The Making of Monica Ch. 07

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Beginning my transition.
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Part 7 of the 8 part series

Updated 06/10/2023
Created 08/24/2021
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The making of Monica. Part 7

My pantyhose fetish and some cock!

Ever since I started crossdressing and feeling more like a woman, a Transgender, a sissy gurl; or whatever words you'd like to use. I had a fascination with pantyhose. The panties started it for me, but when I got those first thigh high hosiery, I was hooked. It didn't matter what kind, what manufacturer, what color or what style. I wanted them on!

When I finally accepted who I was and where I was going, the women's clothes overtook the small little dresser I had bought. Then part of the closet. Then, all of the closet and that "little dresser" I had bought some time back, was filled with nothing but my "man clothes" while the rest of my drawers were peppered with all my female clothing. I couldn't tell you how many times, I stroked my cock wearing pantyhose. Came in them, slept in them, and of course, wore then to work under my regular men's pants. There were even times at work, just feeling them on, got me so horny, that I would stoke myself off in the bathroom, swallowing my own cum.

Every magazine, every fashion model, every classy woman's ad, had a beautiful woman walking around in pantyhose and high heels. And I was going to be that woman! The minute I walked in my door at night -- if I didn't already have them on -- I was sliding a pair up my sexy shaved legs. Every time I went out, whether dressed in pants, or a dress or a skirt, I always had pantyhose on. I was the living revitalization of the 1950's housewife, with her heels and pantyhose on. I would purposely rub my legs to get all turned on, go home from where I was fuck myself with my dildo and cum all over my pantyhose. I was affixed. I was obsessed and I was fascinated!

I still had my fascination and my erotic feelings from my panties and even my bra's. But nothing got me more turned on then wearing my pantyhose. I could envision myself walking into my bedroom, while my naked boyfriend awaited me. Him lying there, dick hard and sticking up as I approached him wearing nothing but my pantyhose and my stiletto heels. Beginning our love making by me leaning down and sucking his cock, then getting fucked while still having both on. Riding his cock until he exploded deep inside of me, while I jacked off, cumming on his stomach and chest.

Fantasies of having my man standing over me, jacking off, cumming on my legs, coating the material of my hose. I'd see my pantyhose hanging in the shower drying off after I washed them, screaming out to me, to put them back on again. Believe me when I tell you the internet, the porns and every one of my toys got full use out of me, when I was wearing them.

After my two experiences with Giovanni, I knew I liked dick. There was no doubt about it. I got overly excited seeing his hard cock coming out of his pants. There was no doubt I was transitioning to a woman. Wearing women's clothes 12 to 16 hours a day, being only "Mathew" at work, while at night and over the weekends Monica was alive. I needed a boyfriend, I needed to dive into this further. I had more fantasies about dick, the most women probably do! I watched "you want cock videos", had my dildo inserted in me more in that year than most "regular couples" have "regular sex." I was obsessed.

But I was still unsure of how I felt about dating men only. There is always a difference between fantasy and reality and as much as wanted cock and trying something more, I was still somewhat reluctant. But the overwhelming desires to lean my head down and start sucking on a big dick was constant. Feeling a hard cock sliding in and out of my mouth was breathtaking. Hearing the moans and groans as I was giving a blow job was something I wanted more and more. I liked feeling hard in my panties, dreaming of getting ass fucked. Getting cum shot all over my face, down my throat, on my back and up my ass. I knew or at least felt; I was in love or at least lust with other C.D.'s or T.G.'s on-line, but outside of one crossdresser at the bar I hung out at, I didn't personally know any others. And wanting to be a woman, I guess my thought process was to date men.

I started looking more intently, put myself on some dating sites and had some luck. But it wasn't everything I was hoping for. I surely don't want to sound like a slut or some back-alley blow job queen, but I did manage a few dates and sucked a few guys off, but never found the lust or passion I was looking for. I still hadn't been crazy enough for a guy to lose my "Anal Virginity". But I if I liked a guy enough on a second or third date, I'd give him a blow job. So, I guess you can say, I sucked a lot of dicks. And I liked it!

