Introduction:
Jen gets me to ask Katey out.
By EFon
Chapter 3 : She set me up for my first time.
I woke up to my mom calling me at my door to get up for school. I woke and wondered if yesterday was real or a dream. Oh shit! Why hadn’t I thought about it earlier? Two nights ago I thought I had dreamed getting my first blowjob in the night by a mysterious girl, but only my mom and sister were home so I chalked it up to a wet dream. But with my waking of listening to Jen fingering herself with my name upon her lips it was all crystal clear now.
It was my sister Jen who had suddenly sucked my cock that night. That was why she was acting so weird yesterday, being all nice with giving me a ride to school and making me dinner. But why? Did she fall head over heels in love with me suddenly? She didn’t know I’d read her diary or overhear her masturbating, so this couldn’t be a ploy or joke on me. Could she really have fallen in love with me when she saw my morning wood?
I’d have to tread carefully. Sure, it was my sister, and I loved her, but not that way. That’s just gross. Besides, she’d been a bitch to me for the years and now, suddenly I have a cock bigger than her current boyfriend so now she wants me? They always say everywhere that size doesn’t matter, but maybe that’s all just a lie? Does size really matter that much? I looked at my morning wood and realized I’d better stop daydreaming and get dressed quick for school.
When I went out to breakfast I saw Jen on her knees in front of her door. I was about to ask what she was doing but then I suddenly knew. She had a wet rag and was cleaning up a little white crusty stain in front of her door. Her eyes locked with mine and for a moment we didn’t speak, move, or even breathe for a climactic and brutal second. Then she casually said, “Can you plug the nightlight back in the wall?” Then she got up and walked into the kitchen.
There is was. I’d forgotten to plug the light back in last night and even must have left some evidence of my incestuous voyeurism at the scene of my peeping last night. I plugged in the little light back into the wall socket and thought about where we were now. I knew she knew now, but she had said nothing. So now what? Did she want more from me? Hey, I wanted to lose my virginity as much as the next guy, but she was my sister. As long as it was just my sketch, or in the dark, sure, but there was no way I was going to start dating my own sister. That’s just gross, and I’d probably get us thrown in jail or something. Maybe I could just play it cool.
I joined her and mom at the kitchen table for breakfast. Mom looked exhausted having gotten home late last night and was already headed back out to work. Being a nurse is a tough job and she always seemed to be out working to put food on our table. I poured myself some cereal and ate in silence while Jen was assuring mom that last night had been fine. She issued us our chores to do when we came back from school today before we goofed off for the weekend since today was the end of the week, then took off for work.
Without Mom, Jen and I sat in silence for a moment. I finally looked nervously at Jen who picked up a banana and peeled it without a glance my way and then dipped in straight into her glass of milk. I’d never seen anyone do this before and was about to ask her what she was doing, but then she took it out while dripping a few drops of milk on her shirt, right on top of her breasts, while she sucked the milk off the banana by sliding it into her mouth. Then she wiped the milk from her bosom and ate the banana for real.
God I was hard, and I had to stop looking at her as I ate and tried to think of something else. I knew I had to say something, so I thought of something to say. “So, I think that Katey likes me.”
Jen swallowed her banana bit and said, “Yup, she does. I’m surprised you even noticed. She’s been hitting on you for almost a year, but you’ve never even looked at her twice.”
“Really? A year?” That’s freaking awesome! How could I have missed that? I cleared my throat and tried to remain composed, “Well, do you think that you could, maybe…” I didn’t know what to ask for. I’ve never been on a date before. How did one do this right?
Luckily Jen stepped in to assist, “Ask her to go out with you?”
I was sweating in my shoes just sitting at the breakfast table thinking about that cute red-head who was a year older than me going out with me. Kissing me and being my girlfriend in school. “Er… Um… Yea.”
