Jean's Diary: First Time

Dear Diary, I need somewhere to record so here I go. I'll have to introduce myself. I want you to picture me here. Say you're reading this in some post apocalyptic society. I want you to picture me. But I can only be counted on a little to help you. I'm no good at describing myself but I'll do what I can.

May, 4, 1989:

So there I am on my bed in the front room of the house. The more comfortable I became with myself, the less clothing I wore when alone. Here I'm doing homework in cotton string bikinis and a cut off tee. I know how lucky I am, considering I wasn't born into the right body to begin with. I was graced with beautiful curves already as a boy, and after years of hormone replacement, I have to admit I couldn't have asked for this body. I'm happy with my little breasts, and With all modesty, almost no one has a better butt.

I was lucky to know early. My supportive parents helped me research, and I wound up starting hormone replacement early through my mother's connections. Everything is great with me except my own fear of getting out there and making it happen. I'm talking about sex. I'm nineteen years old. I live at home, and attend the local college, and I'm a virgin. I don't just mean I haven't gone all the way. I haven't touched anyone yet and none have touched me. I have always had an unreasonable fear of contact. It has worn thinner over time due to my transition. Inertia, however, has kept me standing still. So I still haven't gotten there even though I'm ready (and aching).

May 5th, 1989:

I actually don't want to share. I may edit what I've written to give you the picture of me with less information. You don't need to know exactly how old I am, when I knew, or how long I've been on hormones, blah, blah, blah, etc. All of that is very important but, I'm sorry-it's not for you.

What I want to talk about here is sex, so I thought I had to give you some background on how I came to be, and where I was in my life. I want to tell you about what I dream of doing, and hopefully, eventually, some actual news. I'm sure I'll tell more than that, but that is my guideline.

So what else? I was attracted to girls before hormone replacement therapy. My first attractions were women. guys have taken over gradually to the point where women are an afterthought, except as objects of envy. I'm just dying, and I mean dying, to perform oral sex. As I grew more attracted to guys this oral fixation grew out of proportion. I mean, I seriously want to get fucked. (I'm too nervous to even share my dreams of someone fucking me-they are nuclear). But-well, first of all I want to save that. Plus I feel I could wait if I had some handsome cocks to play with and make orgasm. I'm dying to be the reason someone aches so that I can quench that ache.

May 6th 1989

I'm desperate for a guy. Any reasonably decent looking guy could have me just by making an advance, making me feel safe and promising discretion. Such has my hunger overflowed. I'm cool personified in my daily life, but I'm groaning inside for attention. All day long I pass coolly by guys who's cocks I want to suck.

What I'm talking about is on a daily basis. Every night before sleep I rub myself while I picture one of the boys getting excited while I do it. I picture it happening in the stairwell, or in the locker after school. I'm always in a skirt and blouse. The guy is in a towel after showering. I sit on the thin bench between the lockers and stop him as he passes. I look into his eyes while relieving him of the towel. My eyes lower, watching him begin to grow before my hand even reaches him. I pull him to me.

This fantasy never gets very far. Once he's in my mouth I have to make him orgasm quickly to match my own excitement. The thought of his reaction makes me weak. I see his face contorting. I feel my insides turn warm and liquid like what my mouth is waiting for. Then I'm over the edge. I can't hold back now so I imagine him sighing, "aah," and telling me he's cumming. And then it starts. He gasps, and begins jetting into me. I'm swallowing his goodness. In my bed with eyes closed tight imagining this, I melt, moan, and explode, squirting all over my chest, face and belly, breathing heavily through my nose as I swallow in my mind.

I feel nice as I lie there afterwards, my right index and middle finger still resting on my clit. My left hand might be twirling my long blonde hair, or resting on my glistening breasts when I come back to myself. Whatever I'm doing I begin to plot making the dream reality. That's what I'm doing as I fall asleep.

May 7th 1989

So I have some exciting news. Really a couple of days of news. I'm so trying to stay calm. I have monumental news. Not just big news, like extraterrestrial contact. I'm talking male contact. I don't expect you to believe me but that's okay. I don't believe it either. Okay, so here goes. I'm in my room reliving as I write. Wow! I was walking home after school. It's usually the three of us; Lisa, Helen and me but I'm alone on Avenue Z and down my own block. So I turned the corner onto my block, and heard, "Hi Jean." I stopped, waiting for Michael to cross."How's it going?"

