Caught By My Assistant Emily

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My assistant finds out about my secret gay sissy CD life.

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Author’s Note: This story is mostly true. I’ve kept my secret from everyone in my normal life for many years, until my assistant at work found out. She has promised to keep my secret and so far everything is working out great. There may be other chapters to let you know what happens next.

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It happened on a Friday about a month ago. Usually everyone in the office leaves early and I can indulge in my secret activities, including watching porn and playing with myself. Even though I thought I was alone in the office, I think my assistant Emily heard me say my Daily Affirmations. After I locked my office door, I started saying my Daily Affirmations out loud but then I heard some noise just outside my office. I think Emily had returned to get something from her desk, which she had probably forgot when she left the first time. She didn’t say anything and didn’t come into my office. She just left — but I’m almost 100% sure that she heard me say my Daily Affirmations because I was saying them quite loud.

The next Monday, Emily seemed to avoid me most of the day. She was acting normally when we talked about something work-related but she was very short in her conversation all day. In the afternoon I had some meetings, so I didn’t really see her much and didn’t talk to her until she said “goodbye” when she left at 4:00 (her usual leaving time). When she did, she made a special point of telling me that she didn’t forget anything from her desk, like she has “a few times over the past couple of weeks.” She didn’t mention the previous Friday but she did smile when she said that.

The rest of the week was the same. I was on pins it was only her. So, I unlocked the door and let her in.

I had already pulled my pants up and closed my computer browser so that she wouldn’t see the porn I was watching. She said “so, I thought I’d wait all week to talk to you about what I heard you say last Friday — or should I say shouting out loud — when you didn’t realize I had returned to the office. I figured that Fridays are your preferred days to engage in your secret activities because everyone leaves early.” I decided that I would try to divert her from finding out the truth, so I told her she probably heard the porn on my computer that I was watching. I said I must have had the volume louder than usual. She said “I don’t think so. It was definitely your voice. Let me see what porn you watch.” At that moment she rushed to my computer and before I could stop her she opened my browser and then clicked on some of the tabs of the videos I had been watching.

“Well, well. What do we have here. This isn’t the usual hetero porn or even lesbian porn which most guys watch. This is mostly gay porn. I also see cuckolding videos. And even, oh my god, sissies and crossdressers. My god, Dave, what secrets do you have that you’ve been keeping from me and I assume keeping from your wife too.” It was then that I decided to tell her the truth and hope that she would agree to keep my secret.

“Emily, I will tell you everything but you have to swear to me — really truly swear on your life — that you won’t tell anyone, not a single person, about my secret. My wife would freak out if she found out and would divorce me in a minute. My life would be ruined. Do you swear not to tell anyone, not even your best friend?”

She said “yes, I swear that I won’t tell anyone, unless we talk about it first and you agree. I swear with all my heart.”

“OK then. Here goes.”

I then told Emily, my young (25 year old), beautiful, sexy, voluptuous assistant, everything.

I told her my confession.

MY CONFESSION

“Emily, even though my wife and I have been married for 21 years, we don’t have sex much anymore. In fact, we haven’t had any sex at all in the past 2 years. It’s mostly me. I don’t pressure her for sex but she hasn’t said anything either. I don’t know if she’s been having an affair and that’s why she doesn’t want sex with me. That’s possible but I really don’t know. Anyway, the reason I don’t want to have sex with my wife anymore is that I only really want to have sex with men. It started more than 10 years ago when I used to go to porn theatres when work was slow in the afternoons. I would sit next to guys in the back row and we’d give each other handjobs. Sometimes the guy would lean over and suck my cock. They always seemed to enjoy it. One day I said to the guy next to me — I was actually surprised to hear myself say this — “I’d like to try sucking your cock. I’ve always wondered what it’s like.” So, I leaned over, took his thick cock into my mouth, and sucked it and sucked it and sucked it. I remember clearly, just like it was yesterday, thinking to myself “why didn’t I do this years ago? istanbul travesti This feels so right.” Since that day I’ve been a faggot cocksucker — and I’m never happier than when I have a cock in my mouth.”

