Boys of the 1950s - 10. Chapter 10 There Is a First Time For Everything

Saturday morning Peter’s parents and little brother left on schedule. They told him they would take Ronnie out to a late lunch after the competition. Soon after their departure Tom dropped off Louise.

He greeted her at the door and they hugged. Kissing was not something they were comfortable doing. He led her upstairs and into his room. The rubbers, Crisco and old towels in case things got messy were laid out on the bed. They sat on the bed. Louise told Peter she had discussed their plans with Ann. Ann was sort of surprised. They had had a long discussion. Ann was just as curious as Louise but did not have the nerve to go through with it. Of course Ann expected a full report.

Peter realized he would have to take the initiative to get things started as Louise seemed a little nervous. He stripped down to his white briefs. Louise then undressed keeping on her bra and panties. He pulled her down onto the bed and pulled the sheet over them. He assumed she needed to be prepared the same way Tom did when they first fucked. Remembering the advice from Sean he gently rubbed his hands over Louise’s neck, then chest, then stomach, then the pussy. She still had her panties on. He softly massaged her. Then he slipped his hand under her panties and softly rubbed. He removed her panties and reached over and put a small amount of Crisco on his fingers. Continuing to lightly stroke the outside. Finding the hole he gently inserted one finger. Louise moaned and stated that what he was doing really felt good. He continued with his finger while with his other hand took hand Louise’s and moved it to his half hard cock trapped in his briefs. He then lowered his briefs, placed her hand on his hardening dick and continued to finger her vagina. He went deeper. Louise responded by moving her lower body in rhythm with his fingers. He then gently pulled out and inserted two fingers. Louise told him it was uncomfortable but not to pull out just go really slow. Keeping his two fingers in he stopped any motion. Then he began to gently finger fuck her. She continued to grip his cock holding it tighter as she became aroused. Obviously she was not expected to know what to do with a cock. Holding it tight didn’t do much, a little movement would feel good but he decided this was not the time for instructions on how to make your man happy. Besides he had Tom to do that.

He then pulled out, lowered the sheet and rolled on his back with his cock pointing straight up. He then took a rubber having previously opened the package so there would not be a delay at the height of passion and expertly rolled it down. His cock was not as hard as with Tom but firm enough to hold the rubber. He then moved on top of Louise pushing her legs apart. He applied a small amount of Crisco to his cock and Louise. He then rubbed her and reinserted his finger. He then rubbed his cock against her vagina and pushed in slightly, then more. When he was about half way in he stopped and smiled at Louise. “Is it OK,” he asked. She replied it was but to go slow and that while it did not hurt it felt uncomfortable. He slowly fucked with his cock just half way in. With each slow fuck he push in a little further. Soon his full cock was in her.

Then Louise blurted out, “Oh my God that hurts but feels so good. Keep fucking.” He fucked harder and she responded by moving with him. He felt it cuming and was soon shooting in her praying that the rubber held up OK. While it was not the fireworks explosion he usually had with Tom it was better than jerking off. He smiled at her and asked how she was. She replied that she felt wonderful. There was a little pain but the pleasure was far greater.

He pulled out and got on his knees between her legs. His dick was soft enough to easily pull off the rubber. He held it so she could see the cum floating in it. “This is what would be in you possibly making a baby.” She reached for the rubber and held it studying the creaming substance in it. He then told her that he hoped he had not hurt her and that he assumed there would be blood this being her first time. He had heard more than one guy bragging about fucking his girl and finding blood on his dick or rubber after the event. He had placed a large old towel that he could throw away without being missed under them just in case there was blood.

Louise said, “While no man has ever visited where you were my girlfriend has been there doing fantastic things, thanks to Ann I was ready for you.”

Louise went to the bathroom and did whatever girls did after being fucked while Peter straightened up the room and put the supplies in their hiding spot. She returned and they put their clothes on. Louise had never removed her bra. Peter was glad she hadn’t, a man’s chest was fun to play with, a girl’s tits just seem to be squishy.

He called Tom to tell him the mission was successfully completed and that the coast was clear. Tom arrived soon after with Ann and the four of them went to the bowling alley to have a private discussion and recap of the event.

