Jenny and Jack Pt. 04

I could hardly believe what I was about to do but I just felt I could not resist. My finger tip soon found his tight hole. It already felt oily where the oil had trickled down. I moved the tip of my finger around until I was satisfied that it was in perfect position and then slid my finger slowly up inside him!

Tom momentarily tensed, his sphincter clamping round my finger as I caught him by surprise. I then felt him relax again and pushed my finger in as deep as it would go.
With my finger now moving gently inside him I used my other hand to grip his stiff penis. Never in my wildest dreams did I think I could be so naughty and bold and when Jack said, "now suck his cock Jenny; remind me how naughty you can be." I didn't hesitate; I just lowered my head and took the head of Tom's erection into my mouth.

As I lowered my head down my rear end naturally lifted up. This was obviously a perfect invitation to Jack.
I made a muffled gasp and my lips momentarily let go of Tom's penis as Jack ran the tips of his fingers between my legs, parting the wet lips of my vagina.
As my mouth settled back around Tom's erection I then felt Jack slip two fingers into my wetness.

"Jenny, on more than one occasion now, you've denied Tom the pleasure of having his cock inside you. I think it is time you let him feel the delight of having his stiff cock in your cunt."

Just hearing Jack using the course word to describe my genitalia sent a shiver of excitement through my body. I lifted my mouth from Tom's cock and then slid my finger out from his anus.

"I want you to straddle Tom Jenny. Face him and kneel with your knees either side of him. I want to watch and see what it looks like as you lower your self down onto him and take him inside you."

It felt so wrong but at the same time very erotic to be told by my lover to allow another man's penis inside me while he watched.

I did as Jack asked, straddled Tom and then slowly lowered my self down onto him. I reached down between us, gripped Tom's erection and guided him to me. I could not see Jack. He was behind me and that made the whole situation feel even more erotic. I could sense him gazing between my legs and watching Tom's stiff penis opening my wet labia and then sliding up inside me.

Any feelings of guilt were gone as I felt the wonderful sensation of a big stiff penis filling my hungry body as I lowered my self completely onto him until I had it all inside me.

"Now lean forward Jenny and press your tits against Tom's oily chest."

Still in a kneeling position I did as Jack asked and leaned forward until my breasts were pressed against Tom's chest.

Tom started to move his hips, moving his erection in and out. I knew that in this position Jack could now see every detail between my legs. I tried to imagine how aroused he might be, seeing my labia stretched around Tom's thick erection.

As if to remind me how exposed I was in this position I gave an involuntary gasp as I felt him touch my anus with the tip of one of his fingers.

I then felt oil trickling between the cheeks of my bottom and, at that moment, I knew exactly what he had in mind.

When I had first agreed to come up to Jack's room with the two of them I had been filled with doubt but also curious. I doubted that I could be completely sexually uninhibited with both of them. It had felt wrong but I remembered the previous experience with the hotel owner's son and how I had coped with that first experience of entertaining two males and feeling horny and comfortable. Maybe it was because Tom was an older experienced man whereas at the hotel the owners son had been naïve and very much younger.

But as I straddled Tom, my breasts pressed against his oily chest, my nipples tingling, his big erect penis filling my vagina and Jack's finger about to slide up into my rectum it still felt wrong but I felt unable and more importantly, unwilling to resist.
My whole body felt filled with a powerful sexual desire and just knowing that both Jack and Tom were excited and aroused because of me and that made me feel very sexy.

Tom's penis felt good as it moved piston like inside me. I started to move my hips in a similar action, using Tom's erection to give me pleasure.

I could feel the familiar sensations of another orgasm building inside me.
As I moved against Tom my nipples sent shivers of pleasure through my body as they rubbed against his big strong oily chest. The rhythm of his penis inside me as I rode him felt perfect. I started to move my hips with more energy, forcing Tom deeper inside me, feeling him stimulate my pleasure bud with each thrust.

