Ted and Shirley Friends and Lovers - Cover

Ted and Shirley Friends and Lovers

by Curbstonesetter

Copyright© 2023 by Curbstonesetter

Erotica Sex Story: Description: High school sweethearts reunited after losing contact with one another. their reunion results in the ending that they had so much wanted to do while they were still in high school.

Caution: This Erotica Sex Story contains strong sexual content, including Ma/Fa   Consensual   Heterosexual   Fiction   School   Oral Sex   Pregnancy   .

Author’s Note: This story is a complete work of fiction from the get go and is intended solely for the readers to enjoy. My thanks to Easyspeak for the work of editing this story, so that it makes sense and makes it easier to read and understand.


Growing up in the ‘50’s I was a junior in high school and I had just begun to really notice girls during this year in school. I had classes with many good looking girls in school, some of whom really would not give me the time of the day.

Those girls were the girls that many of the guys and even some of the other girls called “stuck up” or “stuck on themselves.” Most of the other girls were nice, sweet girls who were willing to treat most of the guys as well as the other girls with genuine civility and equality and didn’t look down their nose at them.

Shirley was one of those sweet somewhat shy girls who was not “stuck up” and she was pretty but she was not sought after as were the stuck up girls. I had some classes with Shirley and I began to notice her in class.

She was very intelligent but, she did not need to go to any lengths to show it, and she was very reserved but, she was not conceited. Some of the guys and even some of the girls thought that she was kind of mousy.

She was an excellent student as she was always on the school honor roll. When she was called on to answer questions in class she was always prepared to correctly answer the teacher’s questions about the class study without hesitation.

I soon found out that she was not only very smart and she was very good looking, too. Or at least I thought that she was good looking anyway besides being so smart. I guess that some people would consider her to be a nerd and a book worm.

It seemed that most of the guys were turned off by the clothes she wore that obscured her great figure and her lack of makeup and her hair was not cut and styled the way that most of the other girls’ were. It sure made me think that she was a diamond that had not been set in a pretty mounting, so to speak.

Once I met her I always treated Shirley well and respected her for who she was as a sweet, slightly shy girl who always treated others well. Shirley’s beautiful, shining blond hair came down to below her shoulders and some of it curled just under her chin.

Her hair framed her pretty face and accentuated her gorgeous, sparkling, sky blue eyes. She was a petite girl at only about 5 Ft.-4 in. tall with small breasts probably 34B, a 24 inch waist and 36 inch hips when she wore clothes that revealed her figure which wasn’t very often.

I thought that her breasts were small but I reasoned that the size of a woman’s breasts did not define the whole woman and as far as I was concerned it had no bearing on how smart she was either.

Shirley’s intelligence, her sweet gentle personality, her pretty face, her gorgeous sky blue eyes and her gracious treatment of other people much more than made up for her somewhat small breasts.

More than that, unbeknownst to me at that time, her breasts were likely to get larger after she got married and had a couple of babies. I was told that happens as a gift, or in some cases a curse, of nature to the women who bear babies.

As time went on, during the school year, Shirley and I began to look for one another in class and very often we sat next to each other in class if we could. We would talk to one another before and after class about our mutual class interests and school activities. We both really enjoyed each other and our interactions with each other.

Often times on a Friday, Shirley would tell me, “Ted, I’m planning on going to the football game (or to the basketball game) tonight if my parents will let me and I’m wondering if you plan to go to the game and the dance as well?”

Most of the times, I would tell her, “Yeah, I’m planning on going to the game tonight, Shirley.”

She would usually respond, “I and a couple of my girlfriends are planning on going to the game. And maybe we’ll see you there or maybe I’ll see you at the dance in the old gym after the game if my parents will let me stay for the dance.”

When I went to the games my buddy, Dave, and I generally went there together. Many times we did not see Shirley and her girlfriends at the game. We usually went to the dance after the games and only once in a while would we see Shirley there.

