Paula's Journey (18+ Material)

This is a story about truth, love and loss...

I have been interested in girl's clothes almost as long as I can remember, but it started to take shape around 9 or ten. I don't remember why, but I started to put my mom's stuff on.

We weren't supposed to use Mom and Dad's bathroom, but with three other brothers and sisters, it happened. I had to go one day and while I was on the stool, I saw her hamper. I picked out each item, one at a time, looking and feeling.

That is, until I picked up her panties. The smell was so, so warm and sweet. I think that was the first time I can remember getting hard about sex. I stayed in there smelling them until a rap on the door broke my dreaming.

After that I found out that my getting hard had other benefits. I was trying to climb a poll on the carport. Suddenly I felt something I never felt before. I just held on with my legs wrapped around that pole for a long time, slowly rubbing up and down. I did that many times that summer until an old lady came out of her house and yelled at me calling me things I didn't know the meaning of.

We moved to the Midwest then, 1960 Oklahoma was much like a New World from Philadelphia. My younger sister by 2 years was growing faster than I was. I could put some of her things on. But I liked little boy things: War, cowboys, and spies. Always, I was the hero, captured by the bad guys. Tied up and forced to put on women's clothes. Now I never heard of such a thing, so I don't know how I came up with that.

We lived next to some woods. I would take some of my mother's underwear and my sister's clothes along with some rope. I had two places that I would go. Both were hard to see unless you were right up on it. I would play out the whole seen, right up till dressed; my unseen enemy would tie me to a tree. I would make a loop, put my hands in and then wrap the rest around my arms. I would hook my hands over a low hanging branch and hang there.

One day, I found that the branch was to low. I found this other tree that had a part of one up about a foot higher than I could reach. I would climb up; hook my tied hands over and them let go, just hanging there. I was feeling I loved. I them found, as I was getting ready to climb down that as I wrapped my legs around the tree it unhook, my little member rubbed up on the tree. God it felt good. Dressed, tied to the tree and rubbing brought me to my first climax. I was scared. I didn't know what I did to get the shaky feeling and to get that stuff in my under ware. I didn't go back for a long while.

Latter that year, I was walking to school. It was my start in the 7th grade. Both boys and girls picked me on really bad. On this day John G., the school bully, said that if I showed up, he would send me home bloody. Along the way there was some homes that were to be torn down for something called the Cross Town Expressway. Instead of going to school, and getting a beating, I looked around the empty houses. Stuff was everywhere. In a pile of clothes, was a treasure. All kinds of women's clothes, from little lacy girl's things to mother's. It smelled of mildew, but I didn't care. I loved it. I undressed and put on the silky panties. But now, I could hook my bra like a pro, and then the garters. Slip and dress was the topping. No, wait shoes. I couldn't find any to fit. But there were other homes.

Many homes, with no one around. I looked around, didn't see anyone, and went next door. First, heaven. I found high heels to fit. But then a looking glass. I saw a boy dressed up in girl's clothes. My hair was about as short as you could get it. It didn't stop me from wanting to feel that feeling again. I found some rope, but nothing to hang on. Nothing that is but a door. Looking down at my legs, the dress road up to show my garters and hoes. The high heels, it was too much.

This kept up for the rest of the fall. That winter, it was to cold to go out there and now workers were tearing down my little dream home. But there is always more that one way to skin a cat. I now wanted more. But I still didn't know everything I was feeling. I had one to talk to, to ask anything. Sometimes I would wait till mom and dad were asleep, then I would go to my stash in the bottom drawer. Under my models. One complete outfit of mom's. I would put it on and always would up in the bathroom door. I found that if I opened up the mirror, I could see myself.

One night couldn't wait. Mom had Johnny Carson on the TV. I got up and got dresses in her things. I love dresses that zip up the back. I found that if I take one of my socks, and stuff the top half in the bottom half, it looks like a breast. I would put them in the bra to fill them out. I was just zipping up her new dress when I herd mom coming. I quickly got back to bed under the covers.

Mom came in, but didn't turn on the light. She asked what I was doing up. I told her I had to go to the bathroom.

"I didn't hear a flush, go flush the stool."

My heart was beating wildly.

"I don't feel well, will you do it?" I asked.

She never took her eyes off of me. "What are you warring?" she asked.

"Nothing." I replied meekly, and I hope sickly.

