From My Diaries #2: "Before Curvy Claire"
Howard and I ‘dated’ for a couple of months - starting with the cinema that week, although I think we completely missed the film as we had our lips locked together for most of it - and we went for McDonalds and a KFC, after both of which we snogged each other’s faces off and had our hands down each other’s pants. Then one night we went ice skating, which was fantastic despite me being terrible at it, and I’d set it up so that I could take him home afterwards.
My parents were out all night, and I’d asked Donna to make herself scarce which she’d agreed to as long as I promised to behave myself. I’d even visited the local family planning clinic and been given a huge paper bag full of condoms. I was prepared, mentally and physically for sex, and I really wanted to do it, so that night as soon as we got through the door, I kissed him and dragged him to my bedroom.
It was the first time he’d been in my room, so he took a few minutes to look around and commented on the decoration and such, but I could tell he was just stalling - probably because he was nervous - so I told him to come over and feel how comfy the bed was. Howard sat next to me and bounced up and down a few times, saying it was lovely and soft and then I began to undo the buttons on my top and gave him the sexiest smile I could.
It worked; he smiled back at me, and started to undress himself. That was the first time I realised how hard it is for a man to undress sexily. It’s easy for us girls, but men often make a total hash of it, just like Howard did. He took his shirt off first, then his trousers so that he had his boxer shorts and socks on - which just isn’t a good look for a man, trust me. Even worse, he pulled his boxers off first, so he was stood there in just his socks while he watched me undo my bra then he even tried to follow me under the covers with them on. I stopped him and asked him to take them off, and then when we were finally snuggled up naked together under my big heavy duvet, I slipped my panties down and got on top of him.
We kissed, and then I reached down for his penis, to try and put it in me. I was already wet and horny but to my surprise, he wasn’t getting hard. I’d noticed that his dick was still soft when he’d taken his shorts down but I thought he’d get hard once we started kissing under the covers. However, he hadn’t, so I rolled off and played with him for a few minutes until finally I felt him starting to stiffen but then as I finally got him fully hard again, he began to push my head down again under the covers.
“Okay,” I said to him, “But don’t cum. I want you.”
“I won’t,” Howard promised, urging me downwards, “Please do it though.”
I threw the covers off us, so we were both totally bare and slid down the bed to suck him again. I’d be lying if I said that I didn’t enjoy going down on him - I did, it felt really naughty and really rewarding again to hear him moan at how good it felt - but I really wanted to have sex too. I licked and sucked him for a while, but as he started to get more and more excited, I stopped and reached in the drawer beside my bed for a condom.
“What are you doing?” he asked as I unwrapped the condom, so I threw the empty silver foil packet at him in response. His eyes widened as he realised what it was, and then I began to tricky task of putting the rubber on him. I’d actually done this in school - in sex education, the teacher had shown us how to put a condom on a banana - but doing it in real life was much trickier. I managed to get the condom the right way around, then finally managed to unroll it down Howard’s length, and I looked at the completed and ready dick with pride.
“Fuck me,” I said, rolling onto my back and spreading my legs wantonly. I could feel my cheeks burning with embarrassment but I was that horny I just didn’t care. Howard stared at my pussy for a moment, then rolled towards me, kissing me and feeling my breasts and finally, after what seemed like an age, he slid his body over me and began to clumsily try and point his dick into me.
I felt the end pushing against my labia, but it kept sliding up my slit and over my clit, which was throbbing, so I reached down and took hold of it to help him guide it in. But just as the end started to push against me, I felt it suddenly twitch and Howard groaned into my ear.
No way. He hadn’t, had he?
He had. “I came,” he sighed as he sagged against me. His cock did actually go inside me a little way but then it popped out and he rolled off, giggling to himself. I think Howard thought he’d fucked me, but in my mind, he definitely hadn’t. I certainly don’t count his dick going one inch inside me as losing my virginity. I have no idea whether or not I still had a hymen back then - probably not with doing my horse riding and being quite an active girl - but I don’t think he would have broken it even if I had. There certainly wasn’t any discomfort or blood.
