Trust Fund Baby Pt. 04

She knew exactly how to get me off, and as I started to tense up, she closed her lips around my cock-head, enveloping it within her warm, moist mouth. Her eyes were twinkling as she egged me on, and moments later I blew a huge rope of ejaculate into her mouth. A second cumshot, which seemed equally powerful, was ejected from my nuts a split-second later. Madison had no difficulty swallowing my load, but after my second spurt, she pressed her head deeper into the pillow and my cock fell from between her pursed lips.

Free from the confines of her mouth, my ejaculate spurted all over the place, and she let out a playful squeal as the next rope shot into her hair. As my subsequent cumshots started to lose power, they didn't have as much velocity, and the next one splatted on her nose and cheeks. The last two eruptions ended up hitting her under the chin, and pooling all over her neck.

"Fuck yeah, Pete," Madison squealed delightedly, "that was hot!"

As luck would have it, the Russian finish she allowed me was premeditated, in an attempt to drain my balls sufficiently so that I could handle the events of the following day. When I woke up in the morning and entered my kitchen to grab a cup of coffee, the first thing that greeted me was the sight of that fucking calendar. As it hung on the front of the refrigerator, with a big mint-green perfectly-formed lipstick kiss marking today's date, it served as a stark reminder that I was on restriction for the day, and that Clarkson was due his monthly, edging cock-worship session, that was by now, condom-optional for him.

I hated this one day a month, but as Madison often reminded me "not enough to put a ring on it," which would have guaranteed me a monogamous relationship with her. Even though she had allowed me to tit-fuck her and explode all over her face, I still woke up with a hard-on. Madison completely ignored it, setting the tone for what would be a long, frustrating day for me.

After breakfast, she took a shower, and asked me to bring her a fresh razor blade, the implication being that she was going to shave her pussy. I knew not to ask Madison any questions, as she loved to torture me with tales of her exploits with other men. However, having a freshly-shaved vagina didn't seem necessary if she just planned to blow him. I suspect that she was fucking with me, and this was confirmed when I observed that the mint-green chemise that I had purchased for her the previous day, was hanging up in her dressing room, accompanied by some matching Louboutins, and a garter-belt and stockings.

The SKU tags, indicating a retail price of three hundred and ninety nine dollars, had just been cut from the chemise, and lay discarded on the floor of her dressing room. This blatant attempt at humiliating me did invite my questions, and I spoke up intending to hold my ground.

"Are you wearing that to work today, Madison?" I asked, with as much authority as I could muster.

"Yes," she responded seductively. "Be a sweetheart and help me put it on. The straps on the back need to be perfectly straight."

"But," I stammered weakly, "I just bought that for you. I was expecting you to wear it for me."

"And I was expecting to be engaged by now," she responded coldly. "You can't always get what you want, Pete."

Normally, I would have slinked away after such a complete put-down, but I was pissed at the liberties she was trying to take with me. I had just paid four hundred dollars for that beautiful mint-green chemise, and I wanted to be the one to take Madison first in it.

"Madison," I added lamely, "can't you wear something different to see Clarkson today?"

"Why didn't you mention this earlier?" she responded angrily. "I put the mint-green lipstick mark on the calendar yesterday, and already sent Clarkson a photo of it, so he knows what to expect. I can't change my outfit now and disappoint him."

"Babe, please," I whined, "don't wear that today. You have a closet full of beautiful lingerie. Surely you can find something else he likes."

"I have already made my mind up," she said forcefully. "The last time Clarkson and I were together we went on the LaPerla website, and he told me he liked that particular shade of green. We are just about to celebrate our four-year anniversary of being friends," she added cheerfully.

"Friends," I scoffed, almost choking on the words. "Blowjob buddies," I added, unable to contain my jealousy.

"Don't interrupt me mid-sentence," she said, elevating her voice. "We are celebrating four years of friendship, and I want it to be special for him."

This whole concept of celebrating the anniversary of a friendship was a relatively new phenomenon, driven by Facebook and its relentless pursuit of photo opportunities. It was a ridiculous idea, but people embraced it, and they flocked to post pictures of their first encounter, at a wedding or a concert, or some other memorable event whose date could be recalled by both parties of the friendship. This celebration clearly was not intended to extend to the first time you blew your lover in his car.