Those times when I did not see Shirley at the game or the dance, I saw and asked one of her girlfriends where she was. Most times Shirley’s girlfriend told me that her parents would not let her come to the game or to the dance that particular night.

Those times that I went to the games and the dances afterward and Shirley was not there, I left and went home disappointed for not having seen her there. When I did see her at the dance, I really enjoyed talking with her and dancing with her.

Shirley was a great dancer and she was a good conversationalist with her sweet personality. She was very easy to talk to and I think she really enjoyed talking with me, too.

I always thought that she was able to follow my lead on the dance floor very well when we were dancing. I marveled at how good a dancer she was because I felt like I was a real “clod hopper” when it came to dancing anyway.

I always enjoyed talking to her as time permitted and I was comfortable with her and just enjoyed being with her. Looking back on it I think that I was falling in love with Shirley but, I sure as hell did not know it at that time.

This continued until the end of our junior year but, I did not see Shirley during the summer when school was out. I was working around the house for my parents or for my dad in my dad’s business and I had very little time for socializing.

However, I was happy when school started again in the fall. That meant that I was likely to see Shirley again in class or at the games and other after school functions. Again in my senior year I had a couple of classes with Shirley and was happy to see her and talk to her during or after our classes. During my senior year I saw her several times at the games and at the school dances and I sure got along well with her and wished I could see more of her.

One night at the dance I saw Shirley and danced with her. After our dance ended I told Dave I was going to go get a cold drink and asked if he wanted one. I went outside to get the drinks for us.

The lines were very long so it took me a while to get our drinks. When I returned with our drinks Dave was nowhere to be seen so I sat down with our drinks in hand and waited for him to come back to where we had been sitting. A short time later Dave showed up and I asked where he had gone.

Dave said, “I have been out on the dance floor with Shirley and then I went to the restroom after our dance had ended. Ted, she is a really nice girl and she is a very good dancer, too. I don’t really understand why most of the guys think that she is a nerd.”

Shirley had asked Dave, “Where did Ted go, Dave? Did he leave the dance and go home?”

Dave told her, “No, he just went to get something cold for us to drink.”

Then she told him, “Ok, I’m glad to know that since I want to see him and dance with him again before the dance ends tonight. Let Ted know that I want to see him and dance with him again, will you please, Dave?”

Dave responded, “Ok, Shirley, I’ll do that for you and I’ll let Ted know that you want to dance with him again.”

Just before the last dance of the night I went over to Shirley and asked, “May I have this last dance, Shirley?”

Shirley quickly responded, “Yes, you may. I have been saving this last dance for you, Ted.”

During our last dance she said, “Ted, since this has been the last game and this is the last dance of the year I want to invite you to come over to my married sister’s house a couple of weeks before graduation just for a little get together.

I would like to introduce you to my Sister as I have been telling her about you and how well we get along at school and at these school dances. And I have told her that I really like you, too, Ted. I also told her I think that he likes me, too, Sis.”

Shirley further told me, “It’s coming up on my sister’s first wedding anniversary and she is going to have a small party for some of her friends. She wants me to be there and she said I could invite whomever I wanted to invite, to come to the party with me. That was her way of telling me I could invite you, Ted.”

I quickly replied, “Yeah, Shirley I would love to come over there to be there with you and meet your sister and especially to see you there.”

Then she told me, “There will be soda and other refreshments along with some of my sister’s high school friends. I’ll get you the address, the day and time of the party at school a few days before the party.”

“Ok.” I told her, “I’ll look forward to being there with you then, Shirley.”

About a week before the party Shirley saw me in class and handed me a sheet of notebook paper with the party information hand written on it.

I looked at it and said, “Yeah, I know where this is and I am looking forward to coming to the party to see you and your sister that night, Shirley.”

Shirley said, “That’s great that you’ll be able to come to the party with me, Ted. I’m looking forward to having you there and my Sister is looking forward to meeting you, too. I think we are going to have a good time at the party, Ted.”

I saw Shirley in class several more times before the party was scheduled and she seemed to be very excited that I was going to be there at the party with her. I was equally as excited about being at the party, too, and seeing and being with her that evening.

