cycleryder
Male
Hello, I am not much of a writer so I will write this as if I am writing to a dear friend. However for those who don’t know who I am I will say this. I am Heather. I am 45 and this is about my first time to cheat, eventually my husband would come to know so not cheating anymore. I am an average American housewife, not a MILF. I do not have a stunning figure or huge tits, sorry guys, I am about 20 pounds overweight at the time of this happening and I have gained a lot of confidence over the years and now I have the body I am proud of.
Hey, I know it’s been awhile but I see you noticed that I have changed a lot over the years and when we sat and had coffee you did a double take at the man who dropped me off as he wasn’t Dan, and he was black. I have decided that I am going to take you into my confidence because I don’t want you to think ill of me or especially think that I am cheating on Dan. I am not, he knows. Hmm, let me start this back when I started working for #$))(*&& and associates. Do you remember? I was dumpy and the ******* were all settled into school and during the day I had all that free time at home. I decided to look for a job. I was talking with a neighbor (Jan) at the grocery store, she looked like she had just come from the gym wearing baggy sweat clothes. I was always so jealous of her, she looked gorgeous even when dressed frumpy. She had such confidence and she ran such a tight home, I found out why.
I mentioned to Jan that I wanted to know more about her offer last summer at the pool party about a position at her company. I needed to get out of the house and wanted to do something meaningful, she told me she was stepping sideways from her position at the company (#$009*&& and associates) and told me I would be a perfect fit. I didn’t know, I hadn’t worked since just before the ******* were born and 8 years is an eternity, and I was unsure about being an executive assistant. She assured me that it was the perfect position for me just what I needed. She told me there might be occasional travel and that if her boss (James) liked me, which she was sure he would, that I could really open doors and possibilities. She said look at me, I was where you were 8 years ago, maybe you need the boost that I did. I was worried about the travel and someone to watch the *******, she told me she would give me her nanny’s info. I must have had a look because she said “Don’t worry dear if James needs you he will cover the cost”. So I was sold.
Dan and I talked and he said that I should go for it and while we didn’t really need the money it would come in handy. I reminded him there was the possibility of eventually traveling and he said he would pick up the slack if needed so his mom could watch the *******. I told him about the possible Nanny if I had to travel. He was concerned about just how long it would take to travel and how far away. I had to admit I hadn’t asked. I was thinking of just how accomplished Jan was and how I envied her, a bit, ok quite a bit. Her husband always seemed to dote on her and she seemed so in control and radiant. Yes, that is the word, radiant.
It was settled, I called Jan and told her yes please set something up and she replied she already had spoken with James and basically all I had to do was show up for the interview on Friday at 9am. I was shocked she had done that but I had to admit that was Jan, take charge. I was so nervous that Friday morning running around Todd had spilled a little juice on my blouse as I hurried he and his sister on to the bus I was mortified but I didn’t have time to change, punctuality is key in life (my dad had always taught me that), so I rushed to the building where Jan worked and popped into the coffee shop across the street and got some ice water to blot my blouse, as I was walking cleaning my blouse I bumped into a man who had just bought a coffee. The coffee went flying and I was so scrambled that I almost cried and offered to buy him another coffee. I looked up at him in his piercing eyes he was 6’1” black and amazing, I mean he was right off the cover of some model magazine, a foot taller than me, chiseled chest, I could see even through his high end suit (that I was thankful I didn’t get any coffee on) He laughed it off and said sure thing.
The barista saw it all happen and already had started another when we got to the counter. He said I take it black and they know me well. I said I liked it black as well, and stammered as I realized how that sounded. He asked what had me so out of sorts and I told him that I have an interview in 15 min across the street and that I hadn’t worked in so long having had ******* etc. that I had to hurry over. He asked who I had an interview with and I had to say I didn’t know that my friend Jan had set it up that I would be working for a man named James. He looked me deep in the eyes and said take a deep breath, then asked me point blank if I was ready for the opportunity so I took that deep breath and said yes I am. He said good, my name is James and your interview is with me, let's sit and talk. I will call Jan to cover till we get in.
