Happy Halloween
  • Author - cross-dressing
  • Rating -   
  • Site Rank - 2388 of 2955
  • Story Codes - F-m, consensual, cross-dressing, pegging
  • Post Date - 7/5/2015

Halloween had just ended and my wife and I were talking about costumes from the party we went to. Of course, there were those who went to the costume store and went all out, make-up, wigs, authentic clothing etc... Then there were those who chose to go cheap with the poorly made costumes or they grabbed something at the last minute. Most of those were so drunk by the end of the party it didn't matter to them anyway. We kind of took the middle of the road, went inexpensive, and borrowed some costumes, but looked cute.

My wife, Shannon, told me that we should go all out next year and try to create costumes that not only hid our identity, but transformed us inside. As we chit chatted we drank our wine and discussed what we would do. Shannon said lots of cross-dressers come out on Halloween. How about both of us crossing over with our debut being on Halloween?

We discussed our plan into the night and came up with a timeline to complete our transformation. We knew if it was sudden we would draw attention to ourselves, but if we did it over the next 51 weeks we would be ready on Halloween. Shannon broke out the calendar on our laptop and we plotted our transformations.

First, we felt our bodies would take the longest to change, at least for me. I would start a workout regimen and a diet to slim me down and tone me up, not bodybuilding muscles, but tone. Shannon would try and increase her weight while putting on more muscle by lifting heavier weights. We decided that we would monitor our status weekly.

Next, our hair. I owned my own business and our work environment was pretty casual. We decided to start to let my hair grow in and periodically get it cut to style and clean up the ends. Shannon's hair was quite the opposite, she had thick long hair. And since she is an attorney her appearance was important on a daily basis. What to do???? After brainstorming we thought it best to concoct a story about her shaving her head in solidarity with a friend who had become ill and was going through chemo. We had time on that though and decided we would do it in August.

Shannon felt it would be best to start the removal of my body hair early to slow down the regrowth process and start to let her hair on her legs and arm pits to grow out. That would be a work in process.

As the year progressed we both made progress in our transformations. When Shannon and I made love together it felt different as far as my hairless circumstance and her hairy legs and underarms hair. She loved my longer hair and loved to run her fingers through it.

Since Shannon typically waxed to remove the hair from her legs and her bikini area. She told me shaving was fine, but it left stubble after a couple of days. So she recommended the same for me. When we were prepping Shannon recommended I have a couple glasses of wine to help with the pain I was going to experience. She started on my chest and by the time she finished I had a couple of more glasses of wine. She told me the worst had come and that she needed to do a bikini wax next. By the time she was done I felt as though my body was stinging all over. Shannon brought out some lotion and bathed me in it. It felt so much better. Shannon and I crawled into bed and had incredible sex. Shannon got out of bed and came back with a pair of scissors and the hot wax. She told me she wanted to shape my "bush". She had me lay back and put a towel under me. When she was done she took a mirror and showed me her handy work. It was a perfect heart. She smiled and told me she would help me keep it shaped. On the flipside Shannon's bush was getting pretty full.

When June came around Shannon recommended I get some highlights added to my below shoulder length hair. My hair was brownish blonde to begin with and lightening it up for summer would be nice. When the stylist was done I asked her if they did manicures. She said they did and asked if I'd like one. Off to another chair and had a manicure by Jess. When Jess was done she asked if I'd like a pedicure too? I kind of stuttered and she said don't worry about it, Shannon told us. Tell you what? Don't worry your secret is safe with us. What secret? Jess drew the curtain closed and took my shoes off and went to work on my feet. She asked if I wanted French tips or a specific color? I sat up and looked at my feet. Jess showed me her feet and I saw that she had red toes. I told her to make mine look like hers.

When I got home Shannon asked to see my toes. She screamed about how great they looked and couldn't wait to see my fingers look like them. That would take a little longer. However, Shannon pointed out that I needed to pierce my right ear since my left ear was already pierced. She poked a hole in it and I switched the earring from my left to my right.

