The Web Ch. 05

"That sounds wonderful. I think Cathy will love it." My pulse had picked up and my cock had stiffened. Fortunately, my loose slacks gave some room.

Cathy smiled and relaxed back. "Me too," Desire said. "I've been waiting for this for a long time."

"Thank you, Desire." As excited as I was, I had two more conversations to go. "Now, may I talk to the Protector?"

"This is the Protector."

"Protector, can I ask a favor for tonight?"

"Probably. It depends on what it is."

I went on, knowing that the Protector was personifying any remaining nervousness about anal intercourse. "Protector, I am sure that you are concerned about Cathy being hurt in what we are about to do. She has taken many small steps to get to this point, so she should be more than ready. However, we are still going to take this very slow and let her determine the pace. If she can remain relaxed, she won't have any pain, and she will have a great experience. In your role as protector, will you work to keep her relaxed so she doesn't get hurt?"

"I know she wants to do this, so I will do as you say."

"Thank you, Protector. Now, may I speak to the Controller again?"

"Speaking."

"Controller, I have one favor from you. When Cathy and I make love, she'll be on top and in charge. Can you help her control the pace so she feels the greatest pleasure? You'll probably want to go very slow at first, and then maybe speed up as she adjusts and wants more."

"I'll be happy to do that."

"Good. Now, would you please take us back to the beach?"

We returned, and I outlined a plan to Cathy.

"After we get each other excited and we go over your homework, how about me sitting back against the headboard of your bed with you straddling my legs facing me? You can then sink down at your own pace, and we can be close as we make love this way for the first time."

"That sounds perfect, Brad. Thank you."

"Would you like to get started?"

"I'd love to."

I led her back from the beach. "Cathy, do you remember what we talked about?"

Cathy stretched sinuously, lightly dragging her ass along the cushions underneath her. "Yes—everything." She turned and looked into my eyes. "Let's go to the bedroom."

I got up, seeing Kelly wink at my tented slacks. I moved over to Cathy and took her hand. She stood up and we both moved toward the bedroom, Kelly following. The lamp bathed Cathy's bed in soft light. Kelly's chair stood ready, and I noticed the two butt plugs and the lube resting on a couple of towels on the nightstand.

"I kind of knew what we'd be doing tonight," Cathy said by way of explanation. She looked into my eyes. "I want this."

"I do too," I replied. I took her hand and gently twisted her around, pulling her back into me. I cupped her breasts as she leaned her head back. A small sigh escaped her lips before I covered her mouth with mine. We kissed hungrily. My cock grew rock hard in my loose slacks and Cathy took advantage, rubbing it along her ass as she twisted in my hands. I rolled her nipples in my hands, the fine weave of her top giving me intimate contact. Cathy had now worked her ass over my cock, and the light fabric of her skirt gathered in as she slid my length between her cheeks.

"You feel...really good," Cathy panted between kisses.

"You are so incredibly hot," I breathed back. I pulled her tight and whispered in her ear. "I need you."

"Oh, God," she moaned.

I dropped my hands to pull up on her top and she lifted her arms into the air. I gently pulled the top over her head, letting her hair cascade free. I looked over her shoulder to admire her trim breasts, riding firm and capped with erect nipples. Like a magnet, her nipples drew my hands back, and I lightly pinched and pulled them as Cathy sighed in my ear.

Cathy reached back and tugged at my polo shirt. I turned her back around, and she pulled it over my head. We embraced, the hard points of her breasts dragging across my chest as we kissed. I felt Cathy's hands undoing my belt, and I stepped back to allow her to pull my slacks down. My cock sprung free, and she chuckled at my lack of underwear. As she rose back up, she paused to kiss the tip of my cock. I groaned.

Then it was her turn. She turned her back to me and pulled my hands to her waist. I took the hint and unfastened her skirt. As her tight ass cheeks come into view, we both laughed at her lack of underwear. I kneeled down to ease the skirt over her feet, and then I planted a kiss on each cheek, communicating how much I appreciated her ass.

"You like that?" she breathed.

"I love it," I replied as I stood up. "Every inch of you is the best."

"This too?" she asked as she maneuvered her puckered hole around the head of my cock.

"Especially that," I replied. Cathy sighed and clamped my hands over her breasts. I squeezed and pinched more roughly.

"Yes," she moaned. She arched back and pushed her ass harder against my cock, breathing hard now. We ground our bodies together as I continued to pleasure her breasts.

