Let me start off by saying that I have always enjoyed wearing women's clothing, as far back as I can remember I love the feel of satin against my body. My first experience was when I was 13. I was in the bathroom, taking a piss, when I saw a pair of my mom's black satin panties in the hamper, so I took my mom's panties and off to my room I went. That night was my first experience, with women's panties. The feeling of them hugging my little cock was intense needless to say I came very fast, When I was finished I couldn't very well put them back in the hamper, so I stuck them between my mattress's.
Not too long after that I discovered transvestite website's, I was stunned how these men would dress up, and pass as women, it went from transvestite to she males, even the sissy hypnotic videos, I watched them all, for a long time, the desire to dress up and wanting become a girl grew inside of me I wanted nothing more than to do those things I saw on line. I learned some basic's from them how to dress, do make-up, everything that a girlie boy would want to learn.
My friend George would come over and spend the weekend sometimes. The first time it was hard because of my desire to wear panties, I was laying in my bed wearing a pair of satin pink panties under my gym shorts and stroking my cock through them, it was hard to do with George there, I wouldn't cum, I did want him to know what I was doing.
One night I was rather frustrated wanting to cum, but having George there made it hard. So I just rolled over and fell asleep. I guess it was about two in the morning when I woke up. I rolled over and looked across my room and I saw that George pulled his covers back, and he was jacking off. My heart began to beat fast.
I had never seen, another guy do this except on video, but from the dim light of the night light, I could get a clear look at his cock. I felt a tingling sensation in my own crotch. My cock was getting hard. George has good size cock compared to mine. I would guess it to be about 8 inches, mine was about 5 inches. I watched my friend play with himself.
I started to rub myself. I was getting turned on. "Jack, hey you awake?" he ask. I stopped rubbing myself, busted I thought, so I spoke up "yeah George I am, what ya want?" He laughed "I thought so, so are you enjoying what you see?" What could I do except answer him, "Well I've never watched another guy jackoff before, I was just curious sorry". He laughed, and I saw him get up from the bed across my room. George walked over to my bed his cock sticking straight out.
He stood there smiling, then said "Well then I think you need a up closer view", and began to stroke himself standing over me, an over whelming desire come over me. I wanted to reach out and touch him, but something more strange happen to me; my cock began to get hard again, I was getting turned watching him. "It feels good Jack", he said. I said nothing back, just watched him stroke his cock. I don't remember how it all happen, but George stopped and sat down on the side of my bed, and leaned back, he smiled at me and said, "I seen what you have on under your shorts, how long have you been wearing panties Jack?" I was at loss for words, but knew that if I didn't say anything to him, he would pester me.
"I've been wearing them for about 3 years now". I replied. George smiled, all the time he still was stroking his cock. It was hard not to take my eyes off him doing that. "You like wearing them Jack?" I stammered out "yes". "It's okay Jack, I went through that phase to" he said, he continued to talk, "I think you want to do other things to." he stopped stroking his cock at that point. "Other things?" I ask. George sat up. "Yes Jack other things, we have been friends for a long time, and I've watched you change, how you walk, talk, I mean it has become more feminine, I just thought at first you were playing a game, but it hasn't changed a bit, so tell me what's going on here, you watching me jack off, and all I think I deserve an answer buddy." I told him all of it, me keeping my legs, armpits, and even my pubic area free of hair.
How I would dress up in my mom's clothes, especially her satiny nighties, panty hose. How I was experimenting with make-up. I even told him about the wed sites. He sat there and listened. "Wow Jack, I never really knew, so you want to be a girl?", He ask me. "George the desire has been there, from the very moment I started, the web sites have helped me understand this, sure it's all porn, but there are a few out there that deal with it, and from what I have read and come to understand, it's okay for me to be this way.
George I think I should have been born a girl!" "So if you feel that way, have you told your mom yet?" "No I haven't, but I will one day, I suppose", I replied. "Your mom is a pretty cool lady Jack I think she will understand", George said. "I don't know, maybe she will maybe she won't I just don't know!" George smiled, "don't you think she may have noticed the change in you, like I did Jack?" I was quite, he was right, if he noticed it, then mom did to.
