Jenny and Jack Pt. 01

He slowly moved down my body circling around my buttocks and moving directly to my legs. I felt more oil being trickled all down the back of one leg and then the wonderful feeling of his hands, firm but gentle, rubbing in the oil. He started at my feet and then slowly worked his way up my leg. I could feel one hand on the inside of my thigh and the other on the outside. As he got closer and closer to the top I felt him pull my thigh a little, opening up a gap between my thighs. His oily fingers moved closer and closer to my labia, which I had had freshly waxed a few days ago. With only an inch or so to go he stopped and changed his attention to my other leg. Again I felt him trickle the oil onto the back of my leg and then repeat the same as before. He lifted my leg a little as he massaged my foot and at the same time opened my legs a little further. I could feel that I was already getting aroused and wet and just knowing that as he massaged me he now had a clear view of my hairless labia added to my arousal. I wanted him to touch me between my legs. My expectation started to rise as his hands moved up higher and higher, squeezing and pulling the flesh of my upper thighs but again never quite reaching my labia.

With my face still buried in the bed he lowered my leg. I felt him move away and then his hands were gently moving my feet apart.

I wondered if my face was blushing as he said, "Oh Jenny, you look so beautiful and sexy displayed like that with your lovely smooth and wet lips gazing back at me."

I sensed him move back up and then felt oil being trickled between my buttocks. It felt deliciously erotic as it trickled between my cheeks, over my anus and then down to my wet labia.

He poured some more onto each buttock and then I felt him grip my cheeks, one in each hand and start to massage them. I felt very sexy but at the same time completely exposed to his gaze as I realised he was pulling my cheeks apart and no doubt looking directly between them at my exposed anus and labia.

He was driving me insane with his teasing touches, almost but never quite touching my moist lips. The tips of his fingers moved all around the soft flesh of my upper thighs but never quite touching where I wanted to feel him the most. Very slowly I realised he was starting to concentrate more on the area between my buttocks. Once, twice, three times now the tip of an oily finger had brushed over my anus.

Each time I felt it I momentarily tensed but then gave a shiver of delight. The brushing became more and more frequent until I finally felt one of his oily fingers start to press directly into my tight ring. He trickled more oil between my cheeks as he started to work the oil into my smallest hole with the tip of his finger.

I'm not sure if it was the fact that I was lying on my front and my clitoris was being stimulated as it pressed against the bed or if it was the new experience of having my anus stimulated by Jack's finger. All I knew for sure was that it felt surprisingly good.

I had experienced having Jack's finger in my anus before but this time it felt different. Maybe it was the oil or maybe it was because it felt like it was Jack's only desire.

His oily finger slowly pushed deeper and deeper until I felt his knuckles pressed against my spread buttocks.

With his finger now all the way up inside me he leaned over me and whispered in my ear, "Jenny I'm going to fuck your arse."

Before I could answer I felt him slowly withdraw his finger. The tip of it lingered at the entrance and then I felt the tips of two fingers.

I felt my self instinctively tensing my sphincter as her started to push the tips of both fingers inside me.

"Just try to relax Jenny and push back onto my fingers."

I felt more oil trickling between my buttocks and onto his fingers as I tried to do as he asked. To begin with it felt impossible but as I pushed back and concentrated my mind on relaxing my sphincter I felt both of his fingers start to enter me.

He was very patient, pausing regularly each time I gasped or made a sound but, slowly but surely, he was pushing two fingers into my bottom.

I felt him pour yet more oil over his fingers as he slowly worked them inside me. I could feel him moving the tips of each finger inside and as I relaxed more and more he pushed them deeper until they were completely inside.

With his two fingers still pushed in my bottom I felt him kneel astride me as he said "reach back with one of your hands Jenny". I reached back and was rewarded by him guiding my hand to his erect penis.

It felt very big and I felt my self start to panic saying, "surely it will not fit!"

Jack did not answer immediately, he just poured some oil over his penis and my hand before saying, "make my penis nice and slippery and then I will show you how well it will fit."

I wrapped my fingers loosely around his thick shaft and spread the oil from the head to the base.

I released my hold as Jack said, "Now just relax my darling and experience something new."

I felt him moving as he stayed kneeling astride me. He then lowered his body as he withdrew the two fingers from my bottom. I waited nervous and tense as I felt the head of his penis nudge against my anus.

"Just try to relax Jenny and I promise it will fit."

I remembered the way in which I had relaxed my self and then pushed back when he had inserted his fingers. I tried the same technique again. I could feel the head of his stiff penis pressing into me. It felt impossibly big as it start to enter me.

Jack paused with just the head of his penis pressed into my tight opening. I concentrated on relaxing; breathing steadily and calming my fears.

Although Jack had paused I could feel a slight, constant, inward pressure. Trying hard to relax I felt Jack increase the pressure little by little until it felt as though I had been right all along and it would not fit.

By now Jack had lowered his body onto my back and was constantly kissing my ear and whispering, "Relax Jenny, relax."

All of my natural instincts were making me tense my bottom muscle but I felt determined to try my best to please Jack. I focussed my mind on my bottom, making myself release the tension until suddenly I felt as if a door had suddenly opened. It felt impossibly big but at the same time glorious as I felt Jack's oil covered penis slide slowly but decisively up into my anus.

He whispered into my ear using the crude language he had been teaching me via our emails, "Jenny, your arsehole feels wonderfully tight but welcoming. In a moment I'm now going to fuck your arse and fill you with my hot spunk."

As he spoke he started to move in and out of me; very slowly and gently at first but then gradually harder and harder. He slipped his hands under me and grabbed my breasts, gripping each of them hard as he started to plunge in and out of my anus.

I could feel his hot breath in my ear and could sense his feelings of lust. Each inward thrust of his penis pushed my clitoris down against the bed. I could also feel sensations inside my vagina as Jack thrust between my buttocks.

His thrusts became more and more urgent. His grip on my breasts was on the verge of painful but that just seemed to add my pleasure.

His breath was hot and urgent in my ear as he said huskily, "Jenny, I'm going to fill your arse with my spunk."

His thrusts did not only feel more urgent but deeper. I could feel his scrotum slapping against my wet labia as he tried to get as deep as possible inside me. I felt my self losing control as his fingers dug painfully into my breasts and then, in a huge wave of pleasure I was screaming and writhing in ecstasy as I felt Jack grunting and groaning in my ear, his thick penis throbbing deep inside me and finally releasing its hot semen into my rectum.

I felt his whole weight on my back as he collapsed onto me, satisfied and covered in sweat.

We lay like that for a while, still connected until I felt his penis start to soften and then finally slip out of me.

Jack rolled off to one side and gazed into my eyes saying with a mischievous grin, "I told you it would fit!"

We both laughed and hugged each other as I asked, "Am I a good student Jack, a willing pupil?"

He smiled back saying, "I could not wish for better."

If you have enjoyed reading my story please let me know. It helps to make it worthwhile. Thank you.

To be continued.