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The Pageant

An unusual end-of-summer beauty pageant spices up a young man's relationship
I was happy to finally get a job, a decent job, at Sweeney, Burke, and Garcia, a law firm in Savannah, my hometown of about 25 years. The economy was still hurting and I was days away from making a decision to move to another city, so I was grateful for the opportunity that came my way to remain in my beloved city.

I was hired as a temporary executive assistant for one of their environmental lawyers named Mandy. On meeting her, I was genuinely surprised at how beautiful she was. She didn’t fit the typical stereotype of your average corporate lawyer. She was tall at 5’8,” blonde, long and lean body with shapely legs, perky little breasts, and looked very hot in her professional business attire of skirt, low-cut blouse, jacket, and high heels. She was still very much in her prime at 38 years of age.

At first, I kept all my conversations with her very professional, answering her questions to the best of my ability, and meeting all her office needs. I knew that being temporary, any chance of long-term employment at the firm hinged on doing a “great” job. The first few weeks were hectic for me, learning the ropes and all the “lawyer jargon” wasn’t easy, but I quickly got the hang of it.

Mandy was in the middle of a large and lucrative case for the firm when I came on-board and she had told me that it was important for her to win as she was being seriously considered by the board for partnership. Her previous executive assistant, another male, had recently taken ill and had to take a leave of absence. She said the stress had gotten to him and he was intending on returning at a later date…not good for me.

In the weeks that followed, Mandy won her case and she had taken a liking to me. She said I was very good at staff work and she appreciated my dedication and working long hours. I told her I was happy to be there and that I would always give her 100 percent.

She smiled and said, “Be careful what you say John, there may be a time when you might regret saying that, I can be very demanding at times.”

At the time I thought that was simply what all bosses said…however, looking back, I couldn’t have been more wrong. Despite Mandy being my boss, I had slowly developed an attraction for her and I had thought from time to time what it would be like to have sex with her. She had a lot going for her and unfortunately for Mandy, her work had made it hard for her to have any real boyfriends.

One day Mandy and I had a working lunch at the Chart House. She wanted to go over some details about an upcoming case and felt a change in environment would be nice. In between discussing the case and laying out taskings, Mandy asked me questions about my professional aspirations and what I thought of the firm. I told her it was great and that all the people I met were wonderful and helpful. She said the firm was more like a family and family always sticks together.

Once business had concluded, Mandy asked if I had a serious girlfriend. I thought this strange as our conversations never crossed over into our personal lives. I regrettably told her that I was single and that I had been out of a relationship for six months. That spelled “I’m sex starved.” She said she was on and off with a few men, but didn’t think any of it was going anywhere. Mandy’s tone had changed dramatically and I now saw her in a total different light. She was funny and witty and could hold her own on just about any topic we discussed.

After lunch, we walked back to Mandy’s car and she asked if I didn’t mind making a quick stop at her house to pick up a file. Heck, she had paid for lunch, obviously billing it to the client, so how could I object. She asked me in and told me to make myself at home while she retrieved her documents. As I waited in her living room I checked out her pictures hanging on the walls. Mandy was indeed a looker.

One photo showed her on some tropical beach wearing a two piece bathing suit and looking very good. She was indeed a knock out, too bad her job didn’t lend itself to more free time for her. She apparently was also interested in horses as several of the photos had her in riding clothes and on horseback. I always loved the way tight riding pants and boots made woman look. Her ass was truly grade “A.”

Mandy came down the stairs wearing a very skimpy sundress and told me she wasn’t going back to work that afternoon. She apologized and said she would call a cab for me, but wanted to go over just a few more details of the case we discussed at lunch. Okay, no problem, I was still on the company’s clock.

We sat down on her loveseat and we began going over the material. I took notes and acknowledged the tasks she needed me to work. I couldn’t help but notice that Mandy wasn’t wearing a bra as her sundress revealed quite a bit of cleavage. Her tits weren’t big, but they were perfectly shaped and it took a lot for me not to keep glancing down her dress. As she folded her legs back and forth, I got a good look at her long legs. Her demeanor was professional, but her actions said the contrary. My mind was racing and I found myself thinking about her in a sexual way. She sensed something was amiss and asked, “John, you seem distracted, do you want to pick this up tomorrow morning?”

