The Dating Agency

A jilted lover delivers and receives a sting in the tail

By Paul S

Anna was a young female matchmaker at hotseat.com dating agency, which had an online presence, but also had offices in South London to assist people seeking a new date or relationship, and wanted one-to-one practical advice too. She worked with Elaine who was also a matchmaker who was slightly older at 26, and 36-26-38 with medium length dark curly hair and hazel eyes.

Anna was 21 and was not currently in a relationship, despite being very attractive and a slim and very fit 36-26-36, with blue eyes and medium length ash blonde hair. However that did not bother her in the slightest, as she had many interests outside work, such as playing hockey with friends, and socialising with mates. She had in fact fixed up many of the hockey team with dates through her agency.

The agency was owned by a lovely lady, Sylvia, who was an old school romantic in her late 50s, and saw life through rose tinted glasses, usually in a restaurant or bar. She would spend hours socialising with friends and business colleagues. She was married to Pete and once said: “I don’t know how he puts up with me.” She got on well with Anna whom she adored.

Anna’s job was very varied as she not only dealt with young boys and girls seeking their first dates, but also young professionals in their 30s who found dating difficult, and even people in their 60s and 70s who had lost a partner and found themselves looking for a new partner after not having dated for many years. This could be a daunting and strange experience, so Anna was there to help them through it.

Anna would typically run through applicant’s details and put them into a computer programme to find the best match. That included age, birth signs, aptitudes, preferences, likes, dislikes, interests, type of job and whether seeking just a platonic relationship, a date or a long term relationship.

One day she had an application from Ben, an old school friend whom she knew fairly well, who had just split up from his overbearing girlfriend, Julia. Julia was of medium build, and 36-28-38 with long dark hair and brown eyes. Ben was 21 like Anna, and fair build at 5 foot 10 inches with average length dark hair.

This tweaked Anna’s interests as this was an application which she took a personal interest in. Ben had made an appointment to come in and discuss a possible date and match, and it was Anna who got the job.

Ben came into the office and said: “Hello,” to Anna; who said: “Hi, we haven’t met for a while, have we?”

Ben said: “I didn’t know you worked here now?”

Anna said: “Yes, I have been here 3 months now and loving it. I have matched so many dates already and it’s a great feeling bringing people together. It’s also really nice when it works out.”

Anne then said: “Have you had any feedback yet on your application?”

Ben said yes: “I liked two of the girls I was matched with, which were Laura and Elaine.”

Anna said: “Yes, Laura came back and said she might like a date, as she thought there was a match. Elaine is keen, but quite busy as she works in the city.”

Ben said: “OK, let’s set up a date with Laura and see how it goes.”

So Anna contacted Laura and left her a message to contact Ben direct.

Laura and Ben met at a local wine bar later that week. Laura was 36-26-36 and 5 feet 8 inches high, with medium length auburn hair and hazel eyes.

The date went fairly well, but Ben thought there was perhaps something missing, as there was no ‘spark’ in their relationship, despite getting on really well.

Ben returned to the agency and said: “It went OK but I need something to light my fire.” Ben then suggested: “What about you and me going out for a date, Anna?”

Anna was a bit taken aback by this suggestion, but said: “OK, but can I do a match check first?”

Ben said: “OK then.”

Anna put all of Ben’s stats into the programme and her stats as well to see if they matched up. Anna was gobsmacked when the programme suggested he was the hottest date possible for her, but modestly said to Ben they were quite well matched.

Later that week, Anna and Ben met at the same wine bar as Laura went to and chatted about schooldays and the time they knew each other from before. The discussion then turned to relationships, and Ben said he was coming out of a stormy relationship with Julia, age 23, who was very selfish.

Ben then asked about Anna, but she said she was still young and had time. She had had several boyfriends but nothing serious.

Ben and Anna clearly got on really well, and suggested they go somewhere a bit quieter, as the bar was quite noisy. They went into a ‘snug’ at the back of the building which was less busy, with high back plush seating for more privacy.

Ben and Anna decided to share a passionate kiss, and then another, followed by another. Anna could feel herself falling for Ben and couldn’t do anything about it.

They went outside as it was now dark, and they walked around the corner. Ben and Anna then had a red hot embrace, with Ben running his hand up Anna’s legs to cup her bottom, whilst Anna’s hands went under Ben’s jacket to grab his chest whilst they kissed.

