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Q in the Toddling Town

Q meets exciting fun on the town

Q in the Toddling Town

It had been a great trip to Chicago. Museums, restaurants, clubs and bars.   We were mature friends visiting the “White City” for the first time. The day had been the architecture cruise on the river and a light lunch at Morton’s Steak House.   Back to our near north side hotel we had soaked in the hotel Jacuzzi and partaken of what ever we thought we could get away with beneath the bubbles of the tub. That was followed was a short nap and other bedroom adventures.


Q was rested, rejuvenated but very “randy” when we ventured across the street to a recommended steak house on Dearborn St.   I asked if she was hungry and Q confessed “not really.”   So I suggested a drink and a little early Jazz from a nearby club.

  The club was busy serving dinner and Jazz from a Dixieland Combo on a small stage.   I paid the early evening cover charge and we parked ourselves on two bar stools with a slightly obstructed view of the combo.   Two middle age black guys were engrossed in business with an empty seat between them and Q.   That was soon filled by a fortyish, businessman with more on his mind than Jazz.


As Q sipped her wine and we listened to both the familiar and unfamiliar tunes I gently rubbed her back with my left hand and caressed her right knee with my other.   Her sexy, button down blue dress was about knee length.   I was starting to bunch it up around her leg as I gently stroked the inside of her thigh.   According to our fun-game/practice of unbuttoning a button for every drink, the first lower button of her dress was unfettered.  


At first our nearest neighbor was engrossed in E-Mail and the black pair in their business discussions but as I slid my hand well past Q’s knee I was getting quick sideways glances from the twitterer and the far black man.   Q and I whispered and giggled about her being a “Cougar on the Prowl.”   Her assessment of the nearest bait was not enthusiastic.   I suggested the more distinguished dressed of the black pair but she preferred the other, younger conversationalist.


After a lot of teasing, coxing and massaging of her pure white thigh, she leaned into her closest potential bait, placing a hand on his shoulder with the pretense of getting a glimpse around the obstructing pole that blocked her view of the trombone player. Polite but not interested was his reaction. This was not lost on the black guy who excitingly filled in his friend.


The near guy left.   After another round and this time with a top button loosened we were having more whispered fun.   The black pair got up to leave.   The younger of the two held back surveying Q with a lustful smile.   Before he could depart I made eye contact, smiled, nodded and behind Q’s back pointed with my left index finger to the vacant stool on Q’s left.


He fumbled but then told his friend he was going to stay, have another drink and listen to some more Jazz.   When he sat down he waved his finger over the parts of the bar in front of the three of us indicating he would buy a round.   “Hi, I’m Sam,” he said, extending his hand to me but looking intently into Q’s eyes. Sam’s intense grey stare mesmerized Q.


Conversation established that he was forty-four, single (at least for tonight) and interested.   Visiting from Denver on business and staying at the Residence Inn on Dearborn, the adjoined, sister hotel to ours.   Drinking Makers Mark and water, Q thought he was, handsome, educated and charming.   My observation was that he didn’t lack any self-confidence.  

When my cell phone buzzed I pulled it from my pocket.   A call I could return later.   When I returned my hand to Q’s back, his right hand was already there,   massaging her neck and stroking her back.   He was casually playing with the dress strap over her left shoulder.   I knew he had discovered that she had not worn a bra which magnified his interest. As Q warmed to his attention they both naturally turned toward each other.   She widened her legs so as not to lose my interest on her right thigh.  

 Soon, I saw, he was stroking her calf below her knee but that was not meant to last for long.   He asked Q how old she was.   When she replied 67, he looked surprised but smiled pleasantly.   He complimented her on her great figure and pretty face. He moved his hand further up her leg. Q’s Cougar juices surged.


I could see that Q no longer needed encouragement from me to pursue the role of Cougar. She quietly moved his hand away from her thigh, placing it on her lap. She knew this was not the time to appear too anxious. She failed to realize, though, that the buttons on her dress were spaced in such a way that he could get his finger between the buttons to touch her pussy. He gently massaged the lips of the clit, while watching for a reaction. As this was somewhat awkward, she once again removed his hand. She whispered to Sam that custom and tradition dictated a button be loosened from her dress every time she had a drink. Since he bought the drink did he want to do the honor? “In fact,” Q said, “why don’t you do two?”   He undid a button from both the top and bottom of the blue dress and returned his hand closer to her very wet clit.


