My New Life

Loneliness is something that has followed me throughout my life and it's something that I've simply learned to live with. Even at school I was isolated and seen as 'different' because I had a natural curiosity about life and wanted to do well so homework was always done on time and done to the best of my ability. I was top of the class in most subjects with an IQ of 156 and I soon discovered that boys just didn't like this sort of ability in a girl. They seemed very immature to me and I reasoned that a relationship would only be possible for me once they had grown up enough to appreciate me as an intelligent and independent woman.

Obviously it turned out grown men aren't naturally drawn towards these qualities either! It might have been different if I was 'hot' but I was aptly named Jayne Evans by my parents as I was every inch a 'plain Jane'. It's not that I've ever been ugly, fat or anything like that but I've equally never had any feature that would make me stand out to men. I'm a size 14 so I don't stand out as particularly big but I could stand to lose a few pounds and it certainly means I don't have the slim figure that men seem to love. My breasts are a good size at 38E and have stayed reasonably firm for a woman now in her late fifties but my overall size meant that they have never particularly stood out to a man. I've never been particularly pretty and I've always been so focused on my work and my career that I've never really bothered much with make-up, hairstyles or clothes. The overall result is that I tend to blend into the background and I think that's the worst fate of all for a 'plain Jane' like me because life can be very boring without ever being obviously bad.

I worked as an accountant for a top firm in London and I earned a very good living, allowing me to retire a few years ago but I'd never risen to the heights my intelligence and ability warranted because those in charge were men and they either promote their own or they promote the beautiful women who would project the right image of the company. That wasn't me so having been passed over for promotion yet again, I eventually decided to call it a day and took early retirement. I could survive financially if I was prudent and turning my back on London, I moved to Norfolk where I lived on a luxurious wide-beamed narrowboat moored in a tranquil area of great natural beauty. Life was peaceful and pleasant but also quite lonely.

It was a sunny summer's morning in July and I was lying in bed wondering what I would do to fill my day. The gentle undulations of the boat on the river were relaxing and my thoughts drifted to how nice it would be to share this beautiful morning with a special man in my life; a man who would make me feel special instead of plain and want to make love to me instead of ignore me. Since my retirement, it's fair to say that I'd been thinking a lot more about men! I'd been on a few dates over the years but nothing had ever really come of them other than dinner and a few kisses so here I was, a lonely spinster who was embarrassingly still a virgin. My career had meant that I didn't really stop to think of men and sex too much but now that I was retired and on my own, I was acutely aware that time was running out. I didn't feel I needed to be married anymore as I'd grown accustomed to my independence but I did long for some intimate physical contact with a man, if only to see what it was like!

I closed my eyes and allowed my hands to wander from my breasts, down between my legs and imagined it was a lover who actually wanted me. The area between my legs tingled at the thought but it was difficult to imagine just what it would be like with no actual experience. I'd seen couples have sex on TV and in films before and I'd seen pictures of naked men that certainly aroused me but I was sure that reality would be very different. Sadly, all my vagina had ever known was my own fingers or a modestly sized vibrator that didn't honestly feel very life-like to me. As pleasant as it could be, I was sure a man would feel a lot better. Unfortunately, at my age that was never likely to happen.

Eventually dragging myself out of bed, I decided to go for a walk along the river. I'd gone about half a mile when I passed another narrowboat moored to the riverbank. I'd seen it quite a few times before and chatted casually to the owner, who was a friendly guy called Scott. I never had a strong sense of any attraction to me but I'd never really sensed that from any man. Nevertheless, we did seem to get on well and the conversation was always warm and easy. He was in his mid-forties and quite a good looking guy without being in any way spectacular. Like me he carried a few extra pounds, as you might expect in middle-age but generally speaking he had a good body that looked firm and muscular. He'd been married but lost his wife a few years ago in a car accident and had been living on this narrowboat ever since.