Don't get me wrong, I wasn't doing it because I had to, I was doing it because I wanted to fall in love. I wanted to be able to say, "I have a boyfriend". I wanted to know he was coming by to spend time with me, be part of my life and when the night came to a close, to fuck me. I'd get excited sucking cock and getting my new love interest off, and some would return the favor. But in the end, all of those relationship fell short and I found myself longing for things I just wasn't getting. That is until Jessica walked into my life.

I was at the bar with a few friends one Saturday night. Just sitting at our table, stirring my drink with my straw, kind of bummed out. The music was so loud and so booming, it was starting to give me a headache. I was literally in the midst of taking the last sip of my drink before heading home, when I saw her come in. She grabbed my attention from the first sight. Here stood this beautiful, thin, small breasted, light skinned, gingered haired girl walking through the door. My heart stopped.

She was wearing this long flowing summer patterned dress, with brown open toe flats, that had a strap over her foot. She was carrying this cute little handbag, her hair styled, her face and cheeks rosy, light make-up on with a glow I had never seen on a woman before. I couldn't take my eyes off of her. She walked in with a few friends and for sure, I knew, or at least I believed she was someone's girlfriend. I mean --- were in a lesbian bar for Christ's sake -- and in walks this beautiful woman with a few other women. She's got to be taken? Right?

I had never seen such a beautiful woman in my life. I was till fighting my own sexual ambitions, trying to figure out if I wanted men or women, but I she was available, I wanted her.

I couldn't move, I couldn't breathe, I was staring at her, like she was Madonna. I didn't know what to do. Before I could even contemplate a plan, our eyes met. She was standing at the bar behind her friends as they ordered drinks, when she looked my way. A soft friendly smiled arouse across her mouth. As the night went on, I finally mustered up the courage to stand next to her at the bar, while I was ordering a drink.

After a brief cordial talk, I introduced myself; "I am Monica." I spoke.

She turned extending her hand out, "Hi, I am Jessica."

I won't bother you with a lengthy chat conversation, during this story, but by the end of the night, I managed to get her phone number and promised to call her soon. I don't know If she realized I was a boy or not. By this time, I was pretty damn good with make-up, the proper clothing and I was always thin and had a woman's physique anyway, with the perfect sized breast forms in. What was enlightening to me was during our conversation that night was that Jessica was at the bar that night just tagging along with friends. She wasn't with anyone and was just as lonely and bored with dating as I was.

For the next few weeks, we chatted back and forth on text -- with the occasion calls -- and during our in-depth conversations I had admitted to her that I was transitioning. I knew I had to; I couldn't lead her on either way. I had to start this infatuation with honest form the word go. And strikingly enough, she admitted to me that she was transgender and had been living as a woman for about 5 years now.

I was floored. I would have bet you a million dollars, she was all woman, but hearing that, made me so overwhelmed with joy that I had to see her in person again. I asked Jessica for coffee on a Thursday night and promised I would meet her down by where she worked, so she didn't have to travel far.

I was rushed after getting home from work, throwing on an old dress and some heels as I hurried out the door to meet her. When I walked in, she was already there. She looked amazing in her feminine business attire that she wore for work. We talked for a long time just getting to know each other and it was probably one of the best days of my life.

Even sitting there with her, I still would have bet she was all woman and she was amazing. The next few weeks of my life went by in a flash, with Jessica becoming a bigger part of it. Our first kiss was amazing. It happened after we went to China town for Chinese food and were walking back to her apartment. I was smitten, I was enthralled and for the first time in my life I was in love with a woman who had a dick. And I absolutely knew it.

Jessica text me one night out of the blue and asked me what I was doing. "Nothing" was my reply. She asked if she could come over and hang out. She was bored and lonely in her apartment and wanted to get out.

"Of course," I wrote as I continued the message by typing my address.

This was the first time that either of us, had asked to come by the other's place. Every other time we had met, it was always in public and I was bat shit nervous that she was coming. I did a quick cleanup of my place and made sure I was dressed accordingly. And yes, you know it PANTYHOSE, with a skirt, was the choice of the night.

