Made Into His Girl

I didn't see much of Jake. He had strategy meetings and budget meetings to attend. Instead, I dealt with customers. As assistant manager I got most of the richer and most loyal customers, the women who enjoyed a man's input. These sales regularly added a bonus to my salary that kept me considerably above the girls' income. At least that side of things went alright, even when I had to keep excusing myself. I sold a four thousand pound frock to a woman too old for it, and felt a little better.

Towards closing Jake appeared on the shop floor and approached me for a report on the day's takings. When I'd finished he turned to the nearest rack of dresses and pulled one out.

"I need three or four that would fit Sissy and look good on her. You've seen what she's like. Pick some out for me, would you." And with that he excused himself, saying to meet him at the staff carpark when I'd finished up.

I came down twenty minutes later, feeling flustered, acutely aware of the chastity device locked around my scrotum, and with four dresses draped over one arm. A toot of the horn drew my eyes to Jake's BMW and I went over to join him in it, placing the dresses carefully on the back seat.

"Strap in," he said, flashing me an amused look, and off we drove.

I paid attention to where we were going this time. His apartment was in a Victorian terrace at the far end of Hyde Park. Not overlooking it but close enough that he could have a morning run there, if he was ever tempted by anything so dreadfully healthy. Which looking at him he might be. Compared to Jake's hard-bodied athleticism I was definitely soft. Slim, but soft. My stomach felt a lot better. Well enough to growl with hunger.

"This isn't funny." It took me about five blocks to speak. I still hadn't figured out what was going on or what I wanted from it. Sissy was a very attractive woman and the idea of her sucking me to orgasm again was certainly tempting. My tiny cock even managed to ache with impotent lust at the thought.

"It's a little bit funny." Jake reached out and patted my leg. "Just play along with her. You don't want her going off in a sulk."

"Not with the key!" The idea horrified me. For all my talk of the police I certainly didn't want to go to them -- especially not after the picture that Jake had painted for me. I thought his assessment was probably quite an accurate one.

Sissy was waiting for us in Jake's apartment when we got there. She was wearing another dress that might have come from my department, blue silk with a plunging neckline exposing the inner curves of her very white breasts.

"Lukey!" She greeted me with a wide smile and threw her arms around my neck. I could feel her nipples pressing against me through my shirt. Why she and her brother had both taken to calling me Lukey I could say, but I didn't much care for it.

"Key," I said, holding my hand out once she'd stepped away.

Sissy pouted at me. "Oh, that's no fun, darling. You're going to have to work for it a little harder than that!" She reached over to the sideboard and picked up a bottle of wine, brandishing it at me. "First a drink!"

"I shouldn't." I put a hand to my stomach. "That Merlot last night did NOT agree with me."

Sissy shot Jake an amused glance. "Beaujolais, darling. It's kind to stomachs." She poured us three glasses, holding the tray out for me to choose first as if mocking my accusation that they had drugged me. I selected the one furthest from me. "There!" She beamed at me. "All friends!" She sat down on the leather sofa and patted the spot beside her. "Come and tell me about Jake's first day. Was he awful?"

We settled down, drinking wine and talking shop -- literally -- it was both bizarre, given what was going on between my legs, and at the same time very pleasant. Jake and his sister were entertaining, easy on the eye, consummate hosts. Sissy talked a lot and as the wine set up a pleasant buzz in my head I watched her mouth, remembering how wonderful it had been when she sucked my cock into it and took charge. I thought about the way her head had bobbed up and down determinedly, giving me no option but to come. She might have been the one with her face in my lap but I was the one who had been helpless. We talked about Harvey Nichols, the managers, the staff, the customers, the national news, llamas for some reason. We did not talk about the things Sissy had done the night before, not the blow job, not the shaving, not the locking up.

Three or four glasses into the evening Sissy suddenly sat up and said, "What did you bring me?"

"The dresses?" I asked. "I think Jake took them."

"I put them in the bedroom," Jake said, leaning back and watching us, dark eyes wickedly amused.

Sissy picked up her bag from beside the sofa, took my hand and stood. "Come on, Lukey. You can show me what you chose."

I let myself be led, aware once more of being locked up inside my underwear.

We went into Jake's bedroom. His bed was enormous with fresh white sheets and a powder blue duvet. The four dresses were laid out on it. A variant on the LBD -- Little Black Dress -- with slashed skirts, a red gown, a figure hugging gold lame affair, and a sophisticated black and white cocktail dress.

