First Time as an escort

First Time Escort

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She was shocked when she suggested it first. But then she had an idea that all was not quite as it seemed for some time.

As the information sunk in she took time to reflect on the position and how she had come to be where she was.

One of her best friends was an escort. Was that the right word or was it hooker or something worse? And here she was suggesting to Susan that there was an opportunity for her to join her in the oldest profession.

Susan was 44 and single again following the break-up of her marriage some three years previously. Her 2 children had recently left home, one to study abroad and one to share a place with her boyfriend. So Susan now lived alone in her 2 bedroom apartment.

Her marriage had broken up because her husband cheated on her. She found out the worst way — returning home early from a weekend away with friends to find her husband in bed with the daughter of one of their neighbors. Her husband at the time was 42, the girl about 22, and as she stood unnoticed in the door of her bedroom watching her husband pounding into her slim young body it felt like her whole world was at an end.

Of course, as she found out subsequently the girl was not his first cheat and he had strayed a few times previously, particularly when away with his friends on golf trips overseas.

The marriage finished instantly and thankfully her husband contested nothing. He kept the house (she could never live there again) and she received a good settlement which enabled her to buy and furnish a nice apartment and live comfortably without having to work.

That was until 6 months ago when he left the country and the monthly payments to her stopped leaving her exposed and having to look for work to support her lifestyle.

After the shock of the separation and subsequent events, Susan shut herself off from normal life and even her friends. She threw herself into looking after her children’s needs and buying and setting up her new apartment. Gradually she picked up with her friends again who were anxious to help her recover and resume her normal life.

Initially, she had no interest whatsoever in men or another relationship. Trust would be an issue for a while. Her friends tried hard to get her to socialize and to set her up on dates but for the most part, she resisted. It was a full 2 years before she went on a date. The father of one of her daughter’s friends, also separated, asked her out and she went on several dates which she enjoyed. Both were unsure of themselves and while the dates were good they ended with at most a gentle kiss on the cheek. About 2 months into the relationship the man suggested a weekend away in a nice hotel together. Susan had never contemplated a progression to a physical relationship and the idea scared her and as a result, she refused and ended their brief relationship.

It did force her to consider the physical and to appreciate that if she was to see men that inevitably that would be an expectation. It was not that she did not enjoy sex because she did but the vision of her husband with the other woman had scarred her.

Before she met her husband Susan had been relatively quiet and her experience with men was limited.

Her first kiss did not happen until she was 17, a brief sloppy snog on a dance floor at the end of the night.

A year later she had her first boyfriend who she dated for about six months. After about 3 months with him, she finally relented one night when parked in a secluded place in his mother’s car and let him open her bra and fondle her breasts. A regular play with her breasts seemed to satisfy him for the next few months but when she then refused to let him go further the relationship ended.

Maybe she was keen to show she was mature because the next phase of her sexual awakening followed soon after. The older brother of one of her friends made a play for at a party in her friend’s house. In her eyes, this guy was perfect, older, and hot. She got a bit drunk to let him kiss her passionately and take her upstairs to his room. He said all the right things and as a result, before long her top and bra were on the floor as he kissed and fondled her breasts. The sensations distracted her and he had his hand under her skirt on her panties before she realized. This time she didn’t resist and helped by the alcohol in her system let him explore her. He asked if he could make love to her which made her come to her senses and say she was not ready for that. Thankfully he accepted her answer and resumed the kissing and touching. He told her she had him very turned on and that he needed to be relieved. She watched as he opened his pants and he took her hand and put it on his throbbing erection. To her surprise and relief, just a few strokes of her trembling hand had him shooting his sticky cum on her chest and skirt.

A couple of months later she met her future husband. She knew straight away he was special for her and before long they were a very serious couple. Despite some previous experience with former girlfriends, he did not rush her and their activity for a full year never went below the waist. This was because Susan was aware of how passion had overtaken her in the past and because her future husband did not pressure her. However on his birthday about a year after they started dating she surprised him one night when they were parked in his car by opening his pants and stroking him until he came. On the night he proposed to her about 6 months later she surprised even herself by taking his erection in her mouth and swallowing hard when he came. After that, it was inevitable that he would have regular access to all of her body. While the plan had been to wait until they were married to finally have sex one weekend away at a friend’s wedding she let him come into her bedroom. For the first time they were completely naked together and despite her best intentions, she found herself so aroused that she begged him to enter her and make love to her. Of course, he did and while the first time was awkward and rushed the repeat performance the next morning was much more fulfilling.

So now 19 years later he remained the only man to have had had sex with her. Which made the prospect of dating again so much scarier.

Financially she needed to find work and she was grateful to her friend Helen who got her a job in a company she part-owned which provided waitresses and hostesses for general corporate functions in the city. She enjoyed the work and meeting people and her employers seemed happy with her ability to mix and chat with the customers and add to the ambiance of the events.