I lifted my head and started to moan loudly. My moans quickly turned to screams and my body jerked on top of Tom as I started to cum again. It was at that moment that Jack pushed his oily finger deep into my rectum and I lost control completely.

Jack was fucking my rectum with his finger as I rode Tom's stiff penis. I could feel Jack stretching and lubricating my smallest hole as I writhed around on Tom in sexual ecstasy.

My screaming subsided until I was just moaning gently. I felt as though I was permanently on the verge of another orgasm and could easily reach another peak.

Jack slowly eased a second finger into me. I was surprised how it made me feel 'full' but was not painful.

I felt him kneel on the bed behind me and then a sudden feeling of emptiness as he slid both fingers out from me.

"Are you ready for two cocks Jenny," he said, his voice sounding husky, "two stiff cocks and two lots of spunk?"

"I think so," I said quietly, "but I don't know if I can take both."
I then felt Jack position the head of his penis into my tight entrance.

This is it, I thought. I've spunked both Tom and Jack before but now they are both going to penetrate me together!

I tensed as I felt Jack push an inch or so up into my puckered hole.

"Just relax my Darling," he whispered as he leaned over me.

Tom and I both remained still as Jack slowly but surely slid his big erection deeper into me. He paused as he felt my sphincter trying to resist him but with his usual patient skill his erection slowly but surely slid right up into my rectum.

Although Jack had entered my bottom before, this felt completely different. I felt incredibly 'full' having Tom filling my vagina at the same time but it felt so good.

Gradually the three of us started to move, clumsily at first but soon finding a rhythm.

It felt incredibly sexy and horny having both men inside me.

I felt Jack's hands reach under me and seek out my breasts. His big strong hands were soon lifting me slightly as he held them in each hand and squeezed them.

I had never, even in my wildest dreams experienced anything like this. I could sense and feel both Tom's and Jack's lust as they started to thrust deeply but alternately into each of my holes.

We kept up the same rhythm but now they were thrusting deeper and with more passion. Jack was now cupping my breasts like a second bra in his hands and lifting my body higher so that Tom could play with and pull on my nipples.

I could sense that both of them would soon ejaculate as Jack's breath was hot and urgent on my neck and I could hear Tom breathing hard.

Jack's hands were now squeezing my breasts quite hard, his fingers digging into the soft flesh, but all I could feel was pleasure radiating through my whole body.

The men increased the speed of their thrusts but still managed to keep a steady rhythm. As one thrust deeply in the other was coming out; pounding into each of my holes with powerful alternate thrusts.

I felt Jack start to tense and slightly lose his rhythm. I knew he was about to ejaculate and, as he squeezed my breasts and thrust into my rectum I felt I was about to cum again. My body started to tremble all over as my screams once more filled the room. Somewhere in my orgasmic state I heard him say in a husky voice, "I'm going to spunk in your arse Jenny. I'm going to spurt my hot spunk deep inside you." I could feel Jack's cock, swollen and pulsating in my rectum as his hot ejaculate then flooded out. Almost at the same time I felt Tom tense and loose his rhythm as I felt the new experience of having both my rectum and vagina filled simultaneously with hot salty cream.

My screams and the men's thrusts and groans slowly subsided until the three of us collapsed in a naughty sweaty heap, with both men still inside me.

I felt them both slowly soften as we lay there physically exhausted.

Jack and I must have fallen asleep for a while and when we awoke we were alone.

Jack hugged me saying, "thank you my darling, you were fantastic!"

I looked around the room, starting to doubt that Tom had actually been there. Maybe it was just a very realistic role play. After all, Jack is quite good at erotic role playing.

I was almost convinced that my mind and the wine had been playing tricks again and that I had only been with Jack all evening but then felt the wetness of their joint effort dribbling from both my bottom and vagina.

"Oh wow!" I had really done it; two men at the same time! I could hardly believe that I had been that bold!

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