Feminized at Thirty-Three

This is the story of a man who never realized the strength of his inner woman until he was in his thirties.

It is a story of loving feminization and incest.

The story is fiction. Everyone is eighteen, or older. I would normally post this story under the incest category, but I thought it would fit just as well under crossdressers.

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I was thirty-three years old before my desire for feminization took hold. Let me tell you a little about myself, and about how it came about.

I am not a big man. I stand 5' 6" and weigh 155 on a smallish frame. I had never been muscular, when young I had been slim. When I was in my late teens, and a college student, I had developed man boobs. Boobs with very sensitive nipples.

As I aged my body softened. I put on a little weight, but it was mostly a matter of muscle tone. Too much time sitting at a desk, I guess; and total lack of exercise.

My name is Dan. At the age of thirty I was living with my Mom and working as an accountant for a large accounting firm. A few years before I had been assigned to a branch office, one of the smaller ones, in the midsized city I'd grown up in.

My mother insisted that I stay with her. We had lost my father some years before. She said there was room for me and that she often felt lonely. What had started out as a temporary stay turned out to be permanent. Every time I mentioned getting my own place Mom insisted that she wanted me there with her.

My job was good. I would never become a manager. In fact I had no desire to do so. I was content to be considered a good, and reliable, employee. I made a good salary and yearly bonuses that were usually very good. Of course the bonus size depended on the economy and whether business had been good.

Mom was a woman of fifty-one when I went to live with her. A pleasant looking woman. Very slightly plump with breasts the size of small grapefruit. She had a nice butt and her legs were especially nice. When she wore nylons and heels she looked exceptionally attractive. She was a very feminine woman. One seldom saw her except in a dress or skirt, occasionally shorts.

Mom didn't have to work. My father had left her well off and I contributed generously to the household expenses. She was active in several charitable organizations and with the upscale community where we lived.

As far as I know she never dated, At least not after I came to stay with her.

Mom would often bemoan the fact that I seldom dated either. Make that never. I wasn't attractive to women and the dates I did get never developed into anything. Nor was my personality interesting to women. I had pretty much given up ever finding a woman when I moved in with my mother.

I got by with regular masturbation for a couple of years. I spiced it up with porn on the computer in my bedroom. I had a good collection of porn magazines too. I kept them well hidden.

Not hidden well enough. Mom found the magazines. That led her to a search of my computer. I had most of my porn files password protected, but I, foolishly, didn't usually delete my history.

It was all for the best, though. Mom found a video I had watched of a man eating his mother's pussy. I had a couple of magazines along the same lines. One of my favorites was entitled 'Chubby Mommies'.

Mom confronted me about the videos and magazines. I was severely embarrassed. Until it turned out that she was just as aroused as I was. She insisted that we watch some of the videos together. We sat on the couch and were soon fondling each other's bodies.

She sent me to get my copy of 'Chubby Mommies' and we read it together. That led to more fondling and hot kisses. I ate her pussy, just like the son in the video. She sucked my cock, just like the chubby mommy in the magazine. We fell into bed together and she guided my hard cock into her warm pussy.

I was in heaven. My sexual experience, except with myself, was practically nil. Mom had been with very few men. My father had been her great love and she never strayed. So we were two amateurs learning as we went. We did buy a couple of sex books and read them together. They were a big help, but that didn't help us in the first few days and weeks. We got through our early learning period, enjoyably I must say.

We found ourselves deeply in love, and lust too. We found little quirks about ourselves. I loved to lift up Mom's dress to find her with no panties. I especially loved it when she would come home from a meeting or charitable event wearing a suit with nylons, heels and the whole classy woman outfit. She would have taken her panties off in the car.

I would kneel in front of her and lift her skirt to find her bare pussy. Her juices would be flowing and she would press my head into the wild tangle of her pubes. I would eat her cunt while she sat on the couch and let the skirt fall over me. Her hosiery clad legs would squeeze against my head and the friction of the nylon drive me wild.

