A New Career for Jennifer Jenkins

Jennifer sat at the dining table with Jane, her granddaughter. They were skinning blanched almonds for home-made marzipan. Her daughter Jackie was in the kitchen baking a wedding cake for Jane's brother Greg and his fiancé.

Jennifer was restless. She had to admit that her life was pretty good. She'd never married and, despite having a family, had made a very successful career as a graphic designer.

Her last long-term relationship had lapsed five years before. Mostly because neither she nor her partner could really be bothered anymore. She didn't regret being single again but she sure did miss the sex. Sitting next to Jane wasn't helping. Five foot four, a curvy size 8, the nineteen year-old just oozed sexuality. The only thing that Jennifer would change was Jane's very short and spiky blond hair.

"So Jane, are you dating these days?"

"Gran! Why are you so keen to marry me off! You never married and I don't intend to either!"

"You just seem so..." She trailed off.

"What! Sad? Lonely?"

"Hey love! No. Not at all! Just the opposite. You're just so..."

"Hmmm?"

"...attractive." She sighed. "I'm surprised you don't have to beat them off with a stick!"

"What if I don't want to! Doesn't mean I have to have a boyfriend."

"No, of course not. You can do whatever you want."

Jane lowered her voice. "Doesn't mean I can't have fun... I can get all the sex I want."

Jennifer was amused rather than shocked. She smiled at Jane. "Course you can love. And why shouldn't you -- I did."

"Gran!"

"Just be careful. My mother was very young when had me."

"There's no need to worry Gran -- I'm well sorted on that front." She couldn't resist adding "Have been for years."

Back home in her flat Jennifer stripped off her clothes and headed straight for the shower. As she soaped herself she longed for another pair of hands on her body. She was lonely and horny but still shuddered at the thought of another man sharing her living space. She should take a leaf out of Jane's book -- but how do you get hooked up as a 60+ woman. The memory of her short experience with online dating made her shudder. No, not that way.

She watched a movie on her HDD recorder and went to bed feeling no better. Even a long session with her favourite toy left her yearning for some proper passionate sex.

A few weeks later she was channel hopping on Freeview and caught the last ten minutes of a fly-on-the-wall documentary on male escorts ("and the women who use them").

Days later she still had the image in her head of a slim older woman, with her face in shadows, talking very fondly of a young stud she'd just spent an hour with. Jennifer fetched her laptop and searched for 'male escorts'. She lost herself for an hour or so browsing the beef-cake.

That night she lay in bed and wanked to the mental image of some of the profiles she'd been studying. Even though self-administered it was still the best night she'd had in a while.

The following evening she did some more-directed research and decided to take the plunge and hire an escort for an hotel 'outcall' (she was learning a whole new vocabulary). She picked the second-best hotel in the nearest big town. Well -- big enough to be reasonably anonymous.

Three days later she was sitting nervously in the hotel bar drinking grapefruit and bitter-lemon and wishing it was vodka. She'd got there early to check-in and spent all the extra time that she'd allowed fretting about all the things that could go horribly, spectacularly wrong. She'd changed into a short, tight fitting cocktail dress in electric blue viscose.

When 'James' arrived he looked good. A bit shorter than she was expecting but well turned-out. He noticed her immediately, cocked his head and when she nodded slightly he strolled over and introduced himself.

He was very suave and self-assured but he didn't really capture her attention. She realised that there would be no meeting of minds that evening. She just hoped his tackle was up to snuff.

The deal was quickly agreed and she gave him her room number. She left first and had just got herself settled and reasonably calm when she heard the discrete knock. She let him in and handed him an envelope with the cash.

Remembering her fantasy, she wanted to shower with him first and feel his soapy hands caressing her breasts. But that, it seems, was not one of his 'likes'. She undressed self-consciously while she watched him strip. He really was quite beautiful and his equipment did not disappoint.

He took a condom from his Jacket pocket and laid it on the corner of the bed. He laid a tube of expensive lube beside it.

"So. How do you want it?"

"Er, I don't know really."

"Well, what's your favourite position."

"Um -- I like them all really. Er, doggy maybe?"

"Right-oh. So shall we get on the bed?"

She slid sideways onto the bed and lay awkwardly on her back with her legs crossed at the ankles and her knees slightly bent. Her thighs were pressed tightly together. She resisted the urge to cover her breasts.