"Special," I said contemptuously. "How so?"

"I just wanted to buy him something as a thank you gift," she responded, enjoying the fact that she was getting under my skin.

"Using my credit card?" I responded incredulously.

"Pete," she said softly, lowering the tension in the room, "this is happening. Deal with it. I know you purchased this beautiful ensemble for me, and I greatly appreciate it. However, this is Clarkson's favorite color, and today is his blowjob day, so I am definitely going to let him enjoy me first in this particular outfit. As a courtesy to you, I won't let him know you paid for it. I will pretend that I bought it for him out of my own money."

"That is worse, Madison," I cried out in frustration. "You take home eighteen hundred dollars every two weeks. Do you really want him to think that you spent two days of your hard-earned wages on something cute to wear for his monthly blowjob?"

Madison had heard enough.

"This conversation is over," she said emphatically. "Go and wait in your bedroom while I apply the finishing touches to Clarkson's blowjob outfit. I want to look really cute for his special day."

As I slinked out of the room, I was hit with a certain realization. Being a cuckold is an unnatural state of existence for a man, and causes you to react differently than you would imagine. As I digested the reality that Madison was going to suck Clarkson off, wearing lingerie that I had paid four hundred dollars for, my immediate response was that it felt like an affront, a kick in the nuts. This was undoubtedly my pre-programmed reaction, ingrained in the male psyche, and honed over hundreds of thousands of years of human evolution. My natural state was to maximize my reproductive success by mating as much as possible. Clarkson was cock-blocking me and it triggered me to pushback against this perceived intrusion.

However, my reality, as a cuckold, was much different. As I digested the fact that Madison was making herself available for another man's enjoyment, while simultaneously putting me on sexual restriction, my cock stiffened in my jeans, and the very thought of it was incredibly exciting to me. Madison knew this of course, and was acutely aware of how far she could push me before she ran the risk of alienating me.

For this reason, a few minutes later she called out to me from the living area.

"Pete, I am leaving. Come and wish me luck."

This was my least favorite part of "restriction day." I knew exactly what was expected of me, and I stripped naked before joining Madison by our front door.

"How do I look?" she asked, thoroughly enjoying my misery as I took her in.

She looked phenomenal and she knew it. She was attired from head to toe in mint-green, Clarkson's favorite color apparently. His wouldn't be the first cock to rise under the visual stimulation of her outfit, I thought, as mine stiffened involuntarily at the sight of her. As I ran my eyes over her, I couldn't believe the attention to detail, the exquisite color-coordination involved in the entire ensemble.

Madison was wearing a mint-green silk blouse that was transparent, and showcased the LaPerla chemise that embraced her lean upper torso like a second skin. This particularly exotic piece of lingerie had cost me four hundred dollars and yet Clarkson was going to be the first man to enjoy her in it. Had I known that he and Madison had been surfing the LaPerla website, trying to find a suitable outfit to celebrate their four year anniversary as blowjob buddies, I would have told her to find an alternate way to purchase the outrageously expensive silk garment. However, as she rotated slowly, just to fuck with me, the four hundred dollars became the least of my issues.

The rear of the chemise, as viewed through the completely see-through blouse, was a series of thin silk straps that added an element of eroticism to the beautifully constructed piece of lingerie.

"Are my straps straight?" she taunted. "Clarkson is a stickler for the fine details."

I couldn't offer her an audible response, such was my combination of jealousy and rage, so I nodded my head meekly. Upon my affirmation that she looked perfect from the rear, Madison hiked up her short, tailored silk skirt, revealing her matching garter-belt and stockings. Being from the same collection at LaPerla, they were a perfect match, color wise. As my gaze drifted down her toned legs, her Louboutins came into view, again a very desirable shade of mint-green.

"Do you think he will like it?" she asked with her practiced innocence.

Again, as my cock danced around between my legs at the thought of another man about to get a blow-job from my girlfriend, she gave me a sympathetic smile.

"Wouldn't it be easier for us to just get married, Pete?" she asked, offering me a way out of my continued torture.

