Chapter 1: Red Dress

Caution: This Sex Story contains strong sexual content, including Ma/Fa, Consensual, Romantic, Lesbian, Heterosexual, Oral Sex, Anal Sex, Size, .

Desc: Sex Story: Chapter 1: Red Dress - Dan Helton decides he owes something to the six women he used as surrogates for his late wife Hildie when celebrating the date of their anniversary. An expansion of the story "Red Dress," with Chapter 1 a slighty rewritten version of that story.

"Do you mind if I sit here?"

The voice belonged to a fit looking woman I judged to be in her mid forties, about ten years younger than me. She had dark brown shoulder-length hair, brown eyes, was probably about 5-5 or 6 with a nice trim waist. Her hips flared out nicely and her chest sported a pair of moderate, shapely breasts. Nice!

The reason I knew details about her shape was the bright red dress she wore. It was a spaghetti strap party dress that fit her very, very well, but seemed to be styled so as to make her look younger. I certainly didn't mind having this vision sit next to me. "Sure, have a seat."

After ordering a white wine spritzer she turned and stuck out her hand. "I'm Linda Pearsol."

"Dan Helton. Nice to meet you." Her handshake was firm and she had a positive air about her. No wedding ring. We talked about a few inane things while I mulled over the various reasons why a sharp-looking woman like her would be chatting up an older guy like me.

Eventually she started punctuating her conversation with little touches - innocent at first, on the shoulder and arm, then moving down to the hand. At this point I decided to slow things down a bit.

"Linda, why didn't you put your hair up in a ponytail?"

She looked at me for a moment, then replied "Because that would have been a little too much. You wouldn't have taken me seriously."

"And the dress?"

She grinned. "I'm sure I don't have to explain that to you."

I grinned back. "You're right about that. Now, since you obviously planned this out very well, there must be a point to it."

"Of course! I'm trying to entice you back into my boudoir for a night of limitless passion!"

I slowly shook my head. "Sorry, I can't do that."

Her mouth made a little moue. "Why not?"

"I'm too old to do the 'night of limitless passion' bit."

"You never know until you try."

I looked at her. She looked right back at me, a twinkle in her eye. I believed she was serious. "Well, let's just say I'm not exactly willing to try it tonight. Do you have a backup plan?"

"A nice evening spent with a friend? A little talk, a little dancing... whatever you want."

I raised my eyebrow. "Whatever I want?"

She smirked a little and answered, "Why, is there something you want to do that you think I wouldn't?"

I decided I'd had enought of the sexual inuendo and turned to the bartender. "Tony, what do I owe you?"

"Twelve-fifty Mr. H."

I dropped twenty on the counter and started to push away. Linda grabbed my arm. I stopped and looked directly into her eyes, which had turned a little sad. She held the contact for a moment, then glanced away and let go. I walked out of the bar without looking back.


As a widower who managed to take early retirement I pretty much do what I please. I have no close family or friends, although there are several good buddies and two couples that I maintain consistent relations with. All in all, I like where I live and what I do and manage to keep busy without being tied down.

One of the things I like to do is visit one of the area casinos with a buddy or two several times a year. That was where I had my second run in with Linda about two weeks later.

I was sitting alone at one of the blackjack tables, doing a bit better than usual, when a woman wearing red slipped into the vacant seat to my left and plunked down a small stack of chips. She looked to her left first and then turned to me. I was carefully not noticing her since I was pretty sure it was Linda. I felt her stare for a moment, but didn't turn as the cards were dealt for the next play. I split a pair of eights, drawing a six and a five. I hit both, and busted both. With a sigh, I gathered in my chips and turned to my right to leave. I expected her to call out or follow, but was pleasantly surprised when she didn't.

I wandered off slowly, hitting a couple slots on the run, using the various mirrors to make sure it was indeed Linda. She stayed at the table, playing her small pile of chips and as far as I could tell made no effort to see where I had gone.

