Turned Into a Lesbian Sissy

Tim Howe hurried out of the bar as fast as he could, narrowly avoiding bumping into a re-tressed beauty who was entering. After shooting the departing man a dirty look, the woman approached the bar was warmly greeted by the woman behind the bar.

"Carmen! When did you get back in town?" asked the bartender, placing a glass of wine in front of her obviously familiar customer. She was a large friendly woman with a crew cut and several tattoos.

"I'm just here for a few days on business Marge. Who was the asshole who almost ran me down? I don't think I've ever seen a man in here as a customer before."

"That guy? You hit the nail on the head with 'asshole." Marge chuckled. "He's Tony, my Brother-In-law, well I suppose Ex-Bother-In-Law is more like it. My sister finally had the good sense to divorce his skinny ass after he lost a shit ton of money gambling. She got a shark for a lawyer who left him with next to nothing now. And on top of that he still owes Mike The Bat a substantial sum of money, which he doesn't have."

"Mike The Bat?"

"People call him that because that's what he shows up with when you can't pay up. The asshole had the nerve to come in here and ask me for help. It's no secret he has no love for The Gay lifestyle. The idiot probably thought he'd burst into flames just walking in here."

"You going to help him out? It's funny, he's a skinny little thing, if I saw him from behind, I might have thought he was a woman."

"Hmmm you know Carmen, I wasn't going to give him a dime but you've given me an idea ... "

After getting her call, Tim walked into Marge's office in the back of the bar the next day. The hope in his eyes quickly turned to panic however as he saw someone else sitting there chatting with Marge, a well-dressed large man.

"M-Mike! What's going on? What are you doing here? You said I had 3 more days to get the money!" He blurted out nervously.

"Relax sport, sit down. Nobody's getting their knees broken. Not today anyways. I was just having a beer with Marge here and we were discussing your situation." Mike said softly, with an undercurrent of menace. He continued as Tim sheepishly sat down. "Your Sister-in-law here was quite surprised to hear exactly how much you were into for me Timmy. Then it was my turn to be surprised when she said she'd be willing to take over your payments ... under certain conditions."

"Oh God! Marge, you're a lifesa..." Tim began before Marge cut him off.

"Hold on there Timmy. This isn't charity. I had no idea you owed so much but I'm going to help out for my sister's sake, so she doesn't have to read they found you beaten to death somewhere. I'm going to make the regular payment to Mike here, and until that's paid off, with interest, you ass is mine. Got it? Or, if you don't like my offer, you can always deal with my new friend here."

As Marge said that Mike turned to Timmy and gave him a predatory smile that made his blood run cold.

"Anything Marge! I'll pay you back, you'll see."

"I love a happy ending." Mike said, standing up to leave. "Oh, one thing to bear in mind Timmy. Marge will be making the payment every week as long as you do exactly what she wants. As a gesture to repay her for making sure I'm compensated I told her all she has to do is call me if you fail to comply with her wishes. And then you and I will have a discussion in private that I don't think will be as congenial as this one. Marge, it was a pleasure doing business with you." He said, shaking her hand and departing.

"Marge, I don't know how to thank ...'

"Oh shut up Timmy. I know you never had any use for me of my lifestyle until the wolf was at your door. Let's get down to it." She said, producing a stack of legal looking papers from her desk. "Now hand over your wallet and keys, and sign these."

"What? But why ..."

"Because I'm cutting up all your credit cards. You obviously can't be trusted with them. And we'll be selling your car and putting the money towards paying off your debt. These papers give me complete control over your finances so you can't find some new bookie to gamble with."

"But Marge that's going overboard, don't you think?"

"I don't think so Timmy. Mike is probably still in the parking lot; shall we go ask him? Plus, he gave me his cell number, so I can just call him ..."

"No! I'll do it." Tim exclaimed, passing over his wallet and keys which Marge promptly locked away. She noticed him starting to read through all the documents and barked "Just sign them you wimp!"

'Good." Said Marge, "briefly checking the documents before locking them in her desk. "I now have complete control of your finances and Power of Attorney. Tomorrow I'll give one of my staff the keys to your apartment and we can start selling off your stuff. Anything we can't sell we'll just donate to Goodwill. You won't need any of it, you'll be living here in the upstairs room while you work off your debt."

"What?? Are you crazy? I have a job! I can't live and work here, in a Lez Bar!" Tim exclaimed, then instantly realized he may have said the wrong thing.

"Oh I know what you think of my bar, and of me." Marge said with a smile on her face. "I heard you last Thanksgiving referring to me as a big butch lezbo. Oh don't say anything you wimp, I don't want to hear it. Mike The bat may want to though .... Ah I thought that would shut you up. From now one you only speak when spoke to, got it? Just nod your head. Good."

"Besides, you were right about me. I am a butch lesbian, as you are going to find out. Now follow me upstairs to your new room."

Tim sheepishly followed Marge upstairs and was barely able to hold his tongue as the walked into his new room. They stood in the middle of the frilliest room decorated for a girl in lace, satins and silks that had to be the most

feminine room he had ever seen. A bright brass high post bed was made up in pink satins and white lace.

up along the top. A large walk-in closet door was open showing skirts, blouses, and lots and lots of frilly dresses.