Recently she had even given her phone number to one of the guys she had met and was flattered when he phoned and asked her out. They had a lovely meal out and when he dropped her home she naively invited him in for coffee.

She had invited him in all innocence but he interpreted it differently. When he kissed her as they sat together on the sofa at first she stiffened but relaxed then and quite enjoyed the sensations. They kissed more passionately and then she realized that his hand was on her thigh and moving upwards. She froze and removed his hand saying that she was not ready for that. He seemed OK about it and before long he was kissing her again. This time his hand moved to the zipper at the front of her dress. She froze, feeling silly, but uncomfortable but unable to say no to him again. As she sat there his hands opened her dress, then bra and fondled her breasts. Despite herself, the sensations felt good and she even moaned out loud when he moved his face down to suck on her nipples. She stopped it after a bit and rezipped her dress and saw him at the door. She did not return his subsequent calls but she knew he had awakened desires and needs in her that she thought were in the past.

With money tight, she was working more hours, and instead of just working at corporate lunches she started working dinners at night also. The atmosphere at these was different, fuelled by alcohol probably, and she was surprised on regular occasions to see some of the other girls and notably her friend, leaving with some of the male guests at the end of the night.

So, on this day, at lunch with Helen, she asked her about it. The response stunned her. Yes, the girls were leaving with some men but they were doing so on a professional basis. And as well as running the waitress and hostess business, Helen was actually running an escort agency. Susan struggled to take all this in and to cap it all Helen was telling her that if she was interested she could get her ‘work’ and she would be well paid for it.

Susan refused instantly.

But in the following weeks, it was rarely out of her mind. Money was getting tighter and tighter and deep inside herself Susan knew that she needed to move on and put the past behind her.

At 44 she was in reasonable shape. Her walking and tennis helped and she had shed a bit of weight recently. Her hair was still jet black and the boobs while showing some sagging was still a reasonably firm 36c.

It was Susan who raised the subject again with Helen. Helen gave her more detail and in particular explained the real money to be made was as an escort for businessmen in the city for overseas. Very often they just wanted company on a night out at the theatre, or dinner, or the like, and that many did not even want sex at the end of the night.

Helen said she could set Susan up with one of the regular guys who generally did not include sex in his requirements. She said generally because the option was always there for the client if he wished.

Again Susan said no but again she spent weeks considering it. Helen had given her an earning expectation and it would solve some problems for her and also there was no prospect of her meeting men let alone dating again.

When her car broke down resulting in expensive repairs her thoughts became stronger.

Helen was surprised when Susan raised the subject at lunch and more so when she said she was willing to try with the type of client Helen had suggested.

The week flew by and before long she was shopping with Helen for an outfit for her ‘date’ that evening. She was relieved when Helen pushed her towards smart conservative outfits rather than the tight revealing stuff. The clients want to be seen with a respectable woman Helen said not with somebody dressed like a hooker. Ironic in a way she thought.

As Helen said goodbye and good luck she put a box of condoms into Susan’s hand. I am sure you will not need them she told her but always be prepared.

Saturday night arrived and she sat in the bar in the hotel dressed in a nice dark blue dress and heels. She drank her wine quickly as she waited for her date. Then an older man introduced himself. He was dressed in a suit and with his silver hair, Susan put him at about 60. He was Canadian, in the city for 3 weeks on business.

The evening went well. They went to a nice restaurant for dinner where they chatted easily. He seemed genuinely interested in her. For his part, he was married with grown-up children. After dinner, they returned to the hotel bar where they sat and chatted. Time passed easily.

And then he said it. He said that he rarely invited his dates to his room but as they were getting on so well would she be willing to join him for a nightcap in his room.

Susan smiled and said of course but inside her mind was racing. She had not anticipated this and suddenly she was terrifying.

In the room, she followed his direction and sat on the sofa as he poured some wine. When he kissed her she played her part and responded. His hand found her breast through her dress and cupped it briefly. He paused then to her surprise told her that while he paid for these dates he had never had sex with anybody other than his wife and that that would continue. But that he would like to touch her and for her to pleasure him. He said that as usual the agency was paid direct but to thank her for the evening he slipped some notes into her hand. The tip was fantastic and effectively doubled Susan’s earnings for the night.

Susan was in a way relieved but still nervous about the role she was to play. He suggested that she slip off her dress to save it from getting crumpled. She stood and removed it slowly, feeling awkward, but trying in a way to appear seductive.

He stood, kissed her, and asked her to undress him completely. She took her time and did it slowly, kissing his body as she did. At last, he stood only in his shorts. Despite his age, she thought he was in good shape.

How did she get here she thought as she kissed him and felt his excitement against her belly? He dropped his shorts and she looked down at his erection. She reached out and touched only the third penis she had ever seen. He was hard and aroused and in her trembling hand felt bigger and thicker than her ex-husband.