I shuffled around uncomfortably trying to evade the question, and Madison seized on the moment, kicking me in the nuts once again, for my continued lack of commitment.

"Well Clarkson appreciates your indecisiveness," she said coldly. "I had better get moving."

I inched forward to give her a hug, but taking one look at my leading appendage, dripping as it was with pre-cum, she extended her right arm fully to block me.

"Don't you dare leak on me," she said angrily. "That is the ultimate act of disrespect to have another man's semen visible on your clothing prior to engaging in an intimate act."

Blowing a customer in the front seat of his car, in the parking lot of your work, is hardly an intimate act, I thought. The sunset picnic we had on Malibu Beach a few weeks ago, after which we made love on a blanket by a fire-pit, was an intimate act. The time we checked into the Ritz-Carlton for the weekend, and had a champagne toast on our balcony, before I drew you a bath and pleasured you orally, was an intimate act.

"Thoughts?" Madison said expectantly, as I stood naked before her, swimming in them.

"No, Madison," I said quietly, my voice steeped in resignation.

With that battle won, Madison stepped up to the mirror by the front door, applied some mint-green lipgloss, affixed a very feminine, color-coordinated, silk ribbon in her hair, and gave herself a healthy spritz of my favorite perfume.

"I will be home by 4.15pm," she said matter of factly. "Don't do anything foolish."

I watched her intently through my Nest security camera as she walked down my driveway towards my Ford Raptor, which was running with the air-conditioning on. She looked like a Newport Beach Trophy Wife as her Louboutins clicked against the polished concrete slabs of the imposing entrance. She grabbed a long, black, Tom Ford trench coat from the rear seat, which answered any concerns I had about how she was going to work in such an exposed state of dress.

After she pulled out of my driveway, I lingered in the hallway by my front door for several moments, inhaling the last remnants of her intoxicating scent, before it finally dissipated and was no longer detectable in the air. I was butt-naked, facing my twenty-four hour sexual restriction with a mixture of frustration and excitement, at the thought of her servicing Clarkson.

Sometimes my state of arousal caused me to miss some of the dialogue between us, and as I collected myself I remembered what she had said when I asked her to wear something different to entertain Clarkson.

"I put the mint-green lipstick mark on the calendar yesterday, and already sent Clarkson a photo of it, so he knows what to expect. I can't change my outfit now and disappoint him."

As I digested her words it occurred to me that she had sent him a photo. What the fuck? I went to my computer and logged into the iCloud. Madison possessed a very rudimentary knowledge of technology, and I was able to access the photos on her iPhone with ease. As I scrolled through the photos that she had sent Clarkson, I noticed a distinct pattern emerging. It appeared that she sent him a photo of the calendar on our fridge once a month, just prior to his monthly blowjob. The pictures showed the date of his upcoming oral treat, marked clearly on the calendar with a kiss, that also served to let him know what color lipgloss Madison planned to wear.

While her monthly arrangement with him was infuriating enough, it was an additional kick in the nuts to know that he got to spend some time anticipating the color of the traces of lipstick that she would leave all over his stomach, inner-thighs and genitalia. I am not sure if he chose the color for the following month, or if she simply rotated through her extensive lipgloss collection, to ensure a constant variety for him. As I went back through the photos, I was assaulted by the picture of the bulbous condom covered in traces of bright red lipgloss that I had found in the glove compartment of my Lamborghini. This oversized Magnum prophylactic was bursting at the seams with his load, and was hanging precariously from my stainless steel fridge, as it was supported by a large magnet bearing the name of Clarkson's Hazmat Disposal business. To compound my humiliation, the particularly bright shade of red matched the lipstick kiss on the calendar exactly.

I logged off the iCloud shortly after that disturbing discovery, and began to busy myself trying to wile away the hours until she got home. I got a text around 1pm, which I assume was right after Madison gave Clarkson her monthly token of appreciation for his continued patronage.

"Baby, he loved it!" it read, referring to her new mint-green chemise, I assume.

Madison got home right on time, and I greeted her at the front door the way I always did. She did a cursory check to gauge the level of my arousal, but as soon as she gave my nutsack a playful caress, I dripped pre-cum on the entryway floor, and she was satisfied that I had not masturbated in her absence.

