Discovering Online Dating

The following story is for entertainment purposes only and any similarity to persons living or dead is purely coincidental.

Hello, let me introduce myself, my name is Elaine and I live in Suffolk, I'm 46 years old and a widow. My husband died in an accident at work some 7 years ago. I was just 18 when I married and we quickly had 3 children who have now grown up and left home, so now I find myself living alone having only known the love of one man. Things have gotten increasingly difficult these past 7 years as my children found their own partners and moved on with their lives. I still see them and my grandchildren when they pop round to visit but I miss having a man around, someone to share the long nights with.

My daughter has suggested I join a dating site on the internet, claiming that I could spend my long lonely evenings just chatting with people on-line. She told me I can be very choosy, use an alias and chat to people without them ever actually knowing who I am, she said I could even get men to show me naughty things to help me have 'pleasant dreams' at night.

At first I was shocked that my daughter would suggest such a thing but over the following days I found myself more and more drawn to the idea until eventually I decided to give it a try. I searched the internet and found dozens of sites, it took some days of trial and error, getting to find a site which I felt comfortable with (browsing as a 'guest' to see some of what the sites offered). All of the sites seemed pretty much the same and so I bit the bullet and chose to join one of the sites using a name I felt comfortable with, 'NannaE'.

Filling in the profile for myself I decided to be completely honest, I could have pretended to be a young, sexy lass in her early twenties but felt that if I were to make friends with someone it would just ruin any trust, so brutal truth it had to be; Age, 46. Height 5ft 5. Hair, Shoulder length and currently a deep red. Eyes, Brown. Then it came to the 'body description'. I selected 'pleasantly plump' with 48" DD bust, a cake lover's tummy (but I'm trying to diet) and what I described as 'Motherly hips'.

Then I came to Profile Picture and the site suggested a full face pic with me holding something with my user-name plus the name of the site so that they could mark me as a 'verified member' they assured that this picture would not be posted on site, and for my profile picture I should post 'whatever I felt comfortable with, provided it didn't contravene the site rules.

So, selfie time, I made out the card as required and then took a selfie to submit, I then had to browse all my other photos to find something I could use for my profile that was recent. I eventually decided on one which my son-in-law had taken earlier this summer when we were all on holiday in Spain, sitting at a table in my bathing costume wearing a wide brimmed hat, sunglasses and sipping sangria from a big glass. I was a little nervous about how much of my breasts were on display but at least nobody would be able to clearly see my face.

Finally satisfied with my profile I then submitted for approval and publication. I then had to fill in the 'about yourself' section where you tell things about yourself and what you are looking for on the site. In that I explained that I am a widow and that I am just looking for friends to chat to and that I expected people to be respectful, warning that anyone who was crude or attempted to send smut would be blocked and reported.

When I went on line again later that day I found my profile had been approved and I already had over fifty messages. Over half of the messages were from crude men sending pictures of themselves naked and saying what they wanted to do to me. I deleted and blocked every one of those men after reading their messages and looking at their photos (hey, I'm still a woman with needs and there is no harm in looking). There were even two messages from 'other women' whom I soon deduced were actually men pretending to be women. I have no idea where they thought they would get with that pretence but they too got deleted and blocked. Checking the messages and profiles of the remaining 'candidates' it was obvious that some simply didn't appeal to me, some seemed to be boring and some seemed to be so up themselves I just simply didn't want to know.

I eventually began to converse with just three of those who had contacted me so far, there was Clive, 63 from Windsor, a tall retired gentleman with a neat moustache and posing with a silver-topped cane. He was very much the old-fashioned gentleman and I enjoyed chatting with him but deep down I kinda knew he was 'too old'. Yes, I know age shouldn't matter if all I'm wanting is a friend to chat to - but be fair - who actually puts on those profiles what they are actually hoping to find?

Then there was Paul, 52 from Cambridge who claimed to be a freelance physical education teacher and I don't mind admitting he looked quite a hunk. His chat was nice and easy, relaxed. He would compliment without being over-the-top and he seemed to be able to make me laugh and feel comfortable even though sometimes his comments were a little risque, I found it very easy to flirt with him.

