The Diary

PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

I found my hips moving without me realizing it, sliding my ass back and forth over his lap, his hard cock jerking and shuddering beneath me. I filled my lungs with air but I couldn't catch my breath, my breathing ragged and uneven. It made my breasts heave up and down, something that Michael didn't fail to notice. My arms went limp as Michael pulled my sweater up over my head, seeing dark for a second before he threw it on the floor. His eyes stared at my heaving bosom, my chest pink in shame, exposed to him. His hands slipped down my back, sending goose bumps through my body. He was expert with my bra, unsnapping it with a deft motion, his hands pushing the shoulder straps down. My arms moved up to cover my naked breasts in reflex, but his hands pushed them away like a pesky fly. They hung down at my side as one hand cupped my naked breast, my breathing stopped as his head moved down, his mouth already open. I wished I could have thrust my hand under my skirt when I felt his hot, wet lips encircle my nipple, dragging it deep into his mouth, all the while his tongue lashed at it. I was sure I wet my panties at that moment, my naked breasts fondled by a demanding hand and mouth. For five minutes I endured the pleasure of the constant fondling of my nipples. He knew exactly what to do to me, unable to do anything but squirm erotically on the growing erection beneath my ass.

He finally stopped. I looked down to see my breasts wet with his saliva, my nipples so big that they stuck out over an inch, my white breasts covered with red marks where his hands had squeezed them too tight. He stood me back up, feeling strange to be standing in front of a man, stripped naked to my waist as he stared at me. He took my hand, pushing it down into his lap.

"See what you do to me. You can do that to Steven also."

My fingers curled around the thick shaft, my fingers moving up the shaft until I felt the thick head, my fingers trying to outline it in his pants. I could imagine what it looked like in my head. He stood up, kissing me again, a knee between my thighs forcing me to spread my legs, his upper body pushed up against my naked breasts. He moved his chest from side to side, feeling the multitude of sharp ribbons rubbing hard against my naked breasts, especially my swollen nipples. They hurt, but his hands held me tightly against him, though he did force me to move my hips from side to side against his cock. And later that night when I was home in bed masturbating, the pain from the ribbons were more pleasure and my pussy was drenched from the hard cock pushed against it as he masturbated against me. He left me alone, going upstairs to change his clothes, just in time, my sweater slipping over my head as the front door opened.

Michael left as alone after dinner. We were watching a DVD, a love story though it did have more sex in it then romance. The lights were dimmed, thought he large TV did give off a lot of light. I was curled in Steven's arms, reaching up with my hand to turn his head towards me just as the end of the sex scene. I kissed him, feeling him respond. I noticed the bulge in his pants, the movie making him excited, my pussy still drenched from what Michael had done to me. My tongue slipped into Steven's mouth, my breathing stopped to see if he would think I was being too bold. Surprised, his tongue responded, his kiss becoming more demanding as we French kissed for the first time. And it wasn't the last time that night. Steven kissed me again and again, each time after a sexy scene, each time he French kissed me, leaving me panting for more. The movie was almost over, the girl in bed with two men at once. I could almost see Steven's cock jerking in his pants, wishing he was like Michael and would push my hand down onto his throbbing member. Instead I took one of his hands and placed it on my breast. He stared at me for a long moment, not sure if it were surprise or disgust. But then he kissed me, his tongue more demanding. As well as his hand. He grabbed my breast, fondling it with an inexperienced touch, but my nipple never failed to respond. I was disappointed when the movie ended, wishing I could have touched his cock.

He drove me back to the dorm, kissing me outside, his hand exploring my other breast with more confidence. I moved my hips, sliding my pussy back and forth against his cock. I felt him shudder, sure that I had made him cum. I could almost smell it in the air.

