Falling for a Younger Guy

Story Info
Middle-aged woman suddenly attracted to a much younger man.
3.9k words
4.43
17.7k
16
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
Bisense
Bisense
42 Followers

My Turn to Enjoy Another Man

Michael and I had been married for 20 years when I found out that he had been unfaithful. Even though I always suspected that this would happen, I asked for a divorce because our relationship was dead or dying. The first couple of weeks following our breakup were awful, as they always are, but I surprised myself at just how quickly I came to terms with the position I found myself in.

Truthfully, I did not miss Michael as much as I thought. We took the divorce proceedings very slowly, not wishing to bring any animosity into what had been a good friendship for so many years. In the meantime, our circle of friends rallied around me knowing that I was alone and they wanted to allow Michael to find some breathing space in his new relationship. His new partner was 10 years younger than him and I have to say that I struggled with her age and the feeling that I was washed up at the age of 50.

After a couple of months, I decided to take the plunge and took up the invites from our friends to parties and dinners. It felt odd being there without Michael but our friends were very hospitable. Several times they tried to fix me up with one of their single male neighbours but they just weren't my type and I wasn't ready for any sort of relationship at that time. After several months the invites stopped. I later found out that several of the husbands in our group had been indiscreet about me and their wives were concerned that I was attracting unhealthy levels of attention.

I had resigned myself to living quite a lonely singular life but in a way, I was happy about this. I was enjoying my newfound freedom, engaging a little bit of travel and other sedentary pastimes. The girls who I work with are much younger than me with some in their early 20s. Every Monday morning I would listen to their talk about the weekend and part of me envied them.

One day, Karen, my closest colleague, suggested that I go out with the girls to celebrate her birthday. I didn't really want to take the invite but I felt awkward for Karen's sake. I chose to drive that night and didn't drink any alcohol but the evening was better than I expected. The girls were such a friendly bunch but no matter how hard they tried I could never feel that I was one of them. What surprised me was that the young men who they attracted seemed to want to talk more to me. Even when I explained that I was much older than them, they would not be put off. They seemed to be more relaxed with me and less inclined to show off. I didn't think this was a problem at first until Karen approached and said that I was the talk of the gang because of the attention I had attracted all evening. It really meant nothing to me because I hadn't anticipated going out with the girls again but the following Friday, they asked me to join them just for a few drinks around the town. I instantly said no thank you but as Friday approached I persuaded myself that it wasn't such a bad option.

I don't know what got into me that Friday night but I began to felt feel very anxious and rang Karen a couple of times to say that I might have second thoughts about going out. Karen is an amazing girl and encouraged me just to come out and enjoy myself. I was unsure what to wear but all week I had passed a clothes store in the town where a display had taken my eye. In an impulse, I drove to the shop. There was an outfit in the window which used to remind me of when I was the same age as Karen. It was nothing special, just a short black woollen skirt but the blouse was really stunning. It was made from a see-through black material but around the bust and the collar the material was opaque.

I bought the outfit and feeling still slightly unconfident I passed a shoe shop and noticed some lovely black boots with shiny silver zips. The heels were far higher than I was used to wearing but I thought, 'what the hell. I might as well go the whole 9 yards and buy them too.'

When I got home, I grabbed a couple of drinks for courage and then got ready. The girls at work used to tease me because they were very keen to shave their pubic areas and I used to chastise them for being too vain. However, I decided it was better to adopt the attitude that if you can't beat them then join them and I shaved the whole of my pubic area.

Lingering in the bath, I giggled to myself about how silly I felt but the action of shaving aroused me more than I expected. I wasn't sure whether it was the alcohol or my changing mood but I began to feel more daring. I applied more makeup than I was used to and I decided to dress without any knickers.

Just before I left the house, I had a good look at myself in the mirror. I am lucky that I've still got a lovely slim figure and shapely breasts even though I generally cover them up with thick jumpers. As I looked in the mirror, I noticed that the tops of my holdups were only just showing so I pulled down my skirt. One last look the mirror and I was ready to go.

Karen and the girls were complimentary about how I looked. One of them jokingly said, 'We aren't going to get any attention tonight. AGAIN!.'

