Lord of the Ring: Part Two of the Trilogy [MF]

I’ve been honoured enough to deflower three tight arses: my own Lord of the Rings trilogy.

My second chance to induct someone into the anal sisterhood came a few years later. A year out of university, I met Chloe. Chloe was just tons of fun. Tall, Scottish, redhead, educated, intelligent and willing to try anything once. Chloe was sporty, both in build and approach to life. Hockey, Rugby, Running, Swimming - all with an only just hidden deep competitive streak, and with her outdoorsy nature came a practical, matter of fact approach to most things, sex very much included.

It was Chloe’s competitive streak that brings us to this story. We’d been together probably no more than three weeks (after a long long long distance courtship), and we’d got to the point in the ongoing sex partner interview process of comparing sex CVs. She was only slightly coy, and totally failed to be nonchalant, when she asked “So, have you ever had anal?” It’s hard not to grin when confirming that you have, but I summoned every iota of self control. “Yes, yes I have”. She didn’t probe (insert own joke here), but it clearly left an impression, because the next afternoon she just dropped “I want to try anal. I’ve never done it before and I’d like to see what it feels like” into lunch conversation.

Chloe being a practical country girl had clearly thought things through. No late night student halls inept fumbling for her. No, she’d called what I would come to understand as her man hungry school friends for advice, and step one was a trip to town for lube.

Reader; it was the greatest Saturday shopping trip of all time. Straight in, buy sex groceries, return. No window shopping or dilly dallying. Chloe had decided to have her arse fucked and that was the task of the day.

So back to her flat, and Chloe sets out the plan for the afternoon.

Step one: building excitement. Chloe loved when I went down on her (I mean, who doesn’t love oral but I actually feel like it’s my one marketable skill). So the entrée before we dealt with her other entry was for her to be eaten. A lot. I mean, Chloe had country girl appetites, and Chloe’s own country girl loved to be eaten. She was happy to be licked lying down, standing up or sitting on my face. She was perfectly prepared to lie back and receive, or demand, orgasm after orgasm. So that was the day’s plan. Orgasm 1 was the starter orgasm. Zoe, lying on her back, her head cradled on her pillow, letting me bring her to climax as she clamped her muscular legs around my head as she came. Orgasm 2 was sloppier, legs akimbo, pussy swollen, wide open, wet and hot.

Orgasm 3 was her brown button’s Apollo 10 mission, the dress rehearsal for the moon shot. When she had gathered her breath, she lay down again but this time, my index finger (and yes, my fingers are long) started to work our newly bought lube round her bum, and as her breathing started to quicken, the finger started to turn stroking into pulling, and pulling into pressing until she lifted her hips and, just like her sluttier coterie had advised her, she bore down and opened to take that finger in with a moan. And as I licked her, from the bottom of her lips up to her clit she pushed down more and more, taking in the staggering amount of maybe 2cm of index finger as she came.

This was clearly good enough for Chloe’s Mission Control. With a smile, and a ‘let’s get to work’ look about her, she said “Right, let’s try this”.

She rolled over onto her hands and knees and presented her glorious, round, freckled and now very flushed backside to me.

“Fingers first please, with lots if lube”

And lots of lube there was. All over all my fingers and worked into her bum, until we slipped in first one and then, to our shared surprise, a second. She was squirming, pulling away then gathering herself and pushing back. She was clearly processing the sensations and telling her slightly disobedient arse to get with the programme.

“Ok, let’s try your cock”

“Ok, but you lube me up”

I think Chloe worked half the tube of lube into me. I was so slippery I could have slipped it into Fort Knox. Happily, Chloe’s arse was welcoming visitors, especially those looking to leave deposits. So here was repeated a story known millions of times through the world. Chloe raised her arse, and looked back over her shoulder in expectation, encouragement and affection. I held my cock to arse, and started, like my finger before, to rub her and tease her, pulling up and down and left and right before turning rubbing to pressing. And pressing made her arse close down, squeezing tight before Chloe took the deepest of breaths (thank you yoga classes!), dropped to her elbows and bore down, opening herself and letting the head of my cock (surely its most handsome feature) slide almost, but not quite, all the way in

“Uuuuuuuurggh”.

A breath. Two more breaths. I’m motionless but Chloe gathers herself, takes another breath, bears down and pushes back and the head of my cock is in her, and she looks very pleased with herself.

Remembering her friends advice, yet more lube is squeezed onto the point where we are joined, but this time it gets worked into her by very slow, almost imperceptible movements as we separate infinitesimally then push back together.

As these tiny movements work more lube up into her, Chloe starts to open, get wetter and starts to get into a rhythm. I am harder at this point than i have ever been but a thought pops into my head from a late night 1990s Channel 4 show: if you are lucky enough that she gives you a chance to take her arse, make sure you enjoy all of her arse.

And Chloe had a magnificent arse. Round, country girl but toned and firm, freckled and seemly. As we started to really get into a stride, I stroked her bum, grabbed her hips to pull her onto me, strokes the point if entry with my thumb until I felt her hand brush by balls, as Chloe reached back to rub herself frantically (which I later found out was her favourite way to cum when I was inside her). She started to get redder and redder in the face as she looked back to watch me, and her face started to contort in a way I’d get to know well, jaw clenched and eyes screwed tight as her rubbing got so frantic it was rocking us from side to side.

And then a moan, or really a scream “Oh God it’s soooo intense. It’s so much. I can’t cum it’s too much. Please please cum in me now”.

So that’s when we took it to 11. My hands on her hips I pushed into long hard strokes, driving her into the bed until after maybe a minute I felt the pressure building up. Inwas ready to cum. I wanted to cum. I was desperate to cum. But Chloe’s arse was so tight around my cock that the pressure was trapped. The only way to get it out was to drive through as hard as I could, causing wave and wave of moans from below me, with which I joined in as the pressure, almost painful, finally burst into her arse and I tried to get my cum as far into her as I could, and we finally collapse, me on her and in her, onto the bed.

We lay for a few moments silently catching out breath, before Chloe laughed out loud with joy; a laugh repeated when my cock had shrunk enough to escape her greedy arse, and with its exit came a flow of cum, lube and everything else that her slightly half hearted efforts had no hope of containing.

Chloe’s first anal. But certainly not her last.