Old Folks Ch. 01

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Young man finds out Frank isn't who he said he was.
14.6k words
4.48
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Part 1 of the 2 part series

Updated 09/22/2022
Created 01/24/2008
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I had been cross-dressing for some years, but I had never been with another man. I had been talking on a gay chat site for some months when I found someone who I got on with well. We exchanged photos I was happy with his and he was happy with mine. Deciding to get together, we arranged a date and time to meet and be for the first time with another man.

I had traveled a good 80 miles to meet this chap, who said he had his own place and had a range of clothes in my size. I eventually found the right house and knocked on the door and waited for an answer. The door opened after a few seconds and a much older man than the photo stood in the doorway, he was probably around 50 for a guess.

"I'm sorry, I think I've got the wrong house." I said in embarrassment.

"Is your name Mark?" he asked.

"Yes, it is."

"You best come in then." he said.

I walked into the house, which was actually a bungalow, hoping this wasn't the guy I was talking to on the Internet. He didn't look like the picture I was sent and if he was the guy, I was out of there.

He opened a door and inside were a girl's bedroom, pink wallpaper, pink carpet and four poster bed with white netting hanging down.

"Make yourself comfortable, pick what clothes you want to wear and I'II be back in a few minutes." he said.

"I'm sorry, but I'm looking for a guy called Frank." I said.

"He'll be here in 10 minutes, he'll be back shortly." he replied.

My nightmare was sort of over; at least that older guy isn't Frank, the younger man I had arranged to meet on the Internet chat room.

I looked around the room and it was definitely a girl room, the pink color was nearly on everything. There was also an up to date PC on a desk with a nice leather chair and a decent size TV mounted on the wall. I looked at the cd collection and there were some very girly tracks in the collection, I was starting to wonder whose room this is. I opened the wardrobe and inside was a range of tops, skirts and the tight girly trousers. I opened a chest of drawers and inside the top drawer was a range of underwear: g-strings, thongs, girl boxers the lot. I opened the second drawer and inside was an assortment of bras, Basques and corsets. I opened the last drawer and inside was a collection of stockings in different colors, tights and a few pairs of very girly socks. Next to the chest of drawers was a nice makeup table with a large mirror in the center, the table was littered with perfumes and deodorants along with a deep box filled with nail varnish and another one filled with various kinds makeup.

Suddenly the door opened, I looked around expecting to see this Frank fella in the doorway but instead stood an older woman who was about the same age as the older chap. From her looks it looked like back in her day she used to be good looking.

"Sorry love, did I startle you? My name is Honey. I thought I'd give you a hand getting dressed." she said in a very soft feminine voice.

Before I could answer her she came over and opened the chest of drawers, had a quick rummage through and pulled out a black satin thong with a small line of black lace around the edges. After going through the second and third drawers she had found a black matching boned corset to go with the underwear and a pair of black lace top hold-up stockings.

"You undress and put the underwear and corset on." she ordered in her soft voice. I looked at her for a few moments and she turned and faced away. I nervously took off all my clothes and very quickly slipped the black satin thong on and the corset.

"Ok." I said giving Honey the all clear to turn around.

She turned around and gave me a good look. "Turn around dear and hold the posts on the bed." I turned towards the bed and put my hands out stretched holding the posts of the bed as Honey came behind me unknown what she was going to do. I felt her tightening my corset, pulling the strings tighter and tighter pulling my body in and giving me an hour-glass figure. I was getting out of breath and she kept pulling.

"Enough, you can't go any tighter." I wheezed.

"Rubbish, back in my day we had these things so tight we were like pencils. I need to tie it tight so it will give you a very nice girly figure for Frank."

A few more ties and she was done, my figure must be really good as the corset was really tight. I could just barely about move! I turned around and Honey was holding a red nail varnish in her hand.

"I'II give these toes a nice color and then your finger nails before you put your stockings on." she said as she bent down and started to paint my nails one by one a bright red color.

"You'll be able to get that off afterwards won't you?" I asked.

"Of course dear don't worry, nearly done now anyway."

