I cracked an eye open, the previous night coming back to me as my brain woke up.
Max.
After taking me from behind, I’d collapsed in a boneless, spent pile of goo. I’d planned on getting up to splash some water on my face and leave, but he’d pulled me close. Then I’d planned on enjoying some post-sex snuggles, which had obviously resulted in post-sex sleep. Well, for a few hours. After that, Max had woken me up with his mouth on my pussy.
I’d happily leapt from the bed, racing to grab a condom from my stash in my purse. Rolling it on him, I’d climbed up and gone to town. Once we’d both finished, I was fairly certain I’d fallen asleep on him.
Tiny hints of sunlight began to peek into the room. Taking that as my cue, I carefully slid out from under his arm and headed for the bathroom.
I’m sore.
And turned on.
And now I’m extra turned on because I’m sore and turned on.
The promise of leaving a girl still feeling it the next day was thrown around a lot, but not often fulfilled. Twinges, sure. Maybe the occasional dull ache. But that deep tenderness, leaving them wet and wanting every time they moved?
That didn’t happen often, and it was a shame. Because with every step I took, that pleasant pain reminded me of the night before.
After using the bathroom, I washed my streaky makeup off and headed back into the room. I scooped up my clothes and scanned the room for my bra and panties. Not finding them, I went into the main area before slipping my borrowed dress on.
Hmm, this baby is lucky. Maybe Katie won’t even notice it missing.
Uhh, actually, I’m thinking it isn’t the best idea to steal from a cop.
I slid on my shoes and cardigan, grabbed my wristlet, and left the room, easing the door closed behind me.
Walk of shames didn’t exist in my world. In my cartoon outlook, I pictured confetti falling as I walked through the lobby. Like an athlete leaving the arena, a crowd of cheering people would line up on both sides of my path, waiting for high-fives. Depending on how good it was, there may even be a fog or bubble machine.
If I was going by the night before with Max, there’d definitely have been a parade waiting outside, including floats and those giant balloons. Probably fireworks, too.
When I reached my car, I drove straight to coffee.
I thought about Max the whole way.
*******
My hair was piled up on my head, I smelled, and I hadn’t eaten since the night before.
Okay, I’d had some cheeseballs for breakfast with my coffee, but I hadn’t had many.
The important thing was I was going to make my deadline.
I looked down at my finished ‘Winnie Mae’ comic, feeling like it was one of my best. Using my early morning experience, I’d drawn my black dress outfit on a bedroom floor. Instead of strewn about, though, it was connected with those clips that little kids used to keep track of their mittens. The next panel showed cartoon me holding my sweater and dragging the rest of the clothes in a connected line.
I scanned it into the computer before tweaking it. Once I finished, I put the label ‘In the perfect world’ above the first picture. On the bottom of the last panel, right under the panties and bra at the end of my clothes line, I typed ‘Winnie Mae need new underwear’.
I saved it, grinning to myself like a loon.
My first and middle name had presented the perfect way to put my doodling skills to productive use. A fun and often self-deprecating comic, it often described what Winnie may need or have.
Since my hands weren’t cramping yet, I moved on to another idea. I sketched Emma and Wyatt talking in the first panel, showing them from the shoulders up. I added a bunch of thought bubbles that said things like ‘He’s not tall enough’, ‘So boring’, ‘Why is he telling me all this’, and other random negative or unrelated things. In the next panel, I only did one thought bubble with an extended ‘Squuuueeeeeeeee!’ taking up most of it.
Scanning it in, it took me a little longer to rework. Once I was satisfied, I put ‘What men think women are thinking’ on the first panel. The second had ‘What women are really thinking’. Looking it over, I decided on an asterisk at the top corner with the warning label ‘Only applies if neither of you are a douche’.
The added ‘Winnie Mae have the best friend ever’ completed another comic, but I didn’t send it off yet.
“Holy shit, you’re up,” Emma muttered, shuffling past me on the way to the kitchen. “Or still up? What time did you get in?”
“Like six.”
“Nice.” She fixed herself a cup of coffee before trudging back to me. Looking over my shoulder, she giggled. “That’s insanely accurate.”
“Can I use it?” I asked. I’d added cartoon Emma into other comics before, but I always got her permission before using them officially.
She waved away my question, which was her usual response. “So—” she started as her phone rang. Looking down, her eyes widened and she smiled. “It’s Wyatt.” She touched the screen, putting the phone to her ear. I heard her greeting as she retreated toward her room. The shower started a minute later.
I emailed the comics off to my tech girl who would add them to my site when the time came. I only put out on comic every two days, but I liked to have a backup stock. My fingers were starting to get tense, signaling it was time to wrap things up. I jotted some ideas on sticky notes, popping them all over my giant computer monitor.
“We’re going to brunch and then out,” Emma announced excitedly, hurrying toward the door. She hopped around as she slipped her sneakers on. “I didn’t think I’d hear from him so quickly.”
“I don’t see why you’re surprised; he’s obviously super into you.”
“You think?” She deftly braided her damp blond hair.
“I’ve got eyes and a brain, don’t I?”
