He gives her a kiss on the head and looked into her eyes. alright then, i'll go slow and very gentle so not to hurt you He said and gently as if holding something very valuable pulled her up and he turned her around and let her lay on the ground again. He knew despite not wanting to look at him she'd still want his reassuring touch. He practically layed himself over her and she could fell the tip of his cock nudging her entrance. Alright...now relax that little bottum of yours, and if you ever need me to do something else like stop or touch your other places, say so immediatly He said waiting to see if she could relax her muscles as his cock was ready to enter her.

Riko stared down at the grassy ground - the grass was flattened and a little torn up from where her body had been rubbing against it. On her back was a big green grass stain.

She leant on her hands, doggy-style and felt her ass contract shyly against the dick which was touching it. At the same time her pussy sent out a little dribble of anticipation.

He brushed away all the grassy stains on her lovely back sneding tingles of delight into her and slowly begins to push into her ass. Remeber relax He said as he kept pushing in.

To help he started to play with her breasts and used his massaging trick to play with her wet pussy to help ease any pain she felt.

Riko released a loud moan - half from pleasure and half from pain. He was causing a delightful buzz of pleasure in her slit wit his tickling massage.. at the same time, her little ass stretched painfully to accomodate the new intruder. It hurt - the stretching.. but there was something guiltily pleasurable about it.. she could feel his dick rubbing up against the back wall of her pussy.. "Mmmm...."

He kept pushing in slowly helping drain away the pain with the massaging of her breasts and pussy. He knew this girl if she had been done anally by anyone else it would have been bigger and more painfull. He heard her moan of pleasure and pain and thought it was a start and so far she wasnt complaining so he continued unfazed.

Riko bucked her hips as it pushed deeper inside, penetrating her in a never before touched place... It was new, exciting... but .. it did hurt... Riko let out a light drawn-out groan as she stretched. It could easily be mistaken for a moan of pleasure though, so her discomfort may have gone unnoticed.

She dropped onto her elbows, ass up in the air, still clutching his dick tightly. With each push further inside, it clenched down tighter!

Riko's pussy was clenching too on its invisible pleasurer, wanting more, spurting a little wetness out over the underside of Sintor's cock, trying to help ease the pain and increase the pleasure in her slit.

Her discomfort didn't go unnoticed and he stopped for a minute letting the massages get her into a more comfortable state. The way her ass squeezed his cock was amazing since he had never done anyone this small and this tight so he brough one hand , the other playing with both breasts now, and stuck a finger into her wanting slit.

Where almost there little strawberry He said reassuringly and true to the word 10 seconds of pushing and he was all the way in. He let it sit there waiting to see if she'll ask him to move it yet or wait. He kissed her soft neck nuzzling it a bit and from the corner of her eye she could see him smiling in reassurance, relief, and congratulations.

"Oh... oh..." she moaned softly as his finger distracted her from his cock's entry. The stretching feeling gently eased off, and she was aware only of the delicious pleasure his finger was giving her pussy. It felt really good having something in both holes.. she squirmed and giggled at the soft, slight feeling of breath and skin on her neck.. all of this attention her little body was receiving was just fantastic.. the girl even pushed her hips out so that his finger rushed over her clit at the same time. "Oooh!" she said, closing her eyes and resting her head back against his strong shoulder.