"…I can maybe dress you up convincingly enough, and I'll even admit that I might have some fun with it" I told my husband, "but what happens next?"
"I'm afraid I don't follow you" he tells me, obviously looking for some more resistance from me on the entire concept of feming him out to see what that looked like on him. To be fair it's not the total leap one might expect, he's a great guy and all that, but soft spoken and easy to lead, so not what most would consider massively masculine traits. I don't require such in a life partner myself, ours more of the somewhat equal partnership variety, but to say that I've never had a single second thought on my own life choices would be a lie. Not necessarily trading in my proverbial old dependable car, but maybe driving by the dealership and looking in the windows, with the potential to add a secondary flashy sports car for the weekends to my proverbial garage.
…There had been a girlfriend once for myself, a very close girlfriend. It was between high school and college, a summer of discovery that left neither one of us looking for a young man to become close to, only to leave in heartbreaking fashion as we left in the fall for our own separate futures. We did everything together that girl and I, and I mean every thing, our straight-laced folks never the wiser, as they surely wouldn't have approved. Anyway, sufficient to say that I had that kind of opportunity once myself to try something a bit different and taboo, and it had been wonderful while it lasted, and even quasi-innocent in a way too…
My husband not so much, although he had eventually confessed to what I've come to understand myself is some mild curiosity about what such things would be like, with another guy. I guess it made logical sense, if you were a guy and horned up and willing to do anything for an orgasm, maybe even an oral orgasm; were you just as willing to submit and give such pleasure to another yourself? And then of course what about the other things that he's talked me into experimentally, things I didn't really care for personally? My "man" could theoretically be on the receiving end of all of it; or was this just all talk and no action, a fantasy curiosity never to be realized?
It all came down to givers and takers, and my wonderful husband was most certainly of the former. He could service me for an hour while nakedly kneeling before me, or until his jaw got sore, or my box did. He got off on it, but not orgasm off, more like service to another kind of off. In fact, the more I treated him like a serf, the more into it he got. "Get me this" and "do that now" kinds of things, I even crossed my ankles and rested them on his cute little ass once as he was going down on me, while seated in a chair watching a show on TV; literally using him like a foot stool as he brought me off.
Anyway, if he thought I'd judge him harshly he was mistaken, especially with my own past history, but for guys back in the day that kind of thing certainly wasn't accepted like it is now. I like it better these days to be sure; people are free to be who they'd like to be, no judgments, or at least few judgments…
"If I were to dress you up all sexy and hot, hot looking for an interested guy even; what then? Think of our own first dates, what were you after?"
"Was I really that bad?" he asks, but in a way deflecting from my question. That was a verbal habit of his, and he could be a bit evasive when he wanted to be. He wasn't a cheater, and he didn't straight out lie to me either, but truth be told I could live without this specific character trait of his. I also realize that this was something to put away in the back of my mind for another day, a habit to finally break maybe…
"Not bad, just physically interested, but if you weren't just as sweet and kind as you obviously are it wouldn't have gone any further, and here we are, almost twenty years later."
"So, you chose me? I guess that makes sense, you could have done much better you know," he tells me for the millionth time.
"Of course to the first part. As for the second; I'm not so sure. Anyway, the question stands, sexy for whom, and to what end?" I redirect.
"I don't want to cheat or leave you or anything, I'm just a bit bored though, and I want to try something new."
So, sexy for another man, dressed up as sexy and hot as I could make him and what might happen next; that in his mind wasn't cheating? Interesting? Another woman; cheating. Another man while dressed up as a woman; that was okay. It was hard to follow the logic to be honest, but with an ulterior motive or two of my own I decided to play along. Truth be told, I was a bit bored myself, and opportunities like this don't come very often…
"Oh baby doll, it's not cheating if we know about it ahead of time," I tell him with a sexy smile; trying out a new demeaning name for him as well. I then think to myself, no deflection there at all, that's about as honest as one can be. He's just told me that he wants to do more than just dress up, he wants to dress up and play; live the life of his alter ego for a bit. It just has to be this potential costume of femininity, maybe in his mind "he" wouldn't be stepping out, it would instead be his female alter ego.
…Baby steps, I then think to myself. First maybe panty shopping for him, discreetly of course. I didn't want to embarrass him in any way; he bared his soul to me, shared his desires, and I'd be a monster if I didn't at least try to help him in all this. But he wouldn't be wearing a single thing of mine, that was also for sure. He could try panties as a first step, then maybe a bra and panties around the house if we could find one to fit his little man boobs, depending on how he responded. To be clear the concept was anything but a turn-on for me at first, but this was more about him, or perhaps her, if things went as they might. I would try to embrace this alter ego of his because he wanted to try it, not because it did anything for me though…
So, sufficient to say that our first explorative steps into this "new deal" of ours were inside the house things, and I took full advantage, experimentally pressing him more into the housework that we shared. It was clear by his attitude that he thought he should be submissive to me anyway, and even just wearing panties under his guy clothes amped this up, as did his confessions that he wanted me to take a more heavy-hand with him.
