Becoming Madame Mayor

by Erica Smooth

  Becoming Madame Mayor: BUNDLE 1-3

  Becoming Madame Mayor: Part 1

  By and large, when Tina suggested something unique to me, I was immediately on-board; but, this was insane.

  "You want me to what?" I asked her, as my eyes squinted in her direction.

  "Abe, I want you to consider coming out as a woman," Tina said with a serious tone. "Publicly declare your intention to transition and proceed as a girl."

  Tina was my campaign advisor, life coach, and best friend. She was a beautiful girl with dark curly hair. We had met in college and we somehow managed to play an important role in each other’s lives all these years later. I had graduated with a political science degree and she had a degree in business management. Our academic credentials somehow managed to reflect our unique personalities. I was an assertive, confident leader and Tina was a motivated, strategic organizer. While there was sometimes a feeling of sexual tension between us, by and large we were in a strictly platonic relationship. This, of course, didn’t mean that I wasn’t secretly lusting for her. I just assumed she had me in the friendzone. I was on the small side, but I was a pretty good looking guy. I always wondered why she never showed any interest in me. She constantly had what I affectionately called, ‘The Boyfriend of the Week’, but she never seemed to want to settle with anyone. I had even seen her with a few women. The subject of sexuality never came up, but I concluded that she must be bisexual or maybe just confused.

  After college we had both spent a few years volunteering and working with nonprofits. The altruistic work helped bolster our resumes. The work fostered pragmatic passion in each of us and inevitably ended up pushing us into the cutthroat world of politics. With Tina’s help, my first elected position was on the local school board. This was my first real taste of public service. Riding off that success, the next year Tina helped me campaign and successfully get onto the city council. I held a seat on the council for a few years but now I was attempting to secure my highest position yet: mayor of Riverside.

  Riverside was a unique place in that it was exceptionally diverse and open to change. People in our town celebrated progressive thinking to an extreme. The topics of gay rights, the women’s movement, the ‘me too’ movement, ‘black lives matter’ and every other social justice keyword-of-the-day, were used as a rallying call to the majority of residents that lived here. We were undeniably liberal and Tina and I fit right in. I was proud to call Riverside home. People voted aggressively on these subjects, sometimes to a fault. Therein was my problem.

  I was up against a man named Tom Burken. Tom had been a big-wig lawyer for a local credit union and somehow he ended up getting into politics. He wasn’t particularly qualified for the position; but, he was handsome, charismatic, and most importantly: he was gay. In Riverside, this was a big deal. So here I was in my dining room and my campaign manager/best friend is telling me I should become a woman.

  “Abe, please stop pretending like you think this is a bad idea,” Tina insisted, “I’ve known for years that you aren’t comfortable as a man. You’ve just been so boxed up about it. Every time I try to bring it up you shut down on me.”

  Tina was right. I did have unaddressed feelings; I’ve had them for years. When she tried to bring it up I would quickly change the subject. Ever since I was young I knew I was different. I was more comfortable brushing my sister’s hair than I was playing kickball outside with the boys. In later years, I was jealous that my prom date got to wear a beautiful dress and I was stuck wearing an uninteresting and bland tuxedo. I yearned to put on a dress, makeup, and heels every morning. I was jealous of beautiful women. To this day, I have a lock box under my bed filled with sexy lingerie, bras, panies, stockings and heels. At least once a week I would put on the clothing and look at myself in the mirror. Often I would masturbate and watch porn while I was dressed up. I fantasized about being a woman but I craved femininity in a non-sexual way too.

  I had dated many girls growing up, and I was attracted to them, but I had to be honest with myself. I never truly identified with my masculinity. The idea of being with a dude was never particularly appealing to me. I never felt gay, I just didn’t feel like a man. Maybe it was lucky genetics or maybe it was just pure willpower, but somehow I was able to compartmentalize this part of myself and still lead a productive and successful life. I drove my desires into a dark corner of my mind.

  So here I sat as Tina directly called me out. She once found a pair of panties under my bed. I lied and told her they were from a girl that I had over the night before. There were some other incidents that probably gave away my secret as well. I looked down at Tina’s legs. She was wearing a pair of sunkissed pantyhose. Or perhaps they were stockings; It was hard to tell. The point was, I was jealous. She had a pair of classic black high heels on her feet that appeared to be 4 or 5 inches high. She was also wearing a black skirt and white blouse. If I was being truly honest with myself, to my core, I had to concede that I wanted to be wearing those sexy stockings and heels.

  “Yeah,” I admitted, “I’ve been trying to suppress this side of myself for as long as I can remember. Maybe I should just own it.”

  “Abe, you know that I’m just trying to help you,” Tina said. “I think this would great for you personally, but there is something else you should consider. This would give you the edge you need to win this election. This town would love a ‘coming out’ story; you and I both know that. Sometimes I think these people would elect a bank robber if he or she were LGBTQ”

  “You’re right,” I agreed. “The only reason I’m down in the polls is because Tom Burken is an openly gay man. In all reality, he’s not the best choice for this city. My platform is more comprehensive and valuable for this city.”