"Show me!" she asked.

I slipped one leg out form under the covers, hoping it would look like bare skin. Boy, did I have a lot to learn. Mom grabbed the covers back hard and there I was.

"Get up!" she yelled.

She grabbed my arm and pulled me unto the living room. It was hard to keep up in heels without falling down. She looked at me up and down.

"Turn around." She said with not a little anger. As I did, I wanted to die. "Are you a queer?" she asked, "Why do you have my stuff on?"

Like all kids, only a "I don't know." could come out. She made me take each item of clothing off, right there in the living room.

"YOU wait till your father comes home!"

I did just that, only to face him asking the same old questions only a slap in-between each one.

"Get your ass to bed you fucking little fagot!" he yelled.

As I laid in bed, my face and bottom in pain, I heard them talking. I remember one thing she said.

"He looks better in that fucking dress than I do."

***

But it didn't stop me. I don't know why, I just couldn't stop. That spring, dad started to wall in the garage to make a game room. With both mom and dad working, I found lots of time to dress in there. The girls would never go in there, and my brother was always down the street playing. One day, I didn't have a dress on, but the bra, panties and hoes were lovely. I had just tied my hands and was hanging my self when Bobby walked in.

"Paul?" then stooped when he saw me.

I was just playing a game, I told him. I asked him, "Come on, you can to, here put this on." Holding out a bra.

"No way!" he said.

I picked up a slingshot and aimed it at him. "You put it on right now."

He looked at me. "Go ahead, shoot, I'm not putting them on. Why do you want me to put them on anyway?"

"I don't know, I guess I thought if you put something on, you wouldn't rat me out." I said.

"No way man, you're my friend, I would never do that to won't tell anyone, I swear." Bobby said. "Go ahead, get dressed, I'll wait outside. But hurry, we're going to the movies and we are going now."

I hurried and just put a shirt and jeans over my undies, grabbed my shoes and ran out the door. I did remember to take the socks out of the bra. I put on my shoes and ran next door. They were just getting in the car. Bobby looked at me, but didn't say anything. In the movies, we were sitting down in front. He asked me why I did it. I couldn't tell him. I told him it felt good. So good.

"You still have them on don't you?" He asked looking at me up and down.

"Well, you didn't give much time to change did you?" I replied.

"Can I feel?" and before I could say a word he felt my breast through my bra. "Cool, it's okay, I won't tell. You can to it around me, just no dresses, okay?"

"Deal." I said, and nothing else was said.

The only time he brought it up, we were going to climb up on the garage he told me, "You better go in and take off you hose, you'll get a run in them." I could figure out how he knew until I looked down and saw that I had a hole in my jeans and you could see the tops of my hose.

I had spent the night over at his house many times since he caught me, and it was never brought up, and I never had any thing on. One thing we would do was he would steal his brother's Playboys. We would look at them and generally act like two young teenage boys learning about sex. This time, there was a Christmas cartoon showing a Cross Dresser, putting on his makeup singing "Now we don our gay apparel".

Bobby looked at me, "Hay, he's like you."

"No way!" I said, "I'm not a queer."

"Yes but, you would like to have that on wouldn't you?" he said, pointing to a lovely young thing, a Red Teddy on as she lay back on white satin sheets.

I got embarrassed. "No man, let's not talk about it."

Latter that day, Bob called and asked me if I wanted to stay the night. I said sure. I changed clothes, and ran next door.

We watched TV and he said, "Come on, let's go to bed."

We went to his room and started to play.

"Sorry." He asked, "I have something for you." He got up and reached under his bed and pulled out a wad of clothes. "I thought you would like this. They belong to my sister."

His sister was just out of school and more than a little wild. All black. I thought this stuff was only seen in Playboy.

His mom rapped on the door, "Okay boys, time to go to bed."

He got up. "I have to go to the bathroom, put them on and get in bed. You let me see and feel your sister, I want you to have fun too."

One night when he spent the night, we sneaked in to my sister's room, and I slowly unbuttoned her top while she slept. When I opened her top to show him her breasts, he slowly felt them. He leaned over and started to suck on one. When she did move he reached up and grabbed the back of my head and gently pulled me down to the other one. We both were getting hot. We both got up when Carol shifted. Her breasts were still in view. He pulled down his shorts and started to rub himself. He motioned for me to do it too. Although I had made myself come many times, I had never used my hand. It felt good and soon, we both came. But some landed on her breast.

