Monopoly "Money"

Literotica Readers,

The following is a fictional account told in the first person by Gary Baker. All characters are well past 18.

*

Friday nights was often Monopoly night. At least twice a month Telly and Linda would get together with us and we'd start a game of Monopoly around 7pm and it would often go on until after midnight.

This Friday night, it was our turn to host. I put some hamburgers on the grill and my wife, Shelly, made potato salad. She knew I love her homemade potato salad made with red potatoes.

Telly had been a friend of mine since he began working together with me at the same high school 9 years ago. Telly Robbins taught history and I originally taught English but had just accepted a promotion to be the senior class counselor the year before.

Telly was a tall and imposing figure. He was 6 foot 3 inches and still looked like the linebacker that he was in college. His dark hair had begun to turn gray now that he was in his late 40s, but he was still well put together and was considered at least mildly attractive to the ladies.

Linda worked in the office at the same high school. That had been the only job that she ever had since she was 20 years old. She was now 47. Telly began as a junior high teacher for many years before moving up to teach high school kids. He was continuing his education and wanted to move up to the college level within the next few years.

Linda, to be honest, wasn't the most physically attractive woman...at least to the naked eye. She was very thin and didn't seem to have much in the bust area. She had straight red hair worn in a loose pony tail with sparse freckles. Because she was so thin, she seemed taller than her 5-7 frame. She did have very nice and expressive green eyes. However, getting to know her over the years, I began to see her inward beauty. I saw how she seemed to easily handle the diverse population of teens that constantly stopped by her counter. Most of the kids loved her. She was caring and non-judgmental.

After working with her for over 20 years, I saw a lot more than her obvious physical attributes, as modest as they were. I had known Linda Robbins longer than I had her husband, Telly.

Telly and Linda's daughter had just married the year before and moved with her husband to the east coast when he got a job transfer.

My wife, Shelly Baker, always amazed me at how self-deprecating she could be. She was truly attractive with short blonde hair and a very pretty face. Her blue eyes were bright and she had a very noticeable bust line. She wasn't huge, but her 36C tits always caught my attention even after being married to her for nearly 25 years.

She works as a bookkeeper. That's the only job she's ever had. After working for a large company, she began running her own business out of our home. There are times when she actually takes home more than I do in a month, especially during tax season.

She isn't thin but she certainly isn't obese either. She has always obsessed about her weight. In my opinion, her 150 pounds on her 5-5 frame was perfect.

Every time I'd say something to Shelley about appreciating her beauty, she'd remind me that I never saw myself as much of a catch either. At least not physically. I am thin. I am athletic but not muscular. I am only 5-9 and after a high calorie binge I might top the scale at 155 pounds. My blonde hair is receding and beginning to show gray in the temples. My thick, blonde mustache is also starting to show a little bit of gray as well.

"Gary, I'll start appreciating my looks when you will finally admit that you're a fairly nice looking guy yourself," she'd often tell me. Of course, I never saw that about me and I wasn't going to lie about myself. I would usually drop the subject at that point.

The four of us got along quite well.

Telly's personality is the most difficult to deal with. He is sometimes too honest. I really don't think he ever intended to make anyone uncomfortable. Shelly would sometimes complain when he'd compliment her on her appearance. She never complained to Telly. She would graciously accept the compliment but later on when we were alone, she'd complain about how uncomfortable it made her feel. I always stood up for Telly and reminded Shelly that maybe he was just being honest.

"Well, I'm not sure I like other guys looking at me like that," she once told me. "I feel like he's undressing me with his eyes."

"Nonsense," I told her. "Hey, just because a guy gets married doesn't mean he quits noticing other women's beauty."

"Really? I've never heard you tell Linda something like that?"

"That's because I see her every day at work. I keep a professional distance. When she comes over here, I am friendlier, but I still maintain that safe distance."

"That's bullshit Gary. It's because you don't find her attractive. She'll never know the discomfort of feeling like guys are ogling her."

I didn't like the way she said that. She assumed that I found her unattractive.

