tagGroup SexThe Chaperone (New Boobies end)

The Chaperone (New Boobies end)

byRodrigo Santeria©

(Note to reader, you may want to read my story, New Boobies first, but I think this will stand on its own)


It'd been over two weeks since the yellow pages rep, Krissie, with new boobies, came by. I thought about her every day. She was married. I'd see her again, but left additional contact up to her.

She called Friday morning and told me she'd be by to pick up the check, before I left. I waited. After five, I locked my door to head home. When I looked up, she was there, smiling at me. She looked good, in this wine colored clingy dress that had short sleeves, with a crew neck that accentuated her collarbone, breasts, narrow waist and came down about mid thigh. She wore matching wine colored high heeled shoes with contrasting black heels. Again, not professional, but very sexy.

As I was enjoying her lovely visage, a much younger woman stepped around her in far more business like attire. Still, quite a short skirt to match her buttoned down jacket. All black, her hair, glasses, camisole, jacket, short skirt, stockings and high heeled shoes. Somber would have been my first guess, except for her beguiling grin and forthright approach. She offered her hand, "You must be Kristoff, I've heard some flattering tidbits about you."

"Lies, all lies," I responded clasping her hand, surprised by her firm, masculine grip. She was charming, slender and what she wore, worked really well with her personality. "That's quite a grip, you've got. I'm impressed. I like it." I said stepping into the greeting, standing up straighter and invading her space, just to see how she'd react. I'm tall and I know it's intimidating to do this and sometimes it's just fun. She held her position, we grinned at each other and I began to turn to unlock my door.

"This is Kistacia," she's an associate of mine from work. I'm mentoring her." my agent added. Glancing back, around Kistacia, I was aroused to see Krissie raising the hem of her dress. My heart skipped a beat, it was slightly higher than where it would normally be, but the suggestion made my dick jump. "I see..." pausing for dramatic effect, "and has your mentor explained how she managed to wrangle me as a client? She's very good at establishing a relationship." I added, turning back to the door, but not before Kistacia glanced back.

I opened my office, flipped on the lights, and let them pass. The check sat under my keyboard, but Krissie took my chair and Kistacia sat down in the only guest chair. I was left standing.

"This is cozy." Kistacia added deridingly. True enough, but not what you'd say to a new client. Clearly she needed a mentor. My office was small, fourteen feet by twelve feet with an old Herman Miller L shaped desk from the seventies, a guest chair, an oak filing cabinet that could double as a table and a large bookcase that looked more like an armoire, with maple stained doors on the front.

I was about to point out the result of insulting a client before you've been paid, when Krissie turned toward me and giggled, "This is how he sits." leaning back in my chair, fingers laced behind her head and with her knees man's width apart. It was an accurate portrayal, not nearly as funny as her laughter would lead you to believe, but more importantly, she was flashing me her denuded vagina along with the metal ring of the plug nestled in her sumptuous ass. Positively cackling, she crossed her ankles, brought her knees together and swiveled in the chair to face Kistacia on her left.

Kistacia had to know something was afoot. My tumescence was increasing the more I was being teased and I was wearing dress pants, which simply don't hide much when you're halfway erect.

"Ya want the check?" I asked moving closer to Krissie, trying to diminish my profile from Kistacia.

"Of course," Krissie smiled arching her back, thrusting her chest at me.

"Uh, it's under my keyboard, may I get it?" I asked, as Krissie used her hands on the armrest to push herself up, but not like old people. Feline. Like a cat walking away while you're petting it then coming back to be stroked on demand. She brushed my dick with the back of her right hand as she arose, then stood behind Kistacia. That was it, I was fully erect. I could pound nails with my dick. I sat down, got the check and turned to face the girls, leaning over to hide my erection, while extending my hand, so either could take it.

Krissie had her tits out over the top of her dress, and she was beaming. "Don't you think Kistacia will make a wonderful sales girl?" she asked.

"May I speak candidly, Kristoff?" Kistacia demanded. I nodded watching Krissie tuck the girls back in her dress. Kistacia took the check and laid into me. "It's obvious you have an erection," I blushed, "and Krissie's acting... bizarre. I mean, we were supposed to leave at two, then three and we finally got out the door just before five, plus goody misses two shoes here, changes into the smokingest hottest dress I've ever seen her wear. What the fuck, is going on between you two?" she added emphatically.

"Well, that's a good way to break the ice." I stated, relieved the questions had begun. I leaned back in my chair spreading my legs a little wider, frankly enjoying my hard on, and amused that both women lowered their eyes and gazed at my dick. Krissie, with lust, while Kistacia looked bewildered, maybe intrigued.

