The Making of Monica Ch. 03

The Making of Monica. Part 3

Experimenting online and the beginning of toys.

As the weeks and months went by, I grew a fondness for a specific style, a specific look and a specific way I liked to dress. I ordered clothes that were suitable to my passion, my desires and frankly, looked good on me.

I started experimenting with wigs and at first, I was ordering cheap inexpensive, shitty, poor-quality wigs. Things I would later call, Halloween costume wigs. But as I caught up on my bills and grew my tastes more, I started ordering better quality wigs. Most of which I would select based on their length and closeness to the natural color of my hair. I had shorter, "Business professional wigs" to go along with my business professional women's suits, and long free flowing wigs, for that girl at the party look. Along with other wigs for that dirty, erotic, sexy negligees, fuck my brains out look I was looking for.

I had never been out of the house in anything but panties and occasionally a bra, and I needed an escape. I needed to show the world who I was becoming and I needed friends. I started experimenting online and I found the "dark side of the web," the dark side of a site I like to call Assbook and several other adult friendly places signing up for profiles. I wanted to look erotic and sexy and desirable for anyone looking at them, but I also wanted to portray myself as the classy lady, with the slutty slide. Albeit I had never dated a crossdresser, trans or a man for that matter. And at that point I knew I was still more interested' in women" and would have rather preferred their company. But I was at least "out" in some way shape or form and trying to build a network of people, liked minded to me.

As time went on and my comfort level grew, I would take very erotic pictures of myself, face missing, and display them on these sites. I didn't want anyone to recognize me, especially any friends I'd known for years and/or my co-workers. I would disguise my bedroom, with sheets and blankets that I never used regularly, hanging the on hooks or doors as so the mirror would not show my room.

I would lay on the couch, with blankets sprawled open hiding the materials true color and style, so no one would recognize. I would picture myself as the beautiful CD, showing the world my body, my physique and my sexuality. And by the end of my own little personal photo shoots, I'd usually end up on all four with my ass in the air with a thong on; revealing that thin piece of material running up my ass. Cheeks spread wide open as if I was begging for cock. Looking back now, it was surely the start of wanting cock and being a woman who was wanting to be fucked.

I took countless upskirt photos, or raised skirt phots showing my panties and thigh high pantyhose as an erotic; "Hey look at me," moment. I was screaming out to the world; look how I dress! Unfortunately, a lot of times it fell on deaf ears.

The Lesbian Strap-On Porn opened the door further...

Every few days I would have to shave those all-important areas, so I would prepare a nice hot bubble bath, and/or use scented oils and slide deep into the hot soothing water. I would have all my clothes awaiting me on the sink and I would just stare and be overly excited knowing it wouldn't be long until my clean-shaven body was in them. I would rub and caress myself, putting lotion on and getting prepared for a night of eroticism by myself.

I had purchased some porn through a site and had ordered a variety of seduction style porn, one was cutely named, Strap-on ***. I was lying in bed, wearing my wig, the long flowing blonde one, a pair of white thigh high pantyhose, a white thong, white bra, with my breast forms in and a knee length light pink negligee. I had a light hint of perfume on my wrists and my toe nails painted cute pink. By this point I was painting my toe nails (only), because no one would ever see my naked feet. I adjusted my pillows up against the headboard, got myself comfortable and hit play

I was watching a few scenes of the other lesbian videos I had ordered and I was getting tuned on and aroused, but it hadn't quite reached the height of passion, I was shooting for. I got up and put in the Strap-on porn in. The setting, as a lot of them are, was rather repetitive and almost unrealistic, but when that one actress, pulled out the Strap-on out and slid it on. She had my attention. I watched her tie up this black panty looking martial, with this long pink "dick' attached at the end while the other girl knelt on the bed, literally drooling. My pulse quickened and my body tingled. I watched the second actress, start sucking this fake cock and I about exploded. Both of them naked, pussies wet, but now they have a new toy, a new adventure a new set of fun things to watch. A Strap-On! WOW!

As the scene progressed the girl slid on top of the other and slid that big cock into her pussy. And I was rock hard. I know exactly what it's like to slide into a dripping wet pussy and rock back and forth. So, I knew how stimulating this must have been for both of them. But what drove me over the edge was after they switched positions and after the receiving girl, got onto her knees, the Strap-on queen slid that big cock up her ass.

I couldn't watch it any more closely. I was affixed. This beautiful hot woman, was ramming this big fake cock, up the other's girl's ass and you could see she was actually enjoying it. This wasn't some "moan and groan" fake ass porn scene. She was actually pleasing her with that plastic cock. I couldn't get my panties off fast enough and I promise you that my hand went past my cock and balls and right down onto my asshole.

I squirted enough lube on my hands and under my balls, feeling It oozing down my ass cheeks to my asshole that I left a wet stain on the blanket. I didn't focus any attention on my cock, I just laid there with all my fingers and palm, slippery wet with lube, rubbing up and down my asshole. I felt sensations I had never felt before. My legs were lifted up and I was almost rolled into a ball. I was dying to be the girl in that scene, getting this cock rammed up her ass. Moaning out loud as she was, feeling what she was feeling. Getting fucked like she was getting fucked.

I couldn't take it anymore! I wanted to feel what she was feeling. With one brave push I slid a finger deep inside my ass. I gasped for air as I felt it enter inside me. Warmth and wetness surrounded my finger as I started slowly sliding it in and out further and deeper. It sent sensations through me as I had never had before. I was trying go as fast as the girl doing the fucking on the screen was. My cock still hard, but slowly settling as I was learning how to pleasure a new area of my body.

