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Furthermore, on the rare occasion that I did question one of her more extravagant purchases, she would present the item to me in a purely sexual context. After she had my complete and undivided attention, she would turn on the charm and grind any resistance out of me. By the time I was about to blow my load, I would be in total agreement of the wisdom of the purchase. One such example was when she spent three hundred and fifty dollars on a Cheerleader Uniform from Trashy Lingerie, just before Halloween.
"Madison, surely you could have bought a less expensive costume from one of the numerous pop-up stores that appear this time every year," I exclaimed, referring to the ubiquitous costume shops that materialized right before Halloween.
"It's not for Halloween silly," she said seductively. "I got a cheap nurse costume for Halloween from costume city. I got the Cheerleader outfit just for you," she added with a pout.
"For me?" I added incredulously, "that still seems like a lot of money for a costume."
"Why don't I try them both on?" she said cheerfully, "if you still think the Trashy Lingerie costume is too expensive, I will return it," she assured me.
I knew from experience that she was about to justify the three hundred and fifty dollar expense to me, and my cock stiffened in my jeans at the thought of it. A few moments later, Madison emerged from our bedroom wearing a Nurse Uniform that looked every bit as if she had paid twenty dollars for it. This mass-produced, cotton-blend, white costume was only available in three sizes, and even though Madison had purchased the smallest one, it was way too big for her slender frame, and hung lifelessly from her skinny hips.
The white two-piece uniform had a Red Cross on the front of it, and came with a white Nurse's cap that also bore the Red Cross symbol. My first opinion was one of abject disappointment, both at the lack of authenticity and the absence of any accessories, which could have made it fun, and quite possibly, with a fair amount of imagination, even sexy.
"That's the one you should return," I said, without censoring myself.
"I could exchange it for their Cheerleader Uniform," she offered, "it is essentially the exact same outfit, but in the blue and yellow LA Rams colors. It would save us some money," she said sweetly, although I knew she was being sarcastic.
To be honest, that crappy costume-store outfit wasn't worth half the price she had paid for it. However, I couldn't possibly see how the Trashy Lingerie outfit could be worth three hundred and fifty dollars either. Plus, when would Madison get the opportunity to wear it, if not on Halloween? I think Madison had changed her mind too, realizing that she had got caught up in the moment and made a dumb, impulsive purchase, which is easy to do when you are not spending your own money.
She was taking forever to get ready, and even though I wasn't going to rub it in her face, I felt a sense of satisfaction that she had come to her senses, and realized the folly of her impetuous purchase. Three hundred and fifty fucking dollars for a Cheerleader Uniform, I said begrudgingly, albeit under my breath.
That thought evaporated immediately, the second I saw Madison walk down the hallway between our master bedroom and my open-plan living area. It was replaced instantly with lewd thoughts of how first to enjoy this goddess, dressed as she was in such an overtly provocative costume. Madison had obviously taken more time to prepare herself for this second outfit, and her flawless makeup and long, platinum, perfectly straight hair, definitely added to the allure.
This Cheerleader Uniform fit her perfectly, showcasing her toned frame and accentuating all of her best physical attributes. This was due to the fact that Trashy Lingerie offered a multitude of sizes, skirt lengths, and cleavage options. Custom alterations were even included in the price.
The attention to detail was phenomenal, and it took me a couple of minutes to notice, and appreciate all of the included accessories. The two-piece uniform was in the Green and Gold colors of my favorite NFL team, The Green Bay Packers, with the pinstripe accents in white. The pleated skirt, beautifully constructed of a stretch-silk material, was obscenely short, and would have been wildly inappropriate for a Halloween party. It was held up by a matching short petticoat, and lay around her in a flouncy, extremely feminine manner. The skirt had a white accent running around its hem, and the number 69 embroidered suggestively on the front.
"I got this added for you," she said cheerfully, "I know David Bagdadi is your favorite player, and he wears this number."
While Madison had butchered David Bakhtiara's name, he was indeed my favorite member of the Pack. He was an offensive tackle who had worn the number 69 since he joined Green Bay. However, as my eyes scanned the rest of her uniform, noting that the number 69 adorned it in no less than four different places, I made the decision that no other man could ever see her in this, the sexual implication of this number being too obvious to ignore.
