Penny Wilson Learns to Tease

Penny answered her work phone on the 3rd ring. "Hello Penny Wilson."

"High Penny, Still on for Lunch?"

"Hi Matt, I'll be there in 10 minutes."

She grabbed her bag and headed to the restaurant. Once she got there she stopped at ladies room to freshen up her make-up before heading out their table. Looking in the mirror she saw that everything looked in place but she still put on a little lip gloss to bring out the red of her lips. She also changed from her office flats to 4 inch heels. They made her 5'8" frame a little taller yet she wouldn't tower over Matt like she would have her husband. On a whim she undid a couple of buttons on her blue silk blouse exposing some cleavage without looking slutty. Thinking to herself that it was OK to flirt a little without taking a risk of being misinterpreted. He was a friend from outside of her profession so she had no concern for her professional reputation. She had no intention of ever cheating on her husband but occasionally wanted to feel generally desirable. It was a small idiosyncrasy that wouldn't get her in trouble. She could never do it with a work colleague for fear of it causing problems at work, plus the ladies were very catty and gossiped all of the time.

As she walked through the restaurant she noticed several men had checked her out, including Matt as she reached the table. It gave her ego a much needed rise after the tough week she had been through. She leaned over toward Matt and gave him a kiss on the cheek, noting that his eyes and flicked down to her breasts.

"Penny, you get prettier and prettier all of the time!" he gushed. She smiled back at him and said "You're not half bad yourself Matt!" They both laughed since it was a little flirting ritual they had done between each other for several months. Harmless banter really.

As they enjoyed their meal and conversation Penny had caught Matt checking her out more than usual. She was amused and flattered. She realized that perhaps she had actually left more of her blouse undone than normal and felt slightly naughty about it.

At the end of Lunch as they were exiting the restaurant Matt reached into his suit jacket and pulled out an envelope. "I almost forgot, here's two tickets to a Broadway play that is town. Since Katie is out of town this weekend I figured you and your husband would like to go in our place on Saturday evening. It's supposed to be really good!"

Penny was surprised with the offer and looked at the tickets. "Les Miserable!" she exclaimed. "Matt, Thank you!" She jumped into his arms hugging him enthusiastically her body pressing against him. "I was trying to get tickets but they were sold out right after they announced it was coming to town!"

Suddenly she gave them back to him. "Oh sorry, He's going on a hunting trip this week and won't be back to the following weekend. Darn. You should give them to someone else to enjoy, it is such a romantic play it would be a shame to waste them."

Matt had seen her eyes sparkle and then crash all in that instant. "Sorry Penny." He said with empathy. He Said "No you take them and take a girlfriend! Enjoy yourself."

Penny was tempted but her friends were out of town as well. Then a thought crossed her mind. "Matt, Both of them out of town too. But if want, you and I could go together and enjoy it!" almost pleadingly.

He knew she really wanted to go but wouldn't go alone. "Penny, you've got a date! I'll pick you up at 6:00 and we can go to dinner and then the play. I really wanted to see it as well!" They both smiled widely at each other. "OK, 6 it is. She leaned in again and gave him another hug and a kiss on the cheek.

As they were leaving the restaurant "She turned to him and asked "Are those Orchestra seats? Isn't that a fancy dress area?"

"Oh yeh, I was planning on wearing my Tux. Is that OK?"

Penny thought for a moment, "OK, then I guess I'll wear a cocktail dress."

As they waved goodbye she noticed his eyes glued to her breasts and blushed to herself. "A date! I have a date Saturday Night! What will I wear? I don't have anything that formal."

As she was walking back to her office a couple of men really ogled her and she remembered that her blouse was still buttoned, she quickly closed her coat and proceed to her office building. In the skyscraper's lobby she stepped into the ladies room to change out of her heels and button up her blouse. She was surprised to see that a third button had come undone and Matt obviously would obviously been able to look down her blouse to her skimpy black lace bra. At first she was embarrassed but then smiled. As her college aged daughter had told Penny when she had complained about the daring outfits she wore on dates "Sometimes you have the let the GIRLS work their charms. You're only sexy for so long so - If you got it flaunt it baby!"

As Penny headed up to her office she wondered in one of her daughter's dresses might just be the ticket!

On Saturday she went to the salon and had her hair highlighted and trimmed. While getting a pedi and manicure she decided to get her legs waxed and while they were doing that to get a bikini waxing as well. When she got home at 4:00 she opened a bottle of Chablis and poured herself a glass to calm her nerves while she put on her make-up. She really didn't have a suitable dress in her closet so she looked in her Daughter's closet. She tried on several checking out how they looked on her body while she danced around the room and drank another glass of wine. Each time she took a dress off she found another that was slightly more revealing. The last two were very appealing to her. One was black, tight and very short. The other was red, shear and floor length, but it was slit up to the middle of her left thigh and the neckline plunged well below her boobs. She decided on the Red. She found a tiny red lace thong that wouldn't be visible beneath the thin material and black real silk thigh high stockings. She accented the dress with a couple of strings of pearls that hung to just above the top and to the middle of her firm breasts. Her daughter had a pair of sky high black heels with red souls that perfectly matched the dress. Her daughter called them her "Come Fuck Me Nows" and claimed they never failed her in getting her man.

Penny looked at herself in the full length mirror and was amazed at how sexy she looked. She turned left and right and made a few dance moves to see how the dress flowed. She was very satisfied with the look. Then, Penny tried the famous Angelina Jolie pose where her left leg was exposed through the slit in the dress showing off her shapely leg all the way up to the top of the silk stocking. Penny thought this was much hotter than she had planned for the night.

