I am a young guy in my 20s and had a mind blowing experience last year that I've wanted to write about for a while. I was bored at home one day, browsing the internet and looking at some adult personal ads when one of them caught my attention.
The ad went along these lines:
"Attractive, busty professional woman in late 30s seeks a discrete man to help her live out a sexual fantasy. Please contact me for further details - must be clean, in good shape and discretion is vital. West Mids."
I had never replied to any of these ads before and wasn't even very sexually experienced but was intrigued to learn more. I was just masturbating a lot and hadn't had any sex in a while. So I sent her a polite email saying that I had seen her ad, saying where I lived and that I might be interested. I didn't really expect to hear anything back and half wondered if it was a hoax or even serious. However she replied back, and we exchanged a couple of brief emails before she explained what she wanted:
"I will tell you more about what I want, and if you are still interested and serious, then please reply.
About me: I work as a very successful lawyer in a top firm. I am in a high managerial position and everyday men defer to me. I am single and go to the gym several times a week and I am very fit. I have long, naturally blonde hair, am 5'10", I have curves with large breasts and long legs. Men's eyes follow me wherever I go, but I don't want to get involved with anyone. I've not had sex for several years and I am constantly thinking about sex. I have a big collection of sex toys. However they are not getting me off any more and I need to be fucked by a man. I want to be fucked by a stranger as a one-off situation, and I don't want a relationship. However I want to control the experience, I don't want to pick up someone in a bar that could cause me problems. This is where you come in.
I want you to remain a stranger. I want to see a photo of you from your neck down (I don't want to see your face yet) and I want you to be naked except your underwear. I don't want to see your cock until you are with me. I will need you to sign a legal contract, binding you to do exactly as I request. If you don't do so, I will ruin your life and have you arrested for sexual assault. I will require you to go to a private sexual health clinic twice to get checked out for any disease so you do not have to wear a condom. I will pay for these checks and the results will be sent to me.
This is my fantasy: I have left my office and it is my lunch break. I am walking through the town centre to my house which is about 15 mins walk away to get some lunch. I will wear a business suit with no underwear. As I walk past, you will follow me. You will recognise me as I will be wearing a certain item of clothing and I will tell you where and when to wait. You will follow me home at a discrete distance. When I get home I will go upstairs and kneel on the edge of the bed on all fours. I will move my skirt up to reveal my bare bottom. I will be facing a mirrored wardrobe so will be able to watch you as you come upstairs. I will leave the door open and I want you to come upstairs a couple of minutes after I do. I want you to be wearing smart trousers and a shirt. Do not wear any underwear. Do not speak. In the hallway outside the bedroom, I want you to pause and take our your cock and balls through the fly of your trousers. I want you to leave the rest of your clothes on. Then I want you to fuck me. Fuck me like an animal from behind. Think of your own pleasure. Be rough. You can touch me all over but I want to remain on all fours watching you in the mirror. When you have come inside me or over me - it's your choice, I want you to leave the bedroom and house, and I do not want to hear from you again (unless I contact you).
I want to go to work on that morning, knowing that a stranger will follow me home at lunchtime and fuck my brains out. I will enjoy the anticipation of walking home, knowing that I am being followed. I will enjoy feeling my cunt grow wet as I walk, knowing what is coming.
So, if you are interested, I will have to know that you are discrete, you are healthy, and you can fuck me with a hard cock. In return you will have a free fuck with a powerful woman, and feel free to give it to me as you want to."
As I read this, I grew hard. I couldn't believe what she was asking - a total stranger - to fuck her and then leave. I wondered if I could do it - if I could go through with it. My heart was thumping in my chest even now. But I knew I had to take this chance. I emailed her back and before I knew it, I had signed a comprehensive legal document, sent her my picture (minus my head) and been for a couple of checkups at a very expensive private hospital.
I then received an email from the woman saying that I was healthy and we set a date and time to meet. She said that she would be wearing a grey business suit with her blonde hair pinned up, but she would have a bright red scarf around her neck. I arranged to stand by a particular bank on a corner and wait for her to walk past at the allotted time.
As I got dressed on the morning of the meeting, I found my fingers shaking as I did up my buttons. I was incredibly turned on and nervous at the same time. I felt my cock move around freely inside my trousers, and wondered how I would be able to walk with a huge erection tenting my trousers.