A Gamble Worth Taking Pt. 02

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From the moment I watch the elevator close that morning I couldn’t get Karen and Julie out of my mind. Karen’s mouth and Julie’s tits sent an unbelievable combination of sensations through me. I’d remember them for the rest of my life, if they never happened again.

I returned to my room and cleaned up, taking a longer shower than usual. I put on my “company uniform,” polo and khakis, and drove to my work site with a big smile. Nothing went wrong the entire day. The skies were clear and blue, my meetings went smoothly. I was even told that I would be needed again in a few weeks for a new project. Maybe this was not going to be the last time I’d see Karen and Julie again. They appeared to be regulars in this casino town, at least from what little they had told me the previous night.

I actually wrapped up business before 5, unusual for computer systems work, but this time it was a true blessing. I throbbed faster as I got closer to my hotel, anxious to see my lady friends again. I went up to my room, changed into a sweater and pressed jeans. After I dressed I walked to the elevator. Julie and Karen had a room on the top floor. My heart pounded as the elevator counted the numbers up. I was seriously throbbing now. I looked for the room and discovered that it was a suite. Were Julie and Karen more than just a couple who “played the slots?” I knocked on the door then heard soft footsteps. The door opened and there stood Karen in a silk robe tied tight at the waist. She reached for me with both arms and pulled me in. Then she gave me a wet kiss after she closed the door.

“My sweetie, you’re early,” said Karen. “I wasn’t expecting you for another hour or so. I was just taking a nap when you knocked.” She took my hand and led me into the center of the suite. A bottle was chilling in a bucker atop a dining table. “That’s for later,” she said.

I noticed that the suite had two bedrooms as well as the TV lounge, a small kitchen—this one showed nothing to tell me that Julie and Karen cooked anything here—and the dining table. But two bedrooms?

“Julie went out. She’ll be back in a couple of hours. She took the car and drove to see her daughter. I hope you don’t mind that it’s just us for a little while.” Karen squeezed my hand and led me into one of the bedrooms. Without taking off her robe she laid on the right side of the bed. She made a sweeping motion with her hand, as she had done the night before on the hotel lounge couch, inviting me to join her. “I love to spoon,” she said. “Don’t you?”

Karen turned away from me and curled her legs. I wrapped my arms around her belly and brought her so close that, no doubt, she could hear my heart beat.

“Mmmmmmm, that feels so good, babe. All right if we just cuddle up for a little while?”

I wrapped my feet around her’s to bring her closer still and planted soft kisses on her neck.

“No fair, babe. I’m sensitive there.” She giggled and playfully slapped my thigh. Then she took my left hand and sucked each finger.

I felt slight shivers beneath her silk robe. I put one hand on the knot that bound the robe, the other on her belly to feel more. She snuggled a little closer and we shared a soft kiss.

“Has anyone ever told you how delicious your cum really is?” she asked. “I couldn’t get enough of your taste—and I couldn’t get it out of my mind. I’ve never tasted anyone so delicious in my life.”

I blushed. I’d never been complemented like that before. I’d always thought my cock to be average size. I’d never met a woman who talked about it, even my ex-wife, though she never complained. It’s what you do with everything you have that counts, I’d always thought. For the first few years of our marriage my ex had loved to experiment with different positions and techniques though neither of us went for the extreme.

“No, nobody.” The words came out shaky. “I’m really, really flattered. Maybe you bring out the taste in me.”

Karen laughed. “Not that I’ve had many cocks in my mouth, but they all taste different. Besides, you seem like a really nice guy. Cutie, too. I just had to take a taste. And wow.”

“Thanks.” I rubbed Karen’s soft belly gently and kissed her lips. “I really enjoyed the tasting.”

“Babe, you know Julie’s my darling. It’s been that way for a long time. Our families were neighbors for 25 years, our kids played together. Our husbands, God bless them, were best friends. We took lots of trips together.”

“And you sneaked out to play together?”

Karen playfully slapped my ass. “No. Our husbands knew. Sometimes they’d watch. Sometimes they’d join in. Carl, Julie’s husband, was quite tasty, too. But he’s gone now. So’s Evan, my great love. They passed within three years of each other.”

“You can’t be that old.” Karen’s skin looked too smooth, felt too soft, for her to be a woman in her late 50s.

Karen giggled. “Babe, I’m older than you think. I’m 63. Julie’s 61.”

“You’re kidding, right? You’re gorgeous.”

Karen ran her fingers along my arms. “No, babe. I’m not. Not too old or gorgeous. And illegal bahis there’s no age limit on fun. Don’t you ever forget that.”