“Sure little brother,” she suddenly said happily, “what else are big sisters for?” I wasn’t sure if she was being facetious or honest, but she grabbed her bag and said, “Get your stuff and let’s head to school.” I grabbed by bag of schoolbooks, adjusted my stiffy in my pants behind her back and ran to catch up and we got in her car and we went to pick up Lisa and Katey.
Like always, I was sitting in the back and it would only a few minutes for us to get to Lisa’s house to pick her friends up, but unlike usual Jen started talking to me instead of turning on her music. “So, what do you know about Katey?”
“Um…” Man, I didn’t really know anything. I’d known her for a year as Jen’s friend and seen her several times a week, but never really paid attention to her since she was a friend of Jen’s. “Not much I guess,” I said with a shrug.
Jen shook her head and started talking. I knew they were both on the cheer squad, but didn’t remember that until she’d said it. Then I learned about Katey likes and dislikes. I instantly started commenting them to memory. Likes running, cheerleading, and volleyball, but actually is bored by the basketball and football she cheers for. She absolutely loves having camping trips and barbeques every summer. Her favorite treats are strawberries and chocolate, but hates anything hot and spicy. She cannot resist romantic comedies but hates horror, and likes to sneak peeks at her father’s porn movies. Her favorite colors are red like her hair and green like her eyes. She has pet dogs and loves to ride horses when she went on vacation last summer.
It was all so much I barely had any idea how I was going to remember it all, but I still went blank as we pulled in front of Lisa’s house and Lisa and Katey jumped into the car. I was glad summer was coming soon because the warm weather meant Katey wore a tight low-cut green shirt and skimpy skirt that showed off her ample breasts and long legs like she was showing off for him alone. After what I had read in Jen’s diary yesterday I figure she just might be. She still greeted me with a smile and the standard, “Heya Russ.”
Today I knew what I had to do. Man up. “Hi Katey. I really like that shirt. It matches your eyes.” I’d never realized she’d had green eyes of course until Jen had told me, but now I couldn’t look at anything else. Even her cleavage was secondary to those piercing green eyes that looked like they stared straight into my soul.
She blushed and giggled instead of answering, and Lisa turned and jibed at me, “Listen to this little snottling thinking he’s a Casanova.” Suddenly Jen gave Lisa a discrete bump with her hand and, while I couldn’t see it, I could tell she was giving Lisa the stink-eye. Lisa gave her and me a confused look, then just turned around and turned on the radio.
I returned my attention to the lovely older woman next to me and whispered to her, “I… I want to ask you something.”
She responded in hushed tones getting close to me so our shoulders touched, “Okay.”
“Well… I was going to see this new movie coming out, but it’s a romantic comedy and my friend didn’t want to see it, but I hat going to the movies alone, so I was kind of hoping, I mean, if you’re not busy tonight, that you might maybe…” I was fumbling and I knew it, but couldn’t stop myself from doing it.
Luckily she cut me off with, “I’d love too.” Then she took my hand in hers and held it with a little squeeze.
Boom! My mind was blown and I was on cloud nine. I had a real honest-to-God date with a girl! “Oh! Er… great! So, I’ll meet you there at six thirty?”
I was surprised when suddenly Jen spoke up and said loudly, obviously addressing us, “I’ll give you a lift tonight Russ.” I looked up and saw her peeking at us in her rearview mirror, and couldn’t tell exactly because I could only see her yes, but I think she was smiling.
When we got to school I had to let go of Katey’s hand with regret. I said “See you tonight then,” with a smile and as I turned away, I could see Jen was indeed smiling, but Lisa was definitely unhappy. I headed off to class happy beyond my wildest dreams. I was glad to finally be able to talk about it with a friend. “Dude!” I almost yelled at Jake, “I got a date tonight?”
“Wow, really?” he sounded a little unbelieving and I didn’t really blame him, “With who?”
“Katey… Um… I don’t know her last name,” now I sounded stupid, “Jen and Lisa’s friend, the red-head. She’s a junior.”