"She may not have the natural attraction that you do, Shelly, but she still is very desirable. Whatever she may lack physically, she makes up for in so many ways. Would it make you feel better if I told her that she looks awesome the next time she comes over? Even though she'll probably be in some frumpy clothes that aren't intended to flatter her figure?"

That quieted her. Shelly never tried too hard to look hot but her figure was hard to ignore. Linda just accepted herself as she was and never wore any makeup or any kind of flattering clothing.

Even as I begin this tale, I'm still trying to figure out how or why things happened the way they did between us. My guess is that there were underlying factors in the psyche of our two women that finally got unleashed for all to see. That doesn't absolve us men of guilt. That would be erroneous.

As usual, we started around 7pm. It wasn't a particularly good night for Telly. He was short on cash early on while Shelly seemed to get the good rolls. Linda wasn't doing too badly and I was hanging in. I was unable to monopolize any of the colors but Shelly had all of the green properties covered and had two houses on them both.

Then, Telly landed on one of her properties with barely enough cash to stay in the game.

We had all drank a couple of beers although I think Telly may have had two more than the rest of us, but no one seemed too inebriated. Yet, Telly's stunning remark caught us all off guard.

"Well, I guess I have to pay to park inside your garage. I bet that's a nice tight garage for that price."

Was that an intentional double entendre? Shelly looked up and saw a slight grin coming from the corner of his face.

"I'm sorry Shelly. I just want to stay in the game. I tell you what. What if you make me get undressed in exchange for the rent?"

I expected Shelly to tell him to go to hell. Instead, she thought about it.

"You're kidding, right?" she asked, not sure if she really wanted an answer.

"Not kidding. Hey, we're all adults here. It's not like you've never seen a naked man before."

Linda remained silent with her head down. She showed no interest in getting involved in this conversation. I wanted to speak up but I was going to let Shelly handle it until she needed my help.

"To be honest with you Telly, the only naked man I've ever seen is my husband. What makes you think that I want to see any more?"

Telly couldn't believe her. "I'm sorry, Shelly. I just thought that someone as attractive as you might have known other guys before Gary. I'm sorry Gary, I just made a very errant assumption. Let's drop it and I'll just cough up the money."

"No Telly. No cash", Shelly surprised us by blurting out. "I'm betting that you don't have the balls to really do it. No offense Linda, but you have nothing to worry about. He won't do it."

What in the hell was my wife thinking? It was HIS idea. Was she secretly wanting him to get undressed and using this dare to make sure it happened?

"And what if he does get undressed, Shelly?" Linda asked. "Then where does the game go from there? I don't plan on getting undressed, do you? If I run out of cash, I'll just sit back and watch TV or the rest of this game. I'm not ditching my clothes just to stay active."

Of course, Shelly was in the driver's seat. She had the most money. Barring some bad moves or unlucky rolls, she was probably going to win. Telly getting naked wasn't going to change the outcome. It was only going to delay the fact that he'd be the first to be out of the game.

I'm not sure if Shelly was surprised, but she didn't move her eyes from Telly as he slowly began to remove his shoes and socks. He then removed his short pants and t-shirt. A noticeable bulge was hanging down from his boxers and he wasted no time in removing them.

Linda looked back down at the board. She made no eye contact with any of us. Shelly made no effort to hide the fact that she was checking out Telly's form.

The first thing I noticed is that Telly was at least 2 inches longer than I was. He wasn't real thick, but he easily had 8 inches of flaccid meat hanging down. I'm sure that's what got Shelly's attention.

It was Linda's turn next. I could tell by looking at her that if she had her way about it, they'd go home right then. She hadn't noticed Shelly checking out her husband's cock.

As luck would have it, Linda landed on the same property that her husband did. Linda still had enough cash. She was slightly better off than I was. However, the next roll went to me and I was able to monopolize the yellow properties. They weren't as valuable as the green properties that Shelly owned, but I took a gamble and put two houses on each of the three properties. Maybe I could push Telly out of the game soon and maybe even Linda eventually.

However, all Linda needed was a three on her next roll and she would land on Kentucky Ave. and she'd own all of the red properties and still have enough cash to add at least one house. Shelly might have been planning her winning strategy, but I was hoping for some luck on my part and Linda's to make it difficult for her.

