Chastised, Feminized, Sodomized

"But why do you have to keep me locked up like this?! It's very frustrating!"

"Yes, I'm sure it is. But it gives me great pleasure to see you like this. You said you'd do anything to make me happy. You did mean it, didn't you?"

"Yes," I pouted.

For some strange reason, Erin seemed to derive great pleasure from teasing my restrained organ. She said she loved it, because she knew how badly she wanted me... and it was important to her to be wanted... and I wanted her desperately.

At night after dinner, when we were lounging around in the den watching a movie or the news, she insisted I was nude (except for a short robe on chilly evenings). This way she had constant access to my little peanut, which she teased unmercifully.

She herself loved to relax in a plethora of lingerie. Some of it was conservative, simple satin pants and shirts. A lot of her lingerie was from Fredericks of Hollywood and Victoria's Secrets... sheer black and red teddies, with garter belts, stockings, and high heels... the kind of things that left her breasts half exposed and her exquisite bottom covered only by the tiniest of thongs. All of which was meant to drive me absolutely insane with lust and desire. All of which worked quite well.

After a month into my six months penance, Erin told me to get rid of my apartment and I moved in with her. After the second month she was promoted to the regional manager position, which came with a nice raise. So she told me we didn't need my income and convinced me to quit the bank and to stay at home full-time and become her "house subby." I took care of all the chores around the house, the cleaning, the cooking, the laundry and the gardening, while Erin made a very nice salary at the bank.

Although I loved being with Erin I feared that now I was completely and utterly dependent on her. I no longer had a salary, so if I needed to buy anything, even things like groceries or gas for my car, I had to ask Erin for funds. Erin was quite generous that way, but it was humiliating to have to ask her to pay for even the smallest of things. When I complained that I didn't have the ability to buy her dinner or presents, she just laughed and told me I was letting my "antiquated male feelings" get in the way, and that I should just ask her for whatever I needed.

On weekends Erin loved to go out dancing, and she loved teasing me just as she had done at the Christmas party. On occasion we took weekend trips to the beach. Erin looked absolutely incredible in her yellow bikini. Men everywhere stopped to gawk as she walked past, which made me feel incredibly proud of her, but at the same time it frustrated me to no end to be so close to someone so desirable and not have any release for weeks and weeks. Especially when she would lay on her beach towel and order me to rub suntan lotion into her entire body. As I massaged her gorgeous body, at times I thought I would go mad. My groin ached, and my head seemed to spin. Before I'd met Erin I masturbated every day, sometimes twice. To go eight weeks without touching myself, and to be constantly in the company of someone as intoxicating as Erin, frustrated me to tears.

Week after week, Erin kept my poor, restrained manhood teased and tortured. The key for my chastity device hung from a necklace that she never removed. No matter how much I begged and pleaded she refused to let me free, she just waved the key on the end of the chain, and said, "No way Jose."

Our sex life consisted of me going down on her, not once, but usually several times a day. She liked to start the day with an orgasm... sometimes she stopped home for lunch for a quickie, and I always visited her little "flower" before she fell asleep. She said it helped her to sleep better, plus it relieved all the tension from the high stress of her position at the bank. Each time I gave her release, she thanked me by teasing my poor little peanut. She teased me so much, that after a while it stopped trying to get erect... the pain of the restraint each time she played with me was conditioning my poor tortured little organ to stay soft.

No matter how much I begged or cried for her to let me free, Erin shook her head and said that she was not going to let me loose before six months were up. And that I had no one to blame but myself. She derived great amusement and pleasure out of the terrified look on my face.

One day, halfway through my six months of enforced chastity, Erin came home with two gift wrapped boxes. "I bought something for you. Open them," she said smiling.

I pulled off the wrapping paper and opened the first box to find an authentic black maid's costume inside, complete with garter belts, black lingerie, nylons, white apron, and a pair of 4" stiletto black patent leather pumps.

When I looked up at her questioningly, she grinned. "You can wear it when you're cleaning."

In the other box, from Victoria's Secrets, was a slinky white satin chemise, that Erin said I should start wearing to bed. "Eventually I want to get you a whole new wardrobe. Come on, put on the dress I bought you."

