I met Helena at a party on a Saturday night during early June hosted by Tim and his wife, Emma. Tim is my assistant at work, and he joined my department just as my wife, Mary, was entering the final stages of her losing battle with pancreatic cancer. Tim and Emma were a huge support to me as my world was crumbling, even though they are twenty years younger than me. I could not ask for better friends, and I was really happy that Tim would succeed me as head of my department when I retire, probably next year.
So, it was natural that Tim and Emma invited me to a summertime party to show off their newly refurbished garden. As I was sipping wine and talking to some of Tim’s and Emma’s friends on a warm evening, I spied Emma and her mother, Sue, talking to an older woman. This woman caught my eye for two reasons: she was the only person at the party who looked like she could be over fifty besides Sue and me, and she was devastatingly attractive. Her short salt and pepper hair framed a lovely face that – while showed some years had passed – had aged quite well. She was wearing a pair of red skinny jeans, a tight white t-shirt and an unbuttoned blue shirt over the top. She was also wearing a pair of high-heeled white sandals, and I noticed that her toenails were painted red, matching the colour of her jeans. Of the thirty or so people packed in the small garden on a warm summer night, she was probably the most stylishly dressed.
About twenty minutes later, Emma walked toward me, accompanied by this woman. She introduced Helena as an old friend of Sue’s, and Emma winked at me when she said the Helena was single. The three of us spoke for a moment, until Emma slipped away, allegedly to check on the food that was about to be served.
I really did not know what to say, but Helena did not let the awkward silence last for more than a several seconds.
“So, James, Emma tells me you are on the market. I am sure there are all sorts of divorcées and widows beating down the door of a wealthy, eligible and very attractive older man.”
“Actually, no,” I stammered. “I really haven’t dated much since my wife died four years ago. I am sure that I should, but …
Helena interrupted. “With all due respect, you should get out more. I am sure that’s what your wife would have wanted. I don’t think any woman would want you moping around on the weekends at home being alone. Emma and Sue have told me a lot about you. According to them, you are a handsome, articulate and lively gentleman, and my first impression is that they, as usual, are correct.”
I was a bit taken aback by Helena’s kind words and also by her direct manner, so I asked: “Is this a set-up? Is Emma playing match-maker?”
Helena threw her head back and laughed. “In a way, yes, but not probably in the way you think. Actually, it is more of Sue’s doing. But, let’s get to the point: what woman of my age wouldn’t want to meet an attractive, sexy, mature man?”
Getting bolder with her compliments, I asked her: “And exactly what is your age? I’m fifty-eight.”
“You are pretty well preserved for a geezer,” she replied with a smile. “You can be my toy boy … I’m fifty-nine.”
I was momentarily dumbfounded. I would have put Helena in her mid-fifties. She was very slender, but I could tell that she had a generous bustline under her t-shirt. Her jeans were nearly as tight as those worn by Emma’s sixteen-year-old daughter. I wondered if Helena had benefitted from some cosmetic surgery.
Helena must have read my mind. “What you see is the real me. I take care of myself and still go to the gym three times a week.”
“You are very fetching, indeed,” I said, returning some of her compliments. “You must have a long line of suitors knocking at your door.”
“I am selective, very selective,” she told me. “I have never married; I just never really settled down. To tell you a secret, I have a bit of a wild streak. I have had a lot of relationships, some very short and others a bit lengthier, but I guess I never have really met anyone who I felt was perfect for me. It’s good to know that I can still turn some heads, because in the last thirty seconds you have eyeballed me from my forehead down to my toes.
“I just love men,” she continued. “They are so obvious and indiscrete!”
I must have turned thirty different shades of red, but Helena reassured me. “At my age, I accept any compliments I can get! But, if you want to make your ‘indiscretion’ up to me, why don’t you ask me out for dinner?”
“Would you like to go out for dinner?” I quickly responded.
