Have you ever received a friend request on Facebook that stirs up a whole load of memories you haven’t thought about in years?
This happened to me last year. Out of the blue, I saw a notification from a guy I hadn’t seen in over two decades. I don’t think I would have recognised him from his profile photo – he has changed considerably since we last saw each other in person – but I knew his name in a heartbeat.
I instantly began reminiscing about our time together, vivid images flooding my mind. Over the following days, I started recounting that incredible, transformative period of my life, the years before, with and just after him, and it was only when I stopped and thought about it that I realised just what an important role he had played in my life so far.
Jay was not my first love, nor was he my first lover: he was the guy who taught me how to fuck.
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Before I get into that part of my story, I’ll go back a little bit further to provide some context.
In some ways, I was a late developer when it came to sexual experiences. I’m almost ashamed to admit that I didn’t lose my virginity until shortly after my eighteenth birthday, though I would like to note that this wasn’t due to a lack of enthusiasm on my part.
As a teenager, I was quite shy, very studious, not particularly sociable, and always on the plump side. I’d had a few boyfriends, including a long-distance relationship with a lad I’d met on holiday in Crete, but this had led to little more than a few kisses and cuddles. At school, I wasn’t popular with the boys as most of them preferred skinnier girls or those with a bad reputation. I’d been brought up in a fairly conservative household and had it drummed into me that “good girls wait until they are married” and, whilst I didn’t subscribe to this idea, I did have romantic visions of losing my virginity to someone that I truly loved.
However, once I turned sixteen, the game began to change.
I started going out to pubs with my friends at the weekend and quickly morphed into a confident, flirtatious little minx. Whilst the boys in Sixth Form lusted over willowy, ironing board-esque figures, the older guys we were hanging around with in bars seemed much more appreciative of curvier, womanly bodies. At this time, I had perky 36C tits, a generously proportioned bum, and long legs. I had long, glossy brown hair and was told by several people that I resembled a young Demi Moore (I could never see this myself). I loved wearing tight, low-cut tops, miniskirts, and strappy high-heeled sandals (this was in the mid-nineties when the Spice Girls were huge, and Victoria was my style icon).
During this period of my life, I lived for Saturday nights. I would study during the week and work in a shop during the daytime on Saturdays and Sundays, which provided money for clothes, make-up, taxis, and alcopops (we thought we were the height of sophistication with our bottles of Hooch, Mule or Bacardi Breezer). Rarely did the bouncers or bar staff question whether we were old enough to be in such establishments, and we quickly learned that attaching ourselves to men in their twenties or even thirties would get us anywhere we wanted to be.
My friends and I would spend all our free periods between lessons talking about what we planned to wear, who we fancied and what we had done with different guys the weekend before. It was an unspoken challenge that all the single girls would try to find a guy to dance, kiss and fumble in a dark corner with. Sometimes more than one in the same night. I loved the thrill of the chase; I found it intoxicating to end up in a stranger’s arms, being kissed by “real” men and feeling their hands roaming over my body. Looking back, I can understand how some people may have found this behaviour inappropriate – especially when some of these guys were probably more than twice my age – but in the grand scheme of things, it was all harmless fun and I have no complaints or regrets.
As the months went by, I started to develop a strong sexual appetite. On numerous occasions, I ended up with one of these random guys’ hands in my bra or between my legs, and I lost count of the number of erections I had pressed against on crowded dance floors during the slower songs.
I knew I needed more.
I would go home at the end of the night and get myself off with my fingers (I had already mastered the art of this from experiments involving the true confessions page or “position of the fortnight” in More Magazine, hairbrushes, and mirrors), thinking about what could’ve happened if the fumbling had gone further. There were plenty of offers and, thinking back, my hometown was perfect for this type of action. It’s an old, traditional market town, full of hidden alleyways and opportunities to do delicious things in the darkness (more on that later), so if I’d wanted to lose my virginity leaning against a brick wall or bent over a park bench, it would’ve been an easy mission.
But I still had the idea in my head that I needed to find the right person to ensure it would be the perfect first experience.
The December of that year provided two occasions where I thought I might have met “the one”. Our school had a tradition of hiring a nightclub in a nearby city for the Sixth Form Christmas party, which was a fancy-dress event. Having tried on loads of outfits, I had decided to go dressed as Snow White, albeit a sexier version of the fairytale. There was lots of drinking and fumbling – I recall at one point making out with a guy dressed as a nun (who had two giant balloons under his habit, giving him tits that could rival Dolly Parton’s assets, let alone mine) – and everyone was in high spirits, as you would expect when you mix horny students with cheap alcohol.
Near the end of the night, I ended up dancing with one of the club’s glass collectors. He was several years older than me and a student at the local university. We ended up kissing and he asked for my phone number. The next day, he called me as promised and the chemistry seemed as good as it had been the night before. We arranged a Christmas shopping date for the following weekend, and there was a casual reference to possibly going back to his place for dinner later. I thought that this seemed like a good opportunity to get laid, and it probably would’ve been – if he hadn’t stood me up (which he later blamed on the world’s worst hangover). That was the end of that one.
