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All NYE celebrants are 18+, and most are quite naughty.
Thanks to JuanaSalsa for motivation and editing, and to OliverPride for the subject matter.
I felt like a fucking moron, running around our parents’ New Year’s Eve party dressed in a diaper and a “Happy New year” banner hanging off my shoulder, but hey, $100 is $100, right? Mom and Dad had offered us $100 apiece to dress up. My identical twin brother Phil and I were both a little short on cash after blowing a lot of money on Christmas shopping, so we had agreed, and flipped a coin to see who had to dress as the baby. Phil won the coin toss, so he got to be Old Man Year with a full robe and fake white beard, while I had to pull on an adult diaper and the stupid sash.
Aside from the occasional guest stroking my chest or groping my ass (male AND female), overall it was going well. Most of them were around our parents’ ages, but they looked good — the women especially – dressed up in their party clothes and wearing all kinds of makeup. I have to admit, I’m a sucker for red hair and red lipstick myself, and there were several older women rocking that look. I was only there for the money, but if I happened to score some MILF action, well, so much the better.
By 11:58pm the champagne had been flowing steadily all night and people were pairing up for the big midnight kiss, so being alone I figured it was my time to bow out. I started making my way through the crowded room at 11:59, but the 10-second countdown to midnight began before I could get out; at the 5-second mark a warm pair of hands grabbed me, and I got the surprise of my life.
“Why am I even here?” I asked myself for what seemed like the 33rd time since arriving at the 23-room Taylor mansion. I didn’t know they Taylor family, but was invited because of my volunteer work at the Taylor’s favorite charity. When I received the invitation four weeks ago, my goddam ex-best friend Jackie Lindstrom had put me up accepting it. The place was full of couples dressed in their finest, clinking glasses and canoodling, while I was dressed in the slinkiest green dress I could fit my matronly figure into, not to mention full makeup, and for what? Fuck it. I knocked back my champagne, gesturing to the waiter for another tulip-shaped glass.
The day I got the invitation was also the day my divorce from Glenn was finalized, ending my 19 year marriage. I was pretty down in the dumps about it, but up to that point Jackie had been my rock, keeping my spirits up.
“Oh, go,” she’d raved, “the Taylors have wonderful friends! Go show them you’re still a hot ticket! Maybe you’ll meet somebody nice!” I reluctantly accepted the invitation, then the two of us went shopping for a new dress.
Jackie gushed, “New clothes for your new life! Isn’t this exciting?” I have to admit her enthusiasm was infectious, and I perked up a bit. I also bought some new shoes, 5″ stiletto heels that matched the dress. They were uncomfortable as hell, but they did make my legs and ass look really good! With full make-up on, I felt more like a trophy wife than a 43-year-old divorced mother of two teenaged sons.
An hour before I was to leave for the Taylor’s party, Jackie unexpectedly showed up at my door, enroute to Times Square to watch the ball drop there. “Judy, sweetie, you know I love you, right?”
“Of course, Jackie. Is there a problem?”
“Not exactly but I wanted to start off the new year clean, with no secrets between us.”
A sense of foreboding swept over me. “What do you mean?”
“I wanted you to know that Glenn and I are together now.” I looked over her shoulder, and in the driveway I saw Glenn, waiting behind the wheel of his Jeep.
It took me a second to process that my best friend was now fucking my ex-husband. Suddenly, I felt dizzy, and put my hand against the wall for support. My blood turned cold.
“How long has this been going on?” I demanded.
“I’m sorry, sweetie, but Glenn is a good man, and…”
“HOW LONG?” I shouted, slapping the wall. Thankfully, my 17-year-old who still lived at home was staying at Glenn’s for the week, so he didn’t hear me.
“About a month,” she answered quietly.
“So right after our divorce was finalized, you jumped into his bed.”
“Now, Judy honey, be fair. He didn’t cheat on you, we waited until it was official. Besides, I didn’t jump into his bed, it was more like he jumped into mine. You hadn’t given him any loving for at least 6 months, so he was ready to come get some.”
That wasn’t entirely true. Our divorce was an amicable one; once Terry and Sean had reached the point where they didn’t need much parenting, Glenn and I had just grown apart, with different interests and wanting different things out of life. Apparently he’d not told Jackie that while the divorce was being finalized, every once in a while Glenn would sleep over at the house escort izmir ‘for old time’s sake’.
