Stumpy and Olive

I'd like to see the school girl outfit(although in my fantasy, you're wearing a bustier, and thigh highs, under a slinky silk dress that slides off easily. I'd unwrap you slowly, like the best present I've ever gotten, drop the dress off your shoulders, slip the detachable cups off the bustier and slowly lick your...wait, what were we talking about? Oh yeah, school outfit), those incredibly long legs barely covered by your little plaid skirt, cute little white panties peeking out as you bend over my lap. I'd have to fondle it a bit before the spanking began, then...damn, gotta go, something smells like it's overheating.

And you reek of hotness. My nose knows.

LUBX4, Stumpy.

I pushed back from the computer, looking at the bulge in my shorts. Damn, I needed to be laid in the worst way.

...

I pushed back from the computer table, my face flushed, my breathing ragged. I looked down to see my nipples standing straight out, hard as I've ever felt them. I had been squirming on my chair, and I could smell myself. I'd have to wash that cushion soon. Serves me right for sitting down naked. I left the computer open, and wandered to the bedroom, trying to remember where I'd stashed BOB, and if the batteries were still good.

An hour and three orgasms later, I was finally able to answer him.

Stumpy, darling,

How sweet you are. I don't have a bustier(yet), but I do have one little outfit I bought for myself after the divorce. I'll only wear it when I find the man I'm meant to spend the rest of my life with. It's a sheer lace, baby blue, one piece that can only be worn once, because after I put it on, it has to be unraveled to be removed.

And it has to be done slowly, for full effect.

It's symbolic of me shedding my old life, appearing to my man brand new, just for him, forever. Stupidly romantic, I know, but it means a lot to me.

All the love I have, Olive.

...

I'd never read anything so heartfelt, so genuine, that it hit me hard. All she wanted was to be loved by the right man, and she would belong to him forever.

I had to walk away from the computer for a while, there must be dust in here because I was misting up.

I thought about it a long time, almost a week. I wanted to meet this woman more than anything I'd ever wanted in my entire life. I was on a mission when I emailed her again.

Dearest Olive,

It's time. Time for us to meet, and go on a real date. Time to separate the fantasy from the reality. You may not like me. I might find you irritating. The only way to know for sure is to spend time together.

The thought of being with another woman has me tied up in knots. What if she's a bad person, what if she destroys me again? Could I take another hit that hard? So for the last year I've stayed away from women because of fear. With you, I have no fear. And paradoxically, that scares the hell out of me.

But I'm willing to take that chance. One thing though, if you're willing to do this. I don't want to know what you look like until we meet, or hear your voice. I'd rather see you for the first time face to face, try to catch the emotion in your voice, to gauge your reactions, see how quick you are on your feet. I guess I'm just a delayed gratification type of guy. The anticipation, to me, heightens the experience.

So, Sweet Olive, what do you say? Do we stay anonymous and safe, or go for the real, the raw, the unexpected? Your choice.

Think about it, I'll be waiting.

Just Love, Stumpy

I took a deep breath and hit send.

...

I stared at the screen for a long time. Did I want this? What if he's a bad person, has body odor and an annoying voice? Well, there was only one way to find out.

Stumpy,

Name the time and place. Maybe this time I'll have the bells on.

Olive

...

She actually said yes! Now, I had to figure out how, when and where to meet. I actually talked about it to my sister Emily, telling her the whole story, letting her read the emails. It took her almost two hours.

When she was done she sat back and grinned at me.

"Wow! You guys are made for each other. You need to go for it and meet her, soon."

"I agree, but it has to be perfect. Suggestions?"

We talked for an hour, discussing different options. Dinner? Drinks? A club, a park, anywhere. Finally Em smiled.

"I know just the thing. Invite her to our Christmas party! It's three weeks away so she'll have time to decide what she wants to wear, or even if she wants to go."

The company Christmas party was a big event. All our managers, vendors, and a few select friends attended. The managers because they got their year end bonuses then, the vendors in appreciation, the friends because it was always fun. It was semi-formal, and the ladies went all out, while the men wore really nice suits. There were always between a hundred fifty to two hundred in attendance. We usually booked a really nice venue, had an excellent meal catered, made the mandatory speeches, then opened the bar and let the dancing begin. The band was always top notch, able to play something for every taste. Mom had made us all take lessons, and we usually opened the floor with a slow number, with mostly just family dancing. My ex didn't like to dance with me because of our great height disparity, she said she felt like she was six years old dancing with her grandfather. It hurt me, but I blew it off.