I decided she'd earned another shot at me, so I made my way to the nearest restaurant, asking for and getting a table by the windows.

I was working my way through my salad when she appeared, walking toward the restaurant at a leisurely pace. This time the red dress had a scoop collar and elbow length sleeves. The hem on the ruffled skirt reached just above the knee. Appropriate for the scene except for being red.

I caught her eye, smiled and waved her in. She seemed a little surprised, but immediately smiled back and nodded. Moments later she joined me.

"Hi Linda. Do you come to the casino often?"

"Not really, I've only been here a couple of times and I'm still learning the ropes. How about you?"

"I've been here many times and I'm still trying to learn," I chuckled. "For instance, I was doing well at blackjack earlier so took a chance and split eights, for god's sake! I got just what I deserved and realized I'd better quit if I was going to do things like that." I wondered if she would admit she saw that.

"So that WAS you! I thought so. I must have sat down next to you just before that happened. Frankly, I didn't understand what you were doing with those eights. I didn't know you could do that."

"Well, then, maybe you better read up on blackjack before you try it again. It's not quite as simple a game as the casino would have you think."

"I believe you." She paused and I wondered if she would try to turn the conversation toward personal things. I was again pleasantly surprised. "Since you've been here a few times, I'm sure you have a good idea what to order."

"Well, I usually stick with the T-Bone, but everything I've tried here has been good." I waited for her to order a T-Bone.

"In that case, I'll have the shrimp scampi." She looked me in the eye and grinned. "I don't think a little garlic is going to affect my relationship with you."

Was that a reference to the way I blew her off the last time? I wasn't sure.

We chatted about gambling while we ate, with me giving her a primer on blackjack and craps. She seemed genuinely interested. When we finished our coffee at the end I called for the check. She started to get out her purse and I waved her off. "I invited you in, I pay. If the situation is reversed, then you can pay. Deal?"

She looked carefully at me for a moment, then nodded, held out her hand and said, "Deal," and we shook hands. "What's next for you?"

"I'm headed to the bingo hall to join a buddy for a couple hours."

"I'm surprised. I wouldn't place you as part of the bingo crowd."

"Surprises me too, but somehow I got in the habit and I really enjoy it now." I thought for sure she would ask to tag along.

"Well, that definitely isn't my cup of tea, so I think I'll try putting your knowledge to work at blackjack for a while. Thanks for dinner." She smiled and waved gaily as she took off in the other direction.

Damn! Maybe I had completely misread the situation. I ran over the possibilities in my mind again and decided it didn't really matter. Either I would see her again or I wouldn't. I found myself hoping I would.

Trying not to think too hard about it I headed to the bingo hall.


Hildie passed away over six years ago. To say she was everything to me would be an understatement. Don't get me wrong. I'm not going to bars or casinos to get away from the world. I enjoy good company and conversation, I just tend to limit it to the people I know and trust.

You see, Hildie was more than my wife - she was my best friend, my partner in business and in life, and my only lover. And yet I never felt the lack of not being with another woman. It may be because we had an incredibly active and imaginative love life up until the day she died. Since her death I had felt no need 'dip my wick' elsewhere.

I have continued to celebrate our anniversary, using the night as a way to honor her memory and relive the magic. I do the same thing every year. First dinner at a fine restaurant, then off to a show, and finally somewhere that features a live dance band. And I have used the same escort service every year to provide me with a partner for the evening.

Before you start questioning how this honors the memory of my wife you should know a couple things. My deal with the service is that the woman is not to come on to me in a sexual manner, should be able to dance, and should simply enjoy the evening to the best of her ability.

Oh, yes. And it MUST be a different woman each year.

Apparently Max, who runs the service, picked up on my needs very well. The women have been mostly older (meaning not in their twenties or teens), have dressed appropriately with just a hint of makeup, and either were very good actresses (which in that business should be considered a given) or actually enjoyed the evening.

