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. Letter to an Advice Columnist

Discussion in 'Cuckold Stories' started by sharonsmif, Apr 7, 2017.

. Letter to an Advice Columnist 4.8 5 4votes
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  1. sharonsmif

    sharonsmif Member Author!


    Not all letters written to an advice columnist in your local newspaper appear in print, or are even answered by the columnist. The following letter is an example of one that never received a response.

    Dear Granny Annie,

    I need help, and your advice has always been really good and spot on, so I'm hoping you can tell me what to do about something that happened to my husband and me recently.

    It all started right after our wedding, I guess, which was more than nineteen years ago. Boy, time flies when we're having fun, doesn't it? Anyway, it was actually on our wedding night when my brand-new husband started talking about his best friend, who had been the Best Man at the ceremony. He kept telling me how Randy had the biggest cock he'd ever seen, and how much he wished his own little dick could be that big, and how much a woman would love to have a guy like him as her lovers, etc., etc.

    Well, I'm sure you already get the idea, so I won't keep harping on it except to tell you that he'd say pretty much the same thing when we saw a handsome man in the grocery store, or anyplace else for that matter. On the way home he'd always ask me if I saw the bulge in that guy's pants, or if I thought he was good-looking, or other stuff like that.

    I always told him he was all the man I'd ever want, but at the same time I just couldn't stop myself from wondering if having a lover would make my sex life more satisfying than it had always been. You see, my husband is the only guy I've ever been in bed with, and even though he's never been anything great as a lover, I've always loved him and still do for that matter. I guess the problem is that he got me pregnant when I was sixteen and still in high school, and we decided it would be best for us to get married, so we finally got our folks to agree and we did that. And I've never, ever had relations with another man in my whole life.

    I have to admit that the more Glenn harped on the matter of me taking a lover, the more I began to think of it in a positive light, if you know what I mean. Just about the only time he could make me climax was when he was on top of me and while he was going at it he'd be telling me how much better it would be with the guy in the restaurant, or at the movie, etc., etc. Anyway, it seemed like the more he did that, the more I fantasized about doing it with another guy, and then I'd get off.

    So, by the time one really-important night came around after we'd been married for all those years, and he "popped the question," so to speak, I surprised both of us by saying that maybe it would be a good idea for us to try doing it.

    That was when he said that his boss had been telling him for ages that he thought I was really beautiful, and then he'd say something like how a wife like me could help her husband get promoted if she'd play her cards right. Then he told me that there was an opening coming up as V.P. of the Sales Department, and he really, really wanted it. He'd been a top manager for a few years, and he thought there were only two other guys in the company who were qualified for the promotion, and then he asked me if I'd help him get it.

    Well, I have to say that I was pretty shocked by the whole thing, because up until then it hadn't been anything but just another wet dream kind of thing, but now here was my very-own husband acting like he wanted me to be a whore for him, so he could get a promotion. At first it kind of put me off, but after I'd thought about it for a few days, it started sounding better and better, so I finally told him to tell me what he wanted me to do, and I'd think about it.

    So he did. He said what his boss wanted was for the two of us to come to their home for dinner on a Saturday evening, and then spend the night in their bed. And yes, I meant to say "their bed," because apparently the guy's wife was going to be part of the whole thing, and even though Glenn didn't say anything about that part, I could tell that she was going to be a part of the sex.

    Actually, that part didn't bother me all that much, because my best friend when I was little was another girl my same age, and we spent lots of nights at each other's house and in each other's bed, so it's no surprise that we started having sex. And I really liked it, too. In fact, I've always thought that if I had to choose between being married to a man or a woman, I'd probably choose the woman. That's not to say that I don't love Glenn, because I do. It's just that women are so much better at pleasing other women that men will ever be, so that's why I would make that choice.

    Anyway, when Glenn told me about that part, I made my decision on the spur of the moment, and he just about crapped himself when I told him I wanted to do it. It took him a long time to accept what I told him, but by the time we were falling asleep he said he'd make the arrangements the next day at work.

    So, that's why when Saturday evening rolled around, the two of us were walking up to his boss' front door, and I was so damn nervous that I thought maybe I was going to pass out. All day I'd been going from being scared half to death to being really wet down there, if you know what I mean, and I was still like that when Glenn rang the doorbell on their huge house that looked more like a mansion than a house, by the way.

