Made Into His Girl

"Oh Jake..." I reached up for him and he collapsed onto me, his cock still pulsing in my bum.

"Lucy," he panted. I couldn't see his grin but I felt it somehow.

Slowly he eased his softening cock out of me.

"Mmmmmm...." I wriggled. I knew I'd be sore as hell in the morning but right now it felt wonderful. I felt his come leaking out of me. If I'd orgasmed myself I might have felt that burst of remorse and regret that can follow. But with my cock trapped all I felt was a sense of satisfaction at having pleased him.

"Come here." He gathered me to him and I put my head on his chest.

We fell asleep that way.

Chapter 4

I woke up in a wonderful languid calm, stretching in a warm wide bed. Slowly I became aware of my very sore asshole and a stickiness between the cheeks of my bum. Suddenly I was wide wake, sitting up in an empty bed, clutching between my legs where the hard little button of my chastity scraped the palm of my hand.

"Jesus ... what the fuck have I done?" My heart was pounding, my hangover headache suddenly made itself known again with a vengeance, and all I wanted was to get out of there. I looked around for my clothes but there weren't where they'd fallen the night before. Even the gold dress had gone, but the other three that I'd brought along for Sissy were dangling on hangers from the top of Jake's wardrobe door.

Jake! I remembered all the kissing. In a hot flush of shame I remembered how he'd entered me and shot his load inside me. Where was he? Listening hard I could make out the sound of a shower going down the hall, behind the green bathroom door.

This was my chance to escape. To get my head together. To figure out what the hell was happening to me and how to stop it. I got out of bed and discovered that I was still wearing the black lace panties, now damp with come and lube. I slipped out of the soiled garment and stared at my imprisoned little cock. My hairless balls looked slightly swollen though it had only been a day and a night since I'd drained them both into Sissy's warm mouth.

In a panic I hunted around for my clothes. They'd gone. I wasn't about to wear one of the dresses so I went into Jake's draws and pulled out a pair of his boxers and a shirt.

"A little big for you, Lucy."

I turned to find him in the doorway wearing a towel and a smile. His cock made a very visible bulge under the towel.

"Look, I just want to go." I couldn't look at him. "Last night was a mistake. I don't even remember what happened. I was so drunk..." I held his shirt over my groin to hide myself.

"You can go anytime you like, Lucy--"

"That's not my name," I snapped, glancing at him.

He smiled infuriatingly. "I'm afraid Sissy took your clothes with her. I've got to go to work but she'll be here in an hour. She said there's no way she's unlocking you though unless you're wearing a dress. So you'd better do it. She's very strict about these things."

"I'm coming to work too!" I started to cross my arms then stopped, not wanting to expose myself any more than I already was.

"In my clothes? Three sizes too big for you?" He came towards me and I backed away until his chest of drawers stopped any further retreat. He set a big hand gently to my shoulder and stroked me when I tried to flinch him off. "You deserve a day's holiday. You're hungover. Probably a bit sore." He massaged my neck while I scowled, trying not to acknowledge the reference. "Take the day. Have some girl fun with Sissy." And then, like there was nothing more normal in the world he dropped his towel, gently took the shirt and boxers from my hands, and started to get dressed.

I stood, trying not to watch but hypnotised by the bobbing of his erection as he bent and straightened, unable to believe that I'd had the whole of it up my ass the night before, or that he'd pounded me so hard in those last moments of his passion. I put my hands over my trapped cock as if the sight of it might inflame him and he might rape me. But Jake only looked my way a couple of times, smiling, and each time he did my cocklet tingled under my hands, trying to harden.

Soon he was fully dressed and straightening his tie. He met my angry gaze. "I enjoyed last night, Lucy. A lot." He seemed to sense that he was not getting a goodbye kiss and instead waved from the doorway. "Best tidy yourself up before Sissy gets here. Keep on her good side and she'll give you what you need." He went to the apartment door. "The place is yours, baby girl. Be good."

I watched him go. It was at that point I realised I was still wearing the wig that Sissy had fitted the night before.

I took off the wig first. Initially I put on some of Jake's clothes and ended up looking as silly as he'd predicted. I stood 5'8" with a touch of good will, Jake was a 6'3" all day. The legs of his trousers bagged around my own legs and concertinaed comically around my ankles. His boxers kept slipping down over my hips and all that unused space inside just set me thinking about what he filled it with. Checking I was alone I lay back on his bed and pulled both boxers and trousers down. I rolled back the too-long sleeves of his shirt and tried to play with myself. It had been a huge turn on being fucked the night before -- and whilst I wasn't going to repeat it or even admit it, I would be wanking about it for the rest of my life.

