MF MM transexual story (1 of 2)
story by TV
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 that was fun and exciting, I was approached at the time by a woman that got my name and address from Tapestry magazine, the TV/TS magazine. 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 really a fun and exciting time. The following is taken from my diary entry at the time.
April 1988
A few months ago, I got a letter from a genetic woman that was quite the letter I must say, and included in the letter was the thought of an idea she had and a picture. Her name was Debbie, and was a year older than I. She was attractive, not "supermodel" attractive, but had a cute face, and shoulder length straight blonde hair. She went on to describe her particulars and wanted to know if I was interested in helping her give her boyfriend a special birthday present. She told me that if I was interested to mail her back and we could go from there. I sent her a letter with my own picture and particulars and due to the fact she lived in the city next door, I offered her the chance to call me, and gave her some times when it was best to call. About three weeks later on a Friday evening around 8pm, I heard the phone ring and let the answering machine pick it up, and it was Debbie, she started leaving a message but I quickly picked up the phone and in my feminine voice started talking with her.
Right off the bat she told me how sweet my voice sounded and it certainly matched the picture I had sent along. She said that she could not talk long, as her boyfriend was due home any minute. She thanked me for the interest in helping her surprise her boyfriend on his birthday. She said that she did not want to talk about the details over the phone and wondered if I was available to get together with her for lunch and we could talk. I told her that was not a problem as my work schedule was flexible, and to just name the day. She explained that she was a real estate agent, and that her schedule would somewhat be determined by her clients, but that the following Friday was free so far and generally those are slow days. So we penciled in the following Friday and she said that she would call, before we hung up I explained to her that I do not drive when I am dressed and she would have to pick me up. She was surprised that I would go through the trouble of getting dressed, however, thanked me for being so considerate, and that she indeed would pick me up. I gave her my address and she told me that she should know by the Wednesday before if things were a go.
When I hung up the phone, I immediately started wondering what the heck I was going to wear?, with only a couple of fancy skirts, a few formal blouses, and four formal dresses, I really had nothing to wear for a lunch meeting. I tried on a few of the outfits that I did have and the only thing that looked right for a lunch meeting were some nude pantyhose and a pair of kid leather 2 1/2" black pumps. I gave the idea a thought of going out dressed up shopping, but realized that everything I had in my closet was not appropriate for that either!. As the days lead up to the meeting came, I decided that if on Wednesday Debbie called, I was going to go "shopping for a birthday present for my girlfriend".
I came home from work on the Wednesday evening and there was a message on the machine from Debbie, telling me everything was a go and that she would pick me up a 11:45am and at that time we would pick a place to go for lunch. She also asked to bring any other pictures that I had, as the one I sent her was "darling". After listening to the message I realized that I was going shopping, and that day was probably the best time. Then it struck me, I had no clue what my size was, as all of the clothes that I did have, an ex-girlfriend got me and she did all of the shopping!. I checked all of the tags and found for the most part I was an 11/12, and measured my waist and knew what the size was. After dinner, I had a stiff drink to gather my courage and headed to a local mall to find something appropriate to wear for the lunch meeting.
In the mall was a ladies store called Reitman's, I always loved walking by there and seeing all the lovely clothes. I got to the mall and headed right for Reitman's, and as I walked in and started looking around, a cute blond teenage sales clerk, in a denim skirt and white sweater came over and asked if I needed any help with anything. I blurted out that I was shopping for a birthday present for my girlfriend, she did not even blink and asked me was there anything in particular I was looking for?. I told her a skirt and a top, then she asked me a question that I had to pause and think about, she asked, "is it for work or something more casual". I then thought about Debbie and the fact she was a real estate agent and that she would most likely be wearing something more appropriate for the office rather than casual. I told her it was for work and she lead me to one area of the store that had some more dressy skirts and blouses and such. She asked me if my "girlfriend" had any favorite fabrics she liked to wear?. I had no clue what she was talking about, and she could see it on my face and then said, "you know, cotton, leather, suede, polyester?", always having a soft spot for leather or suede, I quickly said leather or suede. She then took me over to some darling looking light brown knee length suede skirts, and asked what size, and I told her 11/12. She pulled one out, and said, "these are in style now and perfect for the office, I know the exact top to go with it".
