Breaking in Anita Ch. 08

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.

"Annabelle?" I asked, standing aside to let her in.

"I never told you my name - I am Bryce."

"Pleased to meet you, Bryce!" she said, offering a cheek for an introductory kiss. She smelled different - not the normal Opium smell that was Anita's signature. This was a fresh, flowery smell.

I offered her a seat in the lounge area of the suite.

"Champagne?" I offered and when she accepted, I poured her a glass, and topped up my own.

"Cheers!" she said and gulped down half the glass. A little nervous, I suppose.

I refilled her glass. Annabelle slid from the couch, and sat on the carpet, next to my knee, with one elbow resting on the seat next to my leg.

She asked me where I was from, and what I was doing in town, and I spun a long yarn about being an executive at a mining company on the other side of the country, and that I was in town for a meeting the next morning. When she asked whether I was married, I was on my third glass of champagne, and a story about me being a widower since losing my wife in a plane crash four years ago just came naturally. Enough to soften any escort's heart, I thought to myself.

"How about you?", I asked. "Do you have a boyfriend, or am I not supposed to ask you personal questions?"

"You can ask." she said, and went on "I won't say I have a boyfriend, but there is a man in my life. His name is Brian and he is a lawyer. We just have a casual relationship; no commitment - just friends with benefits".

Wow, this is a little close to home, I thought.

"That sounds unusual?" I prodded.

"Yes," she continued "We only see each other on weekends, when we are both available. He does not even know that I'm in this line of work."

"What do you think he'll say if he finds out?" Bryce just had to ask.

"Oh, I really don't know. He may not even mind - he's into weird shit: anal sex, vibrators, BDSM, things like that."

"Wow," I said "he sounds like a real asshole."

"No," she covered for Brian "he's a very nice person actually. I've learned a lot from him, and I experienced things with him that I never knew about, but I think he'll just cast me aside when something better comes along... Or maybe I'll chuck him when I find a man that loves me."

"Don't you love him then?" Bryce asked Annabelle.

"I really thought I did", she replied, looking down "but we agreed on a set of rules of engagement," curling two fingers to indicate a quotation mark, "and I have to stick to it. No love allowed." She suddenly pulled back, realizing that she was sailing a little close to the wind, and asked:

"Enough about me. What kind of sex are you in to?"

Bryce topped up their glasses, and responded: "Nothing too kinky, I suppose. Just regular up and down sex. I like blowjobs, same as any man, and I like going down on a girl. I've been told I'm quite good at that." Not to let Annabelle think he was too conservative, Bryce added "I do like doggy style, though, especially if there's a mirror."

"Is there a mirror in the bedroom?" Annabelle wanted to know.

"There is; I'll show you a little later. But tell me, what are your rules about kissing and oral sex?"

Annabelle smiled "You are paying for a girlfriend experience, and there are no limits as to those things tonight."

"Lovely!" said Bryce "And may I add - you are lovely".

Annabelle rubbed my leg.

"Thank you" she said softly. She put her glass down, and asked to use the bathroom.

"Just over there" I pointed out the bathroom, and when she rose, she took her bag with her.

This is it, I thought. Or Bryce thought. I was so invested in this game, I was not sure who I was. Maybe it was the champagne, but my head was reeling from the stories we were weaving around ourselves, and discussing "Brian" in the third person.

When Annabelle appeared from the bathroom a short while later, she had undergone a complete transformation. She was wearing a lacy purple push-up bra with matching panties, with a garter belt and suspenders holding up a set of black thigh high stockings with lace tops. Through the fabric of the tight-fitting bra, he could see the outlines of her areolas. On her feet were a pair of four-inch black stilettos. She had applied mascara and lipstick in the bathroom, and looked like a million bucks.

"Wow!" Bryce exclaimed spontaneously "You look delectable!"

She walked over to him, slightly swaying her hips, appearing to living in the moment. Bryce noticed that she wore the panties over the suspenders, which meant that those could be removed without unclipping the suspenders. He filed that tit bit for future reference.

"Shall we get to the non-talking part?" she asked, bending down to pick up her glass, and draining the last quarter of champagne.

Bryce was gob smacked at the change from sexy girl next door to professional call girl, and all he could do was nod.

Annabelle kneeled on the carpet between his legs and leant forward, putting her arms on his thighs. She undid his belt buckle and unzipped his pants to retrieved his already half-erect penis from the confines of his underpants. Bending forward, she took the tip of his cock into her mouth, and rolled her tongue around it. She bobbed her head forward to swallow the head, apparently savoring the feeling of the swelling mushroom in her mouth. She adjusted her stance, looking a little uncomfortable, and Bryce asked:

"Are you OK like that on your knees?" he asked.

His cock popped out from her mouth, and she looked up to answer with a smile: "No, it's a killer!"

He said "I'm sure the bed will be softer."

Bryce stood to help her to her feet, but she struggled to get up on the high heels, and instead knelt down again and undid the straps around the ankles, placing the offending footwear under the coffee table. This time Bryce was able to help her upright, and she returned the favour by holding him by the penis, leading him to the bedroom. Bryce noted that her tiny bikini panties barely covered half of her buttocks. Bryce (or Brian, as he then was) had closed the curtains earlier, and had only turned on the two bedside lamps on either side of the king size bed, bathing the room in soft light. The inside wall of the room had a row of cupboards behind two mirror-clad sliding doors stretching from the floor to the ceiling, reflecting the whole room.