"I don't know, sis, don't you think it will be a bit much? Our family is not exactly shy. The poor woman might not have a good time."

"Leave it to me. I'll make sure the family gives you privacy, well, as much as possible. And if you two get close, she'll have to get used to them eventually. Better to get it over with right off the bat."

I looked at her trying to stifle a laugh, and agreed.

...

Olive,

I formally request you accompany to my company Christmas gathering. My company goes all out, and it's usually a lot of fun. If you agree, I'll give you the details. I've thought a lot about this. These are the people I spend most of my time with, and if we become close you'd have to meet most of them eventually. And I promise, there will be a quiet place we can talk, without interruption. Think about it, it's three weeks from Saturday. I really hope you attend, I've told my friends that I've been talking with a really hot woman, and since I haven't dated in almost a year, half of them think I made you up.

Stumpy.

...

I talked it over with my friends, and my mom before answering. I'd hoped for something a little more intimate, wondering why he wanted our first date to be in a crowd. Mom clarified it for me.

"I think he wants you to feel comfortable, honey. You're meeting a stranger, which would you rather, a large open space surrounded by people, or a dark lounge where you can't hear each other talk."

Looking at it in that light, I sent him my reply.

Darling Stumpy,

I accept your kind invitation, if you agree to attend my company function the following week. That's contingent, of course, if we can stand each other. I'm a girl, so I'll need details, dress especially.

Looking forward, Olive.

...

She said yes! It felt better than when Ginny Gilbert accepted my junior prom invitation.

Sweet Olive,

The dress is semi-formal, but I'd be remiss if I didn't mention the women usually went all out, competing a little, I guess. I work for the Stevens Automotive Group, and the party will be held at the Grove Inn. It starts at eight, with dinner, then there'll be a few short speeches, followed by dancing and an open bar.

And I'd love to party with a bunch of lawyers. I bet you guys sit around and tell fart jokes and see who can pass out the fastest. I'm in.

...

Well. The Stevens Auto Group. I knew a little about them through my firm, they were probably the biggest franchise in the state, seven dealerships, and were about to add an eight. I wonder which dealership he worked at? And the Grove Inn? It was almost impossible for a normal person to get to see the inside of the place. Only the cream of the local society set frequented it.

One of the partners at my firm had actually attended one of their parties, a date of one of their suppliers. She said she was sure I'd have a good time. When she described the dresses, I knew there was a shopping trip in my immediate future.

I suddenly had a thought. What if he was really short? I guess I'd have to wear flats. I actually told him I'd be wearing them, and was surprised by his response.

...

Olive,

what's the highest heels you own? Never mind. If the heels you have on when we meet aren't at least four inches, there will be a serious spanking in your future. I'm not kidding, I absolutely adore women in heels, especially when that's all they have on. Oops, did I really type that? Disregard that last(or not).

See you in seventeen days and five hours, Stumpy.

...

Four inches? Really? The highest pair I owned were only two and a half, but what girl needs motivation to go shoe shopping? My friends giggled when they went with me and I tried on a pair, stumbling slightly from the newness.

"Would you look at that! Our girl Amber in high heels. And not just high heels, genuine CFM's!"

The salesgirl snorted back a laugh while I looked puzzled.

"Come on, Amber, you know, Come Fuck Me heels."

I flashed bright red before grinning, eyeing the shoes in the mirror. "Well, I certainly hope so," I said, making them laugh harder.

After three stores and fourteen pair, I finally found a pair I adored. Basic black strappies, but damn they made me legs look great. I made a visit to a very nice lingerie store, picking up three sets of thigh highs, and a really hot looking bustier. It shaped me, pushing the girls straight out and putting extra curving on my bottom.

In a flash of inspiration, I put the basic black dress I'd be wearing on, with a pair of patterned black thigh highs and my new shoes. I experimented in front of the mirror until I got just the shot I wanted, My high heel encased foot and my leg, all the way up to the band of my thigh highs. I sent it to him ten days before our date.

