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Chapter 17
What's next?
Something different Pt1
I moved my hands and began to rub the flawless globes of Jess' arse. She moaned her approval, spurring me on. The part of my head that would've commented that this idea could go one of two ways was dulled by lust and ****, so Jess' noises made me think that this was a faultless course of action. I slowly pulled Jess' cheeks apart. That sight made me even harder and I felt Jess falter for a moment as she bobbed her mouth up and down on my cock. My tongue still pleasuring her, I massaged my thumbs along the crack of other splayed arse, gradually inching closer to her puckered hole.
I dipped a thumb into my mouth, liberally coating it with spit and placed it onto Jess' arsehole, rubbing it slowly. It took Jess a moment or two, maybe delay from being distracted by my tongue; by her own efforts on my cock; or from the **** in her system, but she stopped still and froze her head with only the tip of my cock still in her mouth.
I kept up with my testing of her arsehole, working circles around it with my moistened thumb. Jess remained still for a long moment and I wondered how she was taking this. I slowly felt the pressure on my shaft resume and my heart leapt a little. Clearly this wasn't entirely unwanted, or at least it was tolerable. We continued our attentions on each other in the way for a good while longer. My thumb traced the area around and over her ring as I kissed and licked her rounded cheeks, before darting back to her pussy and clit. Jess' breathing had intensified and gotten louder from the attention I was paying both her pussy and now her arse too. I began to feel certain that my beautiful brunette bedfellow was also starting to ever so slightly press her body back against my thumb. I decided to test my theory and hovered my thumb outstretched while is gently grazed her puckered hole.
Jess took my cock from her mouth, moving to kiss all around my groin, and now began to use her hand on my shaft. Her nose pressed against the flesh at the base of my cock, Jess began to gyrate gently against my thumb. "Unngh" came her moan and heavy breathing. She then raised herself up on her hands so the her back was arched. She was loving this, I thought. The fact that Jess was getting turned on to this degree by me playing with her arse made me feel like grinning from ear to ear. I felt the dampness of beads of sweat running down Jess' body and felt confident enough to push things further. Literally.
Jess bucked and gasped as my tongue pushed into the tight ring of her arsehole. Dipping it into her, I could feel her muscles flex and tighten against its intrusion. Jess couldn't help it, but the winces and flashes of pain and shock from my attention on her arsehole caused her thighs to grip me and nails to dig in to my exposed thighs. I held my tongue in her as she shuddered. I was unclear if it was pain, pleasure or a mix of the two. I pulled my tongue from her arse altogether and kissed Jess' cheek. Jess lowered herself down onto my body in the same position as before and sighed out a long breath. Her arsehole practically winking at me, and now I dampened my thumb with spit from my mouth again and pressed hard against Jess. Jess' reaction to the second, repeated intrusion was more explosive.
"Unnngh!" she grunted and briefly scrabbled at the bed sheets before propping herself up on her hands as before. Holding my thumb inside her as far as the first knuckle, I felt the tightness of her squeezing my lucky digit. We stayed in that position for over a minute, Jess' gentle flexing on my thumb mixing with my spare hand stroking the small of her back. Jess then looked down and saw the diamond hardness of my cock beneath her. Slowly she lowered herself down so that her cheek lay on my thigh and she took my cock in her hand. Feeling bolder, I applied forward pressure and dove my thumb so that about two inches of it were buried in the warm tightness of her hole. She winced and turned her her downwards moaning into my thigh. I was about to stop, thinking that I'd overstepped the unspoken boundaries when I felt a definite and wonderful leaning backward from Jess' body. I'll never forget watching my thumb disappearing inside Jess' glorious arsehole as she let out little gasps and sounds of unexpected pleasure. Best thumb scene ever I thought. Move over Arnie.
Within minutes, the gentle back and forth had graduated into faster thrusts from Jess. When I brought a pair of fingers to her pussy, I found they slid inside with no resistance other than her natural tightness. She was so wet. With fingers and thumb inside her, it took a relatively short time for Jess to cum again. Throwing her hands back behind her and arching her stomach forward, Jess' arse and pussy consumed my digits and she ground her hips downwards as her orgasm hit. This orgasm however, was more of a scream of pleasure than the panting and gasping of before. I was in heaven, and so too it seemed, was Jess.
She flipped unceremoniously to the side after her lingering moment of ecstacy had subsided and my thumb and fingers escaped her with a quiet, wet slurp. She panted and reached out for my hand, which I gave to her. Then she started to laugh and touched her arsehole gingerly. Well, if I wasn't turned on before...
What's next?
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Bonus night
An offer that's difficult to refuse
An out of the blue message from my ex, Jess, leads to an eventual meet up and temptation. Leaving my current girlfriend, Laura, back at our flat in London, I get on a train to take me to see Jess, though Laura has no idea. , circumstance and perhaps a little careful planning might make one thing lead to another...
Updated on Dec 16, 2023
Created on May 19, 2022
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