I am waiting in a nice restaurant in the centre of London. Again, I question if this is a good idea. Before I can change my mind, I see that he has arrived, perfectly on time, so I must go through with the plan. The idea formed about a year ago this meeting is the culmination of a lot of soul-searching, worry, and excitement.
It all started when I watched a video called Caned and Fucked, the title tells you all about the content. It is only a short clip, around four minutes, a man dressed in stockings and suspenders bends over the back of an armchair. He is referred to as she throughout the clip and does look very appealing. Once in position, she receives six strokes of the cane across her panties. She then stands and removes her knickers before bending over for the second six of the best. Following the punishment, her punisher takes her from behind and uses her for his pleasure. Something captured my imagination in the video, I have watched it countless times, and it still excites me.
The funny thing is that I would not describe myself as gay or as a person who would normally dress in women's clothing. In my teenage years, I had a couple of experiences with a boyfriend, but I remain an anal virgin. I still find it strange that this interests me so much, but there is no denying the excitement every time I watch the film. If pushed, I would describe myself as straight but curious. As for corporal punishment, I have played various spanking games with partners in the past, but none have been serious and certainly not as severe as the video depicts, however, the idea of submitting to corporal punishment has always held a fascination.
This curiosity led to today's meeting. After months of searching and many time wasters, I found James, with whom I hoped to recreate the video. We both work in IT--me on the technical side, James in presales--and quickly discovered common interests. Starting with emails and moving to video calls, we honestly shared our feelings and experiences. We finally arranged to meet in central London for its anonymity and neutral ground.
I wave as he enters the restaurant, and he smiles and joins me. In all the stories I have read about these types of meetings, the conversation is easy and relaxed. However, we struggled; the conversation was both forced and stilted. I think we both wanted it to work, after the meal, we stepped outside to find that it had started to rain heavily. James suggested that we go to the National Portrait Gallery, as it was close and, more importantly, undercover.
As we wandered through the various galleries, we both started to relax and feel more comfortable. James is naturally very charming, and this, coupled with his very dry sense of humour, helped to make it a fun and enjoyable afternoon. Neither of us is particularly interested in fine art, but we had a very pleasant couple of hours. After which we went to the café for a coffee.
James asked. "Well, do you want to meet again?"
This was it. I had shared the video with him, and he knew very well what was meant by the question. He was asking if I wanted to dress in women's clothing and then to have my bottom caned and fucked.
"Yes," I stammered. "I think so." And then more confidently, "Yes."
"You can always change your mind, let's agree on Sherlock as a safe word. If you say this at any time, we stop right then. I would like to do this, but I want you to be comfortable too."
He was genuinely concerned, and this only helped to reassure me.
"Yes, please, let's do it. When?" I asked.
We quickly agreed on the following Saturday I would drive over to his house, and finally, my fantasy would become reality.
With this decided, we quickly both went our separate ways. I was already nervous, anxious, and excited about the next weekend, and this only increased during the week. By Wednesday I started to prepare myself, I had thought very carefully about everything I could to make Saturday a success. I needed to shave myself from the waist down. Exfoliating myself took quite some time to get it perfect and smooth. I then admired myself in the mirror. What a change. I bent over and examined my bottom in the mirror. I have a slight build and a small bottom for a man. I thought it looked sexy shaved. I gently pulled my buttocks apart and imagined once again what was to happen on Saturday. I went to bed with an erection and soon dealt with this whilst once again watching the video that started all this trouble.
I decided Thursday evening was to be a dress rehearsal. I had bought all the clothing I was to wear online. I put on the black seamed stockings and attached them to my black suspender belt. I made sure the seams down the back were straight. Once again, I bent to inspect myself in the mirror and liked what I saw. The court shoes with the three-inch heels only enhanced the effect. The sensible skirt and blouse hid what I hoped James would find exciting. I had chosen a brown wig. To finish, I spent a considerable amount of time applying makeup. When I was satisfied, I spent the rest of the evening in my new costume and tried to get comfortable with the new look and walking in the new heels. I was never going to pass as a woman, but I was pleased with the result.
I spent Friday evening in a mixture of excitement and fear. I was both looking forward to and dreading the next day in equal measure, although I went to bed early sleep was a long time coming.
Saturday was a beautiful early spring day. I had already packed my clothes in an overnight bag, so after a small breakfast, I jumped in the car for the hour's journey to the address James had given me. His house was a small cottage at the end of a cul-de-sac. It boasted a very neat cottage garden and looked a lovely residence. James quickly answered the doorbell, and he ushered me into a lounge dining room.
"No second thoughts." He asked.
"I have had second, third, and one hundred thoughts," I replied honestly.
"But you still want this to happen?" He asked in all sincerity.
"Yes, I do. I am very scared but also so excited."
"That makes two of us."
As I looked around the room, I saw the sofa, but I focused on the armchair in the middle of the room. I knew this would be what I was expected to bend over, it was indeed very like the video. I swallowed a large lump that had formed in my throat. I walked into the room and ran my hand along the back of the chair.
"Is this it?" I asked.
"Yes, I expect you to position yourself over this with your bottom fully presented for the cane."
The lump in my throat just got bigger. I then noticed a cane placed on the dining table. It had a crook handle and was around three feet in length. My heart rate jumped, and I imagined what it would do to my bottom shortly.
"Do you want a drink, or are you ready?"
"No, let's get on with it."
"Let me show you upstairs." I followed James up the short flight of stairs. There were two bedrooms. He told me I could change in the spare room and use the bathroom. "Right, I will leave you to get ready. When you come downstairs, we will begin right away. Is that ok?"
"Yes," I whispered.
"Remember the safe word. Take your time, and I will see you soon."
Once again, I questioned my sanity. I could still walk out and forget the whole thing, but deep down I knew that was not going to happen. I had come too far to back out now. Even though now fear overrode excitement, I wanted to see how this played out.
I took my time getting ready. In my previous practice, the seams on my stocking were easy to get straight. Today, of course, it took a long time. I had brought two different types of knickers. I had packed both a thong and a fuller pair of panties. I decided on the larger panties, hoping they would offer some protection. My make-up took longer, probably because I was so nervous, but eventually, I was ready, and taking a deep breath, I went downstairs to face the music. James and I had previously worked out the scenario. What had seemed like fun at the time now seemed very scary.
I entered the lounge. James was dressed in a suit although he was not wearing a tie, he looked very much in charge of the situation.
"Ah, Miss Price, I am glad to see you have arrived."
