Seize the Opportunity

Jeb never forgot how he lost his virginity. He was nineteen and at a low point in his life. It was summer, and he had finished high school and was looking for a job. Nothing felt appealing. He wasn't particularly tall or muscular--more on the scrawny side. His father often said it was because he did not play football at school. Jeb hated football.

His father said many things. He told Jeb to stop ambling around at home after finishing high school. He had a friend who owned a tire repair shop and was looking to hire. Jeb shuddered at the idea; it was smelly, dirty, and heavy work. The pay was lousy as well. His father told him to shut up, swallow his pride, and go to the damn repair shop.

His mother wanted him to start university, but this idea did not appeal to him either. He had finished school and did not wish to return. Besides, he would likely end up in debt for life.

Jeb spent most of his days avoiding conflicts with his parents. Instead, his attention focused on girls. Or lack thereof. Like most teenagers, his hormone-filled mind was most of the time turned on. It made him have an erection all the time.

They say that one of the best periods of your life as a guy is in your early teens. It is at that time that you discover what a marvelous tool your dick is and all the things you can do with it. They also say that one of the lowest periods of your life is when you discover that girls don't share that epiphany. Jeb was at that point in life. He was frustrated to no end that he was still a virgin. He wasn't particularly bad-looking but scrawny and insecure, and no girl looked twice at him. It did not help that he got tongue-tied whenever he tried to talk to a girl.

Internet porn and tissues were his only relief, but it left him more frustrated than before.

Jeb's parents were having a barbecue. It was something they liked to have more than once during the summers. As usual, it was between twenty to thirty guests. Primarily friends from work and neighbors. Jeb did not find the barbecues much fun, as only grown-up people were around. They were eating and drinking and getting rowdy as the evening progressed. Towards the night, everybody was quite drunk. His mother usually made him help in the kitchen. Besides that, he tried to stay out of the way. The only advantage was that he could steal a beer without his parents noticing.

Sometimes, there was drama once everybody was drunk and had their inhibitions lowered. This time, Linda made a scene. Jeb had already driven one of his parents' drunken friends twice to the store on a beer run. It was well past midnight, and everybody was plastered. Jeb did not mind when his parents had a barbecue. He thought it was all right but disliked it when everybody became so drunk as the evening progressed. Regardless, he still hung around. To him, it looked like the barbecue would be over soon.

Linda had a drunken argument with her drunk husband, Larry. It escalated until they shouted at each other. Others began interfering before it turned into blows. Linda accused Larry of being too interested in one of his colleagues at work. She was sure Larry would sleep with her if he could, or he had already done it. Larry angrily defended himself, shouting at her that she was making a scene and a fool of herself.

Jeb's father and a couple of friends separated them and led Larry inside to the living room. Linda slumped down on one of the lawn chairs, still upset. Jeb tried to stay out of the way. The barbecue was winding down, and people were leaving. A couple of Uber cars stopped outside. Guests milled around inside, not realizing their rides had arrived. After a while, the two drivers came inside to try to get hold of them.

Jeb felt thankful that it was over. When his father intercepted him, he intended to go to the bathroom and then to his room. He told Jeb that Larry had fallen asleep on the couch. Then he asked Jeb to help Linda get home safe and sound. She and Larry lived in the area. Their house was less than a fifteen-minute walk away. His father was slurring his speech, and Jeb heard his mother calling for his father from the bedroom. She sounded drunk, and Jeb had a good idea of what she wanted. Jeb shuddered at the idea of his parents having sex and thought it was a good idea to get out of the house for a while.

Jeb found Linda in the garden. She was muttering to herself and waving about with a half-full glass of red wine. She was in a foul mood, and it took a while for Jeb to convince her that they should leave and that Jeb was walking her home. He got her to give him her wine glass, but not before she had drained it. She was unsteady on her feet when he helped her up from the chair.

They went through the house to the front door. Passing the living room, Jeb saw Larry sleeping on his back on the couch. Linda was drunk, and Jeb had one hand on her arm to steady her as they walked. She was droning about her husband, but he ignored what she said.

Outside their front door, Jeb realized something and stopped.

"Do you have your home keys?" Jeb asked.