I soon came to realize that I loved to eat pussy. Mom did too, loved me eating her I mean. She loved it as much as I did. I often ate her for an hour, or more, before she would get my cock into her pussy; or give me a blowjob so I would cum too.

Another thing was tittie play. We soon realized that my man boobs were just as sensitive as a woman's. We would spend long periods lying reversed, kind of like a truncated sixty-nine position, so we could suck and fondle each other's tits at the same time.

It was the tittie play that led to our next discovery.

Mom was in a playful mood one evening, we had been lovers for about six months at the time. She put one of her bras on me. My man boobs filled about three quarters of the cup. She stuffed nylon stockings in the cups to fill them.

Maybe it was the sensation of the nylon hosiery stimulating my nipples. That caused my dick to harden. Or, maybe it was the fact that the bra she had put on me was a very sexy looking black silk. Whatever, I stood naked except for the silky bra and a hard on.

Mom stood back to look at me.

"Oh my God, Dan." She said happily. "That looks so sexy."

She was so deliciously juicy that evening that I didn't want to ever stop eating her cunt.

That's when it started. I was thirty-three.

It took a couple of days for Mom to convince me to try nylons. She had to show me how to put them on, but once she got me to put to try them I was amazed at how sensual they felt. Her next step was to convince me to shave my legs. She insisted that without the hair on my legs, even though it was light and sparse, the nylons would feel even better. Once I tried them with shaved legs I was converted.

Shaving my underarms was a logical next step. Except for my pubes, and underarms I had no body hair. Neither Mom nor I wanted shaved pubes so we didn't go any further. Well except for the fuzz on my arms. I thought that shaving there might cause comments at work, but I usually wore long sleeve dress shirts at the office. Of course I normally rolled the sleeves up a little. I tried it for a while, thinking I could always say I did it because of a rash. No one noticed, though. So I kept doing it.

We also started using a skin softener. It did nice things for me and I began to feel soft and smooth. I liked the feeling.

Mom bought me some bras that fit well. I was a B cup. I found myself somewhat proud of that fact. Mom also bought me a couple of garter belts. I tried them on with the nylons and one of my new bras. Mom was so excited she took me right to bed.

She sat on my face and rubbed her essences on me. She was literally flowing in her lust. Her nectar poured from her, anointing the flesh of my face. I brought her to several very strong orgasms and afterward she licked the juices from my face, all the while telling me how hot my dressing in lingerie made her.

After that I was a little easier to convince. I became quite pliant whenever Mom would buy me new lingerie, or suggest something she thought would be sexy. That's how I started wearing heels and panties around the house.

I found the panties to be the most feminizing thing I did. Much of what I have read about feminization have men, or boys, starting out with panties. For me it was almost the last step, but the one that brought it all home to me. The step that set my future course. It was then that I began to actively study and plan for my feminization

Mom was a big help. She described to me how my feminization made her feel. How seeing me in lingerie and heels made her pussy so wet she could hardly keep from dragging me to the bed.

We enthusiastically started making me up. We studied lots of websites to find ways to make my face more feminine. We found a nearby cosmetologist who specialized in such things. She, at least I think she was a she, studied me and made several recommendations. Some were simple and could be taken care of right away. She also fitted me with a couple of wigs that I found to be delightfully feminine.

Something else was happening. It was a gradual change and neither of us noticed it at first. But when it became obvious to us we realized that this was the direction we had been going since we became lovers. The fact was that we were fucking less often. A lot more of our sex was oral. Oh, we still fucked, but nowhere near as much. My own preference was licking and sucking at my mother's succulent pussy. She was coming to think of giving me a blowjob as sucking on my clitty. My cum she was starting to think of as a woman's squirting. Not realistic perhaps, but it suited the narrative we were developing for ourselves.

So, you see, we were starting to view our lovemaking with a feminine viewpoint. Our realization that this was happening led to a conversation. It was an extended talk over several months. We would take a point and chew on it and discuss it and let it sit for a while then talk about it again.