"I can't stay here, are you mad?" Tim exclaimed, only to be cut short by the sound of Marge's cell.

"Oh hi Mike." Marge said sweetly, turning a steely gaze on Tim. "Oh no, he's being a good boy. No need for you to drop by .... yet. You're a sweetheart for calling, check in anytime. Tim? It's Mike, anything you want to say to him?" Marge chuckled as Tim franticly shook his head no. "Ok Mike, bye, talk to you soon."

"Now Timmy, where were we? And speak to me again out of turn again and I'll slap your smug little face, got it? Good boy. Now this is where you will live until your debt is repaid in full. You will do exactly what I say no matter what. You will work here at the bar, and since this is as you put it, "A Lezzie Bar" you will be dressed a sweet little lesbian doll so as not to upset my customers. Now take those clothes off so we can get started. Or I can get Mike back here and he can break both your knees. No? Good, let's get to work"

"Here's what's going to happen Timmy, though from now on your name is Tina. You're going to be shaved, plugged and caged. I think I have a cage small enough for that little worm between your legs, no wonder you could never satisfy my sister. Then you're going over my knee for your nightly spanking, until you promise to be a sweet little sissy lezzie for me, got it? And say goodbye to 'Timmy,' from now on your name is Tina."

True to her word, shortly thereafter Tim found himself draped over Marge's lap, his cock locked in a tiny steel prison and a small, jeweled plug in his tight rear hole. Marge used one hand to hold his wrists securely and the other to begin to firmly spank his smooth cheeks.

"Ow ow ow stop please!!!" He cried, tearing up anew.

"Quiet Tina, or I'll have to gag you. You'll need your nightly spanking to remind you to be a good girl from now on. Be glad it's just my hand tonight, I have quite a few paddles to try out on you in the weeks ahead." Marge chuckled, watching her new toy's cheeks redden under ministrations.

"Now it's up to you how long this will go on. It stops when I hear all the right answers. Now, what's your name?"

"Ow! Ow! Tim! My name is Tim!"

"Try again sissy girl. What's your name?" Marge asked, intensifying the force of her spanking.

"Ow ow ow! Tina! My name is Tina! Ow!"

"That's a good little lesbian. See, now that wasn't so hard, was it?" Marge purred, stopping momentarily. "Now that you're feeling a little more compliant let's go over some ground rules Tina. Any arguing or fussing and we can just resume your paddling." She added, enjoying the sight of the weeping sissy's bright red cheeks.

"From now on you're Tina, my little lesbian love toy. I like my girlfriends to be as fem and frilly as possible, so you're going to be my sweet little lipstick lesbian, aren't you? Now tell me what you are Tina and I'll decide if you need more spanks."

"I-I-I'm Tina, I'm your sweet little lipstick lesbian." Tim whimpered, between sobs.

"Good girl Tina. Once you've learned to dress properly and apply you make up you'll be helping out at the bar downstairs to work off your debt. Since I'm your employer now you need to Address me with respect, so from now on I'm 'Miss Marge', understand?" Marge asked, adding a slap on her new toy's ass to reinforce the question.

"Ow! Y-Yes Miss Marge."

"Good Girl Tina. Now as a lesbian you of course don't have a cock, not that you had much as a man. That little lump between your legs is your clitty, I better not ever hear you refer to it as anything else. Get used to the cage on it sissy, because that's staying on as long as you're mine. I'll take it off now and then for supervised cleanings but since a pretty lezzie fucktoy has a tiny clit so will you. In a week or so I'll switch you to a smaller cage, and then a few weeks later a nice pink flat cage for a pretty girl like you. Now let's review,' Marge said, resuming the spanking to maintain Tina's nice red cheek color.

"What's your name and what are you? And remember to address me with respect or we will start over from the beginning."

"Ouch! Ouch! I'm Tina, I'm your lipstick lesbian love toy Miss Marge. Ouch!"

"Good Girl, Tina. And what do lesbians like Tina have between their legs?" (smack smack smack)

"A-A clitty! I have a clitty Miss Marge! Ouch! Please stop! It hurts!"

"Just a few more things Tina, you're going to be such a good girl for Miss Marge, aren't you? I won't need to call my friend Mike, will I?" (smack smack smack)

"No Miss Marge, please don't call him! I'll keep being a good girl for you! I promise!"

"You're going to be Tina, my fem lipstick girlfriend, aren't you? You're going to learn to dress frilly and pretty, wear makeup, and do all the things a good lesbian girlfriend does aren't you?"

"Yes! Yes Miss Marge, please stop spanking me! Please!"

"Almost done for tonight, Tina. I'm amazed you have any tears left but you're still blubbering like the pretty little lesbian girlfriend I'm going to turn you into, just like your Fairy Godmother." Chuckled Marge. "That's what you want, isn't it Babygirl? Ask me nicely and I'll stop your spanking for tonight." (smack smack smack)

"Ow! Ow! Please! Please Miss Marge! Please turn me into your little lesbian girlfriend! Please!"

