Andy's Journey Ch. 01

"Things are slow right now," I replied. "I think they will be happy to let me take vacation time."

Fortunately I had got past the bad times I had been going through after my marriage breakup. My work was up to par once again and I was in good graces with my bosses. But the recent developments might well bring on a recurrence. I felt like I would be better off away from the office.

"I'll go into work tomorrow and make arrangements to start vacation right away. I can probably turn my work over to someone else and take the rest of the week off."

"I should be able to get the same days off," Mom said. "In fact I know I can. That will give us four days plus next weekend to work on your problem.

"Let's not start on that just yet," She added. "We can wait until our time off begins. Is there anything special you'd like to do today?"

"Well I have to unpack my suitcases, and probably wash a few things," I told her.

"I'll help you," Mom said. "Would you like to be made-up?"

"That would be nice," I said. "But we will only have to take it back off for work tomorrow. If I could I'd like to use your tub this evening for a bath."

"We'll put a little make up on you. Not too much for now. We can do more tomorrow evening when our vacations start. I'm anxious to see you with one of your wigs. We can do that today."

We finished our coffee and went to my room. We spent a couple of hours unpacking and hanging things up. Mom admired some of my things. Especially an evening gown I had worn for Amanda a few times. She also liked some of my nightgowns. They were all very sheer and quite daring. Amanda had liked me to wear them over a garter belt and nylons.

When we were done with the suitcases mom told me to bring my makeup and a wig to her bathroom. There, after she made me shave closely, she made up my eyes and lips. My eyebrows needed a lot of work. I tried to strike a middle ground between feminine and masculine. I clipped dangle earrings to my ears and she put the wig on my head. Together we looked at me in the mirror. I was still wearing the blouse and wrap around skirt I had put on earlier.

"You look very nice," she said.

I agreed. I felt beautiful too. It had been so long since I had been able to let my feminine side free. She was free now, for a few hours, and reveling in the sensuous feelings flowing through my body.

I tried to tell Mom how good it felt to once more be dressed as a sexy lady, but I didn't have the words to describe the sensation properly.

"I think I know what you're talking about," my mother said. "Women get that feeling when they are dressed for a romantic night out or to join a lover in bed."

We went back downstairs and Mom fixed us a light lunch. After we ate we cuddled together on the couch and watched a movie. Just being near my mom was having a relaxing effect on me. I laid my head on her lap and pushed my face into her bosom. She held me there but did not bare her boobs as she had the day before.

We ordered pizza for dinner. We didn't feel like cooking. I answered the door when for the delivery. It was a man about my age who didn't seem to notice I was anything but an attractive lady. I didn't speak. That would have given the game away. I gave him a little goodbye flutter with my fingers as he left.

I felt like I had passed a test as I closed the door. I hadn't even done my nails and still had appeared like a woman to him.

After our pizza we lingered over coffee and liqueur. Then I thought it was time for my bath. I undressed in my room and went to Mom's bath wearing my robe. As the tub was filling I scrubbed the makeup from my face. I added my favorite bubble bath and luxuriated in the hot bath for almost an hour, it had been so long since I had indulged myself.

Back in my room I chose one of my longer nightgowns. I did not wear a bra or panties under it. I covered myself with my silk bathrobe and rejoined my mother downstairs. Mom was on the couch. She could see the top of my nightgown peeking out where the top of my robe was open.

"That looks nice," She said. "Let me see how it looks on you."

"I better not, Mom," I stammered. "I'm not wearing anything under it."

"I don't think it matters, but just show me the top part if you'd rather. Don't forget you have shown yourself to me in your panties."

I opened the top part of my robe and showed her the upper part of the nightgown.

I sat next to her on the couch.

"There were a few times today when I felt like you were my daughter," Mom told me.

"Thank you, Mom. That makes me feel good."

I hugged her then. "I'm very nervous about tomorrow, Mom. About telling you everything about my life with Amanda."

"I know honey, so am I. Will you be able to sleep tonight?"

"I don't know," I told her.

"Well sleep with me again. That might help," Mom offered.

"Are you sure that's okay, Mom?"

"It will be fine, Baby. You're my little boy and you're hurting."