"Hi," I said looking him in the eye as he drew close. He dropped his gaze, and when he lifted it again his shy, slight smile went right through me. He likes you. I had noticed he had begun looking at me differently, and he went out of his way to greet me one time. In our lives he had never approached me privately like this. We just said hi to each other, you know? And since he was real cute I had sucked him off in my head, dozens of times.

He wasn't one of the popular guys. He wasn't great at sports, and he kept to his few friends. He didn't do anything to stand out. But if you asked the girls in school, after they named all the obvious guys, eventually they would say, "Oh yeah, and that other guy, he's cute." He had a serious look; smart eyes, nice eyebrows, kind of a big nose and a nice grill. He was average build.

I should probably explain. I do get some lewd propositions when I'm walking alone. No one asks me out though. I need a nice boy who won't embarrass or hurt me. Someone just like Michael, who has lived across the street my entire life. Who I played with as a boy, though we had separate groups since grade-school. This was a nice boy who would never hurt me. If he thought I was cute now, he was going to get some loving. This was great. I hadn't hoped for someone like Michael. We began walking down the block. How to do this?

"Are you going out with anybody?"

Okay, there's the sledgehammer approach.

"Aah no," he said. We looked sidelong at each other as we walked slowly. Each passing second without looking away, silent dialog between us. Me: I'm looking for a guy. Him: Well i like you. Me: Really? Him: I think you're beautiful. Me: Beautiful? Him: Fifteenth hottest girl in college, both grades. Me: I'll do absolutely any reasonable thing you desire, as many times as you want.

"Would you be interested in someone to fool around with on the quiet while you're single?" We still haven't broken eye-contact. Michael blinked twice before going wide-eyed. Neither of us can believe what I have just asked. Thus the agonizing, eternal, 2.3 second delay before he nods and says, "Yeah,if it was you."

I nod, stunned. "Go around the back and I'll let you in." I walked faster, leaving him behind. My parents wouldn't be home before six. I let myself in the front door.

I was shaking with nerves between the front door and the back. I took two deep breaths before opening the back door. Michael stood with crossed arms. I gestured him in and closed the door behind him. We faced each other in the small vestibule. His back was to the door. Behind me, four stairs up to the kitchen, to my right nine stairs down to the basement. I held his eyes, not knowing how to proceed.

"Can I suck your dick?" I was just full of subtlety. You're probably embarrassed for me but I wasn't somehow. I just didn't know what else to do. He nodded. "I want to shower first."

I considered. I felt I was in control. Nervous but in control.

"Will you take long to come?" He shook his head, "No."

"Take your pants down." I couldn't wait to even get further in the house. I watched his jeans come down. I knelt and pulled down his shorts. His erection sprang out. He was a nice decent size and handsome. He looked absolutely awesome. He had a good bush of brown pubic hair, and nice size balls. I didn't pause, pushing his back against the door, I took his length into my mouth.

Wow! Having him in my mouth...first the feel and taste of him made me drunk like I had been waiting a lifetime (I had). I moaned, breathing heavy through my nose like I was cumming while I sucked him into my mouth. Then I smelled him too. A thrill surged through me. The reality of what was happening reinforced. His light sweat smelled so nice. I started aching for his cum in my mouth.

He was beautiful to suck. I continued moaning while I sucked him. My body telling him how amazing it was to be doing this. My hands were on his hips as I sucked him in and out with only my mouth. I brought one of my hands under and gently squeezed his balls. He gasped. I tickled his balls and he shuddered. I started sucking him so gently down his shaft, then wrapping my tongue around him.

At that he said, "Oh I'm cumming." The sound of his voice was like a a surprised urgent warning. I slid him all the way in my mouth and he shot so hard into my throat, gagging me. I, coughed, got my breath back, took him back in my mouth and swallowed, sucked and swallowed. Michael moaned and kept blasting but I had it now. "um, um, um, um, um."

The most glorious thing ever, to swallow him. I just couldn't believe what was happening to me. I kept sucking gently after he finished, continuing to praise him with my quiet moans. He was getting soft when I released him. My clit was swollen. I was dying to come. I was so hot from what I had done. I looked up at Michael, Nervous. He smiled softly, gently stroking my hair and face. I felt safe. He saw my skirt.