"Should I...show you...my homework?" she panted.

"Yes," I whispered back. "Show me how much you've practiced."

Cathy pulled away and sat on the bed, grabbing the toys and a towel. As I sat down to join her, I looked over at Kelly. She had her skirt hiked up and was lazily stroking her pussy. She smiled when she caught my eye. I winked back and sat beside Cathy on the bed.

"I'm just going to lie back where you both can see my progress. You've got me so turned on, I can just start right now." Cathy arranged a pillow under her head, angled herself in our direction, and hooked her nearest leg under her arm. Her pussy and ass opened up to our gaze. Taking the lube, she flipped the cap, drizzled some over the small butt plug, and placed it at her anus.

"Ohhhhhh," she moaned as she pushed it part way in. My cock lurched as I watched her anus expand around the plug, accepting a little more with each push. Cathy's other hand brushed over her pussy lips as she continued to fill her ass. Soon, her sphincter closed over the waist of the plug. "Ummmmm. I have to confess that I've played with myself a lot like this."

"I bet. I want to play with myself right now."

"Naughty boy, you'd miss the fun later. Plus, I've got one more to go." Cathy used one hand to slide the plug around inside her while she continued stroking her pussy with the other.

I reached over and tweaked a nipple, causing Cathy to gasp. "You're kind of defenseless there, aren't you?"

"Maybe," she replied, giving me a good view of her hand caressing her ass, "But I think you're kind of defenseless, too."

I laughed. "I think you're right—I can't resist you."

Cathy smiled. "So I pass this homework exercise? Ready for the next one?" I nodded, my head spinning. Cathy eased the plug out of her ass and placed it on the towel. She lubed up the larger one and placed it at her entrance, closing her eyes and visibly relaxing. With her other hand caressing her pussy, Cathy started pushing the plug into her ass. This time, her breathing deepened as she worked it inside. "It feels really good," she whispered.

I watched as she guided the plug back and forth, going a little deeper each time. Her breaths lengthened into deep pulls and sighs as she continued to relax her body. A quick glance at Kelly confirmed that Cathy was holding both of us riveted with her display.

"Ohhhhh, that's it," Cathy whispered as she felt the widest point pass through her sphincter. She continued gently pumping it as she twisted her body in pleasure. "It's so relaxing to do this," she said. "I just feel fantastic."

"You look fantastic."

Cathy continued to play with herself as she guided the plug in her ass.

"Well, I think that you pass your homework with flying colors," I said.

Cathy and Kelly both laughed. "Do I get a gold star?" Cathy asked.

"I was thinking something better. Perhaps an orgasm?"

"I'd like that."

I guided myself between her legs and let her spread her pussy lips for me. The pearl of her clitoris stood proud between her fingertips, and I zeroed in, knowing that she was ready. "Oh, that feels great," she whispered as I rolled her clit around with my tongue. Her other hand grazed my chin as she pumped on the toy in her ass. Her breathing lost its relaxed pace as she pulled up both legs to rest her feet on my shoulders.

Cathy's fingers sunk deeper into her pussy as she squeezed her clit up for my tongue. I attacked the sensitive bud with deep strokes and firm pressure. When I sucked it between my lips, Cathy jumped. "Oh God, don't stop," she moaned, and I kept up the strokes and sucking as I felt Cathy pump the butt plug harder. This time, I wasn't going to back off as she approached climax. I knew she wanted this one fast and hard.

Cathy started bucking against me as she gulped in air. I felt her body tense up and I sucked her clit in deep, clamping it between my lips.

"Ohhhhhhhhhhhhhhh," Cathy wailed as she pulsed in orgasm. I held on to her clit with my lips while she trembled beneath me, the contractions rippling through her pussy. As she came down, I gently released her clit and just nuzzled her pussy. "Wow, that was intense," she said after she dropped her feet from my shoulders. I slid back, my cock rock hard from witnessing her orgasm. Cathy was spread in front of me, her pussy lips deep red and her ass still clutching the plug. I glanced over at Kelly, who winked as she was obviously recovering from her own orgasm.

Cathy sighed. "I could stay like this all night, but I'd miss something even better. Let's get ready, shall we?" She closed her eyes, relaxed her body, and slowly pulled on the plug. Her ass opened up and she slowly guided the taper out, breathing deeply. When it was out, she opened her eyes. "Brad, that was the best. Thank you so much." She put the plug the towel and lifted herself up as I maneuvered myself to lean back on the headboard.

