Vintage photographs of dominant leather masters and the male slaves they put in bondage.
Originally posted 2014-01-11 05:05:55.
Vintage photographs of dominant leather masters and the male slaves they put in bondage.
Originally posted 2014-01-11 05:05:55.
Learning to appreciate gay guys who wear dresses*
As I type this I see someone is searching Google for “self sucking gay crossdressers.” Some sex fantasies can still surprise.
One nifty aspect of writing about yourself is the quickening of memory.Reviving memories almost forgotten.
In 1972 I’d left home and Ebba and Gordon were my roommates. Victor had left John for Nancy and John moved to Atlanta. With fatal foolishness I fell in love with him and moved into our own apartment;; slummy complex on Peachtree across from Piedmont park. The man below us was a Sterno addict and would keep us awake but in stitches mooing like a despairing cow.
Glenn, our building superintendent was an ignorant middle-aged man. He was trying or at least hoping to transition from genetic male to medically created woman.
Christine Jorgensen, the inspiration for Ed Wood’s Glen or Glenda, had undergone her gender transformation twenty years earlier. Her fame survived after a fashion so I’d heard of sex change operations. I think Glenn may have been taking hormones. He was often bed-ridden and so raffish I can’t remember if he went en femme. I didn’t think much about it except for a small doubt: was he sincere or just wanting attention.
Back when I’d been living with Gordon and Ebba I made my second abortive attempt to have sex (having someone’s roommate throw ice water on you through the bedroom door can’t help but spoil the mood). Thinking back the young little ice queen I’d climbed into bed with had on some kind of silken women’s undergarment. It would’ve been mentally if not tactilely invisible to me back then. I hated wearing underwear. Pleasure in wearing a woman’s undergarment wasn’t something I’d hear of for many years..
Bobbie, the ice queen’s roommate excited me strongly. A gentle, sweet guy very much in love with his hustler boyfriend. Bobbie was a naïve Southern boy with the special kind of face that can make a pimple into a beauty mark. Maybe if I’d understood the fragility and inevitable failure of such an entanglement I’d have made a pass at him, I dearly wanted to. Boys like Bobbie were always fiercely faithful (their boyfriends never were). Much later I saw Bobbie on the street dressed as a woman. First time I – knowingly at least – saw a passable transvestite. With wig and make-up he wasn’t a bit less appealing and lovable. My first site of a pretty drag queen, I’d have loved to have the boy under me even in a dress but only in recollection would I see that. Didn’t matter he’d donned drag to go hooking.
androgynous/masculine seeks androgynous/feminine
From my first personal ad appearing outside of The Atlanta Barb the gay newspaper that I helped run. Marc (aka Rose C’est La Vie) was the only person to answer. Marc sometimes wore dresses without makeup or in anyway trying to assume the persona of a woman. He looked fetching in a dress sans makeup, wig, or jewelry. A minor sort of queer political statement: genderfuck. Never gave his appeal in a dress a second thought. I called him and we laughed when told him that the ad was mine. Years later when I was living with Siobhanand visiting Atlanta, Marc and I got to know each other little bit better just before I left Atlanta after a visit. The laughter years earlier might’ve been a mistake.
If the word androgynous hadn’t appeared in the ad I don’t know if I’d remember it. Years later it would surprise me to discover I’d employed it in the first half of the 70s. A preference for a limp wrist aside it was probably that David Bowie’s early days had popularized it. The wild eyed boy from Freecloud then seemed the summa of androgynous male beauty.
Callow hermaphrodite fantasies
While I’d placed a couple of personals, I’d never responded to one until I was living in San Francisco. Off and on again I’d had fantasies of making love to a hermaphrodite. (I hope any pre-operative MTF transsexuals (or intersexuals persons) who see this will forgive me. Your struggles and pains, the misery with one’s biological lot, were unknown to me.) My fantasy image was inspired by the classical myth of Hermaphroditus the child of Hermes and Aphrodite. Honestly, yes it was a chick with a dick, a shemale – did that nomenclature exist back then? My dream boygirls were fuzzy conceptions, no suspicion that they actually existed.
