Jon, Kate and Best Friend Shelly

EDITED

Author's Special Notes:

Note 1: The author wishes to express his great appreciation to Patrick Armagh for his invaluable hard work in editing of this piece and his unique professional contribution to the story which has greatly added to quality of this work.

Note 2: The author has revised and expanded this story for the readers and for those readers who have not had the opportunity to see and read the original story.

Jon and I are 19 year old fraternal twins. We graduated from high school and live at home while in our freshmen year at our local community college. We both have always been good students and have always made good grades and have always made the honor roll in high school. As twins, we've always been close and did as many things together as we could; understanding that boys and girls can't do everything together, of course.

We always planned to go to the same college or university together so that we could maintain our close family relationship and our fraternal love for one another, which I assume is common with most twins. However, our parents also encouraged us to love and get along well with each other, as well as with others. Of course, our parents suggested that we should go to our local community college for financial reasons as well. Obviously, it cost less to go to the local college and not have to pay for our room and board if we could live at home with our parents.

In addition to being good students, Jon and I participated in a number of sports. Jon being on the track team, he ran cross-country and had played intramural sports as well. I played girls' basketball, softball and volleyball in high school which I played with my best friend, Shelly Koehler.

Shelly and I were also both very popular in high school. Jon also had plenty of friends in high school that he played sports with, and went to school sporting events and dances. He was considered to be a handsome guy and playing sports had given him a well-toned muscular body that many of the girls in our high school drooled over. Jon generally had no problem getting dates.

I'm Kate Ryan, or Katie as my family and friends always called me. I was one of the most popular girls in school along with Shelly. Neither of us had any problems getting dates as we looked very much like one another. Two very pretty girls, with shoulder-length blond hair, fair complexions, sky blue eyes and we had shapely, well-toned bodies from playing sports. We share matching figures with 36C-24-36. Next to Jon, Shelly has been my best friend, and we spent a lot of time together; not only at school but after school, and weekend sleepovers. Shelly and I were such good friends that we often double dated; which our dates never really had a problem with.

Shelly and I were also very competitive in academics and sports but, with other people as well, even with Jon. Shelly and I always had a friendly competition with each other, competing with one another for dates with good looking boys. Our individual success rate for dates was about even. How could any guy make an easy, simple choice between two girls who looked very much alike in most respects?

Even though Jon is my twin brother, I began to notice his good looks and his great body and I began to fantasize about him. Unbeknownst to me, Jon had also begun to notice me, and he shared my thoughts. However, neither Jon nor I had ever shown any sexual interest in one another in that regard for obvious reasons.

Jon and Shelly were often in the same classes together in high school, and they were even in some of their same college classes together. I think Jon would have liked to have dated her except for the fact that she was my best friend, but, seemed happy that Shelly and I were best friends and that she was so often at our house and occasionally sleeping over with me in my bedroom. I think Jon enjoyed seeing Shelly as much as Shelly and I enjoyed our sleepovers.

Shelly of course, liked Jon just as much, and whenever she was around him, she was very nice and she was always making eyes at him. She was always quick to accept my invitations to come over and stay the night at our house. Of course, neither Jon nor Shelly had ever made any comments or advances toward each other.

Jon and I had always spent at least one weekend night to watch a late movie together. On one Friday night, thinking that we would be there to watch a movie since there was no home game to attend to attend, I invited Shelly to come over and watch a movie with us. And then she would stay and sleepover in my bedroom. However, Jon had made plans to go out with his friends and wouldn't be home until late. Since Jon wouldn't be there, Shelly and I chose to watch a romantic chick flick. About half-way through the movie, Jon came home and sat down to watch the movie with us.

"What is this movie?" Jon asked.

"It is a chick flick and you may not like it." I replied.

Since it wasn't his type of movie, he kept glancing at Shelly while trying not to be too obvious. Shelly was admiring Jon in much the same manner and she kept squirming in her chair. It was obvious they both had the hots for each other. Knowing Shelly as well as I did, I figured that her panties were soaked as she was making eyes at Jon. Of course, I thought that it was likely that Jon was feeling like he could shoot his load in his briefs since he continued to look so hungrily at Shelly.