"How long have ya worked with Krissie?" I added leaning on the left armrest while I ran my thumb up the length of my dick. Both girls were rapt, unable to look up. I was being objectified and it felt fantastic.

Kistacia swallowed hard, looked up, like the proverbial deer in headlights, then softly, "Umm, since the beginning of the year."

"And did you notice anything different about Krissie when she came back from her vacation?" I offered as I slowly continued to move my thumb up and down the length of my dick.

She grimaced briefly and with a decisively disdainful edge, "Ya mean her fake tits?"

Krissie winced and moved slightly away from Kistacia. "Yes." I stated, adding, "Krissie's fabulous new boobies.They're something to be admired, even worshipped, if you're into that kind of thing."

Kistacia snorted and shot a sideways glance at Krissie, "Mrs PTA? Class mom? The pilates princess? Mrs Manners, never do anything untoward? This lady right here dressed like a high dollar call girl? Please, I told her about you." she revealed, "I saw you at a local restaurant with... it must have been a client about a month and a half ago, down on the Plaza. I got your number from that old woman you took out, and gave it to Krissie. I told her she should try some younger guys and I thought you looked hot, plus that client really liked you. Maybe you had a thing for older women."

"Never anything untoward? Huh." I surveyed Mrs Manners. She held my gaze. I looked down and ran my thumb up and down my cock again, then looked up and saw her biting her lip. Her fingers playing with her hemline, again. "So what were those lies she told you about me?"

Kistacia grinned, glancing sideways and seeing Krissie's hand quickly move away from her hem, "She said you had a great laugh and smile to go with it. She said you smelled good and... veiny, uh what did she say? She liked how your veins stood out. She liked your hands."

Kistacia looked at me, then Krissie, then back and forth, "She said you looked like you knew your way around a pussy. Holy shit, you guys fucked! Didn't you?" Kistacia laughed, being in on the joke, "No luck on your cruise, but the first day back in town you get nailed by a client? Shit Krissie, what the fuck? Why am I here? The sexual tension between you two is off the charts.

"I don't get it." I puzzled, "You said your husband got you new boobies and you went to the Caribbean, but Kistacia says you didn't get laid? Did he lose his dick in some unfortunate shark cage accident, or something?" I was thinking so hard, trying to find the missing pieces my erection began to subside.

Laughter from both girls. "Actually, that's right, but not from a shark." Kistacia embellished, "and her husband never set foot on that boat."

"Ex husband," Krissie corrected, "and it would have been wonderful if some unfortunate accident had taken his dick, or even his life. Everything would have been much simpler."

"You're divorced?" I added stating the obvious and more than a little disappointed in myself for not seeing it earlier. "So... Kistacia... is our... chaperone? Feeling some ambivalence about meeting me last time, are you?" I grinned.

"Not now..." as she was obviously playing with herself under her dress behind Kistacia only to be interrupted by the other girl.

"Why me? I told you, this guy was hot, and why do you think I'd stop you from fucking him. I'd fuck him. 'Veiny,' you were talking about his dick and you were... 'knew his way around a pussy,' ha! I feel stupid." glancing over her shoulder seeing what Krissie was doing, "Oh, Jesus!"

"I wanted you to meet Kris, because I wanted to see if you thought he was as sexy in person as you thought he was in the restaurant, and if you did, I was going to tell you how slutty I'd been, which you'd never have believed." Krissie explained in a sultry voice while looking at me through hungry eyes.

"Oh yeah! You should fuck him. Right here. Don't mind me." Kistacia added pulling her legs tightly together and under her chair glancing at me provocatively.

The tide had turned, and my dick was throbbing again as I unzipped my fly, unclasped my belt and unbuttoned my pants. I wrestled my dick under the waistband of my shorts, tucking everything under my balls, as I instructed Krissie, "On your hands and knees. Crawl over here and suck my dick," and obediently, Krissie was on her hands and knees, kissing my balls, while she reached up and grabbed my dick.

She had her eyes closed as she ran her tongue up between my nuts to my purple head. As she opened to take me into her mouth she looked up at me with wild eyes, like the first time we met. She closed her eyes as she took my cock into her warm and wet mouth. I looked at Kistacia watching us, and pushed Krissie's head down on my cock causing her to choke. I held her there for a second, maybe two before I let her up for air. My dick was wet and she grabbed it tightly and began stroking. "Suck on my balls Krissie. See if you can get both in your mouth at the same time." I commanded watching Kistacia squirm as she watched us.