Since the divorce had been filed the pressure was off, and it actually made no-strings sex-with-the-ex more enjoyable than when we were married, even if he did have to use condoms. (If he’d gotten me pregnant at 42, that would certainly have been awkward, not to mention expensive for him due to 18 more years of child support.)
What really hurt me was Glenn moving on so quickly, while I was still mourning the divorce. Then again, Jackie was a very welcoming refuge for him; she’d always had her eye on my husband, going way back to our wedding reception. I’ll bet the little tramp spread her legs for him as soon as he’d said “Hello.”
Then I wondered how Terry and Sean, at 19 and 17, would react to their doting Aunt Jackie becoming their new mommy. They’d been complete momma’s boys until puberty hit, when suddenly Glenn became their hero while I was relegated to a minor character in their lives. Given that, I was sure they’d adjust just fine.
Not saying another word, as tears filled my eyes I pushed Jackie out the door and slammed it. She and Glenn were both dead to me now.
So here I was, lonely and sad at a party that I only came to because I was running on emotional autopilot after finding out my best friend had stabbed me in the back. After drinking way more champagne than I should have, it was 11:58pm on New Year’s Eve and I was an emotional train wreck. Then suddenly, a very tall baby appeared before me, wearing only a diaper and a banner/sash thingie like Miss America wears, which read “Happy New Year!”
Upon closer examination he looked to be about my older son’s age, and to my alcohol-soaked eyes he was the cutest thing I’d ever seen. As the ten-second countdown to midnight began, I grabbed him and kissed him like there was no tomorrow.
This mystery woman and I kissed about 30 seconds after the ball dropped, her hands roaming my back and squeezing my ass. I hoped my erection would remain within the friendly confines of the diaper, lest everyone in the party get a look at my cockhead peeping over the top.
Finally she pulled away, and I took a good look at her. Despite her smeared red lipstick and disheveled red hair, she looked gorgeous in a clingy green dress. About 5’7″, she was a little thicker than the average party girl, but everything about her exuded sexual energy.
“Heyyyyy, handsome baby, thankssss for the kisssss,” she slurred. I noticed she was none too steady on her stiletto heels. I became concerned she might twist her ankle.
“The pleasure was all mine,” I assured her, “now I’m happy I lost the coin toss and had to wear this stupid diaper. You made it all worthwhile.”
She narrowed her eyes and smiled seductively. “What’s your name, hannndsome baaaaby?”
“My name’s Matthew. What’s yours, pretty lady in green?”
“I’m Judy. Tell me, handsome Matthew, do you believe in love at fffirst ssssight?”
“I’m not sure, but I guess it’s possible.” She leaned in and pulled my face to hers for another long kiss, and this time running her tongue teasingly across my lips.
Then she leaned in and whispered in my ear. “I’m gonnna tell you a secret, OK? I wass unhappily married for 20 yearsss, and didn’t love my husband asss much as I love you right NOW.”
I was probably just hearing the champagne talking, but she was so pretty I had to go along with it. “What does that mean, exactly, beautiful Judy?”
She kissed me again, and did things with her tongue in my mouth that I’d never felt before. I pulled her to me, as much to squeeze her ass as to hide my firm erection from any onlookers. Maybe it was the heat from the crowded ballroom, but I was sweating profusely when she stopped. “It means, handsome Matthew, that I am yours, body and soul. Kill me or marry me, either way it doesn’t matter. My flesh and my heart belong to you forever; you can do no wrong.”
When I woke up, the sunlight blazing in the window made my head throb. I had no idea where I was, but the bedroom I was in was well-furnished and looked to have an attached bedroom. I looked under the sheets and was shocked by my naked body. It was not just me being naked that was startling, but that I smelled like I’d been thoroughly and completely fucked, and my breasts were covered with bite marks. Reaching down to touch my labia, I was shocked as to how tender they were, and how much fluid seemed to be coming from between them.
Just then the door opened, and a young man walked in carrying a tray. Shirtless and wearing some tight jeans, he looked quite familiar, very cute in fact. He sat the tray on the nightstand. Judging by the look on his face, he was quite pleased to see me.
Sitting on the edge of the bed, he extended a champagne flute with orange liquid. “Ah, you’re awake! Excellent! I brought you a mimosa — a little hair of the izmir escort bayan dog — and some toast to get some food in your stomach.”
