It was a Saturday morning in early May, and Caitlin could see the sun streaming through a crack in the curtains. Her alarm clock told her it was just after nine. She smiled and stretched out her arms above her head in an effort to shake a little of the lethargy out of her body. She knew she should get up, but she did like a lie-in at the weekend. She thought she’d give it five more minutes, and curled up in a ball with her hands between her knees.
She tried to work out her itinerary for the day. She was going to have to go shopping at some point, because she knew the freezer was all but empty. She’d recently over-come her fear of getting into a car again, a problem since the accident, and she was going to find herself a runabout. Her son-in-law Ben had promised to help with that when he’d been to football, and she was looking forward to their shopping trip together. She smiled at the little white lie.(XXX Stories)
She was just looking forward to seeing him, full stop. She’d seen him most days since the funeral and when she wasn’t actually with him, she spent most of her time looking forward to seeing him. They had become very close, like best friends. They talked all the time. She knew, for example, that a couple of times he’d been asked out on dates since the funeral, and each and every time had declined the invitation. They told each other everything. Oops, she though, there’s another lie. I’ve never told him how crazy about him I am.
Since the first time her daughter brought him home she’d suspected she had a crush on him. There was something in his eyes that made her want to give herself to him totally. She would be with him, staring into his eyes, and she would realise he’d stopped talking and was waiting for an answer, and she’d have absolutely no idea what he’d just said.
It would be about one when he got back from football, and he’d promised to take her to look at cars straight after. There was an element of planning in that, because she knew he would literally come straight after football – still in his shorts and needing a shower. He had the most perfect legs she’d ever seen. More than once she’d masturbated in her bedroom while he was in the shower next door. There was never a danger of getting caught, because she only needed a couple of minutes to bring herself to a shuddering orgasm at the thought of him. Whether she dreamt of joining him in the shower, or surprising him with a blowjob the second he stepped in the door, the result was always the same.
She could feel that familiar heat from between her legs. She thought she would have plenty of time to take care of herself, so she rolled over onto her back, sliding her white silk nightdress up as she did so. She cupped her pussy in the palm of her hand as she decided which fantasy to select…
She went for the kitchen fantasy, always a favourite. In it, she is doing the washing-up at the kitchen sink when Ben comes in from football. He has on his shorts and a baggy sweat top. His legs are muddy and he reeks of sweat, but he is elated because the team he is captain of has won.
He walks in the back door and shouts a greeting. She shouts one back and announces that she is in the kitchen. When he walks in, he is smiling broadly. His blonde hair is matted with sweat and she can see bl**d above one eye. He greets her with a kiss on the cheek as he would normally, before fetching a carton of orange out of the refrigerator. She asks about the bl**d and he laughs, saying that he had a good tussle with the opposition’s centre-forward, which he won.
When he kisses her she can smell the sweat on him. She loves the smell of sweat; it’s so masculine. They exchange pleasantries for a few minutes while he drinks the orange juice. When he’s done with it, he walks over to put the glass in the sink where she is still doing the washing-up. She turns her head when he comes over and their eyes lock. It’s at this time he realises how hungry she is for him, how desperate and frustrated she has been. Her arms, still in rubber gloves, go around his neck and their lips meet.
She is smaller than him and has to stand on tiptoes to return his embrace. Their kisses are deep and passionate, and very soon his tongue is freely roaming her mouth and she id delighted by the intrusion.
He breaks from the kiss, turning her away from him. Her eyes close as her head goes back against his chest. He leans in to kiss her neck, but the kisses are rough and soon turn to bites. She loves it, loves the pain, loves it when he is rough with her. He grabs at her skirt, hoisting it up before starting to rub her pussy through the gussets of her knickers and tights.
She feels her hole moistening at the attentions of his hand. He uses the other to start pawing at her breast, pleasing himself, hardly considering her needs. She opens her eyes and looks down at her body, but he pulls her hair sharply and drags her head backwards. She starts making noises that become quiet pleas to be taken. Somewhere outside her fantasy, she is aware that she is making the same noises out loud. She used two fingers to spread open her pussy lips, allowing clear access to her clitoris. She used two fingers on her clit, roughly, like she imagined he would in her fantasy.
With rising urgency she puts a hand behind her back to try and grab his cock, when she can feel stiffening against her bum. He is indifferent to her attentions and he pushes her head down low over the foamy water in the sink. She has to brace her arms to avoid being pushed face first into it, but as it is her shoulder length her still dangles in it, turning the tips from their customary chestnut brow into a glistening black.
Squatting behind her, he starts to rub her roughly through her clothing. She is sodden, and he can feel it through her knickers. He makes out that he is disgusted, which she loves. He takes two handfuls of her tights and stretches the material apart, quickly reaching breaking point. She hears the tear of the material and groans with pleasure as he pulls her knickers to one side. Quickly he puts his face into the space between her legs and she can feel the roughness of his short beard on her thighs and bum cheeks. His tongue seeks out the hot, wet slit of her vagina, but he is frustrated by the angle she is standing at. Without missing a beat, he transfers his attention to her bum hole, roughly licking all around it.
