Proceed as planned, but he is met with resistance

He did as he was told and went towards Elena's butt. Like a Christmas present her bottom was still wrapped up in her pajamas. He quickly unpacked his present and grabbed her asscheecks to spread them wide only to be greeted by her bare pussy and her puckered asshole. He took his time in order to enjoy the sight as much as possible. Eventually he grabbed his dick and aimed for her rosebud, only to be met with quite some resistance. As he started to use more pressure, Elena started making some yelping noises. Steve realized this would not get them anywhere.

S: "Elena I know it´s uncomfortable, but it mostly hurts because you don´t relax your asshole" Steve said in order to weaken her resistance.

Eventually he could feel her relax a bit more and he slowly inserted his dick inch by inch, all the while hearing muffled noises coming from Elena. Once he got half way in he realized the whole process took to long and he dried up, so he retrieved his dick much to Elena's surprise.

S: "Sorry Elena, but I will have to use your pussy to lube up my cock again"

Elena's protest only met deaf ears as Steve lined up his dick with her pussy. He actually expected her to not be wet at all and instead found her to be decently lubed up, not dripping but enough for his cause. He was again met with resistance, but it was nowhere near enough to stop his attempt.

He took his sweet time exploring her wet folds, alternating between thrusting in and out and just leaving it inside for a couple of seconds. After a minute of playing around, he was finally well lubed up again. Much to Elena's dismay he went back to her dark tunnel. Again the exploration of her asshole was met with muffled noises, but there was no turning back now. Then Steve was caught by surprise.