The Web Ch. 02


"Mmmmm." Cathy leaned forward and fused her lips to mine. Her breath came fast and hot—her show had turned her on. I ran my hands over her back, her ass, and back up to her chest, rolling her hard nipples between my fingers. She kept the friction light on my cock to draw out the pleasure for both of us.

Cathy drew herself up and looked down, watching her pussy slide over my cock. She then raised her hips, took my cock in her fingers, and positioned it at her opening. She slowly sank down, and I felt my cock slide into her liquid heat. An involuntary groan escaped my lips. I looked up and saw that smile play about her mouth again. She could feel and see my appreciation, and that bolstered her confidence in revealing herself. She stretched and closed her hands behind her head, thrusting out her chest and looking down at me. I let my gaze wander from her face, framed in her arms and hair; down to her breasts, pushed out with hard nipples standing tall; and further down to her pussy lips, encircling my hard cock. I had never enjoyed a sight so beautiful before.

Movement from Kelly's direction caught both our eyes. I looked over to see Kelly pull her shirt over her head, and then undo her bra. She kept going, sliding her skirt and panties off in one motion, throwing a towel down and slinking back down in the chair.

Kelly saw us watching. "OK, I admit it. I'm horny as hell, and I don't want to waste the opportunity. Watching you two fuck is something I've never done before. It's way better than any movie."

"I've always preferred live theater myself," I observed, feeling Cathy's laugh twitch down my cock.

"OK, smarty-pants," Kelly said as her laugh subsided. "You better get back to your starring role," she said as she cupped one of her breasts.

Ordinarily, I would have been hungry to watch Kelly pleasure herself. She was certainly striking naked, with firm, medium-sized breasts topped with hard nipples. However, I had a goddess astride my hips, and I shifted my gaze back to Cathy. She smiled back at me, pleased that my attention was back. She shifted slightly up and down.

"You feel wonderful, Cathy," I said as I brought my hands behind my head. I was going to let her control our lovemaking. I enjoyed driving my cock into a woman, but it was also particularly erotic to lie still and let a woman work her hips over me. The gentle motion could really build up the pleasure in my cock. Cathy took her time, slowly rocking up and down, watching me enjoy her body.

After several minutes of pleasure, Cathy was biting her lip and breathing more heavily. She brought her hands down onto my chest and starting twisting her hips, driving my cock inside her. She looked down and watched her pussy slide down on my cock and then release it as she raised forward. I watched our union as well, knowing that Cathy was getting to experience the visual side of sex.

I felt Cathy drive faster. I looked up into her eyes and saw her concentrating, and I knew that she was climbing her way to orgasm. She locked eyes with me, and we passed our need and readiness back and forth. I remained still and felt the tingling pulse throughout my body. Cathy worked me expertly, lightening the pressure as we both got close, extending our mutual pleasure. I noticed a deep red color spread from Cathy's neck to her breasts.

Cathy's face contorted, and her torso heaved as she wrestled with the edge of her orgasm. Finally, she surrendered, letting a sob escape her lips as the spasms wracked her body. I felt the contractions squeezing my cock, and I could remain still no longer. Grabbing her hips, I thrust upward into her and held on as my body twitched beneath her. I came so hard, it was nearly painful.

When my eyes refocused, I saw Cathy looking down at me, a smile of contentment on her face. Cathy moved her hips slowly, milking aftershocks out of both of us, and she leaned down for a kiss. We let the kiss linger as we rode out the final waves.

Cathy pulled back and studied me. "Brad, I, that..."

"I know," I replied, "no words."


"How about 'Fucking incredible!'" Kelly interjected. "I'm glad I had already cum, so I could pay attention as you two went into orbit. I'm going to get off on that image for years to come."

"I'm glad you enjoyed it, Kelly. And you're right, 'fucking incredible' is literally correct for what we were doing," Cathy observed, trying to hide a smile.

"Exactly, Miss Smart-Ass." Kelly stood up and started finding her clothes. "I had better get dressed before I start playing with myself again, since you two don't look like you're moving anytime soon."

"I would jump up and help, but I'm being pinned down here by this sex fiend," I responded, getting another wagging finger from Cathy.

Kelly finished dressing and looked over again. "You look lovely, Cathy, with that glow of getting fucked really well. You two get a good night's sleep—I'll just show myself out and call tomorrow. Remember, behave yourselves since your chaperone will be gone."

