I had recently returned home to the UK from working overseas in Spain for a summer season. I was back, staying with my mum. This was back in 2007, and I was 23 years old. I had gone to work as a Holiday Rep for a major UK tour operator. I had an incredible season, working in the sun, with the holiday makers, making sure that they had an enjoyable holiday, and didn't lose their phones, their wallets or their passports, but occasionally helping them to lose their inhibitions!
I was only going to be home for a month before heading to the Austrian Alps to do the same job, in a Ski resort, rather than a beach resort. So I had a month of nothing, and time to see my family and friends after 6 months away.
My season working in Spain had changed me a lot. Prior to that, I had not been a particularly confident person when it came to women and relationships. I had only had sex with one girl before leaving the UK for that job. I had been unsuccessful with girls when I was at school and college and didn't consider myself to be conventionally attractive. Being a redhead guy as a teenager usually got you teased, and suffering bad acne didn't help my cause. So I had long since told myself I was not attractive. But working as a holiday rep had given me confidence. For reasons I still to this day find inexplicable, young people on holiday always seem to want to fuck their holiday rep. If we were taking them out to the bars for a bar crawl, or plying them with cheap booze on a boat party, or selling them tickets to the nightclubs. We didn't need to be funny, or interesting or especially attractive most of the time. The uniform and name badge (or 'Shag Tag', as we nicknamed it!) meant that attention came to you, with very little effort. That summer, I hooked up with more women than some guys would have in a lifetime, many who, under 'normal' situations, I would consider out of my league.
So I had returned to the UK a different person from who I was when I left the UK 6 months before. My friends noticed the change in me. Out for a drink one evening, I had confidently asked the barmaid at a bar we were at for her phone number, something I would never have dreamed of doing a year ago. She actually did give her number to me, again, something I wouldn't have expected a year prior. I would have just not bothered asking, assuming she would say no. So I had definitely changed.
As this was 2007, Facebook and social media in general were in their infancy. People were starting to come off of Myspace, and Facebook was becoming the site everyone used. I hadn't really done Myspace, so social media was new to me in general. Having not a lot to do with my time that month, I spent a lot of time sifting through it, accepting friend requests from former colleagues, family members that I hadn't seen in ages, and people I went to school with. It also had the new Messenger function, so I was chatting on and off to people I hadn't spoken to in ages, online, without the need to enter a tedious MSN chatroom! One evening, my notification bell alerted me to a friend request.
Natasha Thomas.
Wow. I remembered Natasha. She had been the most popular girl in school! Every boy remembered Natasha. Every boy had wanted to ask Natasha to the cinema and for a milkshake afterwards. 98% of them, of course, never had the nerve to ask her back then. She only hung out and socialised with the popular kids. The most attractive girls, and the guys from the football team. The ones who were cool enough to smoke at the back of the school fields, the ones who got invited to parties we never got invited to. I had gone to school with Natasha from the age of 10, right up until midway through secondary school, when I moved house and moved school, so in reality, I had not seen her in close to 10 years. But hey, we were adults now, and who was popular in the playground and who wasn't, obviously didn't matter in the world of adding people to your Facebook later in life. I accepted her request. Looked at her profile. She was still beautiful; she still lived in our hometown, and by the looks of it, was engaged to some guy and had been for a year or so. I thought nothing more of it and carried on with my day.
The following evening, I was sat in my mum's living room, laptop on my lap, mother droning on about something that happened at work, and the TV on in the background. My laptop pinged; the Facebook chat icon lit up. Natasha was online and had messaged me.
Natasha: Hey stranger! How are you doing? God, it's been so long!?
Me: Hey Natasha, I am great, thanks! Nice to hear from you, yeah, it's been ten years or so!
Natasha: God! Has it been that long? It feels like yesterday we were at school together. I see from your Facebook pics that you moved to Spain or something? That's really cool!
Me: Yeah! I worked there as a holiday rep; I thought it was a fun and cool thing to do, rather than doing University or something.
Natasha: Deffo! I went to Majorca with my girls last year, and the reps out there seemed to be living it large and having a blast; it looked really cool.
Me: Yeah, I was in Ibiza, so similar kinda vibe to Majorca, I guess. Definitely a fun summer. I wasn't ready to grow up and get a proper responsible job yet!
Natasha: Well, while you are young and pretty enough to do that work, why the hell not!
