A two part with versions written by both Mistress Ruby and Submissive Shawn

**This is a TRUE story

Part 1 - By Mistress Ruby

After a lifetime of living in the closet, Shawn has decided to discover her submissive side. Actually, Shawn is a man, but inside and at heart he is a woman. In fact, he is a submissive girl yearning to be taken like the slut he is. This is the story of how Mistress Ruby took Shawn’s virginity. It is a true story that happened near the end of April, 1999 (with a little poetic license and with the details changed to protect the paranoid).

Shawn showed up at Mistress Ruby’s house looking all the world like a solid businessman. A good looking man with a touch of distinguishing gray hair, fine features, and little yuppie glasses that made him look like the perfect baby boomer. He has a firm body and nice tight buns. Underneath all this respectability however, he wore a pink lace teddy, white garter belt, and silk stockings. He had a hard-on already.

Shawn was very nervous because this was his first foray into dominance and submission. He had dreamed about it for years, but couldn’t find a way to express himself freely. He wanted someone who would allow and encourage him to dress as the woman he was inside. He found this someone is Mistress Ruby, an experienced dominant who had also been submissive for a number of years. She had given him a number of directives prior to their meeting including that he not masturbate for 24 hours prior, and come dressed with femme clothing underneath the business wear. She had also directed him to bring a paddle which he had failed to do. He knew he’d be punished for this, and deep down he wanted it. Not because he was into pain, because he wasn’t, but because he wanted to know that she really would punish him. He knew he deserved it.

Mistress Ruby welcomed him in. She was wearing a see-through purple lace top, purple bra, short black a-line skirt, black garter belt, black stockings and high-laced dominatrice boots. He could see most of her breasts easily, the cleavage deep and the nipples almost in view from the bra. It was almost like her breasts were spilling out of the bra, large and full and teasing to him. He wanted to touch them, to close his eyes and suck the nipples hard. She wore fiery hot pink lipstick which matched her fingernails. After a quick tour he changed into a long black lace nightgown and purple silk wrap. Underneath he had a new bra on, with fake breasts inside, large ones with nipples. He felt terribly feminine with the bra on. It made him feel like his true self. He knelt on a slave pillow, placed his hands behind his back and recited the following litany which he had memorized: “Mistress Ruby, my body belongs to you. Every part belongs to you including my mouth, my tongue, my nipples, my penis, my balls, my asshole and my bottom. Every part of my body and mind and spirit is at your disposal. Please use me as you will.”

Then, he made his first mistake. Shawn stood up and indicated that he would like a kiss and a hug from the Mistress. Mistress Ruby controlled her anger with some effort, and explained that never, never, would he initiate anything of the sort. He was to speak only when spoken to, and keep his eyes downcast at all times. Mistress Ruby knew she would have to punish him for this forward behavior. Shawn knew he had done wrong, and felt his stomach turn over in fear. What would the punishment be? She knew she shouldn’t be too cruel, after all this was a novice sub. Pushing the limits was to be expected. She considered this for a while, and decided to allow him to pleasure her while she thought over possible punishments.

Shawn was an exceptional slave in that he liked to serve, and serve well. So Mistress Ruby allowed him to remove her stockings and boots, and shave her legs. Shawn was new at this (not having grown up as a girl) and was a bit awkward, but learned quickly. He massaged the feet and calves, which were strong and shapely from regular workouts. He felt himself slide into subspace as he massaged. He knew that this was exactly where he belonged, at the feet of a stern, but fair mistress.

Sadly however, Mistress Ruby knew that the time for punishment had to come. She was a fair person and wouldn’t punish unnecessarily, but it was clear that Shawn was pushing the boundaries right off. She bent him over the dinner table and spread his legs wide. It was a beautiful sight, his asscheeks spread wide and white from the winter months. She spoke to him softly, explaining that she was only punishing him because he had been disrespectful and had not followed her orders. He had failed to obey her in five ways, five infractions that would require punishment. She started with her hand, spanking his ass firmly with a good sting. Shawn had never been spanked, and felt humiliation and submission run through him. He felt tears coming to his eyes, but tried to hide it. There is nothing so degrading as being bent over a table and punished like a child. Nothing.

Next she used a wooden paddle on his behind. She varied the strokes from light to heavy, and on differing parts of his tender behind. The cheeks were a bright pink now, and his bottom wiggled around to get away from the punishing wood to no avail. Finally she started in with the leather slapper. It made a lot of noise, and sometimes he wasn’t sure if he could take one more time. He counted them off over and over, 1-2-3-4-5, one for each infraction that he had committed. He was torn between wanting it all to stop, and wanting to be punished because he knew that he had done these things thoughtlessly and irresponsibly.

Finally, she stopped and he thought, hoped, that they were done. But no, he could feel her finger sliding into his asshole and loosening the muscles. If a spanking was humiliating, this was worse! Yet even so, he liked it. He was scared of what was coming, but wanted it too, because it expressed the core of his femininity. At her instruction he raised his ass higher, and loosened his asshole for the onslaught. It came as a butt plug, smallish but still invading, and with a vibration that went up his spine.

