Being an Escort for My Boss

An escort for my boss

I am 27 married and my husband and I have two children. My boss is a distinguished looking man in his early 50s. I have worked for him at that time for a couple of years.

He approached me one day, and said he had a couple men coming that were considering investing in his business. He went onto explain.

He said they had never been to Texas and he wanted to show them a good time. The men wanted to go out drinking and to some gentlemen’s clubs. He said he invited one of his other male friends to accompany them as he had no real experience in such places.

His friend told him that if he could get a couple of pretty women to go with them as escorts he thought it would go far in winning the men over.

He asked if I would consider going with him at least to dinner and a couple of the bars. And if I would, could I bring a friend?

I told him I didn’t think that was going to be something I felt comfortable doing. He further explained and told me that he would pay for everything. He would also pay me and my friend $500 just to drive his cars and hang out with them for the night.

He went on to tell me. He thought, my friend and I would not drink and we could be the designated drivers. That way he and his guest could drink as much as they liked and at the end of the night we would just drop them off at the hotel.

I considered his offer. Basically it was just to be drivers and I would get a free dinner at an expensive restaurant and $250. I told him I would have to ask my husband and ask one of my girlfriends to be the second driver.

He said he would appreciate it and told me to please ask them right away. Because if I could not, then he would have to figure out something else.

I called my husband and explained the situation. my husband‘s response was predictable as he always supported me and whatever I’ve done.

He had met my boss before and said he was relatively comfortable with me doing it, if I wanted to do it.

I’ve been called my friend Lisa. She was also married, and like myself, was considered pretty by most. I explained the situation to her and she said she was happy to join me and drive she could use the money.

So Lisa and I dressed in tastefully sexy dresses. We met my boss at our job. He said we both look very attractive, and think this right away for helping him.

He gave us both the keys to the cars and a list of places to take them men with the addresses included. We waited a few minutes, and then the men arrived.
First, our bosses friend showed up. He was attractive and a polite man, but several years younger than my boss.
The other two men arrived within five minutes of my boss’s friend.

The other two men like my boss, and his friend arrived, wearing suits. Both of the other men seem to be in their 50s. One was Hispanic, and the other appeared to be a very light skin black man. They were polite, but there was a crudeness about them. You could tell they intended to have a good time.

We first went to the restaurant. It went well. The food was fantastic. We all had light conversation at the table. Lisa and I avoided telling the men that we were both married. We knew we were also supposed to be arm candy for the night.

From there we went to a gentleman’s club. We went inside with the men and all set together in a big curved booth. The men seem to be having a lot of fun tipping the women that were rubbing their nipples all over them.

We stayed there for a couple of hours, and then my boss got them to move on and we drove to a bar. Lisa and I went inside and said a table shipping on a couple of cokes. The men were all getting a little drunk. Fortunately, at this bar there were other women, available for the men to dance with.

Eventually, the Hispanic gentleman asked me to dance. Lisa had already danced with his friend a couple of times.
The man was very flirtatious and was trying to talk me into joining him in his hotel room. This was to be expected, so I did not get offended by his suggestions.

At the end of the night we drove them back to their hotel, and went home.
My boss gave me $500 then turned to Lisa and gave her $500. We were both thrilled by this as we thought we were going to split $500.

As it turned out, that was just the first night. The next day I got a call from my boss. He asked if Lisa and I could do it again. I talked to my husband and once again, he of course, said it was up to me. I called Lisa and she said definitely she would be willing to do it.

It went almost, almost as it did the night before. But on this night, the boss said he had rented a limousine. we would not have to drive. We were just going to be escorts. And if we wanted to drink, it was fine he was going to pay for everything. We asked if we were still getting paid the same as the night before?

My boss said definitely. He took out his wallet and paid us both $500 each right then. We all got into the limousine. It went almost the same as the previous night. But this time, Lisa and I both drink a little. By the time we were at the bar, we danced with each of the men.

At the end of the night, the limo driver took us all back to the hotel. Lisa and I had parked our cars there. The hotel was in Dallas at least a 30 minute ride from our homes. We both have been drinking. My boss offered to pay for us a room at the hotel, so we would not be driving home under the influence.

We called our husbands and told them of our situation. Lisa‘s husband said he would drive there and pick her up and bring someone to drive her car back.

My husband told me it sounded like a good idea. I originally told him I would probably be staying in a room with Lisa.

My boss got me a room. We all went at the hotel bar to have one last drink before it closed. The men were keen to tell us what their numbers were. Lisa told them she would not be staying.

They seem disappointed, and then they both directed all their attention toward me. My boss’s younger friend did not stay for the drink. As soon as we got to the hotel, he bid us all goodbye and drove away.

My boss was obviously feeling his drink. I asked him which was his room number. It turned out. He was on the first floor only a few doors down from the bar. I walked him to his room and helped him get inside.

Then I walk back to the bar area. The two men were still there, sipping on their drinks. They called to me and I went back over and sat with them. They both were throwing compliments at me and doing their best to try to get me to go to their rooms.

I got it from the table and went to the bathroom. When I got there, I called my husband I told him would it take place up till then. That I was still there, at the hotel bar a little drunk and the two men were hitting on me.

Both of them? he asked. I told him yes both of them are doing their best to try to get me in their beds. He asked me which one I was going to sleep with?

What? I said in disbelief. I’m not going to sleep with either one of them. Oh, OK then he said if you don’t wanna get some while you’re there. Really? I said, are you serious?

We had often talked about me getting a fuck buddy during our lovemaking, but that’s about as far as it ever went.

My husband kept teasing me, in an encouraging manner to go ahead and fuck one of them. I told him I did not think I would be doing that. Then told him I had to go and I went back to the table.

The bar was closing, and the bartender was wiping the table as the men finished their drinks and stood up. There she is, they said to me.

