Femdom Vacation

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A married submissive businessman meets a Domme online.
1.5k words
4.14
96.2k
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Part 1 of the 4 part series

Updated 06/08/2023
Created 12/20/2014
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Bored with my mundane office job and my sexless marriage, I downloaded an app that allows you to vent and share your secrets anonymously. Like most things on the internet, it became over run with thirsty perverts. Myself included. With it, users can chat with people or post publicly.

Through using this app, I made friends with an American woman living in Los Cabos Mexico. We told each other about our lives, our loves, and our ambitions. Early on we exchanged photos. Mine showed that I was in shape and I was above average looking, but not a model. I used a program that made my photo disappear after 3 seconds so nothing could get back to my wife.

She sent an incredibly sexy photo of herself wearing a classy dress and high heels. She had long brown hair, pouty lips, and what looked like C or D cups. She was a yoga instructor and had the body that comes from that.

Once a trust and friendship was established, she admitted that she cheated on her boyfriend with a somebody from work and though she felt guilty about it, she also wanted to fuck him again. She gave me lots of details about how much larger his cock was than her husband's average dick. How she was on top, where he came, etc.

I admitted that I went to a strip club not too long ago and the dancer gave me a handjob. And that this wasn't the first or second time that has happened. I never asked for one. I didn't pay extra. I think they just want to see me get off during a private dance. She found this odd that it happened multiple times.

We were now even with shared secrets and continued to chat and learn about one another. Mostly about our personal lives, but sometimes sexual desires. I was late 30's, a business executive and powerful in my daily life. My days were generally planned a few days prior, I kept to a schedule and was very successful. She worked as a yoga instructor and sometimes at a bar, more for fun than the money, She loved to party and lived day by day. I revealed over time that I was submissive, extremely kinky and had some twisted desires. She loved every bit of it, would chat about it and then change the subject abruptly.

A few weeks into chatting, she caught me off guard and here's how it went.

Alana - BP from Wendington Ct

Me -???

Alana - What will LP say about BP chatting with a beautiful woman?

Me - Who are they?

Alana - Don't play dumb. I sleuthed enough to find out more about you. You and I both know those are you and your wife's initials.

My stomach sank. This was supposed to be anonymous. I didn't reply to her.

Alana - you said that you like games. I think I have a fun one for us to play.

Me- Ok, what's that?

Alana - It is called blackmale.

Me - You spelled it wrong.

I was trying to make light of a strange situation. I didn't know what to think. I was getting pretty angry because I thought she and I had a connection and now she just wants to extort my hard earned money from me and my family.

Alana - Here's the deal. I broke up with my boyfriend and he moved back to California. I now have dirt against you that your wife will not be happy to hear and you have nothing on me. Sexting with me. Revealing your sexual desires to me. Getting handjobs from strippers. I have a lot of info she would not want to hear.

Me - Ok, what do you want?

Alana - You are going to come to Baja and be my slave for one week. I will dominate your mind, body and spirit. I will control your desires, your emotions and your orgasms. I reserved us a small beach house south of Tijuana. It is ready July 12th. You have some time to prepare yourself. In the meantime, I will message you with a packing list and instructions for where we will meet. From this point forward, you will only call me Mistress or Mistress A.

Me - Are you serious?

She sent me a screenshot of the reservation. My cock instantly got hard and I started to think about the logistics. Calling off of work. Telling my wife that I had a business trip. Packing, etc. This was the most exciting thing currently happening in my mundane life. Outside of going to work, working out, eating, and sleeping, I didn't have much time for other things. I spent about 30-60 minutes a day looking at femdom porn sites and reading femdom stories. This was going to be my fantasy turned reality.

Me - I'm 100% in.

Me - Mistress. :)

We didn't chat much for the next few days. She would send me a text that simply said "Ball Gag" and I would reply, "Yes, Mistress." "5 inch dildo" and I would say, "Yes Mistress." "Strap-on harness. Under ware style." "9 inch dildo - black."

By the end of the week, 2 weeks before our trip. I had arranged with work for a 9 day break. I told my wife that I had a 4 day business trip to San Diego and that I was going to explore Baja California for 5 days to do some diving and camping. She didn't like the outdoors and didn't like the sea. I went diving as a kid and hadn't been since I met her, but she knew I wanted to again. I had a good story, a reason for my passport being stamped at the border, and all looked good.

Over the next week, Mistress A texted me an updated and total packing list:

- 3 pairs of pink panties

- 1 CB chastity device

- 5" dildo

- 9" black dildo

- under ware style strap on harness

- ball gag

- clothes pins

- restraints

It was Friday and we were meeting the following Saturday. My airfare has been purchased and I was excited beyond belief.

That day she sent me a text. "Put your chastity device on this weekend. Make sure it fits properly and on Monday I will send you an address of where to mail the keys."

My cock was so hard I couldn't control myself. I went into the bathroom at work and jerked off, shooting my spunk all over the floor.

I woke up Saturday morning to a new message from her. She said that she fucked the guy from work again and her legs were so weak and her pussy was so sore. His big cock pounded her for what seemed like forever, bringing her to multiple orgasms. He came in her mouth and throat. She then reminded me to put my chastity device on and to mail her the key. I jerked off again, so excited about what was happening.

Monday rolled around and I had the CB chastity device packed with my things to take to work. I was going to mail her the key at lunch break after putting it on. Sitting at my desk, I started to be paranoid. What if she isn't who she says she is? I sent her a text asking her to send another photo of herself holding a sign with my name. I tried to word it in the best possible manner. My text read as follows:

"Dear Mistress A, I hope you understand my odd request. I am about to send you the keys that will give you control of my penis. I have a small worry you are not the beautiful goddess that I think you are. I just don't want to get to Mexico to find a weird old lady or a fat guy pretending to be you. I hope you understand, but I will be more comfortable sending you my keys once I see a photo of you holding a sign with my name on it."

She replied with, "Understood, but first I need a fully nude photo of you with your face holding the chastity cage. You can photobomb it so that it disappears after sending it."

I went to the bathroom at work, took my clothes off and took a photo of me holding the chastity cage, all with an awkward scared smile.

She sent me a photo back of her in a bikini holding a sign with my name on it. Below my name it said, "Is my bitch"

My cock was instantly hard. I went back to the bathroom, jerked off into a wad of toilet paper. I washed my cock off in the sink with cold water and then I put the chastity device on. I put the keys in y pocket and went back to my desk. I had an envelope prepared, so I wrapped the keys in a piece of paper and sealed the envelope.

The lunchtime trip to the post office went smoothly. I kept feeling a little pinch each time my cock would start to get hard thinking about what I was doing, but it was painless. I sent her a text showing her a photo of the stamped envelope.

Her reply was "see you in 5 days."

To be continued...

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