The Making of Monica Ch. 04

The making of Monica. Part 4

An un-expected helping hand.

As I developed and grew both mentally and physically with the Crossdressing, the toys, the strap-on porns; enhanced with shemale porn lifted me to higher levels. But when I found the cock compilation; sissy girl compilations, you want to be the girl compilations, you are a sissy slut compilation (videos) online, that grew my lust more.

I couldn't get enough. I had almost given up on buying or searching the web for strap-on porn and just sat in my room with my lap-top searching; How to be a crossdresser? How to be a woman? Sissy Hypno. Female Hypno. Put your panties on Hypno and a host of similar videos, just watching real girls or Transgender girls getting big hard cock rammed down their throats, or up their asses. I would use my toys and fuck myself to high heaven until I squirted all over my sheets.

I wanted to be those girls. I wanted to be that sissy slut. I wanted cock. I realized it by then. I wanted cock. I wanted to be dressed while being seduced by a man. I wanted cum in my throat. I wanted a dick up my ass. I wanted to be dressed all slutty, being picked up by a guy. I wanted his cock to be twice as big as mine, watching him pound my ass hard, while I laid on my back. I watched retro crossdresser porn, or bi-sexual porn with two boys or a CD and just got off time and time again. I was cock hungry, dressing more, falling further and deeper down the rabbit hole than I had over the past 6 months.

But one day it happened! I got caught!!!

One Sunday morning I woke up early and went for a walk, trying to lose weight and thin out as much as possible. When I returned home, I took a quick shower and got into one of my long flowing summer dresses, my pantyhose underneath, no panties, my bra and a good-sized pair of breast forms in my bra. I had my shoulder length blonde wig on, wearing pair of flats. I was wandering around the house, doing almost nothing when there was a knock at my door.

Forgetting all about the fact that I was dressed in women's clothing and doing what anyone would do when there's a knock at your door. I went over and opened it. As the door swung open, a friendly lady from inside my building who lived two floors up was standing there. Her name was Linda. "Hey Linda." I blurted out.

"Hey, Matt." She said in a long awkward drawn-out way.

I stood there in the doorway for a second until I saw the strange look in her eyes. That's when my brain kicked in and I realized I was standing in my doorway, wearing a wig, with my dress on, with false breasts in. I was standing there dressed as a woman and she had seen me. I panicked. And before I could do or say anything natural reaction took over and I slammed the door in her face and yelling lout, "Sorry can't talk now."

I wanted to rip all the clothes off and open the door again. But there was no denying it, even if I tried. She had seen me. I was caught and I was embarrassed. I went into sheer freight. "Holy fuck!" I grumbled out. What was I to do now? My heart was racing. What if she told the whole building? I wasn't ready to come out. What if she sees me again, how do I explain this?

I started thinking in endless circles on how to handle this? How to do damage control on this? I ran back to the door and looked through my peep hole. She wasn't there anymore. Do I go up to her unit and apologize? Do I hide away for weeks on end? Do I move out? I was nauseous, shaking and in absolute panic.

Of course, I took off all the women's clothing, put my boy stuff back on and went about my day, justifying to myself that, "at least it was a lady in my building and not one of my best friends, or a co-worker, or my boss." Who knows how bad that would have been?

But surprisingly it took a turn for the best. About two weeks later, I walked into my building after work -- dressed a Mathew -- when I saw Linda awaiting the elevator. I tried to veer the other way, deviate to the stairs, instead of getting on the elevator with her. But she saw me and knew I had to go up, so she said, "Common Matthew, I'm holding it for you."

I got in and did not make eye contact with her. My head was down, my heart racing, while riding up the elevator which couldn't have gotten up to floor 3 any faster if I had gotten out to push. But then surprisingly, something amazing happened.

"Matt, I don't want you to be embarrassed about what happened. Everyone has to live their lives the way they feel" She blurted out.

"Thanks." I mumbled as we passed floor number two.

"I think you looked pretty in your dress;" she spoke out. "Is it new?"

I was almost appalled. In my mind I was thinking, "Why is she taking to me about this?"

Shocked and quite overcome that she would even say anything, let alone ask me if the dress was new? I was utterly surprised by her statement and questions.

"Umm.... Yeah, not too old." I gurgled out.

The ding rang for floor three and I couldn't have wanted to get out of that elevator any faster if I had a rocket attached to my ass.

"Bye Linda." I blurted out as I jetted out.

Holy fuck, she did see me. She saw what I was wearing. She saw how I looked and more importantly she asked me about my dress. I am doomed, I thought to myself.

But here's the twist.