When the day of the party arrived, I was very excited about seeing Shirley somewhere away from school. I arrived at her Sister’s house for the party that evening and Shirley met me at the door.

She invited me to come into the house, and she introduced me to her Sister and to her Sister’s husband and to the other guests who were there. Shirley’s parents were not there and I thought that was a little strange but, I decided to ignore it as it really wasn’t any of my business why her parents were not there. Unfortunately I later found out why and how it affected not only Shirley but, it affected me too.

After all the introductions were made, Shirley and I sat down on the couch together to talk. Shirley told me very quietly, “The reason my parents are not here tonight, Ted, is because they did not and still do not approve of my Sister and her husband having gotten married. That is because my Sister had gotten pregnant and she had to get married before the baby arrived. My Sister told me that the damn condom broke.

Her baby boy is six months old and my Sister and her husband are really celebrating his six month birthday which is close to their wedding anniversary. I think that my Sister’s baby is adorable and that she does not want that to happen to me before I get out of school and get married. But, I sure wish I could have a baby like my Sister has.”

For the ‘50’s it was not all that unusual for a couple to have a condom break and the girl ended up getting pregnant. I myself knew and had heard of several instances where that had happened.

Shirley continued, “My parents won’t let me go out with boys because of my Sister and her husband having had to get married. They are afraid that I will get pregnant like my sister did.

They are very strict with me and they will not let boys come to visit me at our house or even talk to me on the phone, either. That is why I was so excited to have you come here to my Sister’s party tonight where we could comfortably see each other and talk with each other without someone looking over our shoulders and listening to everything that we say.”

She said, “I am not allowed to go out without my Mother, my Sister or my girlfriends.” I had always thought that there was something a little strange and now because of what Shirley had just told me it kind of explained everything.

I had asked Shirley many times to go out with me but she always said that she could not go out with me because her parents would not allow her to go out with boys. I could see the tears beginning to glisten in the corners of her pretty blue eyes and it damn near broke my heart to see her so sad like that. I put my arm around her and kissed her cheek to comfort her and help quell her tears.

I thought to myself, ‘Shirley you’re such a sweet and warm girl, I guess that’s what attracts me to you so much.’ and I had to repeat my thought whispering that in her ear.

Shirley told me, “I like you a lot, Ted, and I wanted to go out with you but for my parent’s objections to me dating and going out with boys I could never go out with you.”

I told her, “I like you a lot too, Baby, and I’m really disappointed that we could not go out together.” as I leaned over and kissed her tenderly. I whispered in her ear, “You really look pretty tonight, Shirley.”

Shirley just giggled softly, blushed and kind of wiggled in her seat then she said to me, “Thank you, Ted. That makes me feel really good to hear that especially coming from you.”

She responded hungrily and passionately when she kissed me and whispered, “I really loved your kiss and your compliment, Ted.”

We all had some refreshments and drank soda, then visited with some of her Sister’s other guests.

About that time Shirley’s sister came into the room holding her precious little baby boy in her arms and had him say nighty night to everyone. Shirley’s expression and her body language told me that her Sister’s baby made her really want to have her own baby, too, as she wiggled in her seat and looked lovingly at her Sister’s baby.

Shirley’s Sister told her to put some soft music on the stereo. She did as her Sister had asked and Shirley and I and another couple danced to the music that she had chosen. We both really enjoyed the music and the dancing as both of us began to feel the closeness of one another in each other’s arms and we began to feel very comfortable with each other, also.

As we were dancing I was holding her tightly in my arms against me, my emotions began to rise further as I could feel my hunger for her growing in my lower belly and in my briefs between my legs.

The look on her face and in her eyes told me that she was having pretty much the same response to being held tightly in my arms with her soft, warm breasts pressed tightly against my chest. Man, I could have danced with her the rest of the night holding her tightly in my arms with those soft titties of hers pressed so tightly against me.

