Maggie's Amazing Night Out

We had been talking for a while and met up a few times for drinks a few times. She (I will call her Maggie) was gorgeous. Curves in all the right places. Hourglass figure, 5'9" tall, 38DD breasts and an ass to match. The last time we met up was first time we fooled around, but didn't have sex. Our attraction was magnetic at this point. We knew we wanted more. Texting was our normal means of communication, and we both had the green light to move it forward. I sent her a text at lunch.

Me: Dinner tonight. I will pick you up at 7:30. Wear something to "Wow"

This was me not asking what she was doing, it was me telling her I wanted her.

Maggie: Anything in particular?

Me: Tight black dress and heels

Maggie: I have just the one. See you then!

I was sitting at my desk trying to concentrate, but the thought of her in the dress I was imagining her in and the sound of her heels clicking on her marble foyer to her front door made me hard. The end of the day could not come soon enough. I just then get a text from her.

Maggie: Black, red or purple?

Me: Hmm, Red

Maggie: Good choice!

Me: What did I choose?

Maggie: You will have to wait and see...

Me: Tease...

Maggie: Stop acting like you don't love it

Me: Thoughts of seeing you tonight has had me wound up all day

Maggie: Don't go getting tied up at work tonight and be late

Me: Nothing is going to keep me from it!

Maggie: Until then...

Damn, she knew me so well already. I sat through my one last client call, but I was barely there. I was just staring out the window waiting in anticipation. Once the call ended, my coworker nudged me.

"You alright man? You barely said anything all meeting."

"Yeah, sorry about that. Something came up today and it just... has me thinking about a lot of things."

"Anything I can do to help? It's just very unlike you."

"Let me just get through the day today and I will be like a new man tomorrow. I promise."

"Alright, just relax some tonight."

"Not to worry. Thanks for looking out!"

With that, I went back to my office, started to pack my laptop and some papers in my backpack as usual, but stopped. I wasn't going to let anything interrupt tonight. I left it all on my desk and walked out of my office with nothing but my personal phone in pocket. The work one stayed on its charger on my desk.

"Have a good night!" I said to the secretary as I left the office door and walked to my car. Three hours until I pick her up. I drove to the local florist and was looking over the selection. I did choose red for her, so we will have to match.

"May I get a dozen red tulips please?"

They were perfect. Had them wrapped up and had to stop by the liquor store quick for my favorite after dinner nip, Grand Marnier, then straight back to my house to get ready. By the time I got back, two hours until I see her, ninety minutes before I have to leave.

I put the flowers on the table next to my keys and wallet and the bottle on the bar. I decide to send a quick text.

Me: Just got home. Cannot wait to see you!

No immediate response back. No worries. I took off my work clothes in my bedroom on my way to my bathroom. Looking myself naked in the mirror. I had a little bit of a five o'clock shadow, but I was going to leave that. I did however need to shave up down below. I was stubbly down there. This was usually a Monday and Friday activity, but tonight being Thursday, I had to do it early. I was in the middle of shaving when my phone buzzed. I checked it.

Maggie: Something came up.

Me: Oh no! Can't make it to night?

My heart sank...

Maggie: Just kidding! Wouldn't miss it for the world!

Me: You can be a real jerk sometimes, you know that?!

Maggie: Well, something will be up later. The two of us!

Me: I like the sound of that. Go finish getting ready! See you soon!

Maggie: Can't wait!

I finish my task and hope in the shower. Scrub a dub and all that normal shower stuff. I get out and dry off walking over to my dresser. I sort through my boxer briefs and find my red Calvin Klein's. If she is wearing red, I am going to match her. I put them on, along with my undershirt before walking over to my closet. Hmmm... I sort through my suits, but settle on my silver Hugo Boss slim fit. I match is with my white collared shirt and red tie to match whatever it is she is teasing me with. I topped it off with a brown leather belt and brown loafers. No sock. I got over to my watch collection and select a nice Omega Seamaster with a carbon fiber face plate, chrome surround and black NATO strap. I know, I know. A black strap with brown shoes and belt you say? I will get over it, you can too.