"Could I get you to put out the lights?" Cathy said. "I don't think I have the energy to get up."

Kelly laughed, shaking her head, but she did turn the lights off as she got up. We could see the lights dim in the rest of Cathy's place as Kelly let herself out. As she left, Cathy collapsed down on me. "Good sex always puts me to sleep."

"Me, too," I answered, finding her lips for a kiss. "Let's find the sheets."

We snuggled against each other and were out.

I woke feeling great, partly as the memories of last night, and part due to the soft skin against my cock. Cathy spooned against me, and my morning hard-on was nestled in the crack of her ass. My arm draped across her chest, and her hand covered mine. I couldn't tell if she was awake or not. My hard-on was certainly not going anywhere in this position.

I wondered how our arrangement covered the morning after. If I honestly thought about it, I knew that I was seeing Cathy in a new light. I enjoyed our dinner and conversation together, and I had laughed many times to her dry wit. Of course, the sex was fantastic. Cathy might think she was shy, but she had all the instincts for passionate love, as well as the skills for physical pleasure. Would she be interested in making love outside our "clinical" boundaries?

Cathy soon answered my question. She stirred slightly, and snuggled her hips further back into me. "Mmmmm," she sighed. Her hand pulled mine against her, cupping the bottom of her breast. I took the hint and slowly started caressing her flesh, getting a long moan of approval.

I moved up from the underside of her breast, finding her nipple hard and prominent. I circled and rolled it between my fingers, also cupping her entire breast with the nipple sliding between my fingers. Cathy's breathing deepened as she savored the sensations. After a while, she lifted her arms over her head and luxuriously stretched, pushing her breast into my hand and twisting her ass against my cock. That got a moan out of me.

Cathy responded, lightly rippling her ass along the underside of my cock. I'm sure she could feel my precum leaking out. She shifted along me, and I could feel her ass settle into the junction of my cock and balls. Her grinding became stronger, and I pushed into her, reveling in the feel of her ass cheeks. I moved my hand from one breast to another, tweaking the hard nipples back and forth. We ground into each other for a long time, and I wondered what she was feeling with my balls pushed into her ass. I knew what I was feeling, which was incredible pleasure.

Knowing if I stayed in this position much longer, I would cum over Cathy's ass, I rolled her on her back and climbed over her. After a long, good-morning kiss, I leaned down and captured her nipples in my mouth, letting them pop out as I pulled my lips back. Cathy squirmed under me, and I could feel her need. I traced kisses down to her navel, and worked my way to her waiting pussy. She gasped and spread her legs as I dragged my tongue along her slit. I found her slick, hot, and ready.

Cathy pulled her legs back and rested her feet on my shoulders, giving me easy access to her spread labia. I continued gently working around her pussy until I felt her bucking against my tongue. I took this as a signal to move higher and attack her clit.

"Oh, God, don't stop," Cathy moaned as she grabbed my head and pulled me tighter. I ran my tongue all around her prominent clit, and finally sucked it inside my mouth as Cathy's breathing got ragged and she started tweaking her own nipples. I never left her clit now, alternative dragging my tongue across it or sucking it as Cathy pushed into my face.

"Uh, oh, God, ah, aaaaahhhhhhh," Cathy wailed as she came, bucking against me. I felt her pussy contracting around my tongue and knew she was coming hard. After a long set of aftershocks, she collapsed back and dropped her feet from my shoulders. "God, that was exactly what I needed. Thank you so much, Brad."

"Anytime, Cathy. I loved watching your pleasure."

"Be careful what you say. I could get used to that wake-up!" Cathy laughed. She stretched languorously. "Give me a second to recover, and I've got one more thing in mind this morning. I think you'll like it," she winked.

Cathy rolled over and stretched one more time. "Mmmmm." I enjoyed the sight over her back, ass, and legs shifting under my gaze. She climbed up on her hands and knees and looked back at me. "I want you inside me."

My cock leapt to an even harder level as I positioned behind her. I lined up my cock and she pushed back, her hot wetness taking me in easily until I bottomed out. Cathy dropped her head down to the mattress, looking back between her legs. "Ahh, this feels great."

I started slow, savoring the feel of my cock working deep into her from behind. Cathy kept her head down, watching as she pushed back into me. Her thrusts became harder, and I matched her, feeling her grind her ass into my hips.

"Cathy, you feel amazing."

