Glamour Photoshoot Transformation

My fortieth birthday was coming up in a month and I was a contract IT employee working from home and my wife also worked from home as well. We had been married for ten years but had never had children of our own. We were well off and lived comfortably in our home in the country with forty acres of land. I was five seven and my wife was five five. She had always joked that with my slender build and shorter stature for a man I could probably with a little help be able to dress as her for Halloween and her as me. We had seen an ad online for a glamour and boudoir photoshoots with a female photographer in a larger city a couple of hours from where we lived. They offered hair and makeup services as well as clothing, accessories and shoes to wear as part of the glamour and boudoir experience. I had been letting my hair grow for the last couple of years and it was actually a couple of inches longer than my wife’s hair was. My wife called the studio and made an appointment for two days later for a consultation appointment for a possible photoshoot.

Two days later we got up early and drove into the city and had brunch before heading to the studio for the consultation appointment. The receptionist Heather welcomed us and told us that Gloria the owner and main photographer would be with us shortly. Staci and I waited in the comfortable waiting area. Five minutes later Gloria came out and showed us to her office.

I introduced my self as Alan and my wife Staci. Staci explained to Gloria that my fortieth birthday was coming up in a month and she wanted to do something special and different for my birthday. She explained that she and I had always thought with a little help from makeup, hair styling and clothing I could pass as a woman. Gloria said she had worked with some transgender and crossdressers over the years and she had a great hairstylist and makeup artist who could work their magic in me and make me look like a different person that even my own mother would not recognize. Gloria said with my slender build for a man and shorter height i should fit well into their wardrobe for female glamour shots. They also had fake breast forms and other prosthetics to help give me a more curvy feminine appearance. Gloria took us back to meet Bethany her hairstylist who did a consultation for the hairstyle I would have at the photoshoot. Bethany said my hair was healthy and with the length at mid back almost any style would work. She and my wife agreed that my brunette hair would look great with platinum blonde highlights and honey lowlights as well as cutting it in a more feminine bob style. She also suggested a tight spiral perm to give it more body and attractive feminine curls for the shoot. Gloria took Staci back to her office to discuss the details of the shoot as well as possible outfits and accessories for each part of the shoot.

Bethany led me to the sink and as I laid my head back she went to work washing and conditioning my hair. She seemed very excited about transforming my hair and my look for the upcoming photoshoot. She said that it was exciting to work on virgin hair and be able to show me what she could do to transform it from normal to a fabulous sexy and feminine style. After she dried my hair she started mixing the bleach and getting everything ready. She used a brush applicator to paint different sections with either the maximum platinum bleach as well as alternating sections with the honey lowlights bleach. After she applied the highlights and lowlights to my hair she wrapped foil around each section to allow the chemical reaction to have the proper heat to process and produce the desired results. After she put the last foil in she said we would wait and offered me a woman’s magazine to read while I waited for the color to bake. After a Lille while she checked a couple of the foils and declared I was done. She removed the foils and took me back and washed my hair to remove the bleach.

Bethany didn’t let me see it yet as she led me back to her styling chair and started to brush and used her scissors to snip and trim my hair as she worked on giving me a more feminine layered bob style with bangs in the front. It took her a while as it seemed like she was cutting all over my head. When she finished she brushed and styled it as she sprayed a coating of firm hold hairspray to set my new style. Bethany spun the chair around and revealed my new hairstyle to me. It was still my face but my hair was definitely more feminine and fabulous looking than it had ever looked before. I was amazed how good the platinum highlights and honey lowlights brought out the look of the layered bob style I now sported. It definitely made me look more feminine and it made me appreciate what a change in hairstyle and color along with the other changes they would make with the prosthetics and makeup could do to completely transform my look from drab average male to glamorous sexy fabulous female. Bethany sent me a text message for my next appointment with her in three weeks to come in for my perm, nails, and other prosthetic and facial work so I would be ready the week after that for my final transformation for the photoshoot.

