Tim was extremely frustrated. He had been going out with Bev for almost a year and had not gotten very far. Granted, he was not the best looking guy, but he was honest and sincere. Bev had acted in ways that made Tim believe she was ready for something more than kissing and soft petting but then refused to act. Tim finally had a plan to call her bluff. She was always commenting on how she could tell if a guy was circumcised or not, but they had not even gotten past first base. However, Tim had a plan even if it meant he would be naked first, with no guarantee that he would get to see her naked. If it didn't work, at least he tried and she would get a look at him.
Tim picked Bev up at her parents' house on Saturday around 6 PM. He was pleased that she was dressed in a red tank top and blue shorts and he was in a white golf shirt with jeans. They went out to dinner at a casual restaurant and to a movie. Tim paid no attention to the movie as he was thinking about later when he would put his plan into action. After the movie they went to Tim's apartment where he fixed her a bourbon and coke as well as one for himself. They sat on the couch and talked a while. Shortly, Tim leaned over to kiss her and she responded with a deep French kiss that started the familiar stirring in Tim's groin. Tim rubbed her back during this and repeatedly went over her bra strap; however, when he moved around to the front, Bev stopped him when his hand had covered her right breast. "I don't think this is the time", she said.
"We have been going out for over a year and you won't even let me touch your breasts through your clothes," responded Tim. "Is there something wrong with me? I know you have gone out with other guys and I believe some of them got further than I have, not that I am implying anything."
"There is nothing wrong with you, Tim. It is just as your Dad and mine worked together, that I think of you as more a brother than as a boyfriend. I don't mean to lead you on, but that is just the way I feel," replied Bev. Tim saw his opening.
"Bev, I have a proposition for you that will possibly be a gain for you with no strings attached."
"What is that?" replied Bev.
"We will go into the bedroom and you can remove my clothes with no obligation for you to do anything else."
"You mean I will remove all your clothes and there will be no requirement for me to reciprocate?"
"That's right-no strings attached. You won't have to do anything you don't want to," said Tim.
"I don't know," she replied, "It doesn't seem fair to you."
"Honey, I don't mind or I wouldn't have offered this. I think you know me well enough to know that I will not do anything to hurt you," Bev was silent for a moment and Tim didn't interfere. He let her go through her decision making process. As she was thinking the proposal over, he went and refreshed their drinks and came back and sat on the couch.
Finally she said, "OK, let's do it, if you are brave enough!"
Tim stood up and offered her his hand so he could help her up. They both picked up their drinks and retired to the bedroom. Bev had been in his room before as the bathroom was off the room. Tim had made the bed as he always did whenever he knew she was coming over. After they were in the room, Tim said, "I better check and make sure the door to the apartment is locked. We don't want anyone to walk in on us!"
"I think you are getting cold feet, "Bev said grinning. Tim went and checked the door and put the chain lock on as well. He returned to the bedroom and shut and locked the door.
"That is in case anyone gets through the first barrier," Tim said grinning. "Now it is time to see what you are made of, Bev. Come here and get started if you dare!" Tim took a good swig of his drink as he felt he needed all the courage he could get to keep from chickening out. Bev came over to him, took a sip from her drink and set it on the dresser alongside his. She reached for the hem of his golf shirt and pulled upwards. Tim raised his hands above his head to help her. This required her to come closer and her breasts rubbed against his chest as she pulled the shirt off. She tossed the shirt onto the bed and turned back to Tim and the task at hand.
Bev thought "I am going to get him naked, see what he has and then have him take me home."
As she reached for his belt Tim stated, "No, Bev, you have to remove the shoes and socks first before you can remove the pants." Bev looked at him as if trying to figure out if he had been serious or not. Then realized that suggestion made sense as his jeans would not come off that easily over his shoes and he had said that she would get to see him naked. Bev knelt down in front of Tim and reached for his left shoe. Tim raised his foot for her to remove his loafer and sock. He put his hand on her head to steady himself. They followed the same procedure for the other foot. As she was doing this her tank top pulled away and Tim got a bird's eye view of her breasts encased in her bra.