About an hour later, my bell rang and I buzzed Jessica in. She came in looking a bit bummed and a bit worn from her work week. We sat on the couch and had a soft drink, just spending time with each other. We talked a lot about each of our transitions and the problems, fears, concerns and setbacks we both had had. Bad dates and bad boyfriends we had put time and effort into. I could tell she was troubled, deflated and was questioning where she was going in life.

Jessica laid her head on my chest and I was just holding her, smelling her beautiful perfume mixing with hair shampoo, when I realized I was falling in love with her. Feelings had come over me that I had never felt with a girl, a man or anyone else.

"Jessica," I spoke. "I know we have only known each other a short time, but I am here for you. This has been a hard and confusing, frightening transition for me too. But I feel I am headed into the right direction. Where I'm supposed to be in my life and who I should have met and dated. Just have confidence sweetie, you'll get through this."

With that Jessica lifted her head up to look at me. Her deep brown eyes, tired, saddened and worn out. "Thank you, Monica." She whispered softly.

With that I leaned down and kissed her. The energy and feelings were overwhelming. Her lips lightly coated in pink lip gloss, highlighted her warm soft tongue. Her sensual mouth and her hot body were an aphrodisiac in itself. We never broke from our kiss. We both needed each other. We both were falling for each other and we both knew, we had dicks below the belt and that's what I think we both needed.

We sat there arm in arm slowly making out. I pulled Jessica's T-shirt over her head revealing her soft pink padded bra with her small slowly developing natural breasts (she was on HRT at the time). She unbuttoned my shirt helping me out of it. Her soft hands caressing my breast forms, as my hands caressed her developing tits. Before long, both of our bras were off and I was leaning down sucking on her beautiful light brown nipples. My cock rock hard, held deep and tight in my panties.

Jessica returned the favor, by sucking on my nipples. And even though I didn't have tits, it felt amazing having her warm wet mouth on my nipples. It wasn't long until her hand was sliding up and down between my legs over my pantyhose. The feeling was intense and overly gratifying. Jessica stood up, unbuttoning and unzippering her jeans. She slid the off, showing me her cute panties, she was wearing, with a bulge deep inside of them. She helped me to my feet as I kicked off my heels. Her hands pulling at the zipper of my skirt in the back, letting it slowly fall down my legs. My cock trying to poke out, but still buried deep inside my pantyhose and panties.

Jessica got down onto her knees and slid my pantyhose down, as I stepped out of them. She came back up face to face with me as we entered into a deep passionate kiss. Our bodies pinned against each other standing there wearing nothing but our panties with both of our cocks deep inside of them getting hard. When I broke from our kiss, I took a second to look up and down her body. I could see the tip of her cock poking out of her panties, as my cock was still pitching a tent inside of mine.

I reached my hand into her panties and softly started stroking her. Jessica returned the favor and slid her hand deep into mine grabbing my shaft letting it stand upright and started stoking me. Her cock felt amazing in my hand. It was long and straight and was about the same size as mine. We stood kissing and stroking each other for a while until I guided her back down onto the couch. I wanted to suck her off. I wanted her cock in my mouth, I wanted to make her cum.

I slid Jessica's panties down and off getting my first full view of her gorgeous cock. All shaved, standing erect, her balls the perfect size to match. I kissed up her legs, between her thighs making my way to it. I wrapped my mouth around her and started slowly bobbing up and down. I kept deep eye contact with her as I sucked her cock. Her gorgeous face, developing breasts, her silky-smooth body, ginger hair and those red fingernails heightened my sexual appetite and made me feel more "at home" then I had ever been before.

I sucked her for a long time just enjoying every second of her cock sliding in and out of my mouth. Slurping on it, gong faster, then slower. Taking every inch of it down my throat, all while my cock sat poking out of my panties, throbbing and pulsing in pleasure. When Jessica was getting close to cumming, she pulled my mouth way from her dick and pulled my face up to hers.

"I don't wanna cum just yet." She spoke.

