Absolutely

I recently was tasked with cleaning up the hard drive of a recently deceased relative. I found a file with documents in it and thought I should give it a glance to be sure nothing was important. It was filled with copies of emails sent to an *unknown friend, (*unknown to me), but I know the people spoken of in the email. My eyes have been opened and I have to share.

Hi, Buddy:

I know you have often wondered and asked how we had met our close friend, Alan. I have put it off simply because I wanted to give you the best answer without being too wordy. So, here it is in an email form. I hope you enjoy it and if you share, share it only with people who will not recognize us.

Somber moments seldom last. Sure, there was Queen Victoria who made the world think she grieved for her dead husband the rest of her life, but odds are that was all for political reasons. In life humans are built to move on. Memories fade to an acceptable level of pain and new experiences supersede old memories. Yes, this is an odd beginning to what otherwise is a story of erotic experience, but it is important to give notice to the beginning.

My wife and I had only been married for five years. That statement might lead you to believe we were young at the time. We were not. In fact, I was pushing sixty and she was coming up on fifty-seven. We are both active, but if I am honest, which I hope to be, she was much better looking than I was and definitely hotter than I ever deserve. But, if not for me, she may never have realized her 'hotness" so it works out.

Now, for the descriptions. I was 6ft, dad bod, white hair. With a beard I could pass for a thinner Santa. Isn't that sexy? I have been known to quote the line from the one movie starring that one guy who becomes Santa by putting on the suit. You know, when he turns to his ex, holds his arms open, jiggles a bit and says "What woman wouldn't want some of this?"

My Missus, however, looked nothing like Mrs. Claus. Well, maybe she did if you think of Mrs. Claus as a hot, milfy sex bomb with curves in all the right places, an attitude of sweetness that is charming; a woman who knew just when to turn on the sexuality. Just the mere idea of her is enough to start my blood pressure to rise; in a good way. Standing at just over 5'5", she was tall enough to have legs that look long and sexy, especially in heels, which she wore for me, but still she didn't tower over me when she was wearing them. Her weight was just right. Giving a number would be contrived and since weight always fluctuates, it would not be accurate. Besides, a gentleman never discusses a lady's weight. When she did put on a few pounds, those pounds seemed to find her tits before any other part of her body.

Her tits were C-D cups, (Depending on the above mentioned weight gain/loss). I know some men would love to exaggerate in a story and say that the woman had Double or even Triple D. That just isn't the case. My wife's tits were perfect. They did not sag much, and were not so large that going braless was impossible or overly immodest. (More on modesty in a bit). I loved when she wore certain clothing and went braless. It was the height of fun when I would catch a guy's reaction and see his realization that the hot milf before him is braless and still pointing up instead of at the floor.

So, let's give you some names, ok? Because, right now, you are probably still stuck with that Santa thing. I know, it can weird you out a bit. But, obviously, I can't give you our real names. So, let's call her Charlene. I am Charlie. Believe me when I say those names are closer to being real than they are made up. I just don't have that kind of imagination.

I had known Charlene for years. We were in our college age years when we first met. We met at a church function, in fact. Remember I mentioned modesty? This is where it comes in to play. People of a certain age will understand when I say we had modesty pounded into our heads. It was the number one item on the menu. A girl couldn't wear certain jeans because you could tell if she had a dime in her back pocket. I don't know what those people think of leggings and yoga pants. I don't really care, either. They are a "blessing" in my opinion.

Charlene and I were friends. We would flirt. We never dated and both, in fact, ended up married to our life partners. We lived happy, fulfilled, modest lives with our partners. Lives that anyone might memorialize as a testament to clean, healthy, chaste living. But, we both realized after we were left alone we were tired of living like that. Life was short and we just wanted some fun.

Charlene and I ran into each other at a function. I asked her if she would like to leave and go somewhere to catch up. She agreed. Let's just say that the guest of honor didn't know we left early.... We decided on something nearby, nothing noisy or trendy, and ordered lunch. Catching up happened quickly and resulted in discovering we didn't want to be alone and that we didn't want to continue being boring. And that, folks, was that.

