Andy’s Journey Ch. 01

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This story is about an incestuous relationship. There are also elements of submission and dominance.

All characters are age eighteen or older.


My name is Andrew, usually called Andy. This is the story of my journey, an account of my private ways. Some may call it a tale of degradation, not I. While outwardly a normal American male I had a secret life that, ultimately, brought me joy and satisfaction. But that would bring me disgrace and condemnation if it was ever revealed.

It was my ex-wife who got me started wearing women’s panties. Her name was Amanda. A tall, voluptuous woman who turned men’s heads. Some people wondered what she saw in me. It didn’t matter. She did say once that she was attracted to small men. That was enough to get us together. She had flirted with me to get me to ask her out. I had never thought I would have a chance with such a statuesque woman. When she found out how well-endowed I am it was a whole new ball game.

Our sex life was an adventure. The night before our wedding she urged me to try on her panties. I was in love and could not refuse her. I tried them on and they fit. I am a little on the small side, 5′ 6″ and slim. Although fit, I am not muscular. In fact Amanda was taller than me by an inch or two. She had a well-shaped ass that was broad enough that the silk panties fit my small frame.

I ate her cunt that night while wearing the panties. Somehow it seemed to make me enjoy her aromatic pussy even more than usual. Later she sucked my cock after pulling the silken underwear down onto my thighs, just far enough to free my hard shaft.

I was wearing her panties under my tux the next day for our wedding. By then I had realized that I was enjoying the feel of them against my skin and the silken support for my balls. Over the course of the next couple of years we continued our adventurous ways. Amanda kept urging me into women’s lingerie, and later skirts and blouses. She would spend an hour or more making me up and fitting me with a wig. I never complained. I had come to enjoy the feeling of femininity I had developed.

By the end of the fourth year of our marriage I was regularly wearing a sheer nightgown to bed and acting as a surrogate lesbian lover for her. I was mostly content. Her pussy was wet and fragrant. On occasion she would squirt and I would avidly lap up her cum. I seldom fucked her any more. Despite the fact that I am well hung and that Amanda thoroughly enjoyed it when she did take my cock into her lovely pussy.

Although I would get throbbing hard-ons. I usually had to find relief through masturbation. A couple of times a month she would push me onto my back and ride me until she had cum several times. Only at those few times was I was allowed to cum in her pussy. She would sit on my face afterwards and I would suck my cum out of her lovely cunt. Other times she would butt fuck me with a strap on. I enjoyed that. The stimulation of my prostrate would cause me to cum explosively. She would laugh at the puddle of my seed on the sheets.

It was at the end of that fourth year of marriage that she introduced me to Sam and Jane. Then told me she was leaving me for them. “A real man and a real woman.” She had said.

I was crushed. I tried to talk her out of it. She was the only woman I had ever loved. I was wasting my breath. She despised me now, loathed the creature she herself had created. Defeated, I called my mother and asked if she could put me up for a while.

Amanda had a good income, as did I. We are both accountants. She didn’t ask for much. She only wanted to be rid of me. I slunk home to Mother and gave her the house in the divorce settlement.

My women’s clothing I put in storage. I did keep a few pairs of panties to wear when I was alone.

Somehow I was able to keep my job. It was close, though. I had a few friends at work, they didn’t know about my cross dressing, who helped me get over the worst. They took up the slack for me and saved my job. I have to admit that my boss gave me every break he could. I was sincerely grateful to all of them.

My mother, too, was supportive. She never pried too much into the reasons for the failure of my marriage. She told me I could stay as long as I wanted too. We had lost my father to an accident when I was in my early teens. She said she was happy to have a man around the house again.

Mom, Alice, was in her mid-forties. Like my ex-wife she was a largish woman, but not as tall or as shapely. In fact she is just enough overweight to show a few bulges. Buxom would describe her well. She was 5′ 8″ and weighed about 170, on a large frame. She was a pleasant looking woman and very friendly. She had been a loving mother to me and we became very close after the loss of my father.

Mom had occasional dates, but nothing ever caught fire for her. She had several women friends who would get together for bridge or a night out. Two of the women were especially close friends. Both lived quite close to us and she would often get together with one, bursa otele gelen eskort or both, for coffee or a drink.

