How I Helped Jeff

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"Jeff is a cold fish, and has been for the last few years, at least toward me. Plus I have fallen in love with someone else."

I instinctively raised my eyebrows. I was reluctant to ask "Who?" but my curiosity got the best of me so I did ask.

Rosalind got a diabolical grin on her face, stood up, removed her sundress -- which was the only article of clothing that she had on besides three inch heels -- and walked over to me and sat on my lap. As she stroked my face she said "Why you, silly!"

My mind was not processing the situation -- apparently my dick was because it hurt like a son-of-a-bitch it had inflated so quickly. "But...but...uh..." I stammered until she put me out of my misery with a passionate kiss on my lips. When she came up for air she continued "My question is do I have a chance for a relationship with you?"

There are probably some hetero men somewhere that could resist Rosalind under those circumstances. However, considering that I hadn't been laid in more than a year, that any sighted hetero guy would consider her at least a 9.9 on a 10 point scale, and that I suddenly realized that even before her surgery I had developed feelings for her, I was not that man. I didn't even think about my dear empathetic friend Jeff as I kissed her with the passion of a love song.

It wasn't long after I pressed my lips into hers that I was licking, fingering, and sucking on her delectable pussy and clitoris as she lay spread eagle on my couch.

After her first orgasm my pants ended up around my ankles and I had ripped my shirt off my impossibly hard cock was like a heat-seeking missile going after her honeypot.

My first penetration was so sweet that I barely had a chance to pull partially out and for a second thrust when I came like Mt. Vesuvius. Obviously she couldn't have come from that quick penetration but she squeezed me to her and kept mumbling "You feel so good!"

Once my euphoria had passed I withdrew, quickly finished taking my pants, boxers, and socks off, then lifted Rosalind up and carried her into my bedroom

I ate her again -- the only second time in my life I had eaten a pussy I had just fucked -- until she had another orgasm. By then my cock was recharged and this time I took my time. Our slow, leisurely fuck with her legs wrapped around my waist while I sucked and licked the nipples on her prodigious tits was utterly delicious. As we both approached a climax, however, it turned from leisurely to frantic as I pistoned in and out at 60 mph while she squeezed and released her pc muscles. This time our mutual orgasms seemed powerful enough to blow the roof off of my house (although fortunately that did not happen).

I really have no idea how long it was before we both were physically disengaged and fully cognizant. I suspected that we were among the living again when she tenderly kissed me on the end of my nose and her smile was as wide as the Mississippi. "That was fun," she giggled (I had never heard her giggle before). "Also, does that mean that you would consider a relationship with me?"

I thought for quite a while, until her smile faded a little. Then I spoke the truth. "I have very conflicting emotions. I suddenly realized that I may already be in love with you -- and if not I'm close," I started to say. Her increasingly large smile caused me to stop. I stroked the side of her face then said "But I can't stab Jeff in the back; and there's another thing that you don't know about that may cause you to not want a relationship with me."

Rosalind got a perplexed look on her face and then said "Let's shower together, get some clothes on, and then talk this out -- even if it takes all day and all night."

I agreed so we dragged our asses out of bed and I started up the shower waiting to see if it was warm enough for her before getting in. It was then that I got a long leisurely look at her exquisite body. She saw me staring and rhetorically asked "Like what you see?"

"You look too gorgeous to even attempt to put into words," I choked out evoking an evil grin from Rosalind.

I had never gotten it up three times within 90 minutes before in my life -- which is the amount of time I estimate had passed since Rosalind took off her sundress. Looking at and rubbing her lush body in the shower changed that. Before the water ran cold I had entered her from behind and held onto her tits like my life depended on it as we again had mutual orgasms so powerful that it was a miracle that we didn't totally collapse in the shower.

We finally got clean before the now cold water started to freeze us and toweled off. She insisted that I give her one of my oversized T-shirts (I'm six feet three inches, she's five feet five inches tall), while I just put on a pair of gym shorts. I made us sandwiches in my kitchen which we ate while drinking iced tea and chatting amiably. When we finished she asked "Where should we talk?"

"How about the scene of the crime," I chuckled as I pointed to the living room. She chuckled back so we entered and sat next to each other on the large couch after I tossed my strewn clothes off of it.

I held Rosalind's hands and stared into her eyes. "Before I say anything more I want you to completely understand the following facts, since all contribute to where we are now. 1) you used to be a complete bitch, especially toward Jeff." She actually nodded her head in agreement with that statement before I continued. "No one knew that it was because you had a brain tumor, but that was the reality of the situation. 2) You are as good looking as any woman in the world."