Sitting at a corner table in the noisy snack bar over milkshakes and hamburgers Peter and Louise told the others about their encounter. It was as much as a scientific discussion as a love discussion. Ann asked if it hurt. Louise replied that it hurt some but the pleasure outweighed the pain. Tom then interrupted explaining how Peter had done research on dick sizes and that Peter’s dick was above average in length and well above average in circumference. He congratulated Louise on being able to handle a big dick. Then Peter explained that Tom’s dick was also above average in length so hopefully someday Ann would have a treat of a nice long dick. He also told Ann that the pain would probably be less as Peter’s circumference was average. Ann replied that she was not saying yes, but also not saying no. Peter than said he was sure Louise would gladly prep her for the event. All of them laughed.

Peter then said, “It was enjoyable and I hope we do it again. But, to be honest being with a girl was not like being with a guy and there is something I cannot explain that makes being with a guy more intense and pleasurable.” Peter then took Louise’s hand and said, “However, you are the only girl I have ever wanted to do it with and I sincerely hope we do it more.”

Louise replied, “My sentiments exactly. I enjoyed it, but my skin did not tingle like it does when Ann touches me. Don’t worry, we will fuck more.”

The girls were dropped off at Ann’s house. The boys went to Peter’s. They had at least an hour until the parents and brother were due home. Tom told Peter he wanted to fuck him with a rubber. Hopefully someday he would do the deed with Ann.

Peter got out the Crisco and a rubber for Tom. “OK, I’m just going to lay here naked and you take care of me.”

Tom kneeled between Peter’s spread legs. He then took his arms and held them over his head. Leaning forward he took one of Peter’s hands and sucked each finger. Then he licked down the arm to the pit. He knew since this was one of Peter’s special spots this would really get him started. He licked and softly bit Peter’s hairless pit. Then he moved to the other one. Continuing on down he sucked and lightly bit each nipple, then kissed his way to the stomach moving down he licked and kissed every part of Peter’s body except the cock and balls. After the knees he lifted Peter’s leg, licked the sole of his feet and then sucked each toe. After repeating with the other foot he moved up to the crotch and opened his mouth wide. He placed it over the dick head and took the entire shaft in his mouth before closing his lips around the rock hard cock. Keeping the cock in his mouth he put some Crisco on his fingers and began to gently massage Peter’s ass while sucking his cock. Then he inserted one, then two fingers and continued the massaging. Then he moved up to the pit and while licking and biting it he inserted a third finger. Peter moaned.

After placing a pillow under Peter’s ass to open it better Tom then unrolled the rubber, stroked a small amount of Crisco on it and leaned forward. He raised himself up and looking straight into Peter’s eyes placed his cock against the opening. Gently he pushed in. He waited about half a minute and then began jerking off Peter with his slippery Crisco hand while pumping hard in his ass. Their near simultaneous eruptions weakened both of them and Tom fell onto Peter’s chest. Laying there, both hearts racing they kissed hard and deep.

Fifteen minutes later they were sitting at the kitchen table drink glasses of milk and eating peanut butter cookies. Tom had already told Peter that he had had no problems manipulating the rubber. He also said that he would never fuck Ann as hard as he had fucked Peter, not unless after a few fucks Ann let him know she wanted it hard. Today he believed Peter wanted it hard and fast. Other days easy and slow while other days hard and fast with a quick stop and short break then hard and fast again continuing with fucks and breaks.

Peter replied, “You know me and my ass well. Today you did just what it wanted.” He then leaned forward to kiss as they heard the car pull in the driveway.

Big Brother’s Advice

That evening Peter’s parents went to a neighbor’s home to play bridge. Peter told his brother that he wanted to have another discussion about life with him. He suggested they go up to Peter’s bedroom. He then told his brother that sometime in the future he might want more sex than he got with his hand. That while his brother had sex education at school Peter wanted to discuss some of the fine points. He remembered the sex education as being very general and more medical than loving. Peter reminded Ronnie that the Church taught that being with someone or as commonly said “fucking” was immoral if they were not married. He was careful not to say being with a girl as maybe Ronnie preferred boys. Who knows? However, many boys and men bragged about fucking and some of these actually did it. He told Ronnie that people lie about sex probably more than anything else. So just because a guy says he does it don’t necessarily believe him. While Peter did not agree with the Church on its teaching about sex outside marriage he told his brother that he believed you should never have sex with someone just for the fun of it. You should really care for the person. While saying this he thought about his adventures in Seville with Sean, Frank and Jacob. Thinking he was probably being a hypocrite giving this lecture he would still do it.

