I was nervous, fidgeting, pacing the living room waiting for the clock to wind its way around to 6:00. That’s when my friend was coming by to pick me up for our dates. I had just turned 16 and didn’t have my license yet but Ryan did. He was using his parent’s car for the night. I was dressed for the ball because that’s exactly where we were going, to the Fall Dance at our school. I was nervous because this was my first real date with a girl. I was ready to pee my pants thinking about going to a formal dance with a girl. I’d never dated before. Sure I knew a lot of girls, I flirted and acted like a buffoon around a lot of them but to have one singled out for myself for 5 hours scared the crap out of me. I didn’t know what to expect.
About the 100th time I looked out the living room window, my sister's friend Caitlyn came into the room. “Hey, you look nice tonight. Marcie will be impressed.” Marcie was my date.
I looked at Caitlyn; my heart started tripping when I thought about Marcie. She was cute, hot, and oh so sexy. I got erections just looking at her. It took every ounce of courage to ask her to the dance in the first place and now that she said yes, I was even more anxious.
I looked at Caitlyn and answered, “I hope so, I'm so fucking fucked up in my head I don’t know what I should be doing.”
“What do you mean?” asked Caitlyn.
“How am I supposed to act? I can’t pull the shit I do when I’m with my posse, even I know that. You’re a girl, what the hell am I supposed to do with Marcie for all that time?”
“Talk to her, tell her she’s pretty and looks nice and dance with her. Compliment her dress and shoes. You do that and you’ll be just fine.”
“But what about when we take them home? What if she wants me to kiss her or something? I’m not some fucking Casanova that knows all the moves.”
“Kiss her. If she wants to neck then neck with her.”
I turned away from Caitlyn, ashamed to let her see the embarrassment rising in my face. I’d never kissed a girl, I didn’t know how or when. But Caitlyn could read me like a book, she stepped around and faced me. “You’ve never done that before have you?”
I turned again and left the room, hiding from Caitlyn and the truth.
I was sitting in my own room 10 minutes later when Caitlyn came in. “Hey, don’t be embarrassed about having virgin lips. Everybody does while they are growing up, but then everybody gets over it.”
I asked stupidly, “How?”
Caitlyn stated logically, “By kissing someone.” She came closer. “Stand up.”
I looked up at her. “Why?”
She reached for my hand and pulled me off my chair. “Because I’m going to teach you how to kiss.”
I stood up but moved away from her slightly. “You are going to teach me to kiss a girl?”
Her eyes were sparkling with mirth. “Yeah, I’ll kiss you, then you kiss me back. I’ll tell you how and you do it.”
Caitlyn is a year older than me and she’d been dating for two years so she probably knew what to do. “But you’re my sister's friend, I can’t kiss you.”
“Of course you can, I’m still a girl. You want to practice with Ryan?”
“No, I’m not a gay homo!”
That brought a smile to her lips. “Ok then, do you want to practice on Marcie, or do you want to know how to kiss her before you do? Come on, I promise you my lips aren’t poisoned.”
I stood still watching Caitlyn. She lifted her face and put her lips next to my ear, her cheek rubbing on mine, and said, “This won’t hurt.” She moved her mouth and pecked me firmly on the mouth. “See, you’re still alive.”
I wasn’t sure what I should do so she took my hands in hers and said, “When you walk her to the door, or even to the car hold her hands like this then look her in the eyes and kiss her like this. Caitlyn put her mouth over mine and moved her lips. I was staring at her while she kissed me. She pulled back and said, “Close your eyes, don’t stare at her while you are trying to seduce her.”
“I won’t be trying to seduce her.”
Caitlyn smiled again. “Of course you will and she’ll be expecting you too, that’s how it is between girls and boys. It always starts with a kiss. Close your eyes.”
I shut my lids and felt Caitlyn step closer and put her hands on my shoulders. She kissed me again, her mouth was soft and moist, I could feel the heat on my own lips. The tips of her breasts were rubbing softly on my chest. She didn’t stop, she raised her hands and held my face between them while twisting her head to the side, her mouth opened slightly, forcing mine wider open. She put more pressure on my lips then broke the kiss. My mind was reeling, my heart picked up its pace and I felt my cock lift and warm. It was the same reaction I had when I got too close to Marcie.