I decided to go over and say good morning if he was around, though there was no sign of activity on board. The curtains appeared to still be closed so it seemed he was having a lie in but just as I was about to give up and move on, I noticed a gap in the curtains. I should have just passed by but who doesn't take a quick peek out of curiosity in such a moment? Scott was lying in bed with his eyes closed and the covers only up as far as his navel, exposing his firm and slightly hairy chest. As nice as that was for a frustrated older woman like me, what really attracted my attention was the fact that judging by the movement of the bedclothes, he was masturbating and getting close to orgasm.

Everything told me to hurry away before I was spotted but I was transfixed by what I was seeing and I hoped that at some point he would remove the covers altogether so I might see his erection. With such a barren sex life, I longed to just see a man's erection in the flesh. Unfortunately that didn't happen and I merely heard him moan as he climaxed into the sheets. It looked to be an intense experience for him and I was starting to breathe heavily myself as I imagined him cumming in me. The combination of the sheets and his movement made it difficult to determine much but my impression was that Scott was handling some decent equipment under those sheets and I wished it was at least my hand on his equipment instead of his.

Knowing he would probably be getting up now, I quickly sneaked away and returned to my own boat before I could be discovered. In one sense I was mortified by what I'd seen but I was also thrilled at seeing a man is such a state of arousal. It had never occurred to me that Scott would ever need to masturbate but now I thought about it, I'd never seen him with any sort of female company and he was certainly still young enough to have a normal male sex drive. That would be difficult to satisfy if he was never going out to meet women. This thought fired my imagination and I started to fantasize about Scott finding comfort with me. I knew it was unrealistic to expect a man in his mid-forties to be interested in me but then if it was really possible, it wouldn't be a fantasy.

I spent the rest of the morning in my own bed, using my hands and imagination to give me some sense of the pleasure I was sure Scott could give me. Closing my eyes I imagined the slightly rough texture of the stubble on his chin, his hands roaming over my body and his erection in my hand and finally in my desperate body. It was a lovely way to spend a relaxing day but ultimately it could never be entirely fulfilling.

Days passed and I kept coming back to my fantasy but I couldn't help concluding that it was nothing but a ridiculous dream. As it happened, fate was able to give me a prod in the right direction. It had been a few days since I saw Scott masturbating and I was sitting on top of my boat, enjoying the warm summer sun when I heard a boat approaching from behind. It was Scott and my immediate instinct was to get out of sight but it was too late.

'Hi Jayne, how are things?' he called cheerfully.

'Perfect with this weather, thanks' I replied as casually as I could muster. 'It's good to see you again.' I could feel myself blushing at my unfortunate phrasing but he didn't notice. 'Where are you going?

'I'm heading up to Cromer for a few days, just for a change of scene but I'll be back before long. I prefer the peace and quiet we have here.'

'Me too' I agreed, wanting to say more but unsure exactly what it was that I could say in a conversation that was nothing but small talk. Flirty small talk wasn't exactly my forte given my lack of experience with men.

'Why don't you come over when I return and I'll cook you dinner' he said cheerfully. 'As we live so close to each other and in such a remote area, it's about time we got to know each other better.'

His generous offer was a surprise and I had mixed feelings about the whole thing. He did seem like a nice guy and getting to know him better, especially given my little fantasy, wouldn't be the worst thing in the world but he was right that this was a remote area so how safe would I be with a relative stranger?

'That would be lovely, thank you' I replied before I even realised what I'd said. It was a spur of the moment decision that caught me by surprise but it was said so I had little choice to go through with it.

'Should we make it Saturday evening as I'll be back late on Friday afternoon?'

'Perfect, I'll see you then and have a safe trip.'

With a parting wave, Scott disappeared up the river and I was left to reflect on what I'd done. Initially I concentrated exclusively on the wisdom of accepting his offer. I kept telling myself that I was being silly and he was a genuinely nice man who had never come across as anything but a perfect gentleman but fear also kept nagging away at the back of my mind. Lying in bed over the coming nights I pushed such thoughts from my mind and instead focused on my fantasy. The whole thing still seemed highly improbable at best given that I wasn't in any way beautiful and I was quite a bit older than him but I reasoned that even if that was all true, there was nothing to stop me fantasising about what it would be like to finally have a man make love to me.

