tagFirst TimeSummer Course in Sex Ed

Summer Course in Sex Ed



Bobby Jennings had recently graduated from a private high school for boys. At 18 years old he was still a virgin but he had masturbated many times while he was in school. Once they had a school dance and invited girls from the nearby all girls school and a girl had jerked him off while he finger fucked her pussy. Bobby had a lot of catching up to do if he believed what his friends were telling him about sex.

Bobby was 6'0" tall and he weighed a fit 175 pounds. He had short brown hair, hazel eyes and he was a handsome young man. Bobby knew that his cock was bigger than average as he had checked out his classmates in the shower. The girl who jerked him off also told him he was big but he didn't think much about it at the time. Bobby did cum in buckets when he ejaculated and it did catch the girl by surprise that night of the dance.

He had heard rumors of guys having sex with each other and even with some of the faculty but he was not interested in pursuing that. At times he thought that he might like a blow job to learn what it was like but he always dismissed it. He heard that some guys were butt fucking but he could not imagine sticking his cock into a guy's ass and he was certainly not interested in another guy's cock.

Bobby's father had enrolled him in the expensive private school. His father traveled a lot and he was on his third wife in four years. Bobby's mother had divorced her husband because of his philandering during the freshman year. Bobby's dad married again during the sophomore year and then again in the senior year. Both of the wives were trophy wives and his dad obviously had gotten tired of the second wife.

Bobby was home for the summer when he learned his dad planned a trip to Europe with his new wife and he would be gone for two months. Bobby's father had made arrangements for Bobby to communicate with their neighbor, a 36 year old divorcee named Stella. Bobby liked Stella and she was also very pleasing to the eye. She had been through two husbands and she had made out very well financially both times. In summers past, Bobby had done odd jobs for Stella and they got along very well.

Bobby could still sleep in his own bed in his room but he would check in with Stella every day. Stella had a cool backyard that was very private with a swimming pool and a Jacuzzi. Bobby had been allowed to use the pool in the past and he was looking forward to it again that summer. Bobby didn't know that Stella had a girlfriend who was staying with her from time to time. He also didn't know that both women were bi-sexual.


After Bobby's dad left for Europe, Bobby helped Stella with some inside painting. She could afford to have the rooms painted professionally but Bobby volunteered to help her. After several hours with the paint brush they would clean up and hang out by the pool. Stella let Bobby drink beer while she had her wine. Several times Bobby caught himself checking her out in her skimpy bikini. Stella had a fit 34-26-35 figure that looked good on her 5'6" 130 pound frame. She had long brown hair that looked glamorous. Stella also had an alluring sexuality about her that Bobby found exciting.

One day Bobby was getting set up to paint the master bedroom. Stella had run out to the store and left him alone in her house. Bobby decided to turn on the TV while he was moving items away from the wall. He had no idea that there was a DVD in the player and he was not prepared for what he saw. Stella liked watching porn and she liked to emulate the scenes with her sex partners. Her close friend Samantha also liked to watch porn and carry out some of the lesbian scenes with Stella. Sam, as she preferred to be called and Stella often had sex with guys and played out the things they had seen in the porn movies. The two women were very active sexually.

As the TV screen lit up and images appeared, Bobby realized that it was a movie. There were clips in the beginning highlighting the sex scenes contained in the movie. Each actor and actress was named in the preview. Bobby had never seen anything like it. He had looked at a couple of magazines that some guys had at school but nothing like he was about to see. All the actors and actresses had foreign names and Bobby guessed that they were Italian.

It was an Italian movie but with English voice over. Bobby could see the lips were not in sync with the spoken words, not that that was important. The women were drop dead gorgeous and the men were all well endowed. Bobby was motionless as he watched the first scene unfold. The woman was a gorgeous brunette with a beautiful figure. She had lovely natural breasts, a flat belly, shapely legs and a curvy bottom. It didn't take long for the action to start and it began with kissing a handsome guy.

Within minutes the woman's dress was pushed down to her waist and the guy was sucking on her great looking tits. Bobby's cock spring to attention in his shorts and he had to adjust it so that it didn't hurt. The guy next raised the woman's skirt, pulled the panties to the side and played with her pussy. Then he removed her panties and began eating her pussy. Bobby had never seen anyone eat pussy before but he knew that people did that. Then it was the woman's turn and she unzipped the guy's pants and fished his cock out through the fly.

