My First Time  

keystonenc 43M
28 posts
7/10/2005 5:10 pm

Last Read:
3/5/2006 9:27 pm

My First Time

Since this is my first post...

I can still remember the first time I had sex with a woman. What a glorious day it was, for me anyway . Although, I dare say, she enjoyed our time together as well as she came back for more on several occasions.

Anyway, I got a late start on my sex life as I waited until I was 24 to be with a woman for the first time. I don't know why I waited; I had opportunities before then where I probably could have gotten laid if I had really tried. I guess I just wanted it to be with the right person. I didn't want my first time to be with some drunken random college chick. I wanted it to be with someone I had a personal connection with and I was lucky enough to do so and it made the wait all worth the while.

The lucky lady was a voluptuous African American woman that was a co-worker at the time. We had known each other and worked together for several months and grown to be good friends. Then she got pregnant with the guy she was engaged to at the time and we drifted apart a bit. We were still friends but with everything now going on in her life we did not have as much time for each other. To make a long story short her fiancée ended up screwing her over during the pregnancy and left her for someone else.

Anyway, we grew closer together once she came back to work. In retrospect a lot of what went on in our relationship was due to me being one of the few men in her life that she could trust that was not related to her. After a few months of flirting and the like I felt there was some real chemistry developing between us and I finally got up the nerve to call her on the phone and ask her out one night. To my delight she agreed to go out with me sometime.

Now, comes the interesting quirk to our relationship. We had to try and figure out how to co-ordinate this date with her finding someone to watch her son. So, as this process was going on we continued to talk on the phone during evenings. Mostly about personal stuff we would not want to discuss around work. We were joking around and I said, jokingly, that I was going to kidnap her if we did not go on this date soon. She played along and coyly asked what I would do to her if I kidnapped her. Now, keeping in mind that we were good friends at this point and she knew I was not going to do anything crazy, I playfully responded that I was going to tie her up and have my way with her.

She was silent for a moment. I started thinking I screwed things up with her already. Then she responds back by asking if I wanted to sleep with her. I, being the heterosexual male flirting with a woman I was very attracted to, of course, said yes. One of the reasons I asked her out was because, on top of being friends, I found her to be extremely attractive. Her response to my admission floored me when she said that she would be honored to my first (I had already told her I was a virgin way before then). My reaction was that she must be teasing as she was very good at being a tease, but she wasn't. Now, this conversation was all happening on a Friday Evening. She told me that if she could find a sitter she would be over Saturday Afternoon (she ended up lying to her mother so she would watch the baby for a couple of hours).

I think we can all relate to the anguish and anticipation of an imminent love making session with someone we have been jonesing over for several months. Not to mention being the first time that I was ever going to experience being with a woman. It was so bad that I could barely get to sleep Friday Night and could not eat anything Saturday morning. The anticipation was such that I was walking around like I had just popped a couple of Viagra. She finally calls me and says she is on her way over. This also happens to be the first time that she has ever come over to my apartment. She knew where the complex was but did not know exactly where I lived. So, me being the gentleman that I am, decide I am going to go sit outside in the parking lot and wait for her. I was going to be damned if I let this opportunity slip through my fingers. God, it seemed like I was waiting forever for her to get there.

When she finally showed I must have had this look of relief on my face as she joked about me being worried that she would not be able to find the place. She was not wearing anything special just a pair of shorts and a snug top that accentuated her rather large breasts. Since she lied about where she was going she could not exactly get dolled up for me, but I did not care she looked radiant to me. She may have been anticipating this as much as I was; after all she had not been with anyone for almost two years.

I quickly escorted her up to my apartment to the awaiting fold out futon. At the time I was sleeping on a futon as I was still getting started in the world and could not afford a lot of furniture so a futon seemed to be a good investment at the time. So, here we are sitting on the edge of the futon, me being nervous as hell and staring into the eyes of the most beautiful woman I had ever gotten really close to in my life, not having a clue as to what to do. She was a bit nervous too as I don’t think she knew quite what to expect and I think she was used to having the guys make the first move. She tried comforting me a bit and telling me that we did not have to do this if we did not want to. I assured her I was okay and told her I was a little nervous and anxious. She comforted me some more by telling me to relax and that I should not be nervous. She was great she just kept reassuring me to make me feel more comfortable. Luckily, for me, she was fairly experienced when it came to having sex so after the first few awkward moments she eased in to taking the lead.