For late May, it had been a warm day and a warm evening. Shirley was only wearing a thin sleeveless cotton blouse and thin cotton short shorts which did not inhibit either one of us very much.

Shirley’s blouse and shorts were very much like what her Sister was wearing. And both Shirley and her Sister were wearing makeup with very light lip gloss, rouge and eye shadow. That was the first time I had seen her wear any makeup not even lipstick.

I figured that her sister helped her put her makeup on and, man, did they both look great mostly because the two Sisters looked so much alike. It was no doubt that they were Sisters. Shirley told me, “Mom and Dad really don’t like either me or my Sister to wear shorts or to have makeup on either, Ted.”

It was the first time I had seen Shirley’s gorgeous figure fully and her beautiful, shapely feminine legs which added to my hunger for her. I knew that she had to be able to feel the bulge in my jeans, too, while we were dancing. But, she did not say anything as she just looked up at my face and into my eyes and gave me a sweet knowing smile and a sweet soft kiss on my lips.

Her beautiful knowing smile made me even more excited and I could feel her nervous excitement as she slightly trembled in my arms as we danced together with her pretty head at times laying so lovingly on my shoulder.

Shirley continued to lay her head on my shoulder as we danced and I continued to kiss her on her forehead, her cheek and her neck. Each time I kissed her she had a little shiver, a slight tremble and she softly purred to me showing me just how much she liked it. Then I whispered in her ear, “I like you very much, Shirley, and we need to go find some place a little more quiet and private for us to talk and make out.”

She quickly agreed, too, and whispered back, “Can we go out for a walk or for a ride in your car, Honey?”

I quickly replied. “Ok. Let’s go, Sweetheart.”

Earlier that evening, on my way to her Sister’s house, I had stopped at a pharmacy and had bought some condoms and I had the condoms in my front jeans pocket. I did not know that I would be able to use them but, I wanted to have them with me in case I did need them. I sure as hell did not want to be in the position of needing them and not having them and risk putting Shirley in the same position that her Sister has already been through.

Although I thought, ‘Shirley would have loved to have a baby of her own and she sure as hell would make a really good mother to her babies, too. But, I sure as hell wasn’t ready to be a daddy either. Hell, I couldn’t even support myself right now let alone support a wife and a baby. Do I look like a daddy to you?’

Shirley told her sister, “Sis, Ted and I are going to go out for a walk and get some fresh air. We’ll be back in a little while, Ok?”

Her sister looked at her, winked at her and said, “Ok. You two enjoy yourselves, be very careful and be back here, soon, Shirley.” Shirley knew exactly what her sister was implying.

As I saw her Sister wink at Shirley I thought to myself, ‘I think that I already have the careful part covered and now all we have to do is to get to the point where we needed to be careful.’ I also knew that Shirley and I would certainly enjoy ourselves regardless of what happened whether we needed to be careful or not.

We left the house and got into my car and she immediately slid across the bench seat and sat very close beside me. When we got into the car and as I was starting the engine I asked her, “If your parents will not let you go out with boys then why did they let you come to your sister’s party tonight, Baby?”

She quickly replied, “That’s because they think that as long as I’m here at my Sister’s house it’s Ok and they don’t have to worry about me.”

She went on to say, “My Sister knows what I am going through and she thinks that our parents are way too strict with me and they are not treating me right. She also thinks that I should have been allowed to date in high school.”

I kissed her and told her, “I sure wish that I could have dated you earlier when we first met, Sweetie.” Shirley just blushed a little bit, wiggled in her seat and kissed me back. I was thinking, ‘Damn, it is really good to have her with me tonight regardless of whatever else happens and whatever else we do tonight. I know what I want to happen but whether it will happen remains to be seen.’

After I started the car she told me, “Ted, a couple of blocks over and a couple of blocks down, there’s a secluded tree covered area off the street where we can park and make out. I have seen it when my Sister and I have taken walks with her baby in his stroller in the neighborhood.”

With her instructions I drove to it and parked where no one could see us from the street or from any of the surrounding homes as we were shielded by the trees and shrubbery. Once we were parked we immediately turned to each other and began to make out passionately. I was very hungry for her and she appeared to be ravenous for me.

