SECRET DATE
My First Real Date,
By Joyce Devries, joyce_devries@hotmail.com
October 1986
Note, this a true story, some of the names have been changed, but certainly not the events of the days!, this is taken right from my diary entry of the time.
My (email) name is Joyce Devries and it was a real life adventure I will never forget, my first time I pleased a male as a woman with my mouth. I am 5'2", TV, live near Toronto, Ont., Canada, pass quite well as a woman and have done tons of "real life" things as a woman, but this was my first.
I am about to let you know of something that happened to me approximately 16 years ago, that to this date, my girlfriend at the time, now my wife will never find out about. It is for that reason that the following true story will not use real names, nor places, but all the details are true. I am a TV and a heterosexual one at that, but this incident, something for a brief period, changed my whole look on myself, and how I now treat women, and that is with a great deal of respect and admiration.
I was 20 at the time and was living in an apartment all by myself, I had no current girlfriend and since moving out two years prior to this date, I was totally engulfing myself into dressing and behaving like a normal female. I started dressing very early in life and like to call myself Joyce, I always thought I looked like one. I was about the same height I am now, 5'2", and still have the same long brown haired wig. I have about a 36B chest and loved to wear tight sweaters to show it off. I spent most of my time alone with a camera and videotaped myself over and over, I practiced walking, talking, sitting, eating, sitting, the whole thing. I would often go to malls as a male and just sit and watch females as they went about their normal activities, I would take mental notes and immediately go home and practice what I had seen.
For about a year after I moved away from home, I never appeared in public, but I always thought I could, as my look, walk, talk and dressing style was good. I would always go shopping for my 'sister' and 'girlfriend' and knew exactly what size to get, at that time I was a 12 dress, and 7 shoe, I found those out by accident. I had built up quite the collection, and always was fashion aware and bought many items that coordinated together and accessories that blended in well. Then one day I got the nerve to finally go out. It was a Saturday and the malls were full of Christmas shoppers and I was sure I could blend into the crowds.
I started by getting ready with a ritual I had become an expert in, I shave as close as possible my entire body, so that my skin was as soft as a baby. Next I pampered myself with a long, relaxing bath in scented bubbles, then powdered myself with a sweet scented powder. I then donned my wig, brushing and styling it to perfection, moving to my room and makeup table from the washroom, I applied makeup, bronze and light gold to my eyes, brown mascara, brown eyeliner, soft pink blush and a satin pink lipstick. Choosing my clothes for the day was rather tough as I wanted to appear so perfect yet, not too dressy. I chose standard undergarments, bra, slip, camisole, panties and nude colored nylons, I wore a loose, Flouncy jean skirt, and a light blue turtleneck and low, 2 inch heels. I grabbed my purse and slipped into my coat and walk down to a local mall.
Once in the mall, no attention was even paid to me, I expected to be looked up and down by everyone, but nobody even stared me down, oh except for a few guys and they gave me looks, but they were admiring, not laughing. I slowly lost my nervousness and sort of got a great 'high' as I walked around. I then decided to be like so many females I have watched in my 'staring' sessions and take a stroll into a popular ladies store, and lone behold I got the thrill of my life. While browsing through a rack of skirts, a salesgirl walked up to me and asked if I needed any help, well I was on such a high, I spoke in my practiced feminine voice and said, not really just browsing, she smiled and said, "just ask for me if you need any help, my name is Anne", and I said thank you and continued browsing. I spent the whole day in the mall, walking from store to store, looking at everything feminine, lingerie, dresses, skirts, stockings, I never thought it could be this good. I left the mall a changed 'woman' and went home to bask in my joy, and vowed that next trip would be to a bar on ladies night, and that I wanted to really see if I could prove to myself I was that convincing of a woman.
The big day arrived, I got off work early and came home to shave and dress, it was a Thursday night and I had Friday off. I wanted to be careful how I dressed and how I did my makeup, so I decided on a pretty black velvet skirt and a sheer feminine white blouse with the appropriate camisole underneath. My makeup was done almost the same as shopping, but because of the low light, I used black eyeliner and mascara and did my blush a little lighter, I also let my nails grow for the occasion and colored them the same shade as my lipstick. Along with the skirt and blouse I decided on wearing my black patent 3 inch heels and added a modest spritz of Obsession perfume.
