“…Tell me everything," I commanded my present boyfriend. He came home perhaps a little later than I had anticipated, likely telling me he had a far better time than he might like to admit to, or at the very least a more exciting one. This one actually had potential, unlike the last very serious boyfriend who actually thought he could somehow "own" me; nobody owns me! Finding the limits of that potential had a certain element of risk though, but I was willing to allow him to assume that risk to see if he was truly my version of "trainable," and therefore by extension "keepable" in the long term, as in ‘potential husband material’. I know this might sound harsh, but I finally knew what I wanted in a life partner now, and this man had many of those hard to find attributes. I personally brought a lot to the table myself - all humility aside - but I also expected a lot, as in a high degree of loyalty, and open mindedness to what could become a very non-traditional union a few years down the proverbial road.
I had an epiphany right after that last one had left my life; one "normal" man - even a very good one - just couldn't check all the boxes I personally needed to have checked in life, and the fault almost certainly lies within myself. Did it really make sense to solely focus on the physical, on a stunningly handsome man that could rock my world maybe a half hour every couple of days if I was actually in the mood for such, or even make my friends drool and stare with envy? What about the other twenty-three and one half hours or so of the day? It's obviously very nice to have a man to physically use like that, or even to be seen out with like a trophee holding my hand in public, but those types of men ordinarily don't want to be used either, they're not ideally suited to it, nor are they easily trainable.
Two dominant personalities in one household is a sure recipe for perpetual conflict, and I've had enough of that already for one lifetime…
For me it's almost like swimming upstream in a fast flowing river, and I'm simply tired of it. My solutions were obvious; find a submissive girlfriend and stop looking for a man, settle for a man that's much less than I deserve, or find a more docile and pliable soulmate of a man that would let me have another every now and then, when that kind of physical itch became unbearable for me. Aggressive men don't like to share either, it's also not in their DNA, but neither is cooking and doing the housework, or maybe even just helping me do the same if I felt the actual desire to chip in myself.
I made good money, had a great career with serious potential; is it so awful that I didn't want to come home and clean toilets? I also know that there are people in that business, wonderful people that I could employ, but I didn't want an employee, a liability to also provide for, I wanted a life partner that was pliable and submissive, a proverbial lump of clay that I could shape and reshape as I saw fit; one that would grow with me over time. I wanted a man that would compliment my take-charge business persona, massage me when I came home from the office late, and also cook my dinner, and even accept and be happy with the concept of me "dating" every now and then when "out of town." It's a lot to ask; certainly an understanding to come to well before everybody says "I do!"
"Everything?" my present boyfriend asked, the submissive trepidation in his voice almost delicious, and nearly as cute as the costume he had worn to the Halloween party we had both briefly attended together earlier in the evening. My eyebrows-raised stare told him clearly that I didn't share his concerns for any modesty he might wish to preserve though; there would simply be no secret-keeping in this relationship, in either direction. It's also a trick that I learned in a psych class I had once, when you want somebody to elaborate on a subject, just maintain eye contact after they get done speaking, as if to say with your eyes "is that all?"
…The costume was for Halloween, and the subject of a playful gender swapping dare between us to conveniently test the proverbial waters on my part. I truthfully needed just a bit of Halloween magic here, something to let him try on a new persona, or perhaps explore the one he didn't know he already had buried within. The fact that he didn't put up more than a token amount of resistance to the costume I had chosen for him told me a great deal, but his smeared makeup, dirty knees, and general disheveled appearance as he stood before me told me a great deal more; as did the unique and familiar smell on his breath…
I went dressed as a construction worker, hard hat, tool belt, work boots, and snug men's blue jeans, with a pair of my boyfriend's tube socks rolled and stuffed into his borrowed tighty-whities, making it look like I was a working man that was also hung like a racehorse. That was kind of a tongue-in-cheek thing for me, as I liked muscular hung guys just fine, at least for physical things. What must it be like to have something like that actually swinging around between your legs, something confident women wanted to handle and play with, and less than confident men envied? I wondered in my mind. Anyway, I coupled this "hung" look of mine with a baggy flannel shirt and tight sports bra that hid my assets reasonably well, my long hair french-braided and tucked under my hard hat. I knew full well that there were female construction workers and that my costume was only so effective, but my boyfriend's more than made up for our gender swapping theme.
His consisted of a flippy little - think cheerleader here - pleated pink and white skirt, well, well above the knee, white thigh-highs with a pink bow and lace at the top, and a pair of very cheap high heels with the buckle super glued closed to ensure he didn't slip out of them at some point; when his feet began to hurt as I knew they would. The shoes were cheap and would be disposed of after this night either way, but I hoped this man didn't meet a similar fate himself. I had set this little honesty test up in my mind for him, and I was rooting for him to pass. I had been disappointed before by other men, but in a way those were self-inflicted injuries too…
Anyway, under his short skirt he wore two pairs of rather thick neon-pink panties, with his freshly denuded male hardware tucked back and out of the way, the somewhat flat front presented by his creatively layered faux emasculation likely to fool all but a serious hands-on search of that part of him… just as long as he didn't get himself excited. He did get into them, telling me something without actually "telling" me verbally. It's an interesting human experiment; does your man resist or outright refuse, or does he go along, telling you something about himself that he might not be able to come right out and verbally say. I personally was prepared for any eventuality here, but I most expected some token amount of resistance, followed by submission; it was his established pattern with me.
Anyway, in this case I suspected his tucked guy parts were telling me that he liked the way these things felt and looked, but I pretended not to notice, lest I spoil and contaminate this experiment before it even started. The panties were one small pair, and one medium, the small ones on him first to further compact and contain his guy parts. I also know that they make tiny chastity devices to do the same, just as some in the lifestyle tape their inconvenient genitalia back and out of the way, or buy special "panties" with tubes and other contraptions sewn in to do the same, but for several reasons I just didn't want to go all that far - be that kind of invested - in this first "outing" of his, if you'll pardon the cheap pun.