She lead me over to a rack of sweaters and pulled out a red turtleneck, and asked me if my "girlfriend" ever wears turtlenecks, and I of course told her yes!. She said, "great, then if there is nothing else, I'll take care of you up at the front". As she rang in the skirt and the blouse, she informed me that both were on sale, and then asked if my "girlfriend" had any red dress shoes. I told her I did not think so, and then she suggested that I might go to the shoe store across the hall in the mall and see if they had any red dress shoes, as it would "really set off the whole outfit".
I thanked her and as I left the store, decided to take her suggestion and went across the hall and entered the shoe store and started looking around. The sales girl was busy with another customer, but I found a pair of 2" red pumps that matched the colour of the sweater perfectly. About that time the sales girl came over and asked if I needed any help, and I explained that the girl at Reitman's sent me over to find a pair of red shoes that would match the outfit I just bought for my girlfriend for her birthday. She asked to see the outfit and she complimented me on a good choice and suggested the same pair of red pumps that I was looking at, and then asked me my "girlfriend's" shoe size, and that I knew, and told her 7. She went in the back and then I met her at the counter and I paid for the shoes, and as I was leaving she said, "thanks, and I hope she enjoys them", I smiled back and told her, oh "she" will.
When I got home I immediately stripped and changed into some nude hose, a bra and the new outfit, I left the tags on in case it did not fit and lone behold it was perfect. The skirt fit at the waist was perfect and the length was right at or just slightly below the knee, so it was conservative and the turtleneck was perfect and had shoulder pads to help make my shape look nicer. I then slipped into the new red pumps and it was so perfect I almost cried, I certainly looked like a woman ready for the office!, I could not wait for the lunch meeting on the Friday.
Friday came, and I took the whole day off work to make sure I would look great for when Debbie came. I started the day off with a long shower and made sure my body and my face were "squeaky clean" and lounged around until 10:30am and then started to get ready for Debbie to pick me up.
First was a matching satin pink bra and panty set that was my first I ever got, next came the sheer nude pantyhose that set my legs off perfectly. I then moved to the bathroom and started on my makeup, which I was really careful with as it was going to be a daytime meeting and I was so used to applying heavier, more formal makeup for the more formal clothes in my wardrobe. I applied my eyeliner really thin, and did my eyelids with a light mauve colour, then a coat of mascara, really set my eyes off well. My blush was really light, just to add a little colour to my cheeks, and finally a light reddish pink lipstick set the makeup off perfectly. I put on my "hair" and fluffed and combed it so it looked perfect. I checked the time and saw that the time was 11:30am, only 15 minutes to get dressed and final touches.
I spritzed myself lightly with Halston's perfume on my wrists and behind my ears and then moved back to bedroom to get dressed. I slipped into my outfit and heels and then grabbed a pair of long gold dangly earrings and put on my watch and headed to the mirror to see how I looked. I pulled out a new gold anklet that I recently bought and slipped that on my right ankle, then went back to the mirror and said, "perfect" to myself. I took my mini photo album and packed into my purse and just as I finished doing that, the buzzer to my apartment went off and when I answered it, it was Debbie waiting for me downstairs, and she told me she was parked out front waiting. I slipped on my long winter coat slipped it on and went downstairs and met Debbie in her waiting car.
I opened the door and she immediately complimented me on how pretty I looked, I returned the favor and sat down in the passenger seat. Debbie had a cute face and the way her blond hair framed her face made it look so soft. With her jacket on I could not tell how big her breasts really were, but they certainly were not pushing out her blouse. I had guessed right, Debbie was dressed in a lovely blue business suit, below the knee, with a nice blazer to match, with a pretty cream blouse, I would later see that she had on black heels, almost the same height as mine and sheer black hose.
We right away decided that a roadhouse just up the road from my apartment was where we were going to go for lunch and she proceeded to drive there. We made idle chat for the short ride there, but she did make mention that she loved the smell of my perfume and asked what it was, when I told her she mentioned that she would have to pick some up sometime.
