Joe's Adventure In The Windy City

Received on July 22, 2000


A business trip to Chicago resulted in this guy enjoying the Scottish lass who was his "temp" secretary...  and her young daughter.  A memorable trip that was followed by many more FMF sessions with the two women.  


	I had spent a strenuous three days in Chicago putting together a deal with clients who were more interested in golfing stories than in the details of exactly where the million or so each of them was putting up was going and how it would be protected.  The rich can be a pain in the ass.

	One bright spot in the proceedings was that I worked with a bright, beautiful secretary from a local "temp" agency, a 40ish  darlin', who had the same black hair and blue eyes I did.  The two of us were just a pair of ancient Scottish Highlanders dancing to the tune of modern chrome and steel... and big bucks.

	Her name was Heather Sims.  We got to bantering, and flirting, but that did not detract one bit from her efficiency and production.  About the only difference was that she started calling me Joe instead of Mr. Adams.  I found myself wondering whether she shared the generous, sexually charged impulses of our common ancestors.

	 When our business was all over but the signings, scheduled for the next morning, I invited Heather for a meal and a drink.  After a good meal at a four star restaurant, we ended up at a local bar in the Near Northside.  As we sat down at the bar, I asked her what she wanted.

	"How about a Long-Slow-Screw-Up-Against-The-Wall?"

	"Sounds like a good idea to me..."  I said as pokerfacedly as I could manage.  I don't know whether she really wanted the trendy drink or just wanted to say the name, but I ordered one for her, and a Johnny Walker Black for myself.  "What's the difference between a Long-Slow-Screw-On-The-Beach and a Long-Slow-Screw-Up-Against-The-Wall?"

	"Less sand," she said dryly.

	"I wondered about that. This your local bar? You come here often?"

	Heather's eyes crinkled as she shook her soft raven hair and took another small sip of her drink, "Do I come here often?  Well, I drink here sometimes."

	My kind of banter.

	 Her generous mouth pouted slightly as she brushed imaginary crumbs off her fully filled blouse.  Then she said,  "Something I've been meaning to ask you for three days... where did you get that lovely dark hair and those blue, blue eyes?"   Had she really said that, or was I just having a wet dream?

	"Just good Scottish genes, I guess.  Looks like we've been swimming in the same gene pool," I said,  "You're a brae wee bonny lassy yerself."

	"Aye, I dinna' kin deny it, but not so wee, for ae that," she said as she slid off the barstool and stood fully erect, about five-five, arching her back a little, showing her voluptuous chest to full advantage. She smiled as she watched my eyes travel down her body, noting the trimness of her waist, and the fullness of her hips.  I frankly admired the same luscious, ripe body I had been glancing at for the past three days.

	"Aye, and a grand lass ye are," I said.

	We engaged in the ritual dance of smalltalk and banter for the next fifteen minutes while Heather appeared to come to a decision of some sort.  Finally she said, "Listen, Joe, will you take me home, now?  I gotta' check on my kid.  Make sure she's okay.  Linda.  Now there's a wee lassy with a lickerous eye, for ya."

	.....Pregnant pause....

	On the ride to her apartment in my nondescript rental car, we made small talk and got more personally acquainted.  I learned, for instance, that Heather was a college graduate (no surprise), a single mother who frequently took her daughter on week-long vacations to places like Barbados and 
Singapore.  (On a temp's salary?)   She had also been an erstwhile gogo dancer until "the sonsabitches told me I was too old."

	I made appropriately scornful noises... the fools.

	Heather learned that I was divorced,  and one hell of a guy... (I hoped).

	When we arrived at her apartment, she said, "Well, thanks... say listen, would you like to come up for a nightcap?  Frankly, I may need help evicting the young studs sniffing around Linda.  You won't be required to do anything physical, you understand, just make like a male authority figure..."

	When we walked into the apartment, the first thing I noticed was that it was very expensively decorated, Waterford crystal on the John Lelong coffee table... that sort of thing.  The second thing I noticed was that there was no one there but an adorable little girl of thirteen or fourteen, curled on 
the couch in a short nightie, watching TV and drinking a soda.  "Hi, mom! Oooh... who's this?" ducking her own version of her mother's jet black head at me.

	"This is Joe Adams, Linny, the man I have been working with for the past three days."

	Far from being embarrassed by being found in her flimsy nightie, Linda stood up and walked toward me with her hand extended, seemingly totally oblivious to the light behind her that was turning her short nightgown almost transparent.  I was treated to the sight of a slender, budding, beautiful body within a halo of shimmering light.

	"Hello, Joe," she said, as she took my left hand in her right and pulled me further into the room. She smiled up through short black curls.  My heart raced as I did my best to be totally casual.

	"Linda, is it?  Whatcha watching?"  Was I panting, or was that just my imagination?.

