Josephina and I had a wonderful night. We had sex twice more and fell asleep in each others arms, exhausted. When I got my wake up call, I was a little bummed. I really did not want to leave her arms. Although I tried to be quiet, preparing for my seminar, I eventually woke her up. She asked the time and groaned when I told her. I sat down on the bed and we kissed gently a couple times. She lay there under the covers watching me dress and it made me feel very warm inside. Like I had a girlfriend. We swapped light chat and I asked her if I could take her to dinner tonight. She seemed to think that was a great idea and we arranged to meet in the bar at my Hotel at seven.
I went to the seminar but my mind was not init. I felt words bouncing off me like distant gunfire. I was in love, well in lust at any rate. The time seemed to drag by and I tried in vain to absorb the materiel, and take my mind off of last night and our date tonight. The few friends I had here, noticed I was detached and showed some concern. I sloughed it off as having a bad nights sleep, a strange room and bed and all. They seemed fine with that answer. Finally the clock reached six and I was free. I had some idle chit chat on my
way to the door but managed to avoid any commitments for dinner or drinks and I hailed a cab and went back to the room to clean up. I was brushing my teeth when I noticed the maid had found Josephina's panties and left them neatly folded on the dresser. I went over to them and felt the materiel and reran the night before in my mind, I found myself taking them and rubbing them against my skin, noticing how soft and sexy they were. I folded them and put them in my pocket and made a mental note to return them tonight.
Putting on some cologne, I looked at the clock and hustled downstairs so as to not keep her waiting. I was half a drink in when she arrived. I stood and we kissed on the cheek and I ordered her a cocktail. We sat smiling a lot at each other, not speaking much because the music and conversation was loud, also because what we had to say to each other was very intimate and this was not the place.
I called for the bill and paid it and we went out into the night, arm in arm. We received a few odd glances and suspicious looks but hey this is San Francisco, so anything goes. Hailing a cab, I asked her where to?
Italian? She asked, I smiled and said "Sure, do you have a favorite?"
"Driver, the Gold Spike in North Beach please".
We made googly eyes all the way there, shared a few soft kisses and all in all behaved ourselves, because it was obvious to both of us that our minds were elsewhere.
The restaurant was candle lit and we were seated at an intimate table for two off in the corner, which suited us both just fine.
I touched her leg under the table with her panties and she looked at me quizzically. "Are you missing something from last night? I asked.
"Where on earth did you find them? I looked high and low and decided you wanted a souvenir. Thank you Steve, they are one of my favorite pair. She took them and slipped them in her purse.
"They are so soft" I said. I love the feel against my skin."
She smiled widely and said, I know, that is why I bought them, they make me feel so sexy." She took a sip of wine and then bluntly asked, "Do you ever cross dress?"
I must have turned seven shades of red, I had never had the thought cross my mind.
Her hand was on my arm in a flash, " I am sorry, I embarrassed you didn't I?"
My silence was her answer.
Her hand found my leg under the table and she squeezed my thigh in a loving way.
"Are you new to the scene?" The way you took me last night, I assumed you were familiar with the ins and outs of ladies like me."
Again I blushed. " I , ugh, Well I , ugh!"
She held my thigh and said, "it's ok Steve, you are a wonderful lover and I have never been treated as such a lady.". She leaned toward me and gave me a sweet kiss on the lips.
"Well I guess I was so caught up in the other person, It never even crossed my mind to think of dressing myself. Of course a man my size would never find cloths to fit, so maybe it is just as well." I gave a soft chuckle with a nervous inflection.
"A tear came to her eyes and she smiled at me so sweetly. "Honey, if you would like to shop while you're here, I am at your disposal. I think all guys should have a few soft special things in their drawers, who knows when you want to be sexy by your self?"
"Jo, I called her, I am a former lineman, built like an Olympic weight lifter, how do you think I would look in frilly things...if they had such things in my size?"
She smiled and her demeanor picked up, "This is San Francisco, you can get any thing you want here, you just need to know where to look."
I suddenly had to admit the idea was a good one, who would know but the two of us and what could it hurt? I might take some things home and throw them away later but right now, it might be fun and it would be a trip to shop with her in such places as I could only imagine. I guess my smile tipped my hand because she said, tomorrow, the same place, I will meet you at seven and we will shop, I am going to buy you a few special things to take back from here as souvenirs, so you never forget me or San Francisco.
We kept chit chatting about our lives and how she ended up here and I ended up in Chicago and how special last night was.
We ate Chiappino and drank red wine by the carafe. Soon we were full and mellow and comfortable, so we decided to just go back to the hotel and get in bed. Well it was a great plan but once she slipped out of her dress, I was not so tired anymore. I have to admit I still had a craving for her cock, It might be because it was a new sensation but I think I liked it and I knew I would never sleep with out another taste of her sweet cum.
We slowly made love for an hour, she came twice, I came three times, I was just so excited by my new found life. We nestled in bed under the covers and whispered sweet nothings to each other for another twenty minutes before we drifted off to sleep.
I awoke with a raging hard on and the warm moist feel of her mouth surrounding it. I tried in vain not to cum right away, but she had me in her power. We snuggled a little and then she threw me out of bed and made me go to work. She was fast asleep when I left.
All morning I daydreamed about our date tonight, I realized I was so Horney and so full of anticipation I would never make it through the day, so I began to fake a cough and act sick. At the lunch break, I begged off and apologized for my illness and told everyone I had to go home and rest. It seemed to fly and I high tailed it back to the hotel where I got ready for our date. The seminar was over and I was relieved, so my last night in San Francisco was everything I could think of. I thought about Josephina and had to masturbate, she just excites me so much. Then I thought about the feel of silky women's undergarments against my skin and I had to beat off again. I had to admit that I was turned on by the concept of owning my own panties and bras and slips and also by having Josephina help me shop.