The second festive frolicking incident happened on New Year’s Eve. I was out in town with friends, and it was the busiest night I had ever seen in the pubs. Most had queues waiting to go in, and it was almost impossible to move inside. Near midnight, I got separated from the other girls – they moved to a different pub and, somehow, I got left behind.
Suddenly, a fight broke out and the doors were locked to prevent more revellers from entering the building. I remember feeling terrified, especially when people started throwing glasses around the room, but then a tall, well-built stranger appeared. I realised he was one of the bouncers and noted that he was extremely attractive. He pulled me into a corner, away from where the trouble was, and told me not to worry because he would keep me safe. Strong, protective men are still a weakness of mine to this day, so back in my teen years, a line like that melted me. We ended up kissing, which completely took my mind off the chaos, and only stopped once my friends came and found me. He told me he would be working in the same bar next weekend and asked me to come and see him again then. Naturally, I was giddy at the thought of where this could lead – he seemed to tick all my requirement boxes – but this came grinding to a halt a few days later when a mutual friend told me that my dream guy was dating another girl at my school. She’d got wind of the news he’d kissed someone else and was on the warpath, so I decided not to play with fire and left well alone.
As winter turned into spring, I continued my quest to find someone to provide the first notch on my bedpost, and towards the end of March, I thought my prayers had been answered.
I met Cal on a normal Saturday night out with my friends. We were in one of our favourite bars, dancing and having a laugh, when one of the girls told me that she’d noticed a guy who kept looking at me. I casually turned around to see who this might be, and sure enough, he was staring in my direction.
I know that the idea of love at first sight is considered a cliché by some and an impossibility by others, but I was instantly smitten and fell head over heels for him.
To cut a very long story short, it turned out that he was a sailor in the Royal Navy, but he regularly came back to visit his parents (who lived in the same town as I did). We met up the following weekend, and several times the week after as he’d taken a week’s leave to house-sit for his mum and dad whilst they were on holiday. He invited me back to their place twice, but other than some kissing and touching, not much happened. I convinced myself that this was because he was a gentleman and didn’t want to rush me. Part of me was a tiny bit relieved as I discovered his father was a taxidermist. Desperate though I was to lose my virginity, I wasn’t keen to do so in a house full of dead animals.
After that week, he was away for a month and I wrote to him every single day (yes, this was in the days before email and text messages). We spoke on the phone a few times, and I became more and more convinced that not only would we end up sleeping together, but we would also spend the rest of our lives together! Sadly, that dream would die the next time he came home. Having cancelled plans to see me that night, I later bumped into him in town… whilst he had his tongue down another girl’s throat. To make matters worse, when I challenged him, he casually replied something along the lines of, “Yeah, I guess I’ve fucked up. So, as I see it, you’ve got two choices: either get over it or don’t”. I honestly thought that my heart was going to break at that moment; I can still remember the pain all these years later.
It’s fair to say that the (imaginary) wedding was off at this point.
After this devastating turn of events, I began suffering from panic attacks and became somewhat of a recluse, only leaving the house to go to school or my part-time job. I couldn’t face going to pubs, but I also wanted to find someone to help me get over Cal (even though I was still pining for him and hoping for a movie-style reunion).
I ended up dating a guy in my class who, if I’m honest, was not my type. He was sweet but very immature. I realised quite quickly that he, too, was desperate to lose his virginity and made no secret of it – he was practically humping the furniture some days. And it very nearly happened one day – behind some bushes on the school football field, of all places – but we got interrupted just in the nick of time (his hands had got as far as the inside of my knickers, so he had at least achieved “wet fingers” bragging status). Ultimately, the chemistry wasn’t there, and it fizzled out quickly soon afterwards.
I was still in love with my ex, and no one compared to him in my mind.
As luck would have it, a few weeks after that relationship ended, Cal wrote to me out of the blue to apologise for what he had done and to ask for another chance. He said he would be home for the whole of August and wanted to make it up to me. I admitted to him that I was struggling to go out socially. He was lovely about it and suggested a date walking around a local park. I was thrilled at how thoughtful he was being and convinced that this was a sign that we really were meant to be together. Unfortunately, the day after said date, he had a change of heart and decided that he didn’t want to spend his leave with a boring girl who didn’t want to go clubbing, so the nuptials were off again.
It took a long time to begin healing from this, but by the start of the following year, I started feeling better and going out again. I had lost time to make up for and soon got back into the swing of flirting with strangers and kissing in corners. My confidence was almost back to normal, and I felt positive about my chances of meeting someone new.
