Going Where No One has Gone Before Ch. 03

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A young man and a cougar expand their sexual horizons.
2.7k words
4.59
12k
16

Part 3 of the 3 part series

Updated 06/15/2023
Created 10/04/2022
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byronbert
byronbert
276 Followers

It is recommended that you read "Going where no one has gone before" and "Going where no one has gone before Ch 2" before this Chapter. I am sure you will draw extra satisfaction from the stories if you see how the relationship between the two protagonists starts and unfolds.

Over the next few weeks, we got into a very satisfying sexual regime. I would stay overnight on Tuesdays and Fridays. We spent the majority of the time in the sack but, Mr S was also an excellent cook so both Lust and Gluttony were royally served. We were both thriving in a carnal sense. Indeed, the effects reached beyond the two of us. Mrs S said that people had noticed how positive and happy she seemed (apparently she was blossoming) and my new experiences had given me a self confidence that resulted in more attention from female acquaintances than I had ever experienced or expected.

Although I was feeling nowhere near bored, I was looking for something of a changeup. I also wanted to be a little more assertive in our sexual pursuits. I couldn't put my finger on why but I had a feeling she wanted this too.

Because we had only ever seen each other at her apartment, (I guess "seen" could be interpreted as a euphemism for "fucked"), I thought a change of scene could be titillating. Bringing her to my dorm was absurd. The eyebrows raised would lift the roof. I could not afford to rent a room... but I had an idea.

Why my mother had insisted I take a suit with me to university had bewildered me at the time. Now I was grateful. I was going to use it in an attempt to deliver Mrs Sinclair a proposition she could not refuse. I was filled with an intense feeling of anticipation as I entered the elevator that would take me to the floor Mrs S worked on. My reflection in the full-length mirror on the wall of the lift showed me in full "young urban professional" mode. The brief case was a nice prop. I am not given to vanity, but I had to concede I did look pretty sharp.

As I entered the reception area of the accountancy firm, I could sense female heads turning. I strode confidently to the receptionist and politely gave them my name and asked if I could see Mrs S.

The receptionist picked up the phone and said a few words and a minute later a very confused looking Mrs S entered the reception area. She did a double take when she saw my business exec. look. Her confusion was clearly evident. I took charge. "Good afternoon Mrs Sinclair. I have those papers we discussed. Could we find somewhere to go over them?"

She nodded hesitantly and said, "Follow me."

We passed the desk of what I assumed was Mrs S's personal assistant. She was a matronly figure that must have been in her 50's. I could sense that she too was a little perplexed. Maybe a walk-in visit from a young, sharply dressed male sans appointment was a little eye raising after all. I gave the PA my best amiable grin. She did not smile back.

We entered her office. I closed the door behind us and was relieved to see there was a lock which I engaged. I turned to her, gathered her in my arms and went in a for a deep kiss. She struggled mildly at first but after few seconds, melted in my arms and matched the ardour of my kiss. A minute or so later she pulled away and with an incredulous tone to her voice demanded, "What are you doing here?"

"I thought I would give you a little afternoon delight." My grin was dazzling. She took a moment to digested that and when she recognised the sexual reference, her eyes flew open, and her hand went to her mouth.

"You are suggesting we have sex, now, in my office, surrounded by scores of people I work with?"

I slowly nodded my head. She seemed taken aback. Moving in close to her, I reached down and around her and grabbed two handfuls of prime milf buttock. This ground my burgeoning erection into her stomach. My lips started an earnest assault on her neck.

"We can't. We mustn't. We shouldn't..." Her voice trailed away as she gave herself up to the sensations.

I raised a hand to a bountiful breast. Even through her business suit I could feel a very erect nipple. I declared victory when she simultaneously stroked my penis through my suit and mouthed the following words, "We will have to be quick."

Turning to her desk, she pressed a button and breathlessly announced, "Hold my calls, Miss Smithers. I have some urgent work to deal with."

We rapidly removed the minimum number of items of clothing for sexual congress to be joined. Which is another way of saying we were naked from the waist down. I gallantly boosted her up onto her desk and bade her lie down. I swiped my missile up and down her slit a few times and was delighted to see how wet she was. Although she was lying flat on her back, her head was craned forward to see what was going on. We both groaned as we saw the head of my penis glisten with her oil.