	"Oh, just some old stupid movie," she said, stooping to turn off the TV, and allowing the nightie to ride up her nicely formed pubescent ass.  Where was the remote?  WHERE WERE HER PANTIES?

	"Linny, dear," her mother said mildly, "don't you think its time for bed?  Say goodnight to the nice man and... shoo!"

	Linda gave her mother a pout, and stood before me, as I took a seat on the couch.  "Goodnight, nice man," she said as she bent forward and patted my leg, giving me a clear view right down the front of her nighty at her lovely soft budding body, her little breastlets about the size of big puffy pink marshmallows, wisps of dark hair beyond the flatness of her tummy.

	I waited until she was out of the room.  "Charming young lady."

	"Well, she certainly showed you most of her charms," said Heather amusedly. 

  	She had poured two scotches from an exquisite silver decanter at a little portable bar at the side of the room, and came toward me, swirling the ice.  She handed me mine and plunked down beside me, curling her feet under her so that her skirt stretched tightly about halfway up her thigh.  "She is a handful... so competitive with Mommy!"

	"A little young to be much serious competition, I would think..."

	"You'd be surprised," Heather said cryptically.

	"Well, she's gone now... you have the field to yourself... such as it is," I groaned as I felt the weight of three scotches and the past several days gathering in my head.

	I put my hand on Heather's knee as I set my drink on the floor.

	She looked down at my hand on her leg, then up at me. She set her drink down. "Listen... Laddy, don't you think ..."  I raised my hand and caressed her cheek, stroking the hair back behind her ear.  Right then, right there, she was heartwrenchingly desirable.  She curled her head into my palm, and said, softly, "Damn."

	Her chest heaved as she sighed deeply.  She started to roll up onto her knees, and we met halfway as I reached across with my other hand and drew her closer.  Our noses were two inches apart.  We breathed warmly into each other's faces.  Heather moaned, "I shouldn't... I can't... I don't even know... oooh."

	We began speaking nonsense.  Mouths grazing mouths as we talked.

	"You're so..."

	"You too..."

	"I want..."

	"I know..."

	"Could we just..."

	"Okay."

	Her skirt had ridden higher as she had moved toward me.  Now she sank into me, turning slightly so that her upper body was against the back of the couch. Her legs opened slightly, and my hand was on her inner thigh.  Idly, I noted the old fashioned stockings and garter belt as I caressed the soft, silken, incredible flesh at the top of her leg, my fingers grazing the edge of her panties.

	She began straining her chest forward as we licked deep into each other's mouths.

	I unbuttoned her blouse by Braille, and discovered that the bra had a front clasp, which I fumbled with ineffectually.

	She drew her head away slightly, and panted lightly.  "Ah.  At least... you don't do this... too often."

	Very often?  How about never?  But all I whispered was,  "Help!"

	Freed of their confining straps, her generous breasts virtually poured out, still with enough tone to stay more or less completely in front, her big pink nipples already erect.  I cupped her left breast lightly, then squeezed gently so the nipple came forward to meet me as I bent my head to suck.

	Heather moaned and sank down even farther, so that I was on the edge of the couch, and she was supine beside me.

	Her legs splayed wantonly.  I slid my hand down and cupped her crotch, which was hot and wet through the silky underpants.  I traced my finger down the middle as the lips seemed to puff and part on their own.  Her cunt was sopping... and hot... and opening.

	As she pushed me away slightly and began fumbling with my belt, I caught a glimpse of movement out of the corner of my eye.  Linda was standing in the hallway near the foot of the couch, watching.  Our eyes met and hers widened as she smiled slightly.  The situation became intensely erotic, a pretty pubescent girl watching her mother make love to a stranger.

	Heather and I stood slowly, while I maneuvered her so that her back was to Linda.  She cooperated fluidly.  Slowly we undressed each other, kissing all the while.

	We fucked slowly on the couch while I caught glimpses of Linda fingering herself and masturbating as she stood leaning against the doorway.  Heather was moaning and crooning as she reached orgasm.  I came like a ton of bricks, and sagged to the side.  Linda disappeared.

	Heather and I cooed and talked, and had another drink.  I could barely keep my eyes open.  I was getting groggier and groggier by the minute.  Finally Heather took mercy on me and went to get a blanket and pillow, saying that I was welcome to sleep on the couch if I wanted to.  She said she would invite me into her bed, but she had another temp job lined up for the morning so she needed her sleep.  I was grateful to crash right where I was.  I did manage to stay awake long enough to put my boxers back on.

	About 3 AM I was wakened by the need to piss.  As I was coming back into the livingroom, there was fourteen-year-old Linda, sitting Indian style on the couch (my bed), looking sweet and careless, with one of the straps of her nightie sliding off her shoulder. Her flimsy nightie didn't quite conceal the dark wisps between her widespread knees.

	I stood there, nonplussed, tension gathering in my loins.

	"Hi, stud.  How was my mom?" she whispered in a giggle.

	"Um, your mom is a very generous and loving lady."