He led her to the bed where he lay on his back. She knelt beside him and began to slowly stroke him. She never referred to her breasts as tits but when he asked to take out her tits it sounded strangely erotic and dirty. She obliged and as he fondled her she maintained the rhythm on his cock.

Susan was very conscious of her own rising desire. The situation was surreal but she felt in control and aroused. When he dropped his hands she moved to let her full breasts rub over his erection. Aware of her own wetness she wanted him to touch her but he lay with hands behind his head enjoying her motions.

Before long his breathing had quickened and he was moaning softly. Susan moved and straddled him and rubbed his hardness against the front of her panties. He grunted loudly and threads of white semen shot upwards onto her wet panties and her belly. As he relaxed Susan moved away and returned with a damp cloth and proceeded to wipe him clean.

Some minutes later he thanked her and suggested she could leave. She dressed and left pausing once she had closed the door to release a huge sigh.

In the week following Susan thought of nothing else. Amazed at how easy it had been and amazed at her own needs and at how much she had wanted him to pull her panties aside and slide deep inside her. Her call to Helen told her that she was available for more work if required. When Helen asked if she still wanted a date where sex was unlikely Susan responded that as long as Helen could recommend the guy that she was more open to going further.

And so 3 weeks later she was walking into the bar of another hotel. This time her date kept her waiting nearly 40 minutes. When he arrived he apologized and told her his meeting had overrun and that he needed to shower and change before dinner. He suggested Susan come up to his suite and have a drink while he got ready.

This guy was more Susan’s age. He was quite good looking if a bit on the heavy side. He was from Australia and was similarly married with children. Susan knew this because the first thing she noticed in the suite was a family picture on the locker.

The guy, Mark, buzzed about in the room and made a couple of business calls as he did. Susan noticed how tense and uptight he appeared. At last, he closed the bathroom door and as Susan sipped her wine she heard the shower running. After a while, he came out with just a towel tied around his waist, beneath his heavy belly.

He smiled at her and commented that he was very tense after his day’s business and wondered would she be agreeable to relieving some tension for him before dinner.

Susan said of course not and asked what he had in mind. In response, he dropped the towel revealing a not particularly big but very erect cock. Susan put down her drink and despite her trembling walked over to him and kissed him. He responded held her tight to him and she felt the zip on the back of her dress being opened. She let him undress her and her dress slid to the floor. As they kissed more he pushed forward against her panties. He pulled her onto the bed with him and she started to stroke him as they kissed. When he whispered that her mouth tasted good and would she like to move it lower it took her a moment to realize what he expected.

But dutifully she moved down and took him in her mouth. She sucked and licked him and used her hand on him to maximize his excitement. Thankfully she judged the moment right and pulled away from her mouth just as he erupted and shot over her bra and chest.

She fell back on the bed as he relaxed. Again she was aware of her own arousal and was disappointed that he hadn’t touched her or even removed her bra and panties.

She realized he was dozing and was unsure of what she should do. In the end, she cleaned up in the bathroom and put on a bathrobe over her underwear, and sat by the big window admiring the view of the city at night and sipping mineral water.

About an hour later he woke and smiled dreamily at her. He was hungry and suggested that rather than going out they order room service. He was the customer she thought so that was OK with her. As she looked at the menu he used the bathroom and came out in a robe also.

She was standing by the window looking out as he came over to her. He put his arms around her from behind and kissed her neck. She relaxed into him and felt his hands move up onto her breasts. He fondled her briefly then must have opened his robe because she felt him hard pushing against her bum. Then he pulled up the back of her robe so that he was naked against her panties. She felt him opening the front of her robe then gasped slightly as his hand found the front of her panties. He whispered in her ear to take them off so she did and his hand quickly returned to cup her hairy mound. When he reached lower he told her how wet she felt and how she felt ready for him.

She was surprised when he pushed her forward slightly. She had to reach out to put her hands on the window. As she stood there leaning forward he positioned himself and entered her.

The sensation was exquisite and she was disappointed when he pulled out after a couple of strokes. She looked around to see him rolling a condom onto himself before he roughly entered her again. She moved her hands briefly to let him remove her robe and then again as he removed her bra.

At last, she was naked, her bare breasts being roughly mauled as he pumped into her from behind. Way below her the city traffic buzzed. In her head, the pain of the last 3 years was being erased with each of his deep strokes. This stranger had her aroused beyond belief and when her orgasm hit she felt herself squeezing him inside her as she screamed in ecstasy.

As she recovered he continued to move slowly inside her. Then they decoupled and she led him to the bed. With him, on his back, she straddled him and let him slide up inside her. She pulled his face into her breasts and rode with him, delighting as he filled the condom inside her hotness.

30 mins later she left the room. An envelope of cash in her bag along with her sodden panties. Her new career had begun.

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2 comments

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