We met in the bar and had a martini apiece and then paid our tab. I walked out arm and arm with my new found love and felt like a child in the midst of his first romance. We hailed a cab and Josephina gave them the directions. We were let out in front of a non decrepit building and she paid the fair before I could react. This evening is on me she said and kissed me gently on the lips. We went to the door and buzzed one of the offices and soon a buzz answered us and we went inside. Five floors later we knocked on a half glass door and a lovely , extremely well groomed woman opened up and gave Josephina a kiss on the cheek and a hug. I was introduced and we went inside.
There were what seemed to be hundreds of manikins in all sorts of erotic under wear. Immediately I was aware the manikins were small and I am big and wanted to bolt.
Jo Held my arm and we continued inside.
"Steve most my clients are very large men, I don't want you to worry, the models are just that, models, I can fit you in most anything you see. My specialty is jocks and big men, so have some fun and shop around, it is your playground so to speak. Josephina called ahead and told me you were a special big man, so relax and make yourself at home, I can get you a glass of champagne if you like. I smiled and accepted.
Josephina kissed me long and deep and tender and said " Have fun babe, this is your night and we are the only ones who know what your doing.
After receiving my champagne, I sipped it and looked around and had to admit I was knocked out. I was in my own fantasy and loving it. I guess I am a sucker for slips, because I picked out five full length slips in three colors and then some bras and panties and later some lingerie. Josephina stayed back and let me work until near the end when she said, babe, you need a couple wigs. I realized she was right and went to that section. My instinct was to look at long hair, she waited patiently and steered me to short hair, telling me short hair looks much cutter with big bones and meaty faces. I tried several on and had to admit I was much more attractive in short hair. My champagne glass was never empty, so I was feeling no pain. When we settled up and got ready to leave, I was surprised how little I had spent.
I have another treat for you now, Josephina said. She hailed a cab and we went for ten minutes to a non descript neighborhood that was dark and deserted. She paid the cab and we rang a buzzer. Another very handsome woman answered and gave her a peck on the cheek as we were introduced. In side it was like a hair salon. Lots of stations and private cubicles. Madam Curry as she was introduced to me, looked me over and decided to call in a friend. They discussed me in Chinese I think, for a few moments and decided on my complexion and needs, the two of them pulled out
makeup and from time to time streaked some on my face and then argued in Chinese.
Eventually they gave me a package of makeup and a bill. Jo smiled and paid them.
We left and I was just about exhausted, so Jo hailed a cab and asked to go back to the hotel.
Back in the room, she made my face up. Produced a bag and debilitated my body hair and then asked me to shower and to avoid getting my face wet.. After I showered, my body was naked, nude as a new born baby. It felt great and when she gave me my panties' and bra to put on, it felt even better. She had me sit on the toilet seat added a couple breast forms and did my makeup, then she placed a wig on my head. Before I could move, she asked me to put on my silky slip. I did so and stood up.
She had a true genuine smile from ear to ear.. She grabbed my shoulders and turned me to the mirror and I almost fainted. I was a sight to behold. I was more woman than man, actually, quite a vision. I stared, she stared, we both stared and eventually I began to shed tears. I was a woman, and suddenly realized I had always felt this hole in my life.
I was amazed and Josephina was as well, she asked me to wait while she changed. She scurried off to the bathroom with her bag and I busied myself, posing in the mirror and finding myself vey sexually turned on by the results of the evenings shopping. I did profiles, and straight ion shots, I had to admit I never pictured a big ole off as myself as feminine and was quite taken.
Suddenly the bathroom door opened and Jo emerged in a male tux and her hair slicked back and smelling or cheap male aftershave. I was standing there flat footed. Wondering what was up when she said, "Wow babe, you are hot, Can I buy you a drink?" I was dumb founded and said yes! She approached and made us a drink and then put her arm around me, pulled me to her and kissed me deeply. I responded in kind, we French kissed for awhile. She continued to assume the male role and I grew more comfortable with the female role as the evening went on.. I had never considered the difference between the sexes and now I was s so taken by my mate, I got it. We kissed, she felt me up, she made all the moves and I got hard as a rock and at some point came in her mouth.
I guess my mind went from macho to femme in the act of love and I was in heaven. The silk against my virgin skin, was a real turn on and the feel o being the woman and not the man was very sweet and rewarding. We had sex at least three times in this manner, and I was drained as we went to sleep, her arm around me and my head on her chest. When we awoke. I looked at Jo and was afraid to ask her what was on my mind.
It was obvious she had something on her mind, some agenda. I stayed cool and let her approach the subject. "Steve?" She asked more than said. Babe, I like you a lot, in fact I am thinking I may be in love with you. You are the first man to take me as I am and treat me as a lady all the time and now we have discovered your feminine side, I think I could fall for you! Is this it? Will you get on that plane today and just leave me here?"
"God I hope not, You are my new world and I would be heartbroken if you did".
I sat there in a trance for moments, thinking how lucky she made me feel and how blessed I was to have her love but also how new this all was and how apprehensive I was. I must have made her feel like shit as I mulled it over and finally asked, babe, would you come to Chicago? She burst into tears and gradually shook her head in the affirmative. We kissed deeply and realized that we might be the ultimate couple right then and there.