"No, Mandy, I’m okay. It’s just that I find you very attractive, but please don’t take what I’m saying as me being unprofessional. I’m only human, and I just appreciate your sensual beauty, but I will always see you as my boss and I will never cross that line with you.”

She starred at me for a while and then placed the files on the coffee table. She leaned over and said, “You know John, I too find you attractive, you’re a very good looking young man and I have to admit, I have fantasized about making love to you a few times. If it weren’t for the fact that you work for me, I would have made a move a long time ago. But, maybe we can still be professional and indulge ourselves; after all, as you said, we’re only human.”

I took that as the “Green Light” to make my move. I leaned over and kissed her gently on the mouth. We tongued each other and I slipped my eager hand up under her dress and was surprised she wasn’t wearing any panties. Her neatly-shaven pussy was moist and I started to get hard. I caressed her clit and slipped a finger into her. She moaned with pleasure and responded by spreading her legs and groping my erection through my slacks.

She unbuckled my pants and unzipped my fly. She reached in and grabbed my now rock hard cock. I was so ready to make love to her. I got up and stripped off my pants, boxers, and shirt. Mandy lifted the sundress up over her head, revealing the sweetest toned body I had ever seen. She was definitely in great shape and her beautiful breasts, abs, and ass were such a complete turn on.

I lay her down on the couch and sank down between her legs. I feverishly licked her cunt and probed her pussy and asshole. She tasted so good and the smell of her sex had me ready to blow my load. As I continued to kiss and suck her labia, I slipped a finger each into her vagina and ass. She spread her legs even further to give me complete access. Her tight anus was like a vice on my finger and I picked up the pace on finger fucking both her holes. She was dripping wet and I knew it was only a matter of seconds before she climaxed. Soon she bucked and yelled out uncontrollably with her first orgasm.

Mandy then recovered and had me lie on my back. She immediately went down on me, taking my six-inch cock into her warm and wet mouth. She sucked on my head and shaft and massaged my balls. I was in heaven. Gosh, Mandy had a way of sucking cock and I was trying my best not to lose it. I told her I was about to come and she released my cock, shimmied up on me, and poised herself above my cock. She looked at me with a lustful gaze and then lowered herself all the way down on me. The feeling of that warm and hot pussy sliding up and down my shaft was orgasmic.

She rode me hard, grinding her hips as she raised and lowered her body. I loved looking up at her tits gently bouncing with each of her forceful thrusts. I played with her erect nipples. Her moaning told me she was enjoying herself tremendously. The urge to come overcame me with intensity and I shot my load deep into her. I bucked and moaned with pleasure. Since I hadn’t had sex in a long time, this climax was amazing. Just then, sensing my release, Mandy too came, experiencing her second orgasm of the afternoon. She collapsed on me and we fell into a restful sleep.

I awoke to Mandy’s gentle breathing on my chest. Her head was nestled into the crook of my neck and her sweet smelling hair, mixed with our light sweat, had me thinking of sex with her again. As I lovingly massaged her back, my cock began to swell between her legs.

Mandy opened her eyes and raising her head said, “My, my! My lover wants more.”

Our mouths met and we French kissed. She reached down and guided my now full-erect cock into her sticky pussy. Our bodies remained pressed against each other and she slow-fucked me for what seemed like an eternity. She then began to breathe more heavily and soon her body was wracked with yet another powerful orgasm. My cock filled her completely and I too climaxed. The intensity of this second orgasm was overwhelming and I was left completely spent. Mandy settled down and, with my cock still in her vagina, we fell into another deep sleep.

We finally woke at 6:30 pm. Mandy invited me to shower with her. I enjoyed running my soapy hands all over her slim and firm body. We kissed a lot and although we had plenty of sex already, I was beginning to get hard again. Mandy said to hold off, there would be plenty time later for more sex. Once bathed, I dressed, collected my things and left for the evening. I thought about what had happened and vowed that it would not interfere with our jobs in any way.

The following day, Mandy met me in the office for our usual morning huddle. I couldn’t look at her in the same way, not after what we had shared, but I had promised myself I would remain focused and concentrate on my job. We finished out the week and on Friday afternoon, she called me into her office.

“Okay, John, now that the week is over, I want to discuss a few things with you.”