I tried gingerly to free the pulsing, tingling little bud of my cock from its confinement, but a sharp pain soon put paid to my building sexual excitement. That damn catheter tube had me pinned firmly inside the tiny metal dome. All I could do was squeeze my balls and think of Jake entering me so gently and finishing so fiercely. With a cry of frustration I rolled off the bed and pulled everything back into place. I couldn't find a belt to secure the trousers so I used one of Jake's ties.

After that I began to explore the flat barefoot, looking in every cupboard and drawer for incriminating evidence. He and his sister had basically kidnapped me and forced me to have sex with them. Well, forced was too strong a word. I'd been manipulated.

It was a very nice flat with expensive furniture and tasteful decorations. Jake had a lot of art hanging up but none of it was naughty. I'd had a friend who hung those erotic black and white photos that were popular a while back, and frankly it had just looked cheesy. Jake had a well-stocked wine rack, whiskey in his drinks cabinet, plenty of suits and three pairs of leather shoes, all too big for me. His kitchen was clean, full of professional-looking cookware, and rather modern.

At the rear of his sock drawer I found a pack of condoms though he clearly hadn't used one last night. The only 'naughty' thing I found was at the back of the wardrobe where the dresses still hung: a pair of handcuffs covered in black fur and a vibrator of modest size.

I went to the loo and sprinkled through my chastity, figuring how to aim by pressing with one finger, so that I didn't get my legs wet again. The shower was there, the glass walls still beaded with water from Jake's morning ablutions. I wanted a shower but I also didn't want Sissy to arrive while I was naked. Also, though I didn't like to admit it, I was still getting small thrills from the stickiness left on my inner thighs.

"I should just leave..." I got off the toilet and dabbed my chastity dry. "I'm not a prisoner here."

That's when I heard the key in the lock, followed by a bright, "Cooee!"

Sissy bustled through the front door carrying more Harvey Nichols bags than she could easily handle. She set them down, pulled off her sunglasses, and -- taking one look at me -- burst into laughter.

"Oh Lucy! You've got it bad, girl, dressing up in your boyfriend's clothes. How silly you look."

She closed the door behind her. "Oh, baby, your hair!" She shook her head. "We've got a lot of work to do. Fortunately, I came prepared!"

"Give me the key, Sissy. I've had enough of this!" I held out my hand.

Sissy managed to look surprised, offended, and amused all at once. I'm not sure how.

She crossed her arms under her breasts. "First tell me you didn't enjoy last night. I saw my brother this morning and he looked very pleased with himself."

My gaze slid to the bags at her feet. "I didn't enjoy it. And nothing happened."

"Silly Lucy." She trilled a laugh. "I've never seen someone go so red so quickly."

"I still want to be unlocked," I said, not looking up.

"Of course you do." Sissy came towards me and took my hands. "Look at all the stuff I've got!" she said, excitedly. "Just let me try it out on you and I'll get the key. I promise."

"You haven't got the key?" I said, horrified.

"Shhh... silly." She beamed. "I know where it is." And she led me into the bedroom by the hand. "Let's repair your hair first."

Defeated I let myself be led.

The first thing Sissy did was pull Jake's trousers and boxers off me in a smooth motion and push me onto the bed. She set a perfectly manicured hand to the sticky inside of my thigh. "Nothing happened, hey?" She arched an eyebrow.

"Before we do anything else, you need a shower, missy!"

She stepped me out of Jake's clothes and marched me back to bathroom bringing fresh towels and pointing out the shampoo and shower gel. She waited until I'd unbuttoned Jake's shirt then took it off me. "I'll leave you to it."

I'd half expected her to watch. I washed myself well, enjoying the streams of hot water, imagining that they'd rinse yesterday away, and once I had the chastity off I could start fresh. Jake had been a hell of an experience but I wasn't turning gay because of it, or wearing dresses on a regular basis. Maybe I'd take one home and try it on once a month. But nothing more than that.

I came out damp and refreshed. Wrapped in two large towels I went to find Sissy. As threatened she was dead set on making me pretty again before even considering going to retrieve the key I so badly wanted. Jake had painted her as rather mercurial and I didn't want her vanishing off in huff for a week, so I sat down and let her have her way with me.

