Note: This story was dynamically reformatted for online reading convenience. I have sort of been having a writers block and a friend on here suggested I write about being with an older man. And a couple nights ago I just started writing.. I finished it this morning.. it is compleatly fiction, but was fun imagining myself in the story as it came out.. I hope you like it.. as always let me know what you think.. Thanks, April ( Aprilfirez@yahoo.com ) Titled my private journal entry. I could not tell anyone about this so I have decided to write it down in my journal. I was at my friends house for a sleep over, we had spent the night talking, watching movies, and teasing her annoying little brother. After Annie's (my best friend) mom had told her little brother to go to bed, Annie and I had gotten changed into our night cloths. For me it was just a long t-shirt and panties. While watching the movie I had cuddled up under a blanket on the sofa and dozed off. During the last movie I had fallen a sleep, it had been a long day and I had been worn out from gymnastic practice. I fell a sleep on the sofa down stairs in the family room. I don't know what time it was when something woke me up. It was dark, and Annie must have turned off the TV and gone to bed. I'm not sure what woke me up but in my tired daze I knew I wasn't alone. At first I thought it might have been Annie, but when I felt a hand touch my leg I knew it wasn't her. I was still so tired and in such a daze that I didn't do anything as I felt the hand moving up my leg. Then I felt a second hand at my hip pulling at my panties. My eyes cleared a little but it was still dark and hard to see, it didn't take me long to figure out that the hands that were touching me belonged to Annie's Father. It was like a dream, I don't know why I didn't try and stop him or scream. Instead I just laid there in a dream like daze as he pulled my panties down. His hands rubbed up and down my legs, which I had to admit felt real good, I was still sore from my work out earlier that day. Then his hands wandered farther up, his body moving closer to me spreading my leg around him as his hands went under my shirt. His strong hands cupped my breast and squeezed hard, and at the same time a soft yelp escaped my lips, he froze and just sort of looked at me. All I could hear was my heart beating so hard and the deep breaths I was taking. Then in a soft questioning tone he asked "Annie?" I was stunned, I thought he might have maybe mistaken me for his wife (thinking back on it now I know he couldn't have thought I was his wife, just because as soon as he would have touched me he would have known I wasn't her) but Annie, his own daughter? Again I didn't say anything, then I heard Annie's voice from the other chair in the room. She said in a calm voice "no daddy, that's April". Annie turned on a small reading light that was next to her chair, and we could all see clearly with the dim light. Annie's father is not around much because of his job and when he is he's usually in his office. I had never really paid any attention or notice of him before and here he was kneeling between my legs after pulling my panties off and his hands still holding my breast. Both of us sort of looking at each other in shock and fear, eyes wide open. Annie's dad had big wide shoulders, and thick strong arms, he had the body of a real man. I don't know how long we staid there unmoving just looking at each other with out a word. Annie had walked up behind her dad putting her hands on his shoulder bending over to whisper in his ear as she looked straight into my eyes. She whispered to both of us, "It's ok daddy, April's not a virgin and she wont tell anyone". Annie was my best friend and we told each other everything, at least I thought we did. Annie knew about the couple of boys I had been with from school and also knew I dreamed of being with a real guy, I had often told her of my fantasies about older collage guys. Annie then winked at me and then kissed her own dad on the lips, and it was not just a father daughter kiss, she kissed him hard and I could tell she had his tongue in her mouth. I was in such shock, but when I felt my own wetness drip from my pussy, down between my ass I realized that despite my shock, I was super turned on. I watched as Annie kneeled down next to her dad and her hand went down between my legs and reached into his boxers grabbing his penis. With her other had she pushed his boxers down and for the first time ever I saw what a real mans penis looked like. It was so much larger then the boys from school, even though one had been a senior. Annie had her hand wrapped around it stroking it back and forth, he was so thick that even if she squeezed hard she would not have been able to touch one finger to the next. As she massaged his penis I watched in amazement as it got even harder and bigger. As he grew Annie started to rub the head of his penis up and down my pussy. His hands had started to squeeze and pinch my breast and nipples again. I could not help myself, I was so turned on