Anabelle stood on her toes, put her arms around his neck, and gave him a soft kiss on the mouth. "Tonight, I am your girlfriend".

Bryce had a little mind battle with Brian who wanted to take over the thinking, but Bryce roughly pushed him back to the back of his head. I'm paying for a girlfriend experience, and I am going to get one, dammit.

He put his hands on her hips, drew her closer and kissed her on the lips lightly.

"I am a lucky man" he responded when she broke the kiss to pull his tie from his neck.

She let go of his cock, and started undoing his shirt buttons. He sat down on the foot of the bed, removing his shoes and trousers. He looked up at her, standing in front of him on her stockinged feet.

"Now me" he said, and took hold of the sides of the lace panties, pulling them down. She wriggled her hips, helping him to pull the panties down over the suspenders. His face was almost in line with her pudendum, and he saw that there was a faint landing strip above her clit, the dark pubic hair no longer than a few millimeters. Bryce put his arms around her back, pulling her with him as he flopped back onto the bed, with his face between her bra-encased breasts. Annabelle started shuffling down, apparently on her way to continue the blow job that she had started earlier. When her face was above his, he drew her close to him, stopping her from sliding down any further. He kissed her on the lips. She relaxed, looked at him with big brown eyes, the whites accentuated by the dark mascara, and kissed him back, lightly at first, and gradually more passionately, with her tongue flicking between his teeth, meeting his tongue. Bryce could feel his cock twitching against her leg, seeming to beg for attention.

Annabelle tried to move down his body again, but he took her by the hips and swung her to his right. She caught on, and moved into a 69 position, planting her knees on either side of his shoulders, with her pussy just above his nose. He grabbed her buttocks with both his hands, pulling them apart, and lifted his face and used his tongue to trace each of her labia in turn. Down below, he could feel her lifting his cock to her mouth, where she started giving the tip little lip-nibbles. She held the shaft in one hand, and moved his cock from side to side between her lips, continuing to nibble on the tip while doing so.

Bryce kneaded Annabelle's smooth buttocks and turned his head to the left to look at the reflection in the mirror. He drank in the sight of himself lying supine, with Annabelle's stockinged leg on his side, a bit of naked leg visible between the suspenders, the curve of her buttock, and her bra-clad breasts pressing against his stomach. Her beautiful face was just visible between her brown tresses, where her lips were working their magic on his member. She must have felt the movement of his head, and she turned her head to meet his gaze in the mirror. She smiled at him, turned her head sideways, still looking at the mirror, and nibbled the side of his cock all the way down to her hand that was the holding the base of the shaft. Show off! Bryce thought.

Bryce kept his eyes turned towards the mirror, caressing the smooth skin at the back of her leg with his left hand, from the lace topping of her stocking, all the way up to the rounding of her buttock, and using his right hand to stroke her pussy lightly. She pressed back against his hand, her pussy seeking more pressure. Her moving back lowered her pelvis, and he could feel her clit against his lips. He sucked on it, and at the same time, he moved the flat part of his tongue against it with as much pressure as he could muster. He could hear, as well as feel her emitting a low moan. She had about a third of his cock in his mouth, and he could feel the vibration of her vocal cords travelling down his shaft into his balls. Bryce echoed her moan, making a humming sound while holding his lips around her clit. He could tell that this had a similar effect, as she pushed her clit even closer to his lips. He continued making low humming sounds against her clit, and Annabelle changed her octave to hum as low as she could while sucking on his cock. Girlfriend experience indeed, Bryce thought to himself.

It was time for a change of pace, as Bryce felt the warmness of an orgasm coming on, and wanted to hold out as long as possible. He gave her slit one long lick, patting her on the buttock to signal that he wanted to change position. She let go of his cock, and swung around on all fours to face him. He reached up, kissed her deeply, and flipped her over to land on her back. He crawled down and positioned himself between her knees. He lifted her legs as high as they could go, and she grabbed her upper legs with both her hands behind her stockinged knees, lifting them to her chest, spreading her pussy and crack wide open.

Bryce sat on his haunches, gently rubbing her clit with his thumb, and spent a moment admiring the view: a beautiful, sexy escort girl in a rented hotel room, dressed for sex, and all his to enjoy.

He stretched out on his stomach, holding on to her upper legs with both hands, and went down on her properly - he licked her slit from her perineum to the clit, licking around it in circles, then up and down with a flattened tongue, alternating with humming on it with his lips around the clit. Annabelle gave a groan, and Bryce knew that it had the desired effect; he could only imagine what it must feel like on that sensitive little area, given the terrific feeling in his penis when she did it to him a few minutes before.

He could feel the clit growing under his ministrations, and took his left hand from her leg to push her mons upwards, exposing the little pearl, continuing his licking and humming. He brought his right hand down, pushed his middle finger just inside her pussy, and placed his thumb on her anus to gently squeeze the perineal muscle between his fingers. Annabelle's groans turned to low growls, indicating to him that she was close. He moved his right hand upwards, and with two fingers, gently but vigorously rubbed her clit, pushing her over the edge. She gave an "Aaarggghh!", dropping her legs down onto his shoulders and clamping his head between her thighs. Bryce tried to get his fingers into her pussy to prolong the orgasm, but she held his head between her shuddering legs, jerking it from side to side. When she eventually released her grip on his head, he leant forward and kissed her pussy, causing another jerking shudder.