House Share

My company was opening a new branch in Poole. Although I did not know anyone in the area, I volunteered and was accepted to join the team responsible for getting the operation off the ground. I was happy to turn over a new leaf having just split up with my long-term girlfriend. There were still recriminations and a lot of fallout from mutual friends. The chance of a change of scene was too good an opportunity to miss.

Finding somewhere suitable to live proved a challenge; properties were either too expensive, overcrowded or run down. Eventually I found a house-share property. The owner had been made redundant last year and had been forced to take a job at a lower salary, and to make up the shortfall, he had decided to look for a housemate. He was a nice guy, very reserved, skinny and houseproud the house was immaculate throughout. This suited me, as I am tidy by nature, it made a pleasant change from my ex, who left mess wherever she went.

In the evenings, as many single guys do, I turned to the internet for sexual excitement. I always find myself drawn to sites featuring spanking, usually with female bottoms receiving punishment. Although I occasionally watch videos of men being punished by either male or female dominates. I find myself watching lots of videos but also reading many of the published stories. My fantasy had always been to wield the cane and mark the bottom of some deserving female. I thought, sadly, it would forever remain just fantasy.

The first couple of weeks went well, work was a challenge with the list of things to get done growing every day. I joined a gym and a running group, deciding it was finally time to make good on my resolutions. Nicolas, my landlord, and I started to relax in each other's company, we went for a drink together on a couple of evenings, which was good.

Before the move I had been invited on a lads' boozy long weekend in Prague. It was not my ideal break, but it would be nice to catch up with some old friends. We were due to fly out of Heathrow on Thursday and return the following Tuesday. I took the time off work, which did not please my boss, but decided it was worth the hassle. I left in plenty of time, but I had not counted on the road being closed around Southampton following an earlier accident, there were roadworks around Basingstoke, and the M25 was a car park as usual. As a result, I missed my flight, and the next available seat was on Friday and would cost a fortune. So reluctantly I messaged the guys and headed back through the traffic to Dorset.

I was thoroughly pissed off by the time I got back home, having wasted the whole day sitting in traffic.

As I entered the house, I heard the unmistakable sound of a cane stroke being delivered. At first, I thought I should just quietly go upstairs, but curiosity got the better of me, and I opened the lounge door.

On the TV there was someone bent over with their bottom decorated with several red stripes. They were dressed as the classic French maid, complete with stockings and suspenders. I then saw Nicolas, at took me a moment to recognise him, as he was wearing a blonde wig. What was most surprising was that he was wearing the same outfit as the maid on the TV; he was holding his rapidly deflating penis.

I mumbled some sort of apology.

"I thought you were away for the weekend," he stammered.

I was shocked and embarrassed to be in this situation. "I missed my flight," I replied to help explain why I was here.

"Oh, god." He cried, and he then ran past me and disappeared upstairs.

The movie was still playing on the TV. On closer inspection, it was not a female being caned but a sissy dressed as a maid dressed in the same way as the now-departed Nicolas. It was obvious that I had stumbled upon his darkest secret. I turned off the TV and went to bed myself.

I lay in bed trying to process what I was feeling. I felt sorry for Nicolas, who must be dying of embarrassment being caught like that. I was also curious that we both shared similar desires about corporal punishment. He seemed to enjoy the idea of being punished, and I dreamt of the opportunity to punish someone. Although I had played spanking games in the past, this had only whetted my appetite for more. The question was, would I want to punish Nicholas? Although I only had a brief look, he did look good in women's lingerie. I found this thought very surprising, and eventually I fell into an uneasy sleep.

When I woke up, I was no nearer the answer to the question, but I heard Nicolas moving about downstairs. As it was Friday, he usually worked from home. Knowing we would have to face each other sometime, I thought I would go down and get a cup of coffee and see how things stood. As I entered the kitchen, he looked at me with embarrassment written all over his face. I smiled and said hello whilst trying to act as if nothing had happened.

"Do you want coffee?" I asked him.

"No, it is all right. I am so sorry about last night. I was not expecting you back."

"I should have called you and told you of the change of plans. I had a totally shit journey to the airport and missed the flight."

"It's okay, you don't have to tell me what you are up to."