Last, but by no means least was Trev, 23 from York and a full-time university student. Probably a bit young for me but he was 100% a looker and his attention was a massive boost for my ego. I found myself having naughty thoughts while chatting with him, I would get quite moist if you know what I mean.

So I began chatting with these three guys on a daily basis, just getting to know them and it wasn't long before all three were starting to ask to meet me in person. Trev wanted me to go up to York to 'see his digs' and the historical town. Clive suggested I go to see him in Windsor then he could take me into the capitol to take in a west end show. Paul though was different, he suggested that he would travel to my town and meet me at a place of my choosing so that I would 'feel safe'. I was warming to Paul more and more though I didn't give a definite yes or no to any of them - just a series of maybe's once I got to know them better.

So the correspondence continued and as we got to know each other our messages began to get more flirty and sexual, all three wanted to know if I had more pictures, they were all very careful to avoid asking outright for naughty pictures but it was quite obvious to me that it was those sort of pictures that they wanted to see. I continued to chat and tease and would send them occasional pictures, always fully clothed but maybe showing just a hint of something more until one day after having a very horny dream I woke at 3 feeling very flushed and horny - I sent all three of them the same four word message "Show me your cock" along with a single picture of my naked breasts then tried to get back to sleep, laying naked in my lonely bed playing with myself, using my friendly plastic rabbit to ease the ache I felt.

I must have dozed off again at some point and when I awoke later that morning I was horrified when I remembered what I had done. I simply couldn't face checking my emails as I usually would, I busied myself finding jobs to keep me occupied, changing the bed, putting on the washing, hoovering around the house, I even got around to doing the dusting in every room (that in itself is a rarity if I'm being honest). But eventually, around mid afternoon after a late lunch I nervously booted up my computer and clicked on my emails. Sure enough there were three emails waiting for me, each with attachments (Oh God, what have I done?)

Before going any further I went back into the kitchen and made myself a strong cup of coffee to soothe my nerves then, once I was sitting comfortably I looked at those three emails waiting to be opened. I looked at the times they were sent, all three showed that they were sent before 8 o'clock, three little envelopes waiting for me to click on them and view the responses. I admonished myself "Oh for heaven's sake Elaine, stop dithering and just look at the bloody things!"

I clicked on the first one, from Clive. He thanked me for placing my trust in him and promised to always keep my picture private, he then went on to wax lyrical over my breasts telling me how wonderful he thought they were and ending with the line ' see the enclosed attachment for what I would like to place between those breasts'. Chuckling to myself I clicked on the picture attachment and there it was, his hard cock, it looked quite big though there was nothing to give a perspective, I could see a few grey pubes but I have to admit it made me start to get moist and have naughty thoughts again, thinking back to days long gone when my husband would use my breasts to pleasure himself on the occasions that 'downstairs' was out of bounds.

I then clicked on Paul's response, he, like Clive, thanked me for the picture and said that he would just love to take me in his arms, kiss my lips, neck and on down to my breasts which he said he wanted to gently kiss and tease, drawing my nipples into his mouth. He sure has a way with words and I found myself touching myself and wanting to feel his kisses. I opened the attachment and Oh Boy!! He had sent a full frontal nude in high resolution. He stood naked and proud in a gym, surrounded by all manner of exercise equipment, his whole frame was one of toned muscle without being 'over the top' and his Cock! My God his cock was Huge! It stood erect and I could hardly tear my eyes away - I was beginning to think to myself, 'it's been so long, I so need to feel the pleasure of a man again'. I think it was at that moment that I decided that I definitely wanted to meet Paul.

I reluctantly closed the picture and went on to the last email, the one from Trev. I clicked on that innocent little envelope and his message appeared on my screen:-

"Oh wow Elaine! That's some great tits you have there! I can't wait to have you come visit me so I can suck on those huge tits and fuck your sweet pussy. Is it wet now? Do you long to have my hard young cock deep inside you? Make it happen soon, I'm so horny for you." I clicked on the attachment and his picture opened, again he seemed to have a good long cock, it looked a little slim but it had a slight upturn at the end. I couldn't help but think that it would feel good slipping deep inside, but then, wait!! Elaine? He knows my name is Elaine? How in heaven's name could he possibly know my name?

