A Lost Lover, Changes for Melissa Pt. 01-02

I rolled onto my back and was alert for some time thinking of her gender decisions, how she had remade her own world. Her sex was a bit frightening to me because I had definitely been aroused at least once by a cross-dressed woman. It was years ago when I was in New York and saw these three 'ladies'. They were so blatantly sexy yet dressed as women, dresses and tall heels, makeup and long hair. I started to get hard just thinking of them as Cindy snored softly.

One of them had called to me, "Come on the wild side mister, my mouth is as warm as any of those other girls,".

I was alone and watched them strut down Broadway raising other people's interest. I followed for a block or so but grew embarrassed and turned. The taller one saw me and called back to me, "We won't bite, ".

Cindy had told me of how she had decided after college. Cindy being a woman, I wondered if she thought of herself as a gay person as well before her transition. I think those cross-dressers were comfortable with gay sex. I had not shared the NYC sighting with anyone, not even my Ex. I now recalled the Apple ad's for 'think different'; maybe there was some history I was deeply repressing.

I recalled Cindy saying, "I felt so un-male Thom. I met a girl in my economics class. She explained herself to me, her boy name had been Charlie, but now she was Marie. We became lovers for a while. Marie was a transgender woman who was planning to have a SRS within a year or two, when she had the money saved. She decided to transfer to Yale; she was quite good at mathematics. We lost touch but her thoughts and her views of her womanhood somehow affected my own sense of self. I began the process of understanding my gender."

This was earlier at the bar and she sipped her glass to pause a moment.

"You have been with tons of girls, right?" Cindy asked me.

"And you have never questioned how you fit in?" she paused for affect, "Well there are many different paths to transitioning and mine was difficult and started late but I knew I needed to do this."

Early the following morning in Vegas I had awoken to her sucking me to semi-erect but I wanted to fuck. I had decided something about myself and she deserved to be loved. My nighttime thinking and the dreams allowed me to suspend judgment on whether I was having a homosexual affair.

"Ohh Thom, really? Oh please," Cindy moaned and rolled to her hip.

First I had to use my slick wet finger to relax Cindy's butt. My finger was covered in saliva; there was no resistance at all as my long digit slipped into her pussyhole. She was squeezing my finger as I pushed deeper inside her bottom. I had most of my index finger inside her sexy butt; I pulled free and then I pushed two fingers inside her hot body.

"Ohhh Thom, yeah, oh please fuck me!"

"Is there any pain Cindy," I asked.

"No Thom, but I have used a lot of toys to tease myself and have orgasms. The first rule to anal joy is, go slow, the second, use a lot of spit." I moved into her hot bottom again with two fingers.

"Oh yes Thom, ohh ".

Cindy was moaning as I pulled back and out. I then twisted my two fingers, sort of twirling inside of her bottom while I moved in and outward. My fingers were still wet when I shifted and pulled free of her tightness.

"Come on Thom, don't you want to feel something incredible?"

The sun was coming into the room and she looked magnificent. I moved to kiss her as I reached to caress her breast, "You are ready Cindy?" I asked as I shifted to position my penis.

"Thom, yes, you are ready too, push the head of that great dick into my pussy," I knew I was going to fuck her. Cindy was no longer looking at me over her shoulder as I pushed slightly against her hole.

"Okay Cindy, " I slipped a bit of my cock inside her sexy tight butt while Cindy was on her right hip.

I felt her body open around the fat tip of my cock, she moaned softly as my dick head was inside of her bottom.

"God yes Thom, be with me, yes that is perfect."

My hand moved to her left breast as I pushed slightly. I had enjoyed my Ex's bottom but this was different. Cindy seemed to enjoy the penetration.

"Fuck me Thom, slip your hard cock in deeper," she sighed. "Yes fuck me, yes Thom,".

Quickly I was fully erected and we fucked like school kids, well I didn't pump too aggressively, "Oh Thom, yes, you feel perfect."

A few minutes later I came inside her ass with Cindy panting, "Yes Thom, don't stop, yes, fuck me, ohhhh," I think she came but I could be wrong.

There was no messy stuff and her canal was moist though I hadn't used any lube, only my saliva.

Cindy's ass had fuck me and I saw how much she loved it. She moved to lick me clean and then we kissed. So to hell with what is normal.