"Has she talked with you about?" "No she hasn't, as a matter of fact she has been more understanding of me, I don't know, I just don't know". I said. By now I was thoroughly confused. Here I was telling my friend about my sexual orientation, thinking that my mom knows about it? I really had no idea on which way to go with this. George reached over and grabbed my hand, "what are you doing?" I said.
He just smiled and said "relax Jackie". "Jackie!" I said. George smiled, "sure you need a girl's name and I like Jackie, see if I call you Jackie when you're not dressed up, no one will know, guys go by both names". I smiled, "Okay if that's what you want George" I replied.
"It's not what I want it's what you want Jackie." George said. "Jackie show me what you have on", He said to me. I thought and then did it. I pulled my covers back, and slipped my gym shorts off, exposing my pink satin panties that I had taken from my mom. He smiled, "nice Jackie very nice". he said. "I want you to think about it, but right now let me help you out with something you really want", he said as he placed my hand on his semi hard cock.
I was shocked the only cock I have ever touched was my own. "Go ahead Jackie, feel it", he said. I didn't know what do, except go for it, which I did. George leaned back on his arms. "Um" he said.
I felt his cock grow in my hands. I keep stroking him until his cock became rock hard. "Jackie that feels good", he moaned lowly. I didn't say a word, I just keep it up. It was long before his hips were moving in unison with my hand. "Oh god Jackie don't stop, I'm going to cum". He stiffened up "Oh Jackie don't stop I'm cummmming" he moaned. I felt his cock quiver, and pulse with the first shot of cum that covered his belly.
I keep stroking him, his goo was thick, it covered my hand like a glove.
"Jackie that was good", he gasps out. I felt funny inside, about doing this, but at the same time I felt good about doing it, about talking with someone about how I really felt, but most of all feeling my friends big cock.
"Jackie did you enjoy that?" He ask me. I wasn't sure how I felt, but I did enjoy it, "yes I did" I answered him. He smiled at me, "Good, I need to clean up, and I'm sure you will to", he said as he got up and went to bathroom.
My little cock was rock hard, I wanted to cum so bad, I had George's cum all over my hand, I gave in. I slipped my cum covered hand into my pink panties and began to rub myself to an orgasm, which didn't take very long, my panties were full of Georges cum and my own, but I felt relieved about it. My hand still covered in cum I put my finger tips to my mouth, and tasted Georges cum and mine, it had a slight musky smell to it, I tasted it. A slight salty flavor to it, but otherwise not bad I was going to taste more but George walked back in my room.
He smiled at me, "Jackie looks like you have had your hands full tonight as well as your cute pink panties".
I smiled, "guess so, I think I need to clean myself", I said as I got up and went to the bath room. My whole private area was covered with cum, a hand towel wouldn't do the trick, So I turned on the shower, slipped out of the panties, threw them in the shower, I reached down, and scooped some of the cum off my privates, and tasted it again, it was different but not bad.
I stepped in shower and began to wash myself, and panties. "Morning sleepy head", mom said.
I saw mom and George sitting at the breakfast table. George smiled at me. "Morning" I replied as I sat down. "Late night dear?" Mom said. "Yep it was hard time sleeping" I replied. Mom poured me a cup of coffee, "Here sweetie, this will perk you up". "Thanks mom", I replied. I sipped my coffee, it was good. "I need to get home, dad has things for me to do, thanks for letting me come over Jackie and Miss Thompson", he said as he scooted his chair out and got up.
I didn't realize that he had called me Jackie, until Mom said something about it. "I like him he is such a good young man, "Ah to be young again, the girl that catches him will be a lucky one at that", Mom said with a grin peeking out over the top of her coffee cup.
She sat her cup down; looking down into the warm liquid Mom said it, "why did George call you Jackie?' I opened my eyes wide, not knowing what to say except. "I don't know mom, maybe just giving me a hard time I guess".
Mom got up over to sink, "well I think it's okay, as long as you're okay with. I need to go to town and pick some things, think you could be a dear and clean the dish for me Jackie?" "What?" I replied. Mom turned and smiled me, "I said would you be a dear and clean the dish for me Jackie." "Yeah, sure mom" I replied. She walked by me and patted me on the head, "Thanks sweetie, I appreciate it." While mom was gone I had a chance to dry her pink panties and get them back in her dresser.