What the ad said I don’t remember. “Pre-op transsexual” wouldn’t have meant much to me back then. Maybe she spelled it out: I have tits and a cock. The voice on the other end was creepy, bitter. She required a ‘donation.’ Back then there wasn’t much public help for men wanting to have the bodies of women. That the monetary burden has driven some mtf transsexuals into prostitution I didn’t know.
Back when I was selling callboys I’d intended to eventually pay for sex: half as a lark, half for a quirky sort of self-edification. Many youthful ambitions are never realized; I never did buy a boy even though by twenty-one I knew many male hustlers. Perhaps if the voice had been kinder or vulnerable, vulnerability has always had the power seduce me, I’d have happily made a donation. I can’t fault her. She probably heard from many self-proclaimed real men whose most tender line was that they’d show her what it was like to be a real woman. After the phone call I dropped the idea.
Here’s the kicker: I never connected my admiration for Bobbie or Rose, my call to the pre-op transsexual with my sexuality. I thought of myself as a gay man who only wanted other gay guys. Even when I lived with a woman for five years my sense of myself as gay never wavered. In my coming out story I noted my inner blindness. My eyes liked what they’d seen, my heart stayed shut.
Many years pass.
Have you ever been to alt.com? It is the match.com of BDSM personal ads, although the graveyard of online personals may be more apt. Personal ads are often a tentative gesture toward assuaging an unmet need or suppressed desire. The more atypical the itch the greater the likelihood of a retreat back to self-denial.
Browsing the listings of North Carolina submissives I ran across a photo of a crossdresser: nude except for hosiery, bent over showing his/her butt (I love buttocks, male or female). My body responded much to my surprise. Fashion photos of pretty boys in sweaters, Renaissance paintings of pageboys were my usual idea of erotica.
I like nudity as well as the next human being. OK, maybe not. Naked pictures are fine but I rarely see any that make me smile with delight. Vapid faces bereft of individuality. Without a hint of irony, prankishness, kindness I can’t perform my viewer’s role of investing the photo with sexual glamour. When I made myself healthy and my sexuality reemerged I tried to take advantage of the Internet’s vast erotica archives. (Aggravated my carpal tunnel to no purpose.) Playgirl centerfolds on their motorboats and motorbikes weren’t for me.
Also on alt.com, I saw a facial shot of a very gentle looking longhaired guy. His listing said he was transgendered male in the process of becoming a female. His words matched the vulnerability of his picture.
I made a small evolution. The gradations between male and female became alive, as full of erotic joy as the favored two. I found that the people in between and outside were just as lovely, just as lovable.
As a young gay man to me guys in dresses meant drag queens in bars. Back then, lip synching pop songs they looked like tacky mannequins that had melted under the sun. Their strenuous, aggressive personalities are probably necessary in their world (and dealing with the rest of the world). A little bitchiness is appealing but I don’t like being near loud, pushy people.
That was the early 70s. I hope their lot has since improved but back then even in the bars they perform in they were regarded by many as little more than grotesque oddities. Many of them lived in poverty with hustler boyfriends who were more likely to rip them off than kiss them. Some had regular jobs where they carefully concealed their weekends (like most gay men).
A new color of sex discovered I went exploring. It being the 90s I went online.
Inevitably I discovered the vastness of my ignorance. Most transvestites are straight, many married. Lucky ones even have wives who understand and support them. I ran into them on Usenet when first trying to learn about crossdressers. Finding out that I am gay, they were as intolerant as any other group and told me to find a drag queen in a bar.
I quickly narrowed my conversations to gay crossdressers. Do you think you have a hard life, that people don’t understand you, that you’re an outsider? Try life as a guy whose deepest satisfaction is wearing women’s clothing. The average gay man – who damn well should know better – can’t be expected to regard you any more kindly than the straight punk.