She started off by kissing me on the mouth and we did that for a minute or so to set the mood. However, she was not really into kissing much so she made the next move and took her top and shorts off. Needless to say that really got things stirring in my shorts. She took my hand and guided it to her bra covered breast encouraging me to touch her. I grope her breast for a little while then she removes her bra and eases me on my back and starts to grind her hips into mine. Needless to say this got me really excited and the dry humping did not stay so dry for long, at least from my perspective it was not so dry anymore. She was taken aback by this a bit, it caught her by surprise as she was used to being with more experienced men who were more adept at controlling things. I cannot begin to tell you who mortified I was at this. She, of course, was more than supporting and understanding. Well, I picked myself up and dusted myself off and decided that this afternoon was not going to be a complete disaster for both of us.

The futon was pushed back against a wall and she was sitting up against the wall as I pondered what to do next. I remember thinking to hell with this she is not going anywhere so we can still have some sort of fun. So, I start caressing her body and suckling her breasts and kissing her belly. I start tugging at her panties and she deftly guides them off and flips them onto the floor. I caressed her inner thigh and surveyed the area and noticed a little moisture build up amidst her thighs as I pondered my next move. Once that happened things started stirring for me again. I knew I was going to be hard again fairly soon, but I also wanted to make sure that she got off too. The way I figured it there may be a decent chance that once I got another erection and got to the point where I got my dick inside of her that I was not going to last too long due to the increased sexual stimulation I was experiencing for the first time. I was also cognizant of the idea that if I gave her an orgasm of some kind she would be more likely to come back again.

So, at this time my mission in life was to give this woman the orgasm I felt she deserved and was clearly hoping to anticipate giving the moisture starting to build up around her inner thigh region. So, I said to myself ‘Fuck it I’m going in’ and I buried my head between her legs. I think it surprised her a bit, but soon she was spreading her thighs a little wider for me to get in good. After couple of minutes of kissing, sucking, licking, and fingering her nether regions I feel her thighs clamping down around me as she starts moaning, groaning, quivering, and eventually crying a little bit. This took me back a bit; I was not expecting her to cry at all. She explained to me that she cries when she has an orgasm so that made me feel good, mission accomplished. She told me that I did not have to do that, but I said it would not be right for me to send her home without having an orgasm after I already had one myself. She smiles and tells me that is sweet.

By now I am back at full mast and she notices that I have another raging hard on and we decide to take another run at finishing what we had started a little earlier. I slide off my shorts to reveal my penis to a woman for the first time in my life. I slide a condom on and we try a couple of different positions. But, with me not having a huge penis (I suspect she was used to guys on the large size) and being inexperienced we have some minor difficulties. So she gets on her hands and knees and sticks her ass up in the air to take me from behind. Once I finally got inside her it was like nothing I had ever experienced before. I had often wondered what the big deal about having intercourse was I can jack off and get the same effect. Oh, how wrong I was about that. The experience of being inside of a woman is far superior to masturbation, especially when the woman knows who to suck in a penis and work her vaginal muscles.

Unfortunately, as I suspected, it did not last as long as I would have liked. Although, it did last a little longer than I expected it would. After it was over I lay there in all of my glory. The thing that really surprised me was ultimately how comfortable it felt to be naked around this woman, especially considering I had never been naked in front of a woman before. I just lay there and felt a sudden burst of elation come over me. I had never felt as alive as I did that day laying there next to this naked female body that just let me penetrate her stealing my last bastion of childhood innocence. As we lay there I always suspected that she was probably horny as hell after not being with anyone for a long time and probably wanted this as much as I did. When I asked why she agreed to come over she said it was because she had never been with a white guy before. I think she may have been a little embarrassed to admit she was feeling uncontrollably horny that day. She would never admit to it, but I my suspicions were confirmed to a degree when she was over at my place three days later we were giving each other hand jobs while we cuddled under a blanket on the futon waiting for the baby to fall asleep. Once he fell asleep she was riding my dick like there was no tomorrow, after I had eaten her out again of course. But that is a story for another day.

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