Jake And His Debi
by: Miss Deborah (Debi) Leigh Johnson

 

Jake is my college roommate. We get along really well, and we have been sharing a dorm room for a little over two years now. I guess that you could say we have sort of gotten used to each other, so we do not have a lot of stress between us, which really helps, especially at exam times, when the last thing that anyone needs is a stressful relationship with a roomie.

Jake is almost my complete opposite. He is tall, dark and he is handsome. He has thick black wavy hair, so black that it almost looks blue in certain lights. I am sure you know what I mean. He is built like a professional athlete, though Gawd alone knows how he manages to look like that all the time because he certainly does not work out or jog or anything like that. But, man is he strong. I once saw him actually lift the back end of a car about four inches off the ground. True, it was a small car, but he did it and I do not know a lot of people who could have done that.

His looks get him every kind of chick that you could imagine running after him.

I guess that is why he seems to be so cavalier towards the ladies, I don’t know. If I had the ladies after me like that, well my head would be so swollen that I would have trouble going through narrow doors.

Because we are opposites, I am really opposite to him. I am 5’4", thick long dark blond hair, light blue eyes and a fair complexion (so I better watch myself in the sun shine) kind of fair complexion. I burn really easily.

We first got stuck together by the "powers that be", who were assigning out the dorm rooms, when we first enrolled in college, but after I got over my first four months of being intimidated by his masculinity, not that he ever tried to intimidate me, but he just did. Compared to him, I felt like a dainty little girl, and I was not really sure if I liked that feeling or not.

I grew out of the feeling though and we found that though we had nothing in common with each other that we could actually be of some help to each other. He was weak in some academic areas, and I was very helpful to him. I was very weak in some financial areas, and in appreciation, Jake often gave me little money gifts, and sometimes other kinds of gifts too.

Over all, we grew to become really good friends and to appreciate each other’s differences as something that would actually enhance our own lives, if we let it.

Then, last week, out of the blue, Jake floored me. We were just heading into a long weekend and we both really needed some serious R&R. Mid term exams were just past us and we had slaved for hours to prepare for them. We both felt that we had done well though.

Jake and I began on Thursday afternoon after the last exam, by getting into the case of two-four that he had sneaked into the dorm room refrigerator. Needless to say, by 7 pm, we were both feeling very good indeed.

It was then that Jake absolutely floored me. He told me that he had brought me a present. He went into his bedroom and rooted around for a few minutes then he came out with a large green garbage bag. He handed it to me then went over to drop himself into his favourite depression on the far end of the couch.

He sat there grinning at me as I untied the big knot in the top of the bag. It seemed to be filled with clothes.

I turned the bag upside down and emptied it onto the floor.

It was filled with clothes, all in soft silky kinds of materials. It did not take me too long to discover that every item that was in the bag was of girl’s clothing. Everything that is, except for the makeup kit that was included. I was stunned. I kept looking up at him as I rifled through the pile on the floor.

There was lingerie, all very pretty and all made of satin. There were slips, skirts, blouses and dresses. I realised that there was enough there for a girl to wear for a week.

"Wha…?"

"I got those all for you."

"But, they are all girl’s clothes Jake. Why would you get them for me?"

"Because sweetie, I happen to think that you are the best little wife that I have ever had."

"I am not your wife." I tried to muster indignation, but all I got was the realisation that in a lot of ways, our relationship was kind of like a husband and wife. He took care of our needs like groceries and stuff, but it was me that did the cooking and did the laundry for the two of us and I also did all of the housework, including making his bed for him at least once a week.

I was stunned.

"And because I think you are way too pretty to pretend that you are a boy. You wanna know why else I got them for you?"

My throat was dry. "Yes…" I managed to creak out.

"Because, I watch you all the time around here. You do not realise it but you act an awful lot more like a girl than like a boy. Well, about two months ago I was watching one of those talk shows and it was all about boys who like to dress up as girls, and some of them even went out with boyfriends. I started to think about you. I started to think about how pretty you would look if you had some pretty clothes to wear. I started to think about how cute you would be as a girl. The more I thought about it, the more I thought that I could really dig you if you was really a chick."

"Well, you are not a chick, but I honestly think that you would be happier if you were a chick. So, last time I went home, I got some of my sister’s clothes for you. I gotta admit that the idea of seeing you dressed up as a chick, and taking you out on a date really turns my crank for me."

"Bu… Jake? I am not a chick…"

"Bu… Denzil?" He was mocking me. "You want to be a chick, and I think you would really like to be my chick."

I stared at him for a long minute, trying to understand what he was saying. As I was staring, I was unconsciously holding a pair of white satin panties in my fingers, and caressing the material. I did not know why, but this surreal thing was really turning me on. I actually was getting a hard on.

In a last ditch attempt to try and bring it back to normalcy, I whined, and I admit it now that I whined like a girl would, "But Jake, you want me to dress up like a girl and go out on a date with you like any other girl, and then, like any other girl, you want to bring me back here so I can suck your cock for you, is that it?"

"Well, not completely."

"Not completely? What do you mean?"

"Well, if I really get lucky, you might let me fuck you too, like most of the other chicks that I bring back here do."

"Oh she-it. This is just too unreal."

