This is a work of fiction. Any resemblance to any person, or incident is strictly coincidental.
My Wife's Cross dressing Fantasy 3
Then my wife looked at me and said “Happy anniversary darling.” How did she know the effect this experience would have on me. I was changed forever. It was such a wonderful experience. She deserved that I come up with something just as exciting for her, but what?
I thought and thought, but I couldn't think of anything to equal what she did for me on our anniversary. The days went by and I had nothing, but then, I remembered. A couple of months ago we were talking and she told me that she missed her friends from where we used to live. We moved to this city, because three years ago I got a promotion and was reassigned here and she was unable to find a girlfriend to go out with. She had Kim as a friend, but Kim lived almost two hours away and they could not be spontaneous together.
Before I go much further let me tell you about my wife. She is strikingly beautiful. She is five feet eight inches tall. She is slender, but not skinny. She has long legs, coal black hair that extends past her shoulders, a light complexion, steel gray eyes and a set of 38 D breasts. Every man who sees her wants her. As if that weren't enough, her personality is such that she can melt your heart with just a word.
I was putty in her hands and I wanted to make her happy. She needed a girlfriend and I was going to find one for her, but where to find someone like that? I mulled it over in my mind for a few days and finally I came up with the idea that I could become her girlfriend. I would have to prepare myself a lot more than I have in the past, but I was sure I could pull it off.
I dressed up twice in the past, and both times I was just a guy in drag... a sexy guy in drag, but still I didn't fool anyone and my wife was not going to go out with a guy in women's clothes. Not even if he is her husband, so I had to do something a little more involved than just dressing up.
My wife gets her hair done by a woman who is a transsexual. I went to her shop and laid out my idea to her and asked her to help me become my wife's new girlfriend. The hairdresser's name is Bobbie.. Bobbie is the exact opposite of my wife. She is short, petite, has small breasts, and she is Latin. She talks with a cute Latin accent. When Bobbie heard my plan she squealed, clapped her hands really fast and told me she would she would love to help me. She also told me it would take some work to make me into a believable woman, so I should come back in two days at 5:00.
Two days later I showed up at Bobbie's shop right on time. Bobbie was finishing up with a customer. She told me to sit down and that she would be with me shortly. When she finished and her customer left, Bobbie closed the door, locked it and told me to follow her into the back room. In the room she brought me to, there was what looked like an examination table right in the middle of the room. She told me to take my clothes off and get up on the table.
I thought I would be more shy about undressing in front of Bobbie, but with my recent experiences all my shyness went away, so I did as she asked and got up on the table. A moment later she came over to me with a pot of some kind and a brush. She told me she was going to begin by removing the hair from my legs. I don't have a lot of hair either on my legs or on my chest. Anyway she applied a little of, what I found out later was hot wax, on my leg. Then she pressed a cloth into the wax on my leg.
The wax was a little warmer than I would have liked, but it was okay. Then she took hold of the cloth and ripped it off my leg, along with the hair under the wax. Most guys like to feel they are pretty macho and that pain doesn't mean much and I am no different, but when she ripped that cloth off my leg I came off that table like I was spring loaded.
“Ooowww!! That hurts!”
Bobbie laughed at me and gave me that “you should be ashamed” look that only Latins can give. You know the one. She leans back, tilts her head a little forward, shaking it from side to side, raises one eyebrow and said “I theenk Joo are jus a beeg pussy.”
What could I say? All I knew was that she wasn't ripping any more hair off of my body, macho man, or not. I was even beginning to wonder If I should re-think my commitment to this idea.
Before I said anything Bobbie said “Okay, okay. Come weeth me to thee chower.”
Head down, ego completely shattered, I followed her without so much as a peep. At the shower she gave me a bottle of some kind of lotion. She told me to rub it all over the hairy places of my body. I wasn't sure exactly what it was and it didn't smell all that pleasant. She told me to leave it on for about five minutes, then get into the shower and rinse it off. I did what she asked and low-and-behold, I was hairless from the neck down.
