The Gigolo Page 5

  “Hello Paul,” was the reply. She almost blushed; she knew full well that he knew what she was here for.

  In the bar, they sat beside each other. Paul had bought them both a drink, a gin and tonic for her and a gin and tonic for him.

  The conversation was mainly small talk, light and breezy, just to break the ice; chit-chat about music, films, theatre, what they liked, what they didn’t like.

  Paul would have to steer the conversation slowly and almost ‘romantically’ to the business in hand, sex.

  The ‘ladies’ on Trudy’s agency, would all demand, in different measures, mock romance, mock affection, mock love even, and it went without saying they would also demand sex – that is, real sex of course.

  All very civilised and above board, with not a hint of money exchanging hands.

  Money wouldn’t be mentioned, not now, not ever – that was Trudy’s department. Her ‘ladies’ would pay a monthly direct debit into Trudy’s bank and Paul would get his ‘commission’ paid directly into his bank.

  It was ironic, that the oldest profession in the world would be so modern and up-to-date and internet-driven.

  It was as easy as ABC – with just a few clicks, a woman could pay her fee, log in and pick her man. An hour later she could be wined and dined and romanced and having the time of her life, in and out of her boudoir.

  All for that much sought-after and very precious fee.

  Paul was getting impatient, he would have to make a move soon.

  “Can I freshen your drink?” he asked.

  “No thank you,” Gillian said. “I’m driving.”

  “In that case, why don’t you come back to my apartment and I’ll make you some coffee?”

  It was a simple, time-honoured question, Paul thought, and it could only be answered by a simple yes or no.

  If she answers yes, then the game is on, if she answers no, then I won’t waste any more time.

  The question itself had nothing to do with coffee; men asked it knowing that they had no coffee, women answered it knowing they didn’t drink coffee.

  The question really meant… “Do you want sex?

  Gillian replied… “Yes, please.”

  At last, we’re in business, Paul thought.

  She followed him, in her car, back to his apartment, sitting with the growing thrill of anticipation.

  Gillian was on the one hand a middle-aged widow who didn’t want to rush into another relationship just yet, but on the other hand she was a lonely and bored woman that had needs and desires to satisfy.

  The Summer Nights Agency had promised they could solve all of her emotional and carnal issues at once.

  They walked through the door of Paul’s apartment into the lounge and sat on the sofa.

  “Let me take your coat,” Paul said, and took off the first layer.

  They sat down beside each other and Paul took up the momentum.

  He kissed her softly on the lips at first; she turned to him and kissed him back.

  He was stroking her neck and hair, kissing her lips and mouth hard, and she was responding.

  Her breasts were pushing at her blouse buttons and Paul freed them.

  He unbuttoned her blouse a little and pushed his hand under her bra and cupped her breast, feeling it, soft and round in his hand, then moving on to the nipple, squeezing and rubbing it.

  Gillian was making no effort to stop him and was moaning softly as she was kissing him.

  He moved his mouth to her nipple and licked, then sucked, then bit softly.

  Gillian was laying her head back, with her eyes closed and sighing; her face was flushing pink.

  Paul put his hand on her knee and slowly moved it up her skirt. At the top of her tights he pushed his hand down underneath her knickers, to her shaven pussy.

  He moved down a little and found her clitoris, he rubbed it up and down for a moment, listening to her moan and go limp. He pushed a finger into her pussy; she was already wet and ready to go.

  He got up and led her by the hand into his bedroom.

  Paul turned Gillian around and stood behind her. He took off her blouse and started on the side zip of her skirt.

  Gillian stood there, stay-up blue stockings and matching blue bra and knickers.

  He turned her to him and kissed her again, cupping her face.

  He took off her bra and knelt down to slowly remove Gillian’s knickers.

  He could smell perfume on her fanny and knew she had prepared for tonight.

  He moved her to the bed, where she lay down with her hands behind her head, watching him.

  Paul slowly undressed and stood there, naked.

  He came to her and started kissing her again, taking his time, nibbling her neck, whispering nothings in her ear, about how beautiful she was and how he’d wanted her from the moment he’d saw her.