Even though the skirt was ludicrously short, the waistband sat well below Madison's belly-button, and the small crop-top that comprised the second part of this two-piece ensemble, left a considerable amount of her taut stomach visible. I considered this to be one of her best attributes, and as she strutted around my living area, I could see her abs flexing under her beautifully tanned skin. The crop-top, constructed of the same stretch silk fabric, was very tight around her chest. While this served to showcase her phenomenal tits, the elastene embedded within the silky fabric was being stretched close to its limits, and Madison's surgically-enhanced breasts appeared to be on the verge of busting out at any minute.
No bra was necessary as the crop-top forced her C cups forward and skyward, for all to visually appreciate. The number 69 was adorned on her right cup, although once my attention was on her breasts, the thought of oral-sex was replaced by the notion of tit-fucking her to release. I let my eyes wander slowly down her taut stomach, until the top of her slender toned legs came into view.
Madison typically never leaves the house without wearing a garter-belt and stockings, and always makes its inclusion in her outfit obvious, by selecting a sufficiently short skirt, that the garter-belt straps peek from beneath the hem with the slightest movement. This provocative Cheerleader Uniform had color-coordinated Bobby Sox in lieu of stockings, and their inclusion greatly enhanced the authenticity of the look. The ankle-length, green and gold silk socks were a very feminine touch, particularly as they had a white silky ribbon tied around the top of each one. Madison had chosen high-heels over the expected sneakers, the stilettos being a matching gold color, that contrasted beautifully with the silk socks.
My cock was erect now, throbbing in my jeans and leaking pre-cum into my underwear. Madison, however, was not done with the fashion show. She rotated slowly to her left, the short petticoat elevating the rear of her skirt, as if to invite me to enter her from behind. The back of the uniform was even more revealing, as the crop-top was reduced to a few stretchy straps that criss-crossed her lean back. Her long blonde platinum hair, straightened through the use of a flat iron, had been arranged beautifully into pigtails, which highlighted her youthful beauty. Feminine green and gold bows adorned each individual pigtail, and there was a green butterfly hair accessory visible on the top of her head.
I wanted to bend her over my piano, lift up her petticoat and fuck the crap out of her, such was my initial response to this alluring costume. I wouldn't have lasted long, but at least that would have justified the three hundred and fifty dollar price tag. Once she had rotated the full three hundred and sixty degrees, my attention moved to her makeup. Flawlessly applied, she had also painted the number 69 on her right cheek, and had a cute Green Bay bow clipped onto the top of her platinum locks. There was a similar ribbon around each wrist, and in her hands were green and gold Pom-Poms, which were the perfect finishing touch.
Madison raised her fantastically toned arms, and waving the Pom-Poms enthusiastically around in front of her, broke into a cheer routine extolling the virtues of Green Bay. I moved slowly towards her, transfixed by her femininity and overt sexuality, until we were inches apart. Madison had spritzed herself with my favorite perfume, and I felt an involuntary expulsion of seminal fluids into my underwear, as I inhaled her intoxicating scent.
"I can return it if you think it is too extravagant," she cooed seductively, knowing full well that this was the last thing on my mind.
"No, Madison, I love it," I whispered hoarsely, trying to decide how I wanted to have my first orgasm. "You look incredible, baby."
Madison flashed me a broad smile and then guided me over to my favorite recliner, positioned as it was in front of my eighty-inch television screen.
"Sit," she said softly. "I want you to see what you are in for this season."
After I was comfortably seated, Madison knelt between my thighs and started to stroke my cock through my jeans. I sat there leaking profusely in my underwear, as she looked up at me with her beautiful big blue eyes.
"This is going to be your best football season ever," she said quietly, as she started to undo the top button of my jeans. "I promise!"
The NFL was a big part of my life, and as an avid Green Bay fan, I watched most of their games live on Sunday. They were having a decent season so far, and I fully expected them to qualify for the playoffs this year, especially as they had reached the Conference Championship game the last two seasons. However, unless they made some remarkable mid-season adjustments, I couldn't see how this could be their best season ever. However, as Madison slipped her manicured fingertips through the zipper of my jeans, I had no reason to argue with her.