- - - - - - - -

Our late Friday conversation had started at Happy Hour with the six others. It was dark and past eleven when she'd asked me to her flat. It was late but we had discussed her collections and I wanted to see her bike for myself. Arriving at her small loft she showed me her amazing collection of stuff. First the electronics and her old male toys; the great Ducati motorcycle sat empty of fuel in the front space near the door.

With a glass of wine in hand she said, "I want to show you my coolest collection Thom. I have four historic ball gowns," she took my hand and led me.

As we moved into her dressing suite I was a little apprehensive but we were a bit drunk. There she showed me her wardrobe and something just changed. The surprise was the number of gowns she owned.

"Where can you wear these beautiful dresses Cindy? These are vintage right?"

She stopped and turned to me, "Not dresses Thom. These are gowns and why right here you silly boy. I can dress anyway I choose to make myself happy. Would you like to see?"

A bit later as we sipped the deep red Pinot that matched the color of her gown that she had changed into she told me the history of the garment.

"Three different shades of her red-colored gown were made for Marilyn Monroe during the filming of 'How To Marry a Millionaire'. This one is one of the rejects. I had it altered to fit me. Miss Monroe's breasts were a tad bigger. Strangely the hip and butt fit just right. How does it look to your eyes some fifty years later?"

She was wearing a medium heel and I could see her lower leg only a bit as she spun.

"The purple satin version they used in the film doesn't look as good as this ruby red to my eyes," she said.

She was moving, dancing and I was dizzy watching from the chair.

"It wasn't free but I feel lucky to own it. It is in remarkable shape given the satin is old. They rejected it for the movie and it was stored in a box. The woman I bought it from on an auction site was one of Monroe's attendants and she removed it after the film was completed. It has handwritten notes on the inner liner. Want to see?"

She stepped close and Cindy pulled down the bodice exposing her breasts. I immediately saw the scribble from the seamstress. Shit, my eyes were fixed on her beautiful breasts.

"But couldn't anyone have added those notes?" I asked.

She smirked, "Non-believer! Doubting Thom! But how does it look on me?"

I looked to her face, than to her exposed breasts, her nipples were hardening.

"Are you excited by the dress or me?" I asked Cindy.

She came beside me and grabbed my arm, "Well actually both but I sense you're anxious being around all of this feminine stuff, correct Thom?"

She was more than a bit correct. Our previous sexual affair was quite rudimentary. I hadn't been with someone for whom sex was so in control of her life. Cindy's hormones had helped her with a beautiful yet medium size pair of breasts. The drugs had also affected her penis; it was nearly invisible. Sex meant I had enjoyed her blowjobs and I had fucked her ass. She didn't like to refer to sex in that manner. To her the opening was between her legs and therefore it was her pussy. Though tight it was clearly different than the pussies I had enjoyed previously.

She had her arms about my neck as she swung about in the satin gown and heels.

"Can I dress you? Is that where this is heading Thom? Care to paraded about with me in a corset and heels, hummm?"

Strange but that was exactly what was on my mind. She had somehow cooped my maleness and I couldn't get the thought of her beautiful wardrobe out of my head! I had considered much since the Vegas trip and now I was not willing to hold back. Seeing Cindy in the red Monroe gown was too much and I stood considering her request.

"Thom we can," she came and looked at my face, "but have you ever done this, really dressed before?"

I told her no, "What have you in mind Cindy?"

She walked me to the bath, "Get out of the suit and use this," she turned on the shower.

I stepped naked with the razor into the warm shower, "How can I do my back?" but she was there with another shaver. Ten minutes later I was drying and felt the tingle of my smooth skin.

She handed me the small beige pants, "No that is a panty, Thom, almost a girdle. Slip it on please."

The questions I considered were swept away by the arousal the process was causing.

"Can I help you with that," Cindy pointed to my stiff penis.

A minute later I released into her palm, "Now we can get down to business Thom."

I had not considered what was happening but it was true that there was a desire.

Cindy spoke of her own first time, "I was barely out of high school but my mom's full body girdle just looked interesting. I ruined the hose' she had left to dry. I never told her and she never asked me about them. A year later I left for college and began my transition."

Looking at Cindy holding a wig I wondered and then she turned me towards the mirror and saw the wig settled onto my head.