Caitlyn leaned back and looked into my eyes. “That’s how to kiss Marcie. Now you do that to me, take charge and kiss me like you think I’m hot and sexy.” That was ironic, I did think Caitlyn was hot and sexy, I just never told her.
I put my lips on hers quickly then retreated. Caitlyn shook her head. “No kiss me right. Imagine I’m your date and you want to fuck me then kiss me like you would her.”
I put my arms around Caitlyn and pulled her against my body and planted my lips on hers. I locked up her mouth and kissed her the same way she had shown me. Not only was I concentrating on the mouth to mouth contact, I could feel her body on mine. Her tits were mashed against my chest, our thighs were rubbing, my cock started growing. On impulse I slipped the end of my tongue into Caitlyn’s mouth which was partially open, I felt the tip of it dance lightly on the end of hers. Caitlyn jerked back and pushed me away, a startled look in her eyes. “What the hell was that, you slipped me the tongue?” She looked at my distended crotch and continued, “And you got a boner. Damn, you don’t need any more lessons tonight, you’re ready for Marcie.”
The date went well. The first time I kissed her was during the last dance. I kissed her again in the car and by the time she got home, we were necking with a fresh exciting passion and a little tongue action. My cock refused to die until I abused it later in my own bedroom.
Caitlyn quizzed me endlessly the next day about my date. I held nothing back then thanked her for showing my how to kiss a girl. She batted her long eyelashes at me and teased me with a soft lilt, “Anytime big boy. I’m always ready to help the uneducated. School is always in session.”
My next crisis was three weeks later. I was with Marcie at a carnival and we spent a lot of time on the rides, necking and holding each other. I wanted so bad to make a pass at her but I was afraid she would slap the crap out of me and dump me.
I needed more advise on the opposite sex from the opposite sex. I went to Caitlyn's house.
Her Mum let me in and I found her in her room, on her bed reading a book. “Hey Caitlyn, can I ask you something?”
She marked her page and put the book down. “What’s up?”
“How do I know when I should make a pass at Marcie?
“You want to feel her up, play with her tits and legs and stuff?”
Just hearing her say it like that started blood flowing to my prick. “Yeah, I think she wants me to but I don’t want to piss her off by being a klutz.”
“You’ve always been a klutz,” Caitlyn reminded me.
“Well, maybe, but how can I be sure she wants me to go farther than necking?”
Caitlyn grinned. “She does, I can tell you that without asking. She’s a hot girl, you’re a hot boy, she’s ready, you just have to show her that you want her.”
I sat cautiously on the edge of Caitlyn’s bed. “How do I do that?”
She asked, “Do you two ever lie down together when you neck?”
“We do on her living room sofa.”
“OK then, lie down with me and let’s pretend I’m Marcie again.”
I hesitated for a few seconds; Caitlyn poked me on the arm. “If you want to learn how to feel up a girl you can do it now or fumble around with Marcie and maybe piss her off. No girl likes a guy that fumbles.”
“You want me to feel you up?”
“Sure, why not, I told you school is always in session.” My balls felt a tickle of lust, kind of like I felt when I was holding Marcie close.
I eased onto the bed next to Caitlyn. She had me lay on my back then rested her head on my shoulder, my arm was around her body, her breasts were pressed against the side of my chest. She snuggled closer, laid her knee on my thigh then lifted her face and kissed my cheek. “Kiss me,” she said.
I turned my head and found her lips with mine. I’d been doing this with Marcie so this time I didn’t hesitate; I rolled to my side so Caitlyn and I were face to face, front to front, body touching body. My tongue sought hers and she returned the kiss with fervor. My cock lunged against the barrier of my pants. After a couple of minutes of mouth to mouth schooling we broke the kiss to catch our breath. Caitlyn looked at me with bright wide eyes. “Holy fuck, you learned a lot in just a few weeks! A kiss like that could melt an ice statue.” I didn’t know if she was aware of my hard cock pressed against her leg.
I kissed her again, quicker, softer, a caress on the lips. “We do that a lot but I want to take it to the limit. What should I do?”
