The Diary

Copyright 2008

My name is Jessie and I am going to share with you my most intimate secrets by letting you read me diary. This would be the thing that most girls share with their best girlfriend, but I don't have anyone close. I'm a freshman at a regional State University. I have lived with my Grandmother for the last five years, both of my parents dying suddenly but that's something I don't want to talk about. I share a room with two other girls on campus now, but my Grandmother lives not far from the University so I see her often.

I've never had a boyfriend before. I'm extremely shy, the type that would pass you by and you wouldn't even see me. I have brown hair, what I consider mousy brown, hanging a bit below my collar. My eyes are hazel, my skin fair. And my body is something that boys don't gawk at, even if they could see it. I dress very conservatively. I'm an excellent student, learning comes easy to me so I devote all of my time and energies to school. That is where I met Steven. He's a freshman also, living on the nearby Army base. We had one class together at the beginning of school and were thrown together as lab partners. He's as smart as I am so we hit if off immediately. We've been study partners since that time, almost a year now. That's all I have to say, the rest is in my diary.

Saturday, February 2

Yippeee! I think I have a boyfriend. Now I know you are wondering how come I don't know for sure. Steven. My boyfriend. I wanted to see it in words. We have been close ever since September. It has always been studying, but we now eat together almost all the time. And we even went to a couple of movies on campus. We had been studying almost all afternoon at the library. Steven finally suggested that we go get a pizza on campus, my stomach growling finally signally that I needed food. We were walking through the park, taking the short cut when I felt it. It was his hand. It touched mine. I looked over at him, but he was staring straight ahead, even though he was talking to me. I felt his fingers touching mine and then suddenly he was holding my hand. His hand was damp, as well as mine, but we clung to each other. We continued to talk without saying anything about holding hands. I almost hated it when we had to sit down at the table. I never wanted to let go of his hand. I was nervous when we finished. Would he hold my hand again? He walked me back to my room. Holding my hand all the way.

Sunday, February 3

I barely slept last night. All I could think about was Steven. He's a gentle boy, not like others that make fun of me. We have been close, so close that it was almost like he was my best girlfriend. And respectful. His father is an officer on the military base near the University, so I'm sure that's where he got it from. Just like me, my Father a Chief Master Sergeant. Military grow up differently. They either rebel against the rigid authority of military or they accept it. Steven and I both accepted it. We would never question our elders. I was excited all morning, meeting Steven for lunch and then we were going to study. He also mentioned a movie playing tonight on campus. Would that officially be a date?

Sunday, February 3- 11 PM

He put his arm around me in the movie. Right after it started. I think we are officially a couple now. I never felt anything like it, putting my head on his shoulder, feeling so secure with his arm around me. I could have stayed like that for my whole life but unfortunately the movie ended. He walked me back to my dorm, still holding hands. I hoped he would kiss me, but he didn't, an awkward moment when we said goodnight. It was though we both wanted to kiss, but were too shy.

Thursday, February 21

I went to Steven's house for the first time. I was surprised. His father is a General. His house is this big, brick two story with vines growing up the front as if it were standing for centuries. No one was home, going into a large den to study, a flat screen TV taking up almost one wall. We had a snack as we poured over the notes for Calculus, the mid-term coming up next week. I guess we were lost in studying because we were both surprised, Steven standing up as if we were doing something wrong. I looked over at the door, his father filling almost the whole doorway. Though Steven and him looked similar in features, it was confined to their faces. For his father is an imposing man, especially all dressed up in his uniform, his chest covered with rows and rows of multi-colored ribbons. And he has a large chest as well as large arms, not a bit of fat on a well trimmed body. Steven fumbled for words, finally addressing his father as Sir, introducing me to him, though Steven didn't say the word I wanted to hear. My girlfriend. His father shook my hand, his powerful grip making me weak in the knees. And the way he looked at me, his eyes racing up and down my body, feeling my face get flushed. He didn't look at me like Steven did. We were getting ready to leave when his father came into the room as if he were watching us and knew. He invited me to dinner on Saturday. Or I should say he asked Steven if he wanted to have his girlfriend come over for dinner on Saturday. At least one of them considered me officially the girlfriend. I accepted without hesitation.