Bobby watched in awe as the woman jerked the guy off briefly and then lowered her mouth to the stiff dick. The woman gave the guy a fantastic blow job and Bobby was so turned on that he felt he might cum in his pants. Bobby was afraid to touch his cock as he didn't want to ejaculate. The scene panned in and out and the next thing the two on the screen were naked in a 69 position with the woman on top. Actually the woman was still wearing her thigh high hose with elastic tops and it made her look even sexier. The guy fingered the woman's anus while he ate her pussy as she sucked his cock.

Minutes later the two porn stars were fucking missionary style and the camera angle captured the penetration. Bobby was beside himself as he never knew that beautiful people like the ones in the movie could be porn actors. Bobby's cock was straining in his shorts and he just had to free in from the confines. He unzipped his shorts, pushed his underwear to the side and pulled his cock out. At this point he had to stroke it.

Bobby masturbated as he watched the actors. They had moved to a spoon position and the guy was fucking the woman from behind. Bobby could feel his balls tighten as they always did as his release built within him. He then watched in disbelief when the guy moved his cock from the woman's pussy and placed it at her anus. Bobby could not have imagined a beautiful woman taking a big cock in her ass but he watched as the thick dick spread her aperture and nestled into her rectum.

The woman moaned softly as she was penetrated anally. The guy moved slowly at first and then picked up the pace. Bobby was mesmerized by the act as he watched the cock slide in and out of the woman's beautiful ass. Bobby felt his toes curl and his balls sac tighten as his load traveled through his shaft. He quickly located the drop cloth and aimed his cock at it just in time. His ejaculation was forceful and massive. Sperm shot out of his cock and traveled a couple of feet landing on the painter's drop cloth. Six streams rocketed out of his pulsating dick and it was his most intense ejaculation ever. Bobby stroked his cock and milked all the semen from it allowing the remainder to dribble onto to the drop cloth.

His ejaculation was over in less than a minute but it seemed like an eternity. His cock was still hard and he held it in his hand and he turned his eyes back to the TV. At that point the woman was on all fours and the guy was drilling her ass from behind. Bobby had a good look at her beautiful ass and the anal penetration. He kept stroking his cock as he knew that he could cum again but then he heard Stella return from the store. Bobby shoved his cock back into his shorts but he still showed hard. He quickly turned off the TV and DVD player. Bobby tried to act normal when Stella came into the room but she noticed that he was very flushed.

"Hi Bobby, are you okay? You looked very flushed. Do you feel ill?" she asked.

"Oh no Stella, I'm fine. Just working a little too hard maybe," he replied turning even redder than before.

"Okay well don't hurt yourself. I can always hire some painters," she offered.

"I'm okay really," Bobby insisted. The last thing he wanted now was for her to hire someone. Bobby was already thinking about watching more porn in Stella's room. He wondered what else was in the movie.

"I'll make some iced tea for us and that will cool you off a bit," Stella told him.

The rest of that day Bobby and Stella worked on the bedroom and finished painting the walls. Tomorrow they would move the furniture back in place and re-hang the pictures and artwork. Stella suggested a cookout that evening and Bobby grilled the burgers for them. They ate dinner, chatted, had a few drinks and then cleaned up the area. They agreed to get started at 9:00 AM the next day and then Bobby went to his house.


Bobby went right to bed that night and slept naked in his bed. His mind traveled back to the porn movie and his hand encircled his cock. Bobby replayed the images of the beautiful porn actress sucking and fucking as he masturbated again. He was still in awe of such a beautiful woman doing all those things on the screen. The image of her sucking cock and taking it in her ass was a vivid memory. Bobby jerked off three more times that night and he covered his body in his own spunk. Bobby fell asleep letting the semen dry on his skin.

While Bobby was furiously masturbating in his bed, Stella had got in bed with her favorite dildo and turned on the TV and DVD player. She was surprised to see that the movie was near the end of the first sex session. The movie should have been at the beginning where she had left it the night before. There could only be one explanation for that, Bobby must have discovered the movie. "No wonder he was flushed when I came home," she thought and smiled, "I wonder if he jerked off."

