Ivanka's Secret Affair with a Powerful Businessman

By the time Ivanka and I had sexual trysts, we had known each other for years, we had recently begun to explore each other on a personal level. Our first tryst is at a hotel in Chicago, in an upper floor room with moonlight streaming in the window. The room is large and tastefully furnished, and with a childlike abandonment I 'd never seen in her, she kicks her shoes across the room and belly-flops into the middle of the king-sized bed. " Oh My God, If my dad knew I was with you." came the muffled comment " It's actually exciting." I grin as I step out of my shoes sitting down beside her. She rolls to her side to face me. " I've always loved a dare and a big playground." She shifts closer to me asking, " What do you want right now?" " I want to see all of you."

She stood beside the bed dropping her jeans to the floor then she pulls the t-shirt over her head, I'm standing in front of her. I unclasp her bra sliding it off her shoulders. The kiss is deep, intense, and the warmth of my hands on her bare breasts - teasing and pinching her nipples - sends shivers of pleasure through her body and tingles through her pussy. She feels familiar dampness in her panties. Still locked in the kiss, she tugs at my shirt, wanting to feel my bare skin against hers. I broke away long enough to give her what she desires, and then bent to kiss her again, feeling her nipples stiff against my bare chest as I cup her ass in my hands pulling her body to me. Ivanka feels my hard cock against her belly grinding herself against me. My fingers slip inside her panties. " Wait," she whispers, as she eases my zipper down. Then, she slowly kneels at my feet, taking my cock in her mouth, looking up into my eyes. I groan my pleasure as she licks and sucks.

I twine my fingers in her hair, begin to fuck her mouth. I'm definitely not her type. She firmly believes that everyone has a "type" the one that makes you look twice, and wonder. Her type is a man with dark hair and clean shaven, not a man with gray hair and twice her age. The feeling of my day-old stubble on her breasts and between her thighs gives her a rush like the ones she got with younger men. Taller is better, but height isn't the ultimate attraction for her. The man had to carry himself with confidence. Tentative men - and women, for that matter - just left her cold. We met for the first time in our respective jobs, on opposite sides of the table. To her delight, I'm not afraid to go on the attack to win a point. She knows why I did it - to show her and her dad I could match their own level of confidence, and raise the stakes. My gaze never faltered. Nor did hers. She is intrigued.

Over the years, we had increasing contact as we worked on common issues, and developed a mutual respect, even when we disagreed. After all, it is a job, and we are professionals. I'm always professional, respectful and courteous. I was at first amused by the passion she had for her side of the work, but later began to expect nothing less. There were even times when I encouraged her. Always off the record. From the moment she tastes the warmth of my hard cock, the satiny head grazing her lips as she opens her mouth to take me in, she enters a world of erotic bliss. She took me as deeply into her mouth as she can, and then backs off, teasing me with her tongue as her hand continues to stroke my shaft. When she stole a glance upward, she sees my eyes are closed. My hand grips her hair more tightly and I fuck my cock faster into her hot mouth. She feels my balls tighten, and knew I was close. My question is a throaty groan. " Do you want me to cum?" " Um hmm," she moans.

She swallows almost as fast as the warm spurts of cum erupts. I moan aloud now, and with each one, she feels her swollen clit throbbing, slick with her own juices. My hand lefts her hair as I sat down on the edge of the bed. She stood, kissing my neck and sucking my nipples as she moves downward to take my cock in her mouth again. " Wait," I whisper. " I want to taste you now." After a few years, our jobs allowed them to enter into a less adversarial, and more collaborative relationship. Some of those collaborations were, by mutual agreement, off the record. All of them were successful. So were the after-hours meetings. They each felt freer to express themselves honestly with the understanding that nothing would be repeated. He discovered another side of her – one that wasn't as intense as her public persona. Her father Donald dominated and controlled her in business dealings. All of our after hour meetings were kept very discrete and out of the public eye. When Ivanka started her businesses seperate from her father's businesses, her father refused to give her the resources for the businesses. Ivanka called me asking if I would provide her the resources. I immediately had my lawyers draw up contracts, my bankers to set up accounts with unlimited funds available, and my other business associates and contacts were made available to her.