  He fondled her breasts, kissing her mouth hard. He moved onto the bed, kneeling astride her chest, using two hands to squeeze her breasts, pinch and squeeze her nipples. She was holding his head, stroking his hair, her breathing increasing.

  He worked on Gillian’s nipples awhile, sucking and licking. He wanted a good show tonight, but not his usual two-hour full-blown BDSM session, just a nice, good, satisfying piece of mock lovemaking.

  He moved down to her fanny, lifting her legs into the air at the same time. He parted her legs and kissed them one at a time all the way down to her pussy.

  He watched her but she had her eyes closed, but he could tell by her response that she was enjoying what he was doing to her.

  He would play it by ear and little by little seduce her more and more, with the repertoire of things he could do to her.

  He lifted her ass up a little and splayed her legs wide; she bent them at the knees. He could see her ass and her pussy all lined up.

  He parted the hood on her clitoris and started to lick, up and down, up and down, then side to side, side to side.

  Gillian was turned on more now; he pushed a finger into her ass and one into her pussy and continued to lick and lick and lick, pushing both fingers in and out, in and out.

  She was starting to come and he could feel her body moving up and down. He’d let her have this one quickly, then give her a couple more before sending her home.

  She was coming fast now.

  “Fuck me now, fuck me… please…” she blurted out.

  He ignored her and carried on licking her clitoris and finger fucking her ass and pussy as quick as he could.

  “Ohhhhhh, yeah… yeah… yeahh… ohh… ohh…” She opened her eyes and panted.

  Paul moved up to her mouth and kissed her, then broke off and smiled at her, as if to say how was it but she pre-empted his thoughts.

  “That was ridiculously good,” Gillian said.

  “I’m glad you liked it,” Paul replied.

  She looked at him, as if to work him out. Smiling at him, she cupped his face and kissed him again.

  “Shut your eyes…” he said, and she closed them for him, one at a time, and smirked.

  This was her first command and she’d instinctively obeyed!

  He picked up her two stay-up stockings and ran them over her face.

  “Eyes tight shut,” he repeated.

  He gently and softly rolled the stocking around one of her wrists and wrapped it loosely around the bedpost, he then kissed her mouth, as a reward for not resisting.

  He repeated the action with her other wrist and she was for all intent and purpose tied up!

  He took a vibrator out of his ‘box of tricks’ drawer and put it on the bed between her upper thighs, so she could feel it.

  She twitched a little, but still no resistance; she was smiling more now.

  He moved up the bed and sat astride her chest. Putting his fingers into her mouth, he opened it wide; she tried to suck and lick his fingers, she knew what was coming next.

  “Open your mouth… wider… Suck my cock for me, darling,” he said in a soft but firm voice.

  Paul p
ushed his cock into her mouth and let her do the work, she was sucking and sucking, breathing through her nose. Her rigid tongue was darting in and out all around the top of his cock, licking and sucking furiously. She could feel herself letting go and getting wetter all the time.

  “Make it hard for me, suck it more, that’s good, that’s nice. Lick around the head, that’s good, darling. Put your tongue back in now,” he ordered, grooming her all the time.

  He lay her head on the side and started to fuck her face now, slowly at first then harder and deeper, keeping up a steady rhythm.

  Gillian had never quite had this experience before, a man taking control and letting her live out her fantasies.

  He pulled out and moved to her fanny; she was panting and breathing more heavily now.

  He lifted her legs up, opened them wide and pushed his cock into her pussy in one go.

  It went straight in and all the way, into another soaking wet pussy.

  He started to fuck hard now, in, out, in, out, hard thrusts all the time. He picked up the vibrator and positioned it on her clitoris and switched on.

  Fucking her hard now, like a grudge fuck, pushing as hard as he could and vibrating her clitoris, she was moaning all the time, her breasts heaving up and down, slowly building to her next climax.

  Her pussy was soaking and Paul’s cock was sliding in and out effortlessly, without any friction to keep him aroused, so he decided to change course.

