Two Fantasies in One

This last SexTuesday was the result of two weeks of discussing, teasing, and organising to fulfil one of both our fantasies.

For my part: I’d always wanted to be put over a guy’s lap and fingered while he spanked me. I’d never been spanked but it interested me and I knew D would be the person to trust with this sort of thing.

D: has a thing for me dressing up (it used to be his favourite role play when we first started sleeping together too) He has also just gotten into anal play. He’s been using butt plugs himself before we hooked up and has wanted to try anal sex.

Now I wasn’t so keen on the anal sex, in fact a few months back I was dead against it. I made a comment on twitter awhile back that the next guy who asked me for my arse would have to give me his first. D knows this and didn’t expect it from me, but he said if I was even slightly interested he’d like us to try it.

One of our first hook-ups D asked me to put his butt plug in for him and then fucked me while he wore it. In that same session he lubed his fingers while he had me on all fours and fingered my anus. I was surprised, but he asked permission before going further and after all the carry on from friends and associates about anal sex, I have to admit I’d become intrigued. So I let it happen. Now it wasn’t pleasant, it wasn’t unpleasant. I would say it did nothing for me at all; I still cringed away from the idea of anal sex though.

So a fortnight ago D tells me he’s bought me a present, a homer present (it’s really for him). He explained that I will be wearing this present when he fulfils my fantasy of being put over his knee. The sexting progressed from just spanking and fingering to fingering both my holes, to slipping a butt plug in to punish me for being a naughty girl. By the time Tuesday came around we were both very horny and on edge to get together.

D arrived package in hand and proceeded to remove a little tartan school skirt (let’s be honest it was a belt disguised as a skirt) and a red G-string. I was to play the naughty school girl it seems. I disappeared into my bathroom, stopping in my wardrobe for a moment and got dressed. When I came out I wore the skirt, the G-string, a see-through white blouse with no bra, and knee high fishnet socks.

D’s jaw dropped, “Fuck that’s hot!” was his exact words before he stood, took my hand and walked me to the bed. He slipped into character mode instantly.

“You’ve been naughty. Put your hands on the bed, bend over and don’t move.”

I complied and he spent a few minutes admiring the view from behind. I was then told I would need to earn extra credit and asked how I planned to do that.

This is where the foreplay began, kissing, touching, fingering, my sucking his cock…

D gets a little rough with the mouth fucking sometimes, my hair in his hands as he finds the back of my throat and makes me gag. I don’t mind it, I have to be in the mood for it, and tonight with the build-up we’d had, I was.

He sat on the bed and pulled me over his lap rubbing my arse as his other hand pressed under my hip to find my clit. Then he started spanking me. Lightly at first, then a bit harder, asking if I was ok before making the hits harder. All the while he rubbed my clit so that the pleasure was always there for me. When my butt matched the red of the G-string he slid the panties off took up some lube and caressed the puckering of my anus.

“You want to stop at any time, just say, ok?”

I nodded and bit my lip, this was his part of the fantasy now. He fingered my arse first, yet again there really wasn’t anything in it for me, and when he slid the well lubed Lelo butt plug in, it was slightly uncomfortable, but bearable.

“Good girl” D smiled as he helped me to standing before collecting his butt plug and handing it to me. “My turn”

I took the plug, lubed it up and he bent over for me to insert it. He moaned as I did, I guess he gets more out of it than me, or maybe it was my other hand caressing his hardening shaft. He laid me on the bed on my stomach, one of his favourite ways to be blown. D loves my tight little arse and likes to be able to see and touch it while I’m sucking him. He went to my toy drawer collected my Lelo Ina vibrator then came to stand in front of me again.

I took him in my mouth and started sucking while he leant over me, pushed my legs apart and penetrated me with my vibrator filling all three entrances at once. I do not have the words to describe how it felt to be triple penetrated; true I believe it would be a lot different if it were by three guys (*not* one of my fantasies) but still it felt so naughty and so good.

I put my finger through the ring of his butt plug and gave tiny little tugs while I continued to suck him. D got so engorged he could barely fit in my mouth so I just sucked the head of his cock hard. D pulled away as it got ‘too good’ and sat back down on the bed. He pulled me around to face away from him and sat me down on his cock. You should have heard him moan; the jolts of my lifting and dropping onto his lap stimulated the plug in his arse and he loved it.

I for my part got nothing out of the plug, but having D press into me when he was so thick was heavenly. We moved through various positions, we always do. Our favourite that night was him sitting on the end of the bed, me facing him, my legs wrapped around him and us rocking back & forth. As things got really hot between us D put me on all fours so he could tug on the plug in my butt while he fucked me. He pulled me up, kissed me intensely and murmured in my ear “I want your arse; I want to fill it with my hot cum, let me have your arse”

I swallowed, I had to admit I was scared but it was going to be now or never and I refuse to be a whimp. So I said yes, or maybe I breathed it.

I grabbed my Lelo Soraya, went back to all fours and waited. D removed the plug quickly putting it in the bathroom for cleaning later then returned to me. He pressed into me, lubed as I already was, and his cock already covered in my wetness he was able to gently enter me without any pain, and I have to say once he was in me my opinion of anal sex changed completely. He felt so good in my arse. He started moving back and forth slowly and both of us moaned loudly with how good it felt. I took my Soraya, turned it on and put it inside me. Good turned to fantastic.

D fucked me, I held the Soraya in me and I was shocked to shit when I started to orgasm. I came so hard and D came with me and it was amazing.

So my mind about anal sex is completely changed, however, I am very lucky to have a sexual partner who cares about me, who doesn’t want to hurt me and believes my comfort and pleasure should be put above all else. If I had said stop at any time, D would have done so and not begrudged me for it. He made sure he did the prep work (lots of prep work is needed for anal sex, especially your first time) so there was no discomfort for me. Anal sex is something that really does require you trusting your partner the first time to make sure you enjoy. And guys, if a girl doesn’t enjoy it that first time, if you make it all about you, then she won’t want to do it again.

While it was fantastic, it’s a fantasy fulfilled now and D has told me that his interest was mainly because it’s so taboo. He really enjoyed it, but he said straight out he prefers my tight little pussy or my mouth, so anal sex is not about to be a regular thing for either of us, but I dare say it will happen again. We’ve already moved on to planning the next fantasy to fulfil. He wants me to visit him at his workplace so he can bend me over his desk and fuck me in his office – that will be very interesting.

Xoxo Angel

A closing note:

Now even though I didn’t mention it, you should know D and I never have unprotected sex…usually. This was a first and he wore a condom right up until and even to start with the anal sex. D and I have both had complete STD screens done and showed each other our results to know we are both clean. We’ve also not had sex with any other person for over six months so there is no chance of something lying dormant. If that wasn’t the case I can assure you the condom would have stayed on. And with the after experience I’ve decided all future anal sex will require a condom anyway…unless I’m constipated. Unprotected anal sex is like a natural enema. No one ever told me about that effect and I think it sucks when people only ever tell you the good parts, but leave all the bad parts out so you get a big surprise later. So now you know.