My late wife Mary and I had a wonderful, creative sex life, but we had understandably not been active in bedroom during her losing battle with cancer. Mary apologised over and over for her lack of enthusiasm and even went as far as to suggest that I might want relieve any sexual urges elsewhere as the cancer spread. I wouldn’t and couldn’t consider that. After she died, the idea of sex with someone else was repugnant for about a year, but soon some interest in sex gradually reappeared. I finally mustered the courage to visit an escort, but let’s just say the encounter was a disaster and I left with both my ego and libido deflated.
Now, all those forgotten feelings had returned. While I had several lovers before I met Mary, and my wife had been great in the sack, I had never met someone as overtly sexual as Helena. I certainly had never been fucked like that before in my fifty-eight years.
I then laughed to myself: I had never been laid on a ‘first date’ until this evening. Maybe, I thought, you really can turn back the clock.
I was just beginning to think about the fact that Helena had fucked me without using a condom – and what that meant – when she reappeared at the bedroom doorway. Helena was no longer nude, but what she was wearing did little to hide her body. She had slipped on a sheer, pale peach dressing gown that was loosely tied at the waist. Her nipples were clearly visible through a thin material. The dressing gown was so short that it did not reach more than an inch or two past her ass and, because it was so loosely tied, her shaved pussy was not covered. If anything, Helena looked even more fetching – and more sexy – slightly clothed than when totally naked.
She was carrying a tray on which were two glasses of wine, a bowl of strawberries, and what looked at first like a bowl of whipped cream. However, Helena quickly corrected my mental error.
“I simply adore strawberries and Greek yogurt,” she said.
Helena set the small tray on the bedside table, reclined on the bed and handed me a glass of wine. She picked up her glass and clinked it against mine.
“Here’s to love and sex, particularly sex – for now,” Helena said with a charming grin. “James, have you ever thought about starting a stud service for we blue-haired ladies?
I laughed as Helena snuggled closer to me. As she did, her left breast became exposed.
“Oh dear, she wants some more attention. That’s the problem with tits; they often have minds of their own,” she chuckled. “Could you please take care of her for me?”
I slowly set my wine on the table by my side of the bed and then rolled over to focus on her breast. As I untied the belt holding her wrap together, I slowly looped my tongue around and around her stiffening nipple, giving it a healthy suck every so often. After a minute or two, I realised I was rock-hard again, and Helena had started to moan softly. I looked at the clock by her side of the bed, and it read 23:42.
And then I stopped and rolled back over to have another sip of wine. Just as I raised the glass to my lips, I felt a pillow crash into the back of my head, making me spill about a quarter of the glass on the sheets.
“Oh, it appears you have wet the bed. You are a naughty boy, James,” Helena said sternly, although her acting was betrayed by a sly smile. “I think you owe me something for messing up my bed linen.”
“How can I ever make it up to you?” I asked.
“Well,” she responded, “you could accept my offer of the dessert I promised you at the restaurant. Tonight I feel like having my strawberries and yogurt in a slightly erotic manner. Will you join me?”
I nodded yes, figuring we would feed each other berries dipped in the creamy yogurt. That would be highly erotic to me, but Helena had something completely different in mind. She remained in her reclining position and reached over to select a large berry. She then reached down and inserted it in her still-wet pussy. She then used her fingers to scoop up a big glob of the thick yogurt, which she sensually spread in a circle around her completely bare pubis.
She turned to me, looked deeply into my widening eyes and said, “Your pudding is served. Enjoy.”
As inexperienced as I was, I knew what to do. I scooted down in the bed and began licking Helena’s left thigh. I figured I would take this very slowly and, as Helena had said, enjoy myself. I didn’t want to get it wrong.
I nibbled my way northward, until I started to lick the yogurt from her skin just left of her labia. Continuing my snail-like pace, I slowly lapped up the rest of the ‘pudding’, spending a lot of time making sure that all of the creamy substance was removed from her clit and the opening of her cunt.
Helena reacted to my licking with heavier breathing, increasingly loud moaning and considerable wiggling. I figured that I was getting it right.