While everyone laughed, I think that this girl meant it and was just a little annoyed. After we went to a few pubs I felt that the night was just a waste of time. The girls weren't talking to me so I decided to go home early but Karen persuaded me to go to one last pub where I met my ex-husband's long term female friend, Janet. I had known Janet for over 20 years but she was very close to Michael. She told me that Michael's relationship with his young girlfriend had ended and that if I wanted, she was sure that Michael would be keen to resume our relationship.

I suspected that he was using her to communicate but I did not let on. Janet knew that she was pushing an open door. Michael had been a good husband and part of me felt that I should forgive him.

Janet asked if she could give me some more advice to which I agreed. She said that if I was inclined to start again with Michael, I should leave it a few months until after Christmas. He wasn't interested in other women and never had been until his affair so Janet thought that he needed time to steady himself and perhaps realise that resuming our relationship was still possible and desirable.

'But what am I going to do', I asked Janet. 'I'm just feeling in limbo and the thought of spending time on my own for several more months is starting to wear thin.'

'Do what I would do,' said Janet. 'Play the field'.

'Field', I exclaimed. 'Have you seen the balding fat men of my age who hang around in these bars.'

'No', said Janet. 'I'm too busy looking at the younger ones.'

Janet told me that when she broke up with her husband she had one of the best times of her life going out with much younger men.

'It's just fun,' she said. 'Don't get too serious. They're not going to marry you but in a way that's what attracts them. They know that you're not looking to settle down with them and just want fun, unlike the younger girls they often meet.'

At this point, a young guy came over to speak to Janet. His name was James and he was a contractor that used to work for Janet's company. I was embarrassed when Janet introduced me by saying 'This is my good friend Vicky and she is single.'

James had bought Janet a drink but she had to leave the bar early so she said to James, 'Vicky drinks the same as me so why not give it to her?' He agreed and after Janet left, we stood chatting for a while. James is 29 and just seemed like a regular guy. He was quite good looking and very muscular. After about half an hour, James' friends kept coming over and joking with him to leave me alone.

'Before you know, he'll be taking you back to his flat,' one of them said to which I answered, 'I don't think so. I'm old enough to be his mother.'

James then looked at me intently and said, 'That doesn't matter you are the best-looking woman in this bar by far and I fancy you regardless of your age.'

I recall blushing intensely at which point Karen came over and said the girls were moving to the bar next door. I said goodnight to James and thanked him for his drink.

Within a few moments of arriving at the bar next door, I received a tap on the shoulder and when I turned round I noticed it was James who was smiling at me. 'I'm not following you,' he said and, I don't know why, but I replied, 'Oh that's a shame'.

'Really? Well, my friends have gone home and I'm out alone. We can talk if you don't mind?' He said he was going to buy me a drink and as he moved past me, he placed his arm around my waist just on the upper part of my buttocks. I felt a tingle under his touch and I admit that I felt aroused.

Karen and the girls started to move around the bar talking to prospective boyfriends and left me alone with James. Even though it felt uncomfortable I was enjoying his attention. I fully explained my situation with Michael and he said he'd only just got over a relationship with his girlfriend, Louise, who didn't want to settle down with him. She'd even turned down his proposal of marriage and this had caused him to feel bitter towards her, although they tried to remain friends. After last orders had been rung James said that he had booked a taxi and that I could share it. It seemed a good idea because the girls were going onto the nightclub and I just didn't want to be there anymore. I agreed and we caught the taxi together. I don't know why I did it but when I got to my flat, I asked James if he fancied a coffee. At first, he seemed reticent and then said he would but the added that he would only be able to stay for about an hour because he was working the following day.

I was very nervous when I was making the coffee for James. He walked around admiring my flat, which is open plan. I felt that he was watching me closely and this made me even more anxious. I then felt his hand around my waist and I flinched. James apologised and said that he didn't mean to startle me. I said it was OK but that I was only taken unawares.

'Are you sure you're 50 years of age and not just kidding me,' asked James. I told him to stop this. He didn't have to say nice things to me yet over and again he kept saying that he meant his words.