On a night out to celebrate a friend’s eighteenth birthday, we were dancing away when one of the girls – who didn’t normally hang out with us – mentioned a guy was looking over at me. Intrigued, I turned around, only to see a certain sailor before me once more. With all the maturity of a typical seventeen-year-old, I opted to play hard to get. I wanted to make him jealous. So much so, that I ended up kissing another guy, hoping my ex-boyfriend would see.
Unfortunately, my cunning plan backfired later that night. The guy I was flirting with got steaming drunk and turned nasty when I told him I needed to go home. He had me trapped against a wall, away from where all my friends were, and I thought he was going to hit me. As I tried to figure out how to escape, a figure appeared from behind him, pushing him out of the way. To my great relief, Cal pulled me to safety and told the guy to leave me alone.
“What’s it got to do with you?” the guy I’d been with said.
“When it comes to her,” Cal replied. “It’s got everything to do with me.”
With that, he took my hand and led me outside. I was pretty shaken up by the ordeal, even though I knew I was partly to blame for it, so when he went to pull me into his arms, I didn’t need asking twice.
“You should be more careful about who you kiss, you know,” he said, stroking my hair.
“You’re a fine one to talk!” I retorted. “Have you forgotten what happened last year?”
We both started laughing at this point and it felt good to be with him again. I loved the feeling of having his arms around me, breathing in his familiar scent. He told me that he still hated himself for hurting me in the past, that a day didn’t go by without him thinking about me at some point, and that he would always protect me because I meant the world to him.
We were just about to start kissing when our friends arrived, ruining the moment, and then it was time for me to go home. Cal told me he’d see me around and winked at me in a way that made my knees go weak, and I felt sure that it would be third time lucky, that we would finally end up shagging soon (even if wedding bells weren’t going to be ringing anytime soon). I was still naive, romantic, and holding out for the fairytale first fuck; there was only one man for the job in my mind.
A week or so later, I got chatting with a mutual friend at school. She dropped into the conversation that she had seen Cal a few days beforehand, and I couldn’t resist asking if he had mentioned me.
“I doubt it,” she laughed. “He had his girlfriend with him. Things are getting pretty serious between them. They’re thinking about getting engaged this year.”
And that was the point when I finally accepted that my Popeye would not be popping my cherry.
It was time for me to move on. And move on, I did.
That summer, I left school and got my first full-time job working for a local engineering company. I was one of only three women in an otherwise all-male environment, and the other ladies were much older than me. Needless to say, it was quite the novelty for the guys to have a spirited, young, single female in their midst, and I thoroughly enjoyed all the attention I got.
Just after I started there, I went out to celebrate another friend’s eighteenth birthday at a club in town. Towards the end of the night, I got dancing with a good-looking guy who I vaguely remembered from school and ended up kissing him. We were still there at closing time, so a group of us – his friends and mine – hung around for a while in an alleyway off the main street. It was a warm, summer night and everyone was buzzing, so wanted to stay out later.
The two of us moved a bit further away from the others and carried on kissing. He was sitting on a wall and I was standing between his legs. I can’t recall exactly how it happened – whether it was some sort of dare or just pure horniness – but at one point, I realised he’d taken his cock out of his jeans. Even though I had never done anything like this before, I instinctively bent down and started sucking it. It was like an out-of-body experience – to this day, I don’t know if someone had slipped something in my drink as this was just so far out of my normal character – but I willingly gave him oral in front of an audience. Thank fuck this was in the days before people had camera phones!
We never discussed it, but I think we both knew that this was only ever going to be a one-off, so after waving him goodbye and going home, I never saw him again.
I figured out that work might be a good place to find a new, mature boyfriend; the only problem was there were few single men there and most of them were younger than me, which was a no-no at that point. However, there was one guy who was in his twenties and unattached, and we started chatting most days. I didn’t find him physically attractive, but he was good company and made me laugh. He was generous, hardworking, and close to his family, all of which I felt were more important than having movie star looks. The older people in the office were keen to do some matchmaking and joked that they’d only hired me to help him get a new girlfriend. It felt like everything in the Universe was conspiring to bring us together, so after sharing a passionate kiss at a colleague’s birthday party, Shaun asked me out and I said yes.
As luck would have it, my parents went on holiday a few weeks later, leaving me and my best friend to house-sit. She had recently got a new boyfriend, so I knew she’d be at his house for at least some of the evenings, giving Shaun and me some space to get to know each other better. We arranged for him to come over on Friday night – under the pretence of watching a film together – and I was determined that this would finally be the night I became a woman, so to speak.
I left work earlier that day to get ready, making sure I had time to shower, wash my hair, shave my legs, put fresh sheets on the bed, etc (basically the standard preparation for a woman who thinks she’s going to be having sex soon). Emboldened by nineties Girl Power, I even remember going to buy condoms on my way home to give the impression that I looked like I knew what I was doing. So, by the time he arrived, everything was ready. Or so I thought.