The yogurt was nearly all gone, so now I had to figure how to capture the hidden fruit. Due to my previous efforts and Helena’s thrashing, the strawberry had slipped further back into her pussy. I certainly could not reach it with my teeth to take a bite, so the only thing to do was to stick my tongue in her cunt and lap at it, much like a kitten drinking milk. I could taste the tartness of the berry as a ran my tongue across its seeded surface, but I could also taste Helena’s pussy juices flowing freely around the fruit. I also realised that as I was lapping to get at the strawberry, my lips we pressed firmly against her clit. Helena’s squirming and moaning were increasing measurably.
She finally broke the silence: “James, that is so fucking horny and so fucking good. Keep doing it! Please don’t stop! “
I continued to lick at the strawberry and could tell that it was beginning to disintegrate. The more I licked, the more Helena moaned, and she started to bounce her ass on the mattress. After another 30 seconds or so, I felt her legs lock against my ears, and my newfound lover began to thrash about wildly.
“Ahhhhhhhhhh! Fucking hell! I think my cunt is on fire! Goddamnit, James. I am cumming so fucking hard. Keep licking my pussy! Oh my goodness, this feels so sensational!”
She shouted for at least a minute, mostly gibberish. I finally had to quit licking because my face and beard were completely covered in strawberry-flavoured cum. Once I removed my tongue, Helena began fingering her clit to prolong her orgasm while continuing to moan and babble nonsense. I had never seen a woman come so hard and for so long.
After lying quietly for a moment, she reached back down to her pussy and used her index finger to scoop the remains of the fruit from what could only be described as her juicy cunt. She raised what was left of the strawberry to her facial lips and proceeded to nibble and lick the fruit from her fingers.
After a moment more, Helena raised her head (I was still lying on my stomach with my head between her knees) and said: “Did you enjoy your dessert? I certainly enjoyed mine. Please come up here now and be with me.”
I scooted back up the bed, and was rewarded with a passionate, strawberry-infused kiss. Her tongue explored all corners of my mouth. Without breaking our kiss, she then reached down and wrapped her hand around my cock, which was now as hard as nails.
“I think there is probably some strawberry left down there,” she said softly as she fondled my penis and my balls. “Would this big guy like to have a taste?”
I needed to fuck, so I rolled on top of Helena as she spread he legs, and I began to rub the head of my dick against the wet entrance to her pussy. While I really wanted to take it slow to enjoy every moment, my cock head quickly slipped into her sopping cunt.
As I pushed myself up to assume the classic missionary position, I looked over at the clock: it now read 00.09. I thought to myself: “I wonder if this old goat can last for fifteen minutes?” As I started to slowly and gently maintain a back-and-forth rhythm, I thought it was possible. I had cum so strongly less than an hour before, I wondered if I would be able to cum again. So I increased my speed whilst fondling Helena’s left tit, but I soon felt that familiar feeling. I knew I had better slow down if I were to last for more than a minute. Remember, James, slow and steady wins this race, I told myself.
I switched my focus to Helena’s face, but she had her eyes closed, presumably enjoying the gentle fucking rhythm that I was setting. That would be my luck: I screw a woman for the first time in years, and I put her to sleep!
But then Helena opened her eyes slowly and smiled softly. “This is fantastic, James,” she whispered. “I just love to be fucked slowly and sensually. Your cock feels so good inside me. Can you do the work for now and let me relax for a moment?”
So, I maintained my slow and steady rhythm in relative silence. Every now and then, I would be rewarded with a passionate kiss and, after what seemed like a long time, Helena’s hands began wandering across my ass cheeks. I picked up my pace a wee bit.
“Oooh, that’s really good,” Helena purred. “I think your cock has grown a bit more in the last minute. It’s hitting a really sensitive spot, and it’s fucking fantastic.”
I looked at the clock, and I had been fucking her for nine minutes. That’s pretty good for an old boy, I thought to myself. As I started to pick up a bit more speed and twist my hips to screw Helena a bit harder, I felt her legs rise up and then wrap around my thighs.
“Okay, Lover,” she said more excitedly.