I was so disappointed. “Is that it?” I blurted, rather bluntly perhaps, but I simply couldn’t believe it.
“I’m sorry,” he said, still quite breathless. “Can I do something to you?”
I pointed at his wilted penis. The full condom was hanging from it, which looked quite funny. “What are you going to do? That’s useless to me now.”
I was probably being quite bitchy, but I was angry now. Howard pulled the condom off and threw it on the floor, which made me yell at him - I didn’t want sperm all over my carpet! - but he told me to relax, and pushed me back as I started to sit up.
“Trust me,” he said, and I looked at him confused for a moment, before realising what he was going to do as he positioned himself between my legs, sliding down the bed and trailing several little kisses down my body until he kissed my mound. I’d trimmed down there, so my pubes were in a neat, light brown triangle, which he commented on by saying it looked better. Then I felt a slight sense of panic for a moment. What if my pussy smelled or tasted funny or something? I was certainly very wet, and I was about to stop him when his tongue touched my labia and then flicked up over my clitoris.
It felt like nothing I’d felt before. I’d been masturbating quite regularly, and knew how good clitoral stimulation felt but the warmth of his breath on my pussy and then the sensation of his lips and his tongue pushing between my folds was something completely new. I felt his fingers spread me open and then as his tongue began to lap against my clit, I gave in to the feeling and closed my eyes to let him do whatever he liked.
I lost all sense of time. I slipped into a fantasy world, imagining all sorts of dirty things being done to me, including Howard fucking me and inevitably I felt that throbbing feeling low in my groin, a soft ache, almost painful but intensely pleasurable, building and building until finally it exploded into an orgasm. My back arched upwards and my thighs locked on Howard’s head at first, until I realised then I let him go.
He looked up at me as I recovered from what was my best orgasm ever at that time, and I can still picture his face, grinning like a Cheshire cat with my pussy juices all over his mouth and chin. He touched my clit with his thumb, and I jerked away as it was painfully sensitive.
“Did you like that?” he asked.
“What do you think?” I laughed at him.
Howard hadn’t fucked me, but he’d made up for it with his tongue. All sense of regret at him cumming prematurely disappeared and all I could think of once he’d gone home was the feeling of his tongue exploring my pussy. When I got in bed that night, I couldn’t help but take my pyjama bottoms down and I played with myself until I came again, reliving the experience all over again in my imagination.
I don’t know why Howard and I never went any further than that. We hung around for a while, going on a couple of dates again - the cinema was our favourite thing to do together, but for some reason things never came together to give us the opportunity. When I had the house to myself, which wasn’t very often, he would be busy and vice versa. We saw each other most days, but there were always other people around, so we never did anything more than hang out and play with each other. I wanked him off one night in our local park, and then as we sat talking afterwards, he told me about this other girl who he fancied.
It was very strange because I didn’t feel angry and I didn’t feel betrayed. I really wasn’t that bothered at all and I realised that I didn’t have any feelings for him. It wasn’t even shock or surprise making me emotionally numb or anything like that. Howard and I were more like best friends who fooled around rather than boyfriend and girlfriend, and so after regaining my composure I asked him about her and even ended up giving him some advice on how to ask her out.
So that was the end of Howard and I as a relationship, although we stayed friends for quite a while afterwards, right up to me leaving school in fact, but we never so much as kissed or anything after that night. There weren’t any other boys I fancied or had my eye on at that particular time, so I decided to give up on losing my virginity with boys my own age, and instead began to wonder if I needed someone older and more mature. Someone who knew what he was doing and wouldn’t cum in a matter of minutes.
For a girl of that age with protective, caring parents and who didn’t have a huge social circle, it was difficult to meet older men of course, so it wasn’t until I left school and started studying my ‘A’ Levels at college, that I began to meet people. I wasn’t bothered about having a boyfriend during the period leading up to college. I was quite a responsible (boring) girl, I listened to my parents and the advice of my teachers, and concentrated on my studies and left school with ten GCSEs of a good grade, if not quite all A-stars like my sister had attained, but I was more than happy with my achievements, and it got me into the subjects at college which I wanted to study.