I moved from attending to her belly to massaging her breasts. “I promise, I won’t,” I said, and kissed her neck again.

“Mmmmmm,” she murmered, “gentle now, please.”

I kept the kisses soft as she kept purring.

“Julie and I had a business. Real estate. After our kids got older we wanted something to do. Paid for college for all four of them out of our commissions. They graduated debt free.”

“Do you still have the business?”

“Oh, we sold it two years ago at a good price. Now we just play and take trips like this. We’ve even built a house together. We know each other so well; it just made perfect sense.”

And Karen had called me her “sugar daddy” when we first met. I wanted to peel the layers, get to know her better, and I didn’t mean only her robe. She was not only beautiful; she was brilliant.

“You didn’t need my ‘help’ at the casino last night, did you? Not that I would have been much help. I’m happy to go home with the same fifty bucks I came with.”

Karen laughed. “Babe, I was just teasing. I just wager for fun. Julie and I are not ‘high rollers’ or anything like that. But I get quite a thrill when I see all that money falling into my lap.”

“Does it feel heavy, like this?” I kissed her neck and undid the knot of her robe. Then I massaged the valley between her belly and her pussy.

“Mmmmmmmm, nooooo, not like that, babe.” She placed her hand atop mine and guided it around her hip bone and down the valley as my kisses continued along her neck, then her shoulders.”Ohhhhhhhhh, mmmy baby,” she muttered softly as she led my fingers around her moist pussy lips. She turned her head and bit my ear lobe as she pushed two fingers into her wetness. Her legs closed tight as our kisses deepened. She bit my ear lobe once more as my fingers reached her pulsing clit. It felt long and knobby at the end, sort of like i’d imagine a very small cock. Our tongues danced furiously as her body shook to my touch. “Ohhhhh Jay, I’m gonna squirt, she blurted, as she bit my ear lobe once more. Her nectar poured in a rush.

We uncoupled then she turned on her back and spread her legs. Juice was all over her legs and all over the sheets. I licked her pussy from the inside out, then her thighs and belly for good measure. Then we shared her taste in a kiss.

“Blueberry,” I said. “You remind me of blueberries.” I tasted her lips again.

“Thank you, baby. You really know how to make an old girl feel good, feel sexy,” Karen kissed my lips softly. She got up and retied the knot in her robe. “There’s another set of sheets over there,” she said, pointing to a night stand. “Why don’t you change them while I take a shower?”

I did. But I also discovered that she had cum all over my jeans as well. I either needed Karen to go to my room to get me a change in pants, or go back down the elevator with an embarrassed look on my face. Karen closed the bathroom door after her. I could hear the shower come on. But I all I could do was stand or sit around until she came out.

Unfortunately, the suite door opened and Julie came in. She tossed her purse on the dining room table by the bucket and bottle. She was dressed like the real estate broken she’d once been, a black blazer and matching slacks, a teal silk shirt unbuttoned to hint, but not cry out. She had these cute tiny sunglasses perched on her nose. Had she worn jeans or a denim skirt with a loose cotton shirt or pheasant blouse, I would have thought she was a flower child of the Sixties.

“Jay, Hi! How are you?” Her blue-gray eyes lit up and she planted a kiss on my cheek. Then she saw the mess on my jeans. “Oh you poor boy,” she said and giggled. “I can’t leave you alone with Karen for a minute. Forget about an hour.”

Julie offered to go down to my room and bring up another pair of jeans. I quickly accepted and she took my key. She returned as Karen was coming out of the bathroom covered from her shoulders to her ankles in a towel.

“Sorry I’m late, sweets,” Julie said. “But Carla really needed me. Two kids are quite a handful, even if one goes to school.”

“It’s fine,” Karen answered. “Jay and I were getting reacquainted.” She kissed Julie on the lips slightly longer than her last kiss with me while I put on my change of jeans. I put the stained jeans in a plastic laundry bag and left it on the floor of a clothes closet.

Julie smiled. “I see, and were you satisfied?”

“Oh yes.” Karen licked her lips. “Want to freshen up before we go out?”

When I left Julie and Karen that morning I had no idea where they’d want to go besides the casino or their favorite secluded spot. I had hoped that I would fall asleep with one, or both, of them in a more comfortable place than the back of Julie’s SUV.

Julie fluffed out her silky black hair. “There, I’m freshened up. But what’s this?” She looked at bottle still iced in the bucket by her car keys.

