AdultMatchMaker
AdultMatchMaker
A five-chapter story detailing Lisa's increasing sexual confidence. Anal, oral, sex with toys, and naughty girls. Enjoy!
Story 16 - She Didn't Know the Stakes, But She Bet Her Ass!
It began like this: a bottle of sake, a platter of chocolate covered strawberries, lavender-scented candles, and a boardgame I'd picked up that promised to be "an intimate game for couples to share." A locked door, Coltraine's "Love Supreme," on the CD player, a pair of handcuffs on the bedpost, and of course, Lisa...wrapped deliciously in her new red teddy. It was all I needed that night.I'm 25; she's 28. I'm a Pisces, built short and solid, the body of a high school state wrestling champion grown into a man. She's a Leo, sculpted tall and flowing, with the graceful curves of a dancer, beautiful to behold as a classical ballerina, sexy as hell when she used to dance for cash. I keep my hair short, wear a beard, and have brown eyes...she's got a mane of tawny strawberry blonde ringlets that fall down her back like a waterfall set flame, alabaster skin that's dusted by freckles, and eyes as green as true emeralds. I'm a construction worker; she's a schoolteacher. I like beer and motorcycles; she prefers pot and horses. We're complete opposites, water and fire--which is why we attract.
It was her untamed mane of mare's hair, catching bronze highlights in the fading sunlight. That's what made me set down my beer and turn my head when she walked through the door of the rooftop bar I was in. It looked like it was spun from copper and gold woven together. The fiery tips ended just inches above a perfect heart-shaped ass. I imagined twining my fingers in that long hair, using it like reins as I rode her hard from behind. Then she turned around, and my gaze swept up over her long dancer's legs, circled the curve of her hips, dipped through the small of her waist, and climbed over her twin peaks. My God, what a body! It was a millisecond-long visual appraisal of a woman's body that men, as an unspoken but understood rite of passage into adulthood, quickly and unconsciously develop once we've begun seeking the favors of the fair sex. Our eyes locked, and we looked at each other just long enough to let one another ascertain that we were both interested in what we saw. The dismissive look she then threw my way before haughtily tossing that hair sealed her fate. I'd never seen such a gorgeous woman, and I decided on the spot I was going to have her. Oh yes, she would be mine....
It took all of a month. But I'm getting ahead of my story.
As luck would have it, a friend of mine whom I hadn't seen in a few weeks walked in seconds behind her. We greeted one another and before I could count my blessings I'd been introduced to Lisa and her friend Christine. I joined them at their table. Mike and I made small talk, and Christine joined in, but Lisa was virtually silent throughout the conversation. I lingered just long enough to make an impression, then excused myself to meet the people I was supposed to, promising to return later in the evening. I went downstairs thinking the goddess I'd met was either extremely shy or an ice princess. By the time I made it back upstairs an hour later, the table had filled up with other friends of mine, and Lisa was for all intents and purposes cut off from me. I leaned on the deck railing at the opposite end of our crowd, and got into some serious flirting with a cute girl at the table beside me. She invited me to sit down with her, and I wrote off the gorgeous girl ten feet away from. A half an hour later I left with my playmate for the evening on my arm. I noticed that Lisa was watching with interest as I said my good-byes, and I winked at her just before departing. She turned away as I did so, causing me to break into raucous laughter. I knew her act, and I saw right through it.
I didn't see her again until I threw a Fourth of July party two weeks later. Lisa showed up when the party was in full swing. She cornered me as I was walking into my kitchen. "Excuse me," she said with a distinctly Southern twang, "but do you have any wine?" The way her mouth stretched 'wine,' out had a similar effect on my cock, making it snake down my leg. I steered her to the good bottles I keep stashed in a cabinet above the refrigerator and helped her choose a nice Australian Shiraz. She thanked me profusely as I presented the bottle, uncorked it, and poured her a small amount to taste, treating the process with the professional style I'd learned in my bartending days. I could tell Lisa was delighted by the attention I was giving her. She was all smiles now, completed animated, resting her hand on my forearm as I filled her glass. Feminine body language is a sublime subtlety. "I'll find you when I need some more," she promised, eyes sparkling. I listened to the sound of her skirts swishing around those thighs. Before she left, I had her phone number, and before the weekend was over, I had her.
Six months later, that very same hair was now spread across the forest green flannel sheets I'd bought with her in mind. Lisa loved sleeping in them, and I loved how they framed her like the work of art that she is. She was twirling a finger idly in her curls, her red lips sucking on a strawberry, reading over what she'd written. The game was simple, in that both of us wrote a fantasy or wish that we wanted to fulfill on a card, and then placed both in a sealed envelope. The loser had to honor the winner's request.
"I think I'm ready," she said. I put both cards in the envelope, and offered it to her lips. She stretched her tongue out and lasciviously licked the edges. I felt my cock stir. I couldn't wait to feel that tongue on me.
/////
It was a good game. By the time we had finished, the strawberries were long gone, the bottle of sake sat empty on my nightstand, and the candles had burned low. We were both naked and more than a little drunk. We'd kissed, sucked, fondled, and massaged one another into a near frenzy as the game progressed. After two tries, I rolled what I needed to win.
Lisa's cheeks flushed when she opened the envelope and read what I'd written two hours earlier. Her eyes widened, and then she slowly set the card down on the bed, a faint smile on her lips. "No way," she pleaded.
I didn't budge.
"How about a blow job instead?"
I shook my head slowly in response.
"No?" Lisa licked her lips and slowly sucked a finger deep into her mouth, moaning as she worked it in and out for effect, her other hand reaching over and wrapping around my shaft. "But I really want to suck your cock right now."
"Are you saying you refuse to honor the agreed upon rules of the game?" I asked in mock seriousness.
Lisa stopped stroking my cock, yanking her hand away. She whined "but I don't like that!"
"You've done it before..." I reminded her.