When we got to the roadhouse we walked to the entrance and I loved hearing our heels click together as we walked. I noticed we were almost the same height even with our heels on. Once inside we waited for the hostess to come and escort us to our table. We had just made it in time, before the lunch crowd and we had lots of choice of seating. When the hostess came, Debbie took the lead and asked for a quiet booth as we had some business to discuss. The hostess then said, "right this way ladies" and we were lead to a booth near the back of the restaurant, business to discuss indeed!. Once at the booth, Debbie slid in and I took off my coat and hung it up and right away she complimented me on how well I was dressed and how my "fashion sense" was perfect, and that she loved my accessories, especially my anklet!. I smiled back and thanked her and slid in to my side of the booth.
The conversation was cordial and general as we waited for our waitress and she asked all the "usual questions", how long had I been dressing?, did I have a girlfriend?, when do I dress?, etc. She kept saying how if she had not known, she would not believe I was not a genetic woman. I blushed over and over and thanked her, and when the waitress finally came, and I heard the lovely words, "and you will have mam?", I ordered a glass of white wine and a house salad, and smiled over at Debbie, she placed her order and we were alone again.
After we placed our orders, the real interesting conversation started, about what she was really planning for her boyfriend's birthday. She went on to explain that they both lived at home and that for his birthday she wanted to rent a hotel room so that they could have someplace quiet and romantic rather than trying to make out in the back seat of his car. She planned to take him out to a fancy restaurant, get herself all "dolled" up and then after dinner go back to the hotel room for some romantic "fun". I smiled back at her and asked, "so what is it you need from me to make his birthday special?".
She just smiled and toned her voice down and leaned over the table towards me and I did the same and here is what she said, "I want you to be his 'present'". I smiled and said, "in what way?". She then bluntly asked, "are you gay?", I answered, "depends, I consider myself a woman when I am dressed like this, and I am attracted to other females, so I guess the answer is yes". She sat back and smiled and took another sip of her drink and I could see were she was going with this. She then leaned forward and again bluntly asked, "well, as a woman than you must have had some experience with men in the past?", I gave a little smile back and said, "once". She smiled big and said, "no dear, you are BI, just like me, I too like women and men". She then said, "would you do it again?", I told her if the occasion was right I might. She then smiled wide and asked, "is this occasion 'right'". I smiled back and told her, "how can a girl resist getting all 'dolled up' and taken out for a romantic evening, so maybe?".
After that conversation, she went on to explain that she and her boyfriend had been together for only 8 months and that one night in the heat of passion she let it slip that she had sexual encounters with women in the past. She also told me that not only did he go wild sexually, but that for weeks afterwards he was begging to see her with another woman, just so he could watch that woman lick her to orgasm. He eventually stopped bugging her but every once in a while he would bring it up. Debbie told me that the last woman she was with was a few months before they started dating and that she thought his birthday might be the time to have another encounter. Also she said that it would turn her on to no end to watch another woman give a blowjob to her boyfriend while she sat back and watched and masturbated.
I was confused at this point, and asked, "so why me?", as I explained to her that there was probably tons of BI genetic females out there that would fit the bill. She had a big smile and explained that she thought her boyfriend had a "thing" for she-males, as she found a video tape under his bed one day when she was at his house cleaning up. I asked her if she knew what the difference between a she-male and what I was, a TV. She thought she knew and I went on to explain that I had no desire to get all dressed up and have some male "suck me", if we were to proceed my panties had to stay on no matter what happened. She agreed and after meeting me and talking with me she understood how feminine I was, but still wanted to move forward.
Debbie proceeded to tell me her plan, basically, she would surprise her boyfriend, Carl, with me in the hotel room, then we would go to dinner, the three of us, then back to the hotel room for some romantic, erotic fun. The logistics still had to be worked out, and as the time got closer, Debbie told me she would be in contact with me to work out the finer details. When she was done I just smiled and licked my lips and said the plan sounded "delicious".
Lunch arrived and we carried on more small talk as we ate, then afterwards I excused myself and grabbed my purse and headed to the ladies room. I did my business and applied another coat of lipstick and joined Debbie back at the table. She smiled as I sat down and said, "I cannot believe you?, you use the ladies room and everything?, even knowing to freshen your lipstick?!". I smiled back and said, "well I cannot simply walk into the men's room in a skirt and heels and touch up my lipstick!". She shook her head and smiled, then excused herself and used the ladies room, leaving me to wonder what I was getting myself into.