“I would love it. I’m going to be out of town for work for about a week, but how about a week from Tuesday? Here’s my number,” she said, handing me a plain card with her name and a mobile/cell number. “Why don’t you give me a call during the evening the day before? I should be back in London by then.”
We agreed that I would select a restaurant in the West End and, just as I was about to ask Helen more about herself, Emma’s mother sauntered over and asked Helena if she could help in the kitchen. Helena gave me a peck on the cheek and said that she would be looking forward to my call.
While I tried to find Helena the rest of the evening, she had disappeared. Emma told me that Helena had received a work-related call and had to leave suddenly. When I asked Emma what Helena did for a living, she told me that she was a consultant in the entertainment industry and therefore did a lot of work in the evening. Emma explained that she and Sue had wanted to introduce me to Helena for quite some time.
The next week passed very slowly. I asked Tim a lot of questions about Helena, but he said he did not really know her all that well. He knew that she and Sue had been good friends since they were young and that Helena sometimes attended family gatherings. He said she was high-spirited and friendly, but he had never seen her attend a party with a boyfriend or male companion.
As soon as I returned home for work on Monday, I began pacing the house, trying to decide when to call Helena. I decided I was acting like a sixteen-year-old mustering up the courage to ask a girl out for the first time. While I had been out with a couple of women since Mary died, these encounters had been arranged through ‘mature’ internet dating sites, and almost all of the dates had gone poorly. I also decided to see an escort for some sexual relief about a year after Mary passed away, but performance anxiety got the best of me.
I finally thought, “What the hell,” and dialled her number. Helena picked up on the fourth ring.
“James, I was beginning to think you wouldn't call. I bet you were trying to guess what time would be best to ring me.”
I did not know what to say, so I stammered and finally managed to say, “Are we still on for tomorrow evening?”
“Yes,” she replied. “I am really looking forward to it. I have been Italy for the past week, working non-stop. I will really enjoy talking to an intellectual person rather than some of the really boring, demanding people I have been with.”
I was just about to ask what she had been doing in Italy, when she interrupted.
“Shit, my doorbell just rang. Quick, when and where are we meeting?”
I gave her the name of one of my favourite restaurants in Covent Garden and asked: “Is 7.30 for drinks in the bar okay with you?”
“Perfect, my love,” she replied. “See you then. She then made a loud kissing noise through the phone and hung up.
As soon as I came home from work the next day, I carefully showered and then trimmed my beard. I wore a pair of casual yet classy trousers, a striped shirt and a blue linen jacket … I laughed, wondering whether this was what a sixty-something should wear on a first date.
I arrived at the restaurant at 7.20, but Helena was already perched on a bar stool, drinking a martini and looking utterly fantastic. She wore a black jumpsuit with wide-legged trousers. The neckline was low enough to show a healthy amount of cleavage, and a pendant dangled between her breasts, almost guiding my eyes to what she wanted them to see. She also wore a bright yellow jacket, with stiletto sandals of a perfectly matching colour on her obviously pedicured feet. I am sure, despite her age, she turned a lot of heads upon entering the bar.
I bent down to give her a polite peck on the cheek, but Helena turned her head to plant a sizable kiss on my mouth, and I could feel her tongue quickly trace across my upper lip.
“Don’t worry about anything, James,” she said as I sat on the stool next to her. “I just know we are going to get on splendidly.”
And we did. Over dinner, she asked me a lot about myself, and reached over to touch my hand when I told her about Mary’s final days. By now we were on our second bottle of Sancerre. I learned a lot about her – her tastes in film, theatre and books, her love of travel, wild times at university in the early 1970s with Sue – but she deftly changed the subject when I asked about her work.
We had finished our main courses, but when the waiter inquired whether we wanted dessert, Helena asked for the bill. “Since you asked me out for dinner, I think you should pay,” she said smiling. “But, so I don’t feel too bad, I must insist that you come back to my place for pudding.”