I check the time. Thirty minutes until I leave. I go to check myself in the mirror. Looking sharp! I grab my Polo Black cologne and do two spritzes on my neck and walk out of the bedroom. Now the hardest choice of the night, which car to take? The Audi S4 or the 1968 GTO restomod... The GTO would be more of a "Look at us" choice, but no AC. Probably not the best choice for her. The Audi it is. I walk out and put the flowers in the passenger seat so I don't forget them. Go back inside and open the bottle of Grand Ma and have quick nip while turning on ESPN to get the update for the college football week ahead and to calm my nerves.

Before I know it, its 7:00 and time for me to leave. I fire up the Audi and put on some classic DJ Tiesto In Search of Sunrise 5. Nice beats but not too loud or intense and enjoy the drive across town to her house. Traffic was iffy as usual, but I was able to get through it and still be on time. I pull into her neighborhood and my heart begins to beat faster. Then I pull into her driveway and up towards her sidewalk. It is now pounding. I open my door, grab the flowers, and get out to walk up to her front door. I knock softly rather the use the doorbell. I am guessing she knows I am here. Here door has a frosted glass panel in it, so I cannot see her, but I can hear what I was wanting. The clicking of her heels on her floor. God, I love that. I can feel the blood flowing to all the right places. Just then, the deadbolt unlocks and then the door opens. My jaw drops.

She looked flawless! Her hair has some loose, loopy curls in it, parted off to the side. Her makeup was minimal but accentuated her beautiful brown eyes. Her lipstick was Ferrari red. Her black dress was tight with a low plunging neckline, but was class all the way. She had a red clutch in her hand with a gold tennis bracelet on. The Dress stopped just above her knees, followed by sheer black stockings going down to black heels with red soles. She looked sexy, classy and refined and was going to make her the stand our attraction at the waterfront steakhouse we had dinner reservations at.

I gave her the full once over and I didn't have the words to say. She broke the silence.

"Well don't you look sharp!"

"You... you look absolutely stunning!"

"Stop... Are those for me?!" as she looks at the flowers.

"They are! I hope you like tulips!"

"I do! Come in! Let me put them in a vase before we go!" as I hand them over to her. She gives me a hug after taking them.

"You smell fantastic!" as we both say in unison.

"Jinx!" I said.

"What do I owe you?"

"A kiss will work, for now."

As we look each other in the eyes, we both close them as we lean in for deep, intimate kiss with only mild, but sensual tongue. She breaks away first.

"Ok let me get these in a vase, then we can go!"

She turns to walk towards her kitchen and all I can do is stare. Her ass looks fantastic as it bounces side to side as I can hear the clicking of her heels walking away from me. I then notice her stockings have little black X's going up the back middle of her calf, disappearing under her dress. I am going to have to follow those some more tonight. I hear a cabinet door open and close, then water running, the crumpling of the green paper the tulips were in, and a garbage can open. Then she reappears with a glowing radiant smile. "Ready?!"

"After you..." as I motion to the door, still open.

As she steps out of the door, I close it behind me. She takes out her keys from her clutch and locks the deadbolt. She turns and walks toward me as I position myself to help her down the two steps from her landing to her sidewalk, offering my hand to assist her down. She tilts her head to the side and smirks, thanking me for the help. We walk down to my car as I open the door for her to get it.

"Such a gentleman."

"At your service my lady." As I give her a playful bow.

She sits down first, then swings both her legs in together in a proper ladylike manner. Once she is in, I shut the door and walk around the back of the car to the driver door and get in. I press the start button and the car fires to life with a rumble.

"All ready?" I ask.

"Ready! But you never did tell me where we are going tonight."

"Ahh, we all have our secrets. I called in a favor."

"So, I won't know until we arrive?"

"You got it."

"A man of many mysteries. I like that!"

"Anything particular you would like to listen to do the ride over?"

"What you have on works for me."

As we drive out of the neighborhood and on the highway, its mostly just small talk. How the day was. New stuff at work, etc. As we turn onto the bridge to cross over the bay, she looks at me. "Are we going to the beach?"

"Kinda. It has a beach view."

She thinks for a second, looks at me with eyes squinted and thinks some more. "Are we going to Seagar's Steakhouse?!"

"Wow! Great guess! And yes we are..."

"Oh my god! I have always wanted to go there! How did you manage that?!"

"I told you, I called in a favor."

"You are awesome!"

"I hope you enjoy it! It's my pleasure."

