The Next Step for Jessica and I
Jessica was a cute girl with blonde eyes, a slender figure, and skin of an angel. She had grown prettier every time I had glanced at her from my window next door. Her parents were asian and white, but oddly enough, Jessica had the blonde hair, whilst her sister, Connie, had blonde hair. Connie, the youngest of the both, had a darker complexion than Jessica, but all in all, they were roughly identical minus the hair and the eyes. Jessica was a freshman, going on sophomore, and her sister was an eighth grader going on freshman, I, however, was on par with Jessica.
After the last day of school had let out, I had just broken up with my girlfriend, who I just found cheating on me with my best friend. At first, it wasn’t such a big deal, but then it had started to grow on me, and for the first week out of that 8 hour torture, I had grown into my backyard chair for another 8 hour torture session with myself.
“Hey, Nate, what’s goin-,” Connie had stopped mid-sentence, “Oh, I’m sorry, still going over that break up?”
“Yeah, Monica was something to cherish…”
“Oh, well, if it matters, I’m sorry abou-“
“Don’t worry about it”
“Hrm…”, Connie had paused, wondering when it’d be alright to speak.
“Well, don’t let it bother you,” I said, “What did you come over here to say anyway, freshman?”
“Ha, well, at least you haven’t gotten the very essence of your soul stripped out of you… I was just wondering if… if you’d like to come to the mall with my sister and I, and maybe a few other friends,” Connie’s words were a blessing, I didn’t want to risk running into my ex-girlfriend at the mall by myself without a reason to be there by myself.
“Well, as long as none of your other freshman friends are going to be there.”
“What’s with the freshman jokes, jerk?” Connie gave a sarcastic smile.
“Expect more of it, I’ll be at your house at let’s say… four?”
“Sure, “ Connie had walked over and had given me an unexpected hug, “I’m sorry for your loss, but heck, you might find someone else.” Connie had blushed as soon as those words had left her mouth. As soon as she had noticed she was blushing, she had just turned around, and had somewhat speed walked out of the gate.
Four grueling hours had passed by, and I had wondered if Connie had liked me or not –of course, she was cute and all, but I’m not sure if I was ready for a girlfriend or not… besides, I had taken a liking to her sister over the years that we had been neighbors. I had arrived at their house in a hurry, as I am almost always late to everything. I rang the door bell, and had wiped the lint off of my black shirt. Jessica had answered, and had proclaimed t hat her sister was still getting ready.
“Connie is still wondering what to wear, I’ll be right back to tell her to hurry her ass up.” Jessica’s words were always straight to the point, but I guess that was what had made her so cute, as I have always liked the shy type.
“CONNIE, GET YOUR ASS DOWN HERE, NATE’S WAITING!”
My ears had bled she shouted so loudly, “Jeez, could you yell any louder?” Jessica giggled a bit, and had quickly glanced into my eyes, then looked away. “Well look, I’m going to sit down and wait for your sis.”
I took a seat, and had so had Jessica. Jessica had crossed her legs and turned the TV on. As she was flipping through the channels, I had seen a flip flop dangle off of her foot in a rhythmic motion. Here little toes were painted a bright silver, and from the looks of it, the paint was just a few days old. Her foot was a brilliant crème color, and had looked as if it could be smoother than silk. After around ten minutes of random channel flipping and dangling flip flops, Connie had come running down the stairs, “Shit guys, let’s go, we’re going to be late for the movies!”
“Movies,” I question, “I was never informed of a movie, freshman.”
“Well, you know now, dontcha?”
“I guess,” I took a sigh, and counted the money in my wallet, “Well, I have enough, let’s go.”
The drive had been no longer than six minutes, but it had felt like forever, as I had been glaring at Jessica’s foot slowly push against the pedal, and ease off of it as if there wasn’t a rush at all. All was good until Connie had come up from the back seat and had put her hand on my shoulder, then her sister’s. I had forced a smile, and started to talk.
