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Playing Daddy

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A new life after retirement and bereavement.
13.5k words
4.76
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Part 1 of the 4 part series

Updated 06/12/2023
Created 02/01/2020
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When I retired I had my future and that of my wife all planned out, but of course things never work out that way do they. I had retired at age fifty five, I had sold my business for a goodly sum, that and my pension scheme made our financial future secure, we were all set to travel for a couple of years and then settle down, taking two or three holidays a year.

Well, it didn't happen. On only our third month of traveling my dear wife became ill, her illness didn't last too long, mercifully, but then I found myself on my own. I couldn't bear to live in the house that we had called home for so long so I sold up and bought a small single story house on the coast. The house was small enough for me to manage on my own but still had decent sized rooms and one spare bedroom in case one of my children and their partner came to visit. Besides being a new start for me, the benefits of my new home were a large private garden, and a small pool, not overlooked by any neighbouring property.

My new closest neighbours were a family of four, Mr and Mrs May and their two daughters, Rachel I thought aged about eighteen, and her young sister Rebecca, aged between five and seven. They seemed a nice family, and when I moved in Mrs May came over and welcomed me to the neighbourhood, bringing me a bottle of wine and an invitation to call on them for anything I might need help with.

I have two sons, and they both encouraged me to continue with my plans to travel a bit, take trips to places I'd never been before, see the world as they put it. But, I didn't find it that pleasant travelling on my own, so after a year or so, and a couple of trips I sort of became a bit house bound, I just couldn't be bothered to go places on my own.

My wife and I had always enjoyed a healthy sex life, we had experimented a bit, tried new things, and had few if any inhibitions. I missed that part of my life particularly, so I was inevitably drawn to porn, and then I discovered cam sites. I started to receive dozens, if not hundreds, of unsolicited advertisements for even more porn, and dating sites. They were driving me crazy until one of my sons advised me to get a virtual private network, a few dollars a year and all the unwanted rubbish ceased to be a problem.

I discovered another benefit of a VPN, before having it certain areas of the country were blocked from my ability to view them on the cam sites, going on the internet via the VPN, made those areas viewable.

I was flicking through one of my 'go to' cam sites one evening when a particularly pretty girl caught my eye, there was just something about her that made me stop 'In her room' and look twice. She was quite heavily made up, and her hair appeared to be carefully managed to cover half her face, a subtle but fairly effective way of masking her. Nevertheless, I knew that I had seen her somewhere before.

I wasn't sure that I would remember where I had seen her, but I bookmarked her and hit the 'follow' button before turning off my computer for the evening. Under other circumstances I might have watched for longer, perhaps have sent her a tip of tokens, but I didn't have any for that particular site that evening and I was tired and ready to retire to my bed. Still it niggled me that I couldn't place where I had seen the girl before.

The following day I went for a walk along the beach, it made me reflect upon my life, watching the young girls (young to me anyway) running along in their bikinis, being chased into the ocean by equally young men. It was while I was in that wistful mood that Rachel from the house next to mine went running past and after a quick hello told me that her parents had asked her to invite me for dinner that evening, along with one or two other neighbours. I had met a couple of my other more distant neighbours before I had left on my last trip, but I didn't really know any of them. Our neighbourhood is quite exclusive, most of the properties are quite large and having ocean views are also in a high price bracket. Most of the owners are on the wealthy side of rich, I had been fortunate to get my place at what I considered a reasonable price, basically because it had needed a little work to bring it up to scratch, the vast majority of which I had done myself.

That evening I met a few more of my neighbours, and became on first name terms with Paul and Angela, formerly known as Mr and Mrs May. I also learned that Rachel was actually twenty-three years old and not the older sister of Rebecca, but her mother. I didn't intrude and ask questions, but some of the other guests let it slip that Rachel had gone off to college and come home for her first semester break, pregnant.

They nearly all seemed to concentrate on the way that Paul and Angela had taken to Rebecca so much, and hadn't seen fit to kick Rachel out. For so called 'friends and neighbours ' they didn't seem that friendly as far as I could see, just downright bitchy.