We sat on the sofa, half-watching a movie (he picked Star Wars and I got bored quickly) and chatting. That soon turned into kissing, one thing led to another and before long, I was finally saying the infamous words:
“Shall we go somewhere more comfortable?”
So, we moved to my bedroom and everything was going well. The lights were off, we were naked, and things were hotting up nicely. I wasn’t consciously nervous – after all, I had waited a long time for this moment – but I think I must’ve been, as I suddenly remembered a silly impression he’d been doing earlier when we were downstairs and got the urge to start giggling. The more I tried not to, the worse it got. He sensed something was amiss and that my mind was not on the job, and when he asked what was going on, I descended into a fit of what I can only describe as mild hysteria.
I quickly learned that this is not what guys want to hear in bed; he was certainly not amused.
We carried on making out, hands everywhere, building up the passion again. At some point, he asked me if I wanted to go all the way; I said yes without any hesitation. I remember lying there as he fumbled to put a condom on (he’d also bought some), feeling the biggest sense of anticipation I had ever had. He got on top of me, and I spread my legs, ready for him. I could feel his cock pushing against my pussy, he was wriggling around and making some grunting noises, and then he suddenly said:
“It’s not going to happen. You’re too tight, and if I keep going, it’ll hurt me as well as you.”
I was mortified. I told him that I wanted to do it and asked him to try again, but he was adamant that I wasn’t ready, and he didn’t feel comfortable continuing. I’m pretty sure I was in tears, feeling like a complete failure, and we ended up cuddling in silence for a while until he said he needed to leave as he had to work the next day. We agreed to meet again the following evening, and I can vividly recall lying there, alone, wondering what was wrong with me. I blamed myself and my inexperience for what had happened; it didn’t occur to me until months later to question that he could’ve handled things differently, or that he might have enjoyed the power trip of making me feel inferior.
Throughout Saturday, I constantly replayed the disastrous previous night in my head. Shaun had said that he thought we should leave it a while before trying penetration again, so I knew sex would not be on the cards when he came over in the evening. I felt nervous and awkward when he arrived, but he acted like nothing had happened. We put on another movie and cuddled up on the sofa. There was some kissing and a bit of touching through clothing, but that stopped when my friend and her partner came back from the pub. We all sat up chatting for a bit and then they decided to go upstairs, leaving us alone once more.
Shaun told me that he wouldn’t be able to stay late and, as neither of us wanted a replay of the last time we’d been in my bedroom, we stayed in the lounge. I can’t remember why, but at some point, we moved from the sofa onto the floor, lying on the carpet. There was lots of playful kissing and touching going on, and the energy between us felt good.
Suddenly, we were both naked, his fingers were inside me and he was asking me if I wanted to try again. Even though I was terrified of the same outcome, I said yes. As he reached for another condom, I could barely breathe. Everything seemed to be happening in slow motion as he climbed on me for the second time. I felt him moving between my thighs and willed my body to stay relaxed. Leaning down with his arms on either side of me, his cock began pressing against me, slowly but firmly, until I felt him push further, opening and entering me with each thrust. Neither of us said anything; we just looked at each other, smiling and kissing, as he continued to fuck me. I didn’t care when he came and I didn’t, I was just so thankful that we’d managed to go through with it this time and that I was officially no longer a virgin.
For the remainder of the week that my parents were away, Shaun continued to visit most nights. We experimented a little; I can’t remember exactly what this involved, but I guess we may have tried a few different positions (the fact this part isn’t memorable tells me we probably stuck to missionary most of the time), and I know we gave each other oral. He let slip one night that he had only had sex on one occasion before me (with an older woman who had told him what to do), so I think our combined inexperience and my lack of confidence stopped us from doing anything too adventurous. I remember that I didn’t mention that his wasn’t the first cock I had sucked as he seemed to get off on the fact he’d been the first guy to fuck me, so I let him think he’d been my first everything else as well.
The relationship was great for the first month or so. I ended up being hospitalised twice due to illness, and he was sweet, buying me flowers and visiting me in the hospital. We often double-dated with my friend and her partner and would spend our lunch breaks at work together. Sexual opportunities were quite limited, as we both still lived at home, and some issues with my appendix scar made certain positions impossible. But we did what we could, when we could, and started involving massages, edible body paints and sexy lingerie (for me, not him) to make things exciting.
Unfortunately, as we got towards the end of that year, cracks were starting to show. I was going through a difficult time at home, still struggling with low energy from the glandular fever I’d had months ago, and desperately missing my friends (all except two had moved away to go to university). I lost my mojo and sparkle, and I had little interest in going out. My social anxiety began to creep back in, especially around anything involving people I didn’t know well or going out for meals. Shaun didn’t understand this; he wanted the trophy girlfriend to show off to his friends and family. When I declined an invitation to have dinner with his parents, he told me – rather unhelpfully – that his mother (whom I had only met once) had decided that I had an eating disorder, and he thought she was right. It was clear that his family thought I wasn’t suitable for their son; equally, my family were not keen on his constant bragging and need to make himself look superior at all times. In private, he could be quite negative about me and my body, and he would occasionally make references to our first time together that made me feel bad about myself.