Invisible at the most horrific extreme are the guys who’ve never let themselves put on as much as a garter belt. Many of them want a man to force them to shave their pubic hair or mildly feminize them in other was (I remember the young jocks who wanted me to ‘make’ them shave their pubic hair). Others dress up at home their mirror their only companion. Thanks to the web transvestites can meet other transvestites. A few post photos of themselves anonymously, appearing en femme publicly with little risk.
In the Yahoo clubs and gay.com chat rooms crossdressers try to hookup with guys. Flirting that rarely leads to a meeting; true of most online flirting, least likely for them. Some are afraid of being beaten. Most are afraid they’ll be found unattractive and laughed at. The saddest minority covets the attentions of self-proclaimed heterosexual men, swine that can’t admit to themselves that a guy in a dress fulfills an appetite that a genetic female cannot. (At the risk of sounding defensive: that isn’t why I find crossdressers appealing. At the simplest level they are just part of a spectrum. If they are happy to accept themselves as a gay male even if playfully aping the rules then I can happily place them on a romantic pedestal. Sadly, they are rare.)
The bulk of the men trying to date transvestites mostly boast that they are real men and talking about the magnificence of their penis. Ashamed of their sexuality, unable to admit they are attracted to men. Interestingly they seem most fascinated with the transvestite’s phallus. Meeting one of them is apt to be as romantic as a prison gang rape.
And there is the terrible division between those who can pass as a woman and those who can’t. The latter often despise themselves for their imagined failure. Akin to people who feel themselves ugly but perhaps with more self-hate.
When I was on Yahoo daily I got messages from guys who wanted to meet me (99.6% of which to which I said no). The first transvestite who asked to meet me was a (I thought too young) guy of 25 who I was able to discern lived near me. He was skittish boy, who I felt needed to be able to talk with someone more than sex. Thinking a public place would give him security I suggested we meet at a nearby mall. He was so scared I suspected he’d never shown up. I emailed him the day before we were to meet. He never replied so I didn’t bother going. A public meeting may have been more intimidating than a less safe one in private.
A really smart transvestite emailed me for a date. His confession that he wasn’t passable didn’t’ deter me. I asked my (straight) friends to which restaurants I could take a transvestite without fear of harassment. Wellspring Grocery was my usual place for meeting possible dates from online. Over coffee I discovered he wanted to go to Legends a Raleigh drag bar. Bars bore the fuck out of me; I haven’t been to a bar since I left San Francisco. I assented but he could tell that I didn’t warm to the idea. We never met again. He’d thrown me in an odd way: he said the “man proposes and the girl disposes.” Femininity isn’t passivity, in an erotic context you can tell me where I’ll be and I’ll be there. A weakness for (even the sweetest) Bitch Goddess. Reflecting I’d say my reaction was ignorant. Role play is part of the experience.
A tall, super-slender crossdressing young cop I came very close to meeting. A gruesome series of crimes intervened. Bright and self-aware my interest was very strong. (Even if I have a phobia of police.)
The one I wish hadn’t gotten away: young, soft, tender, he wanted me to pet him and hold him in my arms for a long time before the ‘horizontal boogie’ as he called it. Pretty without any cosmetics, having his own long hair we made an assignment. Crime (not any that he had to investigate) again intervened.
Charles, who wears men’s clothing only (except for the heels he sometimes puts on) arrived and I told both never mind. Both were pissed.(As were a couple of guys who didn’t crossdress. In choosing Charles I implicitly slapped them in the face with rejection.)
Intentionally neglected are the locals wanted ‘motel room fun.’ Many of those were married. I’m a fairly amoral person but have never been up for adultery.
Why all the fuss about crossdressers
Folks who’ve seen my many entries on crossdressers may be surprised that I’ve never had much in the way of crossdresser fantasies. Crossdressers became a romantic possibility, not an obsession. I’ve always loved girlish gay guys. I’d latterly accepted that they might wear skirts and stockings.
