I Dreamed This Was True
Another Fiction by John G. Edwards
All rights Reserved 2017
This Chapter 7, in Part 3, of the Transgender and Crossdressing, A Collection of Short Stories, written by the author. It is shared with Nifty.org for your reading enjoyment. Please support their site with your generous donations.
You know, I never know what to think anymore. I keep having these dreams and they are so life like that I'm almost beginning to not know when it's a dream, or if it's really happening in real time. I turn on the TV and it essentially lulls me to sleep. But these dreams... I'm getting to a point to where I need to do something about them, maybe it's seeing a therapist, or just talking to someone. You see, I see myself as a woman, not the man I am. I wear female attire, I mean everything from lingerie to the cutest outfits you can imagine. My makeup is totally believable, like you can't tell me from the genuine article. I even wear earrings and all sorts of jewelry.
I do those things that would be associated with female behavior, like shaving my legs, my underarms, my pubic hair, and even plucking my eyebrows to make them more feminine looking. If you saw me on the street, I would be, how is it they say... totally passable. The craziest part about this is, I do feel more at ease with myself when I dress. The emotional and physical things seems to be just me. Am I going crazy here?
In this one dream, I was on a date with a really cute guy and it was all I could do to keep my hands off of him. I almost felt like a bitch dog in heat. I noticed everything about him, the way he had his hair cut and styled, the single stud earring in his left ear, and the cologne he was wearing. Of course then, there was his clothes, the button-down dark blue shirt and his flaming red tie, his neatly pressed khaki pants, the braided natural leather belt with a gold buckle that was around his slim waist, the red argyle sox, and his pebble grain brown loafers. His long blonde hair styled so that wore a man-bun on the top of his head. His sideburns were just slightly long, but nothing like Elvis, at all. He was also clean shaven and his perfect skin seemed to just glisten. This isn't like me to even notice what a guy dresses like, at least not to this detail. Yet, here I am, noticing everything about him down to the chronograph watch that was strapped around his left hand, and the heavy gold link chain around his right.
Of course, he pays great attention to me and says flattering things that boost my ego to new heights that I have never experienced before. My makeup is letter perfect and so is the short pink sun dress with cap sleeves and tight bodice that I am wearing. My black 200 denier tights cover my legs perfectly so that there is no skin peaking thru, and my pink patent leather pumps are not over the top high and the ankle straps are very sexy, indeed. My ever so slightly wavy long shoulder-length hair style glistens in the sunlight. We must both be a sight to behold by all others.
In another part of this dream I am dressed just like any other executive secretary with my hair in an up-doo, slightly overstated makeup, a black pencil skirt, a while silk blouse and a very tailored tweed jacket. My legs are covered in black nylons and my 3" pumps with the almond toe are to die for. I'm busy typing something when a man in a business suit comes and asks for my supervisor. I very courteously ask if he has an appointment, which he does and I send him in after announcing him on the intercom. A few minutes later I am asked to come in and take some shorthand notes. All very business-like and completely different from my job as a design engineer with a small R&D company.
Then a few minutes later, I find myself at home undressing myself to go take a bath. I slip out of my navy blue jumper and give it a toss onto my very frilly bed. I then sit on the edge of the bed and undo the buckles on my Mary-Jane shoes and then unfasten my garters and slide my stockings down my legs. The long-leg girdle that I am wearing comes off next, and when it does, I let out a sigh of relief. For some reason, the sight of my small-size penis does not seem out of the ordinary. I reach my long slender arms around to undo my lacy push-up bra and let it slide down my arms onto the bed. Now, naked as a Jay bird, I toddle off to my waiting piping hot bubble bath.
As I sit in the tub full of sweet smelling bubbles, I scoot down so that only my head is sticking out of the water. I pass my hands over my ample breasts and exhale deeply. My nipples perk right up from the stimulation and I squeeze them between my index fingers and thumbs and I just sigh. Alternating my hand positions from cupping my breasts to squeezing my nipples several times just seems like heaven to me. I then slide my right hand down to my penis and rub it gently and it responds slowly to my touch. I think I've touched myself enough and lather my legs so I can shave them silky smooth. Once each leg passes my final inspection, is shave my underarms to the same silky feel.
Next thing I know, its morning and I slightly open my eyes and close them again. I try and remember what my dreams were and savor the memory. My hand slowly passes over my chest and I frown slightly because I don't feel the breasts in my dreams. Oh god, were they nice. Then, I reach further down and scratch my balls to cure an itch. I don't remember having testicles in my dreams, just a small dick. And so this dream cycle goes, me wearing a dress and liking it very much. I get up and throw on a tee shirt and a pair of jeans and I'm off and running, so to speak. Since it's the weekend, I've got a few chores around the apartment to tend to before I get my free time. I'm supposed to have lunch with Sandy over at the Jewish delicatessen around 1:00, so I've got to get a move on. With my chores all done, I leave to go get lunch.