Linda rolled a three on her next roll. She had Kentucky and promptly bought it and put two houses on each, even though it made her short on cash. Linda had been the quietest one since Telly had taken off his clothes. She just looked down all the time. She never looked at her husband's naked form.

"Fine, since my husband wants to trade bodies for cash, I want to make a proposition."

"I don't have enough to put four houses and a hotel. Why don't we shorten this game. Gary, you have the yellow group and I have the red. We each have two houses. Since Gary seems to have no problem showing off his junk to another woman, I propose that none of us buy any more houses or hotels. Each person that's willing to strip down will automatically get hotels on each of their properties."

I couldn't believe what I was hearing. I assumed that Linda had been quietly stewing in her corner of the table. Maybe she had been, but for whatever reason she had done a complete about-face about not removing her clothes.

"Uh, Linda...I took off my clothes to just pay rent. You and the others are getting much more value than I did. I'm not sure that's fair," complained Telly.

"Hey, don't blame me if you sold your naked body for such a low price. This wasn't my idea, it was yours. What's the matter? Are you afraid of another guy seeing your wife?"

"No...but what if you and Gary agree to do it but Shelly doesn't?"

"Tough shit then, Telly. I can't make her get naked. Neither can Gary. All I need is for her to agree to let Gary get naked. I don't need your permission since you've already sold your clothes."

This was getting touchy. Clearly, there was tension between Telly and Linda. Linda wasn't happy about what he did and she was going to make it as tough on him as possible; even if it meant enduring some personal embarrassment.

Shelly looked at me. Suddenly, she looked like she didn't care about the game.

"What do you think, hunny?" she asked me with a concerned look on her face.

All I could think about was that I had a wonderful opportunity to see Linda in her naked glory. Although I had never seen much skin on her, I often wondered if she was much nicer to look at than she let on. This was my chance. All I had to do was convince Shelly to go along with it. Of course, then it would be only fair that Shelly get to do the same. Did I want Telly ogling her naked body? I hadn't seen much of her naked body in broad light in many years. We always made love in the dark and she always locked the bathroom door when she took a shower or got dressed.

The chance to see my own wife naked in broad light appealed to me as well. If it means sharing that scenery with another guy, then so be it. I'd be getting to check out his wife's goods as well.

"Since you asked, Shelly, why not? I just don't think you'll do it. I'm not really sure Linda will, but it was her idea so it's possible. I can't see you doing it."

"I tell you what," Shelly suggested. I don't need the hotels right now. I have a chance to do more damage. If you two want to go for it, I won't stop you."

"I have an idea," Linda suggested. "I'll do it if Gary does it. One item at a time until we're both naked. Then we get hotels on our properties."

I agreed. I'm not sure Shelly expected this but she remained silent. I stood up, pulled off my sandals, and Linda did the same. I pulled off my shirt and again Linda followed. I was bare-chested but Linda still had her bra on. I insisted that she pull off her bra before we started on the bottom half.

She hesitated but slowly removed her bra. What I saw was much more impressive than I had imagined.

She wasn't large, but her B Cups were perfectly rounded. They barely had any sag to them and she had large, puffy, pink areolas with thick nipples protruding from them. I was busy staring at them and forgot that it was my turn to remove an article of clothing.

At the sight of those sexy tits, I had begun to stiffen inside of my pants. I pulled down my pants and my erection poked out of the front of my boxers. I realized that I was no longer covering much and just casually pulled down my boxers as well.

Linda suddenly seemed a little more at ease and removed her pants and panties quickly. Again, I was treated to the sight of a thick patch of red hair between her thighs. She had a much nicer ass than I had imagined as well. She was sexy as hell when she was naked and my hard cock showed its appreciation.

I wasn't intimidated by the much longer package belonging to Telly. My hardness clearly distinguished the fact that I was much thicker. Although Shelly couldn't help but taking peeks at him, I stood proudly while I gave Linda as much time to look as she wanted. Of course, I was getting a good look at her as well.

We sat back down and after two more times around the table, Telly was done. He sat quietly as the rest of us took our turns. I'm not sure if Linda was feeling a little bit of sympathy for him, but she offered to let him sit next to her and she'd rub his cock while she played. Maybe she was doing that to show that he's her territory.

