My first time with an older woman...

When I was 25, I was having a few drinks at an upscale bar/restaurant. This place was (it closed a few years ago) a city landmark, having been around for roughly half a century. It was known for having a diverse crowd, a good mix of older and younger, white and black patrons. I had djed there that summer when this place wanted to have an evening of old school funk and Motown music, which are genres that I know and love.

I continued to occasionally frequent this establishment after their funk music nights ended once summer drew to a close. Part of my motivation was I had gotten to know a bartender during the time I played music there. Sonja, who was roughly my age, was a busty Russian girl (who spoke fluent English). We got along well and became friendly. She lived in close proximity to this bar and had invited me back to her apartment a couple of times. Sex with her was quite enjoyable. (Side note: It was a serious turn-on when, in the throws of passion, she would start talking in Russian without realizing it. I couldn’t understand a word she was saying, but I learned that orgasmic exclamations are not restricted to the border of any one country.)

The evening I’m telling you about was a Saturday. I had djed a nearby wedding, so I was still in my tuxedo. I’m not a braggart, but I think I look pretty good when I’m decked out in my tux. Sonja happened to be bartending that night. Other than another bartender, who everyone called Blonde Jen (to differentiate from Brunette Jen), no one else working there knew we had slept together. She didn’t want to spread her business around, which I completely understood, and neither did I.

By the time the wedding concluded and the equipment was packed up, it was probably close to midnight when I got to the bar. There was still a decent crowd when I arrived, so Sonja was busy, and we only spoke for a few minutes here and there. While sipping on my Captain & Coke (my drink of choice there because Sonja and Blonde Jen poured them incredibly strong for me), I noticed a very well put together older woman sitting by herself, minding her own business.

I’m very much a people person, and I’ll chat with anyone, so I approached her and asked if she was interested in some company. With a slight smile on her face, she said yes and offered me the seat next to her. Her name was Kathleen. She asked why I was wearing a tuxedo and complimented me on my appearance. I told her I noticed her because of how distinguished she looked.

At first, our conversation was light, but it was obvious that she was a very bright and thoughtful person. Our discussion became more meaningful after a short period of time. As it turned out, she was an English professor at the local college, which was the same one that I had attended. She had only been hired a few semesters previous, so there was no chance I would ever have seen her there. At some point, somewhat flirtatiously, I said it was a good thing that I never had her as a professor. With a knowing grin, she said it was probably best that I was never her student.

While Kathleen and I were talking, I got a text on my phone. I waited to check it until after she had excused herself to use the restroom. The text was from Sonja. She apparently had ducked into an unused room away from the bar, taken a quick picture, and sent it to me. In the pic, she had lifted up her shirt and showed me her red bra with her breasts nearly spilling out. She had never before sent me a picture, so I took this as a pretty sure sign that I was again going to be invited back to her place when she finished working. But now I had a conundrum. Potentially, go home with Sonja or continue the suggestive “dance” that Kathleen and I had begun?

Well, you already know the answer. This story wouldn’t be about the oldest woman I’ve slept with if I had waited for Sonja. Kathleen and I continued our discussion, and things progressed quickly. At one point, I asked if she had ever slept with a student. She said she had subtly been propositioned a few times but would never be willing to potentially lose her job over it. She added that her students mostly seemed too young for her tastes.

Everyone knows that you never ask a woman her age, so I basically said, “I’m 25. Is that too young?” She said I looked young, but my personality was of someone older. Hesitantly, she then offered up her number. “I’m 51. I’m more than twice your age.” I think she expected that would be a deterrent for me. In my mind, it was quite the opposite.

Earlier, during our banter, she said she had a mostly enclosed outside hot tub at home. After she told me how old she was, I immediately told her that “if you invite me back to your hot tub tonight, I wouldn’t say no.” She was flustered and emboldened at the same time. She said if I was serious, then she was offering. I said I absolutely was, so I cashed out both of our tabs (I paid them with Blonde Jen when Sonya wasn’t around) and I walked her to her vehicle. I pushed her down on the hood of her car, pretty much got on top of her, and we kissed heavily for a few minutes. We reluctantly stopped, and I followed her back to her house.

Her house was very big and had to be quite expensive. She took me to a guest bedroom (that was bigger than most people’s master bedrooms) and gave me a plush robe, telling me she needed to prepare the hot tub. I stripped naked, put on the robe, and waited. She returned with a glass of wine for both of us, and she was wearing a robe like the one she gave me.

She took me outside and into the enclosed hot tub. There was almost no light outside, so when she dropped her robe and got in, I couldn’t really see her body. (I noticed her athletic figure several times at the bar and was anxious to see it in the flesh.) I followed suit and joined her, but I purposely sat on the other side of the tub. A small part of me thought she was still slightly anxious about me being much younger than her.

We drank our wine and then had another glass of it from the bottle which she had brought out. We continued the interesting type of conversation we were having at the bar, and I made a point of not touching her at all. After about a half an hour, she asked if I wanted to go inside. I slid over beside her and we kissed for a moment.