About an hour later, I was eating my TV dinner watching the news when a knock came at my door. This time -- even though I wasn't dressed in women's clothing -- I looked out the peep hole to see Linda there with a plate in her hands.

My initial thoughts were to hide, to pretend I wasn't home. To not even deal with this or her. But knowing the kind of person I was (am) and knowing I had to face the situation. As scared and uneasy as I was about it, I opened the door.

"I made these for you." She spoke, holding out a plate of Chocolate Chip cookies.

"I wanted to talk to you more, If you don't mind. May I come in? She asked.

I was taken-a-back. I didn't know what to do. I surely didn't know where this conversation was going to go. Unwillingly I said, "Sure Linda." as I slid aside to allow her to walk in.

Linda started out the conversation by saying, "Matt, I am not the nice little old lady who loves upstairs, there's a lot you don't know about me." She continued explaining herself by saying, "I never got married and never had children, because I couldn't commit." She followed, "Not that I couldn't commit to a relationship, I couldn't commit to a man. I always felt I was different. Liked different things and wanted my freedom."

She followed by saying, "I am bi-sexual and have always leaned more towards women, so I could never be with just one man. And it took me years to figure that out. I hid it from myself, from my friends and from my family - especially my patents -- and until I accepted myself, I was never happy."

"But since that time and since accepting who I am, I have spent years dating all kinds of people I wanted to date and having the relationships, I wanted to have. So, I -- of all people -- truly understand what you are going through. Are you leading a double life?"

I felt like I was being lectured by my mother, by the school principal or a cop for doing something I shouldn't have done. With a long soft regretful voice, I muttered; "Yes."

"Then it's time for you to break free." She spoke. "Do you like men or women Matthew?

"Women, I think." I grunted out.

"Have you ever dated men?" She asked.

"No," I answered.

"Have you thought about it?" She asked

"Yes." I replied.

"Then why haven't you? She asked.

"I don't know, I guess I thought it would be "gay." I replied.

"You were wearing a dress and a wig Matthew. I think your beyond worrying about being gay." She spoke.

"Do you like dressing like a woman Matthew?" She asked.

"Yes. I guess." I replied.

"Have you gone out dressed like a woman?" She asked.

"No." I replied.

"Do you want to?" She asked.

"Yes." I replied.

"Then you should do it. Don't hide your feelings and desires away." She advised.

"I noticed you didn't have make-up on? Have you ever worn any? She inquired.

"I have tried putting some on, but I have no idea what I am doing, so it always looks stupid." I replied.

"Do you want me to show you?" She asked.

Shocked by the question and her offer, I got excited. "That would be great. If you don't mind?" I blurted out.

"Show me what you have." She directed.

Linda stopped for a second putting the plate down on my kitchen counter. "These are cookies for you," she gloated.

I walked with Linda to my linen closet, still rather shocked and confused on why my neighbor from upstairs was so interested in my life or my dressing preferences, but already under her spell and guidance. I withdrew a closed box that contained all the make-up I had ordered online. She fumbled through it all asking, "Why did you buy all this if you don't know what you're doing?"

"I don't know." I spoke. "I watched videos online and the some of the girls I was watching were wearing these type things, so I thought it was right."

"No, this is all wrong." She implied.

I actually felt stupid and embarrassed that I had bought the wrong stuff and having a woman tell me it was all wrong, sank my spirits.

"Common." She said as she took my hand. "Let's go up to my place, I have the right things."

Dumfounded, I followed along like a puppy. I followed Linda out of my place, to the elevator and up to her unit. My head was spinning and I wasn't sure where this was going, but she seemed to be caring and curious about my life and willing to help, so I went along. Once there she began a lengthy, evening long tutorial on make-up, eye shadow, blush, eye liner and worked with me defining my look, my style and the best look for my facial features. By the time her lesson was over, I had a whole new understanding of make-up and how to apply it properly.

An un-expected hand led me to the best discovery I had ever had. Someone to show me and guide me through things I would have never figured out by myself.

Weeks later....

After that day, Linda was over a lot. She would come by and hang out with me and see some of the new items I had purchased. She would be the only person at my weekly fashion shows and walk me through things, "I need to know" to be a woman. As far as I know she never said a word to anyone else in our building and kept pushing me to fulfill the life I was looking to obtain.

Our first night out.

Linda coerced me to go out one late winter evening for a long drive with her dressed as a woman. I was very leery at first, but knew eventually I was going to have to step out of my little sanctuary and enter the outside world. I got all dressed up in a long maroon dress, with black thigh highs on, a darker brown long wig, she did my make up and under the cover of a dark winter night, we headed out to the parking lot. As we rode the elevator down from my unit to the ground floor, my heart was racing, what if someone got in? What if someone recognized me? But I must say, looking at myself in the mirror before I left my apartment, I didn't recognize myself. As the elevator doors open, I made a direct B-Line to the front door to get out. I need to be out of that building. I needed to take those first steps. I needed that freedom of knowing I could walk across that threshold and become someone new.

