An anal adventure, a revelation and a gift beyond words

1490 words | 5 |4.44

So, my last diary entry, which concerned me and my way older boyfriend, but he’s my man, so I can’t really call him a boy.
That ended with him having sex with me in my school uniform, again I felt so slutty but it was such a turn on for him, which turned me on.


I was sat at school when my boob vibrated, I don’t keep my phone there, it’s in my top pocket of my blazer, I slyly got it out in class and instantly smiled, it was from S, I love it when he messages me.

“Hey beautiful, I miss you, hope you’re ok? When can I see you? Xxx”

I felt bad because I couldn’t reply straight away, I went off to the bathroom, snapped him a photo and typed my message and pushed send.

I sat there on the toilet waiting for his reply, I knew he had seen it, … typing…. Typing, and then it came through.

“Oh Mia!! It’s a shame I’m at work otherwise I’d be coming to get you xxx”

The photo wasn’t of anything naughty, it was just my tights and skirt by my ankles and my shirt undone if you wanted to know what I sent.

Anyway, so come the weekend I turned up at home, well his house and knocked, he instantly smiled when he opened the door, I went in and hugged my man.

We sat in his lounge and just chatted, but I needed to tell him something, I was so nervous, I didn’t know what he’d say or whether he’d want to. He knew something was off.

“what’s wrong? You’re fidgeting, what do you want to say?”

I thought about it for a few seconds and then blurted it out, I just thought it’d be easier.

“I want to do anal; I’ve never done it before, but I want to, you know with you”

He grabbed me like he did a few weeks ago and just held me, everything just went still, and time seemed to stop.

We spoke about it and what would need to happen to make it enjoyable, it was quite weird to think about but needs must and that.

Fast forward a week and we’re sat in the bedroom, I feel confident in doing it, I’ve prepared as much as possible, he makes me promise things, he almost sounds fearful.

He starts with a toy, it hurt a little but once I got used to it, it felt damn good to be fair, the next thing felt so much better.

His cock felt cold, that was from the lube, but it soon warmed up, he went so softly so not to hurt me, I couldn’t take all his dick before it hurt, but what I had inside me was enough.

He pounded my ass so good; I know I was an anal virgin, but it felt so good, I was so nervous about trying it but once I’d got used to toys and his dick then it was awesome.

I had pillows under my lower back, we were literally staring at each other, and having hot anal sex, it was romantic without being romantic if that makes sense.

He went a bit faster deeper a few times, that bit I absolutely loved, it hurt a bit but he instantly slowed down and went back to the gentle slide of his cock inside me, it feels amazing!.
We finished our sex session and he cum on my boobs, that was a turn on aswell, especially as his fingers were inside me aswell.

The following Saturday I was with him again, I even avoided going to town with my friends so I could see him, I wanted to do anal again, but I was still a bit sore from last weekend’s antics.

We still had some anal fun though, it was mainly toys, I’m determined to have all his dick inside me. he put a blindfold on me and put a toy in my ass, while I sucked his dick. I urge anyone to try blindfolds.

That was a pretty hot experience to be honest, just the feeling of not knowing what he was going to do, I may have to ask him to do sort of thing again.

The soreness started to go the more I train myself, and the more he trains me, he doesn’t dictate to me of course, but if we get to that horny point, then he now asks what I would like and we go from there.

He’s bought me a training kit that I picked to help me in my quest, I’d use it whenever I was alone, or before I go to sleep, I’m normally on the phone to S whilst doing it.

That’s all we did on that weekend, we could have done more but I was on my period, unfortunately that happens at my age! Although I’m on the combined pill, I still have a break, and certain things happen.

A few days later, we’re now in early May, I can’t wait to see my man again, but it’s different, he seems flustered, he sends me a text.

“Hey beautiful, meet me after school, I have some news to tell you, it’s important!! Xx”

Luckily, I was able to reply quite quickly and arrange a meeting place.

We drove to spitchwick, I’ve never been until now, I remember not getting out of the car, if he’s going to ditch me then I’m not going to run off. I became quite hostile and then I snapped at him.

“You could have ditched me by text, us girls don’t like it but we don’t like being driven to beautiful places and dumped”.

“It really isn’t fucking cool, bro!”

he doesn’t snap back, he calmly tells me that he’s not ditching me, but we’re here because it’s our 6-month anniversary, I felt so shit. It was a case of ground swallow me now!

He gets 2 bags, 1 which contains food, and various other items for a picnic etc., the other containing clothes for me to change into, still in my school uniform of course.

We have the picnic, me apologizing every 5 minutes for jumping the gun and snapping at him, it was almost screaming to be fair. I forget he wanted to tell me something. I didn’t care.

FYI, blankets make good shelters to give your man head if the mood takes you. People don’t need to watch me suck my man’s dick on a field. plus i love doing that to him.

It started to rain, which is normal in the uk, I grabbed his car keys and ran off down the hill when he shouted something. I stopped dead in my tracks turned and shouted “what” back to him.


I didn’t know what to do, I was frozen to the spot, I didn’t know what to say, I just stood there in the rain, I was like in a trance.


He said it again, but this time he was right in front of me, looking right at me.

I had to have him, it’s all I ever wanted to hear from him, he put the bag and picnic stuff back, I was already in the back seat, my shorts were off, along with my underwear, it didnt take him long to join me, we had a quickie right there in the car park with the rain falling.


A few days later my mum hands me a brown envelope, remarking that it was there when she got back from work at 7am, I nervously opened it, I instantly started to feel sick, happy, loved, and all other emotions, I know I couldn’t contain myself. I stare at the pieces of paper and card.

“Mia, we’re pleased to enclose your reservation with us”

I look at other items, and in my hand are 2 Taylor Swift tickets for her Wembley stadium show on June 22nd (I’m writing this in June) so not long to go!!

I literally cry, my mum cuddles me, probably to keep me upright and such things, I felt so giddy, I just didn’t know what to do or say, my mum calmed me down before heading off to bed.

I opened my phoned and messaged S.

“Thankyou thankyou, 1000 thankyou’s! words are not enough, I’ll make it up to you! I love you xxx”

“I assume you’ve opened the brown envelope then. You’ll make it up to me? How may I ask? Love you xxx”

“You’ll see 😊 xxx”

thanks for reading 🙂

Mia, xx

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  • Reply BRITNEY ID:1e8sh3tot8dn

    My boyfriend loved fucking me with my catholic school uniform on !! He knew that I don’t like anal but he secretly lubed his cock and had me bend over his parent’s sofa arm rest and ripped my blue school tights and quickly worked his cockhead into my ass, popping my ass cherry as I screamed but after a while I got used to having his 6-inch dick in my ass !! loved your story SmuttyMia !! It brought back a great erotic memory for me !! I gave you a 5 star !! Britney

    • SmuttyMia ID:agya8fi9

      Ahh i wonder if S would do that 🙂
      S loves my uniform – and tbh i love that he loves it! well i just love him

      Glad my diary entry brought back memories
      Mia x

  • Reply BayratPirate ID:1ck646nq5lb9

    You’re such the Romantic!
    Great tale…
    Cannot wait to see what you write next!

    • SmuttyMia ID:agya8fi9

      why thankyou pirate man! 🙂 hope you’re well 🙂
      I’m currently typing the next part, i’ll try to finish tonight – No Promises though
      me and S will then start
      Where the Rose Blooms: A Pirate’s Tale of Passion
      Let S know what you think?
      Mia x