"Hi Sandy, how are you today?"
"Terrific, for a Saturday, how about you Thomas?"
"I'm well, thank you." We ordered our food and found a table.
"So, what have you been doing?"
"Oh, not much, I've been pretty busy at work. I've got this new project that's sort of kicking my ass. It's a new product that I have to design for this tool company."
"Sounds exciting, care to tell me more?" asked Sandy with a big smile on her lovely face.
I told her the short and long of it and she seemed genuinely interested, most women would find the stuff I do very boring and inconsequential to their world.
"Anything else of excitement going on?"
I kind of measured my response, "Well, I've been having these dreams that are pretty weird, do you ever have dreams like that?"
"Yeah, every once in a while I dream of something that is out of the ordinary. I had this one where I was the engineer on a freight train. I was barking orders to my crew and yelling at them because we were behind schedule. Kind of weird huh?"
"I would say, especially since you are a cosmetologist."
"That's what I thought," we both laughed, "SO what was your dream about, Thomas?"
"Well, lately I've had several dreams that I was a female. You know, dressing up and wearing makeup. I mean, I just don't know where that's coming from."
"Well, that is different. How long have you been having these dreams, like is it your first time, or anything?"
"I've had them off and on for a couple of weeks now. I don't know if I should go see someone, or what?"
"Let me ask you, have you ever worn a dress or makeup before?"
"No, not even for Halloween." Sandy took a long look at my face before saying something.
"Thomas, I'm going to ask you something. Please don't take it the wrong way, or anything... But, would you like to come over to my place this afternoon and try on a dress and I can do your makeup. I might be fun, you know? From what I'm hearing, you need to do something like this. There must be something kicking around in your head that needs to be checked out. You might find that putting on a dress and makeup will either satisfy or dampen whatever it is that's causing these dreams. Look, I'm not going to tell anyone, we're friends, right?"
"I sure hope so, I do feel kind of weird even telling you all this."
"Hey, listen... I just want to help you. Don't you think that having someone who is supportive and willing to investigate this to some sort of conclusion isn't a good thing?"
"Yeah, I guess."
"Okay then, after we get finished here we'll go and get you dressed up. OK?" she said with a sincere smile.
I shook my head, yes. Our pastrami skyscrapers came and they we just a fine memory within half an hour. Afterwards, I followed Sandy to her place and parked. Having been there several times to take her out on a date, I knew the trail pretty well. Once we were inside, Sandy asked, "Tell me a bit more about your dream." I told her about taking a bath and shaving my legs and underarms, and how good it felt.
"Ok then, a place to start! I want you do go in and shower, then I will help you shave your legs and underarms. There is kind of a secret to it all, you know. Then, we'll get to the dressing part and then the makeup." Sandy appeared to be getting much more into the spirit of this afternoon than I was, for the moment. I went in and took a somewhat abbreviated shower because already showered earlier. After I was thru, I called her into the bathroom. "Ready."
"Alright, let's get this show on the road dear heart." With that, she gave me a quick kiss on the cheek. "Sit here on the edge of the tub and put your legs on the inside." Sandy handed me a can of shaving cream and told me to lather up my legs. I had already put my briefs back on to cover my privates. I spread the shaving cream all over my legs and almost up to my man things. She handed me a plastic razor and told me how to hold it and then guided my hand to get me started. My leg hairs were not all that course and they came off without any problem at all. I was instructed to shave all the way up to my pubic hairs. As I removed the hair, my legs felt like nothing that I had ever felt before. As I touched them, my heart started fluttering. Oh what a feeling! My hand slipped over my legs like a skater on ice. The feeling was incredible!!! After my legs were properly denuded, it was time for my underarms. I did have rather thick underarm hair and it took several minutes for Sandy to clear them away to her satisfaction. I figured that she had better do this part because when I tried, the razor just got all clogged up. Sandy dusted my underarms with baby powder and they felt marvelous! As I moved my arms, they too seemed to slide like butter on a hot pan.
"Well, what do you think so far? Anything like in your dream?"
"Yeah, kind of. It's the same intense feelings I had in the dream."
"It does feel really nice, huh?"
I just smiled at her and she seemed to understand.
