Troy

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Cyanlot
Cyanlot
1,102 Followers

The worst part of this was at the beginning, as my tongue first touched his bung hole. It was really the idea of the thing that was off-putting. Though there was a slight smell, it didn't really taste bad. After a while I sort of became used to it and I managed to rim him and ream him pretty well. Nina told me to reach up under his legs and feel whether it was getting his cock hard again. She told me that when she did this for Troy, it always got him hard, even if he'd just fucked her. (Perhaps it goes without saying that she'd never done anything like this with me. But I was past being hurt by thoughts like that.)

Troy was getting hard. In fact, he was surprisingly hard and big. While I continued tonguing his anus, I stroked his cock, too. This made him raise his hips slightly, which gave me better access to both of the objects of my attention.

When it was clear that Troy was fully aroused, Nina had me stop and pull him to a sitting position. Then, and she insisted that I look into his eyes, when I did this, she made me ask Troy if he would please fuck my ass.

I don't know whether they'd rehearsed this script but Troy toyed with me. He hemmed and hawed and said that I wasn't really his kind of girl. At Nina's instructions, I had to plead with him, telling him how much I wanted his beautiful cock in my virgin asshole and promising that I would make him feel wonderful.

Finally, Troy consented and instructed me to get on my hands and knees on the bed. He lifted my skirt from the back, just a Nina had done in the bathroom. But he was planning to insert something a good deal larger than she had. First, though, I felt his finger toying with my ass. I could feel the lubricant begin to ooze from my ass.

"Just the way I like my women...really wet and ready for my hard cock!" He went on, "You must really want it, bitch."

Want it or not, it was going to happen. What's that they say? "When rape is inevitable, you should just lie back and enjoy it"?!? Well, he wanted me doggy-style so there was no lying back. But it was inevitable that he was going to fuck me and there was no point in fighting it.

I felt his cock press against my asshole. When he had things lined up right, I felt both hands on my hips. I was afraid for a minute that he was going to thrust into me in a single, fast motion. I'd played with toys in my ass, but nothing nearly as big as a cock—especially nothing as big as Troy's cock. I was getting ready for a very uncomfortable—maybe even extraordinarily painful—sensation. But, to my surprise, Troy didn't just ram his cock in my ass. Instead, he used his hands on my hips to carefully control the motion as he very slowly—in fact, excruciatingly slowly—pressed his rigid shaft into my virgin ass.

I'd thought that such an entry would be the best I could hope for. Now I wasn't sure. Maybe it's like getting in cold water: best to do it in one fell swoop. This slow and gentle pace made me incredibly aware of each millimeter that his cock was violating me. As he got near bottoming out in me, I almost had to fight the urge to rear back and just get it over with. Of course, I had no intention of doing something on my own initiative that Troy and Nina would interpret as wanting to get fucked by Troy.

Once his loins were firmly against my butt cheeks and I could feel the full length of him inside me, Troy began to move in and out of me—slowly at first, but with an ever quickening pace. I put my elbows down and put my head to the sheet. When I looked down between by legs, my view was blocked by my skirt. So with one hand I pulled by skirt up. I watched as my still soft and shriveled penis and testicles swung back and forth to the rhythm Troy was setting up. They looked useless and irrelevant and I now realized why Nina had insisted in draining my balls. She wanted to make it very clear to me that there was only one dick getting pleasured in this bed now. Indeed, there was only one real man in the bed. I was a woman who just happened to have a few lumps of flesh between her legs. The only cock I was supposed to be thinking about was Troy's. And, looking at my now tiny dick flopping between my legs, I really didn't want to think about my own. So I dropped my skirt and just focused on the sensation of Troy's rod reaming my ass.

I began to move my ass to meet his thrusts. The sooner he came, the sooner this would all be over so it was in my interest not to be just an inanimate lump of flesh. Nina noticed my activity and began to verbally taunt me, though she pretended it was encouragement.

"That's it, Scarlett. Doesn't it feel terrific? I always love it when Troy fucks me in the ass." (Another thing we'd never done.) "Isn't it wonderful? He's so big and hard and don't you just love the way if fills you up?" Then she began giving me directions. "Try to squeeze his cock with your ass muscles. Do it especially hard as he pulls back—like you don't want him to pull out of you. You want his hard cock filling you forever."

