Started as A Favour

The wife's gracious favour

It all started back when my wife asked me for a very odd favor. No, it began before then when she was acting all strange and giving me those looks like something was on her mind but when asked the answer was always the same thing, there's nothing. As weeks passed, it wasn't getting worse, but it wasn't going away either. The time has come for me to find out what this was all about. Me: Okay, enough. What's going on and don't you dare say nothing. I've been letting this go and go but it's time to fess up. Carol: Honestly Bill, you... Me: Nope, nope, nope. No honestly, or oh really, or you're imagining things, tell me what's going on. Carol: Tonight, I promise. After dinner, I'll spill the beans. K? Me: I can wait that long. Naturally time dragged on, but I was patient. I waited this long, a few more hours is just fine. We had a good dinner, made some plans for the week, then had a glass of wine before going into the living room and began the talk I didn't expect. Carol: Just a reminder, I wasn't going to bring this up, but you've insisted so I'm all in now. Me: This must be something big. Carol: Remember a few years ago, you told me about a party you went to in college? Me: You're going to have to be more specific than that dear. Carol: The one where you sucked a guys dick. Me: What? I never did that. Where did you...wait, you got that all mixed up. It wasn't me that did that, it was Freddy, our friend who we caught blowing a guy on the back porch. Not me. Carol: Oh. Well, same difference. I want you to suck a guys cock for me. Me: First off, it's miles from being the same thing and secondly, no! Carol: Hear me out. Me: I don't really need to. I'm not giving head to any guy. Carol: Would you just listen for a moment? Thank you. The guy is my brother. Me: Harlen? Carol: No, Jack. Anyways, he's pretty sure he's at least bisexual and maybe gay but he has no real tangible way to tell without being with another guy. That's where you come in. All you have to do is suck him once, and that's it. Done and done. Me: Are you insane? Why on earth would I do this? I mean, I like Jack, he's a good guy, but I don't want to blow him. Carol: I knew it would take convincing so name your price...within reason. Me: No! There is no price. Carol: Think about it Bill. Nothing at all. Nothing you've always wanted but never could have. Me: *this got me thinking and I knew a way out of this* I want to fuck Jen. Carol: My sister Jen? Me: Yes. Carol: If agreed to, you'll do that for Jack? Me: *knowing she wouldn't ever agree* Yes. Carol: Done. We have a deal. I couldn't believe this was actually going to happen. I thought there was no way she would let me fuck her sister but there was not even any hesitation. This must mean a lot to her to go to that extreme. Well, I wasn't happy about it but I made the deal and for the chance to bang Jen? Sucking a dick is worth it because she is super-hot. I love my wife with all that I have but there's always that one out there that someone would give anything to get with and Jen is mine. Not only hot, but real nice and sweet too. No matter my attraction to Jen, I wasn't about to go through with sucking off any man, so I told her that I changed my mind and backed out. She wasn't happy about this, and I couldn't understand why it was so upsetting. As days passed, she became quiet and barely spoke much. I kept trying to find out the reason this was so important to her, but she wouldn't say. She never once pressured me, or laid on the guilt trip, but it was hurtful seeing her so down. So much so that I gave in and agreed to do it. The way I figured was it was in the privacy of our own home, no one else would know about it, and it would make my wife happy. She was elated and thanked me over and over. One benefit was that since I needed to know what to do, she gave me quite a few bj's going slowly to show techniques. I did end up having to practice on a dildo, with her help, but she never made fun of me. She encouraged me and showed me several ways to do things to alter between until I find out what he likes. The day arrived and I was so scared, but thankful it was here so I could get done with this and move on, but there was one more surprise in store for me. He would like me to look like a woman, at least to an extent, which meant I had to cross-dress now too. I was about to back out, but my wife convinced me to go along with it. She dressed me up in some sexy pink bra and panties, a short black skirt, and a white blouse with the buttons down low. There were no heels that fit me, but her brother brought some that would, three inch ones plus I did wear stockings. I felt silly but she said I looked adorable, once she put the blonde wig on that her brother had brought for me as well. When he arrived, I answered the door. I was to be Melanie, my wife's coworker, so