From alt.sex.stories.tg Sat Dec 21 00:45:05 1996 Path: nienor.IN-Berlin.DE!forwiss.uni-passau.de!suelmann ~~Newsgroups: alt.sex.stories.tg ~~Organization: The Testsite ~Lines: 1121 Message-ID: 59f3fb$gd5@nienor.in-berlin.de NNTP-Posting-Host: elros.forwiss.uni-passau.de
I didn't write this nor do I know how to contact the author
TG, cd, mm §§§§§§§§ Oroiginal Filenames: JAKE1.TXT .. JAKE4.TXT
MY FRIEND JAKE
BY
JO BLACK
What can I tell you about my friend Jake? I've known him for 20 years; we even went to grade school together. He's, to put it mildly, a bit eccentric. To be completely honest, he's crazy. That's probably why I like him. Whatever we do, it's fun. For years, he has planned what he terms adventures for us to embark uponm. They are always odd but extremely intresting. This is the story of our latest one.
Naturally, since we've grown up, we don't see much of each other. Once a month or so the last several years has been the extent of our contact. He called last night and asked me over to watch Monday Night Football. I eagerly accepted. Not just because the Bears were playing, but because I have always had a fascination for Jake and his antics. I know that football will not be the only, and maybe not even the primary entertainment of the evening.
Well, I got there an hour before kickoff as he had suggested. After catching Jake up on my life, I asked him what he has been up to lately. Mistake # 1. He told me and I listened. Mistake #2.
Jake told me how he went to a bar called the Queen Mary in LA during his last business trip. He proceeded to tell me how all the waitresses, the entertainers and even the hat check girl were really men dressed as women. For some reason, this entire thing really intrigued Jake.
Now, by this time, you have to realize we had two pretty stiff drinks and were working on the third. This really released any inhibitions I may have had. Or perhaps, I should say, this released any good common sense I may have had. We talked about our senior play at good old St Simon High. Being an all boys school taught by nuns, we didn't really have any girls for our production of Romeo and Juliet. Consequently, we drew straws for the lead parts and I lost. Yes, I was Juliet to Jake's Romeo. And just why did we do Romeo and Juliet in an all boys school? I told you, we had nuns. Jake and I were always in trouble with the nuns, so we were assigned the roles. I have no doubt that the nun's rigged the draw.
I thought back to the costume I wore in that play. Funny, it wasn't all that unpleasant. The director, Sister Mary Paul, insisted that Juliet was to be properly attired, 100%. I always believed that she was just getting back at me. But flashes of rustling silk on my thighs kind of sent a shiver down my spine. I really liked the way the long haired wig would dance on my face as I moved my head. Hey, don't get me wrong. This was my only foray into crossdressing. But it was pleasurable in an odd way.
A couple more drinks and the Bears were forgotten. Jake, as usual, decided that we should do something different. Now, Mistake # 3, and the biggest one, I said, and I quote, "OK, I'm game."
Jake said that he discovered a small bar here in town that was very discrete and VERY friendly. It was, quite naturally, a drag bar. Not only was the entertainment and the employees in drag, but most of the patrons were too. He decided that we were to go and to go dressed. Tonight.
I protested in many ways. I said we didn't have the clothes. He responded that his sister had left her belongings with him. I groaned. Sally was a big girl, not heavy, just big. I was sure her clothes would fit.
I explained that we didn't look like girls. He countered that we only had to look like men dressed as girls. I tried my final plea. "But, I don't want to."
Jake just looked at me sadly and was quiet for what seemed several minutes. Finally, he asked, "Why? You always do what ever we thought of before. But, It's alright if you really don't want to."
Maybe it was the booze, maybe it was Jake's sense of betrayal. Or just maybe my curiosity was also piqued. I don't know. But I agreed. Jake just smiled and told me to come with him.
We went to his spare bedroom. He had two complete sets of clothes laid out on the bed, complete with bra, panties, hose and shoes. He beamed and asked me if I preferred the off the shoulder forest green or the red minidress.
I was almost totally flabbergasted by this point and told him I didn't care; that he could choose. Another error. I got the red mini. And man, was it short. But I had given my word so I just smiled.
Jake then got down to business. He directed me to the bathroom and explained that I needed to take a hot bath in bath oil and shave my chest and my legs in order to be authentic. Strange to admit, I saw his point. That was one thing we always did throughout the years when we would pursue our little adventures. We always tried to be real.
As I soaked in the tub, I went to work on the shaving part. It wasn't easy at first, but was easier than holding a razor to my next neck the morning after a real binge. The chest was easier. A few swipes and I was done. I got out of the tub and toweled off. As I dried off my newly smoothed legs, I found myself lingering as I gently rubbed them and to my astonishment, I got hard. Go figure.
Jake replaced me in the bathroom, leaving me to fend for myself among the alien undergarments on the bed. He told me he wouldn't be long, as he had shaved the night before. So, he had planned this all along.
True to his word, he was out in record time. He asked me why I wasn't dressed yet; I just shrugged, took a deep breath and pulled the bright red panties up my smooth legs and tickled my half hardened cock as I pulled them into place. I then picked up the matching bra, wrapped it around me and hooked in while it was on backwards. Then, I pulled it around and pulled my arms through the straps. Filling the empty cups with foam that Jake had provided, I felt a little restricted after pulling on the pantyhose. But it was a secure type restriction, not unlike being hugged. Glancing in the mirror, I was shocked to notice the body before me. Oh, oh, that embarrassing lump in front had to go. I pulled the hardened cock between my legs, but that just made it worse as it looked like I was growing a third leg. Jake just laughed.
He pulled himself together and produced two leather pouch type things he called gaffs. He claims ALL the "girls" wore them. I took mine and for the life of me, I couldn't figure it out. Jake watched and laughed and snickered. Finally, as tears ran down his face, he took the gaff, gently grabbed my cock and fixed me up. I didn't even breath. When he grabbed me, I could feel myself stiffen up. But it was odd, it felt damned good. Jake just grinned as he did it. I know he held me longer than needed. But I didn't object. This was getting stranger by the minute. But what was stranger, I didn't care. In fact, I think I liked it.
We just stood there for a few seconds. Then together, we turned back to the business of getting dressed. Jake had laid out the most silky black slip I had ever seen. As I pulled it over my head and down the length of my body, I shuddered with delight. I thought back to that play in high school and fondly relived that feeling of silk dancing across my thighs. I just couldn't stand it. I ran to the bathroom, pulled down my panties and the gaff and let my wad go. After regaining some control, I cleaned myself off, got rearranged and quietly reentered the bedroom. Jake was sitting on the bed, silently watching me. I sat down next to him. After a few minutes he gently took my hand and said, " That happened to me the first time too. Nothing to be embarrassed about, it happens."
I just stared at the floor for a few minutes and then looked up at him. I knew. After all these years, I knew something I should have known. I asked," How long have you been gay?"
"All my adult life, though I really haven't been too active until 3 years ago."
I then asked, "This bar you want to go to tonight; is it a regular hangout for you?"
He admitted that since it had opened 4 months ago, he had gone at least twice a week. Like Cheers, everyone knew his name.
I shook my head with a smile. He got me. He kept his secret for years. He set me up to go there with him. That was obvious. But I had noticed that he still had his jeans on. I was his "date". He was dressed to go out. But why me? I never had spoken of any desire to either dress as a woman nor gave any interest in the gay lifestyle. So I had to ask him, "Why me?"