I took English Language, Geography, Music and Agricultural Studies, which was a nice eclectic mix and college was a fabulous experience for me. I had the choice of staying on at school in the sixth form, but I really wanted to study with a more varied pool of students and the school I was at didn’t do agriculture so I used that as an excuse to myself to get out of the All-Girls’ school (which I loved dearly but there were no men!), if I’m being honest.
I did well at college. I studied hard and got good results in all four subjects, but I never went on to university because I met my future husband during this period, and we got married the year I left college and he said he didn’t want me to leave Cheshire to study. He promised that he would look after me - we would buy a house together and settle down and raise a family and then if I wanted to go to university and pursue a career afterwards, he would fully support me and so that’s what happened.
As of now though - ten years later - I’ve never gone to university and while I wouldn’t mind working towards a degree one day, I am quite content with my life as it is. I know I’m not stupid - I don’t need letters after my name to prove it to anyone, do I?
I didn’t lose my virginity to my husband, he was my second lover. I finally managed to get rid of my virgin status during my first year at college. I was seventeen and a half, quite a late age to lose your virginity in today’s world, but I’d learned a valuable lesson during those early failure fumbles with Simon and Howard, and didn’t see the point in sleeping with a man just for the sake of ‘losing it.’ No, instead I would wait for the right man to come along. I wasn’t sure how I’d know he was the right man, but my college friends that I confided in told me that it would just happen when the time was right. I’d meet someone soon enough.
And I did. Mr Right came along during Christmas week in 1999. We were all gearing up for the biggest party in history - the Millennium New Year’s Eve - and there were parties everywhere to go to during the last week in December, indeed the last week of the 1900s - and being a typical student who liked a party, if not a heavy drinker, I intended to go to as many of them as I could. But it wasn’t a crazy student party that I met my first real lover at. Rather, it was a party organised by my father.
My dad was in the local Rotary Club and was also a Freemason, so he had a very varied social circle and knew a lot of the local business owners and their families. Over the years growing up, I had met quite a lot of them, so when I was towed along to one of his get-togethers I knew most of the people there, but this time there was a man I didn’t know but who father seemed keen to introduce me to.
“This is Colin,” I remember him saying, “He’s bought the old dairy...” Father continued on and on, telling me all about how Colin and his family were new to the area, and in particular about his son, who was of an age with me and very well to-do, but I was only half listening because Colin was the most handsome man I had seen for a long time.
He was much older than me, in his early fifties and so actually older than my father, but he had the most piercing, light blue-green eyes I had ever seen and when he caught me staring he gave me a small smile which actually made my heart skip a beat. I don’t know how many women have experienced that flutter when you meet a man who just has that ‘something’ about them that makes them instantly attractive and you feel yourself totally drawn to them, but those of you who have felt it will know what I’m talking about.
Colin was tall and broad, quite powerful looking and dressed in a light grey suit. I remember his shoes were very shiny brown brogues, as I found myself looking down because I was so embarrassed as he took my hand and kissed it.
“Nice to meet you,” he said in a deep, gravelly voice and that was it - I was in love! Well, not quite, but I was swept off my feet by him. Even though his hair was receding, and his face was quite hard-looking there was just something about him that blew me away.
“Hello,” I replied rather lamely. I think I even stuttered.
Colin went on to suggest that I should call around to their house sometime and meet Dean, his son who was looking to make friends. We could drive in to Chester and go to the cinema or something. It was a blatant set-up to try and get us on a date, and I found myself stammering that it sounded like a good idea, just getting more and more embarrassed in the presence of such a beautiful man, and when Colin made his excuses to ‘go and mingle’ I felt a mixture of both disappointment at him leaving me and yet relief at the same time.
“Not like you to be so shy,” I recall father saying, “Don’t worry, I’ve met Dean and he’s a lovely lad.”
I think I nodded and said something back, but all I could think about was the man who was now talking to a tall, elegant brunette at the other end of the room from us. I felt the first twinge of jealousy, despite only having met him once a few minutes ago.