"But it hurt! I did not like it." She pouted, crossing her arms over her lovely 34Ds.
I knew how to play her cat-and-mouse game by now. It takes a while to figure women out. They're all different, and each has her particular little nuances you have to learn to navigate or detour in order to get to your ultimate destination. I picked up the envelope and fished her card out. "I want you to buy me a phaleonopsis orchid with white flowers, and take me to dinner at Sunset Ridge in a limo." I did quick math in my head. A $50 flower. A meal in a suit and tie, which I loath wearing, that would easily top $250 with a half-decent bottle of wine plus tip. Add cruising in a pricey ride all night... I realized how lucky I was to have rolled a win. If she'd won, I would have had to cough up at least half a grand for an evening's entertainment! I'm not the kind of person that welches on his bets. One thing I've learned: Lisa's as materialistic as she is gorgeous. It's a dangerous combination when your wallet is the one picking up the tab.
I leaned back against the pillows and closed my fist around my cock, jacking it slowly. Lisa turned her back and pouted. Neither of us spoke for several minutes. Weighing what we'd both written, I deemed my fantasy wish to be roughly equal to hers in terms of value.... She turned her head and watched me working my cock. I spread a pearl of pre-cum over the head of my cock, making it glisten like a wet plum. Without taking her eyes off of my hardness, she said "Fine. You won, if that's what you want, fine."
My wish card had read this: "I want to have your ass. I will take a week to train you, relax you, and prepare you to not only be ready to take my cock in your ass, but to crave my cock in your ass. During this time, you must agree to any and all training activities I deem essential. You will, within seven days' time, beg me to fuck you in the ass."
She looked me in the eyes. "But I will NOT beg for it." I grinned--victory.
Her head swooped down and she wrapped her lips around my cock, swirling her tongue furiously over my knob. I held my cock for her and pulled her hair back from her face so I could watch. There's something incredibly sexy about blow jobs that make all women's faces exquisitely beautiful when they're going down on you. I can't really explain it, but even the most plain-Jane type of girl looks phenomenal when she's got a thick, veiny shaft crammed halfway down her throat. It's even better when the girl who's sucking the come out of you happens to be a knockout.
When we first got together, Lisa's blow jobs weren't the most enthusiastic. A lot of teasing build-up, a minute or two of sucking, and then five minutes of stroking my shaft absent-mindedly while she talked nonchalantly about topics completed unrelated to the business at hand. It drove me crazy. They weren't so much blow jobs as chit-chat sessions with something for her to do with her mouth when she wasn't talking. When I could get her to keep my prick between her lips long enough to get my rocks off, she'd never fail to pull away and finish me with her hand. For a month I put up with lousy head, because her body was centerfold material. But I found out why she sucked at sucking a few weeks after we started sleeping together. Desiring some oral servicing, I'd spent the better part of an evening dropping subtle hints, coaxing and cajoling her, until Lisa finally gave in and crawled between my legs. "You're the first guy I've been with in over three years," she confessed as she held my cock in front of her face.
"Really?" I was surprised.
"Yeah...I guess I don't feel comfortable doing this. I'm out of practice." She squeezed me in her hand and rested her cheek against my cock, closing her eyes. I wondered if she could feel me throbbing.
"Practice makes perfect!" I replied. She looked away. Shit. Time for a song-and-dance routine. I continued talking.
"Lisa, anything you do feels INCREDIBLE. Your mouth feels sooo good on me...I want you to want to go down on me, I want you to want to please me. Oral sex is a wonderful thing for lovers to share with each other...the pleasures of giving and receiving. I want you to feel comfortable with me in everything that we do together."
"Do you like it when I give you head?" she asked. "Does it feel good?"
"Oh my God, yes, baby, YES! Just... maybe, don't... you know, STOP so much when you're doing it?"
She laughed. "I know, I'm a bitch. I love to tease you."
"I love it too," I lied. Teasing, yes; bad head, no. There's a big difference in the two. I read somewhere that there's a direct correlation between how wild and wanton a woman is in bed and the level of comfort and security she feels in a relationship. She looked up at me, her eyes shining, and I thought, fuck, maybe she'll get better. If not, there's always Vegas. I could've gotten a hooker for the night with what I would have had to drop on Lisa's fantasy, and I could have indulged myself in any and all of mine in that amount of time.
"I guess...I'll just have to practice more often. Sound good?" She giggled girlishly. "Thought it would to you. Just don't come in my mouth, or we stop 'practicing' altogether." She waited for confirmation. I nodded enthusiastically. She immediately lowered her mouth onto me and sucked my cock more vigorously and unabashedly than she ever had before. It was the best blow job she'd given me yet, even though I blew my load all over my stomach.
She toyed with my spent cock afterwards, enjoying how I moaned and squirmed as she stroked me softly. I'm way sensitive after a good hummer. She took her sticky hand off of my shaft and dipped her fingers into the puddle of come pooled on my abdomen. She raised them to her mouth and lapped daintily at my sperm. It was the first time I'd seen her tasting my gift, and my cock grew iron-hard again immediately at the sight.
"I thought you didn't want me to come in your mouth!"
"Nope." She sucked her fingers into her mouth, cleaning my come from them, savoring the taste thoughtfully. "Not yet. You're not too salty," she proclaimed, and licked up some more of my come. "More..." --licking up more of my wad, her lips shiny as she smacked them together-- "sweet...it takes me a while to get used to how different guys taste. Someday, sugar, when I'm ready. If you're lucky."
Patience is a virtue, I reminded myself. A month later she'd progressed to cleaning me thoroughly with her tongue when she blew me (which was still not frequent enough for my liking), but only when I gave her advance warning when I was about to unload. I was thrilled a few weeks later. I told her I was going to come, and started to pull myself out of her mouth, but she grabbed my hips and pushed her mouth back down over my cock. I spurted over and over, emptying my load right on her tongue. She pulled my prick slowly from her mouth, trailing a thick, wet string of saliva and cum from her lips as she did so. She looked at me and swallowed deliberately three times as I watched with disbelief. "Like I told you, when I'm ready." Now, six months later, she can't get enough of my "sugar," as she calls it.