He started slowly, " You have always been my best friend, my partner in crime. This was the only thing I never shared with you. I thought if I made the situation so exaggerated that it was one of our adventures, I could explain to you later about who and what I had become."
There it was. The man who had done everything to everyone just in the name of fun was scared to go it alone. I felt that old sense of obligation again. I stood up, stared down at him with my hands an my hips, my breasts jutting out and said, "Just don't sit there. I need help with my dress before I can put on my makeup. And you need to change too. If you're taking me out, you better plan to wear good slacks and a sports coat. And one more thing, buddy. You're buying."
As I smile passed my yet plain lips, Jake stood up and hugged me! He just held on for a moment and whispered, " I knew you would understand. I know this isn't your scene and that you are doing this just for me. Thank you." And then, all of the sudden, the old Jake was back in control of himself and of our planned adventure.
I picked up the red minidress gingerly with both hands. The fabric was cool and soft to my touch. I stepped into it and slowly slid it up my legs, the fabric sliding up my slip. I felt myself get hard already! Am I doing this for Jake of for myself? I was a little confused. This was a first for me. I was really enjoying the entire experience. I pulled my arms in the sleeves and adjusted my simulated breasts. I turned and with a surprisingly soft voice cooed, " Jake, could you please zip me up."
I could feel his rough hands fumble with the end of the zipper. He grabbed the tongue of the zipper with one hand and my ass with the other. Just for leverage, I'm sure. But I almost exploded inside. The firm grab just felt right. As the zipper slowly slid up my now satiny back, I again felt those shivers running through me. I hoped it would never end. But alas, It did. I turn on one foot and faced him. He just stared back and muttered something about how incrediblably different I looked. I was pleased.
I slid my feet into the 3" red heels that Jake had left on the floor. Perfect fit. That in itself wasn't that surprising. We both wore the same size and knew it from gym class years ago. I walked tentatively around the room. I was pleased to discover that I had no problems with balance. I just needed to shorten my natural stride. I'll say one thing, high heeled shoes are the most feminizing part of female apparel. My all even rolled slightly as I walked. My hips swung slowly with each step. I glanced into the mirror was pleased. And that in itself was a surprise. I no longer felt self conscious or nervous. Hell. I didn't even consider I was dressing like a woman, I felt I was one.
I slid slowly over to the vanity. Jake had laid out enough makeup on the top to paint the Radio City Rockettes. I found the makeup was the easiest of all these peculiar preparations. In high school, we had to learn to do our own makeup for the play. I applied the foundation expertly, covering the heavy jawline. Then I worked with the blush and powder to highlight my cheeks. The eyeshadow was too much, but I felt like showing off. The eyebrow pencil worked perfectly after a quick plucking. I added lip liner and lipstick as red as my dress. The final touch was sable brown mascara which seemed to double my eyelashes. I looked in the mirror and suddenly panicked. My hair! What about my short, conservative hair?
I held Jake bustling about behind me them felt something come over my head. I looked in the mirror and there it was. Cocked to one side, but beautiful just the same was a great mass of curly brunette hair. " Remember, Juliet? I do. The way you tossed your head and the hair would play across your face?" Jake had remembered all these years. I wondered if he suspected what joy I got from being Juliet. I might ask him later.
After fussing a few minutes, my hair was perfect. I glared judgementally in the mirror. Hair, makeup, everything looked just right. I rose slowly, and to my great surprise, quite gracefully. I pivoted on the toe of one high heeled foot and faced Jake. He had changed into tan Dockers and a sports jacket; just as I had asked. Suddenly, a wave of cold went through my body. I whispered, " What now, Jake?"
"Now, my darling Joe, without an 'e', we go to Fantasy Island. No, not the show, the place I was telling you about."
I almost had an anxiety attack. It was enough to submit to Jake's plans. I agreed to getting dressed and going with him. But the mere thought of actually going out in public never really hit me. But, what the Hell, I've gone this far, let's do it and get it over with. I know at least no one will be there that I know.
He magically produced a pure white cape from God knows where and swept it gallantly over my shoulders. I fluttered down my arms and back and I felt myself stir once again. Damn, I've got to get that under control or this could be a longer night than I feared. But I just smiled and turned to Jake and said, "Let's go."
He directed me through the kitchen by gently grabbing my arm and leading me. That was nice. I felt cared for in some way. In his large, attached garage, He gallantly opened the passenger door to the little Mustang. After a moment of indecision, I remembered how my dates entered cars and slowly sank my lovely, silky ass into the seat. I then, not ungracefully, swung my legs in and folded them at the ankles almost demurely. Oh well, it worked.
Jake opened the garage door, started the engine and turned to me and said, "Jo, you'll enjoy this evening. I promise. If I go too fast or try to do something you don't want to, tell me. We've been friends too long to screw it up now. We are going out just like always, as friends. What ever you want to do when we arrive, just do it."
I couldn't respond to any of this. Jake was my friend. I really didn't feel any electricity between us as I had with any girl I had dated. And I didn't feel any strong passion toward me. I honestly think that we are still just friends. Although I am now wearing a slip and a minidress, this felt just like one of our old adventures. We were out for a good time.
The trip to Fantasy Island, Jake said, was 20 minutes. During that time, we made small talk. A few times he grabbed my arm or hand, but he didn't linger. I was his friend, I decided. In fact, I was probably accorded the same status as a sister rather than a date. He mentioned a few things about letting him know if things got a bit intense or if I was feeling uncomfortable with someone, he would rescue me. Now I knew I wouldn't have to ask him about the play and if he knew how much I enjoyed my role. He evidently sensed what I either didn't realize or refused to recognize those many years ago. I was totally enamored at dressing as a woman. He was doing this as much for me as for him! Jake always did know me best.
The club turned out to be at a little strip mall. He pulled around the back. Fantasy Island had a large parking lot that was ringed by one of those 8' high privacy fences. In addition, there was a security guard at the gate. Jake rolled down the window, said a few words and was waved through.
The lot was packed. I estimated over 100 cars were parked in the rows. Jake pulled the car into a vacant space in the back of the lot and killed the engine. He always parked in the back of any lot to protect his doors from dings. He got out of the car. Funny, I sat there, waiting, no expecting, him to come around and open the door for me. Which, of course he did. After all, if I went this far, I was going to be treated as a lady.
This time, he interlaced his arm in mine and gently led me across the lot. I could hear the heels tap in rhythm as we approached the door. I could feel the cool night air run up my dress, which was about 4 inches above my knee. The cool wind flicked at cock and caressed my thighs. God, there are advantages to this. It sure felt good!
When we reached the door, he paid the cover charge and led me to the coat check. There, behind the counter was one of the most beautiful creatures I had ever seen. More than 6 foot tall, bright blue eyes, she was wearing the traditional costume; the flame red, sequined bustier, black seamed stockings and hells that were 4 or 5 inches high. But what I found remarkable was her poise. She was outgoing, even a little flirtatious. But she was acting like a real woman, not a man acting like a woman. I remember the rehearsals for the play and the direction that I was given. Sister made me repeat actions over and over again, until they became natural. These included walking, sitting, talking and even the slight turn of my head that caused my hair to swirl. I got it. If I was here, dressed like this, I would be the same kind of woman as the coat check girl. After all, if it smells like a bear, if it looks like a bear and acts like a bear, it must be a bear.