Too late she realises that he is not trying to stimulate it so much as lubricate it, and her breath is taken away as he roughly works a fingers into her anus. He licked all around his finger as it worked in and out of her whole. The pain she felt was beautiful, and she found she was even sticking out her arse to try and take his finger further in. When he realised she was enjoying it, he quickly withdrew it and replaced it with his tongue, which went straight inside her hole. He moved it around in a circular motion while his thumb started to flick away at her clitoris.
Her breath quickened as he masturbated her. She closed her eyes to concentrate on the feeling, before opening them in surprise as he harshly thrust his thumb into her hole. He searched for the g-spot with the ball of his thumb, while his middle and index fingers continued stimulating her clitoris. She could feel an orgasm rising rapidly.
As if determined to stop her from reaching it, he suddenly stopped everything he was doing. She looked round to the side just in time to see his muddy shorts fly across the kitchen and she knew that he had his cock out. She wiggled her ass at him, encouraging him to enter her. He played with himself while he admired the view, stroking himself with long, slow strokes. He took a step closer and began to nuzzle her clitoris with the head of his cock and she braced herself for it entering her.
In a surprise move, he thrust his cock deep into her anus with one push. She screwed her eyes up and tried to relax so that she could stand the pain of trying to accommodate his member. He began to work in and out of her, never giving her time to get used to it. Her bum hole was tight and she knew the friction on his cock was having an effect on him. After only a couple of minutes thrusting she could hear him intoning, ‘oh yeah, oh yeah, oh yeah… I wanna come.” His thrusts became harder and harder.
Abruptly he stopped and withdrew his cock completely. She knew he was very close and couldn’t understand why he’d stopped. He showed her immediately by pulling her upright using her hair and spinning her round by the shoulders, before pushing down on the top of her head until she fell onto her knees. She smiled and then opened her mouth, reaching up to take hold of his cock. He knocked her hand away and then took a fistful of her hair, pulling her head back so hard she had no option but to kneel there with her mouth open. He started to pump away at his cock with his free hand.
She could see the pre-come leaking from his slit and she looked forward to receiving a mouthful of his hot, salty come. She stole a hand between her legs and managed to make contact with her clit without him noticing, but in truth his attention was fully focussed on himself. He moaned several times before a loud grunt, and his hand stopped. Thick, white sperm flashed across the gap between his cock and her face, splashing her face, landing on her cheeks, her lips, her neck, her tongue. It was her turn to moan loudly as she brought herself to a thundering orgasm as the sperm dripped into her mouth and she lapped it up.
She lay there in the afterglow of her orgasm, listening to the hustle and bustle of the world outside. She could hear c***dren playing, dogs barking and car doors slamming. She shut the noise out and thought about Ben. She was so attracted to him, but she did not dare tell him. She would never, ever tell him how she felt about it. She would die of embarrassment if he ever found out about her feelings, or her fantasy sex life for that matter.
She loved her late husband, Matthew, but she knew also that she had never been truly happy with regards to their sex life. She had a wild imagination and a high sex drive, and neither of those things had been satisfied by sex with Matthew. She sighed as she wondered if she would ever have sex again. Was that really it? At forty-two, was her love life really over? She knew it shouldn’t have been. She was small at five and a half feet tall, with a slim figure inherited from her mother, and a full head of chestnut brown hair. She could pass for a woman some years younger than her real age, but could she be bothered with dating again? What she needed was someone she knew, someone she cared about and who cared about her. Someone like Ben.
They met up later that day, as planned. He greeted her with a kiss on the cheek, as normal, and complimented her on the way she looked, which again he always did. She scrutinised his words more closely than usual, looking for a hidden meaning. Did he truly like the way she looked, or was he just being polite? Was there any masked depth of feeling in the kiss? She told herself not to be silly.
He patiently drove her around several car dealerships without her ever really making her mind up about what she wanted, or indeed having an idea about what she was really looking for. She thought she out to buy something practical, just an economical little runabout with good mileage, but what she really wanted was something completely the opposite – something fast and sexy. She had no idea where these thoughts were coming from. When she thought she sensed Ben becoming a little weary of her indecisiveness, she offered to take pay for tea somewhere, which he politely declined. He must have seen that she looked slightly dismayed.
“I’m a bit sticky from traipsing around in the sun all afternoon. Tell you what, I’ll nip home and get a shower and get changed, then I’ll come up after and we’ll get something to eat at your house. You can cook for me, to make up for having to follow you around all day?” He laughed. She bit her lip for a moment before replying.
“Are you sure? Wouldn’t you rather be out with your friends on a Saturday night?”
“Boring bunch, they’re all married and won’t come out now!” A cloud seemed to pass over them at the mention of marriage. Ben was the first to buck up. “Look, I’ll call at the video shop on the way round and find something to watch. Something cheerful, eh?” She smiled, and they agreed that he would be around about eight.
As it was, it was half past when he got there, having struggled to find a comedy film that he thought they would both like. He wanted to watch something gross, but he was sure she wouldn’t find anything like that funny. He’d also bought a bottle of wine for her, which he presented with his usual kiss. There, she thought, did he just linger a little longer with the kiss, like he was trying to smell my perfume, or something?