A thorough shave of his body and some perfume aided in the overall feminizing deception, and what I was left looking at was most suggestive of virginal innocence, with maybe a touch of teenage cheerleader allure, an altogether fitting look in my opinion as this was his first ever "female" outing. In all fairness his slight build and stature were contributing factors as well, and one of the many reasons I had noticed him in the first place; he was refreshingly different from the men that ordinarily sought me, the same ones that eventually disappointed me too. I perhaps seemed unapproachable to many men, except for those that have a surplus of brutish masculinity, but truthfully men like that can also be rather one dimensional. This isn't to imply that this current man and I didn't have a building closeness, that my heart wasn't involved here, it's just that I needed to know if we should continue; take that next step together, make that kind of further emotional investment.
Muscular manly men obviously had their purposes in my life and likely always would, but this slightly built, open minded and easily trained one perhaps did as well. I was now in the market for the latter, a cross between a BFF and a true life companion, as there was an apparent endless supply of the former. I wanted the quintessential trainable submissive to fall in love with, a lump of clay to shape, and even reshape over the long course of time as I saw fit. This Halloween costume party was merely the perfect excuse to take this one for a proverbial test drive to see if this was "the one," and therefore the one I would perhaps be keeping.
Anyway, on his top half he wore an off the discount shelf padded bra, there to both cover and ever so slightly enhance his slight "man boobs," the overall effect though being no more than at best a barely-there "B" cup physique. It would have been far too cliché to build him up with great big bouncy breasts under the tight long sleeve thrift store sweater I had chosen for him, I instead going for more of a budget friendly feminization this first time, as good silicone breast forms cost money, as do bras to properly hold them. I might be in the market for a BFF, but neither he, nor she, would be sharing any of my clothes, our intimacy wouldn't extend that far.
Nail polish on his properly shaped nails, tasteful makeup, and an effeminate style to his own natural long hair at our local shopping mall's discount salon completed our elaborate preparations, although his expression was one of both fear and excitement later that night as he first got fully dressed up, and then got into my car with me, sealing his commitment. Did the neighbors see us, did they think it was just myself and an unknown natural female friend? Dressing him up inside my house to see if everything fit was obviously one thing, the effeminate hair at the shopping mall a little earlier in the day while still wearing guy clothes another, but taking him out someplace looking like this, femininely turned out, taking this proverbial show on the road, that took courage. Courage and desire, and again a bit of Halloween magic, as one can dress up as almost anything that one day a year and get away with it. It's a ready-made excuse to try on a new persona, to think outside the proverbial box as to what's possible, or so I had hoped.
I was driving us there as per our agreement, but he knew he had to find his own way home - one way or the other - later on that night to keep his part of our bargain. He at the very least was walking home in his cheerleader inspired outfit and heels to get a taste of what it's like to be a woman, or perhaps much more of an experience along those lines if things worked out as I had anticipated. That was ostensibly my excuse for suggesting our gender swapping costume theme, so he could get a little feel for what it was like to be a woman, to walk in my proverbial shoes, to have men look at you like that, to see things from the other side. It's truthfully a lesson this particular man didn't need; but here I think I subconsciously wanted to punish him, as a representative of his gender, for all the dumb and rude things I and others have suffered over the years. It's obviously not fair, but I as well am an imperfect being…
So I intentionally parked far enough away from the other cars so that my guy could get some last minute extra practice in his heels before it was show time, "swish your hips and don't stomp" I told him several times on the way, some things in this little experiment of mine obviously needing just a bit more practice. He was stiff and nervous as hell, but to his credit he didn't back out either. I showed his I.D. and mine at the door, getting a wristband with a barcode on each of us, and putting one of my credit cards on file for the bar tab and entrance fee. There were prizes for both the best and most creative costumes, but neither of us really expected to win. The man at the door looked him over pretty well, and even asked his birthdate and address, as his driver's license photo and his cheerleader persona obviously didn't match at all. The venu was a hotel bar and restaurant, this in my estimation a brilliantly creative way to generate some revenue for an otherwise dead weekend for this business friendly hotel.
My cheerleader had no pocketbook with him, and by design no pockets either, so no place for the cell phone or wallet I didn't want him to have. We entered the actual event floor separately as I had warned him we would, so ostensibly nobody there - except the door guy - would know he and I were together. We both mingled and drank at the party - I watched out for him covertly - but in his case I came to realize somewhat anonymously as we clearly hadn't been seen entering together. That was the actual plan, but making these things happen in the real world can be difficult at best, although he likely decided that if he kept away from me nobody would likely associate him/her with me at some later date.This place was close enough to where I both lived and grew up that it was at least likely that I would run into somebody I knew there. My new guy was from out of town though, so it was unlikely he'd do the same.
I found a man that easily saw right through my gender bending costume, his own store-bought superhero one - plastic face mask and all - perhaps an order of magnitude less creative than my own, something a teen boy might even fit into. It looked like it was opportunistically bought that day, and in talking with him I discovered that's about how it went for him. It was just something fun for him to do as he was staying at the hotel anyway, and once his plastic mask was out of the way - so that we could talk a bit in a more personal way - I discovered what he maybe already had; that we kind of knew each other.