Cathy looked at my straining cock and giggled: "I guess you don't need any more foreplay." She moved over to me and straddled my hips, her face getting serious as she slid my cock along the crack of her ass. "I want this so much," she said as she leaned in for a deep kiss. Our tongues danced while I cradled her breasts in my hands.

"I want this—want you—more than anything," I answered as we broke the kiss.

Cathy answered by raising up on her knees and reaching for the lube. She drizzled a stream on my cock, gently spreading it all over. Then, looking into my eyes, she settled above me and positioned my cock at her well-prepared back door.

"Feels great already," she whispered. Her eyes registered my pleasure from the warm and inviting pressure of her sphincter on the head of my cock. I felt it relax and knew she was pushing out to open herself to me. Then, her eyes still locked on mine, she started to slowly sink down. My cockhead passed deeper and felt her muscular rings expand around it. Cathy kept her breathing slow and steady while she continued her journey. Then she sighed deeply, and I felt the first ring start to close over my shaft. Cathy paused, raised herself slightly, then continued sinking down. The pressure on my cockhead eased, and we both knew that I was in.

Cathy smiled down at me, and then she raised up and slowly sank down again. My cock went a little deeper. After a couple of more strokes, she let go of my cock, confident that I was secure in her back tunnel.

"Incredible," I whispered, feeling the smooth rings of her rectum squeeze my shaft. I took the cheeks of her ass into my hands, cupping and kneading them.

"So good," she whispered back. She placed both hands on the headboard behind me to support herself and then continued her motions, sinking a little more each time. Her muscular rings sank deeper around my shaft, while the head rubbed along her smooth passage. On her downward motions, she started gyrating her hips, attesting to her pleasure. I removed my hands when I felt her butt cheeks start to touch my legs. She twisted a couple of more times and then sank down the final distance, pushing my cock as deep into her as possible.

"Ahhhhhh, that feels good," she said as she rested her ass on my legs. She lifted up slightly and began slowly humping me, bottoming out each time.

"You feel amazing," I answered back. "Unbelievable." My cock reveled in her warm, tight tunnel. I reached up and cradled her breasts again, twisting her nipples to little moans of pleasure. I then reached down to find her pussy, open and wet for my touch.

One of the fun things about anal sex is that you get full access to a women's pussy. You can reach inside to rub the walls, or you can just play with her lips and clit. You're rewarded for your efforts by the squeezing of her ass as she responds to the sensations. I took full advantage, sliding a couple of fingers inside and hooking them back to rub the bumps of her G spot.

"Oh, God," she moaned and threw her head back in bliss, finally breaking eye contact. Her ass clamped around my shaft as she squeezed her pussy around my fingers. She brought her head forward again and started pushing her hips back and forth, starting to make the transition from carefulness to enthusiasm over my cock in her anus.

I slid my fingers out and starting encircling her clit, knowing that I didn't have forever before I went over the edge myself. Cathy gave me encouraging gasps and twisted above me as I rolled her clit in my fingers. Her hips moved faster, and I realized that she was now completely fucking me, no longer worried about anything but fully enjoying the pleasure that her body was giving her.

My cock pulsed with that realization, and I knew that I was on a one-way trip to a major orgasm. I started squeezing to hold back as much as possible, but the pressure building in my balls would not be denied.

"I'm going to—come soon, Cathy," I whispered while I still had the ability to speak.

"Please—I want to feel it," she whispered back between breaths.

I continued frigging Cathy's clit while she humped my cock, the icy heat radiating out into my legs. Her ass smoothly gripped my rod and sent my pleasure to new heights. I am going to shoot into this unbelievable women's ass, I thought.

I pressed my fingers into her clit as I went beyond endurance. Cathy dropped down and drove my cock deep inside her as the cum erupted from my balls and surged up into my shaft, passed the gripping rings of her sphincter, and then spurted into her tunnel.

"Ugghhhh, ugghhh, ugghhh, ohhhhhhhh" I grunted as the pleasure exploded through my body with each spurt. What an incredible feeling it was to have Cathy so deeply connected to me as I came. I existed in awareness only, not conscious of anything but pleasure and Cathy's body tightly clutching mine.