For the purposes of my fantasy, I kept telling myself that Scott was clearly in need of some physical contact with a woman and he appeared to be doing nothing to meet this need. He also lived in a quiet and remote spot so if he wasn't going out, his options were extremely limited and that might mean he would even consider a plain Jane like me. In years gone by I wouldn't have considered a relationship with a man that was based purely on sex because I wanted a proper relationship and that was one of the main reasons I was still a virgin but times change. More recently I had become content that I didn't want a 'relationship' with a man but I did want to experience sex. The problem was that life never seemed to present me with adequate possibilities.

It was getting late on Friday with no sign of Scott's return and I was just beginning to give up when I finally heard the deep chugging of his engine in the distance. Quickly I fixed my hair and put on a pair of shorts that were unusually feminine and revealing for me. A tight fitting t-shirt completed my hasty outfit and I rushed up on deck to greet him back.

'Hi Scott, how was your trip?' I called as casually as I could.

'It was fine but it's good to be back. Are we still on for dinner tomorrow?'

'Absolutely, if you still want to waste your Saturday night on an old woman like me' I joked.

'I think I could do a lot worse Jayne,' he laughed, 'I've been looking forward to it all week.'

It was a brief exchange before he was gone again but one that held great significance for me. He'd been thinking about our dinner date and he said he could do worse than me so although it was a joke, perhaps it gave a hint that he might at least be partially attracted to me. Having dinner with Scott certainly didn't mean anything would happen and I doubted it would. I would certainly be too embarrassed to be too forward with him but perhaps I could drop a few hints and see if he responded in any way. I'm sure most women would simply have piled on the make-up and worn some sexy clothes but that simply wasn't 'me' and I was sure such clothing would look completely out of place on a woman in her late fifties living on a narrowboat.

All day on Saturday I dithered about what I should wear when I went to Scott's. For a while I tried to indulge my fantasy but sense eventually dawned and I concluded that the chances of Scott being genuinely interested in me were too remote to seriously contemplate. No other man had been seriously interested so why should Scott be any different? Even if he was, I was a woman rapidly hurtling towards 60 with barely any sexual experience so I was far from sure how I'd react even if he did make an advance. It seemed safer to stick with what I knew best so I arrived at Scott's with no make-up and in sensible shoes, a cardigan from Marks & Spencer and a skirt to below the knee. I can't deny that I certainly looked my age!

Answering my call when I arrived at his boat, Scott came out to offer me a warm welcome. He kissed me on the cheek, as men do on these occasions, and helped me on board. His clothes looked of good quality and comprised of dark blue chinos and a beautifully woven pink shirt. I liked a man in pink as it suggested he was totally comfortable with his sexuality and had a degree of self-confidence. I wasn't sure what aftershave he was wearing but it had a distinctly masculine aroma and seemed to suit both Scott and our rural surroundings. Things are always a bit cramped on a narrowboat but he had arranged things very nicely and the dining/lounge area where we sat was perfectly comfortable. A lovely bottle of Chablis was already chilled and he quickly poured me a glass and made a toast to developing friendships. I must say that I was impressed. He seemed to be a man of excellent taste and manners so it was easy for me to relax in his company.

We talked about endless things as I told him about my work, early retirement and the contrast of life in Norfolk compared to the city. In turn, he told me of his work as a freelance writer and his wife. Naturally I expressed my condolences for his loss and he accepted the sentiment graciously.

'Have you never wanted another woman in your life?' I enquired.

'At first, certainly not,' he replied, 'but time has a great way of healing and now I'm less sure. I miss my wife and always will but I don't think she'd want me to spend the rest of my life alone and without female companionship.'

'So do you have another woman in your life now?' I asked, hesitantly, not wanting to cause offence with my question.

He paused for a moment, as if trying to think carefully about his phrasing.

'Perhaps, Hopefully at least anyway,' he eventually replied with a slight grin.