I took a sip of the wonderfully cool drink, and my memory started to piece together the events of the night before. His name was Martin — no wait, that wasn’t right. This was Matthew, the young man dressed up as Baby New Year!
I managed to find my voice, although it was somewhat croaky. “Thank you, Matthew. Where exactly am I?”
“You’re one of the guest rooms of my parent’s mansion. That’s Paul and Victoria Taylor, to be specific. You’re one of several people that stayed here for their own safety after having had too much to drink last night.”
HOLY SHIT! I told myself to stay calm, this was no time to panic. “Matthew, I seem to have not been alone last night. Can you verify that?”
A wicked smile crossed his face, and he shocked me by leaning down and kissing me. This was no polite peck, it was a passionate thank-you-for-fucking-me-kiss. That’s when memories started trickling in. “I most certainly can. I was with you most of the time.”
I flashed on my telling Matthew that I loved him more than my ex-husband. Uh oh. Matthew stood up and pulled off his jeans, and not only was he devoid of any underwear, but his cock was fully erect.
“I was with you, and now I’m back.” Slipping under the covers, he downed the remainder of my mimosa and put the glass on the tray, then pushed me back on the bed, spread my legs and entered me.
As he began thrusting, he growled, “Judy Beckman, you were the best fuck I ever had in my life, and I’m afraid you’re stuck with me now. I can’t let you go.”
I winced at his entrance. “Please Matthew, go slowly, I’m really tender. How many times did we do it last night?”
He slowed, and his movements became quite tender. “You and I did it five times. You and my brother Phil did it four. Then we did it one more time each together.”
That’s when another memory hit me — it seemed like at some point there were two Matthews. I had one on either side of me, their fingers probing my pussy while each suckled and kissed a breast; I seemed to recall cumming like a freight train.
“You mean that wasn’t a dream?”
“Oh, no. We’re very close, Phil and I. I asked you if he could join us, and you really seemed to welcome it. We started off doing tag team, where one of us would rest while the other was fucking you, but then we both had you at once. You know, the old spit-roast where one of us got sucked while the other was working on your pussy. You kept saying how bad your ex made you feel by fucking your best friend right away, but we two studs made you feel so good, like the sexiest slut in the world.”
Hearing those words made me shiver, and I felt another climax building. “Matthew, please don’t stop,” I begged, “just kiss me and fuck me harder!”
Lowering his lips to mine, he began plunging harder. I must have been full of cum because the wet squishing sound of his cock pistoned in and out of me was very prominent. Suddenly, I felt it happening. Digging my heels into the mattress, I arched my back and stiffened.
“YESSSSSSS, fuck MEEEE!” I hissed, as an orgasm wave ripped through me. I clamped my pelvic muscles down as hard as I could, and it seemed to do the trick for Matthew as well.
He began to stiffen, but what he cried out as he let loose his load shocked me. “Oh, SHIIIIIT! I LOVE YOU JUDY!”
After his release, we kissed softly as we both lay there recovering, and I realized I might have unintentionally gotten a man – not much older than my first marriage was long – to fall in love with me. Of course, a man in the throes of sexual release will say damn near anything just so long as it results in his cum emptying his balls so this could just be his testicles making him say that, but it would be interesting to see where things went from this point.
I honestly thought that after fucking Judy all night I didn’t have another drop in me, but as soon as I walked in that guest room and saw her, I wanted her again. I had wanted her all to myself when I’d led her to the guest room, but Phil had seen me.
“Dude, you’re going to tap that MILF? She’s pretty fucking hot! Mind if I join you?”
I sighed. Of the two of us, I was the romantic, my brother was the horndog. He was leaving for London in the morning to start a job there, so we wouldn’t be seeing each other for at least 6 months.
“OK, but I get to go first, then we’ll tag-team her.” We’d done this a few times in college, with the girl’s consent of course, and it was always an enjoyable time for the woman in question.
We did this for a few hours, with one of us resting while the other kept fucking, and Judy kept cumming over and over. I’d stop from time to time and take her to the toilet, wipe her down with a washrag, then give her some water to hydrate her before offering her more champagne.