Be careful what you ask for, sister; you just might get it I thought silently.
I wasn't exactly into this heavy-handed part either to be honest, but I also was a bit bored with housework as well, and having a partner that wanted to do more of these things for the kink aspect of it kind of worked for me in the short term. Now I also have to admit that something about this bothered me someplace in the back of my mind; was he more willing to take on chores because he was submitting to my authority more deeply, or was this "woman's work" in his mind, and as he wore more of the costume he took on more of the role?
I suspected it was actually the latter, but it's just a bit less clear what his intentions were once fully feminized, assuming that was his true goal. In my mind, feminization meant that he wanted to have some kind of sex with another man, and I for sure didn't want to watch that, as I knew I could never unsee it if I did.
Anyway, the more comfortable he became in his pantied submissive role, the less often we had actual sex, so if he was doing this as a kinky turn on, I'd say it was a full on failure as far as I was concerned. Not that I'm that shallow, but I had physical needs too, needs that were going without more times than not. Such makes me a cranky bitch too, and a little bit of that started to bubble up through my desire to selflessly provide this kink for my husband. I was still doing it for him, but it got just a bit easier to be cruel while doing so.
A few panties then turned into a drawer full in mere months, his insatiable desire to have new and sexy things without limit; at one point he actually had more than I did. Wash day was a challenge too, as in "are these yours or mine?" even though he generally wore one size smaller than I did, but hell, he has a tiny guy ass, and the tight panties contained and crushed down his guy parts as well. We found padded big band small cup bras online too, shopping together on my tablet every Sunday for the feminine treasures that would arrive sometime the next week. He even wanted matching things for he and I to wear to bed, but I flat out refused, something in that concept pushing a button for me, a bad button.
Where was all this going? I wondered in my mind, I was actually starting to notice other men at work, maybe I'm even projecting these kinds of signals subconsciously to them. I haven't been getting enough at home, and certain guys pick right up on that kind of thing like sharks do blood in the water. Shiny new cars at the proverbial dealership, and I'm really starting to notice some new noises and defects in the old one too.
Around the house his androgynous uniform of service consists of panties, black yoga pants, white V neck tee shirt with a bra underneath, with his man boobs kind of filling out the padded B cup bra too. It's not a straight up fem look, but not masculine either, not by a longshot. I have yet to complete the look, but I'm also looking for some resistance too, as in when/if he tells me that this is enough and we can dial it back a bit. I'm having trouble reading him though; is this still fun for him, or is he just going through the motions because I've been so accommodating? It's almost like we're on autopilot, just blindly seeing where this thing takes us automatically.
A part of me wants to see how far he'll go, because if he goes all the way there and dates another guy, I'm taking a test drive with something new myself. I've been more than good here, but everybody has their limits. I have several very lifelike toys now, also bought online, because I have needs too; generally attended to in the privacy of my shower or bath because I don't want to put on that kind of show for him. One such toy is about my husband's general girth and length, and rubbery bouncy, not stiff like a stick. It's my favorite, it feels kind of like the real thing, without a man driving it anyway.
I need to see where all this is going, maybe give a preview of what's in his future, so as an experiment I take my favorite chair in a short skirt and blouse and call him over. This isn't sex, we're not doing all that much of that lately, like none at all in the last few months. He's serviced me orally every time I've asked though, but even this has lost some of it's magic as there is just no substitute for a real man and deep penetration. Anyway, under my skirt I have a surprise, held tight between my thighs is that favorite bouncy toy, and this time he's going to service that instead, so I can see if that gets him off like I think it might.
He crawls right in there between my legs and I spring my surprise, pulling my skirt up and revealing my "cock." He stops dead in his tracks when he sees it, but when he looks up at me and sees my smile he maybe understands where I'm going here, this proverbial next step of ours. With one hand gently behind his head and the other on my silicone softish cock I pull him towards it and smack him playfully in the cheek with it. I do this a few times and he doesn't pull back, which is telling.
"Kiss it, Bitch!" I tell him half playfully, maybe channeling some harbored female rage at the way guys can be when acting horny-aggressively. I've had exclusively good guys myself, but we girls talk amongst ourselves all the time, and some of the stories are just terrible.