Boy, that was a lot of ground work, wasn't it? But, I feel it was important to give an understanding of who we were and, maybe more importantly, why we did the things we did. So, let's move on.

We married and decided to explore new and unusual things. We started pretty quickly because our number one rule was to be open. It turned out that neither of us ever felt comfortable discussing sex with our late spouses. This resulted in talking about sex a lot with each other. It was during one of these discussions that we decided to visit one of those Adult Bookstores in our area. The conversation went something like this one Saturday morning:

"Babe, have you ever shopped in one of those adult bookstores"

I looked up from my cell phone to question her.

" What brought that up?" I asked. I didn't mind the question, but I was always amazed at how her mind worked.

"Well, we passed one yesterday and I have been thinking about it. I want to go have a look-see."

"You do?" at this point, I was already getting excited. "I would love to take you to one, but I am going to tell you it isn't just a store."

"Are you talking about the video booths?" Charlene asked.

Now, to be honest, I didn't know whether I should be surprised or not. She could come across as an innocent little angel but this woman held knowledge and wisdom of the world that would surprise all of our friends.

"Yes, partly I am. How did you know about them?"

"Well, because they advertise them on the building. Honestly, that is what caught my attention. I want to see what it is all about. Can you take me today?"

How could I say no? But, I wanted to make sure this was an adventure.

"Sure, babe, I can take you. But, you need to shower and dress first."

"Um, ok. Why? What's wrong with the way I am right now?"

I smiled and replied:

"You said you wanted to see what they were ALL about. There is no sense in going unless you go all the way."

An hour (or so more), later we were in the car. Charlene had blown out her hair in that 80's style that guys still seem to like. She was wearing a red knit top that hugged her just right. She was braless. When she walked, her tits bounced nicely. She was also wearing a short, above the knee pleated skirt. At my insistence she was not wearing panties. She looked the part of a sexy milf who wanted to turn heads but was not showing everything off. It was perfect.

We made the drive to the bookstore, about thirty minutes away. She hiked her skirt up so I, and a few truckers, could enjoy the view. When we got to the store, I parked in back, opened her door, took her hand and purposefully led her inside. I did not want her to second guess.

Once inside, it was what you might expect. There was a wall of toys, rows of DVD's and some old style magazines, ranging from soft to hard core. Charlene's eyes opened wide in wonder. She turned to me and said:

"Where should we start?"

Before I could answer, a voice came to us from behind the raised counter behind us.

"Welcome to the Adult Emporium, let me know if you need anything."

We both turned to see who had welcomed us with such apathy. It was a younger man in his mid twenties. He was staring at his phone and had not looked up to speak his greetings. He didn't look greasy or seedy, despite where he worked. In other words, he didn't fit the stereotype. I quickly formulated my brilliant plan, and taking Charlene by the hand, led her over to the proprietor.

"Good day, sir." I said, trying to be whimsical. That caught him off guard, because he jumped a bit and looked up.

" I have the distinct honor of being the very first person to introduce this fine specimen of a woman to the joys of your marvelous emporium. Doubtless we will need as much help as you may be able to offer."

With that, I stepped aside and tugged on Charlene's hand, bringing her in front of me to the view of the young guy. His mouth opened to say something but just hung there. His eyes tried to roam over her body but, to his credit remained glued to Charlene's face. See this, I leaned in and said in a stage whisper,

"Darling. Please inform this young man that he is welcome, nay, encouraged to look as intently at your body as he desires."

Charlene gave me a bemused look.

"Go on. I didn't drive all this way to keep you to myself. Tell him."

Charlene turned to the young man and, with a half curtesy, said to him

"Oh, please do, kind sir. Please look at me to your heart's content."

I could not help but bellow with laughter. I knew this was going to be a very good experience. The young man was suddenly pulled out of whatever interested him on his phone and gave my wife his full attention. Charlene, for her part, was now being both a bit submissive and mischievous.

"Good sir," I intoned, keeping with the mock tone of propriety, "This fine lady, whom I hope you find to be up to your standards "

"Oh, she definitely is!" He squeaked out

"This fine specimen of womanhood'" I continued "Is in dire need of a specialized toy. Her current inventory is paltry, at best and she has been required by the very scarcity of her collection to start at the very beginning and build up her specialty drawer, as we shall call it."