I casually knew this man as we had gone to high school together years earlier; within a different circle of friends though. I even danced close with him, playfully grinding my faux tube-sock crotch on his very real one during a slow number. He was back home visiting friends, but actually staying at the hotel so as to have his own bathroom and not intrude, and under slightly different conditions I might have liked to take the next step or three and go to his room with him for a few hours, or even take him to my own nearby home to entertain me while awaiting my boyfriend's eventual arrival. Doing that though would be just too many steps at once, not to mention deviating from my long term plans. I was doing all this for the long haul, not instant sexual gratification; I've had my fair share of that already in life, and at some point it became time to grow up. He moved well on the dancefloor though, suggesting he might move well elsewhere too…
I also wasn't necessarily that easy any longer, and while my Halloween dance partner was technically already known to me - and surely handsome - he was also receptive to my playful costume-inspired dancefloor boldness. It's also nice to flirt a little, get to know somebody; any other way cheapens the experience for me. Such would also make me a straight up cheater - with my feminized boyfriend in the same building even - and I didn't want to be one of those; I had different plans in life. This isn't to imply that my little cheerleader doesn't do for me quite nicely himself, but I offer an imperfect analogy here; I might own a fine home in a great neighborhood, but it might also be nice to have a summerhouse somewhere else someday, someplace different to visit, maybe spend the weekend "roughing-it" when the mood strikes me every now and then…
…It was truly a bit of Halloween magic to watch my cheerleader embrace his feminine alter ego from afar, the walk and soft spoken voice looking and sounding almost genuine from the distance I had observed them. I knew from personal experience that good costumes can cause one to grow into the role - like myself shamelessly grinding on my own superhero dance partner, or even wearing a "barely-there" club dress in a big city club - but to me it's still fascinating to actually watch it happen. The heels and feminine saunter were a challenge to be sure, especially for someone new to them, but he knew there really was no going back once he stepped into my car in my driveway, and I respected the courage it took for him to do this stunt in public. He looked like he was actually having fun, and of course had his eye on the proverbial prize I had offered. He would be receiving it one way or the other, but possibly not in the way either he or I may have anticipated when I had made the original offer…
I had of course hedged my bets so as to make sure nothing too terrible happened to him on the way home; this was supposed to be fun, and I'm no monster either. I had asked a workout partner friend - who had told me about this party in the first place - to make sure he got home safely, with the understanding that he was welcome to have a little innocent fun with my costumed and crossdressed guy. I didn't spell out any limits on the fun in question, but I also knew my friend's preferences; a "ride home" can obviously mean a great many different things, to a great many different people. This workout friend even had a picture of my dressed "guy" texted to him to ensure he didn't chase the wrong tail, taken discretely just before he got into my car. He was a good guy to work out with, as in he never hit on me; for reasons that will become obvious.
"I drank something strong for a bit of liquid courage, and then danced with some guys, and then when my feet started to really hurt and I noticed that you and your new superman friend had already left I did the same, and slipped out and started to walk home" he told me far too quickly. "Heels hurt after a bit," he added to soften his implied rebuke, noticing the dark look I had given him at the suggestion that I had done something further with my superman friend. Truth be told, I had wanted to, and maybe knowing me as he does he saw my body language for what it was - all the way across the room - but in the end I only said goodnight with a little peck on the lips, nothing more than that.
"So early? Details, I need details if you expect to win this little wager of ours… Oh, and by the way, I didn't leave with superman, we only danced and chatted a bit; we actually went to school together!"
I spoke with a stern look, my voice taking on a masculine power suggestive of the costume I still mostly wore. This was the voice and tone that told him he would never get away with being less than honest with me one single time. This was also the voice that told him that nothing further happened between my friend and I; take that right to the bank!
What did this look like from my cheerleader's point of view though? I had dressed him up, feminized, and dumped at a party where he doesn't know anybody, perhaps in his mind so that I could hook up with somebody else more to my liking for a few hours. He's no dope, he sees the way guys look at me, even when I'm out with him, we've even talked about that, about the way I unintentionally seem to send out a certain vibe, to certain excessively masculine men. Many men would be overcome with jealousy in similar situations, where he instead, dressed as my temporary cheerleader, left to find his own ride to my place and his own clothes as per our original agreement. I had intentionally marooned him in that place and in that costume, and truth be told he knew the plan for that and went anyway, knowing how men like to hit on me at parties. He even did all this, maybe thinking I was someplace private with superman, maybe even thinking I was doing something I had casually thought about actually doing. It was a lot to ponder, more than I actually expected from this little experiment of mine, and I owe it all to a chance encounter with an old school friend.
"Did you walk ALL the way home in your heels, Little Missy?" I asked, using the playful sissy name that I had started calling him while in his cute feminine alter ego costume, trying to get the mood here back to a fun one. I know it's so wrong, but just using that particular name with him/her made it seem as if she became a foot shorter, and I became a foot taller. I was powerfully in charge here, the sensation coursing through my veins like a potent drug. This is what I needed, the free exercise of raw power and domination; I only hoped Little Missy needed the complimentary version of this too.
"No ma'am," he responded, I now suspecting that something profound had happened, more so than the mere concept of my leaving the party with another man; a concept that I had just shut down cold on him though. Did I dare confess that I was actually thinking about it? Does this mean that maybe he had seen something in our interactions and body language, superman and I, that had suggested something was about to happen? Did all this occur and still he didn't come over and say hello, lay legitimate claim to me, while also spoiling the party for me, or even the assumed hotel room after-party with superman?
Anyway, I could always text my workout buddy - the one I had asked to keep an eye on my cheerleader - to see what specifically had happened, and I might at some point to check the accuracy of his story, but having him stand there and confess his transgendered transgressions to me was just too much fun, and good submissive practice in case this one turned out to be "the one." Confessions are good after all, it firmly establishes who's in charge, who's the top dog.
"I hardly got out of the parking lot when a minivan with tinted windows pulled up to me, the driver, who was dressed like a clown, asked me if I wanted a ride home, which I accepted as I recognized him as one of the nice guys that I had danced with at the party, as per our bet. I opened the sliding side door, at his direction, and hopped in, only to find that two of his buddies that I had also danced with were in back - a pirate and a convict - their hands all over me while ostensibly helping me into the very back seat between them before I could even object. The center seat had been folded down, leaving a fair bit of room in the back of the van on the floor, but no extra seating.
“The door was slammed, and the clown drove off. We were apparently dropping off my fellow rear seat passengers first as I was the last to get in. The driver didn't ask me for an address, so this was an assumption on my part, but in the end that's how it worked out anyway."
"SOOO, back up a few, how was it dancing with the guys?" I asked, leading him on to tell the whole tale, fill in the rich details as a distraction to my own distractions. My first proper dance with a boy was a very big deal, so here I assumed his was as well. I was more than anxious to hear how that part went too, but I also knew that he didn't get this half-destroyed costume look of his by just dancing either. This quasi-interrogation was fun, and having a serious effect on me, my own rather dominant alter ego threatening to make herself fully known. This man of mine was about to let me see just a bit of the real him, and he was about to see the real me too, I just hoped he could handle it.
