A rainy late Saturday afternoon - reality or fantasy?
I was walking through Soho, London and it was raining. It was around 17:00 and due to weather I guess, it seemed very quiet. I walked past a bar and decided to go in to warm up. It wasn't very busy. I walked up to the bar and asked for an Irish Coffee, as that seemed the right drink for the weather.
Every bar has a funny person, so had this one. The guy next to me says, is it raining outside. I say, nah, I just fell in the river, and smiled.
I then noticed that the clientele of the bar was, how do I say this, the kind you would find in a gay bar. But, who cares, it was warm inside and I had a seat. Well, as I said it wasn't very busy, so getting a seat wasn't that hard. The Irish Coffee warmed me up, and I decided to have another one. As I've not eaten much that day, it made me feel a bit lightheaded.
The funny man was still there, I then noticed he was actually fairly attractive. So I offered him a drink. He accepted and we went to sit at a table. No names were exchanged. He said, I know this is a cliche, but I've never seen you here before. I said, you are correct, first time. I just went into the first bar I saw. He looked at my hand and said, are you married. I said, yes I am. I smiled, and said, is that an issue? Not for me he said. I said, well not me either, we are just having a drink and a chat. Very innocent. Yeah, yeah was his answer.
What do you mean, I ask? He answers, you do know this is a gay bar? I guessed that I respond. Does that mean, straight people aren't allowed in? He laughed and said, well you are here and we've not kicked out. Does that answer the question?
It turns out he is the owner, his name is Jack. Jack says, you didn't come in to pick up a man or being picked up. No, I just wanted to get out of the rain. Are you not uncomfortable being in a gay bar? Should I be, I respond. Well most straight / married men would be. I said, no issue for me. We chatted and he offered another drink. I said, if I have another Irish Coffee, I may get in trouble. He looked into my eyes, and said, would you like that? I said, get me another drink.
Jack suggest, as my clothes are still at least damp, if not wet, that we go upstairs where I can dry them. That's not an indecent proposal I hope, is my response. Of course not, he says. I'll get you a drink upstairs.
We go upstairs. He points to where the bathroom is. Go there, take your clothes off, there is a clean dressing-gown at the back of the door. The heating rack in the bathroom is on. Use that to dry your clothes. I say, thank you and walk to the bathroom.
When I come back, Jack asks me what I want to drink. You wouldn't have any cognac I say. I own a bar he says, of course I do. He pours me a glass. He then asks if I am up for a surprise. Always, I say. Ok, is his response, give me about 30 minutes. 30 minutes, I say, I'm intrigued. I ask if I can smoke. No problem, he gets me an ashtray and says, there are some magazines if you are interested.
When he is out of the room, I look at the books on the shelves. He has a very eclectic taste. I sit down on the sofa and pick up one of the magazines. It's BDSM/Kink one. Mainly focussed on a TV/TS/TG/CD audience. I light a cigarette and start reading and looking at the pictures.
I've not noticed that my dressing gown exposes me a little, but am too engrossed in the magazine to pay attention. This means I also haven't noticed Jack coming back in. Nice view I hear a voice say. I look up, huh, what, where? The person I see isn't the Jack that left the room, it's a gorgeous, sexy, woman in leather. I've got to swallow twice, before I finally can sort of say, wow. That's it, wow. I'm Jacqueline she says. Then she points at my open dressing gown and says, that's no way to dress for a lady.
I'm sorry Milady I say. She comes over and sits next to me. Are you into BDSM she asks? I say, that I'm interested and have played a little with my wife. Were you submissive or dominant? Submissive I say. I tell her it's been a while. My wife is too busy, and to be fair, so am I. I may get the occasional hand- or blow-job.
I tell Jacqueline that over the years, like I guess many man, have had fantasies about sex with men or shemales. I've never gone any further than a fantasy. But I started to notice that, while masturbating, sex with men and/or shemales became more and more prominent and a much bigger turn on. This lead me to starting to watch that kind of porn. I had decided however, that if it would happen in real, it would have to be spontaneous.
She looks at me and smiles. She asks, do I turn you on, dressed like this. I look at her and say, yes very much. I'm nervous, I admit, but I do like what I see.
What time do you need to be home, Jacqueline asks? No time, the wife is away the weekend with friends. Then she says, do you want to play and be my submissive for the afternoon? Yes please, I say.
Ok she says, do you know what a safeword is? I say, I think so, but please tell me. So she explains it. I choose red.
She then tells me from now on, I can't speak without approval. I can't look her in the eyes. When answering I must address her with Mistress.
I am told to take of my dressing gown.
She positions herself on my lap and starts kissing me. It's the first time I kiss a shemale. I lose my self in the kiss. When I my hands go to her breasts, she slaps me in the face. Did I allow you to do this? No Mistress I say. I'm sorry Mistress.
Just before Jacqueline leaves the room, she instructs me to sit on my knees and my head bowed down. Which I do. I hear her walking back into the room, but as per instruction do not look at her.
