The Best Erotic Stories.

My First "Older Woman"
by Bruce Swain

Surfing the net through the "amateurs'" pages, I have been delighted to find a number of sites dedicated to "mature" women - i.e., those over 40. Some of them, admittedly, should have kept their photographs to themselves, but then there are some incredibly attractive and sexy "older" women.

Looking at them made me recall my first experience with a woman many years older than I - it happened when I was 33, and the woman was, as she put it, "approaching 50".

Her name was Lorraine, and she was the personal secretary to the senior officer under whom I was working at the Department of Defence in Canberra. Everybody knew she was divorced, and quite a few guys tried to hit on her - both seriously and in fun. I was always the epitome of politeness and good manners with her, and must have been one of the very few naval officers who didn't try to chat her up.

On one of my visits to her office, after I'd been in the job for a few months, she asked me why I didn't like her. I was a bit taken aback, and asked her what she meant. She replied that I was always very business-like in my dealings with her, and never hung around for a friendly chat - so she had assumed that there must be something about her that I didn't like.

I assured her that that was not the case, that I was just being "an officer and a gentleman" - and the last thing I wanted to do was make an enemy of my boss's personal secretary! She said I needn't worry about that, as there were many others who had come very close to offending her - but she had been able to deal with them without going to the boss.

So, nothing ventured, nothing gained - and I asked her how could I really know if I liked or not if our dealings were restricted to "purely business". She said I could fix that by taking her out for a drink after work.

Well, "after work" for her was about an hour after everyone else finished, so I had to hang around my office on some pretext while I waited for her. Eventually she knocked on my open door, and asked,

"Ready?"

Not making a point of looking at my watch, I replied, "Sure - my car or yours?"

"Mine, I think," she decided, with a slight smile. "That way I know that I'll get home."

The problem then was to find a "watering hole" that was not frequented by people we both knew - otherwise word of our meeting would be all over the place the next morning. Lorraine said she knew just the place - a quite little bar in a very exclusive guest-house on the outskirts of the city. (It was the sort of place where if you had to ask what the tariff was, you couldn't afford it!") I was dreading what the drink prices might be, but I went along with her.

For our first couple of drinks we sat on the comfortable padded stools at the bar, then Lorraine suggested moving to one of the rather secluded booths by the wall. The place was furnished in dark wood (mahogany, I think), added to which it was very dimly lit - making it perfect for a discreet assignation.

Lorraine slid into the booth first, and as she said she allowed her tight skirt to slide well up her thigh - and show me that she was wearing stockings and suspenders, not panty-hose. That got me very interested right away, but when I sat down next to her she shuffled closer so that our thighs were touching.

Then she asked me the story of my life; I asked her did she want the full version, which would keep us there until after midnight, or the abridged version which take only a couple of drinks. She said the abridged version would do for now - I could tell her the full story later.

Later...?

So I gave her a brief run-down of my 18-year naval career to that date, leaving out most of the "juicy bits", but including the fact that I had a wife and two kids living in Queensland - 800 miles away. She said that I must get pretty lonely - and I knew what she meant by "lonely". So I replied that I didn't really get lonely - just horny. At which point she said,

"Tell me about it!" and took a long sip of her drink.

Taking my cue, I said that surely she wasn't "lonely" - she was a very attractive lady of "independent means" and should have plenty of male friends.

She just shook her head wistfully, and said she wished that were so. She knew that all the guys at work who tried to pick her up would run a mile if she accepted, and that the only other ones who were "available" were just kids - that is, aged 25 to 30.

I replied that I was not much over 30 myself, to which she replied,

"I know - I've got all your personal details on file, remember!"

So then I asked her why she had wanted to hear them from me, and she replied,

"Just to see if you would try to bullshit me - like about being married."

So she had known that I had a wife - my "next-of-kin" - and that she was a very long way away.

"Just testing, huh?" I asked.

"Yep," she answered, over the rim of her glass. "And you passed."

So then I asked her what was her story - and it was a little sad. She had not married until she was in her early 30s, and her husband desperately wanted kids - more than she did, actually. But it turned out she could not conceive, and eventually her husband divorced her to go and find a "fertile" woman. Adoption had been out of the question, apparently - he wanted his kids.

He had, however, given her a generous settlement, which included a house in an inner suburb in Sydney. She had sold that when she got a job in Canberra, and had quite a bit left over after buying her own unit quite close to the city centre. She didn't really have to work, she said, but if she didn't she'd go nuts!