Stumpy baby,

I know we're not supposed to see each other until we meet, but I just had to show you my new shoes. Do you like them? What do you think of the hose? Too much? Give me an opinion.

your Olive

...

I opened the email at work late that evening. Big mistake. It was hot! And I mean HOT! I had to sit at my desk for thirty minutes before my erection went down. I seriously thought of ducking into the bathroom to help it along a little. Then I had a better idea.

Sexy Olive, baby,

I'm not an expert on ladies shoewear, but that is a damned impressive set of footwear! The leg looks really great, I can't wait to see the matched set. Words fail me trying to describe how hot you look, but then again, all the blood is rushing from my brain, making it hard to form coherent sentences. I think a picture is worth a thousand words, so I'm sending you one that will show you exactly how impressed I am.

The days aren't passing fast enough for me, Stumpy.

I know it was juvenile, but I sent her a picture of my erection, plain to see through the khaki pants I was wearing.

...

Wow. I wasn't sure exactly what to make of that. Finally I decided to take it in the spirit of our emails. After all, it was just a bulge in some slacks. I couldn't help enlarging it a bit, deciding it was a really nice bulge.

Stumpy, you little horn dog,

Thanks, I think. It's nice to be appreciated. And I WILL be wearing the bustier and thigh highs to the party, and no other 'foundation' garments under my dress. You won't get to see anything, although if you're a good boy some touching may take place.

Olive

...

Olive, you little tease,

Stop doing that! I read most of your emails at work because of my hours, and my secretary always knows when I get one of your notes. She just grins, looks at my crotch, and asks when she'll finally get to meet you.

When I told her you were my date for the Christmas party she frowned, asking me if I thought it appropriate to expose you to my family so soon. I forgot, but most of my family works for Stevens at different locations. They can be a bit overwhelming. My sister promised me she'd do her best to limit your exposure. She said she'd try, anyway.

See you in 183 hours and forty-nine minutes,

Stumpy.

...

His whole family at once? I wasn't too happy about that. Mom just grinned.

"Better to get it over with quick. I know, tell him you want to bring me along to level the field. I've always wanted to party at the Grove Inn."

I knew she was kidding. Mom had been at loose ends for the past two years, ever since my Dad traded her in for a woman almost as young as me. It took her months to come to terms with it, and she was just now starting to be interested in men again. We were both hit about the same time, and sharing each others' misery had helped us heal. I hadn't spoken to my father but once since, telling him what an asshole he was, and that I'd laugh when she cheated on him. "After all, she as a history of it, doesn't she?" He slammed the phone down. He moved across the country, and I hadn't seen or spoke to him in sixteen months.

I mentioned in passing what my mother had said in my next email, and was surprised at his response.

...

Sweetie,

By all means, bring her along. It would make me feel better about dumping my whole family on you. After all, sooner or later she'll have to inspect me, and meet my family, look how much time we'd save.

Oh, I have a Christmas present for you. My company usually retains a few rooms for those who have just a bit too much fun, and my bosses agreed to let me have a small suite for the night.

Before you get any ideas, I was thinking maybe you and your mother could have it. That way you wouldn't have to be driving, could relax, and have a good time. It doesn't mean I won't be there, I intend to take you both down to the Sunday brunch the Inn is famous for. We'll get to spend even more time together. Tell me soon, there are others who would enjoy the suite if you don't want it.

One hundred forty nine hours and seven minutes, Stumpy.

...

It's kind of hard to shock my mother, but I think he succeeded. When I told her I was going to decline, she slapped me on the back of my head.

"Oh no you're not! A night of partying, a suite at the most exclusive place around, and a brunch that's been written to be one of the top three in the nation? If you don't want it, give it to me. Maybe I can entice your boyfriend up, show him my appreciation."

She ran her hands down her toned body, the result of countless hours in the gym, and grinned. "After all, I know the younger guys in your office have voted me the "MILF I'd most like to..."

"Mother! What's got into you?" She smirked, and I was aware she'd seen the flash of jealousy.

"Nothing, at least not yet. But don't worry, I'll leave your honey alone, for now anyway. I'd hate to have someone expire from overexertion at the party."

She laughed at my expression and walked off, swaying her hips. I had to admit, if I looked like her at fifty-four, I was going to be damn lucky.