When she returned from the ladies room, I noted she too had touched up her lipstick and she smiled at me as she sat down. She stared at me and said, "so are you still willing to be his present?". I just smiled back and told her as long as my conditions were met that it sounds like a fun and exciting time. She grabbed my hands and smiled wide and said, "thank you" over and over again. She told me he was a great kisser and that I was in for a treat!. She sat back took another sip of her drink and said, "now the fun starts, all of the careful planning to pull it off". His birthday was the second Saturday in March, so we had a few weeks to set things up and I told her if she needed any help to just ask and she said she would.
I remembered the pictures and pulled the album out of my purse and handed it to her, telling her there was only a handful that my ex - girlfriend took and I hoped she liked them. She was looking over the pictures and could not stop complimenting me on how well I looked and the fact that most of the blouses and skirts were more pretty than anything she had in her closet. The last three pictures, was when her face lighted up and her eyes grew bigger, she obviously came to the formal dress pictures. She flipped back and forth through them, fixated on them, then looked back up and me and said, "oh my God, those dresses are gorgeous!, even I don't have one as pretty as those in my closet!". I told her I had a new one that I bought from the Fredricks of Hollywood catalog but did not have a picture of me wearing it, and showed her the clipping from the catalog. She just smiled big and said, "I was going to ask you what kind of dresses you have, but girl, that is the one you are wearing for Carl's birthday. Don't get me wrong the other dresses are really pretty, but this one oozes sex, he will probably cum in his pants when he sees you in this one".
The dress she was referring to was a Frederick's of Hollywood, hunter green number, crushed velvet, figure hugging and really short, the bodice and the rest of the dress was crushed velvet but the sleeves were long and lace, there was no back to the dress, it was wide open. With all of the right padding the dress looked like it fit me perfectly and it certainly looked hot.
I told her I had already accessorized the dress with 4" sparkly silver heels and some long crystal and green earrings, a matching bracelet, and a small sparkly silver clutch purse to match the heels. She was impressed that I knew about things like accessorizing an outfit, she smiled at me and said, "already chose a lipstick as well?", I told her "of course, what outfit would be complete without that?". We both laughed and she went on to ask me about the 4" heels and that how could I walk in them, after all they were, "come fuck me" heels. I told her that I usually wear those and one other pair of 4" heels all the time around the apartment, sometimes all weekend long and am quite comfortable with them. She shook her head and smiled and told me that the highest she had ever worn for an extended period of was 3", and even those killed her feet, and that I was "something else".
By this time, the restaurant had started to thin out from the lunch crowd and we continued our conversation and sipped on our drinks. She then told me that if I was going to wear the dress she liked that she was going to be going to the ladies boutique in the mall near her house and get the "little black dress" that she had been eyeing for some time. She described it as a figure hugging dress much like mine, strapless with little spaghetti straps and maybe a little shorter than mine. The dress was $145 and she was reluctant to get it, but after seeing what I was going to be wearing she decided that she was going shopping later today and get it. She also mentioned that she just might go and try and find a pair of 4" heels just so that I was not outdoing her on the night of the birthday. With outfits somewhat set, we talked about what kind of hosiery we both were going to be wearing, I told her I already tried my dress with a garter belt and stockings as the dress was too short, so it was ultra sheer pantyhose for me. She just smiled and said, "my you think of everything, I suppose mine will be too short for stockings and a garter belt?", I just smiled and said, "if the dress is definitely shorter than mine, then yes".
I took one last trip to the ladies room, did my business, fixed my lipstick and as I came back and sat down, Debbie was settling up the tab. Once that was done, she said she had to make a trip to the ladies room and to meet her at the front door. I slipped on my coat and headed for the door to wait for Debbie and about 2 minutes later she came back and smiled and me and said, "ready to go?", I agreed and away we went to her car. As I slid into the car I could feel something between Debbie and I, a kind of "electricity", my coat was open and my suede skirt rode up completely by accident as I did not tuck it under properly as I sat down in the passenger seat. I tried to fix it and Debbie just smiled and grabbed my arm and said, "no need to worry Joyce", I sat back down with my thighs very exposed, almost to my vagina.