This ends Chapter 1. The next Chapter will deal with the bar and my experiences there. Tune in!
Love,
Jo
Jake Part 2
In which your author completely loses control of the situation and learns a lot about him/herself. *************************************************************
As the door leading to the bar opened, I was amazed. I could hear a blues band in the background playing softly. The lights were bright, but not harsh. I guess I had judged this place by Jake's personality. I had expected a frenzy of flashing lights, accompanied by the loud, harsh beat of Metallica. I considered this a good sign. I felt out of place in modern clubs when I wear jeans and a sportscoat; in my red minidress, I certainly was self conscious enough.
Jake again gently wrapped his arm into mine and lead me toward a table right in the middle of the barroom. And this room was huge! There must have been over 100 tables scattered throughout the room. At the head of all this, was the most ornate, mammoth oak bar I had ever seen. And believe me, I've seen a lot of bars in my day. There were at least 40 stools around this wooden Goliath, almost all occupied. The entire middle of the vast room was a polished wooden dance floor. My eyes had not yet adjusted to the light, so I couldn't really see who was who (as if I'd know, anyway). Jake, suspiciously being the perfect gentleman, pulled out my chair and I, surprisingly, glided very gracefully into it, again demurely crossing my ankles. I had to cock my legs to one side because of the heels. Looking down, I noticed how elegant and almost flirtatious this looked. My legs, now long and smooth, assumed an unnatural (for me) shapeliness because of the heels. My silky hose almost made them gleam. I felt a faint stirring in my crotch. Oh no! Not now. At least I could wait until I get a little bit acclimated. No dice. I turned myself on!
Here's the picture. I'm perched upon a chair, looking like some middle-aged siren on the make in the middle of a gay bar. There are at least 150-200 people here, who I presume are all Gay, and with my luck, on the make. I never planned to come here, I really don't believe I am here, dressed like this. I am very uncomfortable and embarrassed. And THIS is the time I choose to get a hard-on?
I realize that Jake is asking me something. I smile nervously and ask him to repeat it. "Scotch ok?", he had asked.
I told him ok, but make it a light one. I thought I would need my wits about me before the night was over. Besides, Jake had laid out a bustier which certainly reduce my waist and given me a more girlish figure. But it was hard to breathe at times and I'm sure it would put pressure on the bladder. That was a scene I didn't want to think of yet.
I glanced at the waitress and almost collapsed. I instantly could tell that this was a guy, about my age. He/she was dressed in a low cut black, satiny cocktail waitress uniform. It was complete with starchy petticoats which made a SWISH as he made any move. Perched on his head was a very realistic wig (I guess). It was blonde and fell to his shoulders. His makeup was very much overstated; almost whorish. On his feet were the highest heels I had ever seen. Jake gave him our order and he slunk away with his petticoats swishing behind him. Now here's an interesting moment. I checked him out from head to foot with a critical eye. Not because of why he was wearing such an outfit, but I was judging his taste on how he was dressed. I recall thinking he was rather slutty! This was a real shock. I could feel myself falling further and further into my role.
Our drinks came rather quickly. Our waitress smiled and flirted with Jake. She slammed my drink down in front of me. Surely, she didn't consider me competition? Jake attempted to make small talk but I didn't know what to say. As we fell silent, I looked around the room. Most tables had a couple at them. Most of these couples were two men. But in the corner, I spied a couple of tables with women at them. Considering my environs, they were probably like me. No, they planned to come here. I wonder what they were like. Jake muttered something about going to see a friend. I panicked again. "No, don't leave me alone!", I pleaded.
"It will just be for a few minutes", he said. "Remember what we talked about. We are here only as friends. I need to circulate so the others realize that. Besides, I think that they others also need to realize that you are available." He quickly added with a sparkle in his eye, "If that's what you decide you would like. I told you, no pressure. Do what you feel like. But," he added cryptically, "give it a chance. I remember that play and I know you do too. For one night, relive it. Explore it further. You may enjoy it. If you don't, at least you'll know that too."
He left a twenty on the table to cover any drinks I would want. I sat there, too scared to look around any further. This entire scene was getting more and more complex. I was used to the clothes by this time. In fact, whenever I moved, I could feel the stiffening in my groin. The underwear, the hair and the makeup was becoming a positive feature. I slowly lifted my head and glanced around the bar again. This time, I noticed more detail. Men were laughing and holding each other. This didn't seem that out of place to me for some reason.
I sipped at my drink and continued to look around. I heard the now familiar tap of heels on the wood floor. I looked over my shoulder and spied a redheaded vision. She was about 5'8", a little shorter than I. Her emerald green dress slid suggestively off her left shoulder. I noticed with some astonishment that her hosiery and 4" heels matched the outfit to a tee. I nodded politely, not knowing what to say to a beautiful woman when I was dressed like one. I heard in a soft, but slightly deep voice, "May I join you?" I just grinned like a fool and nodded again.
She slid into the chair exactly like I did. For some reason, this pleased me. She set down her suede purse on the table and unclasped it, took out a cigarette. Wordlessly, she offered me one, which I took. Silently, she slid two out of the pack, pulled out a gold lighter and lit them both. Not really remarkable, unless you figure I quit smoking 5 years ago.
The waitress came by and she whispered, "Vodka gimlet and freshen up my girlfriend's drink at the same time. I heard the swish, swish, swish of the petticoats heading toward the bar. I gazed at my new companion. She smiled and after our drinks came and the swish disappeared into the dark, she finally broke the ice. "First time I take it."
"Why would you say that?", I wittingly demanded.
"Because you act exactly like I did 3 months ago when I made my debut", the redhead sang. "Look, I was even more nervous than you are. I had only dressed in private. I learned makeup from magazines. I saw you with Jake when you came in. He told us last week that he had a special friend he was going to bring in tonight. Just asked us to be friendly."
I was more confused than before. Not only had Jake planned this entire evening, he was so confident in the outcome, he told everyone except me. I felt my cheeks redden. I'm sure my eyes reflected my ire because the redhead shook her head and said, "Hey, don't be upset. I only came over because I know the first time is almost impossible. You are in an alien environment with completely foreign clothing on and have no idea how you feel about it. I was the same way. Jake told me that you had repressed these feeling for many years; but other than that, I understand exactly what you are going through. This can be fun. However, let's make a little deal. Try it. At least you know that way if this life is for you. I won't stay with you all night because I don't want to cramp your style." (I don't know how to refer to people at this point. From now on, the person's gender will be reflective of their dress.) With a leer, she licked her slips slowly and purred, "I don't want to miss any opportunity myself. Jake helped me that first night. He gave me advice and offered suggestions throughout the night when I needed them. I owe him that so I'm going to help you"
She said her name was Renee. She started with hints on female deportment. I was poised just perfect to her discerning eye. But I was leaning back into the chair. She showed me that sitting straight caused my breasts to highlight my dress. I was pleased. As Renee continued, I honestly grew more interested. She demonstrated how to hold a cigarette and even how to gently puff at it, not take long drags, like a man. When I wasn't using my hands, I learned how to tuck them properly on my lap. She even commented on my walk as I had entered the bar. I learned a lot. Looking at the clock, I was shocked to discover that more than an hour had passed. Renee noticed this and said that there was only one more thing to learn. She instructed me to get the money off the table and grab my purse and follow her. I rose, just as Renee has told me to. I did just fine until I discovered that my right leg had fallen asleep. Shaking a bit, I was able to revive it and suggestively shaking my hips slightly from side to side, I followed Renee to the exit.