The doorbell rang so it was too late to change. Plus with the two glass of wine she had drunk she was feeling a little flirty already. She walked to the door and caught the image of herself in the hallway mirror. At each step when her high heel connected with the floor she could see her breast jiggle slightly. Her nipples were clearly becoming hard and visible. She grinned thinking "Well Girls work your charms!" as she opened the door.

Matt smiled as the door opened and he presented an orchid bouquet to Penny. Then he noticed the dress he was wearing. His jaw dropped open as she stood there with her leg pushed through the slit and her breasts framed perfectly around the pearl necklace.

"Wow Penny you are gorgeous!" His eyes went back over her body and she shivered. She had never dressed like this before.

"It's too much isn't it, I'll go upstairs and change it will only take a minute." As she started o turn he reach out and caught her hand.

"No way Penny that dress was made for you to wear it! I'll have to stand guard to keep the guys from trying to steal you away though. You will definitely be the most desirable woman there!"

Penny blushed but enjoyed the complement immensely. "Does it really look good on me? I was thinking that maybe I was too old for it."

"Nope you look like a movie star. You gotta wear it, please, for me? I'll buy lunch for the rest of the year"

She smiled, the dress really did look hot on her.

So the went down to his car. As she got in she realized he had probably gotten a peak at everything Mother Nature had given her. As he walked around the back of the car she noticed him readjust himself in the mirror. She smiled to herself "Nice to know I can still make a man hard she thought."

Once he got in and started driving she noticed he was constantly trying to look at her.

"You need to keep your eyes on the road for now. I'm your date for tonight so you can look all you want when we get there. But let's not get in an accident before then!"

He laughed "Sorry I think I was just getting a little overwhelmed. Like a teen on his first prom date."

"It does feel kind of like a prom date doesn't it. Let's just pretend it is and have some fun then."

As they drove off, she looked down and his slacks had a large bulge in them. She blushed in the dark thinking about how she had made another man's cock hard.

One they enter the theater she went to the ladies room to check on her make up. As she came out she saw him standing there waiting for her. She put everything she could into a sultry walk right at him. Giving him and unobstructed view of her body as she came close. While she smiled on the outside on the inside she was on fire. Thinking to herself "Come on sell it baby, make him sweat. Give me something back honey. That's it let momma know you want her." And then she saw his pants jerk slightly.

His eyes were glued to the gentle swaying of her breasts as she came up to him. She slid her arm into his and pressed he breast against him. "Now wasn't that much better than a sneak peak in the car? Let's go find those seat."

As they walked to their seats her breast was pushed firmly against his arm pushing it more of it out of her dress. She felt the men's eyes on her again and shuddered. She had never been much of a tease but in the last two days she had thrilled at the attention her body was getting. It was terribly erotic feeling that was starting to arouse her.

When they reached the seats she made sure to sit on his right providing him a full view of the legs. As she sat down she let the skirt fall off her crossed legs. She slipped her hand into his and pulled it onto her legs then as the lights went down she released his hand on to her lean thigh. She leaned her head toward him and whispered in his ear "That feels really good. Just don't go too far and you can enjoy it all you want." Then she rested her head on his should and place her hand on his thigh. By the intermission his hand had finally slid up her leg far enough that his pinky finger was rubbing her panties. She hadn't stopped. And she eventually had slid her hand over his amazingly hard cock.

They went out into the lobby and she retreated to the ladies lounge to freshen up. When she came out he was standing there with a couple of glasses of Champagne and an obvious bulge I his slacks. Once again she walked toward with the sexy walk he had ever seen. He reached out to her to hand her the glass. As she took it she slid something inti his hand.

Penny whispered in a sultry hushed voice "Careful now." He cautiously looked in his palm and realized it was a tiny red thong. As she looked at him while taking a sip of wine she saw his eyes flash in realization of what she had just offered him. As he pulled her to him she let her body mold to his and kissed him back. Then she pulled back "Is there somewhere private we could go? I need you inside me now, right here. Please!"

He guided her through the Opera House to a small alcove off of the third level. It had a terrible view of the stage so was being used for this production. No sooner had they entered the alcove than she was down on her knees unbuckling his pants. Her mouth opened up to his hard cock as he pushed it between her lips. Penny didn't normally like to give blow jobs but tonight she wanted to take him fully into her mouth within minutes she was vigorously deep throating him. Something she refused to do for her husband and then as she cupped his balls and swirled he tongue along his throbbing cock she knew he was about to cum. She rapidly jerked him of and sucked ever bit of cum she could from him all the time staring into his eyes. She made certain he saw her swallow his come and then liked his dick clean. She kept bobbing he head back and for the on his cock until her became hard again. Then looking up from her knees she said, "Fuck me now, fuck me hard and deep. Make me cum. Stick it in me please."

He pulled her up and pushed the dress off of her shoulder. He started kissing her beautiful, tits sucking on her large nipples.

"No she moaned no more teasing put it in me." He lifted her leg up and entered her is one massive thrust. She moaned loudly as he began thrusting faster and faster. "Here, please, harder faster. I'm about to cum. Oh God, Please fuck me, fuck me, fuck me!" Then she came is massive waves. Her body slamming against his, her cunt impaled on him. And then she fainted with his dick buried in her. In a moment she regained consciousness. Both of them spent, exhausted and yet slowly moving back and forth against each other for one last sensation. As his dick slipped out of her wet pussy she grabbed it in and kissed it longingly.

She let him play with her tits for a while, sucking on her nipples until they were hard again. "Let's go back to the play and watch it until the next intermission. I should have caught my breath by then."