	"Yeah?  Generous enough to share her new friend?"

	I groaned.  "Linda, don't you think you're a little young for such things?  And what if your mom were to walk in here right now?"

	"Oh, she won't," said Linda, ducking her head and smiling at me from under her dark eyebrows.  She always takes a pill before she goes to bed.  She sleeps like a baby."

	"But, you... are you sure you know what you're doing?"

	"Try me."

	I groaned softly, betrayed by my growing hard-on, which was threatening to poke through the fly of my boxer shorts.

	She uncoiled from the couch, and dropped to her knees, reaching for my shorts.  "Oooh," she said as she eased my shorts over my erect cock.  "No wonder mom kept you around..."

	She grazed her mouth along the side of my cock, and clasped it to her warm cheek, so that the head of my cock was poking at her ear.

	"Wanna' stick it in my ear?"  She rubbed her downy cheek against the side of my shaft.

	She rose slowly and led me by the cock toward her mother's bedroom.  When I balked, she stopped and backed up into me, fitting my cock into the small of her back.  Her ass brushed back and forth on my balls.  "Com'on, chicken," she said.  "I want you to fuck me in front of my mom.  Fuck me where she could see.  Fuck me, and then fuck her again while she's asleep.  I'll hold your cock and guide it into her."

	A warm purple haze clouded my brain.  I became all cock.

	Linda knelt up on a cushioned blanket-chest at the foot of her mother's bed, and waved her pretty little ass at me.  I came up behind her and slowly eased my cock into her tight little pubescent quim from behind.  She was very hot, and very wet, and very tight!  It was almost like fucking an older woman in the ass.

	Linda groaned and forced herself back against me, plunging me all the way in as deeply as I could go.  I put my thumbs on her shoulder blades. Her back was so small that my fingers nearly reached her budding little nipples.  I slowly, lightly, slid my hands around so that each thrust of my cock made her distended and puffy nipples brush across my palms.  She held onto the footboard of her mother's bed with one hand and brought the other up between her legs, playing with herself and with my sliding cock, and moaning softly.

	My thrusts were forcing her to shake her mother's bed as she held on.  Both Linda and I had been right on the point of cumming, at the point when it was inevitable, when Heather rolled onto her back and slowly opened her eyes.

	Suddenly she started, grabbed for her nightstand and whipped out a small pistol.  Neither Linda nor I stopped.  Heather could have shot me if she wanted to.  I would have died happy.

	Instead, she lowered the pistol just as I shot spurt after spurt of hot cum up her daughter's little cunt.  Linda was herself flushed and bucking.

	Slowly, Heather smiled.  "Your idea, Honey?"

	Linda nodded, "Oh, mom, he's good!" she panted. "Better than daddy, thats for sure!"

	Heather raised an eyebrow.

	"Mom, let's keep him.  Let's tie him up and fuck him to death."

	What the hell was going on here?  Guns?  Daddy?  Tie him up?  I began wilting quickly and started backing toward the door.

	Heather gave a low laugh as she put the gun back in its drawer.  "Relax, lover," she said to me.  "So we share.  I find 'em, and we both fuck 'em."

	" 'Cept for Ralphie," giggled Linda.

	"Yeah well, we'll leave your little friends alone for a while, Sweetie."

	Linda turned to me.  "Ralphie couldn't quite handle Mom," she chuckled.  "He came almost before she touched him, he had just started fondling her boobs.  So we decided we'd only "do" grown-ups."

	I was relaxing visibly, gradually realizing that this was all a con and a set-up.  There had been no sleeping pills.  There was no new job in the morning.  They'd played this whole little game before.

	Heather patted the bed beside her.  "Come on, Stud, snuggle in.  Get some more sleep.  You're gonna need it."

	 As I climbed into the middle of the big bed, Linda followed right after, and I lay on my back with the forty-year-old witch on one side and the fourteen-year-old witch on the other, both nuzzling in my ears and stroking my tired body.

	We all fell asleep.

	In the morning they took turns fucking me as I lay there on my back.  First mom-Heather solidity on my loins with her big soft tits in my face... then, thirty seconds later the pubescent litheness and the little puffy tits of Linda were arching over me.  Each helped and fondled the other, kissing me and each other.  

	They must have orgasmed ten times between them, and when I finally came, it was with Linda's soft little hand jerking me into her mother's mouth.  They grinned at each other and kissed, sharing my semen, mouth to mouth.

	I was only a little late for the signings.

	With Heather and Linda, it was the beginning of a beautiful (if non-exclusive) relationship.   When I am in Chicago I always call Heather and, if she and Linny don't have another "date," we all have dinner like a happy family.  The only difference is that both mother and daughter are stroking "daddy's" cock under the table linen.

	And I have finally figured out how Heather can afford such nice things and expensive vacations on a secretary's salary.   I have to go to Athens next month.  I've booked three tickets.