Jack 5

Jack is my best friend, actually more like an older protective brother. My name is Alexandra, but Jack has called me “Peanut” forever. He only calls me by my real name when he’s upset at me, being his usual “over protective brother” self. We talk about everything, from what we had for breakfast to our dreams and goals, and even relationship stuff. Jack is 22, just 2 years older than I. We’ve known each other for as long as we can remember, we grew up next door to each other. Many friends have come and gone as Jack and I have grown up, but our friendship has never faltered over the years. To tell you a little secret, I’ve always had a bit of a crush on Jack. He’s tall and has short brown hair, lightly tanned skin, and the most beautiful blue eyes a guy can have. He has the sexiest body, everything is in the right place if you know what I mean. He works out and eats right, he’s always been athletic and played a lot of sports in and outside of school. He’s very striking, and I admit that over the years growing up, I was always envious of his girlfriends, but I never let that stand in the way of our friendship.

College was only two hours away, and when he left for school, Jack always made sure to send me letters and emails, and to call whenever his studies allowed him a little extra time. That is, until I graduated and followed in his foot steps. Once I got there, Jack and I spent as much time together as possible, helping each other with our studies, watching movies, meeting new friends, going to the occasional party. You know, the usual college stuff. I’ve survived my freshman year which is Jack’s senior year, mostly thanks in part to Jack, the transition from home wasn’t easy for me.

On his graduation day, I received a bit of a shock. After the ceremony, Jack ran up to me and gave me a huge bear hug. “I posted my resume online, and I got a job! I’m so excited, I just couldn’t wait to tell you!” I told Jack that I was happy for him and that I was so proud of him as I hugged him back. “I start in a week.” He said.

“A week? So soon? Where will you be working?” I questioned, staring up into those blue eyes. I was scared, thinking that Jack would be leaving again. My best friend would be off to see the world, without me. He must have sensed my fear.

“Relax, Peanut. Don’t panic, I’m not going anywhere. I’m staying here in town, I got a job at the Physical Therapy Center across town. I may have my bachelor’s, but I’m not done with school just yet. I can work there while I finish going to school here for my master’s.” A sense of relief came over me and I hugged Jack. “Jack, I’m so happy. You’re my best friend and I couldn’t imagine spending time without you.”

“Peanut, don’t think for a minute that I could spend time without you either. Who would look after you and keep you out of trouble if I left town to go to another college or work? I’m not going anywhere. In fact, my roommate is moving out. Move in with me and out of the dorms. I’ll take care of the rent, you just stick to your studies.”

“I, uh……..Jack,” I just stammered. “Are you serious?” I couldn’t believe me ears. I just kept replaying the last few minutes in my mind. First he tells me he’s staying, then he tells me he wants me to move in with him. What is happening? I stared at him for a few seconds in disbelief, and when I realized I was staring, I turned my gaze to the ground in embarrassment.

Jack put his hand under my chin and lifted so I was looking at him. “Did I say something wrong?” “N..no,” I stammered, “I’m just in shock.” “Good then, it’s settled, you’re moving in with me,” he said as he hugged me. “We’ll move stuff tomorrow.” I didn’t have much with me in the dorms, mostly clothes and a little bit of linens, and a few personal belongings. Everything else was back at my parent’s house.

That’s the day when things between Jack and I started to change. I started to see him in a different light. We got everything moved in with in just a couple of hours, and a couple days later I started my summer job to keep me busy until sophomore year started. When Jack and I would spend time together, I realized I was noticing little things now that I never noticed before. I noticed how the corners of his lips twitched when he smiled, how his eyes glittered when he laughed, the shape of his hands and how soft they were. I also started to notice more about his body, especially when he would walk around the apartment in a pair of shorts with no shirt on. I realized that I was falling for my best friend, I was falling in love. Over the first few weeks of the summer, I also noticed that Jack behaved a little differently around me. If I was sitting reading a book or watching T.V., he’d sneak up behind me and wrap his arms around me, give me a peck on the cheek (the peck on the cheek thing isn’t new, he’s always done that), and a hug. Then he’d say things like, “How’s my favorite girl?” or he’d tease me into a tickle fight.

Then one Saturday morning, I woke up to Jack bringing me breakfast in bed. I scooted over to the middle of the bed and Jack sat next to me. “Happy birthday, Peanut! I made you breakfast.” I was so hungry, and everything smelled so good, I just gobbled it all up. “Jack, thank you, you are so sweet. I appreciate this, but you didn’t have to go to all this hard work,” I giggled. “Nonsense. I did it because I love you, you know that. You mean the world to me, Peanut. You know I’d do anything for you.”

