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“Hey, sexy, how ya doin’?” Karen, a sultry brunette, asked Tommy as he walked by her poolside chaise lounge.
Tommy was breathing heavily from his session in the weight room; his sculpted chest was heaving and glistening with sweat.
What a waste, she thought as she gazed at his hard, flat belly, six-pack abs, and ruggedly handsome face.
Men like Tommy were few and far between, and for the hundredth time, she cursed her bad luck that he is gay. Her fantasies of being held in his strong arms while he thrust his manhood in-and-out of her wet pussy would go unfulfilled.
“Hey, Doc, you getting any?” he asked Karen, flashing her a wide smile and a glimpse of his perfect, white teeth.
“Around here?” she said with raised eyebrows. “I’d have better luck in a convent!”
“Yeah, I know what you mean…it’s been awhile for me, too,” he commiserated.
“Well, if you hadn’t turned Billy into such a pansy-ass, you’d probably still be interested in him,” she said.
Tommy laughed then said, “Yeah, I may have gone a little over-the-top with him.”
“A LITTLE, over-the-top?” she said chuckling. “You had him parading thru the pool area here, in front of everyone, wearing nothing but a white jockstrap and making him swing his hips like a girl—I gotta admit, it was entertaining, and he did have a nice, shapely butt!”
“Yeah, I really miss pounding that sweet ass of his…” he said with a wide smile.
“Too-much-information, Tommy!” smiled the beautiful woman.
“I don’t know what it is, Karen…we’re both in our mid-thirties now—is it possible we’re looking for something more serious than just getting our rocks off?” he asked.
“Bite your tongue!” she said and broke into laughter. “Well…I have to admit, remember Jenny the cute blonde who lived next to me? [he nodded]…I liked her—I wanted to get close with her…I mean, you know I swing both ways, Tommy, and she got to me—I actually pictured myself in a ‘relationship’ with her, but…you know…she didn’t believe in the girl-on-girl thing….”
“Too bad, she was hot…I guess she never heard about our complexes reputation…what about the new kid who moved into her place? He’s a little young, but he’s damn pretty! Have you tried to seduce him yet?”
Karen smiled and said in a half-whisper, “Yes, I want to talk to you about him—he may be more your style than mine.”
“Oh really?” replied Tommy, his blue-eyes lighting up.
“Yeah, not here though—all these faggots and dykes are too nosy—I’ve heard them talking about him—they all want a piece of the ‘fresh meat’—c’mon, let’s go to my place!” she said then stood and led Tommy into the apartment building.
Tommy sat at the kitchen table and watched Karen retrieve two bottles of water from the frig. She’s got a fine, fine body, he thought, and she’s still beautiful, even at her age…it’s amazing she’s alone right now…I wonder if her ass is virgin?
Karen spoke: “The pretty boy’s name is John and he’s from up north—some state like Wisconsin or Minnesota—one of those places…he’s been here a month—he makes minimum wage at a liquor store—outside of me, he hasn’t made any friends, and it seems to me his only hobbies are drinking and shooting pool in the rec room…he’s pretty much a loner, and…I have a strong suspicion he’s gay…he’s a closet queen, Tommy!”
“The boy’s as cute as they come—I’ve had my eyes on him—he DOES get my dick hard!” chuckled Tommy.
“Again, Tommy—TMI!” she said with a smile, immediately picturing what Tommy’s hard dick must look like.
“He doesn’t act like a twink, and he’s not overly effeminate—what makes you think he’s gay?” asked Tommy.
“It’s more of hunch than anything,” she replied. “You’re right—I went after him once we got to know each other at the pool…the kid is bright and funny—he’s interesting to talk with for a twenty-one-year old…a little naïve, but very eager to please—maybe too eager—he does have a strong submissive side.”
“Ohhh, just the way I like ’em!” said Tommy.
“I know, that’s why I thought he might be perfect for you!” she said.
“Yeah, but that doesn’t make him gay—maybe he wants a dominant woman—is there anything else to go on here, Doc?” he asked.
“Well, a couple nights ago he was at my place—we were on the sofa fooling around…he’s a helluva kisser—very good—made me hot and wet—“
“Now who’s giving too-much-information?” chuckled Tommy.
“Yes, anyway, he wasn’t moving along as quickly as I wanted—he’s shy, and I doubt he has much experience with girls, so I decided it was up to me to be the aggressor…I’m caressing his chest and thighs and I notice a very small bulge in his jeans…well, he IS a small-boned boy with small hands and feet so I already figured his dick would be small, too—I didn’t care—I was so horny, if I couldn’t get-off on his cock, I’d have him use his hands and mouth!”
Tommy smiled and nodded his head in approval.