"Can I do something for you?"

I thought quickly. We didn't have time to talk all about it.

"Come on," I said zippering his jeans.

Upstairs I stripped. Michael couldn't have behaved better. I was dying to cum, and he could have ruined it a bunch of ways. He talked to me from across the room, giving me space while I peeled my clothes off.

"God, you're beautiful," he said. "You're body's awesome; such cute breasts, wow, and you got the nicest butt." (I told you).

That's all I needed. I felt his words could make me cum. I lay down on my back and signaled him. "Kneel here." Michael came, and knelt. I reached for his hand. He gave it to me but his left hand went to my face. He caressed me, then leaned to kiss me. I wanted to badly but was afraid to get too...personal or emotional. I know you're laughing at me. I had just sucked his dick and swallowed his come. How much more personal is a kiss? I can't explain my fear, but it involved having my heart shattered.

He must have seen my look but he gently touched his lips to mine and I let him kiss me. He was gentle but passionate. I was becoming delirious. I pulled away and brought his fingers to my clit. He knelt back down.

I took two of his fingers and made him rub just so, just here. I was already boiling. I thought I would have to move his fingers to effectively stimulate me to orgasm, but I was so hot, and I realized what a thrill it would be. I let go of his hand, lifting both of mine to my face. He rubbed.

With closed eyes, hoping I looked good to him, I let myself go. I writhed, resting a hand on his shoulder, moving against his fingers, whimpering as I was both dying to climax, and wishing this would go on for all eternity. I had had no hope of doing this so soon. It was too much. "Oh my God, I'm cumming already."

Michael brushed my nipple with his left hand, sending an electric charge through me while he rubbed my clit steadily, relentlessly. It kept building until my body clenched at last.

I called out. "Oh Michael, oh yes baby..." On and on I called to him and squirted, rubbing against his fingers; there, there, there, there, there, there, there. It was exquisite to be made to cum. He kept rubbing me gently. I was blown away. I wanted to cry and laugh out loud, I was so happy. I shyly looked over at Michael, the first person to touch me. This was the first anyone had...seen me.

"Whew," he whistled. "You're beautiful."

I lolled my head to look better at him. "You liked doing that?"

He moved his fingers a little. "Yes. It was awesome. It feels perfect. I get it. I know why I want you so bad. You're just a beautiful girl."

Did he just say that? We both nodded. "Thanks," I said.

I had been a little terrified about all this, and the first boy was perfect, got it, and liked me for the right reasons. Still I knew I wasn't in love. I winked at Michael.

"I'm not looking for love, Michael, but i'd love to fool around whenever we can."

He looked funny for a second. "I mean it," I said, "I only want sex."

He laughed. "I'm down for fooling around, but I..."

I smiled back. "I'm serious though. No strings attached."

He nodded, "Really?"

I nodded. "Okay. Can I shower?"

"Down the hall."

Diary, I have more to tell you but I have to get to sleep. I'll catch you up tomorrow. Believe me or don't believe me. I don't care. I don't believe it myself anyway. This was the best day of my life. I feel like I'm dreaming.

May 10th 1989

So I stopped last night with Michael going to the shower after touching me to a heavenly orgasm. I cleaned up my body and the room, before heading for the shower. I climbed in while he was was drying. I was out in a minute, toweling off. Michael watched me.

"See how you touched me?"

He nodded. "Understand how I don't want to be touched?"

"Yes. Can I do more with you?"

"I won't go all the way. I'm Saving that. I want to do...a lot else."

He nodded again. "I want to touch you everywhere. I want to fuck you of course. Everyone wants to fuck you."

My head swung around. "What?"

Michael smiled. "You must feel everyone's eyes follow you everywhere you go."

I didn't. He had just made my life. "Get out," I laughed. I must have blushed. "Say that again?"

He laughed. "I've heard lots of guys talk about wanting to fuck you. Oh yeah. I've heard oodles."

I couldn't help but smile. Michael did also. I didn't mind that he got a view of my insecurity. Maybe what we did together would mean more to him if he knew what his attentions meant to me.

"You know," I said, "The way you touched me made me feel...real good." I wanted to say more but I couldn't find it. He saw.

"You're a beautiful girl. Who wouldn't want to make you come?"

I smiled just for him. "Hey, you know I don't want romance, but...could I kiss you for that?"