Honey when I tell you I was entranced that would be putting it lightly I was fucking getting soaked just looking at this man. The way he carried himself, his deep voice, his amazing looks. For some reason I was picturing him just throwing me down and taking me, like in the sluty novels we used to laugh about. Yes he was that charming and, I hate to say it, the ideal man.
We chatted a bit about the job, the responsibilities and it sounded like I was his gopher and yet more like a right hand to be there when he met with clients and keep track of his papers and liaison when he was busy. He then wanted to know about me, just me. He asked about me aside from the ******* and especially my marriage. He just wanted to know me. I kept talking about my youth and growing up and college then how I met Dan. To that point it almost felt like I was on a date not an interview. He stopped me when I mentioned Dan and asked if I wanted to see my new office? Did I have the job? He acted like I was already hired.
We walked across to the building when the security man at the desk saw us enter and he stepped around. I don’t know why I automatically thought the guy was going to say something, a tiny white woman with this very tall black man. He approached and was subservient and asked James if he needed anything and that he hadn’t seen him come in at his usual time. James gestured to me and introduced me. This is Heather. She will be my new companion as Jan is taking over my building in New York. We walked towards a private elevator, when we entered he turned to me and explained that the position was more than an assistant more than a secretary but a manager and a companion in his business ventures. We arrived at the top floor and Jan was there to greet us. She took me by the arm to her/my? office.
Jan was dressed differently than I had seen before. She was almost provocative and I noticed she had a bit of a baby bump if I didn’t know any better. Jan saw my gaze and she said she dressed this way for James, this, motioning to her belly and she giggled a little and said yes she was going to be a proud mom once again. I congratulated her and her husband. She laughed a bit and said that she would explain more later.
The top floor had just a receptionist desk in the middle and then a long hall with doors on either end.When we entered the office it was huge and it had a private bath with shower and then we entered another door where there was a queen sized bed and dresser. We walked back out to the main office where we sat on the couch. I was just a tad overwhelmed. Jan turned to me and asked if I had any questions. Any? I had tons. Jan started with I will be upfront with you, you are here because James sees in you what I do and he sees what he sees in me. I joked and said… him? She said exactly that! I was just stunned, what do you mean you and he? Yes Heather he is an amazing man and the ******* of this baby as she rubbed her slight bulge. But what about Steve, I don’t understand it all. Jan looked seriously at me, Heather, admit to yourself, you found James attractive and desirable? I had to admit it, yes. You want to be more assertive and confident? Yes . You found it thrilling that James also finds you attractive? He did? Yes honey, remember that pool party when I told you about the job possibilityI showed him some pictures of you from it. He has been asking about you ever since. About the time I asked him to give me a baby. James has been looking forward to meeting you, I was looking for the right opportunity, then you brought it, call it fate dear. What about Steve, are you divorcing? I couldn’t do something like that to Dan and the *******. She laughed and said no honey Steve knows and approves.
Jan continued, I could tell that the flame had kind of dropped away for you and Dan the same as it had with Steve and I. When I started working for James 8 years ago I began making more money than Steve, a lot more, we suddenly could afford to travel and get the ******* what we wanted to give them. Both the boys' college is paid for when they are ready. All I had to do was admit to myself I deserved all that and more and James showed me all that and that I am an amazing woman as well. What and in exchange you have to be his .. companion? Yes, and I wanted it. I wanted him, there are no strings I could have walked away at any point no harm no foul. Steve and I are moving to New York and we will be raising James' baby and he will visit from time to time. I am being upfront with all of this James had taken time with me as the woman that had been his companion before me wanted to marry him which he does NOT want. If you take this position you will sign an agreement to that and that any all sex will be consensual. What do you mean all sex? I mean Heather that Steve has been there and even assisted, he is my cuckold husband. You do not have to tell Dan, I didn’t tell Steve at first. That bedroom in there got a considerable workout before I told Steve. By the way, is it all new there and decorated in your favorite colors if you noticed? I did. I wanted you to feel comfortable with your surroundings. So, all I have to do is put out for him? OH NO dear you are so much more, think wife without the paper or ceremony. You will be his other half. He meant all that he told you about the responsibilities of the job part. He is a man of focus and has no time for games. So you understand he is worth Billions with a B.