The restroom! I hadn't considered that. I grabbed her arm and said, " I can't go in there" She just laughed and maneuvered me into the sacred door that proclaimed, "LADIES". I was mortified.
When inside, Renee almost cried, she laughed so hard. Between sobs, she asked, "Just who do you think uses the Ladies room in a gay bar? Come, let's get busy."
I finally found out why it takes women so long in the restroom. Undoing this and that, pulling up slips and dresses etc. It was even worse when I was finished. It seemed that everything had slid up. My breasts were now 6" higher, my dress was 4" shorter and my hose were 4" lower. I worked at it for what seemed quite a while, until it felt right. Exiting the stall, I glanced into the mirror and confirmed I was back in shape. In fact, as I lingered in the looking glass, I was very pleased with what I saw. The Scotch had really brighten my cheeks. My hair was a little disarrayed, which was rather pleasing. My legs just seemed to go on for ever. What was the old saying, O yea, "...all the way up to my ass". I got out my makeup while waiting for Renee. I puttered a bit, not out of necessity rather just to reflect. I was here, I have decided I was pretty. And quite frankly, I was feeling more aroused the longer I was here. But now what. I needed to decide. I either was going to go back out and sit at the table like a lump, find Jake and whine that I wanted to go home. Or, and I don't believe I am even considering this, I could, well, try to make some, well, new friends. That's all. I have decided. I would go back out and participate. Just enough to get a feel for the lifestyle. Besides, I never heard of a gay man wanting a woman. I was dressed as a woman, so therefore, I was the safest man here. What a fool I was. But I knew it at the time. But it was a good release valve. Renee said she was ready. I stood up, still facing the mirror, applied more lipstick in an almost defiant manner. I then clasped my purse with a snap and turned on my heel and headed out to face my destiny.
Renee and I parted. She promised she would be "around" until closing. I stood in the entrance and looked around the room. I didn't see Jake anywhere. I noticed the other girls were still in the corner. But I didn't feel like being with " the Girls". In the restroom, I had resolved to see this little charade all the way through. I figure I'd go to the bar, order a drink and let nature take it's course. The bartender was the most gorgeous creature I had ever seen. At least 6'3", with arms and a chest developed like a body builder without getting that beachbum type look. His black hair was in tight curls which perfectly framed his face. Deep blue eyes finished off this vision of Grecian virility. The sudden acknowledgment of these feelings surprised me but I wasn't really embarrassed by them. I don't know why, but it seemed OK to admire him. I didn't WANT him, but was attracted to his masculinity.
I perched myself on the high stool. I crossed my legs a little awkwardly at first. But with the gaffe I was wearing, my balls didn't inhibit this movement. I sat there with my drink when someone sat down next to me. I stole a glance out of the corner of my eye. My new neighbor was just an ordinary guy, a lot like I was a scant 3 or 4 hours ago. He had brown hair, jeans and a rather ordinary blazer on. He cleared his throat and stammered, " Could, could I get you, you know, another drink?"
I felt an alarm go off in my head. This was it. I was being hit upon. I was at the point of no return. Either run toward the exit or .."No thank you, I just ordered this one. But thanks just the same. I smiled at him friendly like, no in retrospect, it must have been almost eagerly.
He smiled and asked if I would like to join him at a table. I agreed instantly. I was committed. I was with a man and not just a little excited by it! Sam briefly muttered something to the bartender and then turned to me and rather cavalierly swung his arm and turned his palm upward.
He followed me as I looked for a table. The place had really filled up but I spied one, again, almost in the middle. When we arrived, he almost tripped trying to get to the chair before me in order to hold it out. I approved. By God, I've evidently decided when I dress like this, I will be treated properly. This caused another blush to my cheeks. I was no longer a man in a dress, I was a true crossdresser. So be it.
He introduced himself as Sam. I said my name was Jo. He told me how pretty I was. I blushed. I told him how handsome he was. He beamed. This inane conversation went on for 5 minutes until and old favorite of mine, "Michelle" came softly cascading across the sound system. I perked up a little. Sam looked puzzled and then I could see the light bulb go on over his head. "Would you care to dance, Jo?" I said I would be delighted.
He lead me toward the dance floor. There were a few other couples out there, but no one dressed like me. He took my right hand in his and pulled his left arm around my reduced waist. He had the lightest touch I had ever felt! I awkwardly turned and stepped to the music. When the Beatles were finished, Sam released me and we parted slightly. With a puzzled but somewhat endearing little boy grin, he said, " That was nice. But next time, could I lead?"
I was mortified. Here I was feeling that I had caught on pretty well, and now I had reverted to my old masculine ways. Overconfidence will get you everytime. I blushed, of course. That is ONE thing feminine I had picked up rather well. Then, the entire bar seem to fall quiet for a second. From somewhere, a disembodied voice announced, "Now for your dancing pleasure, our manager and owner has requested a special song. He said it is dedicated to a beautiful lady."
The time honored strains of "Unchained Melody" filled the room. I had always loved this song. Sam pulled me toward him. This time, however, he firmly grasped me around the waist and pulled me tight. You remember how we danced at the Senior Prom; both arms around your girl, holding her firm. I felt secure for the very first time that evening. I surrendered myself to his lead. I felt myself go a little limp. To support myself, I draped both arms around his neck and clasped my hands loosely. After the first stanza, I was almost ready to swoon. Feeling lightheaded, I laid my head on his shoulder. There. The deed was done. I had crossed (no pun intended) from man to real woman. I felt protected. I felt wanted. I felt pretty and desirable. And most importantly, I felt the rock hard cock in my beautiful panties. God, was Jake ever right! This was one of the most touching moments of my life. The song seemed to go forever. I was a million miles away in the arms of a man who desired me!
After about a hundred years, the song slowly died away. I finally realized that we were still clinging to each other in the middle of the dance floor and no music was playing. Sam must have gotten the same idea because we let go. I deliberately held firm for a moment. I wanted Sam to know how I felt without any verbal explanation. When I released him and moved back a step, I could see in his eyes that I communicated my emotion very well.
He reached across my back and grabbed my shoulder. Hugging me tightly, he directed me back to our table. He ordered another round of drinks. We didn't say anything; we just stared at each other. I was almost oblivious to anything around me. From my mind's eye, I saw someone nearing the table. It was accompanied by the now familiar swish. swish of the waitress' petticoats. I glanced away and saw the whorish one who had first waited on Jake and I went we arrived. I returned my attention to Sam when I heard a crash.
I jumped but too late. The little bitch and dropped my drink and spilt it. I suddenly felt the cold liquid running down my dress and onto my legs. Looking down, It looked like I had wet myself. I started crying!
Sam was up in a shot. He grabbed the towel from the whore and started to wipe my dress. His face was reddened, I noticed. He was embarrassed! Wrong. He turned to the waitress and said, "Bobbi, you're through. Get out."Bobbi had a little smile on her face as she dropped the serving tray on the table. She spat,"Serves the little bitch right. Who does she think she is, anyway?"