Stella loved the first scene so she restarted the DVD and watched the entire scene. As she enjoyed her porn movie she moved the sizeable dildo around in her pussy. Stella loved to masturbate while she watched porn and this was the best movie she had ever watched. She liked in better when Sam was in her bed and they took turns being the guy. They would fuck each other silly with the strap-on cock. They also both loved anal and would drill each other with the strap-on as they watched the actresses get butt fucked on screen.

Stella had two orgasms with the dildo in her pussy before she moved to all fours and awaited the anal scene in the movie. She lubed her anus liberally and eased the fake dick into her ass just as the actor was penetrating the actress. Stella moved the cock in and out of her ass in time with the guy's rhythm. Stella fingered her pussy as drove the rubber cock into her rectum as she tried to time her orgasm with the guy cumming all over the woman's ass.

Stella screamed as another orgasm rocked her body and she watched as the guy pulled out and creamed the woman's buttocks. She was still recovering from her orgasm when the actress turned around and took the guy's cock in her mouth and sucked it dry. Stella's body shivered at the sight and then she collapsed on her bed. As she lay there she plotted to catch Bobby jerking off. She knew he had a nice package from their days by the pool but she had never seen him hard. She had not even thought to seduce him until now and she wondered if he was still a virgin. It had to be difficult to get laid at that private school. Stella dozed off thinking about ways to seduce Bobby.

The following morning Bobby woke up and the first thing that he thought of was watching more of the movie. He hoped that Stella would have some errands to run that day. Bobby ate breakfast, dressed and headed over to Stella's house. Stella had slept in purposely hoping that Bobby would enter the house on his own. When Stella did not respond to the doorbell, Bobby anxiously entered the house as he assumed she was gone and he would get to watch the movie.

Bobby hustled up the stairs to Stella's bedroom and stopped in his tracks when he saw that Stella was still in bed. Stella was not asleep however and she knew that Bobby was just outside her room. She was still naked and she rolled around as if she was waking up displaying her sexy body to the curious teenager. Bobby watched his neighbor and took in her beauty. Stella was every bit as beautiful as the woman in the porn movie and she even resembled the brunette slightly.

Bobby felt his cock stir in his shorts as it had the day before. He adjusted it so that it was not caught in his pant leg and stood straight up behind his fly. Stella rolled to her back and let her legs splay open giving Bobby a good look at her neatly trimmed pussy. His eyes traveled her body from her cute medium sized breasts, down her flat belly to her vagina. As Bobby looked at her he wanted to do everything that he had seen in the movie. Just then Stella rolled to her stomach and Bobby almost gasped aloud when he saw her super fine ass.

Stella decided that was enough teasing for one morning so she rolled over and stretched signaling that she was going to get up. Bobby ducked around the corner and waited until he heard the shower. He dashed back down the stairs and waited in the kitchen until Stella arrived. She had showered and dressed in very tight short shorts with halter top. It was obvious that she wasn't wearing a bra and Bobby could see her hard nipples poking through the material.

"Hi, good morning, I hope I didn't keep you waiting long," Stella greeted him.

"No, I just got here," he lied unconvincingly.

"I'll make some coffee," Stella said.

Bobby watched her as she moved around the kitchen and his eyes were fastened to her scrumptious ass in the tight shorts. He felt his cock getting hard again and he was frustrated as he did not know what to do to deal with his feelings. He wanted to run to the bathroom and jerk off but he knew better than to do that in Stella's home. What he really wanted to do was do what the actor had done to the actress in the movie but he knew he could never do that with Stella.

"Bobby, would you get this down for me," Stella asked pointing to an item on the top shelf of her pantry.

Bobby panicked as he could not get up at least he didn't want to get up because he had an erection. He knew it would be visible in his shorts and he was embarrassed. Stella looked at him and insisted and then she smiled when she realized his dilemma. Bobby got up and tried to mask the outline of his stiff cock but Stella saw it. She turned away so as not to make him feel uncomfortable and Bobby quickly moved it around in his shorts.

