The Cougar Book

by Jolie Du Prè

  “Justin, be a dear and fold the covers all the way down. Make yourself comfortable on your back, in the middle of the bed,” I said, shrugging out of my silk blouse. “Oh, no, Justin. Keep those pesky hands to your sides for now,” I said when I saw him begin to reach reflexively for his cock while he watched me.

  He actually sat on his hands, poor dear, to keep from touching himself. “Scooch down a bit, away from the pillows, so that I can get behind you. Do you like the smell and taste of pussy?” I asked him.

  He assured me, in no uncertain terms, that he did.

  “Mmm, that makes me very happy,” I said as I lowered my damp, thong-covered mound to his nose. I could feel him slide his hands out from under him and I caught him by the wrists before he could grab my hips.

  “Mmm, mmm, mmm, Justin. No hands, remember?’ I felt him whine into my pussy as I placed his arms back by his sides.

  ‘Do you like my scent?’ I asked him, rubbing myself from side to side against his nose.

  He mumbled something I couldn’t quite understand, but he managed to nod his head. I leaned over, sliding down just a bit and suggested that he tongue my wet thong. He eagerly complied, pushing his tongue against me in a very practiced way.

  “You’re not bad at this, Justin, for such a sweet, shy boy. I might even say you’re pretty good. Seems you’ve had some practice.”

  “Yes ma’am,” he mumbled. “I love to eat pussy.”

  “Well then,” I said, “you go right ahead.” I pushed the brief fabric covering my cunt to the side and lowered myself completely onto his mouth, hearing and feeling a muffled grunt. Leaning forward, I made sure I wasn’t blocking his nose, which rested in the crack of my ass. I could feel his breath tickling me as he began to use his tongue again. He was really quite skilled, and between little shivers, I complimented him on his technique.

  The room became suffused with his musk as his cock dribbled more precome; copious amounts of it ran down his shaft to gather on his balls. I couldn’t resist running a finger through the sticky coating on his sack, which led to fondling and massaging. He had such a lovely pair of balls: large and nicely formed. I could feel the skin becoming taut and feared I’d lose him too soon, so I let him go and rose from his face.

  “No, don’t stop,” he blurted. His face was wet and shiny with a combination of saliva and my juices from the bottom of his nose to his chin. The juices were running off the sides of his cheeks, as well.

  “That was very nice Justin,” I told him, “but I have something better in mind. Turn onto your stomach and get on your knees. That’s right, with your bottom in the air, just like that. I think you’ll like this,” I said.

  I put lube on my finger and pressed it against his anus. He jumped away.

  “No, Baby, don’t be scared,” I said. “You’re just so sweet. No one’s ever done this with you?”

  “No, ah, ma’am. I, um . . . I’m not sure . . . well, that is . . .” He kept clenching his ass and moving it away from me, but without actually getting out of position. “I never did . . . I don’t think . . .”

  “All right,” I said, stroking his bottom gently, relaxing him. “I want you to trust me now. You’re just a sweet, inexperienced boy.”

  He made noises of protest. “Yes, I know, you’ve had lots of experience,” I said in a placatory way. “But, let’s assume I know a bit more than you, in this instance, okay? I know you’ll like this. Trust me.” He began to relax and tacitly agreed by pushing his rear end out in a deliciously submissive manner.

  “Good boy,” I said, as I massaged lube around his opening. He moaned a little as I added more lube and slowly pushed against his sphincter again and again, teasing the opening until I finally inserted my finger slowly, a fraction of an inch at a time. I reached under him and found that, although he had softened a bit, his cock was still semi-erect. I gently stroked the back of his balls and cooed to him as I slowly slid my finger in and out, a bit deeper each time.

  After a while, I felt him begin to hump back against my hand, trying to achieve a deeper invasion. His cock was steel hard once again as I chuckled and said, “If you don’t like this, we can stop.”

  “Oh, god, no. Don’t stop, please,” he begged, continuing to rock against my hand.

  I added more lube and inserted a second finger, widening him a bit more. He grunted but continued to push back against me, and he whined his displeasure when I withdrew my fingers altogether.