"…At first the pirate only wanted a kiss in exchange for a ride home," my man confessed sheepishly while staring at the floor between us, my feminized man suddenly not able to make eye contact with me. Gone was that earlier half-challenge; so much the better from my point of view. The world was full of overly masculine men, and while they are fun, and I am drawn to them physically, they just don't domesticate well…
"Seems reasonable, all things considered," I offered in encouraging tones, just to let him know that I found this exciting, this taboo first man-kiss of his… well at least as far as I knew. I had noticed his dance partners myself the several times I had peeked on him, and like the clown that I had asked to keep an eye on him, all three were just about old enough to drink themselves, meaning I didn't expect any of them to take serious advantage of my guy, no matter how he was dressed. Playful fun was one thing, as I had told my young gym friend when I had asked for his help, and again I knew of his preferences. He was a respectful young man that didn't hit on me, so it was easy to strike up a "gym" friendship, spot each other when lifting, but I digress…
"It didn't to me, at first, but these guys - I thought - still believed I was a for-real woman dressed as a cheerleader, and I had danced with each of them at the party, let them buy me drinks, and likely their friends had seen me dance with them at the party as well. I thought they might not have taken it so well if they discovered that they had danced with a cross-dressed guy who had tricked them, and there were three of them."
"Were you scared; did they threaten you in any way?" I asked seriously. This most certainly wasn't what I wanted out of this little testing-of-the-waters charade. I wanted to have fun with it, but more importantly I wanted him to have fun with it, open his eyes to something he may not have ever considered before, submitting to somebody else, submitting to a man, even a youngish one.
"No… not really. They were nice enough to me and all that, very nice in fact, but I felt… obligated at that point to keep them believing that I was what they thought I was… to keep the illusion alive… for them… And, I figured it was just a kiss." My guy was obviously conflicted and struggling just a little to explain himself here.
…I found this power over this slightly built man of mine intoxicating, it surged through my veins like a potent drug, and I had to fight the desire to roughly take him right there and then, and do what I pleased with him after that, but first he had to finish his confessions to me, to properly seal his fate…
"So, how was it?" I asked with a smile, while trying not to give away too much.
"In a word, rough. Guys apparently kiss rough; well, half-drunk ones do at any rate. And this pirate had his tongue nearly down my throat as he wrapped his arms around mine so I couldn't even go anywhere until he let me. It was very… aggressive… and I… I surprised myself and moaned like a little girl and submitted to his probing tongue as his convict friend took advantage of my pinned arms and half turned body; so he at the same time lifted my skirt and felt up my ass. I even tasted the beer on the pirate's tongue, I actually sucked on it, it was impossibly surreal."
"I could do the making-out part as I was very "in-the moment," it was actually kind of hot as there was more than one of them, but I knew I couldn't let them continue to feel me up… then they would have discovered what… or should I say who, I really was. All kinds of crazy thoughts went through my mind then, but the one I kept coming back to was them driving me into the bad part of the city and dumping me off someplace to find my own way home from there, and dressed as I was with no I.D. or money, or even a phone…"
"…Wow, that's so hot and kinky," I interrupted, with all the lusty tones that I could muster in my voice. This one might just actually be "the one," certainly he had the ability to be bent to another's will, and to me that was the most useful trait for a husband/servant, at least the kind I was looking for. I've had manly muscular men, they're drawn to me like sharks to chum, but they always want to run things and eventually own me though; nobody owns me! And while the sex was sometimes toe curlingly fantastic, even an hour of it every few nights wasn't worth letting any man run roughshod over me, it just wasn't going to happen. I liked sex, liked it a lot, but I just didn't live for it any longer…
"The guy with his hands all over my panty covered ass then started to reach around to where my lady parts would expect to be found, and I clamped my naked thighs shut knowing it would ruin the charade, and possibly put me in serious physical peril. 'Anything but that' I told both of them foolishly between passionate breathless kisses, all as our clown driver stole glances of the back seat action through his rear-view mirror. I was just so irrationally wound up from making out that I wasn't thinking straight; but it was still just… just an insane offer for me to make all the same. 'Anything' can obviously mean quite a bit to some horny half-drunk guys.
"Apparently accepting this restriction, the pirate lifted me like a toy and placed me on his lap facing him, my arms not freed however, as his friend the convict then took to holding my wrists pinned firmly behind my back, the move presenting my chest to the lusty young pirate. Both guys were much bigger than I am, and the pirate specifically was very strong, his body was like a rock.
"My passionate pirate had stopped making out with me with the move to his lap, but with his hands now freed from the task of pinning me in place he took to molesting my tits… that is chest, pinching and mashing the flesh there hard enough to leave bruises… even through my padded bra and thick sweater. It was just so surreal, like some kind of out of body experience, and I surprised myself as a guttural groan of unintended encouragement escaped my lips, even though his rough handling of my tits stung when he somehow found my erect nipples through both my bra, and sweater.
"The pirate I had been making out with was probably not even twenty yet, but quite muscular for his age, maybe even a gym rat of some kind. He was also obviously aroused, his man hardware erect and poking up at me, all while my own remained hopefully tucked out of sight. He told me playfully that I was a little cock tease, then telling me more reasonably that it wasn't fair to send him home like this. It was a logical argument, one I might have even made myself once as a horned-up teen, so I certainly could see his side of things.
"’What do you want?' I breathlessly asked the desperate horned-up pirate, knowing my 'anything but that' offer might just be my undoing, but both young men in that back seat with me had respected my limits so far, my guy hardware was still trapped and hiding, and I was willing to do literally anything to keep it that way.
"'Prove you're not just another dance floor cock tease and bring me off, if you don't want to actually fuck instead,' he told me coarsely. This was definitely uncharted territory for me as I had never even touched another guy's junk - a real other cock before - erect or otherwise…"
"Continue," I told my boyfriend, this he knew was not a request based on my tone alone; this was no time to give a mixed signal of any kind to this man confessing his "sins" before me.
"Okay then… I… I was just so into my faux female tease role, I guess… At any rate, I then felt like such a slut because I told him to make me, and as if answering my challenge, he roughly placed me on my knees on the floor in front of him, as the convict that was holding my wrists firmly behind my back released me. He then wiggled his loose costume pants down, and I was left staring at about the largest cock I had ever seen…"
"Looking led to touching and I eventually found myself curiously handling his erect member in the dark back of the van, after a rather long pause to build my courage that probably looked to him like more teasing. It had actual mass like a fleshy little club, I just don't know how to say it any other way, but I was mesmerized by it; this first ever 'other' cock.