The smile on her face was worth it. Seagar's is like a four month wait list minimum unless you know someone. I happen to know the Sommelier. As we pull up, my car is immediately outclassed by the Bentley, Porsches, Ferraris and Lamborghinis, but I'm not there, yet.

I pull up to the valet (there is no self-parking here) and they open both our doors and we exit. I hand over the key and tag my ticket and button the top button of my suit coat. I walk around the front and offer my arm to Maggie, to which she lets out a little smirk and takes. We walk up the five steps to the doors to which both open gentlemen in suits welcoming us in. I approach the hostess desk and give her my name.

"Can you also please let Nathan, the Sommelier, know we have arrived when you have a chance?" I ask.

The hostess responds, "Certainly sir. If you are ready, please follow the hostess to your table."

I motion for Maggie to follow single file behind the hostess. As we enter the main dining area, all heads immediately begin turning and staring at Maggie. She without question had the desired affect I was hoping for. She was the center of attention and she was realizing that the deeper we walked into the main part of the restaurant. We ended up in a corner table and I offered her to sit in either seat. She took the one with her back to the wall and I sat next to her, looking out over the dining room. I pulled out her seat and assisted her getting into it and pushing it in for her. I walk around to my seat, unbutton and remove my jacket and also sit down.

"Well, what do you think?"

"I don't know how you did this, but this is amazing!"

"Almost as amazing as you look! You are still blushing from all the attention you got walking over here. I am pretty sure every guy is jealous of me right now."

"You are going to make me blush more! Stop it!"

"I'm serious! You saw all of them."

"You're too much!"

Just then, my friend Nathan came over to our table.

"Nathan! Good to see you my friend!"

"Same to you! And you must be the one all the commotion is about amongst the wait staff."

"Nathan, this is Maggie. Maggie, Nathan."

"Pleasure to mean you!" Maggie said.

"No, please. The pleasure is all mine! Thank you both for coming in. We have everything taken care of for you tonight. I will go get the wine ready and the amuse-bouche will be out momentarily. Enjoy you two! Pleasure meeting you Maggie!"

As Nathan walked away, Maggie asked me "What did he mean when he said "everything is taken care of?"

"The chef is making us what he feels like. I hope you don't mind."

"Really?! They do that?"

"Really. I told Nathan to tell him we both do our steaks medium-rare. That's all the more he needed."

"You really know how to impress a girl!"

"Well I hope you like it! This is not something that can be pulled off often."

"Well I thank you for going to all this length to take me out." She leans over and give me kiss on the cheek.

"You're most welcome!"

Just then, Nathan and a waiter come back with the wine and first course. We begin to enjoy and nice Bordeaux and snacking on some of the smaller plates that come out. She places her hand on my knee and slowly runs it up my leg and as we look at each other with a smirk. She runs one finger up my shaft as I am starting to grow. We finish the round as the second round comes out.

We still making small talk eating the second round of food. It's now my turn to place my hand on her legs and start exploring some. Her stockings feel absolutely amazing and I run my hand up her leg. I feel the thigh highs end and hit bare skin. My turn to give a nod of appreciation to her for her selection. I keep going and feel they are connected to a garter belt strap. She has taste in lingerie! I edge just a little higher up, stretching the fabric of her skirt just enough to determine she is either shaved or waxed, and wearing lace underwear. She lets out a little bit of a gentle moan, letting me know this is going well. Now, just before the main course, we are feeling pretty good, having each had a glass of wine and having done our exploring. I stop and admire her. She catches me.

"What are you thinking?"

"How absolutely sexy you look right now."

She blushes big time.

"I'm serious." I say. "Just stunning..."

"Well thank you! But before the main course comes, I am going to run to the ladies room."

She slides the chair back and walks toward the bathroom. Again, every guy is watching out of the corner of their eye or just not caring as she playfully bounces between the tables. If looks could kill...

Nathan seizes the opportunity to come over quick.

"Dude, how in the world did you find her?!"

"I'm a lucky man, good sir!"

"No kidding. Even the chefs are peaking out to see her. Well, let me top you both off quick. The steaks should be right out."

"Thanks again for hooking us up!"

"No worries man, any time!"