  I thought about myself standing at a podium, about to give a speech. I’d be wearing a navy blue business suit, stockings, and modest heels. In this fantasy, I would be hiding a sexy black bra and panties under the suit. My hair would be down around my shoulders and I’d have pretty red lipstick, dark eyeliner and mascara on my face. The scenario playing in my head gave me confidence and relief from years of hiding this huge desire of mine.

  I had to ask myself, what is a successful politician? The answer now seemed obvious. She is nothing more than the manifestation of an individual’s confident identity, message, and plan. My message and plan were loud and clear but I lacked credibility because people were sensing my lack of confidence. This was a defining moment of clarity. I had to be true to myself. I need become the girl I was meant to be.

  As I sat at the table thinking about the pleasures of womanhood, I noticed an uncomfortable pressure in my trousers. I had a raging erection and it was creating a tent that was certainly visible to Tina. I tried to casually cross my legs but Tina called me out again.

  “The thought of slipping on some panties is turning you on, eh?” She looked down at the big circus tent in my pants. “Listen Abe, since we’re sitting here being honest with each other, I’m going to drop some knowledge on you. I’ve always been attracted to you, but I’m more attracted to women. I tried to fight it for years, but I’m definitely into chicks.”

  She went on to explain that the idea of dressing me up as a girl and helping me transition into becoming a woman was a huge turn on for her. She had been fantasizing about this scenario for years. She craved cock, but she also desired the softness of a woman. Just hearing her talk like this was enough to make my dick become even harder. The fact that she wanted to dress me up as a girl made my cum begin to boil. She told me that the series of events leading up to the mayoral election pushed her to finally confront me about all of this. She too, was feeling pretty liberated. In fact, she had even brought some items to help us celebrate.

&n
bsp; Tina pulled a plastic bag out from under her chair. She tossed it to me. “Here, these are for you. It’s just a little something to get you started.”

  I looked down at the bag and slowly opened it. My eyes immediately lit up and my cock lurched. Inside there was a colorful variety of fabric. I placed my hands inside and felt multiple materials: silk, lace, nylon, soft cotton and lots of stretchy elastic. The bag was filled with a few pieces of lingerie, two bras, about a dozen pairs of panties and a black dress. My hands trembled a bit as I ran them across the clothing. Then I heard Tina unzip her purse, and she pulled out three smaller packages. She tossed them at me and said, “I figured you would need some of these too.” In my hands were now two packs of nylon stockings, one white and one sheer black. The other pack was a pair of nude-colored pantyhose.

  “There’s actually more out in my car,” she said, with a grin, “Like they say: ‘Variety is the spice of life’, right?”

  I was speechless. I looked down in my lap at the clothes. I was experiencing a variety of conflicting emotions. Excitement, fear, joy… even arousal. Tears formed in my eyes and all I could do was get up, walk over to Tina and give her a deep hug. I held her tightly and softly whispered, “Thank you so much.”

  Tina giggled. “What’s so funny?” I asked. She pulled away, keeping her arms around my neck and looked down. My raging boner was pushing right into her. “Oh, sorry,” I said.

  “Don’t be sorry,” she said, with a devious tone “let’s take care of your friend down there and then get you dressed.”

  With that, Tina slid herself down me and put herself in front of my bulge. She then reached up, undid my belt, button, and zipper, and pulled down my trousers. She put her thumbs in the waistband of my boxer briefs and swiftly yanked them down my legs. This was the first time either of us had acted on our desires for one another and it was incredible. I couldn’t help but stare at her sexy curves and her pretty face. I was almost ready to burst before she even touched me. Tina brushed away the dark curls from her face before she leaned forward, looked up at me, and maintained eye contact as she took the entire length of me into her mouth. She held there for a moment, at the base of my cock and then began to work her head up and down on my shaft. I impulsively groaned out loud. Then Tina took one hand and groped my balls while she used the other hand to jerk me off while she sucked. I was experiencing a moment of pure bliss. Her warm mouth worked me for less than five minutes before I felt myself tense up. She sensed that I was about to cum and in response I felt her grip tighter and quicken her pace.

  When I could take it no more, I gasped, “Tina!”

  “Mmm hmm,” she hummed, with the entirety of my cock pulsating in her pretty mouth. In this moment, any thoughts of elections, polls, campaigning and politics-in-general had completely left my mind.

  With this, I trembled as I shot spurt after spurt of hot sticky cum into her mouth. Tina continued to bob her head up and down as I released a huge load into her. After what felt like minutes, she skillfully pulled her head away while keeping her lips pursed. She gave me another close-mouthed smile as she swallowed all of my cum. Then she opened her mouth, showing me that it was empty.

  “I’ve been wanting to do that for a long time,” she said.

  “Well why didn’t you? That was absolutely incredible!” I exclaimed.

  “I was just waiting for the right moment,” she replied, “Now that we’ve taken care of that pesky little bulge of yours, we need to get you dolled up.”