He nodded, but I’m not sure he really knew her. When we got to his house we were surprised by little sister Jackie who offered us cookies, “I made them in Home Economics! Try one, there yummy!” Not to be one to pass up cookies we dug in. They were good and I told her so. She smiled and I remembered what Jake had said yesterday; Jackie had a crush on me.
Sure she was young, and still had braces on, and glasses too, and at only thirteen hadn’t yet developed any breasts to speak of, but she wasn’t bad looking. I’d almost have considered asking her on a date if I didn’t already have a real fully developed and curvaceous sixteen-year-old woman, lined up for tonight. I again thanked her for the cookies and Jake and I headed to his room to check the movie times. I didn’t even know what was playing, but it didn’t matter. There’s always a romantic comedy playing, and while I go to see them in the theater, I’d enjoyed them when I watched them on TV, so whatever it was would be good enough.
I didn’t really do any of my homework, mostly joked with Jake until I heard the horn for my ride. It was my mom this time, and boy was she tired. I knew she’d have the next two days off, like she’s supposed to have after a double shift, but my mom could never say no to people in need and the sizable overtime check. She asked me my plans tonight and I told her I was going to the movies with Jen and she said, “Good. I’m glad you two are getting along again.” I still didn’t know what was going on, but I didn’t want to spoil it, whatever it was.
Jen cornered me when we got home and handed me a bag with some bottles in it. “Go shower and use the body wash in the bag. Make sure to wash EVERYWHERE really well, and then spray just twice with the cologne. I’ll pick some clothes out for you and put them on your bed.”
I looked at her confused and she turned me and swatted my ass hard with her hand. Ouch! I hurried into the bathroom and looked in the bag. Strawberry body wash? And Avalanche cologne? Ok… So I showered and scrubbed my body with the gritty strawberry gel, and it felt weird, but smelled good. When I got out and dried off I sprayed myself twice with the cologne. Man does that stuff stink, but if girls like it fine. I wrapped a towel around my hips and went to my bedroom and there were some of my clothes lying on the bed. Just a button up red plaid shirt and trousers, but I was totally trusting my sister’s judgment on this one. I dressed and went downstairs.
“Looking sharp little brother…” my sister smiled and pinched my cheek. How did she suddenly become my best friend? Mom was so tired from working three shifts in two days so she went to bed early and Jen and I just grabbed a quick bite to eat before we headed out. We stopped by the flower store and picked up some marigolds, Katey’s favorite flower, and a packet of seeds for them.
“What are the seeds for?” I asked Jen, who paid for the whole thing.
She smiled brightly and explained, “This way she sees your think of not just tonight, but the future.”
“Oh…” I said understanding, then a second later, “Oh!” as I realized she meant I might have a serious future with Katey. To be honest I was just looking at tonight, and not my entire life. Could I visualize getting married already? Suddenly my head was swimming with thoughts of a job and babies and a house, all with a perky Katey next to me. It sounded great to me, but I knew I had to be over thinking this. I didn’t even really know her.
Then we were at her house. It was still light out and we sat there for a moment before Jen jabbed me in the ribs, “Go ring the doorbell slowpoke.” Right. I carried the flowers and seeds packet to the front door and pressed the doorbell. Then it opened.
Katey stood before me in a cute short green frilly dress that only went down to her mid thigh. Then she was naked all the way down those lovely legs that ended with some bright red heels. Her hair was all curled and bouncy framing her freckled face and beaming green eyes. I was at a loss of what to say, but she took care of that, “Oh Russ, I love Red Marigolds!” and scooped the flowers out of my hands.
I limply added, “And this is seed for it… for the future.” It sounded really stupid, but she just smiled and took the packet from my hand while she kissed me on the cheek. She disappeared for a moment, leaving me at her empty open door, and then she appeared again, obviously having put the flowers away, and closed the door behind her as she put her arm in mine and we walked to Jen’s car and both got in the back seat together like we always had. She hugged my arm and I barely registered that we were driving. All I could think of was her breasts rubbing against my shoulder. Then we were at the theater.