Heather came and took me to another room where I had to strip and put on a robe, slippers, and disposable thong for my next treatments. She introduced me to Alicia who had me take off the robe. Alicia took a gel like substance and slowly spread it over my facial, body, arms and legs completely covering and full coating my body and facial hair. She had me weight thirty minutes as it began to cause my skin to tingle. Afterwards I was led to a shower where she helped me rinse the gel off my face and body. As the gel came off I also noticed it took all my facial and body hair with it down the drain. Alicia patted me dry and except for a small inverted triangle above my groin was silky smooth and devoid of hair. Alicia explained that it was a powerful yet sensitive formulation that totally removed hair from the root and blocked hair production in my hair follicles from producing new hair growth for around eight weeks. Alicia also explained that what hair grew back would be finer and sparser. And with continued treatments it would eventually destroy the treated follicles and permanently remove the hair from my face and body.

Alicia had me remove the robe as she pulled a corset with laces at the back around my midsection. She had me hold on to a column in the room as she had me exhale as she slowly pulled and tightened the laces as slowly my waist was reduced by several inches. She gave me a link to a video and instructions so my wife could keep me laced up over the next four weeks as we worked on training and reducing my waist circumference so I would have a more hourglass shape for my glamour photoshoot. Then Alicia took several breast prosthesis and compared them to my skin color and finally settled on a pair of D cup forms. She cleaned the skin and has me lay back as she applied and adhesive gel to the back of each form and held each one in place for about ten minutes as the adhesive dried and held them in place. Alicia applied a skin colored makeup to the edge of the forms to hide where they connected to my body. When I sat up their weight pulled forward as I now understood why large breasted women had to wear a bra with enough support and lift to keep their breasts from sagging. Alicia wrapped a large ace type bandage around my new breasts and over my shoulders and back to support them until I could go shopping for bras that would give them the support and lift they would need. Alicia informed me that the adhesive would slowly breakdown over the next six to eight weeks. So now I was stuck with breast for the next couple of months.
Then Alicia had me sit in the chair as she cleaned each earlobe and made a mark on each one checking from several different angles for symmetry between the two marks. Satisfied that they looked symmetrical Alicia took a device and aligned it with the first mark on my left ear and she squeezed the trigger as a metal instrument quickly made a hole in my earlobe and left a diamond stud earring in my ear lobe. She quickly repeated the process on my right ear lobe and as I looked in the mirror I now had diamond stud earrings in the freshly pierced hole in each ear. Alicia explained that by the time the shoot happened in four weeks they would bf healed and I would then be able to wear pierced earrings from their collection of earrings to match each of my outfit changes. She explained that after the shoot I could leave the earrings out and eventually the holes would close if I decided I didn’t want to keep them pierced.

Alicia then had me lay back as she took a template and placed it over each eyebrow and used a special marker to color each one. Then she took a brush and carefully applied a small portion of the gel like substance along the bottom and side of each eyebrow. Then she had me wait and after thirty minutes she took a wipe of some sort and used it to remove the gel she had applied. It also removed the markings she had made on them earlier with the templates.

As I was laying back she pushed the chair back further and removed the disposable thong underwear as she pulled stirrups up from the base of the chair and place my feet in them as she spread my legs exposing my male genitalia. She took a bottle and sprayed a generous amount of a numbing agent on my male genitalia. After ten minutes Alicia pushed my testicles up into the canals where they dropped down from and then she spent several minutes adjusting and apply adhesive to the skin in my genital area. And then after she was done she took a mirror and positioned it where I could see my genitalia area. It now looked like a female genitalia area. Alicia explained that the adhesive would give me a more flat feminine groin appearance as well as allowing me to urinate in a sitting or squatting position. The adhesive would break down over the next eight weeks, so I was now going to have to sit or squat to use the bathroom for the next two months.

Alicia took me to the mirror and showed me the results. I know sported very feminine thin arched brows that screamed female and totally changed the look of my eyes. The smooth skin, breast forms and corset gave me a decidedly more feminine look along with my new hairstyle and color. I almost didn’t recognize myself. I kind of overwhelmed me for a few minutes. Alicia assured me that if I didn’t have follow up hair removal treatments my eyebrows and facial and body hair would eventually grow back, I could let my hair grow out and have it cut short as well.
This calmed my nerves as I realized so far nothing was permanent and I could spend the next few months experiencing life from the other side of the gender fence and since I worked from home I could have a better understanding of how my wife experienced life as a woman.