Eventually, after a hideous week during which he refused to speak to me about anything other than work, avoided me at lunchtimes and wouldn’t take my calls, he told me that it was over, because he “didn’t feel like he had a girlfriend”. I could understand his frustrations – after all, these should’ve been exciting times for us – but I wasn’t able to instantly transform into the dream girl he wanted.
Even though the relationship had become truly toxic, I was devastated at the thought of it ending, especially as we worked together and would still see each other every day. He was the only man I had slept with, and I was convinced that we loved each other, even if we didn’t like the other person a lot of the time. I will be forever thankful to our colleagues for helping us move through the awkwardness that followed; they did not take sides and treated us equally. Our joint friends still made the effort to spend time with both of us, albeit individually, and this made a bad situation bearable.
A few weeks after the breakup, my best friend called me to tell me that she and her long-term boyfriend had also split up, completely out of the blue. While I was sorry to see the pain this caused her, it helped me to have a single friend nearby and we were able to support each other with moving on.
We started going out drinking again at the weekend, flirting with strangers, and generally enjoying being young and free. I was saving for the deposit for my first home at this time, so took on extra hours at work and a second job to be able to afford a reasonable social life. One of us suggested that we should book a girls’ holiday abroad and, after hours spent browsing holiday brochures, we picked a destination in Spain. We were determined that we would make the most of our break, sunbathing all day and then partying at night.
However, the month before we were due to go, my friend began dating one of her managers at work, and she made it clear that she would not be looking for a holiday fling while we were away. Naturally, this impacted the fun that I could have as it’s not much fun going on the pull with a non-single friend. What made it even worse was that her new boyfriend asked (and she agreed) to phone him before he went to bed each night, so as this was in the days before mobile phones and roaming were commonplace, we would have to find somewhere quiet with a payphone before 11 pm, which often meant returning to where we were staying.
The only action I got close to having was on the last night. We stayed at the hotel for the evening as there was some sort of fiesta or party going on and we were promised unlimited free sangria. I ended up dancing with a guy who either worked there or lived locally – I wasn’t sure which as he didn’t speak any English and I spoke only a tiny amount of Spanish. Towards the end of the party, I went to the ladies’ toilets and he followed me. We started making out and he gestured towards one of the cubicles, the erection he was sporting making it quite obvious what he was suggesting. I was giving this non-verbal offer some serious contemplation when a security guard came in, started arguing with my new friend in their native tongue and promptly marched him out of the hotel.
This left me ridiculously horny. So much so that I remember waiting until my friend had fallen asleep (we were sharing a room with beds practically touching each other) before fingering myself like crazy and having an intense but silent orgasm with her lying about an arm’s length away from me.
It was around this time that I developed a huge crush on another co-worker, Jay. We hit it off from when I first started working there, despite there being nearly a decade between us. He was outgoing, funny, and always up for a laugh. He was also an outrageous flirt, loved to tease me and constantly made me blush. In the beginning, I didn’t see this going any further as he lived with his long-term girlfriend. When Shaun and I got together, Jay backed off a little as they were friends, and he didn’t want to step on his toes.
Jay could not have been more different to Shaun. He was the stereotypical bad boy: he had a deep, gravelly, sexy voice, a ponytail and a sparkle in his dark eyes that always felt deliciously filthy. Shaun was hardworking and stuck to the rules; Jay loved to mess around and was often getting in trouble for minor workplace misdemeanours. For all that Shaun was entitled, privileged, and spoilt by his doting, rich parents, Jay had had a tougher start in life, becoming independent early on and losing his mum some years ago. He had that incredible ability that some guys possess to make any woman he was talking to feel desirable and seen; all the women who worked there loved his company and his sexual banter, and I was like a moth drawn to a flame whenever I spent time alone with him.
I remember that the month before Shaun and I split up, I bumped into Jay in a corridor between the office. He immediately started flirting with me, culminating in him playfully pinning me against a wall, asking for a Christmas kiss and promising not to tell anyone if I let him. I declined, knowing that my relationship was already rocky and that Shaun was jealous of any attention Jay paid me, but I spent the days afterwards regretting my decision and wondering what it would’ve been like.
Just after I returned from Spain, Jay and his girlfriend split up. I believe that he discovered she’d been cheating on him with one of his friends (though, with the benefit of hindsight, I’m not convinced he’d been entirely faithful to her during their relationship), and he spiralled into a dangerous depression, drinking heavily, smoking weed and getting into trouble. We all rallied around, supporting him and trying to help him move on with his life; gradually, he started getting back to something like his old self. He and I were spending a lot of time together during this time, which varied between having deep conversations about failed relationships and cheering each other up. I think Shaun resented me moving on with my life as he had become spiteful and petulant towards me at work, but Jay spoke to him about this – I’m not sure what was said – and things seemed to improve after that.