Saturday, February 23

I did something that I never do. I wore a skirt, even though it was freezing cold outside. I'm not sure exactly why. Was I trying to impress Steven or his father? Steven picked me up, barely mentioning my skirt, though he did tell me I was "pretty tonight". He told me about his father on the way to his house, though no explanation was needed. I already knew about military men. Officers, especially Generals never had the decisions or commands questioned and that extended to family life. Even more since Steven's mother was missing from the home, Steven never mentioning why, me never pushing it. Like me, it was hard to talk about missing parents. Even with your boyfriend or girlfriend.

Michael, the General, asked me to call him Michael after I stammered Sir too many times while he took my coat. As he slipped it from my shoulders I could almost hear him inhaling my perfume, his head so close that I could feel his hot breath blowing on my neck. He stood back, his eyes going from my face down to my feet and back up, stopping at legs. "Very beautiful tonight Jessie. Steven is a lucky boy. He probably doesn't know how lucky." He turned and walked away before I could say anything, even if words would have come out of my dry mouth.

The food came out of nowhere, I still don't know who cooked it. After dinner we went into the den, Michael lighting up a cigar and smoking it as he sipped a brandy. I excused myself to go to the girl's room. When I came back, Steven was gone, hearing him in the kitchen. By the sound of clinking in a glass, he was making Michael another drink. I was walking by him to sit back down when his voice startled me. It was so loud and demanding. "Your skirt is crooked. Come over here."

It was as if I were in a daze, walking over to him as he sat forward in the chair. His large hands reached for me, my eyes mesmerized as I moved closer to him, his thick legs sliding between my legs until I was straddling his legs. His hands were on my hips, guiding me forward, my body responding by instinct only. His legs were pushing along my inner thighs. He finally stopped me, his hands moving to the side of my skirt, twisting it with a powerful jerk until it moved until it was straight. I felt so strange, a man dressing me. But he didn't stop there. His hands slipped under my skirt, disappearing from my sight as I looked down. I was sure I had an orgasm right then when I felt the hot flesh of his hand on my naked inner thigh. My panties grew wet, not damp. Wet, as if my pussy gushed cum. I could barely stand, but he was almost holding me up, my legs forced apart by his legs between mine, his hands touching my inner thighs, my muscles instinctively trying to close, his legs keeping me spread. He removed his hands as suddenly as they were thrust under my skirt, but not before one hand slipped so far under my skirt I shuddered, sure he was going to touch my pussy as it slowly moved up my naked thigh. But he didn't, suddenly finished with me. Steven was coming back into the room, but not before Michael said it to me. "You have lovely legs. Next time wear a shorter skirt."

I masturbated three times that night.

Thursday February 28

Steven kissed me. It wasn't what I expected. I guess I read too many romance novels, expecting something more. It was nice, his lips soft, but there wasn't much passion in it. I felt more passion when his father touched me. From then on we kissed goodnight each night, but the passion was still never there. My birthday was Saturday and Steven invited me over for dinner. I was disappointed that it was Steven's idea to invite me over for dinner, not his fathers.

Saturday March 1

Happy Birthday to me! I looked into the mirror, even surprising myself. I had bought a short skirt this morning, after Steven had given me his gift. I opened it up, a black cashmere sweater. I never felt anything so soft. I bought a plaid skirt to go with it. A school girl skirt. It felt strange, never feeling so feminine before. I couldn't wait for him to see me. But I wasn't sure if it was Steven or Michael that I wanted to see his expression.

Michael spun me around as if I were a model when he took my coat, the short skirt pulling out as I spun. He whistled a sheepish whistle, his eyes glued to me below my waist. He moved close to me as Steven hung up my coat and whispered into my ear. "Very sexy Jessie."

Michael's eyes stared at my all through dinner, though he didn't see me watching him. His eyes were glued to my breasts. I never had large breasts, though most never even had a hint how big they were because I buried them beneath layers of clothes. Tonight there was only a soft cashmere sweater that clung to them and cling it did. I felt a strangeness, even sitting up straight in the chair, finally arching my back, sticking them out for his eyes to ogle. Michael was cleaning up the dishes and I volunteered to help, Michael accepting.