It was warm, but dark as we walked down the walkway towards her car. Both of our high heels clicking in unison along the sidewalk. The quietness of the night, only broken by our words and the sounds of traffic.

I got into the passenger seat of her car as she climbed in behind the wheel. She started the car and with the turn of that key, my heart lifted and was relieved that we were finally driving away. We drove for a while up and down the roads, side streets and highways. We had no destination, in all reality, this was a practice run for me being out as a woman. We ended up heading to the beach, where we sat on a park bench as the general public walked by us. No one gave us a second look and no one (I think) knew or even guessed I was a man in woman's clothing. We stopped at a convenience store on the way home for some wine and I walked through the place without anybody second guessing, staring or even saying anything to me, before returning to our building.

We were only gone about two and a half hours, but it was the most freedom and opportunity I had ever had -- up to that point anyway. Linda and I celebrated my success with a few drinks and just hung at my place afterwards. That night before she left, she placed a soft gentle kiss on my cheek and said goodnight... and froze mid-sentence.

"I can't call you Matthew anymore, since you've been out as a woman... What should I call you now? She asked.

"I don't know. I never thought about it." I replied.

"Well think about it and let me know your new chosen name sweetie. With that a soft long hug and a second warm closed lip kiss was placed on my lips, as she turned and walked out.

But that kiss. That second. That passion. That hope. That support. That love and admiration from her, lit a flame inside of me like I hadn't had in a long time.

I went to bed that night baffled at what name I should be given. What if I had a daughter, what would I call her? How about my grandmother's name...?

"NO," I didn't like my grandmother's name, it sounded too old fashioned.

How about my favorite female artist? NO...

An actress? A model? A musician? Nothing was coming to mind. I tossed and tuned that night; I couldn't sleep due to the excitement of being out. Of taking the next steps, of being free.

I finally got up and ate a bite and clicked on the TV to catch a re-run of Friends. As I watched I started to realize that with the right wig; the right dress and the right attitude, I looked similar to Monica. The star of the show.

That's it. Monica. I was now going to be Monica.

It fit. I liked it. Actually, I absolutely loved it. I felt comfortable with it and I thought it was fitting and proper.

Monica it is.

After that process cleared my mind, I was settling in for a good night's sleep, when I re-lived that kiss from Linda. That soft, caring, loving and compassionate kiss that lit up my world. Not only did she take me out for a few hours, we celebrated after, and she kissed me. I felt hormones running through me like I hadn't had in a while. I started thinking about those strap-on porns with the girls how sexy it was to be watching them undress from their outfits, eating each other out, then using a toy to fuck each other with.

I started to get hard and started evolving a more deep and erotic fantasy involving Linda and I. I felt us kissing, I felt her touch. I smelled her perfume. I felt her love and more importantly I felt myself sliding my hard cock deep in her ass. Only to have her orgasm, slide on the strap-on and fuck me back.

I got up from my bed and walked over to my dresser. I reached in and found one of my favorite suction cup dildos and grabbed the lube. I suctioned cup the dildo to a large book in the center of my bed. I sucked on it a while thinking it was Linda's strap-on cock. I bobbed up and down on it, getting it soaking wet, while in my mind, my fingers were twirling around her pussy. I squirted some lube on my fingers and started rubbing and caressing my asshole. I slid my panties down and climbed up and over and on top of the dildo.

I slid in deep inside me, my eyes closed, picturing myself climbing all over the top of Linda's strap-on and riding it hard. I could hear her voice and visualize her face, while her fake cock penetrated me. I rode my dildo for about 8 minutes picturing her holding hands with me. Kissing me, making love to me, while I rode her big fake cock, while my real dildo slid in and out of me.

I was overtaken by feelings and emotions and was rock hard. My cock flapping up and down as she fucked me. I came all over the place, hearing her say, "Cum Monica! Fucking Cum!"

I slid off the toy and slid face first down onto my pillows, moving the dildo off to the side. I feel asleep panty'less in my negligee, sweaty, fulfilled and having cum while riding my toy dreaming of her. Part of me, was feeling I should have been fucking her, while part of me was loving the fact she was fucking me.

It was unbelievable.

But that didn't compare to the first actual sexual experience I had with Linda.

I'll tell you all about it in the next chapter.

To be Continued...