As I was chatting with Rachel later in the evening, just before I was about to leave, I had a feeling of Deja vu, the make-up was different, but her voice triggered memories of the previous evening, no, surely not!

Daddy's Girl 1234 didn't put in an appearance for the rest of that week, and when I checked her bio page it informed me that she lived in my local state, and was indeed twenty three years old. There were several videos of her available so I purchased one and after watching her use a very large vibrator on herself for twenty minutes I still couldn't decide if I really recognised her or not. Still, it was worth the purchase, that girl was a serious turn on, and I jerked off several times in one evening watching her.

It was almost two weeks before I got that notification email telling me that Daddy's girl was online. I had seen and briefly chatted with Rachel a few times during the previous two weeks, so when I logged on I was in little doubt that I was looking at my next door neighbour! Again she was heavily made up, but even with her hair covering half her face, I was sure it was Rachel.

I joined in the conversation but kept my knowledge to myself as I saw that sweet young lady from next door strip off her clothes and tease her audience. I watched in rapt attention as she first fingered herself and then used various sized dildos to produce what she advertised as a 'cum show'. And she did cum, several times from what I could see. I tipped her heavily, which elicited a thank you, not only verbally but in a short private message. Again, I didn't let her know either who I was or that I was aware of who she was.

I was rather surprised to see that her show at this point was not over, she was about to actually shock me. I had always considered myself to be a man of the world, I thought that I was experienced in life, and I thought in sexual matters, I was wrong. I watched in amazement as Rachel (as I now thought of her) started to deeply penetrate herself with her fingers. She started with just two, but within a few minutes she was inserting almost her whole hand into her vagina. It seemed many of her viewers were pushing her to go to extremes, as the token count went up she did more and more extreme penetrations, at one point pushing her whole hand, up to her wrist, inside her vagina. I had Never seen anything like this before, and as I tipped her more tokens I was forced to suggest that she stop before she hurt herself!

My messages to her were, as I understand, private because they were attached to tips, she replied in private message mode. She thanked me for my concern, but assured me that she was in no way hurting herself, but if I wanted to see her hurt herself I should stay tuned in!

When she took up a wooden 'paddle' and began beating herself with it to the sound of ever increasing 'pings', the sound made by an arriving tip, I couldn't remain watching; I turned off my computer.

Who was I kidding? Only myself! I turned off the computer because I was ashamed that watching that girl smack her own behind was turning me on, just as seeing her fuck herself with her dildos and hand did the same.

The following morning as I took my normal walk along the beach I saw Rachel approaching from the distance. It was a Saturday, and usually on a Saturday she would have little Rebecca with her, but not today. When she drew up next to me I greeted her and asked why no Rebecca this morning?

"She's away with mum and dad, they have this cabin that they like to go away to every weekend they get the chance. They go upstate a lot to the forests, camping in the woods is the way they raised me, so now they take Becky whenever they can, it gives me some 'Me time', so I like it."

Well, that sort of explained the time frame of her cam appearances, she must only do them when Paul and Angela are away, I thought to myself.

I found it hard to associate the incredibly sexy and wanton girl I had viewed the night before with this innocent looking young lady beside me.

If her parents were away on a Friday night then I reckoned that they would still be away the following evening. I planned to tune in again that evening, but was surprised to get a notification from the website just after lunch. On logging in I discovered that 'Daddy's Girl' was online, out in her yard, and camming from the poolside. The camera angle was such that most of the garden was hidden from view, the naked Rachel was certainly not!

Not only was she naked but she had brought a small glass topped table out with her. After the usual chatting she stuck a huge dildo to the top of it and when her tips hit a certain level she proceeded to lubricate and then ride it, first with her vagina, but then incredibly with her anus. I knew that women could take an erect penis in the anus, my wife had done so on several occasions, although it wasn't her favourite thing to do, but the dildo that Rachel was using must be at least two or three times the size of even an exceptionally large cock! Rachel never ceased to amaze me, what would she, what could she do next? The answer to that came very quickly as she was tipped to do 'ass to mouth'. How she managed to take that huge dildo down her throat I simply could not understand.