And of course they all could dance, usually very well.

During portions of the evening I would feel Hildie there, enjoying it with me.

So I called the service as usual and got ready for the evening. Right on time the door bell rang...

... and the woman at the door was wearing a beautiful, formal, RED dress. It was Linda.


"Good evening Mr. Helton, I'm Miss Pearsol and I'm here to be your escort for the evening." The words were delivered as they always were, with a smile. But there was something in the back of her eyes. Fear? Hope?

"Come on in. It'll take me just a moment to finish getting ready." To this day I'm not sure why I didn't just explode and tell her to hit the road. Maybe I'm just too nice a guy. Maybe Hildie trained me too well. Or maybe I wasn't as shocked as I thought I was.

I went into the bathroom and needlessly adjusted my tie for several minutes. I ticked off the items in my mind. Linda definitely planned this in advance. The red dresses were an admission of that planning.

She had to have known she was the one to be my escort this year and had to have talked to at least one of the other women. And yet she seemed to be ready to treat the evening as if she had never met me. Why?

Did it matter? Well, yes, it did. Did I have to know why right now? No.

In fact, I knew that if I pushed the matter now it would probably ruin the evening, or at least the original purpose of the evening - to celebrate my anniversary with Hildie. Could I still celebrate this night the way I wanted to, with Hildie by my side? I closed my eyes and took a deep breath. Then I thought of Hildie holding my hand and looking into my eyes with that smile of hers and, somehow, knew it would be all right.

When I came out of the bathroom Linda was standing exactly where I had left her, perfect posture and the usual smile on her face. I smiled back and asked, "Are you ready to go?"

The smile became brighter as she answered, "Yes, sir."


After the usual spiel about how I would prefer to be Dan and she allowed me to call her Linda (with a twinkle in her eye, of course!) we set out for the restaurant.

We never mentioned our previous meetings, or even hinted at them. And I found myself enjoying the evening just as I had the other times. We had intelligent conversation about the world and current events at the dinner, laughed and groaned at the show, and finished up, as usual, at one of the dance clubs Hildie and I had frequented over the years. I couldn't be sure, but Linda did seem a little disappointed at my choice of a swing club, but quickly shook that off and danced as well or better than most of my previous partners. And again there were moments when I felt as if it were Hildie with me on the dance floor.

At last it was time for the evening to end. As usual I had driven us back to my home. Normally the evening would end with a hand shake at the lady's car (the money was taken care of ahead of time so there wouldn't be that awkward moment right at the end), and then the lady would drive off into the night and I would enter the house alone.

But when I stopped my car and was ready to get out Linda finally broke character. "Dan, could we please talk just for a moment? I promise I'm not trying to do anything that would change or hurt you. Please?"

I looked at her. It was a measure of how successfully I had immersed myself into the evening that I had forgotten about our previous meetings. Those memories came flooding back, along with the unanswered questions. For a moment I fought myself over which way I wanted to react to this. But the bottom line was I had to know.

"Okay. But if I don't like this it will cost your boss a client."

"No, it won't."

"Huh?"

"For the last three years the women you've taken out haven't been a part of the service."

I sat there, stunned. "What do you mean? I call Max at the same number and send the money to the same place."

"And he gives it to a charity, usually one that helps kids with rare diseases."

"But then, where did you come from?"

She looked out through the front windshield for a moment, then started talking again. "It's a rather involved story, and I would like to start from the beginning." She looked at me. "And I would like to be a little more comfortable telling it. May we go inside?"

I raised my eyebrow.

"No funny stuff. I promise. We all know it wouldn't work, anyway."

"We?"

She sighed. "Please?"

I grimaced and got out of the car. She waited for me to get her door, a question in her eyes. I opened it, handed her out, looked her in the eye and offered my arm. Her grateful smile almost, almost got to me.


After seating her and providing a drink I sat and listened to a tale that I really didn't believe, mainly because of how it presented me.