How could I refuse?
We hopped in a taxi to take us to her flat in Mayfair, just off Grosvenor Square. During the ride, she snuggled close and began to slowly kiss me. At one point, I think her hand wiped across what was starting to become a bulge in my trousers.
She waited while I paid the fare and then grabbed my hand, and together we scurried into the building. As soon as we entered the small lift, her arms wrapped around me and she began kissing me much more passionately. We broke off when we arrived at the third floor.
Her flat was a small one bedroom that was furnished in a modern style: a large leather sofa and matching chairs, with tables and bookshelves made of light wood. It was very classy and obviously very costly.
“If you want to be a darling, could you get a bottle of white wine from the fridge and some glasses from the cupboard by the cooker?” Helena asked. “I will just be a minute.”
Not long after I sat down on the sofa with the wine and two glasses, Helena emerged from the hallway. She had removed her jacket to reveal that the jumpsuit was actually a halter top. She had adjusted it to reveal much more cleavage, and as she turned to switch on the stereo, she revealed that her outfit was nearly backless. However, it also revealed that Helena had the body of a much younger woman; it showed some signs of age, but no one would ever mistake her for nearly sixty.
She sat down as I poured the wine, but she began to snog me full stop. This went on for at least a minute, until she backed away slightly, reached for my hand, placed it on her breast and whispered, “I know it has probably been a long time, but I suspect you still remember what to do.”
Thank goodness I did.
My hands were soon wandering between the material of her outfit and her beasts, and she was slowly exploring the outline of my erection with her left hand, After a couple of minutes of what could only be described as heavy petting, Helena again broke away and stood up.
“We’re both obviously adults and a half, so let’s skip the preliminaries.” She then unhooked the snap at her neckline, allowing her top to completely fall to reveal to lovely B-cup breasts and erect nipples. Her tits sagged a bit with age, but were gorgeous nonetheless. She then reached for a side zipper and slowly stepped out of the bottom of the one-piece. She was only wearing her stappy shoes and a small black g-string.
“I’ve shown you mine, James. Now it is time to see yours.”
I was a bit frightened as I was not in nearly as good shape for my age as Helena, but she sat on my lap, slowly unbuttoned my shirt and complimented me on my chest. Once she had removed by shirt, she scooted over on the sofa to unbuckle my belt and unzip my trousers. My cock immediately sprang up. She quickly pulled down my boxers to release my manhood and handled it softly and sensually. She began kissing me with passion as she stroked a cock that hadn’t been touched by anyone but me in several years.
She whispered softly, “That’s quite impressive equipment for and old codger!” She pulled away, gave me a beaming smile and then proceeded to go down on me. She licked the head slowly for what seemed like several minutes and then engulfed my entire cock all at once, I almost came immediately, but managed to control myself... at least for a moment.
“That was delicious,” she said softly. “However, we are too old to be doing it on an uncomfortable sofa when I have a nice, big, comfy bed that is perfect for love-making. Please come with me?”
I forgot that my trousers were still around my ankles and almost fell flat on my face. However, after shedding the trousers and boxers, I quickly followed Helena into her darkened bedroom.
“Lie down on the bed, darling,” she said in her soft voice. “I know it has probably been a long time, so let me do all of the hard work tonight. I just want you to enjoy.”
So I did what I was told and I enjoyed.
Helena snuggled against me, but with her head near my groin. She kissed me softly in a circle around my erect cock, and then started to very gently lick my balls. After what seemed like forever, she began slowly sucking my cock. For my part, I was able to reach under the small G-string to discover a fully shaven pussy that was already damp with her womanly juices. I was able to locate her clit with my index finger and was rewarded with a little shudder and a soft moan.