“Anyway, I didn't really have a plan though, so I first ran my painted nails up the sides of it experimentally, watching the skin wrinkle and react. I had to work myself up to serious skin on skin touching and stroking, although I know that sounds odd. Anyway, I wondered if I could somehow find even more courage, enough to at least try to give this poor horned up guy a hand job, to release his pent-up sexual tension… that I had obviously caused, all in exchange for my 'free' ride home.
"I realized that the pirate was impossibly hung, neither of my hands fully closing around his hot veiny girth without squeezing, both of my hands stacked one on top of the other with room to spare like I was holding a softball bat, or maybe a giant ice cream cone. It felt so hard that it must have hurt him, the veins standing out angrily just under the pulled taunt thin skin like nothing I have ever seen before on myself, and I felt guilty because 'I' had done this to him. I then gently rubbed the giant purple tip with my thumb, more out of curiosity than anything else, but his leaking precum had already lubricated the sensitive tip, and then it was his turn to groan.
"I rubbed and teased him as his precum really started to flow, his hips left rocking in little instinctive sexual thrusts. I was suddenly curious to see things closer in the dark back of that van for no rational reason that I can explain. I then caught myself licking my lipstick with my face way less than an arm's reach from the largest cock I had ever seen, and both boys in the back of that van with me noticed!
"I then pulled my top hand away and sucked his precum from my thumb like I was on autopilot, it tasted sweet, and nothing like I imagined it would, and I found myself irrationally wanting more of it, if for nothing else but to quench the building lust I was feeling myself. I was still feeling impossibly oral from our earlier make-out session, and curious about what was in my hands now too. I realize this now, but right then I don't know what I was thinking, or even IF I was thinking.
"It shouldn't have been a surprise for me when the pirate's hands came down on the back of my head… gently… encouragingly. And, to be perfectly fair, I didn't need all that much encouragement at that point as I was strangely curious to… to see what things were like on the other end of things…”
"That is about the hottest thing I've ever heard!" I confessed to my visibly relieved and still feminized boyfriend, my hand stroking inside my thighs absentmindedly. If he thought I was about to judge him harshly for his understandable sexual curiosity - that I had in part engineered - I wanted to instead comfort him and let him know that this was instead impossibly hot for me. It took courage to confess this to anybody, not many men have that kind of courage, that kind of pliability either, and I intended to reward him handsomely for such.
"It wasn't all that bad in the big scheme of things, I had already tasted his sweet lubricating discharge on my thumb, so getting this directly from the source was just another incremental step. I started off with a few slobbery kisses, just kind of making out with his impossible large and hard cock, not really having any plan for what would come next."
"’Come next’? That's funny," I interrupted. "Oh, I've made out with a girl before too by the way, just so you know."
"Really?" he asked with a smile.
"Yeah, it was very hot. Sorry for the distraction though; continue where you left off."
"Okay, I eventually built up my courage and tried to do for him what I know I like to have done to me, except in this case I teased him without mercy time and again as I knew the signs of his approaching orgasm better than any 'natural' woman possibly could. I even tried to get him all the way down my throat in a kind of game to see if I could, and he REALLY liked that part, but it was hard to keep him there for more than a few seconds at a time without choking as his cock was frickin’ HUGE! The sounds I made when I did that were just incredible too, and I would have burst out laughing if I heard such noises from somebody else.
"I didn't want to necessarily do the whole deed to completion either, but when I tried to pull away, when I had teased him too far that very last time and felt him about to pop, he instead held me firmly in place with his impossibly strong grip… and sufficient to say that my first ever blow job was a stunning 'complete' success. I coughed a little as the force of his orgasm was so intense, but the reflex to swallow what was squirted into my mouth - and at that point halfway down my throat - overcame any other considerations I may have had. It didn't taste bad at all, and to be fair there was no other place to go with the pirate's cum that wouldn't have left a mess just about everywhere, as he came with incredible volume. I did proper clean up duty afterwards as well, his deflating shaft having some of what I had missed running down it. In any event, the pirate left with empty balls and a clean, soft, and sated cock by the time I was done with him. I even did such an awesome job sucking that first ever cock that his buddy, the convict, wanted his turn next.
"His 'thanks sweetheart, that was perfect' compliment made me soar, I had done this for and to him, and his leaning back relaxed posture told me I had done well. I knew that feeling personally, and it was both confusing and hot to be able to do it for somebody else, another guy I mean. Anyway, I knew I couldn't play favorites, and after catching my breath while still on my knees submissively, I intended to service the convict next, before I maybe lost my lust-fueled courage.
"We shortly afterwards dropped off the freshly de-stressed pirate at his house, he exiting the back of the van after a none to gentle slap on my panty covered ass that made me yelp, but he had been properly sated and didn't need to be all that caring and sweet with me any longer. I knew first-hand how a man's mind changed once he came off, and it would be hypocritical for me to complain about such treatment, and really I'm not. The interior lamp that illuminated the entire inside of the van when the door opened allowed my still kneeling female form to be easily visible to several people on the street where he lived. I was left wondering what they thought, and once again grateful for my feminine disguise."
"That's the most erotic thing I've ever heard, please continue." I encouraged gently, my hand rubbing at myself openly without shame, my heat almost overwhelming me. I had removed the tube socks the moment I got home, so this felt pretty good.
Encouraged, my boyfriend continued, he had clearly seen my hand, and what I was doing with it.
"Well…part of the convict's costume included a pair of handcuffs, he wasn't wearing them at the time as they were more for show, but they were attached to his prisoner's jumpsuit belt as part of his getup. The blow job I was forced into was wonderful and all that, but when he had earlier held my wrists behind my back forcefully for his friend, I'm pretty sure that's what got me hot and going in the first place; hot enough, I think, to want to blow his friend. Or, at least I thought that's what did it. So, in light of this, I told the convict as well that if he wanted something from me, he would have to make me do it for him too, just like his friend did. I then asked him if his handcuffs were real, which I thought was about as direct as I could be without asking him specifically to use his cuffs on me.