Since her divorce she'd had a couple of long-term relationships, but they had not developed into anything permanent.

I asked her what she did with her spare time, and she said she "worked out" three evenings a week, saw every movie that came through town, and did a lot of reading. She was often asked to dinner-parties to "make up the numbers" - that is, to help make the number of males equal the number of females, and she had a couple of women friends who were always trying to find "the right man" for her. So far, they had not succeeded.

"But sometimes," she admitted, "I'll go to bed with one - just to ease the frustration! Unfortunately, more often than not I end up more frustrated - you know, 'wham-bam, thank you, mam'!"

By this stage, by my count, she'd knocked back six drinks - and it was beginning to show.

"Two-minute wonders, eh?" I suggested.

"Two minutes? I wish!" she replied. "If it weren't for my faithful vibrator..."

I must confess that I was starting to feel a little uncomfortable with the way the conversation was going, and I tried to look for a tactful way out of it. I made a point of looking at my watch, and Lorraine asked,

"Anywhere you have to be?"

"No," I replied. "I was just thinking that it's way past my dinner time - got to put something in to soak up all this booze!"

Lorraine put down her drink, placed a hand on the top of my thigh, squeezed gently, looked me straight in the eye, and asked,

"Would you like to eat me?"

I almost choked on my drink! I had been thinking that after a couple more discreet meetings such as this I might get into Lorraine's pants - but I certainly hadn't expected such a direct proposition from her!

I recovered my composure enough to reply,

"Fur pie is one of my favourite snacks - unless you're clean shaven!"

She smiled and shook her head. "Au naturale - just as nature intended."

Her hand moved upwards slightly, and she felt my growing interest.

"That tells me my invitation appeals to you," she said, her smile becoming a satisfied smirk.

"Are you sure about this?" I asked, hoping it wasn't just the booze talking.

"Any man who doesn't seem interested in me arouses my interest - I see it as a sort of challenge. I hope that now you are interested!"

"Is the Pope a catholic? I asked rhetorically. "As they say in ninety-nine per-cent of every movie ever made - 'let's get out of here'!"

On the way to her car, Lorraine handed me the keys.

"You drive - I'll give you directions," she said.

The directions were given as she nibbled my ear and stroked my thigh - but I still managed to find her block of units. She had to move away from me to find the electronic gizmo that worked the security gate on the driveway and then the door to her garage, and then she led the way up an internal staircase to her unit. She asked for her key-ring back, used two of the keys to open the door, then led me inside.

I had no sooner shut the door behind me when Lorraine wrapped her arms around my neck, pressed her open lips to mine and probed my tongue with hers. I responded by grabbing her arse-cheeks and pulling her hard against me - or against my hard-on!

When she at last pulled her lips from mine she glanced down, smiled and said,

"That's the sort of reaction I was hoping for!"

"If this is going where we both want it to, wouldn't it be better to have a shower first?"

"Why? Do you have something against healthy bodily odour?"

"Well..."

"Well what? I don't think I'm going to smell any worse than you - and I don't mind if you don't."

Without further ado she took my hand and literally dragged me to her bedroom. There she turned on the lamps either side of the queen-sized bed, then turned to face me.

"Sit!" she ordered, pointing to the bed. I did as I was told.

Then she started a slow, seductive strip. Off came her jacket, then her skirt, revealing her stocking-tops and black suspenders. The blouse went next, and she stood before me in her lacy black bra, matching briefs, garter-belt and stockings; for just a second I wondered what the guys at work would think if they knew what Lorraine wore underneath her very business-like outer garments!

Suddenly my mouth was very dry, and I tried hard to swallow.

With her eyes smiling into mine, Lorraine reached behind her and undid her bra, then crossed her arms modestly in front of her as the straps fell from her shoulders. The she slowly lowered her arms to her sides, allowing the bra to fall to the floor and revealing her breasts.

I knew many much younger women who would have killed for breasts like Lorraine's - they were full, beautifully rounded, and with only a hint of sag. Her nipples were a dark pink, the aureole about an inch in diameter, and she was obviously already aroused.

"Not bad?" she asked, still smiling at me.

"Not bad at all," I replied hoarsely.

"I know - 'for a woman my age'. Isn't that what you mean?"