"I brought a selection," I said, struggling to keep from slurring, as despite my best intentions, the pair of them had got me drunk again.

"Which do you think I should try first?" she asked.

I stepped back and looked her up and down. She really was gorgeous. "The gold," I said.

She raised her eyebrows at me and grinned. "You first."

"What?"

"That's the price of unlocking."

"I have to try on a dress?" I shook my head, laughing. "Never going to happen."

Sissy pouted at me. "I guess you could stay locked." She shrugged. "We could try again next week."

I suddenly remembered what Jake had said about not making her sulk. The thing to do here was bite the bullet -- jump through the hoops. Once I was unlocked the balance of power would be very different. "Alright, alright!" I raised my hands in surrender. "I'll try it on. But no photos."

"No photos." She nodded.

With a sigh I began to unbutton my shirt.

Sissy came over and started on my trousers. I jumped back, giving her a startled look.

"What?" she asked. "It's not like I didn't see everything you've got last night, Lukey."

I sighed more deeply and let her do it. She stripped my trousers and pants down, made me step out of them, and pulled my socks off. I tossed my shirt aside and stood naked.

"Awwww...." Sissy, still kneeling beside me cupped my balls. "So cute..." She ran her finger over the little dome confining me. "So small."

"Enough." I pulled away. "Give me the dress."

"Panties first." She held out a pair of lacy black ones.

I shook my head but put them on to satisfy her. They had enough room so that my balls didn't spill out. "Did you ... you shaved my legs too?" I hadn't noticed before.

Sissy nodded solemnly and held out a matching bra.

"This is silly," I said. "It's not like I can fill it."

"Can too." And she reached into her bag, bringing out two quivering silicone breast forms. "Here. I'll help."

She did me up from behind and slid the forms in to fill the lacy black cups. "Cs," I said. It paid to know cup sizes by sight in my line of work.

I went towards the dress.

"One more thing!" Sissy produced a blonde wig with a flourish. "Sit on the bed. This will take a few minutes."

She fitted me with the wig, covering my own short brown hair with the lifelike golden curls that framed my face. "And..." she said, forestalling me as I made to stand. "Makeup! She produced lipstick, blusher, eye-liner.

"Oh gods." I lay back on the bed and let her have her way. The room spun gently while she applied her paints. If I were honest I'd have complained less. I'd always wanted to try on a dress and see if I could look pretty in it. I told myself it wasn't a gay thing at all. Lots of transvestites were married to women who supported their kink. And it wasn't a kink with me -- just something I'd wondered about. It would be surprising if I never had, selling dresses for a living. Even so my poor trapped cock tingled and grew tight again.

"Now the dress!" Sissy said. "And let me help. We're not smudging your face. Not after the time I took over it!"

With Sissy's patient help I slid into the gold dress and let her zip me in.

"You really need heels," she said.

"Well, I don't have any and I sincerely doubt you have my size in that bag of yours."

Sissy pouted. "True."

"So you can unlock me now," I said. In truth I desperately wanted to see the result of all that labour in a full length mirror but I wasn't about to admit it.

Sissy rolled her eyes. "We have to show Jake first!"

"Jake?" I had actually forgotten about him. "I'd been so absorbed in the process and so focused on Sissy who had the key I wanted."

"Yes of course Jake!" She laughed. "There's no point without an audience."

"You're my audience," I protested.

"Silly Lucy!" She grinned and reached for my hand. "You look beautiful. No need to be shy!"

"Lucy." I laughed. "It's better than Lukey, I guess."

She led me out of the room, holding my hand. I followed reluctantly, feeling my cheeks turning crimson. I didn't mind Sissy seeing me like this, but Jake? Jake was something else. "I get unlocked after this, right?"

"Of course, baby girl." Sissy squeezed my hand.

She led me back into the living room. Remarkably Jake didn't appear to have moved or to have become pissed off at how long we'd been gone.

"May I present Miss Lucy Lacey?" Sissy stepped back, leaving me exposed to her brother's view.

"Divine!" Jake stood, devouring me with his eyes. "Simply beautiful. You've outdone yourself, Sissy."

I felt very aware of the weight of the two breasts filling my bra. I coloured and felt hot everywhere Jake looked. He reached over for my glass, which he'd refilled, and handed it to me. "A toast to my clever little sister!"