August came and I reminded Shannon of her hair commitment. She told me that she had brought it up at her office and the entire staff agreed to donate $100 each for every inch cut off and to donate it to a research charity. She held out a pair of scissors and asked if I would like the honor. I cut her hair off, 11 inches worth, and raised $23,100 through her office. I ran the clippers over the top and took it down to the skin. Shannon was shocked and kept running her hand over her bald head. She couldn't believe it, she did it! She took her hair and wrapped it in a cloth and walked away from the mirror. As she walked out she asked for a glass of wine, a big one.

We watched a movie and she kept running her hand over her head. I put some lotion on it and massaged her shoulders. I told her I had a surprise for her. I had her close her eyes and I put a box in her hands. She opened it to find a wig like her own hair in it. I told her I thought shaving her hair off was a lot to handle and this might ease the transition. She put the wig on, looked in the mirror and kissed me deeply. We went to the bedroom and made wild love. While Shannon was on top she was bucking wildly and threw her wig off. Having a bald headed woman on top of me was breathtaking. When we lay down to sleep I looked at her bald head and realized we were committed.

September came and Shannon's hair was growing in and she started to keep it combed in a man's style. Periodically, she would wear her wig to maintain her appearance at work, although everyone knew she had cut her hair off. On a Friday night, Shannon said we needed to have a dress rehearsal on our costumes. She suggested we go through each of our belongings to see what our shortcomings were and what we needed to buy to complete our ensembles.

Since I'd been losing weight and toning up nicely and Shannon was bulking up we'd had to add clothing to our wardrobe to be able to look nice in our day to day clothing. We went through my clothes first to get Shannon attired. We chose a nice suit for her and decided an open collar would be more comfortable than a tie. Shannon started to try the suit on and I told her to hold off, she couldn't wear a bra and panties with a man's suit. I laid out a t-shirt, jockey shorts, and black socks. When she put the t-shirt on it didn't look right. I told her to hold on while I grabbed some plastic wrap. I had her hold her arms over her head and wrapped a couple of layers of wrap around her breasts until they were almost flat. We put the shirt back on, looking better. She put the jockey shorts on and the black socks. She started to get dressed in the suit and was looking great. She put my shoes on, a little big. She combed her hair to the side, then back then, up. She said she'd have to work on the hair style. I gave her a watch to wear and took my wedding ring off as well as hers and put it on her finger. She looked great. We made our list of changes, eyebrows, shoes, trimming and cleaning her nails. Also, she left her earrings out to let her holes close a bit.

My turn. Shannon laid out some clothes and undies for me to start with. I put on the bra it was a bit loose and put on a thong. I had to tuck my package and Shannon said it was still too big. She went to the garage and grabbed some duct tape. When she came back tore off a strip and taped my package between my legs. The thong looked better.

She removed my bra and broke out a corset. She put it on me and tied it up tight. But my breasts didn't look good enough. She went into her draw and put a pad under each of my breasts. I had cleavage! She put a white camisole top on me and a short leather skirt and ran her hands over my legs. She told me while my legs were nice stockings would be nicer. She found a pair of high heeled sandals that would give me some room to make up for the size difference. They were tight, but looked nice. My toes looked nice through the fronts. Shannon motioned be over to the make-up mirror. She turned me around and told me to trust her. I'd been using a depilatory instead of shaving my face to cut down on the facial hair.

Shannon went to work, using a foundation first and then going to work on my eyes. She applied false eyelashes, shadow, mascara, liner, and shaped my eyebrows a little. As a last touch she broke out some colored contact lenses and inserted them in my eyes. After working on my lips, and cheeks she turned her attention to my hair. She told me she was going to use a curling iron, but the curls would wash out. She started alternating between hairspray and the iron. Brushing, and teasing, and more hairspray. She put some dangling gold earrings in my ears and suggested a second hole in my right ear. I agreed and she put a small diamond stud in it. She took her wedding and engagement rings and rubbed some lotion on my ring finger. She slid the rings on my fingers and said, with these I wed thee, and lightly kissed me on the cheek. She spun the chair around and I could not recognize myself. I couldn't believe the transformation.

