Sex Confessions, Sex with Strangers, Wild Sex

Sex Confessions #20: My First Lesbian Experience

This is part of our Sex Confessions series, where our readers and customers of our shop share with us their juicy sex tales. You can also send a confession anonymously here.

For my birthday last month my boyfriend Kevin gave me a present I will never forget. My first lesbian experience. It might be more of a bi-sexual experience but whatever you want to call it, it was out of this world. I’m going to write this in two part. I’m not sure if that is allowed Joe but maybe you’ll allow me to tell my story.


Kevin had made dinner reservations at our regular spot at our usual table. After getting dressed up and having a little pre-meal cocktail at his place, we called a cab and headed out.

We arrived around 8 to a small line-up. The restaurant was busy as usual, people talking and eating and all seeming to be having a great time. The atmosphere was the main reason we fell in love with this spot from the beginning. The hostess greeted Kevin by name and guided us to our table by the fireplace. Kevin took my coat for me and pulled my chair out so I could sit. Always the gentleman, I could see other women watching and smiling. Kevin’s chivalry was the main reason I started dating him. He had a great deal of respect for women and it showed in his every move.


As I took my seat I noticed something a little different. There was an additional table setting. Usually our table was set for two but tonight there was a third set of utensils, another place mat and an extra set of drinking glasses. Kevin took his seat as the waitress came to take our orders. When she left I asked him why the third setting. He shrugged his shoulders and said it was obviously a mistake. I nodded and Kevin and I enjoyed the atmosphere and some small talk before dinner.


Dinner arrived and we enjoyed our fabulous meal. The drinks kept flowing and our conversations turned from life to marriage to our situations to love and on to lust. We revisited many different topics but we seemed to keep coming back to sex and sexuality. I have the feeling that the liquor played a major part that.


I had often talked about wanting to sleep with another woman with Kevin in the room. As any other man would, Kevin had no issues with this and in fact supported my desires. We talked about how we would meet another woman, how it might happen and all the things I’d like to try in the company of another female. The waitress came with a dessert menu just as Kevin was turning me on with his views of how a night with another woman might feel like. I was halfway hoping that the waitress heard our words, my imagination fuelled by the liquor and our sexy talk. Kevin asked me if I knew what I wanted for dessert and I blushed, thinking of kissing our waitress right on her full moist looking lips. I said I’d need a few minutes to decide and she left us alone.


Then he told me. He told me that the third place setting was not a mistake. He told me about how he had talked to the girl that we always saw at various parties and functions. Janet and I shared many a drink, talking about our lives and such. We had often used her as a visual aid while we had sex and now Kevin was now telling me how Janet was going to be joining us for some dessert. I felt my pulse race. My thoughts raced to kissing her and feeling her tongue in my mouth. I took a drink and tried to compose myself. Kevin was grinning ear to ear. I’m sure he had his doubts about setting this up and I was going to make sure to show him my appreciation during the night.


I caught sight of her as she walked in. Not that I wasn’t already staring at the door or anything! lol!

She was wearing a sexy little black strapless dress, matching black Ferragamo’s and a cute little purse. Her brown curly hair was in an up-do with a couple of seductive strands cascading down her face. She stood by the front door for a minute, scanning the tables. Then our eyes meet. She smiled, nervously put a strand of hair behind her ear and started walking towards us. Kevin has his back to her but he sees my face redden and my eyes sparkle. He turns just as Janet arrives at our table. He quickly jumps up and pulls out her chair. I can’t help but to sneak a closer peek at her legs as she sits.


Janet, Kevin and I exchange nervous, “Hello’s” while the observant waitress approaches. Janet orders a drink and Kevin and I order some blueberry cheesecake. Kevin blushes next as he asks for some whip cream, his eyes darting back and forth, from Janet’s ample cleavage, to her deep brown eyes, to my fingertips seductively tracing around the top of my glass, back to her cleavage and back to the waitress. Kevin was going be in for the time of his life and me? I was on my way to having not only my first lesbian experience, but also I was about to share an experience so memorable that I now want to share it to the world. Why is this story I cannot tell?


Kevin, my boyfriend, is a professional athlete and had been very married for the last five years. I’ll write the second part of my story in a little while. I’ve left enough for you to stew on. I’m sure I’ll get some nasty comments about how I am a home wrecker, however I have no problems looking in the mirror in the morning. This story is not about what I am doing but what I experienced when I had my first taste of another woman, my first lesbian, bi-sexual experience or whatever you call it. Please suggest another “name” for this encounter if “lesbian affair” is not appropriate. I am certainly not an expert in such terms.


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