My initial entry into the lifestyle was when I had a private tennis coach. I was good but had some issues, and it was decided that I needed a personal coach to get me to that next level.

When I first met Terri, she was somewhat intimidating. She was in her late twenties, almost six feet, and physically fit. She had played in college and was going to turn pro, but a knee injury took that dream away. Just the opposite of my shy self, she was very outgoing.

As the lessons continued, we started to get along very well. She made me laugh a lot, and I became attracted to her. I sometimes even had fantasies about her when masturbating after I became more enthralled with her.

I always had feelings for girls but had never acted on these feelings. Being shy, my sex life before this was limited to one nice guy. Both of us were virgins and a bit awkward regarding sex. So I had no idea how to share my desire for her. Sometimes just had the desire to kiss her when I showed up for practice but didn’t have the guts to do that. And seeing her change in the locker room made me warm inside. I had plenty of daydreams of being with her.

One day she invited me for a cookout with other people she coached. When the party wound down, it was just her husband and I who were left. I had been talking with her so much I hadn't even realized that the party had ended. She told me not to worry about it and that I should not be in a rush to leave. Her husband said he had a business outing and was taking off.

It was a hot summer evening, and Terri suggested we hang around her pool. She knew I would enjoy swimming as I competed on the swim team. So I changed into my swim gear from my car and went to the pool. Terri was already there in a skimpy bikini.

She caught me staring at her barely covered body and said she would change if it made me uncomfortable. She revealed that she usually went nude when she swam at home. I embarrassingly stuttered that her bikini was fine.

Laughing off my embarrassment, she told me not to worry. She mentioned that she was flattered when she noticed me staring at her a couple of times in the dressing room at the club. I wasn't sure what to say, so I just told her that she was a very attractive woman, which led to a conversation about my feelings toward women.

At first, I found it difficult to talk about as I was young and thought women weren't supposed to like other women. Oh, the joys of Catholic school education. Somehow, she got me to open up, and I let her know about my first boyfriend and how I found myself sexually attracted to some women.

She said it was surprising I hadn't been with more. Since she had noticed I shaved my pussy, she thought I was more open sexually. But I was shaved because I was into swimming and had to keep trimmed. And since I never was that hairy, I just shaved what little I had. I felt a bit brave and asked if she shaved because she was very open sexually.

She revealed that she had only been with a few couples and together with her husband, some women. Being just one on one with her husband or with another woman was her preference. This was the first time she told me she liked women, which began to excite and confuse me at the same time. Were we having a nice conversation between a student and tennis coach or was she coming onto me? She sensed I was a bit confused and suggested we swim.

Swimming relaxed me a bit, and we just goofed off as the conversation moved onto more mundane topics. She exited the pool to get a drink, and when she jumped back in, her top came off. She quickly went to put it back on, but feeling somewhat brave and excited, I told her it was OK if she usually didn't wear it. So she threw it on the deck, and we continued to talk.

By now, I was getting more relaxed with her but also excited about where this might lead. Noticing my unease, she offered me a drink and suggested we just sit and chat. Sitting in the shallow end with a glass of wine, I began to open up to her questions about my life. She asked me why I thought liking women was wrong. After stumbling with my answers she told me that a lot of women liked both men and women, sexually.

I asked her about her past sexual experiences and got excited by her answers. She told me about one experience with a woman she had when she was much younger. It wasn’t only sexually exciting but also very erotic. It sparked my interest even more somehow as I was pretty excited already.

Getting bolder, I asked her why she skinny-dipped in the pool. She told me she rarely wore clothes around the house if she didn't have to. Both she and her husband were semi-nudists but didn't go to nude beaches. I told her it was OK if she wanted to be naked in the pool or around it. It took her about ten seconds, and she was tossing off her bikini bottom.

She said I had a wonderful body and asked me why I didn't bring a bikini. This caused me to go nuclear red in my face. I thanked her but said I wasn't that pretty. She chided me and let me know she thought I was very cute and told me I didn't have to wear a bathing suit if I didn't want to.

In a bit of a panic, I excused myself quickly and ran to the bathroom, where I had a moment to consider what she said and thought for a bit. I worried that she might not find me attractive if I was nude. After thinking a bit, I decided she wouldn't even suggest it if she didn't want to see me naked. After getting myself under control, I decided to go for it as I wanted to experience what sex would be like with a woman, with her specifically. I returned to the pool and sat beside her again. But this time with my thigh touching her.