I knew that I would not have much control if I picked up that pace further, so I kept a slow pace but increased the pressure so that the tip of my cock was beginning to touch her cervix. I hear Helena gasp and then I felt her starting to fuck me back, lifting her legs so that her ankles were on my shoulders.
“That so fucking good, James. Fuck me hard and fuck me fast. But, please do not come yet … let me climax first!”
Her breathing had now become a pant, and she was increasingly squirming. She suddenly reached behind my head and pulled my lips to hers. Her kiss was truly passionate, almost violent. She began fucking my mouth with her tongue began in sync with the rhythm of my cock. In and out, in and out. After a moment, she released her grip and shouted..
“Really fuck me hard! Just a moment more!”
I started to slam as hard as I could into her as I stared into her eyes. They were wide open, and I could tell they were filled with lust. I could feel my balls slam into her ass with each thrust. Suddenly, she stopped breathing and moving, and I could feel her pussy begin to heat up. Then …
“Oh my god. Fucking hell! I am cumming so hard! Goddamn, James, you are making me cum again and again!”
She continued to shout, mostly obscenities, and as I plunged into her again, I felt semen rise up through my penis. I plunged as deeply as I could into her cunt, and then I too became perfectly still.
I started to shout as my orgasm commenced, but she screamed over top me: “Yessss! I feel it. Cum inside me! Fill me with you hot cum! I want you to squirt all of your hot cum in my cunt!.”
I collapsed on top of her as my cock continued to spasm. Finally, when both of our orgasms subsided, I looked back at the clock as I began to roll off of her: 00.22. Thirteen minutes of solid fucking … not too bad for a fifty-eight-year-old bloke who hadn’t been laid in years.
Helena cuddled next to me and said quietly: “James, I think I will want to keep you around for a while. I told you the evening when we met that I am highly selective, but you have passed my biggest test with flying colours. Let’s get some sleep now, and we can talk more tomorrow.”
I was puzzled by what she had said, but I was also exhausted. I could tell that Helena, nuzzled softly against me, had fallen asleep as soon as she had stopped talking. I was thinking about my good fortune, how much my life had changed in one evening and about a thousand other things when I also dozed off.
I stumbled into the office about an hour late on Wednesday morning. I woke up in Helena’s bed at about 6am, pulled on my clothes, left a note to say I would be in contact later and let myself out without waking her. I found a cab and went back to my place to shower and put on a suit to be presentable in the office.
I sent Helena a text later in the morning to thank her and to ask her to call me when she had a chance. I heard nothing until the afternoon, but the message did not come directly from Helena. Rather, Tim, my assistant at whose party I first met Helena, walked into my office.
“I couldn’t get Emma off the phone just now,” Tim said. “She was yammering on about the good time Helena had with you last night. She thinks you’re wonderful!”
“Who thinks I’m wonderful? Emma or Helena,” I asked, trying not to hide a grin.
“Actually, both,” Tim replied. “In fact, you can add my mother-in-law to the list. Helena was on the phone for an hour with Sue to rave about how wonderful you are, and then Sue called her daughter to pass along the message. Emma then had to call me to tell me all about it.”
I hesitated for a moment, wondering what exactly Helena had told Sue about last evening.
“Well, Tim,” I replied after the pause, “I guess Helena does not get out much. I can’t see why she would think I was so wonderful.”
If Tim knew what had happened last night, he was not showing his hand, but he did give me some interesting information.
“I wouldn’t sell yourself so short, Boss,” Tim said. “As I told you last week, I really do not know all that much about Helena except that she is really tight with my mother-in-law and that Emma also talks to her from time to time. I had not met Helena until Sue and Emma’s father divorced about five years ago. I try not to listen to the girl talk in my house, but I have a feeling the Helena has a very active social life, although she never seems to have a steady beau and I have never seen her bring a date to our house or to a party that I have attended.