"Oh shit, when that dries, it will hurt. She will know and then so will your mom." He whispered.

"I don't have a wet rag to wipe it off. If I run water, it will wake up mom."

"You better do something quick, it will dry and shrink. It will feel like someone pinching her nipple."

I didn't know better so I believed him.

"What do I do?" I pleaded.

"It has to be wet to get it all off." He looked at me and said, "If you Lick off, that should do it, just be careful not to like it too much, you might wake her up."

I leaned over and put my mouth over her nipple. I had heard it tasted salty, but this was tangy. Just then she stirred. We both almost ran out of her room. Carol never said anything and we never heard about it.

We both sat in Bobby's room and talked about Carol's chest, he told me to go ahead and put the clothes on, "You know you want to."

He was right. One thing I found out about me is it was a real thrill to dress up, but something was missing. I could look like a girl; act like a girl, but I couldn't go out in the real would like a girl. It was like a hollow world. Make believe. Like little girls dressing up like Mommie. But as I looked at the pile of clothes, I know I would do it. Here, I got to dress, and be with someone. Booby acted like he was real concerned about my happiness.

I quickly undressed. I picked up the panties, all black with red trim. So soft. I pulled them on, put the top on. It was different that any I had put on before. I didn't know anything about waist clinchers or the like. It was strapless, with about a dozen hooks in the front. The garters were attached to it. I moved it around to get it about were it should go and pulled on the hose. I had never put on fishnet hose before. My hair had been growing some and was just over my ears.

Bobby walked in and stopped. "Wow Paul, you look like a girl. Here," He held out his hand. He had a bright red lipstick. "If you're going to do it, you might as well do it right."

I puckered my lips like I saw my mom do, and then dabbed my lips on a tissue. We sat on his bed and Bobby got out his hidden stash of his brother's books. In one of them, we saw a girl with an outfit similar like the one I was wearing. She was in bed with a guy. We laughed at it and Bobby leaned over and held me like the couple in the photo.

I looked at one scene with a girl in bed with a guy on top of her. She had her legs around him and her head was tilted back. For the first time I wondered what it would be like.

Bobby said at that moment, "I wonder what it would be like with a girl?"

He started to hug me and feel me but. We didn't go any farther; it was all too new to us. We couldn't be 13 at the time if we did get carried away. It was all in fun, and it wasn't long we were acting up a little too loud. A moment latter came a rap on the door and his mom opened the door.

"Boys, I said go to bed, if you don't quiet down, I'll send Paul home."

I was so happy she couldn't see me from there.

We quickly turned off the light and went to bed. I was up agonized the wall on my side and Bobby was in front of me.

"That was close hush?" I asked him.

"If she came in just a little more she would have really sent me home."

"I wouldn't like that." Bobby said. "Hay, do you have a girl friend?"

"No," I said, "you know I'm not very popular with girls."

"Listen Paul, we play allot, but the one thing I want more than anything is a girl friend. Could we pretend you're my girl friend tonight?"

I liked Bobby, and I felt sorry for him, but something else was in play. I didn't understand most of what I was thinking and feeling.

"I don't want to feel like a dork when I get a girl, I would like to act like I know what I'm doing. Can I try something?" He asked.

"Like what" I replied, just a little worried.

"Can we really pretend like we were in love?"

"No way Bob, I'm a guy and not a queer." I said.

Looking back now, I think I wanted to, but image. You know?

"Oh come on. No one will know." He pleaded.

I softened, and right then he put his arm around me and pulled me to him. I laid my head on his shoulder and was content. Just holding me felt good. It felt right. He asked me how it felt as he was moving his hand. I never saw it coming, but he was feeling my breast before I knew it. I rolled over to tell him I didn't think this was right but as I rolled over, he kissed me. I was surprised, but soon I was caught up in the heat of passion.

We were soon moving out hands all over each other. By accident, I found his cock. I was going to move my hand away, but the look on his face. Such pleasure on his face. He wasn't looking at me. One thing that he did to me that felt great was suck on my neck. I started to suck on his neck as I pumped his cock. Soon he moaned and came all over me. As he came down, I was still hard as a rock.