After a while they agreed to meet Saturday at the cinema but agreed they had a hot first date.

One date became many and Anna and Ben became an item.

News of this gradually spread until it reached Julia, who somehow thought she was still going out with Ben.

She rang Ben on his mobile and gave him grief about this, and said: “Who is this tart you are going out with? You are my boyfriend until I say so.”

Ben said: “You are no girlfriend of mine any more, and leave Anna alone, do you hear!”

But Julia now had the name of Ben’s new girlfriend and went to the agency to confront her. Julia walked in and threatened to cause a scene.

Elaine intervened and said: “You will have to sort this out later.”

Anna agreed to go to Julia’s flat after work at 6pm to discuss the situation with Julia face to face, to keep the peace.

Anna turned up at Julia’s flat, and Julia let her in. A terse discussion followed where Julia made accusations against Anna and said Ben remained her boyfriend, and called Anna a tart.

Anna said: “How dare you!”

Julia said: “I will show you how I deal with tarts who try to steal my boyfriend!”

Anna said: “What do you mean?”

Before she knew it, Julia had pulled Anna across the room and over the arm of a chair. Before Anna could react, Julia had pinned her down, lifted her skirt and yanked down her briefs to her thighs. Julia reached into a drawer and pulled out a leather strap.

Julia said this is how I deal with tarts, and placed the strap across Anna’s now bare shapely backside and brought it down with a firm smack.

Anna cried: “Ouch!” But Julia continued spanking Anna with the strap. Anna tried to struggle but Julia had her in vice like grip and continued tanning her upturned bottom hard.

Anna said: “Please, can we talk about this?”

Julia said: “No, you need to be punished like the tart you are.

Anna’s bottom was reddening as the spanking continued and she tried to struggle free and avoid the pain, but Julia just kept spanking her relentlessly. Anna must have taken a full 50 with the strap before Julia finally released her.

Anna looked at the damage in the hall mirror and her shapely bottom was now crimson and stinging like hell.

Julia said: “I hope that has taught you a lesson, tart.”

Anna said she was disgusted, and carefully pulled up her briefs to avoid catching her sore bottom. Anna put on her coat and left in disgust, slamming the door.

Anna went home and told Ben what had happened.

Ben was furious and said he would come round to her flat immediately and apologised for Julia’s unacceptable behaviour. Ben said he would have it out with Julia and ensure that she was fully punished either by the law or in person. Ben turned up at Anna’s flat and they embraced and kissed passionately on meeting.

Ben asked: “Did she hurt you?”

Anna said: “Not too bad, but it really stings like hell,” and lifted her skirt and dropped her panties and bent over to allow Ben to inspect her crimson backside.

Ben said: “Do you want me rub some cream into that, as it still looks very sore?”

Anna said: “OK,” and lay on the sofa with her upturned bottom exposed, whilst Ben rubbed cold cream from the bathroom into her hot bottom.

Anna said: “Ooooh, you don’t know how good that feels.” She then joked that she must have her bottom thrashed more often.

Anna said: “I never thought that after just 4 weeks of dating, my boyfriend would be rubbing cold cream into my bare bottom.”

Ben said: “Anna, this is no laughing matter. What Julia has done is out of order. Sorry but I need to photograph your bottom with my phone to prove you were assaulted.”

Anna reluctantly said: “OK,” and rolled over and put her bottom up while Ben took a snap.

Anna said: “We will go out again at the weekend once, my backside has cooled off, but don’t do anything stupid, darling.”

Ben kissed Anna and said: “Leave it to me. That girl needs to be taught a lesson she won’t forget, once and for all.”

Ben later rang Julia and said they needed to meet at her flat for her to explain why she had thrashed his girlfriend.

Julia tried to be all ‘lovey-dovey’ with Ben, but Ben wasn’t interested and said: “Julia, it’s over.”

Ben turned up at Julia’s flat early Friday evening with a long cardboard tube containing a newly acquired swishy cane.

Julia welcomed Ben, calling him her boyfriend, but Ben said: “I am no longer any friend of yours.” He went on to say: “What you did to my current girlfriend, Anna, is unacceptable. I am going to make you a simple proposal, Julia. Either you take a severe punishment similar to Anna’s, or I go to the law. Which is it to be?”