That's what flashed through my mind as she went after my sugar. One hand spread my thighs wider apart and the other gripped the base of my cock, pushing my hand gently away. She licked up and down both sides of my cock, switching with every stroke of her tongue, and then brought my cockhead to her lips, rolling her tongue around the head while staring up at me. She took me into her mouth slowly, her eyes never leaving mine, until her lips were stretched and her nose touched my pubic hairs. She sucked hard as she raised her mouth, her tongue lashing at the sensitive spot underneath until I moaned. She flicked her tongue back and forth mercilessly, knowing how this drives me wild. She covered my cock with saliva and began to jack me rhythmically with her hand, moving her mouth down to work my balls. She drew each one into her mouth and washed her tongue over them, caressing them, making them draw tight against my body. She took me between her lips again and slid up and down me with a practiced smoothness. Slow, liquid motions at first, making my eyes roll shut, then picking up her pace until I felt my hips start to rise and fall, and then I was fucking her mouth as she held still, her hand coaxing my load out. I felt myself go over the edge and exploded sticky bursts of hot come into her mouth, thrashing in ecstasy. She swallowed everything I gave her, and held me in her mouth for a few minutes afterward, making me writhe in exquisite agony every time she moved on me. "Mmmm...I love my sugar daddy," she told me afterwards, resting her head on my stomach.
But I hadn't forgotten. She wasn't getting off as easily as I just had! I waited for my body to return fully to my own control, then rolled her onto her stomach and pushed her arms forward. I raised her hands toward the handcuffs and her whole body tensed. "Uh-uh! You're not just going to handcuff me and shove your cock up my--"
I clamped a hand over her mouth and breathed into her ear. "Trust. You have to trust me, baby." I kissed her ear, then her neck, leaving a trail of kisses along her back as her body untensed. I kept kissing her neck and shoulders as I slipped her hands into the cuffs. "I'm going to make you feel just as good as you made me feel." I pulled myself back and spread her thighs wide with my hands. I started by sucking her toes, each one, licking the soles of her feet, kneading her calves. I planted kissed on the backs of her knees, and all over her thighs. I massaged them as I blew hot breaths over her labia, swollen and glistening with her juices. I flattened my tongue and dragged it slowly up the length of her slit. She sighed. I did this again and again, my hands now kneading her ass cheeks, until she was pushing her hips against my tongue. I stuck my tongue out, sliding it as far down as I could, teasing her just below her clit, then thrust it deep into her wet slit, fucking her with it from behind, her breaths short little gasps now. I could tell she was hot, close to coming, and I went back to long smoldering licks along her lips again, tracing further and further up her perineum with each stroke.
I pulled her ass cheeks wide apart, and her tiny hole winked shut. I held her ass apart and began to circle her asshole with my tongue. She moaned, and I tightened the circles until my tongue was doing pirouettes on her anus. I licked her slowly at first, my tongue soft, and I felt her shivering. "Oh my God...." she said. Her head dropped into the pillow and she grunted. "Unggghhh... ohhhh...." She turned to look over her shoulder and I slid the tip of my tongue into her ass, pulling her ass cheeks wide apart with my hands as I speared my tongue deep inside. The effect on her was electric. "Yesssssssss!" she hissed through clenched teeth as she bucked her hips back at me. I slapped her ass hard. She arched her back, and as I tongue-fucked her ass I brought my other hand up to cup her pussy. I spanked her again, thrusting my tongue in as deeply as I could, and then brought my hand down on her ass once more. She screamed into the pillow and I felt her pussy contract before she flooded my cupped hand with her juices.
I stroked her back for a while before I began to kiss my way back up her body. She lay there, still and silent, as I unlocked her hands. I propped myself on one elbow and rubbed her back until she rolled over and looked at me with tender, submissive eyes. It's all part of her game. Good girls don't do bad things...unless bad boys make them, and they love it when we do.
"You liked that," I told her.
She nodded and snuggled close to me, hiding her face in my neck.
"Good." I felt her shiver lightly beside me. "Tomorrow is day two."
__________________-
I didn't hurry home from the job site the next day. I knew that I had captured Lisa's curiosity the night before, and not knowing what I had in store for her would be driving her crazy all day. That's a secret to great sex: anticipation. No matter what I did, she was going to be hot and horny from waiting eight hours for it.
And if I could keep this up all week, I'd have my cock buried balls-deep in her ass long before Friday.
I went to a sex shop in Denver, taking an extra hour for lunch. I knew exactly what I had in mind, and left with a bag of toys in less than a half-hour. I stashed them in my lunchbox.
When I opened the front door and walked inside, I immediately noticed that the house was spotless. She'd obviously been cleaning all afternoon. Which also meant she was in a great mood... I'd fulfilled my obligatory masculine duties well last night! I heard water running in the kitchen and didn't bother taking off my mud-encrusted workboots. The kitchen was spotless (a rarity in a household where three guys shared the rent) and she was making a pretense of washing one final dish. She had on a short, tight miniskirt that showed off her legs, and a tight silk wrap top that offered up her succulent 34Ds like ripe melons to be savored. She pretended not to notice me and wiped at a spot on the countertop. I'd learned that about Lisa; she loved being 'noticed,' and usually waited until I did so. I set my lunchbox down.
"Missed a spot, sweet-tits."
"What? Oh! I didn't even hear you come in, sugar!" She tossed the sponge into the sink and smiled a flirtatious smile, head cocked to the side, her eyes bright. "How was your day? I'll bet you're sore..." she walked over to hug me, then noticed my muddy boots. "You go right back outside and take those off this instant. I mopped less than an hour ago!"
I laughed. "No hug, then?"