The buzzer went off, interrupting us.
“That’s him,” she said, and I could practically hear her internal squeal. “Want me to bring you anything home?”
I shook my head. “I’m finishing up my work and then heading to bed for an hour or seven. Have fun.”
After she left, I grabbed my cell and went into my room. Usually with the place to myself, my battery operated boyfriend and I would be having some quality time together. Since that wasn’t necessary after the night before, I swiped across the screen and reviewed my phone notifications. I was about to set it aside when it chimed, a messenger bubble popping up.
MA7: Did it hit midnight, Cinderella?
I didn’t recognize the name.
WinnieM: Who is this?
MA7: Max.
I was more than a little surprised, and not just because I’d never given him my contact info. Curious, too. Beyond that, though, I couldn’t deny how happy I was. He’d been in the back of my head all day.
What do you say to a guy you had incredible sex with the night before and then ditched in the morning?
WinnieM: Hey.
MA7: I hope you don’t mind me messaging you. Not stalking you or anything, you’re on Emma’s friends list.
WinnieM: So only kind of stalking?
MA7: Very mildly.
MA7: What’re you doing?
WinnieM: About to nap. I didn’t get much sleep last night…
MA7: I’d comment further on that, but then I’d get even more off track. Dinner tonight?
I was tempted. As fun as it had been being Winifred, I really regretted it when it came to Max. By sleeping with him, my harmless lies had turned into major ones. I’d mislead him, and it didn’t sit right with me. But neither did the idea of coming clean.
So, I’m not a horrible person, but not a good one, either.
At that moment, Max was an insanely hot man I’d had unbeliev
able sex with. I didn’t have to worry about things getting messy. It could stay an untainted memory of amazing orgasms.
WinnieM: I have a deadline I have to make. It’s why I ducked out early today.
I knew I should just be honest, but I couldn’t seem to bring myself to make the clean cut.
I’m a bad person.
MA7: Maybe some other time…
It was a message, making it nearly impossible to tell the true tone that was intended. But somehow I knew it was dismissive. We both knew there would be no other time.
And that bummed me out way more than it should’ve.
Chapter Five
Drunken Dildo Decisions
Drunk decisions were rarely good ones.
Tipsy as hell, I blinked down at my phone. I had Max’s message all geared up, but I was trying to convince myself not to send anything.
After our exchange that morning, I’d slept for a few hours before meeting up with some friends. One glass of wine had turned into a bottle, and I was drunk.
And horny.
And I missed Max.
Even intoxicated-me realized it was stupid since I barely knew him. I wasn’t one to ever be blinded by good dick, but I was beginning to wonder.
Maybe I just need an orgasm to clear my head.
Taking out my rabbit vibrator, I slid it in, using my bent leg to keep it in place. Still, I couldn’t help myself.
WinnieM: Hey.
I didn’t even have time to fret before a return message popped up.
MA7: Hey. Nice surprise.
WinnieM: Yeah, sorry, I know it’s late.
MA7: I was up. What’re you doing?
WinnieM: Masturbating.
I couldn’t believe I’d actually typed it. I could’ve blamed the booze, which I’m sure hadn’t helped, but I probably would have still said it had I been sober.
MA7: I just spit beer all over myself.
MA7: I also got insanely hard.
WinnieM: Sorry, that was probably inappropriate. I’m also drunk.
MA7: No, no. That’s the kind of info I think should be shared. Feel free to message me any and all times you decide to masturbate.
WinnieM: I don’t think my phone is equipped to send that many messages.
MA7: I don’t even know what to say to that.
MA7: I’m caught between wondering if this is a prank, and not wanting to know if it is.
I snapped a pic of my face. It probably wasn’t the most flattering angle, plus my hair was a mess and I was clearly drunk. But I sent it.
MA7: Okay, so it is you. I’m kicking my ass for even asking this, but are you sure you’re messaging the right person?
WinnieM: Did we have the best sex of my life last night?
MA7: Best of mine, that’s for sure.
WinnieM: Then, yes, I’ve got the right person.
MA7: Wait. Did you take that pic while you’re masturbating?
WinnieM: Maybe… I mean, I’m not hardcore going at it, but it’s in as a pleasant tease.
MA7: Holy fucking shit.
MA7: You keep me on my toes, Win. I like that.
WinnieM: I’m glad.
WinnieM: I’m tempted to ask you to come over, but I don’t think I’ll be able to wait that long. Or stay awake.
This time, I did hesitate before pressing send. I knew I was leading him on, but I couldn’t stop. It was that connection I’d felt the night before, pulling at me.
Maybe he’d understand about my Winifred antics. He did say he likes that I keep him on his toes.
I pictured his clean cut, professional appearance and mature vibe.
Or maybe he won’t like the real me, and I’ll further taint the memory of amazing sex.
MA7: Call me then.
When the next message popped up with his number, I quickly dialed it.
“Hello?” he answered on the first ring.
“Hey,” I whispered.
“Fuck.”
“That’s what I wish we were doing, yes.”
We spent fifteen minutes having graphic and intense phone sex. The vibrator was a big help, but just the sound of Max’s breathing and low groans would have been enough to get me off.
