Trust Fund Baby Pt. 07

"Yeah, she already warned me," I said dejectedly as I walked towards my Ford Raptor.

Even though I knew that there was a used prophylactic shoved in my glove box or ashtray, it didn't make it any less of an affront. I guess if they were going to leave evidence of Madison's infidelity, I would rather have it be in my truck than in my four hundred thousand dollar Lamborghini.

However, as I approached my truck, I saw the used condom hanging from my rear-view mirror, the copious load inside it causing it to extend halfway to my dashboard. There were traces of peach lipgloss visible all over it, a testament to the show of appreciation they had given Clarkson for his huge purchase. It was tied so tightly to the stem of my mirror, that it was impossible to remove without fear of breaking it, and coating my dash with semen. I took the back streets home, not wishing to have the semen-filled rubber on full display to all of the other road users.

I was infuriated by the time I pulled up my driveway and hid my truck in the garage. Madison had pushed me too far this time, both by offering me up to take Clarkson's new shirts to the dry-cleaners, and by hanging his used condom from my mirror for all the world to see.

I was done with her bullshit, and in a scene that would be repeated dozens of times over our tempestuous relationship, I called my uncle. Without getting into any specifics, I told him that I thought my partnership with Madison had run its course, and he invited me to stay with him for a few days.

"You need a break, son," he said in his usual loving paternal way, the closest thing that I had to a parent in the world.

I should have just grabbed a few things and split, but I took a shower to cool off, as I didn't want to show up at my uncle's house until my rage had subsided. I never wanted him to know the extent to which she tortured me, even as I was starting to recognize that I was in a fucked-up relationship.

While my rage eventually dissipated, I couldn't shake my erection. The more I thought about Clarkson jerking off on my girlfriend as she got impaled on Olivia's strap-on, the harder my cock throbbed. I knew I had to get the fuck out of there, but as sex was still my primary motivator, I felt a surge of excitement when I heard the two girls chatting animatedly, as they exited their Uber in my driveway.

"Thirteen hundred dollars," I heard Madison exclaim enthusiastically, presumably referring to her commission. "We are going to celebrate tonight."

Even though Madison had showered before her boss had arrived and excused her for the day, she still bore the signs of having been well-used, by both Olivia and Clarkson. There is a certain look that women have after sex, and Olivia had it plastered all over her beautiful face.

Madison, by contrast, had a look of sexual frustration, the result of Clarkson having left her high and dry, as he selfishly focused on his own needs. The sounds of female delight that I had heard at the Tom Ford showroom were undoubtedly faked, and Madison had only been dry-humping Clarkson's leg because she was desperate for her own release. She eyed me up hungrily, recognizing that I could satisfy her needs, if she used me in conjunction with her vibrator.

"Where are you off to baby?" she cooed, as the two of them approached me.

I was always receptive to Madison's sexual advances, but as I tried to reject her, she quickly assessed the situation, realized that she had pushed me too far, and made an immediate effort to rectify it.

"Pete, I have a treat for you," she said, as she reached out and gently caressed my crotch. "Something special as a token of my appreciation for your help watching the store earlier."

"I already found the condom," I said angrily, not interested in her games.

"No silly," she countered pleasantly, "Olivia and I talked about it on the drive home," she added, referring to our house-maid in a more deferential tone than usual. "We want to treat you to something really special tonight."

I should have known that Madison was winging it, trying to make amends for pushing me too far. However, she seemed so plausible as she shared their plans with me, and I really wanted to believe that they had talked about it.

"As you know, once a month Olivia will undergo her transformation," Madison began. "The beauticians will do her hair and make-up, she will be moisturized from head to toe, even subjected to a Brazilian wax treatment, in an attempt to feminize her completely for Clarkson's enjoyment."

I felt my resolve weakening as I tried to imagine where this was headed. However, I remained impassive, trying not to tip my hand that I was feeling less animosity towards Madison with every passing moment.

"I am sure you agree that Olivia looked spectacular this morning when we left the house," she continued, reeling me in with every word.

"Yes, I agree," I said, "she looked absolutely beautiful. Still does," I added, as the younger woman blushed appreciatively.

"Well, obviously I can't turn back time, but we feel bad that you didn't have a crack at her well-lubricated asshole before she left the house this morning, as would be your total right as master of this house."

"That would have been nice," I opined, as my cock stood fully to attention.

"Well," Madison said seductively, recognizing that she had me where exactly she wanted me, "what can we do to make it up to you?"

Olivia and Madison looked so beautiful as they stood in front of me, smiling broadly, signaling their total availability. Clarkson had put my girlfriend through the ringer more than Olivia today, and the younger woman still looked very appealing, fresh from her complete makeover. She was still wonderfully scented, and her freshly-shaved pussy hadn't been used much, as Clarkson had indulged in his preferred method of subjugating young women, anal sex.

I decided on the spur of the moment that I was going to take advantage of whatever was on offer, and use Madison one more time to bust a nut before I left her for good. I also was pissed at her for constantly disrespecting me, and part of me wanted to punish her. Without thinking I blurted out what was on my mind.

"I want to make love to Olivia," I said forcefully, feeling like at this point I had nothing to lose.

"Whatever you want, baby," Madison whispered agreeably, as the two of them moved into my personal space. "What position do you want her in first?"

I could feel my anger dissipate as the two of them began to unzip my pants, the familiar stiffening of my cock and leaking of my pre-cum, forcing me to refocus on the task at hand, rather than on exacting any revenge on my girlfriend. It was Madison who sank to her knees first, and as I looked down at her recently touched-up platinum roots, I felt my resolve to leave her weaken.

