I Used to Work in Chicago Pt. 01

Finally I reached around and probed her anus with my finger. I pulled my head back a little and looked her in the eye "finger ok?"

She nodded and I slipped my finger into her anus and thrust it in and out. That was it, and she mewled and writhed as she orgasmed spectacularly, causing me to follow suit immediately.

As we came down from the plateau of orgasm I held her tight, still pressed up against the wall as she panted and moaned.

I kissed her face and neck and massaged her arse and then I carried her to the bed with my wilting cock still inside her. I laid her down and withdrew my cock. I pulled off the condom and straddled her face so she could clean my cum covered cock with her mouth.

Finally I stripped off my clothes and we lay down and snuggled together. Immediate passion spent but now enjoying just being together and the animal warmth we took from each other's nakedness.

We talked about what we had just done. About the pain she had experienced, and how sexy it made her feel.

"It would never have occurred to me that being fucked up against a brick wall would be such a turn on. If I had thought about it at all I would just have thought it really uncomfortable, but it was amazing - as well as being really uncomfortable!" she smiled.

We talked about our sexual fantasies.

She was embarrassed about the depravity of some of hers, which were very masochistic.

As we discussed these ideas we agreed that there were at least two types of fantasies, and probably three.

Firstly there were the really dark and depraved ones which, despite being highly erotic because of their taboo nature, were things which one would never actually want to do in practice.

We agreed that it was really important to understand this. That just because you fantasise about something - and tell someone that - it doesn't necessarily mean you want to put it in to practice. Women who have rape fantasies don't actually want to be raped!

The second type is fantasies which actually you know you would like to try, and are just looking for an opportunity, and the third type are those where you are not quite sure whether you are brave enough to want to take the next step to put them into practice.

"I have lots of fantasies in the first category" she said "and I haven't ever really admitted them to anyone. It becomes hard to reveal these things once you are in an established relationship - without frightening your partner - so I am telling you this now before you have a chance to form any more of an impression of me sexually. So you must promise not to be frightened- or even worse, laugh!"

I looked her in the eyes "I promise - and anyway, I am going to tell you mine in a minute, so I'll have to be careful!"

She grinned and then buried her head back into my chest.

"Most of my fantasies are focussed on submission and forced sex of some kind." she went on. Then, as though selecting items from a filing system, or books from a bookshelf, she reeled off a list of fantasy scenarios. They were not fully articulated. More a list of ideas that she would, presumably, flesh out in more detail in masturbatory solitude, but here being exposed to the light of day, to examination by another person, for the first time...spoken into my chest, avoiding eye contact...

"Slave girl and prisoner. Captured by barbary pirates and sold in the harems of North Africa.

Forced to please prospective clients in the slave market, or be tortured in punishment.

Made to stand naked on a plinth on display to prospective buyers.

Handled roughly by vicious, filthy, old men, testing the merchandise. Made to kneel naked before them and suck their old cocks, which stink, and need a huge amount of coaxing to bring them to life.

Forced to have sex with other female slaves for the entertainment of men.

Strung up by my wrists and whipped.

Forced to serve multiple men.

Given to visiting house guests as a form of hospitality.

Given as a prize to the winning gladiator team in the Roman Forum. Used over and over by these sweaty muscular men for hours at a time. Having no purpose except as a sex object.

Captured by vicious 20th century secret police of some despotic regime. Stripped and tortured with electric clamps on my nipples and vagina."

She listed a few other examples that were, frankly, too extreme to include in this write-up.

"You get the gist? I know that in reality all of these would be absolutely horrific, and completely unerotic, but a small depraved part of my deeply buried psyche finds the ideas a huge turn on"

"I do understand. I am the same. There are things that turn me on that I know I wouldn't want to do in real life. I don't think we need to worry too much about explaining where these things come from - we just need to recognise them for what they - fantasies pure and simple".

"And then there are the fantasies I absolutely do want to act out in real life."

"Like what?"

"Like being spanked by a tall, dark handsome Englishman!" she grinned and kissed me on the lips.

"Hmm, that sounds like a good fantasy"

"And maybe being whipped with his belt, or even caned. Or maybe he makes a whip out of lightweight leather thongs, and whips my tits with it.

"So they are all linked, with the same themes, its just that the ones I actually want to act out are much tamer, more sexy versions of the themes - submission, punishment and coercion. But it has to be with someone intelligent and empathetic enough to understand the difference."

As she spoke I slipped my hand between her legs and started to massage her pussy.

"And there is a third type."

"Oh yes?"

"These are the ones I am not sure about. They aren't crazy and dangerous, but I am just not quite sure whether I am brave enough to go through with them."

"For instance?"

"Like having a threesome"

"Which kind?"

"Well, I was thinking with two men and me"

"I see. And what would happen?"

"Well the fantasy is that the two men use me for their pleasure. Take turns to fuck me in my pussy, in my ass. They make me suck their cocks and cum in my mouth, making me swallow. Then they fuck me at the same time. Both cocks in my pussy, and then one in my pussy and one in my ass simultaneously I have a massive fantasy about double penetration. Trouble is, am I actually brave enough to go through with it?"