She put her hands on her hips and her eyes flashed. "IF you take those boots off IMMEDIATELY, and IF you sweep up the mud you tracked in here, and IF you clean yourself up, IF I'm feeling generous, maybe." She gave me a green-eyed glare, then rolled her eyes. "Men!" She started to walk past.
I moved to let her past, bowing exaggeratedly as I did so. Still bent at the waist, I caught her by the hips and pulled her back toward me. I nipped her playfully on the ass which elicited a yelp from her. I stood and wrapped my arms around her, drawing her close, nuzzling her neck. "Mmmmm....you are one sexy bitch," I told her. "Do you know how turned-on I get when you're angry?" I slid my hands under her breasts, cupping them.
"You smell."
"Uh-huh." I sucked on her neck. She settled back against me.
"Like sweat." My fingers teased her nipples. She cooed. "You need to go take a shower."
I rubbed my half-hard cock against her. "IF I get a kiss first."
She turned around, feigning surprise. "Well, sugah...all you h-ad to do was a-sk!" She made 'had,' and 'ask,' stretch into a two-syllable words, knowing how it drove me crazy when she turned up her Southern accent. We kissed, and soon she had a hand inside my blue jeans, squeezing my prick as our tongues danced. I slid a hand under her skirt. No panties, and she was drenched. Her mind must've been working overtime all afternoon. I spread her pussy lips with a finger and teased them lightly, sliding my fingertip back and forth just barely inside her. She was worked up, no doubt about it.
I broke the kiss and pulled my hand away from her smoldering box. She pressed her tits into my chest and started licking my ear, jacking my prick eagerly. "Think I'll take that shower now," I announced. I picked up my lunchbox.
"But I like you all sweaty..." her breath was hot in my ear as she slipped her tongue around. "Let me help you undress." She took me by the hand and led me toward the bathroom, where she leaned me against the sink and began to untie my boots. She yanked and tugged, succeeding in getting the first off, and then had trouble with the second. I stuck my leg out in front of me and she straddled it, bending to remove my boot which finally came off in her hands. She dropped it and pushed her ass back against me, slowly rotating her hips.
I undid my belt buckle and wriggled my jeans down around my ankles, then roughly pulled her miniskirt up around her waist. She reached back between her legs and cupped my heavy sac. "Mmmm, sugar...I've been waiting for you to get home all day."
I rubbed my prick over her ass cheeks, nestling the length of my shaft between her cheeks and sliding it slowly back and forth. "Today is your second day of training, baby."
She arched her back and reached back to untie her top, pulling it from her torso, and then undid her bra, tossing it aside. She reached back and found my hands, guiding them to her pendulous tits, then stuck her hand between her legs again, fingering her clit and stroking my balls. "I know," she said breathlessly, "but I need you inside me." I slid my cock between her thighs and rubbed the head between her pussy lips. "Mmm, yes. Fuck me, give me your hard, fat cock."
I worked my cock into her hole just slightly, then pulled it back out. She pressed against me, wanting more, and I teased her with just the head, my fist wrapped around the rest to prevent her from sliding me inside. I placed my hand over hers and helped her frig her hard little clit. "Quit teasing...just fuck me!"
I slammed my entire prick deep into her. She squealed and I held my hips absolutely motionless, allowing her to move on me as she wanted. I could feel her clenching wetly around me. I reached out and tangled my free hand in her hair, pulling her head back, and then began to fuck her with long, steady strokes, pulling my cock out to the tip and then burying it all the way. I built into a powerful rhythm and didn't change it as I felt her hand stroke her clit faster and faster. I pulled back on her hair and began to slap her ass with each stroke.
"Oh yes! Oh yes! Oh yes!" she was bucking back against me. She was on fire, and a few strokes later she began to take fast, shallow breaths that meant she was about to come. I pinned her hips to me and roughly ground my cock as deep as I could into her, impaling her on my shaft, and I felt her body shudder through her first orgasm. I held her there against me, listening to her soft cries of pleasure. When she dropped her head, I moved one hand back to her clit again. "Don't move," I instructed her.
I began to rub her clit in fast tiny circles and she started panting. "You bastard...you're gonna make me cum again! Oooohh... ooh, yes..." I stroked her clit faster as she began to squeeze my prick inside her.
"Hand me my lunchbox." She looked around and slid forward to pick it up, taking the time to work her sweet pussy back and forth on me before passing my lunchbox back to me. I opened it with one hand and found what I was looking for, pulling out a bottle of baby oil. I kept rubbing her clit as I poured baby oil onto her ass. "What are you doing?" she asked. "Shhh," I told her.
I moved my thumb down to her asshole and rimmed it lightly. She held still. I worked my pinky finger slowly into her ass with tiny corkscrewing motions. She sighed as I buried it to the knuckle. I kept it there and began to fuck her again. In minutes she was panting as I worked both my cock and finger into her simultaneously. "Come for me, Lisa....come all over my cock, baby. I know you want to. You've been waiting all day for me to come home and play with your ass again, haven't you?"
"Yes!" she screamed, her pussy clamping down hard on my cock. I felt her juices squirting over me, dripping down her thighs and over my balls.
I waited a few minutes before I pulled my cock out. I replaced my pinky finger with my index finger, and slid it in easily. "I'm so horny..." she confessed as I explored her ass deeper. "This is so fucking kinky, I just got so hot thinking about it all day!"
"I knew you would." I let my free hand roam over her body, kneading her tits. "Shower time. But you're not done for the day yet, sweetheart." I pulled my finger out of her ass and kissed her between her shoulderblades.
I turned on the water and climbed in. I was rinsing the shampoo out of my hair when I felt her hands lathering up my back. Lisa stood outside, washing my body. She'd lost her miniskirt and was totally naked now. She moved her hands over my shoulders, massaging them, down over my ass and thighs, then between them to suds my balls and still-hard cock.
