I met Betty through a community social event that occurred several times each month. We occasionally had the chance to chat personally. It was all very benign at first, but it eventually led to one of the more memorable sexual experiences of my life, which unfortunately was never repeated.

We were a few years apart in age. At the time she was just over fifty, and me just under. I knew she was married and had five kids. She had hinted that her marriage was not a good one, but she stuck it out due to her rather strict religious background.

Eventually, I would find out that she struggled to remain true to her faith, but not her husband, who sounded like a real shit-asshole. I’d rather not go into those details, but some of the stuff she eventually told me would have been enough to get him arrested and put in jail. I was never really sure of her reasons, but she stayed with him anyway.

At the time I was in very good shape, probably the most buff I’ve ever been, especially for my age. I imagine many women think of me as “Tall, dark, and handsome”. I like to be charming, and a bit flirty, even if I know it is all just for fun, or only in friendship. I love women though, and most of my friends these days are women. I haven’t had a running buddy in quite a while.

Betty was not exactly frumpy, but she was not what I would describe as elegant either. The term schoolmarm comes to mind, but not in the strictest way. She was a bit shy in nature and had a very average mom look to her. Medium height, a bit on the plump side, with small breasts. Her smile was captivating, however, and her blue eyes would sparkle with delight when properly engaged. Her sense of humor was a bit off-beat, which made her a bit mysterious at times. She was fun to be around though and could be quite charming, in her own quirky way. We pass 1,000’s of “Betty’s” all the time, and hardly ever give them a glance.

After a long series of very platonic meetings we somehow found ourselves at my apartment. It was a tiny studio (under 400sf), jammed full of stuff, and not an entertainment pad of any kind, except for the queen-size bed that pretty well dominated the space. The apartment complex had a pool, and it was pretty nice. That would be what led to a major change in our relationship.

She came to visit me at my apartment one day (I was unattached at the time). I don’t recall now how that came about, but she showed up at my place, ready to swim. After we casually relaxed in the pool for a while we headed back to my bachelor pad.

Once back inside I said I was going to get a shower. There had at times been some sexual tension between us, but it was never overt. I decided now was as good a time as any to take the plunge, and asked her if she wanted to join me. I think this caught her a bit off-guard, and she blushed and stammered a bit. I explained to her how nudity was no big thing. I’d been a naturist (a.k.a. nudist) all my life really and assured her that nothing was going to happen that she did not want.

Betty shyly peeled off her suit and I led her by the hand into the shower. It felt good to wash off the pool smell. I was not getting much resistance, so I eventually snuggled up behind her and wrapped my arms around her. She melted back into me.

I began caressing her soft body and fondling her breasts. It felt wonderful being cuddled up next to her with the water cascading over our naked bodies. Being almost a foot taller than her, she had to feel my erection pressing into her buttocks. I leaned in to kiss her, and she kissed me back. I did not have a big water heater, so we ended the shower session fairly soon.

Hardly a word was spoken as we got out and dried each other off. We returned to the main room and I invited her to lie down with me on the bed. I could tell that she was very nervous, but still, she offered little resistance.

We began talking. A lot of stuff got aired out in a relatively short time. I know she wanted to have sex with me, and it was relatively risk-free, as I got snipped about five years earlier (I never had any kids). Although she wanted to have sex with me, the deal-breaker for intercourse was that I am cursed with “the gift that keeps on giving” (HSV-2). She was understandably too nervous about that, so I let it go.

I offered to please her orally. She said no one had ever done that to her. I was completely floored. I could not believe that a woman over fifty, well educated, and fairly liberal in nature had never experienced cunnilingus. It took a bit of convincing to assure her that there was no danger of any kind involved. In time she acquiesced. I was ecstatic because pleasing a woman with my mouth and fingers is a favorite activity of mine.

I had her lay back on the bed. She seemed really tense. She was obviously breaking a lot of barriers here. She had never had sex with anyone but her husband and had never gotten a good licking. I’m not sure if up to that point she had ever really had a decent orgasm (if any at all).

In retrospect, I wish I’d taken my time more, and tried to get both of us more relaxed. Her tension and nervousness were palpable, however, and I felt a sense of urgency to try and give her a good orgasm before she changed her mind.

Betty lay completely still and silent. I was very stimulated though, and apparently, she was too judging by her wetness. Her breasts were very soft, capped by large nipples that had become very puffed up as I played with them and licked her slit. (Puffy nipples are a huge turn-on for me.) I tried to take my time, and played with her pussy lips, clit, and opening in a variety of ways, with varying intensity. I also continued to caress her incredibly soft skin, in between playing with her breasts and nipples.

I was really beginning to wonder If what I was doing was having any effect. Most women I’ve gone down on really go to town. All of them at least writhed and moaned at the experience, even if just mildly, giving some kind of reaction at some point along the way. Betty was almost completely still, and silent. I was kind of busy, so I could not tell very easily if her breathing was becoming more excited.

I was about to give up, or at least change my tactics by stopping with my tongue and giving her a full body massage with my hands to get her more relaxed. I then noticed her body stiffening up a bit, then relaxing. She let out a gentle sigh, experiencing an orgasm, and then softly said, “I cannot believe that I’ve been missing that all these years.” The reality of this being her first orally induced orgasm once again had me a bit stunned.

I slid up next to her and held her in my arms. She calmed down after a bit and we kissed some. Then we talked about what had just happened. I was still very turned on and had a raging hard-on that was pressing and pulsing into her leg. I asked her if she had ever seen a guy masturbate. She shook her head. I asked her if she would like to watch me. She nodded.

I lay back and began to stroke myself. Betty propped herself up a bit, to get a better view. She seemed a bit spellbound by the scene in front of her and began to idly play with herself… petting her pussy and massaging her breasts and teasing her nipples. It did not take me long before I sprayed my cum all over my chest and stomach. She stared in wide-eyed wonder.

I cleaned myself up, and she expressed a need to leave and tend to her kids that were still at home. I watched her slowly get dressed and we chatted casually all the while. I gave her a hug and a quick kiss as she got ready to leave. She thanked me for the experience.

I regret that we never got a chance to repeat that opportunity. My ego wishes that I could have pleasured her at a time when we were both more relaxed. I’m curious about what heights I could have taken her to. I sensed a strong sexual animal in her that was dying to be released.

After that encounter, our time together tapered off. Over the following months I began to notice that when I saw her at the community socials where we had met, she was frequently with another guy who was a regular with that crowd. I kind of suspected they were sexually involved, and I was happy for both of them.

I eventually found out that she had gotten divorced, and then married again, and moved to another part of the state. I moved out of state during the time she was away. I have a connection with her through social media but have not made a strong effort to communicate with her. I suspect her second marriage may have ended as well. She has apparently moved again to another state (closer to where she grew up), and I can see no indication that she is married now.

Sometimes I wonder how big of a part our sexual encounter led to her finally dumping that jerk of a first husband she had. I hope she is happy now.

I also feel the need to add here that I have since become much better educated about more ethical ways to approach consent and boundaries. I would not approach a situation like this quite the same today, though I would still desire the same outcome.