Then Jack did something I wasn’t expecting. He set the tray on the ground, and as he turned around to face me, he touched the side of my face with his hand, and leaned forward and gave me a quick kiss on the lips. “J..Jack,” I stuttered. “Shhhhhhhh,” he placed his fingers over my lips to quiet me. “Listen, there’s something I need to tell you. Peanut, I love you. I always have. You’re my best friend, and I’ve always thought the world of you. I’ve always been in love with you, I just could never find the words. And I didn’t know if you felt the same way. I’m just sorry it took me so long to tell you, but asking you to move in was the first step. I guess you could say I saved the best for last.”

At that, tears started to well up in my eyes, I was so happy. “I love you, too, Jack. I always have.” I leaned forward and wrapped my arms around Jack, and I kissed him long and hard. His tongue slid into my mouth, and as I sucked on it, I massaged it with my tongue. “Jack, you taste” I started to say before Jack cut me off. “Hush,” he said as he leaned in to kiss me again. My heart started to flutter and I started to get this warm feeling all over my body, a feeling of happiness. I’ve had boyfriends before. I’ve kissed them and fooled around a little, but I’ve never been intimate with any of them before. And I never had these feelings before. I knew that it was love. As Jack and I kissed, our breathing became heavier. Jack began to caress my cheek with one hand, and my arm with the other. His touch sent a wave of chills down my spine. When I shivered, Jack cupped his hand behind my head and pulled me into a deeper, more passionate kiss. His other hand rested on the small of my back.

I could feel his hand rise up the back of my shirt, his skin so soft on mine. I was becoming aroused. It confused me a little because this was Jack, but I was beginning to like the feeling. Jack pulled back the covers on the bed and lay down next to me, and he began kissing down the side of my cheek and down my neck. My body just shivered at his touch. His hand caressed my arm, and then he slid it under my night shirt onto my belly, which he began to rub a little. I moaned a little, and reached over to touch his face. I pulled him up to me, “Kiss me,” I said. As Jack and I kissed, I could feel my panties becoming wet in my pajama shorts. Jacks hands began to wonder up to my breasts and he began to massage them and play with my nipples.

Jack’s tongue slithered in and out of my mouth, mine in and out of his. I lowered my hand to Jack’s crotch, and rubbed it through his shorts. I could feel his penis getting stiff under the shorts and I began to rub a little faster while I kissed him. He moaned, stood up and pulled his shorts off so that he was naked. As he undressed, so did I. He lay down next to my nakedness and began sucking on one of my breasts while his hand played with the nipple on my other. I was almost in ecstasy. At this point, I didn’t think it would take much longer for me to arrive at climax, so I tried to push the thought from my mind. My hand found his stiff cock and slowly I began to stroke it. “Suck it, suck it for me,” he said to me. I looked him in the eyes for a second, and without question, I moved down to his cock, my hand still stroking. I hadn’t noticed before, but Jack was huge. He must have been 10 inches easy, with a pretty good girth if you ask me. I leaned down and kissed the tip, and then down the sides all the way to the balls, which I took each into my mouth in turn and gave a quick suck. I licked back up the shaft and took the tip into my mouth. I began sucking on just the tip, slowly taking more into my hot mouth, my left hand stroking while my right hand massaged his balls. I could taste a bit of precum in my mouth, I never imagined Jack could taste so sweet. As Jack began to moan in pleasure, he sat up a bit so he could reach my leg. He pulled my body around and my leg over his head so that I was straddling his face. The next thing I know, his tongue is sliding deep into my wet cunt, and flickering around my clit. The feeling was so sensational that it was hard to concentrate on sucking him off, so I settled for stroking him. His hands found my nipples and the second he started twisting them, an orgasm rocked my body hard. My whole body twitched and shivered.

“Did you like that, baby?” Jack questioned. “Feel good?”

“Y…yessssss,” I muttered. “You have no idea how good that felt.”

“We aren’t done, yet, baby. Turn around Peanut. I want to hold you in my arms for a little bit.” I climbed off of him, turned around, and lay down beside him, Jack’s arms wrapped around me in a warm embrace. We lay there in each other’s comfort for a few minutes before I felt his lips on mine again, passionately kissing me, his tongue darting deeply into my mouth. As I kissed Jack, we began to caress each other, our hands wandering all over each other’s bodies. Jack found his way to my neatly trimmed patch, still sopping wet, he slid two fingers right in and my body shuddered. I was still sensitive from the orgasm. I tried to pull his hand away, the sensations were just too much, but Jack pushed my hand away. “It’s ok. Those sensations are normal. Just relax, baby. I won’t hurt you. Just lay back on the bed and relax. Don’t do anything. Let me please you, Peanut. I want to please you more than anything.”