"Face it Denzy. I want you to be a girl. I know that you want to be a girl, hell all you have to do to know that is just to look at the way you are playing with your new panties right now… A guy would just never do that sweetie. So why not just do it and see what it is like?"

His words were slapping me in the face like a two by four revelations across the forehead. I was stunned and yet I knew deep down inside of myself, that I could not argue with him. What he was saying had a ring of truth to it.

"You… You want me to go and put these clothes on and come out here and act like one of your girlfriends acts?" I was astounded. And yet when the words were out, they suddenly became the most erotic and enticing words I had ever heard.

"Yeah, I’d say that about sums it up."

I really did not know what to do now. But I knew that he was really expecting me to do it for him. I was torn. I knew that as a boy I should not even be considering such a thing, but there was something inside of me, very deeply buried inside of me that was actually responding to this perverse suggestion.

I was feeling really giddy, and I knew that I was going to do it.

The idea of wearing pretty clothes, especially clothes that would not stop the big lugs hand from going up under my dress if he wanted to feel me up, and of having him kiss me and maybe even make me sit on his lap was really exciting. But I also knew that if I did this, then he would expect me to suck his cock too. He’d really expect me to act just like any other girl acted when she was with him.

Could I be that much of a fairy? I did not want to, but my eyes were drawn to the slight movement of his hand, which seemed to be rubbing his crotch. Wow, I had not even dressed up yet, and I was turning him on already. I felt a surge of feminine power over him, and I loved the emotion too.

"If I do this Jake, you got to promise me that you will not try to rape me or try to make me do anything that I do not want to do, okay?"

"You got it babe. Now, you go and get yourself all pretty for your brand new boyfriend, and I will go out and get us some party fixin’s for later on. My sister is a real fox, and I am certain that her things will fit you perfectly too. Ahhh… I want you to know that she has worn everything that you have there, and she’s looked fabulous in it too. So, I’ll go out now and get the stuff for later on while you’re makin’ yourself all pretty for me."

"Later on?"

"Well yeah, for after we come back from our date."

I felt a wonderful emotion then, like I had somehow come completely under his masculine and very masterful control, and I was amazed to find that I loved how that felt to me. I’d never felt like this before, and it was terribly exciting.

"Are you going to go and get yourself all pretty for your new boyfriend?"

"Yes Jake, I will make myself all pretty for my new boyfriend." I felt a wonderful sense of elation and freedom when the words ‘my new boyfriend’ passed my lips. I had never ever dreamed that I would ever say anything like that, but I had.

Jake got to his feet and came over to where I was seated. He leaned his big frame down and he lightly kissed my lips. It was my first impression of him, looking up at him through a girl’s eyes, and I could not believe how big and strong and masterful that he had suddenly become. I was thrilled that he kissed me too. It was a very light, very brief just a touch of his lips on my lips, but it was my first kiss from a guy, and it was wonderful.

"I’ll be back in about an hour. That should give you time to become Miss Debi."

"Miss Debi?"

"Yeah. Miss Debi, and it is spelled with only one ‘b’ and one ‘e’. That is the cute way of spelling Debbie. I picked that name for you because you look an awful lot like a really cute high school girl I used to date, named Debi. Hell, I bet you could pass as her identical twin because you look so much like her. You even have the same last name. Her real name was Deborah, but we all called her Debi because Debi is such a cutesy name, where as Deborah seemed so formal. And she really was a cutesy too. I… I had always had a crush on her, and so you get to be my sweet little Debi once again, and you get to have me have a crush on you..." Then Jake was gone.

Stunned, I sorted through the clothes. They were all very expensive, I could tell. There were four sets of lingerie, four dresses, four skirts, four pairs of high heels, a pair of pink mules, the kind with the little puff on the vamp, and of course, there were four nightgowns or baby dolls. There were also four slips, two full ones and two half ones with camisoles that matched the bra and panty sets. And there were four really silky feeling blouses and two mohair sweaters. Geeze, any chick that I knew would love to have clothes like these.

I also found a package with six pairs of lacy-topped thigh high stockings that the label said were extra silky. I also found a box that I soon discovered contained a set of realistic looking breast enhancers, just a slightly darker colour than my own skin. I read the box and discovered that they were activated by body heat, so they would stick to my skin once I had them in my bra. Wow, who’d of ever thunk I’d be thinking in terms of ‘my’ bra?

I also found a very pretty lightweight three quarter length car coat. It had three big buttons up the front and looked a wee bit like a trench coat. It has a satin lining that would feel very nice on my arms, when I put it on. There was also a light beige coloured sort of alligator looking leather purse with a long shoulder strap. Inside it, there was a girl’s wallet, empty of course, but decidedly a very feminine looking wallet. I also found in the purse, and pair of light beige leather gloves that would extend up to my wrists. They were very soft and had a small bow on the back near the wrist cuff. And, there was a sky blue silk scarf as well. It was all very pretty, and everything that any girl would need, according to my limited understanding of what a girl would need anyway.

I was really amazed at how he had seemed to think of every little detail for my effemination. I realised that he must have been planning this little project for quite a while, given the completeness of his provisions.

Hell, I admitted to myself, I really loved having clothes like these. I could not help but to know that I was going to love how they would feel when they were actually on me. I also knew that I was going to love wearing them for Jake. I could hardly wait to feel what extra silky would feel like, as I looked at the pack of nylons in my hand once again. I was so hard I could barely believe it.