  “So you like that after all, do you? Don’t worry, Justin,” I said. “I won’t tell.” I slowly inserted the plug, past his sphincter, all the way to the end. Once his muscles had closed around the neck of the plug and it was well seated, his breathing calmed. He jumped and froze when I turned it on.

  “Oh, man!” he moaned.

  I got him turned over on his back again and made him open his eyes so he could look at me as I wrapped my hand around the base of his cock. “Having a good time?”

  The poor boy couldn’t speak. He laid there, eyes wide, staring at me, panting heavily and smiling. “Thought so,” I said.

  Squeezing the base of his cock, I told him he’d better not come. Each breath was a whine, but I continued to hold him with one hand while I put a condom on him with the other.

  “I want to get at least a few good strokes out of you,” I said, lowering myself onto him, but keeping my hand around the base of his cock. Once I had settled myself on his shaft, I removed my hand and just sat.

  “I can feel the vibration in your ass through your cock. So yummy.”

  As I began to move slowly, I placed his finger by my clit and told him to earn his keep. Amazingly, Justin was good at that too!

  He told me he couldn’t hold out much longer, and as I was on the verge, too, I let things take their natural course. I could feel his entire body vibrate right before he came. He tensed and pounded into me twice, and then shook under me. His orgasm wrenched a lovely, deep, guttural moan from him.

  Lying next to him, after turning the vibrator off but leaving it in, I played with his hair. “Justin, how old are you?” I asked.

  “I’m twenty. Why, does it matter? Um, listen, can you take that thing out of my ass please?”

  “No, not at the moment, dear, let’s leave it where it is for now.” Changing the subject, I said, “You seem to know quite a bit about how to please a woman. Just how long have you been having sex?” I asked.

  His hand began to stray toward his cock and the vibrator protruding from his ass. I caught it and brought his arm around his body and held it to his side. “No. Do you want a spanking? Now tell me how you learned to use your mouth and hands like that.”

  “I like older women. Older women teach you stuff, you know? Older women know what they want and make sure they get it.

  “I’m not really into girls my age, but when I have had sex with them, they don’t seem to want to talk about anything. I don’t think they know what they want. Well, if they do, it’s not like they’ll tell me.

  “Older women are much sexier and they aren’t afraid to teach you things. Like you . . . I mean . . . I wasn’t implying that you were old or anything . . .”

  “That’s all right, Justin. I am older than you. Actually, I’m more than twice your age, and yes, I do know what I want,” I said, as I slowly twisted the vibrator in his ass.

  “I’m glad you’re open to learning new things. I’m sure you’ll learn a lot today. For now, why don’t you turn over on your stomach and I’ll give you a nice massage?”

  I put a pillow under his hips and turned the vibrator on low. As I began to massage his balls, the most lovely, gentle moans issued from his throat. I looked at the clock. Wonderful. It wasn’t even noon yet. We had all day.

  Sherry

  Doug Harrison

  To the Cougar Women in my life:

  Memories of you swirl through archetypical

  mists of time and distance.

  My gratitude for your empathy,

  passion, guidance, and love.


  Another Saturday evening. And I didn’t have to rummage around bars for some action. My friend Thelma was hosting a pansexual play party in the waterfront district. A first for her, but her experience and connections in the kink community, coupled with her authoritarian presence, guaranteed a successful event. Besides, I always managed to enjoy myself, regardless of the venue. I donned 501s, denim shirt and boots, stuffed my leather bag with appropriate attire and a few toys, slid into my suburban sedan, and drove across town. The city towers sparkled across the harbor as I entered the warehouse neighborhood.

  I found a parking space under a street lamp a few blocks from my destination, trading the increased protection of my brightly lit car for the decreased personal safety of a longer walk. No stranger to karate, I nonetheless sallied forth with a can of red pepper spray in my pocket. I stood tall and strode briskly, careful to hug the sidewalk’s edge, away from deep shadows and dark doorways, and peered between parked cars like an insurgent expecting an ambush. I only jumped once, and chortled when I realized that the sounds assaulting me from a grimy dumpster were a rat family’s nocturnal picnic. I arrived at a nondescript door illuminated by a dull, red light bulb, without seeing another human, or even a black cat. A late-model Porsche was parked directly in front of the entrance, its pristine black body shimmering under a street lamp.