Unable to contain my excitement, I excused myself to the men’s room. I took a little extra time and when I returned both Sam and Q were gone. Scrawled on a napkin in her handwriting was the message “be back sometime???.”


I saw them on the dance floor.   The band was playing their closing song “Sweet Georgia Brown”.   Sam was slinging Q back and forth with an old fashion Jitter Bug.   As the band broke down their gig, juke- box music filled the gap between the band and the follow on gig.   The music was slow and Sam pulled Q close to him and swayed to the music.   She put her arms around his neck and laid her head on his shoulder.   His hands went to her bottom and squeezed her cheeks hard.   Q showing no restraint, ground her pelvis into his hard cock.   He lifted her short skirt and squeezed her thong-clad fanny.   As he kissed her deeply she seemed to climb into his body. Her hands pulled his mouth into hers.   She broke the embrace only to slip her hand between them to stroke and fondle his cock.   It looked like she was going to fuck him right on the dance floor.


The music stopped and they lingered swaying and grinding their hips together until they were embarrassingly the only ones remaining.   Sam then escorted Q not back to the bar but to a dark booth back off the dance floor. He signaled that I should join them, which I did.


It was a new experience for me to observe Q in action as a Cougar. I could see that she was enjoying the role and was quite at ease with it. They were seated quite close, with his left arm draped around her shoulder at the back of the booth. As she leaned into him, she allowed her hand to rest lightly on his leg and began to caress his dick. A sharp intake of his breath told her what she wanted to know. She had found her mark. She increased the pressure and the speed slightly until the bulge she had noticed on the dance floor returned.


I was seated at her left, and she then proceeded to fondle my dick as well with her free hand. Watching her playing with Sam while simultaneously dealing with me was extremely arousing for me. Having not been a part of this type of activity before, it brought me up short. Would she jack us both off at the same time? Would we find a way to “work” her two-to-one? I allowed my mind to consider the possibilities while feeling my hard-on press against my pants.


Sam ordered another round and without asking unbuttoned another button from the top of Q’s dress.   The top was now open below her breasts which although covered would occasionally peak out as she turned her body.   It also allowed both Sam and I to massage her tits, hoisting them gently while softly twisting her pert nipples between our thumbs and index fingers.   The other two hands were simultaneously busy with her thighs and pussy.   Sam’s two thick long fingers were well inside her searching for her G spot. I gently massaged her clit.   Q starred straight ahead. Her eyes in a daze, mouth open and breathing heavily.


Sam broke the spell by suggesting they dance.   On the dance floor, his hands were busy again subtly exposing more of Q’s chest and the back of her thighs. When they returned, I said, “Q you look like your tired and do want to got to bed?”   “I’m not tired but I might……” she replied.   Her incomplete answer to the last part of the question let us both to ‘ fill in the blanks’.   I took her hand and told Sam we were heading back to the hotel.   I was not surprised when he said he would walk back with us.


We took the four-block walk to the hotel in the warm Chicago night.   Q’s gait was a little unsteady.   She claimed she had a little of the “whirllies”, her term for being light headed after drinking.   I steadied her by gripping her right hand while Sam walked on her left.   At each of the spotlights Sam put his big hand on her soft, round ass.   She acknowledged these advances by wiggling her saucy fanny back against his touch.   As we approached the side-by-side hotels, Q whispered in my ear “why don’t we invite him up for a final nightcap.”


Sam agreed but insisted we go to his room. We went up the elevator. The top floor had all the fancy suites for his Marriott.   When he opened the door it was a lavish suite with a tremendous view.  

Just inside the door, Q wasted no time.   With a wink, a smile and a light squeeze of my cock she pivoted in front of Sam and sunk to her knees and yanked his pants to his knees in an instant.   Her tongue flicked the eye of his black monster tasting the salty pre-cum.   Her mouth quickly enveloped his shaft and she began sucking him to his inevitable climax.   As she attempted to swallow his entire shaft she gripped his ass cheeks and pulled his pelvis closer to the back of her wet throat.   Q had complained not two months ago that she gagged when trying to perform fellatio………..   Either through practice, enthusiasm or a combination of both she had clearly put that limitation behind her.