"Getting out of his jumpsuit-like costume required him to basically strip naked in the back of the van, and he obviously felt that I was overdressed in comparison to him. To fix this little problem he pulled my sweater off over my head and threw it forward to our clown driver, I now reduced to wearing a bra and short skirt while on my knees for this faux convict - cum on my breath and all - my mind wandering to what a real escaped convict would do with the likes of one like me in a similar situation.
"The handcuffs were next, he cuffed me behind my back after I offered my wrists to him, but this made anything I might like to do for him just a bit more challenging. There was just something so… so wild about being so helpless with these guys dressed as I was. It's what I needed, and I think the convict, even though he looked to be a teen still too, I think he understood this at some level. I was doing this now, pretty much no matter what, no matter even if I suddenly changed my mind!
"This mere teenager had absolute power and authority over me, it was intoxicating, I was doing whatever he wanted me to, simply because he could physically make me do it. It's hard to put into words, but that's as close as I can get.
"Does this make me strange?" my boyfriend asked seriously. "For that matter, did I just cheat on you?"
"No, not at all, to either; it makes you open minded and fun!" I offered with total sincerity. "It also makes you impossibly submissive, but I already knew this about you, and don't worry, I have enough of a dominant personality for the both of us, with some to spare" I further offered. This, I hope, implied to this cross-dressed costumed man before me that I had future plans that obviously included him, although maybe not in exactly the same role that he may have envisioned. "Please go on, this is turning me on like mad," I purred.
"But I cheated on you, with another guy?"
"I honestly thought about doing the same tonight…"
"With Superman? But in the end, you didn't, did you?"
"We'll get to that, please finish, I believe you're cuffed on your knees in the back of the clown's van."
"Yes. So anyway, there I was on my knees before this now naked convict, not nearly as large as his pirate buddy, but still hard and erect, and very needy. I hadn't even kissed this one yet though, but I did have fresh cock on my breath so I can't necessarily blame him for not wanting to make out with me first. I was there to service his manly needs, fellate and service him like a human tool, not 'make love' to him. I knew the difference obviously, but I never experienced it personally from this side of things before either. I was a sexual tool for him to use, a convenient cock-socket to dump his pent up seed, nothing more than that to him.
"The handcuffs drove this distinction home for me even more, and I appreciated them for this, although the hard and unyielding cuffs were no toys and felt quite real. I wasn't going anywhere until he was done with me, the thought motivating me sexually. These guys could still toss me from their van on a city street someplace, cuffed and wearing a bra and skirt, or even much less; if I somehow suddenly disappointed them, failed to perform.
"He molested my tits overtop my bra first, taking advantage of my mostly naked top half, my head tipped back as I once again groaned. I had never realized how sensitive my nipples got before, like an erogenous zone for me. He then pinched my nipples much more savagely, but on top of my bra, a part of me wished he would just suck on them instead. I didn't know if I would even like that, but it had to feel better than all that pinching.
"That didn't happen though, the convict was still in charge, and his hard cock still in need as well. I bent at the waist and tenderly kissed the head of his cock as if in greeting, it sticking straight up and looking firm enough to hang a coat on. After my kiss of greeting, I gave several others, touching the tip with my tongue experimentally and swirling it about, his precum not even there yet though. I then gave him several progressively sloppier kisses on his cock, in effect making out with it, but taking it deeper with every one. Nobody knew who I was though, and I knew I could do almost anything with these guys experimentally, without any real consequences.
"There was no teasing this guy along though, like I had the hung pirate; he was hard, but no closer to coming than when I had started. Nothing seemed to work, but I was new to this too, I also had the feeling that we were just driving around until I did the deed and drained this horny teen dry.
"I… I… do you really want to know this next part?" my guy then asked me.
"In for a penny, in for a pound," I told my boyfriend. The only thing better for me than having my boyfriend relate something like this almost directly after it happened, would be watching it happen, as if I were a fly on the wall or something. Then a thought occurred to me, everybody has smart phones these days, did one of the guys get some video to share with me, to document the consensual nature of the deed for any later potential need?
"Okay then, I had a girlfriend once, and one single time right before we broke up she did something extraordinary for me, as a kind of parting blow, if you'll pardon the pun. Well anyway, I thought I would give it a try, especially since I didn't have the use of my hands with which to help. I hadn't thought that would be such a big deal, being handcuffed and all, but in the end it was.
"So anyway, I gently bit my way down the length of him like I was eating a hotdog, from the side kind of, one little nibble at a time, and I could tell that this was new for him too, because he groaned and thrust his hips out. Before I was doing this to him, there was no real interaction between us, but my gentle teeth-thing at least got a reaction. Once at the base of him I totally slutted out and sucked each one of his man bits into my mouth and played with them with my tongue, and he went absolutely nuts. This then got ME going, it's fun to get a response you know, interaction and all that. Who wants to blow a lifeless warm cock anyway? I wanted a reaction, participation, hell I wanted to hear him groan and get into it, grab my head and fuck my throat like a monster, let me know that I was doing 'it' for him. So anyway, as I did that some more I pulled at my cuffs and reminded myself that for all intents and purposes I was his helpless female fuck toy, and wasn't going anywhere until I was released, and this got me going some more. I went up and down him, and then did it some more, I think wiping all my lipstick off on him in the process.
"So, then he finally grabs my head in both of his hands, it felt like being clamped in a vise, and he moves me by my head to where I'm laying on his left knee, his right leg now spread even further out of the way, so I have full access. I'm left straddling his hairy naked left leg, well actually his sneaker, it's between both my legs and spreading them out forcefully. I have no choice at all, he's manhandling me into the position he wants, and this is driving me wild, along with the helplessness of the cuffs and my overall situation. He's playing with me, acting like a brute, but I can tell at the time that it's just an act, although I don't know how.