"Look!" I ordered, as I pulled Krissie's dress up over her ass. Kistacia's eyes grew large seeing her mentor's wet pussy and plug filled asshole. "Is this untoward or would you like it more untoward you? Krissie sat in the very chair you're in now spread her legs over the arm rests and played with herself as she watched me jack off. It was hot, then I saw she had a plug in her ass." To Krissie, "play with your plug for Kistacia."

Krissie nuzzled my wet dick as she rested her head in my lap, while rubbing her clit with one hand, in between her legs, and slipping two fingers from her other hand into the metal ring, pulling it partially out before letting go and sucking it back in her ass. "I can't believe I'm doing this again," she groaned.

I began stroking my dick watching Kistacia watch Krissie. She was wound up. "You should help her and pull that thing out of her ass." I offered, wondering if all she needed was an invitation. I pulled Krissie's hair so her head came off my lap, then held her face as I pulled her up kissing her passionately. "You are such a good girl, sucking my cock and showing Kistacia how to get a client." She had my dick in both hands as I continued to hold her face and kiss her.

Kistacia had moved, and Krissie growled or moaned or some combination as the younger woman freed the plug. "She's so wet, it's dripping down her thighs." Kistacia added now holding the plug as she stood next to us, with a hand on my shoulder.

"Put it in her mouth," I instructed with a devious grin.

"That's dirty. I have a better idea," she countered offering it to me.

"That is dirty. From her asshole into my mouth... ya like that? How bout you Krissie? Would you like that?" I asked. Both girls remained silent, but watched me intently. Krissie's hand joined Kistacia's as the widest part slipped past my lips.

"Fuck! That's hot!" KIstacia managed looking at me in a startled and pining way.

"I want you inside me," Krissie added as she began to stand up. I held her shoulder down as I angled my dick towards her mouth enjoying the scene as the tip of her tongue dabbed at the bead of clear precum that formed at my hole and began to slide down the underside before taking me almost entirely into her mouth.

With my dick warm and wet, I got the plug out of my mouth with my left hand, while catching Kistacia by the back of the neck in my right, muttering, "C'mere."

She bent and I kissed her deeply, enjoying the sensation of our tongues sliding against each other's. I felt the perspiration at her hairline and the fine strands of black hair held up by the clip at the back of her head. I removed it, broke the kiss and as she was about to speak introduced the butt plug past her lips. "Dirty girl! Hold it right there."

Turning my attention to Krissie, I reached down her body catching the hem of her dress and pulled it up, forcing her to release me as I removed it completely, tossing it to the side, like last week. She was already removing her powder blue bra with wine trim, when she caught my gaze, "Leave the shoes on? You like?"

I grinned, "Yes! Magnificent! Definitely, leave your shoes on."

"Sit down there, and watch this." She ordered Kistacia pointing to the guest chair, then to me, "Strip!"

She was standing next to Kistacia, one hand on the top of the chair back with the other continually, playing with herself. Kistacia had removed her jacket and was holding the plug like a lollipop, "Jesus, his dick is veiny, look how swollen his cock head looks."

I kicked off my black suede loafers, Krissie added, "Those are nice shoes, I like 'em."

Laughing I peeled off my socks, then I stood up. From the weight of my belt, keys and wallet my pants hit the floor. "That's great," Kistacia added popping the plug back in her mouth. My dick stood out from my shirt tails in the front and I reached to undo my tie. As I loosened it she added, "That's a good look, undoing the tie with your cock standing out, wow whodda thought."

"There is something very masculine about that," Krissie added.as I slipped the tag end out of the knot and lay the tie on my desk. I removed my cufflinks, then unbuttoned my shirt, removed it and tossed it on the desk. I reached behind my head grabbed the collar and pulled my white undershirt off adding it to the pile. I slid off my shorts and for the first time Kistacia put her hands between her thighs. Not like Krissie who was openly masturbating naked, but it moved the hemline of her skirt up.

"Sit down on the edge of your chair and spread your legs." Krissie directed then stepped forward rubbing the palm of her wet hand spreading more precum over my glan, turning, reaching between her legs and guiding me into her warm, wet and slippery cunt. I moved her hair off her neck and bit lightly at her nape. Licking and biting, as I snaked a hand around her side, running it up, under and over her breast, then squeezed.

"Unghhhh! Fuuuuuck meee!" Krissie sighed as she began to rise and fall on my cock. After a dozen strokes she straddled my legs, opening herself to Kistacia, "Fuck me! Watch him fuck me."