“I gather that Sue and Helena were pretty wild when they were young and at university together. While Emma would never confirm this, the reason that Sue and Howard split up is because Sue was playing around. I think Helena may have been involved somehow … I think Helena fixed Sue up with the guy she was seeing. Emma was a pretty pissed off at her mother for breaking up the marriage, but they seem to have worked things out. However, Sue and Helena have been thicker than thieves ever since Sue and Howard divorced. My guess is Howard, who is a nice guy but a bit dull, did not approve of Helena one bit.”
I thought for a moment, then replied: “Thanks for the information, although I do not know what to make of it. I have to admit that I had a wonderful time last evening with Helena, and I would really like to see her again. No one can replace Mary, but I admit it was fun to get out of the house for a change with someone feminine and attractive.”
“I’m really happy for you, James,” Tim said from his heart. “I know how hard it has been for you the past several years, and I know how much you loved Mary. But, she’s gone now, and I think she would rather you be out and about, having a good time, than moping around your house all the time.
“Besides,” Tim continued with a grin, “unless you’ve been keeping secrets from me, the only pussy you’ve had in the last five years is Roxy, and she doesn’t count. I don’t want to cast aspersions, but I think you will have to get used to the fast lane if you are going to keep up with Helena!”
With that, Tim wandered out the door back to his own office. I had to chuckle at his reference to my elderly, overweight female cat. But Tim had a point. Helena revealed more of her sexual side in a single evening than Mary had revealed in our first year together.
I then again thought about the fact that Helena and I had sex twice without using a condom. Tim said she had a lot of beaus; I did not think for a moment that I had been the only guy she had recently fucked.
That’s when my phone began to buzz in my pocket. I pushed the button without looking at the number, and was greeted by:
“So you think you can slip out of my bed and from my house without giving me a good-bye kiss. Mister, you are in big trouble!”
“It’s so nice to hear from you Helena,” I replied magnanimously. “How are you feeling today?”
“Very lonely,” she replied. “I dreamed I was going to wake up next to a good man who would serve me breakfast in bed, and then I realised I was all alone. I’m really pissed at you.”
“Nonsense. Save the drama,” I said, closing my office door. “You called Sue, Sue called Emma, Emma called Tim, and Tim told me how you were raving about me to his mother-in-law.”
There was a pause on the line, then Helena said much more softly: “Damnit. I hate it when I lose my advantage. Okay, I’m not angry at you. I had a wonderful time last night, and I would hope that we can get together very soon. We have a lot to talk about.”
I thought for a second and replied, “Is tonight too soon? Or am I being a stupid man who is rushing things by wanting to see a woman who had at least three orgasms with me the night before?”
“Only three? I think there may have been another one in there that you missed. By the way, I hope your office door is closed and you are alone.”
I laughed. “Yes, all of your many secrets are safe with me. I am very discrete and do not kiss and tell. By the way, how much does Sue know?”
It’s a shame that it was not a video call, because I am sure Helena was turning a bright shade of red. However, she quickly recovered by saying, “Sue Holton and I have been best friends for forty years. Any secrets of yours that I may have accidentally told her will be safe with her.”
“Does that mean we have a date tonight?”
“Can you cook?”
“Believe it or not, yes. I can do more than just grill a steak.”
“Actually, a steak would be great. Red meat makes me really randy. Listen now, you’ve seen mine, so I want to see yours,” Helena said, presumably referring to my house since she saw every bit of me last night. “Where do you live?”
There’s nothing like being forward, I thought. Still, the idea of having an attractive woman in my house was certainly tantalising, even if I had to cook. Besides, Roxy would like the company. I gave Helena my address in Islington and said: “Can we make it 8 o’clock? I will need to do some shopping on my way home, and I would like to have a chance to hide the pornography, the spent condoms and the assorted ladies’ underwear in my bedroom before you arrive.”
Helena laughed heartily. “I shall see you not a second before the appointed hour, and I shall bring the wine. Casual dress?”
I agreed, and we broke off the call.
I did no work for the rest of the afternoon. All I could think about was fucking Helena. When I tired of that, I thought about her fucking me. I thought about her face, her legs, her tits and her pussy. I finally locked the door to my office and jacked off into a tissue before leaving work earlier to buy groceries and tidy the house.
To be continued …