The first thing she did was lie me back and unwrap me from my towels. The sight of my chastity brought a white smile to her wide, red-lipped mouth. "Roll over, Lucy."

I did and a moment later her strangely cold fingers were between my bum cheeks. "Just some cream, baby. You'll be rather sore, if I know my brother."

It felt good having her slim fingers there, massaging my tender little hole. Too quickly she was rolling me back again.

"Let's check you down here, Lucy." She spread my legs and knelt to inspect me. It brought back memories of two nights ago when she'd sucked the sperm out of me. She placed a kiss on the silver dome covering my cocklet. I could feel the warmth of her breath and I tingled helplessly. She slid her fingers under my balls and lifted them. "Getting full already! Poor baby. We don't want these getting too swollen. That could be uncomfortable." Slowly and deliberately she licked one, bottom to top, then the other. I whimpered in frustration at the tightness under the dome.

"Lucy. Lucy." Sissy pushed my legs wider and took my left testicle entirely in her mouth, her dainty white teeth closing high up, just hard enough to start to hurt. The wonderful feeling of warm wetness, contrasting with the implied threat that she could with one bite take a whole piece of me away, made me shudder and gasp. I realised with horror that I was wetting myself a little, wee dribbling out of the stainless steel hole.

Sissy released me slowly, drawing her head back and letting my testicle slide out over her teeth then between her lips, leaving faint red smears of lipstick. Calmly she took a handful of tissues and patted my groin dry. "Poor baby. The catheter makes these things harder to control. If it's a problem I can buy you some pads to put in your panties."

"It is a problem!" I shouted. Sitting up sharply. "And I don't want any damn pads, or panties for that matter. I want you to fucking unlock me!"

Sissy's face hardened. She stood up and turned for the door.

"Wait!" I remembered what Jake had said. She could vanish for a week. "Wait, Sissy. I'm sorry. I didn't mean to shout. I just really want--"

"We'll dress you first this time then do your hair and makeup after." Sissy turned back, smiling as if I hadn't spoken.

Sissy had come prepared. Her bags held a range of lingerie, skirts, tops, all sorts. I sat as patiently as I could while she dressed me up like her own personal dolly. She chose pink cotton panties for me with the word 'baby' in small neat lettering just above my chastity. They were on the tight side and she tucked my balls in deftly. Then a long skirt. A white bra which she filled with the breast forms. A white blouse. All the time, while she hovered around me, buttoning, zipping, pulling ... my trapped cock pulsed with denied excitement. Part of me was loving the attention and I really wanted to see the results. Another part was seething that I was still being manipulated so successfully, still locked up at this woman's whim, an unpaid whore for her brother. I kept thinking about how he'd fucked me too. Picturing how he'd put me on my back and moved over me, missionary position. For some reason I'd assumed anal sex would happen from behind. I thought of how we'd kissed and bit my lip.

Sissy put on some music and hummed along as she put my wig back on and did my makeup. Finally satisfied she stepped back to admire me.

"One more thing!" She turned away and rummaged in her bag, bringing out two elegant pairs of shoes, one patent leather high heels and the other a low heeled ladies' shoe with rose patterns on cream leather. "Look what I found in your size, darling!"

It wasn't an idle boast. Like Cinderella I found my feet fitted perfectly. Sissy beamed and said we'd save my toenails for later. I would have said that there wasn't going to be a later but I didn't want to spoil the moment or have her storm off. Besides, I really wanted to see the effect after what felt like hours of preparation. "Is there ... a mirror?"

Sissy opened the wardrobe door and tutted as she moved the suit hanging there onto the main rail. The inside of the door supported a full length mirror. She aimed it my way.

"Oh..." I gasped. Sissy had done a magnificent job. I looked almost as beautiful as she did. Rather more fresh faced and flushed. Where she was elegant and full of sexual confidence I looked young, almost teenaged, and nervous. But there was no doubt she'd made me pretty in a casual, understated way. My blouse swelled gently, hinting at my breasts. The skirt looked good on my hips. The shoes, visible below the skirt's hem, complimented the ensemble. "Wow."

"Lucy likes?" Sissy grinned.

"You've done a wonderful job," I said, humouring her. "Really wonderful."

"I have haven't I?" She leaned in and kissed my cheek, then brushed at it to repair the slight disturbance to my foundation.