“Well, I get his shirt off and WOW—he has the most amazing nipples—I’ve Topkapı Escort never seen such long and thick nipples on a guy before—and I swear—his aureola’s are puffed-out, too—he could actually fit into 32-A brassiere! Anyway, his tits have me out of my mind and I start peeling off my clothes…his eyes get as wide as saucers when he sees me in my underwear, and when I sit on his lap he can’t keep his hands off me—well, not me, but my bra and panties!”
“Well, you do wear sexy underwear, Doc,” said Tommy.
“Yes, I know, but he was more interested in my bra and panties than what was beneath them—he never attempted to strip me—he was perfectly happy running his hands over the material—especially the panties—he LOVED stroking my panties…anyway, I saw how much the material turned him on so I thought I’d play along with him…I pressed my hand on the bulge in his jeans, leaned in close, exhaled hot air in his ear and whispered, ‘Would you like to wear my panties, Sweetie?’…and HOLY CRAP—his body starts shaking and bucking and he begins shooting his load inside his jeans—I mean, this kid is a definite panty-freak!”
“Sure sounds like he is, Doc, but, you’re the psychologist, you know having a panty-fetish doesn’t make him gay…I don’t know a single gay man who is into cross-dressing, oh, a guy may force his boy to wear women’s underwear, but it’s more of an issue of control…”
“Oh, I understand all that…what about Pauly—remember your boy, Pauley?” asked Karen.
“Doc, I made him wear panties because it embarrassed the hell out of him—not because he liked it!” explained Tommy.
Karen smiled then laughed. “He REALLY hated it when you brought him to our get-togethers wearing only panties—I’ve never seen anyone whose face could stay beet-red for three-hours!”
“Yes, there’s a huge difference between loving men and loving panties!” laughed Tommy.
Karen smiled, nodded her head, then asked, “How long have we known each other, Tommy?”
He answered, “Oh, what, seven-eight years?”
“Exactly two-months from today it will be ten-years! It will be the tenth anniversary of when I first laid eyes on you—the tenth anniversary of the first night I fantasized about you when I masturbated!” she said.
Tommy laughed and said, “You were wearing a pink bikini at the pool and when I walked by and saw your face and body, I had to ask myself ‘Tommy, are you absolutely, a hundred-percent positive you’re queer’?”
Both of their faces lit up with laughter.
“Tommy, seriously…” she said after regaining her composure, “…I didn’t come to my conclusion after one night with Johnny…”
“I thought his name is ‘John’?” he asked.
“It is—he even corrected me a couple times when I called him ‘Johnny’—anyway, ‘Johnny’ was so embarrassed by shooting in his pants he ran for the door and disappeared—which pissed me off like you wouldn’t believe—he gets-off and leaves me with a wet pussy!”
“Yeah, that isn’t right,” he agreed.
“So the next day I go to the liquor store where he works…his face is red—he can’t look me in the eyes…but I sweet-talk him…make him feel better about himself…then tell him ‘I’ll expect you at six for dinner tonight!’…he mumbled and stuttered and looked down and I simply said ‘Six o’clock, Johnny—okay?’…he blushed and says ‘Okay’….”
“Ohhhh, sounds like he takes orders well,” said Tommy.
“Yes, he does…anyway, I throw a small pot roast in the crockpot and think about a plan…do I want revenge? Do I want to humiliate the kid for leaving me high-and-wet? Or, do I want to be a teacher, and show the kid how to make love to a woman?”
“Doc, you’re not a mean person…” he said.
“You’re right, thank you. I decided to do the right thing and become a mentor to the boy—besides, I was still horny-as-hell!” said Karen with a wicked smile. “If his tiny dick couldn’t do the trick—I’d teach the boy the fine art of eating cunt!”
“Heh-heh—good one, girl…how did it work out for you?” he asked.
“Well, I plied him with the two bottles of wine I’d bought from him earlier and we had a pleasant dinner…like I said, the boy is intelligent and comes up with some humorous lines…afterwards, I excuse myself to go to the bathroom, and at the last second, I decided to experiment—I tell him, ‘While I’m gone, rinse the plates, glasses and silverware and put them in the dishwasher’—the only thing he says is ‘Okay, sure’—oh yes, the boy is definitely submissive!”
“You told him to do the dishes and he just obediently said ‘Yes’?” asked Tommy.
Karen laughed and replied, “The boy is pure gold—he’s going to make YOU very happy!”
“Wait a minute,” Tommy protested with a laugh,”…being submissive and obedient doesn’t automatically make him gay!”