I stopped, simply to see if the young man would play along or if he thought I was a complete moron. To my great delight and perhaps, to a lesser degree, Charlene's horror, he did indeed play along.

"Oh, do go on, Sir. I shall make every endeavor to fill the lady's need." He replied.

I was really beginning to like this guy. He wasn't just some lame brain who worked the counter at the local porn shop. Instead, he now had a genuine interest in the customer's needs. True, he also had an obvious interest in my wife's figure, but the monotony of his day had been shattered. I also really liked how he looked at my wife.

"Where would you fine people care to start?"

"Well," I replied, "As the song says: Let's start at the very beginning. That would be the letter A. The lady needs an Anal Plug. "

Charlene nearly fell over. She was obviously turned on and embarrassed at the same time. Our shopping guide let a laugh escape and looked at her.

"Follow me." Was all he said.

I took Charlene by the hand once again and urged her on.

"Come, come. Let's not dawdle. You started this adventure and it is too late to turn back now. We are too old to not try something new. Let us embrace the unknown with gusto."

"You are really enjoying this, aren't you? Are you just cracking yourself up?" She asked

"Indeed I am, dear lady." Was my reply. I was surprised and pleased when the store clerk turned and said

"So am I!"

I laughed and said "You, sir, are obviously a fine connoisseur with great taste." Charlene groaned but then took in her breath.

"Are these...?"

"They are, indeed."

"I never realized there were so many kinds."

Breaking character somewhat, mostly, I am sure, because he had never discussed butt plugs while attempting to mimic a Charles Dickens character before, the young man smiled and said :

"This is nothing. We have a good selection but this is only a sample. You should see some of the hardcore stuff."

Charlene raised an eyebrow,

"Wait, these are made to be crammed up my asshole and you don't consider this hardcore?"

He laughed so hard he snorted.

" I'm serious! This seems pretty hardcore to me!"

To emphasize her statement, Charlene stomped her foot. While she intended it for emphasis, it caused two things to happen simultaneously. First, her tits bounced up and down, much to the delight of our new friend. Secondly, it caused her short skirt to rise nearly high enough to give a nice view. The young man snapped his head up and down with such force he became momentarily dizzy and reached out to steady himself. He reached for a nearby rack and instead placed his hand on Charlene's left breast. She looked down at the hand, then up into the horrified eyes of the hand's owner. She smiled and said

"Do I get a friend's and family discount now that we are so familiar?"

It was now my turn to snort.

I managed to sputter: "Familiar? He hasn't even told us his name."

To this, he sputtered. "Alan. My name is Alan."

I couldn't help but laugh more.

"Alan, the anal plug analyzer. This is beyond perfect.

Well, Alan, it is time to work your magic. My wife needs her first ever butt plug and we are trusting you to help choose it. How does that sound?"

It was apparent by the front of his pants that it sounded good to him.

I will forego the brilliant conversation and innuendos that passed between us. They were all necessary as they helped to ease Charlene's mind. Alan commented a couple times that we were really cool and fun customers. It was mid-morning so the store was not yet busy and Alan had plenty of time to assist.

We started with color, and he expounded on what each color kind of symbolized. Color led to texture discussions which led to discussions about materials. We eventually narrowed down what Charlene thought would be the most comfortable and wearable, allowing her to walk and sit while also stretching her a bit at a time. We walked our purchase up to the front with Alan. As we did so, I glanced over to the sign above the video booths that read "No purchases beyond this point."

"Alan," I began "One of the reasons my wife so desperately dragged me out today was to check out your video booths. It distresses me to see that you have allowed us to shop knowing full well that your store has a policy against taking purchases into the viewing area. I will have to mention this in my google review."

Quickly, as if he thought I actually meant the part about the google review, Alan said:

"You can leave it here at the front and pick it up when you leave."

I also noticed the basket full of lube samples. I reached over and picked up several. Handing them to Alan, I said:

"I have a better idea. How about you throw in this lube for free. Once I make the purchase, I will send my wife behind the counter with you where you will lube up her ass and insert her first ever butt plug. Then, we will buy tokens and go to the back to view some movies. You will get to be the first man to insert anything into her asshole."