"I know you love football," Madison continued, "and if your team qualify for the playoffs this season, I thought we could watch the games together as a couple. I bought this uniform to show support for your favorite team. I will wear it to all the Packers' playoff games, and I will suck you off at half-time if you want. You can relax with an ice-cold beer and I will give you a loving, edging blowjob."
As she continued to promise me all kinds of sexual delights, I closed my eyes and tried to visualize Green Bay up by thirty points at half-time, as Madison fetched me an ice-cold beer from the fridge, before kneeling and applying her Packers' Green lipgloss to her alluring, perfectly formed blowjob lips. A lot of her words never got absorbed into my brain, the blood supply rendered in short supply, by the more immediate need of blood flow to my genital area.
When I opened my eyes a few moments later, my jeans were around my ankles and Madison's lips were inches from my cock, as it tented in my underwear.
"Did you hear what I said, baby?" she asked, with an agreeable smile on her face. "If Green Bay get to the Super Bowl, you can invite your guy friends over. I will wear this Cheerleader Uniform, and I will serve your friends whatever they need for the entire game."
I flashed Madison an icy glare, my jealousy inflamed immediately, even as my cock danced around in my underwear at the mention of her serving my friends, whatever the fuck that involved.
"Beer and snacks only, baby," she quickly clarified. "Unless of course you are feeling particularly generous that day."
I let out a whimper at that last remark and Madison's eyes twinkled with delight as she lowered her glossed lips to the tip of my cock, protruding as it was through my ever-dampening underwear. Even though it was pure delight having her nibble and suck me through my briefs, I wanted to come and after much moaning and whimpering on my part, she finally extracted my throbbing erection from the confines of my underwear.
"How would you like to come first?" she whispered seductively, as she lowered her soft lips onto my cock.
You would think at some point I would develop an immunity to Madison's beguiling ways, and be able to last at least long enough to ensure that the pleasure was mutual. However, at this point in our relationship she could still break me at will, and as she began to slowly bob up and down on my cock, I felt my nuts constrict.
"Oh, fuck, Madison," I whispered, "I am close."
With that warning issued, she removed her lips from my cock, arose slowly from her knees, climbed up onto the oversized recliner, and straddled me. She was already wet, presumably having self-lubricated from sucking my cock, and I slipped right inside her. A few moments later, as she bounced up and down on my lap, and continued to promise me the world if Green Bay reached the playoffs, I ejaculated deep inside her tight, warm pussy.
I cried out with pleasure as I emptied my nuts inside her, and after I was finished ejaculating, she leaned towards me and began to whisper in my ear.
"Trashy Lingerie has lots of other exciting costumes that I would love to wear for you," she began innocently enough. "They have a very cute Nurse Uniform with lots of sexy accessories. I would wear a garter-belt and stockings with that one though," she assured me. "They have a naughty schoolgirl uniform too, and an authentic looking Playboy Bunny outfit. I could serve you drinks wearing that one."
As soon as I felt my cock start to stiffen, I knew that she had me. I truly found her irresistible, and she used that to manipulate me. I am not sure what excited Madison more, the thrill of having men desire her, or the monetary compensation that often accompanied said desire. Either way, the knowledge that she had once again managed to shorten my refractory period, had caused Madison to self-lubricate, which combined with the huge load I had just deposited inside her, made for a very wet pussy.
As soon as I was hard, she began to bounce slowly up and down in my lap, the squishing sounds an indication of a well-lubricated vaginal cave. At one point my cock slipped out of her, and as she ceased her up and down motions, it rested against her rosebud.
"Did you know most of the Playboy Bunnies engaged in anal sex with Hugh Hefner?" she asked me, an agreeable smile on her face, as her blue eyes twinkled mischievously.
"Really?" I said, connecting the dots between the act of anal sex, and her desire to own the Trashy Lingerie Bunny costume.
"Would you like to fuck my ass with me dressed up like a Bunny?" she continued unashamedly.
Even though Madison had alluded to the fact that her asshole was on the menu for me, we had never engaged in anal sex. I think our disparate agendas had something to do with it, as Madison's goal was for me to impregnate her, and so she sought to end most of our encounters by me shooting my wad inside her. Even when she blew me, or asked me to tit-fuck her, we would still end up coupled, either right before, or immediately after I ejaculated. I didn't try and fight this, as I was protected from the risk of pregnancy by virtue of my vasectomy, and it felt really good to get balls-deep in her and relax after my orgasm.