If I thought I could no longer feel any more embarrassed, I felt it that night as with shaking fingers I put on the black lingerie, nylons, and Erin helped me with my garter belts and getting into my dress. Afterwards she insisted I needed a little bit of makeup. She sat me down in the bathroom and painted my face, giving me careful instructions on how she wanted me to do it in the future.

"I don't understand," I sniffled. "I'm a man. Why do you want me to dress like a woman?"

"Of come on now my little Kimmy," Erin said brushing mascara across my lashes. "You're really not very much of a man now, are you? If it wasn't for your talented tongue, I doubt you could please a woman. Plus, to be honest, I really don't care very much about penetration. Hank was always trying to get me into bed, and I just couldn't stand it. No. I much prefer a boyfriend like you. And you're a very pretty one indeed."

When she finished brushing blush across my cheeks and doing my lipstick she teased my hair out, sprayed it with hair spray, bid me look in the mirror.

I took a step back. I couldn't believe the image looking back at me in the mirror was really me! I looked like a cute young Asian girl wearing a very prim and proper maid's uniform.

"You look lovely," Erin said. "Lovely. I'm going to get you some regular dresses, skirts, and blouses. We're going to throw away all of your old boy clothes and get you a whole new wardrobe. I don't want you ever see you in pants again."

"Erin, you're not serious!"

"I'm completely serious. I like you this way."

That night I wore the cute little white chemise to bed. Being in women's clothes all day and now in bed, was doing something to me. I suppose I'm submissive by nature, but the soft material of the chemise and the feel of Erin's strong arms around me, snapped something inside of me. It was almost as if I could hear my whole past life disintegrating and passing behind me. I knew that from now on, my entire life was going to be different. Things hadn't exactly turned out the way I would have imagined they would, but so long as I was near Erin, I was happy.

Within the next few weeks Erin slowly bought me more and more women's clothes, until she finally announced she'd thrown all my old male things into the garbage. All of which took some getting used to. At home, in the house, it wasn't bad. During the day I practiced with my heels and makeup till I began feeling more comfortable. It was when she came home at night and Erin wanted to go out to eat at our local diner or go dancing at the club that I got nervous. The very first time I was terrified to step out of the house that way.

"Don't worry!" Erin insisted. "You look fine. You look better than most real women. Most would kill for your waistline or your legs. Stop fretting! No one is going to know that you were ever born male. Think of it this way... the only part of you that is male... is so small... and so well hidden... they'll never have a clue."

Erin was right. Wherever we went, to the movies, to the grocery store, to the mall, no one ever said a thing. They looked at my long hair, slender figure, and women's clothes and saw a female. All of which I found quite shocking. After the first few weeks, eventually I began to relax, and even slowly came to enjoy it. Erin would smile at me, with a twinkle in her eyes, as if it was our own private little secret, She got tremendous amusement out of it whenever someone called me "Miss" or a man went out of his way to open a door for me. Once when I was walking down the sidewalk to the post office, a group of construction workers in a ditch even whistled at me! When I told Erin about it later that night when she got home from work she was delighted.

"Do you like men whistling at you?"

"No of course not!"

"Have you ever thought about what it would be like to sleep with a man?"

"Erin no! Please don't even say such a thing! I'm not gay!"

Erin looked at me in my short skirt, high heels, and a red and white polka dotted blouse and just laughed.

Life with Erin was most definitely different, but life was good. Well, except for one thing. No matter how much I pleaded with Erin she would not remove my chastity restraint. Some nights I would literally cry in her arms, begging her for mercy.

"You've still got another two months my beauty," she said, "and you know how hard-headed I can be, don't you?"

Yes I did. Erin was not about to change her mind about this.

"But I'll tell you what," she said. "Now that you've become my pretty little girl, I think it's time you experience some more womanly pleasures."

"I don't understand," I said as I lay beside her in bed in a sleeveless, short white satin nightie.

She smiled at me, her eyes crinkling merrily. "I think we've been living together long enough. Tonight I'm going to make love to you my darling."

"What?"