The party was a fun one, with plenty of alcohol to go around, and I made sure I got more than my fair share so with the combination of the music and the general party atmosphere, I was in a fun and flirty mood which is why when Colin asked me if I’d like to join him for a cigarette outside, I didn’t hesitate.
It was terribly cold, I remember being able to see my breath, and I had left my coat hung up inside, and was only wearing a short-sleeved blouse and skirt, so as we began chatting while sharing a cigarette (I was a social smoker at the time) Colin suggested we go sit in his car instead.
His ‘car’ was an impressive, gorgeous, large, black four-wheel drive and as soon as we sat in there, he turned the heating and the music on and turned to look at me.
“Claire, can I ask you a question?” he asked and I nodded after taking a drag on the cigarette. “How the hell is a beautiful young woman like you single?”
My heart quickened a little as I replied, “I don’t know. I’m hardly gorgeous.”
“Are you kidding me? Look at you - pretty, blonde, big boobs, those legs...” I remember he was gesturing with his hand, almost touching me and as he continued to flatter me and express his disbelief that I didn’t have a boyfriend or a queue of boys wanting to date me, I chuckled, enjoying the attention from such a handsome, older man.
“If I was thirty years younger, I’d be begging you for a date every day until you gave in,” he continued, “Wooing you with flowers, chocolates or whatever it took.”
“Were you a bit of a charmer when you were younger?” I asked and Colin smiled at me and told me that he used to be a real ladies man as a young man, and that he’d had a weakness where pretty girls were concerned. Then he leaned in close and confessed, “I still do.”
I recall laughing slightly nervously because his hand was resting on my knee, and he pulled away suddenly, apologizing if he was making me feel uncomfortable. I told him it was fine but he carried on saying sorry, explaining that he found me incredibly attractive and it had been so long since he’d been this close to someone as sexy as me.
Looking back now, it’s so obvious that it was a blatant line, and that the sob story he poured on me about his wife being disinterested in sex was a cleverly concocted routine to get a girl in bed, but I was a seventeen year old girl, and quite a naive one at that, with a belly full of alcohol and sitting in an incredibly handsome and charismatic man’s flashy car, so I had no chance really.
I told him I thought he was lovely, and rambled on to him about how he should leave his wife and find a nice girl who would appreciate him and when he said he was too old, I responded exactly how he probably intended, by saying that he didn’t look his age and that I was quite sure he could have any girl he chose.
I was playing right into his trap, and he sprang it by saying, ‘Prove it then,’ and, ‘What if I chose you?’ and like the silly drunk teenager I was, I leaned in and kissed him. Colin broke the kiss after a while, and pointed out that it probably wouldn’t go down well if my father saw us, and suggested we go for a drive somewhere, so I skipped into the house, collected my coat and told my Daddy that I was heading home early because I’d got a headache before rejoining Colin and heading out into the Cheshire countryside with him.
I knew what I was doing. I wasn’t quite so stupid that I didn’t know what I was getting into, or where this was leading, but I had come this far, and the combination of alcohol and Colin’s dizzying presence had me incredibly horny and by the time we pulled up in a dark country car park my heart was racing not with nerves, but with anticipation.
I remember Colin leaning in to kiss me again, complimenting me on how good a kisser I was, and feeling his hand sliding up onto my breast, then asking me what bra size I was. I was 36D at the time, which he found quite amazing for a seventeen year old and he asked if they were real.
“Of course they’re real,” I laughed, “I’m only seventeen!” and then he asked if it was too much to ask for him to see them. He kept up his lines, saying how his wife was small breasted and he couldn’t remember the last time he’d seen a fuller bust except for in the newspaper, and I fell for it, not objecting as he unbuttoned my top all the way down, and then gazed at my boobs in my bra.