Sam grabbed my arm and said, "Don't cry. Come with me. We'll get you cleaned up"
I was in a daze. What was he talking about? ******************************************************************************
OK, Ladies. This was part 2. I might have gotten a little long, but it's my story. Stay tuned for part 3, coming to a BB near you soon. I welcome all remarks, private or public, good or bad. Just drop me a line?
Jo Black
Jake Part 3
by
Jo Black
In which I come to grips with some rather hard subjects. (Yes, it's a joke) ************************************************************
Sam led me back toward the bar. I followed defeatedly. After what I had gone through this evening; just coming here, and confronting my feminine side which was hidden from even myself. And then, accepting the situation, and now all that is gone. I am just humiliated. My red mini, in which I discovered who I was and what I wanted, was ruined. And worse of all, I was the focal point of attention and curiosity from all in attendance. As we approached the bar, I saw Jake balancing from leg to leg nervously. When we got that far, he looked at me almost fatherly and said, " I'm so sorry Jo. I didn't mean for this to happen. I wanted this to be your night. Come, I'll take you home."
As I started to nod, Sam cut in. "No, it's alright, Jake. It was my girl who caused all this. I'll be damned if I'll let it completely ruin Jo's big night. If that's OK with you, I mean, Jo."
Part of me just wanted to say screw it and leave this dream and return to my past reality. But some perverse side of me said I'll stay with Sam for a while. Unfortunely, this perverse side also controlled my power of speech! I guess I really wanted to stay. Jake gave me one of those shiteatin' grins of his and said, "Good for you! I'll be around."
Sam then directed me to a door by the end of the bar which declared, "Employees Only". He guided me down a short hallway to a door marked "Manager" and produced a key ring from his pocket and unlocked the door. I heard him snap on the lights and he bade me to enter. Yes, I'm sure that I was the last to realize that Sam was the manager. No wonder that waitress was pissed off; she was jealous of me, little old me. Go figure.
Jake closed the door behind us. He handed me a dry towel and said, "now you just wait here. I'll go see what I can scare up." He left but returned rather quickly. In his arms was an old white fluffy robe! " Here", he offered, " just go into the bathroom and slip out of that wet dress and put this on. Then, after you've had time to compose yourself, we'll see about putting you back together."
I gratefully took the robe and headed into his private bathroom. I slid out of the dress and after a quick inventory, also discarded my slip. The drink had started to dry and I was rather sticky. Spying the adjoining shower, I decided what the hell and undressed and slid into it. I was very careful to keep the water off my face and hair. Stepping out of what was the quickest shower I had ever taken, I then patted my now rather smooth and silky body dry. I noticed some Shower to Shower powder and doused myself liberally with it. I then put on the bustier and panties. Everything else was unfit. I sighed, put my foot into my heels, and opened the door. Sam was seated at his desk. On this desk was a steaming porcelain teapot with matching cups and saucers. He glanced up and smiled. "I thought that tea might help you relax. I know it always helps me."
What a sweet gesture! Only, I have never cared for tea much but the idea seemed just perfect. I slid into the chair across from the desk. I took my tea and it was perfect. I immediately felt better. Sam started to tell me how he had acquired this bar and all. "I had been a loan officer for 8 years at the bank. In this capacity, I was expected to follow up on our clients. I came in here one noon. It was very quiet and empty. The owner, whom I had made the loan gave me coffee and showed me the books. It was phenomenal! In the 2 years in which the bar had operated, he had earned enough to pay off the loan."
" We talked for quite a while that day. He was tired of the business and wanted to retire to Florida with his wife. With my knowledge of the loan history and having seen the books, I asked him flatly what he wanted for the place, lock, stock and barrel. He told me, I gasped, and said, OK, it's a deal. I went down to the bank, got a loan and that was that."
"It wasn't until that night that I discovered that the clientele was rather specialized", he laughed. "But there were no other problems with security or anything, so I held onto it. And I've done well. The only change I have made was updating the decor and putting the security fence in the back. It's all increased business."
He paused a few moments. Then slowly, he continued, "I never thought myself gay of bi or anything. I dated a few women but nothing I really found memorable. Naturally, being in this business, I investigated it some, but never thought I could proceed. Until tonight. When I saw you at the bar, with the light behind you, I was grabbed by a giant fist. I just thought you were perfect. When I was dancing with you, I knew this could be it. You're as beautiful as any woman, but are not. You are as vulnerable as any woman, but are not. What you are is yourself. Even now, sitting there in that old robe, you are definitively female. Not just the way you look, but the way you're sitting, the way you are acting. So, if I'm attracted to you, I still don't know if I am Gay, Bi or straight. All I know is I want you. Let's sort the rest of this out later."
I was stunned. He wanted me. I wasn't shocked about being with a man. No. I was stunned because he wanted me as much as I wanted him! I stammered through my most current blush, " But.but. . are you sure you want ME?"
He laughed. "Oh, yes, my dear Jo. I've wanted you ever sense you laid your head in my shoulder while dancing."
Bingo! That's as long as I've wanted him! But damn, I've never done this before; what do I do? Literally, I have never envisioned how to sexually please a man. OK, it never came up when my parents told me about the birds and the bees. And I don't think now is the time to call dear ol' Dad for the second lesson. I started to shake nervously.
Sam must have noticed because he refilled my tea and his hand lingered across mine. He slowly comforted me. "Hey, I know. I've never done this before either. My customers have given me, in great graphic detail I might add, what they prefer. But, I would prefer we were spontaneous. Do what ever feels good."
I smiled broadly. "That sounds perfect. But I'm such a mess. For our first time, I want it to be just right."
Same said, "Honey, just remember where you are. Let's run down the hall to the dressing rooms and you can pick out just what you'd like."
Now that I had decided to "do it", my mind shifted gears. "No," I demanded, " If I am going to please a man, the first step is dressing to his tastes, not mine. YOU go down the hall and find whatever you think is the sexiest outfit there and bring it to me. While you're gone, I'll redo my makeup and get ready."
Sam explained that the door at the back of his office was also his living quarters. He asked if would prefer to dress there. He had a vanity, he said, and a small bath off that. I thought that really felt more intimate. Imagine, I'll ready myself for my man in the boudoir. He would wait impatiently as I primp and make sure everything is perfect. Then I would make my grand entrance. I quickly agreed.
The living quarters were neat and very masculine. All the furniture was heavy, dark wood. The was a leather couch and matching recliner in the corner. I spied the door to the bedroom, took a breath and entered. I just stood there for a moment. The decor was identical to the antechamber. Heavy, dark woods, but it seemed very comfortable and strangely homey. I looked around for a bit and then sat on the edge of the bed. And I mean the very edge. Here I was at the scene of the crime. I would surrender my virginity here on this bed! I am going to be deflowered! I realized that all these phrases from Danielle Steele seemed very trite. But, whatever gets you through the night.
I heard a knock on the door. Sam had returned. "Are you decent?" he had asked. No, you idiot, I'm preparing to get screwed by a man! "Yes, please come in."
Once in, he deposited the most beautiful nightgown I had ever seen on the bed. It was minty green with delicate little lace around the hem. I picked it up and felt it's silky texture. It was like heaven. The front wasn't cut terribly deep. Rather, it had flows of the green cascading down the front. The back, however, was severely cut to the waist. The right side had a long slit up it. It was gorgeous. He had brought matching pumps with what had to be 5" heels. There was an overnight case also. Sam explained that one of his "girls" had packed everything I would need. I shooed Sam out of the room. "I'll call you when I'm ready; not before."
