Peggy

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Peggy asks questions and then takes control.
1.6k words
4.52
9.5k
11

Part 1 of the 2 part series

Updated 11/24/2023
Created 08/12/2023
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tailtales
tailtales
191 Followers

Peggy

Peggy asks questions and then takes control

I asked Peggy if she'd like to join me at a local restaurant for a meal one afternoon. I was surprised when she was saying yes before I had finished asking her. After realizing what she had done she was a bit confused and finally admitted that she had been anxious to visit the place because it had been getting good reviews. Plans were made and a reservation was setup. We both live in the same high-rise so it was just a matter of meeting and driving away.

The meal was everything that had been promised. As we were having a final cup of coffee, Peggy looked at me and asked if she could ask a rather embarrassing question. "You can ask. But I may choose not to depending on the nature of the question. OK?"

"Well...I...Um...Well I always kind of wonder...If...Um...It's kind of strange but... I kind of wonder what kind of underwear men are wearing. Ya know...Boxers...Briefs. You don't need to answer if you...ya know. But I think maybe you're a briefs kind of guy."

To say I was even more surprised by the question would be an understatement. But I answered anyway, "No."

"Really boxers, I don't picture you in them?"

"No."

"Are you really commando?"

"No."

"Well it's got to be one of the above."

"How about a pouch?"

"What the hell oops excuse me, what is a pouch?"

"How do I say this without being coarse?"

"I've heard it all before. Stop stalling...What's a...Oh...Wait...Let me guess."

"Well the name does kind of explain what it is, right?"

"Ya, it does, doesn't it? Kind of like a holder for man stuff. Then maybe a thin waist band and a skinny strip down the back. Am I right?"

"Yup, that's a fairly decent explanation of it."

"Wow Hank. You are something else. I would have never in a million years... No briefs...No boxers. A pouch...Is that all you ever wear?"

"Pretty much all time. I do have boxers but prefer the pouch."

The conversation kind of died at that point. The waitress brought over the check and I gave her my credit card. As we stood on the sidewalk for a moment Peggy took my hand and squeezed it. "Would you show it to me?"

"What?"

"The pouch...Will you show me the pouch? I've never seen such a thing."

"You do know what you're saying right?"

"Yup, I do. I want to see what a pouch looks like. When it's being worn...On a man...Like on you, without a shirt."

"Well that presents a problem. How about I just show you one from my drawer?"

"No, I think I want to see what it looks like on a body, on your body. Am I being to bold? Or am I being too subtle for you?"

"I may be a bit slow but I'm beginning to catch up."

"I certainly hope so, I have high hopes. Can we go now?"

At my apartment I offered Peggy a cup of coffee and she suggested I quit stalling and show her the pouch I was wearing. I offered her a glass of wine. That didn't work. Neither did a stronger drink. "Come on Hank. Off with your shirt. Should I help?"

I told her I could do and I did. "Whoa, you are in good shape aren't you? OK, now the pants. Shuck em off."

I undid the belt and snap and zipper before I realized my shoes needed to come of first. Hopping around on one foot then the other they came off. "Are you sure about this?"

"Absolutely, drop em. I want to see this pouch thing."

So I did. Something was compelling me to follow her instructions. I was kind of in a daze. I stood there with my pants around my ankles feeling foolish, and hard. While the pouch was good when I was soft it didn't have much strength when I had an erection. It would stretch out and then my testicles would be exposed.

"Oh, Hank, I like it. That's so much more interesting than boxers or briefs. Yes, so much better. Maybe get rid of those the pants around your ankles. Good...Even better yet. Can you turn around? I want to see the back."

As I started to turn, "Wait, stop. Stay sideways a minute. Do you realize in profile you have a most intriguing appearance? The way it's bulging...Your nuts are just there. The only thing I can't see is your pecker. This is great. I love pouches. All men should wear them."

Then she had me turn the rest of the way around. "This is good almost as good as the side view. The way the string disappears between your cheeks is fascinating. How does it feel rubbing against your butt hole? You have a good looking ass, did you know that? I bet you exercise it don't you?"