She knew he liked chicken, so she’d prepared a chasseur for themselves. He’d brought a period comedy, something quite highbrow and intellectual that she laughed all the way through. He caught himself thinking how pretty she was when she laughed, but quickly snapped out of it. The meal was excellent and the wine quite strong, so by the time the movie finished they were both quite tired. She asked him if he wanted the spare room, and then immediately worried about how it sounded to him. Did it sound like a veiled come-on? She told herself to stop being silly, he’d stayed over many times in the spare room. When he accepted he didn’t look as though he thought anything was untoward.
She tidied up in the kitchen, listening to him plod about upstairs getting ready for bed. She thought she might have to stay downstairs until he was asl**p – she didn’t know if she could trust herself not to go and climb in with him (actually, she wasn’t sure she wasn’t going to do that anyway even if he was asl**p). Before she knew what she was doing, she found herself at the bottom of the stairs, asking if he wanted a drink bringing up. A quick ‘yes, please’ by reply started her pulse quickening.
She was in her housecoat when she took him a glass of milk in. He was already in bed, and as she entered the room she caught sight of all his clothes – including boxer shorts – over the back of the chair, and she felt sick with desire when she realised he must be naked under her sheets. She set the milk down on the bedside table, and, managing not to look at him, asked if he wanted anything else.
“Do you still miss them?” came his surprise reply. She was taken aback, and had to swallow twice before she could formulate an answer.
“Yes, of course,” was the best she could manage. She thought about it for a second before perching modestly on the edge of the bed. He was on his right side, facing the edge of the bed she was sat on. She had her back to him, but was half-turned to face him. “I do miss them, and of course I still love them, but after this length of time it becomes a different sort of feeling.”
“I know what you mean. It’s like when United sell a player. You miss the player, and you still look out for his new team’s results, but you realise that things move on and that nothing ever lasts forever. Old players go and new ones are signed, but the main thing is life goes on.” She laughed at his analogy, but she knew exactly what he meant and she nodded in agreement.
There was a pause, a pause in which she though things could go one of two ways. She could either stand up and say goodnight, and walk out of the room knowing she had missed a chance. Or, she could turn round, bend over and kiss him softly, on the lips, and wait for his reaction. What he said caused her to taste the bright, metallic tang of panic.
“Caitlin, do you miss sex?”
She was paralysed. She could not breathe, and she certainly could not turn around to look at him. She stared at her hands, wringing together in the soft glow of the bedside lamp, while minutes passed. She heard his soft breathing and tried to calm herself, convinced he would be able to hear her heart thumping behind her ribcage. She glanced around the room, desperately trying to work out his intentions for asking the question. Was he making a move on her? She tried to think of a non-committal answer that might steer the conversation to safer waters.
“Why do you ask?” She said softly, in her fading Irish accent.
“Do you remember Thursday night? I spoke to you on the phone?”
“That’s right, you said you’d got a re-arranged match and would it be okay to go out in the afternoon rather than the morning.”
“What else did I ask?”
She racked her brain to try and remember what else they’d talked about. Come on Caitlin, think! She shook her head.
“I said I’d left my football boots at your house and would-”
“Would it be okay to call round and pick them up before you went-” she cut off as she realised what that meant. Ben had his own key. He had been in the house this morning while she had been…
“When I came in the house, I realised you were still in bed because the curtains were closed and the paper was still on the doormat. I thought, I know, I’ll surprise her and take a cup of tea up before I go to football.” She cringed, closed her eyes. She knew what that meant. “Your bedroom door was not shut. I pushed it open and saw you.” There was another pause, in which she wanted the earth to open up and swallow her. Ice ages came and went, civilisations rose and fell, but she still could not think of anything to say for a long time. When he reply came, it was in a cracked voice, barely audible.
“You were masturbating.”
She wanted to die. She’d never even let her husband see her playing with herself, and now here she was, sat in her bedclothes with her son-in-law, who she was desperately attracted to, trying to find some explanation for what she’d been doing, anything no matter how improbable it sounded. Just something, so she could convince this gorgeous young man that she had not been fantasising about him, about having sex with him, about feeling his warm sperm as it dripped slowly into her mouth. There was nothing she could say. She decided to brazen it out. The worst was done, he’d seen her playing with herself. If he didn’t like it, it was tough luck. This was a part of who she was.
“Yes, I was. I miss Jodie’s Dad, and I miss sex. I can’t help that.” She found herself wanting to take the plunge now that she’d opened up, to confess everything to him. She paused for a second to gauge his reaction, but none was forthcoming. “I… I shouldn’t even be telling you this, I know, but since the accident I don’t really have anyone to talk to. Everyone’s on eggshells around me, like they don’t want to say anything that might upset me.”
“I know that feeling. They keep giving me easy cases at work, when what I want is something that will take my mind off coming home to an empty house.” Ben worked with young offenders, aged roughly 15-21, helping them with their rehabilitation. It was his knowledge of the pressures on young people that had stopped him and Jodie having c***dren.
“Ben, I never… that is, Jodie’s father and me, we… we were always good out of bed, but in it we were never great. Especially after Jodie was born. I thought I was the one that was supposed to lose interest in sex, but it was him. I thought I’d put weight on, so I made an effort and I was thinner and in better shape than ever in my life. I wanted, you know, to try things, new things, anything by the end. I can’t even remember the last time I had an orgasm with him. I guess I just have a high sex drive, and he didn’t.” He paused, thinking she was going to continue, but she didn’t. She choked back a sob, thinking she’d gone too far and revealed herself as some sad old housewife desperate to get laid.