I sat there and my mind was a blur. Jan stood, walked over to the desk where there was a box, opened it and took out a stunning cocktail dress that left little to the imagination. She had me stand and held it up to me as we stood in front of the mirror. This will look fantastic on you if you decide to take this position you will be accompanying James to a casual dinner party he is hosting for some clients here one floor down tonight. Tonight? Yes. Do you need to think it over or.. About that time James walked in suit jacket gone oh god he was hot. He walked towards us as Jan stood there holding the dress against me. His face showed his approval. He took my face in his hands and looked into my eyes, will you be with me? OH GOD I was drenched. I wanted to kiss him. I wanted him to kiss me… I wanted him to fuck me. Oh Damn all of my thoughts were of taking this man into the other room and fuck him. Dan gone, the ******* gone, just James and I fucking, not making love, fucking.
I stammered for a moment, will I be expected to BE WITH the clients? No dear you will be mine, all mine. I wasn’t certain if that meant that I would not be having sex with Steven anymore but since we hadn’t in 9 months I was dying to fuck this man in front of me. NOW. I meekly said I would have to tell Steve that I will be late. James tenderly leaned down and kissed me on the lips and then turned and left. My legs buckled a little. What? He just left me standing there. Jan spoke finally. That was hot as hell to watch. Girl you are perfect for him. Jan, I need.. Oh honey I know what you need but you will need to Jilloff a little later. I need to start you on the tasks that we will need to take charge of for the party.
I called Steve and told him that I would be extremely late and to not wait up, that I was hired and Jan would be showing me the ropes and that I was helping host a cocktail engagement for the boss. The next few hours were jammed with meetings with the caterer and the staff, I was taken to the other floors where I was introduced to so many people my head was spinning. We ate a light late lunch and I signed the papers that Jan had told me about. After several hours still no sight of James we went to the office where Jan helped me into my cocktail dress. She hugged me and told me to enjoy it and turned to walk away. Wait, you aren’t staying? No dear, the rest is all about you. I will see you here Monday morning and I will finish going over procedures you need to know. You got this girl.
The party was a private little gathering of a number of heavy hitters. I recognized a few celebrities and even a couple of high up government figures. I thought maybe I was just arm candy, if you could call a frumpy housewife in an expensive cocktail dress arm candy, even though James kept introducing me as his companion. As I looked around at the other women, they were your average housewives as well. I was a little shocked that these were their actual wives not arm candy for cameras. There was no press, it was extremely private.
After it was over James and I went to the private elevator and returned to the top floor, I asked him about the purpose of the cocktail party. He took me in his arms and kissed me deeply. It was for you dear, they now know who you are and how important to me you are and they are to afford you the level of respect you deserve and if they fail in that they know the cost. The doors opened and he walked me to my office door and kissed me again and asked me if I had a good time and he would be saying good night. I asked if he had to leave me. He said “Ask me to stay, remember once we go into that bed you are mine, your body is mine”. I grabbed him by the lapels and pulled him down to kiss him with passion I didn’t know I had left in me.
The clothes came off as we made our way to the bedroom. I was literally dripping down my legs. James was perfect as he stood there, body of a god, he laid me down on the bed and removed my panties and I wanted to reach up for his belt but he knelt down between my legs and started to eat my pussy like there was no tomorrow. I came right away as I was coming down from one orgasim another started. After my third he stood and took off his pants and there was a bulge that I was almost frightened of as his cock came into view. I was certain this was going to be like nothing I had ever experienced before. He kissed me as he got between my legs and felt his hardness touch my labia and clit. I came again. Then he began to enter me slowly and steadily as we kissed. God I never had been this turned on. More and more as he slowly worked himself inside me. Girl I am telling you that saying size doesn’t matter is bullshit. It was amazing. I came so many times as he fucked me deeper and deeper then he hit a spot that I had never experienced. He gazed at me and asked if I was ready to enter my posterior Fornix, of course I knew what it was but.. OOH GOD I was out of control. I was thrashing and speaking in tongues. My mind exploded up my spine down my spine. My gut convulsed. Then it happened he came inside me. I was spent, so was he, he slowly withdrew and I knew I was changed. I was full of his cum and I loved it. I thought it had been minutes and I saw the clock and it had been over an hour. Then it hit me, when was the last period.. Oh ok I was good. I will write more if you want to hear more.
