My First Time With A Woman
By request. This is how I remember my first time having sex with another woman.
I just started my new job fresh out of college. I was ready to take on the world! But I was also very scared all at the same time. Being in a financial position for a large company with lots of responsibility scared the crap out of me. My manager was a middle aged woman who was tall and thin with steel blue eyes that could either make you tremble with fear or excitement. She had a beautiful smile too and an aura of confidence that just had me mesmerized from day one. I'd happily do every little task, report, or analysis she wanted. I even would bring her coffee just to do what I could to impress or please her. After 2 or 3 weeks on the job she called me into her office. I was nervous as hell because I had messed up some numbers on a huge order that could have cost the company over $10,000.00. I was sure I was going to get dinged for that. Instead she pointed out how I made the error and what to do in the future to prevent such mistakes. After about a half an hour of being taught and corrected she said we should have dinner one day soon after work, on her so she could give me "more personal and thorough" training. I still remember when she said that looking at me and smiling with her hand on my arm, I melted. I might have been too eager saying sure, whenever you like Ms. Stevens. She said ok how about tonight then at 7 at Antonio's? And call me Kate. Yes Ms. St... Kate!
I had never eaten there since it is mega expensive and out of my universe. Anyhow I get home after work, and have an hour to get ready. I was so nervous but excited too. In hindsight I had a crush on her even though I didn't think of women sexually at the time. I was just totally infatuated with her and wanted to be just like her. So I get there and as luck would have it she arrived right behind me. So we sit down and get a class of wine and she orders for us both. She just took over everything, telling me that she is the boss and will take care of e everything. I just said oh, thanks Ms. Stevens. She said, if you insist on not doing me Kate, we will have to do something about that. She had such an evil grin, we both laughed so loud people looked at us. Anyhow, long story short, we eat a fantastic veal picata dinner and way too much wine. She says we're both not driving home and called a cab for us. While in the cab she's sitting right against me, and was putting her hand on my knee and lightly rubbing up and down. I didn't even notice really except that I was getting wet. My mind was racing and I was wondering what the hell was going on. Then she just came out and said it. I want you then kissed me. I was shocked. But I didn't resist. She said I can object and it won't affect my job status and if we proceed, no one at the company can ever know. I said I've never been with a woman ever. She said but you kissed back. I said I liked it and I'm open to trying but can't promise anything since I have zero experience. She missed me again and said don't worry honey, just let me take care of everything.
The cab takes us to her place... Wow! What a beautiful house on the water, 4 bedroom, swimming pool, jacuzzi... You name it, she had it. So we go to the living room and she brings another bottle of wine and pours two glasses. She then says here are the rules...
You are to submit to .y every request without question while we are off work. At work we will always be professional and our off work relationship will have no affect on our working relationship. At work you call me Kate. Inside my house you call me Miss Kate. I am a dominant woman and you will be submissive to me. No harm will come to you, not will I ever hurt you for my pleasure. I may tie you up on occasion but there will be no whips or stuff like that. Do you agree to these terms? I said, I think so. But what if I don't like sex with women? She said then we will just have our office relationship and this will all be forgotten. We drink to it and then everything changed. She stood up and took my hand and walked me into her bedroom. She sat me on the big beautiful king size 4 post bed and said strip, I'll be right back. I asked if I could pee first so she showed me the bathroom and I went. I might have bolted because I was very nervous but had alcohol fueled courage and I was already wet with anticipation. When I got done peeing, washing up a bit after stripping naked and opened the door to the bedroom she was standing there wearing a black bustier and a black thong with black nylons, garter and heels. She looked so sexy I gasped. She took my hand and laid me on the bed, and started kissing me passionately and had her hands on my boobs pinching my nipples which was sending shock waves through me right down to my dripping wet pussy. It's kind of a blur really but the next thing I know her fingers were inside me and I was cumming. Yes yes she said, you seem to like this. Uh huh is all I could muster. She stopped and said uh huh who? I said Miss Kate? Yes, always use my name when addressing me, my little pet. Then she went back to kissing me and fingering me. I came again. I should tell you that she has a very long tongue which I absolutely loved, very soft lips and almost no boobs at all. The boustier made the look a little bigger but mine were bigger and I was only a 34B at the time. She had tiny pink nipples too that were adorable. She loved mine because they were pretty big even back then. She loved to suck on them too, which I love! The next thing I know is that she had four fingers in me and I'm about to cum again then she slides down and starts licking my clit and I'm convulsing with probably the biggest orgasm of my life at the time. I didn't even notice that she had her whole hand in me. I squirted for the first time ever and she just lapped it up. I passed out from cumming. Honestly. I passed out. I don't know exactly how long I was out but it was only a few minutes. She was lightly slapping my face saying over and over, Trina wake up. I woke and said wow, what was that??? We laughed and kissed and hugged. She told me she loved my sweet pussy and how wonderfully stretchy it was. Lol. Stretchy? I noticed she had taken off everything and was completely naked like I was. She was waxed down there and smooth like me. She said touch my pussyine you line yours touched. So I started lightly rubbing her clit, and then dipping into her wet hole. Even after that her clit was pretty tiny compared to mine which is big by any standard. It's my favorite part of my body. Anyhow she did have nice big labia and I loved the way they parted like butterfly wings. She said lick it now, so I did. I had never thought I would be doing this. But here I was sticking my tongue into another woman's vagina. I loved it. She smelled sweet and slightly musky but it was intoxicating. I licked her juices up and swallowed. I licked her clit and she came. She said, fingers too, keep licking and finger fuck me pet. I continued to lick, put one, then two, three, four fingers. She came again and again. Put your whole hand in me now!!! I did, she came, juices gushing all around my hand and on my tongue. I licked and sucked and drank all I could. She bucked and bucked and nearly broke my nose. I wasn't ready for all that. But I was hooked. I couldn't get enough pussy. I wanted to drink her all up. We both passed out some time later. When we woke the next morning we missed and had more sex. Since it was the weekend we had ..(continue confession)