Jen said, “Call me when you are out and I’ll come pick you up,” and then drove off leaving me alone with Katey. Sure there was a small crowd of people going into the theater, but they were almost immaterial to me. We stood in line, just smiling at each other; I was too happy and nervous to talk. Then I bought the tickets and soon we were in the dim theater, sitting near the back of the half-full theater, with the lights dimming and the movie starting, and still holding hands with this beauty.
The next ninety minutes were actually fun. The movie was funny and we were both laughing through most of it, and I got turned on a few times by some of the steaming sexual references, then there was the climactic kiss. Only an idiot couldn’t see it coming, and I turned to Katey who had glassy wet eyes and as the couple on screen kissed, so did we. My first time kissing a girl and it was great. Her l warm, soft, and wet, and they parted around mine and it was wonderful.
I don’t even know how the movie ended, because we were too busy kissing to notice until the house lights came up and I nervously pulled away. She smiled as we stood and left the theater, arm in arm. “So…Um… Now what do you want to do?”
Katey smiled and softly, “We could go for a walk if you want.” I nodded and we walking into the park nearby. It was already after sunset and getting dark quickly, but I was ready to do anything to be with this angel even another minute longer. The town we live in is kind of small, and the park doesn’t have any lights, and technically closes after sunset, but we walked across the groomed field toward the wooded nature trails by the little trickle of a stream that fed the fishing pond there. Once we were in the woods it got really dark, but I’d been bike riding here enough to know my way around. Then we came to an opening by the brook lit by the moon high and bright in the clear sky, about a quarter before it was full, and I could see her clearly again.
Then our lips meet again and a lifetime passed within her wet lips and warm bosom pressing against my chest. My hands embraced her and caressed her smooth back through the dress that seemed a lot thinner than it looked. Then my hands instinctively reached her hips and cupped her tight ass against my raging boner. She broke our kiss and giggled, “Oh… Someone else wants a kiss?” then descended down by body.
I was paralyzed as she undid the button and zipper of my trousers. Was this really happening? Then her soft hands rubbed my shaft through my underwear a few timed before she pushed my rigid manhood through the folds of my underwear. I’d never really done that before since it was uncomfortable, but I was in heaven as she was now touching and kissing my bare penis flesh. She kissed the side, then the head, then the tip. I was tingling with anticipation as I watched her with riveted unblinking eyes.
Then she looked up and licked the underside of my shaft from the base to the tip. “Mmmm… Tastes like strawberries.” I wanted to thank Jen more than ever before, but she licked it again as said, “I LOVE strawberries,” just before popping my cockhead between her slippery ruby lips and sucking most of it into her mouth. It felt just like I remembered it from the first time I experienced it a few days ago. It was a little different in tempo and technique, but was terrific and I felt like I was flying over the moon. She slowly bobbed her head up and down and I groaned with desire. My hands reached down and caressed her hair as she worked her sucking mouth over me and I was so excited I accidentally pulled her head down onto my shaft, forcing me into her throat, and she suddenly forcefully pulled away coughing.
“Oh Jeez! I’m sorry Katey!” I pleaded with her and hoped she wasn’t mad at me, “I just… I’ve never… well…”
She looked back up at me after catching her breath. “It’s okay. It’s just that I’ve not had a guy as big as you before.” I blushed with pride and that ego boost made my cock throb even bigger. She then pulled my hand and I knelt on the grass with her and we kissed again. Not as lustily as before, but slowly and romantically, despite my raging boner that wanted me to jump her there and then.
Then she put her hand on my shoulder and pulled me close as she leaned back and I slid to lie on the grass beside her and she whispered, “I’m not a virgin, so you don’t need to be gentle with me.”
Oh My GOD! She wanted me! I was going to have SEX! This was awesome! CRAP! “Um… I don’t have any condoms… I didn’t think…”
She placed her finger on my lips and said, “Its okay,” and she pulled up her short dress and spread her legs. In the pale moonlight I couldn’t tell colors well, but she did have some curls on her pubic mound and I moved my hands over her legs and belly, then watched her to make sure it was really okay, moved over those curls and touched the first pussy I’d ever touched since I was born. The tangles of her hair were smooth and soft, and below that was her slit, wet and sticky.