“We can have that now, or illegal bahis siteleri later, your choice,” said Karen with a wink.

“I’m late, so let’s have it now.” Julie pulled out the bottle and read the label. “Mmmmm, my favorite red,” she said.

“Glasses in the cabinet,” said Karen, pointing to me to get them, and I did.

Julie poured three classes—they used up half the bottle—and proposed a toast. “To a taste experiment,” she said, as she and Karen lifted their glasses. I lifted mine as their eyes and smiles focused on me. We clicked glasses, but they did not try to finish. So I didn’t.

Julie stepped towards me and leaned over for a kiss. As my lips touched hers and I wrapped an arm around her, she put a hand between my legs and rubbed below the zipper line. “I better get you out of those pants,” she whispered. “Didn’t see another pair in your closet.”

Karen smiled as she watched Julie work her magic. She remained wrapped in the towel and followed Julie and I into the other bedroom. Julie kept the sensual massage going between my legs while Karen picked up the wine bottle. Julie was the first to lie down, me in the middle, Karen on the other side. As Julie got me harder, sculpting my shaft, Karen dabbed wine along its veins. Then she ran wine-stained fingers along my balls. The wine caused them to burn slightly, but I could handle that. As my hardness satisfied her, Karen began licking my shaft while Julie teased the head; her grasp on my balls remained. Then Karen sucked my balls while Julie did the teasing. They brought me to the point of no return before pulling their mouths away. Karen grabbed my hand and put it on my cock. I pumped and pumped cum over her tits.

Karen took a finger tip of cum. “Mmmmmm, Jewels. Takes good with wine, but better without it.”

Julie licked Karen’s nipples. “Mmmm, yes. It lost a little sweetness.”

Julie and Karen kissed me, then Karen returned to the bathroom to clean up my mess.

“Jay, we really enjoyed getting to know you,” said Julie. “Karen’s hardly shy, but we both really like you. We’d like to take you out tonight. Our treat. And we’d like you to stay the night.”

“I’d love that,” I said after I’d dressed. “You two really are special.”

“Maybe, you’ll come and visit us. Did Karen tell you about our house? Knowing how she fancies you, she probably didn’t.”

“Yes, she did. It sounds really nice.”

‘It’s our heaven, Jay. We just need one more thing to make it perfect.” Julie motioned for me to sit by her on the couch in the lounge space. She put her hand on my thigh and rubbed soothingly, though not enough to make me hard again. “I love Karen more than anyone on this earth. It’s like we read each other’s minds. You know what I mean?”

I looked at the bedroom where they had just tasted and drank me. “I think so.”

“Either one of us could get a man. We know that. All sorts of guys prim up for us. But we’ve never met two men we trusted equally.”

“I guess. Karen told me about you and your husbands.”

Julie took my hand. “Yes, they were very special. We loved them dearly. But we have not been able to remake that kind of relationship over the last six years. I guess lightning cannot strike twice. But we talked after you left for work this morning.”


“You seem like a beautiful man, Jay. Smart, tender, respectful, even a little naughty.” She winked.

I blushed and shivered slightly. “Thanks. I really like you and Karen, too.”

“How old are you, Jay? 35? 36?”

“I’m 40,” I said, my voice shaking.

“A little younger than the men Karen or I have dated since we lost our husbands. But we don’t mind, if we have a chance to get to know you better.”

“I’d like to get to know both of you better, too.”

“I’m glad you said ‘both of you’.” As Julie’s fingers ran along my belly I felt that my heart was going to race to explosion. “We thought you might want one over the other.”


“We can tell, the way you look at us, that you can’t decide. But you don’t have to.”

“You mean?”

“Karen and I share almost everything. But we’ve never wanted to share a lover, a ‘boy toy’. Until you.”

I squeezed Julie’s hand tight. “Wow, I have no clue what to say. Just wow. But you were right. I couldn’t decide.”

“You made us feel loved last night, Jay. You’re tasty, but you’re so much more. We didn’t have to have a long, deep conversation to feel that. But we’d like to. Tonight.”

Karen had closed the bedroom door while Julie and I were talking. She opened the door and, like Julie, she was dressed like the successful real estate broken she had been, but with a greater splash of color. Her bright yellow blouse popped under a black blazer and a print skirt that stopped just above her knees.

I smiled when Karen entered the lounge. “I can see how you two sold a lot of houses,” I said.

“Oh we did, baby. We sure did.” Karen embraced Julie and kissed her smack on the lips. She looked her in the eyes. “I love you, darling,” she said, and kissed canlı bahis siteleri her again. Then Julie turned to me. “C’mon, Jay. Join us. Group hug.”