Anyway, with some encouragement from me he tentatively kisses it right on the head, and he even starts to get into it, tongue and all, but this is something I can't unsee either. I'm watching my husband kiss a cock, and even though it's not real and it's just the two of us, I can maybe see where this will end. In for a penny, in for a pound I then think, and I pull the back of his head further down my faux cock. No man just wants his cock kissed, they want the whole deal, they want you to submit and choke on it, they also expect you to swallow everything like you're starving, and look grateful for the opportunity.
The tiniest bit of encouragement apparently goes a long way here though, because in short order he's giving head like a porn star on coke, like totally out of control. I have to hold the thing by its suction cup base when he takes it all the way down his throat, his nose on my panties. He holds this for a few seconds and then comes half way back up so he can breathe, and then he repeats, his saliva coating the toy sloppily. I suddenly know why some guys get off on this, the power I feel is incredible even though this appendage of mine isn't real, and despite myself I also realize that not all of that moisture down there is due to him, as in his own saliva.
"Suck the balls too, bitch!" I tell him huskily, which he does. These are molded into the toy though, and not very much like the real thing at all, but still he goes for it. The sounds he makes as he's once again devouring my toy cock are just incredible, like choking to death on the best tasting ice cream cone ever. His head is bobbing up and down like he's really trying to get my "cock" to cum, and I tell him to use more tongue, as if I could feel what he was doing, which I obviously can't. He's moaning too, in an almost feminine way, telling me he's really into this game of ours, and that we're likely going all the way there now. He's in for a treat whether he realizes it or not, as most men can be anything but tender and sweet when they're needy, he is, but most men aren't him either.
He's wearing only a bra and panties at the moment and kind of rockin the look with his fair and scant body hair, and I take the opportunity to put my bare right foot between his legs and let him ride my foot. It's an awkward position for me, but I feel the heat and grinding he's reflexively giving it, and like three seconds into it he freezes up tight and orgasms all over my foot through his panties with a mouth-full groan. I feel the wet heat of his considerable mess, realizing how into this he must be to cum so quickly. He's just cum with a cock in his mouth for the first time ever, and I also realize that if I do this often enough I'll reprogram his brain to only get off in this way. It's evil, in a way, but it's also kind of what he's after, so in a way it might be even more evil not to.
He looks up at me sheepishly - half shame, half extraordinary relief in his eyes - we both realize what just happened, but I think I maybe surprised him with my words; "if you're going to suck cock, you better get really good at swallowing too."
He just came with a rubber cock in his mouth, so maybe his mood for kink is now at an all time low, but I press the issue and tell him if he doesn't clean up his mess immediately, he'll never cum again. It's a hollow threat and we both know it, but he tenderly dismounts my bare bouncing foot and kisses his way near his deposited white goo anyway. I really didn't think he'd do this, but that first tentative taste turns into a full lick… and then another, and another after that. I'm rubbing gently on myself through my now soaked panties as I watch my man doing something many would consider anything but manly. I'm not necessarily excited to watch this, but there is no denying the power I feel over him.
It's over too soon, and I just know that there is more submission to be had, and on a whim I tell him to kneel before me. What he smeared all over my foot was what was pushed through the scant fabric of his panties, and judging by the massive wet spot I can tell there is far more in there yet. I'm standing now, and it's obvious that he doesn't know what to do with his hands, so I tell him to keep them behind his back. He looks handcuffed and helpless like this, and my confidence surges; I now tower over this other person in the room with me, both physically, and psychologically.
I pull his panties back and look inside, seeing not only a sticky mess of fresh cum, but a very flaccid "package" hiding from sight. My once and done husband is most certainly done for the day, or at least a few hours. With the saliva covered dong still in my hand I sweep it inside and all around his sticky shrunken guy parts, capturing all the residue mess that I can. With one hand I then hold the dong by the suction cup base over my box, and with the other I once again guide the back of his head. His lips are closed for perhaps a few seconds at best, this being his only real resistance to the event so far.
…It's right under his nose, literally, and I know he can smell his pungent cum, because I can myself…
"Baby doll, your new boyfriend just took you out to dinner and dancing, he not only expects you to swallow, but also to leave his cock just as clean as you found it."
With fresh motivation he gets to the task at hand and pretty much sterilizes my rubber cock hands free, but despite my earlier bravado I really don't know where to go from here. The concept of a lover for him is one thing, but the personification of that lover is the real challenge. Guys in that community probably don't like to be used any more than any other guys, present company obviously excluded. So, do I stop here and put an end to all this, or do I fully fem him out, and then maybe whore him out after, letting him have something taboo and reckless like I did once while in my teens? Would I want him back afterwards, or should I give him away to a man that will appreciate him/her and look for a permanent replacement myself? His own words come back to me; maybe I could do better, and maybe he could too?