“You know, if I were any other sophomore, I’d kill you,” I joked around, “But since you’re a friend, I’m going to let this one slide…”
“Nate, that’s going to get annoying, but since you’re my sophomore friend, I’m going to let it slide…”
“Shut up freshman, hahahaha,” As soon as I had finished my second forced laugh of the day, the car had pulled into the spot in front of the mall. We all got out, and as I had rushed towards Jessica’s right side, Connie had rushed to mine. We had walked, just randomly chatting on how good it was to finally be out of school until we had hit the ticket line. Our best choices were a slasher flick, or some stupid one involving a fat guy and a Jewish guy –almost instantly, I had chosen the slasher as a feeble attempt to see if I can get closer to Jessica.
The line had moved up, and Jessica had paid for her own ticket, but as soon as the next register had opened up, Connie had said that she didn’t have any money, “Ok, freshman, but you owe me.”
“Whatever, just pay my way in, ‘kay?” she tried to let out her cute smile complete with her braces.
I paid for my ticket and her ticket, and we had been on our way to the movies. I had grabbed some sour candy along the way, and a soda for the three of us. We had chosen our seats and sat down to 20 minutes of previews. It was then that I had felt Connie’s had slip onto my armrest and touch mine, no biggie, but as the movie had progressed, she had claimed that the armrest was bothering her,
“Yeah, but I feel like I’m out of room, besides, you’re just using it to touch my arm and bug me,” she whispered, “come on, I won’t bother you again.”
“You’d better not, Connie”
The movie had progressed, but every time I had tried to make a move at Jessica, Connie had nudged me, telling me that she was scared. I offered my hand, and said that she could squeeze it as hard as she wanted to if she ever got scared.
As soon as it was over, and the lights started to get brighter, I took a short glance to my right –to Connie- and had noticed that her cheeks were doused in a pink color. I had smiled a bit, and didn’t know what to say, so I didn’t say anything at all. Connie must’ve noticed me staring at her, and had looked into my eyes and had giggled. I quickly looked away with a smirk on my face, and had then looked at Jessica, who was somewhat shaking after the last scare at the very end. I had felt bad, as throughout the whole movie, Connie didn’t even squeeze my hand once, I had even heard her laughing at the phony character lines and the ridiculously overdone gore.
After the silent car ride back, we had finally stopped at their house, where I stepped out of the car.
“You know, Nate, if you wanted to come in, you’re more than welcome to,” Jessica had said, “our parents are out for the week, and from what you’ve shown my sister, you could be quite the manly figure.”
“Sure, I’ll stick around, only if you never tell anyone about that. Ever.”
Jessica laughed, but Connie turned away.
I had ran inside my house and got a spare change of clothes, and my toothbrush, because heck, I’m not going to leave them alone. I asked my parents if it was fine to stay over there for a while, and they said I was pretty much in the clear, as long as I won’t do anything stupid while I was over there. I then stepped out my place, and went into theirs.
Jessica had greeted me at the door, and had told me to put my stuff wherever I wanted to. I just dropped it on the table in front of their couch, and jumped on their couch. Jessica soon followed. I grabbed the TV remote as Jess said that Connie had already fallen asleep, I then told her about what happened with the whole hand ordeal, and how it was not a big deal. She smirked, but had then looked into my eyes as if she had something important to say. And then she said it.
“Nate, I want you to know that I like you, maybe a bit more than just liking you, but you’ve always been there when I had needed a friend, even when you might’ve not known it.”
That had shocked me, as I had always stuck around, and had given the occasional hug when she was having a bad day, or the extended hug for when her family was fighting, or her friends had done something to evoke tears, but I ultimately never did anything important without me knowing. Heck, for the longest time, I thought that she was even a lesbian, since she had never brought a boy around the house.
“Jess, I kinda like you too,” those had been the only words out of my mouth, as that was pretty much all I had to say at the moment, “say, how about another movie before bed?”
“I’d love it.” She gave a smile, and looked into my eyes for the first noticeable time.
I found another movie with blood, guts, and gore, and had left it there. I held her hand as she lay in my arms, and we had watched the movie without a care in the world. Instantly, I had forgotten about my ex.