“What do you want to do then?” He asked quietly.
“What do you mean?”
“Well, you said you wanted to try things. Anything, you said. If you had your wish – say you found some sort of nymphomaniac genie in a bottle (she giggled slightly) – and he offered you anything you wanted, what would you ask for?” She thought about it for a long time, not sure what her answer should be.
“I think I’d want to be young again, the age I was when I got married. I want to feel alive, and desired, and attractive to someone, and it’s a heck of a long time since I felt any of those things.”
“Why do you need to be young? I mean, what’s stopping you now?”
“Oh Ben, no-one wants a forty-something widow. No, seriously, I don’t even know where I would start. I think I’m a little old for going on the pull!” She laughed in spite of the way she felt inside, a girlish laugh that amused Ben.
“What if someone could… arrange… something for you?”
“Like a blind date? I’m not sure…”
“No, not quite. A blind date would be a lottery, when what you want is a cert, a banker. Someone that can be discreet, someone who knows what you want, who can arrange things just as you want them. Someone who can get you what you want, whatever that may be.”
“A-ha, back to your nympho genie in the bottle! And how, exactly, am I supposed to find someone like that?”
“I’m right here, aren’t I?” She knew he was going to say that, somehow. Just knew. So he was putting a move on her. Almost imperceptibly, she loosened the cord on her housecoat to make it easier to remove, then turned to face him.
“Obviously we can’t sl**p together, Caitlin, that wouldn’t be right. But if you tell me what you want, I know I can arrange it for you.” She was crushed, she didn’t know what to say. He continued. “So if I asked you what you would like to try first, what would it be? Think about it before you answer, I’m absolutely, 100% deadly serious.” She didn’t have to think. If she couldn’t have him, then she knew what her second favourite fantasy was on those long, lonely nights in bed.
“Sex with a stranger. A nameless, faceless nobody, who never tells me his name, who never even speaks. He comes in the room, and we do it, and he leaves. End of story.”
“Caitlin, do you want me to arrange it for you?” She looked down at her hands, folded in her lap. She knew the answer and suspected he did, but she still had to vocalise it.
“For tomorrow night?” She nodded, three short nods, barely there.
“Stand up, please.” He said with quiet authority. Nothing if not an utterly obedient housewife, or at least former housewife, she did as she was told.
“Would you undo your housecoat for me?” She could not look up at him, but meekly untied the cord. It fell open at the front, revealing a white silk nightdress that was so long he could not even see her feet.
“Well, don’t be shy, let’s have a look at you then.” She shrugged her shoulders and the thick woollen housecoat fell to the floor. The nightdress revealed almost no cleavage, and the straps looked thick enough to support boulders the same size as her.
“Hmm… that’s not going to do at all. A man sees you in that, he’s going to think you’re some sort of arctic explorer, not a hot bl**ded Irish vixen!” She giggled again despite her embarrassment. “Let’s see what else you’ve got. Would you go into your room please, and put on whatever you think your sexiest underwear is. Go on, now please.” She went.
It took her ten minutes to select something to wear, and another five minutes to summon up the courage to put it on. It was black, a bra and panties, lacy and sexy in a middle aged way. Jodie had selected it for her, to wear under a long black dress she wore at one of Matthew’s Christmas work’s meals. She stood and inspected herself in the mirror. She was slim, having never bought anything bigger than a size eight since Jodie was a toddler, with slightly wavy brown hair. A few laughter lines, she supposed, but nothing she couldn’t minimise with make-up. If she were f***ed to, she would admit that she had a figure that girls half her age would be pleased to have, but it was a long time since anyone had told her that, or eve looked at her like that. And yet here she was, in black lacy lingerie, about to parade herself in front of her son-in-law. She shook her head.
It was several more minutes before she had the courage to go in, and even then she’d put her housecoat back on. He merely raised his eyebrows at her, as if to say, well, what are you waiting for? She opened her coat and slowly removed it to stand there in front of him, almost naked. She could feel herself start to get wet, despite the massive trepidation she felt. He looked her up and down, and she felt almost used, like a hooker in an Amsterdam sex shop window. She thought she could see movement beneath the sheets, but quickly averted her eyes, lest she blush. Was he getting an erection?
“Well, that’s much better,” he said, “but still room for improvement. Shall I tell you what we’re going to do tomorrow?” She nodded, still not looking at him. “We’re going shopping. We’ll check out all the big department stores, and find you something sexy to wear in bed, and we’ll throw that white thing away. After that, we’ll find you something sexier to wear out of bed, because there’s little chance of you being able to show off your slinky new look in bed if you still dress like a Sunday school teacher out of it.” She smiled, her embarrassment lessening by the second. “Then, we’ll find something to wear underneath all the foxy new outfits, something that will turn men red hot with desire. How does that sound?”
She thought it sounded fantastic, but she was desperately worried at the thought of going underwear shopping with Ben. She could feel herself soaking wet already. Just the sound of his voice, the authoritative way that he decided what she should be doing… she was a wreck inside. Her stomach was filled with butterflies and she had no idea if she would be able to walk out of the room.