"I have a surprise for you," she said seductively, as I followed her into our master bedroom. "Kneel."

Madison sat on the edge of our King Size bed, and as I knelt naked before her she kicked off her Louboutins. She lifted up her stockinged foot and nestled it right under my swollen nutsack. The expensive silky material felt divine as she rubbed her toes under the base of my shaft, causing me to leak copiously onto her feet.

Madison reached into her designer purse, and extracted a sealed envelope, that bore the simple inscription, "Pete."

It was with trepidation that I opened it up, and inside was a thank you card containing four crisp one hundred dollar bills. The card was pre-printed with the words "Thank you for your thoughtful gift," and was signed "Clarkson." His business card was in there too, "Clarkson's Hazmat and Environmental Clean-up" and on the back he had written "nice to have someone else on clean-up duty for once," a veiled reference to my ingestion of the melting ice cube, I assume.

I tossed the card and the hundred dollar bills across the King Size bed, annoyed that he felt the need to fuck with me, by offering to pay for the mint-green chemise that she had sucked him off in. Madison tried to calm me down, insisting that it was a genuine token of appreciation on Clarkson's part, but it felt like he was trying to humiliate me.

"No baby," she assured me. "He even asked me to forgo your restriction period this week," she added cheerfully. "You can have an orgasm if you like. Kneel there while I prepare myself."

While on the surface this appeared to be fantastic news, I met it with a certain degree of skepticism, based on my history with Madison. Nothing was ever as simple as it seemed with that woman, and so it was no surprise to me when she returned with an empty glass containing a single ice cube. I knew exactly what the ice cube was comprised of the second I saw it, and a cursory look at its milky complexion confirmed my fears.

Madison alternated between seduction and taunts as she climbed onto our King Size bed, reclined on some comfortable pillows, and spread her legs wide open. In the beginning of our relationship, Madison routinely faked orgasms in order to trick me into thinking I was a better lover, thus increasing the connection between us. Now she made no bones about the fact that I was a premature ejaculator, and we both knew that the only way that I could get her off, was with a prolonged oral session, preferably in conjunction with her vibrator. Madison placed her cordless massager on her clitoris, and I put my tongue between her legs. She came twice on my face before she decided it was time for my release. As I watched on intently, she picked up the ice cube and slid it inside her well-lubricated pussy.

Grabbing me by the ears, she pulled my face back between her thighs, and with a certain amount of trepidation, I extended my tongue until it came into contact with the melting ice cube, containing Clarkson's load. I could taste the familiar salty residue of another man's semen, but far from making me want to throw up, it made my cock throb with desire. She kept my face between her thighs until the ice cube had melted sufficiently that she deemed me ready to enter her.

Apparently Madison had chosen to disregard her initial assertion that it was extremely disrespectful to wear lingerie that was soiled with another man's semen. As we started to fuck in the missionary position, I noticed it first on her silky shoulder straps, the flaky residue having dried and giving me a clear indication that Clarkson had eschewed the condom for today's session.

Out of disgust I averted my gaze from her shoulders, and lifting myself further up on my elbows, I looked down to admire her surgically-enhanced breasts. I couldn't help but notice that his ejaculate was matted in the lace that supported and uplifted her breasts. This was supposed to be a monthly blow-job to thank him for his continued patronage, not a multi-orgasmic session that include both oral-sex and tit-fucking in his car.

It was tough for me to focus on my own orgasm, when the evidence of his, was so "in my face." I raised my eyes to Madison's and she looked completely disinterested, like she was going through the motions. She had already had her orgasms, and she was just laying there as I struggled to reach mine. Her pussy was chilled now, the ice cube that Clarkson had instructed her to insert, having done a very effective job of making her vagina cold and uninviting.

"Do you want me to suck you off, Pete?" she asked. "Clarkson said you can have whatever you want tonight."

Once again, Madison had me teetering on the brink of madness, as I struggled between the joy of knowing that I was about to get some release, and the torture of knowing that it was at the behest of Clarkson, and his new-found generosity.