I'm easily old enough to be her father, if not her grandfather, but I was beginning to have very inappropriate thoughts about her. She looked so young and innocent when not on cam, and still looked very young when she was on camera. Pumping myself was a great relief as I watched her, it took all my self-restraint not to go out back and somehow look over our dividing privacy fence to watch her in the flesh!

Over the following month or so I got to watch Rachel several times on that website. School was out for the summer break so Paul and Angela were able to take young Rebecca away more frequently than previously. Both Paul and Angela were real estate agents, jointly owning their own agency, Rachel was working for them doing home presentation work, so they were able to more or less decide their own working times and practices. Rachel seemed to take every opportunity to get on camera, I'm pretty sure that she didn't need the earnings she made from camming, so I assumed that she just enjoyed being an exhibitionist.

It was one Saturday afternoon I think when I had to break my cover, hinting at who I was, watching her.

She was out by their pool once again, slowly and teasingly playing with herself, rubbing her labia, opening herself to the camera and gently inserting a finger into her very obviously wet passage. I, as usual was entranced by her activities.

I needed a drink, so getting up from my chair to go into my kitchen to get one I glanced out of my window. There, in the distance, coming along the road was very obviously Paul and Angela's car. I'd know that huge station wagon anywhere. They were probably about three to four minutes away from arriving, so I very quickly went back to my computer and sent a large tip to Rachel, with the tip note... "Parent's car coming down road, now!"

Within seconds 'Daddy's Girl' was offline!

I watched from my window as the car pulled up the drive to the house, and a moment later saw Rachel at the car helping remove bags from the trunk. We can't actually see each other's doors from our houses, but the car was parked far enough down the driveway for me to observe the goings on from my window. As she helped with the unloading I saw Rachel glance up at my window, I don't think she could see in, but I could clearly see her, and the puzzled look on her face.

I didn't see Rachel or 'Daddy's Girl' for several days, but it was about four days later that I again received an email notification that she was online.When I logged on I found her dressed, which was unusual, although when I say dressed I do mean in her underwear, a very fetching matched set of black lace! The text box next to her cam window welcomed me to her room, and almost immediately I received a private message.

"Thank you for the other day, it was just in time!"

"My pleasure."

"Am I safe with you?"

"Always!"

"You are who I think you are, aren't you?"

"That depends on who you think I am! But please don't say it, these sites are not as secure or private as you might think."

"Yes, I know!"

"Please 'R', take a bit more care."

"Ok, might I see you on a beach one morning?"

"I wouldn't be at all surprised!"

Camroom is offline!

So our mutual cover was blown. There might have been a possibility that she thought I was someone who lived much further down the road, but as far as I was aware I was the only one that took morning walks on the beach, it was pretty obvious that she was now associating my user name with me.

Two weekends later Rachel was online again. Our conversation was remarkably 'normal', carried out entirely in the PM mode. (Private Messaging)

How were we both? What did we think about the projected new shopping strip, was I getting on ok with the heat wave? All very run of the mill stuff. One thing she did say was that she felt bad about me tipping her, she would feel better if I didn't. I agreed to stop.

It was only a couple of days later that I was at the turning point of my usual daily walk when I met Rachel on the beach. We chatted about the usual nondescript things and when I asked if she would like a coffee at one of the innumerable coffee shops she agreed. We were sat outside, there was no-one close to us when she asked...

"It is you, isn't it? You know, who warned me a couple of weeks ago?

There was no point denying it. "Yes, that was me."

"I wasn't 100% sure, thank you. How did you find me on the site?"

"Quite by accident, I still have my needs, and I was browsing one day and there you were, I didn't fully recognise you at first, I'd only just settled in, after travelling , but there was something about you so I bookmarked your room and followed you. I hope you don't mind, but if it is too embarrassing for you then I will stop viewing you."

"No, that's ok, it's actually kind of reassuring, and a bit of a turn on knowing that there is a genuine real person out there watching, I kinda like it."