I moved into my new home in August of that year and was super proud of it. I felt it was a huge achievement to get a mortgage on my own at just nineteen years of age, without any help, and I couldn’t wait to start inviting friends over to see my house. One evening, I was sitting back relaxing after work when I got a text from one of my best friends from work, Adam. He told me that he and Jay were hanging out together – they were also good friends – and asked if they could come and see me. Delighted at the prospect of having some company, I said yes, and they turned up about an hour later.
The three of us sat around talking, drinking, and watching TV. After about an hour or so, I went to the kitchen to make some coffee. I was sitting on the worktop, waiting for the kettle to boil, when Jay walked in and shut the door behind him. I can’t remember exactly how the conversation began, but he told me that he’d fancied me for a while and asked me how I felt about him. One thing led to another, and we ended up kissing passionately, me still sitting on the counter, him standing between my legs.
I could sense that Jay was incredibly horny. He pulled my t-shirt up and started playing with my tits. I had never experienced breast attention like this before (it would go on to become one of my ultimate turn-ons), and when he undid my bra and started sucking my nipples, I thought I had died and gone to heaven. It was unlike anything I’d experienced in the past, he seemed to know exactly what I needed and provided the perfect combination of hand, mouth and tongue action. It all felt so naughty – the kitchen blinds were open, allowing anyone walking by a view of what we were doing, and one of our friends was sitting just the other side of the door – but this just added to the excitement.
At one point, I think I started moaning out loud (possibly when he pulled my skirt up and started rubbing my pussy through my knickers). Jay put his free hand to my lips, urging me to be quiet, and his other hand slipped beneath the soaking cotton. He knew exactly what he was doing, and it drove me wild. When his fingers found their way inside me, I thought I would pass out.
Taking his hand away from my mouth, he began to undo his jeans. I looked down and saw his cock for the first time, which was already rock hard. That was the first time I realised that he intended to fuck me. A sudden wave of panic came over me, not because I wanted him to stop – I had never felt desire like this before – but because I had a flashback of my first, unsuccessful experience of sex. I was terrified that the same thing would happen again.
I whispered to him that we should stop, that it felt too soon (I didn’t want to tell him what I was really feeling). In response, he gave me a mischievous grin and said we could still have some fun without going all the way. With that, he pulled my underwear to one side and started rubbing my clit with the head of his cock. This was another new sensation for me, and it was exquisite. It took everything I had to remain silent as he continued to pleasure me with his hard tip, but just as I felt an orgasm approaching, he stopped.
“You’ll appreciate it even more if you have to wait for it,” he whispered as he pulled his jeans up.
I sat there stunned, wondering what had just occurred as he returned to the lounge, leaving me half-naked, needy and drenched. It took me a few minutes to compose myself, replace my clothing and rejoin them. When I did, Jay acted like nothing had happened. After he left, I questioned whether I had imagined the whole thing. It was only when I got a cheeky text from Adam the next day, asking if I could turn the music up the next time I was having sex in the kitchen to drown out the noise, that I knew that something had gone on.
For the next few days, Jay continued to torment me. There was one occasion when he came to my desk and stood behind me, pretending to look at an order on my screen, then surreptitiously unhooked my bra without anyone around us knowing what was going on. Another time, he pulled me into a store cupboard when no one was looking and played with my nipples through my blouse. My longing for him grew every time was near me.
Towards the end of that week, I was chatting with one of the guys in the office about my new home. He asked what the pubs were like in my village, to which I said I didn’t know as I hadn’t visited any of them yet. Jay happened to overhear this and told me he didn’t have any plans for Friday night, so would take me on a pub crawl if I fancied it. I was slightly apprehensive as I had started my period that day, which I thought would be a problem if we were going to continue what had started the last time he’d been to my house, but I didn’t want to turn down the chance of spending time alone with him.
It turned out not to be an issue and we had a fun evening regardless. We walked from pub to pub, discovering that we were overdressed for such traditional establishments, which caused people to stop talking and stare at us as we entered. Eventually, we accepted that we might be a bit young for these sorts of places and went back to my house. We’d both had a fair bit to drink by then, so when I told him that I was temporarily out of action, he was happy to do some sexy snuggling (I’m fairly sure I used my hands to make him cum) and fall asleep. I loved the feeling of dropping off in his arms, and I think he was happy knowing he was the first guy to visit my new bedroom.
He left early the next morning (I had to go to my second job) and I didn’t see him again until work on Monday. That week was much the same as the previous one, with him finding opportunities to kiss and touch me whenever possible. It was exciting that we were the only people that knew what we were doing, that we had the most incredible, sexy secret between us.