James walked to the foot of the bed and bent over her. He took her ankles and pulled sideways. "Open up Jen or we'll not get anywhere."

She allowed him to open her legs. He laid across the bottom of the mattress and lowered his face towards her crutch. He sniffed at her pussy and then started to lick the outside of her lips. He set to work with his tongue.

Jennifer felt mortified. He sounded like a pig at a trough. He did occasionally hit her clit but, she supposed, mostly by luck. It was at least getting her wet. Horribly wet in fact, she could feel his spit running down her bum-crease.

After what seemed an age he lifted his head and scrutinised his handiwork. Finding everything to his satisfaction, he knelt up on the bed between her legs. He wiped the moisture off his face with his hand and wiped it on the counterpane.

"You ready Jen?"

She nodded -- not that she was, she just wanted to get it over and get him out of the room. He tore open the condom packet and covered his penis. Then he covered the rubber with a thick coating of lube.

"Hands and knees then -- and I'll do you from behind."

That sounded like a good idea to Jennifer. At least she wouldn't have to watch him! She rolled onto her side and assumed the required position.

He placed a hand on the base of her spine and she felt his slippery cock prodding around at her rear. More by luck than judgement he hit the spot and the head of his cock penetrated her. Even given the circumstances and her deep embarrassment it felt good.

He held her hips and worked his tool in and out until he was fully inside her.

He started to thrust into her steadily. She felt confused. His casual attitude and complete lack of empathy was a big turn-off. But his cock was big and hard and fucking her cunt. It had been a long time since she'd had a man inside her and it did feel good. She realised that if she mostly ignored him and concentrated on the feelings in her cunt (and assuming he could keep going for long enough) then she could probably get off.

She tightened her muscles around his cock and pushed back.

"That's it baby. Squeeze that cock." He carried on his steady fucking, pulling her back onto his cock as she thrust back.

His hands were warm on her hips. She focussed on the warmth of his body -- better than plastic at least.

She bent her elbows and lowered her breasts to the quilt. She could feel the smooth fabric rubbing her nipples. She rested her cheek on the pillow and reached back to her cunt. She spread her second and third fingers and slid her hand to cover her mons. She could feel his fat cock sliding between her fingers.

She started to massage her lips and clit. Yes, as long as he kept going she'd be able to cum.

James felt her hand moving. "That's it Jen -- cum for me..." - "Cum for me girl!"

She didn't welcome his patronising chatter at all. She gave him a little grunt of assent and he increased his pace slightly. After another five or six minutes she was breathing hard and definitely heading in the right direction.

"Are you going to cum..? Are you Jen?"

He was getting annoying. She hated to be called Jen. Still, she supposed, he couldn't know that. Maybe she should have used an alias.

But this was just distracting. She concentrated on her orgasm and tried to ignore him.

She rested her middle finger on her clit and rotated it gently in time to his thrusts. She started to tremble as her orgasm neared.

"That's it Jen. Come on honey... let it happen." He increased his pace again.

"Cum for me girl! Do you want me to cum? Do you want me to shoot my spunk for you?"

To be honest she didn't care -- she had no interest in his orgasm at all.

She rubbed harder. She had to hurry her orgasm before his inane chatter turned her off completely.

She wanked harder and squeezed down on his cock. She was almost there.

"Faster!"

He started to slam into her. Jamming her back onto his big cock.

She cried out as her orgasm started and shook her way to completion as James slowed down smoothly. Then pulled out and pushed her left hip sideways. She tumbled onto her back.

He pulled off the rubber, wanked his cock a few times and shot a huge wad over her tits.

"There you go Jen! Feel better?"

She was breathing hard and looking at the mess on her chest. The mixture of pleasure, relief and disgust was too much to bear. She wanted him out.

He tried to kiss her on the mouth but she pushed him away.

"Please -- I have to shower -- please go."

"Hey Jen! There's no rush!"

"Oh please go! Go now!" She started to cry.

"Oh love -- there's no need to cry! Come-on." He moved to hug her and she cringed away.

"Get out! Go! Now." She batted at his hands. "You've got your money -- go!"

He stood up and moved towards the chair where he'd left his clothes. "OK -- I'm going -- there's no need to be rude." He started to dress.

"I know! I'm sorry -- it's not your fault. I just need you to go and leave me alone."