About a month later, Jessica and I were very close, and couldn’t be seen together without holding hands. I had never attempted to make out with her, as she proclaimed to never have had a boyfriend before, and I didn’t want to make her first kiss into a “first makeout”. Connie, on the otherhand, had grown a bit more irritable, and bitter towards our relationship.
During the middle of July, her father had gone away to a two week business trip, and her mother had gone to visit Jessica and Connie’s grandmother across the nation. I had asked my parents to stay over for another week, just like in the beginning of the summer, and they had approved. Once again, I ran and got my stuff for the night, and went back to Jessica’s house. Connie had opened the door, and had rudely escorted me to the room where I could put my stuff.
“You know Connie, if you’ve liked me in the past, I’m sorry for dating your sister, but I hope you’d understand.” I felt like a jerk saying that, but it had to be said.
“Whatever, I’m over that now, honest.” Connie had uttered that in a depressed voice, and had left the guest room.
I met up with Jessica downstairs and had propped myself on the very couch we sat on during our first “date”. She sat down right next to me and had hugged me. I had ordered a pizza and after about 30 minutes of cuddling and watching TV, the doorbell rang. We ate, and Connie had then escaped to the confines of her room. I sat on the couch once more, and held my lovely companion.
“Babe…?” I said.
“Yeah?” Jess answered
“ I just want you to know that I love you, and I really mean it.”
“…….I….I love you too,” Jessica had said that for the first time to me during our relationship, “But if you really love me, then you’ll give me a foot rub, I’ve been doing chores all day.”
Jessie had thrown her feet on top of my lap, and had wiggled her toes through her socks. I took her socks off slowly, and played around, just talking. I had then seen her feet. They were somewhat pale, but still that crème color, and they had the scent of what I recognized as lotion. Her toes were painted black, and the complexion had made it very erotic. I then placed my hands on her feet. She giggled, and had started to tell me about her day. I had rubbed her feet, occasionally tickling them to keep her awake (it was getting late), and she had squirmed around, giggling, and telling me to stop.
“Babe, are you falling asleep again?” I tickled her once more.
Jessica had jerked her foot up, and her big toe had gone into my mouth.
“Oh my god, I’m so sorry! You must be grossed out! Babe, I’m sorry!”
“Don’t worry about it,” I said, wiping the slobber off of my face.
“Nate, take five, we’ve been doing this for an hour, it’s almost midnight now, and I’m really tired!”
“Okay,” I said while guzzling down my soda from the pizza delivery, “But before you go to sleep, I’ve got something to give you.”
I stood up, walked over to her side, and kissed her on her lips. I crouched there, enjoying the smooth texture of my sweet’s lips with my eyes closed. She let out a small moan, and had held my head into place. I couldn’t tell how much time had passed, 30 seconds, a minute, 5 minutes, but we finally let go of each other. Her blue eyes shot into mine, and my heart was racing inside my chest. I sat down next to her and held her hand in between both of mine. We kissed again, and then I took her to the bedroom with me.
I led her into the bed, without a guilty conscience, and got under the covers. She got under too. As I was drifting off into my dreamland, I had her in my arms, with her feet resting on my legs, most likely for warmth. I then dozed off.
I woke up with the usual morning wood, but there was a different sensation –it wasn’t my underwear, and it definitely wasn’t me boning the bed… SHIT! It was me ramming my dick onto Jessie’s back! I quickly, but rather delicately, curled up to hide my shame. Innocent. She was so very innocent… But she soon woke up soon after.
“Hey honey, what was with the poking? It wasn’t cute, but I’ll be damned if you were trying.”
“S-sorry, babe, m-my bad, ha…ha…” I stuttered as I tried to make a feeble attempt to apologize, but I could already feel my face getting hot.
“Just trying to let you know that your dick really hurt.” She rolled over, but I could swear, I caught a glimpse of half of a smile.
The day went on, and our day was occupied with the constant bickering about what classes we might get together, and wondering if we should start our summer reading project for our English class. Our argument on whether we should wait a few more days ended up with me going out to Blockbuster and grabbing a few movies. Lately, we had gotten tired of grabbing the horror movies, as that was all we had watched, so I just picked up a random comedy and some popcorn. When I got back, I threw the movie in and got some soda from the fridge. I ran back before the movie started, and threw myself on the couch next to Jessica.