A few moments passed to let the nail varnish dry as Honey told me about Frank and how he's always wanted to meet a girl like me. Honey handed my stockings and I slowly slipped them up my hairless legs as I always shave my body hair off and pulled them up to the top of my thighs. Once I had this done Honey had picked some clothes for me out the wardrobe. On the bed was a dark blue denim skirt about knee height, a figure hugging black strappy low cut top and a high cut long sleeve top with see-through sleeves. I put the clothes on one by one and then Honey led me over and sat me down at the makeup dresser. She took my left hand first and started to stick on false nails, which were about half an inch long. I asked if they would come off after and she assured me they would. Once she put all the nails on both hands she painted them a bright red to match my bright red toe nails which stood out from underneath my black stockings covering my smooth hairless legs.

Honey then applied a light coat of foundation and a little blusher on each cheek to give me some nice color, she followed that by a blue eye shadow which she covered from my eyelid all the way up to my eyebrow. I was watching her do this in the big mirror on the makeup table and I could see a good looking girl starting to form out of me, black eyeliner was next on with a slight flick at the end of my eye and some eye lash curling mascara was next. Finally pink lipstick was put on my lips with several coats of lip gloss which gave my lips a wet look and made them look fuller too.

"What you think?" asked Honey.

"Very good, I'd fuck myself I look that good." I joked.

Honey smiled back at me as she put some medium size clip-on gold hoop earrings, a necklace with the play bunny symbol on, a gold watch, bracelet and ankle bracelet set and a few rings on each finger. Last but not least a shoulder length light brown wig.

"Stand up and let me see you."

I stood up as Honey admired her work. "You look good love, you look real good. Like a real young woman, Frank will be pleased. FRANK. FRANK. Come in, she's ready now." shouted Honey. I was nervous that Frank was coming now, but I did look very good, you couldn't tell I was a man really except I had no breasts. The door opened and to my horror the older man who answered the door was Frank, not the young man I was expecting in the picture.

"What do you think of her Frank? I thing she looks good." asked Honey.

Frank came over to me; he was actually about another foot taller than me as I was just about 5 and a half foot tall. He walked around me; looking and staring at me he went behind me took a squeeze of my ass and stroked my legs.

"Yeah, she'll do." he said as he winked at me.

"I think we've got our wires crossed somewhere, the photo you sent me was of someone a little younger. I really appreciate Honey how you made me look, I actually look stunning, but Frank you're not the picture you sent to me." I said.

Honey suddenly slapped me hard across the face and pushed me down onto the bed.

"You listen here you dirty cross-dressing whore." she said in a very angry voice "You want to dress like a woman and I've made you look like a woman, not like that embarrassment in that picture. You came here with the intention of having your ass fucked by Frank and sucking his cock, well you might be sucking his cock but he won't be fucking your ass you dirty bitch."

"You see we're getting old now and we need some money, so we needed a good little whore to be our hooker and get us some money in and you was right on the money. So you see we're just giving you what you want. Now you're going to do as your told and be a good little cock sucking slut of a hooker, make us some money and live here for the rest of your life!"

"I don't think so bitch!" I bellowed as I quickly stood up but was slapped again by Honey and pushed back on the bed.

"Quick Frank grab her, and I'II attach it." she ordered.

Frank quickly jumped on the bed and held me down. He was too strong against me and I was unable to push him off. I felt Honey lift up my skirt, pull aside my underwear and attach something round the base of my cock. It felt cold like metal and was a ring shape.

"OK Frank let her go now, she'll behave."

Frank let me go and I sat up on the bed.

"Right slut, you're going to do as you're told. I've attached a cock ring to the base of your dick, but it's not a normal cock ring. This baby can put lots volts through your cock and barbecue it in a few minutes. Let me show you."

Honey pressed a red button on a small black remote and I felt an huge shock of pain around the base of my cock and surge up my shaft and down into my balls. The pain was unbearable as she kept the button held down for a few moments as I held my groin area in pain.

"I'm glad you understand." Honeys expression and voice turned back again to her softer side. "You're going to live here and be our niece, your job will be a she-male hooker and me and Frank will be your pimp's. You will give all your money made from selling yourself to us. In return you will live in this room, which has everything you want. You can go on the Internet; we have book-marked all the gay chat rooms for you, she-male porn sites, trans-gender help pages and trans-gender shopping. We can see everything your doing on the computer in another room, so don't try anything funny. If you want any clothes, jewelry, etc., just ask us and we will pay for it. You will not have to do anything else, we will look after you and pay for everything as long as you make a good day pay of whoring. We will also pay for all the treatments you'll have to make you more feminine. Do you understand me?"