"I'm going to take your virginity," she whispered, kissing me gently. "Just as a woman experiences some pain at first... it's going to hurt. But I promise you that I will be gentle, and once you get used to it... it will give you some relief."

I had no idea what she was talking about. Her, make love to me? My virginity?

I didn't fully understand until Erin climbed from our bed and disappeared into the bathroom. I lay there waiting, heart pounding, nervous as a bride on her wedding night.

Eventually Erin returned wearing a long black nightgown. She fiddled with a CD-player on her entertainment center. Ravel'sBolero played through the speakers. Erin hid a smile, and tried to look serious. She came back to bed, and let her satin peignoir fall from her shoulders.

My eyes widened. "Oh my God no!"

Around her waist she wore a leather harness and a very life-like strapon dildo. It had to be a good 7" long, more than twice the size of my own little peanut, and artfully designed with veins and testicles so that it bobbed and moved between her legs like the real thing.

"There, there, my blushing little bride. Don't look so frightened. I know it's going to hurt the first time, but I promise you that in a few weeks you will be begging me to make love to you. Now, take down your panties... spread your legs... and lift your knees to your chest."

Trembling in fear, I did as told, feeling frightfully exposed.

Erin climbed up onto the bed between my outstretched thighs.

"My darling Kimmy," she said softly as she positioned herself, looking down at me, "you look so beautiful like this... so timid... so vulnerable. Don't be frightened. It will all be over soon enough my love."

Erin knelt between my legs, placing the well-lubricated head of her lifelike dildo at my tiny opening. With her hands gripping my ankles, pushing them back toward the headboard, she raised my bottom to meet her phallus. I whimpered as the head pressed against my anus. Then without warning, she rammed her hips forward, taking me in one quick and painful thrust. I cried out shrilly in pain and surprise. Just one thrust, and she completely took my breath away. I lay there gasping for air in short quick gasps.

I thought she was going to be gentle!? "It hurts!" I wailed. My insides were ripped apart and bleeding. Her penis felt like a man's fist shoved inside of my most tender of openings.

Erin's eyes flamed with lust as she watched me squirm and bleat like a slaughtered lamb upon the altar before her. She placed my ankles over her shoulders and leaned forward and kissed me passionately. "There, there, little one... I'll give you a minute to recover. Don't worry. It hurts at first, but I promise you that you're going to enjoy thisalmost as much as I do."

"I thought you said you were going to be gentle," I cried, tears in my eyes.

"I want you to feel some pain my love... that's why I did not use too much lubricant. I want you to know how a real woman feels when her husband tears away her most sacred virginity. I want you to remember this, your first time... and I want you to remember me. Your first." She kissed my lips tenderly. "It's okay. I promise you, from now on, I will go slow."

She rested against me for a minute, allowing me to catch my breath. A tear slid down my face. She kissed it away, covering my face with soft, fluttering kisses. Then carefully, skillfully, she began to raise and lower her hips, easing her plastic extension in and out of me in long, deep thrusts. At first it was excruciatingly painful, and I cried piteously.

As she made love to me, Erin rose and lowered my ankles, tilting my hips, and listening to cries. Finally, she found my sensitive prostate gland with the blunt knob of her phallus. When she did, I let out a surprised moan of pure pleasure.

Between half closed lids, I saw her... grinning down at me. "I think I found the spot," she whispered.

Her hips undulated like a dancer. As Ravel'sBoleroquickened, she began to thrust faster and faster. Her strapon slid back and forth across my sensitive little cherry till I was groaning loudly and uncontrollably.

"That's it my pet... didn't I tell you this would give you some relief?"

I thrashed about beneath her like a fish on a hook, torn between pain and pleasure. My poor little peanut tried to lift his head, and was strangled by the straps of my chastity belt... such exquisite bondage.

But I wasn't focusing on the peanut. My entire epicenter focused on my here-to-for untouched, virgin cherry that Erin was ravaging quite totally with her 7" strapon.

Never had I ever experienced pleasure like this before. It was mortifying to be used such a way by a woman, especially such a beautiful woman as Erin, whom I loved and adored totally and without reservation. In the back of my mind framed images of me ever playing the role of the man with Erin were being shattered like picture frames smashed by a sledgehammer.