I told her I would like to go nude if she was serious. She responded by slowly pulling both my straps down and helping me pull off the bathing suit while I stood up. When her hand lingered on my rear, I got embarrassed again and quickly sat down. For a while, there was a long silence where I just leaned back and let the water wash over my nude body sitting next to her. I could feel the warmth of her leg against mine. I was excited. My nipples were erect and hard. Glancing over I saw hers were too. She caught me looking and asked what I thought about them. I told her they were beautiful.

She looked me in the eyes and told me that she thought I was beautiful but would not force me into anything, nor would she hold it against me if I just wanted to talk and never bring it up again. I told her that it was fine. I had sunk into the water up to my neck covering my excitement but finally sat up straight as I started to feel more relaxed with her. She placed her hand on my thigh. I quickly grabbed her hand in an automatic reaction to take it off, but I didn't remove it.

After a bit, I released her hand, and she took it as a sign. I was now feeling my pussy was very wet and hot. I reached over with my hand to touch her thigh, and she grabbed it instead and kissed it. She leaned in and kissed me. At first, it was a light kiss, but soon, we wrapped our arms around each other and kissed deeply. We continued to kiss, and her hands wandered all over me. We finally took a breath, and she took me by the hand and led me to the shower, where we rinsed the pool water off our bodies. She slowly dried me off and brought me, by the hand, to her bedroom.

Nervousness was beginning to add to my excitement, but she never gave me a chance and started kissing me and gently pushing me onto the bed. We kissed and rubbed our bodies together for a while, and then she gently pushed my head down to her breasts. Getting the hint, I kissed and sucked her nipples while she gently rubbed my head. Then, as she gave my head a slight nudge, I started kissing my way down her body, down past her belly to her pussy. First, I just kissed her outer lips and down her inner thighs. She smelled nice, and I had tasted myself before, so I wasn't afraid to taste her as I started licking and kissing her pussy.

She guided my head and gave me gentle instructions to me about how to make her cum. She told me to insert my fingers into her and keep licking like I was. I could feel her getting wetter in my mouth as she tensed up and grabbed my head tightly. Finally, her thighs squeezed my head, and she started cumming. It didn't last long, but she relaxed, pulled my head back up to hers, and kissed and licked my face clean, tasting herself as she did.

After she had recovered, she had me lie on my back and retrieved a vibrator. I had never used a toy but relaxed enough with her that I was eager now. She gently rubbed it over my hard nipples, at first making them achingly sensitive, and then lowered it to my pussy. She began gently rubbing my clit with it. It took a bit of time but I became very aroused and wet. She knew and slowly inserted it in me and began to fuck me with it gently. Feeling the sensation of a vibrator in me for the first time was so exciting. Having a woman doing this to me was also an exciting first. I could see her smiling lustfully as I got wetter and much more excited. Seeing her very hard nipples and how excited she was making love to me only excited me more. Immediately, I started cumming. She quickly pulled out the vibrator and told me to get all fours.

Her excitement was so obvious that I had cum so quickly. I quickly did as she asked. She strapped on a dildo and slowly eased herself into me again. I was so wet, I didn’t need any lubrication. This was a very different experience as I had only made love with a boy a couple of times and never in this position. The dildo was significantly larger than he was, making me feel very full. Allowing myself to be penetrated in this position, I felt very dominated and vulnerable, but also incredibly turned on.

I was flattered and happy that she wanted to make love to me in this way. As I got used to the size of the dildo, she increased the pace. I started pushing back against it to feel its size deeper in my pussy. With that and my breathing now coming in small gasps, she must have known I was getting close again. The feeling of being filled up into my core brought me over the edge.

When I started cumming, she continued breathlessly pounding me. I could tell by her excited breathing and frantic thrusting that she loved doing this to me. She made me cum several times before she finally stopped. I was dominated but in a very caring and loving way.

I finally keeled over and collapsed on the bed in the fetal position. Gently pulling my legs apart, she went down on me and started cleaning me up. Her licking of my very hard and sensitive clit made me cum yet again in one final orgasm. I was spent. Sensing I was done, she relented and gave me a big hug and kiss. We showered, and I cleaned up. As I was leaving she kissed me in a lovingly caring way.

Heading for home I felt so fulfilled and happy. Happy that I had made real my fantasy about her. Happy that it was so much more than my masturbatory imaginings about her. Happy that I had broken that taboo of a sexual experience with a woman. Happy and fulfilled that it was such an incredible experience. It was the first time I had cum other than by my own hands, masturbating. It was the first time I had multiple orgasms.

It had been a wonderfully memorable day, and I had discovered how exciting sex could truly be. She had made sure this would be an unforgettable first experience of sex with her. I had enjoyed my experience with the boy prior to this night, but this was a far deeper, more satisfying experience. I now knew how good sex could be and how much I loved it.

Thankfully, tennis practice was only two days away!