I thought that was great and there was no pain. Then I got this brilliant idea. If it worked that well on my body why wouldn't it work just as well on my face? So I rubbed a generous amount on my face... Big mistake! I must have left it a bit too long, or facial skin is just not made for such things. When I rinsed it off and looked in the mirror the hair was gone, but in its place there were several chemical burn marks.
When Bobbie came into the room she got this big frown on her face/ She grabbed my face, turned it from side to side, clicked her tongue several times and complained that now she would have to fix it. She was not happy and when she was not happy, I was not happy. She then sent me home with the bottle of lotion and told me to apply it every time the hair began to grow back. She told me to come back in a couple of days, freshly SHAVED, and we would work on the next step of my transformation.
Two days later, after surviving becoming hairless, I was again in good spirits when I went back to Bobbie's shop. Today was the day that she would show me how to apply makeup. Apparently there is an art to it. She told me that if I did it wrong I might end up looking like a street walker and that wouldn't do. She sat me down and had me watch in the mirror as she first applied a base coat and then two shades of eye shadow, one complimenting the other. After that there was lipstick. When she finished I looked in the mirror and I was astonished at what a difference a little makeup can make.
I was getting more excited, because I saw in the mirror that I might actually be able to pull this off for my wife. In the middle of my admiring myself, she gave me a washcloth and told me to go to the bathroom and wash the makeup off. When I came back she sat me at a table filled with bottles of lotions and powders in various colors. She showed me which she had used on me and told me to reapply the makeup myself. Needless to say, when I was finished I looked like some kind of circus clown, so she told me what I had done wrong and told me to do it again.
I spent the next three hours putting it on and washing it off, putting it on and washing it off. Each time she told me how to improve my look. By the end of the three hours I became more proficient at it and I did not look bad at all. I at least gained enough confidence at applying makeup that I did not worry much about being seen in public in makeup.
The next step was wardrobe. She said if I wanted to go out as friends with my wife I should dress casually. She told me that on Saturday she would take me out shopping. When Saturday came she took me to a huge specialty store across the bay that sold items specifically for cross dressers. I was amazed at the variety of things they sold there. I didn't know where to start.
One of the first items we looked at were breast forms. She said we had to build the body before we can dress it. Many of the breast forms looked and felt very realistic. I was immediately drawn to the big guns, the 44 D at least, but Bobbie said, I would look more realistic if I chose a more moderate size breast form. She suggested set of 36B glue-ons.
Then we looked at gaffs. The gaff is supposed to hidemale bulges. We looked at several and chose one that looked like it would do the best job. It had butt and hip pads to give me the curves to look more feminine. Next were a bra and panties. I picked out a matching panty and bra set in white. I chose white, because white goes with just about anything. I don't like much the feel of thongs, so I bought a pair of low rise satin panties. The bra was also satiny and soft.
The blouse I picked out was very conservative. It was a black Diane von Furstenberg Bentley Top with side pleating. It was very elegant looking, but not flashy. Bobbie found a lace front wig in honey blond that was very close to my natural hair. It wasn't very long, jus barely shoulder length and straight.
Then I bought a pair of skin tight blue jeans. I like tight jeans on women and with the new gaff I thought it would look good on me, too. Bobbie agreed. I was really getting excited about my new wardrobe and what my wife would think when she saw me. It was great fun for me to think about that.
The shoes were the last item I purchased. It would be very awkward for me to try to wear pumps, or special occasion shoes, so I settled on a pair of black Lauren wedge shoes. They had just enough height to look stylish, but not so much as to make me seem awkward. I tried on everything that I could at the store and everything fit fabulously, but I couldn't put everything on together, so I didn't really know how I would look completely dressed in my new outfit. I had to wait until I got back to Bobbie's shop to do that.
After I finished shopping, Bobbie brought me back to her shop. There I applied my makeup and dressed in my whole ensemble. The gaff with the panties looked great; my butt and my hips looked delicious. The gaff is actually panties designed for men, but they looked quite plain and not the look I wanted, so I wore panties over it.
The gaff/panties felt really feminine, but when I put the bra on with the breast forms I felt... I cannot describe the feeling that came over me because of the bra. Let me just say that if I could I would love for Dave to see me dressed to kill like this. I felt like I would drive him crazy looking like I did. I felt so sexy.