He turned to Steven and asked him. "Steven would you do me a favor and take a quick ride over to the OC (Officers Club) and pick up a bottle of brandy. I'm out and you know how I like to have a glass of brandy with my cigar after dinner. I phoned ahead, they will give it to you. All you have to do is drive to the back door. It will only take ten minutes. Jessie and I will clean up while you're gone." Steven went without a hint of hesitation.

I was surprised that I made small talk with Michael, not my usual self. "Did you see the sweater Steven bought for my birthday?" I almost wanted him looking at my breasts again.

"I helped him. I made sure it was cashmere. Nothing is too good for you. And I personally like cashmere."

"You like the way it looks?"

"No, it's tactile. I like the way it feels. Especially when touching such lovely soft orbs."

And then he made a request that sounded awfully like an order. I went into the bathroom. I locked the door and sat down on the toilet seat. I knew what would happen if I did as he ordered. But I was afraid of what would happen if I didn't. My hands shook as I pulled the sweater over my head, staring into the mirror as my plain, white bra came into view. I reached around back and unsnapped the bra and let it slip down my arms, my naked breasts popping into view. My breasts weren't big, but firm. It was my nipples that surprised me. They were hard, like pencil erasers, sticking out as if Michael had touched them. They swelled as the soft cashmere material slid over them, looking into the mirror again as they disappeared from sight. My nipples stood out hard. You could tell I wasn't wearing a bra.

Michael was waiting for me, feeling my face flushed as he looked at my breasts. I could almost feel them moving as I walked. No one had ever seen me like this before, wondering what I was doing. What if Steven came back and saw us? What was Michael going to do?

His voice was loud and demanding. I did as he said, turning to face the counter, feeling him move close behind me. I jumped when his hands touched my waist, his voice soft and reassuring in my ear as though it was Steven, not Michael. His hands moved up my side, fighting to stop from laughing as they almost tickled. My hands clutched into fists at my side as I felt the first touch of his large fingers on the side of my breasts. It was so soft, almost feathering along the soft sides, feeling my nipples explode. I blushed brightly as his hands slid under my breasts, lifting them up, my nipples scraping painfully against the soft cashmere, the arousal almost hurting. They wanted to be touched. His hands became more urgent, his grip on my young, firm flesh harder. I could feel the blood rushing to the tips. I looked down, seeing his hands caressing my breasts as if it were happening to someone else.

I almost came when his fingers touched my nipples, slowly circling each one, feeling them stiffen to hard points, roused by his touch. His fingers pinched them, harder, pulling them, feeling them stretch. I couldn't believe the pleasure between my legs from the fingers that teased my nipples. It felt like hours as he played with them, forgetting all about Steven.

"I love youthful, firm breasts Jessie. Do you like them played with?"

I couldn't have said anything if words could have come out of my parched mouth. I was just barely breathing. No one had ever touched my breasts before. And now it was my boyfriend's father, not my boyfriend. And all I could do was hold the counter tightly until my knuckles turned white and think of masturbating as soon as I got back to my room.

He wasn't finished. Though he might love the feel of cashmere beneath his fingers, that didn't stop him from slipping his hot hands underneath the sweater. I arched my back, pushing back my ass until I felt him behind me, his hands rolling my naked nipples as my breathing became rapid and shallow. I felt his cock, my ass pushed up against it. It felt huge, like a babies arm. Would Steven have a cock like that, the thought racing through my head? I was technically a virgin, though I didn't have a hymen. His fingers were insistent, sending illicit pleasure through my nipples, fondled against my will. Or was it a deep desire that I tried to quell?

I almost came when he nuzzled my neck, his tongue slipping into my ear, rolling around in the tight hole as his fingers continued their fondling. His fingers gripped my nipples tight, feeling like they were trapped in a powerful vise, but all I could do was arch my back and stick them out as he yanked the hardened flesh out of shape. I jumped when the door shut, but Michael took his time, slipping his hand out of my sweater slowly.

"Next time I'll see them naked and suck them." Michael moved away from me, but not before he took my hand and placed it against the front of his pants. My fingers instinctively curled around the thick shaft as if I had done this a million times. He pulled away as Steven entered the room.

"You okay?" He asked me as he kissed me.