"No - for a woman any age!" I assured her.

She seemed to accept that, and then hooked her fingers into the waistband of her briefs, and bending forward slid them down to her ankles and stepped out of them. She then struck a pose, standing there in nothing but her garter-belt and stockings, allowing me to feast my eyes on her. Whether it was the "working out", the fact that she had never had kids, or what - I don't know, but her figure, while full in all the right places, was that of a woman at least 25 years younger. As I admired her shapely body I got shakily to my feet and began to hastily divest myself of my clothes. I was down to just my underpants when Lorraine said,

"No - that's my treat."

So I stood there while she knelt in front of me and slowly drew my briefs over my hips. My cock, which had been straining for release ever since Lorraine had started her sexy strip, now sprang free, almost hitting her in the chin.

She licked her lips seductively, and without taking her eyes from my throbbing organ said throatily,

"Now, that is a sight for sore eyes!"

Whereupon she gently took hold of the shaft with one hand, drew it down until it was level with her mouth, and closed her lips around the knob.

"Mmmm," she moaned, as her tongue started to swirl all over my crown. As she worked on it, her other hand moved up the inside of my thigh to gently cup my balls. With my cock now firmly held by her full lips, she took her hand from my shaft and used it to gently push me back until I was again sitting, then lying, on the bed. And not for a second did her lips leave my cock.

For the next ten minutes or so she didn't just give a blow-job - she made love to my cock. She used her lips, her tongue, and her fingers; she would lick the shaft from the tip to my balls and back again, then run her wet lips all over it, then take it in her mouth and suck hard on the top half while her fingers gently but firmly stroked the bottom half. She kissed it, she breathed on it - she seemed to worship it, as if it were the first one she'd seen in years! But I couldn't believe that it was...

She was kneeling beside me, leaning over my crotch as she worked on me, and eventually I reached out, put my hand firmly on her beautifully-rounded arse and tried to pull her towards me. She quickly grasped what I wanted, and still without taking her mouth from my cock she swivelled around, swung one shapely leg over me and positioned her crotch right above my face - just where I wanted it.

I inhaled the musky smell of her womanhood, then lifted my head so that I could bury my face in her pussy. When my tongue found her clit, she did remove her mouth briefly from cock - just long enough to say huskily,

"Yes - lick it! Suck it! Eat it!"

And I did. I used all of my oral expertise to lick her from arsehole to clit, to probe her cunt with my tongue, to suck and lathe her swollen love-bud. Her pubic bush was thick and silky, her labia full and tender. It was indeed a feast fit for a king, and I used the enjoyment of it to take my mind of what Lorraine was doing to me.

I guess it must have been a long time between drinks for her, as I had been eating her for only a few minutes when I saw the muscles on the insides of her thighs begin to tremble and her clit began to swell even more between my lips. For only the second time she released my cock from her mouth, holding it firmly in her hand, as she threw back her head and let the orgasm sweep over her.

She let out a long, moaning, "Ooohh, God -yes!" then ground her loins down into my face, her thighs clamping around my head as the ecstatic spasms racked her body.

When she had calmed down, she swung her leg back over me so that she was kneeling alongside me again. As she gently stroked my cock, she asked,

"Do you want me to go with this, or...?

"Or what?" I asked, teasingly.

"Or fuck me, for God's sake!" she replied vehemently.

"Well, I've sampled the entrée, so now I think I'll try the main course," I replied.

"Dinner is served, then," Lorraine said, lying on her back, spreading her shapely legs and bending them at the knees so her thighs were raised. I got between them, and did not even have to use a hand to guide my cock to her waiting pussy.

I just lowered myself onto her, and my knob seemed to find the fleshy portals to her pussy of its own accord; I then sank my shaft balls deep in one easy movement.

"Nice fit," Lorraine said, smiling up at me then pulling my head down to give me a long, deep kiss. She hooked her ankles over my legs so that we were firmly locked together, then began to slowly squirm her hips.

Again, for a woman her age she was incredibly tight - but at the same time incredibly wet, so that when I began to slowly fuck her I was able to slide by cock back and forth easily.

I was taking my weight on my hands and knees, but Lorraine said,

"Come down here - I'm sure I can stand the weight!" So I lowered myself onto my elbows, so that we were pressed together from breast to loins.