Friday Week of March 10

We are more like boyfriend-girlfriend making out until we were both panting. His hands explored my breasts, my hands at my side as he worked them over until my nipples ached. Thursday night we were at his house, Michael not home, out of the state until tomorrow. We were watching a movie, really it was just playing on the TV. Steven and I making out. Yes, I was making out with a boy! Before long we were lying on the couch, on her sides facing each other. I felt his hands fumbling with my bra, letting him do it until I felt the pressure released. His hand moved under my sweater, wearing Michael's favorite cashmere sweater. I almost came when his fingers moved the bra out of the way and his hands touched my naked breasts. I pushed my pussy into his as his hands found my nipples and rubbed them to erection. I came that night, his cock pushing against me driving the orgasm from my body. It was the first time that anyone but myself had made me cum. Even after I came, I continued to rub my pussy against his cock. This time I knew it. I had made him cum, Steven holding me tightly against him as he rubbed his cock against me as he masturbated, moaning softly as he came. He was a bit humiliated as he excused himself to go to the bathroom, sure that he was cleaning up the wet cum in his shorts. I never felt as proud of myself as I did that night. I masturbated and came three times that night, barely sleeping at all. Each time I came, it was either Steven or Michael in my head as if did.

Friday March 14

We were studying at Steven's house. Michael was home, but I didn't see him. Steven was watching the end of the movie as I got up to go to the bathroom. As I walked down the hallway, I could see the bathroom door closed, the light shining beneath it. I walked slowly, hoping that Michael would come out soon. I stood outside the door for a moment before I heard the doorknob turning. Michael came out, surprised to find me standing there.

"That's convenient, I don't have to look for you."

He pushed me against the wall, his hand holding something. He held it in front of my face. It was a condom. A used one, the reservoir filled with a white, milky substance.

"I just masturbated for you Jessie. Open your mouth and stick out your tongue."

I don't know why I did it. Yes I do. Michael could control me with just his voice. I opened my mouth and stuck out my tongue as I watched him move the condom up over my outstretched tongue. The reservoir was filled like a small balloon. He tipped it down, squeezing the other end as I watched the milky cum slide slowly down the condom and begins to drip off the end. It hung in a clump, the ropey fluid stretching down until I felt the first thick clump of cum fall on my tongue. It felt like it was burning, the cum still hot from his body. I couldn't believe all the cum that filled my mouth, the thick, salty crème permeating every crevice in my mouth. When I thought there was none left, he reversed the condom, slipping the wet inside over my tongue like it was a cock. I sucked it into my mouth, submissively holding all of his cum in my mouth. It tasted terrible, almost making me gag it was so thick. But it also made me aroused, forced to drink his cum as he stood and watched my discomfort. He pulled the wet condom from my mouth, my cheeks still bulging from the cum in my mouth. I did as he said, swallowing it, choking twice as the thick cum slid slowly down into my gullet. He left me in the hallway. I went back to Steven. Unfortunately he wanted to make out. I was sure that he could taste his fathers cum when he French kissed me.

Tuesday March 18

I got a strange phone call. It was from the Generals Aide inviting me to dinner tonight. I accepted even though I know I shouldn't have. I knew that Steven was out of town for two days. He didn't tell me where, though I suspected it had something to do with his mother. I was nervous as I raced around all afternoon. I took a shower as one eye kept and looking at the clock. Michael was sending a car to pick me up. I was so nervous as I got into the car. A young Private was driving, his eyes looking into the rear view mirror catching a glimpse of me. My coat had parted and my short skirt left a lot of leg showing. I didn't make any move to cover my legs. I was beginning to enjoy being a girl. A desired girl. He asked me how I knew the General. I told him that Steven, his son was my boyfriend. I think he was trying to figure out if I want the Generals Mistress. I liked that. People, men began to notice me.

Michael was waiting with the door open as the car pulled up. The private opened the door for me, not so much a gentlemen, more he wanted to see my legs. Or between them. I got out of the car awkwardly, showing him more then I should have. I'm sure he could see up under my skirt. I smiled to myself, feeling I felt naughty.

"I was afraid you wouldn't accept."

He took my coat, standing so close that he was almost touching me. I wondered whether we would even get to dinner. His eyes feasted on the new cashmere sweater I was wearing, spending the last of my money for it. I'm sure that he didn't miss that I wasn't wearing a bra. To make sure I rubbed my nipples in the darkness of the back seat of the car before it pulled up in front of the house. My skirt was shorter then the last. And I was wearing high heels, the first time in about five years. I tried to walk on them naturally, but it was hard. I was afraid of what he was going to make me do. Or do to me. "I was afraid to come." As soon as the words came out my mouth I knew it sounded bad. As if I was afraid of having an orgasm. "That's not what I meant," I stammered.

