Regrets... Me?... No, not really... But...

Story Info
Three tales of what did happen and what could have been.
14.7k words
4.33
5.4k
4
0
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

At sometime or other, we must have all been presented with an opportunity that was a dead cert, but chose to walk away. For whatever reason. Whether it be the wrong time, the wrong place or even the wrong person. We've all done it.

I try not to dwell on such matters, but every now and then a memory will come back and prey on my mind.

This has happened to me recently. Three times, no less and I thought that while I am waiting for inspiration to drop with my tale of those "Afternoons With Amanda".

I thought I would share these three short stories with you.

I have written them as they actually happened and then as the fantasy that my mind has created.

DEBBIE (Fact...)

Back in the late 80's I enrolled on a creative writing course. I write songs and music but lyrics have always been a pain to write. It's not something that comes naturally to me. My best songs are always ones when the words seems to fall out of the ether and into my head. I thought that by signing up to the course that it would unlock my talent further. In reality, all it did was help me to write better stories.

It was a night school class and I fell in with a nice bunch of people.

Our tutor was a professional actor and screenplay writer, not that he had written anything that you would know. But apparently he got paid for his writing skills more than his acting skills. His name was Ben and he was always accompanied by his wife, Julie.

The course was over eight weeks and as time went by, I was becoming increasingly more proud of the work that I was producing. He taught us everything we needed to know about writing plays, screenplays, poetry and it's various forms, shorts stories and novels.

We eventually came to our final night together and Ben suggested that we spent it in the pub. The premise was that we should observe people and make up stories about them.

After the third or fourth round of drinks that idea was clearly out of the window and we just sat and talked about anything. The topic eventually moved around to sex and one of the women in the group, a large girl by the name of Brenda, announced that her secret to keeping her husband happy and making sure he did as he was told, was to give him a blowjob two or three times a week.

I feel that I should tell you that at this time I was married and had been for about seven years. My wife and I had been like teenagers in the beginning of our relationship, as most people are and shagged at every opportunity we had. But after we got married, the intimate side of our marriage dropped off a little and after our son was born, she lost interest in sex completely. No amount of therapy would have helped and it seemed I was to be consigned to a life of midnight masturbation, in the bathroom, with porn magazine.

I didn't inform the group of this, of course, but I realised that it had been a while since I had felt the warm, wet mouth of a woman wrapped around my erect cock. Hearing how this woman happily gave a her husband a blowjob regularly made me a little envious of her husband.

Eventually it was closing time and we all hugged and embraced each other, exchanging phone numbers and planning to all meet up again in twelve months time. Something, I might add, I am still waiting to happen, thirty years later.

As I was exiting the pub, I heard a voice say, "Could I trouble you for a lift?"

I turned around to see a young woman, whom I remembered was called Debbie.

She was about 5' 6" tall. Her blond hair was permed and pushed high on her head. Her make up was slightly overdone, for my taste. Bright pink lipstick and lilac eyeshadow. Red blusher adorned her cheeks. She wasn't slim or slender, but then again she wasn't overweight or rotund either. I would describe her as cuddly.

She wore a black leather bomber jacket, skin tight, stonewashed denim jeans and a white t-shirt with the photo of a pop band printed on the chest. Quite a nice chest too.

"Where do you live?" I asked.

"Colthorn Avenue," she replied. "Number xx."

I thought about it for a moment, trying to place where Colthorn Avenue was.

"Ah yes," I said. "It's on my way home. Jump in."

As I drove, we chatted generally. She said that she could tell I wasn't from the area and I told her that I moved with my wife, so that she could be near her aging mother. Debbie wanted to know how long we had been married and so I told her.

She replied that she lived with her boyfriend. He worked away from home for a months at a time, out of the country. She didn't say what he did and I didn't ask. But she also told me that she was tired of him being away so much and wanted him to stop. But the pay was good and he was reluctant to quit his job.

She added that she signed up to the course in order to meet new people.

I got the impression that she was lonely.

We came to her house and I pulled the car to a halt outside her front gate and switched off the engine.

She thanked me for the lift and was about to open the passenger side door.