"So do you, Brad. Don't hold back, I want it all."

I grabbed her hips and pulled her into me with each thrust, picking up the pace. Cathy was moaning now, and she crossed her arms under herself, playing with her nipples. I watched her ass push back into me, and I felt the cum boiling in my balls. I looked down at my cock plunging in and out of her pussy and felt my balls tighten. "Uhhhh," I groaned, getting the same response from Cathy.

I held the pressure back as long as I could, feeling the pleasure mount in the base of my cock. Just as I was about to cum, I pulled Cathy back against the underside of my cock to hold back just a little bit more. Somehow I noticed Cathy shuddering beneath me, and I finally surrendered to the explosion within me. "Uhhh, uhhh, uhhh, aaaahhhhh," I cried out as I shot into her spasming vagina.

Well, there aren't many words to adequately describe a really great orgasm, so I just existed in mindless pleasure as my cock continued to spasm. I kept my cock deep within Cathy, and she continued to grind her ass around it as she milked her orgasm for all it was worth. We stayed like that for a long time, whimpering our contentment to each other. At last, I slumped forward and kissed Cathy between her shoulder blades.

"Mmmmm," Cathy said. "What a way to wake up."

"I could do that every day for the rest of my life," I answered, only then realizing how much meaning might lie behind those words.

Cathy turned her head and cast me a sideways, appraising glance. Then she smiled. "Thank you, Brad. It was really, really, good."

"You have no idea," I answered. "Care to lie down beside me?"

"I'd love to." I pulled slowly out of Cathy and we both groaned as my cock dropped free. We lied down and I wrapped my arm around Cathy, spooning against her again.

"Mmmmmm," Cathy said. "This is so relaxing."

"Even after a great night's sleep, that huge orgasm is making me sleepy again," I replied.

"Me, too," Cathy replied, and I felt her breathing slow and deepen. I took that as permission to let myself drift off, happy that Cathy and I shared a desire to nap after sex.

I woke when I felt Cathy stir against me. I stretched behind her, thoroughly satisfied but starting to get hungry.

"Time for some breakfast?" Cathy asked.

"You bet. All that activity has worked up a good appetite!"

"Well, let's see if you can cook breakfast as well as you make love."

"I don't think that's possible, and I'm a pretty good cook!" I replied.

"Oh, yes, I forgot how wonderful it is to wake up with a comedian," Cathy sighed playfully, as she stretched and got up. She turned around and saw me watching her. "Don't let your eyes bug out."

"I'll have to be careful about that," I said and started reaching for my bag beside the bed. As Cathy went into her bathroom, I pulled out an athletic outfit that was good for lounging and got some underwear and pants on. After a few minutes, she came out in an athletic outfit of her own, winking at my bare chest as she moved toward the kitchen.

I went into the bathroom, cleaned up, and finished dressing.

"What's for breakfast?" I said as I walked into the kitchen.

"Omelets, toast, and some fruit," Cathy replied. "Why don't you look in the fridge and see what fruit you can find? Also, do you like coffee or tea?"

"Tea, please." I looked into the refrigerator and was pleased to find a good selection of strawberries, blueberries, mangoes, and other fruits. No wonder Cathy looked so good.

I got a good fruit bowl cleaned and cut up, and helped Cathy chop the onions for the omelets. She deftly moved through the kitchen, and I found myself admiring the way she carried herself and carried on a sparkling conversation. In short order she had an omelet at my place with a mug of steaming tea and toast.

"This looks fantastic!" I said.

"Thank you. Here's to a wonderful evening and morning of new experiences." Cathy clinked her mug against mine, and we fell to our breakfast. We lingered over our plates as only the weekends allow, talking and laughing about all manner of things. We cleared the plates, and before things got awkward, I walked over and gave Cathy a hug, stroking her hair. "Thank you for a wonderful breakfast."

"You're welcome. I enjoyed sharing it with you."

We held each other a bit longer. Finally, Cathy tilted her head back and looked up into my eyes. "Brad, thank you so much for everything. I became more the person I wanted to be last night, letting go of some fears that were holding me back. Better yet, I had a fantastic person to share it with. I'm really glad that we're doing this together."

"Cathy, I can't tell you how powerful this has been for me, and how lucky I am to be sharing with you as well."

Cathy smiled, and then we both got quiet. We saw the confusion in each other's eyes, and we broke the embrace. I think we both needed some space to assimilate what had happened between us. "I'd better go collect my things," I said.

