Author's preamble
This story is a work of fiction, any similarities with people and places is purely coincidental. The text remains the intellectual property of the author and may not be published elsewhere without specific permission from the author.
The narrative contains scenes of explicit mutually consenting sexual activities between twins, including spanking and cross dressing. Sexually active characters are over 18 years old. If this kind of story is illegal where you are reading it, perhaps you should navigate to another site. Similarly, if you don't like such stories, I wonder why you are surfing a site that contains such material.
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End of preamble; let's get on with the story ...
Aunt Em's Legacy
When they were seven years old, Patricia and her twin brother Thomas were orphaned. Their parents had been in the front coach of the train bringing them back from a business convention when the train left the tracks and their coach was thrown into the side of a bridge. The children were staying with their aunt at the time and subsequently they were adopted by their mother's sister who had been widowed five years ago. Aunt Emily was the headmistress of a high-class girls' school with a reputation for being strict with the pupils and this attitude was continued with her nephew and niece right from the time they came to stay with her. This was in the 1950s when corporal punishment was acceptable. Any infringement of Aunt Em's strict code of conduct was met with a variety of punishments from being sent to their rooms, being made to leave the table with their meals unfinished, a slap on the thigh or being made to strip naked and receive a spanking on their bare bottoms. For reasons known only to Aunt Em, if one had to strip for a punishment, the other had to strip too.
Aunt Em had one further peculiarity: she did not like little boys. Every evening, when the twins got home from school, Pat had to take Tom to her bedroom and dress him in her clothes. Tom would remain in his sister's clothes at weekends. If truth were told, Tom enjoyed wearing Pat's clothes and she enjoyed dressing him. This regime continued through their childhood and even through puberty. When Pat developed breasts, Tom also had to wear a bra stuffed with cotton wool. He even had his own wardrobe after he had outgrown her so much. He had to wear makeup when his sister started on that phase of growing up. They both stayed with their aunt even when they were old enough to leave home. Aunt Em, although strict, was very careful to hug them after her worst punishments and tell them they were forgiven. She loved her adopted children and showed it in everything.
One morning when the twins were twenty, Aunt Em was not in the kitchen to cook their breakfast as usual. Pat went to her aunt's room and came back in tears: their aunt had passed away in her sleep. This obviously meant there was a big change in the twins' lives. They were just a little surprised when they found themselves the sole benefactors of their aunt's estate except for a few charitable donations. Their late parents' assets were also held in trusts that would become theirs in a few months time on their 21st birthday. Thus, Tom and Pat found themselves independently wealthy so early in life. Their aunt's solicitor put them in contact with a successful financial advisor who recommended a series of trusts and low-risk investments so they would never need to work. Instead, they devoted their energies into charitable works.
Somehow, it seemed natural for Pat to continue dressing her brother and Tom now has his own wardrobe full of feminine clothes and had invested in a set of silicon breast forms. He was so comfortable dressing up that he would usually go out in public as a woman, often with his sister's company. They would go to pubs, restaurants, the cinema or shopping at the Mall, to all intents and purposes as two sisters. One Saturday morning while she was dressing him, he made a confession: "Do you know what I miss most about Aunt Em, Pat? The spankings. Would you believe, I used to enjoy them."
"I know you did Tom. I saw your erections when you went to your room afterwards. But I know just what you mean. Did you masturbate when you got to your room? I know I did after I got a spanking. They made me feel so horny. I think Aunt Em must have known we got pleasure from the spankings: if I could see your erections, she must have seen them too."
"I'm sure she could see the juices trickling down your thighs just as much as I could see them."
"Maybe the spankings were her way of loving us. Even when we had not been naughty, she usually found an excuse for it." She hesitated before continuing, "We could always spank each other, if you like." Tom looked at his sister and saw her eyes were shining. "I even got turned on watching your bottom getting red," she confessed.
"We are so much alike Pat," he responded. "Watching Aunt Em's cane making red stripes on your bottom sometimes almost had me ejaculating in front of you both."
"Let's go to the kitchen, Tom." The kitchen was where their punishments had taken place. When they got there, they stood staring at each other for a long minute then Pat started undressing and Tom copied her. When they were both naked, Pat said, "Spank my bottom hard, Tom, but just your hand this time." Aunt Em had bought a paddle and a cane for their punishments because, she had said, she didn't want to hurt her hand.