It seems that the first three women who had been my escorts had all quit the service soon after our outing. None of the three went on more than five more 'appointments' before deciding they didn't want to do it anymore.

That's when Max decided to go outside his stable to provide me with an escort. Apparently his sister, who had no direct connection with the service but knew about it, volunteered for the next one. And it was from her circle of friends that the last two had come. They were the ones who demanded that the fee be given to charity.

At this point I stopped Linda. "This doesn't tell me the question I'm most interested in. Why?"

"Because of you, of course," came the reply.

I shook my head. "I don't get it. I'm not a handsome young man with something to offer women like you. In fact, I make it plain what the evening is about, right up front. And I've never led any of you on."

"I know," she said softly. "And you severely underestimate your effect on women."

I continued to shake my head in denial. "Look, Linda, I happen to know a lot about men and women and relationships. I have counseled many couples over the years, very successfully I might add, so I think I know a little about this. And I don't see how one night, one date, especially with a man who is admittedly using you as a surrogate, can lead to the kind of behaviour you are talking about."

"He has eyes but he cannot see," I thought I heard her mutter. Then stronger, "Dan, describe this evening to me. Tell me what happened from your point of view."

I shrugged. Why not? "We went to Pierre's for a steak dinner. I ordered for both of us, and chose the wine as well. We chatted about a wide range of topics, including the mideast and the Columbia disaster. I found that you liked Cagney and Bogart movies, and we discussed many of them in detail. We talked about skiing in Colorado and fishing off the Florida Keys." I was starting to slide back into the evening. "We talked about having been to Paris once and planning to go back some day. We discussed having a party on the fourth of July and..."

I realized with a start that suddenly I was acting as if it were me and Hildie talking, not me and Linda. I buried my head in my hands. "I'm sorry, I'm so sorry. I never knew... I shouldn't have treated you like that."

Linda was at my side, shushing me and saying "It's okay, really, it was a wonderful evening. Please, please just listen to me for a little longer."

I finally nodded my head for her to go on.

"Dan, it isn't just you that seems to change us and make us feel the way we do. It's you AND Hildie. The love you HAVE for each other is a wonderful thing, something we haven't had in our lives as yet and may never have. You give us a glimpse of something we never really believed was possible. And for a brief time, we are a part of it. The look in your eyes as you plan something, when you are sharing a laugh, when a dance is done. We know you are seeing Hildie, and we wish we WERE Hildie. Oh, God do we wish we were Hildie."

She paused for a moment, and I looked up at her. She was smiling, but with tears in her eyes. "Don't worry. None of us would ever try to take Hildie away from you. None of us could. Somehow you've made us love her as much as you do. I didn't even understand that part myself until tonight."

Her mention of tonight reminded me. "If you didn't know until tonight, then why the charade at the bar and the casino?"

She blushed. "Well, that came about because of a plan the other women wanted to try. They thought maybe you would be more open to seeing them again if I could show you we could be good companions on our own. I'll admit, I thought I had blown it that first night. They had warned me not to be too suggestive, but I got a little carried away..."

"Yes, I remember. I wasn't too nice about it, was I?" I hung my head, thinking about how cold I had been. And here I had thought I was a nice guy.

"Dan, don't go beating yourself up. It's who you are. I had an inkling of it after talking to Nancy about what happened at the bar and after tonight I know it. And you more than made up for it at the casino. Considering what I know about you now, I'm even more surprised you gave me a second chance."

"That's easy. You made yourself worthy of a second chance by not forcing the issue. You took a shot, and when it didn't happen you let it go. To me, that showed you were thinking of me as a person, not as a 'mark, ' and that impressed me."

Linda smiled at that. "Thank you. That means a lot to me, more now than before." Then she got serious. "I know I only hinted at it before but now I have to lay it on the line. All six of us would like very much to have the opportunity to go on outings with you." I started to say something and she interrupted "... let me finish, please."

