Tranny Trouble

Copyright Oggbashan September 2018

The author asserts the moral right to be identified as the author of this work.

This is a work of fiction. The events described here are imaginary; the settings and characters are fictitious and are not intended to represent specific places or living persons.

*************************************************

"Tom, you can buy one. I don't mind."

My sister Angela was by my side as we were looking at a stall in the local large boot fair. It was selling Indian clothing. Unlike our stall of books we were selling for a local charity, this stall was covered by a large marquee.

I had just picked up a saree from their pile of sale items. It was very cheap and worth buying just for the length of printed material. Most of the sarees were in transparent bags. The one I was holding was a sample for people to handle.

"Twenty per cent off if you buy our sample one, Sir," the woman said from behind the display. "Or you can buy a set, saree, blouse and petticoat for less than for the total for the individual pieces."

Angela picked up a packet. The blouse size was labelled. The saree and petticoat would adjust to fit almost anyone.

"I like this pattern, Tom," Angela said.

"For you?" I asked.

Angela just grinned at me.

The blouse size would be slightly too large for Angela, but right for me.

"OK, Angela, you've convinced me. Yes."

+++

That purchase wasn't all. The Indian clothing stall was preparing to close, as were most of the other stalls. Rain would be arriving soon and everyone wanted their goods packed away before the rain.

Normally I would have helped the others who were packing the unsold books into my Transit crewbus but I had fallen off my bicycle yesterday, avoiding an opened car door. My back was hurting from pulled muscles and bruising. I had tried unloading the books but it had been too painful.

I had rigged a tarpaulin canopy to the Transit. I had spent most of the morning sitting in the shade of a hot summer Sunday. Unusually for an August Bank Holiday weekend the sun was out and the temperature was high. I had felt useless as Karen and my sisters looked after the stall. Only when the van was nearly packed did I feel that I could walk around the boot fair. Even so, every step had been painful. I couldn't conceal my winces from Angela. She knows me too well.

Angela had to carry the two large carrier bags back to our stall. She had encouraged me to buy so much -- several saree packs, some salwar kamese, a couple of packs of long scarves and the display saree.

"Karen knows," Angela said as we got close to my Transit.

"Knows what?" I asked.

"Knows you are a tranny," Angela said.

I stopped and looked at her.

"How?"

"I didn't tell her. She went to university with Chloe and is still in touch with her, even in Australia."

Chloe had been my girlfriend until she was offered a two year placement in Australia. Although we had been together for nearly a year, she and I agreed that her career was more important than our casual relationship. Chloe had known I was a transvestite and had helped me buy some clothing. She didn't really understand what sexual pleasure I got from dressing up, and being tied up while dressed. She played along but without enthusiasm.

"Karen had seen some of your dressing up clothes in your bedroom over a month ago. She had suspected almost as soon as you started going out with her. She asked Chloe who gave her the details."

"And?"

I was worried. Karen and I had been going out together for about six months and I had hoped we might continue to develop our relationship.

"She doesn't mind. She likes you, likes the way you behave with her, and that you are nothing like her previous boyfriend. She gave me the impression that she would be willing to help you dress up -- in private, of course."

In private? Yes. I dress up behind closed doors. I have no interest in being a woman in the street. It excites me sexually to wear women's clothes in my bedroom. I have dreams of being forced to wear them, and possibly to be a woman's victim but it had never happened. Angela and my other sister Janice knew I was a tranny. Since we became adults sometimes they had taken me shopping with them and helped me to buy my outfits. They had appreciated a brother who had a driving licence and a transit van, especially as I enjoyed clothes shopping with them.

Now they have their driving licences and their own small cars but sometimes only my van would do, like today for the boot fair. It had been painful driving to the boot fair but I couldn't let my sisters and Karen down.

As we reached the van I could see that Janice and Karen had packed everything away. Janice was just shutting the van's back doors. We could leave. Karen pulled me into a hug and kiss. I winced as my back objected.

"Oh dear," Karen said. "I'll have to work on you later. You're a poor advertisement for a trainee physiotherapist."

"You can have him to yourself this afternoon and evening," Angela said. "Janice and I are going out as a foursome with our boyfriends. We're going to stay at Janice's boyfriend's house tonight if there is any of the night left. You could have your hands on Tom all night if you want."