Lorraine met every downward and inward thrust with an upward thrust of her own, so that each time I went as deep as possible. When I varied my pace, she matched it each time; then I began to sense that she preferred fast to slow, so I started to piston my cock in and out with increasing rapidity.

"Yes, I love that!" she moaned. "Fast and deep - don't stop!"

I had no intention of stopping until she came again, but I was surprised at how quickly her second orgasm hit her. She closed her eyes, tossing her head from side to side on the pillow, and slammed her loins even harder against mine. I felt her pussy muscles fiercely gripping my cock as she climaxed, then they relaxed as the last wave of pleasure swept over her.

"God - twice!" she gasped, opening her eyes to again smile into mine. "And you still haven't!"

I smiled back at her and said, "Not without incredible restraint!"

"Well, you don't have to hold back any more! How would you like me?" she asked - I told her on her hands and knees, and withdrew my cock from her soaking pussy so that she could get into the desired position. She then looked back over her shoulder at me and asked,

"Do I stand well? Like a good mare - or bitch?"

"Perfectly," I said, admiring the two half-globes of flesh before me. Her little star-shaped anus looked very inviting, but I thought it might be a bit early in proceedings to try that - perhaps later...

Using one hand I rubbed my cock up and down her slit a few times, then sank it deep inside her once more. With my hands on her smooth arse-cheeks I began to pull her back to me each time I thrust forward, but after the first few thrusts Lorraine was rocking backwards and forwards in time with me.

"Doggy" had a always been my favourite position, as I seemed to receive the ultimate stimulation along the underside of my cock - especially just below the knob - and after just a couple of minutes I could feel that my balls were about to empty their load.

Lorraine had moved one hand underneath to gently squeeze my balls, and felt them contract as my jism began its short journey to the end of my cock.

"Yes," she moaned softly again. "Give it to me - give it all to me!"

And I did - slamming into her as hard and as deep as I could, thrusting violently with each spurt. Lorraine accepted each one with a grunted "Uh!" then kept rocking back and forth slowly even after I had stopped. Only when she felt my cock start to wilt inside her did she allow herself to flop onto the bed, apparently not caring about the considerable "wet spot" that she would make on the bedspread as a result.

I squatted on my haunches, getting my breath back, my cock a sticky mess of our combined juices. Lorraine smiled at me over her shoulder and asked,

"Need a clean-up?"

Thinking she meant a shower, I glanced at my slimy shaft and replied,

"You could say that."

Whereupon she swivelled around, took my cock in one hand and began to suck and lick it clean! When she was finished to her satisfaction, she ran her tongue along lips the said,

"A bit salty - but tasty all the same."

Then she suggested a shower, and we took it together, soaping each other all over (paying particular attention to the "naughty bits") then rinsing off. Stepping from the cubicle, Lorraine produced a huge bath-towel which she wrapped around both of us. With our bodies pressed together again, my cock began to stir and reached semi-hardness before she glanced down and said,

"Looks like that might be ready for more before too long!"

I replied that it felt like it was ready right then, but she said,

"No - I think I'd better feed you first. Food this time!"

I followed her back to the bedroom, where she opened the wardrobe and took out two towelling robes. "This should fit you," she said, handing one to me. "Souvenir of a very rare dirty weekend," she added, indicating the motif of one of the city's most exclusive hotels on the robe. "And not a very satisfying one."

I didn't press for details, but donned the robe and followed her to the kitchen. Within a few minutes she whipped up scrambled eggs on toast, and brewed coffee. I hadn't realised how hungry I was until I'd wolfed down the eggs and toast, and emptied two cups of coffee.

"That should give you your strength back," Lorraine said a grin as she took away my plate and cup.

A minute later we were back in the bedroom, stark naked on the bed; she'd stripped off the bedspread, taking the "wet spot" with it.

We then took time to explore each other's bodies with our fingers, lips and tongues, until my cock was so hard a dog couldn't have chewed on it and the juices pouring from Lorraine's pussy were soaking my hand up to the wrist. Still lying on our sides, I lifted Lorraine's leg and entered her, my cock slipping all the way into her until I was nudging her womb.

We then screwed like rabbits in a number of positions for about half an hour, until Lorraine gasped,

"I need a break!"

I had been on the point of saying the same thing - only my stupid male pride had stopped me.

Despite our frantic fucking, Lorraine's pussy was still as wet as when we started, and I started to slowly finger-fuck her as we lay side-by-side for a few minutes.