Crossdressers are special to me in a couple of ways. Many of guys I’ve loved were picked on at school or had “Freak!” or “Faggot!” shouted at them from cars. My erotic tenderness has been dangerously reinforced with a hope to protect and uplift them. Crossdressers are outsiders even among gay males; they live more deeply with the outsiderness that still lingeringly colors queer life. Transgressive is a word that I’m tired of it but crossdressing is more transgressive than merely being gay. (When I was online more I’d get slammed for caring about them. Why would I be interested in an embarrassing freak when real men were to be had? I grew up with a violently ‘real’ man Even if you, like Big Mack, can bend bolts in your hand and pick up the back of a 1960’s care, you aren’t going to warm my heart. And there were the inevitable hasty readers who thought I was a crossdresser.)
Differently but maybe more importantly: my evolution either occasioned or coincided with much self-discovery. A new source of self-insight is more exciting than, say, a new fuck. My weblog is about nothing if not my own self-absorbed self-exploration.
Not that discovery of new erotic possibilities didn’t enrich my daydreams.** But come the dawn, come reality.
For me crossdressers inspired notions of playing with, teasing, toying with, ultimately transcending gender. The woman that I lived with never shaved her legs, wore a dress of carried a purse. Many male crossdressers want to be a woman in an icky way.
That crossdressers wanted to emulate bourgeois values shouldn’t have surprised me. Clothing aside they are just like the other happy Wal-Mart shoppers and Big Mac eaters.
Many of them wanted to be female in a dated housewifely way. I never wanted to live with Donna Reed or June Cleaver. Role-play can be fun but not taking it in dead earnest. Aesthetically the bad wigs and impossible clothing put me off. Bourgeois garments alienate me regardless of the frame beneath.
A big slice of them wanted to be dominated, overpowered, humiliated. BDSM is OK but the consistency was appalling. Few genetic women want to be told to “Get down on your knees, bitch!” or slapped in the face. I’d flattered myself with feminist insight but the gender stereotyping implied by this was a real revelation. I wrote a story to help me explore the idea of satisfying a submissive crossdresser.) In an odd way they mirror the surprising male sexism to be found in heterosexual male submissives. (That I was looking at listings of submissives on alt.com but cavil at some of their motivation isn’t as contradictory as it might seem. Pleasure in submission and pain is fine, self-hate isn’t.)
Simply put I like crossdressers who even if wish they could spend every hour en femme don’t hate being a male. Maybe they would’ve been born a girl if they’d had the choice. But they can accept being of both worlds.
The person above possesses clarity, elegance, individuality, competence and compassion . Because of his joy in wearing clothing not designed for males he’s mocked, he might even be beaten. Because of his rare quality, his nobility, if you will, even though crossdressers have never been an important part of my personal life I’ll always try to remember their status. I’ve always sent transvestites to his web site.
Dressing sexily & drably.
** I’ve segregated this part fearing that it will hurt or anger some crossdressers. This is a sifting of my tastes, not a manifesto on crossdresser fashion.
Pouting, yet sure of himself, the womanly curve of his back. Girlish and boyish in equal measure his image was part of my growth towards an appreciation of transvestites. (And if the copyright holder would email me I’ll remove the image or provide a link to your website which appeared to be dead.)
I’m susceptible to plenty of erotic clichés. (I’ve often wondered where they come from, having nothing from my youth to relate them to: probably fetish by osmosis.) Typical tawdry fantasy: a boy dressed like a girl hooker in hot pants. Less tritely: a guy who could use makeup to look like a girl in t-shirt (or halter top) and jeans: just a casual boygirl relaxing. The last is the imaginary crossdresser I can most easily imagine being with.
That I found this picture strongly appealing startled me. Momentarily I felt like a pervert. Really it is a very lovable image.
I’ve seen pleasing images of crossdressers in long stockings, short skits, Dresses? Sure. But a dress that looks comfortable, something you can relax in. Fancy dresses can be appealing but they are hard to pull of even if you were born with tits. Office worker’s drag, heavily constructed gowns – well I wouldn’t warm to those on a woman, nor you. Humor, strong stylizations are erotic; not emulating the commonplace.
