From My Diaries #2 - "Before Curvy Claire"
Part 2
I’ve always loved horses, and with growing up in a farming family, I was familiar with them from a very young age. Daddy wasn’t a breeder or a trainer, but we had a large L-shaped field on the back of the farm that wasn’t in use because it needed flattening to make it suitable for farming and so instead, he invested in some stables and converted them into a paddock for people to house their horses.
My first ever paid job was mucking out and feeding the ponies and at quite a young age, I expressed an interest in riding. Daddy paid for lessons for his Princess, of course, and I never looked back. I wasn’t quite brave enough for racing or even jumping, but I loved eventing and dressage events and when I was old enough Daddy got me my first horse, a beautiful dun gelding that I promptly named Biscuit. For a long time, Biscuit was my world, but I won’t bore you with my love for horses.
Daddy closed his paddocks when I went to secondary school and we relocated Biscuit and the other horses to another stable which was just a bike ride away. I spent a lot of time between being twelve to sixteen at the stables, helping out for a small amount of money and looking after Biscuit, and it was there that I met Simon and Howard.
Simon was my fantasy boy. He was tall, dark and handsome, a couple of years older than me and I remember thinking he was so mature and totally dreamy. Howard was his best friend who worked there with him at the weekends. He wasn’t quite so dishy, in fact he wasn’t really that attractive at all as I remember (sorry if you’re reading this Howard) but he had something about him. Unlike the friendly and gentlemanly Simon, Howard was sullen and sometimes moody and I don’t know whether it was the ‘Edward Cullen/Mr Darcy’ effect or what it was, but I did find myself something thinking about him too.
If you’ve ever been involved with horses or worked at a stable, you will know that it is far from a glamorous job. I wasn’t a girl that wore a lot of make-up anyway back then, in fact despite having a very womanly figure, I was still quite tomboyish in many ways, but I found myself beginning to dress a little more daringly that what was really appropriate for the tasks I was doing, and making more of an effort with my hair and make-up, just to try and get the two boys’ attention.
It worked. Simon and Howard both started regularly asking me when I was next going to be at the stables, and then they would just happen to be there the same days as me. We got to be friends, but of course I wanted it to be more, and I flirted with them outrageously, having not yet mastered the subtle art of seduction which a woman learns as she gets older. I would quite often ‘accidentally’ leave my top unbuttoned ridiculously low, and wear skirts which was ridiculous in such an environment, but I loved the attention such actions attracted, especially as I didn’t really have any other boys in my life with going to an all-girls’ school.
It was booze again that instigated things - this time it was cheap bottles of Lambrusco rather than white cider, but it had the same effect on me when the boys invited me to a party at Simon’s house one summer evening. The ‘party’ turned out to be just the three of us and Simon’s younger brother, who was roughly the same age as me. We hung out in his back garden - Simon’s parents were away on holiday - then listened to some music, ate some horrible barbecued food as I remember, and drank copious amounts of Lambrusco and beer.
Some of you might be thinking, ‘Weren’t you a bit scared?’ or ‘Are you stupid?’ because it’s obvious what the boys were after, but you have to understand that I knew the boys quite well and trusted them. Perhaps I was naive, but I was always quite desperate to impress and if I’m honest with myself, I really wanted to ‘get off’ with one of them, especially the lovely Simon.
My parents knew where I was, and called me during the evening to make sure I was all right. Daddy told me to be a good girl, he knew the boys quite well too - in fact, he was quite good friends with his father - although he probably wouldn’t have been quite as relaxed if I had told him the truth that I was on my own with them, rather than the lie I spun about it being a party and Sarah and some of my other friends being there with me.
Once Simon had managed to dispatch his little brother to bed, the two boys asked me if I wanted to watch a blue movie, and somehow took my quite non-committal response to be one of eagerness, with the speed that they rustled through some old VHS tapes until they found a suitably dirty one. I began to feel a little uncomfortable, watching a woman on all fours being taken by a man at each end - a new concept for me back then - although the porno film did get me a little bit horny at first, I soon tired of it, a lot quicker than the boys did, both of whom were sitting there with tented jeans. They ended up either side of me on the sofa, and Simon put his arm around my shoulder, which all added together to make me feel a bit nervous.
However, I was slightly excited and giddy too and if it wasn’t for the booze I would probably have run a mile but I didn’t. Simon began to kiss my neck and whisper how gorgeous he thought I was into my ear. It was weird for all this to be going on with Howard sitting on the other side of me, so I didn’t respond straight away and when he put his hand on my bare thigh (I was wearing a short skirt) I pushed his hand away instinctively.