Through the years, she has fleetingly wondered what I was like outside of work. Now, those thoughts turn to wondering what I'm like in bed. One night, we talked about it. About how – or whether – a sexual relationship can work. Both of us are concerned about our work interfering with our fun. I'm more cautious than she is. As far as she is concerned, anything personal between them would have to be separate from our jobs. She knew she could do that, because she had before. Her professional life might be very public, but her personal life is off the record. She lay back on the bed as I explore her with my hands, lips and teeth, listening for the quickening of breath that tells me I had hit a sweet spot. I slide her panties down tossing them on the floor. I didn't say a word as I finger her pussy. She is already so wet. I feel the physical rush of realization - sucking my cock has turned her on. Stroking her clit with my thumb, I look up at her face. Her eyes are closed. She arches her back slightly, forcing my fingers deeper into her pussy as she caresses her breasts, fingers tweaking her nipples.

" Oh, yes. Harder, baby." I rub her clit harder, and I'm rewarded with a gasp of pleasure as her eyes fly open. " Oh God, Yes. Yes." I bend down inhaling her scent. Still fucking her with my fingers, I suck her swollen clit into my mouth, and my tongue teases her with rapid flicks. As I feel her hand cradle my head, I knew she is close. My cock hardens with her moans. She feels her pussy tightening on my fingers. " Oh now, baby...now!" Her world explodes in a rush of sensation, wave after incredible wave radiating from her pussy and resonating deep inside her. She moans louder, grabbing my shoulders, wordlessly pulling me up toward her.
Instinctively, I know what she wants. She wants to feel my cock inside her while her orgasm still ripples through her body.
As I slam into her velvet depth with hard, steady strokes, she whispers into my mouth. " Baby, fuck me harder and deeper."
I thrust deeper into her tight heat and her hips rise to meet me with each stroke. She grabs my ass with both hands, urging me on. She tightens her pussy around my shaft arching her back, hair splayed over the pillow beneath her.

I begin cumming as soon as I feel the walls of her pussy milking my cock. My throaty moans mingled with her cries of delight as I continue to thrust into her as long as I can before I stop, pulling her close to me as I roll onto my side with my cock still twitching, buried inside her. Afterword, she nestles next to me, listening to my heartbeat as it gradually slows. Together, we shifted slightly until we found a comfortable position. Later I puffed happily on my cigar as I watched Ivanka undressing for me again. When she is down to her pale yellow bra and matching panties I'm thinking of the shock her fiance would have knowing his future wife is sharing her delicate charms and beautiful body with me. " You're beautiful, Ivanka," I mutter, as I took long drags on the cigar. " A very lovely fiancee. How long have you been engaged?" " Just six months, John," She replied. " I fantasied for years about you. For the last two weeks I planned this tryst with you." She stammered. " So you have Ivanka" I chuckled. " Now you are back again after our earlier quickie." I enjoyed taunting her, loving her obvious embarrassment and guilt. " I'm anxious to see you without those panties. Ivanka is about to bare her charms to me again. What would your loving fiance say if he could see you now!"

I enjoyed embarrassing beautiful young women and wives in this way. With her eyes glued to my bulging cock again, I slowly un zipped my fly. I watched her eyes widen and heard her gasp when my long thick cock came into view. My cock twitching knowing it will soon be fucking her again. Ivanka was grateful knowing I did use a condom the first time and that I was using one this time. Ivanka could not afford to get impregnated by me, so close to her wedding. I would prepare a surprise for her again. I had made sure the condoms are deliberately punctured with holes large enough to let my thick seed to ooze into her unprotected womb. I took her in my arms. She smells so sweet, her body so soft and sexy. I embraced her curvy body, as I cup her tight ass cheeks and caressed her soft pink nipples. Ivanka is trembling as she submits herself to me again, knowing that her fiance would be devastated. While I kiss her soft lips, I fingered her soft pink nipples, which soon begin hardening and growing. Ivanka kept her eyes closed but can't suppress her moans from the stimulation. As I kiss her deeply, my cock is painfully hard, hot and heavy. I grasp her hand placing it on my throbbing cock, letting her know I'm hard.

