Chapter 8: Roleplay: Renting a Girlfriend for the Night
This is the eighth chapter in this series, and although it is a stand-alone story that can be enjoyed on its own, you may want to read the previous published chapters (or at least Chapters 1-3) first, as it gives context to the somewhat peculiar carnal relationship between Anita and I.
I admit that I like to watch pornographic videos, especially when there is some sort of storyline instead of just sex. I remember that I once found a site called "Girlfriend for a Night" (or something like that; please remember I am trying to remember details from long ago) with thumbnails of different videos. The story went something like this: a guy on a business trip, alone in his hotel room, would phone to order an escort girl who would come to his room and after chatting for a bit, would go into the bathroom to change into sexy lingerie before treating the businessman to a wild night of sex.
Although the storyline was fairly similar in all the videos, there were different actors in every film, and some of the actresses were obviously experienced porn stars. The girls were invariably beautiful, and I enjoyed looking at their bodies and outfits, trying to guess when they would go into the bathroom, and what they would dress up in. Invariably, there was a "gift" of cash in an envelope which the call girl would count in the bathroom before putting it into her handbag. I've never paid a woman for sex, but found it titillating to imagine myself as the businessman.
I thought that Anita and I should try this type of role play, and one night, after quite a few glasses of wine, I told Anita about my fantasy, and role that she was supposed to play. When she sounded intrigued, I showed her one of the videos I'd seen - I chose that particular one especially, because the actress reminded me of Anita: she was youngish, with brown hair and a similar lithe tanned body, and I hoped that Anita would identify with the character.
We've never watched porn together, and initially Anita just sat there watching quietly, sipping on her wine. Although I had seen the video before, I was aroused again, imagining myself as the actor in the video, and Anita as the call girl. When the sex got going in earnest, I realised that Anita was just as turned on as I was: when I casually put my hand on her upper leg, she took it in both her hands, pulling my hand to her crotch under her skirt. I could feel that her G-string was wet already, and started rubbing her pussy through the thin fabric. In a flash, Anita had my trousers undone, and extracted my already hard cock. We both came well before the actors in the video did, lying on our sides watching the screen, me having entered her from behind. We were almost fully dressed, save for the fact that I had my trousers around my knees, and Anita was
sans
panties, with her skirt bundled around her waist. To call this episode frantic fucking would be about right.
After the video ended, we agreed that we should give it a try "for real", but unscripted, ad libbing as required. I told her that my apartment was too familiar, and suggested that I would book into a hotel to give the fantasy a more real feeling. I insisted that I would have to pay her in real money, as the hiring of the escort was central to the storyline. Although Anita protested a little, she eventually gave in to my demand (as she usually did) and agreed to the money part. For added realism, we agreed that it should happen on a week night instead of our regular weekend liaisons, and arranged to do it the next Thursday, depending on the availability of a suitable hotel, and a babysitter for Anita's son.
When Anita phoned to say that she had arranged the babysitter for the evening, I booked a hotel room at a four-star hotel in the city, not too far from Anita's apartment. I told Anita that she should be ready to expect my call on Thursday evening, not telling her the name of the hotel.
Escorts don't know these things in advance now, do they?
After work on Thursday, I went straight to the hotel, carrying my briefcase and a small overnight bag with a change of clothes and toiletries, as a businessman on an overnight trip would. I had an early dinner in the hotel's restaurant, and went up to the room to prepare. I had brought a couple of bottles of wine with me, but when I opened the bar fridge to put the wine in, I saw that there was an ice-cold bottle of French Champagne in the fridge. What the hell, I thought to myself - I am spending a lot of money on this fantasy, and might as well splurge a bit more on an overpriced bottle of bar fridge champagne. I showered and put on a fresh set of office clothing, even putting on a tie, which I loosened to look like a businessman after a day in the office.
I gave Anita a proper chance to prepare herself for the evening, and just after 7:30, I phoned her landline.
"Hello?" she answered, not identifying herself as she usually did.
"Uuhm, hello", I said "who am I speaking to?"
"My name is Annabelle. May I help you?"
The fantasy had gotten off to a good start.
"Yes, I think so. I found you on the Executive Escorts website, and since I am in your city, I was wondering if you are available tonight?"
"I may be", she teased "This is supposed to be my night off, but I could make an exception ..."
She let the suggestion hang in the air, giving me a chance to negotiate.
"I'll try to make it worth your while. I saw on the website that your rate for outcalls is seven-fifty for two hours. Will a round thousand do?"
She hesitated, and I realized that although I insisted on paying her in real money, she did not expect that much. Little did she know that escort girls that looked like her could easily demand that much, and more.
"That will work. Where are you?"
I gave her my room number and the name and address of the hotel.
"Oh, that's close," she said "I can walk there; I'll be there in 20 minutes".
"Uuhm, Annabelle?" I said, wanting this play-acting on the phone to continue a little longer "I just saw that there are two Annabelles on the web site. Which one are you? - the short blonde with the big boobs, or the beautiful brunette with the splendid legs and tanned body?"
"Which one did you want?" she played along.
"Well, I would much prefer the gorgeous brunette."
"Thank you. That would be me" she said, suppressing a laugh before she rang off.
I sat back on the couch, looking forward to an evening of fun and excitement. I took the envelope stuffed with cash from my briefcase, and removed five bills, leaving the agreed thousand in there. I had budgeted for more, but "Annabelle" was satisfied with the agreed amount. I put the envelope in a conspicuous place against the bathroom mirror to make sure that she'd see it when she entered the bathroom.
To keep myself busy while waiting, I opened the champagne, and sat back down, sipping on a glass of bubbly, staring at the files that I had strewn around the coffee table to create the image of a busy businessman.
Just before 8, there was a soft knock on the door. When I opened, there was Anita, pretty as ever. She was wearing a pair of tight blue jeans, a white half-button halter top with bare shoulders, showing off her tan, and a pair of flat white sandals. The top had most of the buttons undone, and although she showed off some cleavage, it did not look slutty, just very, very sexy. Over her shoulder, she had a fabric bag which I supposed contained her alternative outfit.