There were two main topics, with numerous sub-topics.

What did I want?

And

What did Mom want?

We had to get past the 'Oh, whatever you want I want' phase. That was bullshit. We had to look at things realistically. We had to drag our fantasies out into the cold light of day and look at them. One thing we realized right away. Unlike most people's fantasies many of ours had already come true. That was a great place to start.

The answers came. Slowly, laboriously, but they did come.

I wanted to be as feminine as possible and still be a man. I had considered a sex change, but I liked fucking Mom too much and loved her wonderful blow jobs; even if we did think of my cock as a clit.

There was my job to consider if I was going to feminize myself much further. We decided to look at our options.

What Mom wanted was a pretty woman with a cock, or perhaps a well-developed clit. One who would make love with her often. It was really that simple.

With the basic questions answered we started work on the implementation. For the next couple of years we investigated feminization products. We checked out numerous websites and read even more articles. We wrote to transvestites who had taken hormone treatment we asked questions and got answers.

I started on hormone treatment. My boobs grew, a little. The biggest change was my nipples. They had already been sensitive, but now my areolas were larger and my nipples looked like nipples. The thrill was magnitudes greater when Mom sucked on them.

Other questions involved sex. To be sure, our sex life was great. I was happy, as was Mom. We thought there might be ways to improve it, though. Once again we perused websites, and blogs. Most of what we read didn't appeal to us. But we found a strap on belt that had a vibrator to stimulate Mom while she fucked my boy pussy. We bought it and Mom took my virginity the night it arrived. My orgasm was stupendous, like nothing I had ever experienced before. She was thrilled with the orgasm she experienced too.

Once my anal cherry had been taken we tried a little anal with Mom. She found that she liked my boy clitty sliding into her ass. But far more than that she loved it when I ate her pussy and slid a vibrator into her back door. I loved it too, Mom's juices would pour from her pussy for me to lap up.

I decided to be upfront with the company I worked for. I set up an appointment with the personnel people at the home office. I talked with my boss at my office first. He made the arrangements so that the company would pick up the tab for airfare and hotel.

The personnel department was, if not supportive, at least reasonable. They told me my job would be secure. That if I needed it I could get an unpaid leave of absence. My insurance would cover only half of the cost of elective surgery, so I had to be a little frugal there. Recovery from any surgery could be covered by sick leave, or vacation, as long as I had enough time built up.

It took another year. Much time with a cosmetologist and a couple of plastic surgeries. Along with the hormone treatments I was at the point that I could pass in public as a woman. Even my voice was now feminine. I went full time female at work.

I look like a slightly overweight woman in her thirties. But that's just what I think of myself as, isn't it? I'm pleasant faced and, If I do say so, I have nice legs and butt; especially with nylons and heels. When I wear a tight dress I show a few bulges, but Mom thinks they're sexy. Apparently a lot of men do too. I get a lot of second looks.

But I still have my cock, for Mom; to her it is my boy clitty. My ass, of course, we think of as my boy pussy. I love it when she is on top fucking me. I wrap my legs over her ass and hold her tight as she sucks at my tits and thrusts into me with her strap on cock. After she has cum a couple of times, and her pussy is flowing strongly she will pull the belt off and sit on my face. I will suck at her clit and drink of her essences.

We still fuck. Mom will usually ride me until I cum. By then she will have had two or three orgasms. I always warm her up good with my tongue before she takes my clitty into her pussy; that way she gets lots of cumming before I squirt into her.

With her pussy full of my creamy cum she will sit on my face and I will eat our mingled juices from her lovely, fragrant cunt. I love the taste and I love the way she spreads our cum over my face as if scent marking me. It is such a lovely, thrilling sensation.

I so love my life as an almost woman. I love my mother, I love myself as I am. I am more than satisfied sexually and loved by a wonderful woman. Life is good.