She blushed and demurely sighed "No I'm not..." but I interrupted her with a gentle finger to her mouth.

"Continuing, 3) Jeff, along with my mother and sister, saved me after Sarah died. Without him I would never have gotten through it. 4) Jeff really wanted to divorce you because of the way that you treated him but in view of your prenup which would give you half of his business unless you were cheating on him he couldn't afford to do it," I stated.

"You know about the prenup?" she quizzed.

"Yes; I've read it and talked to Jeff about it."

She nodded her head.

"Further, 5) I was willing to do anything to help Jeff since he had helped me when I needed it most. 6) As part of my plan to help Jeff -- by the way he didn't know any details of my plan just that I was going to help him -- I started to ingratiate myself to you."

This made her eyebrows rise. I squeezed her hand "Before the really hard part, number 7, I need to make it clear that while I started out only getting you to like me to set you up somewhere along the lines I started to get feelings for you, despite your bitchiness. Now, today, after the best sex of my life, your operation, and the tenderness that went along with the sex, I know that I've fallen in love with you. Can you believe that -- can you feel that?"

She smiled again. "Yes I can believe that, because I could feel it overlay the sexual gymnastics that we just engaged in."

"OK; now the hard part; I really, really, do not want this to ruin our relationship going forward whatever it might be, but I have to be honest if we are to have any relationship at all even if this turns into a one day stand and you hate me afterwards." Rosalind had a puzzled look on her face as I sighed and then continued.

I then told her about hiring a male escort, spiking her drink, having a hotel room set up with cameras, and then changing my mind, dismissing the escort and trying to toss out her drink when she fainted because of the effect of the Ecstasy combined with her tumor.

When I finished Rosalind silently stared at me for a painfully long time. Finally she said "Well I guess now that you've fucked me you can tell Jeff to get that divorce."

"No!" I barked, more loudly and harshly than I had intended. "You're a different person now, I already started to look at you differently before your operation, and now that I know that I love you if you don't dump me I'm going to work things out between you, Jeff, and me. If you do dump me Jeff will never learn about what happened today between us from me."

After another few minutes of her silently staring at me she said "I have a lot to think about; I'll call you once I reach some sort of preliminary conclusion."

Rosalind removed her oversized T-shirt, of course exposing her consummate naked body once again and causing my over-worked cock to try a resurrection, put on her sundress, and moved toward the door. I gently grabbed her arm "I love you," I whispered. She gave me a quarter smile, a quick kiss on the end of my nose, and was out the door.

Despite the best sex of my life, concluding little more than an hour ago, I felt like shit. My betrayal of Jeff, near betrayal of Rosalind, and my weakness in telling her three times that I loved her today when I only just now realized it myself, all weighed heavily on me. I was more or less a zombie the rest of the weekend; however I did get my head out of my ass long enough to start developing a plan in case Rosalind did contact me in the future.

************

Monday morning I had two dozen roses delivered to Rosalind at her office. There was no message, only the imprint of a kiss on the card accompanying the flowers.

I was anxious for the next few days, not having heard from Rosalind -- or Jeff -- but work was busy and in my free time I fleshed out my plan.

Thursday night after work Rosalind showed up again at my house. "Thanks for the flowers," she said with only a hint of a smile.

"Glad you liked them," I replied as I moved out of the door and swept my hand in a motion entreating her to enter.

We sat next to each other on my living room couch. She didn't pull her hands away when I held them. "If you have a plan I want to hear it," she firmly stated.

I shrugged my shoulders then replied "I go to Jeff and tell him that I might be able to talk the new you into a divorce where you split assets 50-50 except that you leave his business alone although you get a payout of 2% of its value each year for the next ten years. If he is agreeable the three of us talk together. At that time you tell him that you have fallen for me and want to start a romantic relationship with me. I act surprised, but indicate that I'm agreeable if it wouldn't bother Jeff. If he doesn't object we can date for a couple of months then you can move in with me. You and I will sign a prenup that protects us both but is more generous to you than the deal you conclude with Jeff."

Again Rosalind silently stared at me for the longest time; this was getting to be her trademark. After a while she said "Actually, it's a good plan; however I need confirmation that my last time with you wasn't a fluke. Jeff is out of town tonight so after you make me dinner and our food digests we need to revisit your bedroom until tomorrow morning."

When I woke up Friday morning totally emotionally and physically drained with Rosalind sucking my cock trying to do the impossible and get me up for a fourth time since nine o'clock the previous evening I wondered whether I could survive a relationship with her. When I felt my cock expectantly come to life followed shortly thereafter by being buried in her asshole the extent of my thinking was only "But what a way to go if she does fuck me to death."

