Frustrated Guy

Story Info
Girl hasn't responded to a boyfriend.
4.6k words
4.08
28.7k
1
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

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.

She ran her tongue across her lips in anticipation. Tim stood in front of her as she again put her hand around his shaft and pumped lightly. The break had really helped Tim as his cock had lost some of its stiffness, so he was in no immediate danger of losing his load. Bev noticed and thought, "this will be fun as he is not as excited." She also cupped his balls with her right hand. "It looks like someone is not too stiff, but I will take care of that right now!" she said looking up into his eyes.

She started licking up his shaft causing Tim to come to complete attention. It caused him to release moans as she went upwards. When she got to the head she teased him by running her tongue in the slot. She also got a taste of his precum, which she liked. Bev then slid the tip into her mouth and sucked. His moans got louder so she knew she was pleasing him. She took more of him in until he hit the back of her mouth. Bev had never tried to deep throat a guy even though several had tried to force their cocks down her throat. When they did that she dumped them as they were untrustworthy as far as she was concerned.

She pulled her mouth back until only the tip remained inside and then lowered her head again until she developed a rhythm. She felt Tim's hand on her head and thought "Here it goes. He is going to try to push his dick down my throat and that will be the end of this!" But he didn't, he just assisted her bobbing. After a few minutes Tim reached down and pulled her to her feet and kissed her.

He pulled her close, "Baby this is the best thing that has ever happened to me." "I'm glad you like it, but why did you stop me?" she replied. "Don't you like the way I am doing you?"

"I love it," Tim replied. He then kissed her deeply and she responded in kind. During this kiss he roamed his hands over her back gaining a more enthusiastic response from her. He reached for the hem of her tank top and started pulling it up.

"What are you doing?" she asked.

"It would be so much better if you were naked too," said Tim, "but you don't have to do anything you don't want to as I said earlier. You have done more than I expected anyway. If you decide not to, I hope you will finish your fantastic blow job. I just thought it might be better if you weren't wearing clothes. Anyway, I needed a break as I was about to explode and I want this moment to last as long as possible."

Bev was very quiet and stood there not moving with no expression on her face. "I think I have screwed up again. She is going to get angry and want me to take her home. "Why can't I ever get things right? Then maybe I would be more successful with women," thought Tim. Finally, after what seemed years she smiled and raised her arms over her head for him to remove her top. He gently pulled it up and over her head, exposing her black bra holding her breasts. Tim pulled her close to kiss her once again as his hands went to her back to open the clasps on her bra. When it opened, Bev stepped back and shrugged her shoulders causing the bra to fall away from her body and he saw her wonderful breasts for the first time. Tim gasped at their beauty. They were small, with no sag and stuck straight out from her chest proudly. The nipples were a dark red and he could tell she was somewhat aroused by their erection. "Do you like what you see?" she asked.

"Yes they are beautiful!" he responded.

"You can touch them if you want," she said. "But you have to remove the rest of my clothes."

Tim reached out and cupped each breast gently in his hands. He hefted them and ran his thumbs over the nipples causing a moan to come from her lips. Her eyes were closed as he did this and opened when he knelt down to remove the rest of her clothes before she could change her mind. He took off her shoes and socks as he made her do to him. He reached up and unfastened the button at the top of her shorts and pulled down the zipper. The shorts parted and he pulled them down as she put her hand on his head to steady herself. She raised each leg for him to remove the shorts. She was standing there with only her bikini panties separating her from Tim's eyes. The panties were black but Tim noticed they had a wet spot indicating she was getting off on this. He reached up grasping the panties on each side of her hips and lowered them. When they were on the floor she stepped out of each side and kicked them to the side. Now she was completely naked and Tim was in the presence of something greater than he could have imagined. As he looked up he saw her trimmed dark curl covered pussy, further up her magnificent breasts and her erotic lips that had been wrapped around his cock a few minutes ago. He hoped they would be there again soon.

Tim started kissing his way up her body by kissing back and forth over her legs. He really liked kissing up her thighs as she responded with gentle moans. Tim continued upward, planted a good kiss on her pussy, proceeding to navel and then her breasts. He didn't linger at her pussy even though there was a strong scent of arousal so as not to piss her off where she called a halt. He continued kissing up across her throat, around to her ears and eyes finally reaching her lips. As he kissed her he pulled her naked body into him and slipped his tongue her mouth. As they kissed his hands roamed over her back and he covered her cheeks pulling her closer to him. So close he could feel his hard cock trapped between their bodies. He noticed her breathing was as heavy as he had heard all evening.