“’You gonna hold me? Because I don’t want you to poke me in the back again.”
“Oh come on, Jess, that was one time!” I said, trying to hide my embarrassment once more.
“I’ll tell you what, how ‘bout you just tell me one thing, and I won’t bother you again.”
“Whatever happened to you being the quiet girl next door?” I playfully questioned, “But what were you going to ask?”
“Well, I love you and all, but are we ever going to…” she trailed off, looking at the floor.
“To what?” I was curious, what she could ask other than –well, I wouldn’t expect that type of talk from her.
“Well, I know it hasn’t been a long time since we’ve been together, and forgive me if it sounds a bit dirty, but… when are we going to ever-“ she motioned her head, then waited for my response.
I was really in shock, I had no idea that she would actually ask something like that, since I’d expect myself to ask such a question, “Jessica, we haven’t even really kissed yet, and you expect me to…” I motioned my head.
“Well, I love you, Nate, I really do, and I was just curious if you’ve wanted to, after all, when I woke up, I was expecting for you go to all out on me, ever since I felt that… thing on my back.”
“Jess, I love you, but you’re just so innocent, and young, and for me to do something like that, I’d just feel like I’d violate you.”
“You wouldn’t, because I actually feel comfortable around you, I feel like I could have sex with you-“
I cut in, “Babe, you haven’t even had another boyfriend before, and I’m not sure if I’d be able to do it right…”
She got misty eyed, and just looked at me, “Nate –baby- I think that you’re really special, and I really wouldn’t mind, I just –I just wanted my first to be you!”
“I’m sorry, I just can’t do this, not now.” I bent in, and kissed her, but all of a sudden, she grabbed my head, and shoved her tongue into my mouth! Not knowing what to do, I played along, returning the favor. We were on the couch, holding eachother, breathing hard, and passionately sharing our feelings. My heart was racing at a hundred miles an hour, and my mind was trying to process what will happen afterwards, then, all of a sudden, she stopped. She let go, and pushed me off of her. Her hand had reached out and grasped my manhood. I couldn’t help but notice that my soldier was giving a standing ovation, and once again, I turned a deep red.
“Ok, Jess, if we’re going to do this, we have to make sure that your sister is asleep.”
“She was out early, I made sure of that.”
“Well, in that case, meet me in the bedroom in 5 minutes, I just have to get some stuff real quick.”
She eccentrically nodded, and ran up the stairs.
Five minutes had passed, and I had just reached the guest bedroom, and low and behold, she was still dressed. I wasn’t surprised, but at the same time, I was shocked. The only difference between her now and her then was that she had no socks on. Her feet were on the floor, with her same silky smooth skin, same crème color, and that dark nail polish.
“Hon, get undressed, and close your eyes for me.”
“Fine, but on one condition, the bra and panties stay.”
I didn’t know what to think, but I played along as she got undressed.
Her panties and bra were a black color, and her blonde hair was around her shoulders. Her skin was delicate, lacking any bruises or scars. Her body was slender, with the hint of what looked to be a four pack coated in just the slightest amount of baby fat, and she had a piercing in her belly button. From what I could see, there was a small wet spot in her panties and where she had sat on the bed.
“Okay, lie down on your back, and close your eyes.”
She did so, but her legs had remained closed. Innocent. So very innocent.
I brought an ice cube from the freezer, which was already melting in my hand. I put it in my mouth, got undressed down to my boxers, and did my best to keep my soldier down. I got on the bed grasped her shoulders, and started to kiss her neck. Playing around with the ice cube, I had felt her shudder once it came in contact with her smooth skin, then relax and let out a barely audible moan. I had went from her neck to the nape of her chest, then picked myself up, avoiding the breasts, and moved towards her navel. I dragged my lips downward, played on her adorable stomach, then moved on. I was at the legs now, the smell had been a bit odd, as I have never had sex before, but it was somehow familiar. I moved downwards, and with the ice cube almost gone, I stopped at her feet. I brought myself up back to her mouth, and kissed her passionately, slipping the ice cube into her mouth, and then releasing –but she brought me closer and nibbled on my lip, then had proceeded to stick her tongue into my mouth, exploring every inch, fondling my tongue.