“Keep doing what you just did only this time I’ll guide you a little.” I wasn’t sure what she meant but I wrapped my arms around her again and began to neck heavily with her. She reached behind her and took my right arm by the wrist and pulled it from her back, down her thigh then and across her ass. When the palm of my hand was on her butt cheek she began to move it slowly in small circles across the fabric of her pants.
Caitlyn twisted her face from mine. “Kiss my neck, just under the ear, little kisses, not one big one.” She moved her hand off mine and put it on my butt while I played with hers. I was tickling her neck with my lips and the tip of my tongue. I could smell a light perfume on her neck which heightened my awareness of her. She pulled me closer to her so that my stiff cock was pressing on the junction of her legs. I grabbed her rear and pressed her even tighter on my cock, sliding my hand lower, over her ass and between her thighs. Caitlyn flexed her hips and started rubbing her crotch on the bulge. She broke out of my arms, took a deep breath, looked into my eyes then came back for another tongue lashing kiss. She moaned softly, held her arms tight around my body, crushing my cock between us then rolled away from me, her cheeks were flushed, her eyes large and round but slightly out of focus.
She caught her breath. “Those were good moves, don’t go too fast, or too slow. Remember, if you want her hot for you, don’t’ attack her, just keep up what we just did, don’t get fast or rough.” She glanced down and the outline of my erection but she didn’t say anything about it.
“I want to feel her tits too; sometimes I just want to rip off her blouse and put my head on them and stay there forever.”
Caitlyn smiled. “At least you’re a normal guy. Every red-blooded man wants to play with a girls tits.” She nudged a little closer to me then we began to neck again. This time as our tongues danced she took my free hand and pulled it up until it covered her breast. She put her hand over mine and pressed it into the soft mound; I could feel the bump of her nipple under the clothes she was wearing. I pushed harder but she stopped the kiss. “Don’t squash it, massage it, feel it, tickle the nipple with your fingers.” She buried her face against my neck and started to suck a hickey under my ear.
I pulled away from her. “Don’t make a mark on me! I have to go out with Marcie tonight.”
Caitlyn blushed. “I’m sorry, I just wanted to let you know I like it when I get felt up.”
I needed to take a break. Caitlyn was not only teaching me how to feel her up, she was seriously turning me on. My balls were aching; my erection felt like it was splitting from the internal pressure. We rested quietly, I didn’t want to leave her room and she wasn’t trying to get rid of me. Caitlyn put her head back on my shoulder; I put my arm around her again.
We stayed like that for a few minutes, each of us thinking private thoughts. My cock refused to shrink. Finally I decided to find out how much Caitlyn would teach me so I reached over and began to unbutton her blouse. She looked down at my fingers as I opened the first two buttons then lifted her head, smiled and kissed me lightly. She put her head back down and let me finish undoing the buttons. When the blouse was open I pulled it apart, exposing her bra. She had on a bra that hooked in the front, between the cups. Caitlyn twisted the clasp with two fingers and let it fall apart. I moved her hand then covered her left tit; I felt the nipple grow hard on my palm. She relaxed to her back and I rose up on an elbow and looked at her body. Her breasts were standing proud from her chest, the nipples stood firmly from the puckered brown skin at the peak of the soft mounds. Caitlyn put a hand on the back of my neck and pulled my head down until my mouth was over a nipple. I hear her gasp when I kissed the end of it.
For the next few minutes Caitlyn’s breasts were the focus of my life. She managed to tell me how to kiss, suckle and lick her breasts and nipples. While I was busy with that part of her my hand migrated down her body until I slipped it between her legs. Caitlyn arched her back and kicked her legs apart, giving me more room to feel her crotch. She was hot and damp between the legs; I could feel the crack of her body under her pants. Her legs were moving restlessly as I stroked between them. Caitlyn moaned then struggled to move away from me.
I flopped back down beside her; she grabbed a pillow and covered her chest. “You learn fast,” she panted, “I think Marcie will like what you can do for her”.
I had been running on hormones and adrenaline for over an hour. My nuts ached, I was hot and tired. I closed my eyes to rest them. When Caitlyn saw that I was relaxed again, she settled down beside me. I drifted into a nap.
I came awake slowly. A glance at the clock told me I’d been out about 20 minutes. I didn’t look at Caitlyn, I didn’t let her know she woke me up by fingering my erection lightly and I didn’t want her to stop. I kept quiet and still but I could feel my nuts filling with even more lust, my cock twitched each time she ran a finger tip down the length of it. My jeans were tight and my erection hurt like hell but I wasn’t about to move.