At the shop Bobbie taught me some of the more abstract mannerisms that I, the woman, needed to know to make the full transition into womanhood. With the shoes she taught me to walk, one foot almost directly in front of the other. Walking like that accentuated the movement of my hips.
She instructed me how to raise the tone of my voice just enough to sound feminine, but not strained. She went over how to stand and how to sit. She also taught me how to glue on my breast forms and do my nails. After that I felt I was ready to become my wife's new friend.
At home I put everything away and waited for the right moment. A few days later at breakfast, she mentioned that she would like to shopping for a new dress. That was my cue. I suggested to her that we go to the mall on Saturday and she readily agreed.
We planned to leave at ten o'clock in the morning, so at nine I locked myself in the bathroom and proceeded to dress and beautify myself. It was great fun, so exciting. Up to this point my wife did not suspect anything. That made this thing even more fun. Anyway when my makeup was perfect and my new clothes were on I went out to greet my wife as her new friend.
I went into the kitchen where she was sitting sipping on a cup of coffee. She looked at me when I came in. Suddenly a look of shock came over her face. Her jaw dropped, her eyes got wide and she seemed frozen in that state. Then a smile came over her face. She put her fingers over her mouth “Wow” she said.
“What did you do?”
“You are gorgeous!”
That, of course, made me feel proud. I explained that she had no girlfriends here, so I thought maybe I could fill in and be her best friend and that I did all this for her. She chuckled, came over to me, hugged me tight and told me how much she loved me. As we were leaving she told me that we are going to have such a fun day.
She talked, almost non stop, all the way to the mall. We laughed and talked about everything from fashion to men. It made me happy that she was having so much fun. At the mall, instead of going directly to the store for the dress she wanted, as I the man would have done, we walked by several stores and looked in the windows. We talked about the various things we saw and how they would look on us.
We walked by the Victoria's Secret store. My wife said “let's go in here and look around.” It is a log different going into a store like Victoria's Secret as a man, than it is as a women. The things I saw I visualized myself wearing and thought how sexy I would look wearing them. We went first to a shelf filled with various styles of panties. She picked up a pair of light blue boy short panties and told me that I would look great in them. Together we looked and laughed.
Then we looked at the sexy sleepwear. She picked out a beautiful satin teddy and told me to try it on. We then went into the dressing room, each with some things to try on. When I tried on the teddy she liked she said it was such a turn on for her seeing me in it and told me to buy it, because she wanted to sleep with me wearing it. I loved it too and that was the first thing I bought. After Victoria's Secret we wandered around the mall for a while looking at this and that. Then we came to the store in which was the dress she wanted to buy.
The dress she wanted was a Solid Red Belted Waist A-Line Cocktail Dress, but we didn't go directly to that dress. Instead we looked at several other dresses first. She picked some she thought I would look good in and I picked some for her. Together we tried them on and studied ourselves in the mirror. We had such a great time together. By the time we left that store we had each purchased a couple of dresses and two or three tops.
In another store she spotted plum colored silk chiffon pleated one shoulder drape evening gown. She took it off the rack, held it up to me and looked for a while. Then she told me to try it on. I took it to the dressing room and put it on. Being a one shoulder drape I had to take off my bra to wear it. My breast forms were glued on, so that was not a problem. When I came out my wife sucked in her breath, put her hand over he mouth and looked at me for a while. She told me to turn around a couple of times.
She told me she really loved how the dress looked on me and that she wanted us to go out for an evening with me wearing that dress. I hadn't thought about going out for the evening when I conjured up the plan to become my wife's friend, but at that moment it seemed a fantastic idea. I felt so sexy in the dress and that made me anxious to show it off in public, so I agreed and bought the dress.
Now I would have to buy a pair of pumps and learn how to walk in them. We then went to a shoe store where my wife picked out several pairs of shoes. I put them on to see how they fit, but I didn't dare try walking around in them. The shoes we decided upon were a pair of blue bird silk four and a quarter inch pumps.