I went to my room and located the clothes in my closet and drawers. I selected what I was going to wear for my debut as Miss Deborah, also affectionately known as Miss Debi. I was pretty sure by now that I was going to love being a ‘miss’ and a girlfriend… A girlfriend to my new boyfriend… I could not stop the smile that played with the corners of my lips.

Then I took a bubble bath and shave the very little hair that I had on my body, including my face though I usually only shaved once a week as it was. Then I went back to the bedroom and sat on the bed, to put on my very first pair of girl’s panties.

The lingerie, since it would be my first time as a girl, was naturally enough, the pink set. The nylons I had chosen were the light beige ones. I had also decided that I would wear a dress, after all it was true that skirts and blouses were also just as feminine, but in some cultures boys also wear skirts and blouses, but I did not know of any culture where boys also wore feminine looking dresses. It was going to make me feel just a wee bit more feminine to know that I was wearing a dress, and not only that, but a dress that a very pretty girl had worn before me. I’d seen pics of Jake’s sister, and she was a fox.

I picked up the panties and raised one foot. I looked down into the panties and knew that only girls and other fairies ever got to see panties from this perspective. I knew that Jake’s sister had seen them, and that the cotton gusset that I was looking at, had also caressed her feminine vagina before.

Probably, if he was lucky, Jake was going to get to feel that gusset from the outside, while I was feeling him from the inside of the panties. I almost creamed right at that moment because the thought of being so intimately connected with a real foxy chick was so exciting to me.

The closer the moment drew for me to be a girl with him, the more turned on I was getting.

I worked the satin lace trimmed leg hole over one foot, then over the other. I pulled up my first pair of panties, relishing how delightful the cool soft delicate satin felt on my skin as I raised them up my legs. Then I stood and pulled up my pantywaist to my hips. The softness caressed and clung to my little cockette and it was the most wonderful sensation that I had ever had. I reached around and lightly caressed my bum cheeks through my panties. I knew at that moment that I was going to be throwing out my male underwear, and I was never again going to wear anything but the finest of lingerie for underwear from now on.

I slipped the straps of my new lacy bra up over my shoulders. I’d never put on a bra before, so it was a bit of a discovery process and experience. I had to admit that I really loved the tightness around and over my shoulders. It was something that girls felt, and it excited me to know that I was feeling such things too. Then the pretty little enhancers went into the cups. Suddenly I have a very convincing looking bust. I loved it. It felt so completely and utterly girlish. It also made me feel strangely like I was at peace with myself for the first time in my life.

I carefully slipped the lovely extra silky nylons up my legs, and I marvelled at how sensual the material felt. I loved the way it clung so tightly and almost transparently to my legs. It was no wonder that girls loved wearing this stuff. When I stood up, I felt the delightful tug of the material all over my legs and it was very erotic. Yeah, again I knew why girls like to wear this stuff. Guys were really missing out on it for certain. Thank you Jake for making me do this thing for you.

I held the slip up over my head and looked up into it. It was a sight that only Jake’s sister had had before, and now I was enjoying the same intimate feminine experience as she had enjoyed. I shivered as I felt the lovely satin slowly begin to caress my skin as it slithered down over my head. As it descended, I had the eeriest feeling that I was somehow becoming enveloped in the femininity that it was designed to enhance.

I nearly swooned because it felt so nice to me. I loved how it was making me feel like a real girl. Geeze, if girls got to feel this way, why on earth would they ever become libbers and give up wearing stuff like this? Were they all nuts?

I went to the bathroom. In the small mirror, I experimented with my makeup. It took nearly half an hour, but I was actually pleased with the results. I knew that I really needed lessons, but I loved how the blue shading on my eyes and the pink glow to my cheeks and the plum glossy look on my lips looked. I was very careful with the mascara to enhance my lashes, and I was very pleased with how utterly feminine my face looked when I was done.

I parted my hair in the middle and brushed it down on the sides and back till it started to look glossy. I had always loved how Marcia Brady had looked in the old television show, and now I was glad that my hair was so long. I thought it was very feminine looking, and at that moment, I wanted more than anything to look completely feminine.

I went back to the bedroom and applied Opium to my inner wrists and behind my ears. I put on a collection of jewellery that I had found in the makeup kit bag. There was a small very pretty watch for my left wrist, a silver bracelet for my right wrist and a small delicate silver 20" chain with a small crystal heart pendant for my neck.

I left doing the fingernail polish till the last of the makeup. I was glad that I did. I was so nervous that my hands kept shaking. This was such an overtly feminising thing to do to myself, and it caused me such excitement that my hands shook. I ended up doing them nearly three times before they were smooth and shiny looking.

Then came the moment of truth. I was about to put on my very first dress. I was so hard that I was afraid that I was going to erupt in my panties, but I made the super human effort of self will to not touch myself, and save myself to let my new boyfriend take care of me.

The dress that I had chosen was kind of simple, but that was why I liked it. It had those cute little puffy sleeves that only went half way down the upper arms, and was trimmed in white lace. The neckline was also trimmed in white lace, and it was a deep round neckline. A white elastic belt with a gold coloured butterfly for a fastener pulled the dress in tightly around my waist. The pale pink dress then fell in three white lace trimmed tiers to about three inches above my knees. It was so pretty and so very feminine.