I nodded my head in agreement. I knew I'd escape shortly and didn't want to risk having Honey press that button again.

"Right we need a new name for you dear, what shall we choose. Frank, do you want to decide a name for our new niece?"

"Ok Honey, hmmmm, I think she looks like an sexy Maria to me." Frank has just christened me my new female name, which I would now be called while imprisoned by these two maniacs.

"Ok Maria, I'm going to take you out shopping and make you more girly. Here put on these boots and this coat." said Honey.

I looked at the black knee high boots and the long black warm coat and sat there on the bed. Suddenly I felt the pain again in my cock, this time longer than before. I looked at Honey and she looked back at me. I reached and picked up the boots and slipped my feet into each one and zipped them up to my knees, I then put the coat on. I caught a quick glimpse of myself in the mirror and I did look very attractive and convincing.

"Bend over the bed Maria." ordered Honey softly.

I bent over the bed worried I was going to be electrocuted in my cock again; my ass sticking up in the air worried what she's going to do. I felt her lift up my coat and skirt then slip my sexy black thong out of my ass.

"Do you want do the honors Frank?" asked Honey.

"Ok sweet-pie, I'II christen her ass too." he replied.

I then felt something cold and wet slide in between my cheeks and up my ass, it was getting bigger and bigger it started to hurt a bit as something big was trying to be squeezed in, suddenly it went straight in and I could feel a thin part again of whatever it was. Honey pulled my thong, skirt & coat back into place.

"I thought I'd stick a nice girly clear butt plug up your ass seems you come here for something in your ass, and you need to get used to having things up you too. Here take this handbag, as well." she said as she turned me back round.

Honey passed me a small black handbag which I slipped over one shoulder.

"Right then, lets get you sorted Maria. Follow me."

I followed Honey through the kitchen and through a door which led into the garage where their car sat. I opened the passenger door and got in as Honey got round the other side and jumped in the drivers side and we was soon off on our shopping trip to make me more "girly" as she put it.

We had been traveling in the car for about 20 minutes to where ever we were going when Honey's mobile rang. It was Frank and they were talking on the speaker phone over the hands free system.

"Hi Honey, is Maria behaving herself?" asked Frank.

"Yeah Frank, she's been a darling so far." she replied.

"So you haven't had to use the button yet?"

"No, no she's been sitting here just fine."

"Good. I'm so excited Honey, she's going to bring in a lot of money for us when you've finished with her and I know once she's got over her upset she's going to love us."

"Yes Frank, I know, I'm excited too but we have to be tough with her."

Their conversation carried on for another 10 minutes before Frank hung up. I thought now I'd use the time to get some answers on why they were doing this.

"Honey, why are you doing this for? You know you're keeping me prisoner and your both going to get in serious shit," I questioned.

"Maria, nothing is going to happen. No one is going to get into trouble, and if you open your pretty mouth when we're out you'll have no penis left. You understand me." she replied.

"So why are you doing this for?" I asked again.

"Why? As I said we need some money, and the best trade is being a hooker. With you been a sexy she-male hooker your going to be reeling them in, you wanted this at the end of the day so we've just helped you. You want to dress like a woman, so we're helping you dress like a woman and you want sex with men so we're helping you have sex with men. Plus we're giving you a roof over your head, keeping your warm and fed and will provide for anything you like. Even if you did tell someone they wouldn't believe you because we have covered all ends and once we have finished with you, you will look nothing like you did before you'll look like a beautiful pre-op transsexual."

"Actually I think it would be better to say your going to look like a girl with a dick as I'm going to make you look so beautiful, I used to be a beauty consultant so I know what to do and how to use it. Right we're here now so you best behave yourself and do as I say or else it will be fried penis for you!"

I got out the car and Honey and I walked across the car park towards the shopping center.

"Maria I'm going to give you some tips to help you pass better." she said.