"Go ahead, do your self, I can't right now and it would be neat to watch. Sit up so I can see, okay?"

I sat up and started to pump my own little cock. It wasn't long till I shot out hard. A big glob hit my mouth and the rest on the bed and wall behind me. I started to wipe it off.

Bobby said. "No, wait, don't move." I looked over and he was already hard and pumping. "Wow, that is so wild, now please Paulie, don't wipe it off, lick it off, slowly, please."

I did it for him. I realized that it wasn't that bad. I mean, it wasn't a turn on for me, but it was a real turn on to see Bobby turned on by me.

I licked up that glob and Bobbie looked at me, "Paula, you are my girl friend, could you please help me?"

I knew what he wanted but I couldn't. I just used my hand again. As I leaned over to get to him, Bobby grabbed my head and pulled my head down to his cock. It was so sudden that I went over, not fighting it. I thought, okay, I think I want to do this. My face was just about six inches when he erupted all over my face and in my mouth.

I cleaned up, changed clothes and we went to sleep. The next day Bobby never said a word, but when I got home, mom told me to go wash up, my mouth was stained red from candy. What she didn't know...

The next week, Bobby asked if I could stay the night. I didn't know, but he talked me into it.

"Please Paul, please?"

"Okay." I said.

That night, just like the week before, he had the clothes. But this time he had make up. I didn't look very good on my first time, but it looked good to me. His mom and dad were out till late, so we had the house to ourselves. He had a hot little dress his sister had that looked hot. Bright red velvet. Long sleeves and real short. With the black undies and red heels, it was an outfit to die for.

We were sitting on the sofa watching TV arm is arm, like a young boy and girl when in came his brother. Tim was older, about 16 or so. A real tough guy.

"Well, well, well, what have we got here. My little brother and his girl friend."

At first I thought Tim didn't know who I was and I muttered something about I had to go.

"Go ahead and go if you want. But you're walking out like that." Tim sneered, "I'll bet the school would love to know all about you, the queer next door."

I knew I was had. Bobby never looked at me or said a word. Tim came over and sat next to me. As he put his arm around me he looked over at Bobby.

"You better just go on to bed, me and your girl friend are going to become real good friends. You will thank me when the next time you two make love."

As Bobby left the room, he looked over at me, "Sorry, he found out and said he would beat the shit out of me if I said a word."

With that, he left me alone with Tim.

Tim started to feel me up but not with the tender care Bobby did. "Come on bitch, get going, I don't have all night."

He pulled down his paints and with no underwear, his cock stood out, hard. Much larger than Bobby's member, his cock was odd looking. He grabbed my head and pulled me to his cock. I tried to get up and he started to slap me. He hit me time and time again. Just then there was a loud bang. I went down to the floor. When I looked up, I saw Tim, face down on the floor. Bobby over him with a baseball bat.

Bobby grabbed my arm and pulled me up, "Come on let's get out of here before he gets up." We just ran.

There was an old motel not far away, Old 66 Motel I think, or something like that. West Tulsa has some small places on old route 66. We were standing out in fount when an old woman came out and asked us if we were okay. Well, two kids, out at 11 O'clock at night wasn't something you saw around there. I had been crying, my make up smeared. Bobby looked over to her.

"My mom and Dad are out of town and my brother started to beat my sister and I, we ran away."

"You poor dears," she said, "do you want me to call the police?"

"No mam," I said quickly, "it has happened before, we will just find someplace to hide for the night and we'll go home tomorrow when they get home."

Bobby added, "This has happened before. Boy, dad will beat the tar out of him for this."

"Do you have anywhere to go, can I call anyone for you?" she asked.

"No mam, we'll be okay." Bobby said.

"Nonsense!" the lady said, "I have plenty of room, come in here." Inside, she gave us a room key. "Don't tell anyone I did this kids. I could get into allot of trouble. But I think it's okay, what with your being brother and sister and all."

"Yes mam, and thank you." Bobby said as he took the key.

"Wait here Hun," the lady said as she went out the back of the office. She came back in with a cute nightie, "here honey, this was my granddaughters, but she has out grown it. You need something to sleep in. The room had two beds. Have a good night. Just leave the key on the night stand."

We walked out to find the room. The place only had about 20 or 30 rooms. Not hard to find. I slipped on the gravel. I forgot I still had heels on. Bobby put his arm around me.