Then the big one came. A large ruby red dildo, pressing hard against his asshole. He wanted to safeword, to say no, to escape. But even more he wanted to be fucked in the ass with that dildo like the girly slut he was. Mistress Ruby talked to him, told him to accept being fucked like a girl and to accept the pain as his submission. At her insistence, he begged her to push it into him, to sodomize him like the slave he was. When the dildo was rammed completely in, he felt so full, so helpless, so submissive.

Then Mistress Ruby moved behind him and shoved it in and out hard, like she was fucking his ass herself. She gripped his hips tightly and forced him to take it over and over until he was crying and begging and thanking her all in one breath. She kept up the pounding for minutes, hours it seemed, until she saw he could take no more. Shawn squirmed, wiggled, and begged for more, and squirmed even more when she turned on the electric vibration while she sodomized him. It was the ultimate of everything he had always wanted and he cried out loud with the pain and the pleasure of it all. Suddenly Mistress Ruby stepped back, and withdrew the punishing dildo from his ass. She ordered him to kneel again on the pillow and he did, still reeling from the rape of his ass. She kissed him gently on the cheek and told him he’d done very well and to get dressed again.

After getting dressed, they sat at the very same table and talked over cold drinks. Mistress Ruby was considering releasing him, but knew that he had not yet been allowed to come. She had been considering for days whether or not she would allow him to orgasm. She liked seeing a man come in front of her, his vulnerability completely at her mercy. Yet even more than that, she wanted to teach Shawn the joy of withdrawal. The pleasure in turning over his pleasure to her, in NOT being allowed to orgasm. She took him into the bedroom where she allowed him to masturbate, and even allowed him to suckle and touch her breasts. He was like a girl child, suckling and hugging and trying desperately to get off. Mistress Ruby still hadn’t decided what do; did he deserve an orgasm? No, she decided, he’d had five infractions which was pretty serious.

So, she allowed him to masturbate right up to the orgasm, but the moment just before she made him stop and stand up. It was so difficult and painful for him to stop, his hands were drawn again and again to his cock and balls even standing there. A supremely submissive moment for him. Mistress Ruby knew that this was a good start, that one day she could order him to stop and he would snap to attention without the face of pain and the wandering fingers. When that day came, when she could control his sexuality completely, then she would allow him to orgasm for her. Mistress Ruby Smiled.

**

Part II - Slave Shawn’s Version

SPECIAL NOTE: Slave Shawn sent this story nearly three days after the required deadline, and as a result will be punished as follows: He will be tied naked to hooks in the ceiling with clothespins on his virgin nipples. He will receive 15 whacks with a wooden paddle and 10 stripes with my leather belt. If he had planned a little better and written this short piece on time, he would have received no punishment. He will also receive punishment for the seven spelling errors in his story. - Mistress Ruby.

My tits thrust outwards through the filmy materials of the gown she had loaned me. It was like a dream come true, to there with her alone, to be shown the beautiful gown that I was to wear, to be specifically instructed to change into these pretty clothes, with my large titties showing through.

Before changing I had used my disposable enema, as she had instructed earlier, “to shower inside and out,” to be clean and ready for her use. I felt nervous in my stomach and a wonderful sense of warm, sensuality and anticipation as I walked out of my dressing room to meet her gaze. As I stood in front of her with eyes downcast I could feel her eyes flitting over me carefully, lustfully. This made me feel so full of unfettered happiness and joy, to be lusted after by a large, beautiful, buxom woman. I wanted to fall to my knees and kiss her hem but I knew that this would not please her so I waited........my penis stirred as she spoke. “You look very nice, Miss Shawn.” This alone was enough to propel me into her arms, but no, I knew I must wait for her command, as I was now her slave, her novice girly.

She commanded me to kiss between her legs and raised her skirts daintily. I felt that I was in a beautiful dream, too good to be true.

Later, she instructed me to examine the collection of dildos on the kitchen counter. As I moved closer to see them better I felt that I would melt, swoon, for pure joy, that I might actually be taken by her. I wanted nothing more than to be used for her pleasure. As I followed her command to bend over her kitchen table, raise my hem and expose myself to her I knew that I had done the right thing, that it was well and good to have followed my heart, all these lonely, desperate years, to her feet. My heart was opening, melting, scintillating in quiet joy. Her finger slipped in me, easily, and she teased me with gentle, firm thrusts, then came the smaller of the vibrators; it felt so wonderful. My cock started to harden under me, on the hard table.

Too soon the vibrator was withdrawn and Mistress announced that she was now going to use the largest of the dildos on my tight little hole. I suddenly felt afraid, knowing that it would hurt, that she might not be as gentle as I would like, but yet I felt so calm, and happy to be there for her, still. The large head went in quickly, and the sudden stretching of my sphincter sent a flash of white pain through my body, then she quickly thrust the rest of it in me asking, “Have you been a bad girl? Tell me, tell me you’re a bad girl!” I was startled when I heard my own voice moaning, “Yes, Mistress, I’ve been a bad girl!, but please be gentle with me!” Suddenly she grabbed my hips firmly with her strong hands and slammed her pussy hard against the butt of the dildo, charging it fully, finally, into my love hole.

My ass burned hot and felt wonderfully filled, spread, fulsome, as she continued to slam at me with her wonderful, power-pussy, while I heard my voice echoing off the walls, as if from another person, moaning, “please, please, please, Miss, fuck me, fuck me, fuck me!, Please fuck me!”