She had a good job and was financially secure. Mom’s background, like mine, was accounting. She had worked her way up to an executive position with a regional bank. Even though she had a good income, and was scrupulously honest, Mom had always seemed a little grasping to me. She was always looking for a way to make more money. I could ignore her trivial greediness. She is my mother and I love her.

I tried to make myself useful to my mother. I had offered, several times, to find an apartment; but she wouldn’t hear of it. I didn’t want to impose on her so I tried to be as helpful as I could. I helped with the housework and some of the cooking. I took over the laundry too.

I liked to put on panties when doing the laundry. I would wear my male clothing over them. Doing the laundry gave me a chance to wash the panties I wore without Mom finding out about them. There was another reason for taking care of our washing. I was able to sniff and taste Mom’s panties. Amanda used to rub her soiled undergarments over my face. I had found myself looking forward to it. Mom’s were even nicer, I was soon anticipating putting on silky panties and using laundry chores as an opportunity to bury my face in her savory underwear.

Mom had never said she disapproved of Amanda, and when I came back home she didn’t say anything against her either. That is until she ran into Amanda at a nightclub while out with her friends. I had been back home for several months by then. Amanda was with Sam and Jane. She introduced them to Mom as her new family and then asked snidely, “How is pantie boy doing. Does he still dress up?”

Mom asked her what she meant and Amanda said. “You mean he wears man clothes now?”

Amanda walked away from her after her last remark. Mom resisted an urge to run after her and make her explain. It would have caused a big scene that would only have hurt me, her son. Mom looked around to see if any of her friends had overheard, but no one was close.

After a restless night Mom decided she had better talk to me. If for no other reason to let me know what my ex was saying about me. It was a Saturday so work wasn’t a problem for either of us.

Mom was in the kitchen when I came downstairs in the morning. She smiled at me and poured my coffee. After I had enough to get me going I asked her. “How was your night out?”

“Not too good,” she told me. “I’ll tell you all about it after breakfast.”

After we ate she told me what had happened. I was stunned, and almost speechless.

“I am only telling you about what happened, Andy. That bitch is spreading lies about you.”

I broke down completely. “It’s not a lie, Mom,” I sobbed.

I started to tell her the story stammering and stuttering in my grief. Soon after I started to tell my sad tale, between snivels, Mom took my hand and led me to the living room couch. She sat close to me and put her arms around me drawing me to her ample bosom.

I couldn’t tell her the details of my married life, only the fact that I liked to wear women’s clothing. I would break down in tears whenever I started to talk. Mom hugged me and petted me. “It will be alright, Andy,” she told me in a soft voice. “I know you’re a real man.”

We sat like that all morning. Occasionally I would try to tell her more of my story, but would break down again after on a couple of sentences. I couldn’t eat lunch and Mom led me to my bedroom.

“Lie down and rest, Honey,” she told me. “We can talk more later.”

My sobs had ceased, but could start again in an instant. Mom sat on the edge of the bed and leaned down to kiss my forehead. I clutched at her like a drowning man. “We’ll prove you’re a man, Andy.” She said.

She stayed with me for a half hour, or so. I was starting to doze off when she leaned down to kiss me again. “You can dress like that for me, Andy, if you want to. I think it would be fun.”

I opened my eyes wide and looked at her, surprised at her words.

“Really,” she said. “You’re my little boy and I love you. Get some rest now.”

I dozed off for a couple of hours. I woke up thinking about what Mom had said. Did she really think it would be fun for me to dress up for her? It was almost too much to hope for. I got up and took a quick shower. It made me feel a little better and I put on a pair of my favorite panties instead of my boxers. The panties were silky with a couple of small bows and lace trim. I covered myself with a robe and went downstairs. Mom insisted that I eat something since I hadn’t had lunch. She fixed me a small snack and then we went to sit on the couch again.

She held me close, as she had earlier, and encouraged me to tell more of my story. I was able to get a little more off my chest, but soon dissolved into tears again. In distress I lay on her lap and rubbed my face against her breasts trying to feel the comfort bursa eve gelen escort bayan that I had got from her as a small child.

Mom responded like the mother of a baby. She held my head as if I was suckling her and made soothing sounds to calm me. My mouth found its way to her tit. In my torment I sucked at it through her dress and bra.

Mom slipped the straps of her dress off her shoulders as I continued to suck at the fabric. She pushed me back far enough to let the bodice fall to her waist and opened the clasps at the front of her bra.