  I pummeled the wooden door with my knuckles; the doormen at these affairs usually paid more attention to the action in the play area rather than to their sentry duties. Surprisingly, the peephole squeaked open almost immediately.

  A gruff voice assaulted me. “Get lost, kid.”

  “I’m over twenty-one.”

  “So what?”

  “My name’s Brad. Thelma’s guest.”

  A shuffle of papers, a grunt, and the door swung open on shrill hinges. I jumped sideways and entered. A grizzled guard dashed into the cool night air, checked the black car, glanced up and down the sidewalk, and rushed back inside. He bolted the door shut, put a checkmark against my name, and shoved the clipboard at my face.

  “Sign here.”

  I scrawled my signature, and skimmed the list of attendees. The sentry scowled and yanked the clipboard from my hand. We each took a step backward. My eyes blazed. I puffed out my chest, and rested one forearm on my toy bag and my other fist on my hip. My nemesis scanned me head to toe. His eyes settled on my bag, he formed a half smile, and finally held out his hand.

  “Welcome. My name’s Tom.”

  I returned the handshake, but not the half smile. “For the record, I’m pushing thirty. Now, where do I change?”

  “Locker room’s over there,” Tom answered as he threw his thumb toward a dimly lit doorway. “Hope you brought your own lock.”

  “Always do,” I said and turned away. I come face-to-face with a scurrying Thelma who braked rapidly despite her three inch spike heels.

  “Brad! I was hoping you’d show up. Don’t mind Tom. He’s getting used to his new job.”

  “He needs more practice.”

  Thelma guffawed, I chuckled, and we fell into each others’ arms.

  “It’s been a . . .” we exclaimed in an impromptu duet.

  “Ladies first, Thelma,” I said.

  “Haven’t been called that in a long time.”

  “It’s not a woman’s profession that entitles her to be called a lady—it’s the woman herself.”

  “Spoken like a true gentleman, Sir!”

  We both howled. A few heads turned our way, not from annoyance, but in appreciation of unrestrained laughter.

  “What’ve you been up to? Thelma asked.

  “Well, I’ve been knocking about the city, doing my usual thing, and—”

  A cascading tenor voice shrieked at the upper limits of its range. “Thelma, over here! Quick!”

  “Damn. Some newbie probably can’t untie his shoe. Catch you later, Brad. You know where the changing room is?” I nodded. “Drinks against the far wall. They’re on me. Tell ’em Thelma sent you,” she bellowed over her shoulder. “I know you’ll have a great time!”

  “Thanks,” I shouted back as she disappeared into the crowd.

  I entered the makeshift locker room. Coed, as usual. Still, I wasn’t used to this. A double-decked train of lockers leaned against a long wall. Light from an almost-full moon made its way through a narrow window above the lockers and fought two small light bulbs at either end for the brightness trophy. Must have been the boiler room. A few wooden chairs were scattered about. A musty smell, not quite disguised by pot smoke, hung in the air.

  I found an empty locker, grabbed a chair, and collapsed onto it.

  “Whew.” I slid my bag between my feet, stretched, locked my legs, and crossed my arms over my chest. I looked around.

  Not many people. Yeah, it was still early. Two women, one chunky, one thin, stared at me as they removed their bras. Chunky turned away and unfastened her straps, while her partner did a subtle strip tease, wiggling her hips as she slowly lowered her garment. I returned her smile. A group of men huddled in the far corner, the obvious source of the pot smoke. Raucous laughter followed the pipe around their circle, along with coughing and hacking. Several of the men had changed into leather outfits: a vest here, chaps there, and a few studded, leather thongs that attempted to sparkle in the dim light. Two wore street clothes and there were no toy bags at their feet. Voyeurs? If so, Thelma would boot their asses out, pronto. We were here to add energy, not drain it.

  A straight couple had finished their preparations. She wore a black corset that thrust her ample breasts toward her chin and boots that stretched up her thighs and almost grasped her bare pussy. Her partner wore red leather wrist and ankle cuffs that matched his collar and briefs, including dark blue piping. He picked up their toy bag and followed three paces behind. Two guys searched for a locker, giggling arm in arm, each carrying a huge toy bag. They couldn’t possibly work through all the crap in their bags. Still, be prepared!