Linda stopped her tirade and looked at Jeb with a drunken expression. It took her a while to work out what he had said.

"Nah," she said, "it's my asshole husband who has them."

Jeb sighed. What a mess. At least, he had asked before they walked the short distance to Linda's house.

"Wait here," he said and went inside again.

Larry was snoring on the couch. Jeb shook his shoulder and called his name. There was no reaction. Jeb shook his shoulder harder and called his name louder. Still, there was no reaction. Jeb felt at a loss, but then he spotted a lump on Larry's front pocket of his shorts. Gingerly, he touched it. It felt like a keyring. Jeb did not know what to think as he slipped his hand into Larry's pocket. Luckily, he got hold of a key ring and fished it out. There was no reaction from Larry, and Jeb felt grateful.

Back outside again, he found Linda sitting on the front porch.

"Got your keys," he said, motioning for Linda to get up.

Linda leaned forward to get up but fell back again, giggling drunkenly at her clumsiness.

"Help an old lady, will you?" she slurred and held out her arms.

She made a new attempt to get up, and Jeb pulled her outstretched hands. She got on her feet and stumbled forward into Jeb's arms.

"Oopsie," Linda giggled. She clung to him while regaining her balance.

Linda had a generous bust, and her boobs pressed into Jeb's chest for a few seconds. The feeling made a switch flip in his mind, and his cock stirred. She might be old, but he felt her boobs. The hormones fueling his imagination started running through his veins.

Linda disengaged from Jeb and began walking towards home. He came out of his momentary daze of having felt her boobs and hurried to catch up with her. She was unsteady, and Jeb put his hand on her arm to steady her as they walked.

They were quiet, but then Linda resumed complaining about her husband. She complained about Larry in general and him not paying her attention. She waved about as they walked together. Jeb held her upper arm, and his hand brushed against the side of her swelling boob every time she swayed. Jeb was acutely aware of her boobs since the moment they had pressed into his chest. His heart jumped every time he felt her boob brush against his hand.

Linda tripped several times in her high-heel pumps. She made an annoyed sound when she once almost fell. She stopped and kicked off her shoes. Jeb still held her arm, and it made her ass press into his hip when she leaned forward to scoop up her shoes. It made his heart jump not only once but twice.

Covertly, he checked out her ass when she stood up again. She was too drunk to pay attention to where he was looking, so he checked her out a second time longer. Her ass was as nice and round as her boobs. She had a few extra pounds, which only accentuated her curvy look. Someone her age would say she was voluptuous. He was aware of the age difference. Linda was not as old as her mother. He guessed she was about thirty-five. She and her husband were not close friends of his parents, but they had been neighbors for a long time. He was familiar with them. Jeb knew she had two children, aged seven and nine. He also knew they usually spent the night with Larry's parents, who lived nearby.

They continued walking. Linda had been almost Jeb's height in her four-inch pumps. Barefoot, she was distinctly shorter than him. Somehow, the height difference made Jeb feel more male next to her rather than a skinny teenager.

He looked down at her boobs again. There was a tempting valley showing between her boobs over the neckline of her low-cut top. She was too drunk to pay attention to where he was staring. She was again complaining about her husband. She complained again that he was not showing her any attention. She was sure he was interested in 'that skank' at his office.

His cock began to feel uncomfortable in his pants as he stared at her boobs. She was less unsteady after taking off her shoes, but he still held onto her arm. On purpose, he let his hand bump into her side boob. She did not pay attention and continued talking about her husband. He could not tell why, but something was alluring and sexy about how she looked with one high-heel shoe in each hand.

A while later, Jeb dared push on her boob again. This time, he did it hard enough so that he felt the soft mound mold around the backside of his hand. Still no reaction from Linda, who was complaining about her husband's lack of attention. His cock got even more uncomfortable in his pants. He looked over her back, at her ass swaying as she walked beside him. Still, she did not pay attention to what she did. Her voice was angry, and she had increasingly worked herself up in her complaints.

She stopped and looked at him with an earnest expression.

"Tell me!" she said, sounding angry and slurred. "Is it too much for a girl to ask for some cock once in a while?" she demanded.