Linda had a run of very good luck suddenly combined with some disastrous rolls of the dice by Shelly and she had Shelly being forced to sell her houses on her properties to make a rent payment on Kentucky Ave.

"Or, you can remove your clothes and I'll skip the rent. I'm sure Telly won't mind. Besides, you're the only clothed one left."

"Not just for rent, I won't. You two got to build hotels when you stripped down."

"You could have too, Shelly," Linda reminded her. "You chose to wait until you needed the cash."

She knew Linda was right.

"Well, if I'm going to strip, I'm getting more than just a few hundred dollars of rent. I tell you what. I've been watching Telly over there. I'll cash in my money, leave the game, and he can sit next to me and I'll play with his cock while you two finish."

Holy shit! I sat in stunned silence as I listened to my still-clothed wife make that suggestion. More surprisingly was Linda's response.

"Fine with me. Just understand that no matter whoever wins this game between me and Gary, I'll get to do the same with him that you two do. Otherwise, I won't agree to it."

Nobody asked my opinion. I enjoyed the voyeurism. I loved seeing Linda's beautiful naked breasts above the side of the table. I wasn't expecting it to go any further than possible Shelly getting naked. I was about to say no to the idea when Shelly spoke up emphatically.

"Sure, why not? That's fair."

Before I could even respond to that, Shelly was removing her clothes at a rapid pace. I was enjoying the show too much to even voice an objection. I hadn't seen her completely naked in full light in at least 3 years.

Oh yes. Those large breasts with her light brown areolas and perpetually hard nipples. Her wide hips and the beautiful patch of blonde fur that nestled between her legs. Not surprisingly, Telly appreciated what he saw (as did I) and his cock showed its growing appreciation.

He sat next to my naked wife while Linda and I took turns. The game went back and forth with each of us looking like we may finally finish the other off yet not quite be able to do so.

Both Shelly and Telly had stood up and Shelly was jerking on his cock while he fingered her pussy. I wasn't real happy about that but I wasn't in a position to put a stop to it. I knew that I would get the same privilege with Linda.

In the middle of Linda's next roll, we heard a grunting sound from Telly. He had shot his load all over Shelly's chest and some had gotten on his belly as well when they embraced. Again, if it weren't for the fact that I would get the same treatment later (if Shelly didn't back out on her promise), I would have just stopped the game and given the win to Linda.

Linda grinned at me. "You're next."

"No, it's still you're turn. You just rolled a seven."

"No, Gary. I mean, when this game is over you get the same treatment."

Shelly looked at me and shrugged her shoulders. What in the hell did that mean?

Shelly left the room to take a shower to remove Telly's juices from her chest.

Telly followed right behind. He needed cleaning as well.

There was a part of me that just wanted to concede the win and get my hands all over Linda. After nearly 20 minutes, our spouses still hadn't returned from their shower. I could still hear the water running.

I conceded the game to Linda. The way we were playing, she was probably going to win anyway. We walked to the bathroom to find Shelly against the shower wall and Telly shoving his hard meat right into her. Telly's back was to us and although Shelly was facing towards the open door, her eyes were closed as she was enjoying Telly's meat pounding inside of her.

Now, both Linda and I were angry.

"Gary, no offense to you but my plan was just to do some touching. Later, I figured I could jerk you off since that's what Shelly did. I'm not sure I can go further, although I really do like you."

I wasn't even in the mood to do anything. I just wanted to get dressed. We sat with our clothes on and passively watched TV until our spouses finally came out, still naked of course.

"Wow, that was quick? Did you already jerk Gary off?" Shelly asked.

I was going to answer honestly but Linda stopped me.

"Oh yeah. It was quick. Next time maybe we can take more time. You were in there for quite a while. Did you jerk him off again?"

"Yes, I hope that's okay since you only did it once."

That lying piece of shit. Not only did she lie, but Telly went right along with it. Obviously they didn't realize what we saw.

Telly got dressed and they went home. Shelly was in a great mood and wanted to do more but I wanted nothing to do with her.