We drank a toast. Sissy put on some music and made me dance with her. We drank some more. I did a few twirls for them. There was laughter and conversation.

"I must go to the loo." The wine had filled my bladder.

"The little girls' room, Lucy," Sissy corrected with a laugh. "The green door on the left." She pointed.

I went off, suddenly very aware of Jake watching me go, eyes on my bottom. I was glad I wasn't in heels since walking in a straight line wearing a tight dress was proving difficult enough without them. I hurried through the green door.

Sitting and pulling up my dress to pee was a new experience. I'd quite forgotten I was wearing the lacy black panties and slid them down to my ankles with a sexual thrill. The chastity I'd not forgotten about -- though seeing quite how completely it had made my cock vanish still surprised me. I resolved to demand that Sissy let me out now. I'd played the game. I sat sprinkling my wee into the water below and trying to sober up. It had been a very very strange 24 hours and I was ready to go back to boring old normal.

After dabbing myself dry I pulled the panties back up and straightened the dress out.

"Sissy!" I came out of the little girl's room with a determined set to my mouth. "Sissy!"

Jake was waiting in the living room, reclined on the sofa.

"Where's Sissy?" I looked around.

"Have you tried the bedroom?" he asked.

I turned and walked towards the door, conscious once again of him watching my ass.

"Sissy?" I opened the door. The room was empty, the dresses gone from the bed.

"She left." Jake was behind me, his hands on my hips.

"Left?" I turned my head since he was stopping the rest of me turning. "But ... the key?"

Jake bent and kissed my neck. "You really are gorgeous, Lucy."

It felt wonderful, warm thrills ran the whole length of my body, starting where his lips touched my skin.

"I'm not gay," I protested weakly.

"Good." He kissed my ear, his warm breath making me shiver deliciously. "I'm not interested in a gay Luke. It's a straight Lucy I'm taking to bed."

"No..." I tried to break away but my legs felt weak and I didn't try very hard. The idea that it was Lucy he wanted, that it was Lucy he was kissing, seemed to make everything far more reasonable. "I need to get that key from Sissy."

"She's gone," he breathed, stroking his hands down over my hips, pressing himself up behind me, just the thinness of my dress and the lace panties between my bare bottom and the hardness I could feel through his trousers. "Stay here tonight and we'll catch her tomorrow before work. I'll take you in."

"I should go." I turned for the door.

Jake walked past me, taking my wrist and pulling me gently but firmly into his bedroom.

"I'm not sleeping with you," I said primly.

"We'll just share the bed." He nodded. "It's the only one."

"I could..." I pulled towards the door. "There's the sofa."

"Silly girl." Jake pulled me down onto the bed, taking me into his arms. Before I could stop him we were kissing. I opened my mouth to protest but just gave him the invitation he needed to slide his tongue past my lips. For several long minutes the wine took over and I just let him kiss me, pressing his firm body against me, squashing my fake breasts with his hard chest.

"This is crazy," I said softly, pulling away.

"I really like you, Lucy." Jake let me go. "Let's sleep on it." He dimmed the lights with a bedside remote and began to undress. "You too, baby," he said. "You can't wear that dress all night."

Part of me thought 'watch me' but it retailed at six hundred pounds and might still be salvageable. My shopkeeper's heart had me stand and unzip myself. I slid quickly under the duvet while Jake was taking his shoes off, and freed myself from the bra, letting it and its squishy contents drop beside the bed. I couldn't help watching Jake finish undressing after that. He undid his trousers and stepped out of them before skinning off his underpants. His erection was huge, possibly twice the size of mine -- when I was allowed one -- a good thick eight inches for sure. He climbed into bed naked and reached to pull me to him.

"No, Jake." I felt very vulnerable, my cock locked away and nothing but an ounce of black lace to keep him at bay.

"One last kiss and then we sleep," he murmured.

"One." I said uncertainly and not a little drunkenly. "And only one."

Jake pulled me close. My lips opened under his. I felt his hard cock against my groin and I was lost. I felt so feminine in that moment. All my resolve melted away. My limbs were so weak I could hardly lift them. All I wanted to do was let Lucy surrender to him. Luke would never know.

We kissed and I started to explore his muscular body with my hands, glad that Sissy had only painted my nails and not given me false ones so I didn't have to worry about scratching him. My left hand found his cock.

"Oh my God, Jake," I murmured. "It's so big!"

He kissed me. "I'll be gentle."