After Sam left, I opened the overnight case. I guess Sam's "girl" did pack all the essentials. I started to layout the contents on the vanity. I found several different types of lipstick, mascara, powder and the such. I found one packet which contained fake fingernails. Now there's something I've never had. The stockings were the most sheer I had ever seen or touched. They had a tint of green in them. I just pulled them slowly across my face and felt my cock stir again. There were panties, the same shade of green and as sheer as the stockings in the bottom of the case. The matching bra was strapless, with cleverly placed wires in the soft curves of the cups. She had even enclosed what I determined could only be fake breasts. They were firm but had some give to them. In the front, there were even nipples in the appropriate places. The last item in this Pandora's box was a bottle of "Passion" with a note wrapped around it. Pulling the note off, I read:
You lucky Doll. Most of us have wanted to be the
first with Sam. I saw you when you came in. You
are just right; pretty but also real. Remember,
Sam's a real nice guy. Don't hurt him in any way.
But good luck and enjoy.
Cindy
The evening keeps getting curiousier and curiousier. This is the second "girl" that I know envies me. Well, this must be worth pursuing. I turned my attention first to the makeup. I corrected my slightly disheveled face. I added some longer fake eyelashes that I found into the case. I then turned to the task of the fake nails. I read the directions which seemed clear enough. And, for the first hand, they were. Have you ever attempted to pick off those little backing sheets with the fake nail. I persevered and finished them up. I held my hand out and was amazed how they appeared to slenderize. The long, red nails seemed to flicker like lighting bolts out of my fingertips. They were energizing. I felt a surge of power throughout body. I was excited that I could feel such strength from such a feminine thing.
I then turned by attention to the underlayments. The panties felt almost like a whisper as caressed by thighs as I pulled them up my legs. I then adjusted the gaff and all semblance of my gender were gone. The bra was trickier. I finally snapped it in front and spun it 180 degrees into place. To my delight, I found the falsies filled the cups perfectly. I looked in the mirror and was shocked. I was close enough so I could see only my body in the looking glass. The supple curves blended perfectly with the gossamer like panties. I slowly slid my long tipped fingers down the sides of mt panties. I could feel the straining in my gaff. I stopped and took a deep breath. I needed to wait.
I slid the garter in place and started the long journey from my toes to my thighs. As I brought the stockings up the leg, I could feel the touch of butterflies, flitting at my now engorged crotch. I grabbed the towel I had laid on the vanity and quickly pulled the minty panties down, undid the gaff and felt the warm, milky liquid pump into my towel covered hand. It seemed I would come all night. Finally, the pressure had relieved itself. I just sat there, feeling a calm running over me. It was drained my physical tension but I felt an emotional tension that was even stronger. I just wanted Sam more now.
I got up and quickly cleaned myself off and repowdered my upper thighs, cock and balls. After rearranging myself, I slid into the green heels. I had never felt so vulnerable as I did with those shoes on. I could only take short, mincing steps. I felt that my newly acquired breasts were pulling over in front. I continued to pace across the room toward the bathroom and back to the vanity until I felt some type of grace; or at least some type of balance. It was time for the crowning touch, the gown.
I found that my hands were shaking now with anticipation. I slowly raised the gown toward me and just clutched to my chest. It was so soft and so incredibly silky. I raised it over my head and let it, ever so slowly, slither down my now soft, feminine body. It felt the lace at the hem as it tickled my nose and cheeks. As it made it's descent, I swear I could feel it hardened my nipples as it passed. Then it flowed across my flat stomach. And then, it made contact with my panties and stockings. I was hugged by the silk. It had completely encased my body. I realized that I hadn't breathed at all as it fell across by skin.
I glanced in the mirror and was delighted. There was someone else here now. My former self was gone. Now, only Jo remained. The vision in the mirror could only be female. The gown had covered me like melted plastic. It took the exact same line as the body underneath. When I breathed, I could feel it expand and contract, rise and fall, just like my it wasn't there. It was almost like a second skin. But this skin was silky and shimmery in the lights. I posed in the mirror. I put one foot in front of the other, tilted my chin up a bit, cocked my head to one side with my one hand on my hip, the other on my thigh. God, I was gorgeous! This one moment was worth all the hassle tonight. I smiled rather wickedly. I then applied a redder shade of lipstick, very heavily. My lips glistened as though they were wet from the rain. Well, the time had come. My lips would be wet, but not from the rain.
I spun on the ball of my right foot and floated to the door. I was now complete. This body in this gown was unmistakably in charge. (Helen Reddy should be so proud). I slowly opened the door and let in sort of creak open. I waited until it stopped on its own accord and then confidently strode into the next room and struck my pose. "Sam, I'm ready now."
Poor Sam was thunderstruck! He just sat in the recliner in obvious shock. He just stared. Then he slowly got to his feet and walked toward me, step by step. His eyes never left me. I could feel his gaze as it jumped from my face to my breasts, from my feet to my crotch. He was hooked. He muttered, "God, I didn't expect you to be THIS beautiful."
He had made opened a magnum of champagne and deftly poured each of us a drink. Still, he never took his eyes off me. The champagne tickled my nose but warmed me inside. He poured another. I intertwined our arms with the glasses in it. We drank as lovers drink. He had put unchained melody on the stereo and we danced again. But this time I lead and Sam had no objection at all. I led us toward the bedroom. He got the hint and took over. As we entered the room, he kicked the door closed with one foot, never missing a step. The music magically ceased as we reached the bed. Sam suddenly wrapped his arms around me, hugged me tight and kissed me. I felt his breath across my upper lip. Then I opened my mouth slightly and he slid his tongue in and out, teasingly. I opened it wider and he forced his tongue in deeper, filling my mouth. As he probed, I started to unbutton his top button. Understanding my motion, he released me enough to continue my way down his chest. I unbuttoned the last button and ran my finger through his coarse chest hair. It was heaven! His chest was lean and firm, not rock hard (like my cock right now), but very strong. I pulled the shirt off his arms and threw it on the floor. We then broke. I gently pushed him back and he sat on the bed. I slowly sank to my knees. I undid his belt and pulled down the zipper. I could now see the massive lump in his underwear. Probably for the first time in my life, I found white, cotton jockey shorts sexy as hell! I reached out, not at all tentatively and grasped in firmly in my hand. I pulled and pushed a few times and got great reaction from him. I released his manhood and pulled his pants off. I then slowly crooked a finger into the elastic band and gently started the long trip down for his jockey shorts. There. I had exposed his throbbing cock. It was actually straining at me. Without hesitation of forethought, I pulled the shorts off and sunk my head into his crotch.