I took out a pair high cut purple panties, and took them to my room, slipped them on, the satin feeling against my skin caused my cock to get hard. What I did to George only fueled my sexual arousal higher; I was getting turned on again.
I lay back on my bed and pulled my cock free and started stroking it. I closed my eyes and thought about the night before. In no time I felt the ticklish feelings of my orgasm begin. With my first shot of cum I was picturing Georges cock in my hand; I came hard, very hard. I held on to my cock until it went soft. I got up and went to bathroom and cleaned up. I had to change panties again so I washed out the purple ones, dried them and took a pair of red ones to wear. I slipped my pants over them.
Mom made it back from the grocery store. I went into garage, to help her. "Here sweetie take the groceries for me", I noticed a couple of sacks from her favorite women's clothing store, "I'll get these", she said as she grabbed her sacks and walked into the house. I had finished unloading the food, when Mom came back into the kitchen. "So what would you like to do today Jackie?" she ask me. "Mom, why do you keep calling me Jackie?" I ask her.
"I like it, that's why". she said with a smile, now what would you like to do today?" I gave up, "I don't know Mom, just hang around I guess". "Hang around it is then", came her reply. We didn't do much that day, talked a bit watched a few movies, just an ordinary relaxing day. With one exception I couldn't keep my mind off Georges cock. After supper I help Mom clean up.
"Mom I'm going to my room, gonna surf the net" I said. "Okay sweetie, don't stay up to late, you have school tomorrow" she replied. "I won't" came my reply as I walked to my room. I clicked on my computer, clicked on my E-mail, and opened it. There was one from George I opened it. "Hey Jackie, thanks for last night, I really enjoyed myself, think we can do it again?" I waited to reply, yes I want to do again is what I wanted to write.
I closed his mail, and would respond later to it. I went from there to my favorite she male site, and cruised for about an hour. They were so lucky I thought to be able to have it both ways, the best videos I liked was the ones that the guy's seduced the girl's, had sex with them, and then the girls would cum while having anal sex. I really didn't care to much for the ones that guys sucked the girls off, I didn't find it arousing at all.
I went to check out and see if there were new hypnotic sissy videos, and found few short ones and watched them. The images I loved, so subtle but had an impact on me, I found myself getting more aroused watching them. I knew that I had to answer to George, so I went back to his e-mail and began to type, "yes I would like to do it again, but you can't ever tell anyone&hellip.
Jackie" I took all of 15 minutes for him to answer, "Cool, but I can't this weekend going out of town with dad, maybe next weekend to, George". We had one month of school left George wasn't able to come over, he did call a few times. His e-mails always told me that he couldn't wait for it to happen again. Mom was hard at work, and me well I keep watching my video's doing house work, and fantasying about George's cock.
It seemed like every night I would jack off thinking of Georges cock, and when I came it was always good. It was a week before school was out when Mom approached me in my room. "Jackie honey, we need to talk", she said. "Sure mom". We went into the living room and sat down; Mom reached over and grabbed my hand, and looked me straight into my eyes.
"Jackie what I have to say has been on my mind for a while, I know that you have been wearing my panties, I know that you like to dress up also". I was shocked I didn't know what to say to her but I knew I had to say something. "Mom how did you how did you know?" She smiled at me, "Honey a woman knows her panties, and I found a pair here and there that you used to masturbate in, I thought it was just a phase every boy went through, my brothers did it, but it passed for them.
I keep finding a pair here and there, well over the years one would begin to wonder if this passing phase wasn't passing at all, anyway remember when George last stayed over here, and just before he left he called you Jackie".
"Yes Mom I do remember" I replied. "That had me wondering for a bit, well about a week later he called you, you were out mowing the lawn and I ask George why he started calling you Jackie, he finally came around once I threaten him by no letting him come over anymore, he told me the talk you two had, he told me that Jackie was your girl name, and it all made sense then.
Now mind you Jackie, don't be mad at him, I think if it was any other boy, there would have been rumors spread all over, and probably you would have had quite a hard time at school, so no I don't think he told anyone, to me that is a mark of a true friend, to keep another's secret like the one you have, so with all this being said, you will have all summer long to think about this, but I don't want you wearing my panties anymore." Mom got up from the sofa, "Come with me Jackie".
