Trust Fund Baby

Almost two hours after the game ended, with about half of the men having already left and most of the cleanup taken care of, Olivia announced her intention to leave.

"Do you want me to stay and keep you company, Madison?" Jody asked.

"I am fine," my girlfriend responded. "I am comfortable with these guys. You can go ahead and leave too."

The two younger women left shortly after that brief exchange, each of them skipping happily out of my front door clutching approximately twenty one thousand dollars in cash, the sum total of their ten grand "appearance fee," and their share of the football pool winnings that was blown on sexual favors.

The alcohol had done its job, lowered the inhibitions and heightened the level of arousal in the room. A few moments later, sensing that the party was over, three other guys drifted away from my place. A cursory glance at the security camera revealed Baldwin, Clarkson, two other guys that had kept a fairly low provide, and the recently divorced Arts Center benefactor, were still in attendance.

Once the two younger women had left, it seemed to me as if Madison had exercised very poor judgement by remaining alone with five men, who were presumably liquored up. It was fairly obvious from the touchy-feely nature of the group, and the prominent erections visible in most of their pants, that they were ready for a crack at Madison. The subject of additional payment never even came up, but I think that the guys felt that she was obligated to get everybody off one more time, particularly as they all knew that so much money had already exchanged hands. As they groped and fondled her, telegraphing their intentions, she seemed resigned to accept her fate.

This resignation quickly turned to enthusiasm as Baldwin tossed a stack of hundred dollar bills onto the top of my piano.

"There's a ten grand bonus for you, sweetheart," he said condescendingly. "Why don't you dress up in something sexy, and take care of me and the boys?"

"Let's adjourn to the master bedroom," Madison suggested coyly, to an appreciative murmur of approval from the five guys.

The fact that Madison had asked the party to adjourn to our master bedroom confirmed that her sense of right and wrong was about to be overridden by the prospect of ten grand in cash. The guys followed her into my bedroom, and Baldwin spoke first, assuming control of the situation.

"Where do you keep your sexiest lingerie?" he asked her, "I want to see you in something cute and silky."

"How about that mint-green ensemble I tit-fucked you in?" Clarkson added. "You looked cute wearing that."

The men descended on her wardrobe, trying to reach a consensus of what they wanted her to wear to service them. After a couple of minutes of snooping through her intimates, during which most of the guys held up something cute for the group approval, Clarkson emerged with an unopened gift package. Contained within the signature silver box, with LaPerla stenciled in black writing on the front, it was packaging that every man in the room could instantly recognize. It was finished off with a pink bow and there was a card attached to the front of the box.

"Somebody has been a very good girl," Clarkson said condescendingly. "Good enough to get a gift. A very expensive gift by the look of things. Open it up Madison," he added assertively.

My heart sank as he handed Madison the box, and she began to open the card. Super Bowl Sunday is the first Sunday of February, and as such, always precedes Valentine's Day. After my conversation with my uncle about the importance of intimacy in a relationship, and the role that lingerie can play if treated as a private, and personal gift between two lovers, I had gone to LaPerla and purchased Madison a Valentine's gift. It was a beautiful silk and lace chemise in an exquisite shade of baby blue, to match her eyes. I really took my time with my selection, browsing through dozens of different pieces before finally selecting the one that I felt would look the best on her. The sales clerk had wrapped it beautifully, scented it using Madison's signature fragrance, and attached my card to the front of the box.

When I got home I hid it in the back of her closet, thus ensuring that it wouldn't get opened until Valentine's Day. I could barely watch the scene unfurl, as Clarkson grabbed the card from Madison's hands, and began to read it aloud.

"To my beautiful girlfriend," Clarkson began, as the other guys listened with mock interest. "Can't wait to enjoy a night with you wearing this, love Pete."

"Open it," Clarkson ordered. "We are going to have us an early Valentine's Day celebration."

I could see the reticence on Madison's face to open the beautifully packaged gift, and when her trembling hands were moving too slowly for their liking, the guys took the package from her and tore it apart like a pride of hungry lions.