I admitted that I did a few exercises each morning. "Yep I can tell, now back around so I can get another look at the front. The back is delightful but the front is wonderful. I'm torn. Which is better, the side view or the front view? Go sideways again. Yes, just like that."

I had never realized it before. I was enjoying showing off my body, really enjoying it, maybe because Peggy was so enthusiastic. Her apparent joy was catchy. And of course at this point I was expecting that sex would be next. I knew she was tall, slim, with long legs and could picture them wrapped around my waist or maybe wrapped around my head as I spent some time sharing my oral skills with her.

I was wrong. "OK, big guy, drop em. Let me see the rest of you, the part hiding behind the bit of fabric."

"Let's go into the bedroom. It'll be more comfortable."

"No. Take em off here. I want to see it. Show it to me."

Can I first help you to take off your"

"No. Just do it. Take that pouch off. I want to see your penis, your hard cock. Just show it to me."

So I did. I hooked my fingers in the waist band and pushed down. It was hung up on my erection but it finally slipped down and I stood there naked. "Yes...Just like that. Let me look. Put your hands behind your back. Thank you, much better. Maybe kick that away. It spoils the scene with them around your ankles."

Peggy slowly walked around me. I could feel the heat from her hands as she almost touched my buns. Then she asked, "Move your hand please...Thank you. Is it OK if I touch you? Back here. They look so firm."

Before I could answer she was doing it. One hand one each cheek she was squeezing, firmly. Then she pulled and spread them open me open. "Ya Hank, that's a neat asshole. You are one good specimen of manhood." Then let go.

As she moved back in front of me her hand slipped along my hip. When I thought she was going to take my cock in her hand she pulled away and just stood there, looking up and down my body. She had a satisfied expression on her face. "Yep...You look good."

I asked, "Are we going to move into the bedroom?"

"No."

"Move to the couch?"

"No."

"Where are you thinking we're going to"

"We are not. You are going to masturbate for me."

"What?"

"Jerk off. You know how. I want to watch you do it. Wrap your hand around it and move it up and down, slowly at first. I want to watch it swell up bigger and bigger. And when you get close do it faster and faster until it all comes shooting out. Warn me first. I want to be ready when you explode."

"Take off you blouse. I want to see your tits."

"No...This is you showing me what I want to see. Get started. Jerk it."

So I did. Slowly like she wanted and then faster as the pressure built up. "Here it comes. It's coming."

Peggy stepped to the side just in time. I don't think I have ever shot so hard and so far from masturbating before.

"Well done Hank. I am very impressed. I may want to see you do that again one day. Yes...Yes indeed. A great body, a wonderful cock and you follow instructions very well. And the finish was outstanding. Such distance and the volume was huge, ah yes very nice. Would you be willing to do this again someday?"

I could only nod my head yes. It was the most surreal event in my life. I was dumbstruck. I let a woman control me. I had never been treated like it in my whole life and I loved it.

"How about I stop by next Saturday? At let's say three."

A week and a day to recover, I nodded yes that would be OK.

As she moved toward the door, "Maybe I could bring my niece along. Yes I think I'll do that. It's about time she learned a little about controlling the male species. She's a freshman at the U but will be home for the weekend. Yes...I'm going to do that."

She stopped and walked back to me. "Thank you Hank. I really enjoyed our lunch and everything." She kissed me on the cheek, the one by my nose. "Marty will be so interested when I tell her what you've agreed to do. Yup, she'll be so excited." And out the door she went.

The end

If enough readers enjoy this little tale I have an idea for a sequel.

tailtales
tailtales
191 Followers
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6 Comments
AnonymousAnonymous5 months ago

Good premise.

Had REAL potential. But was so rushed. It was like a drag race. Short. Fast. Over almost before it started.

Three stars.

lc69hunterlc69hunter6 months ago

know where this is going

Norway_1705Norway_17056 months ago

"Her apparent joy was catchy"!

Pay no attention to the number of comments! Most readers are very quiet and never make comments.

That woman's joy is precious! A follow-up would be necessary

AnonymousAnonymous8 months ago

Fun story. Look forward to the sequel

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