I got up and followed her to her room. On her bed was seven pair of French cut satin panties, black, red, green, gold, pink, purple, and a peach color, four packages of panty house, black, and tan. Three pairs of shoes, all heels, three bras', pink tennis shoes, some pink ankle socks, several black nighties, four different satin pull over tops all white, some shirt's, a few mini dress's.
Two black panty girdles, some jeans and high cut offs. "These are yours', I expect you take care of them, and last you all summer long, as time goes on I will replace the worn ones, and will expand your wardrobe, if you so desire to continue to do this, so once school is out so is the boy, besides you have the skin and looks to be a girl, almond shaped eyes, small nose your brown soft hair, which also you let grow another indicator to me", mom said with a giggle.
I really didn't know what to say. I was relieved with Mom knowing, things wouldn't be so tense for me. As for George, what mom said about him being a true friend had a ring of truth about it, so I wasn't too mad at him for it.
"Thanks Mom" I stuttered out. Mom smiled at me, "Now get your stuff Jackie and take it to your room, I think you need to change for mom" I didn't know how to answer that, I mean it was all fine and dandy that I could dress up in the freedom of the house, but to be in front of my mom that was different.
"Jackie you may as well get use to, like I said this summer the boy is out and the girl is in, so get to it daughter". I gathered everything up and took them to my room. I went into the bathroom and ran the shower.
I heard the door open, and Mom said "use the Lavender soap Jackie I like how it smells, and don't forget to use hair remover first, no body hair young lady." I did what she told me, to do, mom apparently was getting into all this.
When I got out, I had noticed that Mom had put a black satin rode, and matching panties on the counter, with a little note attached to them "Jackie be sure to use the body lotion, on your arms, legs and bottom, I will help you with your hair and make-up." I did it, feeling the panties slip over my freshly shaved legs seen tingles up my spine, slipping on the robe, I walked to my room.
The sensations were tremendous turn on for me. Mom had me sit down at my desk. "Jackie drop the robe, and try this bra on".
She handed me a small black lace and satin one. Once I got it on, mom handed me to things she called falsies they looked real.
"Put these in, honey, got to make it all look real". I did as she told me. The both fit real nice, and it was hard to tell that they were fake tits. "Jackie put this top on", she said.
I slipped the white pull over on and watch the front fall over my fake tits. Mom had finished my hair. "Jackie I want you to slip these panty hose on, and shorts, I think you will look cute in them." I opened the tan panty hose up, and sat on the side of my bed.
"One foot at a time Jackie you don't want no runs in them". I did as Mom said, they fit nice. Mt cock had gotten hard, and Mom had noticed it.
"Jackie we can't have that, take off the panty hose, and panties now, a good girl don't show off", she said. I was embarrassed, but I don't know what caused me to follow her orders like a puppy, but I did it. "Good, now wait, you must never show your excitement, it will go down" she said as she slapped it.
I cringed. "Jackie now stop that you want this don't you?" she ask.
"Yes mom I do, but it hurt when you slapped it", I said. "Well young lady its working" she said pointing to my now limp cock. "Put the panty hose now". I sat down again and slipped the panty hose back on, and the black panty griddle. "Good, now push you little cock between your legs the griddle will keep it nicely tucked away". She was right you couldn't tell I had a cock.
it felt strange with my tucked between my legs, it wanted it to get hard but the position it was in it wouldn't get hard at all.
I slipped on the cut offs, they were tight, but they fit nice. Mom had gotten me a pink pair of tennis shoes, and some pink ankle socks, and had me put them on. "Stand up Jackie, let mom see her new daughter".
I stood up. "Turn around slowly". "You know Jackie you really do have a bubble butt, no pads will be needed there, come on let's get a soda" I followed her into the kitchen got a soda and sat down at the table. "Jackie this is going to be a big step for you, I will help you, but there are some rules you will have to follow." "Rules? What kind of rules mom", I ask her. "Nothing to hard to follow, no boy's here, except George, I can trust him, you will have to always dress like a prim and proper young lady, you will practice your make and hair every day, basically everything that I want you to do, but the biggest rule you must follow is that once school is out, you will be my niece, Jaclyn who is coming to stay with this summer and my son Jack is staying with my sister, but above all never hide anything what so ever from me again, pretty easy so far isn't it?" "Well mom it sounds easy so far, but what if you're not home and someone shows up, what do I do?" I ask her.