I pretended I was. I've never done anything like any of this and I was shaking nervously. He was nice, and treated me like a woman, having a good and polite conversation. He ramped up the talk to more adult topics, asking about sex and I made up some things to go along with the person I was play acting as. He pulled me in for a kiss, pressing his lips to my red rose tinted ones slipping his tongue into my mouth. I was kissing a man and the first thing I thought was his breath was fresh. I felt his hands caressing my sides, along the edge of the stuffed bra, down to my hips, then a squeeze of my butt. I hopped in a place which made him, and my wife, giggle. What was she still doing here? I broke off the kiss looking at her. She said not to mind her at all. I wanted to tell her to leave but I got sidetracked by him lowering me to the floor and putting me between his spread legs. This is the closest I've been to a man's crotch, and I could see the outline in his slacks of his hardening manhood. I gulped at the size of it, much bigger than mine. He unzipped, and pulled it out, and it was just as big as I thought it was. Not talking like huge, porno size but easily seven inches and a good thickness. I heard next to me whispers of encouragement from my wife, she had slipped down to sit beside me. I stared at his member as he wrapped fingers around it and guided it to my mouth. I was so scared, but he didn't stop. It hit my lips and I could smell the scent of a musky pine as he held it in place. My wife gently nudging me to do what was natural. I closed my eyes and parted my lips slightly but that was all he needed because he used that small opening to press forward and slide that cock over my tongue and kept on going. I was starting to gag already but there was no end to it, my wife even saying to keep going. The spongy head hit my throat and I began to choke and even then, he didn't quit. Not until he was all the way in, by then I had drool pouring out the side of my mouth and was choking heavily. At last, he withdrew to let me get my air and recover but not for too long. However, from that point on he was conscious of my gagging and would stop and let me catch up. My wife praised me, saying how well I was doing, thanking me for going along with this. Occasionally she would raise my skirt and spank my butt making me whimper. The man picked up his pace and began to let me move on my own which wasn't much, but he seemed happy with it. The texture was a mix of soft and rigid, the taste in my mouth was a bit salty, and his moans grew louder and longer. He was holding on for as long as he could, which was making my mouth sore, but he couldn't last forever. He asked something and I heard my wife say down the throat. It didn't take long to understand what she was talking about, especially since my head was held tightly. I squealed trying to get away, I didn't want to swallow his cum, but my choice was taken out of the equation. He tightened up, then convulsed. His body spasmed shooting spurts of his seed in my mouth, throat, and into my stomach. He took a few moments to finish sending into me all he had, then collapsed back onto the couch, he softens cock still in my mouth. My wife let my head go and I immediately pulled my head back and gagged. She handed me a towel, then a glass of water but said to wait a moment when I went to stand up. She pointed to the front of my skirt which showed that I was semi hard beneath my girlish clothing. I had no explanation for it other than the body reacts to stimulus in various ways, it doesn't necessarily mean anything, but it did have me wondering why it happened. I was lifted back onto the couch, and he gave me a soft kiss, and thanked me for the fine job I did saying he can't wait for the next time. We all chatted a while, and I felt more relaxed with general conversation, then he kissed me goodnight and left which is when I turned to my wife with a burning question. Me: Next time? As far as I know there is no next time. Carol: Oh, I'm sure it was just said in passing. Me: *eyes narrowing* I know when you're lying Carol. What did you tell him? Carol: I maaaaay have insinuated, possibly, maybe, that you'd do it more. That this wasn't a one-time thing. Me: You did WHAT?! Carol: Calm down, calm down. I'll sort it all out I promise. I mean it now go get cleaned up and changed. Me: You better. I went off and took a long shower, washing all the make up off and dressing in my normal clothing. I felt better now, and I trusted her to get this fixed because I wasn't doing that again. It took several gargles to get that cum taste out of my mouth and throat. So life went back to normal; work, eat, talk, sleep, rinse, and repeat for about a week then she came back at me with news. Carol: He would like another evening with you. Me: Nope. Just tell him no. Hhn! None of this, only one more