One lunchtime, we had a conversation about hidden talents, and I mentioned that I’d learned some massage skills from a video I’d watched, but I hadn’t had the chance to test them out on anyone yet. Jay texted me that afternoon, something along the lines of I could use his body anytime I wanted to, and we agreed that he would come to see me on Friday night again.
Everything was ready by the time he arrived. I’d spread a large towel out on the lounge floor and filled the room with tealight candles to give a warm, sexy glow. There was music playing and I’d purchased a sensuous oil to use. I think as soon as he walked in, he knew that I was hoping for more than just some massage practice, but he played along with the idea that was why he was there. I watched him undress, down to his boxer shorts, and asked him to lie down. His body was so incredibly masculine; just looking at him sent shivers down my spine.
As he lay there waiting for me to get started, I decided to move things up a notch.
“It’s probably best if I take my clothes off as well,” I told him. “I don’t think that oil stains will wash out of the fabric if not. If you want to lie on your front, I’ll be ready in just a moment.”
I waited until he had rolled over until I stripped down to just my bra and knickers, then knelt at the side of him. Warming the oil in my cupped hands, I got to work on his legs and gradually moved up to his waist. At this point, I straddled him so that I could use both hands on his neck, back and shoulders. Although I was taking it seriously, kneading his muscles with my palms and fingertips, my mind was preoccupied with what would happen next.
My unspoken question was answered when he turned over, onto his back, and pulled me down on top of him. We kissed passionately, his oily skin rubbing against my body as we moved around on the carpet, hands exploring each other in detail.
He practically tore off my underwear as well as his own, before going down on me. The oral I had experienced in the past was what I would probably describe as nice and efficient, i.e. it did the job. But Jay ate me like he was ravenous and I was his last meal. He devoured me as if my juices were the most delicious cocktail he had ever tasted, stopping just before he tipped me over the edge.
“Would you like to do it down here, or upstairs?” I asked.
“Both,” he replied. “First I’m going to fuck you down here and then I’ll have you on your bed.”
He was a man of his word.
Pushing my legs apart, he rubbed his cock against my clit as he had done before. This time, I moaned out loud – I didn’t care if the neighbours could hear through the flimsy walls, all I cared about was Jay and this moment. Before doubt could enter my head, he had entered me. I clung to him as if my life depended on it, my arms around his neck as he took me with long, deep thrusts.
I have no idea how long it lasted as it all became a lust-filled blur, but after exploding inside me (I didn’t ask him to use a condom – I was on the pill and wanted to feel the full “natural” experience of sex), I’m sure that he used his fingers to bring me to orgasm.
We stayed downstairs whilst we recovered, either listening to music and chatting or watching TV. It amazed me how we could go from doing what we’d done to chatting like best mates so effortlessly, but he was great company and willing to talk about anything and everything. He made me laugh and showered me with compliments, and I loved every moment we spent together.
Through my inexperience, I had assumed that he hadn’t meant it when he said he would fuck me twice in one night. Shaun and I had rarely spent a full night together, but even when we did, it had been a case of fuck, get a full night’s sleep, fuck again the next morning. So, when Jay and I eventually went up to my room, I was surprised – and excited – to see him hard again.
This time, it was different. He took his time, almost as if he was trying to give me a lesson in sexual pleasure. He was so in control, and it turned me on as he took charge, telling me what to do. I vividly remember the feeling of his hands in my hair as he fucked my mouth; he knew exactly what he wanted and made sure I knew how to give it to him and when to stop.
One of the most exciting aspects for me was the way he told me what to do. Still to this day, I find it arousing when a guy gets dominant and gives orders in bed, and I think part of that came from my experience with Jay. At one point, he told me to ride him. I was unsure of what to do and didn’t want to look stupid, so I asked him to go on top. But he was having none of this; he rolled me on top of him and used his hand to guide his cock into my pussy, then thrust from underneath.
He didn’t make me feel stupid or inadequate: he showed me what pleasure was all about, making me feel like a complete fucking goddess.
After a while, he decided that he wanted to finish doggy-style and again, I was unsure of what I was meant to do. I can still hear his voice in my head as he told me to get on my hands and knees and “hold on tight”. I gripped the edge of the mattress as he pounded me, filling me with hot cum for the second time that night. If I recall correctly, he then encouraged me to use my hands to make myself climax as he watched me. I don’t think this was laziness on his part, I feel sure that he was trying to push my boundaries and build my confidence.
We slept for a few hours and fucked again, him on top, before he left the next morning. He didn’t say anything about when or even if we would hook up again, and I spent the rest of the weekend feeling puzzled as to the status of our situation.
Did this mean that we were in a relationship now, or were we just friends who were fucking?
I would soon find out.
Jay continued to be friendly and flirty the following week but dropped into conversation that he was going away to London with some friends that weekend, the inference being that we wouldn’t be spending any time together. This wasn’t a problem for me as I had extra shifts on both of those days, so had plenty to keep me occupied. When I saw him on the Monday afterwards, he said he’d had a great time and seemed no different to normal. I waited for him to suggest hooking up again, but nothing was said.