I was a little apprehensive at her casual tone, but she surprised me by saying that she wanted to see more of me. I was relieved. We discussed the ground rules for our relationship, so it wouldn’t interfere with our work. Mandy and I spent most weekends together and having plenty of great sex.

Then one day I was called into Mandy’s supervisor’s office and he offered me a full time position working for Mandy. Apparently, her old assistant wasn’t coming back after all. I was excited and thankful. Mandy congratulated me and said she’d now have to work especially hard to keep erotic thoughts of my cock fucking her pussy from distracting her all day.

I said, “Hey, anticipation goes a long way in making sex so much better.”

Then in mid-August, an email came out stating that this year’s end-of-summer office party would be a beauty pageant. First prize was an all-expense-paid trip for one week to Jamaica. No sooner had I started reading the memo, my phone rang. It had the two-tone ring alerting me that it was someone from within the building. I looked down on the phone display and saw that it was Mandy.

I answered the phone, “Well hello Ms. Beautiful Mandy Fletcher, what can I do for you today.”

“Did you read the end-of-summer memo yet,” she said excitedly.

“Ah, as a matter of fact, yes, I just finished it. Why, are you going to doll yourself up and win us the trip to Jamaica,” I said.

Mandy replied, “No my silly John, you obviously didn’t read the entire memo. It’s the men who are going to enter the contest; it’s a beauty pageant for men. I thought we’d dress you up in a pretty little gown and high heels and you’d win us the trip to Jamaica.”

I was stunned, dress up as a woman, no way, I’d be the laughing stock of the firm. I quickly reread the memo and saw my apparent error. Although, my body wasn’t large, I wasn’t a petit little thing either. How could I possibly win dressed as a woman?

Mandy said, “Hey, before you say anything, remember you said you’d give 100 percent effort for your boss.”

“Well, yes, I do remember saying that, but that didn’t include feminizing myself and strutting up and down in front of a panel of judges,” I said.

Mandy sighed heavily and said, “Now, now, my dear John, won’t you just think about it for me? A trip to Jamaica at company expense is such a wonderful deal. We have a few weeks before the pageant, so think it over and if you decide to indulge me, I’ll be sure to make it up to you. After all, I think we can take the prize because I’m looking at our potential competition and it looks weak.”

So, that weekend at Mandy’s we had another round of mind-blowing sex. I couldn’t remember ever having that many orgasms in one day. She loved to fuck and we now had added anal sex to our list of routine acts. On Sunday morning, Mandy said she really wanted to win the trip and that a few of the other lawyers were talking about who was going to enter and the prospects for them to win. She said my name was thrown around and it made me feel a little strange, but hearing that gave me a sense that I now belonged to the firm and the staff and lawyers had accepted me as one of their own. “Please John, I know we can win, it’s only for one evening” she pleaded.

I had thought about it and decided what the heck, no big deal, I was confident in my masculinity. “On one condition, I get the aisle seat,” I said jokingly. We both laughed.

Mandy squealed with joy, “Oh thank you John, you’ll see, I know we will win, this will be so easy.”

The party was on a Saturday at the Ritz Carlton Hotel, so Mandy had me come over to her house around mid-day to get started with my transformation from dull John to sexy Mindy, my new feminine name. Mandy had me strip off all my clothes and hop into the shower where she had me shave my legs, chest, and under arms. I thought this excessive, but she assured me it was necessary as we had to make me look as close to a real woman as possible.

Afterward, she lathered me up with cocoa butter lotion to sooth my freshly-shaven body. The scent reminded me of my older sister as that is what she always used in the summers after bathing. It smelled wonderfully sexy and I actually felt my cock starting to get hard.

Mandy looked down and said, “Not now Mindy, there is no time for sex, save those urges for later.”

Mandy had prepared thoroughly as she had measured me up the week prior and went shopping for everything that I would need to make a fine and sexy looking female. She tucked and taped my penis and balls between my legs and then had me slip my legs into a very feminine looking black satin panty which she called a gaff. She said it would hold my cock in place no matter what and it would give me a nice flat appearance where it meant the most. Next came a very pretty satin waist cincher that squeezed the crap out of my waist. She leaned into my back with her knee and pulled hard on the strings, cinching off about five inches from my waist. I could hardly breathe.

Then Mandy fetched a pair of 36B false gel breasts from a small box. She had me hold them to my bare chest over my nipples.