I thought he was going to lose it at that point.

"Are you serious?"

I looked over to Charlene who was looking at me with an expression that also said

"Are you serious?!?"

I looked at her and gave her a signal with my head that she understood meant

"I am in charge now." She became her submissive self, looked at Alan and said:

"Yes, he is. He is very serious;"

Alan put the lubricant in the bag, finished ringing up our purchase, handed me the bag and said

"Just a minute."

He moved to the door, turned the lock, flipped over the sign that said closed for lunch and came back to where we stood.

"Let's move over to the office. It will give us more privacy."

We followed Alan over to a door marked employees only. He opened it, and stepped aside to allow us entry. In a very unusual move, I stepped in front of my wife and entered first. She followed after. I did this not only to allow Alan a view of her ass in the skirt, but I also pulled up short. Charlene walked into me and stepped back. When she did, she backed into Alan who reached out to keep her from stumbling. His hands found her waist and briefly moved to her hips. He liked what he felt.

"Alan, my new friend, we are in an interesting situation here, wouldn't you agree?"

"Yes, sir, we are indeed."

"Here is the proposition I am going to make to you. I am going to allow you to insert this buttplug into my wife's ass. This will require copious amounts of lubrication. I do not want it to hurt. I also do not want the lube to stain her clothing. Therefore, I feel it will be necessary for her to strip completely. However, I need your solemn promise that you will not attempt to fuck her once she is nude. Do you understand? You can obviously play with her tits. You will be inserting a buttplug which will require you to lube her hole well. I am sure that some of that lube will slide down and need to be wiped from her pussy. I am asking you to be as much of a gentleman as you can while my wife is naked and bent over this desk. Do we have a deal?"

Alan was shaking like a leaf by this point. Charlene had resigned herself to the fact that she would soon be naked if Alan said the correct word. Alan looked at me, then looked at my wife and then back at me and said:

"Abso-fucking-lutely. I mean, no fucking. Just helping. Yes. Whatever the right answer, yes, I understand."

I smiled, turned to my wife and said: "Woman, strip naked and wait for instructions."

Charlene stepped back a few steps, unzipped her skirt and let it fall to the floor. She unbuttoned what few buttons were on her shirt and pulled it off. She handed it to me and waited for what I would say next. From my side I heard Alan breathing hard

"You ok there, buddy?" I asked

"Oh, man, I am more than ok. Your wife is fucking gorgeous."

"You mean no fucking gorgeous."

"Right, that is exactly what I meant."

"Babe," I said, turning to Charlene, " Come here, give Alan the lube and turn around. Bend over the desk and wait."

She did exactly what I said to do. Turns out I wasn't thinking about how long it would take to open the package with the plug in it. Once she was in place, I told Alan to start lubing her up as I opened the package. You know how those packages can be. I struggled with the damn thing for way too long it seemed. Alan, however, didn't seem to mind. He had begun to squeeze the lube into Charlenes crack. She had reached back and was spreading her cheeks for easier access.

"Shit! Too much! Sorry."

I looked over and saw a large glob of lube sliding down onto my wife's pussy. Alan stood there with his hand cupped under her spread legs to catch it.

"Hey, Alan? I think it would work better if you just scoop it off that pussy and maybe rubbed in what was left."

He looked at me with a bewildered expression.

"Really?"

"Let's be clear. You cock stays in your pants. But, you have to use your fingers. IF I were you, I would be taking full advantage of the situation. Just make sure that hole is ready for this plug."

I returned my attention to the packaging. I wanted to get it open and watch the show. It was just packaged too well. As I concentrated on the package, I could hear the sounds of Alan's wet fingers doing their best to capture and use every ounce of lubricant. I soon began to hear Charlene's grunts and then moans as Alan seemed to be hitting all the right spots.

"Oh fuck. O fuck. Oh FUUUCK.... He has fingers in both my holes. I have never felt this before. It. Is. So. Fucking. Good."

I finally had the package open. I looked up to see Alan adding more lube to my wife's asshole while he worked her pussy with his left hand. It was a wonderful sight.