"Ok then, Mom. I know I'll feel better with you close."

We watched TV for an hour cuddled together on the couch. Then Mom said it was time for bed. I was feeling a little sleepy. The hot bath had relaxed my body and even calmed my tortured thoughts a little.

We went upstairs, Mom held my hand as we went to her bedroom. She told me to go ahead and get in bed while she changed.

I laid in the bed and watched Mom's shadowy form disrobing near the open door of her closet. A couple of nightlights provided the only illumination. Mom put on a cotton, full length nightgown that was rather sexless. She came back to the bed and laid next to me. She kissed me once, lightly, on the lips and said good night.

I told her goodnight in turn and drifted into a restful sleep. I woke when it was just starting to get light outside. Unlike the night before I did not have a hard-on. Instead I felt safe and secure. Mom and I were lying close together, each with an arm over the other's body.

I would have been content to lie there all day like that, but nature called. I eased out of bed and dashed to her bathroom to pee. I had to go to the hall bath to brush my teeth. Then I went downstairs to start the coffee.

When I got back to Mom's bedroom she was sitting up stretching. I hadn't put my bathrobe on yet and was wearing only the filmy nightie I had slept in. Mom looked at me with my cock, and the shadow of my pubes, dimly visible through the gauzy fabric. She didn't say anything, just nodded. I felt myself turning red in embarrassment.

"Coffee will be ready in a minute," I told her.

I found my robe draped over a chair. I put it on and went back to the kitchen to wait for my mother. She arrived soon but didn't say anything until she had finished most of her first cup of coffee.

"That is a very sexy nightgown, Andy. You look very good in it." Were her first words.

"Thank you, Mom. It's one of my favorites."

We didn't say much more except for normal morning talk. We ate a light breakfast, mostly pastries and juice. While we were having our breakfast Mom mentioned that she thought she could probably take off a few hours early. I thought I might be able to also and I told her I would try to be home early too.

After breakfast I asked Mom to check for any signs of makeup I may have left on my face. She didn't find any and I dressed for work. Mom got ready for work too and we left the house about the same time.

The first thing I did at the office was to ask my boss for some vacation time to take care of some family business. He agreed readily. I am a good employee, when not consumed by emotional torment, and had plenty of vacation time built up.

I had everything that needed to be done taken care of by two o'clock and took the rest of the day off. I told my boss, before I left that he could get me by email if he needed me for anything while I was off.

I was back home a little before Mom. I was debating with myself whether to change into panties, or not. I decided to wait until Mom got home. I was more than a little nervous. I had been fine at work when I had things to do to keep me occupied, but a vague fear was starting to creep into my mind. Even so I knew I had to do what needed to be done, and the sooner the better.

Mom got home shortly after me. She was dressed in a well fitted suit with a skirt. With her nylons and heels she looked very professional and very feminine. I decided that my mother is an attractive woman. The fact that she was overweight only added to her beauty in my eyes.

Mom suggested we have a drink and mixed us a couple. We sat on the couch and sipped them. Mom had shed her suit jacket to show a very pretty white blouse.

Mom turned to me and took my hands in hers. "How would you like to dress, Dear? I think you will want to be comfortable."

I knew then that we were going to go through with it. That Mom would make me tell her everything. The vague fear I had been feeling was growing.

I swallowed and tried to instill a little courage into myself. "I think I'll change into something I feel at ease with." I told her.

I went upstairs and put on a pair of my favorite panties and a silky camisole. After thinking about it for a minute I decided to wear nylons. I thought the sensuous feel of them would help me relax. I added a pair of sandals, with two inch heels. I put on my silk robe and went back downstairs to my mother.

Mom had mixed us another drink and she handed it to me as I sat next to her on the couch. I sipped at it gratefully.

She waited until I had finished my drink before she drew me into her arms and told me to tell her everything.

I began to talk. I tried to tell her about the pleasure I got from fine lingerie, from wearing a skirt and blouse, or even a simple housedress. About how I wanted to dress like a woman, but I was sexually attracted only to females.

Mom listened and asked only a few questions. When I ran down she urged me to talk about my life with my ex-wife.

That was harder for me. I soon found myself, once again, sobbing in her lap. She knew how to calm me though, she had prepared. While I was changing she had removed her bra and put her blouse back on.