After that we went to one of the restaurants in the mall for lunch. At lunch we laughed and giggled like small girls. I noticed, to my amusement, that several guys were checking us both out while we sat eating our lunch. After lunch we went into the restroom to freshen up.
While we were fixing up our make up my wife asked me if I saw those guys checking me out. I said yes and giggled. We talked about how good looking and sexy they were and what great asses they had. I have never had a conversation like that. I never even thought about having a conversation like that, but this one excited me. I actually thought about those guys as sexual object as we talked about them and I was really getting turned on by it.
When we left the mall and started home my wife was in such a happy mood. My offering to her to be her friend was a great success. At home she told me she really enjoyed shopping with me and she hoped there would be many more occasions when she and her new friend can go out together. Then she hugged me tight and kissed me deeply. It was a strange feeling for me to be held and kissed like that by her. I could feel her breasts against mine and taste her lipstick mixed with my own.
It didn't feel like husband and wife, but more like two women in a tender embrace. It was sensual. It was erotic and it touched my soul in a way I have never before experienced. It was not hot and passionate. It was more like we connected heart to heart and soul to soul. I wanted more at that time to pleasure her than to pleasure me.
It was then she reminded me about our first time with me as a woman and her as a man. She said she wanted to make love like that again. She also told me about how she had talked to Kim about our first time. She said that Kim became excited and confessed that she always fantasized about making love like that. She said she wanted to watch Kim fuck me while she watched.
I remembered the reaction by Kim when I was dressed in front of her before and a sudden rush of excitement filled my body. I could hardly breathe I was so excited. My wife asked if we could all go out clubbing and dancing together. It donned on me then then that she wanted me to buy the evening gown for just such an occasion.
She then inquired about my single friend Jerry. She said he was cute and had a great ass and she wondered if I could convince him to dress up and be her date for the evening. I immediately liked the idea and I cannot deny her anything, so I told her I would talk to Jerry.
Let me tell you about Jerry. Jerry is very outgoing and really fun to have at a party. He is shorter and a little more slightly built than I am. He also looks a little effeminate. People often mistake him as being gay. He has dark hair and is lightly tanned. If he agreed I knew that he could become a beautiful woman. We have been close friends since childhood and I knew I could trust him, no matter what he thought of my wife's request.
The next day I called Jerry and we went out for coffee. We chatted casually for a bit then I told him about some of the things my wife and I have been doing and about my dressing as a woman and going out with her. I explained to him how exciting and what a turn on it was to go out as a woman. I didn't tell him about being fucked by my wife. If it happened I wanted it to be by being seduced by my wife.
Jerry didn't seem too shocked. He was quiet and he thought about it for a while and finally he agreed. He told me he would need some guidance to make the transition, but it sounded like it might be fun. I told my wife that Jerry had agreed and was excited at the thought of going out dressed as a woman. That made my wife really happy and she immediately called Kim. They talked a long time on the phone making plans for our evening out.
The next day I brought him to the same store Bobbie had taken me. We bought pretty much the same things that I had purchased there, with the exception of the blouse and jeans. Instead of white panties and bra he bought blue bikini panties and matching bra. He bought a black, wavy shoulder length Jon Renau wig.
We then went to the store where I had purchased my evening gown. We found a royal blue Sheath V-neck Floor-length Chiffon Evening Dress. It was the right length for him and looked like it should fit him. We obviously couldn't try it on, so we took a chance and bought it. Then, at the shoe store, we bought a pair of black Adalyn Wedge Sandals. They looked very elegant and would not be difficult for him to walk in them.
At his apartment he tried on all his clothes and makeup. The evening gown fit him perfectly. He was so beautiful that it made me hard looking at him. I knew my wife would be thrilled with Jerry's ravishing appearance. Then I taught him everything I knew about makeup, breast forms, sitting and walking. He learned quickly and in no time he moved and acted like the beautiful woman he was.
Saturday was the day of our evening out. A couple of hours before it was time to go out I went to Jerry's apartment. Together we did our makeup, put on our clothes and made sure we looked perfect for our dates. At about seven o'clock there was a knock at Jerry's door. When he opened it there stood my wife and Kim dressed as men.