At a lull in the movie Jon got up and said he had some beer in the fridge and asked if we wanted to have one with him. Even though neither one of us particularly liked beer we both agreed. Jon went to the kitchen and came back with a beer for each of us and one for himself. He also brought a bowl of corn chips with melted cheese on them. He later went back to the fridge and got all of us another beer which we all drank as we ate the remainder of the nachos. When the movie ended, he got up and told us he was tired and was going to go to bed. We both said "Good night, Jon" as he headed to his bedroom.

After Jon had gone to his bedroom I whispered to Shelly. "I saw you two checking each other out during the movie, Girlfriend, and I saw you squirming in your seat also. Your panties had to have gotten sopping wet."

"How could any girl keep her eyes off of him? He gives me a warm feeling in my lower tummy and in between my legs whenever I look at him, Katie. And when he looks at me, I can feel my panties getting wet, too."

I just rolled my eyes, smiled and shook my head. Later, as Shelly and I were heading to my bedroom I told her, "I have some new perfume that I think you'll really like. It is really great. Do you want to try it?"

Shelly quickly replied, "Yeah, let's go. If it is as good as you say it is I can't wait to try it."

When we got to my bedroom we each stripped down to our panties and bras to be more comfortable since it was a little warm that evening in my bedroom. We dabbed a little of my new perfume on ourselves especially between our breasts.

"Oh I do like this, Katie." Shelly exuberantly exclaimed.

"I think that Jon will really like it too, Shelly, don't you""

"Oh, yeah, he will. It should make him really want to get close to me or to you, too, for that matter if you really want him to."

The movie we watched had been very sexy, and we were both still a little turned on from watching it. So we sat down at my computer and began to surf the net. We clicked on a porn site and began to watch some porn videos. We found a video of a sexy young couple making love with one another. The guy had a big dick, and his face and body looked a lot like Jon. Of course neither Shelly nor I had ever seen Jon's penis, but we both became very aroused by the video. I wasn't sure about Shelly but my panties were about to get drenched and I suspected her panties were getting as wet as mine were.

When the guy slammed his big dick balls deep into the girl, then repeatedly rapidly and forcefully thrust into her tight pussy, he quickly began to bring her to her orgasm. He pounded her through another orgasm and started cumming inside her; both of them were breathing hard and moaning very loudly. When the video showed his cum running out of her pussy and down the crack of her ass onto the sheet, we both became very excited, our panties becoming much wetter with each of us having had our own orgasms.

"Have you ever been with a boy like that and had sex with him, Katie?"

As close as we were, this was the one subject we had never really talked about in the past. "No, my mother and I had a talk and she said if I did, I'd probably get pregnant and it would totally destroy my future. Have you ever had a boy inside you like that, Shelly?"

"No, I've never had sex because of I'm afraid of getting pregnant and having to drop out of school and not being able to finish college and do the other things that I want to do."

"Well, if you could make love with someone who would you most like to have sex with your first time?"

"Please don't be mad at me, Katie, but, I would really like to have Jon be my first. He is really hot but, my mother told me that I should make sure when I do make love my first time, it is with someone I really love and who really loves me. I don't know, but I think that Jon really likes me and maybe he even loves me. Why do you think Jon hasn't ever made any advances toward me, Katie? We always make eyes at each other each time we are around one another."

"Shelly, I know that Jon really likes you and I think he has never hit on you because you and I are best friends."

"Oh. Well, how about you Katie? Who would you like to make love with your first time?"

"I know it's wrong, but I also really want Jon to be my first, for pretty much the same reasons you just mentioned. We have always been so close that when we got to be about sophomores in high school I have wanted him very much."

"Wow! Have you and Jon have ever flirted with each other?"

"No! I've been afraid to hit on him and I also think that Jon is afraid to hit on me, too. Besides, if our parents ever found out we had sex with each other, they'd absolutely kill the both of us."