Once again, Jack’s fingers found their way to my wet cunt and he slid two fingers in again. “You’re really tight, you know that?” I just moaned slightly and gave him a little nod. He started pumping them in and out, his thumb slowly roaming circles around my still sensitive clit, which was sending slow shivers through my body. Eventually I began to relax a little and get used to the feeling. Jack sensed seemed to sense it too, because the next thing I know, he was sliding a third finger inside me. I let out a little squeal and he stopped pumping and let his fingers rest inside me. “Oww, Jack, that hurts,” I whimpered. “I know, baby, it’s tight. You’re a virgin, aren’t you?” I looked away from him, embarrassed. I couldn’t answer him. I grabbed the covers beside me and pulled them over me. I didn’t want him to know I wasn’t that experienced. “Baby, baby, look at me. Peanut, look at me. It’s not a bad thing, ok? In fact, I think it’s something precious. I always wanted to be your first.” Jack gave me a kiss on the cheek. “Don’t be embarrassed. It’s me, Jack,” he whispered in my ear. With his free hand, he pulled my face toward him and gave me a quick kiss on the lips before leaning down to suck on one of my breasts.

The sensation of his tongue and teeth stimulating my nipple began to relax me and I pushed the covers aside so that I was exposed again. Jack asked if I was ok and I nodded, unable to speak. Jack took that as a sign to move ahead, and slowly began to pump his fingers in and out of my pussy. “Baby, just lay back, you don’t have to do anything. Let me do all the work, let me please you.” As Jack worked his fingers in and out, that little twinge of pain I first had slowly dissipated and waves of pleasure started running through my body again. I began to rock with the motion of his fingers. “Baby, I think you’re about ready for my cock. Do you want me to fuck you?” Jack asked. I was a little shocked at his choice of words, and I let out an inaudible mumble of “I’m scared.”

“What’s that, baby?” Jack asked, his fingers still working inside my cunt which was dripping. “Jack, I’m scared. It’s going to hurt. Go slow.”

“Yes, baby, I won’t lie. It will hurt. But it will hurt a lot worse if I go slow because it tears slower. I have to do it fast, and once I get in, I can go slow. It will be better that way, ok?” I nodded, still rocking against his fingers. Truthfully, I was terrified. I don’t take pain very well. “Baby, just lay back and relax, ok? Spread your legs a little wider for me.” Jack climbed on top and lowered his body close to mine, soft kisses on my forehead and my cheeks, and then kissing my lips. He was trying to distract me, one hand stroking his cock and guiding it toward my brown patch. He began to rub the tip between my lips, getting the tip of his cock nice and soaked. Jack entered me about an inch and I let out a little yelp, not out of pain, but of fear. “Relax baby, just lay there and relax, I’m barely in, nothing to worry about yet. I’ll stay here for a little bit. I love you, with all my heart and I’m glad to share this with you. I couldn’t think of any other way than to spend this day, than being with you.” And with that, Jack rammed his rock hard cock into me, not all the way, but enough to do what needed to be done. I screamed from the sharp pain, tears welling up in my eyes as I looked up into Jack’s beautiful blues, my arms wrapped around Jack, my nails digging into his back. “There, Peanut, the bad part is all over. Just relax, sweetie, everything is fine. You can cry, it’s ok, this is something special between you and I.” I whimpered a little, trying to hold most of it in, not wanting to let Jack know how scared I was and how much it hurt. He lay there inside me for a few minutes, letting me get used to the feeling of him being inside me. Slowly he began to pump. It still hurt a little, but that began to fade and a feeling of fullness started to take over. Jack reached down to my clit and began rubbing it as he glided in and out of my cunt. “Oh my god, baby, I was so scared, but it’s starting to feel a little better now,” I whispered in his ear, my voice faltering a little, a tear running down my cheek. “I love you.”

As Jack began to pump, his cock, which had gone down a little, began to rise again and I could feel it getting a little tighter. He lowered himself just enough to suck on my nipples while he fucked me. I just lay there, holding him, feeling him slide in and out of me, enjoying this new sensation inside my body. As Jack rubbed my clit, I could feel my body rising toward climax and I told Jack I was going to come. He furiously started pumping, fucking my wet warm cunt and rubbing my clit. All at once, my body shuddered. The muscles inside my vagina squeezed Jack’s cock with every shudder of my orgasm and at once, I felt Jack’s body shudder with mine. The sensation of my body squeezing his cock was enough to send him over the edge and I could feel his hot liquid spurting inside me. He pumped until the last bits of juice were drained from his stiff member and then he lay down beside me. He nibbled on my ear and whispered, “I love you, Peanut.”

“I love you, too, Jack.” I climbed off the bed, pulling Jack up with me, and I led him to the bathroom. I ran a nice hot bubble bath and the two of us relaxed in the warm suds, reveling in what just happened. I leaned back into Jack as he kissed the back and side of my neck, “Alexandra, will you marry me?”

I didn’t even hesitate. “Yes, Jack. I want to spend the rest of my life with you. I love you.”

The rest of this summer Jack and I have been closer than ever and he is showing me a few new things. I have been preparing for my sophomore year and together we have been working on wedding plans. We are getting married next summer and we couldn’t be happier!