“Later, about 5 or 6 years ago, I would also go to adult video places where I’d watch movies in video booths and hook up with other men who were there. That’s when I kissed a man for the first time. He actually took me by surprise when, after he was sucking my cock, he stood up and kissed me right on the lips. We started french-kissing and it felt so right and natural to be making out with a man. Again, I thought to myself, “why didn’t I do this years ago? This feels so right.” From that day on, I enjoy making out with men — it turns me on and is like foreplay for me. Then, later on, after sucking a few cocks I started swallowing cum — not every time but some of the time.”

“Then, about 3 years ago, I was fucked for the first time. This was when I lost interest in having sex with any woman. I lost my anal virginity to a wonderful older man, Bill (he was 58 yrs old at the time), who is a gentle lover and the best kisser ever. He’s been divorced for over 15 yrs, he’s only with men now (he openly admits he’s gay); he’s a bottom with some guys and a top with others. At first, I was a top with him and fucked him the first 2 or 3 times I went to his place. He became my regular guy and we’d get together every month or so. After the first few times of me fucking him, I said that I wanted to try it and I wanted him to be my first. I was worried but it actually didn’t hurt. He’s average size, not too thick, and he’s a gentle lover. It was wonderful that first time and every time since then. I became his bottom and he fucked me many times, until he had to move out west 2 summers ago for work. I found myself having feelings for him; I felt that I was falling in love with him. He was the one who made me realize that I wanted to be a bottom, and I’ve been fucked a few times since then — about 6 times by Bill and then about 10 times by other men since he moved out west.”

“Emily, I have to tell you that I still find myself physically attracted to women. at least sometimes. I’ve always been a “tit man” and you’ve probably caught me a few times staring at your wonderful young breasts” (she said “yes”, she’s noticed that many times). I then told Emily, “if I had to choose between a man and a woman, I have to be honest with myself, I know that I just love cock so much, I’m truly a faggot cocksucker; I’ve accepted it and I actually embrace it. There would be no doubt — I would choose sex with a man every time.”

END OF CONFESSION

Emily was stunned. She said that she had no idea my secret was this extensive. When she heard me say one of my Daily Affirmations ‘I want to find a cock and worship it’, she thought that I was just watching some porn and was expressing a sexual fantasy of mine. She didn’t have any clue that I had been having gay sex for many years. However, she did say that she had always thought I was feminine and probably submissive in bed. A big smile then appeared on her face.

“I noticed that you watch sissy and CD porn too. Are you a crossdresser? Do you wear panties and nylons? Oh my god, are you wearing panties right now?!?”

My face turned beat red. I couldn’t help it. She now knew not only that I’ve been having sex with men but also that I’m a crossdresser. My red face gave it away.

“Is that true?” she said. “It is, isn’t it.”

I couldn’t look at her; I was so embarrassed. I looked down at the floor between us and said “yes, it’s true, but you have to swear — again — that you won’t tell anyone. If it ever got back to my wife she would freak out if she found out. I can’t go through a divorce.”

She said “I won’t tell anyone unless you agree. But you have to be fully honest with me. You didn’t tell me about your crossdressing, so now I want to know the full truth.”

“OK.” I said. “Remember I told you about Bill, the older man who was the first man to fuck me. Well, he was also a crossdresser — some of the time. He didn’t always dress up but he told me that he really enjoyed becoming feminine and pleasing men, especially married men who weren’t getting what they wanted from their wives. During some of the times we got together he dressed up for me and it really turned me on. Then, after 3 or 4 months I asked him if I could try on some of his women’s clothes. He helped me and it actually felt fantastic. I felt so feminine, so pretty (even though I wasn’t really that passable) and I also felt very submissive. So, the next few times we got together we both dressed up and had hot CD sex with each other. It was so hot and felt great. He fucked me while I was wearing sexy lingerie. I became his CD lover until he moved out west for work.”