    Both of them answered the door, and as soon as we got inside Glenn introduced me to them and vice versa, and then Bill took my arm and led us to what he called "the study." Bill told me to sit on one of the couches, and then he and Mandy sat down beside me. Glenn was sitting on another couch on the other side of a coffee table, and I felt a little uncomfortable about the whole thing until a servant brought a silver bucket with wine bottle in it. Once we were all sitting there sipping the wine, I relaxed a little bit, and when Mandy popped a really dirty joke and everyone laughed, I knew it was going to be okay.

    After we'd each had two glasses of the wine, the servant came to the door and told us dinner was served, and so Bill took one of my arms while Mandy took the other and they led me out of the room. We entered the dining room where this huge table was already set and the servant was standing behind one of the chairs and he asked me to sit in it, so I did. Glenn sat across from me and Bill and Mandy sat at opposite ends of the table.

    The servant had a little cart that had the food on it and he started with me and then Glenn, and after our plates were full he served Bill and Mandy. We had some white wine during the meal, and it tasted pretty good and I probably drank too much, because to tell the truth I was still pretty nervous about being in bed with a man and a woman I'd never met before. Still, I thought it'd probably be kind of exciting and of course Glenn would get the promotion and we'd have more money, which would be nice, wouldn't it?

    After the dinner Mandy volunteered to show me the powder room, and so I said that'd be nice, because to tell the truth all that wine was making me pretty full. When we got to the bathroom, she went right in with me, which surprised me because it felt kind of strange to be in there with someone else, but she just acted so normal about it that it seemed like the right thing to do.

    After we met Bill and Glenn back in the study, Mandy thought it was time for them to give us a tour of their house, and before I knew it they had taken my hands and were pulling me up a huge staircase. We went right to a room on the end, and as soon as we walked inside it, I knew it was their bedroom, because the biggest bed in the whole world was sitting across the room, and the covers were already turned down, which hit me pretty hard, because it meant that push had come to shove and it was time for me to show them that I meant what I'd said about trying another man, and probably his wife, too.

    They led me right over to the bed and then Bill took me in his arms and gave me the hottest kiss I'd had in a long time. Then as soon as he was finished doing that, Mandy did the same thing, and it was even hotter than his had been, and I was feeling pretty light-headed, but that was probably because of all the wine, but I have to admit that I was getting more than a little turned on by then.

    Bill was standing behind me while Mandy was kissing me, and the all of a sudden she was unbuttoning my blouse from the top and he was doing the same from the bottom, and then they pushed it over my shoulders and I was feeling pretty embarrassed, even though I was wearing a bra to cover my boobs.

    Bill took care of that part right away, and I could feel his fingers unfastening my bar and then all of a sudden Mandy was pulling it off me. Then Bill's hands were reaching around me and playing with my boobs while Mandy was doing her best to do the same thing, and it felt so good that all I did was lean my head back against him and enjoy the sensation of my nips getting bigger and harder than they'd been in years.

    All of a sudden Mandy dropped down on her knees and started taking off my pumps and anklets, and at the same time Bill was unfastening my slacks. Mandy helped him pull them down, and then they did the same thing to my panties and before I even knew it I was stark naked. Mandy leaned forward and started kissing my puss, then running her tongue up and down my slit while Bill was pinching my nipples and pulling them way out from my boobs. God, that felt so good that I thought I was going to cum right then and there, but it distracted me when Bill picked me up and almost threw me on the bed, right in the middle.

    I just lay there trying to breathe while they both got undressed, and then they were just as naked as me, and I was trying to look at his huge cock at the same time as I was trying to look at her huge boobs and smooth puss, which I'd never, ever seen on a woman.

    I guess they couldn't wait even a second longer and all of a sudden he was on one side of me and she was on the other and they were both kissing and licking me all over, and I was just out of my mind and hotter than ever in my life. Bill pulled my legs apart and got on his knees between them and started rubbing the head of his monster up and down my slit, and then Mandy told him to get it inside me as far as it would go, and to make it hurt.

    Well, he did that all right, and as soon as he was about halfway in he was in virgin territory, so to speak, because Glenn's little dick had never been in that far. He kept pushing deeper and deeper while Mandy kept telling him to rape me for all he was worth and to give me a really hard fucking that I'd never forget, and he did all that and more.

    She got up on her knees beside my head, just like my girlfriend used to do, and I knew what she wanted from me. I reached out to the leg that was closest to my head and lifted it up and over and all of a sudden she was sitting backwards on my face, looking at her husband raping me. My tongue knew exactly what to do, and it licked her up and down and frontwards and backwards, so to speak, and she was getting wetter and wetter with every lick and I loved the taste of her juice with all my heart, and wanted as much of it as I could get.