"Turn around for me," she told me. I did so, and she moved her hands over my tight chest, playing with my nipples until they grew hard, raking her long nails over them. One hand moved down to stroke my cock again. "You haven't come yet." She pulled me forward by my cock and knelt down in front of me, looking at my pulsing prick. "Rinse," she commanded. I stood under the water, letting it wash me clean, my eyes closed. I moved back in front of her and saw that she had the bottle of baby oil. She poured it over her tits and squeezed them together, rubbing her pink, stiff nipples. I pushed my hips toward her and she stretched her tongue out to lick the tip of my cock. She closed her eyes and kissed it softly, then brought both hands up to coat my cock and balls generously in baby oil. She leaned forward and wrapped her tits around my shaft, working it back and forth between them as she squeezed them together. I reached down and cupped them, playing with her nipples. Lisa has fantastic breasts, perfect for fucking. She reached around to squeeze my ass, her eyes on the engorged head of my cock as it poked in and out of her cleavage.
"You like titty-fucking me, huh? Do you want to give me a pearl necklace?" I could only nod as I fucked the valley between her tits. She kneaded my ass cheeks and gently spread them apart. I felt her fingers exploring my ass, rubbing it all over. I looked down at her and she had a wicked look in her eyes. I felt one fingertip pressing against my asshole, then push tentatively inside. She moved the other hand back to rub the head of my cock. She looked up questioningly as she continued to press her finger deeper into me. I grunted as I felt her begin to stroke it in and out, and I moaned loudly. "Ungh...Lisa..." She giggled. "What's good for the goose is good for the gander. Tell me when you're gonna cum."
I felt my knees begin to buckle from all the stimulation I was receiving. "You're close," she murmured. I was. "Yeah...gonna come soon," I told her, my voice ragged. She licked her lips. She wrapped her hand around my prick and pulled her tits away from me, her finger busy in my ass. "Shoot it for me. Cum on my tits. Aim for my mouth." She stuck out her tongue and jacked me hard. Her finger was massaging my prostate and I felt my cock expanding even further as she finger-fucked my ass. It was too much. I felt my ass clench around her finger and she milked my cock, moving her open mouth toward it as my hips pushed forward. My first shot burst out and splattered on her chin, and she held still as the next shot deep into her throat. She closed her mouth, gagging slightly as my come hit her tonsils, and swallowed with a surprised little sound, her hand never stopping on my cock. I spurted again onto her cheek, and sent three more big volleys of semen onto her tits, and then dribbled several more weakly out the tip of my prick and over her closed fist. She looked up at me adoringly as I moaned with pleasure. "Oh, you had a big load in there, didn't you?" She rubbed my cock against her face, smearing my come on it. I felt her finger slide out of me. She lapped at the come oozing out of my dick and gently squeezed my drained nut sack in her oiled palm.
I heard my voice answer weakly. "That...was fucking...intense." My head was spinning.
She climbed into the shower with me and hugged me. The water was hot as it coursed over our bodies. We stayed that way for some time, not speaking, just letting the steam build up around us.
_______________________
I gave her another rim job when we got into bed that night, surprising her by slipping the small vibrator I'd purchased into her pussy as I tongue-fucked her. I took my time, luxuriating her ass and cunt with my attentions, making certain she came more than once. She told me I had a fabulous tongue and a wonderful cock. The sheets were soaked. We'd be sleeping on a few layers of beach towels from the looks of things.
"I'm starting to enjoy having lost our little game the other night," she confessed.
"I thought you would. But you're not done for the night yet."
"I'm not?" she asked.
"Nope." I had bought more than just baby oil and a vibrator that afternoon. I pulled out the two butt plugs I'd selected. Her eyes grew round. "What are those?" she asked. "And do I have to ask where you're going to put them?"
"I don't know. Do you?" I laughed. "'Any and all training activities that I deem essential,' if I remember correctly?"
"Shit." But her hardening nipples gave her away. "What do you want me to do?"
I handed her the smaller of the two. It was firm but pliable, about three inches long, with a wide cupped base that would rest snugly against her ass. It was tapered, a slim head flaring to a wider middle, just under an inch or so in diameter, decreasing in width again as it neared the base. I had looked carefully for one that was small enough so she could easily accommodate it. She flipped it around in her hands, examining it curiously.
"You're going to go get ready for bed, do whatever you need to doo-doo, and when you come back, you're going to lay down with your head in my lap. I'm going to massage your breasts with baby oil, and you're going to play with yourself until you're good and ready to put this in your ass."
"Do I have to?"
"Yes."
"How long do I have to leave it there?"
"All night."
"No!"
"Yes."
She made a face. "I won't be able to fall asleep."
"Only if you lie there thinking about it. I won't be surprised if you finger your pussy all night long."
"Why do I have to leave it in all night?" she whined.
"Because--" I put the larger of the two butt plugs in her hand, and her eyes got even wider. It was smooth and rubbery, more phallic, with several ridges along its' 4" length, larger in diameter than the center of the other I'd chosen, but still smaller than my cock. It had a battery-powered low speed vibrator inside a flesh-colored latex sleeve. "Tomorrow night I'm going to have you wear this one. You need to be stretched slowly." Her nipples were stiff little nubs at this point.
"What if I get constipated?"
"We'll take care of that, if necessary. You can take it out if you feel the need to, but only for an hour. If I find you've disobeyed me, you'll have to be...disciplined."
She left, and less than a half an hour later she was making small cooing noises as I caressed her breasts. I'd coated them generously in oil, rolling her nipples between my thumb and forefinger, kneading her flesh firmly. Her head lolled in my lap, eyelids fluttering as she bit down on her lower lip, riding a series of small orgasmic waves as the vibrator hummed gently in her. She was working it slightly in and out of her lips, touching the hood of her clit once in a while, legs jerking slightly each time she did so. With her other hand she was gingerly fingering her ass. I'd propped her hips up with two pillows.