Wigs are a problem. Good wigs are expensive. Some guys are lucky enough to be able to wear their hair long. Contemporary women do fine with short hair, it is a matter of styling. Old-fashioned whores and 60’s country music stars aren’t the best models.
Appropriate dress is a rare knack anyway. Probably if I were to go and look I’d find today’s crossdressers looking more like Pink than Martha Stewart.
* The safest phrase to use – finical quibbling over crossdresser vs. transvestite vs. drag queen merely wearies me. Drag queen is probably best left to the guy show perform in bars, the other two words seem merely matters of preference. I prefer crossdresser, transvestite – like homosexual – sounds like something in need of a cure.
NB: this is strictly about gay male crossdressers. Hetero crossdressers and MTF transsexuals are ignored for the sake of focus.
To quote the title of one of my Live Journal entries: Small town diva boy your mascara is smeared and I love you.
Richard Evans Lee, May 2003
Originally posted 2013-12-26 23:40:38.
Chain Male #1 – Three of Four
Vintage Leather BDSM photography.
Originally posted 2013-12-26 04:00:13.
As I envision my first meeting with you Sir, I am immediately told to strip and to change into my “slave uniform”. You tell me that this uniform will be worn by me at all times while in you presence.
I remove my street clothes, and my briefs and socks, and pick up the ankle and wrists straps, as well as the black leather collar and leash. You are watching intently as I apply these items. My cock is swelling as I continue to prepare myself appropriately for you Sir.
Finally I complete my task. As you gaze upon my nakedness, I am asked to turn around, to bend over and to spread my cheeks for your inspection. My arousal is constantly building as I imagine a new world of submission to you Sir. I am told that my body is adequate at best, and that I should follow you to the bathroom as there is much hair that needs to be removed. I am chastised by you Sir for allowing my body hair to cover my asshole and genitalia as it is. This you tell me is not acceptable, and that it must be removed immediately, afterward my punishment will follow.
I am soaped up and you assist me in removing my hair from my back and asshole area, as I remove it from my chest and cock and balls. Again, you inform me of additional punishments will follow for making you work by removing my body hair.
Once clean shaven, I am led to the punishment room, or actually the bedroom converted for our D/s punishment scenes. I am draped across the horse, my arms are pulled out in front of me and my wrists are tied with my straps. My legs are bent at the knees, and the straps on the side of the horse bind my knees in a bent up position. Finally, my legs are spread wide and a spreader bar attaches my ankles to my straps down there. In this position, I am secured face down, with my newly hairless body to accept the punishments that I have earned. First, you stand in front of me, and I watch as you slowly remove your pants and offer your engorged cock to my lips. You order me to take you, into my mouth, and pleasure your cock with the respect and adoration that you are due. You warn me that if I fail to bring you the utmost pleasure, I will most certainly be severely punished!
I open my mouth for you Sir. I smell your cock as you bring it to my lips. I feel the heat of your sex pressing against my mouth. Slowly you feed me your penis and I try hard to accept it without gagging. I close my lips around you and my tongue swirls against the head of your cock. You sense this and stop pushing it in. You just wait for a few seconds as I get used to your cock in my mouth. I am sucking and swirling my tongue around you now. Slowly you pull back and again force your penis into my wet lips. I am sucking you and slurping at your cock as you slowly begin to fuck my face with it. You are surprised at my eagerness and abilities as I am making you moan in pleasure now. Soon I will bring you over the edge and taste you for the first time! Your orgasm is building and try as you might to stop it, I continue to suck your cock, and work on your climax. Your moaning tells me you are ready and you unload a large blast of cum into my mouth! I am suddenly unable to contain all of it as it gushes out of my mouth. I wasn”t ready to swallow when you ejaculated so I lost some of it out of my mouth. You continue to pump into my mouth forcing more and more of your cum into me!
You withdraw your cock after I have licked it clean. You tell me that you are more than disappointed with me, for having wasted your cum that dripped out of my lips! For this and my other errors, I will now suffer the consequences with a very sound spanking and paddling.