Hey, I know it’s been awhile but I see you noticed that I have changed a lot over the years and when we sat and had coffee you did a double take at the man who dropped me off as he wasn’t Dan, and he was black. I have decided that I am going to take you into my confidence because I don’t want you to think ill of me or especially think that I am cheating on Dan. I am not, he knows. Hmm, let me start this back when I started working for #$))(*&& and associates. Do you remember? I was dumpy and the ******* were all settled into school and during the day I had all that free time at home. I decided to look for a job. I was talking with a neighbor (Jan) at the grocery store, she looked like she had just come from the gym wearing baggy sweat clothes. I was always so jealous of her, she looked gorgeous even when dressed frumpy. She had such confidence and she ran such a tight home, I found out why.
I mentioned to Jan that I wanted to know more about her offer last summer at the pool party about a position at her company. I needed to get out of the house and wanted to do something meaningful, she told me she was stepping sideways from her position at the company (#$009*&& and associates) and told me I would be a perfect fit. I didn’t know, I hadn’t worked since just before the ******* were born and 8 years is an eternity, and I was unsure about being an executive assistant. She assured me that it was the perfect position for me just what I needed. She told me there might be occasional travel and that if her boss (James) liked me, which she was sure he would, that I could really open doors and possibilities. She said look at me, I was where you were 8 years ago, maybe you need the boost that I did. I was worried about the travel and someone to watch the *******, she told me she would give me her nanny’s info. I must have had a look because she said “Don’t worry dear if James needs you he will cover the cost”. So I was sold.
Dan and I talked and he said that I should go for it and while we didn’t really need the money it would come in handy. I reminded him there was the possibility of eventually traveling and he said he would pick up the slack if needed so his mom could watch the *******. I told him about the possible Nanny if I had to travel. He was concerned about just how long it would take to travel and how far away. I had to admit I hadn’t asked. I was thinking of just how accomplished Jan was and how I envied her, a bit, ok quite a bit. Her husband always seemed to dote on her and she seemed so in control and radiant. Yes, that is the word, radiant.
It was settled, I called Jan and told her yes please set something up and she replied she already had spoken with James and basically all I had to do was show up for the interview on Friday at 9am. I was shocked she had done that but I had to admit that was Jan, take charge. I was so nervous that Friday morning running around Todd had spilled a little juice on my blouse as I hurried he and his sister on to the bus I was mortified but I didn’t have time to change, punctuality is key in life (my dad had always taught me that), so I rushed to the building where Jan worked and popped into the coffee shop across the street and got some ice water to blot my blouse, as I was walking cleaning my blouse I bumped into a man who had just bought a coffee. The coffee went flying and I was so scrambled that I almost cried and offered to buy him another coffee. I looked up at him in his piercing eyes he was 6’1” black and amazing, I mean he was right off the cover of some model magazine, a foot taller than me, chiseled chest, I could see even through his high end suit (that I was thankful I didn’t get any coffee on) He laughed it off and said sure thing.
The barista saw it all happen and already had started another when we got to the counter. He said I take it black and they know me well. I said I liked it black as well, and stammered as I realized how that sounded. He asked what had me so out of sorts and I told him that I have an interview in 15 min across the street and that I hadn’t worked in so long having had ******* etc. that I had to hurry over. He asked who I had an interview with and I had to say I didn’t know that my friend Jan had set it up that I would be working for a man named James. He looked me deep in the eyes and said take a deep breath, then asked me point blank if I was ready for the opportunity so I took that deep breath and said yes I am. He said good, my name is James and your interview is with me, let's sit and talk. I will call Jan to cover till we get in.
Honey when I tell you I was entranced that would be putting it lightly I was fucking getting soaked just looking at this man. The way he carried himself, his deep voice, his amazing looks. For some reason I was picturing him just throwing me down and taking me, like in the sluty novels we used to laugh about. Yes he was that charming and, I hate to say it, the ideal man.