I knew that my face was flushed and I was almost ashamed that my nipples stood out so provocatively. He looked at them, but not like his father looked at them. I kissed him back. "I missed you." I pressed up against him, just like his father had done to me. For the first time, I felt him. His cock. It wasn't as big as his fathers, but I had this desire to reach down and touch it as I did to Michael's. But I didn't.

We watched a DVD, Michael leaving us alone after he had his cigar. Michael caught me looking at his crotch, his hand reaching down to touch himself unashamedly. Steven kissed me while watching the movie, a chick-flick that he had picked out for me. I wanted so much for him to touch my breasts, but he was a gentleman all night long.

I came almost every night next week, my fingers teasing my nipples as Michael had done to me, though I didn't pinch them as hard. But it still made me cum over and over.

Friday March 7

Finals are over, Steven and I spending almost the whole week together at his house studying. I insisted, saying that it was less distracting at his house, though that wasn't true. I anxiously awaited Michael coming home each day, but ended up going home disappointed. Until today. We were just getting ready to leave, Steven to drive me back to the dorm when he walked in. He surprised me, almost bumping into him. He looked at me, my pussy growing wet as soon as his eyes stared at my half naked legs. In spite of the cold, I had begun to wear skirts. Short skirts. Even Steven didn't fail to notice, his eyes looking down at my legs when my skirt rode up too high. And my eyes never failed to spot the growing erection in Steven's pants when he did. I had two men lusting after me after a life of no one.

"Leaving already," Michael stated to Steven. "Why don't the two of you stay for dinner? Pizza, my treat."

"Is that okay Jessie?"

I could barely babble yes to Steven, already wondering how Michael would plan to get rid of Steven for a short time. His mind was quicker then mine.

"If you pick up the pizza, I'll make the salads. We have to have something nutritious. Jessie has that lovely figure she has to keep to keep you interested."

"Want to come along Jessie?"

I already had my coat on, trying to think of a way to say no when Michael's voice boomed loudly.

"You want me to make the salad by myself. I need the help of a good woman."

He took my coat before Steven could protest, if he would have. But Steven, like me, obeyed without question. And Michael counted on that. I kissed Steven goodbye as if he were leaving for the night, not sure why. Maybe to make Michael jealous. Maybe to feel his cock against me. Was I becoming feminine? Using my girlish charm to lure two men to me. I never thought of doing such a thing in the past.

The door slammed shut, the car starting outside. I went into the kitchen, Michael following me. I could almost feel his eyes staring at me, trying hard to keep my ass from swaying from side to side as if I were teasing him. I went to the refrigerator, Michael pulling out the vegetable tray to reveal a large salad already made in a big plastic bowl. His hand slipped around my waist as he led me to the den, the salad left on the table next to the cutting board, a knife placed on it, Michael sprinkling tiny bits of lettuce on the board. Michael had planned far in advance. What else had he planned?

He sat down in the chair leaving me standing before him, his hands on my hips. He lowered me down on his lap, my eyes on the bulge in his pants, feeling it pressed up against my ass as I settled on his lap. I felt so comfortable on his lap as if I belonged there. He asked me if Steven kissed me yet. I answered yes, but told him how it didn't spark any passion in me. His fingers circled my lips, Michael telling me how he would teach me and I could teach Steven. His finger entered my mouth, running over my teeth and tongue. I tightened my lips on his finger and he began to push it in and out. I knew how it must look. As if he was fucking his cock in my mouth. His cock jerked beneath me, it affecting me in the same way. His hand lifted my head up and turned it towards him. He told me to open my mouth, his lips covering mine. I was surprised that his lips were as soft, his kiss almost gentle. My mouth was open and then I felt it, his tongue slipping between my lips and entering my mouth. My tongue met his, dancing against it as his hands tightened around me, pulling me closer to him. His kiss became more demanding, his lips crushing mine. All the while his tongue explored my mouth, over my teeth and gums, finally pushing deep into my mouth so that I almost choked. I couldn't believe a tongue could move that far. He never broke the kiss, my nose flaring as I tried to breathe, my heart racing from the excitement. He turned me sideways towards him, our lips never parting. His hand slid up my side, his large hand encircling one of my breasts, his fingers tightening on it until I felt the blood rushing to the tip, pounding hard. I wished I hadn't worn a bra.