Helena continue to suck softly, as if she knew that anything more aggressive would probably make me cum. We continue to explore each other’s nether regions – she with her tongue and I with my finger – for several minutes, until she finally sat up, shifted around where she could whisper in my ear and said:
“You have a delightful cock, and I want to enjoy it fully. The best way for me to do that is to get on top of you and fuck you ever so slowly. I think that would be best for you under the circumstances, and I know it would be very good for me. So, do you mind if...”
And with that she shifted again, removed her thong and slowly mounted me, rubbing the tip of my cock against her pussy lips and then her clit. She then lined me up with her opening and slowly descended down on my penis as if it were made of glass and would shatter if she did anything quickly. Mary and I had a great sex life when we were younger, but I had never been fucked as sensually as this.
I began to moan slowly as I felt her pussy engulf more of my cock. It took several minutes for her to finally accommodate my entire length, and it was only then that she began to rock up and down and back and forth, slowly fucking me.
"Oooh, you fill me so nicely, James," she told me. "I'm sure Mary must have told you often what a nice cock you have."
Through the dim light I could see Helena above me, slowly rocking on my manhood, smiling gently at me. Every once in a while, she would bend down and softly kiss me, sometimes on my cheek and sometimes on my lips. I finally mustered the courage to place my hands on her breasts and, after a moment, began to explore her erect nipples with my fingers.
“That’s it, James. Squeeze my nipples, first gently and then harder,” I followed her instructions and I could feel her nipples begin to harden as she started to moan. “A bit harder now, my darling,” was all she said as I started to pinch her left nipple as I squeezed her right breast. She quickened her pace as her breathing became more laboured.
After several more minutes and more experimentation in handling her breasts, she began to moan loudly and started to grind her pelvis against mine. I stretched upward, so that I could begin sucking her right nipple.
“Jesus, that is perfect; please don’t stop,” she growled. After about thirty more seconds, Helena threw her head back and said, “Shit, you’re good at this. I am about to...”
I felt her body tense and I could feel warmth envelop my cock. Helena pushed me back down and then held herself still for a moment. Soon, I felt a flood of warm liquid begin to gush from her pussy. At the same time, she began shouting:
“Oh fucking Christ, I can’t believe how good that feels! Jesus, I am cumming; I am cumming so hard!”
Mary had never had an orgasm like Helena’s in our thirty years of marriage,
After shouting gibberish for a moment longer, Helena finally rolled off my cock. For a moment I was disappointed, both because I was no longer inside her hot pussy and because I figured that she was probably spent. I was wrong. She began attacking my cock with her mouth, sucking like a vacuum. Mary would never have considered sucking my cock after it had been inside her pussy, but Helena was devouring my penis, even though it was covered by both her and my juices.
Helena within minutes had my entire shaft in her mouth and down her throat. I could feel my orgasm beginning, and was disappointed again when I felt her pull away.
“C’mon, James. Spray my face with your cum. I want to drink it; I want to wear it. Please come all over me.”
I thought I sprayed everything inside me on my first spurt, but I kept on spewing cum all over Helena’s face and hair. While I still masturbated often, I had not come that forcefully in many, many years.
When I finally stopped, I could see clearly that Helena’s lovely face was covered with my goo. She smiled at me, removed a glop from her eye with a finger, stuck it in her mouth and then said: “I know some guys do not like this, but what I really want to do right now is kiss you.” She pressed her lips against mine and shoved her tongue nearly as deep down my throat as my cock had been down hers. My beard was now covered with my own spunk as it dripped from her face onto mine.
She finally collapsed next to me, and we held each other without speaking for several minutes. She finally broke the silence by asking, “Think you can do it again?”
“No way, it will take me several years to recover.”
She giggled. “That’s okay; I think I am fucked out for now. Let me go get that wine, and then we can have a little chat.”
I watched as she left the room, totally naked, wiggling her ass a bit on purpose. I laid back and thought, “Not bad for an old fart”. To be continued
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<a href="https://www.lushstories.com/stories/mature/helena-part-1.aspx">Helena (Part 1)</a>