"Oooh... give me that oil!" The smaller butt plug lay on her stomach, jerking erratically as her pelvic and stomach muscles clenched and unclenched. I rested it against her side. "Open it for me."
I did as she commanded. "Pour some in my hand." I puddled some in her palm. "Is that enough?" she panted.
"There's always more." I watched as she coated the sex toy in oil and moved it down to her ass.
"Don't watch me do this!" she said, her voice rising to a higher pitch.
I chuckled. "Okay..." I closed my eyes, leaving them slitted, but realized she was too absorbed in her own body to notice what I was doing. Her breathing had quickened, and she was tensing up. "Relax, sweetie...take deep breaths for me."
"Okay," she said meekly. She waited, feeling her body loosen up again. Lisa began to press the tip against her small hole, and her hips rose ever so slightly. She worked it slowly in and out until she had it halfway inside, scared to go further, stopping at the widest part. "You can do it," I assured her, continuing to stroke her tits softly to help relax her. "That's it... take your time... go slow... when you're ready...."
She froze all over except for her forearm, which quivered slightly, her own body resisting itself. I heard her suck in her breath, then moan low in her throat as her ass stretched to allow the widest part past, sucking the rest in quickly after it.
"Oooh... that feels... good... in a weird sort of way...." Her thighs trembled and I saw a dribble of moisture ooze out of her vagina. "What if I can't get it out?"
"You'll be able to."
I kissed her face, her eyelids, her cheeks, the bridge of her nose, her chin, her lips. We talked until she settled down. I cupped her breasts, telling her to go to sleep. She tossed and turned for a while, then finally dozed off, a contented look on her face. I fell asleep soon after.
I wasn't surprised when I woke up in the middle of the night. I only opened one eye. Lisa was lost in an orgasm, her hand busily working her pussy, the other pinching and pulling a nipple. She didn't notice that I was conscious. I smiled inwardly, knowing she didn't have classes the next day. Wonder what she'll keep herself busy doing? Sometimes losing is really winning, I thought to myself as I drifted back to sleep.
________________
When I got home the next afternoon, I wasn't surprised to find my baby fast asleep in my bed. I stripped out of my clothes and climbed in beside her. I kissed her face softly until her puffy eyes fluttered open. She looked exhausted.
"Long day?" I asked her.
She rubbed her face sleepily. "I don't know why I'm so (yawn)... tired," she mumbled. "I didn't sleep very well last night."
"I noticed."
She giggled guiltily. "You did?"
"Uh huh."
"Mmmm...good. Did you watch me?"
"For just a little while." I pulled the sheet off of her naked body. She still had the smaller butt plug in her ass, and her pussy was swollen, her pubic hair stickily matted with her juices. She smelled of female sex. "Did you take it out today?" I asked her.
"Only for a while. I had to this morning. But I put it back in after I had breakfast!" She was proud of herself.
"Good girl!" I kissed her, and we snuggled. Soon she was fast asleep again. I climbed out of bed, dressed, and watched TV for an hour or so. I started dinner, talked for a bit with one of my housemates who came and left again, headed to his girlfriend's place, and then woke Lisa up. By the time she came out of the bathroom I had dinner ready and we sat down to eat. She did the dishes, and I watched her from the couch. I was getting a hard-on knowing that I had this sexy creature willingly wearing a butt-plug--at my request--as she performed domestic duties like a happy little housewife.
She came over and laid her head on my shoulder when she was finished, wrapping her arms around me. "I'm sleepy...let's go to bed soon." She snuggled close, and soon we were fooling around on the couch. I wondered if I was going to have to wait all week to fulfill my fantasy.
"You've been doing very well with your training," I whispered between kisses.
"Mmmm...thank you," she responded. "I have an excellent trainer."
"Do you think you're ready for the next size up?" I asked.
Her response was to hump her pussy against me and ram her tongue down my throat. I guess so! I reached around to squeeze her ass and she started humping my leg with more fervor. "What..." (kiss) "are," (kiss) "you," (kiss) "going," (kiss) "to make me do," (extra passionate kiss) "tonight?" She was clawing at my shorts to free my cock. She fished it free of my boxers and began stroking it heatedly.
"You'll find out soon enough. Give me ten minutes. I'll call you when I'm ready."
"Okay, but hurry. I'm so fucking hot for your cock right now. Don't make me wait long." She had worked a shiny drop of pre-cum out of my shaft and saw it. She sucked the head of my cock into her mouth and I felt her tongue all over me. I groaned with pleasure and pushed my hips up, feeling her slide my cock deep into her throat. She sucked me hard on the way back up and teased the tiny eye with her tongue. "Mmm... gotta have my sugar. Hurry, honey."
I pulled my shorts up over my erect cock where it jutted out obscenely. Lisa squeezed it lovingly with her hand once more before I was able to extricate myself from our clinch. I went into my room and got the things I was looking for, then went into the bathroom. I locked the door, lit some incense, and spread several beach towels on the floor. I put a pillow down, and set a few candles on the tub. I lit them, and finished the last few things I had to do. I stripped nude, and checked on the incense before I called her in. Good. At least fifteen minutes left of burning time. "Lisa," I yelled. "Come in. But I want you naked when you are."
I didn't have to wait long for a knock at the door. She came in. "Lie down on your stomach," I instructed. She did. The red butt plug was still snugly tucked inside her anus.
"Spread your legs for me, and get comfortable."
I stroked her back and ass as I told her what tonight's training consisted of. "You were worried about being constipated last night? Well I need to make sure you aren't. I want you nice and clean for my cock."
"What do you mean?"
"I'm going to give you an enema."
"No! I don't want one!" But she didn't move.
I reached out and pushed on the butt plug a little. She sighed. I began to work it in and out of her ass, but not past the wide part in the middle. "You will have one, and you will like it." Her thighs were trembling slightly. I pulled the enema bag from where I'd hidden it under my clothes and held up the nozzle. "Look at me." She turned her head around to face me.