Baldwin emerged with the prize, holding it up against her naked form as if to imagine her in it. It was exquisite, a mid-length chemise fabricated of the finest silk and lace, in the most beautiful shade of baby blue, to complement Madison's eyes.

"Put it on, Madison," Baldwin instructed her. "We want to see you all dolled up in your boyfriend's special Valentine's gift."

"Accessories too," Clarkson added, intimately aware that Madison possessed drawers full of garter-belts, stockings, chokers, hair bows, and high-heeled shoes, in a myriad of colors.

You could see the doubt in Madison's eyes as she retreated to my walk-in closet, in order to pretty herself up for the assembled men. Driven to please them by the prospect of the ten grand tip, she was nonetheless aware of the level of disrespect she would be displaying, by allowing several men to enjoy her while she was dressed in my surprise Valentine's Day gift. Once she was in the closet, she closed her eyes momentarily, as if she was on the precipice of a huge decision. I was praying that she would go back into the bedroom and throw the money back in Baldwin's face.

However, as she opened her eyes and took in a deep breath, I realized that she was preparing herself for the inevitable. This was confirmed when she reached into her extensive lingerie collection and began to remove color-coordinated accessories from the cedar-lined drawers. The LaPerla garter-belt was extracted first, and was, predictably, knowing Madison's attention to detail, an exact matching shade of blue. I noticed that the tags were still attached to the three hundred dollar piece of lingerie, and wondered if Madison was okay with forfeiting her ability to get a cash refund in the event she needed it.

The thong panties emerged next, and once I saw the tags were still attached to this piece, I knew it was by design rather than accident. I knew for a fact that Madison owned several pairs of these panties in every single color that LaPerla offered. The company would even email her when they introduced a new shade, such was her importance to them as a customer. It stood to reason then that Madison left the tags on so that the assembled men could unwrap her for their enjoyment, safe in the knowledge that nothing she was wearing had been viewed by another man. This was a kick in the nuts for me, but for Madison it was just another day at the office, justifying her exorbitant price tag.

Once she was ready, she emerged from the walk-in closet looking every bit the fuck-toy that the guys were expecting. When I dropped four hundred dollars on Madison's Valentine's Day gift, I was planning to be the one to enjoy her in it, but the sight of her being visually devoured by all of the men triggered something within me, and I felt my cock stiffen, against my will.

Madison did a quick twirl for the guys, and handed Baldwin a pair of scissors, evidently considering him the lead dog of this pack.

"I am yours to unwrap," she said seductively, as he moved forward and with a ceremonial flair, snipped the tags from her ensemble.

As I watched the tags flutter to the ground, signifying to the salivating guys that Madison was wearing over one thousand dollars worth of lingerie and accessories, in addition to the color-coordinated Louboutins, I was filled with regret knowing that my Valentine's gift to her was being unwrapped prematurely.

Madison flitted between the guys, and they took turns in feeling her up, under the guise of admiring the exquisite details of her outfit. As she stood there in her matching "fuck-me pumps" awaiting further instructions, her blue eyes sparkled, indicating her complete availability for whatever the men desired.

"If you were my girlfriend, I would have more respect for you than to pass you around Newport Beach like a joint," Baldwin said, to a round of laughs from the guys.

"Being available is my choice," she responded confidently, "Pete knows the price of monogamy is to propose to me."

I did know it too, although hearing her verbalize it was another kick in the nuts. As long as I dated her, no matter how much I elevated her life-style, she was going to fuck and suck other guys. At least she had been brutally honest about it. It would have been much worse for me had I been under the impression that my loving faithful girlfriend was waiting patiently for me at home, and I had discovered her about to engage in a gang-bang, after a routine check of my security cameras.

Even though Madison definitely wasn't waiting patiently for me, she was apparently prepared to wait for the assembled guys. After Baldwin told her to "get up on the bed and assume the position," she stayed motionless in the doggy-style pose, beautifully displayed in her Valentine's Day gift.

George had just enjoyed her asshole, and had made her orgasm several times, so her pussy showed the obvious signs of having self-lubricated, while her anus showed similar signs of having been manually greased. Predictably, in a group of Alphas, the men began to argue about the order in which they were going to take her.