We chatted a bit about the job, the responsibilities and it sounded like I was his gopher and yet more like a right hand to be there when he met with clients and keep track of his papers and liaison when he was busy. He then wanted to know about me, just me. He asked about me aside from the ******* and especially my marriage. He just wanted to know me. I kept talking about my youth and growing up and college then how I met Dan. To that point it almost felt like I was on a date not an interview. He stopped me when I mentioned Dan and asked if I wanted to see my new office? Did I have the job? He acted like I was already hired.
We walked across to the building when the security man at the desk saw us enter and he stepped around. I don’t know why I automatically thought the guy was going to say something, a tiny white woman with this very tall black man. He approached and was subservient and asked James if he needed anything and that he hadn’t seen him come in at his usual time. James gestured to me and introduced me. This is Heather. She will be my new companion as Jan is taking over my building in New York. We walked towards a private elevator, when we entered he turned to me and explained that the position was more than an assistant more than a secretary but a manager and a companion in his business ventures. We arrived at the top floor and Jan was there to greet us. She took me by the arm to her/my? office.
Jan was dressed differently than I had seen before. She was almost provocative and I noticed she had a bit of a baby bump if I didn’t know any better. Jan saw my gaze and she said she dressed this way for James, this, motioning to her belly and she giggled a little and said yes she was going to be a proud mom once again. I congratulated her and her husband. She laughed a bit and said that she would explain more later.
The top floor had just a receptionist desk in the middle and then a long hall with doors on either end.When we entered the office it was huge and it had a private bath with shower and then we entered another door where there was a queen sized bed and dresser. We walked back out to the main office where we sat on the couch. I was just a tad overwhelmed. Jan turned to me and asked if I had any questions. Any? I had tons. Jan started with I will be upfront with you, you are here because James sees in you what I do and he sees what he sees in me. I joked and said… him? She said exactly that! I was just stunned, what do you mean you and he? Yes Heather he is an amazing man and the ******* of this baby as she rubbed her slight bulge. But what about Steve, I don’t understand it all. Jan looked seriously at me, Heather, admit to yourself, you found James attractive and desirable? I had to admit it, yes. You want to be more assertive and confident? Yes . You found it thrilling that James also finds you attractive? He did? Yes honey, remember that pool party when I told you about the job possibilityI showed him some pictures of you from it. He has been asking about you ever since. About the time I asked him to give me a baby. James has been looking forward to meeting you, I was looking for the right opportunity, then you brought it, call it fate dear. What about Steve, are you divorcing? I couldn’t do something like that to Dan and the *******. She laughed and said no honey Steve knows and approves.
Jan continued, I could tell that the flame had kind of dropped away for you and Dan the same as it had with Steve and I. When I started working for James 8 years ago I began making more money than Steve, a lot more, we suddenly could afford to travel and get the ******* what we wanted to give them. Both the boys' college is paid for when they are ready. All I had to do was admit to myself I deserved all that and more and James showed me all that and that I am an amazing woman as well. What and in exchange you have to be his .. companion? Yes, and I wanted it. I wanted him, there are no strings I could have walked away at any point no harm no foul. Steve and I are moving to New York and we will be raising James' baby and he will visit from time to time. I am being upfront with all of this James had taken time with me as the woman that had been his companion before me wanted to marry him which he does NOT want. If you take this position you will sign an agreement to that and that any all sex will be consensual. What do you mean all sex? I mean Heather that Steve has been there and even assisted, he is my cuckold husband. You do not have to tell Dan, I didn’t tell Steve at first. That bedroom in there got a considerable workout before I told Steve. By the way, is it all new there and decorated in your favorite colors if you noticed? I did. I wanted you to feel comfortable with your surroundings. So, all I have to do is put out for him? OH NO dear you are so much more, think wife without the paper or ceremony. You will be his other half. He meant all that he told you about the responsibilities of the job part. He is a man of focus and has no time for games. So you understand he is worth Billions with a B.