I did, kissing each lady on the cheek and lips. Then we left the hotel, Julie driving. Only this time Karen sat up front.

Julie and Karen seemed to know everyone at the restaurant, a five-star Fusion place not far from the casino, from the host up front to the waiter who took care of us. They took turns cutting their food and sharing morsels with me. The meal felt just right, many delicious flavors, but not too filling. Just like Karen and Julie. Between courses we held hands beneath the table cloth, Karen’s in my left, Julie’s in my right, away from potentially prying eyes. They described the home that they had built together as well as “war stories” from the real estate business. I shared my tales about my “more interesting” clients. It was nice that we could all laugh at ourselves as well as each other. We’d each made our mistakes in building businesses.

“Why’d you pick software, Jay?” Karen asked after she finished her dinner.

“Coding’s a lot like writing, or music,” I said. “It’s a chance to compose something on your own, even if you have to share credit. Like a musician needs a band.”

“Hummm, interesting,” said Julie. “You like music. I don’t like to dance, but I love to play R&B or classical through the porch speakers at home. On the right night it really gets me in the mood.” She squeezed my knee cap and gently rubbed my thigh.

“You know, Jay, when you come over, there’s a porch swing out back,” Karen said, as her hand coaxed a throbbing. “It faces a lake, and it’s roomy enough to share.”

Karen and Julie tipped our server generously then we went to the casino where Karen showed me her lucky slot machine. Pulling the lever brought me nothing but Karen really had a golden touch. She turned ten dollars into fifty within an hour before we moved on to the roulette tables. Then we moved on to play roulette. Julie bought $500 worth of chips, more than I’d ever spent in a casino in my whole life. We actually left a hundred dollars ahead.

We returned to our hotel, again Julie and Karen sat up front and looked more subdued than I’d seen them since we first met. They held hands for a moment when we had to stop at a light, but that was the only hint of romance I saw on the brief journey. But when we got into the elevator, once again alone, we exchanged kisses as we cuddled together in the corner.

There was no one at the waiting for the elevator door when it finally opened. So we held hands together as we walked anxiously to Karen and Julie’s suite. Julie slid the key in and opened the door while Karen playfully smacked my ass.

“Babe, you know what I want for dessert,” Karen whispered. “Salted caramel.” She licked her lips after the door closed behind us. There was still half a bottle of wine left. But Karen didn’t want it. She quickly coaxed my hardness and led me to her bed as Julie rubbed my ass, teasingly pressing her thumb between the cheeks.

I lifted my sweater and t-shirt over my shoulders while Karen and Julie undid my jeans. Karen undressed while I unbuttoned Julie’s blouse then sucked her tits. But once Karen was totally nude, she stopped me and took over. I laid down in the center of the bed and watched Karen take her lover, while I played with myself. By the time Karen had totally undressed Julie I was ready to feed them my cum.

“Chestnut praline,” said Julie. “Yummmmm.”

Karen grinned. “Different tastes taste different to different people,” she said. “But we both find you so incredibly delicious. We can’t get enough of you.”

Karen and Julie were used to three in a bed, even four. I was a novice, but they didn’t make me feel uncomfortable, even though they had been lovers for so long and knew each other’s bodies so well. The way they kissed and tasted me, I’d never felt so wanted. Boy toy or not, Julie was right. I could not decide between the two of them.

It was a month before I could make firm plans to hook up with Karen and Julie though we Skyped morning and evening, sometimes both, every day until I could get time off for my visit. They were more fortunate than I. They had each other while I had to resign myself to my online and off-line visions. I’d never been one to play with myself before I met them. But even from three hours from home, I couldn’t resist. The way they enjoyed each other, as I watched through my Internet TV set-up, swore me off porn for the rest of my life. And when Julie played her music, I beat to the rhythm for their pleasure.

“We can’t wait to see you, babe,” said Karen. Her tits filled my screen. “We really, I mean really, miss you.”

“All looks good. I’ll leave around four tomorrow and should be there by dinner.”

Karen and Julie embraced and kissed deep, sending my cock into a frenzy once more. Then they turned and blew me kisses.”

“See you tomorrow, sweets,” said Julie. Then they faded from view.

I laid on my back in bed and rubbed the evening wood that my lady friends had created. I’d shot fountains towards the ceiling every night since I’d come home. I was scheduled to return to that casino town in three weeks, but I couldn’t wait that long to see Karen and Julie again.

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