But I had also chosen it because I knew that because of the way the skirt flared out, I would not have to worry about someone seeing evidence of what was in my panties. That also meant that I would not have to bind myself back between my legs, which meant that I could enjoy the softness of my panties on the ultra sensitive cockette. It also meant that if Jake decided that he wanted to feel me up, that I would be able to enjoy every second of it.

I hoped he would want to feel me up too, I really hoped he would.

I stepped into a pair of white pumps that had three-inch heels on them. It did not take me very long to learn how to walk in them. I was soon walking in them as though I had been born with the right to wear them, as though I had been raised as a girl.

I was standing in front of my full-length mirror, brushing my long hair some more, thoroughly enjoying the image that I saw of a young lady looking back at me, when I heard the keys in the front door. I caught my breath, both in fear that he would not like me as a girl and in the anticipation and fear of what would happen now, if he did like me as a girl.

"Debi? I’m home…" He did a really sick imitation of Ricky Ricardo from the ‘I Love Lucy’ show. I could not stop myself from grinning. I spritzed some more Opium on the crown of my head, and then I walked to the door. My heart was beating wildly. I could hear him moving around in the kitchen. My hands on the doorknob were trembling. I could not believe that I was actually going to do this. I was going to let my best friend see me all dressed up in his sister’s clothes. WOW!

I waited till I heard him drop himself back into the favourite indentation in the couch, and I forced myself to open the door. When I pulled it back, he was sitting there staring at me.

His eyes went up and down me very slowly, like he was eating me alive. I could almost feel the caress of his eyes and it made me feel so utterly vulnerable and exposed to him. I loved how that felt. I knew it was how girls got to feel.

"Ho-ly she-it"

I forced myself to step out and stand in front of him. A delightful sense of naughtiness came over me, and I decided that I was going to really cement my effeminate status with him, by executing a pretty curtsy. I did so, and as I did so, I asked, "What, is there something wrong Jake?"

"Ohhh nooo… Gawd no… You are gorgeous. You are so fuckin’ foxy. Man, I just cannot believe it. I knew you would be hot, but man you are fabulous."

I curtsied again, and in my best imitation of a southern belle’s drawl, I thanked him. "Why thank you kind sir, you are such a gentleman to say a thing like that to li’l ol’ me."

He stood up and slowly came over to stand a scant six inches away from me. I had to crane my neck back in order to look up into his eyes, his very pretty smokey dark eyes. I felt even more wonderfully feminine, if that was possible. I loved it too, I loved it and I knew that it was going to be like a drug. I was addicted to feeling like this.

I trembled in tiny little shivers all over my body. My cockette felt like it was going to explode in my panties. I was so acutely aware of how the soft silky lingerie and the clingy nylons and the pull of my bra straps and the sweet constriction on my upper arms felt. I felt like I was going to feint away. My eyes drifted down to look at his lips and I wanted so desperately to feel them kissing me, kissing me the way that a boy kisses a girl he wants to possess.

I looked back up into his eyes.

He spoke very softly. "Debi, you are so fuckin’ pretty and sexy. Man, all I want to do is jump your bones you look so fine. You have this look in your eye that tells me that you really love this. Is it true? Do you love being a girl, and being my girlfriend, Debi?"

I could not say anything. I had a very painful lump of joy in my throat. I nodded my acceptance of his words.

Then, for the first time in my life, a man put his hands on my waist and he pulled me against him. I was shocked to feel a very hard cock pressing into my belly. I was amazed that I was turning him on like this. I must be much better as a girl than I had thought that I was.

Then he lowered his face to me. He looked in my eyes.

"I want to kiss my new girlfriend. The question is, does she want me to kiss her?"

I was trembling in my joy and all I could do was to nod to let him know that yes, ‘she’ wanted her boyfriend to kiss her.

His lips lightly brushed mine at first, so light that I wondered if I was imagining that he was kissing me. Then he became more demanding and more possessive and he pressed his lips against me. I felt the tip of his tongue lightly begin to caress my sensitive lips, and involuntarily I parted my lips to welcome him into my body. As I felt his hard huge tongue invade me, my arms involuntarily went up and I clung to his neck so that I would not fall to the floor.

As he kissed me, his cock was slowly being rubbed against my tummy. He kissed me, and then he would whisper in my ear to tell me how pretty I was and how pretty I smelled then he would kiss me again. I could do nothing else but to cling to him and to suck on his big tongue, almost as though I was trying to make him push it further into me.

I’d never felt so electric, so erotic and so completely and utterly alive before in my life before. It was as though every nerve ending in my body was reacting to the lovely sensations of the clothing that I was wearing, and my mind was being overloaded with the totality of the femininity of my experience.

I knew now why I had never really felt like I belonged anywhere, it was because I was never anywhere before, as a girl. As a girl, I was a complete personality and I loved being Miss Debi, and even more so, I loved being Jake’s girlfriend.

I never wanted this moment to end.

He moved his leg and I felt him brush against the cockette through my dress, slip and panties, and I almost died it was such a lovely sensation. He saw my reaction, and he rightly guessed why, and so he very slowly insinuated his right knee between my beskirted thighs. I could have died at that moment and known that I had really known true happiness for the first time in my life.