I decided to try to calm his embarrassment. Looking directly at him, I said. "Look, how you dress and what you get up to in your own house is entirely up to you. It is none of my business." He nodded, and I asked. "Did you use to dress as a woman before I moved in?"

He went red. "Yes, I spent a lot of my time being my alter ego."

"It must be difficult with me here?"

"Yes, you are great to have around, but it does restrict me."

Before I could stop myself, I said. "Don't restrict yourself on my behalf."

He looked relieved.

"You looked really good," I said before I realised. I also went red as I said this.

He went even redder. "Thanks, thank you very much."

There was silence for a minute, then he asked, "Can I cook you dinner tonight by way of an apology for last night? I guess you are at a loose end since missing the plane."

I was surprised but accepted.

"Dinner at seven." He smiled and looked relieved.

I took my coffee upstairs. The day passed, and we both stayed out of each other's way. I went into town, got a haircut, and then went for a run along the promenade to Bournemouth. When I got home, I showered and went down for dinner just after seven o'clock.

Nicolas looked stunning. He was dressed in a short black dress that looked amazing on him. He was wearing heels and a blonde wig that transformed his look. I stared for a while and said, "Wow, you look stunning."

He smiled and blushed. "Thank you, I decided to take your advice and just dress as I like."

"Good, I am glad."

"Sit, let me get you some wine. I love cooking and don't often have a chance to entertain people."

With this, I was poured a large glass of wine, and soon I was served a wonderful starter of seafood, which I was assured was fresh from the sea that morning. It was delicious.

I was curious, so I asked how long he had dressed as a woman. Nicolas told me he had started in his early teenage years; his sister, who was very close to him, had recognised his feminine side. She was interested in the beauty industry and had started practising using makeup and dressing him in women's clothing. She was able to achieve a good look. He had loved that time in his life; school was hard, but the attention and love from his sibling made up for it. He was still very nervous and unsure of his sexuality, but he now knew he was attracted to men more than women. As he relaxed, he revealed more of his backstory and the difficulties he had before having to accept a lodger. He had got into debt before deciding to share his house. He concluded with, "So, I am still on a journey of discovery but slowly finding myself. My sister and now you are the only two people who know my secret."

I felt very sorry for him being unable to live life as he would choose.

We had salmon for the main course, and Nicolas continued to be the perfect hostess.

After the meal, I said. "Wow, Nicolas, you really can cook. That was delicious."

"Thank you, I usually see myself as Nicola when dressed this way."

"Then thank you, Nicola." I sat and looked at this attractive person in front of me and found myself asking. "What was the video you were watching?"

Nicola blushed. "I am sorry I did get carried away. But I do imagine all sorts of things when I am dressed like this. It does allow me to escape the conventions of normal society."

I nodded. "I can see that, but I think most people would think what you were doing was very naughty." I smiled as I said this. She looked down at her feet and nodded. Then, fortified by a few glasses of wine, I asked. "What should happen to naughty girls?"

There was silence.

"They", she paused, then whispered. "They should be punished?"

My cock twitched. "How should they be punished? The girl in the video had a very sore-looking bottom."

"They should be spanked." She whispered.

"I thought the maid in the film was caned, am I wrong?" I was enjoying the game.

There was a pause. "No, she was caned."

"I thought so." Silence fell. "Do you think I should punish you in the same way?"

"Yes." This time, there was no pause.

"Tomorrow evening, you will present yourself for punishment. At any time, you can change your mind, but if you are dressed as the maid in the video tomorrow evening, I intend to punish you."

"Yes, Sir. Thank you, Sir." My cock twitched. Being called Sir was always a fantasy of mine.

"Do you have a similar uniform?"

She smiled. "Yes, almost exactly the same."

"Please wear it for me tomorrow."

"Yes, Sir."

My cock twitched again.

"Do you have a cane?"

"No."

"I will get one." I didn't know where to find one, but I was determined to succeed. "Could you tell me the name of the video you were watching? I want to recreate the scene if I can." He told me what I needed to know and where to find it. "I will see you tomorrow." With this, I went to bed. My cock was fully erect, and there was no doubt Nicolas was aware of the fact.