She let me cry for a while stroking my head and shoulders. She tried to get me talking once more, but I broke down again. My body was racked with sobs as I lay on her lap. It was then that she opened her blouse and gave me her tit.

I was flooded with gratitude as I sucked at her nipples. As she held me to her breast like her baby. She let me suckle at her for fifteen minutes, or so. She gently pushed me away then and urged me to sit up.

"Let's take a break and have dinner," she told me.

I was ready for a respite, even if it was a little early for dinner. Mom warmed up some leftover pizza and we ate a light meal. After we ate she fixed me another drink but poured wine for herself.

Back on the couch she let me sip at my drink until I had finished it. "You've told me how much you like dressing as a woman, Andy, but you haven't said anything about how it started."

So I snuggled up to my mother and, with my head on her shoulder, told her about the early days of my marriage. Those times when my ex-wife and I were happy and adventurous in our sex lives. I was trying to tell Mom about our oral escapades when she interrupted me.

"Andy, quit beating around the bush. Use the terms that are in your mind. If you ate her pussy say you ate her pussy. If she gave you a blow job call it a blow job. Believe me, I've been around long enough to have heard all the terms."

I was surprised at my mother's words. But it did make it easier for me. We talked for another hour. About how Amanda and I would suck and fuck all weekend. About how she used to dress me in silky lingerie and I would eat her pussy and she would suck me. I went on to tell her how we progressed to makeup, jewelry and dresses. About how I would wear my evening gown and we would have a candlelight dinner as if we were two attractive women seducing each other.

Mom called a halt about then. I had gone through that session fairly easily. But, I hadn't been discussing the break up. My life had been one of contentment until it crashed around me.

"We'll talk more tomorrow," Mom said. "Take your robe off and let me look at you."

I stood in front of her and dropped my robe. Mom looked at me and said, "Yes, I can see what attracted her. You look very appealing."

She let me sleep with her again that night. But this time I woke up with a hard-on. Like the first night we had slept together I was spooned into her back. My hand was on her tit and my hard cock lay against the bare cheek of her ass. Somehow, during the night, both our nightgowns had slid up to our waists.

I eased back away from my mother, reminding myself as I did, that she was my mother. That it was not appropriate to let my lust take control, even if I was asleep.

I peed, brushed my teeth, threw on a robe and went downstairs to get the coffee started. I was on my second cup before Mom showed up. After she finished her first cup I poured her another and sat back down.

She looked at me levelly. "It appears that we got a little more intimate last night."

I started to stammer out an apology.

"Don't worry about it, Andy," she told me and patted my hand with a smile.

She didn't say any more on the subject. After breakfast Mom said we should do a little housekeeping. I volunteered to clean the kitchen and bathrooms and do my regular laundry chore. Mom said she'd take care of everything else.

I didn't have to hide my panties while working. It gave me a little bit of a thrill to be doing housework in my feminine undies. Mom's panties were especially aromatic, as if her pussy had been producing more juices than normally.

We worked steadily and were done a little before noon. Mom hugged me and thanked me for the help. "Let's have lunch," she said. "Then we can continue what we started yesterday."

"Ok, Mom," I told her. "I think I might dress up a little more today. Will that be okay?"

"I think that will be fine, Andy. In fact let's make you into a real lady this afternoon. I'll help you."

"Thanks. Mom. I appreciate it."

I made a salad for us for lunch with lots of chicken and ham chopped up in it. It was quite good and Mom enjoyed it. I am a pretty good cook, like doing it.

"Let's go get dressed now," Mom said. "I need a shower after all that work this morning."

"Ok, Mom. You shower first. Then I'll get mine."

In my hall bathroom I shaved carefully as I listened for the sound of Mom's shower to stop. When I was satisfied that my face was smooth enough I took my own shower. I was really looking forward to getting dressed up. I was especially excited about my mother helping me. I thought that it showed she accepted me as I am.

After my shower I shaved carefully. Back in my bedroom I put on panties and a bra then drew on a sexy pair of seamed nylons. I put a lacy garter belt on too. I was mulling over what to wear over my lingerie when Mom came in. She was in a knee length robe. I could see she too was wearing nylons and had on a pair of stylish pumps. Her hair was fixed nicely. A little more relaxed than for work. Her face was made up and she looked very feminine and attractive.