You tell me that you will spank me first with your bare hands, to warm up my butt for my real punishment! Then you show me the paddle that will be kissing my tender butt cheeks hard for my punishment. I see a rubber coated paddle, that looks much like a Ping-Pong paddle. Sir, you then inform me that I must be punished for three things that I failed in. The first one being, that I dared to allow hair to cover my cock, balls, and asshole. Second, for having to have you shave the hair from my asshole. And third, for spilling your cum when I didn”t swallow all of your ejaculate! And this last punishment paddling will be the hardest of the three. You tell me that you intend to paddle me hard for this error especially!
I slowly anticipate your first swat with your bare hands. Your spanking is hard on my naked flesh. Over and over you continue to spank my butt! I wonder how you can keep up the pace! My butt feels hot as you give me my warm-up spanking. Finally after about five minutes of swatting away at my butt you tell me that it is warmed up enough for you to proceed with my paddling! I am breathing heavy from this, and I can feel my ass must be hot! Now you come around to my face and tell me that you have a little surprise for me! You show me two things; one is a red rubber ball gag, with a harness attached. The other is a medium sized butt plug. You tell me that I must be punished for my failures, and that you intend to punish my butt very good, and you don”t want to hear me begging for you to stop! So you fit the harness over my head and then the ball gag. My mouth is stretched open wide as you stuff the ball in, and allow me to bite down on it. Once secured, you show me the butt plug again. You ask me if I want you to use any lube before inserting it into my tight asshole” I see the smirk on your face and I nod my head frantically “Yes”. You chuckle slightly as you find my actions humorous.
You bend down and grab my cock, which is oozing pre-cum, and wipe as much of it you can around the head of the plug. You tell me that the plug will be worn most of the time when I am in your presence too! Slowly you force the plug into my tight asshole. You stop when it is in at the widest point!
“How does that feel slave”” you ask me.
I moan, as the feeling is painful! I feel like the plug is going to rip me open! You remove the plug and coat it some more with my precum, which you are milking out of my cock! Then you slowly push the plug into me again, stopping when the widest part is at my sphincter! You repeat this over and over, working my clean-shaven asshole. Then with a hard push you jam the plug into my ass, and it is sucked in to the base! My anal muscles pulling it in tight! I feel you pulling it out and rotating the plug, reversing the torment on my anus as you did before. Stopping just when the widest part is stretching me open! Then you hold it there letting me feel the stretching pain! Over and over you punish my asshole, as I moan in my gag!
Then you just let go of the plug as my rectum pulls it in past the taper. You push it into me, making sure it is embedded deep into my hole. You tell me that this little bit of anal torment was punishment for having pubic hair on my genitals! Now it is time to accept my punishment for my other transgressions. You tell me that my paddling will go on and on, and that you will only stop when my butt is the right shade of RED!
With that you begin the paddling that I will come to love. It is a hard and severe punishment, but as your slave, I must learn to not fail the tasks that you give me. Yes, part of this punishment is for something that I did not know. But you tell me that I will be punished for these things as well, regardless of whether or not I knew all the rules. But you also warn me that when I break the rules that I have been given, then the punishments that follow will be severe, as I am showing you disrespect and deception, both of which are unbecoming of your slave!
I made it through my first punishment session, and although my butt went from burning to almost being numb, I feel closer and more attached to you Sir then before. Thank You for punishing me. You gently rub my backside, and it feels like it is aflame, like the skin has been removed! You remove the ball gag, and you noticed the tears that have run down my face. With the gag removed I quietly make out a Thank You again Sir. You smile and tell me to thank you properly, and you once again offer me your cock. I open my mouth and again suck and pleasure you again Sir. This time I try not to loose any of your cum. It takes me much longer to bring you off this time, and I am almost glad when you do cum! I swallow right away when you first start to spurt and I catch all of your cum. You allow me to suck the last drops from your cock and then you withdraw from my mouth!