Even though the office door was locked, the thought of discovery added a real electricity to our tryst. Looking down at Mrs S I could see she was staring at me with a steely look. Through gritted teeth she was quietly growling at me. "Fuck me. Fuck me now." Well, that was enough of an invitation for me, besides I could hold back no longer. With a powerful pelvic punch, I lodged myself into her almost to the hilt in her sopping sex slot. She let out a wail that had me seriously concerned that her PA or anyone else near her office would conclude something was afoot. After a few more lunges I was wholly entrenched in her. She was gulping like a goldfish at my forceful entry but was bucking back against me enthusiastically.

Our engagement was cruelly interrupted by a sharp rapping on the door. We both froze. The voice of Miss Smithers was urgently enquiring if everything was all right. Mrs S cleared her throat and said in a slightly shaky voice that everything was in hand and not to worry. "Very well," was the dissatisfied reply from beyond the door. We both sighed with relief and then giggled with the bizarre state of our affair.

Getting back to business, I lowered my hand to her clit and started a swiping motion with my thumb in time with my thrusts. Her eyes started flitting erratically around. They seemed unfocused. After only a minute or so she started a whining sound that gradually became louder and louder. I took the extreme decision to clamp my hand over her mouth which subdued her a little, but the sound was still disturbing. I accurately assumed she was close to climaxing, so I decided to give her a race to the finish line. I went into overdrive. Now I was the one making detectable noises. I later learnt that the oft vaunted simultaneous orgasm is a rarer beast than I believed at that moment but that is what we achieved on that desk, on that day.

We were both puffing like we had just finished a 100-metre race. Mrs S looked like she was crying, she was almost sobbing. I was worried enough to ask if she was OK. She assured me she was fine, and her distress was actually extreme satisfaction with the strong sexual chemistry we seemed to have. I processed it as post-orgasmic emotional turmoil. POET!

As I pulled back from her, I took a sinful delight in seeing several voluptuous globs of my discharge fall languorously from the sodden mass of her pussy onto the floor of her office. She attempted to sit up but failed. She tried again but fell back with a sigh. I took her hands and helped her into a sitting position and then to her feet. She was trembling. Looking up at me her face was full of awe. "I can't believe the sensations you stir in me. You generate in me the most profound sexual feelings I have ever experienced. Thank you." She reached up and, pulling my head down, chastely kissed me on the cheek.

I expressed a similar sentiment. Although this little sham business meeting booty visit was brief in terms of time, it was profound in terms of intensity.

We quickly tidied ourselves up, not wanting to feed Miss Smithers suspicions any more than we needed to. I unlocked and opened the door. For the benefit of Mrs Smithers, I loudly announced, "Thank you for your contribution to this proposition Mrs S. I hope the deposit that I have left will satisfy you. I greatly appreciate your participation in our joint venture." I leaned towards Mrs S and quietly whispered. "You can audit my ass, I mean assets, anytime you want." Her eyes flashed in silent rebuke at my risqué comment, but the corners of her mouth then curled in salacious amusement.

Ms Smithers accusatory expression softened under my beaming smile. I moved to the exit with an unintentional but palpable swagger. My grin swept around the room like a search light. I was walking on air.

The next day was a Tuesday which meant another evening of carnal capers. As was normal, I approached her front door with an eager spring in my step. I rang her doorbell and the door opened momentarily. She beamed at me and I returned her grin in an inane Cheshire cat fashion. The sexual anticipation we shared was electric. She quickly closed the door and we fell into each others arms.

The normal pattern of our sexual rendezvous' was firstly a swift, feverish coupling which saw us both galloping frantically to orgasms. It was as though we couldn't do anything until we had sated our initial sexual demons. This was then followed sometime later by a more considered and thoughtful love-making experience.

I started undressing her as we shuffled towards her bedroom. I loved the trail of garments we left in our wake. By the time we crossed the threshold of her bedroom, we were both naked and our hands roamed freely over each other bodies. We were shivering with eager excitement.

She crawled onto the bed and in a lascivious cat like movement. Her expression was coquettish She lay on her back and spread her thighs. I could already see liquid evidence of her arousal on her fleshy labial lips.