"Walk slower in high heels, take your time in them and when you walk try and swing your hips a little bit the butt plug should help you a bit. When you talk to people soften your voice, make it sound more feminine. Say something to me"

"Let me go." I said in my normal voice. I felt the sharp pain again in my cock and I stopped on the spot.

"Let's try again shall we Maria, say I would like to go shopping."

"I would like to go shopping," I said like an obedient puppy in a soft voice.

"Ok, do it again but a little softer." she ordered.

I said the same words another five times before she was happy. "Right Maria walk over to that poster over there and walks back, remember make you hips swing and if you try anything funny there'll be trouble."

I slowly walked over to the poster, which was about 5 meters away on a wall swinging my hips as I went and walked back. I couldn't run in these high boots and if I could I wouldn't I be able to get out of range before she pressed the button. I walked back to Honey and she gave me some rubbish to put in a bin about 6 meters away and swing my hips more. I came back to her and she was happy.

"You're doing good angel. I think you actually want to be a woman as your doing a very good job," she said as we went inside the gigantic shopping center.

We had been shopping about an hour and we had been in plenty of clothing shops. Honey encouraged me to say if I liked anything. Since I was a cross-dresser looking at women's clothes was exciting and been outside in public dressed as a woman was a thrill, although it was a shame about the circumstances. A lot of things I told her I did like, which I actually did like them and not out of fear of having pain in my penis again. When I said I liked something Honey looked at it herself to decide if it would look good on me or not. If she thought it would look good, she would buy it. So far I had ended up with two strappy tops, one long black skirt, a new Basque, a few pairs of underwear, a black knee length strappy dress and some strappy black high heels and Honey told me we still had plenty of shops to go.

"Right lets stop here and have a loo break." said Honey I followed her into the women's toilets worried that some woman might spot I was really man even though I did look very convincing. There was quite a few other women in the toilets looking in the mirror doing there makeup, chatting, etc.

"Remember to sit down, Maria love, if you're going to the toilet. When your done, wait here. Don't think of doing anything else." said Honey as she issued a warning to me.

I went into the cubicle hung up my long coat, dropped my skirt and underwear and sat down on the toilet doing my business as the butt plug hung out my ass, it was a good thing that I only needed to pee. I came out the toilet and Honey was talking to a few women who all stared at me when I came out. Honey moved away from them and stopped talking and went over to the mirror checked and re-applied her makeup.

"Maria, come over here you silly girl and check your makeup."

I went over to her and put my handbag on the sink units.

"Do your makeup bitch, or you'll give the game away." she muttered.

I opened my handbag and found the same makeup in there which Honey used on me earlier. I put on some more lipstick and little more gloss and that was enough for me and we left the toilets with my bags of shopping. I followed Honey around the shopping center carrying the bags of goods the best I can with my high heel boots clacking on the tiles floor, I had also managed to get a few looks from men I hope it was for the right reasons though. We eventually came to a store which was called Transformation; it was a shop for trans-gendered people. I followed Honey inside my eyes roaming around the shop looking at all the feminine clothing for men who wished to look like a woman; we went straight to the main cash desk where a young but definite transsexual stood behind the counter.

"This is my nephew who now calls himself Maria. As you can see he's been a brave chap and changing his appearance to be like a beautiful young woman. We're after some breasts for her, can you help us?" asked Honey.

The assistant turned to me "What size you after honey?" quizzed the shop assistant.

I felt a light pain from the cock ring around my penis I knew I had to answer, my cheeks also glowed bright right in embarrassment but I doubt the shop assistant could see because of the makeup I was wearing. "Err...C Cup please." I managed to murmur in my feminine voice.

"Follow me," said the sales assistant.

"You stop here and find some nice clothing, Maria. I'II go and pick some nice breasts for you." ordered Honey.

Honey left trailing the assistant to the back of shop; I knew it was my time to escape. I slowly made my way to main entrance of the shop stopping and pretending to look at various underwear but really checking if Honey was looking. She wasn't, she was more interested in selecting some fake breasts for me. I got to the entrance of the shop I was about a foot about from stepping over the threshold and being free when I felt a hand on my shoulder, I was dreading if it was Honey. I turned around and a small female shop assistant was behind me.