"So, he then forces me to deep throat him, ramming my head up and down on him ferociously, and I moan like a little girl again as he basically rapes my mouth. He laughs, but not at me, more like that this was something HE was waiting for. He then picks his left foot up, the one between my legs, and he grinds it into my tucked guy stuff. Despite myself this feels very good, I mean like really, really good! I moan some more around the cock that's nearly choking me. He does this progressive rougher to me, kind of bouncing me off the floor on and off on his foot, and I wonder if he can feel what's there, as opposed to what's supposed to be there, because it's getting hard. He is wearing sneakers though, so I don't know for sure what he can feel with his foot.
"As I get him closer, or more accurately, as he gets himself closer while using my clutching mouth, he gets so rough with me down there that he's holding me clear off the floor with my legs dangling, my full weight supported by my guy parts. I then realize that I'm gonna pop off too, while giving my second ever blow job in the back of a moving van, handcuffed and half dressed as a high school cheerleader. This is sure to give away what I am, and possibly get me kicked out of their van with my panties full of sticky cum and no shirt even on my back. When he finally starts to go I nurse on him like my life depends on it, on the quality of this one very hot blow job, it's part of the fantasy for me, the peril part.
"It's all too much for me though, and as he holds me deep onto him, with my knees clear off the floor and his muscles locked and trembling… I pop off myself and crush his leg with both of mine. It's bittersweet though, as this is a painful feeling for me with my guy hardware still tucked back, all while grinding roughly on his foot; it therefore doesn't even feel like a real orgasm. I don't even know that it felt good, but I can obviously feel the warm spreading mess, creaming my panties for him in spectacular voluminous fashion. I smell it too, or at least I think I do, the pungent aroma of spilled fresh cum in the close confines of the closed-windows van. I've swallowed every drop I've been given so far like a hungry little slut, and that only left one other source for the smell I thought I noticed.
"'What have I done?' I remembered asking myself, my kinky passion for this instantly gone, and I was wondering what these two remaining guys are going to do with me now, nice guys or not. I'm not a girl, and these two guys at least have to know that now, and one of them might even have a good reason to be really pissed off at me for tricking him so, even though I just de-stressed him and gave about the best head that I could."
"What happened next?" I asked, I totally caught up in this, although I obviously know that it turned out okay in the end, because he was here to tell the tale, apparently not much worse for the wear. I was past excited, this malleable man dressed in drag before me, possibly the one, this surely a bit of Halloween magic if there ever was any.
"The pirate got dressed, but left the cuffs on me. I was exhausted and laying with my chest on the seat next to him just trying to catch my breath; getting my head wrapped around letting another man bring me to orgasm while simultaneously sucking him off and grinding on his foot. He could have done anything to me at that moment too, anything at all, but he seemed rather happy with himself, despite what he had to know about the 'gurl' that just had serviced him. I then heard him call forward to his buddy the clown in the driver's seat, asking to be dropped off now, and telling his friend that he just HAS to try out this 'hot little bitch' back here for himself."
"The two said a few more words to each other, telling me they were good friends, but I didn't know exactly how good. Well anyway, once the convict had been delivered to his house, (and thankfully nobody saw me this time), the driver called back to me, telling me he knew a secluded place where we could park and talk some. I suspected talking wasn't what was on his mind, although with my kind-of orgasm, I wasn't really into anything else any longer as my kink had been temporarily drained."
"He told me that he's been looking at my tight little ass all night in the rear view mirror, and seeing how it's his van, he thought he deserved a little something special for giving me a ride home in it. I told him I was exhausted, which was the truth, but I also knew that anything but another blow job would surely reveal what I was. In what seemed like minutes the clown parked his van near some railroad tracks on a trail, the area dead silent once he shut off the engine and locked the doors.
“He climbed in back with me, looking down on me and sweetly telling me that I looked especially good, all handcuffed and half naked on his floor. He also told me he was horned up enough for the both of us, sensing, I think, my reluctance.
“I confessed that his buddy the convict had made me orgasm, a part of me hoping that this would explain everything, and get me off the hook with servicing his needs too. It's hard to describe, I just felt so defeated, but the other part of me, possibly the larger part of me, wanted this clown to do what he wanted anyway…
"What's wrong with me?" my guy asked rhetorically, this the perfect opportunity to bear MY soul.
"Nothing at all, you might have noticed that I have been denying you anything sexual for the last two weeks or so. A man's sex needs to be managed, and I learned some time ago that if the right man is denied an outlet for his passions, he can become quite pliable. At the same time, this pliable man's sex drive builds, and makes him suggestive of almost anything to get the orgasm he biologically needs."
"I feel like a science experiment," my boyfriend confessed, not angrily though, he sounded even more defeated, as if this was the end of our relationship.
"No, not at all. I don't know how to say this in a humble way, so I'll just confess it myself; it seems only fair seeing as how you're telling me such intimate things yourself. I know you've seen the way some men look at us when you and I are out together, primarily big muscular brutes I mean. You even said it yourself once; do you remember what you said to me?" I asked.
"Yes. 'What is she doing with HIM?' Or, it was something like that, I overheard it once or twice, to be honest. You're a magnificent looking woman, and I could 'feel' those guys looking at you like a piece of raw meat, like they wanted you, and except for me physically standing there next to you they would have gladly taken you away in a heartbeat. You dress nicely, your body and smile screams, 'sex, here we come!' Your hair is even sexy. I'm the luckiest guy in the world to be going out with you, but I can't help to think that you would look more natural paired with one of those big muscular gym rat type guys." It was sounding to me as if he was offering to step aside, so I could have one of those instead.
"I've had a few like them to be honest, since we're having such a nice candid conversation. They're good for scratching a particular kind of itch I sometimes get. Sometimes I just need a serious brute to roughly manhandle me, to take what I may or may not be offering at that particular moment. A handsome movie star looking man is always nice too, but both kinds of men are in the end far more in love with themselves than they ever could be with another. Physical fun is just wonderful, most especially with a guy like either of those if he's aggressive, and truth be told I might need some of that in the future; our future. I've also discovered that not all big and muscular gym rat guys are big all over, so don't go getting all self conscious being around them," these last words of mine especially surreal to me, seeing as how my "man" was still mostly dressed in his cheerleader costume, and had just felated two guys.