"That's my good girl." Marge purred, letting the weeping sissy slide off her lap at last. "Now stay on your knees baby girl. There's something very important that fem little lezzies like you do for their girlfriends, and I'm betting you're going at need lots of practice to get good at it." She said, standing up and starting to unbutton her Jeans.

3 Months later Carmen was back in town and decided to drop by Marge's Bar to have a drink and catch up. She sat at the bar and was greeted by Marge with a hello and a glass of her favorite wine. As they began to chat Carmen's attention was drawn to the woman cleaning off one of the tables.

Tina was the picture of femininity, with blond wavy hair to the small of her back. Her figure, 34, 24, 36 was not hidden by her sheer chiffon, loose blouse that showed how delicate and lacy her lingerie was underneath. Her lacy bra accented her beautiful breasts that could be seen faintly through her delicate bra and sheer blouse. A pink taffeta skater's skirt accentuated her tiny waist and broad round hips. Sheer nude pantyhose covered her shapely legs that were perched in pink patent leather 4-inch heels. Her makeup was perfect, including her bright red lipstick and pretty chandelier earrings dangled sexily brushing her shoulders.

"Wow Marge, who's the new girl? She looks just your type, all dolled up like that." She inquired.

"Remember my asshole Brother-In-law?" Marge asked, lowering her voice and leaning in. "Well Timmy is Tina, my submissive little lesbian sissy."

"What? That's a man? No way!"

"I'll prove it to you." Chuckled Marge. "Oh Tina, come over here, would you?"

"Yes Miss Marge." Tina answered in a soft husky voice, immediately going over to where the 2 women were talking.

"Babygirl" Marge said to the sissy, "Show Miss Carmen here your clitty, would you?"

"Yes Miss Marge." Tina replied, lifting her skirt. Carmen's eyes grew wide as she saw Tine was wearing pink and white frilly crotchless panties, framing the pink steel flat chastity cage between Tina's legs.

"Good Girl Tina, now get back to work sweetie." Marge directed.

"How on earth did you do it Marge?" asked An Incredulous Carmen. Marge then told the story of the gambling debt owed Mike The Bat and how she had agreed to pay him back in exchange for Tim living under her thumb until it was fully paid.

"You do all this in 3 months Marge? You're a magician!"

"It was easy once the little wimp signed everything over to me, plus I had the constant threat of calling Mike as an added incentive." Marge said, lowering her voice. "The first few weeks were a little rough, but mostly on Tina if you get my drift. Once she started getting better at dressing and putting on her makeup, I knew I had broken her. The nightly maintenance spankings helped too. And after the first month she finally learned how to eat pussy like a pro, which helped her stay on my good side. Getting her to French Kiss my ass was cake after that."

"I think what finally broke her was the flat chastity cage. I had to special order a metal one in pink, but it was worth it. The look on her face when she saw I was using a permanent rivet, not a key to secure it was priceless. That was the night I used my strap-on to christen her new pussy for the first time. She pretended to love it, but lately I've noticed her clitty drip while I'm fucking her so I think she may have actually learned to like it."

"Are those real tits on her? If not, they're the best falsies I've ever seen." asked Carmen, enthralled.

"Oh yes. For the first few months we used falsies but then I asked Mike to drop by and we discussed getting her implants. She didn't dare refuse, she's terrified of him, and by now she's my obedient little pet too. I'm thinking of getting a little more work done too. Maybe touch up her face just a little to make it more girly. The corset training and hormones have helped her with her girlish figure, but I'm thinking of having a rib or 2 taken out for more of an hourglass figure. I keep threatening her with tongue lengthening surgery so she can lick pussy better, but just the threat seems to keep her motivated"

"Wow Marge, all that must have cost a bundle. What will happen when the debt to the loan shark is finally paid off? How long will that take?"

"Well ..." said Marge, lowering her voice and leaning in conspiratorially "Remember that land my folks left me that I never had any use for? I sold that for a tidy sum and paid Mike off completely in the first month, but he agreed to keep it just between us. He got such a kick when I told him my plans to turn Tim into Tina he actually gave me back enough to pay for the surgeries. He drops by now and then to have a drink and blow her a kiss though. I think Tina's going to be working off that debt for a very long time."

"Wow Marge that's the hottest thing I've ever heard." Said Carmen "Almost makes me want to get a Tina of my own."

"Well, if her story got your motor running, we can fix that Carmen. Oh Tina, come over here."

"Yes Miss Marge" replied Tina, quickly coming when called.

'Tina, I think my friend Miss Carmen here needs a demonstration of your pussy licking skills. Would you mind taking he upstairs and servicing her? I need her opinion on whether to have your tongue stretched."

'Yes Miss Marge, whatever you say." The sissy replied submissively.

"You're a doll Tina." Carmen said "Are you sure it's no trouble.?"

"No Miss Carmen, it's what I live for. I'm a lipstick lezzie love toy who loves to eat pussy." Tina replied softly as she led Carmen upstairs, a small tear forming in one eye.

The End (Dedicated to Miss C)