I sat there and my mind was a blur. Jan stood, walked over to the desk where there was a box, opened it and took out a stunning cocktail dress that left little to the imagination. She had me stand and held it up to me as we stood in front of the mirror. This will look fantastic on you if you decide to take this position you will be accompanying James to a casual dinner party he is hosting for some clients here one floor down tonight. Tonight? Yes. Do you need to think it over or.. About that time James walked in suit jacket gone oh god he was hot. He walked towards us as Jan stood there holding the dress against me. His face showed his approval. He took my face in his hands and looked into my eyes, will you be with me? OH GOD I was drenched. I wanted to kiss him. I wanted him to kiss me… I wanted him to fuck me. Oh Damn all of my thoughts were of taking this man into the other room and fuck him. Dan gone, the ******* gone, just James and I fucking, not making love, fucking.
I stammered for a moment, will I be expected to BE WITH the clients? No dear you will be mine, all mine. I wasn’t certain if that meant that I would not be having sex with Steven anymore but since we hadn’t in 9 months I was dying to fuck this man in front of me. NOW. I meekly said I would have to tell Steve that I will be late. James tenderly leaned down and kissed me on the lips and then turned and left. My legs buckled a little. What? He just left me standing there. Jan spoke finally. That was hot as hell to watch. Girl you are perfect for him. Jan, I need.. Oh honey I know what you need but you will need to Jilloff a little later. I need to start you on the tasks that we will need to take charge of for the party.
I called Steve and told him that I would be extremely late and to not wait up, that I was hired and Jan would be showing me the ropes and that I was helping host a cocktail engagement for the boss. The next few hours were jammed with meetings with the caterer and the staff, I was taken to the other floors where I was introduced to so many people my head was spinning. We ate a light late lunch and I signed the papers that Jan had told me about. After several hours still no sight of James we went to the office where Jan helped me into my cocktail dress. She hugged me and told me to enjoy it and turned to walk away. Wait, you aren’t staying? No dear, the rest is all about you. I will see you here Monday morning and I will finish going over procedures you need to know. You got this girl.
The party was a private little gathering of a number of heavy hitters. I recognized a few celebrities and even a couple of high up government figures. I thought maybe I was just arm candy, if you could call a frumpy housewife in an expensive cocktail dress arm candy, even though James kept introducing me as his companion. As I looked around at the other women, they were your average housewives as well. I was a little shocked that these were their actual wives not arm candy for cameras. There was no press, it was extremely private.
After it was over James and I went to the private elevator and returned to the top floor, I asked him about the purpose of the cocktail party. He took me in his arms and kissed me deeply. It was for you dear, they now know who you are and how important to me you are and they are to afford you the level of respect you deserve and if they fail in that they know the cost. The doors opened and he walked me to my office door and kissed me again and asked me if I had a good time and he would be saying good night. I asked if he had to leave me. He said “Ask me to stay, remember once we go into that bed you are mine, your body is mine”. I grabbed him by the lapels and pulled him down to kiss him with passion I didn’t know I had left in me.
The clothes came off as we made our way to the bedroom. I was literally dripping down my legs. James was perfect as he stood there, body of a god, he laid me down on the bed and removed my panties and I wanted to reach up for his belt but he knelt down between my legs and started to eat my pussy like there was no tomorrow. I came right away as I was coming down from one orgasim another started. After my third he stood and took off his pants and there was a bulge that I was almost frightened of as his cock came into view. I was certain this was going to be like nothing I had ever experienced before. He kissed me as he got between my legs and felt his hardness touch my labia and clit. I came again. Then he began to enter me slowly and steadily as we kissed. God I never had been this turned on. More and more as he slowly worked himself inside me. Girl I am telling you that saying size doesn’t matter is bullshit. It was amazing. I came so many times as he fucked me deeper and deeper then he hit a spot that I had never experienced. He gazed at me and asked if I was ready to enter my posterior Fornix, of course I knew what it was but.. OOH GOD I was out of control. I was thrashing and speaking in tongues. My mind exploded up my spine down my spine. My gut convulsed. Then it happened he came inside me. I was spent, so was he, he slowly withdrew and I knew I was changed. I was full of his cum and I loved it. I thought it had been minutes and I saw the clock and it had been over an hour. Then it hit me, when was the last period.. Oh ok I was good. I will write more if you want to hear more.
