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Fingering Helena

When I was twenty I had been dating a woman for about six months. We started talking about marriage. Or more specifically, she kept bringing up the idea, and I just knew it wasn’t right for me, at least not at that age. That was the end of that relationship.

I thought about my disinclination toward marriage long and hard, and concluded, at least for the time being, that it’s OK that I wasn’t like most others. I didn’t want to be glued to one person and maybe even throw off some children. That just wasn’t for me.

Despite that, I started seriously dating another woman, Helena. We got serious enough that I was able to share my thoughts on marriage and family, thinking as I did so that I was committing relationship suicide with her. To my surprise and delight, Helena lit up and said, “Me too!”

Until then, she and I had been fucking at least weekly, thinking that’s what people do, so we should too. We even had simultaneous orgasms a couple of times. Don’t get me wrong. We enjoyed the hell out of it, but for me, something wasn’t quite as fulfilling as I’d like. It turns out that she felt the same way about that, too.

This discussion was turning out to be very engaging! Naturally, I asked, “So, what kind of things do you like?”

Helena said that she does enjoy her orgasms, but just hates condoms. Bingo, that’s a pet peeve of mine too. She then suggested that I might try to do something for her with my fingers. Of course, I did and she had a very nice orgasm almost instantly once I got two fingers in her cunt.

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Asking me what I might want, I was a little shy to tell her that I might like to try the same thing. Seeing the puzzled look on her face, I asked, “Could you put a finger in my ass?”

You might think I was kind of innocent, and actually I was at 20 years old, because no one had ever fingered me. Well, I put a finger just an inch into my own ass maybe once or twice, but wasn’t particularly sexual. Yet, I somehow knew that I’d love her to try.

So she did. Helena didn’t use enough lube – actually, she didn’t use any lube at all, and pushed in way too hard. It fucking hurt! I kind of combination yelled and laughed, and she pulled out right away. We tried again with some coconut oil, and her going much more slowly. Within sixty seconds, I was squirting cum all over the place and she hadn’t even touched my dick.

As I was calming down from that, she let me know she’d like to understand what I experienced. So of course, I finger-fucked her butt. It took perhaps two minutes, but at one point when I curved my index forward against what I assume was the back of her vaginal canal, she orgasmed big-time. I mean, she really came, moaning and basically convulsing so hard I had to hold her so she wouldn’t throw herself off the bed. Her pussy hadn’t even been touched, yet she came hard.

It turns out that she was the one. We dated for six years, then we married. By then, my life had changed, and especially my attitude. I wanted to hold her close forever. I wanted a family. So did she.

That was twenty years ago. We’ve got three boisterous but happy and successful children currently 14, 16 and 19 years old. While we have fucked, without annoying condoms, as our three children prove, we have continued our alternative play. It didn’t take us long to graduate to two, then more fingers. She has successfully fisted me. She reports that there’s a constricting bend about 10 inches (25 cm) inside my insides that she can’t get past. I’ve asked her to try, but she’s afraid, perhaps rightly so, of hurting me.

I was always unable to fist her in either place. As soon as she recovered from the birth of our first child, fisting her vagina was easy. That always brings on strong orgasms. I should point out that when she has fisted me, I’ve never orgasmed, but have enjoyed the play. I have yet to successfully fist her ass. My big hand just doesn’t fit, although we have tried many times. She does very much enjoy the attempts.

We do more, too. She just loves it when I pinch her inner labia as hard as I can between my thumb and first finger. Then, I’ll pinch her clit surprisingly firmly, when I can get a grip on it. It’s generally slippery and small, so hard to pinch properly, but she loves it when I get it right. I had no idea that any woman would like such rough play. Perhaps she’s unusual, I don’t know.

She tried reciprocating by pinching my balls. That just brought on an instant ache. I have to say I don’t care for that at all. Instead, we have learned what I really like. There are a couple of things, actually. One is she’ll pinch my frenulum between her thumb and one finger, not hard, but she’ll start shaking up and down. That’s all it takes to get me to cum.

Then, when we’re feeling particularly frisky, she’ll pinch the tip of my cock with her other hand so when I ejaculate, it’s trapped inside. That kind of stings a little bit, and it stings when I pee for the next day or two. But, it’s such an intense feeling! I feel so out of control. So vulnerable. I really want her to let go – to let the cum out, but she just laughs and holds it in for at least a minute until the insides of my urethra start to itch. You see, the urethra isn’t used to ongoing exposure to sperm. They are different than all other cells of the body in that they only have half as many chromosomes. The urethra doesn’t recognize them as part of me, so that sets off an immune action inside my penis. It tries to kill the sperm, and therefore the itching. But then, she’ll just keep holding the cum in even longer. I laughingly beg her to let it out, but she just keeps it there for another full minute.

Another thing she’ll do to me is to polish my scrotum. She squeezes my ball sack in such a way that the balls are compressed loosely outward, away from my body, then she rubs the tight scrotum with the lubed palm of her hand. It’s not orgasmic, but I really enjoy the feeling.

Finally, when we’re in a really crazy mood, after I cum, Helena will polish my glans, the tip of my penis, with the palm of her hand. I squirm, I yell, I go crazy, but the only way out is to go soft. There’s no safeword because it’s not dangerous. Of course due to the continuing stimulation, I stay hard for quite a while, and have to take her ongoing torment.

We do have a nudist household. Yes, our children are nudists also within the confines of our house, our yard, and sometimes the nude beach. They are aware of our crazy sexual play, and I dare say, they are probably more sexually balanced than almost any American children. When my daughter was around 18, she met a boy who was a good kid. We endorsed their relationship. It wasn’t long before she reported to us that she and her boyfriend had been practicing many of the same techniques that she has seen Helena and I doing.

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