I only had a two-seater sofa in my flat while I was waiting for my new furniture to arrive so we sat together. Our legs rubbed and there was a pleasant but nervous tension between us. When James went to leave, he kissed me on the lips and said that he hoped to see me in the bar again and that I shouldn't hide myself away. I watched him depart when he was collected by the taxi but my phone rang about 15 minutes later. I thought it would be Michael and then suddenly I heard James's voice. He asked if he'd left his wallet in the flat and I saw straight away this it was on my sofa. He hadn't any money to pay the taxi driver so he asked if he could return to my flat and pick up his wallet. I said of course and waited for him but after about half an hour there was no sign of him. I thought he wasn't going to come back so I took off my skirt and blouse and put on a comfy dressing gown over my hold ups.

Just as I lay on my bed, the intercom rang. It was James. He advised that the taxi would not bring him back and an argument had ensued over payment. The taxi had another booking so the driver reluctantly accepted that he could ring his office once he retrieved his wallet and could pay over the telephone. I did not want to go downstairs in my dressing gown so I asked James if he wanted to come up. When he came through the front door,he was shocked to see me in my bedclothes. 'God I'm freezing cold,' he said. 'I've walked nearly a mile in the rain and I'm wet through.'

I brought him a couple of towels and he asked if he could call the taxi office from my flat. I agreed and made him a cup of coffee to warm him up. James' jeans were wet through and as he sat on my cream sofa, I was concerned that the colour from the denim would leach into the material. He apologised and said he would sit on the floor but he was soaked and I said to him that it was okay to take off his jeans and I'd put them in the tumble dryer.

It was only after I was placing the garments in my tumble dryer that I realised how forward I had been. James had taken off his jeans quite coyly and handed them to me while I pretended to look away but I couldn't help noting he had on a pair of skimpy briefs.

I turned up the heating and Dan came to sit back next to me on the sofa. We started laughing at how ludicrous the whole scene was and I said, 'I bet you didn't expect to be sat half naked next to a woman old enough to be your mum.'

'Stop saying that,' he said. 'I don't think of you as anyone old enough to be my mum. You are just not like anyone of your age. You look and act so much younger.' I decided to take the compliment for a change and I admit that I was falling for him.

I made and excuse to go to the toilet just to get some head space. Looking in the mirror, I whispered under my breath 'What are you doing? Don't be so stupid. He won't fancy you.'

When I walked back into my living room, James was stood with his back turned. I noticed how muscular his legs were and he had a beautiful plump ass. He was staring into my gas fire, warming himself up and I approached him from behind. This time it was his turn to be startled. I asked him if he was alright and I placed my hand in the centre of his back. He wrapped his arm around my shoulder and pulled me close. We stood there for several moments, not saying a word before James then turned to me and kissed me on the cheek. I wasn't offended but I did turn my head slightly to avoid him kissing me on the lips. He said, 'Sorry I shouldn't have done that but I just couldn't help it.'

'It's ok,' I exclaimed. 'I'm just a little confused at the moment.'

We walked back to the sofa and sat closely next to each other. I was embarrassed because I noticed that my dressing gown had opened and the tops of my hold ups were again showing. It must have looked obvious to James but it was purely accidental. James reached over and curiously, he slowly pulled the dressing gown together but he left his hand on my thigh where it lingered. I placed my hand upon his with the intention of moving it but then I decided that he wasn't intending anything untoward and I simply held it there. How do these things occur? I found myself stroking my hand over James'. He then gently pulled my gown to one side to once again reveal my stocking tops. I did not resist. His fingers traced a line until they came to the flesh of my thighs. He hesitated a while and gently stroked my thigh.

'Oh God,' I said. 'We shouldn't be doing this.' I pulled my gown together again.

After a while James bent and placed his head against my breast. In the dim light and the warmth of the fire it was too easy for me to submit to him and I instinctively kissed him on the lips. To his (and my) surprise, I dipped the tip of my tongue into his mouth and gently circled it. I don't know why I did this, maybe just to tease him or maybe I was even teasing myself because I knew I wasn't going to submit to him. Yet the kisses became more passionate. James started to move his head and without using his hands he parted the top of my gown to bear my left breast. He moved his hand and pulled open the gown so as to expose my hard nipples. I could see he was aroused by the sight of my brown, erect nipple. He started suckling upon it in such a gentle manner that I gave in. I opened the other side of my gown and invited him to kiss my other breast, which he did so without a murmur.