That was when I started getting quite horny, and I knew right then that I wasn’t going to stop him doing anything he wanted. That might have the been the first time I ever felt submissive with a man, I’m not sure, but I didn’t stop him as he lifted the bra up and over my breasts, exposing them to him fully. I reached around my back to take the bra off altogether for him as he first touched them, then cupped and squeezed them with both hands, rubbing his thumbs over my nipples which were incredibly sensitive back then.
“Can I ask a personal question?” Colin asked after another long, passionate kiss. “How many boys have you slept with?”
I don’t really know why I lied and said, “A few,” or why when he pressed me on how many, I told him that I’d been with four boys, I guess it was because I felt foolish at being a virgin at seventeen. It was lucky that I didn’t tell the truth though because he smiled and said, “Good. I couldn’t have done this if you were a virgin.”
That prompted a moment of panic. What if he could somehow tell that I was a virgin? I knew my hymen had broken, but what if he could somehow tell in other ways? Surely, Colin had been with more than his fair share of women in his past, so he would recognise an inexperienced girl, wouldn’t he?
I didn’t get a lot of time to worry because he started kissing me again, and now his hand moved back down to my leg, sliding up my thigh until it rested on the outside of my knickers. I knew I was wet down there, and I felt another moment of worry that he would laugh or something but of course he didn’t. His fingers expertly pulled my panties to one side, and then his finger went inside me.
I don’t know how long he kissed and fingered me for, or exactly when my hand roamed to the front of his trousers, but I know I was rubbing the outline of his hard penis when he finally stopped kissing me and asked me if I’d ever sucked a man.
“Yes,” I said truthfully this time, but then followed it up with a lie by saying, “Lots of men.”
“Ah,” he said, unbuckling his trousers, “You like giving blowjobs?”
“I love it,” I said. What was I thinking? I’d only ever sucked one boy off, and only done it to him twice. I suppose I was just trying to impress Colin but I realised I’d got myself into a bit of a situation when he eased his trousers and shorts down, to reveal a very hard and thick cock. It was probably only average in length, but it was just the fourth one I’d seen and I still wasn’t sure what ‘average’ was so it seemed quite daunting as I lowered my head down and began to kiss the end.
Colin had eased the seats back, so I could make myself comfortable and I began to explore his cock with my tongue, trying to remember and copy the techniques I’d seen pornstars do on the internet, and the older man seemed to be enjoying it, putting his hand in my hair and pushing me deeper onto him. I think I gagged a couple of times, but I daren’t stop, or he’d see me for the inexperienced kid that I was.
His arm reached behind across to play with my pussy while I gave him the best blowjob I could, and he literally had me almost on the edge of orgasm by the time, he finally pushed me onto my back and stripped my knickers down and off my feet.
‘This is it,’ I realised as he positioned himself between my legs, but I didn’t have any time for nerves. One second his cock was slipping up and down between my labia, then the next he just shoved it in. One smooth movement, and then he was deep inside me. I didn’t even get the chance to savour the moment, he put his hands beneath my legs, lifting them and spreading them and then beginning to fuck me right there in the passenger seat.
It was so intense, the feeling of his cock penetrating me, the weight of him above me, his kisses on my neck and the sound of his breathing in my ear and of the impact of our bodies. A steady slap, slap, slap and the slightly embarrassing wet sounds of my pussy as he fucked me.
I was lost in the moment. I don’t know how long it lasted for, I only remember noticing the lights of a car as it went past but I didn’t care and then Colin made me climb into the back so I could get onto all fours for him. I felt very exposed, and he didn’t help by spending several minutes playing with my throbbing pussy from behind, commenting on my ‘sexy arse’ and how great my tits looked hanging down. All I could think about was how fat and wobbly my bottom probably looked and that my breasts more closely resembled udders in this position, but just as I was starting to feel more uncomfortable than horny, Colin shoved his hard dick back inside me, and began to have fast, hard sex with me from behind.
I wasn’t sure if I was enjoying the rough treatment I was getting. He switched between pulling my hair to pushing my face down into the seat as he approached his climax, talking dirty the whole time, but while my mind was undecided, my body was definitely liking it. My clit felt like it was going to explode, and I couldn’t help but reach underneath and within just a minute of rubbing myself, I came loudly.