Peter continued. “When you get to the point where you are ready to fuck you must only do it with a person you really care about. You must never force yourself on someone. Make sure the person wants it as much as you do. To force yourself is a crime. Never do it after drinking. First if you have been drinking you might do something you will regret later and secondly you will not be able to perform 100% and that would really set you back in your development. Especially if that was your first time.”

“You must know what you are doing. If not sure, go slow. Be soft. Be tender. I know someone who works at the downtown Burrough’s bookstore. I’m going to call him and ask him if he has or can get me a book for you. A book that would not only explain positions and techniques but how to do it from a loving prospective.”

“When you are ready to have sex with a girl you must protect yourself and the girl. This is the most important part of my lecture. I know you learned about making babies. You know babies are created when the little fishies or sperm in your cum attaches to an egg in the girl. It doesn’t happen every time you have sex but it does happen sometimes. You do not want to be a father yet. I do not want to be an uncle yet. And, mom and dad certainly do not want to be grandparents anytime in the near future. I am sure that they want us to find the right girl when we have completed out education and am able to support ourselves. They want us to fuck and create grandchildren. Just not too soon.”

The best way to protect yourself and the girl is to not fuck. But, when you do the best protection is a rubber. Do you know about rubbers?”

Ronnie replied that he had heard guys talking about them and that he knew there was a machine at the bowling alley where rubbers could be bought but he had never seen one and did not understand them.

Peter then pulled out three rubber packages. He handed two to Ronnie. Then from the other package using a banana he had brought upstairs he showed Ronnie how to roll a rubber onto a dick. He told Ronnie how it might be helpful to put a very small amount of Crisco on his dick prior to rolling on the rubber. He also told him about using Crisco to lubricate the dick and girl. He then told Ronnie to practice. He told Ronnie hide and keep the other one for future use emphasizing that it should be years until the actual act happens. If needed more could be purchased at the bowling alley.

Ronnie said, “Thanks brother. I sure am lucky to have a big brother who isn’t afraid to talk to me. I just have one question. With all this talk you sound experienced. Are you and Louise doing it?”

Peter replied, “A gentleman never talks about a person he cares about. The guys you hear bragging about getting it probably aren’t. The silent ones don’t need to brag. As far as I’m concerned, let’s just say I am very happy with my sex life. My hand keeps my dick very contented. Who and what I do with someone else is very private and I will not discuss it.”

“I understand,” his brother replied. “Now I have a request. You told me to practice. Would you demonstrate putting on a rubber.”

Peter replied, “Only if you go along with me.”

Peter then dropped his pants and began stroking his not totally soft dick. Ronnie did the same. Peter was very happy that Ronnie had a very healthy full sized dick. They both got hard. Peter opened a package while Ronnie did the same. They both jerked off and both filled the rubbers with cum in about a minute.

Then Peter said, “Removal technique is very important. Pull completely out of the girl. If you are still really hard it will be hard to pull off. Wait until you get a little soft. Then just pull from the end. Wrap it in tissue and throw away in a safe place. Do not flush it down the toilet. I have heard sometimes the air in the rubber will act like a balloon and you might think it went down the toilet only to discover that it did not. That would be tragic if you were someplace where you did not want anyone to know you were fucking.”

Both boys then pulled off the rubbers. Peter handed Ronnie a tissue to wrap his in. Peter then took both of them and told Ronnie he would dispose of it safely. Ronnie pulled on his pants, thanked his brother again and went down to the kitchen to get something to eat.

A few days later Peter called Mr. Johns at Burroughs and told him about his brother. He asked if there was a book that would explain sex from both a physical, how to, and emotional viewpoint. Mr. Johns told him to call back the following week and he would let him know what was available.

Another First

Classes, studying, band practice, attending basketball games kept the four friends busy. Tom and Peter had quick blow jobs and a couple of fast fucks. Louise and Ann had serious discussions about getting fucked and did what girls in love do behind closed doors.