In no time the lacy panties drop to her ankles. In another few moments, Ivanka is lying naked on the bed with me anxious to mount her again. All things had to come to a halt when Ivanka kept a grip on my throbbing cock. " Please John, you promised!"
I reluctantly stopped reaching over to get my condom. I see her sigh with relief as I rolled the white condom, with a red tip, over my oozing cock head. I wanted to laugh knowing that the punctured condom would not prevent my seed from fertilizing her womb. I guided my cock against her moist pussy lips, pushing my rubber coated cock inside her hot tight pussy sleeve. I draw my mouth away from hers in a low voice, I ask, " How long is it made love to your fiance, Ivanka?"

" It's been about two weeks, Mister Malone. My fiance's been too busy with his job" she replied. I chuckle as it is rather bizarre and very stimulating to have this attractive young woman calling me " Mister," with my thick cock buried deep in her womb. "How many times has your fiance done this to you since the engagement, Ms. Trump?" I chuckle adding emphasis to Ms., for this newly engaged woman, and giving a twitch of my monster cock. She blushes in embarrassment wondering how she willingly can take my cock and yet talk about lovemaking with her fiance so soon after her engagement. " Only once ... just once," she mumbles. " He has been worried about his new job that he's been too stressed." I almost laughed outright the young fool of a fiance. Less than a month since their engagement and Ivanka is being deprived of sex. I will see to it that she will look forward to more " business" trips in the near future. It is little wonder she is so anxious and willing to submit to me. Even if that lover is despised by her father in business and personally.

I ease myself over on top of her, driving my cock hard and as deep as possible, right into her womb. I watch her face contort from the pain caused by my monstrous cock but also the pleasure it brought her. This innocent woman is going to be taught what a real fucking is all about. I feel her tight pussy gripping and clamping to my cock like a glove. Ivanka moans and it is obvious she is loving it. I got my feet to the bed frame to use the bed itself for more leverage. I want to feed into her every inch of my cock. To make sure I give her more than her fiance, I rear back slamming forward with all my might. Over and over I withdraw and slam back inside her. I see Ivanka's eyes glaze with ecstasy as orgasm after orgasm overtake her. There is nothing more enjoyable, more lustful for me than to watch a beautiful woman's face contort in passion. To see her reactions to this second fucking with me other than her fiance, and less than a month since she has returned from her engagement party!

Throughout the night, the hotel bed continues to creak under the constant stress. No sleep will be obtained on this night. I'm glad that I had brought an entire box of my specially prepared rubbers. When I tried to enter Ivanka without the damn rubber, she put up a fight. I chuckled when she said " Please Mr. Malone, you must put a condom on. I must be true to my fiance!" As if she is being faithful by letting me fuck her with a rubber on. This young bitch had some logic in thinking she isn't being unfaithful. I only smiled each time as I twitched my oozing cock to force the thick cum into the rubber tip, forcing it through the porous holes. I had a suspicion that Ivanka would have stayed another night with me in Chicago. But my plane was set ahead of time and I had other commitments. It is an added bonus for me to find Ivanka's young fiance waiting for her at the airport when we got back to New York.

I watch the young couple kissing and embracing, the fiance giving a passionate kiss on his girlfriend's sweet creamy lips. I smile wondering if the unsuspecting fiance would kiss his beautiful girlfriend so passionately, or at all, if he knew that just before the plane landed at the airport, his lovely girlfriend was on her knees being fed a pint of creamy hot cum. My 9 inch long cock had erupted deep down her throat and I pulled out to paint her soft lips with glossy cream. I had ordered her to lick her lips and to kiss her fiance when she greeted him. The young fiance would be shocked if he felt up his lovely woman, what should be his private possession was coated by another man's potent cream. I watched them lightly kissing as they headed to the parking lot. I smiled looking at the young couple, only recently back from their engagement party, yet the young woman had already sampled another man's prick. A cock that is twice her fiance's size in length and thickness. Was the beautiful young woman on the pill? I smile as it is quite doubtful, especially with the fuss she put up insisting I wear a raincoat each time. Well, if she wasn't, she is likely to find herself with a puffy belly in a month or so. Lucky I had poked holes in each one ahead of time. I loved to see the young beauty's tummy swell with my offspring. I had bred her well. I'd enjoy seeing her reaction when she discovered she was pregnant