"Almost there Thom, " Cindy said softly.

She quickly adjusted the hair and I looked at the reflection.

"Wow, oh Cindy what have you done?" I saw a woman. It was me sitting with Cindy just at my shoulder. I saw the bra straps and the face, full of desire and a smile. She had made something new of me. I looked up and she saw my eyes. She bent and hugged me.

"Now the dress,"

I stared and thought of the girls I had seen in New York.

"There Thom, you do look feminine, stand please," and we both saw the affect of the shape wear. She took me into her dressing room and it began. The night would change me forever.

The late Friday night with Cindy ended with me not getting home until nearly six on Saturday morning. My Ex was asleep but I caused her to stir when I sat softly on the edge of the bed. She turned and slightly opened her eyes without truly seeing me.

"What time is it Thom?" she sighed as she rolled over onto her right hip and again closed her eyes without noticing how I was dressed.

"You smell good Thom. What are you wearing?" she quietly said but still did not focus on me.

Cindy had dressed and prepared me all night and had applied White Linen on my neck and wrists. I didn't answer but stood tall as my Ex became alert.

Cindy had helped me shave my legs and crotch and she had sucked me off. I had participated in this full feminine experience though I could never have done so on my own. Having her direct the process seemed fun at first but my arousal grew as the details were manifested by Cindy's magic. The panty girdle held my dick back and hidden. Even as aroused as I was I could not become erect.

"Perfume?" My Ex said as she turned back now to look at me, she saw me and bolted up in the bed. She was wearing a beige nightshirt.

"What the hell? Who's clothes are you wearing? A wig and jewelry?"

She jumped to her feet, "Thom what the fuck! What the FUCK!" she screamed and walked nearer and away from our bed.

I was wearing what Cindy referred to as an ultra corset. Together with her waist cincher, which was beneath the corset; the taut pair of support garments had taken Cindy nearly an hour to get my tummy flab down to a twenty-nine inch waist. The support combination allowed the size-ten little black dress to look pretty good on my body. The nude hose' and Cindy's makeup work together with a long natural wig in soft blonde completed this vision that I presented to my Ex this early Saturday morning.

She had slipped back to sit on the bed edge as she wrapped her nightdress about herself.

"How did I miss this Thom? That you were dressing, I mean what the fuck Thom, I mean like this?"

She just sat looking at me but her face wasn't red with anger like I had thought might happen. I hadn't expected to actually go through with Cindy's plan. But as the night progressed and I saw the woman she was creating I got quite excited. Our relationship was nearly over and now I wondered. What was my Ex thinking as I stood less than four feet from me with her near nakedness?

But the look on her face had shifted, "I guess you did what you were intending Thom. I'm so shocked I can't think of an appropriate statement, well other than, "

She paused and then stood, "no, I'll be honest, you look remarkable Thom, or is there another name for this 'Lady' in my bedroom? Did you,"

She started a statement but changed her thought as she stood and paced, "What the fuck, you expected me to run, to throw you out?"

I had the ride over to consider what her reaction would be. What did I want from her? It was complicated. I felt anew, not anything like the person ' Thom '. Therefore, I wanted her to be surprised but I had expected revulsion because in my head there was a perverse joy in causing her some hurt. She had left our bed for another, though I had no proof. Clearly she wasn't responding like I had expected. I stood tall in Cindy's three-inch heels with the posture that Cindy had taught me; my faux breasts pushed out and forward. The silicone falsies were the lead. I caught a glimpse of myself in the mirror and smiled.

She saw this, "I see you are happy with yourself, the waist does the trick, but your face is becoming, for a man wearing a dress."

I told her it was okay for her to mock me, "I can't tell you why I did this last night but now it feels right."

She had stepped back toward the bed but paused and stepped closer now and her fingers touched my dress. She felt the support garment beneath the fabric at my narrowed waist.

"I figured there was a corset, but still. You've got a figure. Has my lack of focus allowed you to lose twenty pounds?"

Now standing at my side in her bare feet meant she was shorter than me in the borrowed heels. We were actually very near the same height. Cindy had tightened the laces of the cincher three times over the hour that I had sat while she had applied the foundation to my face and neck. As my body had adjusted and she finished with my face we had worked the ultra over my hips and tightened the strings.