"All night? That could be interesting," Karen said.

"And you could help Tom unpack his shopping,"

Angela added, lifting the two large bags she was carrying for me.

Despite myself, I blushed.

I climbed into the driver's seat. Karen sat beside me. My sisters were behind. I put the key into the ignition and turned. The engine spluttered but didn't run.

"I'll sort it," I said, releasing the bonnet.

I lifted off the air cleaner, poked the butterfly valve on the carburettor that had stuck -- again, replaced the air cleaner, shut the bonnet.

This time the van started.

"Does it do that often?" Karen asked.

"About once a week," I replied. "I should replace the carburettor -- or the whole van. I can't afford that and the mortgage. Maybe next year if I can keep the Transit running that long."

I drove to Angela and Janice's flat. It was above the charity shop that they had been supporting with the book sale. Angela is a volunteer in the shop on Saturdays when she's not working, and had been since she returned from university. She and Janice rent the flat at a discount because the access is only through the shop. They are in the process of buying a small house together. That's another reason why I am short of money. I have increased the mortgage on my house to help my sisters with the deposit. When they move into the house another volunteer from the shop will take over the flat but that is a secret. The other volunteer has fled an abusive marriage and is in a women's refuge now.

As I stopped outside the shop I winced. Braking the van had tweaked my bruised muscles.

"I'm going to get my hands on you this afternoon, Tom," Karen said.

"Is that a promise or a threat?" I asked.

"Depends..." Karen replied.

"Treat him gently, Karen," Janice said. "We love our brother and don't want him beaten up just for you to practice as a physio."

"OK, spoilsport, I'll be careful with Tom." Karen said.

+++

I sat in the driver's seat while the three women unloaded the books into the charity shop. When they finished they all disappeared upstairs to the flat. I was worried, because even though it was a Sunday morning I was parked on double yellow lines. That was permitted while we were unloading but we weren't now.

Ten minutes later the three came back. Karen was carrying a sports bag and had a large soft bag slung over her shoulder. Angela was carrying a cardboard box carefully. She put it down on the van's floor.

"Drive gently, Tom," Angela said. "That could spill if you brake hard."

"I won't. My back would object."

Angela leant over the seat and kissed my cheek.

"Karen will look after you -- and your back. The box contains your evening meal. That's a thank you from your sisters for driving today even when you were hurting."

"Thanks, Angela... And Janice."

Karen climbed beside me. Angela shut the door and I drove off slowly. Just around the next corner I saw a traffic warden approaching.

"We were lucky he wasn't around earlier," Karen said.

"Perhaps. But on a Sunday he probably wouldn't give me a ticket because we were unloading and I had stayed with the Transit. Soon my sisters will have their own off-street parking."

"In their house? I know you're broke Tom, but only because you're helping them. That's why they provided the meal. They know you can't afford to take us out tonight. We're going to have a quiet evening together, perhaps with your purchases..."

"Angela told me you know, Karen. You don't mind?"

"Mind? No. It's part of who you are, Tom. You might enjoy this evening although your back could limit what we do."

The Transit refused to go into reverse gear when I wanted to get onto my drive. I had to engage first, drive forward a yard or two, and bang the gear lever to get it into reverse. I swore under my breath because that bang had jarred my back again.

"Give me your house keys," Karen said. "You sit there until I've unloaded."

I'm not used to having simple things done for me but I appreciated it. Karen even had to help me to climb out of the Transit. I was leaning on her as we walked into the kitchen. I sat down at the kitchen table, lowering myself carefully.

"Right, Tom," Karen said. "You can't go on like this. Sit there while I unpack lunch. Afterwards? You're going to soak in a bath before I try to relieve your pain. But now..."

She kissed me.

"...sit there while I work."

Karen made a salad to go with the quiche. All the ingredients came out of the box Angela had loaded in the Transit.

"Tonight we're having a casserole. It's in the fridge now. I'll take it out about five o'clock. It will need a couple of hours in the oven. You don't have to do a thing."

"Thank you, Karen," I said. "But I feel so useless."

"You're not. You are temporarily injured and have done too much this morning. You shouldn't have driven the Transit."