Julia tried to joke her way out of the situation by saying: “I was waiting for a proposal!”

Ben said: “Either I punish you, or I go to the law.”

Julia said: “Please don’t go to the law, darling.”

Ben said: “Right, punishment it is then, and don’t call me ‘darling’.”

Julia then tried to wrestle with Ben and plead with him, but Ben said: “I should have done this a long time ago.”

He then manhandled Julia by the arm despite her protests and told her to bend over the back of the sofa. She reluctantly agreed and slowly walked over to the back of the sofa in the lounge and bent forwards right over it, with her skirt riding up exposing her panties.

Ben followed and lowered her black panties to her thighs, exposing her plump size 38 bottom, readied for a thrashing.

Julia said: “What are you doing?”

Ben said: “Giving you what you deserve.”

With that, he opened the cardboard tube and produced a newly acquired swishy cane, and gave it several swishes through the air very close to Julia’s upturned bottom. She could feel the cool air moving past her sensitive bottom as he did so.

Ben said: “Are you ready?” Then he lined the cane up across Julia’s lower seat.

Julia said nothing until the first swish landed across her backside, and then a few moments later let out an Argh! with the pain. The second swish landed just above the first, producing another Ugh! from Julia. The third fourth, fifth and sixth strokes followed as the pain increased. Julia tried to protest, but had to concentrate on the searing pain increasing all over her plump size 38 backside.

Ben paused and said: “Perhaps you will treat Anna with respect from now on because she is my girlfriend and I love her. If you don’t, I can repeat your punishment until you do.”

Julia said: “Please, no,” getting up and rubbing her bottom which had six red tramlines across it.

Ben said: “Bend over, Julia,” and promptly lined the cane up and gave Julia another six swishes of the cane, with Julia panting after each stroke.

He then allowed her to get up and rub her increasingly red bottom for a few moments, then said: “Right, bend over again,” and gave her another six stinging strokes.

Julia reared up after 18 strokes of the swishy cane, and said: “Ben, please, I really can’t take any more of this. It’s really stinging.”

Ben said: “Well, Anna’s bottom was really stinging, too, after 50 strokes from you. Bend over, you slut, and take your punishment.”

Ben then proceeded to administer the final six strokes, which swished across Julia’s now crimson backside. Julia took her punishment, but then got up panting heavily and gently rubbing her now crimson bottom.

Julia said: “That really, really stings!”

Ben ran his hand across Julia’s bottom which was now red hot; and said: “I asked the shop for a cane to teach a young lady a lesson she won’t forget, and it’s no less than what you deserve. Oh, and if you are thinking of going to the police, then Anna will just make a counterclaim. Touché!”

Ben and Anna never heard from Julia again, who later moved away.

These days Ben and Anna just laugh about it, but Anna had found her unplanned spanking experience very stimulating.

Ben had really punished Julia, but not really punished a girl since. Anna was impressed that Ben had severely punished a former girlfriend to defend her honour, and wondered if he would punish her.

They had continued dating as an item and, when they embraced, Ben would run his hand up her stockinged legs to cup her bottom.

Anna had noticed this and one day left her panties off to see how Ben would react.

Ben was surprised and said: “Anna, you naughty girl!”

Anna queried: “Do you still have that light, swishy cane you used on Julia?”

Ben said: “Yes, it’s in the spare room.”

Anna said: “As I have been a bit of a naughty girl, I will let you give me six of the best with it.”

Ben said: “OK, are you sure?” And went to fetch it.

Ben returned and Anna said: “Yes, I deserve it,” and leant over the sofa, and her short skirt rode up exposing her bare bottom. Ben lined up the swishy cane, and gave her a moderate stroke right across Anna’s seat.

Anna reared up and said: ‘Wow! That’s hot!”

The second and third strokes swished through the air, with Anna panting after each stroke.

After the fourth stroke, Anna said: “Ooooh, that hit the spot!”

The fifth stroke swished across Anna’s backside and she said: “Ooooh, that makes me feel so naughty!” It was followed by the final stroke, after which Anna stood up, lifting her skirt to inspect her well striped shapely bottom, which was now pleasantly hot and tingly.

Ben asked how it was for her, and Anna said: “It felt wicked! Every time I am naughty I will need this, please.”

The End

© Paul S 2016


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