We got out, put on our robes, and she took me back to the guest bedroom. She stopped at the foot of the bed and turned towards me. I undid the tie from her robe, opened it up, and slid it off her shoulders, allowing it to fall to the floor. I pushed her back on to the bed, just as I had done on the hood of her car in the parking lot. A took off my robe and climbed between her legs. I started kissing her thighs. I did this for quite a while before slowly working my way up.

By the time I finally slid a finger between the lips of her pussy, she was very warm and very wet. As much as she was enjoying it, there also seemed to be a bit of apprehension on her part. A light bulb went off in my mind. I asked if she was nervous and she said yes. I asked if it was because of my age. She said it was, that she’d never been with a much younger guy, and that the moment we got out of the hot tub, she started getting inside of her own head about what we were going to do next. I moved my face from between her legs up to hers, gave her a long kiss, looked her directly in the eyes, and said, “Just relax and enjoy. Concentrate on how it feels and let me do all the work.”

I was pretty proud of myself, because it was like a switch flipped instantly for her. It was exactly what she needed to hear. Her breathing slowed down and her body went somewhat limp. She immersed herself in what I was doing instead of thinking about it. She was able to focus on her enjoyment. As in, she really focused on her enjoyment.

She told me to put her clit in my mouth. I did, first licking it, then sucking on it with little swirls. She put her hand on the back of my head and started guiding me. It didn’t take more than a few minutes and she was ready to go over the top.

She quickly said, “I’m about to cum,” and her body began to shudder. I knew some girls could squirt, but I had never been with one who had. It was as if someone turned on a fire hose. She let go three huge projectile streams. I was drenched. Liquid was dripping from my face and hair. Even my shoulders and chest were wet.

She laid there, completely quiet for a moment. Then she looked down at me, my face still between her legs. Her eyes had almost rolled back into her head. She simultaneously thanked me and apologized. She said she hadn’t squirted in several years and didn’t realize until the last second what was about to happen or she would have warned me.

I was fascinated and she had serious afterglow. I put my head on her thigh and allowed her to enjoy the moment. I told her I had never been with a woman who had done that and would she mind if I asked her about the experience. She told me how it felt, her first time squirting, all kinds of wonderful details. Then, without me asking (I wanted to ask, I just hadn’t yet), she volunteered that she had never released near that much liquid before.

I’m not going to lie, I felt like a king at that moment. To be able to give her that kind of pleasure was exhilarating. I performed oral on her one more time. She told me as I was doing it that she probably wouldn’t squirt again. I was ready when she orgasmed, but this time it was a slight trickle.

Needless to say, the bed was basically a swamp. We both got up, she grabbed me by my cock (so fucking hot when she did that), led me to her bedroom, and told me how badly she wanted to suck my dick. She told me to lie back and get comfortable because she really wanted me to watch.

Her mouth was like a vacuum. She took my dick between her lips and down her throat. I’ll never forget seeing her look up at me as my entire cock disappeared into her mouth. She dug her nails into my thighs and sucked out every last drop of cum I had to offer. Then, like a good girl, she swallowed it all and opened her mouth wide to prove it. I told her how tremendous it felt to watch and feel her blow me. I still remember her words, “At my age, I know what I’m doing. But it takes the right guy with the right dick.”

We were both pretty spent at this point, so we laid in bed together enjoying the post-coital bliss before falling asleep. I woke up the next morning to her rushing around, as she was late for the Sunday school class that she was in charge of. I watched her nakedly walking about as she got ready after showering. She pulled a few dresses out of her closet and told me to pick which one I wanted her to wear. I chose one and told her I wanted her to go to class with no underwear on.

When she was completely dressed (I was still nude in her bed) and in a panic from how late she was, I sat up, pulled her on top of me, lifted up her dress, and held her down. I told her she wasn’t allowed to leave until she rode my cock and got me off. Knowing she had little choice, she whispered in my ear, “you have to make it fast,” put my dick inside her, and started moving up and down. It didn’t take more than a few minutes, as I was beyond erect and her pussy was really tight. I came hard inside her.

She then jokingly cursed me out, telling me that it didn’t seem fair she had to teach Sunday school to a bunch of kids while also thinking about how much of my semen she had inside of her. I quickly threw on my clothes, we kissed at her door, and then we departed. I will never forget that night.

There was one unintended, yet predictable outcome from this experience. Sonya texted me the next day and asked if I had went home with the “older woman.” I told her I had. She wasn’t upset, but said if the bra picture she sent me wasn’t enticement enough to get me to go home with her then she probably wouldn’t be inviting me back for sex again. And she never did. But… about a month later, when I was at the bar and she was working, I asked where the room was where she took the bra picture. She led me to it, unzipped my pants, and gave me a hand job. It was a literal and proverbial “happy ending” to our sexual experiences together.