After yet another tongue-tangling kiss, Lorraine asked,

"How do you feel about the back door?"

"It's a handy way out when the husband comes through the front door," I joked.

She poked me playfully in the ribs and said,

"You know what I mean! I really like it that way - but some men seem turned off by it..."

"They don't know what they're missing," I said.

"Then you like it?"

"Like it? I love it!"

"Do you mind if I get on top? To start with, anyway."

I said I didn't mind at all, and lay there while Lorraine straddled me, her loins poised above mine. She took my cock in her hand again, rubbed it back and forth along her soaking slit to get it nicely lubricated, then placed it against her tiny opening. She then rested both hands on my shoulders as she lowered herself onto me, and I watched as my cock slid slowly into her arse until her cheeks were pressing against my short and curlies.

"Another nice fit," she said, wriggling her hips a little to settle me firmly inside her. "I was afraid you might be a bit too thick."

"I'm sure glad I'm not!" I replied, sincerely. Her arse was beautifully tight and warm, and I could feel the rubbery walls gently clasping the entire length of my shaft. "How long have you been into this?" I asked, as she seemed really keen on it.

"Ironically, I started doing it so I wouldn't get pregnant - before I discovered that I couldn't. I used to find it a bit uncomfortable, but then I got used to it - and finally came to love it!"

She was slowly riding me now, sliding her arsehole up and down the length of my cock - stopping with just the bloated crown inside her before squatting again to take me deep into her bowels. It was fascinating to watch, and even better to feel - but after a while I had had enough of being the passive partner.

"How long do you want to stay on top?" I asked.

"Oh - I'm happy to move now, if you want to. I just like to start that way so I can take it in in my own time." With that she rose from me, my cock slipping from her arsehole with a wet, sucking sound. She lay down beside me, on her back, and lifted her legs until her knees were almost against her shoulders. Looking down I could see that her arsehole had remained stretched open to a diameter of about half-an-inch; I placed the tip of my cock into the hole, then slowly lowered myself into her dark depths.

Lorraine's eyes opened wider and wider as my cock sank deeper and deeper, until my pubic bone was pressed hard against her arse-cheeks.

"God!" she gasped. "It's so deep I can almost taste it!"

I ploughed into her in that position until she said that her legs were getting a bit tired, so I moved my arms to let her lower them. The by lifting her left leg, I managed to get us both lying on our left sides without removing my cock from her grasping arse. In that position I was able to reach over and massage her clit, which, in a couple of minutes, brought her to another orgasm.

When she came her arsehole closed so tightly around my cock it was almost painful, and for a while I was unable to move. As her body relaxed so did her sphincter, and I was able to resume shoving my cock fast and deep into her again.

When I told her that I thought I was close to coming again, she rolled onto her belly, then got up on her elbows and knees - again without us disengaging. I was now virtually squatting over her beautiful bum, thrusting almost straight down into her. Once again her hand went between her thighs to squeeze my balls, and once again this spurred on my orgasm.

As she felt my knob give its pre-cumming twitches in her arse she tightened her sphincter again, which almost stopped my jism in its tracks. However, it managed to fight its way past the restriction and burst from my knob into the dark depths of her rectum.

As I groaned through the intensity of my climax she uttered a soft, "Mmmm!" as she felt the warm, sticky liquid splashing around the silky walls of her arse.

My balls were empty some time before my orgasm subsided, and I kept moving slowly in and out of Lorraine's arse, still enjoying the feel of it. My knees were threatening to give way, however, and eventually I was forced to withdraw my cum-soaked cock from her cum-drenched tube.

As I collapsed beside her, I exhaled with a gasping "Phew!"

Lorraine leaned across to kiss me again, then smiled and whispered,

"Thanks."

"Don't mention it," I said. "The pleasure was half mine."

"Would you like to do this again some time? Or will I be just another one-night stand?"

I put my arm around her and drew her over until her head was resting on my chest. I kissed the top of her head and said,

"I would very much like to do this again - and very soon."

"I was hoping you'd say that," she replied, and lifted her face to kiss me again.

Our "office affair" lasted six months after that, until she told me that while I was away on leave she had met a divorced guy of 50 in whom she was very interested - and that the feeling was mutual. I told her - honestly - that I was very glad for her; three months later I was the only one from our department to be invited to her wedding.

But I shall never forget my first "older woman"!

 

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