For reasons other than those Nina was describing, I thought this wasn't such a bad idea. If I could milk his cock with my ass muscles, maybe he'd cum faster and this could all be over sooner.

So I worked Troy's cock with my ass muscles. I realized as I did this that it was better for me when I was actively involved. When I just knelt there, passively allowing Troy to penetrate me, I was a victim. Now I was an active participant.

Of course I knew that Nina and Troy would interpret my activity as a sign that I was enjoying what was happening. Well, let them interpret as they want. If you live your life based on how others will respond to your actions, you're certainly not a real man.

In one respect, it was pretty obvious how Troy was responding to my actions. My anal milking of his cock was driving him toward an intense orgasm. I could feel his muscles tighten as did his grip on my hips. And suddenly he roared and thrust deeply into me, holding that position as his cock erupted in my ass. I imagined enormous loads of seed filling my bowels.

Troy held perfectly still for a few moments and I used that opportunity to squeeze his cock repeatedly, drawing out whatever cream was left in his shaft. I guess this was too intense a sensation for his now very sensitive cock and he pushed away from me slowly. When we uncoupled, I felt a small stream of his juice run down on to my balls. Once again, I lifted my skirt, this time to watch Troy's cum drip off my balls onto the sheets.

I was emotionally and physically drained. I realized that causing a crashing orgasm in your partner can involve a sort of emotional climax in you, even if you don't have an orgasm. Troy had collapsed next to me on the bed and I lay down beside him, with my back nestled against his chest.

"Isn't that adorable?" Nina said in a mocking voice. But I didn't pay her any attention now. For a few minutes, I just rested and tried to make my mind a blank. I didn't feel bad, really, but I was pretty sure that if I thought much about what had just happened, I would. So a blank mind seemed desirable.

I didn't get much time to just veg. Nina told me, in no uncertain terms, that I needed to go to the guest room for the night—that she and Troy wanted to be alone now. As I pulled myself up and headed for the door, I could feel more of Troy's deposit leaking from my stretch anus.

"Wait," Nina barked. "Don't forget your panties." She bent down and picked up my panties and handed them to me gently. "A girl's got to clean up after herself. Right, Scarlett? Oh, and we'll have breakfast in bed tomorrow. Let's say about 9:00."

With that, I was dismissed. As I closed the door behind me, I could hear Nina giggling something to Troy. I couldn't hear what she said so I decided not to torture myself over it.

I went to the bathroom to undress and clean up. The first thing I needed to do, though, was to take a piss. As I sat on the toilet, holding my skirt up like I'd seen Nina do and looking down on my stocking-clad legs and at the garter belt holding them up, my mind filled with recriminations. What had I done to deserve this treatment? What the hell had become of me? I didn't have any good answers. I was distracted from thinking about them when I felt more cum oozing from my ass into the toilet.

I finished and wiped my tender asshole gently. As I flushed the toilet, I realized that, in many ways, I'd just handled the toilet needs exactly like a woman would.

Now it was time to get out of these clothes. That was all about relief. First the shoes. I'd gotten pretty skilled in walking in them and wasn't finding them too uncomfortable while I wore them but when I took them off, I felt a wave of pleasure. I realized why women complained about their feet hurting so much. Then, I untied my apron and unzipped my dress. I could finally breath normally again. It was a terrific sensation.

Looking at myself in the mirror, I realized that I still looked like a very attractive woman. The illusion hadn't been broken yet. I lowered the toilet lid and sat down again to unhook my stockings. I rolled them down my legs carefully so as not to snag them. Then I unhooked my garter belt and dropped it with the stockings.

Now, about the bra. It clipped in the back but I'd seen Nina hook a bra in front of her and then turn it around. So, I reversed the action and took off the bra. The breast forms were another matter. The glue was holding tight. Attempts to tear them off hurt. I finally decided that it didn't make sense to take them off tonight, especially since I was sure that Nina and Troy would insist on Scarlett as their maid tomorrow morning.

It felt weird to have the breast forms glued to me and no bra on; they pulled down on my skin in an uncomfortable way. So I decided to put my bra back on. There was no harm in sleeping in my bra and, if it felt more comfortable, then that's what I should do. And, then, looking in the mirror, I didn't like the look of the bra and my breast forms with hairless dick and balls showing. So, I decided to put my panties back on. At least there was some semblance of consistency to my appearance then.