Jeb blushed. He was unprepared for the question. He had been too busy checking her out to follow what she had been discussing. He was also not used to an adult speaking so crudely to him.

"No, I guess not," Jeb mumbled, blushing. His cock felt even more uncomfortable in his pants.

"Damn right!" Linda exclaimed, and she resumed walking as abruptly as she had stopped. Jeb tagged along, still holding her arm.

She complained more about her husband. Jeb tried to follow what she was saying, but she was mostly incoherent. He understood it was more talk about Larry's performance or lack thereof in the bedroom. She seemed to have lost all her inhibitions about what she was saying. Jeb had seen her drunk before but never this drunk.

They entered her street, and soon, they walked up her driveway. Jeb had mixed feelings. Delivering her home and not listening to her ramblings was a relief. At the same time, he was aware of her soft body and how her boobs had felt. He did not bother to hide his erection as he fished out her keys from his pants. She stood to the side as he unlocked and opened the front door.

Neither of them realized they were at a crossroads. Linda could have gone inside and let Jeb go home, and he could have gone to bed as intended when his father asked him to escort Linda home. That would have been the end of the night for them both.

Instead, Linda motioned for Jeb to enter the house before her. She closed and locked the door behind them. Jeb looked around. He had visited Linda and Larry's home several times when his family had been invited for dinner. Linda dropped her shoes on the floor with a clatter and went to the kitchen. Jeb dropped the keys on a table by the door and followed. He guessed Linda wanted to drink some water or something. Instead, she went to the counter, where there was a bottle of wine and two glasses. The glasses looked used, and the cork was sticking out of the bottle. Jeb guessed she and Larry had started the evening with a glass of wine before leaving home.

Linda picked up the bottle and one of the glasses. She pulled out the cork using her teeth and noisily spat it out on the floor. She poured herself a glass of wine. She was swaying and sloshed wine up over her hand while she poured. Then she put the bottle on the counter with a bang, loud enough to make Jeb jump.

She looked at him seriously and gulped down a mouthful of wine. She was swaying, and it made him feel uncomfortable. He was not used to being alone with someone drunk, especially someone adult.

"Perhaps you should stop drinking," Jeb suggested, feeling ill at ease.

"You sound like my stupid husband," Linda replied sarcastically. "He is always trying to be in control, trying to decide for the both of us."

Her expression darkened. "As long as it is not in the bedroom, where he has lost all initiative." Her expression darkened further, and she looked angry. "Unless limp-dick can get it up for that harlot at work. I swear to God, I'll kick him out if he does."

She paused and took a swig from her glass of wine. She looked at Jeb with a shrewd expression.

"I bet your father could do it," she mused. "I've seen how he looks at me when he thinks I am not noticing. If I let him, I bet he would give me a thorough work-over."

Jeb felt his cheeks flush with embarrassment.

"How old is he? Fifty?"

"Fifty-two," Jeb replied. His father was ten years older than his mother. Older than most of their friends.

Linda's smile widened. "Even older, and it doesn't seem to hold him back. At least your mother seems satisfied in that department."

Jeb felt his cheeks grow even hotter. He knew Linda could be outspoken and had few filters for what she could say. He guessed the combination of being drunk and angry made it even worse.

"Do you mind if I use the bathroom?" he asked, changing the subject. He usually had no problems talking about sex; it occupied his mind day and night. But it felt weird talking about sex when it came to his parents.

"Nah, go ahead," Linda replied. Clumsily, she waved her hand towards the bathroom, spilling more wine on the floor.

Jeb had a raging erection when he locked himself into the bathroom. He needed to pee. At home, he had been on his way to the bathroom when his father asked him to accompany Linda home. It took him at least ten minutes to wrestle down his erection enough so that he could pee.

He waited about ten more minutes before he left the bathroom. He wanted his erection to go down completely. The idea of talking more about sex and his parents with Linda felt weird. He wanted to leave as soon as possible and go home.

However, the kitchen was empty when he came back. The wine glass that Linda had been guzzling was on the counter, but she was not there.

He went into the living room to see if she was there. It was as empty as the kitchen. Surprised, he walked around. She was no longer downstairs. He came to a stop by the staircase. He had never been upstairs. He hesitated. He should go home but felt it was wrong to do it without telling Linda. She should lock the door as well.