My wife was wearing black dress pants, a pale blue shirt with a purple tie, and dark blue blazer. Her hair, albeit a little long was brushed back. She had sideburns and a small mustache, both matching her natural hair color. Kim was wearing tan slacks, a white shirt with a blue striped tie and a black blazer. Her hair is shorter than my wife's and brushed nicely into a mens hairstyle. She also had sideburns, but no mustache.
Kim had not seen me dressed this good before and she was speechless. She told me I was beautiful and she was really excited about our date. I introduced Kim to Jerry. Then my wife took Jerry by the hand, told him how beautiful he was and asked him if he was ready to go out. Jerry was so excited that he could hardly speak, but managed to say he was ready, so we left. For the evening I was to be Joanie and Jerry was to be Angie.
My wife drove, so Angie sat in front with her. Kim and I sat in the back. Kim took my hand in both of hers as we drove to the club. We made small talk and were totally focused on each other. My wife and Angie also talked about things a man and a woman would talk about on a first date.
At the club the lights were low and the music loud. My wife found a table in the back, so we sat down and ordered drinks. The club was crowded with people, some dancing, some standing around and some, like us sitting at tables talking.
There was a great band playing a rather fast paced piece. My wife got up and asked Angie to dance. He got up and walked with her to the dance floor. Angie was actually doing pretty good, seeing as how this was his first time dressed up. Kim and I sat at the table talking and watching my wife and Angie dance.
After a couple more fast paced songs the band played a slow song. My wife and Angie were still on the dance floor. My wife took Angie in here arms, held her close and started swaying with the music. Kim took my hand and asked me to dance with her and we went out to the dance floor hand in hand. She put both her hands around my waist and pulled me close. I put my arms around her neck.
I was intoxicated the music and the closeness of Kim and the cologne she was wearing. It was very masculine. It was clear to me that she was in control and I melted into her as if it were the most natural thing to do. I dreamily gazed at her. She pressed her lips to mine and kissed me deeply. She reached down with one hand put it on my ass and pulled me even closer. When she pulled me close I could feel what seemed like an erection pressing against me. It turned out to be a strap on she had purchased for this evening.
I looked at her with a surprised look on my face. She just smiled and kissed me again. I looked at my wife and Angie. They had all but stopped moving on the floor. They were engaged in a deep passionate kiss. His hand was rubbing the front of My wife's pants. She was caressing his ass and they were oblivious to everything else around them.
I looked back at Kim. There was pure lust in her eyes as she gazed back at me. I put my hand behind her head and pulled her to my lips. I tickled her lips with my tongue. She opened her mouth and let me in. I explored her mouth with my tongue. Her tongue met mine with equal passion. She began to carress my ass and then with one hand she reached up and touched my breast. I was so turned on I could hardly stand it. I had to have Kim. I yearned to feel her cock in my mouth and I couldn't wait to feel her push her cock into my waiting pussy take me with all the passion that we felt at that moment.
I was so turned on that I could hardly breathe. I walked over to where my wife and Angie were still locked in a passionate embrace. I tapped her on the shoulder and told her I couldn't wait any longer and that we had to go. She broke the embrace, took Angie by the hand and the four of us left the club and headed to my house. The entire way home Kim and I kissed and fondled each other. I touched her thigh and gently stroked a massive cock. I told Kim that I wanted her in my mouth and in my ass. I told her I wanted her to fuck me like the slut I am and that I wanted to look into her eyes when she did. She just moaned and kissed me all the more passionately.
Meanwhile Angie was stroking my wife's cock and she was caressing Angie's leg. I knew she was in a hurry to get home, because she was driving much faster than she normally does. When we arrived we almost ran up to the front door; so great was the passion we were feeling. Once inside I almost tore Kim's pants off. I needed her cock and I couldn't wait any longer. I got on my knees and rubbed my face on her manhood before I removed her pants.
It felt wonderful. Then I reached in her boxer shorts and felt her cock with my hand. It was hard and warm. Almost in a panic I pulled it out, stroked it a couple of times and put it to my lips. I was in heaven again. I let it slip past my lips and savored every inch as it slid into my mouth. Kim put her hands on my head and fucked my mouth in long slow strokes.