"Would you like to come in for a cup of coffee?" she asked. "Or are you under a curfew?"

I replied that I'd love a cup of coffee.

I feel that I must point out that at no point was I remotely thinking about whether I was being given the come on, or that this was leading to anything else other than a cup of coffee. Despite what my wife and I were going through, I wasn't the kind of guy that cheated, no matter what the circumstances.

Once inside the house, we removed our jackets and hung them up.

Her front door led immediately into the lounge and directly in front of the front door was a steep staircase, which I assumed led to the bedrooms and bathroom.

As you walked into the lounge area, a wall created a small space to my left into which a dining table with six chairs was situated. There was door along the left wall which led to the kitchen and a bay window opposite provided daylight for the lounge. Set into the middle of the far wall was a fireplace. Once, it may have had a roaring coal fire burning, but now it just added to the decor and an electric bar fire sat in front of the hearth. To the right of the fireplace was television set, on a stand, with a VCR placed beneath it and to the left there was a bookshelf.

There was a couch set in front of the fireplace and a wooden oblong coffee table in front of that.

"Make yourself at home," said Debbie. "Put the TV on while I make a brew."

There wasn't any remote controlled televisions in the 1980's, so I switched on the TV by pushing the "ON" button in the front panel of the set. The screen spluttered into life and I settled back onto the couch and half watched a documentary about a pop star from the 1970's who was trying to make a comeback. Don't they all?

After a few minutes Debbie came back into the room with a tray laden with mugs of steaming hot coffee, a milk jug and a sugar bowl.

I placed my mug on the table and spooned in a generous amount of sugar, stirring as I went.

Debbie perched herself on the arm at the opposite end of the couch and cradled her mug. Time passed silently as we both watched the TV. Occasionally one of us would comment on the program.

Then the silence was broken when Debbie said, "It was fun tonight, wasn't it."

I turned to her and smiled.

"Yes it was," I said. "It's a shame that the course had to end. I was just getting to know people tonight. I'm going to miss it."

She slid off the couch arm and onto the cushion.

"You're quite a talented writer," she said.

"Do you really think so?"

"Yes," she replied. "Your stories are quite descriptive and sometimes very graphic too."

I smiled.

"When you read them out aloud, I can just close my eyes and it's like I can see it all in front of me like a film, in my head."

I was cradling my own coffee mug at this point and set it down on the coffee table.

"I was hoping that it would help unlock something inside me to help me write better songs," I confessed. "But I have enjoyed writing the stories. I must admit that I didn't know I could do it, until I tried."

The conversation died once more and we resumed watching what was clearly a very boring documentary.

Quite out of the blue, Debbie suddenly said, "It was interesting how the conversation in the pub turned to the topic of blow jobs."

Suddenly my heart rate shot up a few beats and I could feel my heart hammering in my chest. My body temperature rose a few degrees too.

I could feel sweat trickling down the back of my neck. I was suddenly very nervous.

"Yes, it was," I replied, my gaze never straying from the screen.

I had never been in this situation before and as such I had no comparison to make in order to answer her statement. I glanced nervously at my watch as I felt Debbie's eyes burrowing in the side of my head.

My inner voice was yelling, "Look at her you idiot! Don't rude! Look at her!"

I looked once more at my watch. It was almost midnight and I knew that if I stayed any longer, I would be facing an inquisition either when I got home or in the morning. Either way, it was not a prospect I was either looking forward to or wanted.

Slowly I turned my head and looked at Debbie.

I could feel that my cock was showing interest in the situation but I was pleading with it to behave. My mouth and throat were dry and my breathing laboured.

Debbie was smiling, but slowly that smile faded when she realised that I wasn't ready for what she'd had in mind.

"It's getting late and I think I'd better go," I said.

Reluctantly she agreed and so we both rose from the couch and I walked towards my jacket was hanging up.

She helped on with my jacket and I turned to face her. I could see some pleading in her eyes and in an instant our lips met in a very passionate kiss. Tongues entwined and bodily liquids were exchanged. My cock thought this was it and decided to make his entrance and I wrapped my arms around her shoulders and pulled her in hard, grinding my groin against her stomach. I knew she could feel my erection as it grew.