“Well, that’s the plan for tomorrow then.” The cheekiness returned to his voice as he continued. “And in the morning, I’ll have tea and toast, orange juice, and the Sunday papers in bed please!” She laughed, and was about to raise an admonishing finger when the authority was restored to his voice and he continued. “And I think I’ll have it served like that, please,” he said, indicating the black lingerie.
She returned to her room on fire. She carefully laid the lingerie out for the next morning and slipped between the sheets naked, grateful for their cooling touch. Despite the knowledge that he was next door and almost certainly still awake, she could not help herself but to use two fingers on her swollen clitoris, bringing herself to a crashing orgasm. A short time later, she rolled over and withdrew an anonymous red volume from the top drawer of the bedside cabinet.
Excerpt from Caitlin Young’s diary:
I can’t believe that all just happened. I can’t believe that he saw me, and I can’t believe that he asked me about it. Most of all I can’t believe that I told him all that stuff! What was I thinking of! What must Ben be thinking of me? I can’t go through with it, I know I can’t. Maybe it was just the wine talking. Must be. We’ll have forgotten all about it in the morning.
The sun woke her up the next morning, just as it had the day before. She began her usual elaborate stretching ritual until suddenly she stopped, mid-stretch. Her eyes had fallen on the black underwear, arranged exactly as she had left it the night before. She shrank back under the covers. Everything hinged on the choice she had to make right now. If she ignored the underwear and brought him breakfast dressed normally, it would send him the unequivocal message that his offer had been turned down, and she knew she would never have the nerve to bring it up again. Her sex life would, in effect, end this morning. On the other hand, if she put it on and it had been the wine talking the night before, what sort of message would that sound to him?
But if his offer had been earnest… then finally she would get the attention she was craving, and of the particular sort that she craved. And if their strange relationship continued, and they became more intimate, then just maybe there was a chance that they might end up together some time. That tenuous hope decided her. She showered quickly, as normal, and stood briefly listening at Ben’s bedroom door. She detected only the sound of his breathing and presumed he was still asl**p.
She thought that making some sort of effort was in order; so, removing the scrunchy that she customarily held her hair in while showering, she shook it loose and examined it in the mirror. She heated up her curling tongs and curled the ends of her hair under, paying attention to the front, curling that so that it curled under her chin, framing it nicely. She applied just a hint of eye make-up and some mascara. She glossed her lips to perfection, before selecting her favourite perfume and dabbing it on her neck lightly.
Finally, she dressed carefully in the black lingerie. Looking herself up and down in the bedroom mirror, she was again happy with what she saw. She was excited just at the thought of getting dressed up and making an effort for a man again. A wicked grin curled her lips as a thought occurred and seconds later she was rummaging around in the walk-in closet, and the grin became a smile as she emerged triumphant, clutching a piece of folded white material.
Fifteen minutes later Ben was awoken by the sound of the curtains being drawn back. With an effort he peered through half-closed eyes, which soon widened with surprise at the sight that greeted him. A cooked breakfast, a full toast rack, coffee and orange juice, and the Sunday papers, served by Caitlin who, as promised was wearing her black underwear topped off with a tiny white apron. She had a broad smiled on her face as she bustled about in business-like fashion, greeting him with a cheery ‘good morning’ as though serving men in her lingerie was normal behaviour for her. He beamed back at her, announcing that everything was indeed in order when prompted.
He could not take his eyes off her as she fussed un-necessarily around the bedroom, making a big show of picking things up and putting them down again so as to give him the maximum number of views of her ass and cleavage. He loved the show, and he had someone in mind who would similarly appreciate it. When she’d left the room he fished in his jacket pocket and produced a small silver mobile phone which he snapped open. He tapped out a message to a friend asking if he fancied a beer later that night. Five minutes later a familiar tone rang out to say that a message agreeing to said plans had been received, and with that the enactment of Caitlin’s first fantasy was confirmed.
Later that day they set off on the discussed shopping trip, the destination a local shopping complex of over 200 stores. She was nervous and it showed, but Ben had been at pains to put her at ease and bolster her confidence and she readily smiled at his compliments. Their first destination was a huge department store where he said he had shopped at with Jodie.
He took her first to the clothing department because, he reasoned, it would make her feel more at ease before they went on to the more risqué stuff. They selected a denim skirt, faded and finishing just above the knee. Stylish and smart, but not especially sexy. Part of the easing in process. Then, a couple of blouses, cut so as to emphasise her slim waist and appealing cleavage. He insisted that she undo a couple more buttons when she tried them on, so that the delicate lace between the cups of her bra could be seen. It was the most daring thing she’d done, dress-wise, in years, and she felt emboldened just from doing that.
He then took her round the footwear department, where against her better judgement they selected some knee high black boots and some very flimsy high heels, which had straps which wrapped around her legs many times. It took her several minutes to fasten them up, and she had the distinct impression that he was looking down her top, and when she was parading up and down to see if she could walk in them, he definitely appeared to be staring at her body rather than the shoes. His looks left her excited. Maybe he was coming to appreciate her more?
After a coffee he decided that they should go and look for underwear. She was slightly more hesitant, but knowing that that was the real reason for the visit she could hardly refuse. They visited a shop rather than mill around the busier department stores, as he said the shops would be quieter and more discreet. They browsed the racks and she found herself surprised and aroused by the goods on offer. She felt a tap on the shoulder and turned to find that Ben had selected several products. “Time to try some on!” he grinned. He leaned in close as he handed them to her.