"Can I ask you, why do you do it, I'm sure it's not just about the money?"

"Partly it is, it's good to know that I can earn my own, without mom and dad subsidising me. I mean, I know I have a proper job and all, but I work for them and I know they pay me more than they should, but camming is me, earning my own money."

"Yes, I can understand that, and the other reason?"

"I enjoy it, it's a massive turn on for me, it's difficult to explain. When I'm on cam I feel kind of free, unrestrained. Once you get past the obvious perverts and nasties, there are some nice people out there, even if they are not real, just putting on a persona, like me I guess, I change my personality somehow, I become slutty and horny and need to finish myself."

I think at that point she realised how much she had said because she put a hand up to her face and covered her mouth. My attempt at reassurance seemed to work, at least a little as we left and made our way back to our homes. She told me she was sorry if she had embarrassed me, I assured her that she hadn't, and told her that it was sometimes good to talk about things, to get them off your chest.

We chuckled together as we walked and she explained that having Rebecca had driven a wedge between her and her few friends, so now she was more or less reliant on her on-line friends. I took what I thought was a big gamble and said that I hoped she now counted me in with those friends and whenever she felt she wanted to she was always welcome to come to my house to talk in person. "I make good coffee and only buy good wine."

Over the next few weeks I discovered that Rachel liked good wine. She never drank to excess, but she did like a couple of glasses, to 'mellow' her. And if I'm honest I did the same. Our chats were not exclusively about her, I also felt the need to talk. I talked about my life with my wife, our plans and the ultimate disappointment. She talked about her life both on and off camera.

It was one evening when Rachel had come over for a chat and a glass of her favourite Argentinean Malbec that she let slip what was no doubt her most closely guarded secret.

I had asked her if she had ever thought of going back to college and after a moment's pause she had laughed and said she had never been in the first place!

"But I thought..."

"Yeah, that's what we told everyone, but that's not what happened!"

She looked at me for a drawn out moment or two and then asked, once again if she was really safe with me? Just like previously, I assured her that she was.

"I was pretty useless at school, I just never seemed to fit in, how I ever graduated I'll never really know. I didn't know what I was doing with my life, mom and dad were so successful, and I was just a loser, a complete failure. After mom had me she and dad tried for another baby, but after years of trying and undergoing every procedure they could find they were finally told they were wasting their money and time, mom was infertile. They were offered other alternatives."

She took a good gulp of her wine and continued.

"They eventually discounted all those alternatives and mom came to me as a last resort. They had been offered surrogates, but for one reason or another, they didn't like them, so she asked if I would be a surrogate? We could use a clinic for artificial insemination using dad's sperm, or we could just do it ourselves, privately. I agreed and chose to just do it the natural way."

I looked at this pretty young woman drinking my wine and staring not at me but through me, like I wasn't even there, reliving her memories.

"We told everyone that I was going off to college, what we actually did was go to New York and put me up in a hotel. That's where my website user name comes from, I was daddy's girl 1234, he visited me in the hotel 1,2,3,4 times. And when he was with me we had sex 1,2,3,4 times a day. After his fourth visit I confirmed my pregnancy, waited until the normal end of a college semester, and then went home. So, now I have a well-paid job, and a lovely daughter, and mom and dad have the second baby that they always wanted."

That was quite a revelation, and I was happy to think that she had trusted me with that knowledge, even if she had been a little drunk. It seemed that we had become more than neighbours, we had become friends.

As I watched her doing her cam shows I noticed that quite a few of her viewers asked her when she was going to cam with her 'daddy'? I asked her if they really believed that her dad would cam with her?

Her response was to laugh out loud and explain that the term 'daddy' In this context meant a father like figure, a man who looked after her, rewarded her when she was good and punished her when she was bad. He was expected to be older, that way he could play the role of an actual father, but that wasn't set in stone. It could equally be a younger, dominant man, a boyfriend. But it wasn't expected that he would be her actual father, just a make believe one. I didn't realise how much that conversation was going to change my life!



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