I met my wife Staci up front in the reception area, she was impressed with how feminine I looked, even without any makeup on. We left and headed to a department store nearby. She took me to the MAC Cosmetics counter and explained that I was spending the next couple of months as a woman and need some makeup to help complete my new look. Sharon the MAC artist had me sit in a chair as she pulled several foundation shades and compared them to my skin tone. After she found one that matched she asked what kind of look I was going for. I told her and my wife agreed that I needed a day time look and also a more dramatic evening and weekend look as well.

Sharon applied moisturizer to my face and said she would give me a day time look first and explain what she was doing. Then she wound show me how to transform it to a very dramatic evening and weekend look for going out. My wife Staci used her phone to film the application so I would have it to practice with on my own over the next couple of months. Sharon applied a concealer under my eyes and then applied a layer of the foundation to my face and showed me the results. It was amazing how just the concealer and foundation changed and evened out my skin tone and hid the imperfections on my face giving me a smooth flawless canvas to add color to. Sharon then explained how she was adding both highlights and lowlights to my face in different areas to either emphasize or deemphasize different parts to contour and make my face look more feminine. Sharon showed me the results and I was amazed how even without my eyes and lips done I looked very feminine now.

Sharon applied brown eyeliner and added subtle muted colors to my eyelids to give me a fresh daytime look to my eyes. Then Sharon applied black everyday mascara to my eyelashes and used a brow pencil and brush to give my arched brows a hint of color. Sharon then applied a light peach color to my cheeks and a pink rose colored gloss to my lips.

Sharon showed me the day time look and I was totally blown away with how just a little color and the other changes from earlier had totally transformed me from a drab male to a beautiful feminine person.
Sharon then started working on my face for the evening look as she described what she was doing to make it dramatic and very feminine. She applied a very black liquid eyeliner around my eyes and extended the line out from the edge creating what she called a cat eye effect. Then she applied a heavy application of very dark eyeshadow to my lid and a dramatic lighter shade across my brow-bone. Sharon added false lashes to my own creating long full eyelashes. Then she coated my lashes in a very black waterproof mascara and added several coats letting each coat dry in between. I could feel the weight and see the dark lashes every time I blinked. Sharon took a pencil and outlined my lips and then applied a dark cherry color lipstick and a clear sparkling gloss to add an extra pop to my dramatic look. Then Sharon brushed a rose gold color over my checks and set everything as she had me look at the finished results. It was an even more dramatic contrast from the original day time look and made me wonder if it was too much. Staci thanked her for her help as we purchased all the products she used plus a few more that I would need for the next two months.

Next Staci took me to Victoria Secret and we picked out several bra and panty sets along with baby dolls, chemises, and garter belt and stockings. After trying everything on I left the store wearing a red sheer bra and a matching high cut sheer panty. Then we stopped back in the women’s section of the department store and I tried on several daytime and evening dresses, skirts and tops. I also tried on a one piece swim dress and a bikini as well. We also tried on several pairs of heels, flats, pumps and stilettos. It was definitely an eye opening experience as I ventured for the first time into the world of feminine fashion!
I left the store wearing a sexy black dress with tights and the stilettos on. Staci said I was a natural at walking in heels and that I must have been a sexy woman in a past life. It was definitely a new experience for us.

Staci drove as we went to a local club to end the adventure. We sat at a table and had a couple of drinks and talked. I had been practicing my feminine voice and it was definitely improving. Soon a couple of guys came over and bought us a round of drinks. We talked and then they asked us to dance. It was an interesting experience being the one being led around the dance floor and also dancing in heels for the first time. Staci and I told them we had a great time and we headed home.