“No-no…let me finish,” said Karen. “So I go to the bedroom and put on my red babydoll and my sheerest red panties…I’m about to go back to him when I think ‘Whoa, girl—you don’t want to scare him—he might run away again!’…so Topkapı Escort Bayan I call out from the bedroom ‘Johnny, I need your help’…and sure enough, within three-seconds he was standing in front of me—you should have seen the look in his eyes when he saw my outfit—priceless!”
Still smiling, Tommy said, “I never knew you were so devious.”
Karen chuckled and said, “Oh, it gets better…”
Tommy was seeing a side of Karen he’d never known. He enjoyed hearing her story.
She continued: “Well, I make fast work of getting him naked, and yes, I was right—his dick is tiny, and not only that—it wasn’t even hard…we lay on the bed and I’m kissing and fondling him trying to get his dick to stand-up…so I take his hands and place one on my breasts and one on my ass—his dick goes BOING! and he moans ‘Oh God’…the boy got excited only when he felt the material of my nightie and panties!”
“Are you sure?” asked Tommy.
“Oh yes…anyway, I take his prick in my hand, and, sure enough, I figured it to be about three-inches, and it wasn’t very thick, either…I knew it wouldn’t do anything for me so I decided I’d have him eat my cunt—I also knew from kissing him his tongue was small, too, but it would at least be able to lap at my clit!”
“Wow, I never knew what a dirty woman you are, Doc—I like it!” said Tommy with a grin.
“Heh-heh-heh…Tommy, you and I have been around long enough to know what to do with shy and submissive boys…anyway, I peel off my panties so he’s not caressing them any longer, and, you guessed it—his dick goes limp again…so I climb on top of him…I’m facing his dick…and then I sit on his face and grind my pussy on his mouth…right away I feel his lips and tongue working on me—like I said, he’s a bright boy—he knew what was expected of him!”
“Hmmm, I like it—I have to admit, Doc, you got me picturing myself mounting his face and fucking those pouty lips of his—he’s such a pretty boy, I’d love to make him gag on my cock—I’d love to see the expression in his eyes when I make him take my entire scrotum in his mouth!” said Tommy.
She smiled and said, “I just KNEW you were interested in him! I had a hunch you’d love turning him out and making him your bitch!”
“Of course I would, girl, but you haven’t convinced me he’s queer—only that he’s a shy and obedient boy with a serious panty fetish…you know, maybe I shouldn’t care whether he’s gay or not…after a week with me, his whole world would be turned upside down anyway….”
“That’s the spirit—now you sound like the Tommy I’ve known and loved for years!” she chuckled.
“So how was the boy? Was he able to bring you off?” asked Tommy.
“He IS a peculiar boy…I mean, he kept his lips and tongue moving on the right spots, some girl must have taught him what to do, but I could tell his heart was NOT into it—he continually made retching noises and his dick stayed limp…so I rubbed my panties on his penis and—OH MY GOD—it becomes as hard as a little steel pole, and then it pisses me off that it’s my underwear that makes him hard and NOT my pussy!’
“You know, Doc, I’m beginning to see a pattern here, you might be right about this boy,” he said.
“Tommy, you could turn him into anything you want—a leather or jockstrap wearing twink, or you could keep him in women’s underwear and make him a sissy-boy…I really believe he is ready to be turned-out, but he just doesn’t know it yet!”
“I think I’m starting to agree with you…the boy has a problem with denial…he needs a strong man to give him what he’s too afraid to ask for….”
“Just wait—it gets even better…so I’m grinding my pussy on his mouth and stroking his dick with the panties…I take his scrotum in one hand so I can determine when he’s about to cum…and sure enough, I feel his hamster-balls rising so I gently push them back down—you should have heard him whimper and groan—you would have thought the world was coming to an end…you may want to consider having him wear a scrotum strap while you’re training him!”
“Girl, I make ALL my boys cinch their balls!” answered Tommy.
“Anyway, I press my pussy even tighter to his mouth and now his lips and tongue begin working faster and harder…I keep saying, ‘Good boy—good boy’ and I meant it—his little tongue was doing a great job…I’m seconds from cumming so I stroke his cock with the panties as fast as I could…just as my orgasm begins, I feel his balls rise, and again, I push them down and deny his climax…I was screaming so loud all I could hear was him mumbling incoherently…so anyway, when I’m finished, I smear my pussy-juice all over his face and go back to stroking his cock with the panties…I shift my hips and say to him ‘Lick my asshole, boy’ and would you believe it—he not only didn’t protest, he never even hesitated!”
“I don’t know, Doc, it sounds like you might want to keep him and train him yourself,” remarked Tommy.
“Well, if it wasn’t for his needle-dick, I probably would,” she said. “No, I need Escort Topkapı a man-sized cock inside me—not a little boy.”
“Heh-heh—did you ever let him climax?” asked Tommy.