The car ride home was definitely different than the ride to the roadhouse for lunch. As Debbie drove she gently caressed my arm up and down and eventually her hand ended up in mine, she squeezed it and looked over at me at smiled. She then softly said, "well if we are going to be lovers in a few weeks, perhaps we should get to know each other a little more before then?". I smiled and started to think what she had up her sleeve and she asked if I was "busy the rest of the afternoon?", I smiled back and told her I have the whole rest of the day off. We were about 2 minutes away from my apartment and I started to get excited, and her pager went off, damn!, she looked at it and told me it was one of her bigger clients and we would have to cut things short. I was disappointed, but was encouraged when she drove by the driveway of my apartment and then found an out of the way parking lot at the back of the building.
She pulled into the secluded back corner of the lot and turned off the car, and all the while still holding my hand. She then looked over at me and slowly caressed the side of my face with her other hand and looked me in the eyes and our eyes locked together as she continued to caress my face. She then softly said, "I was hoping to spend some special time with you this afternoon, you look so pretty and smell so delicious, and your legs are so pretty, it would have been a treat". Our heads then slowly moved together and we gently kissed, then she flicked her tongue out a little and I followed her lead. As we kissed she started caressing my breasts outside of my sweater, I reciprocated and gently caressed her breasts through her silk blouse. Her nipples were pushing out through her blouse, and I concentrated on them. She then broke the kiss and said, "my your breasts are cute, just like mine, a full A cup, and Carl always says, more than a mouthful is a waste, he is going to love yours, just like he loves mine". She commented on how lovely my lipstick tasted and wanted to know if I would be interested in switching lipstick and perfume for the evening of the date, as it would drive Carl nuts if he new it was mine. I said that would be great and she apologized and said that she really had to run and started the car and drove me back to the entrance to my apartment. Once back at the entrance to my apartment we gave each other a quick kiss and I left the car and went back upstairs, relishing a wonderful experiencing.
Over the next few weeks, Debbie would call me every Tuesday and Thursday evening, when she knew her boyfriend was playing hockey and we would talk for hours. We talked about everything from sex to fashion and work, we were really beginning to build a friendship between us. On the Thursday of the week that we were to get together we had a 4 hour conversation, she told me all of the final details of the Saturday evening that were set. She also told me that she broke down and bought a pair of strappy 4" black heels to go with her dress and she had been practicing so she would not break her ankle on Saturday night and had no clue how I walked in them all day long.
These are the exact details she told me about, Debbie would go and check in at the hotel and pick up two keys and arrange things in the room. She would then come and pick me up, around 5:30pm, ready and dressed and give me one of the keys and drive me to the hotel. She would then drop me off, and would then go to her house and dress and get ready for Carl picking her up at 6:30pm, dinner was set for 7:15pm. Her house was only about 10 minutes away from the hotel and told me that I should be waiting for a single ring of the phone indicating that they were on the way. Once they arrived, Debbie would have Carl close his eyes and she would lead him into the room, and I would be standing in the middle of the room with a "Happy Birthday Carl" sash on, she would tell him to open his eyes. I was then to sing Happy Birthday to him in my sexiest voice and then move to him and kiss him. The plan was then to leave for dinner, and then after dinner come back to the room for some romantic fun, Debbie had even gone out and got us matching red satin and lace peignoir's to change into when we got back. The big question we both had was, when do we tell Carl about me?, at what point?, we decided to leave that to the events of the evening and what would happen and when. The Thursday evening was the last Debbie and I talked and I told her I would be ready to go for the Saturday when she came to pick me up.
I tried on the dress for Saturday night several times over the next couple of days and since I had never worn it outside of the apartment, I realized that with the wide open back, I could not wear a bra at all!. I thought and thought about what I could do and decided to sew a couple of breast pads into the dress to give myself a little more shape and it would look natural. I already had the breast pads and on Friday evening I sewed them in and got into all of the pieces of the ensemble for the next evening. I looked hot, I had to admit it, even I would have gotten excited if I saw a woman that looked like I did.
Story posted by TV
on Friday, April 16, 2004 @ 21:17:19 PDT
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