I'm told to position myself in a doggy position. Ass up, head down. A gag is put in my mouth, but I'm asked if that's ok. I say, not sure Mistress but I will try. I feel her fingers stroking my ass and I feel a finger going up my ass. It's well lubed, I think. A second, third and fourth finger go up. They are pulled out without a warning and replaced by a butt-plug. My eyes are filled with tears, but I love it. It's a mixed up feeling. Jacqueline tells me that this is my training to be stretched.
She says, take your time. Let it settle. Which I do. After a while, I'm told to stand up and follow her. We reach a room, which is basically a BDSM dungeon. It's not huge, but has just enough of being fully functional.
I'm restrained onto a bondage bench. As I've not seen Jacqueline's cock I don't know what to expect. I feel the plug being pulled out of my ass and replaced with a bigger size one. Jacqueline stands in front of me and says, we need to stretch you up a bit more. When she shows me her cock, I nearly faint. It must be at least 12 inches. She takes the gag out of my mouth and slowly puts her cock in my mouth. It's not even hard but it's enormous. I feel it grow and going deeper and deeper into my throat. There is no force as she realises this is new to me and she pulls out to ensure I'm not dying or throwing up.
She then makes me kiss a paddle that is will be using to spank my bottom with. 10 on each cheek. The paddle is swapped for a whip, which she makes me kiss before she starts using it on my back. As this is all new to me, I'm overwhelmed by a myriad of feelings.
Jacqueline stands in front of me, and tells me to suck her cock until it's hard. Which I do. She pulls it out of my mouth and walks away. I feel the butt-plug being pulled out. I feel a huge amount of lube going into my ass. Then slowly but surely her cock is making its way into my ass. My eyes are filling up with tears and I start to scream. I hear her laugh, but as I'm not using the safe word she goes in deeper and deeper and then starts to fuck me. First slowly and gently, then harder and faster. I'm in pain, I'm in lust. I just love the feeling.
She pulls out and comes over to my face. She removes the condom and starts fucking my throat. No compassion, just hard. Then she explodes in my mouth. I try to swallow as much as I can, but it's so much, well I think, I can't. She pulls out and there is cum dripping on the floor, from my mouth and chin.
I'm untied and forced to lick the cum of the floor. I'm taken to a bench where she ties me up and starts to play with my cock. Only her hand because as she tells me, I'm not worthy of her mouth. Then finally she allows me to come, catches it on her hand and makes me eat it.
She unties me. Tells me where the shower is and tell me to be back in less than 10 minutes.
I quickly shower, we walk to the living room. We chat about the experience while smoking a cigarette and having a drink. I tell her that it was one of, if not the most intense sexual experience I ever had.
She takes my phone number and says, she'll call me for a next catch up. Once she decides if I was good enough.
I say goodbye and leave. "Praying" that I'm receiving a call from her. If I will, that will result in another story.
Every bar has a funny person, so had this one. The guy next to me says, is it raining outside. I say, nah, I just fell in the river, and smiled.
I then noticed that the clientele of the bar was, how do I say this, the kind you would find in a gay bar. But, who cares, it was warm inside and I had a seat. Well, as I said it wasn't very busy, so getting a seat wasn't that hard. The Irish Coffee warmed me up, and I decided to have another one. As I've not eaten much that day, it made me feel a bit lightheaded.
The funny man was still there, I then noticed he was actually fairly attractive. So I offered him a drink. He accepted and we went to sit at a table. No names were exchanged. He said, I know this is a cliche, but I've never seen you here before. I said, you are correct, first time. I just went into the first bar I saw. He looked at my hand and said, are you married. I said, yes I am. I smiled, and said, is that an issue? Not for me he said. I said, well not me either, we are just having a drink and a chat. Very innocent. Yeah, yeah was his answer.
What do you mean, I ask? He answers, you do know this is a gay bar? I guessed that I respond. Does that mean, straight people aren't allowed in? He laughed and said, well you are here and we've not kicked out. Does that answer the question?
It turns out he is the owner, his name is Jack. Jack says, you didn't come in to pick up a man or being picked up. No, I just wanted to get out of the rain. Are you not uncomfortable being in a gay bar? Should I be, I respond. Well most straight / married men would be. I said, no issue for me. We chatted and he offered another drink. I said, if I have another Irish Coffee, I may get in trouble. He looked into my eyes, and said, would you like that? I said, get me another drink.
Jack suggest, as my clothes are still at least damp, if not wet, that we go upstairs where I can dry them. That's not an indecent proposal I hope, is my response. Of course not, he says. I'll get you a drink upstairs.
We go upstairs. He points to where the bathroom is. Go there, take your clothes off, there is a clean dressing-gown at the back of the door. The heating rack in the bathroom is on. Use that to dry your clothes. I say, thank you and walk to the bathroom.
When I come back, Jack asks me what I want to drink. You wouldn't have any cognac I say. I own a bar he says, of course I do. He pours me a glass. He then asks if I am up for a surprise. Always, I say. Ok, is his response, give me about 30 minutes. 30 minutes, I say, I'm intrigued. I ask if I can smoke. No problem, he gets me an ashtray and says, there are some magazines if you are interested.