    I could tell by looking up her back that the two of them were kissing and hugging as he fucked me and she enjoyed what my tongue was doing to her crotch. He was pushing his big thing as far inside me as it would go, and every time it hit bottom it hurt, but in a really good way, and if I could have said anything, all I'd have done was to tell him to push harder and faster.

    Mandy was bouncing up and down on my face and I knew she was really close to cumming, so I reached up with one hand and started pinching her clittie, which was probably bigger than Glenn's little dick ever had been. The more I pinched and pulled it, the more she bounced, until at last she started cumming and like a miracle had happened, I did, too. I guess right about then Bill did the same thing, because I could hear him praising Jesus.

    Both of them got off me and lay down beside my almost unconscious body, and if it hadn't been for them kissing and caressing me all over, and telling me how wonderful I'd been, I'd probably have fallen asleep right then and there. I guess they didn't want me to do that, because they all of a sudden started turning my body crosswise on the bed, which didn't make any sense to me until I opened my eyes and saw my poor husband on his knees beside the bed. I had completely forgot that he was even in the same room with us, but it was easy to tell that he'd been watching what was happening because his eyes were as big as silver dollars and his mouth was hanging open as he kept gasping for breath.

    Well, as soon as I saw him waiting there, I knew what Bill and Mandy wanted me to do. I moved down the bed just far enough so I was lined up with my husband, then scooted my crotch toward him. Bill and Mandy lifted my knees up on his shoulders, and before I could even tell him what to do, his head shot forward and he started licking my puss just as fast as he could

    That part of me was still hurting more than a little because of the way Bill had stretched it, and Glenn's tongue felt real good, let me tell you. Then when I heard him moaning deep in his throat, which told me he was turned on just as much as I'd been a few seconds ago, I started getting hot all over again. Of course, since Bill and Mandy were still kissing me and playing with all my parts, I'm sure that helped, too.

    Anyway, I could feel Glenn sucking Bill's cum out of my puss, and then Mandy started pinching and pulling on my clittie, and I just lost it. I don't ever remember climaxing again just a few minutes after I'd already done that, but I sure did right then. I could actually feel Bill's cum squirting into my husband's mouth, and when he started moaning louder and swallowing so loud I could hear it, it made me cum even more. Boy, that was good!

    After I was through doing that part, they got me turned around the right way and in the middle of their huge bed, and both of them got down beside me and caressed me all over and told me how much they loved me, and that relaxed me so much that I just fell asleep. I do remember Bill telling Glenn to get undressed and get in there with us, but then I didn't know anything else until the next morning when I woke up.

    We had breakfast with them before we left for home, and while Glenn was driving I asked him if anything had happened after I fell asleep. He told me that Bill had made him give him a blow job, but he'd tried to be quiet about it so it wouldn't make me wake up. I asked him if he'd liked sucking another man's cock after it'd fucked me, and he just said straight out that having my juice on it did nothing but make it taste better.

    Damn, I wish I could have watched Glenn sucking off another man, because I just know it'd have been a really-exciting thing to watch, for sure. Then I remembered that as we were walking out their front door, Bill told us that he expected both of us to come back next Saturday, and he wouldn't take no for an answer. I decided that the next time we were in bed together, I make sure to stay awake so I could see Bill shoving his cock down Glenn's throat.

    And that brings up my question for you, and I need an answer real soon, so please reply to this e-mail just as soon as you can.

    All day Sunday there was something bothering me, but I couldn't figure out what it was. Then, just as soon as Glenn left for work Monday morning, I had a flash that it had something to do with something I'd read when he'd first applied for a job with Bill's company, several years ago. So, I rushed into Glenn's home office, looked in his file cabinet, and sure enough, there was a file labeled "Employment Papers."

    I quickly read through the printed forms until I came to the part entitled, "Conditions of Employment," and then I slowed down and read slower. Sure enough, right there was the thing that had been bothering me for hours on end. In the paragraph headed, "Sufficient Cause for Termination," was a list of things that could get an employee fired, and the number three cause was, "Homosexual Activity."

    And now you know the problem. I'm afraid that if Glenn sucks off his boss when we go back next Saturday, he might get fired rather than get promoted. Do you think that could actually happen? Please tell me what I should do. I'm just dying to see my husband doing that to another man, but not if it would cost him his job.

    Please write to me just as soon as you can.


    Questions or comments? Please write to me at: [email protected].
    Last edited: Jul 16, 2017
    AllenJ likes this.
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