I flitted my tongue like a snake at the smooth head. I could taste salt. The penis seemed to keep getting larger and larger. I slid my lipsticked mouth over the hood and into the shaft. The lipstick provided a very good lubricant as i took more and more of the shaft into my mouth. I felt myself start to gag a little, so I backed out a little and then proceeded. After a very short time, I had him all the way to the back of my throat. He tasted wonderful! The salt mixed with the natural skin to create a delicious dessert. I started to move my head back and forth slightly, then a little quicker. I could hear him moan a little. I started to go faster and faster, sliding my tongue all around the cocksickle in my mouth. I felt him stiffen quickly, and then felt the rush of cum into my mouth. I was able to get my tongue on it as it shot out and it was creamy and warm and made me warm all over. Finally, he relaxed. I cleaned up his cock with my tongue and released him . I slid my tongue across my lips and looked up at him. Only one thing crossed my mind. In a very sultry and suggestive voice, I stated, You ain't seen nothin' yet.
So ends Part three of my great adventure with Jake. PART 4 will available hopefully later this week. I need to go take a very long, very cold shower now!
Hugs and Kisses,
Jo Black
JAKE PART 4
BY
JO BLACK
In which things get stickier and stickier as I attempt to decipher what has happened and determine what will occur.
As I sat on the floor, my head in his exposed lap, I felt spent. Never before had I experienced such great exhilaration during sex without even being touched. I believe that is a result of the knowledge of giving such exquisite pleasure while being in total control of the entire act from beginning to end. I will always relive that moment when Sam reached climax while I took, not accepted, but took his love in my mouth. Perhaps the greatest thing about being female. You are at once demure but forceful; you crave security but control; you are beautiful and delicate, but are in charge. I wonder when all this great philosophy has occurred to me. Maybe I always knew it subconsciously but repressed the knowledge because I was living a masculine life. Not any more! I am woman, hear me roar.
Sam recovered slowly and started to pull me toward him. I cooed softly, "Not now Baby. Just lean back and relax." I gently prodded him backwards onto the bed. I then pulled myself next to him and started to massage his chest. Everytime he tried to reciprocate, I gently but firmly stopped him. I now knew control; I was hardly ready to relinquish it. I worked my self lower and lower down his torso. I moved my head onto his chest, knowing that the wig hair was now tickling his skin. I paused briefly at the navel and slowly licked and tongued it. I felt his muscle ripple and stiffen. I silently glided my hand down until I contacted his coarse pubic hair. I found and slowly rolled his balls in my hand, just like Captain Quegg in The Caine Mutiny. Sam started to moan and slide his body from side to side. I continued to massage and kiss and tickle; not giving him a chance to do anything but rebuild his expectations. I then continued to flow down his body, trailing my hair across his now nerve heighten belly. I reached his cock and grabbed it with my free hand. I saw the long, red nails resting on the shaft. I then traced the nails ever so slowly up and down the shaft. The cock grew in front of my greedy eyes. It thickened then extended itself. I kept dragging the red nails up and down, up and down, up and down as the blood started to engorge the rockhard cock. I knew that he was good for a while because I could still taste the salty, creamy cum in my awaiting mouth. I released his balls and brought my hand below him, again, agonizingly slowly, letting his every nerve be stimulated by my touch. I stuck out my finger and inserted it's sharp, dart like nail into his ass. He stiffen the muscles upon first contact, but I persisted to slowly grind the finger deeper and deeper into his rectum. Suddenly, he relaxed and I then drove the finger into his prostrate and then Sam really moaned. I backed off and then jammed it again. I repeated this and Sam really responded. He was ready to come but quite frankly was still spent. What I delightful time I was having!
It's funny, but while I was tending to Sam's needs, I never got hard myself. As I continued to manipulate the balls in one hand and tend to his asshole with my other, I marveled on this. I was quite satisfied at this point with just the emotional release. I have read many things about orgasisms being as mental as physical. Evidently, this has a lot of truth to it. Enough analyzation; back to thee task at (or in) hand. I could feel him go even harder in my hand. I instinctively knew the time was right. I pulled my finger out of the rear and slid my head back to his steel shafted organ. I ran my tongue down the top and up the back. I slowly licked the entire crown of the hood. I then started to suck it in like a strand of spaghetti. As I slurped it into my mouth, i gently worked my tongue across the breadth of the now seemingly enormous organ in my mouth. I could taste the sweat mixing with the precum. I sucked harder and harder. This time, it felt like I was swallowing the head of his cock. I just tried to relax my throat and then he came. It seemed like a tidal wave had hit my tonsils. The relentless attack by the wave of cum seemed to last forever. I felt him relax. I disengaged from his groin and moved up his chest and gave him a great big kiss, wet with his own seminal juices. He just hummed with delight. I must have ingested a quart tonight, but it was unbelievably erotic.
I must have dozed off for a few minutes when the phone rang. Sam answered it and turned to me and whispered, "It's Jake. Do you want to talk to him?" I nodded yes.
Jake wanted to know my plans for the rest of the evening. Feeling drained from my experiences, I told him I would be ready to leave in about 20 minutes and would meet him in the bar. After I hung up, Sam laid on the bed with a scowl on his face.
"Is there something wrong?", he asked. "I thought everything was perfect; at least I KNOW it was for me. What can I do to change your mind."
I had sort of planned on this happening. "Sam, everything was great; better than great. It's just that I'm tired and I need time to think about what has happened and exactly how I really feel about it. To be completely honest, this entire evening was 100% better than I could have possibly imagined. Besides," I vamped, "if I stay here, I sure won't get any sleep."
Sam nodded, "I think you could be right. Let me offer this. I need an assistant manager right now. I will pay you handsomely and provide your wardrobe. And this is a real job. There is too much for me to do alone. I need someone I can trust and like to spend time with. Don't say anything yet. Think about it. If you decide yes, come in tomorrow. If not, thank you for the best night of my life." He kissed me deeply and soulfully and then released me. I quickly donned my red minidress, that venerable garment that made this night possible and left to meet Jake downstairs.
I found Jake on a bar stool in the now empty bar. The lights were fully on and in looked like an empty theater after a play. I slid on the stool next to Jake and he said, "Man, you OK?"
I responded quickly. "More than OK, I'm better than I ever have been. I'm a little confused but I'm happy. Come on old buddy, take a lady home." He nodded and we retraced that earlier trail to his car, now the last in the lot.
We drove in silence for a while. Finally, flirtingly asked, "Don't you want to know what happened? Huh, Huh, come on, it's got to be killing you."
Jake's eyes recovered their sparkle. "Yea, got lucky, did you?"
"A lady never kisses and tells, big boy"
"Well", he drawled in a newly found southern accent, "you shore are right, Ma'am. Good thing the only ones here is a man and a filly."
I couldn't help laughing. Jake's attitude had returned to the old sense of humor. We quickly traded notes on our latest adventure. It was just like always. He did this, then I'd top it. This comradierie continued all the way home. Pulling into the garage, and with a great flourish and an awful British accent said, "May I take your hand, M'Lady."
I, in reaction, offered my hand and he gentlemanly assisted me from the car and closed the door. He in turned opened the door to the kitchen and allowed me first entrance. I could feel his eyes on my now practiced wriggling walk. I purposefully exaggerated the swagger of my hips. I put one hand on my hip and almost taunted him as he followed back to the bedroom. After we entered, I turned to him and said, "Why don't you come up and see me some time?"
He just laughed and we entered the bedroom. I sat on the edge if the bed and Jake sat next to me. "Did you really enjoy it?", he wondered. "I mean, did this evening open any doors or at least resolve any conflicts you had?"