“Is this truly necessary, couldn’t we just use tissue paper or something,” I said.

Mandy cocked an eyebrow and gave me that “you-aren’t-serious” look and said, “No, the breasts are the first thing judged, they have to be as real as we can get them and since you haven’t been taking female hormones for the last six months, you don’t have a real pair to flaunt in your sexy matching bra.” “Oh, sure, that makes complete sense,” I thought.

So, Mandy placed the bra around my chest and ran the straps through my arms and up over my shoulders. She fastened it and then adjusted the breasts and straps. I have to admit, the breasts felt very nice gently tugging on the straps. The fake nipples protruded slightly against the thin material of the bra’s cups and Mandy said a little nipple showing would be desirable as it would drive the judges wild. I really hadn’t thought about turning any male judges on!

Mandy had picked out a very slinky over the shoulder black dress with a deep V-neck front. It was very tight fitting and was made of a stretchy material, so it clung to my now beautiful breasts and slim waistline, giving me a truly feminine appearance. The hem of the dress was very short and fell about eight inches below my bottom. Mandy then had me sit on her bed as she rolled up a pair of black seamed stockings. The tops were made of lace and they matched all the other lingerie I wore. Mandy attached a set of garters to the waist cincher and then fastened them to the stockings. The dressing part was complete.

For the next two hours, Mandy applied just about every cosmetic she owned to my face and neck. She used all sorts of brushes and powders to get my complexion just right and then painted my eyes and lips. A false set of very long and thick eyelashes and three coats of jet-black mascara left no impression that Mandy wasn’t out to win. She then carefully applied a set of nail extensions to each of my fingers and then painted them to match my lips. She said the deep red color would definitely stand out and make the sultry statement that Mindy was a serious contender.

To complete my womanly transformation, Mandy had me try on several brunette wigs, all of which matched my natural colored eye brows, which I may add had been tweezed to nothing more than a very thin arch. She settled on one that had bangs and was slightly layered to frame my face. It felt uncomfortable to be wearing a wig, especially since it was summer, but Mandy assured me I would get used to it, just as I had gotten used to my new breasts.

Lastly, Mandy dolled me up with jewelry, perfume, a small black over-the-shoulder purse and a pair of three-inch black stiletto-heeled pumps. She walked me over to the full-length mirror and I couldn’t believe the dramatic change. I was definitely a woman, a very hot and sexy woman. Totally unbelievable! Mandy had done it; I truly looked like a real woman. The makeup she applied was flawless and my beautiful eyes and lips appeared sultry and seductive. I was ready to win this darn pageant.

We drove to the hotel and I was not in the least anxious as I knew other men would be there, dressed to the nines, and competing for the grand prize. Once we arrived, Mandy pulled up to the front entrance where a valet opened my door for me. He said, “Good Evening, Ma’am, you look very nice tonight.” I was floored, here was a young man and he didn’t see anything amiss with me. That was a good sign.

We made our way up to the Cypress Room, which had been reserved for our event. There was even a stage erected at the front, apparently for all of us “girls” to strut across later. Mandy and I found our seats and we began chatting with another couple. I looked around and saw a few dolled-up men, but other than those few, I couldn’t recognize anymore. The evening progressed and the couple at our table commented on how interesting it was to have a beauty contest for this year’s theme. Last year’s theme was come dressed as a fairy-tale character and that was okay, but not as fun as watching the boys sashay their little rears across the stage.

Mark, a guy from corporate and who was sitting to my left, commented on how sexy I looked and said I was a shoe in. The more he drank, the more he openly flirted with me. He commented on how beautiful I was several times and how my sexy outfit turned him on. His wife kept kicking him under the table. Obviously drunk now, he commented on how he’d love to have my pretty painted mouth wrapped around his cock.

His wife got up and left the table, apparently annoyed. I thought it was hilarious, but deep down his comment struck a chord, I actually felt different about myself. The thought of sucking another man’s cock was always repulsive to me, but now I actually thought about what it would be like to suck another man’s cock. “What was happening to me,” I thought.

Then the big event of the evening finally arrived. All the contestants were called behind stage and Mandy kissed me gently and wished me good luck. I walked as carefully as I could in my heels. I didn’t have much practice in them, but all I thought was “Please don’t fall, please don’t fall, you will blow it if you do.”