Even after coming, the sound of him catching his breath was turning me on.
“Fuck,” he growled again. “I’ve never had phone sex before.”
“‘S’good?” I asked with a yawn as I put my toy to the side, working up the energy to go clean it.
“Yeah, it’s better than good.” His voice softened. “Tired?”
“Uh huh,” I whispered. “Wine and orgasms make me sleepy.”
“Get some rest then. Message me tomorrow, even if it isn’t for a repeat.”
“‘Kay.”
“Night, Win.”
“Night, Max.”
Drunk decisions are the best decisions.
*******
Vrrrrooooooommmmbbbrrrrvvvvvaaaaabbpppprrrrrr.
Swatting at my face, I tried to open my eyes. When only one of them opened, I looked to see my bright pink bunny vibrator right in front of me, pressing on my closed eye. I must’ve switched it on in my sleep, because the thing was revving at high power.
I’d had a lot of interesting mornings in my life. But I was fairly certain a vibrating dildo to the eye was top of the list.
There has to be a ‘Winnie Mae’ comic in this somehow.
Still bleary eyed, I grabbed my phone to check the time. There was a waiting message from Max.
MA7: Morning. Thanks for the fun call last night. Feel free to message more often. Daily, even.
WinnieM: It was fun, and worth waking up with a vibrating toy trying to have its way with my eye.
Pressing send, I saw it was obscenely early, meaning it was before noon. I rolled onto my side and was back asleep within a minute.
*******
Grabbing a new sharpened pencil from my hair, I drew some extra details on the small and abnormally shaped penis before scanning it into my computer. The comic had the cartoon version of me noticing she had over thirty new app messages. The next panel said ‘Now to delete the unsolicited dick pics’ and had the weird dick drawing. Cartoon me was irked in the last panel, a big ‘Zero Messages’ label over her head. ‘Winnie Mae need to delete her online dating apps’ ran along the bottom edge.
I was really happy with how efficient I was getting. I sent it to my tech girl, and leaned back, stretching. As I was trying to decide whether to start another one, my phone dinged.
Like Pavlov’s dog, the noise caused an immediate and automatic reaction. Hopefully unlike Pavlov’s dog, my reaction was my heart rate speeding up and my panties getting wet.
For a week, Max and I had messaged nearly nonstop. I had to guard what I said to him, but I had started being more open. It went well beyond naughty messages and phone sex, although those were regular occurrences, too. Everyday, he asked me out to dinner. And everyday I said no.
I was sick of saying no.
MA7: What’re you doing?
WinnieM: Thinking about tiny, weirdly shaped dick pics. You?
MA7: Well now I’m thinking about tiny, weirdly shaped dick pics, too. If that’s a hint you want one from me, that kind of flattery will get you everywhere.
WinnieM: Ha. I was thinking about unsolicited ones. Yours would definitely be solicited. Wait, I’m pretty sure that’s a crime.
MA7: Only if you pay for it.
WinnieM: Well, that’s good to know.
MA7: Any reason you’re thinking about tiny dicks?
I needed to tell him the truth. I wasn’t being as careful with what I said, and he still seemed interested. I started to type my response, but then deleted it.
WinnieM: I’m not anymore. Now I’m thinking about your dick, which is far from tiny, as you know. And, as I said, very solicited.
MA7: It’s still nice to hear. What’re you thinking about?
Liking where this was headed, I went into the bedroom before answering. By the time I undressed, got into bed, and got a toy set, there were two messages waiting.
One was a picture. Max’s fist was wrapped tight around his hard cock. I took my time zooming in, not that it needed it, of course. But between the hand and the cock, there were a lot of veins that deserved a close-up look. There was even a little moisture on the tip.
MA7: Thinking about how it felt when I was in you? How hard you came? What about how good I could make you come again?
Previously, I’d run the show when we messed around. Max was an active participant, but I’d taken the lead.
Apparently, that was changing.
I was good with it.
Inhaling, I lowered my phone and snapped a picture. I cropped it so nothing but my pussy and toy were showing. The bunny ears perfectly surrounded my clit. I was tempted to add some filters and editing, maybe an inspirational quote, but I sent it before I could lose my nerve.
Less than thirty seconds later, my phone rang.
“Fuck, Win,” Max said by way of greeting as soon as the call connected.
“I figured it was only fair.”
“What I wouldn’t fucking give to be the one sliding inside you right now.”
I gave a soft laugh that turned into a gasp as the toy hit my clit just right. “I think that would constitute the illegal kind of soliciting.”
“Worth it.”
A silence fell between us. Well, not so much a silence, since there were a lot of moans, groans, grunts, and sighs. But no words were spoken. Instead, we just listened to the other getting off. It was strangely more intimate than had we been talking.
My breath caught as my orgasm began. I told myself to stop, not wanting this to be over yet, but it was too late. I came hard, vaguely aware of Max’s matching low groan.
We stayed quiet for a few minutes, long enough that I began to wonder if he’d fallen asleep.
“I miss you,” he said finally, making my breath catch for a new reason.
Little Black Dress Page 16