Tom’s mother told him there was a company regional sales convention soon in Buffalo. She would accompany his father and attend wife’s events while his father attended business meetings. The meetings would be on Friday and Saturday ending with a dinner Saturday evening. They would leave for the six hour drive to Buffalo Thursday and return sometime on Sunday. She hoped he didn’t mind staying home alone. Tom assured her that he would be OK. He reminded her that next year he would be on his on at Kent State. He asked if it was alright if Peter stayed over one night. His mother replied that of course it was fine.

As soon as his mother was out of ear sight he called Peter and Ann suggesting they meet at the bowling alley. Peter called Louise and picked her up in his parent’s car. The four of them met, Ann arriving with Tom. The two couples were firmly established as girls/boys in love by their high school peers. Hanging out together like this solidified their smokescreen.

Tom told the group about his parents plan and the total availability of his home from midday Thursday to Sunday. He asked Ann if she still wanted to do “it”. Ann replied that she had had long discussions with Louise. She was willing if Louise could be with her. The four agreed on Friday evening. There was a basketball game. They would tell their parents they were going to the game and go to Tom’s home. The boys would take care of supplies such as rubbers and Crisco. After discussion about school and joking with some of their friends also at the bowling alley that evening Peter and Tom excused themselves to “take a leak” before going home while the girls went to their bathroom.

Tom and Peter stood at the second and fourth urinal. They would have preferred to be shoulder to shoulder but that wasn’t done unless it was break time at a sporting event and the room was packed. They looked at each other and Peter stepped back stroking his hard dick. Tom moved back and did the same. Just as they were both about to cum the door opened. Both boys stepped forward and covered their dicks. Two middle aged, chubby, half drunk bowlers came in wearing their bright blue team shirts. One went to the first urinal and the other the third. One belched, the other farted. Tom and Peter both noticed the guy between them pull out one of the smallest dicks they had ever seen. This series of events caused their dicks to completely deflate. Although neither had pissed both were ready to zip up and get out of there.

The girls were just coming out of the ladies room. They told the girls about the fat guy with the little dick joking that they may never get hard again if they couldn’t get his image out of their minds. Both Ann and Louise told them they would help with the mind readjustment on Friday. Each couple went their separate way.

Both boys went to their rooms upon arrival home to do homework. At least that was what they told their parents. Tom easily put the fat guy out of mind and began stroking his cock. Meanwhile Peter first took out the tool handle and some Crisco. He laid on his back. He first lubed his ass, then the handle and finally his cock. As he started to stroke it he fingered himself. Then using the handle fucked himself while jerking off. At a the same time, in different parts of town, Tom standing in the middle of his room looking at himself in the mirror, Peter fucking himself on his bed, both boys blasted their loads. Tom’s sprayed the floor while Peter covered his chest and face with cum. The girls were each home likely doing their girl things. All four had sweet dreams that night. Ann was conflicted but more happy with anticipation of being fucked than fear of being fucked.

Friday Tom picked up Peter, Ann and Louise. The girls ducked down in the back seat as they turned into his road. After pulling into the driveway Peter got out and opened the garage door. Since his parents were away Tom was able to pull into the garage. Peter then closed the garage door. The girls then entered the house from the attached garage with no possibility of neighbors seeing them. Before turning on any lights Tom had the girls stand in a corner where they could not be seen from outside. He then turned on the lights in the kitchen and living room. He went upstairs and turned on the lights in his bedroom. The shades had already been pulled and drapes closed so no shadows could be seen. Then turning off the kitchen lights he told the girls to go upstairs to his room. As soon as the girls were upstairs he turned the kitchen light back on. He and Peter then went to the refrigerator and got cokes and snacks for the upstairs party.

The room shades were pulled down and drapes closed. There were blankets to spread on the floor. Since this would be a group project Tom’s bed would not be adequate. When Tom and Peter entered the room the girls were sitting on the bed. The boys put the snacks on Tom’s desk and sat next to the girls. There was an awkward silence.