Once upstairs, I fired up my laptop and quickly navigated to the video. It was a common enough story that the maid had upset the master of the house and was given a choice between punishment or dismissal. She obviously chose punishment; she was initially hand spanked, this was followed by a hairbrush spanking over her panties, before receiving six hard strokes of the cane over her knickers. Her punishment concluded with six further strokes on her bare bottom. I was very excited by the thought of recreating this. At the conclusion, the maid remained bent over the back of a chair and was buggered by her master. I was less sure about recreating this.

I watched the video several times, making a note of the language used and the treatment the maid received. Obviously, if Nicola enjoyed watching the video, I wanted to excite her fantasies as much as possible. Finally, I searched for local outlets to obtain a cane and found I would have to drive to Southampton in the morning. It was a small price to pay.

Saturday morning dawned with a beautiful, sunny day. Having put the postcode of the Southampton sex shop in the sat nav, I drove through the New Forest, my mind was in a whirl about exactly how the evening would progress.

The shopping trip was successful. I bought a cane, and although I knew it was not in the video, I couldn't resist buying a tawse the shop had on display. I headed into the centre of the city and visited several department stores looking for a suitable hairbrush. Eventually, I found what I was looking for, and I bought a fearsome-looking wooden brush. Happy with my purchases, I headed back to Poole. The car was filled with the strong smell of leather from the tawse.

There was no sign of Nicolas or Nicola when I got back. I made my way to my room and spent the next half an hour practising with my new cane. I did not stop until I was confident that I could land a reasonable stroke where I intended it. If Nicolas was in the house, I was sure he could not fail to hear the swish of the cane. I wondered how he was feeling.

I showered and dressed in a formal suit, trying to recreate the look of the master in the video. I heard Nicola going downstairs just before seven o'clock. I waited for a couple of minutes before collecting the cane and the hairbrush, then, taking a deep breath, I followed her down.

As I walked down the stairs, I tried to get into the role I was to play. When I entered the lounge, I found Nicola dressed as an almost replica of the maid in the video we had both watched. She looked very nervous.

"Right, young lady, you know why you are here?"

"Yes, Sir." Mumbled Nicola, nervously rubbing her hands together whilst failing to make eye contact.

"I cannot have my staff stealing, even small amounts of money. I gave you a choice, dismissal or punishment. Which is it to be?"

"Punishment, Sir, I have nowhere else to go, but Sir, not too hard, it will never happen again."

"The severity or otherwise is not for you to decide, and I fully intend to ensure it does not happen again ever."

"Yes, Sir."

"Let's start with a uniform inspection. Stand up straight, arms by your side." She jumped to obey; we were both into our roles now. She did look just like the maid in the video, wearing a short nylon dress edged with white lace, which barely covered her stocking tops. She was wearing three-inch-heel shiny black court shoes, with black seamed stockings and a black suspender belt. I was pleased to see the seams were perfectly straight. I slowly walked around her, and I liked what I saw, which was a surprise to me.

"Hold your skirt up." Again, she quickly obeyed and showed me her black nylon panties that were struggling to contain her erection. She had a small, tight bottom that the panties hid to perfection; it was a bottom crying out for punishment. Her legs and, I assumed, her pubic region were shaved bare of any hair.

"Well, at least you are dressed properly, that is something."

"Thank you, Sir." Nicola sounded very nervous, which was understandable in the circumstances.

"Now, for your punishment, I have given a lot of thought to this. You will go over my knee for a thorough spanking to warm you up, then I will firmly apply the hairbrush to your bottom."

"Yes, Sir."

"That will prepare you nicely for my cane. You will receive twelve strokes, six over your knickers and the final six on your bare bottom. That should teach you never to steal again."

"Yes, Sir." She looked very nervous and almost tearful now.

"Have you been caned before?"

"No, Sir, please not too hard."

I ignored the comment, "Have you been spanked?"

"Not for a very long time." This surprised me, but I decided I would find out more later.

"Well, you are in for a very enlightening evening, both painful and enlightening."

"Yes, Sir."

"Let's get this unpleasant business over with." Even as I said this, I knew I didn't mean it. I was looking forward to this immensely. I was not sure I could say the same for Nicola.