When we got home and changed into baby dolls and my wife Staci started kissing and caressing me. Then she had me lay down on the bed and close my eyes. Then Staci started massaging my rectum with a gel like substance. Then she slowly pushed a moist finger inside my rectum and started massaging and moving it around and in and out. It felt a little strange at first but soon it started to feel good. After a few minutes she pushed two and then three fingers inside. Then she pulled her fingers out and I felt a cool moist rigid pressure pushing against my rectal opening. The pressure increased and all of a sudden the head of the object suddenly popped inside my rectum. Staci slowly pushed it deeper and then pulled it slowly back leaving only the head inside me. As the intensity of the dildo sliding back and forth increased, I felt a pressure as it massaged my prostate. Then Staci pushed a vibrator against my penis head that was inside the glued together skin. With both the massaging of my prostate from the glass dildo in my rectum and the vibrations against my sensitive penis head my body started to tingle as a wave of pleasure swept through me from my head to my toes like a burning fire inside me. Then I spurted and cum dripped out of the hole where my male genitalia had been inverted. It was a different type of orgasm than I had ever experienced before. Not just the quick explosion of passion I had previously experienced as a man but the slow and growing full body intensity. It felt good.

Over the next three weeks I explored applying my own makeup using the cosmetics and watching Sharon’s application video. After some trial and error I become quite adept at applying makeup and making it look feminine and natural. I continued to work on projects for work and Staci was busy with her work. Our sex life had definitely taken a turn since I couldn’t penetrate her in my current situation with my male genitalia rearranged to appear female. Plus I had really learned to enjoy being fucked in my rear and had also started wearing glass plugs during the day and sometimes after sex at night to keep the fullness in my rear. I also found that I was enjoying the new wardrobe possibilities that were open to me as I was living the female role for the near future.

A couple of weekends after the start of my foray into the feminine role my wife suggested we take off early on Friday and drive four hours to a small beach resort town on the coast for a fun and relaxing girls beach getaway! Staci had always enjoyed her girl beach getaways in high school and college. We packed our things and headed out. We arrived and checked into the resort. Saturday morning Staci convinced me to don the swim dress along with a cover up and beach bag and head down to the chairs on the beach. I rubbed the suntan lotion over Staci’s body and she rubbed it into my skin as well. We layed back and bask in the sun for a while and then we turned over and spent more time in the sun. Then we headed down to the surf and at first walked along the shore as the waves crashed over our feet. Then we waded out into the waves and swam and played in the surf for a while. Early afternoon we packed out things and headed to our room to take a shower. Then I put on a bra and panty set and donned a beautiful sundress and a pair of three inch sandals as we headed to a local restaurant for seafood and a few drinks. After our meal we decided to head to a club for dancing and then back to the room for a night of pleasure. The next day we swam and laid by the pool. Staci had convinced me to wear the bikini today. It was definitely an experience and a little more revealing than the one piece swim dress I wore the day before. We went back to the room showered, dressed and packed and headed back home. I noticed I had feminine tan lines from the swim dress and now the bikini I as worn over the weekend.

We continued to work and have fun together over the next week. On Saturday I left early and drove to the photography studio for my appointment for the spiral perm and also some other enhancements for the photo shoot the next weekend. Heather welcomed me and soon Bethany came and escorted me back to her studio. She commented on how natural and feminine she looked and moved. I told her the last three weeks had been an eye opening experience. Bethany told me to be careful because I could end up deciding I didn’t want to go back to my male life after this two month experience living as a woman. I agreed and thanked her for helping me. Bethany washed my hair and then had me sit in her styling chair. She brushed and sectioned off my hair and soon was rolling it in very small tight rods. After all the rods were in place she wrapped a roll of cotton around my head below my hair and then began applying the perm solution to my tightly wrapped curls. She walked me over and put me under a dryer and gave me a magazine to read as I waited for the perm solution to work its magic on my hair. I read several articles about dating and fashion and makeup before Bethany checked a rod and declared my hair done. She took me back to the sink and washed the perm solution from my hair. Then as I sat again in her styling chair she removed the rods and style the curls. She finished and showed me the results. If I thought I was feminine before I definitely looked feminine now with my tight spiral perm and curls all over my head. Bethany then had me lay back as she inserted a needle into my lips and slowly pushed the plunger in as she used a special fat deposit solution to fill and temporarily plump my lips giving them a full and pouty look. She said it would last for about four to six weeks. Then she had me gargle with a special solution which caused a tingling sensation inside my throat as it paralyzed part of my vocal cords. Bethany said it would temporarily for the next two to three weeks paralyze a portion of the vocal cords and would raise the pitch of my voice into a more feminine vocal range to make it easier to speak and sound like a woman. Then Bethany filled in my nail extensions and repainted both my finger and toenails in the sparkling rose gold polish. She then took my diamond stud earrings out and put a pair of silver hoops in the holes. It felt different as I felt them sway with each movement my head made.