There was a large mirror for us girls to check our makeup. I applied another coat of lipstick, just as Mandy had taught me earlier and was now ready. I was third out of eight lovely looking women and my heart immediately went into overdrive just thinking of what I was about to do. I calmed myself down just as I was called to walk out onto the stage.

As I walked around the curtain I was blinded by all the camera flashes. Everyone was clapping and this actually made me feel that I was in a real beauty contest. I sashayed out walking as a model would on her runway debut. I paused at the far end of the stage, just as I was taught, gave a twirl, and returned to the other side.

The judges wrote in their note pads and I wondered how I fared. I went back behind the stage and nervously chatted with the other contestants waiting for the end of the first round. They all looked very passable as woman. I felt weird that I was attracted to one of them. Like me, she had gorgeous shapely legs and a tight little butt.

Her stage name was Tiffany and she looked fabulous wearing a long red asymmetric sequined red gown. Her hair was all pinned up on top of her head and small little tendrils of hair dangled down from her temples, which framed her pretty face. She worked in accounting and said she was forced into entering the pageant because she lost a bet with one of her friends. Hell, she looked great. If I hadn’t known she was a he, I would have asked her out.

Then we waited for the judges to announce the winners of the first round. Happily, I was called out onto the stage with Tiffany, of course, and another beauty named Shelly. Shelly was also hot, but you could tell she was a man dressed as a woman because she had a very pronounced jawline and broad shoulders. We then each struted across the stage one last time. I gave it my best to sway my hips and extend my long heeled legs as I walked across the stage. I was really enjoying this wonderful feeling of playing a woman. As my heels clicked away I felt my breasts gently sway within the confines of my lacy bra. It was truly a remarkable feeling and experience.

Then the moment of truth was upon us. I actually felt sick as I so much wanted to win. Here I was, dressed completely as a woman and wanted to win this silly pageant, not just for Mandy, but now for me. I now knew how women on Miss America felt as the judges lined them up for the announcements of the runner ups. My knees were weak and it took everything I had not to pass out. I looked over at Mandy and she smiled at me, giving me that reassurance I so desperately needed. The third runner up was Shelly, thank God!

It was now down to just me and Tiffany. Then something odd happened. I instinctively reached down and clasped her hand in mine, just as the women do on Miss America. I stood there holding onto Tiffany, hoping the judges would pick me as the winner, but the thought of Tiffany losing made me sad for some reason. Something deep inside me was going on…I had a feminine side and it was coming out full steam.

The judges paused for effect, then announced the second runner up…Miss Tiffany. It took a second to sink in, I had won! I had taken first place in the beauty pageant! My heart raced and then it hit me like a freight train, the emotions overtook me and I began to cry. I was crying. What the heck was happening to me? I covered my face and tried desperately to gain control.

Everyone was cheering and whistling and as I opened my eyes, the lead judge was placing a shining tiara on my beautiful head. I fanned my eyes as to not ruin my mascara. I was then handed a large bouquet of flowers and a large pink envelope with the tickets to Jamaica. We won; Mandy and I had done it! We were going on vacation. I proudly strutted off the stage where Mandy was waiting for me with open arms. She embraced me and gave me a long congratulatory open-mouthed kiss.

Everyone clapped and shouted, “Congratulations Mindy.”

After everything settled down, we made our way to the valet station. Tiffany was there waiting for her car. She congratulated me and said I deserved to win and that she was happy for me. God, she looked so adorable, sad, and vulnerable. I leaned into her and gave her a soft kiss on her cheek. To this day, I do not know why I did that, but it just felt right, again, my female persona taking over. I whispered in her ear, that in my eyes, she was the true goddess of the competition. She smiled and said thank you.

Mandy looked at me and said, “My, if I didn’t know any better, I’d say you really loved being Mindy tonight. What’s up with you kissing Tiffany? I’m a little jealous.”

I looked at Mandy and said, “She’s a sweet girl, I’m just sorry someone like her had to lose.”

Mandy then gave me a big smile and said, “I think I see Mindy being a regular part of our lives. Perhaps we should invite Tiffany over next weekend for a threesome. What do you think?”

From the look on my face, I didn’t have to answer that question.

This story is protected by International Copyright Law, by the author, all rights reserved. If found posted anywhere other than with this note attached, it has been posted without my permission.

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