"Take me," she growled. Naturally I was not going to disappoint my erstwhile sexual significant other. I knelt between her splayed thighs and she quickly went to work lining up the relevant bits of anatomy until, with a lunge that made us both gasp, I made my way deep into her. I proceeded to give her a good old-fashioned pounding which she seemed to greatly enjoy. Normal operating procedure was for us to make her come and then I could finish inside her. Her hand was between us, frantically frigging her most sensitive button. She always came relatively quickly which suited everyone involved. I knew from experience that the erratic head shakes and discombobulated vocalisations she was making that she was close to the big release. This excited me to a level that meant I too was charging down the raceway to the fornicating finish line. She bellowed and I responded with an animalistic roar. It announced that I was spray painting her cervix with my creamy concoction.

I reluctantly rolled off her. Both our hearts were pounding and our breathing was ragged. We looked at each other. Our smiles were impossible to control. More Cheshire cat impressions.

As was our usual custom, we then had a delightful meal that Mrs Sinclair had prepared earlier. She was only wearing a small apron which hid little of her charms. I couldn't keep my hands off her and she squealed with what I hoped was delight at my groping, exploring hands. Those celebrated nipples drew me back again and again like an alcoholic to a mini-bar. After the meal and an hour or so of discourse and digestion, we went back to bed for another hour of depravity and degeneracy!

She was soon astride me with her hands on my chest. Her movements were as though she was riding a trotting horse. I was selfishly lying back with my hands behind my head looking up at her as she did all the work. Her breasts gambolled freely in delightful synchrony with her bucking motion. I stilled their wild and weighty motion by filling my hands with them and, in the process, gave those staunch nipples a muscular squeeze. She threw her head back and bucked harder. It was like using stirrups on a horse.

Unexpectantly, she moved off me and assumed the all fours, doggy-style position. The glance she gave me over her shoulder smouldered with lust. I shuffled up behind her and she, as we were accustomed to, took control of the targeting of my missile and I sunk appreciatively into her. We settled into a very satisfying rhythm. As I looked down at her magnificent ass, I was intrigued to see her little asshole winking at me with each thrust. Anal sex was another particular practise that was high on my carnal bucket list. I wondered how to broach it.

Feeling a confidence that I was totally lacking only a few short weeks ago, I moistened my thumb in my mouth and then placed it on her little date. I rubbed it around her ass hole and she looked over her shoulder at me with a look of trepidation.

I quietly stated my aspiration, "I would love to have anal sex with you."

I saw her gulp and her eyes flickered like a candle in the wind. She was clearly apprehensive. I didn't want to press the issue too much but I did increase the pressure of my thumb until it was embedded in her up to the first knuckle. She was not avoiding my intrusion into her ass but there was clearly a degree of trepidation about this suggestion. I continued a stalwart barrage of deep thrusts.

Just as I sensed she was on the verge of coming, I forced my entire thumb into her clasping chocolate honey-hole. I could feel her anal muscles spasming on it.

My duty done, I set about selfishly satisfying myself. My ardour was fuelled by imagining what it would feel like to have my penis where my thumb was. This thought had me quickly scampering to an explosive orgasm.

We separated and lay on our backs for a few minutes until our heart rates returned to something approaching normal. She climbed on top off me and picked up my left hand. She sniffed each of the five digits. Disappointedly she dismissed the hand to explore the other. She soon became captivated by the aroma emanating from my thumb. After several deep snuffles, she stunned me by taking my asshole explorer into her mouth. Her tongue and mouth gave it a royally effective cleansing, all the while staring fixedly at me. She gave it another smell test and seemed pleased with her efforts. Looking down at me again she lowered her head towards mine and whispered. "Wanton enough for you?"

I groaned in appreciation.

She sat back up, still straddling me. Her expression changed from sultry to serious. She began addressing me in an apologetic voice. "You're just too big. And I've always been scared of the pain involved." I quickly realised she was talking about my anal desires. "I have never even tried it. Just about all the anal play I have ever experienced has been with you." I greatly relished the idea that I had more familiarity with her Hersey highway than anyone else but I really craved taking it to the next tier.

As we snuggled and slowly drifted off to sleep, my imagination could not abandon the fantasy of conquering the tight little ass of this middle-aged cougar. Claiming her anal virginity would be both intensely satisfying from a psychological perspective as well as, presumably, a physical experience of apocalyptic proportions! I was wholly determined to go where no one had gone before!

byronbert
byronbert
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AnonymousAnonymous9 months ago

Really love this series. Just hoping you take a more sensible preparation approach to first time anal sex than the usual just shove it in there because it's assumed that all women that excruciatingly painful experience.

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