"That's easy Jaclyn, be the girl you always wanted to be, with a little more practice no one will ever know, except myself and George". She said. "As for George, he is your friend; don't lead him on, about anything okay?" "Yes momma I will do my best", I replied. "Good, now remember you got one week of school left, every day practice hair and makeup." I got up and went over to mom and gave her hug, thanking her for all the understanding and gifts.
On my way to my room, I stopped in the bathroom, and looked at the makeup job mom did, "WOW" is what I thought, it would hard to tell that this face was the face of a boy. My brown hair had a wave to it, the blue mascara highlighted my brown eyes, the foundation was light, mom highlighted my check with some rose colored powder.
I looked like your typical teenage girl, I thought. I got on line, and E-mailed George, and told him everything. It wasn't long before he answered me, "Jaclyn I like that better than Jackie, I can't wait for school to be out, wish I could come over, but dad has been working my tail off this past month, he said I would have some free time in a couple of weeks, would love to see you right now Jaclyn&hellip.George." Mom came by my room, "Hey Mom", she stopped "yes Jaclyn?" I turned from computer, and ask her "think we can get a picture of me?", Mom stood there for a minute.
"Why Jaclyn?" I knew that if I didn't tell her she would get mad, so I just blurted it out, "I want to send George one". Mom turned and went to her room, I thought she was mad at me, but she returned a few minutes later, "Okay stand up, put your hands on your hips and smile". I poised for her, she took several snap shots and we loaded tem onto my computer.
"Thanks mom" I said. "Now Jaclyn remember what I told you about George, don't lead him on at all." she said. " I won't mom he's is my friend, and I told him all about today and what you had done for me, and he just wants see what I look like" I said. "Well okay then, send him one and only him Jaclyn." I turned and began to type away. "George here's a picture of me, I hope you like it…Jaclyn". I attached it to E-mail, and sent it. It took George a while to answer me.
"Jaclyn I can't believe it's you!
You look so pretty……George. I got up and went back into the living room, mom was on the phone, I sat down and started watching T.V. When mom hung up, I told her that George liked the picture, she smiled and said "I thought he would, how do you feel about that, him liking you this way?" I thought for a moment before I answered her, " I thinks it great mom, he has always been my friend, and it really got to me hiding this from him, like it did, as for him liking me being this way, I don't think it makes different to him." "I think you right, he's a good boy and I'm sure that once he gets to know as Jaclyn, he will like what he sees." I wanted to tell her, that he does like me as Jaclyn, but if I did, she wouldn't allow him to come over, so I keep my mouth shut.
We talked about boys that night, and I had to look at them with a girls prospective, and once I started doing that, it became clear to me that most boy's wanted only thing and that was sex, which when I think about it, mom was right.
I really not thought to much about it. All's I ever wanted was to be a girl, so those boy thoughts really never crossed my mind. It was getting late, when Mom and I went to bed.
Mom told me that I was to leave the panty griddle on, under my nightie, she also told me that from now on at home when I use the bathroom, I was to sit down, no more standing up. I slept peacefully that night. This was our routine for three weeks, I had gotten really good at doing make up and my hair, mom even had some fake nails and she applied them to me, that was hard getting use to the nails, as was the heels, but like Mom said I had to practice, which I do, my voice was changing don't know if was the talking like a girl, or what.
Mom had gotten home early from, she had told that she needed to go her sisters this Friday night, and would be back late Saturday afternoon. "Is there anything wrong mom?" I ask. "Oh no Jaclyn, your auntie just needs some help with the work she is doing, and she knows how good I am with numbers a statistic's," Mom replied.
"While I'm gone Jaclyn, I don't anyone in the house", that made my heart sink, I had been so looking forward to seeing George, this Friday was a night off from his summer job at the pizza parlor. Mom sensed something was wrong, and I told her.
"Aw Jaclyn, it's okay if George can come over I don't believe anything will happen, he's the one boy I do trust", she said.