He sat up straight, and I had this horrible conflicting moment where I both didn’t want anything to happen too fast, yet I also didn’t want to offend and lose the chances of what I did want - a bit of a naughty kiss and a sexy cuddle. So, I reacted by putting my arm around his neck and drawing him into a kiss. His face went from one of dismay and disappointment to one of pleasant surprise in an instant, and the second time his hand went on my thigh I didn’t move it.
He didn’t go straight for the kill - his hand just rubbed up and down my thigh a few times, slipping under my skirt without ever going too far, but as we ‘made out’ it eventually moved upwards, hesitatingly stroking across my breasts and then eventually cupping and squeezing one. Now I was really starting to get excited and I whispered into his ear that I wished Howard would go away so we could lie down. He stopped kissing me as we looked at each other for a moment, probably while he decided what to do, then he took me by the hand and led me upstairs.
I let him take me into his bedroom, which I remember was full of football posters and the like - he was a Liverpool fan - and after we barricaded the door shut with a chair and a box, we started kissing on the bed. How exciting is it when you’re that age, to be kissing and ‘fooling around?’ I remember the radio was playing “I’ll Be Missing You,” by Puff Daddy and Faith Evans as he lifted my top up and pulled my bra down. It was the first time that someone other than Toby had seen my breasts and I was so incredibly turned on that I actually pulled his head down for him to suck my nipples.
His hand went under my skirt and pulled down my knickers and my hands were rubbing the front of his jeans and after his fingers had found my wet pussy hole and fingered me for a few heart-racing moments, he helped me to undo his belt and zipper and it was then that I felt my first cock in my hand. He yanked his trousers and boxer shorts down and I just grabbed it and started to stroke it - he must have thought I was a total slut, I was that eager!
He wasn’t as good at playing with my pussy as Sarah had been, he didn’t touch my clit, instead he just finger fucked me as fast as he could, with first one, then two fingers, but to be fair I probably wasn’t giving him the best hand job ever either. I was just tugging on it, but it was my first time doing it, so I shouldn’t be too hard on the young Claire, I suppose.
It was the first penis I’d seen since Toby’s and I remember thinking it was slightly bigger and less hairy. I had fun pulling the skin back and seeing how shiny and slightly wet the end of his cock was. I felt his balls too, something I’d never done with Toby. I thought they felt very strange at the time. Simon was getting incredibly horny, and was pumping his hips in time to my hand stroking his cock, like he was fucking my hand, and seeing how aroused he was getting only served to make me more turned on too, especially with his fingers working my pussy.
As drunk and as turned on as I was, when he tried to get on top of me to fuck me, I stopped him and asked him if he’d got a ‘rubber Johnny.’ The look of disappointment on his face was crushing. I really, really wanted him right then - it was all so perfect - but naive as I might have been, I wasn’t stupid. My parents and my sister had all given me the talk on being sensible when the time came, and as nice a boy as Simon was, I wasn’t going to risk catching something or getting pregnant.
Simon got a little bit upset, as boys do when they’re denied at the last minute, but luckily his little brother came to my rescue by banging on the door and shouting, ‘I know what you’re doing in there!’ in the most annoying voice possible. Simon and I got dressed rapidly and headed outside where Simon beat the hell out of his kid brother, while I made my excuses to go home.
Despite the night ending in a bit of a disaster, I’d had the most brilliant time, and like the silly young girl I was back then, I thought he and I were an item. All sorts of crazy romantic notions went through my head over the next few days, until on my way to my friend’s house the following week, I saw Simon standing at the bus stop with another girl. As I walked over to say hello, they started kissing and I felt my heart break for the first time.
Isn’t it funny how life at that age is so full of extreme feelings? The most intense of loves, and the bitterest of disappointments. Everything is so magnified - you’re feeling emotions for the first time, and they either totally thrill, or they completely crush you.
Simon even looked at me, but didn’t break the kiss, in fact his eyes lingered on me and when I felt my own eyes brimming with tears, I turned and walked away. I’d been on the way to see one of my friends, but for some reason I went instead to the stables.
When I got there, I went and consoled myself by giving Biscuit a brush and filling his trough with fresh water and food and then as fate would have it, I saw Howard sweeping the yard and went out to speak to him.
He could tell I was upset and once he’d done, he asked me if I wanted to go back to his mum’s house for a drink and a chat about it, an offer which I gratefully accepted. His parents were lovely, they made me a cup of tea and a sandwich while I phoned mother to tell her where I was, and once we’d eaten, we went up to Howard’s room where I poured my heart out to him about how Simon, and how betrayed and heartbroken I felt.
