tagTranssexuals & CrossdressersThe Neighbor's Boy Ch. 03

The Neighbor's Boy Ch. 03

bylauratmd©

Welcome to Chapter 3. Thank you all for the wonderful feedback. Laura's story with Matt continues.

Again, I would appreciate your reviews/comments/suggestions.


*****

During my run the next morning, I started to think about what to wear tonight. Even though I was planning on letting Matt down easy, I wanted to look good! Unfortunately, I wasn't going to have time to get home after work to change.

I settled on a black sheath dress that stopped an inch or two above my knee. It was form fitting and showed some cleavage, but not enough to be scandalous in the office. A black blazer would make it more professional.

And finally a chance to wear the blue Manolo Blahnik stilettos that I'd bought a while ago, and had been saving for a special occasion. They were a D'orsay style that with a pointy toe, cut to show some toe cleavage as well.

"Cleavage up top and cleavage down low" I thought to myself and chuckled.

Back home after showering and doing my hair and makeup, I finished the look with black sheer nylons and gold jewelry.

As Barry was out at a client, the day at the office was fairly uneventful, other than lots of admiring glances from the men, and compliments from the ladies, especially about my shoes. Finally, the time came for me to meet Matt. On my way out, I stopped in the ladies room to freshen up, redo my makeup, and put on some more perfume.

My perfume of choice when trying feel sexy is Victoria's Secret Velvet! While not a big fan of their lingerie or clothes (too expensive and way too cheaply made), their perfumes are amazing!

A I pulled my BWM into Chef Paolo's parking lot, a text from Matt came in, "I can't wait to see u! At the bar."

"OK, Almost there." I texted back, and pulled up to valet parking. Looking this good, I had to make an entrance.

While I got my things together, the valet opened my car door, "Welcome to Chef Paolo's!", when I looked up, I noticed that he was staring at my legs, not at the rest of me. Purposely, I took a minute to gather my things, and check my makeup in the mirror.

When I was ready to go, I swung my legs out, in such a way that my dress rode up to show off the full length of my legs. As I stood up, I noticed a very obvious erection in the boys pants.

"Please take good care of my baby" I told him, while handing him the keys, and then turned and walked inside.

"Poor boy, I hope he can do something about that" as I walked away. Inside, the restaurant was very chic and modern. The lighting was just enough that you could see. They were playing a soft jazz music. Perfect ambiance.

Looking over in the bar area, Matt was waiting for me. He looked so handsome! He was wearing black slacks, with a dark burgundy shirt, that looked like silk. He had a beer in his hand, but I didn't say anything.

"Mrs. T! You look amazing!" As he looked me up and down, then kissed my cheek.

"What are you having?" The bartender asked.

"A glass of Pinot Noir, please!"

"Coming right up!" as he was staring at my cleavage.

"What a slime-ball" Matt said to me, noticing the bartender ogling me. "Our table should be ready soon. How are you? How was your day?"

"My day was good. How was yours?" and we started making small talk. Matt kept staring at me.

Usually looking into my eyes, but sometimes letting his eyes wander down over my body. On occasion, he would brush his hand or arm against me.

After some time, the hostess comes over to Matt, "Sir, your table is ready. Please follow me," She was really cute, but Matt didn't take his eyes off me, as he said "OK." to her, and asked me, "Are you ready?"

"Sure, let me settle up here."

"No, don't worry about it. I got it" and he pulled some cash out of his pocket and left it on the bar. For someone who was 19 or 20 max, he sure behaved like an expert at the bar.

The hostess seated us at a table for four that was against the wall. Matt pulled out a chair for me, then sat down on the bench seating against the wall.

"Hello, My name is Allyson. I'll be your server tonight. Would you like anything to drink? Or are you still good with your drinks from the bar?" As she filled up, our water glasses. Looking from Matt to me, back to Matt, and then finally to me, looking at me for a long time.

"A bottle of Pinot Noir, please." Matt told the girl.

"What kind? Do you have a preference? or just the house Pinot?"

"The house is fine."

"May I see your ID sir?" She asked Matt.

"This happens all the time", he said to me as he showed her his ID.

"Thank you, Mr. McLovin" she said smiling.

"Mr. McLovin?" I said to Matt, to which he shrugged his shoulders and chuckled. "Can I see it?"

He passed me his ID. It looked pretty good. I couldn't see any real difference from mine.

"Mack McLovin! Are you a SuperBad fan?" I teased, and kept looking at it.

"I love that movie."

"This looks really good. Where did you get it?"

"I know a guy."

"But it says your name is Mack. In the movie, his ID just said McLovin?"

"I asked for that, but my guy wouldn't do that. He said it would set off some alarms."

"It also says you're 37." Once again, he just smiled and shrugged. "I'm glad you're 37, otherwise, I'd be robbing the cradle."