All this time I questioned what I was doing but the dampness between my legs was giving away my feelings. In one quick motion, James left the sofa and bent down on his knees resting his head in my lap. He teased apart my gown and began to kiss and nibble at the bare flesh of my thighs. It was no good even pretending to resist because at that point I knew what was going to happen. I let him open my gown fully and his breathing grew heavy. I don't think he expected to see me without underwear and he gazed longingly at my shaved cunt.

James placed his strong arms underneath my thighs, parted by legs and exposed my vagina. His head went down and he began to suck, lick and penetrate my vagina with his tongue. I reached out and ran my hand over his shaved head. With my right hand, I circled my clitoris just above where James was continuing to suck and lick me. It was there, that feeling that I'm going to cum and I started to move my hips upwards towards him. James moved forward and started to kiss me deeply while his fingers penetrated my vagina. Occasionally he'd move his fingers out and with my juices still flowing over them, he circled my anus, sending me wild.

I closed my eyes to try and relax under his spell. He then pushed upwards again and I could feel the bulge beneath the thin material of his briefs pushing across my vagina and onto my clitoris. Waves of pleasure started to overcome me and at last I surrendered and place my hand under the waistband of his briefs. It felt so good to feel such a rigid cock. I pulled on his foreskin and felt a large quantity of precum flow around the tip of his penis.

James then turned his attention to kissing me on the neck, almost as if he knew that that was my one weak spot. My breathing grew rapid and I started to masturbate his cock. I felt his hands move and he pulled his briefs down. My hand slipped beneath his balls and I was surprised to find that these were hairless and that he was fully shaved. He was ready and I knew it. I knew that he wanted to enter me but I couldn't bring myself to allow that.

'Sorry', I whispered to James but I am not ready yet. He pushed the head of his cock against my opening so I instructed him to start wanking off but said, 'Don't come inside me.'

James looked me squarely in the eyes as he rapidly wanked his rigid cock. It didn't take long before his breathing became laboured and then rose in tempo as quickly as his hand moved over his penis. He placed his left arm underneath my right thigh and pulled me further forward towards him. This had the effect of raising up my cunt in expectation of what was to come. It all happened so quickly. He grunted and groaned as a thick mass of his cum shot out from his penis onto my naked vaginal lips. At the same time, I pushed my hand down across my clitoris and rubbed it vigorously. To my surprise, because I was always slow to orgasm, I came almost immediately and let out a cry at the same time. This seemed to encourage him even more and despite the fact there was no more cum shooting from his penis, he wanked it furiously.

I was exhausted and suddenly realised how I must have looked. My dressing gown was fully open, exposing my breasts and hard nipples. James had pulled apart and raised my legs so my vagina was completely exposed to him. It was covered in his sticky cum and I used this to lubricate my fingers. Suddenly I felt another wave of ecstasy overcoming me and I circled my clitoris with vigour until I came again, this time arching my back and letting out long and deep cry.

I think both of us must have been a little embarrassed because James stood up quite soon and pulled up his briefs. He said sorry but I said to him that he had no reason to be apologetic. I admitted to him that I had really enjoyed what had just happened and we kissed. Our lips didn't carry the same passions as before but were more loving.

For a while James rested in my arms partially asleep until he realised that it was the early hours of the morning and he had go home to get ready for work the following day. We walked to my front door where he kissed me again and this time James did not hold back. His hands swept across my bum cheeks and breasts, which he squeezed tightly. I told him to take care at which point he said, 'See you again?' I wasn't trying to play it cool, how could I when I was so much older than him, but I do recall saying something to the effect of, 'Let's just see shall we?'

Bisense
Bisense
42 Followers
Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
3 Comments
OnlyHappyEndingsOnlyHappyEndings4 months ago

This was very loving and romantic. Much different from some of your other stories. Not that I didn't enjoy those as well.

AnonymousAnonymous5 months ago

Who is Dan?

Toemmy28Toemmy285 months ago

Great story, I hope there's more to come.

Share this Story

Similar Stories

My Mom’s Best Friend Lucky nerd seduced by MILF at his parents’ Halloween party.in Mature
Dating Ellen -- My Best Friend's Mom Falling in love with my best friend's mother.in Mature
Fucking Her Friend's Son Serena bangs her best friend’s son.in Mature
A Friend's Dad A teen wants her friends hot dad.in Mature
Every Schoolboy's Dream Sex with MILF teacher + dating her hot cheerleader daughter.in Mature
More Stories