"And who are these men? Your fiancé?"

"Yes, I think so. We have sort of discussed it in general terms."

"And who is the other man?"

She looked at me coyly "maybe a certain Englishman?"

Suddenly the elephant in the room was too big to ignore and I said

"I was too selfish to ask earlier, but what is the situation with your fiance? How come you are in my bed tonight? Where is he?"

She looked at the ceiling, suddenly awkward again. Not looking me in the eye.

"We love each other, but in some ways we are not really sexually compatible. I have an incredibly high sex drive and - to be honest - some tastes which are not particularly mainstream. As you now know..."

She glanced at me "I like you because you are tall and strong and make me feel petite and sexy. As you know, my fiancé is shorter than I am and not exactly ripped. He is a very creative and sensitive lover, which is what I want most of the time, and I also love him as a person out of the bedroom. But I also need what you did to me just now - and frankly a lot more besides - and he doesn't, and can't really, give me that. It just isn't in his make-up, and if he tried he would just be faking it.

Whereas with you I can tell that you genuinely enjoy dominating me, and you are good at it, especially because you do it in a way which, whilst rough, allows me to trust you. So I can relax and give myself to you, knowing that you are going to hurt and degrade me, but also knowing that you instinctively know how far you can go without actually scaring me. I can't get that from my fiancé, and he knows that, but he knows I need it, so he is OK with me finding it elsewhere, as long as I tell him what I am doing."

This had all come out in a rush. A sort of stream of consciousness. She paused.

"He knows I am with you tonight. I think he actually likes the idea of being a cuckold."

"OK. That makes sense. Or at least it is all a bit clearer. Although it may seem a bit disingenuous to say this now, I am actually relieved that your fiancé knows about us. I don't really like deceiving people - even though that didn't stop me fucking you this evening, when the obvious assumption was that he was being deceived!"

"What other fantasises are in that third category?"

"Well, there is the other kind of threesome, with another woman"

"Aha yes- excellent!" I said in a comically lascivious tone "and what is stopping you pursuing that one?"

"The issue there is the worry about the other woman having a better body than mine"

"Are you serious?"

She looked at me "Yes."

"Well I think that is very sad. You have the most amazing body I have ever seen. If you could find a woman who didn't make you feel insecure would you do it?"

"Well, that's the bit I don't know. I think so. I would like to. But it is a bit Groucho Marx. It has to be someone who I find attractive enough to want to sleep with, but not have a better body than mine!"

She laughed at herself. "I know, I am difficult!"

"So what would that woman look like?"

"Well I suppose she would have a pretty face, but her body would be larger or fatter than mine - I realise I am shallow!"

"What if you didn't have a choice. What if I were to make you sleep with her?"

She buried her face in my chest, and gripped me hard. She nodded. "Yes, maybe."

"I do actually have someone in mind who I might introduce you to. Let me have a think about that. Maybe I could invite her to have a threesome with us..?"

"Well, we'll see" she said pensively, and then continued.

"And then there are same gay men fantasies. I like watching gay porn. I raised an eyebrow. "I don't see why it should be so odd. All men seem to fantasise about lesbians - you obviously included! Why shouldn't women fantasise about gay men? I actually would like to have that threesome when I am fucked by two guys who are bisexual. They fuck me and then start fucking each other. I'd like to watch my fiancé being fucked by the other guy. She buried her face in my chest to avoid looking me in the eye "would that still work for you?"

"Yes it might do actually" I said quietly.

"Have you ever had a gay experience?"

Nervously I said I had, but not for a few years.

She was intensely aroused by the idea and hugged me close. "That is so fucking hot. I would love to see you fucking another guy - especially my fiance."

"What would he think about that?"

I think he is a closeted bisexual. He is certainly happy to watch gay porn with me, and is open to the threesome idea with another guy, but as far as I know he has not actually acted on that in real life.

Honestly I think he wants to be made to do it. He won't do it of his own accord, but I think that in a threesome situation if the other guy - you? - were to "force" him he would comply. I would need to talk to him about it first to make sure he really is comfortable with that scenario"

My fantasies were quite nicely symbiotic with hers. The fundamental themes were similar / power exchange, inflicting pain, contractual sex in exchange for other benefits, sex with people who one doesn't find attractive.

My "act out" versions were sort of watered down domestic versions of her slavery, rape and torture fantasies. All of mine had the essential element that the person submitting to the "rape", "torture" and "punishment" actually was a willing participant in the scenario That willingness was what leant it its eroticism. So we saw enormous potential to indulge in safe, sane and consensual versions of her deepest, darkest desires.

We discussed all these things as we nuzzled together in the dark. Barely able to see each other's face.

Unburdening of secrets that we hadn't dared tell anyone before.

We chatted in like this for a long while, discovering each other.

In the course of this we both became aroused again and continued to talk as I slipped inside here and we closed the evening with a gentle missionary fuck.

Hungrily pressing our naked bodies together, her soft breasts pressed to my hard chest. My strong hands holding her face; kissing her gently as we made love. Our confessions had created an unusual connection in such a short time and we both knew there was a lot more to explore together...

(To be continued)