Afterwards I went back to see Alicia who checked my breast forms and the genital areas and then checked my waist to see that it has shrunk some more from the waist and corset training and now I had a definite hourglass appearance. My measurements were 36 D chest, 28 waist and 38 inch hips. She encouraged me to keep training and I might be able to shrink my waist another inch or two by the following weekend for my photo shoot. I told her it was definitely an experience and I looked forward to my photo shoot the next weekend and seeing the results. I received a text to confirm my makeup early the next weekend as the first part of my photo shoot session. I thanked her and headed home.

Staci loved my curls and said they made me look very hot and sexy. She grabbed me and put on her strap on double ended dildo and harness as she pushed me across the bed and started to fuck me doggy style. It felt wonderful and soon we were both panting from our intense shared orgasm. I had definitely taken on a more submissive role in our love making over the last three weeks. We had dinner and Staci fucked me again as I rode her dildo reverse cowgirl style as I was able to lift up and plunge deep on her dildo and soon we both exploded in an intense full body orgasm again. I rolled over and push the lubed rose gold flower glass plug inside my rectum and drifted off to sleep.

We had a busy week ahead and after work Staci and I tried various positions as she fucked me and rode me hard with her double ended dildo.

On Friday afternoon we drove to the hotel we were staying in for the weekend in the city where the photo shoot would take place the next day. We had dinner and a night of passion in the hotel. We got up early Saturday and showered and headed to my appointment. I took off my dress and put on a silky sheer robe on as I let Bethany cleanse my face and begin the hour long makeup application for the shoot. I was amazed at how dramatic I looked afterwards and I definitely didn’t recognize my self in the mirror. I went to the wardrobe area and met Alicia as she helped me into a very dramatic evening gown with sequins and sheer lace. I slipped into the five inch stilettos and she led me onto the set where Gloria and my wife were waiting. Gloria had me pose as the stationary and also the 4K video camera rigs captured my poses and movements. Gloria also had another high end camera that she was using as well. Then Alicia took me back and put me in several different dresses. The next was a very short dress that was red and showed my stocking tops and garters as I moved as well as revealing my cleavage from the fake breasts. My wife had encouraged me to wear the rose gold but plug so I felt the fullness and it slowly massaged my prostate as I moved through the poses. It helped give me a more sexy look and movement as I posed for each picture.

The next attire was a skimpy polka dot bikini that showed off my feminine tan lines from the beach and laying out at home as well. I posed with a volley ball, beach ball, and other beach accessories.

Then I wore a school girl outfit and posed in a classroom setting as I leaned over a desk and also made provocative gestures.

The next outfit was a sexy safari leopard print dress and wide brim safari hat that left little to the imagination. I posed with a giraffe, lion, and elephant fake models.

The next outfit was a very sexy wedding dress with sheer lace and pearls with a long train and sheer veil. Gloria had Alicia and Bethany pose in bridesmaid dresses with me in some of the shots. Then a man in a tuxedo came out and I found out he was a model Gloria used from time to time named Stephan. He was tall and very muscular. I posed with him and she had him out a ring on my finger and even lift the veil and kiss me. If felt different kissing a man.