"Can you turn for me sweetie?" my Ex asked with a soft voice as she settled back to the edge of the bed.

Her tone now shocked me but I was strangely enjoying her looking at me, at the 'woman' in her bedroom.

I did as she asked but missed a step and almost fell atop of her. She caught me with her left hand and then ran her fingers about my hips.

"It's quite an impressive outfit Missy. Did you have help?"

As she said this her fingers came to the back of the dress and she felt the tight corset strings. As she took in the details I thought more clearly about why I had decided to follow Cindy's suggestion. It was at first a desire to try something quite different but it became somehow me as I witnessed the transformation. It astonished me and baffled my mind that there would be a female within me and Cindy could root it out from the deep part of me.

"How can you breathe?" my Ex asked. "Maybe you've had your body modified without my knowing?"

Now her fingers explored the tight garments concealed by my black dress.

"Oh Thom, you've had to have had help to get your waist this small!" Her hands held me at my narrow waist.

Getting the ultra on seemed easy until Cindy began to pull on the special wide laces. This corset did the true trick as it held the silicone breast forms in the bra cups. I had sat quietly as my body adjusted and Cindy applied the mascara and eyeliner. She even adjusted my eyebrows.

I stood watching my Ex quietly wondering when her rage would rise but she seemed to be enjoying me this morning. We had not had sex in over four months.

"I must say that this Saturday surprise has me excited. Can I assume that you're also admitting that you are having an affair? With that bitchy little boss I'll bet. What's her name?"

I simply said "Cindy," and stood tall in my sexy heels.

"Give me ten minutes to get ready and we'll run out to get some coffee. My god I think you can pass as a woman. Anyway, it's a bit of a test, for me at least."

Cindy had thought so as well, after the shave and working on my face for over an hour though. It had been the wig that convinced me that I might not look ridiculous.

Once we were in my Ex's Camaro I became a little uncomfortable with her plan.

She looked at my sexy legs as she turned the key, "You've always had great legs but shaved they look stunning Missy."

I felt I looked okay, but I didn't really have a clue; and then I realized as she moved down the road that I was overdressed for a Saturday morning in the borrowed LBD and heels.

"Tell me how you came to the decision, to dress, I mean to play correct? With Miss Cindy all night?"

I now wanted to have her turn the car around and asked her to do so.

"Please, let's just make the coffee at the house."

She giggled, "No way Missy. You and me are going to have a fun day and I need you alert. Besides, I want to hear you order the Grande and a Venti for yourself."

When we arrived she turned off the car as I started to get out, "Sorry Thom, you do look remarkable but there is no way I will let you present yourself dressed quite yet. You need a lot more coaching and other details settled. I'll be right back," she slipped out giggling.

When she returned with the two coffees she volunteered telling me of her affair.

"Yeah, I've been letting a woman fuck me for almost three months. She is quite pretty but she is somewhere between a full stud and a chapstick dyke. She treats me as her pillow, but a femme too, she knows how to love a woman's body quite well. I've come to realize I like sex with women Thom."

She handed me the hot brew and giggled, "But you've known that since we met. Wow, now I'm married to a true femme huh?"

I considered this a moment; she had been with several women in college and I had been told by her of the joy that my lips and tongue brought her, 'almost that good'.

The car speaker indicated that she had an incoming call; 'Lindsay' it announced.

"Please dear don't take the call," I asked.

She shushed me as she hit the steering wheel control button, "Yes Lover?"

The speaker was quite clear, "What time after two did he get home?"

"Lindsay I shouldn't talk right now? Not here at least. Can I bother you to come by the house, say near noon?"

I couldn't say anything now to stop her but I could simply leave before noon. Shit I could simply change out of my dress.

The voice on the call said, "Sure, anything important?"

"Please Lindsay, can we talk at the house?"

Just then the fuel light came on the dash. She quickly pulled over into a station.

"Lindsay, I mean, please, I have got to take care of something with the car. May I please say goodbye for now?"

She hung up and turned to me before getting out to start the pump working.

"You will have to decide Missy. I think my girlfriend and I could enjoy your present situation. You need to understand Thom. You and I will surely be meeting with attorneys on Monday if you runaway. Could you allow me to understand how committed you are to the outfit? To the way of life that a transwoman lives?"