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."