The chick flick, the beer, the porn and having our conversation about sex had both of us very hot for Jon. With my impudent nature, my excited state, and in accordance with our competitive friendship, I challenged Shelly. "I dare you to go into Jon's room and make love with him. Jon always sleeps in the nude. All you need to do is go into his bedroom without your clothes on. You won't have to worry about his underwear or his pajamas getting in the way or getting them off of him to make love with him."

Shelly giggled and squirmed. "I'd like to take that challenge but what about him getting me pregnant, Katie? I can't let him get me pregnant, Katie. And I don't think that you would want me to get pregnant like that either."

I thought for a moment. "You don't have to worry about that just wait right here for a couple of minutes and I'll be right back." I went to my parent's bedroom as they were out of town for the weekend. I got my mother's contraceptive foam kit out of her night stand drawer and brought it back to my bedroom. "This is my mother's contraceptive foam kit, Shelly. It will prevent any problems with a pregnancy if you use it before you make love with any boy or a man including Jon, Girl."

We read the instructions on how to use it and Shelly quickly began to apply the contraceptive foam into her pussy. She had a pained expression on her face when she inserted the applicator into her pussy having a little difficulty in getting in into through her hymen but, she succeeded and I guessed that she was protected from getting pregnant. I saw the pained expression she had on her face when she was inserting the foam in her pussy and I wondered if it was always that painful when my mom used it and would I have the same problem that Shelly had.

Shelly had one condition to my challenge, "Before I accept your challenge, Katie, and do this, I challenge you to make love with Jon, too, just like I'm going to do. If you're not going to agree to that then all bets are off." With a slight hesitation, I agreed and planned to apply the contraceptive foam to my pussy just like she did, just before I went in to make love with Jon. With that Shelly took off her bra and panties, put on my robe and left for Jon's bedroom. As Shelly slipped off to Jon's bedroom to meet my challenge, I smiled to myself. She had done just what I hoped, and now that my plan was in progress, I thought it had an excellent chance of succeeding.

Shelly entered Jon's bedroom very quietly opening his door. She stepped inside his bedroom and very quietly closed the door behind her without waking Jon. She dropped her robe by the door and crawled into the bed next to Jon both of them completely in the nude. She very gently grabbed his soft penis with her small delicate hand and began to slowly and gently stroke it to bring his penis to full erection. Jon somewhat woke up from a sound asleep and in the dim light from his night light, he recognized Shelly. He could smell the perfume she had on which he liked so very much.

Since Jon really wanted her, he immediately responded to her advances. He put his hands on each side of her head, pulling her face down to his and kissed her very passionately. He whispered in her ear, "Lay your warm body on me, Baby. I want to feel how hot soft and wonderful your titties feel pressing tightly against my body, Sweetheart."

Without a word she laid her soft, warm breasts on his chest, and he moaned his approval and delight to her. He then raised her up as he slid both his hands up to her chest, taking each of her breasts in his hands gently caressing and squeezing them between his hands. He tenderly began to lovingly kiss each one of them, firmly sucking on her hard, pink nipples. Shelly's heart beat began to race toward the red line. She had gotten very nervous, her breathing becoming very erratic with anticipation of what was about to happen and that she was about to have Jon's dick fill her wet virgin pussy.

Jon wordlessly flipped her over onto her back and got between her thighs. He slipped his hand between her legs, cupping her very wet, well lubricated pussy signaling she was ready for him to enter her sweet, hot pussy.

Shelly softly whispered to him, "Jon, please be gentle and careful with me as this is my first time and I'm still a virgin."

Jon nodded and slowly inserted his hard dick between her inner pussy lips and slowly began to push it inside her until he felt the obstruction that he knew was her hymen. He paused for a moment, allowing her time to adjust to his size, and then quickly thrust his hard dick into her pussy rupturing her hymen. She squealed very loudly from the sharp pain as he achieved his full penetration into her depths. Once there he paused again giving her time to adjust to the shock of his full penetration and to recover from the sharp pain of her newly ruptured hymen.