When she had let me go, I proceeded to say, “Jess, this might feel a little weird, and forgive me if this is perverted, but if it feels too gross, just tell me to stop.”
She nodded her head, then closed her eyes and rested her head on the pillow.
I had dragged my tongue along the route where the ice cube had gone, but I had stopped at the inner thigh. The sharp smell was invigorating, and the fluids had started to run down the side of her panties. I lopped at her inner thighs, stopping only when I hit the lining of her panties. She giggled, and started to tense up. As soon as she relaxed, I went down to her feet.
I couldn’t believe how beautiful they were. I picked her right foot up, and started to rub it. Then I commenced to lick her heel. She shuddered, then giggled, but didn’t tell me to stop. I ran my tongue up her arch, enjoying every second of it. I licked up and down twice more. I then licked her toes. Her skin was so soft, and tasted so good, I couldn’t help but moan myself, I licked the big toe and nibbled the top, then started to suck all the other little piggies. I had felt the nail with my tongue, circling around each individual toe, then took my mouth off of her right foot and started on the left. I don’t know how much time I took, but all I knew was that the smell from her nether region had grown into much more of a wandering scent, it had grown into a strong wave of smell, invading my nose, telling me that she’s ready for an entrance.
“Just one more thing that I have to do, hon.”
She nodded with impatience.
I went up to her breasts, and reached under her. I then undid the hook, and pulled the bra off. It was a marvelous sight. Her perky breasts had then fallen to the side, nipples erect. I took one breast, and put my mouth on her nipple, circling around it, delicately nibbling. She moaned. I was rubbing the other one, delicately pinching it, twisting it every so carefully. Another moan.
I moved down to her panties, and took them off. They were moist and had a sticky feel to them. I opened her legs, and moved in. the first lick made both of us shudder. The taste was strong, much stronger than the smell. And she had put her hands on my head and ran her fingers through my hair. I licked at her perfect cameltoe (I didn’t know what it was back then), and prepared myself for what I was about to do. I got my index and middle finger, and had proceeded to insert them into her. I entered the lips, but ran into a barrier –I instantly knew what it was. My more experienced friends called this a cherry, and as I had always been intrigued by this, I had decided to leave it alone –at least for the time being. I ran up and down her lips, but focused on the part just above the lips, as I had gotten the most response from Jessica that way. I stopped. I looked up at Jessica, more beautiful than ever, and looked in her eyes, and bent in for a kiss.
It must’ve been about three minutes long, but finally, it broke, and a string of saliva had been shared between her and my lips.
“Are you ready?”
“More than ready, honey.” She splayed her braces, and her pearly white teeth, then motioned me in for another kiss.
“Here we go…” I said, pulling my boxers down.
My member was more erect than ever, at 7 inches, I had moved forward. Jessica had blushed, and smiled once more. I moved in, but before I could go for the gold (or would you say pink?), she raised her legs, and touched me with her feet. Her skin was so soft, I couldn’t help but wait for the grand finale. She stroked my cock with her feet, putting it between her toes, rubbing it up and down until I had almost come. She then put her fingers between her toes, and it drove me crazy. I went in and kissed and carresed her feet. I licked every bit of it, not particularly happy that they had touched my cock, I went in anyway. I licked between her toes, up and down her arch, suckled her toes, and then went on to the other foot.
Finally, done, I had moved towards her glinting pussy. I fit the head in, and she had tensed up. “It’s okay, relax, baby.”
“Okay, I trust you.”
I fit my head in once more, and found the hymen. “Now babe, this might hurt a little, so grab my hand.”
She grabbed my hand, and I proceeded. I went through it fairly fast, as to not torture her, and she squeezed my hand. I kissed her hand, and went on. Her pussy was so moist on the inside, and felt so warm. The vaginal walls had closed in on me, and the sensation was incredible. I thrusted in and out once, just to get the feel, then continued on. My bare skin was almost numb from how hard I was, so I just kept going. In-out-in-out-in-out-in-out, I was in heaven, and from the sounds of it, so was she. I continued until she had almost shouted at me.