Mom helped me pick out a skirt that was a little on the short side and a nice printed blouse. I was pleased because they were some of my favorite clothes. I had a good collection of wigs. Mom picked one out for me, blond, chin length, a relaxed style. We went to Mom's bedroom next. I sat at her makeup table.

Mom did my nails first. Then made my face up. She used a minimum of makeup, but used it expertly. She put my wig on next using tape to hold it in place. Earrings and bracelets followed and a necklace. Last she knelt in front of me and put on the three inch heels I had chosen.

Mom led me to the full length mirror and I looked myself over. I must say that I was very pleased with my transformation.

We went downstairs to the living room and Mom fixed us a couple of drinks. We sat chatting for a while. I asked Mom if she was going to finish dressing, she was still in her robe. She answered that she would later.

I finished my drink and snuggled up to Mom. I was feeling more secure about telling her my story, even though I knew the worst was still to come.

The first part of what I talked about that afternoon was more about the happier times in my marriage. Then came the part about how things started to deteriorate and I didn't even realize it was happening. I told Mom about Amanda butt fucking me and about how it thrilled me. I described how she would impale her pussy on my cock then sit on my face as I joyfully ate my cum out of her wet cunt. I told my mother how those were the only times I was ever allowed to cum inside my wife. I described how a blowjob for me had become a distant memory. About how she would giggle as I masturbated after I had satisfied her; but left with only my own hand to relieve my throbbing hard-on. I told her of my shock and dismay when she had described Sam and Jane as a real man and a real woman.

I told my mother all these things between bouts of gut wrenching crying. I used the words she had told me to use. They made the story real to me, as if I was reliving it. But now it was agonizing. When it had happened I had been oblivious.

Mom pushed me back from her and held me with her hands on my shoulders. She looked me in the eyes and told me. "You tried to be both her lesbian lover and her stud. You failed at both.

"But that does not mean you will fail with other women. You will succeed. I know it."

Mom was giving me a glimmer of hope, even as she made me face reality. She pulled me back close to herself and put my head on her shoulder. She hugged me tight. We stayed like that for what seemed a long time. But not long enough for my tortured soul.

I heard Mom ask me if there was more I had to tell her. I started to say no then realized that I had not told her of the empty spot in my life. About how much I missed the bouquet of Amanda's cunt. Of how I longed for the slick taste of her cum when she would squirt. Of how drab my life now seemed. I had to tell her all of that.

"I think I'm done, Mom," I told her after tearfully getting that off my chest. "There may be more that I will remember later."

"I think there's something else," Mom said. She sounded a little stern. "You need to tell me everything no matter how painful it is, or how embarrassed it will make you. I promise, nothing you tell me will make me love you less. The rewards for you will be great if you cleanse your mind."

She was right. I knew it. It took me a while to realize what I had held back. I told her then of the excitement I felt when I sniffed and tasted her panties. I didn't break down in tears over that, but I was very embarrassed. Mom wasn't upset though. She hugged me and said, softly, "I'm glad you found me tasty."

"I think that's all, at least for now, Mom."

"I'll go make us a drink," Mom said. "Wait here."

"I need to pee, Mom. I'll be right back."

I ran to our downstairs toilet and peed. I saw myself in the mirror and noted that my tears had made a mess of my makeup.

I got back to the couch just before Mom. I was using a tissue to wipe at residual tear tracks on my face when Mom came back with our drinks. She sat close to me and handed me my glass.

"I hope we helped you, Andy. It was hard for both of us, but much more so for you. I need to ask you some questions now, but finish your drink first."

Mom had made my drink pretty strong. But I was already recovering from the ordeal. I felt strangely free of the bonds that had tied me to memories of my ex-wife.

We finished our drinks and I told mom with a little laugh. "My makeup is a mess."

"Yes it is," she agreed. "We'll fix it later.

"I have some questions, Andy. Please think carefully before you answer them. The answer doesn't matter. There is no right or wrong, but we both need to understand you. Are you okay with that?"