After about five minutes she pulled out of my mouth and announced to me that she was going to fuck give me the best fuck I have ever had. I was ready. I needed her inside me almost as much as I needed breath. She put a few couch cushions on the floor and told me to lay down on them. I was on the floor before she finished telling me to move. She moved between my legs, laid on top of me and began kissing me with great passion.
Our tongues made love to each other for what seemed like hours. Then she started kissing her way down my body. First she teased my breasts and then my she liked her way to my navel. I was so aroused I thought my heart would burst in my chest. She ran her finger down my panties, across my dick to my pussy. She spread my legs and began to lick my pussy through my panties. I was going out of my mind with desire.
Finally she took off my panties and began to tongue my pussy. I couldn't take any more and pleaded with her to put it inside me and fuck me hard. She had some lubricant close by. She opened it and rubbed some on my pussy and some on her cock. After that she moved up my body and positioned her cock against my pussy. She looked me in the eyes as she pushed against me until her cock entered me. She stopped for a few seconds, still looking into my eyes then pushed all the way in. I sucked in my breath when I felt her all the way inside me and she smiled.
Then she pulled nearly all the way out and pushed back in. She did it again and again. She developed a rhythm and started going faster and faster, harder and harder. It was wonderful. She used me for her pleasure and called me a slut as she did so. She was fucking me so hard that my body jerked every time she thrust into me. I put my legs around her ass to pull her deeper into me as she fucked me. She fucked me at a fever pitch until she had one of the strongest orgasms I have ever seen in a woman.
She screamed and threw her head back as she climaxed. Seeing her climax brought me over the edge and I came also. It was one of the deepest, most satisfying orgasms I ever experienced. That was by far the best sexual experiences of my life. I wanted it to last forever, but all too soon it was over. As I came down from my sexual high I began to become aware of my surroundings.
My wife was in the same room fucking Angie with all the energy that Kim had fucking me. She had a look of intense pleasure in her eyes as she thrust into Angie over and over again. I have seldom seen something so beautiful as she was at that moment. Angie was moaning her pleasure also. She screamed “I am cumming!” and she ejaculated all over her stomach. When he shot his load my wife reached down, collected some of his cum on her fingertips and brought it to her mouth to taste him. It was such an erotic thing to watch her tasting my friend's cum.
I moved next to them and whispered in her ear that I wanted to taste him too. She looked at me with a glazed look in here eyes, reached down, gathered more of Angie's cum and brought it to my mouth and I licked her fingers clean. She more cum, put it in her mouth, then leaned over and kissed me deeply swishing his cum around my mouth with her tongue. Then she began her own grunt and moan louder. She screamed, and started fucking Angie with greater force. Her whole body trembled and shook violently while she was in the throws of her own orgasm. After her orgasm subsided she collapsed on top of him out of breath. When it was over she looked at me and smiled the most beautiful smile I have ever seen on her face and closed her eyes.
It was too far to go for Kim to drive home that night, so she stayed in the guest bedroom. After I cleaned up I put my satin teddy on and crawled into bed with Kim. Angie did the same and climbed into bed with my wife. I loved the feel of Kim's warm body, which had given me so much pleasure, laying in the bed next to mine. Needless to say I rested in the sleep of the angels. I was completely satisfied, as a woman should be after pleasuring her man.
In the morning Kim and I fucked each other again, kissed passionately and then she said she loved our time together this weekend and would like to do it again soon. Then she left for home. I could hear my wife in the bedroom fucking Angie again. They were very loud and passionate. When they were done Jerry told me this weekend was the wildest weekend ever. He said if I needed someone to go out like this again he is my man... or woman. Then he drove himself home. My wife hugged me and told me that was the most exciting thing she had ever experienced and with that our lives had changed. We look forward for the next night out.
Later that day we sat at the table talking about the events of the past evening and then the phone rang. It was Dave on the phone. He told me he was going to a party next week and wanted me to go with him and that he wanted me to dress sexy for him. How lucky am I!