That line made me pause. "Young and pretty enough"? Was it just a figure of speech? Or was Natasha Thomas telling me that she used to fancy me at school and I was too much of a coward to say anything to her? I didn't make anything of it; surely it wasn't the latter! We chatted for a little while longer. I told her that I was home for a few more weeks before disappearing off again.
The next day, she messaged me again and asked if I was free the following day. She said that chatting online was all well and good, but it might be nice to catch up properly in person. Would I like to come round to her house at lunchtime for a cup of tea and a catch-up? It did amuse me how British that was, being invited for a cup of tea! But I thought it would be nice to see her, so I accepted her invitation. I tried to ignore the voice in the back of my mind saying something could happen at Natasha's house. Of course it couldn't! The 'young and pretty' comment was just an off-the-cuff comment. Plus, she was engaged, and we were not kids anymore. This would just be two old school friends, catching up after 10 years, whilst one of them was back in the country for a little while. I ignored that voice all the way on the bus ride to Natasha's house the next day.
I knocked on her door, and she appeared, smiling and flung her arms round me. "Oh my god! How mad is this?" she squealed as she embraced me, almost slightly too over the top. "Come in, come in," she said, gesturing me in.
I sat, slightly awkwardly, on the sofa, and she sat in the chair opposite. We both said nothing and then looked at each other and laughed at the awkwardness. She suggested we go into the kitchen and make tea. Once we had our drinks made, we went back to the living room and re took our seats and chatted quite freely. We talked about how the last few years had been, what she was doing for work, how she met her now-fiancé, and other topics, as free-flowing chats often do.
"So, do you still see Jade and Jenny and Zak and the others much? I remember you guys always used to hang out at school," I asked her.
"Jenny and Jade, yes, and sometimes Vicky as well. You remember Vicky?" she replied.
"Oh yes, Vicky, her older sister was Becky? They used to live in the same street as Paul and me back in the day."
"Oh, Paul Richards? He was your best friend at school; I remember you two always used to sit together in class."
"Yes, that's right. He is still my best friend now. He and his girlfriend came to visit me in Ibiza during the summer," I told her.
"That's nice that you are still best friends; it's good that you didn't lose touch after school. I am glad I am still friends with Jenny and Jade."
We finished our tea, and she went to make another. When she returned to the living room, she took a seat next to me on the sofa, rather than on the chair opposite. She sat a bit nearer than technically the next seat along was; she knelt and tucked her feet under herself, her knees, leaning against my leg. That voice in my head was at it again. I was telling it, it's nothing; she is just being friendly and not sitting at the other side of the room. This is just polite. She asked me more about my job, and how my summer had gone. I was telling her some stories about the crazy things that some people do on holiday and the mad situations they get themselves into. But she seemed to want to know about my exploits with the ladies. Asking if it's true that all holiday reps are male slags. I laughed, and admitted that I did ok, but there were reps I worked with who were much worse than me. She said it again.
"Well, whilst you are young and pretty enough, then do it while you can!" she laughed.
"Well yes, we are still young! I don't know about pretty, but thank you," I scoffed.
"Oh, don't be silly," she smiled. I always thought you were at school.
"Really? I didn't think you knew, or cared who I was. You and the rest of the cast of Mean Girls seemed too popular to notice the likes of Me or Paul back then."
"Yeah, I am sorry that I was such a bitch back then. Weren't we just awful!" she said, hanging her head a little. "But I always liked you. I guess I had to keep up appearances with the crowd I hung out with. But you were always so nice, and some of my crowd gave you a hard time. Sorry if I ever laughed with them."
"That's ok," I reassured her. "We were kids."
"Thanks...oh! But you did make me cry once! Do you remember that!?" she asked me.
"Yes, I am sorry about that. I said something about your braces on your teeth, didn't I?"
"Yes, you called me 'metal mouth'; I was so upset. Because I liked you, and I knew you were nice, and when you teased me, I was so hurt; I didn't think you would be cruel."
"I know, it was because I liked you, but didn't think you cared; it was self-preservation," I told her. "If we had been any younger, I would have pulled your hair and pushed you over in the playground. That's what kids do to the girl they like in school!" I said sheepishly, looking at her. "I am sorry I made you cry." She smiled.
"Well, it was a long time ago." She said, looking back at me. "Oh, this is nice," she said, catching sight of the tattoo that I had on my upper arm, visible just above the line of my T-Shirt sleeve. She ran her finger over it, lifting my sleeve to see it properly.