I clung to him and tried to swallow his tongue. I’d never been so turned on in my short little life.

We kissed like that for a long time, and I got to enjoy one more experience that normal girls get, that I had never thought of before. I got to feel a man’s hand as they explored the outline of my bra straps, and then as they slowly inched my skirt up so that he could grasp my pantied bum cheeks.

He whispered in my ear that I was turning him on because I was acting more feminine than most of his other girlfriends did. All that I could do in response was to suck on his tongue and moan out my pleasure as I gave myself completely over to the feminine experience.

After we kissed like that for a long time, I managed to whisper in his ear that he must be really hurting because he was so hard. He told me that it was really uncomfortable for him, but that he liked being so turned on. I asked him if he wanted me to help him with it. He stood back and looked deeply into my eyes. I could see in his eyes that he understood that I was a girl now with a girl’s desires to please her boyfriend.

He said that he wanted me to do that, but before I did that for him, he wanted me to know what it really felt like to be a girl. He told me that he was going to take me out on a date so that I could find out what really happens to girls when they were in love.

I was terrified at the idea of leaving the dorm room dressed as a girl, but he assured me that I was very pretty, and that if any one did look at me, it was going to be because I was so beautiful, and because I was so beautiful, I was just going to have to learn that being looked at was a fact of life for a girl who looked like me.

He was so sweet. I kissed him. I told him that I was scared witless, but if he promised to protect me that I would do whatever he wanted me to do, and I would go wherever he wanted me to go. He smiled and told me that this was exactly what a guy wanted to hear from his girlfriend.

I went back to the bedroom and slipped my arms into the coat. I was right. The soft cool satin lining felt fantastic on my arms. It sent little electric thrills up and down my spine. Then for the first time in my life, I slung a purse over my left shoulder. It just seemed to feel so right somehow. I decided not to wear the scarf, but I did put the lipstick, some tissues and my perfume into my purse. I also decided to slip $40.00 into my new purse, just on the off chance that I might need to pay for something, though I knew only too well that one of the privileges of being a girl was that you had boys to pay for things for you.

I giggled. This was really living.

I went out to the common room again, just as Jake was emerging from his own room. He had put on sharply creased slacks in stead of his blue jeans. He was also wearing a clean shirt. I knew that I was being treated special because he only dressed like that for special occasions. I could not keep the smile of pride and pleasure from my lips as I admired how good he looked, for me.

Gawd, he was a handsome man.

He took my nervous Nellie hand in his and he lead me out of the dorm. We walked down the hallway to the elevators. I was glad that we did not encounter any of our friends. I was certain that they would know who I was and brand us for the rest of our lives on campus as femme and butch girlfriends. It was like them to do things like that. Jake held me close and assured me that I was far to pretty for anyone to associate me with his roomie. His words made really me feel a lot better.

Still holding my hand, he led me from the elevator and out into the parking garage and then over to his car. He even opened the door for me, treating me like I was a real princess. I was heady with the experience and I knew that I would really love to have to get used to this life style.

I sat in the car and reached over to unlock his door. I had seen a movie once where the star had said the he always helped his girls into his car, and then waited to see if they thought about him enough to reach over and unlock his door. If they did not do that, he would dump them, assuming that they were too selfish to think about his needs.

I wanted Jake to know that I was the kind of girl who thought about her guy’s needs.

I folded my hands on top of my purse which I held on my lap. I was so nervous and excited that I was actually trembling. I was still completely aware of even the tiniest physical sensation I was getting to feel, like the coolness of the leather seat under my skirt and the way the car heater blasted cold air up my skirt when he turned the car on. It was very exhilarating, and so completely different from anything I had ever gotten to experience before.

I was also acutely aware of how lovely the soft panties felt on me. Gawd I loved wearing panties. I knew that I would never wear boy’s underwear again, not unless I was forced to wear them.

I did not know where we were going. He was the guy, so he was making the decisions for us. We headed out onto the highway and headed towards the far side of the city. When we saw the signs for the mall exit, he turned off there. I was so scared of what we were about to do. Jake must have noted my fear and my trembling hands. He leaned over, placed his big strong paw on top of my hands, and he kissed me, and he told me that he was really looking forward to letting the world see what kind of a beautiful chick he could get interested in him.

He was really trying to make me feel good about being his girl, and it was working. He seemed to know exactly what to say to make me want to be his loving girlfriend. I raised one of his hands to my lips and I lightly kissed the back of it as I looked up into his eyes with a grateful expression in my eyes.

In the mall parking lot, he raced around the car and opened my door for me, then gave me his hand to help me out. I needed it as I was not used to getting in and out of cars gracefully while wearing high-heeled shoes. I knew that he was going to make me feel as much like any other of his girlfriends ever felt with him, and I was thankful for that. I don’t know how the other girls ever let him slip out of their grasps, as he was such a gentleman to me.

He took my hand and led me into the mall. I nearly froze up in terror, but he put his arm possessively around my waist as though what we were doing was the most normal thing in the world to do, and he sort of pulled me against him as we walked. I soon realised that I was getting only three kinds of looks.