He kissed me, the door closing at the same time, cut off from the probing eyes of the world. He pushed me against the door, his knee pushing between my legs until I relented, spreading them submissively his tongue searching deep into my mouth. His hands fondled my cashmere covered breasts, his hand insistent as they pinched and prodded my growing nipples. He took my breath away with his kiss my hands going around his waist and holding him against me as I do with Steven. My legs spread wider until I felt it, his hard, demanding cock jerking against my pussy. He began to grind against me as if he were fucking me. Would he take my innocence from me tonight? I knew that before I left, he would have taught me so much more. Sexually.

It was long minutes before he broke off the kiss, my lungs trying to fill with precious air. "I hope you're not hungry for food. I plan to feed something else to you."

I followed him like a puppy. We didn't go into the den, but the living room instead. It was more formal, almost naughtier for what he was going to do to me. He didn't kiss me again, but pulled my sweater over my head and threw it on the sofa. I was standing bare breasted in front of him, my hard nipples sticking out so far that it looked as though they were trying to reach his fingers. His large hands encircled them with a familiarity, the tips springing to life as his calloused fingers raced over them. Even when he pinched too tight and yanked them out, I stood firm, the delicious pain in my stretched nipple flesh racing between my legs to soak my panties. His mouth was even more demanding, his teeth capturing one of my nipples, grinding back and forth over it, feeling like a knife slicing through it. The pain mixed with the pleasure, my legs barely able to keep me up.

He pulled away from me, looking at my glistening breasts from his spit, teeth marks encircling one of my swollen nipples. His hands moved to my shoulders, feeling him begin to press down on them. I knew what he wanted. I gently kneeled on the floor in front of him, looking up to see his cock outlined on the front of his pants only inches from my face.

"Touch it," his voice commanding me to do his sexual bidding.

My hands went to the front of his pants, my tiny fingers outlining the thick shaft that threatened to tear from his pants. I pinched it, but it felt like steel, pushing up with my fingers, surprised that it was so long. It went up almost to his waist where I felt it thicken to a dome. I had seen pictures of cocks, but not erect ones. And this one was definitely erect. I licked my lips, getting my lips wet subconsciously. I knew that I would have to take it in my mouth, there was no other reason to be on my reason. He didn't want my hand, but my mouth. It was bad enough when he emptied his condom in my mouth. What would it be like when his cock spewed his cum directly into my mouth? I followed his instructions and they were detailed and explicit. My hands slid his zipper down, the noise breaking the silence of the room. I unbuckled his belt and undid the top button, pulling his pants back. He was wearing boxers and his cock strained to get out. I reached in, touching the hot flesh of a hard cock for the first time. I pulled back, surprised that it was so hot, but Michael encouraged me back. My hands curled around the thick shaft, my eyes trying to catch a glimpse of it. I didn't want to, but I released it so I could pull his boxers down his legs. He had thick, muscles thighs, covered with black hair. But my eyes were on his erection, the thick throbbing cock bobbing so hard that it almost touched my lips. It was heavily veined, dark blue veins running up the side to disappear when it got to the almost purple dome. A thick ridge around it made it look more like a helmet. I blushed as I saw Michael looking down at me.

I kissed it, just like Michael ordered me to. My lips pursed as they moved close to the tip, covered with the shiny cum that had already leaked from its tip. My tongue licked all over the head, lapping up his slick cum like a kitten with a bowl of milk, filling my mouth with the familiar taste of his salty cum.

"Open wide," Michael taking hold of his cock, rubbing it all over my lips as he tilted my head back until I was looking into his eyes. He wanted to see my face as his cock entered my virgin mouth. I opened wide, surprised that the head of his cock barely fit in my lips.

"Lick the head Jessie," Michael encouraged me. It jerked in my mouth when my tongue raced around the thick helmet, finding the sensitive area just beneath the rim as though I had sucked a thousand cocks before. "It likes that Jessie."