Now you untie me from the horse, and rub my arms and legs to help get the circulation back in them. You tell me that I must now do the chores of cleaning the house. But first, you noticed how much pre-cum has leaked out of my penis, and first you have me clean this, with my mouth of course! I lick up my own pre-cum, and obey your commands.
You then tell me that I am forbidden to touch my cock and that I may not be allowed to masturbate. I will only be allowed to cum when you decide to reward me with an orgasm. My orgasms will only be given as a reward for excellence, and for rewarding me for above normal performances! I will be required to wear a type of cock cage during the day, and it will be fitted so I will not receive any stimulation from brushing against anything either! At night when I am to sleep, I will be laid face-up on the bed, and my arms and legs will be secured to the bed. This will prevent me from having any orgasms by masturbation or by “humping” the bed! If I get to the point when my stimulation”s and actions are so overwhelming and my desire to cum so strong that I actually orgasm without touching myself, I can expect to be severely punished. My punishment will be two to three times as severe as what I just received!
I watch as you apply my cock cage. Now you have me tend to the domestic duties of your house. You carry the paddle with you, and warn me that if I should miss anything while cleaning, I will be bent over the nearest chair, table, couch, or your knee and given twenty swats for each area or item that is missed. You also tell me that I should ask you to inspect each area I clean first before going on to the next. This way, if I have missed something I will only receive twenty or forty swats instead of a lot more on my already flaming butt!
Throughout the afternoon, I continued to clean your house, and suck your cock! I was slow to pick-up on the hints you were giving me as to how meticulous you wanted your house cleaned. As a result I received about a hundred more swats with the paddle! My backside is so sore and HOT I will probably not be able to sit down for a week. But still, I appreciate you training me Sir. I Thank You over and over for punishing me, because I know you are making me a better slave!
I was to the point of cleaning your bathroom when I realized that I had a need and an urge to pee. I was about to relieve myself when you saw me grabbing my cock to aim it into the bowl. You grabbed my arm and sternly reminded me that I was NEVER to touch myself unless you directed me to! And you certainly did not here! You told me that I could only use the muscles in my cock to aim into the bowl, and that now I would be punished for touching myself! You also warned me that if I missed the bowl with my pee, my punishment would be doubled and I would have to clean the mess up as well !
I tried to concentrate to relieve myself, and finally, I was able to pee. I leaned way over the bowl and pointed my cock down but when the pee started to come out my cock started to rise up! I frantically readjusted myself and was able to keep it flowing into the bowl. I sighed with relief as I finished, but then I wondered I would I get the last few drops out if I couldn”t shake” I wiggled my hips to shake my penis, but that caused a drop to hit the edge of the bowl. I don”t know if you saw that or not Sir. I was very alarmed, because the last thing that I wanted or needed right now was a double punishment! I would certainly be receiving another hard spanking for grabbing my cock, but you said a double if any missed!
Once again, I was lead into the punishment room, and fastened securely to the horse! You came around to face me and told me that for touching myself and breaking the rules required a severe punishment! And since my butt was already raw from all the spanking you told me that you would punish my asshole now! Or I would be given the option of getting the paddle followed by the crop for a blistering ass beating! Which would I accept” Punish my asshole Sir, I asked. I wasn”t sure that I wanted either, but I now I was wrong and needed correcting!
You brought three dildos of varying sizes over and laid them out in front of me. Next you pulled on the butt plug that was buried in my hole all day! Ooooh what a feeling that was deep inside when you moved it! You pulled hard and it was out! You laid it next to the others and told me that my punishment would be an ass reaming with each dildo. Once the biggest one was in, I would wear it the rest of the day! Each dildo would be worked into my asshole for a good 20-30 minutes! I noticed that the butt plug I was wearing was about the size of the first dildo that was laid here. The biggest dildo was huge, at least twice the size and length of the butt plug! Then you grabbed the butt plug and brought it to my lips. You told me that I was to clean this plug and at the same time it would be used to silence my cries as I accepted my punishment.