One was from lecherous guys who did nothing to hide their admiration of what they were seeing. One other kind of look was from other girls. There were mostly interested in what my dress looked like, and what Jake looked like. More than once, I also saw the green-eyed monster looking out at me when another girl passed us by. That was the third look.

Once I began to really begin to understand that people thought I really was a girl, I began to relax in his embrace as we walked along, and I began to enjoy the envious looks that the other girls were giving me. It felt kind of neat to be envied by them, for the kind of a guy I was able to attract to myself.

Meow!!!

I loved being a girl.

He took me for a long walk through the mall. He told me that it was too early to eat dinner and too early for the shows to start, so he wanted me to know what normal girls got to feel walking through the mall. He asked me numerous times what I was thinking and I was honest. I told him exactly what I was thinking. He seemed to really be tickled because of the typically feminine nature of my thoughts and feelings.

By the time that we had made our way through the mall once, I was entirely comfortable in my role as his main squeeze. I liked it too. I liked it a lot.

Jake mentioned that if we had some supper now, we’d be done by the time the late movies started and he asked me if I wanted to go to a restaurant for some dinner. I was not hungry, as I was too excited about my adventure in Jake’s sister’s dress, but I did want to know what any other girl would feel on a normal date, and being taken to dinner certainly seemed like a normal thing for a girl to experience.

I agreed. Jake decided on a big name chain restaurant that we both agreed that we liked. I kind of had the feeling that whether I liked it or not, Jake would have taken me there anyway. I also knew that I kind of liked that decisiveness about him. It was such a guy thing. I’d never been like that and I admired him for being like that by his nature. If I tried to be like that, it would have been something that I would have had to consciously struggle with.

He led me into the restaurant. He held my hand as we waited to be shown to a table. He nudged my shoulder and pointed with his chin. "That is where the ladies room is if you need to go to freshen up or something. That idea had never even dawned on me, but I knew that it was something that I would have to know if I was going to be wearing dresses in public for extended periods of time, which I was becoming more confident that I would be doing as time passed. I loved it too much to stop doing it now.

I was addicted, addicted to how wearing dresses made me feel so wonderfully feminine… And addicted to how it felt being treated like I was a real girlfriend. I also suspected that I was also going to be addicted to acting like a real girlfriend when he took me home again.

The waiter actually pulled out my chair for me. I smoothed out my dress under me as I had seen ladies do, and let him seat me. He was so friendly and smiled at me a lot. He obviously thought that I was a pretty girl too. I could really get used to this kind of treatment, I thought to myself as I picked up the humongous menu card.

I read it over but I was so excited that nothing that I read stayed in my mind. The waiter came back to take our orders. I told Jake that I did not know what I wanted. He ordered me half a carafe of medium dry white house wine and a seafood salad. I would never have thought of that, and I was thankful because when he said it, it seemed like just exactly the right thing for a girl on a date. I let him know I appreciated it with a glowing warm smile.

I was almost aghast at what he ordered for himself, though I had seen him eat like that before. It just seemed that compared to my very feminine meal, his seemed to be humongous. He ordered a half chicken, and order of ribs with extra fries and a jug of draft beer. He grinned at me, knowing fully well that I was the woman and he was the man, and that I was getting to experience this new and totally unexpected aspect of being a girl on a date with a virile young man.

He beamed at me when he saw my smile. It was obvious that being with a pretty girl who appreciated him was really stroking his ego too. I’d have to think some more on that aspect of being a girl, but I loved it none the less. I also idly could not help but to wonder if his ego was the only thing that he was going to expect me to stroke tonight.

I sighed because I did not care what he wanted me to do. If it was what a girl did, then I wanted to know how it felt to do it too. I wanted to know everything that a real girl got to feel as a normal part of her every day life. I was in love with my newly discovered girlhood, and I did not care who knew it. I wanted to feel everything that girls got to feel. And I wanted to do everything that girls were expected to do too.

I realised that Jake might actually think of me as a fag now. Well that was just too bad. I was not a fag. I knew that now. I was a girl with an extra thing in her panties that she was born with and had no control over. If Jake wanted me to take care of him in that way that girls take care of the guys they love, I was pretty sure by now that I was going to really love to do that for him.

I wondered if he thought that I was pretty enough that he would want me to take care of him. I hoped so.

All too soon the supper part of the dream passed before I even realised how late it was getting. I truly felt like I was on a pink cloud of bliss that was just so intense that I could think of nothing except how pretty and sexy and wonderfully feminine I was feeling.

I let Jake help me get out of my chair, and I stood by like a girl, waiting passively as he counted out a tip and then took the bill to the cash register to pay. I loved having the guy, my boyfriend, pay for my dinner. Then he placed his arm around my waist in a rather possessive way that made me feel absolutely under his strong masculine power, and I was thrilled with how that felt too. I surrendered to his leading, and I followed him to the movie theatre. I did not even care what we saw. I just wanted to see a movie, with my new boyfriend.

We were a bit late as the movie had already started. He located two seats for us in the back row, far enough away from the doors that we would feel a sense of privacy. I sat down and he went to get me a soda. When he came back, I was glad to see him. I accepted the soda and he sat beside me. His left knee pressed lightly against my right nyloned knee, but I liked how it felt, and I did not move my leg. I actually pressed back lightly, to let him know that I liked how he was treating me.