Finally, the spasms wound down enough for me to use my limbs again. I pulled my head away from Cathy's chest and looked up into her eyes. They searched mine, witnessing the depth of my experience in my expression. With that, I saw her excitement and need growing, her eyes getting wild around the edges. I gently encircled her clit again.

"Yes," she whispered. She raised up and started lightly humping my cock again. She smiled and sped up as she felt my cock remain hard within her. For some reason, I don't get as sensitive after cumming in a women's ass—I think it's the fact that the muscles squeeze the shaft more than the head of my cock. Inside a pussy, the head seems to get more stimulation than the shaft, so it's gets more sensitive. Whatever the case, I was happy to remain hard and able to concentrate on Cathy's pleasure while she rode me.

I played with her clit as she regained her rhythm, twining her hips hard as she filled her ass with cock and pushed her pussy into my hand. She wrapped her arms around my neck and cradled her head against mine as she climbed to orgasm. I felt the sweat break out on her skin as her body tensed. With her throbbing clit clamped between my fingers, she hugged me tight, leaving just enough room between us for my hand at her pussy. She moaned continually now, her muscles tensing more and more, her hips continuing to piston my cock in her channel. Her muscles quivered with the effort...she held her breath...still she climbed...and then she exploded.

"AAAAAaaaaaaaaa," she screamed as a giant contraction lashed through her body. Her rectum pulsated with continuous spasms, and I felt a gush in her pussy as her clit quivered in my fingers. She rammed herself down, collapsing around my cock, her body not her own. Wave after wave passed through her, and she sobbed in response, taking big, wracking breaths. She rocked against me, holding on for dear life as she cried through the aftermath. I held her tightly back, knowing that she needed my presence to bring her back from the depths of emotion she was going through.

"It's OK," I said soothingly as I started rubbing her back. She cried again, and I felt the slight jerks in her chest as she fought to control her breathing. "Shhhhhh," I cooed, "it's alright, it's alright."

Finally, she sighed deeply and pulled her head away from mine. I looked into her red-rimmed eyes and straight into her soul. I saw love, and I saw the shock of powerful emotions. I saw the fear of being truly naked in front of me, of how I would react, of being defenseless. My eyes welled up in response, and I surrendered my expression to my own emotions, letting my love for her pour out, not even completely knowing what I communicated. Her eyes widened in surprised, then she leaned in and clamped her lips to mine, finally breaking her gaze when she twisted to the side.

She broke the kiss and leaned back. We locked gazes again, and a lot things went back and forth at a level I didn't really understand, but knew was very good. Finally, Cathy smiled shyly. "That...that was...really good."

"That was really, really, good," I said back, widening her smile.

"Thank you for being there for me."

"Always," I replied, and she kissed me again. We held each other for a while.

"I better get up before I can't move anymore," she admitted. I nodded and released her pussy as she slowly raised herself off of me. My cock had softened a little, but I still felt the smooth rings slide up my shaft. Cathy gasped slightly when her sphincter closed around my retreating cockhead. I slid down to where I was lying on the bed, and Cathy pillowed her head on my chest. I caressed her hair as we both relaxed.

Remembering Kelly, I turned my head to look over at her. She was a mess, sweaty, disheveled, and streaked with tears from crying.

"It was emotional for me, too," she said after blowing out a shaky breath. She lifted her hand, and I saw her swollen pussy. "Very fun, but also very emotional."

Cathy lifted her head and looked over at her friend. "Thanks for being there, Kel."

Kelly smiled. "That was the most intense, gut-wrenching thing I have ever seen, Cathy. I will never forget that. Thank you for sharing yourself."

Cathy nodded and sighed contentedly, relaxing again. Her fingers traced over my arms and chest. "Is it always that powerful?" she wondered aloud.

"I figure the first time had something to do with it," I replied, "but you're also a natural. I think it will always be pretty intense for you."

"Maybe it's the guy I'm with," she wondered again.

"No doubt that's a big factor." I laughed quietly. "But I think that you're wired to deeply experience your body and share your love as well. Any guy would be an idiot to let you go."

I felt Cathy's lips brush against my chest in a kiss. "Thanks, Brad."

We lied there a while longer, then I heard Kelly get up and walk into the bathroom. She washed her face and toweled herself down. "Got to dry off so I can get my clothes on," she said from the door. She came back in. "I think that I've completed my chaperone duties for tonight. I don't think you can get into any more trouble than you already have." We all chuckled as she got her dress back on and pulled her hair into a ponytail.