and hot from what both of them were doing to me, I let out a loud moan. That's when Annie slapped me really hard on the side of my hip as she looked at me and told me to shut up, if I woke up her little brother or her mom we would all be in a lot of trouble. Annie's father told me that if I couldn't hold it in to use the pillow next to me to quiet myself with. Still in sort of shock and a daze from all this I just nodded. Annie kept massaging her dads penis and moving it up and down over my pussy. I could hear him breathing hard and it all felt so good I just laid back and closed my eyes. I was so wet and each time Annie moved his penis down I could feel the tip of him go in my pussy a little. Then with a startled voice I heard him call out "Annie!" at the same time I felt him enter forcefully into me. Annie had guided his cock and pushed him into me with out any warning. Almost forgetting, I had to turn my head as I screamed into the pillow next to me. Annie's father managed to stop her from pushing all the way and asked me if I was ok. I could not catch my breath and wasn't able to answer, but Annie told him I was fine. She moved down next to me and softly whispered in my ear that he was only half way inside me. Annie then kissed me so softly and caring. She told me just to relax, she confided that her first time with him it had hurt to but in a little bit, if I relaxed it would start to feel better then anything I could imagine. I felt her fathers hands move under me grabbing my ass as he lifted me up a little with his strong arms. Annie's still kissing me, her hands finding my breast. I could feel her father press harder into me. He was so big it really did hurt, I tried spreading my legs wider hoping that would lessen the pain, but when I did he just pushed harder into me. I couldn't help it as tears came to my eyes, but Annie just wiped my tears away and told me just to relax. I put my arms around Annie hugging her hard to fight off the pain between my legs. Then he pulled out and I could breathe again. I felt his hand tighten around my waist as he suddenly and forcefully rammed into me hard. I think it was then that Annie could see that with my tears and with the last sudden penetration, me not being able to catch my breath or breathe, that I wasn't taking it very well. She pushed her dad away from me, and when his penis fell out of me you could hear a wet sort of pop. I couldn't help but feel bad that I wasn't able to handle or satisfy her dad. Annie said it was ok that she would take care of me as she got up and moved down between my legs. I could feel her breath on my wet pussy as she got close. She blew on it a little and it really did feel good. Annie was now on her knee's bent over with her head between my legs. We've played together before so other then having her dad there watching us I was comfortable with her looking at me. I saw her dad move behind her and push her panties down and he sort of grabbed her bottom like some one would grab a bowling ball, pushing his two middle fingers into her pussy. Annie started to lick and suck my pussy and I was able to start relaxing as the pain slowly left my abused pussy. Annie was being very gentle with me, softly massaging my breast and giving long soft licks up and down my pussy. I watched her dad as he ripped open a condom rapper and put it on. I just laid back and closed my eyes as her mouth and tongue made my aching pussy feel so much better. When I felt her bumping into me I opened my eyes to see her dad behind her grabbing her hips so hard his fingers pushed deep into her skin as he was now moving in and out of her, pumping his huge penis into his own sixteen year old daughter. I looked down into Annie's eyes as they looked up at me from between my legs and saw a twinkle of delight as her own father was moving inside her. Annie let go of my breast and moved her hands down to my pussy, with one hand she spread my pussy wide exposing my clit to her tongue and with the other hand I felt her push two fingers deep inside me. Each time her father pushed into her she would push her fingers into me. The pain I had felt from her father being inside me had completely subsided and all I felt now was the wonderful warm sensations Annie was giving me, as I also felt my first orgasm of the night building deep inside me. I totally lost control when she sucked my clit hard into her mouth flicking her tongue across it super fast and pushed a third finger into me all at the same time. I had to grab hold of the pillow, biting into it to hold back my screams of pleasure and Annie had to fight to hold me down as I had started to buck, moving my hips back and forth as I came so hard. I think that soon after I came, Annie with watching me and feeling her dad inside her put her over the edge and orgasmed soon after I did. She pressed her face harder into my pussy and I felt her get all stiff as a long moan escaped her lips, making wonderful vibrations to my pussy. I was so wet then that when Annie started moving her fingers inside me again you could hear the slushy