Now that it had been established that everyone present was clean and free of STIs, it really didn't matter who went first. It was just like everything else in their lives that they competed for, the best table in a restaurant, the half-court seats at the basketball game, or the first new Ferrari model to be shipped to Newport Beach. They just wanted to be first inside Madison for the bragging rights.

Even amongst this well-established group of multi-millionaires, there emerged some more dominant males. Baldwin was one of them, emphatic that he deserved to be first, as he had put up the cash. There wasn't any argument with his assertion, and while a couple of the guys seemed prepared to wait their turn, others had clear motives for determining the order of succession.

"I just don't want to go after Clarkson," one of the guys remarked, to a chorus of laughs which totally broke the ice.

Apparently that was something that everybody understood and could agree upon. I had always suspected that Clarkson was hung like a donkey, particularly because I had the misfortune of handling his used Magnum condom on more than one occasion. However, after gauging the reluctance of the group to follow him in any act of sexual penetration, it was obvious that his friends were aware of his considerable endowment.

"The bitch has three holes," Clarkson said, in his own defense. "We don't all have to enjoy the same orifice."

That was just about the last thing I wanted to hear, as I watched the security tapes. As unappetizing as the prospect of my girlfriend having vaginal sex with five guys was, I really didn't want to witness her getting spit-roasted by two of these wealthy pricks at the same time. Even worse was the thought of her getting double-penetrated, and sucking a cock simultaneously.

This was apparently not my girlfriend's first rodeo because Madison, to her credit, waited patiently on all fours, as the order was determined. I would have characterized her actions as being totally passive, although she did wiggle her ass seductively a couple of times, as if to invite the first lucky bastard to step up and get balls-deep inside her.

Finally, after several moments of increasingly heated discussion, it was Madison that spoke up, the apparent voice of reason.

"Surely the host should have the first crack," she suggested. "No pun intended," she added demurely, to a chorus of laughs.

"Then it is decided," Baldwin said, as he stepped forward to take his rightful place at the head of the line.

And just like that, with the artfully chosen words that one would expect of a skilled courtesan, Madison broke the ice. Without alienating any of the men in the room, she managed to determine who at least was going to go first.

Judging by their level of familiarity, most of these guys had been intimate with Madison before. In a pattern that would be repeated over the years that she was my significant other, Madison and I would bump into one of the Newport Beach elite, and immediately upon the perfunctory introductions, I would be apprised of their dating history. I use the term "dating" loosely, as many of the encounters had been one-night stands, some had been threesomes, others even group-sex or gang-bangs. The only common thread was that money had exchanged hands, and that future encounters could not be ruled out, at least until I was engaged to Madison.

Baldwin sidled up behind Madison, and as if trying to decide which hole to take first, rested the tip of his cock against her taint. Madison seemed relieved that she had some say in the matter, and quickly reached around behind her ass, and guided Baldwin's large member into her wet pussy. She let out a loud moan of pleasure as he got balls-deep inside her.

I knew I should have fast-forwarded through this intensely difficult to watch scene, the second Madison began to squeal with delight, and approach her, albeit faked, first orgasm. To the uninitiated, her pleasure seemed real, and as she writhed and frolicked on his cock, one could certainly have been forgiven for believing that she was about to come. Not me though, I wasn't fooled for one second. I had witnessed that manipulating bitch fake multiple orgasms, and as far as I was concerned, this was just the next one in a long line of deceitful displays of feigned pleasure.

It seemed to encourage Baldwin though, that self-entitled prick slapping her ass and pulling her long platinum hair, that he had instructed her to bleach almost-white. He had ordered her to undergo an increased tanning-bed regimen too, before making an appointment for the Brazilian Wax Treatment to apply the finishing touches for his visual enjoyment. Now as he fucked her from behind, enjoying the total lack of tan-lines that her month long sun-bed schedule had achieved, he fast approached his release.