Today, however, she wanted something from me, and was offering her anal cavity in return. My cock was resting right at the entrance to her anus, heavily lubricated from the combination of our secretions, and at that moment I made the decision to fuck her in the ass.
"Why don't you let me ass-fuck you first, Madison?" I suggested. "After I come, we can order your Playboy Bunny costume."
The sheer audacity of such a quid pro quo proposal made me tense up, and I half-expected her to slap me for the impropriety of it. However, Madison was a materialistic courtesan, and was apparently very comfortable with the transactional side of the business, because she relaxed her sphincter, and started to lower herself onto my cock. I was expecting much more resistance than I encountered as I slipped inside her, and before long I was balls-deep in Madison's anus.
Truth be told, it wasn't any tighter than her pussy, which was contrary to everything I had read on porno websites. At eighteen years of age I didn't have much frame of reference, although as I engaged in anal sex more frequently in the coming years, I would look back on Madison's asshole as one of the most stretched-out that I had ever fucked. I couldn't tell if it was from being overused by paying customers, or if it was because she had endured vaginal reconstructive surgery twice, and this had reduced any noticeable difference in the rigidity of the two canals.
It didn't take long for me to come inside her ass, especially as she started to taunt me about the fact that Steve Baldwin had sodomized her the night she flagged down his Ferrari.
"I think he fucked Jody in the ass, too," she added. "An ignominious start in Newport Beach for a runaway eighteen year old," she added dispassionately, "losing her anal-cherry to an old man. She squealed like a little pig too," Madison added with a giggle, once again creating the perfect visual for me.
I had no clue what Jody looked like, however the thought of an eighteen year old runaway trading her anal-cavity for a warm place to sleep, resonated with me, and I came hard inside Madison's asshole. After I ejaculated, Madison and I kissed tenderly in my recliner until my cock softened, and finally slipped out of her.
"Take a quick shower, Pete," she suggested, "I will make us something to eat."
Once I was clean, I returned to the kitchen and the two of us enjoyed a nice lunch. I offered to do the dishes, and Madison excused herself. I was in a very contented state for an eighteen year old man, having a full stomach and an empty nut-sack, and at that moment in time, I felt like I wanted for nothing.
I picked up her scent before I saw her, that intoxicating blend of her favorite perfume and her pheromones that I found completely irresistible. I caught myself reflexively inhaling and to my surprise, I felt my cock twitch in response. Madison entered the room seconds later, with her laptop in her hand, although it was her outfit that captured my attention.
She was wearing a white stretch crop-top that tied underneath her tits, and barely contained them. As I lowered my gaze I noticed the red plaid garter-belt attached to some matching plaid stockings, complete with a red thong that she had put on over her garter-belt straps to facilitate its removal. Her look was complemented by a pair of bright red Louboutins, that served to elevate her to almost six feet tall, and showcase her beautifully toned legs.
As she passed me, she extended one of her dainty hands and lightly brushed the tip of my cock, causing it to slowly rise. Then with a seductive wiggle of her tight ass-cheeks, she moved over to my desk, opened up her laptop and beckoned me over.
"I want you to see the detail of these fantasy costumes," she said sweetly. "They are incredible."
As she stood against the leading edge of my desk, I sidled up behind her, taking in her aroma as I kissed the back of her neck. I put both of my arms around her, and looking over her shoulder, I began to view the Trashy Lingerie website. I hadn't seen many websites of this kind, preferring much more hard-core offerings on the occasions that I turned to porn for my release. In fact, my only frame of reference was the Victoria's Secret catalog that I had retrieved from my previous girlfriend's trash can. This high-quality, glossy publication, was artfully crafted in every way. From its use of actual fashion models, to the playful seduction utilized in the way they posed, it was very titillating, if not overtly sexual. The Angels, as they were collectively known, attended charity events, and routinely appeared on talk shows and on breakfast morning television. Their names were internationally known, Adriana Lima, Kylie Jenner, Bella Hadid.