I suddenly was ready to throw caution to the wind and give this woman the fucking she was asking for, but I had blown it.

After our lips unlocked, she gently pushed me away and opened the front door.

"I could stay, it that's what you want," I pleaded.

Shaking her head and looking at the floor, Debbie answered, "No. It's right that you should go. You're married and I've a got boyfriend. We've got our problems, but we need to work them out with our partners. Not like this."

I kissed her one final time on the cheek and left.

On the drive home, my inner voice and I were having a massive argument. I knew I had done the right thing, but my inner voice was cursing me for letting an opportunity slip away.

Ironically, my wife and I split up and divorced some years later. But I still think about that night sometimes and imagine how it could have gone...

DEBBIE (Fantasy)

We came to her house and I pulled the car to a halt outside her front gate and switched off the engine.

She thanked me for the lift and was about to open the passenger side door.

"Would you like to come in for a cup of coffee?" she asked. "Or are you under a curfew?"

I replied that I'd love a cup of coffee.

"Make yourself at home," said Debbie. "Put the TV on while I make a brew."

Debbie perched herself on the arm at the opposite end of the couch and cradled her mug. Time passed silently as we both watched the TV. Occasionally one of us would comment on the program.

Then the silence was broken when Debbie said, "It was fun tonight, wasn't it."

I turned to her and smiled.

"Yes it was," I said. "It's a shame that the course had to end. I was just getting to know people tonight. I'm going to miss it."

Quite out of the blue, Debbie suddenly said, "It was interesting how the conversation in the pub turned to the topic of blow jobs."

Suddenly my heart rate shot up a few beats and I could feel my heart hammering in my chest. My body temperature rose a few degrees.

I could feel sweat trickling down the back of my neck. I was suddenly very nervous.

"Yes, it was," I replied, my gaze never straying from the screen.

I had never been in this situation before and as such I had no comparison to make in order to answer her statement. I glanced nervously at my watch as I felt Debbie's eyes burrowing in the side of my head.

Slowly I turned my head and looked at her.

"It's been so long since I had blowjob, I think I may have forgotten what it feels like," I said, half laughing.

I explained to her that my wife's interest in sex was non existent and the only way to get any kind of relief was through masturbation.

"She caught me once," I confessed. "I was up in the bedroom watching a Sunday afternoon war movie on TV.

For some inexplicable reason, I was overcome with the desire to have an orgasm."

As I continued, Debbie slid off the arm of the couch and onto the cushion next to me.

"She came up stairs to ask me if I wanted a cup of coffee and caught me with trousers around my knees and my cock in my hand."

Her hand strayed to my thigh as I looked down at the carpet.

"It sounds kind of sad when I hear myself say it," I said.

Her hand moved from my thigh and closed around my hand, which was resting on the couch cushion.

"It seems to me that you are desperately in need of some care and attention," she said. "So am I. It's been weeks since I felt the touch of a man and Scott, my boyfriend, rang me earlier to say that he's going to be away another three weeks. The bastard!"

I put my arm around her shoulder and she leaned into me. I felt her nuzzle into my neck and it felt nice. I moved my head and looked down at her as she looked up at me. Our lips met in soft but very long kiss.

"Mmm, you have lovely soft lips," she said, as we broke apart. "You're a great kisser too."

She leaned back into me and our lips met in a more passionate kiss. Her mouth parted enough for my tongue to slide between her teeth. As she felt my tongue searching through the warm wet confines of her mouth, she started to suck on it.

I felt her hand move across the front of my jeans as she searched for a way to undo my belt. I helped out and she tugged it apart and began undoing the button on the waistband.

My cock was hardening quickly and in the seated position we were in, I was starting to feel uncomfortable and longed to have my penis set free.

Button undone, she began undoing my button fly, before sliding her hand inside, rubbing the front of my briefs.

She moved back from me, her hand still in my trousers, with a look of astonishment on her face.

"Ooo, you feel huge and thick," she said. "I think I need to take a look at this."

She tried to tug my jeans over my thighs but she needed help and I lifted my butt up off the couch to ease removal of the clothing. She pulled the jeans to my ankles and tossed them over the back of the couch.