Peter stood up and said, “OK folks, let’s get this show on the road.” He pulled Tom up and Peter started to remove his clothes down to his new Fruit of the Loom white briefs. Tom also stripped to his white briefs. They then stood in front of the girls and helped them remove their clothes down to panties and bra. Both girls were wearing new, sexy underwear. Tom took Ann’s hand and guided her to the blanket. Louise followed Ann. The girls laid on the blankets, Ann on her back and Louise on her side facing Ann. Tom laid on the other side of Ann. Ann laid stiff looking straight up not making eye contact with anyone. Louise began caressing her face. Then moved her hand down to the breast. She gently moved in and turned Ann’s face so they could kiss. Ann shut her eyes and responded to her girlfriend’s kiss and touch. While the girls kissed Tom softly took Ann’s hand. He stroked it. Then he leaned in and kissed it. He then moved his hand to her belly, softly fondled it and moved down to the panties. Gently massaged her panty covered pussy. Soon Ann was moaning with Louise deep kissing her and caressing her upper body while Tom massaged her vagina opening. Tom slipped his hand into her panties and continued to massage. He then lowered and removed the panties. Ann was now very responsive and moved her hips up to help Tom with the removal. Peter had the Crisco ready for Tom. After putting a small amount on his finger he gently and slowly moved it into her vagina. As he slowly finger fucked her Ann became more animated. He took off his white briefs. Peter applied a small amount of Crisco on Tom’s dick and rolled a rubber on it. Peter then stroked Tom as he moved in between Ann’s legs. Tom leaned forward with a finger still in her vagina and double kissed her with Louise. Their three tongues explored each other while Peter continued to stroke Tom’s now very hard dick and also applied Crisco to it. Tom placed his dickhead against the vagina. He slowly pushed in less than an inch. Ann gasped, Tom stopped and held steady for a moment. He then moved in about another inch. Gradually he pushed all the way in. Tears were coming from Ann’s eyes. Louise was holding her and stroking her face. Tom asked her if she was OK. She did not reply. Tom told her to ask him to stop if he was hurting her. She did not reply. Slowly he began fucking her. Now Ann and Louise were holding each other firmly with their arms locked around each other. Tom was in a very awkward position with his arms and body extended in the up position of a push up. When Tom cried out “I’m cuming.” Peter kneeled next to him and wrapped his arm around him. Tom rolled off Ann into Peter’s arms while the girls continued to embrace.

After what seemed like an eternity but was actually just a few minutes Ann finally spoke, “Wow, thank you, all of you.”

Peter said, “My dick is so hard it is going to explode. Either we fuck or I jerk off, it’s your choice Louise.”

Louise replied “Let’s fuck,” as she pulled off her panties. She laid on her back and Peter massaged her vagina opening. Neither needed foreplay. Peter already naked rolled on a rubber and lubed both of them with Crisco. After her intense experience holding Ann she was hot, wet and ready. As horny as Peter was he remembered to be gentle. When he placed his dick against her vagina opening Louise grabbed Peter and pulled him forward and in to her wet, ready pussy. With just a couple of strokes Peter soon shot his load.

Tom got hard watching his boyfriend fuck Louise. Louise still laid there with her legs open. She looked at Tom’s hard dick still covered with the cum filled rubber and said, “Tom, please fuck me more.”

Tom obliged wearing the same rubber that had been in Ann’s pussy. This fucking lasted longer. Tom finally shot his second load of the evening. Peter watched and was hard and horny from watching his boyfriend fuck. Louise looked at Peter and said, “My God you are big but I have had my fill so to speak.”

Peter pulled off the rubber and began stroking himself. When he started to moan Tom leaned over and took him in his mouth. Peter shot his load down Tom’s throat. They then kissed.

In unison the girls said “Gross.”

Tom’s reply “A man’s got do what a man’s got to do.”

While dressing they had cokes and snacks. Being famished from all the activity they decided to go out to eat. Within fifteen minutes having followed the reverse procedures of the clandestine activities of getting the girls in the house they were at Manner’s ordering Big Boys, shakes and strawberry pie. Some of their school mates were there. They discussed basketball, band practice, science projects and next week’s sock hop. They did not discuss sex with their friends. The four of them were extremely content with what they had and had no desire to share it with others. Since they never discussed sex their school mates assumed they were a square group of virgins totally clueless.

Tom dropped each off at their homes. He and Peter made plans to meet the next day. That night four very content teenagers slept soundly with visions of fucking in their heads. Of course just the thought of what happened that evening got each of them aroused and each in her and his own bed took care of themselves manually in the way girls and boys as well as women and men do.