The Diary of An Older Man

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October 5, 2018

Dear Diary,

Last month I had a great experience that was not only unexpected, but also very unforgettable. I was working on a side job over the weekend doing some restoration work at a client’s house, which the homeowner was somebody I went to high school. He seemed to be happily married now and had three c***dren from what I observed from the family pictures on the walls. The family had been staying at a motel in town now for almost two weeks now, paid for by their insurance company until their house was back to order. The majority of the restoration was completed by a corporate company, but I offered to help out with some of the unfinished work that they didn’t complete, when I ran into Seth at the grocery store parking lot. After minutes of useless small talk, he asked if I could maybe help him out, after he noticed my work shirt which had the logo of another restoration company. I agreed, since I could use any extra money to save, for sure.
She lived with her parents and like I explained earlier, I had known her dad from long before, even before I decided to take this side job. His youngest daughter, Madison, was still in middle school, and was a gorgeous young girl of **teen, and she was twenty years younger than me. While I was working in the kitchen that one Sunday, she had come back to the house after her friend’s mother dropped her off from a sleepover the night before. For some odd reason she must’ve thought that everybody was back home again from the motel. I guess communication doesn’t run deep in this family. After I told her the news, and that I would be finishing up in a few hours, and with no answer from her parents after she texted them, she became very worried and than mentioned that she wasn’t all that comfortable on texting her friend again to have her mother pick her up again to drive her to the motel.
I suggested that she just stay here at the house and when I finish the job, I could drive her to the motel to meet up with her family. That is if her parents don’t respond back with a call or text to their daughter. When she agreed I told her to just relax in her bedroom or wherever and that I will find her when I’m about to leave.
After three hours of flood cutting and treating the structure of the kitchen and the final clean-up, I put a couple of frozen dinners in the microwave to heat and opened a bottle of cold beer. By the time the dinners were ready, Madison had come back down from upstairs. I was now working on my second bottle of beer, while both dinners were now eaten, the conversations between us went surprisingly well, moving from one subject to another with ease.
After our little meal, accompanied by a few more bottles of beer, we continued to sit at the kitchen island. Madison said she liked the taste of wine and had been encouraged to drink at times by her parents from the age of ten. I don’t think her parents would think that two bottles of beer would be sensible, but they weren’t here anyway.
While we talked, I told her that I’d thought she looked very pretty from the pictures I saw on the walls throughout the house, as this seemed to please her. I placed my hand on her bare leg, as I moved in and kissed her gently. She surprised me by returning the kiss very passionately. I imagined the beer was having an effect on her.
After talking and drinking the remaining bottles of beer in the fridge while listening to music from my work radio for another hour, I told her I had to lay down for a bit, as I was somewhat buzzed now. Madison grabbed my hand and showed me to her bedroom upstairs. I sat on the edge of her bed as she went to the bathroom. I didn’t know what to make of all this, so with a little anticipation I got undressed and got into her bed.
A short time later there was a quiet knock on the door as she came in, looking anything but **teen. Her t-shirt just reached far enough to cover her sweet little pussy. After getting into bed beside me she was quite embarrassed and nervous, she told me she had never been in bed with a man before, much less a boy her age. She asked me to promise that I would not do anything to her as she was still a virgin.
I told her that I would not do anything to her unless she wanted me to as I put my arms around her and kissed her a few times, saying how beautiful she was and how fantastic it was being in bed with a young girl like herself. I knew I would have to take things very slowly and keep talking quietly, if I hoped for any success. Every time I said how beautiful she was she snuggled up a bit closer and answered softly with a light giggle or a sigh. After a while I slowly slid my hand over her smooth body, held her young firm breast and felt her little nipples getting hard.
By just brushing my fingers over her nipples they were soon hard and erect. Each time I did this her little body would rise up to meet my hand and she would start to take deep breaths and hold my hand there before slowly exhaling. I considered the time was right to proceed slowly and gently, as I slid my hand down the outside of her thigh. After doing this a few times I brought my hand upwards on the inside of her thigh. She pushed back a bit as my fingers pressed up to briefly touch her sweet teenage pussy lips, but I didn’t linger there for very long.
When I thought she had relaxed enough I slid my hand down further and gently drew my fingers up and down between her smooth ass and her sweet moist honeypot, as her body twitched every time I did it. She soon started to get quite wet and slippery and as I quickened the action it made her whimper some. Then as I drew my hand upwards again my fingers moved slowly up to the closed lips of her little tight teenage pussy, until I located her tiny teen clit. This almost made her jump off the bed, so I whispered in her ear by asking if she wanted me to stop. I knew that she was getting wet, as she said no, but she begged me to be gentle with her.