I nodded for her to go ahead.

"We do not, repeat do NOT intend to replace Hildie in your life. What we would like is the opportunity to try to be an addition to Hildie, going to the places you want to go, doing the things you want to do. However, we do ask that you try to think of us as individuals. We don't mind you taking a moment to commune with Hildie, but we would hope you could 'commune' with us a little, too. If you can't, it would become too frustrating for us."

She hung her head for a moment, then continued softly, "and now that I've said it, I have to say I can't do it. I can't even think of doing something that has a chance of taking a part of Hildie away from you. I'm sorry, let me get my things and I'll be leaving."

I put my hand on her shoulder as she started to rise, holding her down. "I accept."

For a moment she just sat there, not understanding. "What did you say?"

"I said, I accept."

She quickly looked up and into my eyes, trying to determine if I really meant what I said. "But what about Hildie?"

"Hildie is alive inside of me, and now you. If I spend time with you, I strengthen that bond. You know, you reminded me of something someone once said to me that I dismissed at the time, but turns out to be true. She said, 'I'm sure she wouldn't want you to stop living just because she did.' And she's right.

"Here I thought I was handling her passing so well. I had some buddies, I was nice guy, I was comfortable in my little world. I even came up with a way to celebrate my life with Hildie." I shook my head as the tears started forming. "And I can see now that all it did was keep me from sharing her life with others. God I was selfish!"

Linda held me as I cried, and before long I could feel wetness that couldn't have come from my eyes. I turned, looked into her eyes and kissed her forehead. She smiled through the tears and sniffed, then we both looked for tissues.

After we had repaired the damage somewhat, we talked a little about what comes next. She gave me a list of all of the women with their phone numbers and said the next step was up to me. I told her to tell the others it might take a while, but I was planning to give each of them another outing, and would be in touch.

She was at the door and ready to leave when one last question came back to me. "Linda, before you go, could you solve one last mystery for me?"

"If I can, sure."

"It appeared to me that you were a little disappointed when I told you we were going to a swing club to dance. Why?"

She blushed a deep red. "Uh, are you sure you want to hear this?"

Of course, that just made me more curious. "You bet I do."

"Well, remember last year, with Nancy? You danced a tango with her."

Now it was my turn to blush. "Yes, I do. I think I would have taken her right there on the floor if she had been Hildie."

"Yeah, she thought so. In fact, I think that's when the women started talking about this plan. Are you sure you want to hear this? It might change your mind about us."

I was beginning to think I knew where this was headed and I closed my eyes for a moment. Oh, Hildie, forgive me but I just might enjoy this. Then from somewhere I got this feeling that said 'me too!' "I'm not letting you off the hook now. Spill it."

She blushed again. Such a lovely shade of red, and it seemed to go all the way down. Hmmm. "Well, Nancy told us you were, well, um, or at least felt like you were..." she blushed even more, "Damn it, she said you were hung like a horse and it felt great even through the clothes." She quickly looked down and then back up, blushing again as she did.

"Fourteen inches."

She looked startled and couldn't help but take another, slightly longer look.

"When fully aroused, of course."

Now she was really nervous.

I raised my eyebrow. "And you thought that maybe, if I got used to you, that you might be able to convince me to share that with you, too? Linda!" I said in an imperative tone. "Come here!"

She looked a little frightened at the tone, but came forward. I opened my arms and beckoned. Her eyes widened but she came into my arms and and hugged me. I placed my hands on her ass and moved our pelvises together, grinding slowly. "Oh my god," Linda simpered. As I continued the pressure and my manhood continued to rise she became glassy eyed and started moaning "Oh my fucking god!" and finally looked up at me with those unfocused eyes and asked "Are you for real?"

I smiled as I led her into my bedroom. "Let's find out, shall we?"

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Ma/Fa / Consensual / Romantic / Lesbian / Heterosexual / Oral Sex / Anal Sex / Size /