She took the goods and approached a disinterested shop assistant, who gave her a blue plastic tag and motioned over her shoulder without a word. Assuming that she was indicating the location of the changing rooms, Caitlin explored the back of the shop before finding a row of curtained booths that served as changing rooms. Seeing that they were all empty, she entered the closest one, drawing the curtain shut behind her.
She looked at the underwear that Ben had given her. There was a black set, shiny and seemingly quiet plain compared to some of the others that she’d looked at. She read the label and discovered it was designed to enhance the cleavage. The second set was white, intricate lace patterns with cute white bows between the cups, and on the waistband of the knickers, which were tiny. The last item was black, a boned lace basque with underwired cups and detachable suspenders. She looked at it in wonder, having never worn anything even remotely like it before. She decided she would try that on first.
She started to unbutton her blouse, but was interrupted by Ben’s voice from somewhere in the shop saying, “I’ve found the stockings you want, hold on!” and before she could say anything else, the curtain slid open and Ben was there, in the cubicle with her. He grinned.
“Pretty sly, huh? Pretending you’d shouted me to fetch you some stockings. Although to be honest, I think if I’d stripped off out there and walked in the shop assistants wouldn’t have said anything!”
The cubicle seemed to have become a whole lot smaller since there were two of them in it. She was aware of the scent of his aftershave, and her own breathing. Everything seemed intensified in that dizzying small space with him.
“Come on then now we’re here, let’s have a look at you in them! Are you going to stand there all day, or do I have to undress you myself?”
She stood there for a moment looking at him, wondering whether he was serious about both getting undressed in front of him, and doing it himself. Fortunately for her, she didn’t have to wait long for an answer as he carried on unfastening the remaining buttons on her blouse. He’d only done a couple when she took hold of his hands and stopped him.
“It’s okay, thank you, I can manage!” she said flirtatiously. She took over the process of undoing her buttons before he put his hands gently on her waist. She looked up, wondering if this would be the moment that he kissed her, but to her dismay he whispered to her, “turn around, I want you to watch yourself in the mirror.”
She did as bidden, turning round slowly. She looked herself up and down, then looked at Ben’s reflection over her shoulder. He seemed to dwarf her. He smiled patiently, appreciating that this was all new to her. She seemed transfixed, looking at their reflections, her arms hanging limp by her side. Before she knew what was happening, Ben was undoing the buttons on her blouse. Watching in the mirror, it was as though someone else was being undressed, so she watched contentedly. One by one the buttons popped undone until her blouse hung open and the lacy material of her bra was clear to see.
He slid the blouse over her shoulders and down her arms, allowing it to fall to the floor. They both watched the mirror intently. He ran the tip of his finger down her arm from shoulder to wrist, and she smiled at the pleasant sensation. Next, he popped the button on the side of her skirt and drew the zip down excruciatingly slowly, the monotonous clicks of the zipper like the ticking of a clock. With the slightest touch from his fingers, the skirt slid over her slim hips and came to rest on the floor with her blouse.
For the second time that day she stood in front of him in her underwear. This set was white and lacy, pretty but not overly sexy. She was also wearing a smart but serious pair of shoes, not too high. He leaned in close, so that his lips were practically touching her earlobes, and yet he seemed to speak so quietly she still had to strain to her him.
“See, this is what I was talking about last night. Everything you wear is smart, and pretty, but never sexy. What I have in mind for you to wear will make you look sexier, and if you look sexy you’ll feel sexy. Then other people will come to regard you that way, and you’ll be fighting them off, you’ll see.” She smiled as he continued. “You have a fantastic figure, women half your age should be jealous.”
“Look at this tummy. Flat as a pancake, and mmm, skin so soft…” he started stroking her tummy, first with the tips of his fingers, then with his whole hand, slowly backwards and forwards across it. His fingers touched upon the waistband of her knickers and for a moment he seemed to be massaging the area of her tummy and inch or so below the waistband. Then he was talking again.
“I like your shoulders and neck too…” he leaned further into her so that when he spoke, she could feel his lips on her neck, and she instinctively tilted her head sideways so he had unhindered access to her neck. He used his hands to gently massage her shoulders and the tops of her arms. “I love kissing a woman’s neck, they always seem to respond to it. How about you Caitlin, do you like it?” She murmured her agreement, but by now her eyes were half-closed as if in a daze. She was content with the touch of his lips, and the sight of his hands all over as she watched in the mirror.
“I’ll tell you what else I like Caitlin. I think you have the most fantastic breasts too…” Her eyes snapped wide open as she felt the clasp of her bra undone, and with a feather light touch he’d dragged the straps down her arms, allowing the bra to drop to the floor. Then his hand were on her tummy again, just inches below her breasts. “Look at them, so firm.” Unbearably slowly, his hand moved up her body until he was cupping them gently with his hands. She allowed her head to lean back against his chest and she watched in the mirror as he held them. He wasn’t doing anything with them, just taking their weight gently in his hand. “Hmm,” he said, “I think I’ve guessed just about right” and with that his hands were gone.