She helped me to my feet standing me in front of her. She rubbed and caressed my cock over my panties, just getting me even more aroused than I already was. Jessica slid my panties down and slid her body closer towards me. She grabbed my shaft and slid my hard cock deep into her mouth. The feeling was immeasurable. This was probably only the 7th love interest I've had in my life to suck my dick and so far, this was the best.

Jessica slid back and forth on me for what seemed like ten minutes but probably was only four or five until I felt "that feeling," men get just before you're about to cum. I pulled her mouth from my cock and lifted her off of the couch. We stood kissing, naked, both of our cocks' rock hard and pinned up against each other, as we fell deeper into this sexual experience.

I got down on my knees and slid Jessica's cock in my mouth. I felt her hands rest on top of my head, as I bobbed back and forth.

"You're going to make me cum." She blurted out.

I pulled her cock form my mouth, whispering, "Go ahead and cum baby."

I slid her cock back in and started sucking as hard and as deep as I could. Her moans and groans increasing; her hips starting to thrust back and forth as I was excitedly waiting for her to explode. I was in heaven feeling her saliva covered shaft sliding in and out of my mouth. Feeling her boner diving in and out across my tongue. Watching her shaft advance then recede from my lips. The taste of her cock and pre-cum dancing along my taste buds. Her balls swaying back and forth, her belly button coming forwards, then back from my vision. I was in love. I was sucking a cock, her cock, a cock I've thought about for weeks and I was becoming cock crazy for her.

"Monica, Oh Monica. I'm gonna fucking cum!" She bellowed out as her hands grabbed my hair tightly and her hips were swinging back and forth harder and faster. Her cock gagging me, as she was driving it so deeply in my mouth.

With a few heavy whimpers, I felt her start squiring her cum in my mouth. Her body quivered and her mouth was mumbling unintelligible moans and groans as she was blasting my mouth full of cum. I was so fucking hard and so turned on that I felt like I was going to cum, without touching myself.

When she finished shooting her cum down my throat, and I began to slow my pace, Jessica pulled me up to her kissing me deeply. She was sweating all along the top of her forehead and I knew she wanted to ram her cock deep in my ass and fuck me until she came again. And to be honest, I would have been a very willing participant!

"Your turn!" She moaned through our kiss.

Jessica edged me down onto the couch and got down on her knees. She smiled up at me as her head drifted downwards; as she put my cock back into her mouth. She bobbed up and down on me for a just a bit until I blasted my load deep in her throat. When she finished, we laid on the couch together, just cuddled in.

Our naked bodies were entwined as we kissed and talked more and more. Two women lying there cuddled in with our cock spent from shooting cum by the blow jobs we had given. That night began a relationship with her that was; and still is the best thing that ever happened to me. She didn't spend the night that night, but did about a week and a half later. That's the night I lost my anal virginity from her dick, to her and to the person I was falling for. It was a long wait, but it was worth the wait.

Ill tell you all about it in the next chapter.

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SissyBoy1WarszawaSissyBoy1Warszawa3 months ago

@SamanthaMeyers I am very enchanted by your story about Matthew J. Smith/Monica and her individual fates, transformations from dressing up in women's panties and bras, through meeting girls and then their departures and even ridicule or subsequent attempts to dress up in women's clothes and taking on the personality of a woman, taking the name Monika until meeting a person with a similar trans personality and falling in love with her Jessica. Like Monica, I would love to meet a person like Jessica and be understood and loved. I really hope that Monica and Jessica's path will lead them to get married and create their own home and family.

ps. Sorry for any errors and linguistic inaccuracies, I don't speak English.

Best regards, SissyBoy from Warsaw, Poland. 🧒🏻⚧️👧🏻❤️👩🏻

jrrtolkien420jrrtolkien420over 2 years ago

Another great story. Please continue.

AnonymousAnonymousover 2 years ago

More please!

LatexZashaLatexZashaover 2 years ago

I love it. Can you do their wedding? Also I like how your stories seem to be about saving the character's soul, in my opinion anyways

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