A few days later, he came into the office to show one of the older ladies I worked with the photos from his trip (this was back when people used cameras and had to get the film processed afterwards, only to be disappointed to find they’d had their thumb over the lens).
I casually wandered over to have a look, but it soon became obvious that although he’d gone to London with three other people, nearly all the pictures were of just him and a stunningly attractive female. I stood there, trying to play it cool as my colleague – who was completely unaware that Jay and I had been sleeping together – teased him about whether the mystery girl was his new girlfriend.
“Not yet,” he replied, looking all starry-eyed. “But I’m hoping that she soon will be. She’s one of the most amazing people I’ve met.”
How I acted oblivious to this, I will never know. I was dying inside, but obviously couldn’t say anything. At the time, I felt used and almost cheated, even though I knew that I had no claim on him. But it still stung.
It was only later in my life, when I went on a life-changing spiritual awareness journey (which I’m still on), that I realised that Jay had unintentionally taught me a valuable lesson about the importance of living in the moment and not creating heartache through expectations. His purpose, I would come to realise, was to repair my sexual confidence and show me what all the fuss was about when it came to fucking. Had he not played the part in my story that he did, I may have gone through life believing that okay sex was all there was.
So, lesson learned about not dating or sleeping with my coworkers, I moved on with my life and stopped actively looking for guys to get involved with; if I was meant to find someone, I would, but only when the time was right. I was too busy with my two jobs to socialise much at this time, which continued right through until December.
My school friends had planned a big reunion on Christmas Eve, and I couldn’t wait to see everyone again and catch up on all their news (this was how it was in a world without social media). I was standing talking to one of the girls when a few of the guys from our Sixth Form class came in, including the guy I had briefly dated back when we were students (wet fingers guy). I chatted with him briefly and was amused to see he hadn’t changed at all; he was still giving off horny and desperate vibes and seemed very excited by the prospect of me having my own house.
As the night went on, his friends (and some of mine) were nagging me to give it another go with him, while others were saying stay clear. It was like the devil vs angel on my shoulder scenario; I had one side going, “It’s Christmas, a no-strings shag will do you good!” and the other saying, “If you sleep with someone you don’t fancy, you’ll regret it!”. I got bored of everyone trying to tell me what to do, so went off to dance with another group of girls I knew from our school days.
“Hey,” one of them shouted above the music as the DJ played a Robbie Williams song. “There’s a guy over there who keeps looking over at you. I think he’s trying to get your attention.”
I was laughing as I turned around, fully expecting it to be a certain seafaring lothario from my past.
But it wasn’t.
It was a guy I’d never seen before. The first things I noticed were his amazing eyes and heartwarming smile. He came over and asked me to dance, which we carried on doing until the pub shut. He asked me for my number, but couldn’t find a pen anywhere (smartphones, how you’ve made pulling so much easier!), so he got his friends to all remember a few of the digits. I didn’t imagine that this method would be successful, so I was pleasantly surprised when he called me a few days after Christmas.
We arranged our first date for New Year’s Day, 2000 – the first day of the brand-new millennium (thankfully the world didn’t end, as some had predicted, or we would have missed out) and this year, we celebrated our twentieth wedding anniversary.
Jay got sacked from the company we both worked for a few months into the new year after faking yet more sick days and getting caught. He texted me a few years later, just to see how I was, but we have never spoken since.
His decision about not wanting a relationship with me did us both a massive favour. It put me on the path of meeting my future husband and, when I checked out his Facebook profile (I didn’t accept the friend request as I didn’t feel there was any benefit to doing so), I saw that he was also married – to the girl he fell in love with after shagging me (and she’s still annoyingly attractive all these years later).
While I was writing this, I thought about how I felt about these experiences now that I have the benefit of hindsight. I don’t regret much – I know that it doesn’t do anyone much good, and no experience is ever wasted if you learn from it – and there is little I would change about this period of my life, with two exceptions. I would tell my younger self not to waste precious energy and months chasing a guy who never loved me; getting my heart broken three times by the same person says more about me than it does about him.
And I would definitely wait longer for the right guy to lose my virginity to if I had my time again. Shaun wasn’t a bad person, but he wasn’t the right first lover for me. If I could go back in time, I would choose someone I encountered in more recent years to do the deed because I know in my heart that he would’ve made it the perfect experience I craved (even if the jury’s still out on whether his dick would’ve been suitable for a beginner). But, hey – maybe in the next life, right?
So finally, to the guys that have played a role in my tale of love and lust so far: thank you, because you either gave me something (thankfully nothing requiring antibiotics) or taught me something. A few very special people did both, and I consider myself fortunate to have encountered some truly incredible people, both in the physical and spiritual worlds.
For now, I’ll look forward to discovering what lessons are waiting for me in my next chapter(s).