Bev reached up for the belt buckle and hesitated, "You are sure there is no strings attached to this?" she asked.
"That is what I said," replied Tim, "Are you starting to get cold feet?" With that challenge she reached for his belt buckle and started opening it. She got the belt open, but had a problem with the button on his jeans. Tim reached down and undid the button. Bev reached up to the zipper and hesitated. "If you don't want to go any farther you can stop now," offered Tim, even though he wanted her to go farther and he might get to see more of her breasts than the shot he was getting now. At that comment, Bev pulled down on the zipper. And the jeans parted. She reached to his sides and pulled the jeans down. Tim again placed his hand on her head to steady himself as he raised one leg and then the other for her to remove his jeans. Bev didn't even bother to put them on the bed, but just tossed them to the side. She realized she was getting hot. Her breasts were stirring with her nipples starting to harden and moisture forming between her legs. Tim was right that other guys had gotten further than he had, although none had gotten a home run. The closest anyone had gotten was their finger in her pussy. She had let him take her to orgasm, but no further. Meanwhile Tim was grateful that she had undone his jeans as he had a hard-on that was the Mother of all woodies.
Bev looked up and saw that Tim was obviously aroused and she started to have doubts as they were in his locked bedroom and he was stronger than she. However, he had never ever done anything other than as he said, so she relaxed and decided to enjoy the moment. Tim's cock was so hard that the tip was above his jockey shorts. "What have we here?" she asked with a smile as she reached up to pull down his briefs. However, as she pulled Tim's dick got caught. He reached down to help by pulling the band out, but Bev gave a jerk and the briefs came free. Tim's cock sprang upwards and smacked into his abdomen. Bev pulled them down and Tim stepped out of them as before again getting a view of her breasts as her top fell away. She flipped the briefs away toward the jeans and was face to face with his cock. Bev knew she should get up, but she was fascinated that a guy would do what Tim did without any strings attached. "OK, you have done your part Bev and like I said, there are no strings attached," said Tim. Tim noticed she was staring at his cock and saw an opportunity. "Go on touch it if you want," he said. "But there is no obligation." Bev reached and touched it and it seemed to jump. She studied it. The dicks she had been in contact with before were either in dim light or darkness. She wrapped her hand around it and stroked up and down. In the process she saw some pre-cum ooze out of the tip. She took her finger and smeared it around the head. Understandably, Tim was going wild and fighting to keep from cumming too soon and spoiling his plan. Bev took her other hand and cupped his balls and gently massaged them. This definitely caused Tim to struggle to keep from shooting his wad.
"This isn't fair to you," Bev said. "You are so aroused it has to be uncomfortable. Would you like me to give you a blow job?" Tim almost shot his load right then.
"Yes I would, but please wait a little bit," Tim finished his drink and noticed Bev's could be refreshed also. "Let me go make us a couple of fresh drinks."
"OK," Bev replied, "that will be great." Tim picked up her glass and left the room.
"I needed to get out of there for a minute to calm down," Tim thought as he went to the kitchen. "This is going better than I thought and I'm definitely going to enjoy this. Maybe something else will happen, but if not it has been a successful evening. I will make her drink a little stronger."
Bev was still sitting on the floor while Tim was gone. She was thinking about how she had teased him and not delivered. Yet he was the nicest guy she had ever known and the one with the most potential. "I owe him and I will make it up to him," she decided.
Just then Tim returned with their drinks. She giggled when he came into the room. He sat their drinks down while he relocked the door. "Why are you laughing?' inquired Tim as he handed her drink to her.
"You look so funny walking in here naked with your cock swinging back and forth. I have never seen a guy walk naked before," she took a big swallow of her drink and set the glass down. "Now where were we?" she said with a smile and returned to her knees.