After a while he stopped kissing and placed his hand on her shoulders, "Do you want to finish the blow job you were giving me?" Bev was also breathing hard and shook her head in the affirmative. Tim then applied gentle pressure downward and she knelt in front of him and took his cock on her hands. She slid up and down while her lips caressed his balls. She licked up the shaft to the top and engulfed him. Tim moaned his pleasure and she really started going up and down his stick licking as she went.

Bev thought, "This is so great. He is truly a gentleman as most guys would have tried to fuck me as soon as they got my panties off. I am going to give him the best blow job he has ever had." And she delivered! Tim felt a stirring and knew he was about to cum.

"Bev, I am cumming," to warn her but she kept pumping up and down on his dick so he put his hand on her head. "Here it comes!" he cried as he shot his load into her mouth. She kept sucking and when he was dry moved her mouth to the tip of his dick and sucked some more. The sensation on this sensitive part almost brought him to his knees.

After the euphoria subsided Tim reached down and pulled Bev up. He put his arms around her and held her naked bodies close to him, feeling her breasts press into his chest. "I don't see how it can get any better than that," he thought. He moved to kiss her and they shared a deep, full kiss. "That was amazing," Tim said. "Now it is your turn to get pleased." With that he slowly backed her to the bed. As her knees touched the bed she became a little frightened,

"You promised there were no strings attached, Tim, and I don't want to be fucked."

"Don't worry. I am not putting you here to fuck you, but to make you feel as good as you made me. But if you don't want to, we will stop right now."

"You promise?" she asked.

"Yes," Tim said. "I want to make you feel good because I know you are worked up and need release. Nothing other than what I am going to do will happen, even this, if you don't want it."

"Ok, but you remember your promise," she said with a tone of reluctance.

"This has been a very enjoyable experience and I just want to make it so for you," Tim said as he laid her on the bed and got in beside her. Tim kissed her deeply and long as his right hand caressed her shoulders and eventually came to rest over her left breast. He noticed her nipple was even harder than before and as he massaged and tweaked it, it grew even longer and harder. He adjusted his position so he could massage her right breast and suck on her left. During this Bev started moaning and pushing her breasts into him. Finally he was sucking on her right nipple and moved his right hand downward and lightly brushed her curls as he passed toward her thighs. He lightly massaged her right thigh up toward her pussy and just around it to her left thigh. Bev spread her legs and moaned more. Finally he moved his hand to cover her mound and travel around her lips. He then inserted his middle finger into her and she responded with moans and undulations of her hips trying to get more of his finger into her.

"Man, she is hot and wet," thought Tim. "I wish I could fuck her right now!" But he knew he had to stick to the plan. He started kissing down her body sticking his tongue into her naval which got a pleasant response from her. He continued downward until he was kissing her right thigh downward and back up toward her pussy that he was pumping with his hand. As he approached her pussy he removed his hand and barely brushed the hairs as he passed to the left thigh with the same down and up move. As he approached her pussy again he saw it was glistening with moisture. This time though he used his hand to spread her lips open and then licked up and around on them; purposely avoiding her clit which was sticking out from previous ministrations with his thumb.

Tim then stuck his tongue into her love canal as far as he could get and started moving it around. She reached down and pulled his head in closer. Finally he moved up and took her clit in his lips and started sucking as he put his finger back into her. She really started undulating and moaning, "Oh God don't stop, I am CUMMING!" she screamed and there was a flood of juices that Tim eagerly lapped up. Her pussy was grasping his finger like mad. He knew he had scored some points with her by the way she was acting. He kept at it until she reached down gently pulled on his hair indicating she wanted him to come up. He then kissed his way back up her body to her lips where they shared a long kiss.

"That was AMAZING!" Bev exclaimed. "I have never experienced anything like that!"

"You mean other guys haven't gone down on you?"

"Yes they have, but they just kiss it and want to stick their dick in. Where did you learn to eat pussy like that?"

12