It felt nice. But again, I had to tell my brain to stop it. She isn't flirting. She fancied you at school...that is, of course, nice to know. But she has a fiancé; this is their house.
She went back to the kitchen to refill the drinks again. She returned, this time with a half-drunk bottle of wine and a couple of glasses. "Care to join me?" she asked, waving the bottle at me.
"Oh, ok, sure, just one," I replied. We clinked glasses and carried on chatting. I had to admit that I was starting to listen to that voice in my head. Things were now seeming like they were getting flirtatious. She noticed the pattern on my ripped jeans, running her finger around one of the holes on the top of my quads. We discussed how I had been a bit overweight prior to going to Spain, but had lost it all over the last few months.
"Oh, that will be all that sex in Ibiza, I am sure!" Natasha teased, prodding my arm.
"Ha! Well, I don't know about that!" I replied. "It's more like holiday reps earn a pittance, and I could barely afford to eat! We spent all our money on cheap Vodka!" I laughed. "Well, you are looking trim, having a fiancé; I guess you must get plenty of exercise?"
"Oh, that's all from the Gym." She said, rolling her eyes. "He works so hard all day, comes home exhausted, and barely has the energy for that! Sometimes I feel like a single girl," she said, looking a bit sad.
I was starting to feel what was almost certainly sexual tension in the room. She was touching me whenever she could find a reason; she was asking me to describe my sex life from Ibiza, wanting to know specifics and have me describe it in detail. And now, here she was, telling me, wanting me to know that she is not getting any attention from her fiancé. She asked if I wanted to join her in the kitchen to get more drinks. I followed her through.
She began to open a fresh bottle of white wine from the fridge. I didn't want another drink. It was still only mid-afternoon, and I was supposed to be meeting some family for dinner later, and didn't want to turn up a bit drunk.
"Not for me, thanks. I will switch back to tea," I said. "It's a bit early, and I don't wanna get drunk!"
She turned to me in surprise. "Oh, come on, another won't hurt; don't be such a pussy!" she mocked.
I tilted my head and looked her in the eye. "What did you call me?"
"A pussy," she said, stepping towards me.
"Oh, I'm a pussy am I?" I said back, taking a step toward her, closing the gap. We looked each other in the eye. She dropped her glass on the floor as we grabbed hold of each other and kissed frantically and passionately. 15-year-old me inside was going nuts; I was snogging the face off Natasha Thomas! This was insane! We practically dragged each other out of the kitchen, still kissing and groping at each other and into the hallway. We didn't make it further into the living room or to the stairs. I pressed her up against the hallway wall and lifted her crop top up and over her head, and tugged at her bra, spilling her breasts out of it. She grabbed at the back of my head as I sucked on her nipples, which hardened at the touch of my tongue circling them. She frantically grappled with the zip of my jeans, unbuckling my belt and freeing my cock from my underwear, which was rock hard, and she took hold of it between her fingers, stroking me as I nuzzled her chest. My mind was spinning, not quite believing what was happening.
She began to undo her own jeans and pull them down. "Fuck me," she breathed in my ear. "Here, now," she pleaded as she kicked her jeans off and across the floor. Her knickers were black lace; I will never forget that.
"Do you have any condoms?" I asked, in between kisses.
"No, don't worry, I am not on my cycle; I won't get pregnant or anything, just do it," she urged.
I pulled her knickers aside and ran my fingers through her folds. She was soaking wet, and I couldn't wait any more and slid myself inside her, both of us gasping as I entered her. I fucked her frantically against the wall. Both of us gasping, grunting, moaning as we had sex. It wasn't romantic or especially dignified, but it was the hottest moment of my life up to that point.
"Oh my god! Oh, Natasha, I'm gonna fucking cum! Oh fuck!" I cried out as I got close. She pulled me out of her and sank to her knees in front of me, taking me in her hand and jerking me to completion, opening her mouth as I spilled my load over her tongue. I groaned deeply as I came, and almost laughed.