I began to tell myself, ‘I believe that my hopes are going to happen tonight, Ted.’

Shirley whispered to me, “Seeing my sister’s baby and knowing how it happened makes me really want to have you so much, Ted.”

“And I really want to have you, too, Honey, but, we have to be very careful that you don’t end up in the same situation as your sister.”

She startled me when she said, “You know, Ted, I don’t know if I would really care if I did get pregnant tonight especially if it is your baby.”

“Well, Honey, there is no one else I would rather want to have my baby with than you.” Then she hugged me even tighter and laid her cheek next to mine.

She began kissing me passionately and she began to take my shirt off. When she removed my shirt she laid it in the back seat and began to kiss my neck and chest. I began to unbutton and remove her blouse and then I laid it in the back seat of the car along with my shirt.

I unbuttoned her shorts, unzipped them and pulled them off of her hips and put them in the back seat, too. At the same time she was taking my pants off, she reached down, fondled and gently squeezed my hardening dick.

Shirley exclaimed, “It is so big, Ted, that I don’t know if it will fit inside me.” As she pulled my pants off, I reached into my pants front pocket and got a condom package out of it and laid the package on the top of the dash board of the car.

I kissed her and said, “Let me take your bra off.” as I reached around behind her and unclasped her bra freeing her young, luscious, soft titties. I kissed her and immediately bent down and kissed each one of her somewhat small, creamy white titties with their light brown areolas and their hard, pink nipples standing up proud above the globes of her titties.

I briefly sucked on each of her dark pink nipples that were standing so proud of her creamy, white titties. I reached down to her waist and with her help I pulled her panties off of her hips and removed them laying them in the back seat, also. Shirley held my head and purred to me as I was kissing her globes and sucking on her nipples.

She immediately started to take my briefs off freeing my erect dick and she gasped at how big she thought it was. I reached up to the dash and got the condom and tore open the package. She pulled it out of the wrapper and she helped roll it onto my already hard dick. Then I gently and carefully laid her down on the seat of the car, got between her thighs and kissed her bush and her very wet pussy.

I began kissing her and asked her, “Do you want my hard member inside you, Baby?”

Shirley whispered to me, “I really want to have a precious little one like my sister has and would like for you to give me a baby, Ted.”

I replied to her, “As much as I would love to give you my baby, Honey, neither one of us is capable of supporting ourselves nor a baby right now either. So we really can’t have a baby especially now, Sweetheart. We each have four years of college ahead of us before we can take responsibility for having and raising a baby.”

Shirley reluctantly agreed with what I had just told her saying, “Yeah, I know, Ted, but, I still want to have a baby like my Sister has. He is such a beautiful baby boy, too, Honey.” Then she said, “And I still want you very much, too. I’m still a virgin so please be gentle and careful with me, Sweetheart.”

I told her, I’ll not do anything to intentionally hurt you, but, when your hymen is broken as my penis enters your vagina you’re going to feel a very sharp pain and you probably may have a little bit of bleeding, too.”

I also told her, “The pain should quickly ease up after the initial sharp thrust when your hymen is broken and you should soon begin to feel the pleasure of having us together with my penis slipping in and out of your vagina.”

Shirley replied, “I know, Ted. My Sister has told me about that and I was expecting to have some pain when that happens. But, I still want you to be the first one to be inside me and I can’t wait to feel your hard member slowly sliding inside me filling up my vagina.”

Reaching down between her legs touching her soft bush I put my hand on her warm, soft pussy, cupping it with my fingers and the palm of my hand. I found that her pussy was very wet and she was ready to have me enter her.

I gently raised and spread her legs while rubbing the head of my condom covered dick all along inside the length of her pussy lips to generally spread her wetness and get my condom covered dick lubricated with her vaginal fluids. I placed the head of my dick inside her inner pussy lips at the opening of her pussy and slowly began to push it in until I felt the obstruction of her hymen.

