The Making of a Cuckoldress

Hi there Diary!
Molly and I had so much fun yesterday. You know we are all about the helping these days, but we never expected to get a chance to help on our teasing trip.   It all started after breakfast when we were sitting in the bar waiting for our taxi that would take us to the marina.  There was this really hot, but conservative looking woman sitting at the bar talking on her cell phone.  She looked to be not too much older than we are and she seemed sad and a little angry.  She was sitting a couple of bar stools away from us, but we couldn’t help but feel sorry for her when we overheard her problem.  And I promise, Diary, we only had to eavesdrop a little bit!

She was telling someone on the other end of the conversation what a loser her husband was, turns out it was her sister, who really had no answers, but we know how to handle a loser hubby and scooted closer.  While she talked we looked at each other, obviously thinking about ways we could help this woman.  By the time she’d gotten off the phone, Molly and I had a plan to change her life.

Beautiful Woman in Distress

First we introduced ourselves and said that we couldn’t help but overhear her conversation about the loser husband (we were already thinking of him as a cuckie to be honest).  Then we said that we might be able to do something about it.  The woman looked at us curiously and then a smile began to grow on her face.  She asked us to explain what we meant.  Molly explained what we wanted to do for her as I dialed a number into my phone.  As I had hoped, the ever so sexy driver that had taken us to the airport in Chicago answered on the other end.  I told him that we had a lady here that was in dire need of a real man.  He laughed his deep, sexy laugh and told me that it just so happened that he had a few days off and would catch the next flight out and be available in a few hours.  I told him that that would be great and that I was looking forward to seeing his gorgeous face soon.  I hung up and filled Molly and the woman in on everything.  Now it was time to get her ready for her rendezvous.

After I called and cancelled our plans, (we can go out on Dexter’s boat and pretend to drop off bodies any time!), we took her shopping, of course.  Molly and I love to shop, not in a shallow way, but because we deserve new nice things and there is never a time there isn’t someone to tease.  However, even more than shopping for ourselves, we  love to help a woman in need.  While we looked for the perfect outfit for dinner and some sexy lingerie, she told us about her husband.  She said that she had only had one other lover when she married him in college and hadn’t been to bed with him before the wedding.  So she had had little experience with sex and no idea that he had a useless tiny penis that she couldn’t even feel when they had sex.  She had decided to just live with the problem because he was going to have a good job and be a good provider.  Five years later, he had proved not to be good at making money, but his teenie weenie hadn’t gotten any bigger.  “He’s such a loser!” she said a million times.  “I want someone better!  And I want that deadbeat loser to watch how a real man is with a woman.” Molly and I assured her that this could and would be arranged.

The Cuckold’s Big Surprise

Soon we had everything we needed and got back to the hotel.  Mr. Handsome Driver was already at the hotel looking as stunning as ever.  The woman told us what her hotel room number was and gave us her soon to be cuckolded husband‘s  cell phone number.  After we introduced them, the two went up to her hotel room hand in hand.  Molly and I went back to our room and watched television for a little bit, and then made the call to the loser.  We told him that there was an emergency in his room and his wife needed him right now.  He said that he would be at the room in less than ten minutes.

Molly and I raced to the elevator, giggling all the way, and got to the floor just in time to see the cuckie running down the hallway to her room.  He fumbled with the card key as we approached.  Finally he got it to unlock and went into the room.

We smiled and snickered quietly as we heard him yell, “OH MY GOD!!!”, then something about “He’s HUGE!”   At that, we went back to our room to call the front desk and order a late massage in our room.