time. It was only one time. I did the one time. No more one times. Carol: You won't even think about it? Give it any consideration? Me: What's there to think about? Do I want to suck his cock again? The answer is no. Carol: You admitted it wasn't that bad. Me: What I said was it wasn't as bad as I thought it would be. That doesn't translate to I want more, and I didn't want to bring it up, but there's still your end of the bargain. Carol: You're that eager to fuck my sister? *folded her arms* Me: Don't. You're the one that agreed to it. Don't make me the villain. Carol: I tell you what... Me: Carol! Carol: Listen. If you do one more time, hear me out...one more time, and you get both of us at the same time. Me: *ready to cut down her offer, I had to pause* Wait, what? Carol: You heard me. Me: You. And her. And me. Same time. Carol: That's what I said. We're not going to do any lesbian stuff; she is my sister! Don't be gross. Me: I didn't even say anything like that. Carol: I could hear you thinking it. Me: Fine, you want to put words in my head then I have one stipulation. You two have to make out. Full on, tongue and everything for at least one minute. That's my counteroffer. You agree to that, and I'll do one more time. Carol: You're disgusting. Me: Take it or leave it. Your call. Carol: *huffed, huffed, sighed heavily* Fine. But for the record, you're sick. Me: You are too dear. It was the following Saturday night, and I was all dressed up as Melanie again for him. Since we had more time this evening, Carol did more makeup work which really changed the look. I don't think I'd pass as a woman up close, but maybe in a dark bar or across a room? Nah., He arrives, and we start off with a light dinner, some wine, and conversation. This time my wife left when Jack made his move. We kissed again for a good while though this time, his hands roaming all over me, groping his way around. I was once more put to my knees and within moments, he has put his dick into my mouth and holding it there. He asked me to look up and he took a picture. I pulled back and complained about that, but he promised it would go nowhere and to no one, just a memento. I didn't get a chance to debate because he thrust his cock back into my mouth and began slowly face fucking me. He didn't do this last time, so it was new and different. Then a strange sensation washed over me as the wine began to hit. I wasn't drunk, but like a touch high would be more like it. I don't drink much at all so that wasn't a shock for it to happen after three glasses in a short amount of time. My head moved in time with his hips until he stopped altogether and let me bob up and down in his lap gently. I didn't even realize I was doing it at the time, but he did and was loving it. He said lets try something different and I said sure, no problem. There was some moving around and repositioning. When I felt the cock pressed against my rear entry, I caught up on what was about to happen. That explained why I was put on hands and knees. Why did I feel a change in temperature when my skirt was lifted up and panties pulled down? Why I giggled when he smacked my ass. What it didn't explain, as I gritted my teeth and groaning in pain with the head of his cock passing the rim, was why my wife was watching me with her phone out. I was in so much pain, the lube did little to help with that, but I was thankful for it. It made a large difference when soon he began to fuck my completely virgin ass. I wailed in pain, but my wife tried to console me saying I was doing great, just a bit more and it will be all over with. But it wasn't a bit more. I was shoved back and forth like a doll beneath him as he fucked me. It was nothing at all what I ever imagined it would be like. It was heated, meaningful, feral almost. He wasn't fast either. He lasted a long time, through a few positions, cumming once but not done with me yet. He bent me over the end of the couch, plowing into me with such force, that I jerked around back and forth. After he filled me up the second time, he wiped his dick off on my ass cheeks, gave them a spank, and left for the night. Carol helped me into the shower and got me cleaned up. I was sore and exhausted, so I didn't notice when she put panties back on me to go to bed in. I laid there barely talking to her about what happened, and how that wasn't a part of the plan. Carol: Yeah. I didn't expect it either. But you looked so good I had to film it. You should've seen the look on your face. One of bliss. Me: Not a chance and even if so, it was the wine. I was so lightheaded I didn't know what was happening until it already was in progress. Carol: He did take advantage of that, and I'll talk to him about it. For now, dear, get some rest. We'll talk more in the morning. Me: *yawns* Goodnight, dear. Carol: Nite Melanie. *softly giggled, her plan starting wonderfully*