  He pulled his cock from her pussy and slowly pushed it up her ass, with no resistance from her at all.

  Slowly and gently, in an out, in and out, deeper and deeper with each stroke, until he could fuck it as hard as he fucked her pussy.

  He turned up the vibrator setting to max and kept it on her clitoris all the time.

  He could feel she was coming again and would let her have number two as soon as she was ready.

  As he fucked her ass and vibrated her clitoris, he looked at her – she was in heaven.

  She rode back on his cock, spreading her legs as wide as she could, panting and moaning all the time.

  She climaxed and as she did, her stomach tensed and her legs flayed then tightened on his cock.

  “Arhhh… Arhhh… Arhhh… Yeah… Yeah… Harr… Hard… Ohhhh.”

  She knew that she would have sex with Paul tonight, but she could never have envisaged this.

  She was completely satisfied with this evening’s activities. She had gone further sexually then she had ever thought possible.

  Paul had done things sexually to her in an hour, that her late husband had never done in thirty years… and there was more to come.

  She lay there panting for breath, with a rather pleased, happy expression on her face.

  “I’ve wanted to do that since the moment I saw you…” lied Paul.

  “…And I’ve wanted you to do it…” replied Gillian, truthfully.

  He started kissing her again, slowly and passionately, keeping up the romantic momentum.

  One of Gillian’s hands had come loose and she stroked Paul’s head as she kissed him.

  He broke off the kiss and untied her other hand, that’s when Gillian thought it was all over, but it wasn’t.

  He turned Gillian over and onto her knees, retying both hands back to the bedstead.

  He pulled from his drawer a small blindfold and put it on over her head.

  “This will make it more fun…” he giggled.

  “Ok, let’s try it then…” she said.

  He got of the bed and waited. He reached for his second vibrator, the one he could tape into place, and put it on the bed, between her knees, so she could feel it.

  Gillian was again full of anticipation – this was another new twist, she thought, and she liked the way Paul made sex into a game.

  He stood by the bed and touched her ass, stroking it and feeling the roundness. Gillian flinched, but liked it.

  He felt both cheeks one at a time, squeezing them as if they were breasts, savouring them.

  Paul got onto the bed and knelt before her nicely rounded ass. He slowly felt between Gillian’s ass cheeks and softly stroked her asshole.

  “Open your legs wider, always wider,” he said firmly.

  Gillian obeyed. He used the thumb of his left hand and started to stroke her asshole up and down, up and down.

  “Oh, I like that,” she said, “I like that a lot,” breathing harder now.

  He used his right hand to find her clitoris and stroke this up and down, up and down.

  She was enjoying this, it was like being sexually pampered, she thought.

  He put his left hand around her knee and found her clitoris; he pulled the hood up and with his right hand picked up the vibrator head, which was only an inch long, and put it into place on her clitoris, taping it to both sides of her pussy.

  Now he was ready…

  He pushed his cock into her still-wet pussy and started to fuck – long, deep, hard strokes – building up sexual momentum all the time.

  Long and hard, in and out, in and out, as deep as he could.

  Gillian was moaning again. This was wonderful, she thought.

  He was ramming harder now, he could hear his balls slapping against her ass cheeks.

  He then pulled out his cock and pushed it straight up her ass without hesitation.

  “Ohh my lor’… that’s nice,” she moaned.

  Paul continued to relentlessly fuck her ass, he counted the strokes…

  “1, 2, 3, 4, 5, 6, 7, 8, 9, 10.” Then out came his cock, straight into her pussy…

  “1, 2, 3, 4, 5, 6, 7, 8, 9, 10.” Out came his cock into her ass again…

  He was holding onto her ass cheeks, with the vibrator control in his hand; he switched it on…

  “Ohhh yes… yes… yeah,” was the grateful reply from Gillian.