Caitlyn tired of stroking the denim over my hard-on so she opened my belt. She twisted the button with her thumb and finger and opened it. Next was the zipper, she pinched the pull then slowly eased it down to the stop, even though it was still in my shorts, my cock expanded into the free space. Caitlyn slipped her fingers under the waist band of my briefs and felt the end of my hard-on. It was getting very hard to ignore her, to pretend I was still sleeping. She pushed her hand completely into my underwear and gripped my erection then began to pump it gently. She lifted her head and whispered into my ear, “I know you’re awake, it’s time for another lesson, kiss me, play with my body.”
I opened my eyes and looked into hers. They were burning, flashing sparks and fire in my direction. I’d seen Marcie’s eyes like that and now I understood what it meant. I broke out of her embrace and got off the bed. She looked at me puzzled, wondering what I was doing. I stripped off my shirt, dropped my pants then got back on the bed naked. Caitlyn watched me carefully; her eyes traveled over my body then settled my cock which was, solid, long, and rising at a slight upward angle from my pubic hair. She sat up and took her clothes off.
I fell into her arms and we began to neck. I was touching and caressing any part of her I could reach, she was stroking my cock and balls while she licked and kissed my body. My heart was hammering a drum tattoo in my chest, my skin burned everywhere she touched me. She ended up on her back breathing heavily. She stretched her arms over her head then straightened her legs and body taut. “Look at me,” she said, “this is how Marcie is going to look to you later.” My head was going to bust from the pressure of my pulse, I was close to firing my load all over Caitlyn’s prone form.
Caitlyn held her arms up and asked, “What are you going to do if you get her like this?” I could only shake my head and stare at her breathtaking body. She spread her legs apart then invited me, “Get over me, I’ll show you what you are going to do.”
I crawled over her and got to my knees between her legs. My erection was leaking drops of clear fluid onto her. Caitlyn grabbed my arms and pulled me down; my cock was crushed into her pubic hair. She reached between us and grabbed the shaft and bent it down and slid the end of it along her slit. When she had me in the right place she moved her hand and thrust her hips up, my cock slipped into the hot wet tunnel between her thighs.
Caitlyn was impaled on my erection. She began to hump her ass and I started pushing in and out of her. She was smiling at me, her eyes watching mine. I leaned down for a kiss and got a long hot tongue probing my mouth, searching for mine. I’d never felt anything like what I was doing. I dimly realized that she had just taken my virginity and I was thanking the lords for letting her do it.
My sex lesson was over long before I wanted it to be. Caitlyn and I had been necking, petting and turning each other on for almost two hours and my balls couldn’t handle the stress. My orgasm started in my nuts and blew out the end of my cock, filling Caitlyn with shot after shot of boiling cum. I was hammering her cunt while she bucked under me. Never in my life had I ever felt anything as incredible as ejaculating into Caitlyn that first time. She wrapped her arms and legs around me and held me tight as my nuts emptied into her.
We fell apart to cool off. Gradually we started talking again. She asked me, “Do you think you can handle Marcie now?” I wasn’t ready to answer that question so I fended it off with one of my own.
I asked her the question every boy asks after his first piece, “Did you like what we did? Was it ok?”
“I didn’t get off if that’s what you mean, but that doesn’t’ matter right now, you did. Now if you fuck Marcie tonight you will be ready and can last longer.” I told her I felt guilty about leaving her hot and horny but she shrugged it off. “That just means that my boyfriend is really going to enjoy himself tonight. I’m going to use him until I get what I want.”
“But what if I get Marcie to bed and can’t do it right with her. How will I know if she enjoys me?”
“Tell you what Justin, tomorrow you tell me exactly what you did with Marcie and I will teach you how to bring a girl to an orgasm.” She reached for my cock and pulled on it lightly. “You need some more lessons and I know you’ll like your homework assignments.”
I pushed her to her back. “I’ve still got an hour before I get ready.” I put my lips on her neck and slipped my fingers between her legs.
Caitlyn sighed deeply them murmured, “I’ve got a feeling you are going to be a star pupil.
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