When he is out of the room, I look at the books on the shelves. He has a very eclectic taste. I sit down on the sofa and pick up one of the magazines. It's BDSM/Kink one. Mainly focussed on a TV/TS/TG/CD audience. I light a cigarette and start reading and looking at the pictures.
I've not noticed that my dressing gown exposes me a little, but am too engrossed in the magazine to pay attention. This means I also haven't noticed Jack coming back in. Nice view I hear a voice say. I look up, huh, what, where? The person I see isn't the Jack that left the room, it's a gorgeous, sexy, woman in leather. I've got to swallow twice, before I finally can sort of say, wow. That's it, wow. I'm Jacqueline she says. Then she points at my open dressing gown and says, that's no way to dress for a lady.
I'm sorry Milady I say. She comes over and sits next to me. Are you into BDSM she asks? I say, that I'm interested and have played a little with my wife. Were you submissive or dominant? Submissive I say. I tell her it's been a while. My wife is too busy, and to be fair, so am I. I may get the occasional hand- or blow-job.
I tell Jacqueline that over the years, like I guess many man, have had fantasies about sex with men or shemales. I've never gone any further than a fantasy. But I started to notice that, while masturbating, sex with men and/or shemales became more and more prominent and a much bigger turn on. This lead me to starting to watch that kind of porn. I had decided however, that if it would happen in real, it would have to be spontaneous.
She looks at me and smiles. She asks, do I turn you on, dressed like this. I look at her and say, yes very much. I'm nervous, I admit, but I do like what I see.
What time do you need to be home, Jacqueline asks? No time, the wife is away the weekend with friends. Then she says, do you want to play and be my submissive for the afternoon? Yes please, I say.
Ok she says, do you know what a safeword is? I say, I think so, but please tell me. So she explains it. I choose red.
She then tells me from now on, I can't speak without approval. I can't look her in the eyes. When answering I must address her with Mistress.
I am told to take of my dressing gown.
She positions herself on my lap and starts kissing me. It's the first time I kiss a shemale. I lose my self in the kiss. When I my hands go to her breasts, she slaps me in the face. Did I allow you to do this? No Mistress I say. I'm sorry Mistress.
Just before Jacqueline leaves the room, she instructs me to sit on my knees and my head bowed down. Which I do. I hear her walking back into the room, but as per instruction do not look at her.
I'm told to position myself in a doggy position. Ass up, head down. A gag is put in my mouth, but I'm asked if that's ok. I say, not sure Mistress but I will try. I feel her fingers stroking my ass and I feel a finger going up my ass. It's well lubed, I think. A second, third and fourth finger go up. They are pulled out without a warning and replaced by a butt-plug. My eyes are filled with tears, but I love it. It's a mixed up feeling. Jacqueline tells me that this is my training to be stretched.
She says, take your time. Let it settle. Which I do. After a while, I'm told to stand up and follow her. We reach a room, which is basically a BDSM dungeon. It's not huge, but has just enough of being fully functional.
I'm restrained onto a bondage bench. As I've not seen Jacqueline's cock I don't know what to expect. I feel the plug being pulled out of my ass and replaced with a bigger size one. Jacqueline stands in front of me and says, we need to stretch you up a bit more. When she shows me her cock, I nearly faint. It must be at least 12 inches. She takes the gag out of my mouth and slowly puts her cock in my mouth. It's not even hard but it's enormous. I feel it grow and going deeper and deeper into my throat. There is no force as she realises this is new to me and she pulls out to ensure I'm not dying or throwing up.
She then makes me kiss a paddle that is will be using to spank my bottom with. 10 on each cheek. The paddle is swapped for a whip, which she makes me kiss before she starts using it on my back. As this is all new to me, I'm overwhelmed by a myriad of feelings.
Jacqueline stands in front of me, and tells me to suck her cock until it's hard. Which I do. She pulls it out of my mouth and walks away. I feel the butt-plug being pulled out. I feel a huge amount of lube going into my ass. Then slowly but surely her cock is making its way into my ass. My eyes are filling up with tears and I start to scream. I hear her laugh, but as I'm not using the safe word she goes in deeper and deeper and then starts to fuck me. First slowly and gently, then harder and faster. I'm in pain, I'm in lust. I just love the feeling.
She pulls out and comes over to my face. She removes the condom and starts fucking my throat. No compassion, just hard. Then she explodes in my mouth. I try to swallow as much as I can, but it's so much, well I think, I can't. She pulls out and there is cum dripping on the floor, from my mouth and chin.
I'm untied and forced to lick the cum of the floor. I'm taken to a bench where she ties me up and starts to play with my cock. Only her hand because as she tells me, I'm not worthy of her mouth. Then finally she allows me to come, catches it on her hand and makes me eat it.
She unties me. Tells me where the shower is and tell me to be back in less than 10 minutes.
I quickly shower, we walk to the living room. We chat about the experience while smoking a cigarette and having a drink. I tell her that it was one of, if not the most intense sexual experience I ever had.
She takes my phone number and says, she'll call me for a next catch up. Once she decides if I was good enough.
I say goodbye and leave. "Praying" that I'm receiving a call from her. If I will, that will result in another story.
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