At this point in my young life, I had never participated in a gang-bang. I had experienced threesomes but had never shared a woman with other men. Despite my total lack of involvement in such activity, it did seem like there would be some basic ground rules, out of respect for the other participants. Judging by the vocal remonstrations from the other guys, Baldwin violated the most obvious of these rules by withdrawing his cock from Madison's pussy, and blowing his load all over the back of her chemise, and the tips of her platinum extensions.

Madison didn't complain, quite the opposite. She squealed enthusiastically, wiggled her tanned ass and egged him on, as he continued to rain his semen down on her lower back. Once he was finished ejaculating, he stood up and walked away.

"Sloppy seconds, anyone?" he said in a disparaging manner, as if he wanted to rub everyone's face in the fact that he went first.

I was hoping that Madison would recognize the potential for things to get out of hand, and call it a day, but she didn't appear ruffled in any way.

"Give me five minutes to use the ladies room," she said demurely, as if she was going to powder her nose, instead of wipe a man's ejaculate from her ass, back and hair.

A few moments later, as the realization dawned on these guys what the potential downside was of going last, and as my girlfriend resumed the doggy-style position, all four of the remaining men approached the bed. Clarkson, having over the last four years demonstrated a strong preference to be pleasured orally, stood in front of Madison's face and she began to fellate him.

I had always assumed that Madison treated Clarkson to a loving, edging blow-job, when they hooked up once a month. The traces of lipgloss all over the condom that he would periodically send home with her, bore witness to that. However, today, in the company of his fellow Newport Beach millionaires, Clarkson was showing off, and began to fuck her face in earnest. Madison struggled to breathe as he held her firmly by the ears and violently deep-throated her. There was nothing loving or intimate about this blow-job, which would more accurately be characterized as forced oral-copulation, and wouldn't have seemed out of place had it occurred in a prison cell.

The recently-divorced Arts Benefactor claimed her asshole, kneeling behind her as the other two guys looked at each other, figuring out that there were two dicks left, but only one hole. Madison couldn't really do much to encourage or assist the benefactor, but she did manage to wiggle her ass as he lined up with the entrance to it. Dispensing with the condom, he entered my girlfriend's anal passage bareback, and without giving her any time to adjust to his invasion, began to fuck the crap out of her asshole.

"My ex-wife fucked me in the ass," he said venomously, presumably referring to the acrimonious divorce he had been through. "Time for some payback."

Believe me, it is tough enough to watch a guy make love to your woman, but it was heartbreaking to watch Madison being pounded at both ends by a couple of misogynistic rich guys, who seemed intent on punishing her for her wanton behavior. Luckily the benefactor was a quick come, and as I watched him contort his face in ecstasy and blow his load inside Madison's asshole, I wondered if his sexual deficiency contributed in some way to the demise of his marriage. While he couldn't match Baldwin's theatrics of ejaculating all over her back, the benefactor did have one final act of disrespect left in him, and he wiped his cock clean on the back of Madison's four hundred dollar chemise.

Clarkson had no such issues with premature ejaculation, and as he withdrew his cock temporarily from Madison's mouth, so that she could change positions to accommodate the last two guys, he was still fully erect and nowhere near climax. Madison changed into the cowgirl position, and lowered herself onto the erect cock of one of the lower profile guys, as he lay on his back. The second lower profile guy pushed her upper body forward, and eased in behind her doggy-style, so that they double-teamed her. Once both guys were balls-deep inside Madison in their respective orifices, Clarkson, reentered her mouth.

Once again, presumably because he enjoyed Madison's oral delights once a month, Clarkson outlasted the two guys who were fucking her bare-back. They came within a few seconds of each other, and as she continued to fellate Clarkson, semen dripped from both of her holes. At some point, with the other four guys having recovered and now half-heartedly watching the show that he was putting on, Clarkson decided that he wanted to finish in my girlfriend's asshole. He didn't ask her either, knowing how much discomfort he had put her through four years ago when they first met, and he sodomized her in exchange for a twelve thousand dollar purchase at Tom Ford.

Clarkson simply released his grip on her ears, withdrew his cock from her mouth, and asked her where he could get a condom.