Shannon had me stand and sprayed some perfume on me. It was intoxicating. I went to the medicine cabinet and grabbed some aftershave I rubbed it in my hands and told her to get ready. I patted each cheek and her neck. She cringed as it burned. After passing I told her she should try it after shaving.

We looked at what I needed for the next day, and made a list: bigger shoes, stockings and a garter belt, we decided it was time to let my nails to start growing longer and we needed to get some clothing with a theme for the party.

After dress up we looked at each other offering criticism. I saw that Shannon's package was lacking. I grabbed a pair of socks and shoved them down her pants into her shorts. Crude but effective. We spent the rest of the evening drinking wine and watching a movie. Afterwards we turned into bed. The sex was amazing. Shannon took on her male persona. She mounted me from behind and motioned like she was penetrating me. She came and came and told me to fake an orgasm, like a bored woman lover faking it for her man. I tried to fake it, but did a poor job.

As Halloween got closer, a week away, I told my office staff Shannon and I were going on a vacation for two weeks. Shannon also did the same and made sure her case load was set up with other attorneys and continuances in court.

When we got home on that Friday night we talked about the steps we were going to take. We had a week until the party. Shannon said we needed to get to work on me as I would take the longest. She started by plucking some of my eyebrows and shaping them. She called her friend at the stylist's shop and asked her if we could come in after hours for a pedicure and acrylic nails. We were set for Saturday night.

Jess went to work on my nails and before I knew it I had long French tip acrylics and my toes matched. When she looked at her handiwork she smiled and asked if I'd like a nose piercing on the house. I looked at Shannon and she shrugged. Jess said it would heal up quickly after removing it. What the hell, go for it. Jess came over cleaned the site, and quickly pierced and inserted a stud. I was shocked how little it hurt. Jess added, how about your belly button too? She said that it would hurt a little more, but really complete the look. I laid back and Jess had it done in minutes. When I looked at the piercing she had a star piercing hanging in the opening of my belly button.

Shannon also mentioned that she had arranged through a friend who was a doctor to have saline injections in my breasts. She explained that they were temporary, lasting a few hours. I agreed to try it out. We met up with him Sunday morning and he explained the procedure to me and that they would be back to normal in about 10 hours. If I liked them he would repeat the procedure on Friday afternoon, Halloween. He also offered a cream to temporarily plump my lips for a couple of days. I agreed and he went to work. He numbed the injection site and proceeded to slowly inject the fluid. When we got to a c-cup he asked if it was enough and Shannon went into her purse and pulled out a d-cup bra. The doctor smiled and continued to push. The second breast was next and it was incredibly tight almost painful. The doctor told me that the skin would stretch and the saline would start to absorb. I put the 36-D bra on and it fit nicely. When I stood up I noticed I couldn't see my toes. Oh my god, what have I gotten into.

We got home, and Shannon quickly styled my hair into a pony tail, gave me a shirt which was now tight, some jeans, and some white deck sneakers. She touched up my make-up and said' Let's go shopping. We were two girls out for a day of shopping. We went wild shopping at a mall in another town. We bought shoes for me, skirts, shirts, and all sorts of things. I really began to think this was a lot for a party. Shannon, got some guy things to make her look complete, but she went off to a store by herself for a while. When we got home we went through our purchases showing off our new things, except for a bag Shannon bought. She said it was for the party.

The rest of the week went quickly and before we knew it Halloween was here. We went to see the doctor where he added more saline to get me back to a D-cup. He plumped my lips a bit and out the door we went. Over to the stylist again where Jess trimmed my hair, and styled it up. My neck and ears felt naked. Jess leaned over and said I'd get used to it, and it would make my earrings and necklace look nice. She touched up my nails and gave me a hug and a kiss and told me to have fun.

After a year of prepping for this I was starting to feel relieved it was almost over. When I got home Shannon said we had to be there by 9:00 p.m. Shannon went to work on my face and told me to get dressed. She had laid out my clothing and I started off with a black corset. Shannon pulled the strings while laying me on my abdomen, and putting her knee into my back, she tied the back of it with a double knot and used a padlock to lock the front. She helped me with the stockings and securing them to the garters. She helped me put on a little black dress and zipped it up the back. When I went to step into the pumps she asked me to hold on. She went to her dresser and brought out a fake pussy. She showed it to me and told me that I would slip it on like a pair of shorts. When I did this she readjusted the garters and smoothed out the pussy. As fake as they looked, it completed the transformation. Shannon broke out another pair of pumps, the kind with a strap and lock. I put them on, but they made me three inches taller. She smiled, and said she wanted the five inch pumps, but that would have been tough to get used to in one night.