"You can kiss me anytime."

I turned my back to drape my towel, thinking of what he had just said. I delayed, on tip-toe, straightening the towel, hoping he was watching me and liking it. I turned around, took two demure steps toward him. I slid my arms around his neck, "Thank you," I said, and kissed him deeply on the mouth. His hands came around and rested on my ass. He removed them quickly.

I stopped kissing him long enough to place his hands back. I moaned softly into his mouth as he caressed and teased my ass. Now I knew just how desperate I was to be penetrated, to be fucked. Michael's hands told me all. But I had decided to save that for someone I really loved. I now realized how difficult it would be to wait.

I wanted Michael in my ass right now, but I couldn't. I had an idea. He was hard again, and I was swelling. "Come on," I said, grabbing a towel, and baby oil from the shelf. I took his hand, and led him back to my room. I spread the towel over my bed, turned to him.

"Ah," I was still getting used to talking like this. "I can't let you fuck me but would you...like to grind me." It was difficult to talk, but Michael nodded enthused. I took some baby oil in my hand, and covered his dick. I looked up and we shared a smile (Oh my god, he's so cute), then I lay down on my belly, and oiled between my cheeks for him. I put my hand under myself to rub. "Come on," I said.

Michael got over me and pressed his cock flat between my cheeks. We gasped together at the feeling. "Oh yeah," I said involuntarily. He pushed, and I moaned, "Yes." I had lost control over what came out of my mouth. I pushed up against him and felt the underside of his cock sliding against my hole. The feeling was incredible. I spread my legs to allow him deeper. My clit throbbed. I knew if I reached back and guided Michael into me I would cum immediately. I fought the desire.

"Oh my God," I cried. Michael softly groaned, pushing against me. Sliding against my ass. "Yes, just like that." I felt it start where his cock rubbed my hole. The tease up my crack sent shivers through me, his balls kissing me with each thrust. There was a hum expanding through my mid-section. Then Michael said through heavy breaths, "You...are...so...beautiful."

"Oh my God I'm cumming," I cried. My whole body felt the contraction. "Aah!" I lifted my ass against him as I began squirting underneath me. "Ooh." Then Michael was cumming, his groan rumbling in my heart as I felt his cum landing hard over and over on the back of my head and down my back while I whimpered, "cumming, cumming, cumming, cumming."

The satisfaction was better than complete. I felt hot and scrumptiously naughty. I also felt thoroughly desired. Michael's moans of delight, his hands on me, his orgasm (he came on me, all over me) spoke volumes. No pun intended.

He kept sliding between my cheeks. I reached my hand down and took his hand. I squeezed his hand hard. A few tears leaked from the corner of my eyes; the intimacy of the moment hitting me. I felt so grateful to Michael for how I felt, it was difficult not to be a little in love with him right now because of how he had just made me feel, and the closeness of our bodies. My instincts were correct about not going all the way. I had to be careful with my heart.

He squeezed my hand back, slid sideways and pulled me into a spoon position, his dick still between my cheeks. He wrapped his arms around and held my breasts. Everywhere our skin met felt like heaven. This was what I thought to avoid. I had thought it would be no problem. Still so insecure, I didn't think I would move a boy like this. I couldn't have hoped, with my big clit, to already be in someone's eyes, what I felt I was. But I'm telling too much, though this needed to be told.

I gently disentangled myself from Michael and stood. I felt my hair. I was all full of his cum. I giggled, looking down at him. "Now we, or at least me," I laughed. "I have to shower again." He rolled off the bed and stood. "Let's go." The clock showed four PM, lots of time.

In the shower Michael asked if he could put his hands on me. "I mean, to wash you."

"I'll tell you what. If we're alone together you can put your hands anywhere. I'll stop you if I don't like it. This way you don't have to ask."

We looked at each other. Michael said, "I want to put everything all over you so you direct me please to everything you are willing to do."

"I don't have to want to? I just have to be willing?"

"That's right," he said. "I'm a guy." He smiled at me, and I couldn't believe his intelligence and maturity. He knew what that meant to me.

"So go ahead and wash me," I said, directing the spray down to my legs and placing my hands on the tile wall like I was under arrest. Michael covered my body with soap, and passion, gliding all over me with his fingers. We both became hopelessly aroused. Michael was feeling my breasts when our eyes met. "Can you come again?"