James dressed quickly. He turned back with his hand on the door handle. "Well -- you've got my number. Give me a call next time you're feeling horny!"

He gave her a cheery wave and left. As soon as the door closed she rushed to the shower to wash him off her.

She felt empty. She'd always loved sex. And she'd always loved men. She loved cocks, and balls, and cum. She loved to suck and wank a nice cock and then watch the cum shoot out. She used to wank her first boyfriend until he blew his load over his belly then suck it all up. Then she'd get him hard again and let him fuck her and fill her cunt with more lovely spunk. She loved travelling home on the bus feeling his cum leaking out into her knickers.

'James' though had made her feel used and grubby. The Irony was that she'd been using him!

She dressed and sat on the bed for a while. What should she do? Stay the night anyway? Go down to the bar and get wasted? Head out into town and party? Or give up, check-out and go home?

She decided to head to the bar for one drink. She picked up her clutch bag, checked her key-card was in it and headed for the lift. Just as she rounded the corner she heard the ping of the arriving lift. As she hurried to catch it before the doors closed a trim young woman with long straight dark hair stepped out of the lift and studied the floor guide.

Jennifer took in her very short scarlet lycra dress and matching four inch stilettos and thought "I obviously picked the right hotel -- this is where the whores hang out!". The woman turned in her direction. Her lipstick matched her shoes.

She glanced at Jennifer as they walked towards each other and staggered. She put her hand on the wall as Jennifer hurried forward.

"Gran! What are you doing here?!"

"Jane? Is that you? What have you done to your hair?"

Jane stood up straight. "Gran. I have to go, I'm a bit late." She still hesitated. "Why are you dressed like that? Are you staying here? Why are you here?!"

Jennifer realised what sort of appointment Jane was most likely late for.

"Eh -- you go. Um. I'll be in the bar." She stroked Jane's powdered cheek. "Don't worry love -- I'll see you downstairs. She turned and hurried to the lift.

Despite her increasing desire for a stiff vodka Jennifer stuck with the soft drinks. She sat in a distant corner of the lounge, turning away quite a few hopeful bar-flies for nearly an hour and a half before she saw Jane in jeans and jumper heading her way. The wig was gone. She sat down next to Jennifer looking flushed and happy.

"Gran...?"

"I think this evening you can call me Jennifer -- don't you?" A waiter arrived with a chunky glass of expensive scotch.

Jane took a sip. "Jennifer what are you doing here? Have you been following me?"

Jennifer could see she needed to put Jane's mind at ease and there was an easy and quick was to do it. "Jane. I came here to meet a male escort called James. I had no idea that you'd be here. I'm very sorry to have embarrassed you."

"You! Gran, you've no need to book an escort! You're still a fox!"

"Is that what you tell your clients?"

"Ah -- so you've guessed."

"Jane -- why? Do you need money? Are you in trouble?"

"No Gran. The money's good of course but that's not why I do it."

"Why then?"

"Because I love sex! And all my so called boyfriends have been limp-dicked control freaks." She took another slug of whisky. "I choose my clients very carefully. They are charming, attentive and talented. Not to mention rich and generous! I do it for the sex -- the money is my excuse to get all those lovely hunks into bed!"

Jennifer thought back to her recent experience and felt like weeping.

"Gran -- what's wrong? I'm ok -- in fact I'm fine. There's no need to shed tears for me!"

Jennifer sighed. "Not for you dear... for me. My experience this evening was far from satisfactory."

"Why? What happened?"

"Jane! Do you really think I'm going to tell you about my sex-life?"

"Who else are you going to tell?"

Jennifer sighed -- she had a point. As she started to try and explain she realised that he really hadn't done anything that wrong. The problem was her expectation rather than his performance. Jane seemed to understand though.

"You see? That really is the whole problem with men -- no empathy. He'd probably be deeply hurt if he knew what he'd done to you but for them ignorance really is bliss." She signalled a waiter and held up two fingers. "I can help you know? I know a couple of great male escorts. I can hook you up with one of them or both if you prefer."

"Huh! And why would they be any better?"

"They'd be better 'cause they're gay -- and they really are a couple by the way."

"Oh! And they have sex with women?!"

"Only for money!" The waiter arrived with two large whiskys. "Well... not entirely true perhaps." She sipped her whisky. "This really is a great job you know. Maybe you should try it?"

Jennifer picked up the other glass and took a slug. "And how would that help?"