"I'm going to grease this up," I lifted the nozzle so she could see it. "And then I'm going to slip it into your ass, and fill you up. Then I'm going to put this--" tapping the butt plug "--back in and make you suck my cock until I come, or until that incense burns out." I pointed. I figured she'd have somewhere between five and ten minutes of being filled up. She was saying "no, no, you're not," even though her head was nodding in agreement. I checked the temperature of the bag. It was still warm. "You may empty yourself when either of those conditions have been met."
I began to pull the butt plug out and she whimpered ever so slightly as I withdrew it. I coated it with oil again so it would go back in easily. "Are you ready?" She remained silent. I moved the nozzle over her asscheeks, brushing them with it. "No," she whispered. "No...no...." I placed the tip against her asshole, which was stretched open enough to slide the nozzle tip inside with no resistance. Her pleas changed as soon as she felt this. "No...yes. Yes! Do it!" She raised her hips up for more. I slipped it inside all the way and raised the bag. Her whole body jerked and she began a series of low moans as I felt the bag slowly drain itself into her ass. "Oh my God... I feel so fucking full," she groaned. I slipped the nozzle back out of her and saw water dribble out of her asshole. I dropped the enema bag and quickly slid the butt plug back into her ass. She cried out when I did this and I saw a hand reach down to her pussy, where she began to rub herself vigorously. I moved around and presented my cock to her face.
Her face was flushed and her eyes were closed tight. She was groaning. "Oh, you fucking bastard... I feel so goddamned full... I have to take it out!" She opened her eyes and looked at the incense, which had burned down to the last quarter of the stick. She grabbed my cock and started sucking it furiously, moaning around my shaft and fingering her box the whole time. I could smell her pungent odor overpowering the incense. She pulled her mouth off of my prick just long enough to look at me and say "I hope you know I'm going to give you this exact same treatment when you least expect it!" before stuffing my knob back between her lips.
She was sucking and jerking my cock like a woman possessed, her spittle all over her hand and my groin. I didn't know how long I'd be able to hold my load. I could feel my balls tightening as she worked my shaft with everything she had. I looked at the incense and thought it would be close. Then I felt her arm reach under my balls, between my legs, and her middle finger searching for my asshole. She found her target and I felt it spear into me up to the knuckle. I grunted as she found my prostate and began rubbing it with no mercy. In seconds I was pumping come down Lisa's throat, both of us moaning as I climaxed.
She barely let me finish, pushing me back. "Give me some fucking privacy, you son-of-a-bitch!" I couldn't help laughing as she pushed me naked into the hallway, seeing her crab-walk to the toilet even as the door slammed shut in my face. A large glob of my come dripped off the end of my dick and splatted on the hardwood floor. I was in my bedroom when I heard her groan loudly, followed by several wet sounds. Maybe I'd gone too far....
It was almost a half an hour before she came to join me, wrapped in a towel, carrying one of the candles. Her face and the hair around it was wet. I hoped she hadn't been crying. She'd been getting off so much on the whole thing so far, I prayed silently that I hadn't humiliated her and fucked my plan up. "Lisa?" I said questioningly.
She didn't answer or look at me. She turned off the lights and walked to the nightstand, where she set the candle down. She turned on some soft music and I heard her set something else on the nightstand, then the soft rumple of her towel as it fell to the floor. She got into bed beside me. What to do? We both lay there, not touching, for about thirty seconds, before she started cracking up. I started cracking up too, and then we were both hugging each other, laughing together. We finally subsided.
"I didn't know if..." I began when I could talk again. She stopped by putting a finger to my lips. "Shush," she told me. "I've been thinking about our 'training,'" she said. I shut up and listened to her talk.
"I was pissed at you for about five minutes after I pushed you out of the bathroom. No one's ever done anything like that to me, no one's ever made me do anything like that before! It was so kinky, so erotic... so naughty! When I was all cleaned up, I had to masturbate myself twice before I felt ready to come out of the bathroom."
I felt relief wash over me. She laid her head on my chest and began playing with my hair with her fingers. She raised her head up and kissed me softly, reaching down to play with my cock. "You get me so hot, sugar." I grew stiff again under her manual ministrations. "I think you're ready," she whispered to me. "And so am I."
______________
Lisa looked at me with desire in her eyes. She leaned forward and kissed me hotly, our tongues tangling together. I wrapped her in my arms and we rolled around the bed until she was back on top again, straddling me, holding my hard cock with one hand like the pommel of a saddle. Her chest was heaving, and her tits jutted out from her body, capped by rosy pink nipples. I craned my neck up and sucked one into my mouth, grazing it with my teeth. She sighed and cradled my head to her. I alternated licking and sucking her tits as she cooed happy little noises. Her pussy was soaking wet. She spoke while I had my face buried in her chest.
"I want it."
"What do you want?" I asked her, drawing an erect nipple back into my mouth.
"I... I...." she faltered.
"What do you want?" I repeated.
"I want you to fuck me in the ass!" The words tumbled out of her mouth and she had an almost shocked look on her face. She blushed, and her chest grew flushed as well. She reached over to the nightstand and grabbed the bottle of baby oil. So that's what she'd been hiding under her towel. She set it on my chest, flipping the top open, and poured a liberal amount all over my torso. She lay down and rubbed her tits all over my chest, her skin glowing softly as she sat back up. "I want us to both be slippery as eels. I want to feel all of your body sliding over me."
I was amazed. The last several days I'd spent preparing Lisa to receive my cock had paid off. She'd was loving everything I'd been submitting her to!
She poured more baby oil all over my cock, letting it run down and drip from my balls. She coated it generously, stroking me until its' polished helmet gleamed in the candlelight. She kissed me again and then raised herself up on her haunches, panting as she did so. She gripped my cock at the base and began sliding her pussy lips and ass along the head. I reached a hand down to stop her. She looked at me, a mixture of lust and confusion in her eyes.