Howard was normally the quieter of the two, and because he was normally quite unapproachable and nowhere near as charismatic or friendly as his best friend, I didn’t expect him to be so sensitive but he was. However, I was even more surprised when he quietly told me that he’d gotten really jealous when Simon had bragged about what he’d done with me.
I was angry. Simon had told him? I had to know exactly what had been said, so I asked a quite embarrassed Howard to tell me what he’d bragged about. That was a little insensitive of me, as Howard was basically trying to tell me how much he liked me, but I was fuming at that particular moment. He didn’t want to say, but I insisted and eventually he told me that Simon had boasted of playing with and sucking my ‘big tits’ and that he’d fingered my ‘hairy pussy.’ I cringed slightly at that, but told him to continue and with burning cheeks Howard said that Simon had gone on to say that I’d wanked him off and that he could have fucked me if he’d wanted to, but his little brother had interrupted them and spoiled it.
But then Simon had got off with another girl that he’d fancied for ages, and who was slimmer and prettier than me. He’d even told some of the other lads that he was friendly with that I was now fair game and that they should ‘give me a try.’
I was devastated at that, and Howard began to apologise, saying he shouldn’t have told me - but I thanked him for being honest. He was upset as well and I felt I should say sorry too, for ignoring him. If I’d known what a dick Simon was and that Howard was as nice as he was, I would have gone out with him instead.
I remember realising that I was crying. I don’t know when the tears had started coming - I only knew when Howard reached up and wiped them away. He was staring at me, and it was one of those moments that just happen. Howard leaned in and kissed me and before I knew what was happening, I was kissing him back passionately. We went from kissing to dry humping on the bed, and then I took the initiative and took my t-shirt off. Howard’s eyes went as big as dinner plates when he saw my boobs in my bra. He was already hard, I could feel it rubbing against me through his trousers, but I bet he got even harder. His hands went to my breasts, squeezing them enthusiastically but he didn’t make any attempt to take my bra off.
I’d got trousers on that day and I remember wanting to be really naughty and because he didn’t make any moves at all to progress things, I popped the button and pulled my zipper down and eventually he took the hint, sliding a hand slowly down my belly and into my panties. I shrugged my knickers and trousers down to give him better access to finger me and then I reached behind my back and unclasped my bra for him.
This was it; I was going to lose my virginity. I decided there and then that even if he didn’t have a condom, which he most likely didn’t, I was going to let him have me. Even if it was just to get back at Simon, I didn’t care. I just wanted someone to want me, and Howard obviously did.
After several more minutes of frantic kissing and groping, I was more or less naked, in only my socks basically, so I pulled his shirt off over his head, then undid his trousers and pulled his shorts and trousers down. Of course, Howard was already rock hard, and I remember thinking his dick was huge at the time - it was certainly much bigger than Simon’s and Toby’s, and had very little hair around it at all. I grabbed the shaft and started stroking it, then he pushed my head gently downwards and at first I wondered what the hell he was doing, then it sank in that he wanted me to suck it.
I was so scared, but I took a deep breath and moved so that his cock was right in front of my face. His penis was very hard and felt hot in my hand as I pulled the skin right back and first kissed and then licked the end tentatively. It didn’t smell or taste of anything in particular, I don’t know quite what I expected, but it wasn’t unpleasant at all, so I put my lips over the end and began to slowly suck on it, moving more of it into my mouth as I dared, nervous I might choke on it if I went too fast.
The end was so smooth as I ran my tongue over it, and It felt so wonderful when Howard began to moan and started to move his hips a little. It seemed to grow in my mouth, getting even harder and it was so rewarding to know that I was doing it right - he was obviously enjoying it - so I began to suck it a bit more confidently, trying to remember how I’d seen women do it in the porn videos I’d seen. Howard’s hand stroked the back of my head, then suddenly he announced that I should move - fast - and I realised he was going to ejaculate. Quick as a shot I pulled away and just in time, because a thick stream of white fluid jetted out, landing all over my hand and his thigh.
I was disappointed that he’d finished already - but I also felt a huge thrill at having made a man cum. It was almost like a feeling of pride in myself. I was so happy I felt like I was going to burst! Howard was embarrassed at having cum so soon and apologised for it, but I kissed him and told him it was fine. He cleaned up and we kissed again for a little while before I made my excuses to leave, but not before we made plans to go on a ‘date’ soon. The cinema - on the coming Friday. I couldn’t wait! The kiss at the doorstep as I left was the tenderest, loveliest thing that I’d ever known.
I went home, realising that I’d got a boyfriend. My first boyfriend!
Part 3 following soon... xxx Claire
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