It was 7pm and I left for the bar, it was in the same mall I was in the previous week. I sauntered around to the door and was greeted by a gentleman who addressed me, "welcome madam, hope you have a good time", and was escorted to a table by the waitress. I ordered only a salad and some drinks and sat by myself as the bar started to fill with very attractive girls and guys. Then it suddenly donned on me, I needed to go to the washroom, and that is one thing I was not really prepared to do. I was not going to spend the whole night in pain, nor was I going to leave the bar, so I grabbed my purse and headed for the washrooms.
As I passed the men's washroom, a chill ran down my spine as I could now hear my heels echoing down the hallway. I gathered my courage and swung open the door and to my surprise there was nobody in the washroom, and that was lucky as it was so small, only three stalls, a sink, and large mirror. I entered a stall and sat down to do my business, when the door swung open and in walked two other girls, I was in shock and didn't know what to do, I quickly did my business and pulled up my nylons and adjusted the front of my skirt. I then left the stall and noticed my lipstick was smudged, and thought it be better to adjust it in here rather than at my table, so just as I took out the tube and started to apply it. Then out walked one of the girls that came in earlier, I was petrified, but was relaxed when she smiled and said high and started to do the same as me. I left before the other came out of her stall, and as I walked back to my table I thought 'this is great, nothing can stop me now', that's what I thought.
By the time I sat back down, the time was 9pm, and most people had stopped eating and started drinking, including myself. I then thought it appropriate to stroll up to the bar and sit on a stool and listen to the music, my plan now was simple, to watch other people dancing and sipping on a few drinks before heading home, when suddenly I met Rick.
I was approached by a man, about 5'6", with black hair and a mustache, he was alright looking and I was a little nervous as he sat down next to me and started some small talk. After about two minutes I knew he was comfortable with me and I decided to enjoy the conversation. He asked my name, profession, which I made up, my likes dislikes and so on. I was so thrilled as now I was seeing what it was like on the other side of the coin. Rick then made the offer to dance and I accepted, I had never danced much with girls, much less with a guy while I was wearing heels, but the song was fast and everything worked out well. I even followed the lead of other girls on the dance floor, and placed my purse close by on the floor.
The rest of the evening was spent talking about likes and dislikes and I found myself making a whole new life for Joyce totally separate from my male side. Before I knew it the last call was being hailed and Rick like the perfect gentleman offered me a ride home, and like the perfect woman, accepted. The ride home was interesting, because I could see my male self in Rick's eyes, I knew he wanted to ask me out and I was hoping he wouldn't, but I had the line that I was seeing someone else all ready. Rick stopped in front of my apartment and I thanked him for the ride, he said it was no problem at all and felt quite secure as he made no moves towards me as we were departing. Then it came out, Rick said, "look Joyce, I've only known you a few hours, but would like to know you much better. My company is having their Christmas party this Saturday night, care to go?, I sure would like to escort you on my arm". I was shocked, a date?, mmmm I thought, what an opportunity, I had always loved to watch as girls at formal occasions really turned me on, so I accepted and he agreed to pick me up out front of the apartment at 6:30 the next night.
At first the idea was thrilling, dressed to the nines and being treated as the perfect lady, then it donned on me, what shall I wear?, my wardrobe was mainly casual and semi-formal, and this was sure to be a very formal occasion, so I decided, Friday would be a shopping day and I would find my perfect dress, as Joyce, not my male self. When I went to bed, it was as usual all dressed in lace and satin in a sexy teddy. As I lay there I thought of what lie ahead and dreamed as I slowly relieved myself through the satin material, and that as when the first thoughts of actually what might happen if things got carried away might do. Mind you they were not entirely disgusting thoughts in the frame of mind I was in.
As the day begun, I started to get ready, I decided to go for the 'just from the office' look and found a conservative yet pretty blouse, it was cream colored with a lace colour and decided on a straight 'A' line black skirt. I wore black pantyhose, some jewelry and my patent black shoes that I wore the other night, with the 2 inch heel. I took my time and did my makeup very soft and highlighted all my best features, I was also very light on the perfume. Colours I used were my usual for dressing for 'work' and they were soft pink on the upper lids and light blue on the lower lids, brown mascara, and brown eyeliner. I did my blush very soft and used my favorite light pink colored lipstick. I grabbed my coat and purse when I was ready and headed out the door.