Tiring to make me feel better he said, "Well, first time I ever took a girl to a motel, is this you first time here with a boy, or do you do this all the time?"

I swung at him, but was just glad he had been there.

We unlocked the door and got in. First thing Bobby did was pick up the phone. "Mam, I had better let my older brother know that we are okay, but I won't tell him were we are. He will get real worried. Yes, thank you, you too, good night." In a few moments. "Tim? Bobby. We won't be coming home to night. Tell mom we went over to Paul's. If you say a word, or do anything to us, we will both tell everyone in school you tried to dress Paul up in a dress to make love to him because you like little boys." With that, he hung up.

"Thanks Bobby," I said.

"No problem, it's the least I can do for my girl." He said as he sat down on the bed with me.

With that, we both broke down laughing. I was still shaking and Bobby came over and held me.

"It's okay, it's over now."

It felt so good in his arms, I looked up at his face and he kissed me. Not hard, but slowly and with care. It felt right and I put my arms around him and soon we were on the bed kissing and feeling each other. Learning more that night than in a life before.

Still dressed, he was hard, and I really wanted to do something for him, so I slowly move down. I looked at his small cock, and kissed it. I then put it in my mouth. I was able to take the whole thing since it was so small.

He stopped me and said, "Paula, I love you, and I want this to be our honeymoon. I want to do for you as well as you for me."

With that, he spun around and we were in a 69. I came first. He pulled off just as I started to come, but he kept on pumping with his hand. I kept his cock in my mouth. I wanted to find out what it was all about. Soon Bobby came. I swallowed all I could. We both went in to the bathroom to clean up I weren't feeling self-conscience any more. I really felt like a girl with her man.

I dressed in the nightgown and climbed in to our bed. Wow, our bed. As we lay there, bobby had his arms around me soon; we were back at it.

"Can I fuck you sweetheart?"

I didn't say anything. I just moved around on my back. Bobby got on top and we made love. After a short while, he reached down and grabbed his cock, guiding it to my hole. It wouldn't go in and it hurt.

After a few tries, I told him. "Bobby, it won't go in. It hurts."

"Wait, I have an idea."

With that, he spit in his hand and put it all over his dick, then he tried again. This time, it started to go in. I'm glad he was so small, it hurt like hell, but soon Bobby was on top of me, fucking away. Soon, real soon, he came. I could really feel it. I'll never forget my first honeymoon. The felling of his member in me. The wonderful felling that I brought such pleasure to him.

Well next Monday, it was all over school, I was a queer that tried to come on to Tim, and been fucking Bobby for a year. To say that things were not fun was, well you can guess. But I don't think anyone believed it. But Dad had to transfer to Va. A new start for me.

Things didn't change for me. But I had my own bedroom in the basement. I dressed every night. Then came the night Martin L. King was killed. Mom and Dad were out of town and I wasn't going to go to school. I dressed up, put my make up on. I had rolled my hair the night before, so I had started to brush it out when mom came in. I never heard them come in.

She just stood there and all she could get out was, "Even my earrings?"

Dad yelled down, "What the hell is going on?"

Mom told me to get out of the dress and wash my face, quickly. Then she told Dad that I was home sick, to go to town and get the other kids.

Mom asked me what was going on. I told her the same thing every boy has told his mom, "I don't know."

"Well, get my dress off quick. Your father would kill you if he saw you now." She told me.

I had trouble getting the zipper so she told me to hold on and she unzipped me. I pulled it off and started to pull off the bra.

"Hold on," she said, "we don't have time. Get your face clean and wet your hair. Just pull in some paints and a shirt, you father will be back in a minute."

I did what she said, and thought I would change before he got back. But Mom was right. Dad got back before I could get my hair brushed out. But it wasn't to bad, I thought.

Dad was in to big a hurry to get the guns and stuff in the car. You see, we only lived 16 miles from Washington DC, and the Blacks were already starting their riots. We were going back to Levittown Pa. To stay with friends. When we got there, I met Lewis for the first time in ten years. Lewis was my age and was my best friend back then, but as you know, Tom Wolf said it best, "You can't go home again."

I went it to his room to change before anyone could before anyone could guess. He came in just after that and saw the bra there on the floor, but never said anything. But he didn't act like my old friend. It was close. Mom never brought it up.