Colin was calling me filthy names while he fucked me, and my shuddering orgasm only served to make his vulgarities even more profane, but for some reason I didn’t care, in fact it turned me on even more and I think I was actually pushing back on to him during the last couple of minutes until he finally pushed deep into me and I felt him pulsing inside.
“No,” I said suddenly and urgently, and tried to push him away, but it was too late. I felt the cool stickiness of his sperm inside me, dribbling out as I sat up in a panic. “I’m not on the pill,” I said, not knowing what else to say. I suddenly felt sober from the shock of what I’d just done. How could I be so stupid?
“You are kidding me?” Colin said, equally shocked, then he began to apologize for making assumptions but I couldn’t blame him. I’d made out that I was promiscuous and I’d never asked him to use a condom or anything, so of course what else was he to think other than I must be on the pill?
He kissed me and said that I’d be okay. Even though he’d cum in me, the chances of me getting pregnant were slim - and that I shouldn’t worry. He took me home, and I pretended to be fine but as soon as I got to my bedroom, I threw myself on the bed and cried myself to sleep.
The following month was hell, waiting for my period to come. I did several pregnancy tests, which all came back negative but I was terrified until finally at the end of January, I got my period and then the world was all okay once more. I’d learned a valuable lesson though, and I never made such a silly mistake ever again.
The horrible scare wasn’t a nice thing to go through at all, but it hadn’t completely ruined my first time. Even through the stress and worry, I would quite often think of that night in the car, the way he fucked me so roughly, the smell of the sex, the physicality of him and how strong he was. I masturbated numerous times at night in bed, imagining him behind me and the feeling of his cock inside me, using me like the slut that he thought I was.
Colin phoned me regularly, concerned about me, and we met up for a coffee a couple of times, and I even went on a date with his son a couple of weeks after Christmas, who was a nice young man, but it was a total disaster because all I could think of was that I might be pregnant, with his brother or sister growing inside me.
Once a very-relieved Colin found out I wasn’t pregnant, he stopped calling me for a little while, but out-of-the-blue in the middle of February, just before my father’s birthday, he arrived at my front door. He had a card for Daddy but I think that was just an excuse, because once I told him that Daddy wasn’t home, he asked if I’d mind a quick chat, and thinking it was about his son, or something like that, I invited him in and made him a coffee.
Again, in hindsight it is quite obvious that he’d set this up. He didn’t waste any time in getting to the point. He told me that he was sorry he’d put me through the agony of wondering if I was pregnant, but said that he’d really enjoyed that night in the car and he would do anything if he could see me again sometime. He promised to be discreet. He didn’t want a relationship, just some fun, and when I said I wasn’t sure, he even said that he would treat me right and if there was anything I wanted from him, he would buy it for me. He said he would pay for driving lessons, even get me a car. He had lots of money, and would enjoy spending it on me, if I was willing to be his ‘special friend.’
I was shocked and had no idea how to respond to what amounted to being offered money for sex. I didn’t want to offend him, so I told him I would think about it, and to be fair to Colin, he didn’t pressure me at all. He finished his coffee and told me to call him and let him know either way. If I didn’t want to see him again, he totally understood, and he hoped I wouldn’t tell anyone.
The money never tempted me because I’d never been without money. It was something I’d always taken for granted with such a gracious and generous father, but for some reason the fact that someone (especially such a good-looking man as Colin) wanted me so much as to actually buy me gifts caught me off-guard. It was hugely ego-boosting that he must have enjoyed that night so much that he wanted to do it again, and it had only been my first time. I wondered if that meant I was good in bed? I hadn’t even known what I was doing that night. With practice, I’d get even better, right?
But still, I wasn’t going to sleep with someone just for the sake of it. The night with Colin had just happened. The alcohol and the party season spirit had got to me, and I’d got carried away with myself. I’d very nearly screwed my entire life up.
So why, one lonely and boring night just a month or so later, did I pick up my mobile phone and flick through the contacts list to Colin’s number, and press the call button?
To be continued...