"We have a future, despite this little adventure I had tonight?" His tone was telling me this wasn't the way he thought things might go, and still he had the courage to tell me the truth; to confess his "sins." He got points for that, a lot of points.
"We certainly have a future, if you still want it with what I've just told you myself? Not many guys could deal with a partner who had to go out once in a while to get something she needs on the side; discreetly though, that I would promise to you. I haven't done that since we've been dating… YET, but I have physical needs that's hard to provide for, unless you're a complete brute just looking for another conquest. I would certainly be discreet, for both of our self interests, but I couldn't guarantee that some of your friends or coworkers might not find out at some point."
"Up until tonight I would have said no way, but I have to tell you that there's something about this whole thing that turns me on now."
"Good, but now I want to hear the rest of your story," I commanded, my guy needing this level of control, this exercise of raw power over him, I could feel it now!
"Okay. The clown, without even asking, reached down and unzipped my pleated skirt. I lifted my legs one at a time cooperatively so he could strip me further without complaint. He threw it forward onto his front passenger seat along with my sweater, my wet panty covered ass left facing him, my torso laid out on the rear seat, still handcuffed behind my back. In a word, I was helpless.
'"I've been listening to you all night,' the clown told me. 'You're a natural cock tease, whether you realize it or not. But, you like being made to do things too, you possibly even NEED to be made to do things. So, I'm going to make this easy on you, because I think you're a fun 'gurl,' and of course you come highly recommended.'
"The clown purposely mispronouncing 'girl' told me I might not be quite so much of a surprise for him as I originally thought, my Halloween costume was apparently not that good! I told him I didn't understand what he was asking, not even sure he was asking something.
"'I'll make this simple then,' the clown advised, not out of malice, but kindness.
"'What terrible kinky thing would I have to threaten to do, so as to motivate you toward doing that which we both know you're just dying to try?"'
"I realized that this was the best gift ever, and I had two obvious things on my mind that would give me no choice but to satisfy both our curiosities. 'Strip me naked and dump me on a street someplace in just my heels and the cuffs,' I offered. ‘or, paddle my naked ass with a belt.'”
I myself already knew about the getting dumped off someplace thing to be honest, it's why I came up with this Halloween party adventure in the first place as I knew it tripped his trigger, but the belt, the concept of using a strap on him, that had serious possibilities. I can't say I started this night expecting to learn that my guy might need some corporal punishment to keep him on track, but I was game to give it a whirl at least once. Such would further empower me and deflate him, but to be fair he was fairly easily controlled anyway, so the belt or a strap might not get used all that often between us.
"So anyway, the clown steps out of his clown costume and he's nude underneath it, and boy howdy does he have a body. Six pack abs, arms and legs like a greek statue, skin shaved bare; but not exactly one hundred percent ready to perform either. I feel like I've let him down, that I'm not doing it for him, and as a result I feel unworthy. He's a handsome young man, fit and strong, and I've even just given him the keys to my kingdom, the keys to motivate me.
"He runs his hands from my ankles to my shoulders, spending some extra time on my ass, and I expect to maybe get paddled anyway, just to spur me on. I don't even know if he has a belt, but he has hands, and as he rubs my ass with his open one I catch myself thrusting back into it. He then kneels with one leg on the seat I'm laying on, and when I turn to face his hanging man parts he playfully smacks me in each cheek with his half hard cock. I try to catch it in my mouth, but he's teasing me with it, not letting me have it. An hour earlier I would have been horrified by something like this, and now I find myself disappointed that I can't catch his cock with my lips. It's already been one hell of a night for me, and it's obviously not over yet.
“I eventually caught the clown's cock and nursed it like my life depended on it. It's part illusion, part real, because I'm still cuffed and nearly nude myself, and it would be an easy thing to dump me almost anywhere. I eventually manage to fluff him up pretty well, but he has other ideas for what's next. My panties are in the way though, so he slips them down as I again cooperatively lift my legs, he I think surprised to see the massive mess I've made in them, and that there are two layered, one over the other. The inner ones he stuffs into my mouth, gagging me with my own cum soaked panties, the taste both lingering on my tongue, and making me mute. I could still spit them out, but his placing them there tells me he doesn't want any more conversation, and his thick fingers in my mouth felt almost as intrusive as his cock…"
I've tried to be good here, but I've also just shucked my jeans and I'm rubbing directly atop my borrowed tighty-whities, grinding on my girl parts ferociously. Not that I'm super into porn, most of it is painfully fake and lifeless, and the "actors" almost exclusively seem stoned, or high on something while "performing," but this instead is like my own personal porno. It's like I'm there and watching, not only a very new "first" for this man of mine, but I'm also seeing my unique plans come to fruition.
My phone then pings; "Thanx for lending us your hot little cheerleader, can we take her camping next weekend?"
"Yes, I think so, have a new friend in town, and that might actually work out perfectly for me," I text back.
"Did she behave?" I ask, as an afterthought, opening the door to a whole bunch of possibilities. I was reading this guy of mine like a book, and it seemed most unfair of me to be out on a date and potentially hooking up, without my guy having the same opportunity with his own new friends.
"She was the hit of the party," my friend answered, although not exactly answering my original question.
"Get over here, on your knees," I command, I don't really need to hear what comes next anyway; I have a perfectly perverted imagination in such situations. Borrowed and now soggy underpants in a heap on top of my jeans, and his face where it properly belongs I put him/her to work. She's extraordinarily good with her mouth, but I had no idea that skill would easily translate to being submissively good with other men as well; maybe a little Halloween holiday magic, maybe a little fate instead. Humble service is humble service though, and I can only imagine how good she'll get with a bit of practice. She's been oral with her girlfriends since she was a teen, so a little catch up might be in order. This however is MY reward, for being a good girl and not going up to superman's room with him like I wanted to, like he wanted me to as well. We did exchange numbers though, and he was a very desirable man too, cape or no cape…
I'm being just a little rough with my cheerleader, but the guys were as well, and she seems to respond best to this anyway. Wow is this good, I think to myself, but I'm also ashamed to say that I'm half thinking about Superman, nothing like a brand new - but still familiar - superhero to rock a naughty girl's world. I love Halloween magic…
