Tag: short-story

  • The Widower

    I met Gary on a beautiful warm October afternoon at a national trust property with picturesque gardens extending down to the river Helford. He was new to the whole sugar daddy thing, so we were meeting to discuss what he was looking for and whether it was something I could provide. I knew very little about Gary, so was curious to find out what had brought him to the site. 

    It was here, overlooking the river, that Gary explained how earlier that year he’d sadly and unexpectedly lost his wife. She’d become ill very suddenly, got a nasty infection and died. I don’t know how old she was, but Gary was only 58, so she can’t have been that old.  

    They’d been together since they were young, working hard to provide for their children; now was their time to relax and enjoy each other’s company, to retire and do all the things they’d wanted but never had time to do.  

    It’s difficult to know what to say when someone divulges something like this, what can you say? No words can take away the pain of such an enormous loss, so I just listened; being with him in that moment, holding space for his grief.  

    As we continued to explore the grounds, we spoke about lots of things, not just what he wanted and what he was looking for, but about life in general and how unpredictable and unfair it can be. As he’d been so vulnerable with me, I opened up and told him a little about my past, and how I’d ended up as a sugar baby; which isn’t something I normally do on a first meeting.  

    After our rather emotional walk we drove to a nearby pub for a drink. Gary had enjoyed our afternoon together and was keen to arrange a ‘proper’ meeting where we could get to know each other on a more intimate level. He was feeling guilty about wanting to see me and for having these feelings of lust and desire though, and was worried about what other people would think if they discovered that he was being intimate with another woman; especially his children who’d become very protective over him since losing their Mum. 

    He was frustrated having lost a huge part of his life, and although his friends and family had rallied around him, none of them had been able to provide the physical intimacy or closeness he was missing. Of course, Gary wanted to have sex again, but it was more than that, as it so often is; it’s lying in bed naked next to someone, feeling the warmth of their body against yours, holding hands, stroking someone’s hair, all the little intimate touches and gestures that you share with a lover. He wasn’t looking for his next great love, just someone to bring back some normality into his life. 

    Whilst sipping our drinks we discussed his sex-life with his wife, and how it had dried up (literally) when she went through the menopause; even before that though, it had all been very vanilla and boring. She didn’t like giving or receiving oral, and the few times she’d gone down on him it had been painful and unpleasant.  

    Gary loved his wife though and wouldn’t even have considered looking elsewhere for sex (unlike many married men in that situation). They didn’t talk about it and Gary never complained; the lack of sex was a small price to pay for what was otherwise a happy marriage. However here was a man who’d been given a second chance, and Gary was keen to explore new things in the bedroom and find out what he’d been missing. 

    He was curious and asked lots of questions, he wanted to understand what I liked and where he should start if he wanted to try something new. We talked about toys, bondage, role play etc; all the exciting things he’d yet to discover and which I was only too happy to explore with him.  

    I was impressed with Gary’s philosophy regarding what had happened to him. He wasn’t angry or bitter like lots of people would be in his situation; nor was he rolling over and giving up, despite the fact that his whole life had been turned upside down. No doubt he’d been through all the various stages of grief, but he’d come out the other side knowing that life is short and determined to make the most of it. 

    Do I think we will have challenges going forwards, yes of course. Gary’s not had sex for a few years, and the last time he did was with his wife; so, no doubt the first time will bring up some difficult emotions, but we can talk through them. I’m happy (as with all my men) to take it at his speed; and have reassured him that he’ll never be under pressure to do anything he’s not comfortable with.  

    It’s a sensitive situation, and I’m all too aware of the need to respect what’s happened; to allow him time and space to talk about his wife if he wants, whilst also providing a safe place to discover who he is without her, and what he wants as a widowed man. 

    I think Gary’s probably one of the nicest sugar daddies I’ve ever met; just a really kind and genuine man. He’s certainly too good to spend the rest of his life on his own and deserves a second chance at love. It’s not something he’s ready for yet though, it’s too soon to even consider getting involved with someone on a romantic level. Seeing me is an intermediate step, a chance to rediscover his sexual side, and build his confidence.  

    Hopefully by the time he’s ready to fly the nest (so to speak) he’ll have explored everything he wants and will be the confident sex God I know he can be; ready to make some lucky lady very happy! 

    For anyone who thinks my job is just having sex with men for money, hopefully you can see that it’s not, it’s so much more then that; and I love the fact that I get to help people in ways that others can’t.  

    Till next time. 

    Emily-Rose xxx 

  • The farmer and his whore

    Being only in his forties, Kevin is one of my younger sugar daddies, and of all the men I see, the most ‘wham, bam, thank you mam’. There’s no wining and dining or romancing here, he knows exactly what he wants and doesn’t waste any time getting it. 

