Written by Anonymous

Meetings
Oct 29, 2018


Sharon is 48, married with 2 teenagers. He has a great career as a pharmacist in Ottawa. Many would consider her to be a MILF. She has dark brown hair with bangs framing her sensual green eyes, a great figure for a woman of her age and frim breasts with ever so slightly puffy nipples. She keeps fit and lives a healthy lifestyle. Keith is 50 and recently separated. He is in sales and based out of Toronto. He manages to stay reasonably fit by working out 2-3 times a week. He has a masculine frame, athletic with broad shoulders, vibrant blue eyes all topped off with short salt and pepper hair. Many consider him to be sexy but he has no clue just how much.

Keith recently joined an online dating site. Now that he was separated he was eager to explore new experiences – especially sexual after having been in a long, monogamous and rather mundane relationship. Sharon was equally curious and motivated to step outside of her sexual comfort zone. While still married, she was not comfortable asking her husband to be more adventurous so she turned to the same online site as Keith to investigate her options. The thought of hooking up with someone completely new with no strings attached was very exciting to them both.

Since Keith was going to be visiting Ottawa for client meetings he decided to try his luck at finding a local woman to meet. He reviewed several profiles before landing on Sharon’s and instantly knew that she was the one he wanted to connect with given that she was seeking some NSA exploration like him. After some chatting they agreed to meet at a café downtown near Keith’s hotel.

In the days leading up to their meeting, Sharon’s excitement turned to nervousness. She was beginning to feel conflicted and afraid of what might happen if her husband found out. At the same time, her mind raced with all sorts of salacious thoughts and scenarios she might experience with Keith. The anticipation had her in a state of hyper-arousal. She must have masturbated 3 times a day during this time. Keith was super excited too but was also experiencing nerves of his own. What if she didn’t find him attractive/sexy? What if he let her down sexually, assuming that they would even get to that point? But, as the day of his trip to Ottawa got closer, he too began to mull fantasies of his own.

The day had arrived and they were to meet at the café at 1 pm. Sharon had taken the day off and enjoyed the quiet of her house with her husband at his office and the kids at school. She had a relaxing bath and shaved her legs and armpits. She paid extra attention to her pubic area. She found it sexy to keep her labia smooth with a nicely trimmed patch above. Hopefully Keith would like it as well.

When Keith arrived, Sharon was already there. The café was quiet and they recognized each other immediately. Keith was wearing business casual attire – dressy jeans, a crisp white dress shirt and navy blazer. He was handsome and sexy beyond Sharon’s expectations. Sharon was wearing her favorite sexy, form fitting burgundy suede skirt which accentuated her nice ass, a white and grey striped blouse which was open just enough to highlight her healthy cleavage, and her knee high, black leather boots. Their first embrace was very warm and longer than one might expect for a 1st meet. At this point, Keith was utterly captivated and couldn’t stop himself from wondering what delightful pleasures were concealed by that skirt.

They ordered cappuccino and spent the next hour talking mostly about what they liked about Ottawa, Toronto and Montreal. They also got real about the reasons why they were there. Sharon found it very liberating to be able to express her sexuality freely without fear of judgement. She was also getting turned on as her mind began to wander. She wondered what Keith’s cock was like. Was it very big? She began to imagine taking it into her mouth, tasting him and pleasuring him. She then noticed how warm and wet she was getting as she started creaming her panties. Before excusing herself, she asked Keith to confirm his coordinates – hotel and room. When she returned she handed him a small bag and bent down to whisper softly in his ear “I want you…to open this when you get back to your room then start thinking of all the naughty things we are going to get up to this afternoon. I’ll see you in half an hour”.

Back at his room, Keith slowly opened the bag to reveal a pair of black lace panties. They were absolutely soaked and still slightly warm. He brought them to his nose and inhaled deeply enjoying Sharon’s sweet, musky scent. He was imaging her wet pussy and what it would taste like as his cock began to grow and tingle. It was all he could do to restrain himself from jerking off right then and there – but he knew better things were to come.

When Sharon arrived they were all over each other, hands exploring and eager tongues probing deeply – with such intent. Piece by piece they removed each other clothes until they were completely naked, except for Sharon’s boots. Keith insisted she keep them on because they were just too dammed sexy.

Keith stood behind Sharon, fondling her breasts and playing with her perfect nipples. They became so hard, erect and sensitive that the slightest brush of his fingers sent her into ecstasy - a warm tingling sensation travelling directly to her loins.

They made their way to the bed. Sharon laid down 1st, expecting Keith to lie down beside her. Instead, he turned around to face her feet and straddled her head, assuming a 69 position with him on top. She had never 69’d before – it was a huge turn on. She looked up to see his lovely engorged cock and full balls. The head was glistening, dripping with pre-cum – she wanted it so bad. He lowered himself to her waiting mouth. As it touched her lips she could feel how hot it was and enjoyed the taste of his sweet pre-cum as it dripped onto her tongue. As Keith lowered his head Sharon spread her thighs wide for him. He could feel the heat rising and reveled in her womanly aroma. Her labia were already swollen. She was so wet the juices were literally running down between the cheeks of her lovely ass. She was so horny, about to burst and raised her hips to meet his eager tongue. He slowly licked up and down, tracing her lips and every so often paying attention to her clit which was now so sensitive that he knew that he could bring her to climax at any time. The taste of her pussy was such a huge turn on for Keith that it sent more blood to his already engorged cock which Sharon now had completely in her mouth. It felt massive and she had to fully open her jaw but she wanted to take it all in. She wanted to give him as much pleasure as he was giving her. Right to the back of her throat, saliva now running down her face. Keith sensed her readiness and took her clit firmly between his lips and began to tongue it in rapid strokes while fingering her ass using her dripping juices as lube. A huge wave comes over her as she experiences an orgasm which is so delightfully intense that, for a moment, she fades out. When she composes herself, she gets back to pleasuring Keith with long-slow deep throating while stroking his full, smooth balls. He feels that most pleasurable warm, aching sensation as he is about to cum. Sharon feels his balls tighten and shaft begin to pulsate. She slowly releases the grip of her mouth and, with her lips wrapped around his now massive glans, the 1st stream of hot, salty/sweet cum shoots to the back of her throat followed by several equally large spurts. So much that she cannot take it all in her mouth but she so wants to taste his ejaculate and swallows as much of his huge load as she can – something that she would never do with her husband.

