So, why didn’t you sleep with both of them?

Or what a girl wants, what she really really wants

As I sat regarding my most recent lover Linda, I could tell that she had reached that restless stage in a relationship where a woman wants some extracurricular cock but is either too reticent or too embarrassed or too afraid of upsetting the apple cart to say so.

I had known her since we were children. We even used to play together regularly when we were six, which is unusual at such a young age. As we grew up, I tended to observe her from a distance, blonde, pretty, popular and sure of herself as she led an all-American teenage life from what I knew of it, deflowered on her sixteenth birthday, captain of the cheerleaders in Junior High and High School, gymnast, athletic, and always a big smile radiating a healthy wholesomeness.

At some point at university things went off the rails for her. I ran into her randomly one day and it was clear that things were not well. She had stopped going to class, was flunking out and not sure what she wanted or what to do with herself.

I invited her to dinner.

I had inherited a lovely estate with a mansion with river frontage. I had extended the terrace to be able to entertain al fresco in the warm summer months and built an orangery for the winter. In addition, I built a gazebo which opened onto the water to take advantage of the hot, humid summer nights when a certain level of steamy intimacy was called for.

I’ll never forget that first discussion over dinner. She poured out her woes, a recent and painful break up, the death of her father, some financial struggles, an abortion, a total lack of interest in her classes, and fatigue with keeping up a front of being a happy-go-lucky person.

Of course, we got around to discussing sex and she told me some tales of her relationships, a few triumphs and some misadventures.

I suggested that she could stay at my place until she figured out what she wanted to do. I had six bedrooms and plenty of space.

“I also keep a few horses and I’m pretty sure that you like riding, and not just thoroughbreds”.

That was my opening gambit. In negotiating for sex, it is always advisable to start with a probing reconnaissance. One has to ascertain where the defenses can be most easily penetrated.

From the way that she shifted in her chair and blushed I knew that I had hit the mark and that there was nothing guarding the breach besides a thin piece of flimsy cloth that was now wet with anticipation. The only real barrier to entry is always in the mind. Win that battle and you’ll soon be celebrating victory. In this case, I calculated that it would be in less than an hour.

“Do you have a girlfriend”?

“Yes, I have a couple and an arrangement”.

“An arrangement”?

“You remember Anita? She was a pom pom girl in High School”.

“Yes”.

“We’ve been intimate since 10th grade. We came to an arrangement that whenever we wanted to have sex that I would pay her. It’s worked pretty well for the last six years. I get the sex that I want, she gets some money, and we both have our freedom to do as we wish with anyone else”.

There was some hesitation on her part. I figured some good girl versus the bad girl moment was about to happen.

“Do you think I could have a similar arrangement? Only I won’t be with other women with you. I couldn’t do that”.

The deal was done and two years later we had reached the point I mentioned at the outset of this narrative.

Our first year together had a few ups and downs as she had to get used to my other ‘guests’ coming around, particularly Anita. There was some animus between them but as they were both competitive it brought out the best in their respective performances, so I couldn’t really complain when there was the occasional sniping at one another.

The second year was more settled, and I could tell the basic stability that my circumstances and our relationship provided her had improved her mental state significantly.

A couple of things to bear in mind about her were that she had a certain vanity and craved to be admired. She loved attention from men and although I gave her a fair amount I could tell as things developed between us that she wanted more.

She had the free pass that the ‘arrangement’ entailed but if she had used it, she had been discreet about it. But the restlessness was certainly becoming more apparent. I frequently caught her checking out other men when we were out, and more than once noticed her gaze falling on a fellow’s crotch.

So, I resolved to help her out.

I organized a dinner party and invited a couple of my other paramours for my satisfaction and four or five likely lads among whom she could choose for hers.

When I told her about my plans a sly smile crossed her face, and I knew that I had made a good choice.

On the morning of the party over breakfast we were discussing the preparations for the evening.

“Just so you know I intend to make tonight really hot for you. The guests are coming at seven so I’m going to fuck you at five so that you’ll be nice and hot and prepared for later. I believe it used to be called ‘Ladies’ choice”.

She let out a gasp, “Why don’t you fuck me now”?

“That wouldn’t be right. You should build up to it and think about it all day for the extra frisson it will give you”.

She stood up, threw her napkin onto her plate and stalked off towards her room with a parting shot.

“Fine, I’ll just do it myself”.

At five, I found her lounging in the den. I walked in, grabbed her ankles and flipped her onto her stomach on the sofa, pulled down her sweatpants and was inside her before she had time to react. I slipped my hand under her so that I could stroke her clit while I fucked her. She was soon coming volubly and after ravishing her properly I came inside her. It was a bit of territorial marking on my part for whoever was to come after me. It felt wicked and oh so gratifying.

The party came off perfectly. She looked gorgeous and had chosen to wear a sheer black shirt that showed off her assets. She wasn’t holding anything back, and she was the center of a huge amount of attention. I watched the scene with interest and as the evening wore on it became clear who her choice was going to be.

I decided to take my dates to bed and excused myself. I had a limo standing by to take the rejects home. Although I figured that she was going to spend a bit more time flirting with all the putative suitors before consummating matters with her chosen inamorata.

Before I left, I gave her a kiss on the cheek and whispered in her ear, “I’ll come for you before dawn and fuck you again. You’re not going to forget this night ever”.

Sure enough, at around 5:30 I woke up and crept to her room and carefully and quietly woke her. He was fast asleep, sated with drink and sex and not likely to wake up. I contemplated fucking her on the floor next to the bed but decided that although it would be exciting it wouldn’t be all that comfortable, so we crept to another bedroom.

In terms of raising the level of excitement, this kind of surreptitious activity can’t be beat. It’s incredibly arousing to have sex in close proximity to other lovers you have just enjoyed without them being privy to your heightened state of lust. I had two naked women asleep in my bed, she had a naked man asleep in hers and there we were in a nearby bedroom intensely and familiarly making love in the dark.

As an aside, and this is one of my peeves about pornographic writing, semen does not make a particularly good lubricant. It doesn’t possess the correct texture to act as an aid to lubricity, and the way that it coats the vaginal walls makes them feel as if they are thin rather than conveying the deeply voluptuous texture that they actually have. But since her pussy was filled with his cum, I had to put up with this moderate inconvenience.

As I fucked her, I talked to her. Women love aural sex. By engaging the imagination together with the body, she will always enjoy a deeper, richer more rewarding pleasure than if a man concentrates on nothing but the physical.

“I know you and I know what you’re like. I know that when I finish fucking you that you’re going to go back to your room, wake him up, get on top of him and fuck him again”.

She came.

“Then tomorrow you’re going to spend a good part of the day fucking him some more. What I don’t understand is why you didn’t take two of them. You could have. I know you’d like that even more wouldn’t you. You’d love getting fucked by two men, wouldn’t you”?

Weakly, “Yes”.

“What did you say”.

“YES, OH GOD YES”!

“I know you’d love to have two men in bed with you with a cock in your mouth and one in your pussy”.

She came again.

“I saw you looking at Jack with lust. Why didn’t you invite him to join you? You could have had both of them eating out of your hand and eating something else as well”.

She came again.

“Next week I’m inviting them back. I’ll tell them both what they have to do. I know that they’ll jump at the idea of both of them taking turns fucking you. You won’t have to do anything except lie back and take it. Do you like that idea”?

“OH GOD YES, OH, OH OH! FUCK ME HARDER! JUST DO IT”!

When I finished with her, she did exactly what I predicted she would. She went back to her room, woke him up and slid his nice hard cock inside her before he really grasped exactly what was going on.