Once inside the mall, I was not even nervous, mind you it as not as crowded as Saturday, but still, I felt at home and relaxed, I even got a few approving smiles from other women, who were out from work. I made my way to the cash machine and withdrew, $150, I thought that would me more than enough for my dress, I was about to realize how wrong I was. I had a good idea on what to buy, it had to compliment my obvious small hips, even with the padding, and have a high collar. I flipped through a few fashion magazines at home before I left and was sure I knew what I wanted.
The first store I entered I was immediately aware that the prices were going to be high, I was greeted immediately by a salesgirl and found the look inside to be very elegant. I was greeted then asked what I was after, I explained that I had a Christmas party to attend and that I was looking for a gown that had a high collar, but one thing I forgot, colour!, one thing I have found to be so important to females. I then decided on basic colours and nothing too flashy. I was then asked what I intended to spend and the salesgirl smiled and politely said that I would not find anything like that in that particular store, but she was helpful and offer a couple of stores as solutions. I then thanked her and headed off to one store she had suggested.
Upon entering that first store, I could tell I would probably find what I wanted, I had a feeling. Now used to the salesgirls, I smiled back as a well dressed girl in her early twenties came up to me and ask if she could be of any assistance and readily agreed. She was beautiful and wore a short blue shirt dress with heels almost the same height as mine. I explained to her all the details and she immediately lead me to a rack of dresses and started pulling out different shapes and styles. I was having a great time and was in even more awe as she pulled out a black velvet dress with a satin bow around the waist. She could instantly tell I was interested and said, "come on, let's see how this looks on you". The dress had a peplum style skirt, which ingeniously hides your hips and a high collar, as not to expose your breasts.
As I entered the change area, I was thrilled and very excited and I started to undress as the salesgirl carried on small talk. Then the next problem, I did not really have many dresses with zippers and was having problems with the zipper. She asked if everything was OK, I said the zipper was a bit of a problem and she asked if she could help, I accepted of course and as I appeared from the dressing room she asked me to turn around and proceeded to do up the zipper. The dress felt great and the salesgirl was complimenting me and said how it really pampered my figure. As I stared at myself in the mirror, I could see she was right, the padded shoulders were making my waist appear small and it seemed that I had a sexy figure. I was thrilled and decided right there and then to buy the dress. The salesgirl kept showering me with compliments and helped me by undoing the zipper at the back. As I dressed the salesgirl kept on talking to me and wondered what heels I was going to wear with the outfit, heels?, what was wrong with the ones I had?, I then decided to ask her what she thought best, and she suggested that a pretty 4 inch pair would compliment my stature and make my legs better looking. I thanked her and after shelling out $125 for the dress left the store and headed for a shoe store. I found several in the mall but really wanted one with a female attendant to serve me, and I found one with a pretty blonde girl in the store.
I entered the store and glanced at the prices and was somewhat impressed. I expected higher prices. I was greeted by a young lady who introduced herself as Michelle and offered to be of assistance. I explained that I was shopping for shoes that matched an outfit I had just bought, and Michelle then suggested that she see the outfit to get a better idea as to what would be best. After looking at the outfit, Michelle suggested the same as the girl in the dress shop, a 4 inch pair of patent black heels and proceeded to measure my foot. I cannot tell you how excited I was as Michelle fondled my stockinged feet in the measuring device, I was afraid my gaff on would not hold as I could see right down her blouse and could see a lacy bra covering two lovely breasts. "There, you are an 7 with medium width, I'll be right back", said Michelle as she finished her measurement.
About one minute later she returned and removes two beautiful, yet high heels and proceeds to have me slip into them. They felt fantastic and as I stood. I am just a tad wobbly and Michelle suggests a few practice steps are necessary, and as I walk back and forth I can feel my calf muscles start to bunch up and realize that my walk is much more sexy. All the time I am walking, Michelle is asking how they feel and I can only say great. I then sat down and Michelle removed them from my feet and I said that I would buy them and Michelle smiled and said, "well if you are going to be wearing these soon, I suggest you practice, they take a little getting used to OK". I said OK, and proceeded to slip back into my low heels, and went to the cash and paid.
I left the store feeling great and on may way out decided to check out one of the little jewelry store to see if there was in fact something to match the outfit and there was. I immediately spotted some fake diamond clip on earrings and matching bracelet, they were perfect, and the salesgirl complimented me on my purchases and I headed for home.
I spent the rest of the day dressed and relaxed around the house dreaming and wondering about what the next night would be like. I spent Saturday, making sure I was perfect, I must have shaved about four times just to be sure and watched all my tapes to be sure that I was going to be the perfect date for Rick. Around 3pm, I decided that it was time to get ready for the big date and proceeded to take a long hot scented bath, one that both relaxed me and allowed for my body to absorb all of the lovely smells.