He lifted up the black basque, and disentangled the straps and the g-string from their hanger. As she held it in her hands, it seemed so petite; she thought she would never get into it. “Oh, I didn’t realise it came with its own g-string. Let’s try that on too.” He looked up and caught her gaze in the mirror and she realised with dread that he meant for her to take her own knickers off in front of him. She gulped, and paused, but then she was doing it, allowing them to rest on the floor with the rest of her clothes. She stood naked before him for the very first time. She stood still, allowing his eyes to roam over her reflection. He snaked his right arm around her until it was resting on her groin, just millimetres above the top of her pubic hair. He started to rub his hand slowly in a small circle.
“Very nice, very nice. One day, do you know what we’ll do? We’ll trim this a little, make it nice and short, and tidy.” And with that he was rubbing his hands in the soft down of her pubic hair, allowing his fingers to become entangled in the tight black curls but never allowing himself to come into contact with her sex. She held her breath for what seemed like hours, before his hand was removed and he patted her ass. “Let’s get a move on then, they’ll be sending a search party for us.”
She dressed slowly and deliberately, pulling the tiny black g-string on first, then the basque. He presumed to fasten it for her while she stood with her head inclined, holding her hair up. She rolled the stockings up and fastened the clips one by one, and then slipped back into her shoes. Finally she looked up and stood in front of him in the lacy black basque. His eyes feasted on her, and right at that moment she could not ever remember feel as aroused as she did at that moment. Ben swallowed hard. “Well, if that doesn’t make a man want you, nothing will. Let’s get these bought.”
They drove home and discussed the plans for that night. Dean revealed that he’d arranged to meet someone he knew. She was to be waiting in the bedroom from eleven onwards in her new lingerie – whichever set she wanted from today’s expensive new acquisitions. He would send her a text when they were on their way back, after which she was to wait in the bedroom, in the dark.
As arranged, Ben went to meet his friend. Over the next couple of hours, Ben was careful to make sure that his friend had more to drink when he did. He didn’t want him to have too much to drink, but he certainly needed him to be more open to suggestion. But Ben had selected his target well. He asked his friend about his love life, knowing full well that his girlfriend had walked out on him a couple of months before, and since then the man had not even had so much as a one night stand.
“Well, to be honest Ben, I don’t seem to have had a lot of luck with the girls since I became single. I just don’t seem to have the confidence to approach girls anymore. I’ve even thought about joining one of those online dating agencies.”
“That seems a bit desperate!” Ben laughed.
“That’s how it is mate. If nothing else, I’m absolutely desperate for a shag!” He laughed. “I’m going to get another round in, do you fancy one?”
Ben drained his glass and waved it at his friend to signal his agreement. Once he was alone at the table, he produced his mobile phone and began to tap in a text message.
With a couple of hours to go, Caitlin bathed and pampered herself, before selecting the black basque. She applied her make-up carefully and then dressed slowly, enjoying the feel of the material on her skin. She could feel herself getting wet, and as she lay on the bed in the darkness, she began to wonder how she would keep her hands off herself. She was helped in that quest by the beep of her mobile phone with a text message:
Everything going okay. Back about half eleven. Be ready. Ben
She shivered with anticipation as she snapped her mobile shut. She still couldn’t believe that she was going through with it, but the thrills that she felt merely from choosing underwear made her think that she was right. There was no way that she should, or even could, turn her back on her sexuality. She lay back in the darkness.
She had no way of telling whether she’d been waiting minutes or hours. The thick curtains precluded almost all light from the streetlamps and it took some time before her eyes became adjusted to the dark. She’d gone with the basque in the end, and once her eyes became adjusted to the dark, she could make out the contrasting black panels of material against her china white skin. The thought of what was to come was torture, both arousing and daunting and the same time.
Some time later, she heard the key turn in the front door. Lost in her reverie she had heard neither car door nor footsteps. The front door click quietly shut and she could hear someone moving about, but could not discern whether there were one or two people downstairs. After another almost intolerable wait, her ears picked up the soft pad-pad of feet on the staircase carpet.
Someone eased the bedroom door open, and a shape appeared in the doorway. There was yet another wait until the newcomer’s eyes acclimatised to the gloom, then he made straight for the bed, sitting on Caitlin’s right with his back partly turned to her. He reached over with his right hand and slowly ran a hand up and down her stocking-clad leg, stopping before her made contact with her tingling flesh at the top. Long, sensuous strokes, designed to make him as well as her feel at ease with his presence. Caitlin watched him while he did it, trying to work out his features, but there was far too little light to attempt identification. Eventually he stood up, pulling a t-shirt over his head. Her heartbeat quickened as he knelt on the bed by the side of her, kissing up and down her legs. She parted them everso slightly and he took the hint, running the tip of his tongue around the elasticated band of her stockings.
He kissed his way up to the quickly dampening crotch of her panties. She was acutely aware that he must be able to smell her becoming aroused, something she’d always been embarrassed of even with her husband. If so, he didn’t appear to care. He kissed her through the flimsy material of her panties, and then began to lap at where he approximated her pussy lips would be. He wasn’t quite right, but his attention served its purpose. He adjusted himself so he was between her legs with his bum up in the air. With a free hand he drew aside the gusset of her panties. The air felt like electricity to her exposed sex. Hungrily and without finesse, he started to lap away at her, his tongue and lips frequently coming into contact with her straining clitoris but with no rhythm or method. She bucked her groin up at him, trying to produce the friction that would take her on to the next plateau.