***********

I was truly shocked that my plan worked to perfection -- normally at least a small glitch could be expected. Jeff was agreeable in principal to my divorce plan, although I started out at 3% for the yearly payout over fifteen years but he negotiated it down to 2% over ten, which was what Rosalind and I were looking for anyway. The following meeting with the three of us was cordial and I thought that I suitably acted surprised when Rosalind expressed romantic interest in me. What followed was about the most amicable divorce in history because the only major financial issue was settled, and neither Jeff nor Rosalind had any interest in a continuing relationship with each other.

Once the divorce terms were agreed to and the papers filed I took Jeff out to dinner. "Jeff, there's something really bothering me that I have to get off my chest," I said just as our steak-lobster combos arrived, food that he liked so much that he wouldn't bail on me despite what I had to say.

"What's up?" he smiled before cutting off a piece of sirloin and sticking it in the melted butter supposedly for the lobster. However, before I got up the courage to answer he said with what appeared to be a grin even though I couldn't tell for sure because he was soon chewing his meat. "You're not going to bore me by telling me that you fucked Rosalind before you negotiated the divorce deal, are you?"

With my fork full of lobster tail poised in mid-air I almost choked. "You knew?" I finally blurted out. "How?"

After he finished chewing and swallowing he smiled and said "You don't think that I could tell how Rosalind looked at you, and the fact that you looked happy for the first time since Sarah died? You had to be fucking," he concluded with a chuckle.

"But...but...but...you could have gotten away without any payments from your business," I gulped.

"Yeah, by making you embarrassed by having to testify and possibly ruining your newfound happiness when I worked for a year to get you back on your feet. Your proposal was eminently reasonable since Rosalind and I did have a few good years, and after her operation my health improved quickly enough to get me off blood pressure medication, so I was happy as a pig in poop to let you have her," he replied before cutting another piece of steak and dipping it in the melted butter.

I got teary eyed and said "You're the best friend in the world..." but he cut me off just before "world."

"Don't get all wimpy on me, dude. No more talk about this; just name your first kid after me. Now when are our local Bozos ever going to recruit a quarterback that is worth a shit?"

************

Rosalind and I didn't go through a pretend dating period. She moved in with me as soon as the divorce papers were filed. The divorce papers included a paragraph specifically allowing that. Fortunately she never fucked me to death, although it wasn't due to lack of trying on her part for the first four months of our sexual relationship. Even after four months I was easily coming to the conclusion that I should propose to the hottest woman I'd ever seen who now tumor-less was as pleasant as she was sexy when my time line was accelerated. After a beautiful love-making session she got nose-to-nose with me.

"I didn't tell you the truth about something," she said with a serious face. "I didn't really lie; I was just misinformed about the facts."

All sorts of heinous possibilities flashed through my brain. "Uh...what's that darling?"

"I told you that I couldn't have kids; since I'm six weeks pregnant seems like that isn't correct."

"You're what?" I asked with a demeanor that was clearly excited, not upset.

"You're gonna be a proud papa, no way around it stud," she chuckled.

"Will you marry me?" I blurted out at the same time that I got out of bed, ran to my dresser, and opened up the top drawer. I dropped the little box twice before I finally got to her and opened it up exposing a diamond engagement ring that had more carats than Bugs Bunny.

"Hmmm..." she said with a pensive look on her face. "Let's see, I'm in love, I get better sex than I have a right to expect, and I'm going to have his kid in a few months; let me think about it."

I tickled her until she yelled "OK, yes I'll marry you, now stop with the tickle torture and make love to your baby mamma."

I did.

***************

We did not name our first kid after Jeff. There was no decent girl's name that we could come up with that was anything similar to any form of "Jeff." However, our son is Jeff Simon and his godfather Jeff Phillips is proud of him and already has his position on the High School football team picked out despite the fact that he is now only two. Jeff and his new wife Brittany and their daughter (not named Rosalind, ha, ha), are frequent visitors to our house.

I could not have been happier the last six years of marriage with the tumor-less sextastic hellcat Rosalind as my wife.

Life is strange.

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  • COMMENTS
43 Comments
oldpantythiefoldpantythief29 days ago

What a screwed up situation, but I loved it. What an ending, everyone getting what they wanted and being happy about it. Glad they could all stay friends.

MarkT63MarkT6311 months ago

Good story. At least Jeff didn't cheat...

GuyfromShadesGuyfromShades11 months ago

Good story, enjoyed the path it took. Thanks for your writing.

AA82ndAAAA82ndAAover 1 year ago

Great moves at the end. Makes the story a bit unrealistic but hey I think it worked.

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