  “1, 2, 3, 4, 5, 6, 7, 8, 9, 10.” Into her pussy…

  “1, 2, 3, 4, 5, 6, 7, 8, 9, 10.” Into her ass…

  “1, 2, 3, 4, 5, 6, 7, 8, 9, 10.” Into her pussy…

  “1, 2, 3, 4, 5, 6, 7, 8, 9, 10.” Into her ass…

  “Ohhhhh… Fuck me harder, Paul… Fuck me harder… Ohhhh, I’m coming… coming…” She tailed off.

  She came and she came big, a shuddering climax that shook her body from her shoulders to her toes and everywhere in between.

  Gillian lay face down, exhausted. Her hands had fell out of the bonds and she was gasping for breath.

  “My love, you should get paid for this,” she said, jokingly, laughing out loud.

  He sat down by her head and cupped it, kissing her forehead.

  I do, he thought, but he said, “I’ll make some tea.”

  On the way to the kitchen, he went into the bathroom and ran the tap in the sink. Lifting up his balls and cock, he washed them with soap and put disinfectant on them.

  He laughed to himself. A modern version of the whore’s dip, he thought.

  *

  Trudy sat behind her desk, drinking her cup of tea. She wasn’t in a very good mood and she hadn’t been for a while now.

  It was Paul’s complete lack of interest in her that was slowly getting to her; his complete indifference was starting to annoy her, but she wasn’t admitting it, not even to herself.

  She decided to call Gillian, just to see how the night went, she said to herself.

  “Hi Gillian, Trudy here from Summer Nights. I just wanted to see how things went with Paul.” Her heart was beating quickly, waiting for Gillian’s answer.

  “Hi Trudy. Yes, the night went well, very well indeed. Better than I could have hoped for, I had a wonderful time,” Gillian said, without hesitation.

  “Oh, that’s great news, I’m glad you’re pleased. Of course I knew you would be, he comes highly recommended. He’s a favourite with all our ladies,” Trudy said, almost biting her lips.

  “I can see why,” replied Gillian, almost giggling. “There’s a man that knows how to please a lady. I’m looking forward to seeing more of him in the coming weeks,” Gilli
an said.

  “I’m so glad you hit it off. Let me know when you’re free to meet up with him again and I’ll arrange it for you,” Trudy countered.

  “I will, I’ll be in touch as soon as I’ve rearranged my diary,” Gillian said in a naughty, devilish tone.

  “I look forward to hearing from you. Bye for now, Gillian,” Trudy replied.

  Her mixed emotions were making her feel anxious; she wanted Paul as a business asset, drawing in these paying clients, which she had no doubt he could do easily, but she also wanted Paul in her bed, exclusively, pleasing only her.

  Her mood was getting worse now, knowing how Paul had easily worked his sex magic on Gillian, without a second thought for her.

  Having Gillian tell her that she had also sampled the sexual highs that Paul was capable of taking a woman to, it angered her to know that Gillian, and any other woman for that matter, could be getting what she was craving for, but couldn’t have.

  Trudy was starting to feel a little bit angry now. Paul was a business asset, yes, but he was her business asset. She was supposed to use him, he wasn’t supposed to use her, or her agency.

  She was still annoyed when she remembered his distant and aloof attitude towards her.

  Trudy was a ‘diva’; she liked her male employees to grovel around her and to flirt with her, the director.

  She in return let them know that she could sack or sexually use any one of them, any time she liked.

  She didn’t like it the other way around, as it was with Paul.

  Her heart was pounding, she was feeling the venom in her growing, she was feeling the jealousy in her growing, but she was also feeling the love growing in there too.

  Oh noooooo… she thought. Not again…

  *

  Later in the day Paul had a phone call from Trudy.

  Trudy had rallied around and was now in control of her feelings.

  She had a rather special lady on her books and she wanted Paul to meet her.

  The lady in question was Belte Gilday, a Latvian woman, tall and dark-haired, slim built and still married to a local business man, who had decided to move into another house with his mistress, but was quite happy to pay Belte’s bills as long as they stayed married.

  Trudy wasn’t interested in Belte’s domestic situation in the slightest, what was important to her, was that Belte was quite prepared to pay above the going rate to satisfy her ‘needs’ and to have the utmost discretion in doing so.