"But," I said, nervously, "this chastity thing is getting really uncomfortable, Sissy. I'd really really appreciate it if you could let me out. Even for a little while."

Sissy pressed her lips together, her blue eyes studying my face intently. She nodded as if reaching a decision. "You've been very good today, Lucy." She started to gather her bags, taking a few things out and putting them on the bed. "I'll leave you the stockings and the blue thong. I can get refunds on the hot pants, they didn't really work as well as I thought they would..."

"The key?" I asked softly.

She nodded again. "You make sure you're just as pretty when I get back, darling. I'll be as quick as I can. My husband's back from his business trip tonight so I need to get ready myself!"

She left in a bustle of bags, sunglasses back in place. The front door closed behind her and I went to sit in the living room, lying back on the sofa and thinking of how she'd held one of my balls in her mouth. The memory of her teeth on my delicate skin, so close to meeting, made my cocklet tingle inside its shiny prison.

Jake came home at six. I rushed to the door, still holding out a faint hope that it would be Sissy, though knowing deep down I'd been betrayed. Again.

"Lucy!" He stepped back. "You look like a million dollars!"

Chapter 5

Jake was so nice and caring. He immediately took me over to Sissy's place in his BMW to get the key. I stood by the car feeling exposed while Jake ran across the road to ring the doorbell of Sissy's impressive townhouse. Either both Sissy and Jake came from money or Sissy's husband was loaded.

Several men gave me glances as they passed by and I looked down each time, scared that they'd seen through me, though really it seemed that they saw the same pretty girl I'd seen in the mirror.

"I'm sorry," Jake said as he came back. "They must have gone out. We can try them again later."

I pressed my lips into a thin line. "This is getting ridiculous. I can't spend the whole week locked in this thing."

Jake spread his hands. "She's a terror!" He smiled. "We could go for a meal. I know a great little restaurant--"

"I just want to go home," I said, terrified of the idea of being on display. Someone would see through me and everyone would laugh.

"We can do that." Jake opened the car door for me. "But you've got nothing to worry about, Lucy. I saw that last guy checking out your ass. You look great." He grinned.

I ended up letting him fuck me again that night. He was so attentive and pleasant once we got home. There was a glass of wine then one more. Jake put the wine away after that. "Don't want to get drunk every night!"

He sat beside me on the sofa. Took my hand in his. "You were very beautiful last night."

"Sissy knows her job."

"I mean once the dress came off and it was too dark to see your makeup." He smiled.

I blushed. "I don't plan to make a habit of it."

"My little virgin." He kissed my cheek and my whole body tingled.

We were kissing open mouthed moments later. He took me to bed and undressed me. I escaped beneath the duvet in bra and panties. He followed me in his own bulging underwear, leaving the light on. We spent an age kissing and in the end it was the throbbing in my chastity that made me reach for his cock and ask for more.

"I want to see..." I said nervously and pushed back the duvet. He was huge. So much bigger up close than I had imagined, though to be fair it had felt like a barge pole when he had eased it into me the night before. "I want to taste it," I said, feeling suddenly braver. I took the thick, heavily veined length of it in both hands and angled the shiny purplish head towards my parted lips. I was going to suck a cock. Or rather Lucy was. It made sense if I thought of it that way.

"Baby..." Jake rested a hand on my hair, steering me where he needed me.

I licked the tip of his penis, tasting a man for the first time and feeling like a complete slut. I opened my mouth as wide as I could and let the head of his cock fill it. It felt so nice and the warmth between my legs increased so much that for a moment I worried I was wetting myself. I sucked on him as if his cock were my own personal lollipop. He pushed forward, trying to get deeper.

I gagged and pulled back. "I can't take more than that." I looked up at him along rippled muscles of his abdomen. "I'm sorry..."

He pulled me up and kissed my mouth sweetly. "We can practice, Lucy." He rolled me onto my front then skinned my panties down, moving down to pull them over my feet. I lifted my bum expectantly, thinking he was going to enter me and bracing myself for the pain. He parted my butts with both hands, but then I left his lips, his tongue. It was so unexpected and so delicious that I buried my face in the pillow, moaning.

Jake kissed my sore little anus, licking it softly, pushing his tongue into me in an unexpected French kiss, holding my cheeks apart as I raised up for him. I was enjoying it far too much to think about how slutty I must look.