Sharon was now feeling very kinky and still very horny. She craved more and, before she could give it a second thought, told Keith that she wanted to be restrained, for him to take full control. She told him to use her body in whatever way pleased him the most. Using a couple of his dress ties, Keith bound Sharon’s wrists behind her back and blindfolded her. She was instantly turned on – electrified. Never before had she experienced such a high degree of sexual stimulation and anticipation.

He held her still damp panties under her nose and, as she became even more aroused by her own scent, place them in her mouth as a gag she could taste her own juice. He told her how absolutely gorgeous she was and just how horny she made him. He told her he was going to take great pleasure in fucking her senseless – like she’s never, ever been fucked before. She could feel her own juices welling up in her cunt, the flood gates about to let go. She tried to play it slow but wanted to submit to him fully that she immediately kneeled face down on the bed with her precious ass in the air and legs parted to expose her succulent, dripping pussy. She felt completely at his mercy and it excited her to no end. Taking in the view of Sharon from behind in this vulnerable position with those sexy boots, Keith stroked his cock which began to grow steadily again. Like Sharon, never before had he had this type of experience but he was all in, as was she, and had every intention of enjoying her sexy MILF body to the fullest.

Starting with some teasing and stroking of her thighs from behind, Keith traced her ass and lightly stroked her pussy which was just aching for his cock. He got down and licked her from behind, probing her pussy and ass and driving her wild to the point that she was moaning loudly, begging through her gag to be fucked. Suddenly she felt a sharp, stinging heat as he slapped her ass hard. At 1st she was really startled but quickly became hyper-aroused. He continued the spanking, a little harder each time. It was so painful yet sensual – she loved it immensely. At this point she was completely ecstatic. Moving behind her propped up ass, Keith ran the head of his now very hard cock slowly up and down between her swollen labia which were waiting to envelop his entire length. Again, Sharon moaned this time with a muffled “Fuck me, please fuck me now”! He entered her slowly in one long continuous stroke until he was balls deep, her juices now running down his scrotum. She took a deep breath and realized that this was the fullest that she had ever felt. His thrusts began, 1st long and slow, then harder and deeper. As he picked up the pace his balls slapped against her sensitive clit as the head of his cock hit all the right places. She pushed back hard as she came and Keith could feel the intense sensation of her vaginal walls pulsating. She was shaking and let out a scream of unadulterated pleasure.

Thinking that they were finished, Sharon was surprised when Keith did something that she was not expecting but had fantasized about and hoped she would experience one day. He told her that she was going to fuck her slutty MILF ass. She nodded up at him approvingly with a muffled “yes, oh please yes”.

Again, Keith proceeded to lick her from behind this time starting with her perineum and working his tongue up to her anus. He tongued her hole while stroking her clit with his thumb. It was an unbelievable new sensation for her. She found it to be incredibly hot and pleasurable and was soon aching to be fucked in her ass for the 1st time. She moaned wantingly – she was ready.

Keith was very aroused himself from the ass play. His cock, fully erect and still glistening with her juices. He reached back to grab a condom and some personal lubricant from his travel bag. He kept the lube handy for masturbating. With condom on and shaft well lubricated, he worked some of the lube into her anus with a finger. Ever so slowly he pressed the head against her anus which yielded at 1st. He was so horny but had to restrain himself from forcing it in – waiting for her body to relax. She was equally aroused with the anticipation of what it was going to feel like to have a man’s cock in her ass. She was also enjoying the heightened sensations of being restrained. She felt naughty and vulnerable at the same time.

At last she relaxed and the head slipped in with a slight pop. Her body immediately tensed and he waited. She could feel the head of his cock pulsating in her ass. Another couple of breaths and Sharon relaxed allowing Keith to push his whole length into her. He did this in one continuous motion and, to both of their surprise, she orgasmed immediately. After she settled, he started to fuck her as he had intended. He was amazed by the extraordinary tightness around his cock but yet how he was able to fuck her with relative ease. Sharon now understood why anal was so popular with many people. It was such a unique feeling – erotic and taboo – but ultimately extremely pleasurable. He balls were now slapping against her pussy and thighs. He gripped her hard by the hips – she was screaming “fuck me, harder, harder, please fuck me hard”. She knew that he was about to explode which excited her to orgasm for a 2nd time and, with a single hard thrust, Keith let go and came so long and hard as Sharon’s assed milked his balls dry.

He untied her wrists, removed the blindfold and gag. Utterly exhausted and thoroughly satisfied they cuddled naked in bed, kissing passionately. They made love one last time in the shower that afternoon before it was time for her to return home and him to meet clients for dinner.


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