Once finished in the bath, I dusted my whole body with my body powder, leaving me smell fresh and feminine. Next I made my way to the bedroom and proceeded to don my lingerie, first my special and most favorite, black lacy padded bra. Following that there was a gaff, the matching panties to the bra, a dark blue full slip and I thought about my choice of pantyhose versus garters and stockings and decided to go with the latter, and finally my silk housecoat and next I was ready for the makeup table.
I applied my makeup darker than usual with dark blue on the lower lids and a shade above my normal pink, on the upper. I applied my blush heavier than normal, making sure my cheeks were visible and chose a bolder colour of pink lipstick for the overall appearance. I was all finished my makeup application, when it donned on me, how an I going to do my dress up?, it was easy in the store, I had a hand, but that didn't stop me, I came up with the idea of tying a string to the zipper and doing it up and simply cutting the string off when I was finished, and amazingly enough it worked, although I lost a few hairs in the process.
I then slipped into my new heels, which for the first while were killing my feet, but the nervousness calmed that pain. After that I donned my jewelry, spritzed myself with some obsession perfume (Rick loved when I wore it the other night), packed my purse with all the necessary makeup and that was it, I was ready. So there I stood, staring at myself in my full length mirror and I looked fantastic, even I would want to date me, then the same thought that haunted me the night before came to mind, was I too good looking?, what would Rick really want from me, and more importantly, would I be so aroused or mystified to go along with anything?, I was scared at that point but like everything else decided to play it as things came. I then sat down, relaxed and waited for the time to come, and around 6:25, I donned my winter coat, and grabbed my purse and headed down to the front lobby to wait for Rick.
Rick was promptly on time and made a point of coming out of the car and escorting me to the passenger side, were he opened the door and made sure I was comfortably seated before closing it. Rick then scurried around the car and jumped in, he complimented me a few times in a row at my appearance, I was taken back and think I managed to blush. Rick was such a gentleman, he presented me with a corsage and I pulled my coat back and allowed him to pin it to my dress. I was already in seventh heaven before the date really had begun, I thanked Rick and then thought, what would a real girl do if she in my shoes. I very quickly, went up beside Rick's cheek and kissed it lightly, not sexual or anything, just light and friendly, Rick smiled then put the car in gear and were off. Rick was wearing a blue sport jacket and white shirt with a red tie, he also had on Grey pants and good looking shoes, he wasn't exactly Burt Reynolds but he was ok. On the way we chatted about different things and just generally discussed the weather and music I was into etc., Rick also once again, complimented me on my dress and said that I would really like meeting his friends and I looked forward to it.
When we arrived at the hall, Rick quickly made his way to my door and opened it, just like the perfect gentleman, and I slowly slid my legs across keeping my knees together and accepted his hand as I left the car. I felt great walking to the front door, I allowed Rick to escort me by grabbing his arm. As we got closer to the door I could hear the clicks of other girls heels and felt that much more feminine as I knew mine were part of the 'choir'. Once in the door, Rick took my coat and went and checked them in, I was left sitting just outside the door to our banquet room and got a good look at the other girls walking in and just about died. They looked fantastic and I fit right in, I got a few smiles from some and hellos from the men.
When Rick returned he offered his arm and I accepted and away we went. Rick found his friends and I was really nervous as I approached the table, but I had come too far to turn back and I smiled as I was introduced. There were three of his friends there and they all had dates, I was seated next to one, Carol, as Rick went and got me a glass of white wine. Carol immediately started talking to me and I was even more nervous as I had never really talked 'girl' talk with another girl, but I seemed to make out ok. She asked pretty small-talk style of questions, including how long have you and Rick been together?, I managed to answer that one without too much difficulty.
Rick then returned with the drinks and we sat and sipped and talked, I was having a great time. After awhile Carol grabbed her purse and said, "care to go to the washroom Joyce?", at first I was thinking?, I don't have to go?, but then I remembered always seeing girls going to the washroom in pairs, "tag-team", we called it and then grabbed for my purse and said, "sure". The trip to washroom was fantastic, the washroom was big and very well lit, especially the makeup mirror area, and all the girls in the washroom were all dressed up and some were definite knockouts. I went to the stall and went the best I could and when I came out there was Carol at the makeup mirror and I walked up to the counter and joined her. Both her and I were applying lipstick and I felt fantastic, we then left and headed back to the table, and at this point I was getting very aroused.