I poked and rubbed it with my untrained fingers, then she grabbed my hand and placed my fingers at a little bump at the top and she giggled as I rubbed her there. “Make small circles around that,” she whispered her instructions and I did as she asked. In moments her giggles turned to moans. Suddenly she pulled down one side of her dress and her boob closest to me came into the moonlight. “Oh… please suck my boobie… Oh…”
I didn’t need to be asked twice. I nearly launched myself at her and she shrieked with a giggle. “Take it easy! Take your time and don’t use your teeth.” I licked at her pointed nipple on the mound of soft flesh and continued to rub her nub that I figure must have been her clit. Then I traced my tongue on the bumpy flesh around the nipple until finally I pursed the tip between my lips and sucked on it.
Soon her moans became orgasmic shrieks. She startled me with her loud sounds of pleasure, but it also really turned me on knowing I was doing a good job. Then she grabbed my hand that was diddling her twat and said in a husky breathless voice, “I need you inside of me.”
I moved like lightning and knelt between her splayed thighs and bent over her, holding myself up with one hand and grasping my shaft with the other. It was dark, and having never done it before was unsure of exactly where to aim. I poked forward a few times obviously missed the right spot as I couldn’t push in. “Lower,” Katey said. I went lower and poked again, “A little to the right.” Again, I tried and suddenly instead of firm flesh I pressed against a smooth wet glove that immediately enveloped me as I slid in and moaned as I was in euphoric bliss. “Ahhh… bull’s-eye,” she giggled.
I moved gently against the tight flesh of her vagina, the first one I’d ever been in before and it was amazing. The sensations were terrific; so hot and wet and tight. Then she said, “You don’t need to be gentle, and wrapped her flexible legs around my hips. “Fuck me hard,” she almost grunted harshly as she thrust her pelvis up to mine. After that I lost any control I had; I started rocking on my knees, banging into her hard and fast, and felt like she was clinging onto me for dear life now through her screams and shouts.
Suddenly everything went white and I knew I was coming. I thought I should say something or try and pull out, but her grip on me was too tight and suddenly I became a rigid as a post and my cock began squirting my sperm, over and over again, like a machine gun into her quim. I groaned while she shrieked and when it was over I collapsed on top of her quivering body with my shrinking member still leaking little twitches of my cum into her overfilled love canal.
Soon my flaccid and used penis flopped wetly against her but as it withdrew from her on its own and she released me from her leg wrap. I rolled onto the grass beside her and closed my eyes in peaceful and exhausted bliss. She placed her head on my shoulder and asked, “Was it everything you hoped for?”
I opened my eyes and kissed her forehead, “And more…”
We relaxed for a bit until the dark night air started to finally chill us. I called Jen and asked her to pick us up at the park entrance, and she said, “I was wondering if you were ever going to call.” After I hung up I noticed the time on my cell phone. The movie had ended almost two hours ago. I asked Katey if she was going to get in trouble, but she didn’t seem to think so. We walked back to the park entrance and only waited a few minutes before Jen showed up.
We climbed in, still snuggling against each other and Jen smiled and drove us to Katey’s place. When we got there we got out and I walked Katey to her door. It wasn’t until then, by her porch light that I could see her properly since we left the theater. Her hair was mussed up, and her dress was wrinkled, and her shoes were a little muddy, but she still looked beautiful. We kissed again and I asked if I could see her again. “You’d better…” she whispered, then was gone inside her home.
I was so happy I’m not sure I touched the ground once on my way back to the car. I got in the front passage seat with a broad grin on my face and Jen smiled back at me as we drove home. “I take it the date went well?”
“Yea…” I sighed with contentment.
Via: https://sexstories.com/story/39330/milk_of_desire_chapter_3_she_set_me_up_for_my_first_time.