I placed the cane on the dining table, then I took a dining chair from the table and put it in the middle of the room before finally putting the brush on the floor next to the chair. I sat down and patted my lap. "Over you go." Nicola looked nervous but quickly positioned herself as requested. I looked down and could see her bottom covered in her short black skirt. What a sight it made. I was sure she could feel my obvious erection pushing into her tummy. Although Nicola was scared, her erection was obvious to me as well.

"I expect decorum from you during your punishment. It is going to hurt, but I don't want any shouting or swearing from you. Try to act like the lady you wish to become. Are you ready?"

"Yes, Sir."

"Here goes." I lifted her skirt and laid it over her back. I briefly rubbed my hand over her panty-covered bottom before delivering the first smack in the centre of her left buttock. I heard the first gasp from Nicola. The second smack was delivered to the right buttock, accompanied by another gasp. I was going to take my time and enjoy the experience. I got into a rhythm and continued to spank her whole bottom. I could see the redness of her skin at the edge of the panties. The earlier gasps from Nicola had become small cries of distress, and she had started to wriggle and kick her legs.

"Right, that has got you nicely warmed up, could you please pass me the brush."

With a groan, she picked up the brush and awkwardly handed it to me whilst remaining over my lap.

"Remember, keep your bottom still."

"Yes, sir," she mumbled.

"Stealing is very naughty. You only have yourself to blame." With this, I smacked the brush down; it made a very satisfactory slapping sound, and Nicola jumped in response. Her cry of distress was louder. Although I was enjoying punishing her, I had no intention of pushing her beyond her limits. This was a game I was enjoying, and certainly I wanted to play again. I had to ensure Nicola also wanted to play again, too.

I continued to use the brush on the whole of Nicolas's bottom and upper thighs; she was clearly showing her distress before I ceased.

"Right up you get and stand in the corner for a few minutes to compose yourself before your caning. Nicola levered herself upright, and immediately her hands went to her bottom to try to relieve the sting. She had tears in her eyes.

"You know you have been naughty, don't you?" I reminded her.

She nodded. "Yes, Sir."

"And naughty girls get sore bottoms, don't they?"

"Yes, Sir, I suppose so." She sounded very sulky.

"There is no doubt about it, into the corner. Hands on head, that's enough rubbing." She reluctantly went to the corner I indicated and put her hands on her head. This raised her skirt so I could clearly see her red bottom and thighs that her panties failed to cover. I put the dining chair back and pulled one of the armchairs into the centre of the room; it was a perfect height for Nicola to lean over and present her bottom for my cane. I picked up the cane and gave it a swish. Nicola visibly jumped at the sound. I could only imagine what she was feeling, knowing that shortly, that same noise would end when the cane contacted her bottom.

I stood behind Nicola and gently rubbed her bottom. "Does this feel sore?" I said unnecessarily.

She pushed her bottom into my hand and nodded.

I continued to rub, and she now moaned in pleasure rather than pain. "Do you deserve this punishment?" I whispered in her ear.

"Yes, Sir," she confirmed.

"Good girl, let's get this over with. Place yourself over that chair, bottom uppermost."

She took up the position I requested of her. Her bottom did look very small and vulnerable. It would be a delight to cane her.

I swished the cane a couple more times, and her bottom tensed each time.

"Please, Sir, not too hard, my bottom is already very sore."

"That is for me to decide; your job is to keep your bottom presented properly and push your bottom right out." She pushed her bottom upwards. "Perfect, keep that position."

I laid the cane across the centre of her bottom and gently tapped my intended target area. There was a tense silence in the room. I brought the cane back and delivered the first stroke. It was not very hard but enough to make Nicola jump, and she cried out in discomfort.

"That is number one, bottom back in position."

More reluctantly, this time she pushed her bottom back, and I delivered the second stroke. This was followed by another, louder cry of distress. This pattern continued until the sixth stroke.

"Stand up," I asked. Nicola stood and immediately started rubbing her bottom. "Stop that, you can rub later." She stopped. She now had a couple of tears running down her face, and she looked very sorry for herself. "You have been brave, but you still have the final six coming." She nodded. "Pull your panties down."