About ten minutes into the movie, he placed his arm around the back of my seat. His left hand rested lightly on my shoulder. I took the hint. I wanted to know what it felt like. I turned slightly and lay back so that my head was laying on his shoulder. I could feel the strength in his arm and I really liked that.

A couple of minutes later, I felt the fingers of his right hand under my chin. I turned my head up to look at him. I could see his eyes gleaming in the luminescence of the movie screen. He was looking at me with sheer lust, and while it made me feel very week and small, it also made me feel very desired.

He lowered his head and I closed my eyes. Soon I felt his lips lightly kissing my lips. His tongue began to probe at my lips and I parted them. I wanted to him to know that I wanted the girl role with him. I wanted him to know that I welcomed his romantic attentions.

His tongue entered me and I could not believe how big it was. I loved the way it filled my mouth out. It was so demanding. I could not stop myself from sucking on it, welcoming it even further into my body, if that was at all possible.

He kissed me like that for a very long time, and I just melted into his arm.

Soon I felt his hand on my nyloned knees. I could not resist him. I knew that like any other girl, I was about to find out what it felt like to get myself felt up, and I wanted that desperately. I encouraged his explorations by parting my legs a bit to let him know that he could have access to me up under my skirt if he wanted it.

I was glad. He did want it. His hand moved slowly but it did make its way up under my skirt, all the way up to the front of my panties. I nearly died when I felt his big strong fingers caress me through the delicate silk of my panties. I nearly screamed on his tongue the moment I felt the big hard end of his fingers lightly caress the front of my panties. It was just so sweetly wonderful.

I felt like his fingers were so big that he could break my little cockette right off if he had wanted to. I loved how it made me feel so wonderfully under his strength and power. He grasped me lightly and started to stroke me. I could not help the moan the pass through my lips as his tongue invaded me.

His fingers went down to the crotch of my panties, right where my vagina should have been. I felt him push up into me, and for the first time in my life, I desperately wished that I had a hole there for him to enter into me. It was such a girlish thing to feel and I knew that I could easily fall in love with this man, and I knew that I wanted for him to do to me whatever he did to girls.

I also could not stop myself from reaching over and placing my hand on the front of his pants. Gawd he was so fuckin’ hard. I could not believe it. He throbbed under my hand, and I could feel his power. He was so hot too. I felt the heat right through his pants. And he was big, big compared to me that is. I felt such a sense of power to know that as a girl I could make him want me so much.

He moved his lips to my ear. "Debi, I want to take you home and make love to you. Do you want to go now?"

I could hardly breathe. I whispered the only thing that I was capable of,

"Yesss…"

I was light headed, and I could hardly breathe. It was so erotic and so exciting to me to be treated like a real girl. In almost a trance like state, I enjoyed his arm around my shoulder as he led me out of the movie house and out to his car, where we spent a long time in a delightful embrace. I also could not keep my hand off the front of his pants. It made me feel strangely very free to be able to touch him in the way that he only ever let girls touch him, and I loved how that felt to me.

Finally, we made it back to our dorm room. I felt like a teenybopper with her first major crush and it was very exhilarating to feel. It was liberating. It was the most exciting emotion that I had ever had.

When we got back to the room, as soon as we stepped inside of the room, he took me into his massive arms again and he crushed me against himself as he buried his tongue in my mouth once again. I melted. I put my arms around his neck so that I would not fall to the floor.

After a long moment, I stepped back from him.

"Jake, are you going to hate me for being such a fairy?"

"Debi, I could not hate you. As for you being a fairy, well, I guess that this is what a guy is called who likes to wear girl’s clothes and have other guys kiss him. If you want to think of yourself as a fairy then that is okay with me. I do not think of you like that. I have never been able to think of you as a regular guy, ever since I first met you. I cannot think of you as a guy, especially when I see how you look and act right now. Hell, ever since the first time you walked into this room, I could not help but to wonder how you would look in a dress. You do not realise it sweet heart but you are far more of a girl than you have ever been a guy, no matter how hard you try to act like a guy. You just can’t pull it off. I think you were meant to be a girl, and that is what I thought when I first met you, and I made the decision to see if I could do something to get the girl out of you, because I wanted to meet her and see what she was like."

"You… Wow! That is a lot to say Jake."

"Yeah, but I bet you feel better about yourself right now than you ever have."

I blushed furiously. "Yeah, I do." I stepped back to him, raised up on my toes and I kissed his lips, and I thanked him for caring so much about me.

"So, what now Jake?"

"What now? I want you to be just like any other girl."

I hesitated for a long time. I knew what he wanted, and I knew that I really wanted to know what it felt like to do it too.

"You want me to take care of this for you?" As I said it, I put my hand on the front of his pants and was delighted to find out that he was still as hard as a rock.

"It is what girlfriends do for their boyfriends, ain’t it honey?"

"Yeah, I guess that it is."

"But Debi, I only want girls to take care of me who really want to take care of me, who get pleasure from taking care of me. You understand?"

"Yes Jake. I understand. I… I never did anything like this before… But…. But I want to try it." I knew that I had just sealed my fate in my friend’s eyes. I had just so much as told him that I wanted to suck his cock, like a girl or a fairy.