"I'm the only one insured to drive it, and the only one who knows how to deal with its problems. If Angela and Janice had passed their tests a few years back instead of this year, I could have added them. In their first year as qualified drivers the insurance for them would be more than the Transit is worth. Next year? I might have a better vehicle. Until then we need the Transit to move them to their new house."

"And they need a Tom in working order too."

"Yes. But their move is not for six weeks. I should be OK by then."

"Hmm. Maybe. You haven't seen a doctor, Tom, have you?"

"On a Bank Holiday weekend? No. All I could do is go to A & E and wait for hours and hours."

"You'll have to make do with a part-qualified physiotherapist girlfriend. I know enough to work out whether there is anything serious wrong with your back. If it is only pulled muscles and bruising I should be able to help. If it is more? I'll find out and take you to A & E."

"How? You haven't got a car, Karen."

"Not here. I left it at home because Janice brought me and is taking me back on Tuesday morning. We're going shopping together then. But I could borrow Janice's car, or Janice could drive us to A & E."

"Then three of us would have to wait for hours..."

"You don't get it, do you, Tom? Your sisters love you and would do anything for you because you have done so much for them. You might be a pain sometimes, play the big brother too often, but they know you will be there for them whenever you need them. So do I."

My response was prevented by a kiss that went on and on. We were out of breath when the kiss ended. Karen placed her hand gently across my mouth so I couldn't say anything.

"And I love you too, Tom," Karen said. "You have let me moan on and on about that arsehole of a boyfriend that I dumped. You have shown me that you love me as I am without trying to make me someone I'm not. You've given me confidence to rebuild myself. I asked Chloe about you. She sometimes regrets leaving you to go to Australia but you let her go because it was best for her. That sort of love is rare."

I pulled Karen's hand away.

"I love you, Karen. Yes, I loved Chloe but we knew it wasn't the love of our lives. We enjoyed each other's company, liked each other, but the real spark was missing. We were too different. She was and is adventurous and impulsive. I'm staid, boring..."

Karen's kiss silenced me again. Her hand replaced her lips over my mouth.

"...generous, loyal, reliable and a real friend. Chloe said all that to me. Her version of you was just what I needed, Tom. I was doubtful at first but every word she said was true, yes, including the staid and boring but they don't matter. Now we'll have lunch followed by coffee and a bath for you."

"A bath? I'm not sure I can get into the bath, Karen."

"You will with professional help."

+++

An hour later I was in the bath and Karen was gently washing my bruised back. She was naked down to the waist. I was appreciating the view of her breasts and their softness whenever they touched me. As she washed and rinsed my hair my face was in her cleavage. It didn't need to be, but we were both enjoying the contact.

"Stay there while I get something for you to wear," Karen said.

I relaxed in the bath. She took longer than I expected and only came back with a pair of clean Y-fronts.

"Let's get you out," she said.

She had to help. She wrapped me in a bath sheet and dried me carefully. I put my Y-fronts on as she dried her wet breasts.

"Come on," Karen said.

We went into my bedroom. I had expected her to have got out jeans and a T-shirt. Instead she had opened a packet of the Indian wear. She pulled a saree petticoat over my head and down to my waist. There were soft cord ties on both sides. Karen knotted them, leaving long ends.

"OK, Tom. Put your hands by your sides, please."

She tied the ends of the petticoat strings around my lower arms above my wrists. She picked up the saree and the instruction leaflet. She looked at the leaflet before putting it down on a chest of drawers.

"This end of the saree tucks into the top of the petticoat," she said, doing just that.

"...and wraps around..."

Karen wrapped yards of the saree around my legs pulling each layer tight.

"Now sit on the edge of the bed, in the middle, please."

I sat. The saree constricted. I could barely move my legs.

"Face down..."

She had to help me to get in position. My tied arms meant I couldn't do it myself. My face was in my pillow. I felt her wrap something else around my legs below my knees. I tried to look around but Karen's body obstructed my view. When she had finished my legs were clamped together.

"These long scarves are useful, Tom. You're not going anywhere until I've finished with you. Another couple of scarves..."

She tied those two to the lower end of the bed frame and to the scarf binding my legs.

"Now I'll work on your back."