"Well, we are nearly finished with the bathroom chores, dearest." She had me sit on the commode and she straddled my legs to tweeze away at my eyebrows. However, there was a bulge starting within my briefs, but a quick flick with one of her fingers made the slight bit of manhood that I possessed go, as if by magic, back t sleep. "Let's not have any of that, now!" I just sat there and blushed. After what seemed forever, she was finished and when I stood up to look at myself, I was sporting a pair of fairly feminine eyebrows.
"Is that too much?"
"Not really, I could have gone all out and gave you some pencil-thin brows, but the guys at work would probably given, you a lot of shit about that. I've got a few things laid out for you to put on. Stay here, I'll go get you something to put on instead of those awful briefs." She laughed as she left.
A minute later, she stuck her hand in thru a crack in the door and told me to put the garment on with the shinny side forward. After removing my underpants, I had to somewhat struggle to put on the black girdle. From outside the door, Sandy told me to pull my 'man junk' between my legs and pull the girdle into place. The satin tummy panel was truly a thing of beauty as well as something that was very electric to the touch. As I glided my hands over my tightly squeezed butt, I couldn't believe how it felt.
"Ok, quite feeling yourself up, and come out here."
How did she know??? I opened the door and came out. Again, I was blushing.
"Stand right here," she pointed to a spot on the floor. "Let's see about getting a bra on you. That's the one piece of underwear that will make you look feminine beyond belief. You certainly don't have anything on top, but that what these are for..." She held up a pair of breast forms that must have been the size of Texas! She laughed once more. "I don't have much on top either, I wear a A-cup bra and can hardly fill some of them out. But, when I put these in, I have a rack that won't quit!" Sandy placed a black bra around my chest and the cups just sort of hung there.
"This is called an underwire bra and it gives your breasts a lot of support when you have big hooters. This bra is meant to be used with breast forms, that's why it looks big on you. It does the same thing when I put it on, too." Sandy adjusted the straps to fit my torso and then turned me around so she could put the forms into the special pockets built into the bra for such purposes. As they slid into place, my chest took on a whole new dimension, literally! The D-cup forms gave me a chest of prodigious proportions! Oh my god, they were magnificent!!! Once she was satisfied at the way I looked, she stepped back to take a gander. "Oh my, aren't we just the sweetest looking thing, take a look." As I looked at myself, I trembled slightly, there staring back at me was a very beautiful representation of the female form. I turned sideways to get a better view and as I did, I instinctively cupped my hands around my new appendages and closed my eyes in ecstasy. My man thing, was struggling to life, but that was not to be.
"Wow, you look terrific with breasts, Thomas!"
I just stood there and stammered, "Thank you." I gave Sandy a big hug, but there was now something between us that was not natural!
"Alright, gets get you into some pantyhose." Sandy handed me a pair of nude hose. As I held them, I could only think, I'll never fit into these things. She showed me how to roll them up into my hand and then carefully pull them into place, one leg at a time.
Once the pantyhose were coerced into place, my legs looked lovely indeed. And the feel of pantyhose on my legs was like no experience that I had ever felt before. If you could measure the voltage that my finger felt as I rubbed my legs, it for sure would have been a million volts, at least! Oh man, did these feel wonderful, or what!
I thought that this was the end of my undergarments, but nooo, Sandy handed me another girdle to put on, this time it was a long leg, high waisted, model. As I pulled the new girdle into place, it just seemed to slip and slide right into place. The top nearly came up to my bosom, and the long legs hung down about 4" below my crotch. My boy toy was now fully hidden clean out of sight. And this girdle felt even better then the first one I had put on initially.
We could have stopped right there and I would have satisfied the things that I had experienced in my dreams. But, now, the dress had made it emergence and I was about to put it on my female looking body. Sandy had chosen a blue and white check dress that had a fitted bodice and no sleeves. The skirt was full and was made even fuller as Sandy had me put on a crinoline. The scoop neck came down a reasonable depth, but not so much that I would show anything. Anything? I had no cleavage!
Now, I was taking on more of the female form than ever before, but now it was time for my makeup and this was the area of expertise that Sandy made living for her. Her plan was to do something fairly simple, some mascara, eyeliner, and some lipstick. It took her all of about 10 minutes for her to apply everything. The pinkish red lipstick was quite fetching, in a feminine sort of way.
I couldn't stop staring at myself in the mirror. Sandy had a long blonde fall wig in her hands and was getting ready to put it on my head. "I think this will look darling on you Thomas. What do you think?"