For the final outfit of the shoot Alicia helped me into a sexy sheer white babydoll nightie, garter belt, sheer white stockings and stiletto white pumps. With a sheer satin white robe over it all. I was in a bedroom scene and was supposed to be the bride getting ready for her wedding night. She had me pose in many different and provocative poses. Then she had me pose on the bed with my head down and my rear up in a sexy ready for sex pose. After a few shots she had Stephan come out in a g string speedo leaving little to the imagination. Gloria had him pose near me as if he was admiring me and getting ready to fuck his bride on her wedding night. As his speedo pushed against my backside I could feel his penis began to harden. Soon it was rock hard and poking the rear of my panty covered rear. Then Gloria had him remove his speedo and push his hard member against the back side of my sheer panty as if her were getting ready to fuck me. Gloria came over and pulled my panty down exposing me rose gold but plug flower in my rectum to the camera as Stephan put his penis head on the flower and pushed it around in the next few shots. Then Gloria had him reach and pull the plug from my rectum and had him out the head of his penis at the entrance of my rectum as if he was about to deflower his bride on their wedding night. Gloria said these shots were hot and very sexy! I looked towards my wife but she was massaging her clit through her panties with her hand under her dress.

Then I am not exactly sure what happened next but since my rectum had been relaxed from the plug and either I shifted or Stephan did or maybe we both shifted. But in an instant the head of his engorged cock popped fully inside my rectum as a let out a moan of pleasure. Gloria was snapping away as quickly as possible and then before I could respond she directed Stephan to start fucking his bride on their wedding night. Soon his cock was buried fully inside my rectum as I adjusted to being filled and moaned in pleasure as it was now filling me completely. Then slowly he started to pull back and then push forward as I was now being fucked by a man with a real flesh and blood cock pounding my rear as it massaged my prostate with each movement back and forth. Soon Stephan was pounding me with a passion and speed I had never felt before as I started moving back to meet his thrust. After several minutes I was moaning in pleasure as my first female full body orgasm from a real cock was pushing me over the edge. Then as a second wave washed through my body I felt him plunge deeper than before and then I felt his cock spasm deep inside me as I felt his warm sticky cum spurt deep inside my bowels filling them with his baby makers. We both collapsed on the bed as his cock slowly softened inside me and our breathing was slowing back down again. As he pulled out Gloria reinserted my plug trapping his semen inside me.

Slowly I regained my composure and went back to the dressing room where my wife meet me. I looked at her and she said it was so hot seeing me as a woman being fucked by a strong muscular stud. She was wet and extremely turned on as she kissed me and pulled me close. I changed into my dress and clothes as we went back to the hotel room. I was still I shock and confused at what had happened just an hour ago. I had been fucked by a man in my rear and I had enjoyed it. Was I cheating on Staci since she arranged this photo shoot? Why did I want to feel a cock in my again? Am I gay, am I bisexual? Have I always been female on the inside? I collapsed in a heap on the bed and cried myself to sleep.

The next morning I awoke and Staci and I had a talk. She apologized for putting me in this situation in the first place without asking me. We agreed to go to counseling and I would also see a counselor to make sure I didn’t have any repressed gender dysphoria or other sexual orientation issues or questions.

Epilogue: Two years later:
I woke up and had to go to the bathroom. I pulled my panties down and sat to urinate as I had been doing for the last two years. Then I wiped and pulled my panties back up and headed back to bed as my husband snuggled up against me. I have been married for two weeks now. Sexual intercourse with my husband pounding my new vagina and filling it with his semen has been the best thing to happen to me since my gender reassignment surgery. Two years ago counseling revealed that I had been suppressing my gender dysphoria and my feminine identity for years. Staci and I remain best friends even after we divorced so I could pursue my transition to full time womanhood! I still have the pictures where Stephan and I had our first of many sexual encounters from the photo shoot over two years ago. Now Stephan is my husband and gets to fuck his wife in her pussy with his large hard member anytime he wants to. Staci started dating again and married a man named Randall six months ago. I was her maid of honor in her wedding and she was my matron of honor at my wedding two weeks ago. I still do some IT coding on the side but I also started female modeling and have been doing fashion shows and commercials and photo shoots for almost two years now! If Staci hadn’t pushed me to do that glamour feminine photo shoot I may have kept my feminine side repressed for ever! Now I get to be me and have a wonderful husband and a great best friend who I get to go on girl trips shopping and to the beach with!