Just at the top of her pussy lips I could feel the firm swollen member of her clitoris. I took it between my fingertips and slid the hood that covered it back and forth. She began to whimper louder as her kisses became even more deeper and passionate. Then I slid the hood gently back so that her tiny clit was totally exposed, and as I did this I gently held her clitoris through the hood for about a couple of minutes, I could feel it swelling and beating like a heartbeat between my fingers, and all the time she was moaning softly, whimpering, as her body began to sway in motion.
I then began to gently spread her little pussy lips wide, as this had a terrific effect on her. Her body started to jerk upwards as if she was already being fucked. I next placed my finger at the entrance to her virgin vagina and applied slight pressure, but without letting it enter. Soon I pushed a bit harder and my finger went into her up to my first knuckle. It was still very, very tight and she pulled back slightly. I kept my finger quite still until she got used to it, then she relaxed slightly. I was soon able to slowly rotate my finger gently around the tight rim of her **teen year old honeypot. When I thought she was ready I slipped my finger in up to the second knuckle. Her tight little pussy was now becoming really wet and slowly oozing by this stage, as her interior muscles were going frantic, tightening and relaxing.
Before long I was able to slip another finger into her and gently spread her apart as her hips rose and fell. She was now reaching for my rock hard cock with her tiny little hand, but I would not let her get to it as I thought my size might frighten her. I kept on telling her how beautiful and sexy she was, and shifted our positions slightly so that I could reach other untouched areas of her little teenage body.
She now seemed quite brave and confident and I now knew it was time to attempt to steal her virginity. I took my hard cock into my hand and started to rub it around her wet swollen teenage pussy lips until I was sure that she was slippery enough for me to enter her. She got a bit nervous at this stage and made me promise not to hurt her. I told her not to worry and just relax, as I told her to spread her legs wide. After a few times trying to gain access, I finally pushed my way slowly but firmly and felt my cock slide past her golden gate. This made her gasp, and I attempted no further until she had relaxed a little. Her tiny pussy muscles were going wild at this moment, as they were clamping and gripping my heard older cock, so I adjusted myself and pushed my cock deeper into her, about another inch or so.
Every time I went to push a little further she began to cry, so I had to be content with easing back a little before any further attempts. Without trying to go any further, I just let my cock rest inside her, feeling every bit of the throbbing action. This had an incredible effect on her, and although I teased her with this for awhile, I still had about five more inches to go.
At this point I suggested that she get on top so she would have total control of how much she wanted to take. She agreed, and by now she wanted every inch inside her. I said that we should roll over still joined together. I cheated a bit on her, as I pretended it was very hard to keep my balance, and made strong thrusts as we changed position, and on the second thrust I was home. She had been too occupied with not falling off the bed as she didn’t notice how much I had in her.
I told her that she now had every inch of my cock inside her little girl pussy and how proud I was foe her. For a while I began to thrust in and out of her, as Madison responded beautifully. Then I increased the speed until I was slamming her little girl bed into the wall. Our bodies were tight together, as Madison began to whimper that got more loud as she finally had her first ever orgasm. Naturally, this finished me off, as I pushed deeper into her as I came so hard, squirting my hot older man cum deep inside her little girl vessel.
It had been a long sex session and we were both sweaty and exhausted, as I slowly withdrew my cock from her. She rolled back on the bed and I curled up against her curved back. That could have been the end of the evening, but not so much. Less than an hour later I was starting to get urges again with such a gorgeous little girl next to me, as I slowly moved my hands from her breasts down to her warm pussy and although she pretended to be asleep she responded by moving her pelvis. Soon she was rapidly fucking my fingers. It didn’t take long to enter her from behind as we laid beside each other. I told her we could stay like that for a few more hours and we could both do anything we wanted to since her parents weren’t home. By 11:30 pm, she said she really needed to go to the motel.
“Ok. No problem. I can do that for you.” as I responded quickly.
I then explained to her there is another position, and I could show her really quick, before we leave. She agreed, and so I asked her to get on her hands and knees and I would show her how. When she got into position it was somewhat easier to enter her, but still tight as fuck, as she was still juicy and wet. I asked her to lower her head onto the bed and keep her ass up as high as she could. This enabled me to get right up into her, balls deep. After a few hard thrusts, she said she was getting closer to coming again and that she would like to finish off having me lying on her back, so that is how we finished a glorious long session of sex, with her legs spread as wide as she could get them as I pushed them away from her body as far as possible.
As she came, I cummed once again, squirting even deeper inside her little girl body, up into her little tummy, as I laid on top of her, exhausted. I told her that I would look forward to seeing her again if she considered it and that she must know that nothing would ever replace the fantastic time we together when she lost her virginity to me.

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Telefon Numaram: 00237 8000 92 32

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