She took a bottle of baby oil out of her bag. Slowly she spread the oil from my shoulders down to my waist. Her hands stroked gently and softly, easing the tension in my back muscles. She kept going for a quarter of an hour before I began to doze, lulled to sleep by the lack of pain and her gentle touch.

I woke up later as her hands slid something underneath my chest. Was it? Yes, it was. She was fitting the bra with breast forms on me. Carefully she rolled me over and pulled me into a sitting position. I hadn't noticed before but my arms were free and the scarves tying me to the bed had gone. Karen eased my arms into the cropped blouse and fastened it.

"If you can stand up for a minute or so I'll put the saree on properly."

She helped me to stand, unwound the saree, and then pleated it before tucking the pleats back into the petticoat's waistband. She draped the end over one of my shoulders.

She stood back, looking at me.

"Not bad, Tom. You need something more."

She walked over to the chest of drawers and produced my long black-haired wig.

"This is right for an Indian woman. Stand still."

She even had the double-sided tape to hold the wig in place. I felt the hair sliding down my back.

"There you are, Tom, cross-dressed as an Indian woman. Perhaps some cosmetics might help but I don't want to wait this time. It's your fantasy, being transformed by a woman, isn't it?"

I nodded.

"But if Chloe is right, I need to do some more before I can enjoy myself. And you can enjoy yourself too."

Karen picked up one of the long scarves. She tied one end around my wrist, fed it around my body, tied the other wrist, and knotted it behind me. My arms were restrained again. She repeated the process just above my elbows.

"Back on the bed, Tom, face up this time." Karen ordered.

She had to help even though my legs could move inside the saree and petticoat.

"I put these on just for you," she said.

I didn't understand what she meant until she reached under her skirt and produced a pair of blue satin French knickers. She straddled me, sliding her skirt upwards, and held the knickers above my face. She lowered them until my face was hidden by blue satin. She stroked them over my face.

"You can't stop me doing anything, Tom, can you?"

I shook my satin sheathed head.

"So..."

Karen lifted the knickers, scrunched them up into a ball, and held them over my lips.

"Open wide. You're going to eat them."

I opened my mouth. Karen's fingers pushed them in to fill my mouth. She reached behind herself, grabbed the third long scarf, and wrapped it round and round my head, forcing the knickers deeper. She knotted the scarf.

"Can you say anything?"

I grunted, all I could do.

"OK. I haven't given you a safe word. It would be useless anyway since you can't speak. If you want me to stop and release you, just move your head slowly from side to side three times. Got that?"

I nodded.

"Show me the safe signal, Tom, please."

I moved my head side to side three times.

"Good. Well done. If you do it again, you're released. Now..."

Karen climbed off me. She lifted my feet before sliding the saree and petticoat up above my waist. My hands were swathed in layers of saree. She eased my Y-fronts down and off, revealing my erection standing proudly.

"I need this," she said, producing a condom from her skirt pocket, "but you're wearing it."

I groaned into my gag as Karen's finger slid the condom on to my erection. I was so close to a climax. Karen was fulfilling my fantasy of being cross-dressed, bound, and at the mercy of a woman who loved me.

"Just contemplate your predicament, Tom. I could do anything to you. I won't, yet. I'll leave you while I put the casserole in the oven. Back soon."

Karen walked out of the bedroom. I groaned. It was ten minutes or more before she came back. She was wearing a bra now.

She straddled me before stroking her hands over my face. Slowly she rubbed her warm cleft over my erection. She stopped, moved up my body, and pressed her bra-covered breasts on my face. She sat back, unfastened her bra, put it down beside my head, and pressed her naked breasts back on my face.

"Want an eyeful?" She asked.

I couldn't reply.

She pushed her breasts together before lowering her erect nipples onto my eyes. One of her arms slid behind my head to hold it tight against her softness. When she relaxed her hold she slid down me again to feed my erection inside her. She moved up and down, squeezing with her lower lips until I felt that I was at the point of no return.

Suddenly she grabbed her bra, covered my face in a moulded cup, and pressed down. I was breathing her perfume and surrendering to the woman who had dressed, tied and smothered me. My hips bucked upwards as I came into her. Immediately afterwards my back muscles reminded me that I was injured. Karen could feel my body tense.