Kistacia removed the plug from her pretty mouth and chimed in, "God that looks so hot watching his veiny cock move inside your greedy little pussy."

I added, "You should feel her tits. That's how this all started with me."

Kistacia stood, and came over to us, she pulled out the plug, "Hold this," popping it into Krissie's mouth, then I felt her hand over mine, "These are huge, shit! It's kinda fun playing with you titties." I didn't know exactly what she was doing, but it was having an effect on Krissie. She jerked and spasmed, moaning around the butt plug in her mouth. She tried talking and although it was indiscernible, it was clear she was cumming on my dick and I guess, Kistacia was sucking a nipple, while squeezing her other breast with me. Then I felt her hand cupping my balls which were tightening up.

"Oh shit! That was hot!" Krissie added after taking out the butt plug, "You've got to try his cock. I want him to cum inside me, but you've got to ride his dick."

I had fucked two girls in a day before, but never two girls at once and Krissie was urging Kistacia on. The thought had me close to the edge. Krissie climbed off and went to the chair, sitting kinda on her side with her knees wide apart as she fucked the plug in and out of her mouth, then her pussy, and finally her asshole, only to repeat the scene.

Kistacia wavered a moment, turned away from me and hiked her skirt up to her waist. Everything in black, stockings, garter belt, and about the wispiest thong ever made. It was a thrill as she reached back and pulled it to the side, exposing the sexiest asshole I'd ever seen and her already partially opened pussy. I spit into my hand spreading it over my purple glan and down the top side. I could see my heartbeat in my erection and it electrified me that she was going to take my cock despite the fact it just came out of Krissie.

She grabbed the armrests and backed up allowing me to line myself up. I couldn't resist pushing my head against her asshole and then pushing it forward spreading her lips until the slit of my cock was pressing against her clit. She froze, allowing me to play with myself in her oily folds. "I want your veiny cock inside my slutty fuckhole. Fuck me, like you fuckeid her. I want to cum all over your cock. Use me! Show me what a dirty fuck you are! Prove to me you know your way around my slutty little pussy"

I lined up. She took me halfway, raised up and enveloped me, balls deep. I pulled her black hair so I could talk right in her ear. "That's all of me, shoved up your pretty little cunt." I growled, "Ya still want it? Want to be used? Everything I did with her?"

"Fuck me! Make me feel you. Yes, I want..." then she orgasmed like nothing I'd experienced before. Kistacia gasped and I felt warm liquid coat my balls and inner thighs. It felt amazing as it washed or splashed over me and she was squirming on my dick, moving in ways I'd never felt.

"Did she just squirt?" Krissie asked incredulously. Then I felt it again, and something else. Krissie was on her hands and knees. I could only see the curve of her left hip, but she was gently lifting my wet balls, then I felt her tongue, spread wide licking between my balls and up my shaft.

"Your tongue..." Kistacia cried with a telling squeal as she forced herself down on my shaft.

I began a mad dash to strip Kistacia, wanting to feel her skin against mine as she squirmed on my dick and Krissie's tongue. I had her camisole off and on the floor, followed quickly by her bra. She had to stand to remove the skirt and her tiny thong.

"I want to eat your pussy, as we stuff his cock up your ass." Krissie growled, first forcing Kistacia's legs apart and then spreading her ass. It was a remarkable view, my wet cock, throbbing with my heart beat, next to KIstacia's tiny pink star and long labia, slightly above Krissie's shaved cunt, through Kistacia's open legs. Fill her ass, like you fucked me, she wants it." Krissie continued.

Kistacia reached behind her, guiding me, lined up for the push, but bending my cock ever so exquisitely, before stuffing her little cunt. Down all the way. Again I felt Krissie licking Kistacia and then onto my balls, then scolding her. "Take him up your ass, you dirty slut... and squirt in my mouth."

When she came off, Krissie positioned me farther back and I watched fascinated, my slick head began to prod open her little butt hole. She squealed, and the edge of my crown suddenly disappeared, engulfing at least a third of my prick. Krissie was awash in Kistacia's pussy juice. It was running all over her head, neck, shoulders and tits. I had the simultaneous urge to force my aching cock though that wonderful friction impaling Kistacia and if it hurt her, all the better, versus the undeniable desire to wait for her to take as much as she could and build up to pounding her while Krissie licked my balls.

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byRodrigo Santeria© 2 comments/ 11983 views/ 7 favorites

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