At which, he laughed out loud. "How old are you? If you don't mind me asking."

"Not at all, I'm 38."

"Oh, you don't look it."

"Well, I am."

The waitress interrupted and brought us menus and glasses. "I'll be right back with your wine."

"Matt, what do you see in me?" I asked.

"You're beautiful, sexy, intelligent, and different from anyone that I've ever met. All of the girls I know are so immature."

"Well, I am different, and have experienced more than you have."

"I LOVE that you're different! You are amazing!"

The waitress came back with the bottle of wine. I laughed as she unscrewed the bottle.

"Why are you laughing?" he asked.

"Have you ever seen Night Court?"

"What's that?"

"A TV show that I grew up with. I'll explain it to you later."

"Sir, will you be tasting the wine?" the waitress asked, as she started pouring for Matt.

He looked at the half pour, then drank it one quick swig.

"It's good!" he proclaimed.

"An expert at the bar maybe, but he still has a lot to learn about wine.", I thought to myself.

"What do you for work?" he asked me. "Looks like you do pretty well."

"I'm a management consultant. I help companies figure out how to streamline their operations and expand wisely when they're ready for that."

"So you lay people off."

"Not usually, but some companies have to many people, so I help them become more efficient. Sometimes, it means layoffs, but usually we try to assign them to places where they can have more of an impact. The part of my job that I enjoy much more is when a company is looking to expand. I help them make sure they do it an a sustainable way, and don't over expand."

"I see, but don't you want to give as many people jobs as possible?"

"That would be great, but history is loaded with companies that over expanded, that ended up going bankrupt and having to lay off everyone."

"Oh, that's not good."

"No, it isn't. What are your plans? I know you leave for the Marines in a few weeks. What do you want to do there?"

"Two and half weeks actually. After basic, I'd like to get to into the pilot training program and learn to fly a harrier, or better an F-35."

"A pilot? Very nice!"

"I think it's hard to get to pilot training, so my just end up in infantry."

"You're very smart. I'm sure you'll do well, and can get wherever you want."

"Thank you, Mrs. T." That comment alone, made me feel like a mom, when I was having a wonderful night so far. Without realizing it, I downed the rest of my glass of wine, which Matt promptly filled for me.

"Here are your menus. We have some specials tonight. A very nice lobster..." she continued on, but my mind drifted off. "I'll be back in a few minutes for your your order."

Until she came back, we talked about the menu, and had some more wine.

We continued chatting about Matt, his future, his parents, and other things while until our dinner came, and over dinner. All the while having more wine. Matt ordered a second bottle with dinner.

When we were finished eating, I excused myself to the ladies room.

When I came back, "Mrs. T, why don't you sit next to me?" Matt said and moved the table a few inches to make it easier for me to get in.

Perhaps, my mind was a bit cloudy from the wine, but I found myself sliding in next to him. He was so hot. As we gazed into each others eyes, Matt's hand found my thigh under the table, which immediately caused me to shudder.

"Would you two like any desert? or an after dinner drink?" the waitress interrupted.

"I would like a glass of fifteen year port." I told her.

"We only have ten, twenty, or thirty year port."

"I'll have the twenty then."

"Make that two!" Matt added, "What's port?" he whispered to me.

"It's like a desert wine." I answered, as my hand explored up his thigh.

"Sounds great." as his hand moved down to my knee. The touch of his hand on my nylon covered legs was electric. I was getting so excited. I was glad that I'd thought to wear a tight gaff today.

He kissed me, as my hand found his monster through his slacks. I slowly started to rub it, as we kissed.

His kiss was amazing! Very strong, but gentle. His taste was masculine. A truly wonderful kisser. I wonder how he learned, or if this was natural talent.

Again, the waitress interrupted. "Two twenty year tawny ports. Anything else this evening?"

"No thank you, just the check!" I said. We started giggling, and puled apart, and sipped our port while looking into each others eyes.

The waitress brought the check, which I quickly took, and pulled my American Express card from my purse.

As the waitress walked away with the check, "You don't have to pay Mrs. T. I have money."

"No Matt. It's OK. Save your money for when you're in boot camp." I had no idea if there was any need for that, but it sounded good.

"Thanks Mrs. T."

"It's getting late. I should be headed home."

"Do you have to?"

"I do have to work tomorrow. But do you have an idea for where we could go?" I knew that drinking more wasn't a good idea, and taking Matt home again wasn't any better option.

"Have you ever been to The Hill?"

"No, what's that?"

"Its a lookout point with a great view of the whole town."

"That sounds nice."

"Great, I'll drive. Let me get my truck." Matt got up and left, as the waitress brought back the check. She had interrupted so many times, that I was tempted to give her bad tip. But that isn't fair. She did a great job otherwise, and the food was really good.