"Here, let me help you." Cathy followed me back to her bedroom. I gathered my bag while Cathy retrieved my toothbrush from the bathroom. As I walked out, I paused and looked at the disheveled bed, reliving what had transpired there.

"Afraid you won't see it again?" Cathy startled me, and I jerked my eyes up to see her leaning against the doorframe, a small smile in her lips.

"I've learned that in this life, you have to enjoy and savor each moment as if it's your last," I said. "You never know what might happen."

"Oh, I've got at least a session or two left before I'm cured, so I think you'll get back," she said lightly.

"That's great news. I want my patients to be fully healed before they leave my care," I replied in my best doctor's voice. "Please be sure to schedule your next session at your earliest convenience."

"Yes, Doctor. I'll check with the receptionist," Cathy chirped back and led me back to the front door.

We reached the threshold. On impulse, I stopped and pulled Cathy tight. "I won't forget last night. It was, well...."

"Hard to describe? I think I know what you mean." She hugged me back. "Good-bye, Brad. We'll talk soon."

I walked out the door and got into my car, waving at Cathy in the door. Driving home, my mind was in a whirl.

When I got back, I decided to go for a long run and do some thinking. The day was warm but not oppressive, so I got into a running zone and tried to sort out what had happened. Cathy had become a good friend—a really good friend—I laughed to myself, but was there something more? What had happened this morning? Was that just an extension of our session the night before, with Cathy following through on her desire to get laid from behind? Normally, I felt like I could follow a woman's signals reasonably well, but this situation changed the game. Intimacy was part of what we both signed up for, and it could easily lead to assumptions that went farther than Cathy wanted to go. At the same time, she was suspending some of her judgment in our voice sessions, and that could lead to her identifying with me more deeply than she would otherwise. I needed to sense her mood in the times where we weren't working with each other, where she was more naturally enigmatic.

I had to figure out my own emotions as well. Let's face it, it's easy to fall in love with a woman when you lust after her beauty and you're sharing mind-blowing orgasms. The real question is whether that feeling has staying power, and the answer comes from the other times you're together. How much did I like to be around her? Did we fit together? It was early, but I had to admit that I wanted to find out. I would have enjoyed our dinners without the sex, and would be looking forward to seeing her again. And looking forward to getting in her pants, I thought to myself, smiling inwardly.

The rest of the run was good to get my mind calmed down and reconnect with something besides sex. I got back and showered, and kicked back to rest a bit.

When the knock sounded, I could feel Kelly's presence, and I was right. "I wondered how long it would take before you came over. How many times?"

Kelly stuck her tongue out. "Let's just say you weren't the only ones enjoying yourself this morning. I collapsed like you did when I got home, but I woke up horny as hell. I wasn't kidding last night—you two were totally hot. Watching Cathy display herself for you, and watching your eyes devour her, that's what really did it. I'll have to play with myself again after hearing Cathy's account of this morning. Cathy said you had a talented tongue."

"I'm a man of many talents."

"I guess modesty isn't one of them," Kelly shot back.

"Yeah, well, I've sacrificed some virtues in my quest to be the ultimate lover."

"Whatever, lover-boy." Kelly got serious. "Speaking of talents, how comfortable are you with where Cathy might be going with this?"

"What do you mean?"

"You heard her last night, when Desire was speaking." Kelly emphasized the word. "She said this was a first step. If what you did last night and this morning was a first step, she could be taking you to some pretty far out places!"

"I guess I hadn't thought about that."

"Well, maybe I'm trying to do that for you. I wouldn't want Cathy to suggest something and you back out. She's invested a lot of trust in you, Brad, and it would be devastating for you to reject her desires. It would make her retreat again, after she's made so much progress. So I'm going to ask some personal questions."

"When have you not?" I wondered aloud.

Kelly laughed. "You have a point there. Anyway, let's start with the obvious. How comfortable are you with anal sex?"

"Why's that obvious?"

"You're stalling, big guy, but I'll tell you anyway. When Cathy bent over for her 'daring' pose last night, I knew what you were seeing just as much as you did and Cathy did. It doesn't take much women's intuition to connect the dots. I'm guessing that Cathy wouldn't show you her most private place unless there is a future reason. Women as smart as Cathy always know how much they are showing."

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byAntonio_y_Cleopatra© 11 comments/ 48982 views/ 8 favorites

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