  I stood next to the dining room table for a moment and tried to digest everything that had just happened. In my post-orgasm state of mind, it was a bit much to comprehend. "Don't just stand there," Tina said eagerly, "lets get you dressed." I followed her into my bedroom as I wondered what clothing she was going to have me try on first. My body hair was naturally pretty sparse so I wasn’t too concerned about shaving at this point. I was also fortunate in that I had grown out the hair on my head to a decent length, for a guy. I already had a sense what I looked like as a woman because I had been doing it in private for years. With Tina’s help, I expected a very passable transformation.

  “Strip naked,” Tina instructed, “Come on don’t be shy.” I did as I was told, stripping off all of my clothes and throwing them to the other side of the bed. She pulled out a pretty black cocktail style dress made from soft sheen silk. As she brought the dress up to my body to check the fit, it glimmered in the light. “I was thinking we’d start you off with something very feminine,” she said, noticing my eyes widen as I stared at it. “That is an incredibly sexy dress," I replied. Then she went to the bag and pulled out a matching black bra, panty and garter belt set, followed by one of the packs of brand new sheer stockings. “Black lingerie is the sexiest lingerie. It’s standard for any woman that wants to feel risqué under her clothes.” Tina proclaimed. “I agree,” I said, “I often fantasize about this kind of outfit.”

  Tina then grabbed a different bag and pulled out a pair of breast forms. She sat me down on the edge of the bed and applied them to my flat chest. "It looks like you’re not too hairy, which is great. We’ll still get you shaved up for next time but I’m eager to see you all put together right now," she said. She picked up the lacy bra and held it up to me. Then she wrapped it around me. The bra had a clasp at the front but it also had shoulder straps also had to be adjusted. "Perfect fit, I got lucky" she noted. “I really didn’t want to have to go back to the store and exchange all this stuff for a different size,” she laughed. “Okay now let’s get those stockings and that garter belt on!”

  My favorite part of dressing had always been the stockings. Tina bunched up the first one in her hand and then she slowly slid it over my leg. I shivered with delight, as the feeling of someone else putting them on you was even more incredible than doing it yourself. She then slid the second stocking up my other leg and had me stand up. Then she grabbed the sexy little panties and had me step into them. She slowly pulled them up my stocking-covered legs with a look of determination on her face. She had to tuck back my slightly soft cock. "You’re enjoying this as much as I am, aren't you?" I asked. "More than you can imagine" she replied. "But it looks like you’re the one having the real fun,” she teased, as the bulge in my panties began to grow a bit and stick out the side. "I can’t deny it. This is the hottest thing that’s ever happened to me," I agreed. My mind was a whirlwind of excitement.

  Then Tina looked at my nails. “These will need some polish,” she stated. She grabbed a container with a dark red color and sat me down again. She had me hold out my fingers and she carefully applied polish to each of them. My nails weren’t particularly long but the nail polish made them look pretty damn sexy anyway. When they were dry she got up and took a step back to check me out. "You look hot as hell, now we just need to get you into that dress." she said. She had me put my arms up and she slipped the dress over my head. I stood up to let it fall naturally. There were no buttons or zipper, but there was a small clasp at the back. Tina pulled it down my body and adjusted the fabric near my chest so I was showing a little bit of cleavage. Then she fastened the clasp. I moved around a bit and noticed that my stocking tops were showing through a small slit on the side. "Do you think this is too short?" I asked, sarcastically. "Yeah, but you’re no cheap whore," she said, "you’re a classy lady of the night. Just make sure you take small steps when you’re wearing something like this. Overall I think it fit you perfectly." she said.

  At this point, I momentarily shifted my focus away from myself and looked at Tina in her little skirt. "I feel compelled to say that you are sexy as hell" I said, as her sexy boobs bounced up and down as she was dressing me. “Thank you,” she replied, “It’s weird that you’re choosing to tell me this now. Better late than never I suppose.” Then she grabbed a pair of black leather open-toed heels. They looked to have a heel that was about three inches. "These should work for now. I doubt you have much practice walking in these things." she said.

  She helped me slip my fee
t into the shoes as she rain her dainty hands across my stockinged legs. They slipped in easily because of the stockings. Then she had me walk around the room and she gave me some tips to help keep my balance. I found her advice made it a lot easier compared to when I was secretly crossdressing alone in my bedroom.

  "How do the shoes look?" I asked. "They look fantastic" she said "as a matter of fact, you are looking damn near perfect. We just need to get some makeup on your face and fix your hair to complete the transformation." Tina brushed my hair for a bit and worked her magic until it was looking perfectly feminine. Then she started to put some makeup on my face. She put on foundation, blush, eyeliner, mascara, and lipstick. When she was done, my face was looking flawless.

  So the transformation was finally complete. I stood up and walked over to the full-length mirror. Before me stood an extremely attractive woman. I couldn’t believe what I was seeing. I kicked back a heel and admired my shapely, stocking-clad legs. I looked at the nice little bubble-but at the hem of my skirt. I even had great-looking tits! Suddenly I felt my cock start to stiffen in my panties and poke into the material of my dress. Tina walked over to me and gave me a tender kiss on the mouth. The pressed herself against me and took notice of my cock. She reached down and played with it through my dress. “I guess i’ll have to take care of that again,” she purred. “Before I do, you need a name. I’m thinking Abigail. What do you think?”