Instant Messaging - Cover

Instant Messaging

Copyright© 2004 by hankj

Chapter 8: The Date

Erotica Sex Story: Chapter 8: The Date - A man struggles with his desire to be a cuckold. He shares a conversation with an online stranger. She's trying to be objective about his fantasies and definitely makes him see his very descriptive life as it could be! She's struggling to give him honest advice but she's not sure he's truly getting it. It's about to become real!

Caution: This Erotica Sex Story contains strong sexual content, including Ma/Fa   Consensual   Blackmail   Heterosexual   Fiction   Cheating   Slut Wife   Wimp Husband   Cuckold   Humiliation   Masturbation   Cream Pie   Exhibitionism   Voyeurism   Slow  

"When the times comes, if it does come at all, I'll reveal myself if I think it's important! Let's just drop it and we'll chat some more during the week. Don't forget on Friday that you must have your laptop! Pleasant dreams, cucky!"

Wednesday before the date.

"Hey there cucky! Were you able to get everything you wanted for Friday?"

"I think so. Kristina's dress came in today and I dropped it off to get it altered. I'm supposed to pick it up tomorrow."

"Did you get the other things as well?"

"Yeah. I picked up the heels to go with the dress yesterday. So far, I've got everything except the dress in a nice box in the trunk of my car."

"So I take it that Kristina has agreed to the date on Friday?"

"Yeah. I don't know how you knew she'd agree, but Kristina seemed to think it would be fun. She didn't even hesitate to say that she would like to go out on a date like that! She was even ribbing me that I'd really have to outdo myself if she was to let me pick her up! She thought the lack of wedding rings would be romantic. I've got a feeling she's going to have a little fun with me."

"Can you describe the dress to me you got for her?"

"The dress is actually a very simple design. It's made of a very thin clingy material that stretches when it's worn. I guess a good analogy would be like a long tube top. Kristina won't be able to wear a bra because the dress fits so tightly to her curves and dips low between her breasts and in the back. The top of the dress is held in place like a halter-top with two straps of material that cross above her breasts and tie behind her neck. The opening the straps and the dress create is like an inverted teardrop in front. To go with the dress, I got her some modest three and a half inch white, open-toed heels that have a strap at the ankle. I didn't think she'd be able to wear stockings so I got her some sheer to the waist tan pantyhose. I know that part doesn't sound romantic, but hey I'm only a guy! I'm dying waiting to see Kristina in that dress!"

"It seems elegant was NOT the look you were going for then."

"Not really. Like I said in one of our chats, when Kristina and I were dating, she was a lot less conservative in the outfits that she wore than she is now."

"Am I to presume that she would have worn this kind of dress when you were dating?"

"She might have, but it would not have been a typical dress for her by a long shot! Short dresses she would wear, but this dress would probably have been a little too thin for her taste. I almost forgot. I also got Kristina some panties to wear as well. They're kind of dainty but not the thong type. I know for a fact that Kristina hates the thong style. She says it creeps up too much!"

"If the dress is as thin as I imagine it, she may opt to forego those anyway."

"That wouldn't bother me!"

"Like I told you in our last conversation, I doubt very much whether you'll get to touch Kristina very much at all on Friday anyway! I want you to also do something really corny, like adding a card to the package. Make it romantic and say something like you'll always want to date her. You get the idea. Something corny would probably be exactly what she would expect from you."

"I can do that!"

"I don't want you to harp on it, but I want you to compliment Kristina and make a comment or two during the week that you're looking forward to seeing her in the dress you've gotten for her. Don't describe it though. Save it as a surprise. Tell her how much you appreciate the effort she's put into working out but a little more elegantly. Like I said though, not too much about that but enough to say you recognize her efforts. Any more and you're committing suicide for insinuating that she needed to do it! Another thing is, I don't want you to make any negative comments at all this week or weekend. Pretty much agree on whatever Kristina says. The one exception is sex. No more sex until the weekend if you get that lucky! When you catch up with her after your date, NO temper, ill-spoken words or even a hint of jealousy! If you do or don't get to have sex then, accept it graciously and be thankful that she'd even let you after what we've put into motion here!"

"Kristina really has toned up a lot in the past couple of years, so that won't be a lie. Not that she had any weight problems at all, but I know she's worked hard to keep her figure! Oh and I get it; Kristina gets to be the queen of the house the rest of this week and throughout the weekend! Is there anything else I need to do?"

"No, I think you're all set. I've made you a reservation at the hotel already. Make sure you get something to wear that complements Kristina's dress, maybe some tan slacks and a nice dress shirt, since you'll be getting there after work."

"I know I should ask how you were able to get me a reservation but you'll have some sarcastic comment so I'll pass on that. Oh, you should like this. I talked Kristina into letting me shave her pubic hair just a little. Actually, I just shaved around her pussy to get rid of those sparse little hairs. She's said that she's thinking she might shave me so I get to feel how uncomfortable shaving there can be as it's growing back in! She did say though, that it makes her skin more sensitive to my touch that way."

"Well you're finally using a little initiative. Not what I would have suggested, but at least it's something! Here's the last few details; Explain to Kristina that on Friday you two officially don't know one another after you leave in the morning. Some time Friday afternoon, I want you to get back to the house and leave your present with the card for Kristina on the bed. Beyond that, it sounds like everything is set. You and I will chat again on Friday evening. I'll be looking for you on line about 8:30. Have fun, Cucky!"

Friday evening at 8:30.

"Hey there cucky! Are you nervous yet?"

"Yeah. The more I've thought about this, the more I've decided all kinds things can go wrong!"

"Don't worry. It'll be fine! We're just going to throw a few additional snags into this evening's events. If Kristina calls before you get to see her, I don't want you to pick up the call."

"So I'm supposed to be late and rude!"

"Put it this way; you don't know one another, remember?"

"How late am I going to be?"

"Not too bad, only about an hour or so. Just sit there in the room and relax. Schedule a wake-up call for 7:00 tomorrow morning."

"I'm staying here all night?"

"Yep. You'll be going down to meet Kristina about 9:45 or 10:00 but you're going to tell her that you have to go back to the office until morning to finish your reports for your boss."

"What about the ride home for Kristina? I'm supposed to be the designated driver tonight."

"Make sure Kristina has cab fare and apologize profusely!"

"Actually, I'm letting you go downstairs a little earlier to observe Kristina undetected. I seem to remember you have a fancy for being the voyeur from one of the descriptions you've given me. You can observe but don't get seen! Then sometime after 10:00 or so casually walk by. Do NOT interrupt Kristina if she's engaged with someone, just be casually seen. Let Kristina approach you when she's ready. That's when you'll explain the situation about your job and that you have to head back to the office. You just didn't want to blurt it out over the phone, because she might still be playing the part of not knowing you. As soon as you and Kristina finish talking, you're to come back to the room. That should make it about 10:30 or so. I don't want you loitering and spoiling Kristina's fun."

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