In a state of near panic I clicked reply to sender. Just one single sentence. How did you find out my name? Then I clicked 'send'.

I needed another drink, something a bit stronger than coffee. I got myself a bottle of wine and just sat there in a daze. Halfway down my third glass the email pinged, new message, a reply from Trev. I immediately opened it.

"Don't panic Mrs Lovett. When you sent me that wonderful picture of your naked breasts you did so from your personal email, perhaps you didn't realise that your personal email discloses your name? Armed with that little piece of information it was a simple matter for me to use the university internet access to find your electoral register entry. So I know your full name, birthdate, address and I also know that you live alone at that address. I might have to pop down your way after term and have some naughty fun with you. You could pretend you've taken in a lodger and then I could fuck you every day. Would you like that Elaine? Having your sweet pussy fucked by a virile young cock over and over? P.S. Please send me more pics, I want to see your pussy xxxx. PPS. Please don't worry, your details are safe with me, I won't let anyone know.

I just sat there in a daze staring at the screen. Dammit, how could I have been so stupid? Another couple of glasses of wine later I was still staring at that message, my heart was pounding in my chest but I was starting to feel very horny as my brain started to imagine sharing my house with a young 'lodger', making my morning breakfast and my lodger walks in and just takes me over the kitchen table, or perhaps walks in on me taking a shower and fucks me up against the wall with the shower cascading over our bodies, or he sneaks into my bedroom at night and ties me to the bed and then has his wicked way with me.

Damn my imagination! Now I was sitting in front of my pc, touching myself and getting so very wet and horny. Well damn you Trev! I decided to call his bluff. I quickly shaved myself 'down there' and then took some pics of my smooth pussy, one with my pussy held open showing how wet it was, then I took one, full frontal, standing in front of my mirror. Then I sent the whole lot off to Trev with the message "Think you can handle this big boy?"

Then I just sat there contemplating what had just happened, what I had just done. I knew it was stupid, I knew I shouldn't have reacted as I had - and yet - I felt so alive, sort of tingling with anticipation. I don't know what had happened to my common sense because I then started thinking that I was being unfair to Clive and Paul and I was feeling so incredibly horny that I just had this urge to show myself off. So yes, I sent exactly the same pictures to both Clive and Paul with the same message "Think you can handle this big boy?"

I got no responses from anyone for simply ages, eventually rational told me that its Tuesday afternoon, all three guys would be going about their daily business probably wouldn't be on line until later in the evening. I got myself properly dressed and went out to do my bits of shopping, intending to potter about in the garden later on, I loved my garden and found it so relaxing, weeding, pruning and at times just snoozing in my garden lounger. Today though, once I had done my normal little bit of shopping I popped into the local Ann Summers and treated myself to a few little bits of naughty lingerie. I wanted to look good as well as feel good, I was starting to enjoy this new, daring to be sexy, me. I also treated myself to new make-up and perfume. I was trying to shake off the frumpy old widow woman image and create a new and vibrant, sensual woman. Time would tell if I was successful.

I eventually got back home around 7 in the evening. I had bought myself a nice Indian take-away which I devoured while watching TV. Feeling pleasantly full and relaxed I then got ready for bed. I wore my brand new crotchless teddy and over that I slipped on my new shortie silk gown. I then went back to my pc, booted up and checked for emails. Feeling nervous but also excited and aroused I selected Clive's email to look at first.

"My word, that was a pleasant surprise opening those picture files you sent me. When I first started chatting with you I never dreamed that you'd turn out to be a horny, cock-hungry slut. I think we had better meet up soon and then I'll show you just how well I can handle a slut like yourself. I can't keep calling you NannaE any more, what is your real name? (I hope you enjoy the enclosed pictures) I clicked on the attachments and when the pictures opened before my eyes I was astonished to see my 'gentleman Clive' holding some naked woman by her hair and forcing his cock into her mouth. I should have been offended but all I could think was 'I wish that was me'.