“Yeah, after I had him pushing his tongue in-and-out of my asshole I told him if he ate my cunt again I’d let him cum…oh my, he was such an eager and docile little boy, I think my pussy actually squirted when I came…and you should have seen the load he shot into the panties, my goodness, he positively soaked them…of course, I made him take the wet panties in his mouth and clean them…he whimpered, but he obeyed me.”
“Well, I’m not convinced he’s gay…he sounds like he’d make a better play-thing for a woman than a man!” said Tommy.
“Well, how about you and I make a little wager to make it interesting…” she said with a cat-like grin. “You say he isn’t gay, but I’ll bet he is—does that work for you?”
“Heh-heh—what are the stakes? What’s in it for you if you win?” he asked.
“Well, Sweetie,” she said, “…something I’ve wanted for almost ten-years now—your cock—if I win, I want to slide up-and-down on your beautiful cock…”
“Karen, I’m gay—the last time I was with a woman I couldn’t even get it up…you might win the bet but you wouldn’t be able to collect your winnings!” Tommy said bluntly. He briefly wondered if she was playing one of her psychologist games.
“Heh-heh-heh…my dear, we’ll simply have Johnny be your ‘fluffer’—he’ll keep you hard for my pussy…in fact, once you cum inside me, we’ll have Johnny eat my cream-pie, too…wouldn’t you like to see that, Tommy?”
“Yes, I think I would…so, how do we find out the truth about him? How am I going to seduce him without scaring him away?” asked Tommy.
“Not so fast, handsome…there’s one more thing I want,” cautioned Karen.
“And that is?” asked Tommy.
“I want to be the one who breaks his cherry—I want the little sissy-boy wearing my panties while I fuck his virgin hole with my strap-on!” said Karen.
Tommy laughed and said, “Now that’s the Karen I’ve known and loved all these years! But like I said, how am I going to seduce him without scaring him away?”
Well,” giggled Karen. “I already KNOW the truth—the boy is as queer as a three-dollar bill, Tommy.”
“Get outta here—what do you mean?” he asked.
“Tommy, he and I sit side-by-side at the pool…those big-framed sunglasses he wears might hide his eyes from everyone in front of him, but I can clearly see his eyes from the side and what he is looking at…and Sweetie, when you stop by and talk to me, he can’t keep his eyes off your crotch…and when you go into the weight room, and I try to make conversation with him, he gets distracted, and I can see his eyes staring at you thru the glass…you know what? He gets a boner whenever he looks at you—that is no lie, Tommy!”
“Why didn’t you say that earlier instead of all the panty-talk?” asked Tommy, somewhat agitated.
“If I’d said that you wouldn’t have made the bet with me!” she exclaimed.
Tommy softened and smiled. “You really are a devious woman…I assume you already have a plan to make this happen?”
“Have you ever shot pool with him in the rec room?” asked Karen.
“No, not yet,” he answered.
“Okay…does he know how good you are?” she asked.
“I don’t know—I doubt it—he and I don’t hang out with the same people,” said Tommy.
“The only thing he comes close to bragging about is his pool game…I think it’s the only thing in his life that gives him a measure of pride…you can use his pool game, his drinking AND his panty fetish to soften him up…he once told me when he shoots pool, and has between three and five drinks—he almost never misses a shot…but when he goes over that number, his game goes to hell.”
“Good Lord, how much does this kid drink?” asked Tommy.
“Not sure, but you have to understand he drinks to sublimate his sex life,” she said.
“Meaning what, doctor?” asked Tommy.
She chuckled and said, “He uses booze to curb his sexual urges—he gets drunk to suppress his ‘naughty’ attraction to men!”
“His parents must have done a real number on his head, huh?” said Tommy.
“Well, between them and his religious upbringing, and my guess, extremely homophobic friends and culture…yes, I’m positive he has demons in his mind shouting—pussy-GOOD—penis-BAD, but his own urges and desires tell him it’s the other way around…he’s a very conflicted and confused boy.”
“He seems pretty normal to me,” said Tommy. “If what you’re saying is true, he has a damn good defense—how am I supposed to break thru to him?”
“By playing a damn good offense! Remember your boy ‘Timmy’ from a few years ago?” asked Karen.
Timmy’s name brought a smile to his face. “Yeah, he was cute, too…but I had to use blackmail to get him into bed,” he said.
“I see a lot of similarities between Timmy and Johnny,” she said.
“How so?” he asked.
“Timmy was in deep denial concerning his sexuality, too—he was deathly afraid to admit his attraction to men…even after you had him move in with you he claimed the only reason he shared your bed was because you threatened to tell his parents and his boss at work he was queer…it took months to turn him out before he would finally admit his love for men.”
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