sounds it made easily, even over Annie's heavy breathing as she recovered from her orgasm. Annie again added another finger pushing four into me, spreading my pussy open wide and filling me up even more. Annie's father was still pumping in and out of her and I couldn't help but be a little amazed that he hadn't cum yet. The two boys I had been with would not have been able to last after my orgasm, and often times would not even have lasted that long. Annie rested her head on my belly as she let her dad pump her a little more, all the while with her four fingers moving inside me with varied rhythms. I was feeling so good and had started running my fingers through Annie's long hair as a feeling of such closeness filled my heart for Annie. Annie looked up at me and smiled and with out speaking (reading her lips) she asked me if I was wanted to let her dad try me again. I still felt sort of bad for being such a baby when he first entered me. Thinking that he had to be close to coming because he had been pumping into Annie this whole time, I figured that even if it did hurt like before it shouldn't last to long. I sheepishly nodded to Annie letting her know I would try again. Annie's smile grew larger and she moved up on top of me and started kissing me. As she moved she pulled away from her dad leaving him kneeling there with his condom covered penis standing there wet and shiny. After the first long passionate kiss she softly whispered to her dad that I wanted to feel him again. I was surprised at how fast he moved up behind us and had lifted my legs up to his shoulders. And then all at once he pushed into me hard and fast. If Annie hadn't been kissing me then I would have screamed again. I felt so full, if I didn't know better I could have sworn that he was even bigger now. But I think the time Annie spent licking me and stretching me with her fingers made it easier for me this time. It still hurt but at least this time it didn't hurt so bad I couldn't deal with it. I hugged Annie tight as her dad started to move faster and faster inside me. Annie just kept kissing me over and over again, and the feeling of such closeness, such love consumed me completely feeling her on top of me her warm skin next to mine the weight of her body pressed to mine. Annie was right earlier when she said if I could relax if would start to feel good. I couldn't imagine the feelings I had getting any better but they did. It's hard to describe, I became so relaxed, so filled with joy, love, such a warm fuzzy feeling filling me completely. And the feeling of his huge penis moving inside me filling me so completely, so deeply, made me feel like I was a real woman. I have to admit now that the little bit of pain I was still feeling from how big he was and the pain from the deep penetrations as the tip of his penis slammed against my cervix hard with each thrust he made, is hard to explain, it hurt but it was sort of an enjoyable hurt. His hands wrapped around my legs pulling him even closer to me and deeper into me with each thrust. (Annie told me later I sounded like an animal grunting every time he pushed into me.) I was again lost, as this orgasm hit me harder then anything I have ever felt before. Annie said my eyes rolled up and she thought I might have passed out. But I knew I was awake when I felt him slam into me really hard and hold himself there as he exploded inside me. It felt like he got even larger as I felt hot jets hitting deep inside me, his penis jerking with each blast. Feeling him loose control inside me I lost it for a third time, squeezing Annie so close to me she was not able to breathe. When my senses caught back up to me I realized that I should not have been able to feel him cum inside me. I freaked thinking that the condom he had on must have broke. In stunned shock and fear I expressed this to them, Annie just kissed me and I just heard him laugh. Annie then said that "Daddy only wears a condom with me" Saying something about not making retarded babies. Annie's dad then told me not to worry that Annie would take care of me and lick it all out and clean me up, winking at us as he said it. Annie's dad patted her on her butt and left us alone then. Annie did take care of me, doing what her dad told her to she spent a lot of time pushing her tongue inside me and sucking out as much as she could. Then we went out to the patio and got into the hot tub were she told me to use one of the jets like a douche. A trick I will never forget because of how good that felt. I really don't know how many times I had an orgasm after that but it will be a night I will always remember. And now that I have written it down in my journal I'll be able to remember every detail about the first time ever I was with a real man, an older man. Also looking back now I guess that was also my very first 3sum. (Side note: 1 month later to the day, I was so worried because my period didn't come until today. Annie and I were trying to figure out ways to explain how I got pregnant. But it's such a huge relief now, I'M NOT PREGNANT!!! YAY!!)