    He’ll normally call in on his way back from work; dressed in a shirt and tie, smelling of coffee, and desperate for a wee… typical salesman. He sells farm machinery and has his own small holding.  

    He knows my dad, which isn’t surprising as everyone in the farming community in Cornwall knows each other. He’d never say anything though, I mean, how would that conversation even go, “oh by the way, I know your daughter, yeah I pay her for sex”, I don’t think so…  

    The moment Kevin sees my naked body, his cock is rock solid and he’s ready to go. He makes me kneel down in front of him so he can ram his hard cock down my throat. He doesn’t care how much I gag or choke, he’s got a big cock and makes me take it all. Sometimes he’ll throw me on my back on the bed, with my head tilted over the edge so he can stand over me and push his cock straight down my throat. I can feel my throat pop as he pushes his cock all the way in; there’s no way to breathe, and it makes your eyes water. When I can’t take anymore, he’ll turn me over on all fours and fuck me from behind, pushing my face down into the bed and pounding me hard.  

    I have a full-length mirror in my bedroom, so sometimes he’ll get me to stand facing away from him, spreading my legs slightly, bending over to touch the floor so that he can fuck me from behind whilst watching himself in the mirror.  

    If you’ve ever tried this position, you know it’s not easy to maintain and eventually (if you’re unfit like me) your legs give out and you end up on the floor. I did this with a guy one night when I was pissed and hit my head on the kitchen floor; I swear I had concussion for weeks afterwards.  

    Unlike most men who need time to recover after coming, Kevin can just keep going. His record with me is four times in one session; he’s a fucking machine (literally).  

    One day he messaged to say that he was coming over to spunk in each of my holes (mouth, vagina and ass, in case you were thinking anything else). His cock is on the big side for anal, so I don’t let him fuck me up the ass every time we meet; when he does, I know about it afterwards and it takes me a few days to recover.  

    If you’re thinking of going for the ‘holy trilogy’, as I’ve decided to call it, just be careful what order you do it in, you definitely want to pop the brown last is all I’m saying… 

    Kevin is one of my biggest sugar daddies (cock wise), and probably one of the biggest I’ve had (or at least top 10); not just a good length, but girthy with it! I know men can be obsessed with the size of their penises, but believe me, there’s such a thing as too big, and Kevin is bordering on it.  

    When he’s fucking me hard and deep, he’ll say that he can feel my contraceptive coil, which isn’t surprising, I’m sure the end of his cock is smashing into my cervix and trying to penetrate my uterus, which isn’t always a pleasant feeling.  

    Whilst I enjoy sex with Keven, I’m glad my other sugar daddies aren’t so big, my poor vagina would be destroyed (and as for my asshole…)!   

    As well as being dominant in the bedroom, Kevin also enjoys talking dirty, calling me a naughty little slut whilst spanking my ass; getting me to repeat it back to him, whilst telling him how much I want his massive cock. He gets off on hearing about how many men I’m fucking, and how many I fuck bareback, so I play my part and tell him what a filthy whore I am etc. It’s all very boring, but he absolutely loves it….  

    When he can’t see me because he’s either too busy or doesn’t have the money, he likes getting dirty messages about the other men I’m fucking, and I’ll send him sexy photos (of me, not other men) to keep him going. I let Kevin film a few of our sessions, so he can always watch those if he wants to see me sucking cock or being fucked. 

    Kevin seems to be fairly typical when it comes to younger guys and the way they treat sugar babies, in the way he likes to talk dirty and call me names. Yet although he can be rough in the heat of the moment, he’s always a gentleman afterwards and there’s something quite sweet about him. He’s got a vulnerable side, although I can imagine him being a right bastard when he wants to be.  

    Unfortunately, I don’t see Kevin that often, which is a shame since it’s quick and easy, and I don’t have to leave the house; in fact, I don’t even need to get dressed.  He works hard yet is always short on money, having just paid some big bill or another. He’s one of those guys though, it doesn’t matter if I haven’t seen him for ages. We just pick up where we left off…. the farmer and his whore. 

    Emily-Rose xxx

  • I get a big surprise…

    Every now and then I’m contacted by a guy who’s taken a wrong turn and accidentally signed up to a sugar daddy site; wondering why (despite having no luck in the past) they’re being bombarded with messages from attractive women who are way out of their league.  

    This guy was one of those guys, naive and clueless, coming up to 50 and living at home with dad on the farm; never married, unable to get a date, and probably still a virgin (though maybe I’m being harsh). 

    Thankfully I got to him just after he’d signed up, before too much damage had been done (new guys are easy prey for less honest girls on the site). Despite not realising what he’d signed up for, and being slightly shocked by it all, he still wanted to meet; saying that he wasn’t against the idea of paying for female company or sex. His photo wasn’t great; but I’m nothing if not optimistic, so agreed to meet for coffee.  