I reached over and took his hand, rather shyly I might add. "Jake, You don't know what a favor you did for me with this evening. I hadn't thought of this since High School. Not because I didn't want to, I think, but because I just plain blocked it out. I answered some questions tonight. I like wearing these clothes and being feminine. It's just right for me. I know now that I am attractive and I want more. But There were new questions brought up tonight I just don't know about. The sex thing really threw me for a loop. I was never more turned on and more satisfied in my life than I was with Sam. But I don't know if this means that I am simply Gay, or if I'm really female having straight sex. I'm really confused over this. Tell me, what do you think?"
Jake pondered all this for a moment. He then glanced down at my hand in his and said, "I think that it doesn't really matter. Look at it this way; you and I are friends. But you are holding on to me for dear life. In the past, we would never had made physical contact like this. But I don't feel it's strange and you don't either. But are you Gay; are you female; I don't know. I suggest you take that job at the bar. Give it a chance. Don't be scared of what happen tonight nor let it sweep you off your feet. Your consulting business can function without you for a while. You told me that. Call and tell them you're on a sabbatical. Move out of the company apartment for a while. Hell, move in here with me. I'll help you explore all this. It will be just another grand adventure."
And that's just what I agreed to do. A neutral ground is a much better atmosphere to make decisions. I asked, "Just where do I sleep. You only have one bed and your couch is lumpier than Mom's mashed potatoes."
"Well, I guess in here with me. Hell, we've done it a million times in the past."
This seemed quite innocent on the surface, so I readily agreed. His couch was impossible to sleep on unless you've passed out on after many, many drinks. I then realized that I knew WHERE I was going to sleep, but didn't have an idea in what I was going to sleep. Good ol' Jake to the rescue again. "Man, I mean Jo, my sister has quite an extensive collection of clothing here, including some of the wildest nightgowns you could imagine. Just help yourself, they are in the hall closet. I nodded rather apprehensively, but quite gratefully. I didn't really have to make this decision and was quite glad about it.
After rummaging through the closet, a rather large walk-in I should explain, I was amazed at the selection. There must have been over 100 different garments hung up in there. These ranged from business suits, peasant blouses, miniskirts to the most wonderful lingerie imaginable. I was torn between a gorgeous white silk gown with a slit up the front and a navy blue form hugging satin gown with no back and very thin straps. Finally, after my earlier activities, I felt I wasn't entitled to wear white, I settled on the other. I collected it and noticed a pair of dark backless, 4" heeled pumps on the closet floor. I took my selections into the bathroom and got ready for bed. I bathed rather quickly in the same bubble bath I had earlier. I was sticky and smelled of sex. After drying off, I powdered my chest, legs and genitals. I then let the satiny gown drift down, across my perfumed body. Again, my cock rose to meet the challenge of the soft, sexy material as it tickled my chest and flitted across my thighs. I then sort of tousled my hair and it fell in that sexy, half askew, half curled look. I checked myself in the mirror and was shocked. Here I was without a wig, no restraining underwear and no makeup and I was still gazing upon one hell of a sexy looking broad. Granted, the lights were a bit dim, but then, I thought, so am I. As an after thought, I placed my breast forms in the front and the tight, clingy gown held them in place perfectly. I ran my fingers across my thighs and discovered that I still had those long nails on. Good. I turned sideways in the mirror to catch one last look of my now sexy profile and entered the bedroom.
Jake had turned down the bed and was already under the covers. The lights were low and the stereo played a little Dizzy Gillespe in the background. I wriggled my way to the bed and kicked off my heels and swung myself into the bed. By the way, it's a real bitch to keep a nightgown pulled down so your privates aren't exposed. I lay on my back, just recalling Sam and his offer. Is this what I really want? I know that Sam is really smitten with me, or at least Jo. But before I can address that situation, I need to be more sure of my femininity; is this for real or just a lark. I had never even considered kissing a man before, let alone giving him what I feel was the world's greatest blowjob! Well, there's one sure way to find out. I will take Sam up on his offer. That means I can dress full time and be in public to really see the entire picture. The other way to study this is close at hand.
I rolled over on my side and ever so gently draped my arm across Jake's chest. He said nothing, but his breathing increased. I felt the now familiar stirring in my groin. Saying nothing, I slid my satin encased body across the sheets and pulled myself up on Jake's body. I was getting harder. I planted my lips on his lips and he immediately responded in kind. He flicked his tongue in and out from between my lips. He pressed harder and I pushed back. His hands found my smooth ass and he squeezed it softly and then harder and harder. Suddenly, he rolled over and I was on the bottom! How many times had I seen that move in High School wrestling? He was as strong now as he was then. His hands began to explore my body, rubbing up and down, up and down. Trapped under his weight, I felt a little panicky for a second. I wasn't in charge as I was earlier. But I still liked it. I began to follow Jake's lead. He would grind his hips, and I would grind his hips. Only I did it softer than he. He was really getting hot! He began to pant and I could feel his hot breath on my neck while he nibbled at me. I felt like I was trapped and it felt good, kind of secure and wanted. He turned me over and started to massage my ass. Suddenly, he raised the skirt of the nightgown and I could feel the strength of his hands as he rubbed me. I heard a door open and I turned around. Jake had opened the nightstand and removed a tube of KY Jelly and a rubber. I propped myself up and took the package from him. Opening it, I pulled the rubber out and pulled down his red cotton briefs. I had forgotten how huge he was! His cock was already standing at attention when I coddled it in my hands. I inexpertly slipped the rubber across the rubber, only after kissing the head. I could taste the salty precum and I wanted him!
Jake then opened the jelly and smeared it on the rubber. Oh, oh, here was a new experience. Well, I was so hat by this time, I would do anything. Besides, after tonight, I don't think I'll be easily shocked. He rolled me back on my belly and lifted up the skirt. I felt the shock of a great glob of the jelly being shoved up my ass. It warmed quickly and was rather pleasant. Jake laid on me and started to tickle the inside of my thighs with the slick cock. He pulled my up onto my knees and I knew it was showtime. Thank God. I wanted and I wanted it now!
Then I felt it. The tip of the now metal rod was throbbing in anticipation. It started to slide through the jelly and I then felt the pain. It shot through my body like a knife. Jake, evidently sensing this, withdrew a bit and then gently began to reinsert the cock into my ass. As it went deeper, the pain began to subside. Jake continually pulled back and then gave me a little more. Over and over; it was like I was being reamed out to fit his throbbing manhood. I forgot any discomfort as he completely filled the canal. I was almost pinned like a butterfly on a mat. It was exquisite! My body began to move toward his thrusts and I felt myself lose control completely. The cock now slid back and forth and back and forth; easily, with just enough resistance so we were both reaching higher degrees of ecstasy. Then one last desperate plunge contacted my prostrate and I came. "At exactly the same time, Jake also let go. I could feel the hot, rushing cum as it filled the rubber up. Jake grabbed my organ and let my seed fill his hand. We must have ejaculated for several minutes it seemed. Spent, he withdrew from me and we rolled next to eachother. He brushed his cum soaked hand across my lips and I tasted myself for the first time. I smiled. Jake then licked off his hand and grabbed me and just held me. We slept that way, intertwined. We both had things to think about and resolve concerning our friendship, but not now. I felt warm and sticky and just about perfect. I slept. I'll worry about that tomorrow.
This concludes my first date. If there is any interest in continueing this series, please let me know. If not, I'll start a new series soon.
Ta-Ta,
Jo