As time went on, I joined the Navy. I only dressed up once. After I got out, I moved back home. I felt it was behind me. But it is never like that. I started once more, but not very far, just underwear.

I got married, and tried to live a normal life. I sometimes would put Karen's clothes on. It helped when we worked odd hours. I would but on her underwear, then I would play with myself until I came. One day, I did that, and then fell asleep.

She walked in and found me in her bra. "What the hell is going on?"

I didn't have an answer to give her, and she dropped it.

But we did get divorced a few years later. I then started to dress more. Over the next eight years, I tried to raise my son, and find happiness. I went to night school. I used to laugh as I was standing there in a suit and tie, with lacy underwear on. As I left school, I would stop around the corner, put on make up on and change to a dress. I loved driving home dressed.

Once, I was driving home and saw a young man with his thumb out. "What the hell." I thought. "What can he do?"

I stopped to pick him up. He said thanks and he jumped in, most likely glad to get a ride at 11:00 at night in the winter. I told him no problem.

Now, let me say, I can't pass. No way. I'll give him this, he never batted an eye. I asked him where he was going.

"Oklahoma City Mam." he said.

That did it, I took him to Oklahoma City, over a 100 miles. Why? Like I told him, he treated me like a lady. We talked about things there, we stopped and he went in and bought me a hamburger and coke. He asked my name and I became Jennifer.

I dropped him off had he said, "Thanks Jennifer, you're real sweet."

Then I got married again. But this time I told her right off the bat. I like to dress up. I was cool with her until we were married a few years. After 12 boy friends, I divorced her.

But this one is very hateful and vengeful. Now everyone knows. My kids, her folks, some of our friends. She made sure of that. We fought many times. But Juanita found out something. When I was Paul, I was hateful. When I was Jennifer, I was much more understanding, mellower to her. Many times she would call up when fighting and ask to come over to talk to Jenny about this fight.

But after I got my own place, I dressed whenever I could. Sometimes I would go out at night and pay a bill in the night drop. But one night, I decided to go to an adult store and get a toy.

I dressed down. I had my wig and make up, but I put on slakes and a blouse. A coat with a hood topped it off. I was so scared. I went in at 11 at night. Only two customers there. I picked out a nice one and went up to pay for it. I was so scared. I had on fake nails and I fumbled with the money.

As I went out to the car, a man stepped up, but not to close. "Mam?" he said. "I saw you in there and I was wondering, would you like to sit with me and watch a movie?"

Okay, I didn't know what to do, but something in me wanted to say yes. I told him, "Don't go thinking someting is going to happen, but yes, I will."

We went to my place. He put in his tape. I went in to change. I put on a very short skirt and came in and sat next to him. As we watched some chick sucking some guy off, he, acting like a 15 yr. old, slowly put his arm around me. As we watched the porn movie, he asked if he could touch my breast. I didn't say anything and he slowly, very gently cupped his hand around my breast. He told me that they felt so real.

Soon, we were kissing. I'm a non-smoker, and he was. The smell, plus his man smell. His one day beard growth. His hand worked its way up my dress and I was in heaven. As he kissed on me, I felt too wonderful. I couldn't believe what I was doing. I worked down his paints, and looked at his cock. I went down and started to kiss it. I thought them, I want him to fuck me. I let him into my mouth. It was so sweet. I tasted his pre cum. But I wanted him in me. I still remembered the sweet times with Bobby. We went up-stairs. I pulled down his paints and sucked him some more. Then I got on my hand and knees. But he had been taking drugs. He couldn't get hard enough. He was so ashamed he left. Shit!

I then meet someone on the web. A young guy about 18. I was 47 then. I was dressed up, and he asked if I would loan him some clothes. I did. Soon, I was sucking him. I sucked him till I felt him explode in my mouth. God yes. I sucked every drop. While I had him in my mouth, I started to play with my self till I came.

That has been three years ago and I still dream of him. I did meat one girl, Tracy. I told her right up front about me. She said that she worked with a TS and had no problems about it. She lived with me for 8 months, before she found other interests.

She had also changed to, "Do what you want, I won't change you. But not around me." I wonder what part Jennifer played in this.

Now, here I sit. I stay dressed when I don't have to go out to work or when I don't have the kids. I hope to find that special someone. But I don't see a change. I think because of our society, a 'girl' will always be alone.