I felt the rubbery head of his cock in my mouth, my lips stretched tightly around it until they tugged beneath the rim, trapping it. My tongue went to work on it as if I knew what I was doing, his jerking cock making it as though I was doing the right thing. I began to suck on it, feeling spit dribbling down my chin. My mouth was filled with the salty taste of cum, sure that he had already cum. Michael smiled down at me, his hands gentle as they pushed the hair from my forehead, only mumbled sounds coming from my stuffed mouth. I was trying to breathe, my nose flaring as I sucked in air through my nose to fill my starving lungs.

My head moved up and down, as the slippery wet cock began to slide easier between my stretched lips, trying to stop the gurgling sound that came from my mouth as I began to suck his cock. Yes, I said it. I was sucking his cock. I was kneeling half naked in front of Steven's father, his thick cock in my mouth and I was sucking him with all my inexperienced but youthful exuberance. His hands slid down my chest until they found my nipples, tugging and pulling on them until he aroused them to hardened tips. All the while I was taking more and more of his cock in my mouth, not believing that four inches of it was still outside my lips even though the thick head was pushing against my tonsils. I gagged once and almost swallowed the head of his cock by mistake when my throat opened up.

His hips began to move, rhythmically thrusting his cock in and out of my mouth as if it were my pussy. Wishing it was his cock taking my virginity between my legs, not my mouth. My hand reached out instinctively to feel his balls, the prickly hair tickling the palm of my hand. I squeezed until I felt the twin balls inside, my hands following them around as they moved mysteriously. I heard Michael moaning, knowing that my mouth and hand was having an affect on him. I wondered where all his cum would go when he came in my mouth, his cock already filling every nook in cranny in my mouth. His hands left my breasts and stroked my head, guiding it up and down in rhythm with his thrusting hips.

It hit me hard, Michael's hand getting tighter as he pulled me onto his throbbing cock like one would put a sock on their foot. It pushed to the back of my mouth and then I was sure that it grew bigger, my lips aching as they stretched to accommodate the thick shaft. Michael bucked as he came, trying to get away when a jet of hot cum flew out the end of his cock and shot directly into my throat as I choked and gagged. But he held me tight, my mouth filling as he shot a second load of cum that made my cheeks bow out from the abundant crème that filled my mouth. I felt it leaking from my stretched lips, the thick cum slowly running down my chin, the fluid still hot from his balls. And my hands milked his balls of his cum instinctively. He shot one more time before his hands relaxed on my head. As he pulled his cock out of my mouth, he left a trail of thick cum on my lips. His finger scooped up the cum on my chin and pushed it back into my mouth. He lifted my head back, his hand caressing my outstretched throat.

"Swallow it. Show me how much you like drinking my cum." He massaged my throat as I struggled to swallow the thick cum, feeling it sliding down into my stomach slowly. It took me a couple of minutes until I was finished, my stomach heavy with his cum. He helped me up like a gentlemen, as if I was kneeling in prayer, not sucking his cock. We went in for dinner, Michael not letting me put my sweater back on, feeling embarrassed each time he looked at me and my naked breasts. I had to be careful not to spill anything, afraid of burning my breasts. And my nipples stayed erect all through dinner.

Michael had his brandy and cigar in the den. I was kneeling at his chair like a servant girl as he fed his cock into my mouth again. This time he guided my head, taking his time, making me suck his cock for over a half an hour. His cock never left my mouth, struggling to breathe at the same time I sucked his cock with enthusiasm. By time he finished his cigar, my tongue was tired, but Michael was just getting going. My hands gripped the side of the chair as he pulled my face down over his cock until I felt the head of his cock tickling my tonsils. I gagged, but Michael's hands became more insistent. Before I knew what was happening, I choked and gagged, the thick head of his cock breaching the tightness of my throat. I struggled to pull back, but Michael was stronger, gurgling and babbling incoherently as his cock filled my throat with his thick flesh. I never felt anything like it. It was like a giant snake moving down into my stomach. I choked and gagged, but Michael only pumped his cock in and out of my throat. I didn't taste his cum that time for he pumped it directly into my stomach, his cock swelling in my throat as my muscles rippled up and down the shaft. He finally pulled his cock from my throat, my throat rubbed raw. His cock didn't leave my mouth until my tongue licked every inch of his softening cock.