Dear Stumpy,

Mom says thanks, we'll buy matching bells. She's kind of hot for her age, but don't get ideas or fantasies about a mother/daughter combo into your twisted little mind. I guess I need to tell you now I'm a bit territorial. All right, I'm a LOT territorial, something you need to be aware of if we get into a serious relationship. If you're mine, you're MINE, understand?

Seventy four hours and nineteen minutes, damn you, now you've got me counting. Olive.

...

Sweetheart,

I understand. But if your mother shares the least bit of your hotness, it might be difficult. And I'm a little possessive myself, you can ask my exwife and she'll verify that pretty quickly. I'm sure she would be glad to tell you how I react to betrayal.

I'm going to ask you to trust me a bit. I want your address, but not your name. I want to give you a little token of my appreciation. It will arrive the day of the party. It's a little thing, but I think you will like it.

Forty-nine hours, Stumpy.

...

Finally! I was glad it was Saturday, I would have been worse than useless at work. Mom didn't help much, two women stressing in one house was a little nerve wracking. We'd both been to the salon, having our hair styled and makeup professionally applied. We dressed carefully, and I have to say the results were stunning. Mom had on an ivory silk sheath that came three inches above her knees, four inch heels, her blond hair shining, diamond studs and a matching necklace finishing the image. She looked midthirties, not midfifties.

I had on the basic black dress. It went three inches below my knees, and had a dangerously high slit in the back. The bustier made my figure even more appealing, and the feel of the silk on my bare bottom was exciting me. I slipped a black thong in my purse, in case I had moisture issues.

The black hose felt delicious when my legs rubbed against each other. I finished the outfit with pearl earrings and a single strand round my neck.

I admired myself for a moment in the mirror, loving the curves, the way my auburn hair glowed in the lighting. I licked my lips, deciding the shade of my lip gloss was perfect. I saw mom grinning over my shoulder.

"Damn! I did good with you, girl. He won't be able to talk with his tongue hanging out and the blood flowing away from his brain."

I patted a stray curl. "I hope so. I wasted a lot of time and money if he doesn't"

Mom went to collect our coats while I went out to warm the car. It was thirty degrees outside, with a threat of snow. I felt a tinge of sadness, the gift he was supposed to send me never arrived, and it had me wondering.

Opening the door, I almost got hit in the face. A woman, in a white uniform and cap, hair back in a bun, was about to knock on the door. She grinned when she saw me jump.

"Sorry, traffic slowed me down a bit." She handed me two small packages, one plainly marked Olive, the other simply Mom.

"Stumpy says hello. Can I come in, it's kind of cold out here."

I recovered and invited her in. Mom came to see who it was. The woman held out her hand.

"I'm Caroline. I'll be your driver tonight. I'm to wait until you open the packages, then drive you to the Grove Inn."

She stood, enjoying the look of shock on our faces. "Go on, now, open them. I want to try to beat the weather."

I collapsed on the couch and tore off the obviously expensive paper.

Bells. Little silver bells on a silver chain. I looked at them closely. There were nine bells, each engraved. I stretched them out.

H O T N E S S X 10.

Mom opened hers, surprised to see a variation of the same thing, four slightly larger bells on a silver chain. M I L F, and a note for both of us.

"You both deserve the bells. It'll help me find you in a crowd."

My hands were shaking so bad I couldn't close the tiny clasp, so Caroline volunteered to hurry us along, As she wrapped it around my ankle she glanced up. I was so distracted that I didn't notice I wasn't in the most ladylike of positions, dress hiked up and knees opened. She grinned while I flamed red.

"Looks like someone is going to have a good time tonight." Mom saved me from embarrassment by smirking.

"God, I hope so. I haven't been laid in ages. Some little boytoy is going to find a MILF under his tree tonight."

"MOM!" I squealed out. They both laughed at me and hustled me outside. The limo turned out to be a Hummer.

Caroline apologized, saying it was supposed to be a Mercedes, but with the weather situation the Hummer seemed more prudent.

Snow had just started falling as we pulled under the portico at the grand entrance to the Inn, the massive marble columns glistening under the lights. The outdoor chandelier that had been written up in so many magazines twinkling brightly. Suddenly I was terrified. This was it.