Suddenly all kinds of doubt assailed me. Not least the practical ones of small holes and large objects. I'd never had that kind of sex with a woman and had no real idea how it worked outside a porn film. What if there were problems? What if it ... smelled? "I don't know," I said, more firmly, sobering up fast. "I think we should take things more slowly." Glacially slow. Tectonically slow. I needed to read up about this. Think it through. Get out of this chastity. Change my mind.

"Lucy." He held me against him, one big hand cupping the left cheek of my bottom, his enormous, scary cock sandwiched between us. "It's going to be fine. Don't worry about anything." He laughed softly and kissed my forehead. "You're all cleaned out, so don't worry about that."

He was right. I'd been on the loo all morning. "How did you know about that?" I asked, suspicious and embarrassed.

"Sissy is nothing if not thorough." And he rolled me gently on my back, spreading my legs with his. I loved the sensation. Like he was opening me.

"Oh..." I said softly. "This is really happening, isn't it?"

"It is," Jake agreed, bending to kiss me again. The blunt head of his cock nudged between my ass cheeks, pressing against the lace of my panties.

"It won't fit," I said faintly.

Jake reached out beside the bed and when he brought his hand up between my legs, pulling my panties to the side, it was full of warm, wet, slipperiness. "There are other ways to lube you, Lucy, but this is best for a sweet, shy little virgin." His fingertip found the little pucker of my anus and slid back and forth across it. He kissed my lips and dipped the finger into me. I gasped, squeezing tight around it.

"Sweetie." He began to finger-fuck me slowly but firmly, working his finger in a little deeper each time. I parted my legs wider and lifted my bum for him. Lucy parted her legs, I told myself. Lucy is a slut. My breath came in nervous little pants and I clutched at his shoulders. Inside my chastity my little cock tingled helplessly. "Baby girl." He slid his finger in as deep as it could go.

Jake lifted up on both arms and brought his lubed cock back to nudge between my cheeks again. "My little virgin," he said.

"Lucy," I breathed, letting myself be carried away by the fantasy and the alcohol.

The blunt head of his cock nuzzled against my anus. He was going to fill me to bursting.

I reached down to take hold of his hips, to keep him back if he grew too eager. "Be gentle."

"Always." And slowly, very slowly he began to push.

"It's too big," I gasped. "You're too big for me."

"Relax, angel." Jake bent to kiss my mouth. "Don't squeeze shut. But trying to push me back out is good -- that actually opens you up and lets me in."

"Oh." I tried to do what he said. I wanted him inside me now. We'd come too far for anything else.

"Good girl."

I whimpered as my tight little hole made the biggest O of its life and slowly Jake's cock began to ease into me. I gasped and took rapid shallow breaths, clutching at his shoulders. Inch by slippery inch my poor little asshole devoured his erection. Soon he began to pull back a fraction then push forward two fractions. Micro-thrusts, each one getting him a little deeper. I wondered how many girls had lost their virginity to him. Part of me wished I were still wearing the gold dress and we had the lights on. Lucy was quite slutty, I decided.

"Oh god..." I whispered. Jake had finally reached his limit. I could feel his balls against my bottom. I had the whole of his engorged penis inside me, filling my rectum while my own tiny cock was trapped in a thumbnail of space, prisoner to my lover's will.

Jake lifted my arms above my head and kissed my throat. He kissed my armpit next and I realised that Sissy had shaved those too. So thorough. I was glad she'd let me fuck her mouth before she locked me away. I gasped as Jake adjusted his position, his cock moving inside me.

"I want to come into you, Lucy," he whispered in my ear.

"OK." I felt helpless beneath him. Very feminine. Very weak. Very his.

Slowly he began to fuck me. Gentle thrusts. Out an inch, in an inch, not surrendering any territory he'd already claimed. I moaned and spread my legs and let him have his way, my trapped cocklet throbbing all the while.

Slow short thrusts became slow long thrusts. Slow long thrusts became more rapid as he began to pump me. I lay gasping, torn between the pain of it and the wanting more. Wanting to be his girl. Wanting him deep every time he drew back. Wanting him to orgasm inside me and fill my ass with his come.

I didn't really have a clue what I was doing but clearly my cluelessness was a turn on because after a few minutes Jake sped up and his thrusts started to become harder and more erratic as he lost control. With a low cry he began to orgasm. My ass squeezed convulsively around him while he spurted away very deep inside me.