"Sure, why not," was all I could say. A couple minutes later the wig was on my head and it looked like my own hair. Now when I looked in the mirror, there was a young lady staring back at me. Gone were all of my masculine traits of Thomas, you would have never been able to tell that this body actually belonged to a person of the male persuasion, never!
"Ready for the finish line?"
"I thought that I had already crossed it?"
Sandy just smiled, "Not quite yet." She held out a pair of clip-on earrings for me to see and then proceeded to put them on me. They were 3" hoops and when they were securely clipped onto my earlobes, I looked way more than just spectacular!!! "Oh shit, I almost forgot your shoes! Here, put these Mary-Jane flats on."
As I dawned the white leather shoes, I had truly become more than a reasonable facsimile of a woman. If you didn't know my former self, you would have thought that I was a female, nothing less. My breasts stood proud and made me look so girly. Flashes of bright white lit up the room as Sandy took several pictures of me in my female finest. Click. click, click went her camera. I was told to strike various poses as she clicked away.
"Ok, like those shoes?"
"Yes..."
"Good, I think you might like these better, though," she said as she held up a pair of high heels in her hands. "Get out of those Mary-Jane's, and let's get these on your feet."
My eyes must have bulged out of my head as I savored the thought of wearing real high heels for the first time! Sandy helped me to my feet as I stood up in her white 4", nose bleed, high heels shoes. I wobbled around like a kid on skates for the first time. As I took my first steps I hung on to Sandy for dear life!
"Take small steps at first. Point your toes downward as you walk, you will find it much easier that way." I took a few more steps and it was easier, just like she said. Lucky for me, these were not spiked heels! The heel was about an inch in diameter, but I still managed to nearly fall down a few times. How on gods earth do women wear these damn things, was all I could think. But after a few minutes, I was walking unaided all by myself. Sandy's hose was somewhat small, but I seemed to navigate around very well after more minutes had passed.
Sandy instructed me in how to walk and swish my hips as I did. The hand gestures would take a lot more time to perfect, that's for sure. The afternoon had slipped quietly away as we giggle and laughed. "Are you getting hungry yet?" asked Sandy.
"Yeah, kind of," I said. "What have you got in mind?"
"Well, I don't have much in the fridge, why don't we go out?"
"OUT, what do you mean, OUT?"
"Yes, out! We can go to the chicken place on the Avenue. We can do the drive thru, if you don't want to go in."
"Not on your life! I would just die if someone saw me dressed like this!"
"Come here a minute, please." Sandy took me by the hand and stood me in front of the full-length mirror, "Now, what do you see here?"
"Me in a dress and makeup."
"Let me tell you what I see, I don't see Thomas, but I do see a beautiful young lady looking a whole shit load better than most of the women I know. Now, you are going to get out to the car, you are going to get in and sit down, then were are going to Chuck's Cluck, and get something to eat. Understand me?"
As I stood there, I mumbled, "Ok," and off to the chicken place we went. To say I was a nervous wreck going there would be like asking if the people on the Titanic if they were nervous as the ship was going down. Hell yes, I was terrified!!!
As we drove, no one seemed to be paying attention to me, except a couple of guys in the car next to us at the stop light. I did get a wolf whistle, I just smiled and turned my head as if I was talking to Sandy. "Oh my, I'm going to have to be careful with you Thomasina, you are attracting too much attention from the boys! Huh?" Sandy had to laugh. I did too. Chicken in hand from the drive-thru, we headed home. On the way back, I couldn't believe the emotions that flooded my head when the guys whistled at me, I was flattered beyond belief!
Once we got back and ate our dinner, it was time to get undressed and head home. "Sandy, I can't thank you enough for doing this for me today. And thank you for making me go out. You have given me a whole bunch to think about, now. I'm sure that I can maybe resolve this thing now. Thank you." I reached over and gave her a hug, she returned the hug and gave me a kiss full on the lips.
"Thank you for allowing me to be a part of all this today. I sincerely hope that this helped you. I have to admit, you do make an attractive looking woman, if I do say so myself." She then gave me another kiss and as she did her hand cupped one of my breasts and she gave it a good squeeze and then she slid it down and gave my butt a nice pat. "Would you like to stay over tonight?"
I quickly agreed.
"Would you like to go dancing, tonight?"
"Thank you, no. The trip to the chicken place was adventure enough for me tonight." The words had no sooner left my mouth and Sandy was pulling me towards the bedroom. After much sexual release, the two of us fell fast asleep. Once again, my dreams were about crossdressing and how it made me feel like a whole person. About 3:00am, we had another bout of the most wonderful sex you could ever imagine. I wondered if this would be my last time in a dress, or what?