"You haven't begged for it yet."
She grimaced and I thought for a second she might climb off and tell me to go fuck myself. She closed her eyes and opened her mouth. After a few seconds I heard her quietly say "please."
"Please what, Lisa?" I asked.
Her voice was meek. "Please... please fuck me in the ass."
"You want me to fuck you in the ass?"
"YES!" she shouted. "I need you to fuck me in the ass! I am so fucking hot, I have to have your cock in my ass. Please!" She added again.
"Of course, anything you want, baby," I agreed. Finally! I pulled my hand away and let her mount me.
She positioned herself so that her asshole was directly above the tip of my cock. I was rock-hard, despite how hard she'd made me come earlier. She looked over her shoulder a few times, and between her legs, until she felt confident of herself, and then she slowly lowered her hips until I felt the head of my cock touching her anus. She was breathing hard.
"Go slow. Take your time to work me into you."
She nodded and I felt her pressing down onto me. "You aren't going to fit!" she exclaimed after a few seconds.
"Yes I will." I handed her the baby oil again and she put more onto my cock. "Push harder. Just take the head inside," I instructed.
I felt her bear down and watched her face. Her eyes were shut tightly and she was alternately biting her lower lip and darting her tongue out to wet it. She settled more of her weight onto my cock and I felt my prick pushing at her asshole. She backed off and repeated this several times, panting as she did so, until I felt her push down harder and she allowed herself to accept me. I heard her gasp. "Oh!" She immediately tightened back up, allowing only the head of my cock to press inside her. I could feel her small hole clenching tight around it. She started to raise her hips and I reached out to catch her.
"No. Just stay like that for a while, until you relax." She nodded. "Does it hurt? Are you okay?" I asked her. She nodded again.
"Play with my tits," she told me breathlessly. I took them in my hands and began to squeeze them the way she likes. She held still, her breath slowing, and then reached down and started to rub her clit.
I felt her body relax and then she was slowing bearing down on me. I felt resistance, and then she unclenched herself and I felt her ass open up to take me in another inch. She groaned out loud. "OhmyGod...OH MY GOD! I feel like you're splitting me in half!"
"Go slow. You're doing fine. You'll loosen up."
She stayed motionless. I could feel her asshole throbbing around my cock. The hardest part was past. All she had to do was let herself become comfortable enough to slide the entire length of me into her. She began to raise and lower herself slightly, moaning as she did so, accepting a little more of my steely shaft every time she sat back. She was rubbing her clit in fast up and down motions as she settled back fully, taking me right to the hilt. I felt her rock back and forth on me, her asscheeks resting on my balls. She was as tight as a vise made of velvet.
"Oh... I never knew you'd feel so good inside me!" She was riding slowly up and down my cock, groaning and panting. "You're so fucking big!"
I watched, not moving, as she rode my cock. I took her hips in my hands and began to raise and lower her. She frigged her clit faster, threw her head back, and cried out. I saw her pussy bloom open like a flower before she squirted hot juices all over my abdomen. "Fuck me from behind!" she commanded, raising off of me and turning around on all fours.
I got on my knees behind her and spat in my palm, rubbing it on the head of my prick. "Hurry up! Put it back in!" she yelled. I spread her ass apart and positioned my cock at her dilated hole. I pushed forward and felt less resistance as I pierced her. She urged me on by reaching between her legs to grab my slippery balls and pull me into her by them. "God, yes!" she cried. "Ungh! Oh, I love it!"
I sank in, buried balls-deep in her ass. "Go on! Fuck my ass, you bastard! Fuck my ass hard from behind! Give me everything you've got!" I pulled back out of her tight passage, leaving just the head inside, and then pushed back in. She groaned. "Do it faster," she said. "Didn't you hear me? I said fuck my ass HARD!"
I grabbed her by the hips and started pumping my cock into her ass. She loved it! I began slapping her cheeks hard with each stroke and she buried her face in my sheets, biting them and screaming. I caught a handful of her hair and pulled on it, raising her head again. I worked her good, listening as she screamed incoherent nonsense and called me every dirty word I'd ever heard, slamming her hips back at me. I kept paddling her ass with my hand and felt her drench both of our thighs with pussy juice as she came again, wailing. After that she began to jolt all over with each of my thrusts, and I realized she was lost in a sea of mini-orgasms. She quit speaking and began making animal noises, her ass squeezing me like a fist, juices from her cunt running freely down her legs. The sheets were soaked. I grabbed her tits in my hands and pushed my weight down on her, sinking to the hilt as I drove her down into the bed. Lisa was jerking like she had an electric current running through her body, tearing violently at my sheets, moaning loudly, then I realized it was me that was moaning, and I was going to blow my wad any second as she milked my swollen cock with her ass.
"Coming!" I shouted.
"YES!" She screamed, bucking under me. "SHOOT YOUR HOT FUCKING CUM UP MY FUCKING ASS! FILL MY ASS UP WITH YOUR CUM!"
I slammed my cock one final time into her as hard as I could and felt my balls contract as my seed erupted like a volcano, boiling hot bursts spewing from my shaft. My balls contracted with each spurt as I bathed her insides in my come. She was sobbing and clawing at my hips, trying to force me further into her. I realized I was grinding my teeth together as I saw stars behind my eyes. I throbbed over and over, my orgasm wracking my entire body with spasms, emptying what felt like an immense amount of sperm into her ass. I felt myself finish and fell down on top of her. We were both exhausted, gasping for air, covered in sweat and oil. The sheets were a ball around us, soaked with her come. I held her, and we lay there, stuck together as our skin cooled and my cock quietly grew soft in her ass. An eternity later I found myself kissing her neck as I slipped free of her.
She still had her eyes closes. "I love you, baby," I told her.
She weakly opened her eyes. "I love you, too," she said, reaching up a hand to stroke my cheek. "And I'm so glad we haven't made plans for the weekend yet."