"Jennifer." She looked at her granddaughter. "Just replay that encounter in your head - " Jane paused " - with you in charge and him as the client."

She waited and watched her grandmother ponder.

"You know that you'd have done it differently and that you'd have had a great time." She waited for it to sink in. "And you know he'd have had a great time too and still think he was in charge."

Jennifer thought about it. She had to admit it probably was true. In all her sexual relationships she'd controlled everything. Allowing her partners to 'take her' in exactly the way she wanted to be 'taken'.

"Are you trying to recruit me?"

"No -- well not as such but you know you'd have a lot of great no-strings sex and make a bit of spare cash too. Why not give it a go?"

"Jane -- I'm over sixty. Who'd want to -- do it with me?"

"Jennifer -- as I said. You're a fox. You're slim and beautiful. You'd get plenty of business. Do you still do your Kegels?"

"Yes -- everyday."

"Then you'll get plenty of repeat business too."

"You're serious aren't you?"

"Yes! Why not give it a try?"

"I wouldn't know where to begin."

"You begin by getting some raunchy photos and setting up a profile." She reached into her bag and pulled out a tablet. "Hold on -- I'll show you mine."

She tapped the screen a few times and handed it over. "Don't click on the private gallery -- even you're not completely unshockable."

Jennifer took her time. She read the Profile and the FAQs. Had a look at the Gallery. Glanced at the Interview and the Blog. Then she noticed 'Rating 37'. "Jane. Does this mean you've had sex with thirty-seven men?"

"No Gran -- they're just the ones who've left feedback for me. I'm way past the hundred mark."

Jennifer gave in to temptation and clicked on the Private Gallery. She sighed "It's a long time since I had a threesome."

"Gran! You shouldn't be looking at that!"

"And you shouldn't be having unprotected sex! This isn't the seventies!"

"Oh don't worry about the boys -- they're professionals. That's the gay couple I told you about."

"Really? They seem to be having fun."

"Well. We've done quite a lot together. Me and Annie did all the pictures for their profiles."

"And who's Annie?"

"She's behind the camera -- she's my girlfriend."

Jennifer gasped and looked at her. "Are you gay too?"

Jane laughed. "No Gran -- I prefer to think of myself as omnisexual. Basically anything with a pulse!" She watched while Jennifer scrolled slowly through the hard-core images. "Annie and the boys would be happy to help you with a portfolio."

She reached out a hand. "Here, give me that." She took back her tablet and tapped at the screen. "Here." she handed back the tablet. "That's Alex's solo profile. Just look at that bod."

Jennifer looked through the profile. He really was attractive. If she'd found his profile earlier she may well have ended up with him in her bed that evening.

Jane could see the glint in her grandmother's eye.

"Go on Gran -- don't give up. Book the two of them for a couple of hours and have that threesome. It won't be a bit like -- whatever you said his name was."

By the time Jennifer and Jane decided to call it a night Jennifer was too tipsy to drive home and since she had the room booked anyway she decided to stay. Jane took a cab promising to fix up a 'social meeting' with the boys.

A fortnight later Jennifer arrived at a smart town-centre apartment above a classy high-street shop. The door was opened by a very tall, attractive, asian woman.

"Hi! You must be Jennifer. Welcome. I'm Annie." She took the small valise that Jennifer had brought and stood aside for her to enter.

She entered a large open-plan living space with a lounge area, a kitchen and a dinning area. Sitting around a low table were Jane and the two men she'd seen in Jane's private photo gallery.

The two men rose as she approached. Jane was right, they were both quite beautiful. Tall, slim -- very masculine. Jeremy was fair-haired and blue-eyed with broad shoulders and a square chin. Alex was darker, slightly olive skinned with an oval face and deep brown eyes. He took Jennifer in his arms and held her close as he kissed her cheek. She felt her heart speed up.

Alex released her and she turned to Jeremy. He took her face in both hands and kissed her very softly on the mouth. She was flushed and slightly breathless as Annie took her hands and led her to a small leather sofa. "Sit with me Jennifer. Alex will make us some tea."

They sat and sipped fine Darjeeling with Jeremy's home-made butter shortbread and chatted away. Jennifer was a bit on-edge at first -- she would likely be naked with these three strangers before evening. But they were all so easy and comfortable with each other that she rapidly relaxed and just enjoyed their company.