    When I arrived at the agreed location, I walked straight past him, that’s how dodgy his picture was and how rough he looked. He was wearing old dirty work clothes and had come straight from the farm, you’d have thought he might have made an effort, but apparently not. My heart sank, my optimism had been misplaced, he looked like a fricking hillbilly; it sank further when he started talking in a thick west country accent about the farm, which was all he had to talk about.  

    We had our coffee though, and he enjoyed our time together and thought I was gorgeous… obviously. He’d led a very sheltered life, and didn’t get away from the farm very often. I felt sorry for him, so feeling generous, let him go in for a little kiss and a quick grope; which was probably the most action he’d had in years.  

    I explained the deal, that if he wanted to see me again he’d need to rent a room and pay for my company (his place wasn’t an option, and there was no way he was coming to mine); and although he still seemed hopeful (delusional) that he might get a girlfriend out of it, he understood the situation and agreed to my terms.  

    Before arranging our next meeting, he asked for some saucy photos, which I sent him, thinking it might encourage him to book somewhere and part with some money. I didn’t ask for anything in return, yet despite this, was treated to a couple of photos of the biggest cock I’ve ever seen; it really was a sight for sore eyes, and potentially a rather sore pussy. 

    When we arranged to meet the following week, he couldn’t get away for the night, but was keen to see me, so we arranged to go for a drive and see how far we could get in his car. Not how I usually do things, but for some reason (against my better judgement) I said yes; possibly the thought of his massive cock had something to do with it… 

     We met in a local carpark, where I jumped out of my car, and into his. Now, I’ve been in some dirty cars in my time and mine isn’t exactly clean, but his was absolutely disgusting; every surface covered in mud or shit, and rubbish everywhere, it was gross! He didn’t look much better, in dirty farm clothes, and a holey jumper which he had on inside out; I wasn’t impressed!  

    We drove around looking for somewhere quiet to stop, and eventually found a secluded parking area, which was empty but for one car. Unfortunately, there was a man in that car, however he didn’t complain so I can only assume he enjoyed the show. Should have charged him too really…  

    We got into the back of the car, which wasn’t easy with the amount of crap back there. I pulled off my panties and spread my legs, showing him what he was paying for and inviting him to take a closer look. I don’t think he could believe his luck, his hands were all over me, pulling my top down, groping and sucking my tits like a randy teenager. As for what he was doing down there, fuck knows, but whatever it was, it wasn’t doing anything for me.  

    As I leaned over to place my hand on his crotch, he got a bit funny and told me that he had a confession to make; the pictures he’d sent weren’t of him, he’d taken them off the internet. He then pulled down his dirty jeans, revealing some very old and suspiciously stained pants; which were then pulled down to reveal one of the tiniest, and saddest looking cocks I’d ever seen. It was like a sick magic trick, with every layer that came off, revealing something more revolting.  

    I was annoyed that he’d lied to me and lured me there under false pretences, although I was also a bit disappointed, I’m not going to lie…. I had no choice other than to be professional though and reassure him that it was fine; size didn’t matter, and the pictures he’d sent me were ridiculously big anyway (which they were). Saying all this whilst using my thumb and two fingers (all I could fit on his tiny cock) to encourage it to come out and play, which it didn’t seem to want to, probably too embarrassed!  

    He then apologised for not having had a shower that day, explaining that they had no hot water; before suggesting that I put his tiny smelly cock in my mouth to see if that helped the situation. I didn’t have the heart (or strength of character) to say no, so I did; checking for dick cheese first and being conscious not to breathe through my nose.  

    Not much happened, so as soon as I thought I’d done enough to show willing, I suggested that we get out of there before someone caught us and did us for indecent exposure.  

    On the drive back I asked him why he’d sent pictures that weren’t of him. I hadn’t asked him to send any, so why send anything at all. His answer was, “it got you interested though, didn’t it”, which really pissed me off.  

    He knew that we were going to meet, and that I’d find out the truth; how did he think he’d get away with it. Also, why put yourself in that awkward and embarrassing situation in the first place; men are so stupid sometimes…  

    The most annoying thing was that he didn’t think he’d done anything wrong, and felt that his actions were justified; which is weird as when we first met, he mentioned how he disliked people who were dishonest or fake… Rather ironic, don’t you think… 

    When I got home, I stripped, put my clothes in the wash and scrubbed myself clean in the shower; after which I updated my spreadsheet, highlighting his name in red, and vowing to never go there again. 

    It’s worth mentioning that this (like so many disasters) was at the beginning of my career, when I didn’t really know what I was doing, and was chasing money at any cost; I’m more cautious now. 

    The lesson here is that if something sounds or looks too good to be true, then it probably is. 

    Emily-Rose xxx