The doorbell rang and I looked at Shannon as if she was going to open the door. She told me it must be the trick-or-treaters. She handed me a bag of candy and slapped me on the butt. Oh wait, she applied some perfume to my neck, wrists and breasts. I went to the front door and found a handful of kids at the door yelling trick or treat. I handed out the candy and started to close the door when I heard another trick or treat. Jess stepped out from the side and she was wearing a suit and hat and ushered me to a waiting limo. She took me by the arm and told me Shannon would join us at the party. Inside the limo was an open bottle of champagne and Jess urged me to get primed.

We drove for about 45 minutes and stopped at a nice home in an upscale neighborhood. When Jess opened the door she placed a fur coat around my shoulders and whispered into my ear. Enjoy!

As I walked up the walkway I felt like I was floating. I could see partiers inside and rang the bell. A woman in a witches' costume came to the door and invited me in. She asked where my costume was. In my manly voice I said I'm wearing it. She smiled and said, "I'd love to meet the witch who cast a spell on you".

I entered the room and men turned to look at me like candy in a candy store. A waiter walked up to me and handed me a glass of champagne. I knew being a man in a room with other men was always difficult to strike up a conversation with a smoking hot woman, but now they wanted to talk to me. I tried to avoid the attention, but everywhere I went a man came up to me. Finally the witch grabbed me by the arm and led me into the bathroom. Once inside I saw there were other women who were in their costumes and fixing themselves up.

One woman asked what gives? Did you not get the 411 on what kind of party it was? I responded, "I did". They all went silent and then started to laugh aloud amazed at my transformation. Questions flew left and right and I tried to answer, but next the touching and the feeling started. They were all over me! The door flew open and Shannon shouted, "What are you doing with my bitch"?

Everyone stopped, smiled, and got the I get it look.

The rest of the evening went awesome. We danced, traded partners, and got totally smashed. We really had a great time. When the costume contest started we had a great time hamming it up and the crowd loved us. We won first place and received a gift certificate to a spa for two days. After the party ended Jess drove us home and we were all over each other on the ride home. As we were feeling each other up I ran my hand between Shannon's legs and found a bulge between her legs. I asked her what it was and she told me it was a surprise.

When we got home we went to the bedroom and Shannon let me strip her clothes off, leaving on her t-shirt and jockey shorts. The bulge fascinated me. Shannon removed my dress, leaving everything else on. She asked me to get her a drink. When I returned, I saw that Jess had joined us and was lying naked in our bed with her legs together. Shannon jumped into bed with Jess and started kissing her. She took her finger and motioned me over. She put a blindfold on me and guided me between Jess' legs. As I reached the middle I found that she had a dick, a real one! She guided it into my mouth and put me to work on her. As I was on all fours giving Jess head, I felt Shannon coming behind me and between my legs. She entered my pussy with her finger and lubed my ass. Next I felt a dildo slowly enter my ass. I thought this might be going too far and tried to protest. Jess took my head had pushed me back down onto her cock.

Jess pumped my mouth and Shannon pumped my ass. I felt Jess getting more intense and she blew her load in my mouth. When I tried to pull away Shannon pushed my head down and told me to swallow like a real woman. She continued to pump my ass and started to cum herself. We all lay together in bed and took in the moment. After a little while I pointed out I didn't get to cum yet. Jess rolled over onto her back and spread her legs. I pulled the fake pussy off and duct tape off. I entered her ass and Shannon sat on her face. I pumped, Shannon ground her pussy into Jess's face and Jess moaned her way to cumming again as Shannon and I came too.

We lay back down and talked about next Halloween and what we would do next year.

Shannon said she had an idea, and asked for a week to work it out.

Details to follow in 51 weeks.





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