Once back at the table we sat and chatted, then ate dinner and killed two bottles of wine, which made me rather lightheaded. The music started and once that did, Rick asked me to dance and I of course accepted. The dancing was different than before, this time, it was either the wine or the clothes, but I truly thought I was a female and was feeling quite aroused towards my date. The song was slow and it seemed to go on forever, and Rick hugged me gently then started to caress my velvet covered backside and I actually enjoyed it, I made no attempt to stop him and just hugged him even more.
Rick then continued to caress and I was getting quite aroused by his touch and allowed him to continue, although my own sex had started to harden and I could feel it pressing quite hard against my panties and gaff. I did my best to push slightly away from Rick in the crotch area to avoid being found out. The petting and caressing of my rear was the first step and as the night and the drinks flowed along, so did Rick's advances. I made two or three more trips to the washroom and one of them Carol joined me and at the makeup counter we chatted and she mentioned that Rick and I make a cute couple and that Rick never really has had a girlfriend before.
I left the washroom and returned to the table, it was getting near the end of the night and I was glad because my feet were just killing me. I was about to suggest that we leave when a really slow song came on and Rick asked to dance again and I accepted. Within 2 minutes after we started dancing, Rick had his hands on my rear again, this time I reciprocated and then about 2 minutes later, looked up at Rick and stared at him, he was lost in thought, staring at me like I never will forget. Then I don't know who moved first, but our heads merged together and he kissed me, gently and romantically, I accepted and then as if it was natural, lower my hand to the front of his pants and 'accidentally' caressed his now very hard cock. I was lost at this point, I started reacting to feelings I had never had before, I was drunk both from the alcohol and from the lust and thrill of being an attractive female.
After the song Rick suggested we leave and we finished our drinks said our good byes and headed to the car. Once inside the car we kissed again, this time harder and longer, then the fateful question, "Joyce, care to come back to my place for a drink?", and that is were I drew the line, I would not spoil a whole evening for Rick nor place myself in an danger, so with my 'new' personality, offered Rick a solution, and that was to find a quiet place to 'park' and he liked the idea.
He took me to the favorite area make out spot and shut the engine off, he then suggested we go into the backseat to get more comfortable and I agreed. Once in the backseat, Rick moved quickly to have me in his arms and kissed me passionately, I graciously accepted and made a point of gently caressing his cock, which by now was so wet that I could feel it through his pants. Rick was enjoying my breasts through my dress and then suggested we get more 'comfortable' and that is where I drew the final line. I felt sorry for Rick that I had lead him on so long and that I never could live up to his date and felt like I really had cheated him and made a fool of him. I explained that I was on my period and that if he liked I could relieve him in another way. I was scared and very nervous at this point and as it turned out Rick was lost at what I was talking about and then I committed myself to giving Rick his first and me giving my first blow job. I laid Rick back and slowly undid his belt and pants, all the time telling Rick to relax and enjoy. I undid the belt then the pants and pulled them off, and staring at me was a pair of white underwear and a large rod holding them out like a tent.
Rick was nervous as I slid the underwear off and lone behold I was staring a rock hard cock. It was not that big and I proceeded to lick the head while caressing the balls. This was all very new to me, yet I had watched enough videos to know the technique. Soon Rick was enjoying the caressing and was moaning and squirming his hips. I then took the whole cock in my mouth and began to pump up and down, and all the while Rick was caressing my hair, I actually felt quite feminine and started to enjoy the sensation. Then Rick started to tense up and his cries became louder and louder, I knew he was going to cum and braced myself for it, he shot a huge load and I swallowed each and every drop, I was actually quite proud. Once Rick had finished I licked him clean and came back up to kiss him, he didn't like that idea too much, but was grateful for the relief. We chatted a little more about the future and I had always told him that I had a steady boyfriend who was out off town, and started to give him the idea that this was the be all and end all of our relationship. Rick then drove me home and dropped me off, not before a long a lingering goodbye kiss.
I then went up to my apartment, kicked off my shoes, managed to get out of my dress then put on my favorite teddy and headed to bed were I relieved myself onto the silky material and thought about the days and nights events, and fell into a blissful sleep.
If you liked this true life adventure, let me know, maybe one day it might be you?
Joyce_devries@hotmail.com