Tom sat on the kitchen chair Aunt Em had always used for their punishments. "Over my lap then Pat, I'm going to thrash your bottom until you beg me to stop."
"Oooohh, Tom, yes please."
Carefully she draped her naked body over her brother's equally naked lap, conscious of his erection poking into her. She liked the feel of his hand as he first stroked her bottom then that hand lifted and smacked her right cheek hard. Aunt Em had always insisted that they make no noise during their punishments: no shouting or crying out, they were to take her smacks in silence. Pat let out a moan of desire at that first blow from her brother then kept true to form and remained silent for the rest. Tom liked the big red handprint he had made on his sisters soft and shapely bottom and repeated it on the left cheek. He couldn't resist stroking over the marks gently with his hand, soothing the stinging flesh. He gave her four more hefty smacks then another round of soothing caresses. Pat loved it. She had enjoyed Aunt Em's punishments but Aunt Em had never relieved her bottom lovingly as her brother was doing.
She was not given a lot of time to luxuriate in this unexpected tenderness: Tom started spanking her in earnest, blow after blow landing on her bottom all over the fleshy globes and even down the backs of her thighs. Pat's nipples were rock hard and sensitive to every wobble of her breasts with each stroke of her brother's hand. The pain was no longer a pain, just extra warmth that spread from her bottom to her pussy and clitoris then through her belly. The trickle down her thighs had become a flood when he stopped smacking. "My hand can't take any more, Pat. Now I know why Aunt Em got the paddle and cane."
"Thank you Tom," she panted as she levered herself off his lap. "Now it's your turn."
"Do you want to use the paddle to save your hand?"
"No Tom, but maybe the next time we do this I'll use it. This time I want to feel your bottom under my hand."
He positioned himself over her lap, his erection between her thighs and his bottom high. She copied her brother's tactic of stroking over his bottom before delivering the first few strikes. She liked the feel of soft, smooth skin of the twin globes and he enjoyed her gentle hand in the short respite. When she stopped again briefly, once more stroking his buttocks tenderly, she said, "I wonder if Aunt Em used to enjoy spanking our bottoms. Do you know, I think she did. Do you remember one very hot day when she wore those khaki shorts of hers? That day, I can't remember what it was for but you got the worst punishment ever. She used the paddle and then you got caned and she seemed to on forever."
"Oh yes, that really hurt and I remember I couldn't stop masturbating when I got to my room. Am I crazy or what."
"If you are, we are both as crazy. I had a wonderful orgasm just watching you being caned. What you didn't see because you were in such a rush to get to your room right after Aunt Em's hugs," Pat started a rhythm of spanks again, "was when she stood up from the chair. There was a big dark patch around the crotch of her shorts. I thought at first she had peed herself but, when I looked at her face, she was breathing hard. It was then that I realised she had had her own orgasm. Tom, she looked down between my legs. I was conscious of the fluid running down them and when I looked down, I saw the pool between my feet. I must have gushed; I sometimes do that with a really special orgasm. Aunt Em looked me in the eyes with a grin on her face and winked at me before going to her room. I had my fingers in my pussy as I went upstairs."
Pat was stroking his bottom again. Tom loved this treatment and determined that, the next time he spanked his sister, he would give her more of the same tender intervals. Pat interrupted his thoughts, surprisingly asking, "Would you use the cane on me as much as Aunt Em did on you that time?"
"Certainly not today," he responded. "I enjoyed spanking you and, for now, that is enough. But if you want a good caning in the future, I can do that. While we're telling secrets about Aunt Em, I never told you but maybe an hour after that caning, she came to my room. I had just cleaned up from my third masturbatory session when she walked in, as usual without knocking. She had me lay on my front and she covered my bum and thighs with a cream that eased the pain a little when she smoothed it in. You know how loving and tender she could be. Then she whispered 'Let Aunt Em kiss you better,' and she bent down and kissed my bum cheek. I was masturbating again as she left."
"Oh you lucky boy, I never got that treatment." Pat resumed her spanking although her arm was getting tired and her hand was almost painfully tingling. "I wonder if it was the arnica cream in the cabinet. Probably. That's supposed to be good for bruises and such. We'll try to remember that when we really start punishing each other, which I'm sure, we will be doing soon." She patted his red bum cheeks a couple of times as she would pat a dog then helped her brother stand. They stood facing each other, both of them breathing heavily: the silence was palpable, the atmosphere charged. Tom finally broke the moment, bent down to pick up his clothes and made to move towards the door.