Almost immediately, I pulled out, and she put her hand on her clit, and had started tense up. She wasn’t totally screaming, but wasn’t totally quiet, but after about five seconds, she shot a liquid out of her opening. The warm fluid doused my abdomen, smelling not of urine, but of her juices.
“Oh, I’m sorry, so sorry, baby!”
“Don’t worry about it.”
I gathered some of that liquid off of myself, and lapped it off of my hand.
“Hrm. Just right.” I said, with a grin on my face.
Then she surprised me. She got up on the bed, still clutching her pussy, and motioned me lay down on my back. I did so, then she got in a position where my dick was practically staring her in the face, and her pussy at mine. She then put her mouth on me, and started bobbing her head up and down. I had gone a bit softer since she shouted at me, but I soon got back to my original stiffness. I lopped and lopped her pussy, tasting her sweet, yet salty juices, drinking anything that came out. I started to tense up, my balls were tightening, and I felt myself release into her mouth. I had scared her, since even when we learned about the reproductive organs in classes, she recognized it, but she didn’t totally know how it jutted out. She picked herself up, and lied down next to me, my fluids still on her mouth and chin. We smiled.
“Are you worn out yet?”
“A little –why, what do you have in mind?” she asked
“Sit on my face.” I replied.
“Wha –what?” she questioned.
“Just do it, I’ve got an idea.”
She got her leg, and swung it over my face, and my mouth fit on her opening. I put my hands on her smooth ass, and started to rock her. I devoured her pussy to say the least. I stuck my tongue inside of her, trying to kiss her as I would kiss her mouth. She was moaning, screaming, and I was having the time of my life. I felt a jut of her juices shoot into my mouth, and she got off of my face. I quickly drank them, savoring the flavor.
“You’re so great, but now I have an idea.”
“Oh,”, I said, “and what is that?”
“I want you to stick it in my ass.”
I was speechless. “You want me to… stick it in your ass?”
“Did I stu-stu-stutter?”
I took a deep breath, trying to get myself stiff again.
“Okay, just, get on all fours.”
She dropped to the floor, and got on all fours.
I gathered up as much of our fluids as possible, and smeared it around her anus, then coated my cock in them.
“Just tell me when it’s too much, I don’t want to hurt you.”
I inserted my head in her ass, and she started breathing hard. I went in but slipped out, it was a lot tighter than I had imagined.
“Try harder, I still want it inside of me!”
Inch by inch, I invaded her. The walls of her rectum were tighter than her pussy, and I could tell that she was responsible for some of the tightness. She was screaming every inch I went in, until I was completely inside of her. I waited for acknowledgement, then started to pump slowly. It was the most pleasurable experience I had ever felt, but she started to collapse on the floor. She got up on the bed, and lifted her legs past her head, and then I saw the gape. It was incredible, but it still had the same tight look to it. I put myself back into her, and started to pump again. I grabbed her foot, and started sucking on her toes while still making love to her backside. This girl never ceases to shock me. She grabbed her own foot, and started to suck her own toes, licking them with a grin on her face. Her adorable face –she was so beautiful. The familiar tightness came back, and I released my seminal concoction within the deep confines of her ass.
We got back on the bed, and I glared into her big blue eyes. She knelt in closer to my face, and kissed me. It wasn’t a full on “fuck me” kiss, but one filled with love, one that had melted my heart. She was perfect.
“I love you so much, Jessica.”
“I love you with all my heart, Nate.” Then she got under the covers with me, and journeyed to the dreamland once more, with her in my arms.
I woke up to the bed gently shaking, and low and behold, she was pleasuring herself! She must’ve heard me wake up, and I got her attention.
“Morning, baby.” She smiled, then stuck her moist fingers into my mouth. I sucked her fingers which were coated in the same black nail polish as her toes. When my eyes opened, I saw my love staring at the doorway. I then turned my head to see her sister with her mouth open, glaring at our mess…