Having sex with a mature woman

Chapter 1 https://steemit.com/sexual/@moneytino/true-story-6-yo-fondling-a-older-woman
Chapter 2 https://steemit.com/nsfw/@moneytino/young-boy-losing-his-virginity-to-a-16-yo

THE SECRET ME

Chapter 3

Office Affair

Fresh from high school, now 18 years old getting my first office job. I was going to work at a prestigious Bank with years in the market and an image that made other companies glare with envy. I was so excited, as I have been home for months, that seemed like years. I even started missing High school, all my friends and the things we use to do to pass the time. But now, I was about to start a new chapter in my young life. I was a Collector, calling customers who had not paid for a month up to three months. A tie and shirt was a part of the dress code too, and as uncomfortable as I felt I knew I looked good. I had to work with other departments to get certain information on clients and Debra was in one of those departments. She was a light skinned cutie with large voluptuous lips. She never wore make up though, I guess maybe because she was a Christian and her denomination frowned upon a woman doing so. There were more attractive women at the office but they weren't interested and I saw that Debra was showing me a lot of interest. Smiling at me and laughing at my corny jokes. Always asked me where I went when I would be missing from the cafeteria. This is the time I would normally take a walk by myself just to get to know my new environment a little better.

We exchanged numbers and this began our evening conversations, after work ended. We spoke for hours, fell asleep on the phone. Soon both our bills were going sky high, but we never minded. Her company was good and I saw her in a different light. She was a 24 year old virgin and this intrigued me because I had a rule back then. I would never ever go down on a woman that had a dick in her before. I never made her know of this rule, but she knew we were nearing the point of being intimate. I had my little adventures before but this one would be different. All my other adventures before I was half naked, stealing a quickie before someone got home. Debra lived on her own and we had all night if we wanted. She told me that I was mature for my age and that all those things we talked about on the phone she was ready to experience them. I was so excited to hear those words come out of her mouth, because I thought I would never see a woman naked again at the rate I was going.

I kept it at a level because oral sex or O.S. as we referred to it, was a bit taboo at that time. So I told her about kissing her and making love to her, but never of my thoughts of finally experiencing a woman's cunt on my lips. The day came after three months of talk and lovemaking on the phone, getting blue balls the next day and having to go to work with that uncomfortable feeling. She told me that she was ready one day while we were at lunch together. I was shocked and excited all at the same time. Not much work was done after that because, I could hardly concentrate for the rest of the day. I was literally counting down the minutes. The day seemed to drag on and my mind ran wild with expectations of the evening. She seemed to be just as eager and was ready to leave the office as soon as the clock was on five- o-clock. We both took the bus and the driver must have been reading our minds because he put the pedal down hard and we were at the entrance to the road her house was on in no time at all.

My heart was beating hard as we both walked to her house. She seemed calm and so innocent. Nobody at the office would believe me if I told them what were about to do. We got to her house and she fumbled with the bunch of keys, to find the right one. Soon we were inside and she started undressing herself and headed to the bathroom. It was my first time to her place so I was left standing there. I guess her mind was in that moment too. I took out my wallet and searched through for a condom and placed it under her pillow, so that it would be close by when the action started. I heard her call out for me from the shower, "Are you not coming in with me?" "Yes! I exclaimed. 'I was just about to". My clothes hit the ground in a pile and I was soon in the shower with her. Her breasts were so firm and her body so curvy and soft. She soaped up a wash cloth and started lathering my body with it. My cock was so hard it was getting in the way of me and her because the bath was so small. I didn’t mind and she didn’t either. She held my manhood and washed it gently, while my hands were busy caressing her breasts and kissing her gorgeous lips. She stroked my hardness with a firm grip and moaned loudly has my finger ran up her slit. I tried getting my finger in, but it wouldn't go all the way in like it did with Cindy.

I don’t believe I ever had a virgin before, but today I will be taking Debra's virginity. I felt so good having an older woman like this, fully naked with no hopes of being interrupted by anyone. After that foreplay, we both dried off and went to the bedroom. I saw how nervous she was and I couldn’t show that I felt the same was so I took charge. I laid her down gently and started kissing her again and sucking her nipples. She was so wet, I never knew a woman could get so wet. Her eyes were closed and her legs were wide open inviting me in. As I kissed her I reached for the condom and slipped it on. I whispered in her ear," are you ready?" She nodded yes, and I tried to go in. It was a difficult task and she said it hurt but I knew I just needed to get past the front door before she started enjoying it. It was a bit awkward for awhile, especially when she said to me, "I thought you said you have done this before?" My ego was a bit bruised but I persevered and finally pushed my way past that security guard of a hymen. I was lost in a zone when that happened and excitement got the best of me. I forgot that I was to be pleasing her and not just myself. Uh-oh too late, I was cumming, filling the condom with my thick juices that I had been saving for her these past months.

We spoke about it after I left, and I had gotten home. She told me that it was painful and that she didn’t know what the fuss was all about. I assured her that it would be much better the second time. She wasn’t so sure but we were in a relationship officially now so that was a part of the package. The next time came around that same weekend. I didn’t bring along any condoms because I didn’t think she would be ready after the pain she felt the first time. I was so wrong. She was in her short shorts and had her own condoms ready. She undressed me and kissed my body before I took over and returned the favor. I felt like going down on her so bad. Her pussy was so cute and as voluptuous as her lips were. I held back the urge as we never discussed that before, and I never wanted to ruin the moment. She really enjoyed it when I sucked her nipples though; I could hear her long moans and feel her wet pussy. My finger went all the way this time and she gyrated on it as I kissed her.

I hastily opened one of the condoms she had bought, slipped it on and slid my hard cock slowly inside her now wet pussy. There was still a lot of resistance while entering her, as she was still very tight. I saw her cringe a bit too, but then she relaxed as I slowly moved my hips massaging her inner walls with my hard-throbbing cock. I asked her how it felt and she told me it was good. We made love for about two hours before I came. She never knew what cumming was and I never knew what to tell her. She knew that it felt good but had no idea if she had an orgasm. All she knew, is that it was way better than our first attempt. A prouder man than I, could not be found. I had just made love to a woman six years older than I was. I went home on a high, and thought of all the things I wanted to explore with her. This was my opportunity to bring that subject up that I have been wanting to bring up for so long. So, I asked her about fantasies that evening. I steered the conversation to the topic of oral sex, just to get a feel of where her mind was on the subject. She told me that she watched it in porn but never liked how the men came in the women's mouths. I assured her that if we did it I would tell her when I was cumming and she agreed.

Hope you all like it so far.

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Valentino out!!