  I stood. Vest off. Denim shirt off. Leather arm bands already in place. Vest on. Boots off. 501s off. Leather jock already in place. Boots on. I shoved the locker door shut, secured it, and put the key in a zippered pocket in my toy bag. On with the show!

  I crossed a lounge area and walked past the bar. I’d pass on the free drinks for now. Couldn’t take a leak in the middle of a scene. Still, if I wanted to piss into or onto someone . . . well, that would take care of it.

  The huge play area had probably held semis in better days. Or maybe it was an old warehouse. Or both. The walls were draped in black cloth. The nondescript disco music was loud, but not overwhelming; you could actually hear yourself think. Better yet, you’d be able to hear your partner’s breathing and gasps of pleasure and pain. I wondered if the disc jockey had ever played for an event like this. But, after all, it was San Francisco; he had probably seen just about everything.

  The area was well-equipped with the usual paraphernalia: crosses, slings, T-bars, fuck benches, mattresses, and cages. Thelma had done a good job. Must have called in lots of favors. A few pieces were conspicuous with their elegance, highly-polished walnut instead of plywood laminate. A dungeon monitor paid particular attention to the activities at these stations.

  I observed a few scenes: flogging, no-escape bondage, let’s-look-pretty bondage with multicolored ropes, play piercing. I tarried at a group grope where numerous appendages protruding from a tangle of bodies reminded me of an overcrowded crab tank on Fisherman’s Wharf.

  By far the most intriguing scene was located in the center of the room. A spot light shone directly onto a metal cage. It was two feet wide, three feet tall, four feet long, and was constructed from metal bars spaced five or six inches apart, including the top. It had a swinging door at one end. An effeminate brunette sat scrunched at the far end, his hands and torso secured by ropes, his legs stretched in front of him. He couldn’t reach his hard-on. A redhead was prostrate on all fours, his ass protruding up and out through the cage’s open door. He was nibb
ling the captive’s toes in slow sequence. Yuck! Not for me, especially after I noticed the captive’s bright red toenail polish which, incidentally, matched the color of his fingernails. But, I supposed, being plowed from behind by an eager blonde Adonis spurred Red on. I considered extending the conga line by fucking Blondie, but a heavyset woman with white hair approached and began pummeling Blondie’s ass with a ping pong paddle in time to his strokes. Oh well.

  I scratched my head and began a slow walk around the perimeter in search of a partner, male or female, or perhaps both. I smiled and flirted. Halfway around, I halted, removed my vest, and tucked it into my bag. I resumed my cruising and sensed that someone was watching me. I scanned the crowd, but couldn’t pinpoint my observer. I moved back into the pack.

  Finally I plunked down onto an empty mattress, and leaned back on my elbows. Whatever was going to happen would happen all in good time. I closed my eyes and relaxed, and let myself slide into a dark, peaceful world.

  I opened my eyes, how much later I don’t know, feeling refreshed. This, of course, meant extra horny.

  Again, I felt two eyes staring at me. Only this time, directly ahead. A ravishing redhead in a black pants suit and white blouse had captured me in her gaze. I almost blushed.

  She was dressed as though she was about to chair a business meeting. What was she doing here? Another voyeur? No, not if Thelma could help it. What was going on?

  I stood up, conscious but nonetheless proud of my almost-naked torso. I tried to subtly square my shoulders, sauntered toward her, and stopped at arm’s length.

  “Hello, my name’s Brad. Nickname’s Puma.”

  “And I’m Sherry. A Cougar. How interesting.” She held out her hand. No ring, nails well done, light polish, gold bracelet, not from Woolworth’s.

  “You have me at a disadvantage.” I stared at my crotch.

  “On the contrary. I like my men totally naked, particularly a man who’s comfortable with both men and woman. But you look good in that leather jock. Leg straps set off your bubble butt. And the snap-on pouch acts like a chastity device.” She smiled provocatively. “Waiting for the right person to yank it off.”