Before I knew what had happened, it was 10.00pm and I'd enjoyed quite a bit of wine with my meal so I was feeling a little lightheaded. I've never been a heavy drinker so I felt completely out of my depth and got up to leave. Scott immediately stood up and expressed his disappointment that I was leaving as he was enjoying my company. I felt a certain sadness too but it was getting late and I didn't feel it was entirely appropriate to stay so late at Scott's place, even if there was nobody around to see us or pass judgement. Standing right in front of me and very close, Scott looked at me intently for a second.

'You're a very special woman Jayne; I wish you could stay longer'

With that, he put his arms around me and I thought he was just giving me a hug to say goodnight and another kiss on the cheek. Instead, he held me far more closely and before I knew it, he was kissing me on my lips. I was absolutely stunned but after a moment's hesitation, I relaxed into his embrace and responded to his kissing by slightly parting my lips. I'm unsure how long this kiss lasted but it wasn't rushed and as our lips parted, my heart was pounding.

'Scott... I... what are you doing?' I stammered incoherently.

'I'm sorry Jayne,' he quickly replied, 'I didn't want to startle you but somehow, kissing you just seemed like the right thing to do.'

'But... But I'm so much older than you and certainly nothing to look at,' I protested.

'You are to me,' and with that he kissed me again and as we kissed, I was guided back to his sofa.

This time I responded a bit more and allowed him to continue kissing me. It felt good to have my arms around his broad shoulders and feel him holding me tightly. We kissed for a while like that and I had no idea what I was supposed to do next so I did nothing, deciding instead to just see what happened. After a few minutes of our kissing, which I confess was making me quite wet, his hand dropped to my breasts and he started to fondle them and squeeze them through my clothing. It felt good and I wanted him to continue but again, I had very little idea what I should do.

Slowly he started to unbutton my cardigan and then my blouse until there was only my bra separating him from my flesh. He seemed to pause for a while, as if he was unsure how to proceed, probably because I was so tense that I wasn't really responding as he might have expected. Eventually he decided to take another step and as he reached around my back, he expertly flicked my bra strap and before I knew it, my bra was undone and his hands were cupping my breasts. It felt so good to feel his hands on my bare skin, massaging my breasts and playing with my nipples. They were like bullets and yearned for his attention but just as I was getting used to this sensation and coming to terms with the wetness between my legs, his hand moved between my thighs and I could feel his fingers touching my wetness.

This was all going so fast! There was no doubt I was receptive to his touch and I knew I wanted more but I also had the powerful feeling that I was out of control. More than anything, I became acutely aware of my own lack of experience and I was afraid that I would either embarrass myself by doing something wrong or I'd be so inexperienced that he would find it a totally underwhelming experience making love to me. I'm not sure which possibility worried me more but I was suddenly struck with a feeling of blind panic. In my confused state I pushed him off me while shouting at him to leave me alone and keep his dirty hands to himself. Holding my clothes together to protect some of my dignity, I rushed home as quickly as I could, leaving Scott with a very confused look on his face.

Once back in the safety of my own boat, I burst into tears at the tragedy that was my life. I'd longed to be intimate with a man and even fantasised about Scott yet just when it looked like my fantasy would come true, my fear of embarrassment at being found out as an old virgin led me to ruin my one chance to change the situation. I was also acutely aware that this was desperately unfair on Scott as he had done absolutely nothing wrong yet I'd acted like he was a rapist.

When I awoke the next morning, my first thought was of how different things could have been if I'd been more sensible. I may now have lost my virginity and I could be waking up next to the man who had finally taken my cherry. What a fool I'd been! Suddenly I heard a knock on the side of my boat:

'Hello? ... Jayne? ...Are you there?'

I cowered in my bed, drawing the sheets up around me and hardly daring to breathe for fear he'd hear me.

'I know you're there Jayne. I just wanted to say how sorry I am about last night. I honestly hadn't meant to upset you and I'm mortified that I didn't realise you weren't interested. Please believe me that I would never do anything to hurt you or upset you.'