Just then I see her come around the corner, walking back towards the table. I rest my right palm under my chin and elbow on the table to enjoy watching her walk back. Normally I am not a man of few words, but the appropriate ones are currently escaping me. I stand up as she gets close to help her back into her chair. As we both get readjusted, I feel her hand go to my knee and tap on it twice. I look at her quizzically.

"I left you something on your knee." She says with a wink.

I slowly run my left hand down my knee and feel something there. It feels like lace... I look at her out of the corner of my eye.

"Those are for you, for now. I will need them back later."

I pull a red lace G-String out from under the table cloth and look at her with a look of amazement.

"What the?"

"I'm not going to need them for a while. And anyways, they are a little wet..." she says with a double raised eyebrow.

Unsure what to do with them, I look at them one more time and shove them in my pocket. Just then, the steaks arrive.

"These look good!" She said like nothing happened. "Don't they?!"

"Absolutely they do! Thank you gentlemen!" as the servers walked away.

"We should eat these and get dessert to go..." Maggie said.

"I second that thought."

They were only six ounce filets, so they didn't take long to eat. After I was done and she was still finishing up hers, I left hand was right back up her leg. She adjusted herself some and gave me access to herself. She definitely waxes. Smooth as can be. Maybe even laser removal. I used my left middle finger to ever so gently glide up and down her soft, and wet, opening. She squirmed a little as she was bringing her fork to her mouth. I moved my finger tip up to here clit and ever so gently, did circles around it. Her hips were starting rock ever so slightly as she was chewing and took a deep breath. She looked seductively over at me. She looked down and only had one bite left.

"Keep going until I am done." She whispered.

Her blinks were getting longer and it was taking a lot for her to keep chewing. I could feel her legs now starting to twitch some. She covered her mouth and looked me.

"We should get the check."

I let my hand slide down her leg as I motioned over to the wait staff and they came over.

"Everything was excellent, but she isn't feeling herself at the moment. If we could get dessert to go and the check quickly, I would appreciate it!"

"Certainly sir, we will get it taken care of for you." As I handed them my AmEx.

"Are you a good driver?" Maggie asked me.

"I can handle my car, yeah. Why?"

All I got was couple raised eyebrows. Either she was down for some fun while I was driving or she wanted me to get home as fast as I could. Either way, I am ready for it.

The server came back out about 2 minutes later with the check and bag with our desserts in.

"Here you go sir. Two pieces of our famous cheesecake for you. Thank you for coming in tonight and I hope to see you two again soon!" He said in Maggie's direction.

"Thank you kindly! Everything has been great! Please let Nathan know we had to leave unexpectedly and I will catch up with him soon."

"Absolutely, sir. You two have a great rest of the evening."

"We will! Thank you! Good night!"

I signed the surprisingly smaller than expected check and left a quite generous tip. Nathan gave us the hook up, for sure. I stood up and put on my suit coat, buttoning the first button, and then moved over to slide out Maggie's chair. She stood up and we could feel all the eyes of the room on us (her) again. I motioned for her to lead the way and she grabbed the bag of dessert, walking around the table and making her way down the aisle towards the door. I caught a surprising number of women looking at her in jealousy, no doubt, but not paying me the slightest bit of attention, as it was intended. We got to the double doors leading out of the dining room and into the reception area, where the receptionists and doormen both wished us a good evening. To my surprise, the Audi was already waiting for us with the two valets holding our doors open for us. That's efficiency and sign of perfectly run business. I have my ticket and $20.00 bill to the valet and my side and they both wished us good evening and closed our doors for us. I pulled my phone out to plug it in and put on some music before buckling my seatbelt and starting to drive away.

As I got down to the stop sign at the bottom of their horseshoe shaped drive way, Maggie immediately leaned over and started kissing my neck.

She then whispered in my ear. "I want you in me so bad..." and slide her hand down my chest to find my hard cock and began rubbing it through my pants, still kissing my neck. I let out a soft moan.

"Very soon! Are we going back to my place or yours?" as I pulled onto the main road making my way back to the bridge.

"Mine." She said as she undid my belt. I was having a little bit of a hard time concentrating on driving at the moment. Then she undid my pants and slide the zipper down, relieving the strain my cock hard against my pants. I had to take a deep breath and regain some composer as I put on my turn signal to get onto the bridge. She pulled my shirt up and saw my red Calvin Klein boxer briefs.