It was crazy; I had just fucked Natasha Thomas, and I came in her mouth afterwards. This was incredible. She stood up, wiping her mouth, and I led her through to her living room. I laid her back on the sofa, parted her legs, and knelt on the floor. I pulled her sodden knickers down her legs and off, her wet pussy on full display to me. It was the most beautiful thing I had ever seen...possibly just for sentimental reasons. I had furiously masturbated as an adolescent, imagining having Natasha's cunt available to me, and now I was looking right at it. I leaned in and flicked my tongue on her clit, making her gasp and almost jump clean off the seat of the sofa. Taking hold of her hips and thighs, I got to work, lapping at her folds, tasting her juices which were flowing, sucking and licking her clit, sucking at her inner labia and pushing my tongue into her hole. I must say, I was not the most experienced at going down on girls at this stage of my life, but I was enthusiastic and took her moans and grabs of the back of my head as guidance and continued doing what I was doing when she expressed enjoyment at anything.
"Oh fuck! Oh fuck!" she moaned as I circled her clit with my tongue; she grabbed hold of my head and pressed me hard against herself as she convulsed in a very vocal orgasm. I looked up at her, her head back and her back arched off the sofa. She caught her breath, looked down at me, and smiled. She stood and took me by the hand, leading me toward the door and to the stairs.
I was going to Natasha Thomas's bedroom. My cock stirred just at the thought and was ready to go again. She took hold of my cock and led me by it, up the stairs and to her bedroom. We didn't say anything. She climbed up onto her bed, and I joined her. I climbed up over her. She reached out and placed her hand on my shoulder and neck, and pulled me down onto herself. With her other hand, she took hold of me and guided me back inside herself and moaned as my cock breached her again.
I was consciously aware that this was her and her fiancé's bedroom. I was fucking her in essentially her marital bed. But I was too far gone to care. I wrapped my arms underneath her shoulders and pumped my cock in long, slow, deliberate thrusts. Less frantic than fucking her against the wall. I enjoyed the sensation of myself stroking against her inner walls. Hearing her moaning, looking into her eyes as I had sex with her. Realising a fantasy I had had since I was a teenager, one that I never ever dreamed would come true.
"Oh god, I'm close again, don't stop!" she pleaded with me.
It became clear she was telling the truth about there not being much action with her fiancé recently; she was hungry for this. If I was just the right person at the right time, I really didn't care. I knelt between her legs, staying inside her, and lifted her legs up and onto my shoulders, getting as deep as possible and carried on thrusting into her.
"Oh! Oh god!" She cried out as she came again. Her cries brought me to the brink as well, and I emptied myself inside her, filling her welcoming pussy with my cum, and I flopped down next to her on the bed. We were both sweaty and breathing heavily.
We lay there next to each other for several minutes. She glanced over at the clock on the bedside table and, in slight panic, quickly got up and started to find some clothes to put on. "What's wrong?" I asked.
"He will be home from work soon; you are going to have to go. I really wish you could stay longer, but he normally gets back from work around this time," she said, apologetically.
We managed to locate my jeans and shoes that had been kicked off in the frantic grappling earlier, and we kissed at the door before I left. "Thanks for inviting me round....it was interesting finding out what I missed out on all those years ago. Wish I had said something to you back then!" I said, feeling happy with what happened, slightly guilty for the fact that she just cheated on her fiancé with me, and a tinge of regret that I should have opened my mouth back at school and just asked her on a date back then.
"Me too...I am so glad you came over."
As I walked to the bus stop from Natasha's house, it was like I became 14 years old again. I took my phone from my pocket and texted my friend Paul.
Me: Mate, you wanna hear something mad?
Paul: Of Course....
Me: I've just had sex with Natasha Thomas!
Paul: Bullshit!
Me: Honestly mate, I barely believed it myself, but I promise, I am just walking back from her house now. I promise it happened.
Paul: Oh mate, you are so lucky, she's like the most popular girl in school!
Natasha and I messaged a bit over the next few days, and initially tried to organize me visiting again, but never managed it. She eventually removed me from her Facebook, and I didn't see her again until some years later. There was sort of a festival street party in the town we grew up in, and I was home and went with some friends, and I saw her from a distance with her, now, husband, and she looked embarrassed and worried that I might say something. I found out years later from Vicky that she had felt bad for cheating on her fiancé, and that she had felt like she was getting married too young and wanted to sow some wild oats before committing for the rest of her life. I guess my living abroad and moving about all the time and not being a permanent fixture in our hometown made me a less risky option. Did I care that she used me to get some thrills before getting married? Hell No. I got to fuck Natasha Thomas. She was one of the best afternoons I ever had!