He knelt up unexpectedly, and for a brief moment she wondered whether he had had a sudden attack of nerves. But she needn’t have worried. All he wanted to do was gently raise her bum from the bed so that he could slide her panties down, which he did with gentle ease. He sat still, and nervously she began to wonder what he was doing. She took matters into her own hands, inserting one finger into her own pussy and gently flicking it in and out. He must have appreciated what he saw, because the next moment she heard the zip of his trousers go down. From his silhouette she deduced he must have been masturbating himself slowly as he enjoyed the view.
Emboldened by this new turn, she stopped masturbating and reached over to the top drawer of her bedside cabinet. She’d always been far too nervous to buy her own sex toy, but what she had retained was a hairbrush with a pink, ribbed rubber handle. This brush never left the drawer save for those precious times like this when she used the long handle to masturbate with.
She licked the handle up and down, savouring the lingering remains of her own juices. When it was nicely lubricated – not that she would need much help in that department – she quickly rolled over and presented him with her bum. She lay with her bum right up in the air, him between her ankles, and her face pressed against the cotton quilt cover. She manoeuvred herself so that the hand with the hairbrush had plenty of free play, then she began in usual fashion by rubbing the tip of the brush against her clitoris for a few moments. She could see that he was still masturbating to a slow and consistent rhythm.
When she couldn’t wait any longer, she eased the hairbrush handle inside her pussy an inch at a time, until she had the full six inches of the handle inside her. She sighed as she felt the juices flowing around it, and for a few moments she just left it there. Then with practiced ease she started to work it in and out of her sex, at a steady, never varying pace. She heard her partner’s breathing start to quicken, and he put one hand onto her butt cheek as he masturbated. She loved the though of putting on a show for him, even if it might be a little too dark to make everything out. Stealing her other hand between her legs, she used her index and middle fingers to spread her pussy lips wide apart.
He was massaging her butt now with his free hand, and before long the ball of his thumb started to come into regular contact with her anus. He seemed unsure of what to do next, as though he wanted to penetrate her with it but was unsure whether to proceed. Caitlin didn’t really care one way or another, the consistent rhythm of her favourite toy was bringing her closer to her first orgasm, and combined with the erotic situation she found herself in – living out one of her favourite fantasies – she was on a sure-fire winner, no matter what he did right now.
He leaned over to plant big, slobbering kisses all over her butt, being surprisingly considerate and avoiding doing anything that might spoil the rhythm of Caitlin’s masturbating. Slowly but surely, his attentions edged closer towards Caitlin’s anus until he was licking it up and down, trying to penetrate it with his tongue. When he used his thumb on it again he found success, piercing her tight bum hole until his thumb was inserted as far as the first knuckle. He seemed content to leave it there, just waggling and twisting it in random fashion as they both continued masturbating.
She felt the headrush associated with her first orgasm seconds later, muscles clenching on the hairbrush handle inside her. She sighed luxuriously and withdrew the hairbrush, concentrating on the feelings her partner was producing in her anus. She felt invigorated from her first orgasm and wanted to seize the initiative. She took his hand by the rest and pulled it gently away, the soft plop as his thumb left her bum hole making a hole in the silence. She spun round and buried her head in his lap, using a hand on his chest to f***e him to lean back. She took his erection in her left hand. It was a good size, not the biggest she’d ever had, but thick and smooth. She flicked her tongue over the head a few times before gorging on it, deliberately slurping and sloshing it around in her mouth for effect.
She felt the salty pre-cum, and silently cursed him for paying too much attention to himself whilst masturbating over her. She’d smelt the alcohol on his breath and wondered whether he’d had a drink too many, and whether he would last long once he was inside her. She worked on the head of his penis for several minutes, slowing down once or twice when she thought she detected an involuntary thrust of his hips.
She stopped and lay back, legs wide apart and knees in the air. She wanted him inside her sooner rather than later if there were any questions about his staying power. He took a moment to cotton on to that but was soon on top of her, guiding his erection into her wet sex. It slid in easily, and in one movement he pushed it to the hilt, where he lay still for a moment. It produced a wonderfully light-headed sensation inside her and she smiled in the darkness. Then, he began thrusting into her, gently at first with long, slow strokes to the full extent of his length. She thought he would slip out of her if he kept drawing back that far, but he always seemed to know exactly when to stop. Then he was inside her again, his hot shaft filling her up.
He began to speed up, slowly at first, then accelerating and shortening the outward stroke. Their pelvises began to bang together, and she closed her eyes and bit on her bottom lip as her unknown lover pounded away at her. This was the first man other than her husband that she’d had in over twenty years, and she was by now loving every single minute over it. She allowed to him to hammer away at her, almost using her for his own means. She had her nails digging into his butt cheeks, which only served to spur him on.
She felt the familiar spasmodic thrusts from his hips, a sign that he was not far from his orgasm. She was not going to orgasm from penetration, and she’d wanted it to last a little longer, but the main thing was that she had had sex at long last. So she drew him closer, squeezing his shaft with her vaginal muscles. He grunted, and with that final thrust, loosed his sperm into her. He paused to catch his breath for a minute, his quickly shrinking cock still inside her. She made no effort to move him. Eventually he clambered off her and stood up, ferreted around on the floor for his shirt and left without looking back.