A few moments later, Jon began to slowly stroke back and forth inside her velvety softness, increasing the speed and forcefulness of his thrust. Shelly moaned softly, her breathing growing more erratic as she involuntarily bucked her hips up to meet his downward thrusting. As Jon sensed her impending climax, he began to thrust faster and deeper into her warm, wet vagina. Within moments, she squealed loudly as her orgasm rolled over her and engulfed her like a tsunami. Jon managed a few more thrusts as his orgasm swept over him, collapsing on top of her, his hard dick still inside her.

When their orgasms had subsided, Jon gently kissed Shelly, telling her how much he enjoyed their love making. "I loved being deep inside you, Baby, and I've been in love with you for a long time, Shelly."

"I loved it very much, too, Jon. And, I've loved you for a long time, also, Honey." Shelly got out of bed to go clean herself up in the bathroom. Saying before she left the room "I have to use the bathroom. I'll be right back after I get cleaned up." Shelly picked up her robe, quickly left his bedroom and came directly into my bedroom looking and acting exhausted from her love making with Jon. She handed me the robe, laying down on the bed still gasping for her breath. I watched as some of Jon's cum was running out of her pussy, down her leg and down onto the bedsheet beneath her. Shelly looked at me with an exhausted but satisfied smile. "Now it's your turn, Katie. I have had and enjoyed my turn now it's your turn, Girl. You can't welsh on you bargain with me."

"How do you feel about what you just did and what has just happened, Shelly?"

"In a word, it was wonderful and I can't wait to have Jon do me again. I know that once you have had him inside you, you'll feel the same way, Katie. Now get in there and fulfill your part of our bargain."

I quickly inserted the contraceptive foam inside my vagina. Like Shelly, I had difficulty getting the applicator inside my pussy and fought through some pain as I inserted it. However it felt, I concluded that I would be protected by the contraceptive foam from Jon's cum. With my pussy prepared, I put on my robe and went into Jon's bedroom, crawling into bed with him. Jon smelling the same perfume and the very dim light should believe that Shelly had returned to him for another session of love making. I lay down on top of him. My warm, natural breasts pressing into his chest and I began to kiss him passionately. He whispered to me just how wonderful it was to feel my warm, soft titties on his chest. My heart rate began to increase along with my nervousness as I ground my wet my pussy against his big dick.

Jon's erection was revived very quickly, and he began to passionately kiss me, his tongue slipping into my mouth. He flipped me over onto my back, kissing and sucking on my hard, pink nipples. He slowly kissed me between my breasts, down to my tummy button circling it with his tongue before dipping his tongue into it. He continued to kiss his way down to my love mound somewhat hidden behind my neatly trimmed, blond bush.

Jon lowered his face between my thighs, kissing along each crease where my thighs meet my pussy. I let out a loud moan and gasped for my breath as Jon gently lifted and slightly spread my legs and he kissed the cleft of my pussy from the top to the bottom, his tongue gently separating the inner petals of my pussy before snaking his tongue inside my pussy. The sensual feeling inside my pussy slit gave me such a pleasure that I loudly moaned his name repeatedly during the time his tongue was inside my pussy lips.

Jon moved up to kiss and suck my clitoris causing me to loudly moan and squirm and move my hips beneath him. He moved up over me, passionately kissing me and whispered, "Are you ready for me to slide my hard dick back inside you, Honeyoney asdkjflskjs dj?"

I nodded and whispered, Yes, Baby, and I can't wait to feel you inside my pussy."

He reached down and cupped my pussy with his hand as I squirmed with anticipation. He gently placed his hard dick inside the opening of my pussy and slowly began to enter my sweet secret love treasure.

I very softly whispered "Please be careful and very gentle with me, Jon."

He slowed his advance inside me when he felt my hymen. He hesitated as he had with Shelly and then with one quick, forceful thrust, he fully penetrated my vagina fully to my depth. I groaned and then screamed very loudly as he broke my hymen with my tears streaming down my cheeks. That caused him to pause again; allowing my pussy to adjust to the size and presence of his large dick fully inside me. He began to slowly thrust in and out of me as he had done with Shelly and after a few moments, he began to increase the speed of his thrust. I was moaning quite loudly and my breath had become very labored and erratic as I neared my orgasm.