She filled me not only with her penis, but with feelings of excitement I never knew existed... feelings that we both knew were about to shape our relationship for years to come. All of which was exciting Erin terribly.

She impaled me deeply, moving her hips with the music, grinding the soaking wet folds of her clitoris back and forth against the base of her phallus. "Oh God, I'm close," she gasped. She thrust hard against the base, eliciting from me a high pitched cry of both joy and frustration, just enough to trigger her orgasm. Her body shook and jerked like a puppet on its strings, as she let out a loud, satisfied roar of release.

After she finished shaking and twitching, as the last electric impulses faded away... her gorgeous, voluptuous body fell like a mighty oak, landing on the pillow beside me. As she did so, the strapon was ripped from my body, leaving me empty and groaning in throbbing frustration.

For a few minutes she lay there, catching her breath. Her breasts and belly shone in the candle light with a sheen of clean sweat.

She'd kept me on the edge of orgasm, but without the final release, all of which conspired to make me more horny and frustrated than ever. I turned away from her, and buried my face in my pillow, sobbing.

"There, there, my little Kimmy," she said. She snuggled up behind me, still wearing her greasy stapon, which pressed against my bottom, a dull reminder of where it has just been. "Why are you crying?"

I turned to face her, wiping away my tears. She pulled me into her arms and kissed my sweat soaked hair. My face nuzzled her neck. "I haven't cum in five months. Please Erin, please, I'm begging you to take it off me. Just this once. You are going to make mecrazy!"

Erin chuckled, "But my darling, you did cum. See?" Her fingers massaged my flaccid, restrained, numb penis, and played in a puddle of goo on my tummy. "You came a lot. Five months worth."

"But... but... but!"

"You've just been milked my darling."

I didn't know it then, but in the days and weeks ahead, as Erin continued to make love to me, I realized that the pressure of the strapon pressing against my prostate forced the semen out of me. But because my little peanut was restrained, I was not able to experience a normal male response. It was an orgasm, without ejaculation.

"You still have another 30 days, before I set you free," Erin said. "But I promise you this... I'll make love to you with the strapon whenever you want. All you have to do is ask."

I blushed hotly. "But Erin, shouldn't I be the one making love to you?"

"Put those old-fashioned notions out of your head, my little Kimmy. Face reality. You are not physically equipped to please a woman that way my pet. Which is quite fine with me. I much prefer your tongue, and to take you like this. So if you want to stay with me, you mind as well just give in and get used to this. You'll never make love to me like a man.It's never going to happen. If anyone is going to penetrate anyone in this relationship... it'll be me, making love to you."

Tears welled up in my eyes and glided down my cheeks. "All right," I said. "It's okay. You know that I would do anything for you. Anything. Because I love you... I really dolove you!"

Erin smiled and hugged me even tighter. "I know you do my pretty little sissy."

No matter how embarrassed I was to be taken that way, Erin's milking my prostate was the closest thing I could get to any kind of sexual release. In the beginning it left me moaning and sobbing in frustration. Still, our love-making bonded us closer together still.

After she took my virginity, I was sore for several days. At first I worried that she'd take me again the next night, but she didn't. She said, "I told you... if you want me to make love to you... you're going to have to ask."

At first I was too timid, too shy. At first I thought if she made love to me the very next night, I was so sore... she'd damage my insides.

After a two days of lapping at Erin's little flower every morning and every night, I began to crave her. It became like a hunger. I wanted her to take me, to penetrate me... I wanted her inside of me... almost desperately so, but I was afraid. Not matter that I dressed as a woman all day long, there was still a male ego deep inside of me, and it tore me apart to have to ask Erin, my beautiful Erin... to fuck me.

Finally after three days, I could take it no more. One night as we climbed into bed, I snuggled up against her. Shyly, I asked, "Erin... will you... will you please... make love to me again? Tonight. Please."

With her elbow in her pillow, Erin lifted her head up into her palm and stared down at me. Her eyes danced playfully. "Beg for it."

"What?!"

"Come on. I want to her hear you beg for my cock."

"Erin!"

"Do you want it?"

"Yes!"

"Do you want me to fuck you?"

"I want you to make love to me."