He smiled and placed his hands on my shoulders, palms down and lightly applied pressure. I did not need a second invitation. I felt such a wonderful emotion of surrender to him, as I lowered myself to my knees in front of him. His belt was just above my eyes, and I could see the big bulge throbbing in his pants. Man, he was so hot for me. He really wanted me. I was flushed with pride that I, as a girl, could make this stud muffin react to me like this. I was so pleased.

I reached up with both hands and pressed against his cock. It was still so hard, it must be painful for him. I watched as my red tipped fingers began to lower his zipper and then undo his belt. Once I undid the button, his pants fell to his ankles like a dead weight. His tight white jockey shorts were strained to the limit.

I carefully lowered his jockey shorts, and as I did so, his cock leapt out and smacked my cheek. I giggled. Only his other girlfriends would know what this felt like, I thought. He was not huge, but compared to my little cockette he seemed to be rather massive.

I ran my fingers all over his shaft, admiring and studying it. It was rather smooth, but rock hard. It was shaped kind of like a rocket, big at the base and narrowing as I got to the end of it. He trembled and sighed when he felt my fingernails on his cock. He was ready to fire off for me, for sure. I traced my nails on his cock again and again, just because it made him lose control. He’d shudder and sigh, and I knew he was under my control, just as much as I was under his control.

I felt such a power over him in a way. He was trusting me with his family jewels, and he did not trust very many with them. I knew that he was proud of his cock, and now I knew why he was so proud. It was a beautiful sight to me.

I let it rub along my soft cheeks and then turned my face so that I could begin to kiss it all up and down. It seemed so right for me to be honouring a man in this fashion. It just seemed right, and it felt very good to me to know that I was getting to feel what other girls felt with him.

Finally, I kissed my way up to the circumcised head. It was right on my very lips, and I was kissing it, and beginning to taste the sweet saltiness of his cum. I kind of liked the taste of it.

I parted my lips, to receive my man.

I felt him move into me, very slowly. I loved how it felt to feel his cock moving across my lips, opening my mouth with his girth as he entered into me. I could hardly believe that I was actually dressed as a girl and making love to her boyfriend but I was, and it was intoxicating.

I could get about half of him into me before a strong gag reflex kicked in.

I backed off a wee bit, sucking hard as I did so.

When I had only the tip of his cock inside of my mouth, I looked up at him. He looked so strong, so big, and ever so masculine. He was looking down at me with pleasure and masculine superiority written all over his face. I wanted him to feel that way with me. I was pleased. I wondered what he was seeing as he looked down at me and lightly played with the hair on the back of my head.

I sighed and sucked him back into me.

He trembled and stiffened and cried out that I was going to make him cum.

Then he jerked at my face, and I felt the first load of his ejaculate. I was surprised that I could not taste it too much. It did trigger the gag reflex though as his cum hit the back of my mouth. Then he jerked again and again and I encouraged him to give me everything that he had to give. I felt like it was a kind of a reward for me to draw his cum out of him, in the way that women were designed to do from the beginning of human history.

He went very tense, not moving, just throbbing inside of my mouth, and I licked and sucked him to drain every drop from him. He actually sighed and started to relax his body and I felt him start to shrink inside of my mouth. I let him take it out of me, and I kissed his cock head as he withdrew it.

I just stay there for a long minute, kneeling there, looking up at him. I felt like a maiden who had just honoured her lord and master, and I must admit that I did like the way that felt to me. I really did like it.

He smiled down at me. "Debi you are a natural at this. That was the best I ever had. Thank you."

Fearful of losing my mouthful of his cum, all I could do was smile up at him.

"Debi, the other girls all swallowed."

Wow! I had never thought of that before. It would be the first time that I had ever taken something living into my body.

Well, if the other girls did it, I would experience just one more thing that the other girls got to know what it felt like. So I swallowed it, all of it. It was a very strange feeling indeed, to know that those little sperms were in my belly, looking for my eggs, so that they could make a little Jake inside of me.

I loved it.

Jake helped me to my feet and he held me tightly, letting me take the time to bask in the joy of pink bliss that he sensed that I was experiencing. I knew that I loved this man now. I loved him just as much as any other girl had ever loved him and it was a lovely sense of tenderness for him. I loved every second of it.

He pulled me tightly against him, lifting me, making my legs part around his waist as he lifted me, and he backed me against a wall, so that he pelvis was crushing me in my panties. I sucked on his tongue and I nearly feinted as I clung to him and let his gyrations against the front of my skirt make me erupt into the most wonderful sensations that I could have ever dreamed were possible for me to feel. I’d never even dreamed that being made to cum like that, while this big man was holding me in such a manner was possible. I screamed onto his tongue as the pressures of his gyrating pelvis pressed the intimate girl material of my panties into the only boy flesh that I had, and it made me want to be his girl for all time.

If being his girl felt like this, I wanted to be every inch of a girl for him that I could be.

For the first time in my life, I slept while wearing a pretty nightgown and matching panties, wrapped in a loving man’s arms. It was the way that I always wanted to sleep from that moment on.

 

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© 2001 by Deborah Leigh Johnson. All Rights Reserved. These documents (including, without limitation, all articles, text, images, logos, compilation design) may printed for personal use only. No portion of these documents may be stored electronically, distributed electronically, or otherwise made available without express written consent of the copyright holder.