles signaling her impending climax. I immediately frigged my fingers hard against her clit, driving her over the edge.

"Uhhhhhhhh, uuuggggghhhhh!" Kelly expelled as her orgasm wracked her body. I felt the convulsions billow up from within and wash through her body. Her ass clutched at my thumb as her pussy contracted around my dancing fingers. With each contraction, Kelly whimpered and trembled, and she would have collapsed if not for my arms. I marveled at the intensity of her orgasm as I shared each spasm with her.

Finally, I didn't feel any more contractions, so I slowed my hands to gentle caresses as Kelly twitched with the occasional aftershock. As her panting relaxed into breathing again, I slowly lightened up on her pussy while my thumb came out a little more each stroke. Once I eased it out, I gently massaged her ass, keeping a connection as she recovered.

"Ohhhhh, God," Kelly exhaled as her eyelids fluttered open. She eased her knees back and settled down onto the bed. "I don't know if I'll ever get up."

I patted her ass and chuckled. "I could feel it. You must be exhausted."

"Yeah, but a good exhausted."

"Brad?"

I whipped my head around to Cathy, who had that wild look in her eyes.

"Looks like you enjoyed it too." She pointed at my rigid cock. "You want me to help you with that?"

"I'd love it."

Cathy jumped up from the chair and hopped on all fours on the bed, looking over her shoulder at me. "Pound it into me hard and fast. Please, just do it."

I turned to her and lined up my cock with her swollen pussy. When she felt the head at her entrance, she jammed back as I pushed. I impaled her until my hips slapped her ass, then I grabbed her hips and started pounding. Cathy was right, I needed a good fuck after watching and feeling Kelly, and I could tell that she needed one too. Our bodies slapped against each other as we drove to climax. I saw Cathy slip a hand between her legs, and I felt her fingers graze my balls as she diddled herself.

Fortunately, my earlier orgasm kept me from cumming too soon as Cathy worked herself over. She panted and moaned as she repeatedly rammed back into me. Her fingers went into overdrive, then I felt her pussy tense up and spasm as she came all over my plunging cock, never stopping her backward thrusts. Watching her head thrash and her body heave drove me to a new level of excitement, and when I looked down to her gorgeous ass getting flattened by my hips, the cum started surging through my balls. I pushed a few more times and then pulled her hips tight as I spurted into her clutching pussy.

"Oh, God, that felt good," Cathy purred from below me when we had calmed down. "I needed that so bad."

"I needed it too. You are amazing, Cathy," I answered. "I'm one lucky guy."

"Glad you realize it, Brad," Kelly interjected. "I almost had to play with myself again, watching you two fuck your brains out beside me."

"We were going at it pretty heavy, weren't we?" Cathy giggled.

"Yeah. Who would think that cool, collected Cathy would be on her hands and knees, ramming herself onto a hard cock and moaning like there was no tomorrow? Damn girl, I didn't know you had it in you."

"I had a good example to follow, Kelly," Cathy replied smoothly.

Kelly laughed. "I guess you're right. I was getting off pretty good myself." She turned to me. "Brad, where the hell did you learn to do that?"

"I just let my hands follow your body, Kelly. You did the rest."

Kelly narrowed her eyes. "Nice, safe, answer, bud. I'll ask again sometime."

"Of course," I replied evenly. "Now, I think I need a shower. I'm sorry Cathy, I guess I just grabbed your hips without even cleaning up."

Cathy turned to me. "Brad, it's OK. I kind of...invited you to grab me, didn't I? I'm glad you listened. Now, about that shower. Care if I join you?"

"Um, not at all," I replied, seeing her eyes dance as they registered the surprise in mine. After all the things we'd done together, Cathy still hadn't really moved outside the boundaries of our original deal. Even our unplanned encounters could still be chalked up to me helping Cathy loosen up sexually. I had taken care to keep our interactions somewhat neutral, giving Cathy the space to act on her desires without a relationship getting in the way. Now, however, she was offering to just spend some time with me, with a twist. We'd be naked together, but too worn out to do anything besides enjoy each other's company.

"Give me a sec, and I'll call you in." Cathy got up and closed the door.

"Well, well, well..." Kelly called out when the door closed. "Miss Cathy is showing some interest. What are you going to do about it, Brad?"

"What any guy with half a brain would do. I'm going to show some interest back!"

"Good idea. Now, I figure it's time to ask again. Where did you learn to play with a girl's ass like that?"

"Old girlfriend. She taught me what she liked with her ass. I figured that you would like something similar, so I gave you some hints and went ahead when you approved. When I said that I was following your body earlier, it was mostly the truth."