I then continued “after he moved, I decided I would explore crossdressing istanbul travestileri further. I’ve bought some of my own clothes, including some nylons, a few pairs of panties, some bras, a couple of tops and a short tight skirt. I don’t have any shoes yet or any wigs. I also haven’t done any make-up. I’ve had a few hook-ups with men, mostly married men, who I meet on the gay chatline. Just like Bill told me, their wives don’t give them blowjobs anymore and some don’t get sex very often if at all. So I fulfill a need for them — I suck their cocks and some of them fuck me (safely of course — we always use condoms when they fuck me). Some of them also enjoy kissing. Those are the men I really look forward to seeing because making out with men really turns me on. It’s like foreplay for me. I’m not sure why but I’m actually attracted to older men. Maybe it’s because of Bill. He was 58 when we first met and I was only 45 at that time.”

Emily’s response was simply a big smile because now she knew the whole story of my secret life. She then said “do you sometimes or always wear women’s clothes to work under your male clothes? Are you wearing anything now?”

I decided that since she already knew that I’m a crossdresser, I might as well show her. After I said “yes”, she said “show me.”

I then unbuckled my pants and slid them down my legs. She saw my pink panties and beige nylons. I then unbuttoned my shirt, took it off and she saw my favorite red lacy bra. It was embarrassing and humiliating but I also actually felt turned on, very excited, standing there in front of my young beautiful assistant in my secret sexy lingerie.

Emily then started laughing. “Oh my god !!!” she said. “I’m sorry for laughing but this is unreal. I can’t believe it. I thought for the past year or so that you might be gay or at least bi — after all, I’ve caught you many times staring at my boobs — but I never thought in a million years that you were a gay sissy crossdresser.”

I said “you agreed not to tell anyone, not a single person, because I can’t let my wife or my family or friends find out about this. My life as I know it would be over. Please Emily you agreed and swore on your heart.”

She said “yes, I’ll keep your secret but there’s 2 things that we need to agree on. First, I want to tell Shelly (she’s Emily’s best friend, who looks like but doesn’t sound like Bernadette from Big Bang Theory — very sexy redhead with a great body). She’s my best friend and we tell each other everything and we do almost everything together — even some things that might surprise you. I promise you, she won’t tell anyone. It will just be us two, no one else, I promise. I swear on my life and my heart. The only other thing is that you agree to do whatever we want you to do with us. Right now I don’t know what that might be. After I tell Shelly we’ll talk about it and figure something out. It won’t be anything involving pain. I’m not into S&M or anything like that. But it might be us going with you to a porn theatre or an Adult Video Store and watching you suck a guy’s cock and even getting fucked. That would be hot. I’ve watched some gay porn but I’ve obviously never seen it in person. I think both me and Shelly would enjoy watching you. What do you think?”

I wasn’t totally happy that she wanted to tell someone else my secret but then again I really had no actual say in the matter. She could do what she wanted even if I didn’t agree, even though she did promise not to tell anyone. When I thought about it, it actually turned me on thinking that Shelly would be the other person to find out my secret. She works at the same company as Emily and me and I know they are best friends — everyone knows it. If they keep their promise and not tell anyone else at all, then this might work out. Doing things with them like going to a porn theatre or an Adult Video Store sounds like it might be fun. Maybe I might even get to see their boobs — both of them have great bodies. But that’s getting ahead of myself. For now I just have to accept that Emily is going to tell Shelly and I hope they can keep this secret.

I told Emily “OK, but only Shelly. No one else. You promise?”

“Yes. Only Shelly. I would go crazy if I had to keep this from her. Honestly, I probably would have eventually told her anyway. So it’s better that we both agree that she knows and we can all then have some fun with it. I know she’s going to be so exciting to see you all dressed up. Maybe we can even help you with make-up. What do you think?”

That got me excited. I had thought about getting some help with make-up but I didn’t think it would be from someone I know. “That would be great. I have no clue what to do with make-up, so if the 2 of you would help me that would make me feel even more feminine when I dress up. I also need help buying shoes, high heels. I’ve been wanting for about a year to buy some heels for me travesti istanbul but every time I think about it I’ve chickened out. I’ve bought my lingerie from thrift stores and I’ve even told some of the salesgirls that the clothes are for me. It’s always embarrassing and humiliating but it always gives me a hard-on when I tell them. But I haven’t gone into a shoe store yet. It’s different from the thrift stores, which never have the type of shoes I’m looking for. So, if the 2 of you could go with me, that would be great.”