Every time the scene ended and/or they switched positions; I'd rewind to the anal sex penetration portion and start over. After watching it several times, I started to fast forwarded to other scenes, and watch other girls take that big fake cock in their asses. By the time I had finished that night I had managed to get two fingers deep inside my ass, while my other hand was stroking my cock to orgasm. Of course, focusing way more on my ass than my dick.

I had never felt such a deep and meaningful masturbation as I did that night. When I had finally finished, my asshole was still open, like it was begging for more. My cock still partially hard, still capable of a round two if needed. I was enamored. I found a new, enlightening, erotic place to play and I wasn't going to waste any opportunity.

My erotic pictures on the adult sites, became more provocative, my online chats with Crossdressers and / or their admirers got more intense, more sexual, more deviant and drove me deeper into this fetish, this world and this place.

I had more people -- from all over the US -- sending me their pictures of them dressed, or in their best erotic possess. More cock pictures and videos came in and I tell you; without a doubt, I stroked myself off to a host of cock pictures and cock videos. Of course, I'd return the favor and send back images and videos.

I had given up on traditional dating and was falling in love with other CD's I'd meet on line, wishing they were closer to me in real life so we could meet and have sex. My world was changing, the tides were changing and the anal play had only just begun.

Countless, countless, countless; I really mean countless night were spent with my fingers up my ass, while my other hand was wrapped around my shaft. I started looking for items around the house I could start using to fuck myself with. I tried long candles, wrapped in condoms. I tried toilet paper role holders. Large markers. Anything I could find that would simulate a hard cock. But it wasn't until "the brush" that I began growing my needs and wants more.

I was shopping one day after work at the local chain drug store and I was wandering through the Make-up aisle, (I was still trying to figure out make-up and what I would need), when I came across this rather big bristled hair brush with a very long, smooth, rounded handle. No rubber or plastic, no holes in it. Just a long piece is charcoal colored handed. It had to be about 5 inches long and thin. Surely not the width of my cock, or others I would later have, but one hell of a good start.

I bought the brush, even though I didn't have hair long enough to brush it with and brought it right home. What I found rather quickly that night, was the thick wire bristles, would stick to the material of the couch right in-between the couch cushions and since it was a fairly long handle, I could climb up on top of it and slide it in and out of me, like I was getting fucked by a lover on my couch.

The first night I used it, it was amazing. I was trying to use it lying down, but it was such and odd reach under for me, coupled with my lack of experience, that I just wanted to stand it up on edge and ride it. But it wouldn't stand erect on my bed. I tried putting it in between two pillows or clothing so it would stick straight up. I thought about taping it to a book or a pillow, but that wasn't going to happen. Nothing worked.

That's when it hit me; "the couch". I rammed the bristle end in-between the cushions and it stuck there, without moving, staying in an upright position. I brought out my lube, and the video I was going to watch, dimmed the lights, closed the blinds and started watching another (more recently ordered) Strap-on porn. After teasing and a bit of foreplay with myself, getting hard and horny watching the girls, I slid up and over the brush. I gently slid myself down onto it and felt it slide deep inside me. I gasped for air as I began rising and falling on that handle. It wasn't in very deep, but it was in and I was riding "something".

I was so fucking hard and so ready for this "new toy" to be penetrating me. I reached back and held my heels as I bounced up and down it. I was mimicking the girl in the video as she bounced up and down on her lover's fake dick. The feeling was unbelievable. I had a "cock" in my ass, and I was riding it like I was a girl being fucked by my lesbian lover. My legs tightened, my muscles ached and my cock almost went limp as I bounced up and down on it. Moaning like the actresses were. Feeling pleasures, I had never felt before, cupping and caressing my breast forms, cupping and pulling on my balls. Just letting my cock flap up and down, as if it didn't matter. I had a 'cock' in my ass and I was getting fucked!!!

"Holy fuck!" I bellowed out as I felt it sliding in and out of me. This is incredible.

I must have fucked that brush -- or better said -- that brush handle must have fucked me three dozen time, until I need more. I needed bigger, I needed longer and I needed something that looked like a dick. Not hair brush handle. A dildo. A realistic toy. A realistic cock.

Of course, once that aspect of anal play began, I started ordering dildos and vibrators and bullets. I was making frequent trips to porn stores, with bra's, panties and nylons under my clothes as I sought the perfect dildo, that I was going to fuck my ass with coupled with the perfect video to watch doing it.

I found the shemale and crossdresser porn section(s) and started buying those videos, switching from lesbian porn to watching "men' dressed or men transforming into women, getting cock. What an absolutely eye-opening experience it was watching these video; coupled with a sudden realization of what life could bring. And more importantly, What I wanted to become!

Over the next few months, there were a multitude of nights, I was dressed in full dress watching those crossdresser and tranny porns, riding my dildo, cumming all over the place. Sucking my dildos like they were real cocks. Wanting to be the girl on her knees giving head, being on her back, or on my knees getting rammed by a big cock. Those nights, the clothes, the images, the videos, the dildos opened the door even more than I could have ever imagined. I was becoming a cock wanting, crossdressing sissy and I had no complaints.

I (at that point) would have just wished I would have met some of the crossdressers from my online sites instead of just chatting online and by text, to have that first sexual CD to CD experience, but that came about a year later and was surely something worth waiting for. And even though I had friends, both in the real world; as well as my online world, I felt rather alone. I needed that human touch, I needed to be seduced, made love to, whether a man or a woman, was irrelevant. I needed someone! And as things progressed inside me, dressing like a woman, feeling more feminine, wanting to experience gay se, I was looking more at CD's and TG's more than genetic girls.

But then, an unexpected helping hand - I mentioned last story - presented herself and my sex life with another human being -- started again. Which lead me even deeper into the Making of Monica.

To be continued...