He tiptoed upstairs. There were several doors. One was open and led into a typical children's room. At the end, there was a half-open door, and looking inside, he could see it was the primary bedroom. The room was cast in shadows. The curtains were open, and a nearby streetlight supplied the only illumination. Jeb could hear Linda's heavy breathing before his eyes adjusted to the dark room. After a while, he could make out her form on the bed.

Linda was lying diagonally across the bed. Her back was towards the door. One leg was straight, with the foot off the bed. She had pulled up the other leg so the knee was bent at ninety degrees. It made her skirt pull up high, displaying a mesmerizing amount of thigh. It was also drawn tightly over her generous behind, outlining it perfectly.

Jeb's cock grew hard again when he saw her. His mind filled with the urge to feel her ass. His heart began thumping hard. It was inappropriate to touch her while she slept. He realized that, without thinking, he had taken several steps into the room and closer to the bed. He looked around. The room resembled his parents' bedroom. One wall was covered with closets. There was also a vanity table cluttered with makeup and other things. A chair stood in the corner, covered in clothes that belonged to Larry.

His gaze zoomed in on Linda's ass again. His cock strained in his pants. His feet had a mind of their own and took a few steps closer. He heard blood pulsing in his ears, and his palms became sweaty. He wanted to feel her ass, but it was so wrong. His vision blurred until only her generous ass was in focus. It was terrible, but she was drunk and sleeping. He took one step closer to the bed.

She would not wake up if he were careful in feeling her ass. He was almost by the bed, only a couple of more steps. His cock was straining so hard in his pants that it was painful. He was holding his breath, but Linda was breathing slowly and deeply. He would be able to feel her ass only a little bit, and she would not know. However, somewhere in his hormone-filled mind, there was a voice of concern. He knew that no one was downstairs and that Linda had locked the front door. But he hadn't checked upstairs.

With an effort, he tore his gaze away from Linda's ass. He tiptoed out of the bedroom. Outside, he looked around. He had already seen one children's room, but to be sure, he rechecked it. He opened the door to the next room and found a second children's room.

When he opened the last door, it was the bathroom. The lights were on, and he guessed Linda had been there before stumbling to bed. His gaze was drawn like a magnet to a pair of black panties lying on the floor beside the toilet. His hard cock became like steel. Was she in bed naked beneath her tight skirt? He had to know. The house was empty, and Linda was sleeping.

He stepped out of his shoes by the bedroom door and returned to the bed. Linda was in the same position and breathing as before. He looked down at her. He felt almost revered for how sexy she looked. His cock was painfully constrained in his pants. The house was empty and quiet, and he felt secure even if his heart was beating a mile a minute because of what he was doing. He undid his pants and dropped them to the floor together with his underwear. He almost sighed in relief when his cock was released.

His gaze shifted from her mouthwatering ass to her bare thigh. It looked alluring how it disappeared under her tight skirt. He had been drawn to her ass and wanted to feel it. Instead, the idea of her being naked beneath her skirt was even more exciting. He had never seen or felt a pussy in real life. As much as he wanted to feel her ass, her pussy was more compelling.

He reached out and placed his hand on the inside of her thigh. His hand was clammy, and she felt soft and smooth. Her warm skin felt burning against his hand. He squeezed her thigh, testing the firmness. There was a dull throbbing in his cock from excitement. He ran his hand down her smooth thigh to her knee and back again. She felt amazing. But then he continued up, his hand going under her skirt, searching for the grand prize.

His fingers found smooth skin and a humid dampness. His heart nearly stopped. He was touching a pussy. Tentatively, he ran his fingers along her slit. He had seen many pictures and movies, so he knew what to expect. But he was a novice beginner, and he did not see. Trailing forward, he felt soft curls of pubic hair. Trailing back again, he felt dampness and then a distinct crack. It was not humid, and he had no problem probing his fingertips into the crack. There was a rubbery area, and feeling around, he realized he was fingering her butthole.

A shiver ran down his spine. He looked up at Linda's face. She was sleeping undisturbed, oblivious of him fingering her ass. His cock twitched. It was so wrong what he did, but his hormone-fueled desire propelled him forward.