I washed my face, taking off all of the make-up, but decided to leave my wig on for the same reason I put my panties back on. Tonight, I was going to be sleeping as a woman. I was so tired, I couldn't wait to get to sleep.

When I got into bed, though, I found myself tossing and turning, unable to get to sleep. Then of course, I became haunted with tonight's events. Images of my humiliation began flashing through my mind. These images kept me from sleeping. They also got me completely hard.

Sure, all the while Troy was fucking me, my penis hung there, a wilted flap of useless skin. Now, though, it was ready to party. I don't think it was just from recollecting tonight's activities, either. The silky feel of the panties against my skin, especially the underside of my cock when it began to get hard, was feeding the desire.

I wasn't going to get to sleep with this woody so I decided to take care of it. I pulled my panties down, just so that the front was behind by balls and began to stroke my cock. As I got more and more aroused, I slipped my other hand underneath me and down the back of my panties. I slid my finger between my ass cheeks and touched the still tender opening. As I jacked off, I poked my finger gently in and out of my rosebud. This brought me to an orgasm quickly. My jism shot up my abdomen and onto my bra.

After I'd recovered slightly, I managed to clean most of it up with my hand, licking it from my fingers. I decided I'd have to do a little spot washing of my bra with a hand cloth, but that could wait until tomorrow morning. I was exhausted and now felt as if I could sleep.

And sleep I did. I was startled when I awoke and saw how light it was. I saw that it was 8:30 and realized that I'd gotten myself in a time-bind. I had a lot to do before I served Nina and Troy breakfast at 9:00. I had to shower, clean up my bra, do my make-up, dress, and cook breakfast. I was going to be a busy little maid.

Over the next few months, things continued pretty much the same. Nina would date Troy once or twice during the week and spend most weekend nights with him, usually at our house. Often, they decided to do a replay, more or less, of me as the maid, satisfying Troy's needs. And these were pretty much exact replays, though Troy experimented with different positions. He took me standing up from behind and lying flat on the floor on my stomach with him pounding me from behind. He took me missionary style, too. I didn't like that because I had to look at him and I could see the smug dominance on his face.

Troy also had me ride him. Since Nina was usually careful about attending to my "needs" in the bathroom like she did that first night, this typically resulted in my limp dick flopping wildly up and down as I bounced on and off Troy's hard cock. Once, though, Nina was off her game and I got incredibly hard while I was riding Troy. Then my cock bounced up and down, but not as a limp flap of skin but as a rigid rod. Both Troy and Nina kind of liked that, too. They'd made it clear enough that I wasn't going to get off myself so they didn't worry about me forgetting my place. And they found it amusing that I got aroused by being fucked in the ass.

So, for months, with a few variations, it was really "same old, same old." But then things changed, and changed dramatically. And, surprisingly, I was the agent of the change. I may never understand why I did what I did. I certainly haven't come to any understanding of it yet.

Nina had to go out of town for a business conference for a long weekend. I'm sure she wanted Troy to go with her. (She never thought to invite me, of course.) But Troy had some sort of commitment in town that made that impossible. So, the two love-birds were going to have to spend a weekend apart. I wasn't heartbroken over this. I figured that I'd get a break from the humiliation. Maybe that would let me get some distance from the situation and, perhaps, start to put my life back together.

I took Nina to the airport Friday afternoon and was looking forward to being in charge of my own life for the weekend. I picked up Chinese—no sense cooking for myself—and ate in front of the TV. After I ate, I went into the study to download some new porn. I spent most of the evening watching a variety of genres of explicit porn. I found myself gravitating, though, to stuff that featured transvestites and transsexuals. I'd always found this stuff kind of exciting. It did, after all, break down conventional categories and startle the eye with novelty. Perhaps now, they had a special significance for me and stirred up complex and vivid emotions.

When I have a long time by myself like this, I don't like to rush myself to an orgasm. I look at things that get me hard and stroke for a while but don't work to bring myself off. It's fun to be in an aroused state for an extended period of time and, then, it's especially exciting to unleash all of that pent-up sexual tension with a crashing orgasm. That's what I was working on that Friday night.