Emily then said “so it’s a deal. I’ll tell Shelly and we’ll come up with some ideas of how to enjoy this, all 3 of us. You may not know but neither me or Shelly have had much luck in the sex department lately. We’ve had some dates but most of them have been losers. One of the guys I went out with lately was actually married. He didn’t tell me and only wanted to fuck me. I’m looking for more. I want to find my future husband. But in the meantime, if Shelly and I can have some sexy fun with you, that would at least give us something to tide us over until we find our future husbands.”

I was surprised to hear that from Emily, who is so beautiful, so sexy and such a nice person that I can’t believe she’s having a tough time finding someone. Shelly too. She’s just as sexy and beautiful as Emily. Anyway, if I can satisfy their wish to see some gay and CD sex in person live instead of in a video, then if they keep my secret it will be worth it. I’ve always fantasized about hot sexy women watching me having gay sex. I noticed that I was getting a hard-on when Emily was talking about these things. I think she noticed too.

She then said “I really want to hear what you were saying last Friday. I heard some of it but can you tell me the whole thing?”

I told her that I have my 3 Daily Affirmations written down in a file because even though I say them almost every day, it’s easier to have it in front of me while I’m saying it. It’s actually a turn-on to see the words that I’m saying. I then opened up my Daily Affirmations file and showed her. She asked me to read all 3 of them out loud. So I did.

DAILY AFFIRMATION (from the Church of Cock)

I will find a cock today and I will worship it.

I will take it into my mouth and feel the warmth on my tongue.

I will feel the cum flow down my throat, over my body, into my mind and my soul.

I will drink the cum freely and experience true bliss.

COCK IS MY UNIVERSE (from the Church of Cock)

Cock is my universe.

To take cock into my mouth or into my body is to let the universe exist within me.

It is my sole purpose in life. I crave cock. I need cock.

I want to be a cum dumpster. I want cum in my mouth. I want cum on my face.

I need to have a cock in my mouth. No matter where I am, I crave the taste of cock.

Being a cocksucker is my purpose in life.

Cum sustains me. Cock is life and cum is bliss.

SISSY AFFIRMATION (original by Cindy)

I’m a sissy girl. I love to wear panties and sexy clothes.

I’m a sissy girl. I love to be a girly girl, so soft and sexy and pretty. I love to be dressed in my favorite pink panties, my black fishnet nylons, my favorite red lacy bra, pink babydoll, and sexy high heels.

I’m a sissy girl. I’m not a real man. I want to look and feel like a woman.

I’m a sissy girl. I have a pencil dick — no, I have a pencil “clitty”. Hee hee hee

I’m a sissy girl. My lips were made to be covered in lipstick and my mouth was made to be filled with a big juicy cock.

I’m a sissy girl. I love to give myself to a man, fully and completely. To have a man make love to me.

I’m a sissy girl. My wife needs to know.

Emily started laughing. “You really are a sissy faggot, aren’t you?!?”

“Yes I am. It’s something I’ve been struggling with for a few years but I’ve come to accept it now. It makes me happy to be with a man, to please him, and I just love cock so much I can’t explain it. I’m still attracted to the female body — you know that I admire your sexy body and especially your nice tits — but my love of cock is so strong I can’t help myself.”

She responded “you say at the end of the last one ‘my wife needs to know’. Do you want your wife to know or not?”

“That is only a dream and a fantasy — to have my wife know and accept me as her sissy gay crossdressing husband. If she made me her cuckold, that would be my ultimate fantasy. Sucking her lover’s cock to get him hard, then guiding it into my wife’s pussy, and then watching him fuck her deep and hard with his big cock — bigger than my thin average one. Then eating his cream pie from her cunt while he gets behind me and fucks my sissy man-pussy with his big beautiful cock. That is my fantasy. That is what I dream about all the time. But I know my wife wouldn’t be into it. I know she would freak out. She’s very straight, conservative and not kinky at all. I can’t take the chance of telling her or having her find out from someone else. I know about 99% sure that she would end the marriage right away.”

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