I decided to respond to him immediately. You naughty man, Clive. Here I thought you were a true gentleman and yet you appear to have a dominant side. Do you always force your ladies to suck your hard cock? I guess you don't always take a lady out to catch a west-end show then? My name is Elaine. Who was the lucky lady in your picture? As for me being a 'cock hungry slut' as you called me. If I'm cock hungry then that's because I haven't had one for 7 years. By the same logic that would preclude me from being a 'slut'. Though the idea is tempting. I clicked on send and then went on to my next message.

The next message was from Paul and he simply said 'Oh wow! I would consider myself truly blessed to be allowed to handle that. You should see the raging boner you've just given me! Changing the subject slightly. My current contract with the university fitness studio is approaching it's end and I have applied to fill a place over in Ipswich. I have an interview this coming Friday so I'm travelling over on Thursday. I shall be staying at the Mermaid hotel and I was kinda hoping I could meet you somewhere for a coffee perhaps. I'm coming over by bus and was sort of hoping you might be able to show me around?

My heart was pounding, he would be here the day after tomorrow? What should I do? Should I meet him? Dare I meet him? I sat for ages pondering these questions but when it came down to it I had to admit to myself that I actually quite fancied him and would like to meet him but I vowed to keep to well populated areas so I would be safe from any unwanted advances. I tried to make my response appear casual. 'I'm sure I could meet you, what time will your bus arrive? There are plenty of coffee shops in the town where we could go for a chat. I look forward to seeing you. Regards, Elaine.' I kept the message very short and to the point so as not to reveal how nervous (and horny) I was actually feeling and ended the message of course, with my real name.

The third message was another one from Trev. 'Hi again Elaine, just thinking, end of term is in just three weeks. Would you like me to buy you a train ticket to come visit me or would you prefer me to come down there and be your horny young lodger? The choice is yours, my sexy MILF. My young, hard cock is longing to pleasure you, let me know what you want a.s.a.p. Xxxx

I chuckled to myself, I couldn't have him turning up on the doorstep here. I've never been to York so perhaps I should let him pay for me and in return I'll fuck his brains out and then he might move on to his next conquest and leave me alone. I replied immediately. 'OK Trev, get me an open return train ticket and a nice hotel to stay at (I'm not going to stay at some smelly student digs) and I shall come up to York and drain you dry xxxx

I noticed then that I had continued to get messages from the dating site, they had all been going to my spam folder and when I looked there was page after page of them, there must have been hundreds. To be fair to everyone I went onto the site and suspended my account until further notice. Once I had done that I saw that Paul had replied again. He said his bus would arrive at about mid-day on Thursday and he was looking forward to meeting me. I was a bag of nerves already! I retired to bed and tried to sleep.

Wednesday morning saw me very busy adding a little colour to my hair (I didn't want Paul seeing grey roots on our first meeting). I then epilated arms, legs and my 'lady garden'. Eventually I was as smooth as a babies bottom and oh so pink so now I gave myself a gentle 'fake tan' treatment, nothing too severe that would look orange or leave obvious 'tide marks'. By the time I was finished I was really proud of the results (so much so that I took a few selfies, naked ones.) The rest of Wednesday was spent experimenting with clothes and make-up. Men have no idea the time we spend just making ourselves look good for them!

Then suddenly it was Thursday already and I was up, getting ready by 6am. I did my hair, applied my make-up then came the 'getting dressed' bit. I wanted to look sexy and appealing without looking cheap and trashy. First came the underwear and I decided on a matching half-cup balcony bra and crotchless panties in a soft, pale blue. If the day got so 'hot' that he got to see the underwear I wouldn't care if it looked trashy. I decided on a white loose fitting button front top, see through but with silk embroidered patterns helping to hide my breasts, I left the top three buttons undone to show my generous cleavage. My skirt was cut just above the knee with a slit at the side in what I call a secretary grey. I was toying with stockings or tights and decided on shiny, satin finish 'hold-ups' and finally sensible, low heel black shoes (comfortable for driving and walking). A good application of perfume and I was 'good-to-go'.