My cock was now rock hard and straining against the flimsy material of my red briefs. Its outline clearly visible, as was the small damp spot produced by my pre-cum. I didn't shave my pubic area back then and some wisps of my pubic hair sprouted from the legs of my underwear.

I am not huge in the cock department, but I am not average either and quite happy with the seven inches I was blessed with. To Debbie, it appeared to be the biggest penis she had ever seen.

"Bloody hell, is that for real?" she gasped. "Scott's cock fills me up nicely, but he's no where nearly as big as this."

Slowly and tentatively, she hooked her fingers around the waistband and began to tug my briefs down.

My cock lay there surrounded by my thick pubic bush and she whistled loudly when her eyes fell upon it.

"How could your wife lose interest in a monster like this?" she asked. "If you were mine, you would never get a moment to yourself and I certainly wouldn't need the dildo I keep in my bedside drawer."

The image of Debbie fucking herself with a dildo drifted into my mind and my cock twitched in approval.

Debbie gasped.

"It's alive and has a mind of its own, it would seem!" she said.

She ran her fingertip along the length of my shaft from where my cock met my scrotum to the tip of the head. Sticky, clear pre-cum was dribbling from the hole on my cock-head and she ran her finger through it and then slurped it into her mouth. I watched as she made a point of slowly pushing the digit between her delicious lips and licking the clear sticky fluid from it.

I was aching to fuck this woman, but she had other ideas for now. She curled her fingers around my rock hard shaft and pointed the bulbous mushroom head of my cock towards her open lips.

The feeling of her mouth slowly closing around my hard shaft and her tongue wrapping around my cock head was almost indescribable. She held my cock fast in her hand and rocked her head back forth along my length. She used the tip of her tongue to flick the underside of my cock, close to the head and ran her tongue along the length of my shaft until she reached my scrotum. She sucked each of my testicles into her mouth and let her tongue lap at them like a kitten licks its milk.

She was very experienced in sucking cock.

It had been so long since anyone had given me a blow job and now it was really happening. I could feel my sap rising and felt like I was close to coming, but I really wanted this to last.

I placed my hands on either side of her hand and slowly pulled her off me.

"Are you okay?" she asked. "Did I do something wrong?"

"No," I replied, smiling. "You've done everything right. In fact you're very good, almost too good and I felt as though I was going to come. It's been so long and I really want this to last. So is there anything I can do for you?"

She smiled, stood up and began to remove her t shirt, revealing a white padded bra, with lace trimmings. She tossed the t shirt on to the couch with my jeans and reached around behind her to unclasp her bra. I pulled off my shirt and socks.

I looked at her breasts. They were small, but not as small as my wife's which were very small indeed. Her dark pink nipples were swollen and erect and surrounded by darker coloured areola.

The bra followed the way of the t shirt and then she set about removing her jeans. But she decided to put on a show and turned her back to me.

She slowly tugged her jeans over her thighs and to her knees. She bent over as she pushed the garment to her ankles.

Her bottom was adorned by a pair of royal blue satin panties that rode up the crack of her arse slightly. As she bent over, I could make out the bulb between her thighs that was her vulva. I closed my fingers around my erection and began to rub it gently. She kicked off the jeans and turned around.

"You had better stop that, if you don't want to come yet," she said. "Anyway, I think that's all for me."

She walked over to the couch and climbed astride me.

I felt the warmth of her crotch as she lowered herself onto my lap and began to gyrate her hips along my cock.

Our lips met and I moaned into her mouth.

I reached up and placed my hands on her breasts. Her nipples were solid against the palms of my hands and she moaned as I massaged them.

Tongues overlapped and searched as I rolled each of her berry-sized nipples between my thumbs and forefingers.

I felt her stiffen and then she broke the kiss.

"Shit!" she gasped. "I must have been as desperate as you, 'cos you just made me come doing that."

She grabbed my right hand and thrust it in the gap between her crotch and my aching cock. I probed her vulva with my middle finger and felt a damp patch in the gusset of her panties. She had come alright and had come wet too.

"I never come like that," she said. "At least not with Scott, at any rate."