As she continued to devour Sam’s pride, I knelt down and pulled up her dress.   Reaching from behind to her crotch I felt a very wet and open pussy.   I stroked her clit and inserted two fingers deep Q’s pussy.   She was now humping my hand in time with the bobbing of her head.   I put a dad of lube on the index finger of my other had and after gently teasing her puckered asshole, inserted my now slipper finger into Q’s rectum.   She was going nuts but the angles for by hands were impossible to sustain.   I said to Sam, “let’s find a bigger playing field.”


With that he pulled her up by her tits and led her to the big round bed.   I laid on the bed with my legs apart.   Sam put he knees on the edge of the bed and pushed her face into my crotch. She resumed her task with the same great enthusiasm.   She quickly swallowed my smaller cock and massaged my balls with her right hand.   Sam stood at the foot of the bed and buried his stiff penis into Q’s gapping cunt.   The rhythm was established immediately.   Q was quickly groaning loudly and massaging her nipples with her free hand.


Sam suddenly pulled out.   Q pulled off of my cock and looked over her shoulder with a wail and a questioned look on her face.   “Don’t stop,” she said.


Sam gestured that we should reposition ourselves. With Q still wondering what was happening, Sam slid under Q and resumed his lovemaking.   Pumping her from the bottom and feasting on her perfect tits.   Sue was now back with it and was ridding him like a sex-craved cowgirl.   Sam put his arms around her back and pulled her close to his chest.   This was perfect.   Her winking brown-hole presented its self to me.   I wasted no time fulfilling a long held fantasy and sunk my hard aching cock into Q’s ass. She squealed but never missed a stoke sliding up and down on Sam’s black pole.  

We three quickly reestablished a rhythm.   Q was starting to go catatonic.   Both hands now massaged her nipples.   She started to shake from her legs, up through her hips and finally her whole body. She closed her eyes and opened her mouth.   Her entire body stiffened and she moaned loudly every two seconds.   After about 30 seconds and multiple waves of orgasm she collapsed onto Sam’s chest.   We both explode shortly after.   Sam was deep in her cunt and I in her now familiar warm and tight ass.


Exhausted I rolled off and we all quickly fell asleep with Q in the middle spooned up against my chest and pelvis.

I awoke early and went down to the lobby for some coffee. Since I didn’t have a key I left the door propped opened with the bolt.   Both Q and Sam were asleep on opposite sides of the massive bed.   After the glancing at the paper, nibbling on breakfast and downing my second cup of coffee, I loaded up two fresh cups and headed back for the penthouse.  

I was not surprised when I pushed open the door and they were not interested in coffee.   Q was on her knees on the bed.   Her ass was high in the air and her face moaning in the plush pillows.   Sam was slamming her hard from behind.   Her groans and the slow moving of her hips left no doubt that she had recovered from last night’s activities. I took the only opportunity I had.   I replaced the pillow with my pelvis and grabbed her ears.   She swallowed my dick with great enthusiasm.  

Sam signaled for me to toss him the KY, which I did. He put a large dab on Q’s upturned asshole. The cold jelly made her jump and his thumb mad her tense.   Sam said,   “You had so much fun ass fucking her last night I thought I’d try.”   That really got Q’s attention.   She tried to complain but I pulled her mouth farther onto my hard cock and down most of her throat.   Sam’s tool was not only longer than mine it was a lot thicker.   Sam was as gentle as possible and used his thumb to loosen her soon to be filled ass.   When he dislodged his thumb Q stiffened with the anticipation of what was sure to happen next. He slowly slipped his manhood into Q’s well-prepared ass.   I was worried she might bite down on my vulnerable member.   As he slid in she started to pleasure moan again.   When I slipped my leg under her and massaged her swollen clit with my sock clothed toe Q was back to her groan and wiggle.  


Q came several times with violent orgasms before Sam and I were through. After she recovered she gave Sam a big kiss and penned in a date for early spring. Same place different time.



This story is protected by International Copyright Law, by the author, all rights reserved. If found posted anywhere other than with this note attached, it has been posted without my permission.

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