I was really enjoying myself immensely. After a few glasses of wine, though, I needed to make a trip to the bathroom. After I'd taken a leak, when I was washing my hands at the sink, I saw in the mirror the reflection of my bra and panties that were lying over the shower rod, drying after they'd last been washed. I don't know what came over me then. Maybe it was the fact that I'd just been looking at the pictures and movies of transvestites, I don't know. But I pulled my clothes off and slipped into the panties. Then I fastened on the bra.

It was all wrong, of course. I didn't have on any make-up or my wig. And the cups of my bra hung empty on my chest. "Oh, shit!" I thought, "in for a dime, in for a dollar." I pulled off the bra and panties and started running a hot bubble bath. While it was running, I went to the bedroom to pick out some clothes. I knew I was going to go into this whole hog, but I didn't want to wear the maid's outfit. It was just too tight to be comfortable.

I found some very sexy negligee that Nina sometimes wore for Troy. I'm not much bigger than Nina so this would work. In fact, I thought, I might try on a lot of different things to see what I liked the feel of.

Back to the bath for now, though. I just soaked in the tub for a while, luxuriating in the foam and inhaling the scent of the bath soap. I felt as if this would help to get me in the mood. Before I got out, I shaved my legs (and more) to be sure that I was very smooth. It wouldn't feel right to pull sexy nylon stockings over stubbly legs.

Since I was going to make Nina's underwear drawer my private lingerie wardrobe, there was no need to limit myself to the bra and panties she had given me. I went into the bedroom and pulled out the items that I thought would look, or feel, sexiest. Before I began dressing, I needed to do some work to get into the proper persona. The wig was easy, of course. And I didn't have much trouble gluing on the breast forms. But I still struggled with the make-up. I'd had practice, of course. While Nina had always at least helped me when I'd dressed in the evenings for Troy, I'd been on my own the mornings after when I needed to dress to make and serve their breakfast. I still couldn't do it nearly as well as Nina could, but I managed to make myself passable.

I began trying on different combinations of bras, panties, teddies, negligees, night gowns, and things I didn't know the names for. I was having so much fun that after the first few outfits, I got out the camera and tripod and began taking pictures. Of course, then I needed to get back into the first few outfits I'd tried on to get pictures of those.

Before I knew it, I'd spent nearly three hours dressing, undressing, and posing in Nina's things. Of course, I was frequently aroused and took lots of pictures with my cock sticking rigidly out of pink lacey panties or blue silky panties or lavender translucent panties. Sometimes my erection would recede and I'd take a picture with my penis tucked so far back that you couldn't tell that I had a package. Sometimes I'd take a picture with my limp cock and balls hanging out the side of a skimpy bikini panty. I tried about every variation and every pose I could think of.

Finally, when I decided it was time to move on to getting relief, I set the camera up to take video and aimed it at the bed. I was wearing a short, powder blue negligee with slightly darker blue bra and panties. I started the camera and lay down on the bed.

My aim was to do something quite different from just whacking off. My aim was to make love to myself. So I began very slowly. I ran my fingers gently over my body. I felt my fingertips drag across my abdomen, under my nightie. I licked my fingers and slipped them down in my bra, pretending that I could feel myself playing with my nipples. And then I slipped my finger down into my panties and played with my dick.

Then I realized that I hadn't planned very well. Something was missing and I set about to change that. I had to pause the camera while I went to the bathroom and found the douche bottle that Nina had been using lubricate my ass. I filled it with lube and squirted enough into my ass to get me well lubricated.

I picked a nicely sized dildo out of Nina's stash—not the biggest, I couldn't take that, but a good-sized one—about the size of Troy's cock, I realized as I held it in my hand. It was a realistic one, with a nicely shaped helmet, veins, and even a set of balls at the base.

Turning the camera back on, I lay down again. I played with the fake cock with my hands. Then I licked it and sucked on it like it was a real cock. Finally, I pulled off my panties, lifted up my knees and spread my thighs. I decided to try to talk in a reasonable facsimile of a female voice. I things like, "be gentle," and "you're so big; go slowly." And I eased that cock gently into my yearning asshole.

Cyanlot
Cyanlot
1,102 Followers