I very softly asked her, “Are you hurting in any way, Honey?”

And she breathlessly whispered, “No, not yet, Baby.”

I then asked her, “Are you ready for me to break through your hymen, Sweetheart?”

And she nervously said, “Yes, Honey, I’m ready for us to start.”

With a slow, continual, forceful thrust I slowly pushed my dick all the way into her pussy getting full penetration into her and she cried out loudly with the sharp pain that she felt. I bent down put my arms around her holding her closely to me and kissing her forehead and her cheeks.

Lovingly, I kissed her and told her, “I really did not want to hurt you, Baby.”

Then I could see the tears streaming down her cheeks but, she whispered softly to me “Don’t stop now and keep thrusting in and out of me, Ted. The pain is beginning to quickly ease up.”

I held my dick at full penetration for a few moments to allow her to become somewhat accustomed to the size and presence of my dick in her. Then I resumed thrusting my dick deep into her. Slowly, I started to stroke her and I could see in the dim light that she had a slight smile of pleasure on her pretty face.

I paused and asked her, “Are you still having any pain, Baby?”

She softly replied, “It has mostly gone away and now I want you to make us both climax by stroking us faster and harder.” I increased my speed and forcefulness and within a few minutes she was breathless and moaning loudly.

Then I felt her begin to tremble and shake as her orgasm rolled over her and my own orgasm arrived within moments after that as I was squirting my hot load of cum into the condom.

After our orgasms, I leaned down and kissed her very passionately. She wrapped her arms around me and whispered in my ear, “I love what you have just done for us and I love you deeply, Ted.”

I whispered back to her, “I loved it, too, Honey, I loved having my love member fully inside you and I have loved you for a really long time since the first time we met in school Sweetheart.”

I then softly said to her, “I really wished that I had not had to use that condom. I would rather have squirted my hot love cream deep into your sweet, hot love passage and left you a baby in your warm, soft tummy, Shirley.”

Shirley replied with tears streaming down her cheeks, I would have liked that, too, but, I understand the reason we can’t have a baby right now, Ted. Besides, my parents would have kicked me out of the house if I got pregnant like my Sister did especially after all of the things they have done to keep me away from boys and getting pregnant.”

Leaning down over her with my deflating dick still inside her pussy, it slipped out of her. I held her, kissed her fervently and told her, “We need to get dressed and get back to your Sister’s house, Honey, before they get to thinking that we have been gone way too long.”

When I pulled the condom off of my dick, I noticed some slight streaks of red on it. I told Shirley what I saw and gave her my handkerchief and told her to put that in the gusset of her panties when she put them back on. She took my handkerchief and wiped her womanhood with it and put it inside the gusset of her panties as she put them back on.

Then we both began to get dressed again. As every guy and girl knows who have made love in a car it is not easy to get undressed in the car and it seems even worse to have to get dressed again in the car.

I was concerned that her parents might come over to her Sister’s house to pick her up and take her home. I did not want them to find me there with her and cause her to be in big trouble with her parents.

Shirley told me “There is no worry about that, Ted, since I’m going to stay the night with my Sister and my parents will not be coming to get me tonight. And my Sister doesn’t care how long we have been gone.

I also want you to stay the night there with us in my Sister’s house; too, as my Sister said that you and I can sleep in the living room while they are sleeping in their bedroom. I think that she may even be hoping that I get pregnant tonight.”

I replied to her, “I would love to stay the night with you at your Sister’s house, Shirley, but, my parents will be looking for me to come home sometime tonight even if it is very late.”

After we had gotten dressed we returned to Shirley’s Sister’s house and most of the other guests had already left. When we walked into the house her Sister and her husband were sitting in the living room talking with the one remaining couple drinking a beer. Her Sister greeted us with a broad smile and asked us “Have you two enjoyed yourselves tonight?”

Shirley quickly responded, “Yes we did very much so and we were very careful, too.” with a sly smile on her face. Shirley’s Sister knew what had happened by the way Shirley was walking when we came in the door.

 
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