By the fourth hour she was covered with sweat, and her hair izmir escortlar was a real mess, but that just made me want her more. And every time I told her how beautiful she was and what an idiot her ex was for letting her go, it was like a switch had been flipped in her and she was urging me on, begging me to bite her tits and fuck her harder. When I told her my twin brother thought she was hot and wanted to join us, she was all for it. We spit-roasted her for a while, and honestly her mouth was as fuckable as her pussy.
But it was when we were simultaneously sucking her nipples and fingering her that she shook so hard from the resulting orgasm, I thought the bed was going to collapse before she did. It was about 4am when she passed out for good, and Phil took off for the airport. I spooned with her and kept caressing her tits before I finally fell asleep myself. Despite me being exhausted and my balls being totally depleted, I found myself still partially erect and wanting to fuck again, even as I surrendered to the arms of Morpheus. Once there, I fucked her in my dreams.
It had been an eventful 8 weeks since I woke up after my night of debauchery in the Taylor mansion.
First, my 19-year-old son Terry announced he’d joined the Navy. I found this quite ironic because his father was hydrophobic. Then my 17-year-old son Sean dropped the bomb that since he now had a girlfriend who lived close to his dad’s place, he wanted to live with his father full time to always be near her. Ah, young love. He’d be turning 18 in a couple of months, so there was no point to me objecting. It hurt, but that’s parenting for you. I just hoped that my son would invite me to the eventual wedding, even if Jackie would be the mother of the groom. (Was I being overly dramatic? Sorry, not sorry.)
Of course it was bound to happen that Jackie got engaged to Glenn three fucking months after our divorce was finalized, because my ex is the kind of man who needs to be married. He may have been a tiger at his import/export business, but at home he was a weak man-child who needs a strong woman to make decisions for him. With me out of the picture, my ex-best friend stepped right up to be that woman.
On the positive side, there was Matthew Taylor. As it turned out, my Baby New Year man was older than he looked, 26. He and his brother worked as investment bankers, Matthew in Manhattan, and Phil in London. When I finally managed to get out of bed to get breakfast and take my walk of shame, I was shocked at what I saw in the mirror. My makeup was smeared so I looked like the Phantom of the Opera, my hair looked like a veritable rat’s nest, and yet… I was happy. Happy that despite my earlier fears I wasn’t just some boring middle-aged divorced homemaker, happy that I’d sexually satisfied two young and very handsome men, happy that one of them even kept telling me he loved me, even in the days following when I was certain he’d chalk me up as just another quick fuck and forget my name soon after.
Since New York’s financial industry work day went from 9:30am to 4:00pm, after Matthew had gone to the gym to work out or play squash, he’d often bring by flowers or carryout dinners to my house out in Cambria Heights. Emptied of my two sons it was now a terribly lonely place, and I’d repeatedly considered selling my half to Glenn. On the other hand, Matthew’s presence made the place bearable. And by bearable I mean we’d made love on damn near every flat surface in the place — every bed, the dining room table, the kitchen counters, you name it.
That was the thing about Matthew, he was a real romantic at heart. Recalling our night of debauchery with his brother, I realized that while Phil had fucked me roughly, Matthew was the one tenderly making love to me, telling me how wonderful I was, and telling me — repeatedly — that he loved me. I shiver thinking about it to this day.
Despite my occasionally telling him he needed to find someone younger, his devotion never wavered. When my sons both forgot to call me on my 43rd birthday, Matthew knew how hurt I was and stepped in, taking me to a little bed and breakfast place on the beach in New Haven Connecticut. While we were there, he mentioned the idea of getting married.
As much as I was growing to love him, I reminded him I was 16 years older and didn’t see him still loving me when I was an aging 55, and he was a youthful 39. I also told him how I was perimenopausal and my doctor had told me my fertility was dropping like the S&P 500 in a bear market, so I doubted I could give him a family.
Being Matthew, his response was to quote Wayne Gretzky, saying “You miss 100% of the shots you don’t take”, then promptly stripping me naked and taking me on the floor in front of the fireplace, then again in the shower afterwards.
What was most worrisome was, in the past few weeks I’d started not feeling well. I began experiencing nausea, fatigue, slight soreness in my back and in my breasts, and my feet were a little swollen. A quick trip to the doctor resulted in her requesting a sonogram for me. I laughed, telling her “I can’t be pregnant, you told me my fertility was basically vanishing, right?”
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