After signing the check, I walked back to the front of the restaurant. Noting how much harder it is to balance in four and a half inch stilettos, after a few glasses of wine.

Out front, Matt waited for me in his jacked up Ford F-150 pickup. I had noticed that him driving around in it before, but it never seemed so fitting to him before.

Climbing into the truck was a quite a chore while wearing heels and a dress. I'm sure that I was giving the valets quite a show. After finally getting seated and putting on my seat belt, a quick glance at the valets confirmed it. They were all smiling, and laughing to each other.

Matt drove us for a fifteen minutes on roads that I'd never been on, that seemed to go up and and up. Finally it leveled off, and we pulled into a clearing, where lights from the town spread out before us. A gorgeous view.

While I was taking in the sight, I noticed Matt staring at me, then he pulled close and kissed me again. We started making out like crazed teenagers. Matt's hands wandered all over my breasts

through my dress and bra. One moved to the back of my dress, trying to figure out how to get it down. At the same time, my hand found the zipper to his slacks, and slid it down. In another second, I'd freed his monster from his pants and boxers.

I looked down at it, then started rubbing it with my hand, kissed him deeply, then moved down to kiss the tip of his cock. I pushed back the foreskin, then started licking the head. Tasting his delicious

pre-cum, swirling it all over my tongue.

Matt was just moaning now. His hands had moved to the top of my head. He started to push my head down rhythmically, as I took the full head into my mouth, and started to swallow more of it.

Suddenly, there was a tapping on the window, then a bright light shown in.

"Stop, what you are doing. Show me some ID!" I looked up and saw a Police Officer through the truck window. He was shining the flashlight around the truck, and obviously knew what we were doing.

"How are our officer? Lovely night, isn't it." As Matt managed to pull his wallet out, and hand the officer his ID.

"Where is yours, Miss?" The officer said to me, ignoring Matt.

"One second officer" I said, as I tried to get myself straightened out. I fumbled for my purse, and then fumbled for my ID.

"Any day now lady." The officer said sternly. I passed him my ID.

"OK, Be right back", as he walked away.

Matt and I looked at each other, and broke out laughing. We quietly talked about what he was going to do to us when he returned. I was borderline panicking about going to jail.

The officer came back, "We've had some complaints about the activities going on here. I'm going to let you go, if you promise to go straight home, and only return here during the day."

"We promise Officer" we said together.

The officer shined his flashlight on me, looking me up and down. "Congratulations son!" and turned and walked back to his patrol car. He then sat in it and watched us, until we left.

"It might be time to go home. I'll take you to your car." Matt said.

"I think you're right." I answered. "What are you doing this weekend?"

"Tomorrow, I'm going up to the mountains with the guys."

"That sounds like fun."

"We'll fish, hunt, it will be a blast."

We made small talk about the mountains, until we got back to the restaurant. After I gave the valet my claim ticket, I wished Matt a great weekend and told him to have fun.

"It will be fun, but I wish I could see you."

I blushed and gave him a kiss good night. Not long after he drove away, the valet came with my car.

I gave him a few dollars, and took my keys. I wasn't really interested in flirting anymore, so quickly got in my car and drove home.

Upon returning home, It felt so nice to take my heels off, but I had some real pressure built up. I took my hose off, then my panties, which were really wet. My gaff was soaked! I had no idea that I had leaked so much. When I took my gaff off, my clit sprung up.

After getting fully undressed, I got in the shower. With the hot water running, my mind drifted to that fantastic evening. One hand started rubbing my breast, and the other started rubbing my clit. I finally climaxed and shot a load all over the shower wall, and slunk to my knees.

When I regained my strength after a few minutes, I cleaned the mess from the wall, rinsed off again, turned off the water, then dried off, and climbed into bed.

I fell asleep very quickly tonight.

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by Anonymous

If the above comment contains any ads, links, or breaks Literotica rules, please report it.
by Anonymous02/24/15

the whole mclovin part pissed me off

But i'm loving your story so far

If the above comment contains any ads, links, or breaks Literotica rules, please report it.
by WhiskeyIsGood01/25/15

I agree with everyone else so far

This is definitely a good story, and I enjoy reading it. It's just a little to rushed, and the chapters could be a little longer. I would definitely recommend talking to Joscelyn, she has been helpingmore...

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by kamperman4501/24/15

Almost like the beginning vision was it

Still a lot of plot development but no action. Why not save the postings until you have a good, strong story with the wanted action we are looking for as seen in the first short preview (Ch 1) you posted.more...

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by Bobluvs01/23/15

take your time

please take your time at the end and don't rush it. you can always have more then one page.

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by Joscelyn2tg01/23/15

I Think Its A Good Story...

...And it shows a lot of thoughtful insights about how the characters are feeling, why they're thinking is following the course it is, in other words, basically good writing. But you're rushing it, andmore...

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