Her plump tits sprang free and she pulled my head back to suckle again, at her bare breast now. I sucked at her nipples feeling them harden between my lips. I nipped her a time or two and she sighed when I did. Sucking her tit had a remarkably calming effect on me. I stayed at her breasts, switching between them, for about a half hour.

I had gathered some courage as she calmed me. I looked up at her and asked, “Did you mean it when you said it might be fun for me to dress up?”

“Yes,” she replied, but she didn’t say anything more.

“It wouldn’t disgust you?” I asked.

“You’re my son, Andy. I love you however you want to be.”

“Everything’s in storage,” I said. “Except for some panties.”

“We can go get it if you want to,” Mom said. “It’s still early enough.”

“Yes, let’s,” I said. I felt excited. “I’ll get dressed.”

I jumped up and started for the stairs but Mom called me. I stopped and looked at her. Her breasts were still bare and she looked beautiful to my biased eye.

“Are you wearing panties now?”

I nodded and she said, “Show me.”

I was embarrassed but managed to open my robe and show her my pantie clad loins.

“Take your robe off and turn around,” she commanded.

I obeyed and dropped my robe to the floor. With my hands on my hips I playfully turned full circle, like a model, to give her the full view.

“They look nice,” she said. “You don’t need to hide yourself under a robe.”

“Thank you, Mom. I’ll be ready in a couple of minutes.”

I turned to go upstairs but changed my mind and ran back to Mom to hug and kiss her. My heart was full of gratitude and love for her. I wanted her to know it.

“I love you so much,” I told her.

Within a couple of hours we were back at the house with my things and some Chinese carryout for dinner. Mom helped me to carry my bags to my room.

Mom stayed with me as I picked out a lacy bra that matched my panties. We, my ex and I, had found a shop that catered to cross dressers and had bought several that were designed for men to wear. We had preferred those with little, or no, padding. Rather we liked the bra to mold the fleshy parts of my chest into a pair of small breasts.

Mom watched me put it on observing as I pushed my breasts into the semblance of a bosom. She smiled at me when I had it to my satisfaction.

“It looks very nice, Andy, sexy. I like it.”

I got a silk robe from my suitcase and put it on. Together Mom and I went downstairs. Mom suggested a drink before dinner and I agreed. She made one for each of us and we sat on the couch and chatted.

Our conversation was not about my failed marriage or my cross dressing. Rather we talked about our work and her friends, Bridget and Myra. Bridget was married with a daughter in college, Myra had been divorced for many years; she had no children.

We finished our drinks and ate dinner. Afterwards we sat together again on the couch. Mom let me snuggle up to her, but did not offer me her breast again. We turned on the TV but weren’t really watching it. The sound was low so we could talk. We still avoided the subject of my marriage but Mom seemed interested in my feminization.

I mentioned that I would have to shave my legs so I could wear my nylons.

“That would look nice,” Mom exclaimed. “I’ll look forward to it. You can feel free to dress like that around the house, Andy. So far I find it quite erotic.”

Mom’s words surprised me, but I refrained from commenting.

We talked a little longer. Then Mom said it was time for bed. I agreed. Before we went upstairs Mom looked at me and said seriously. “Andy, I think you have to talk all this out. About your marriage and Amanda. You can tell me whenever you feel like talking.”

“Thank you, Mom,” I responded. “That’s nice to know. There is much I haven’t told you.” I was on the verge of breaking down again and Mom hugged me until I was calm again. We went upstairs then.

In my bedroom I got a sheer nightgown out of my suitcase and put it on after taking my bra and panties off. I enjoyed the feel of the sheer fabric again my bare flesh. I went to bed, but could not get to sleep. Alone in my bedroom the angst returned to haunt me. I found myself racked with sobs and alone in my bed.

Mom must have heard me. She came and sat on the side of my bed trying to calm my shattered nerves. She lay down next to me bayan eskort bursa and held me. As before her embrace calmed me. She caressed me and petted me until I fell into a calm sleep.

I woke in the morning to find myself in bed with my mother. She had slept with me to keep me calm. It had worked. I felt rested. My feeling of tranquility vanished when I realized that I was spooned behind my mother with a hard-on nestled in the crack of her butt. My arm was over her and my hand inside her nightgown fondling her tit. Her own hand covered mine.