I went with them to the elevator. They both continued, asking me to join them in the room arguing between each other which one I preferred.

The black man’s room was on the third floor. The Hispanic man and I were actually only two rooms apart on the fourth floor.

The black man got off, reminded me of his room number and told me if I changed my mind to just go knock on his door. I kept my response, flirty and friendly as I sent him on his way.

The Hispanic man and I went to the fourth floor. When we got out, we discovered that our rooms were just across the hall from each other.
I must admit my drinking, and my husband‘s conversation had me thinking ever since I talked to him about which one I might sleep with. Hispanic gentleman stood in front of his door before he opened it, he asked me one more time if I wanted to join him in his room.

I’m not sure why I did it. But I responded by telling him. Why don’t you join me in mine. That’s all he needed. He walked straight over to me and said he would be glad to. I opened the door and we went inside. As soon as we got inside, he started taking off his jacket and pants.

I couldn’t believe what I was about to do. I have to admit I was quite excited at the time. The thought of seeing another man’s cock after only being with my husband for many years. Was making me quite horny. Even though the man was twice my age.

As he got undressed, I removed my clothes as well. I could tell he was quite excited. Seeing me naked, I sat, on the edge of the bed and waited for him to finish getting undressed.

As soon as he was done, he walked over to me and got between my legs and began licking my pussy. it felt really good and he seemed quite content while doing it. After a few minutes, he pushed me further back on the bed and climbed between my legs. He had a nice uncircumcised cock. He slid it inside me. I must admit it felt really good. He fucked me in a couple positions, and then finally I felt him come inside me.

I did not bring any condoms with me any it appeared he must not have had any, because we definitely did not use one.

When he was done, he rode over and laid there like he thought he was going to stay in my room. I told him it wasn’t going to happen he needed to go to his own room. I helped him put his pants back on and then bundled up all of the rest of his clothes, and his shoes in his jacket, put them in his hand and pushed him out into the hall.

I looked through the people and watched has he went into his room.
I looked at the time and realized his fucking me only took 45 minutes. I thought my husband was probably still awake so I called him and told him what happened. I could hear his excitement on the other end of the phone.

He told me it was the hottest thing he ever heard me say. I laughed at his comment. And said back to him so me telling you someone else was fucking my pussy is exciting to you?

He said yes definitely! He asked me to tell him one more time. I did.
Then he surprised me by asking me if I was going to fuck the other man?

Are you kidding me? I said. He said no he wasn’t kidding. He thinks it would be hot if I fucked the other one too.

I could feel the Hispanic man’s cum still draining from my pussy. So I told my husband I still had the first man come inside me. he told me to call the other man since I knew his room number with the room phone. And if he’s awake, tell him you’re on your way, then just go in the bathroom clean up before you go down.

I couldn’t believe it. My husband was giving me instruction to go and fuck another man. And right after I just told him, I cheated on him with someone.

I picked up the phone and called the other man while I was still on my cell phone with my husband. He said he was still awake. I asked him if he was still interested in having sex with me. he said he definitely was. I then told him I would be down in about 15 minutes and hung up the phone.

I asked my husband if he heard the conversation as I held the cell phone up so that he could. He said he did hear the conversation and it got him so hot. He was now so horny. He felt like he needed to jack off his cock.

I couldn’t believe it. But at the same time I was getting very horny thinking about fucking two men in the same night.

So I hung up the phone with my husband, went in the bathroom, freshened up and put on my dress wearing nothing underneath it.
I went down to the black man room and knocked on his door. He opened the door, wearing nothing but a pair of boxers. He was grinning obviously glad to see me.

I went inside, and he stood and watched me as I removed my dress. Then I looked over at him and watched as he removed his boxers. Like his Hispanic friend. He had an uncircumcised cock. But it was a nice size at least 8 inches. Which is at least 2 inches longer than my husbands.

I never seen a black cock before, so I got on my knees and started sucking it if only to get a good view of his cock and balls. he stood as I sucked his cock, but he was impatient. After just about a minute, he raised me up and put me on the bed. Without any more foreplay, he climbed between my legs and shoved his cock deep in my pussy.

I was surprised by his stamina and energy. Especially after our night of drinking. He fucked me hard and several positions over the next three hours.
I had several orgasms. And for once my pussy felt thoroughly fucked. I got up and started to put on my dress to return to my room. he held out his hand and said oh it’s late or rather it’s early why don’t you just sleep here.

I wanted to say no, but I was wore out. I climbed back into bed with him and dozed off. I woke up hearing him moving about in the room around 11:30 AM.

He saw that I was awake and asked if I wanted to go get breakfast. I told him no I better get to my room and get cleaned up. He was walking around the room naked I couldn’t help but look at his cock.

I once again picked up my dress beginning to put it on, and as he did before, he came up to me and showed me his cock was hard. he asked me if I wanted to fuck him one last time before I left.

It was as if I had no power over myself. I dropped my dress and laid back on the bed. He climbed on top of me, and once again we fucked. And once again, I was impressed by his stamina as it was 1:30 p.m. by the time he was finished fucking me.

I finally put my dress on and rode the elevator up to my room. I was relieved that my card key still allowed me access to the room as my underwear, bra and shoes were left in the room. As I only put on my dress and went barefoot it to his room.

I cleaned myself up and put on my dress, and once again look like a respectable woman. I called my husband and told him about what happened.

He was very excited. He told me he had jacked off multiple times during the night thinking of me having sex with the two men.

I told him I only did them one at a time, although I did the last one twice. I was on my way home.

As I drove home, I thought about my boss. Surely I helped him seal that deal.
I thought if the men invest in his business, then they might be around more. I might just fuck these two men every time they come in town. I know my husband would love it.

I know my pussy did.