Stella made a light snack for them and then it was time to get to work. They started in the guest bedroom and had everything moved away from the walls and all the furniture and flooring covered with drop cloths. Bobby was stirring the paint when Stella told him she had to run out for a minute. Stella went downstairs but she never left the house. Minutes later Bobby headed into her bedroom and turned on the TV and DVD player. He was relieved when the movie appeared on the screen as Stella had not removed it.

This time a pretty blonde with a different actor performed. She too was gorgeous and the guy well endowed. Bobby watched as the two of them performed oral sex partially clothed and then fucked with their clothes off. The woman was naked except for her thigh high hose and Bobby found that very erotic. The guy was completely naked. Bobby freed his cock and began to beat his meat as he watched the incredibly handsome and sexy couple. The guy was fucking the woman missionary style but then he pulled out and pushed it in the woman's ass.

Bobby watched as the guy repeatedly fucked the woman switching between her pussy and her ass. Then the woman was placed on all fours and the guy fucked her in the ass. Bobby liked that position best as the woman had a beautifully shaped ass and he liked watching the cock enter from behind. Unbeknown to Bobby, Stella had come back upstairs and found what she wanted to see. Bobby was jerking off to the porno and Stella watched him for a few minutes.

She was impressed with the 18 year old cock. Using her dildo as reference as she guessed it to be close to 8" long and over 5" around. Stella wanted to see Bobby shoot but she also wanted to be careful. He turned off the TV and player as soon as the guy came on the woman's face and Stella moved away and hid. Bobby came out of her bedroom with his erect cock in his hand and headed for the guest bedroom. Stella peeked in and watched as he jerked off and shot a huge load onto the drop cloth. His ejaculation seemed endless and Stella had never seen anyone cum that much in person. Her pussy was tingling and she could feel the dampness in her panties. Stella went back downstairs before Bobby put his cock back in his shorts. She waited several minutes and then she returned to the bedroom where he was working.

"Everything okay?" she asked.

"Yeah, fine," he replied sheepishly.


Stella told Bobby they were going to take a day off and hang out by the pool. Bobby was normally all for it but he had become addicted to the porn movie and he was disappointed that he wouldn't get to see any that day. Stella purposely wore her skimpiest of bikinis and one that left little to the imagination. Bobby was horny and uncomfortable all day but then Stella fixed that. She walked to the end of the swimming pool and as she did she untied the strings on her bikini bra and bottom. Bobby watched as she dove into the pool with near perfect form. The bikini floated away from her body as she swam to the swallow end. Bobby didn't see the bikini come off but when she stood up to get out of the pool it was clear what happened. Bobby was lost for words and then he stammered.

"Stella, your bikini," he cautioned.

Stella looked down and pretended that she was surprised by the absence of her bikini. Bobby could not tale his eyes off of her beautiful nude body. Stella calmly walked over to her Jacuzzi and climbed in.

"Come and join me Bobby," she offered.

Bobby had a woody in his Speedo and it was very obvious. "Come on, I have seen erections before," she urged.

Bobby walked timidly to the Jacuzzi questioning whether he would have the nerve to get in with the naked Stella. As he swung his leg over the side Stella looked right at his crotch. "Bobby why don't you lose the Speedo, it's much nicer in the nude."

Bobby trembled as he did not know what to do. "Come on, I'm naked and you should be too. It's weird with only one of us naked."

Bobby slipped off his swimsuit and his impressive cock sprung out. Stella stared at it and she liked what she saw. Bobby quickly slid under the bubbly water and he was relieved that his stiff dick was out of Stella's sight. He hoped that his erection would subside but it didn't.

"So Bobby, do you like watching porn?" Stella asked.

Bobby blushed and answered, "I don't know what you mean."

"Porn, x-rated movies, people having sex, its okay I know that you have been watching the movie in my room."

"I'm sorry."

"Don't be, I love to watch it too. That movie is my favorite. It is Italian made and I love all the characters."

"The women are beautiful. Just like you," Bobby managed.

"How nice of you to say that," Stella replied as she slid over to him.

Bobby jumped when their skin touched. Stella slid her hand under the water and across his thigh and grabbed hold of his erect cock. Bobby almost came on the spot when she touched him.

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bywalterio© 2 comments/ 113045 views/ 53 favorites

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