Aghast I tried to move away before she woke. I was even more shocked when she said, “Don’t move.”

After short while she said, “I guess I better get up. I need to go to the bathroom.”

She moved my hand from her breast and stood. I saw that she was dressed in a cotton nightgown that, although low necked, did not reveal much. She came back after her trip to the bathroom and sat on the side of the bed. She leaned down to kiss me. On the lips this time. The kiss lingered for a moment, just long enough to be more than motherly.

“I’ll start breakfast,” She said. “Come downstairs when you’re ready.”

She started to leave but turned back to me. “I meant it,” she told me. Her voice was a little husky. “Dress like you want to.”

I lay in bed for a few moments wondering about my mother. Her voice had sounded like Amanda’s had, early in our marriage, when she was aroused. There was also the fact that Mom had not only accepted my hard cock against her ass, she had even held my hand to her bare tit.

I got up and put on a pair of panties and my silk robe. I would dress later.

In the kitchen I found mom, with a light bathrobe over her nightgown, fixing breakfast. She gave me a cup of coffee and I sat at the table.

Mom served us both breakfast and I cleared the table afterwards. I sat back down and my mother looked at me.

“I have a question,” she said. “But I don’t really know how to ask it.”

I didn’t say anything, only looked at her with an eyebrow raised.

She went on after a pause. “You were hard this morning, and feeling my boob. Almost like you were horny.” Mom was having a tough time with this. She was clearly embarrassed.

“Was it only because you had to pee, or were you aroused?”

“I was asleep, Mom,” I told her. “But, yes, I was aroused. I’m very sorry it happened.”

“Don’t be sorry about it, Andy.” She said. “I’m only curious because I didn’t think women would stimulate you.”

“Oh, Mom. You mean you thought I’m gay?”

“Well yes, Dear. I did think that.”

“I’m not, Mom. I’m only attracted to women.”

“I need to think,” Mom said. “Let’s talk more later. Right now I’ll go shower and dress.”

I followed her upstairs. I waited until I heard her shower stop before I started my own. I didn’t want to compete for hot water. Mom used her own bathroom attached to her bedroom. I used the hall bath. We had two guest bedrooms that the hall bath would also be for, but they were seldom used. In fact one of the guest rooms had become a storage room. Mom’s bath was quite large with a tub and a separate, large, walk in shower. The hall bath only had a shower, but it too was quite roomy.

I showered and shaved my legs, under arms too. Back in my room I dressed in panties and bra. I dug out a wraparound skirt and a silky blouse. I adore wraparound skirts. There is something sexy about them that really turns me on. As I was putting it on I had a memory of Amanda wearing one in our happier days.

I didn’t put on any makeup but I did draw nylons over my freshly shaven legs and decided to wear a pair of pumps with moderate heels.

It was the first time since I had left Amanda that I had been able to indulge in my fetish for women’s clothes. Then I had a flash of reality. I was only fooling myself by thinking things like since I left Amanda. The brutal truth was that she had kicked me out.

Downstairs I found Mom in the kitchen with a cup of coffee. She wore a dress that was a little low cut in front showing just a hint of cleavage. I noticed that she wore nylons too and heels similar to those I had on.

She got up and brought me a cup of coffee as I sat opposite her. We were silent as I took a sip of coffee. Then Mom said, “You look nice, Dear. Do you ever wear makeup?”

“Often,” I replied. “And jewelry too.”

“I can help you with the makeup,” Mom said. “If you need help, that is.”

“I’m not really too good at it, Mom. I can handle lipstick and rouge, but that’s about all. Amanda usually did my face for me.”

“I’ll help you then,” Mom said with a tone that indicated that the question was settled.

Mom went on then. “I must admit, Andy, that I thought you were gay. I was surprised to find out you weren’t.

“I think you should tell me more about your life with Amanda.” She continued. “I realize it will be hard for you, but it may be cathartic if you do talk about it. You need to purge the demons that are haunting you. I don’t mean your dress, or your femininity. I mean the pain inflicted on you by her.”

It was a relief to hear that she wasn’t going to try to change my ways. But she had said before that she thought it might be fun and had even offered to help.

“I think,” Mom said. “That it might be a good idea to take a vacation from work. Both of us. Do you think you can get any time off?”

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