She obviously knew that she had pushed me too far, because in an uncharacteristic display of submission, she allowed Olivia to remain standing, as she began to suck my cock. Olivia raised her dainty hand to the side of my face, and raked her fake press-on nails across my temple, before leaning in to kiss me. We ended up making out for several moments as Madison blew me. I was determined not to allow my girlfriend to have it too easy, so as I approached my orgasm, I told her to stop.

Madison looked up at me, a confused look on her face as this was just about the first time I had ever delayed my orgasm.

"Eat my ass," I ordered her, again feeling like I would just split and head to my uncle's house if she gave me any pushback.

I didn't even wait for her response, but just closed my eyes and resumed my tender French-kissing with Olivia. Even though I had an exit strategy, I was pleasantly surprised when I felt Madison grab my buttocks and spread them apart. A few seconds later, with her having seemingly made the decision that she needed to make amends, I felt the tip of her tongue lap away at my taint.

"Oh yes," I blurted out, "right there baby."

Once her lips were removed from my cock, I was no longer in danger of blowing my load, and I was able to enjoy my protracted make-out session with Olivia, as Madison rimmed me. After a few minutes, after we came up for air, I told Olivia I wanted to make love to her in the missionary position. She seemed flattered that I had chosen the most intimate way to couple, even referring to it as the lover's position, which probably pissed Madison off as she knelt behind me, assuming the duties of the rim-job girl.

My goal was to engage Olivia completely as we lay face to face on the bed. Using George's seduction, and eventual sexual fulfillment of Madison as a benchmark, I lowered myself slowly onto Olivia, and slid inside her very wet pussy. As I started to thrust slowly in and out of her, I looked back over my shoulder to see Madison looking on enviously.

"Keep rimming me, Madison," I said confidently, not waiting for an answer, before I resumed kissing Olivia.

Mimicking George's motions, I began to grind my pelvis into Olivia's on the inward stroke, hoping that the additional stimulation of her clitoris, would expedite her release.

"Oh fuck, that feels good, Pete," Olivia said, as Madison lowered her head to my ass, and began to lick between my buttocks.

I wish I could say that I brought Olivia to several earth-shattering climaxes, the way George had skillfully satisfied my girlfriend. However, under my favorite stimulation of sex combined with analingus, I felt my nuts constrict, and knew I was close. For this reason, I slowed my thrusts slightly, and put more pressure on Olivia's clitoris by pressing my pelvis deeper into hers.

"Oh yeah, Pete," Olivia whispered, as she responded to the additional stimulation. "I have never come in this position before, but I think I may be getting close."

When Madison heard this, her desire to prevent Olivia from enjoying an orgasm encouraged her to push me over the edge.

"Fuck that tight pussy," she said, as she withdrew her tongue from my taint. "You deserve access to other snatch. For your birthday treat, I am going to let you fuck Jody."

As her words sank in, she inserted the tip of her tongue inside my ass and began to wiggle it around inside me. I knew Olivia was probably getting closer to her orgasm, but I was unable to prevent mine, and shortly after Madison's promise, I tensed up and ejaculated inside Olivia, leaving the younger girl high and dry.

If Olivia felt any disappointment at being denied release, she didn't show it, choosing instead to focus on my pleasure. I spread my legs slightly, a signal to Madison to continue with her rim-job, as Olivia and I started to kiss tenderly.

It wasn't very often that I held the upper-hand in my relationship with Madison, but as she seemed intent on making amends for her earlier disrespect, I decided to push my luck. I basically ignored Madison as she ate my ass, and focused on making out with Olivia. As I composed myself, I had the overwhelming urge to fuck Olivia again, although I hoped that she might get some release this time too.

Madison, being a virtual mind reader when it comes to my needs, didn't need to be asked, but simply removed her tongue from between my buttocks, and goaded me back into an erection.

"Jody will dress up really cute for you on your birthday," she began, as my cock twitched inside Olivia. "You can enjoy her however you want to on your special day. Especially as she is now truly a three-hole girl."

I grunted at the thought of sodomizing the gorgeous young blonde, and began to slowly thrust into Olivia as my cock continued to stiffen.

"He's hard again," Olivia said, with a giggle, as she digested my ridiculously short refractory period."

"I think the thought of Jody on her knees looking up at him with her angelic face is turning him on," Madison said, reducing my hostility towards her with every spoken word.

This was a scenario that would be repeated countless times over the years that Madison and I were a couple. She would push me to my limit of endurance trying to get me to propose to her in order to stop the insanity of it all. On the rare occasion that she crossed the line, and I decided to end the fucked-up relationship, she would repair the damage by offering me promises of pure delight, usually involving young girls that she knew I was attracted to.

When the two of them were done with me, I fell asleep on my bed, completely satiated. My nuts were drained, having come twice inside Olivia's tight pussy, before busting a nut tit-fucking Madison, as Olivia took her turn with her face between my buttocks.

I can honestly say, that at that exact moment in time, I had no unfulfilled needs or desires. I slept soundly for almost two hours, before Madison gently woke me with a beautifully presented fruit platter. Having seemingly anticipated my possible dehydration, she propped the thirst-quenching snack upon a folding bed tray, and as I selected a slice of pineapple, her lips descended upon my cock.

Even though she managed to coax one last load out of me, as I relaxed on my bed enjoying the fresh fruit, it was a dribble at best, and for the first time in my life, I knew that I needed a break. Not from Madison, of course, as she had successfully wormed her way back into my favor, but unbelievably from further sexual activity.

Of course, being a teenager, this lasted hours rather than days, but by the time we crawled in to bed together that night, any ill-will I had felt towards Madison had evaporated, replaced by admiration and desire for her.