You then pushed the musky smelling butt plug into my mouth and I reluctantly closed my lips around it. Then using an “ACE” medical bandage, you made a couple of wraps around my head to keep it in. You went behind me and I could feel the cold lube being smeared around and into my hole. Slowly you started the first dildo into me. You pushed it deep until it was completely buried inside of me! Then you started to pull it back out. My body was loose enough in my bindings that I was pushing back when you were pulling it out. You suddenly stopped and jammed the plug back into me and slapped my ass cheeks hard!
“Don”t move your body slave! This is your punishment. I want you to feel me punishing your asshole. I want you to feel every inch of these dildos as they force your hole open for me!” “You will also get the double punishment, as I saw that drop of pee hit the edge of the toilet bowl!” After I have finished thoroughly raping your virgin asshole, I am going to give your butt the paddling and cropping too! You will endure all of the one hundred swats of the paddle, and the fifty swats of the crop as your punishment, and with the largest dildo still stretching your asshole open wide!
A deep guttural moan escaped my stuffed mouth! How would I ever endure all of this, I wondered” But I reminded myself that you are my Master Sir. You know what is best for me. I tried to hold my body still for you as you worked the dildo in my ass. You very slowly started to pull it out and the feelings were teasing me causing me to push my body back to you! Each time you repeated the same thing, jamming the dildo in all the way, and spanking me hard. Then I would try to stay still as you dragged the dildo out agonizingly slow!
I eventually gave into the feelings of having my asshole stretched and raped by you. I made it to the largest dildo now! My asshole was stretched wider than it has ever been. You did not let up at all with my punishment. Over and over you forced it into to me, then slowly you pulled it all the way out and started over! I lost track of time and actually might have blacked out, but it was just a blur of my senses! After a couple of hours of relentless raping of my asshole, you pushed the monster dildo into the hilt and left it there!
You came around to face me again, and asked me if I was ready to accept my punishment now! I looked into your eyes with a pleading look while I shook my head up and down. You told me that since I was just given the house rules only hours before I broke one, that I must receive a severe punishment! The one hundred hard paddling followed by fifty swats with the crop would be the severe punishment. My backside was still glowing from all of the abuse already. I was as ready as I would ever be I guess!
You grabbed the paddle and started with a very hard whack! That swat really got my attention! Over and over you landed the very hardest swats with the paddle! I could also feel you hitting the dildo forcing it into my rectum even deeper! I was crying hard from the searing pain and burn you were laying on my backside. I couldn”t possibly keep track of the number I was getting, and I couldn”t see how you were either! I was totally at your mercy! Over and over the swats rained down on my butt! Then finally, you were standing in front of me again. I didn”t even know you hard stopped! The burning was so intense in my backside now!
You held the crop to my nose as you told me how the leather would soon heat up as it kissed my flesh with a severity I never knew! Then as I waited for the sting, I literally saw colors as the first swat of the crop hit me back there! You were slow with the crop. Forcing me to feel each and every one of the fifty or better swats! My ass was so HOT and numb I couldn”t stand it much more! After crying my eyes out, and moaning uncontrollably, my punishment was finally through! You removed the ace bandage and then the butt plug from my mouth. I was breathing very heavy, and gasping when you removed the plug, but still I managed to say “Thank You Sir”. “Thank You for punishing me!”
You left the huge dildo still buried inside me, and again offered me your cock to pleasure once more. I was totally drained of energy as you force-fed me your penis. You grabbed a hold of my head as you pumped my face with your cock! I tried to suck but was not doing much more as I was still recovering from the punishment. Soon, you unloaded again into my receptive mouth. I swallowed and continued to suck the last drops out of you. When you pulled out you told me that this blowjob was not very satisfying. You asked me what the house rules said about unsatisfactory behavior and performances”
“They get severe punishments Sir”,” I answered.
“Yes slave. And since you are not able to take another severe punishment, you will owe me one session then.”
“Thank You Sir”
“Tomorrow, I will demand your butt for another severe punishment!” You must learn to pleasure me better slave. Now get some rest, for tomorrow will come quickly, and your severe punishment will be delivered!”
Originally posted 2013-12-24 22:29:23.