| Once he saw the two pieces of the puzzle so close together, he knew it was going to be a difficult task. Becky pulled at his massive unit until it was at the door of her pussy. There was absolutely no give at all. They were both terribly excited, which did not lend itself for their first attempt at copulation with such an awkward difference in the size of their genitals.
Joe pushed forward trying to penetrate his lover, but nothing. It just didn't seem to work. They both fumbled, trying to make their first attempt successful, but it seemed more hopeless the more they tried.
Just then Becky forced herself up and told Joe to stop. She realized that she was indeed attempting to have sex. She was about to try unprotected sex, with a guy seemingly equipped well enough to get the job done if penetration ever was successful. She pushed him away as she got up naked and disappeared out of her bedroom door again leaving Joe confused and raging with lust. She returned with a condom from her brother's supply and asked him to wear it before they tried again. It did say lubricated condom, so Joe thought it might even be of some help.
Becky was wet, and Joe was beginning to have a slow and steady leak coming from his penis as he prepared for what he hoped was the inevitable. He opened the small package and attempted to don his first prophylactic. He noticed right away that the condom's rubber ring's diameter seemed to be small when compared to the diameter of his penis. But he knew it had to be that way to make sure that Becky wouldn't wind up unintentionally having his child. It must have been made like that for a reason. Everyone must encounter this obstacle when getting ready to use this form of birth control or so he thought at the time.
He placed the condom at the end of his penis at the cock head right over his piss slit and tried to roll it over his glans, which had an even larger diameter than his shaft. It was turning out to be more difficult than he thought it should be. The condom pulled tight as he started working it over his dickhead. After it was rolled past the ridge of his penis' head it snapped around his cock very tightly. He wondered if this is the way it should feel. It was uncomfortable, but he continued to roll the condom over the shaft. Again he lost grasp and the ring snapped hard around his shaft. He flinched and Becky asked him if there was a problem. He told her it hurt when he let go of it. The pain started becoming more apparent to her, as his penis was starting to become soft from the pain of wearing the condom. She grabbed him and stroked him back up to his full erection, but the ring continued to grab him and cause pain.
She was becoming desperate. How could this happen? Their first attempt to fuck and they would have to be stopped because they were taking the appropriate precautions. Joe took a chance and asked her if they could go back to trying with out it. But the look on Becky's face told him that would not be an option. She asked him if there was any way he could use the condom that it wouldn't grab him so much. He told her no, but it was better when the ring rested right beneath his cockhead. He rolled it back toward his tip, and stopped right below the ridge. He kept his erection, but it wasn't ideal. It still gave him negative feedback, but it was bearable and it was wearable right were it sat.
He looked at his predicament and laughed. When Becky wanted to know what was so funny he gestured to his throbbing penis. She let out a laugh too and asked him if it still hurt too much. He said it wasn't the best but it would work. The strange thing was that the position of the condom seemed to make the deep color of his glans look dark blue instead of its normal purple/pink color. It may have been from the blood flow being stopped some how by the tightness of the condom around the head of his big boner. Whatever it was, he felt he was now properly dressed for the occasion.
He told her he wanted her really bad after all the stimulation he had gotten to this point. She got back on her bed and spread her legs inviting him to try again. He didn't need a better invitation than that and was back into position in no time. He played with his penis at her pussy, trying to get the mood and excitement back. He needed no further encouragement, but her telling him that she was ready was an additional bonus.
He grabbed his cock and aimed for his target. He slowly started the forward pressure. He was once again right at her door way and knocking, but she wouldn't let him in. He thought more forward pressure would help, but he was not making any progress. He thought he was doing something wrong, but she reassured him that he was pushing at the right place.
Joe was afraid that forcing too much would hurt Becky, but he didn't see an alternative. She told him to do whatever felt right to get in. She wanted him. So he decided that a slow steady onward force might be the best chance to get things moving. He slowly started pushing. Nothing. He kept pushing, and pushing at her entrance. He was pushing against her, but not going in. He was just pushing.
After he had pushed as much as he could he heard her yelp. He let up and looked at her. He could see that it wasn't working and it was beginning to be uncomfortable for her. So he decided the best thing to do was to try something smaller. He thought starting with a finger would be easier for her and give him an idea about what to expect inside her.
He started touching her entrance. Probing. It was moist, and he started pushing his digit in. It was so warm, hot. He watched her for any sign that she was uncomfortable. She was apprehensive, but didn't seem to mind his gentle invasion. He got more comfortable with his new surroundings and began to feel her insides. He could only imagine what his cock would feel like inside of her.
He thought having two fingers would relax her more as he massaged her from the inside. It was then that he understood the reason for his unsuccessful attempt at lovemaking. It was a snug fit with two fingers. He continued probing with two fingers moving around. As he spread his fingers apart he noticed that Becky seemed to give a bit. She seemed to get used to the size of her two-fingered invader. After a while he inserted another one in the same fashion. This seemed to be the key. Start slow until she relaxed a bit, and then insert more, that was the secret to success.
Joe decided that after his three fingers, he would go back to his throbbing penis and try it again. He noticed his glans was still quite a bit larger than his three fingers together, but she was opened more than the first time he tried. He once again positioned his penis at her entrance and slowly pushed.
This time his piss slit was touching the warm moist entrance a bit inside her. It was a better place to start from. Now he could feel his goal's warmth and wetness through the thin rubber. He had a renewed sense of urgency to complete his mission this time. He wanted to be inside her so bad that he started pushing too hard again, and was once again getting nowhere.
He started to get frustrated, but the look on Becky's face told him to keep trying. He put his free hand right above her insertion point and massaged her. He could tell it felt good to her. He told her to calm down and relax and it would happen soon. This was helping. As he massaged her, he was very slowly pushing into her.
It was such a slow pace that she didn't seem to know it was happening until almost the first quarter of his dickhead had found home. She began to feel him encroaching into her. Things went smoothly until about half of his cockhead was inside her, then it seemed no matter what he did his approach didn't seem to be working anymore.
She asked him why he had stopped and he told her he wasn't able to get in any further and he was afraid he'd hurt her if he pushed harder like before. She convinced him that she was ok and now that they had started he should push forward until he was in.
He wanted nothing more than to get into her, and since it was her suggestion he started pushing with vigor. It just didn't seem to work. His penis had simply gone as far as it could go. Becky was getting anxious and hot. She told him that she wanted him and to please get it in her. This only made matters worse for Joe. It was such a turn on, but what could he do differently?
She was begging for him to get it in. So he kept up his pressure. Then all of a sudden her cunt seemed to give up some of its resistance and over half of his cockhead was in her warmness. Both got wide eyed and smiled. Becky was breathing heavy and Joe was becoming more and more determined. He tried it again.
Keeping the pressure up, he pushed forward once again hoping the same thing would happen. He figured once the head was in it would be downhill from there. He found out later that is not quite how it worked. His cockhead was really acting as a kind of crowbar inserting itself into cracks as they appeared. As the crack got bigger, his penis was allowed to move forward before finding another tight space to steadily pry open.
Both of them were in need. Joe kept the pressure up and without warning he found his cockhead almost completely buried in Becky. She let out another yelp and told him to stop…the pain was now starting to mount for Becky. He did as he was instructed and removed the forward pressure and backed out of her to his previous depth. She recovered quickly and told him to try again.
He put pressure on her again and he was back in her as deep as before once again, she winced but told him to keep going. As he pushed she gave way once again and loudly told him to stop. He did, but it felt different almost as he was locked into place. His cock head was inside her now. They had gotten past the huge ridge on his massive cockhead and her body told her to stop the invader…it was too much. | 
