Exploring My Feminity Pt. 01

It started as an obsession with porn. Any kind of porn, mostly men's magazines like Playboy, Penthouse, and Hustler, then after a time photos of nude women began to get stale and I moved on to things more explicit. My first hardcore porn came in the form of a catalog for XXX rated films. This kept me interested for several years, then it too became old and stale. My search for new excitement led me to some fetishes and most importantly hardcore swingers magazines. Though most of the ads didn't have photos, the ones that did displayed various acts of real people like me. It was in these magazines that I found something that would eventually change my life.

One of my swingers magazines explored a wider range of interests. One of these was crossdressing and though the photos were terrible, they awoke something inside of me, something that sparked fantasies and even dreams. I was fascinated with the subject and began seeking more on the subject. The shemale magazines came next, but they were much like everything else I had collected over the years, good only for a short time. In those days there wasn't much on dressing, not nearly as much as transsexuals, so I only found some stories and more swingers ads to satisfy my curiosity.

Then one day, an opportunity arose that really got me started down the road to crossdressing. I was working as a maintenance man and happened upon a bag of discarded women's underwear. The bag had several pairs of panties, a few bras, and some other lingerie. Something inside me grasped at the opportunity and I stashed the bag in my truck. The rest of the day was tough to get through because I found myself excited by the prospect of going through the items after I got home. After what seemed like hours, I finally finished up for the day and headed home.

I was married at the time but I got off work a couple of hours before my wife and had time to myself before she got home. As soon as I walked through the door, I headed up to the bedroom with my prize. I dumped out the bag on the bed and spread the items out to get a better look at them. An inventory found that I now had 8 pairs of panties, 4 bras, and two nighties. It was the panties that drew my attention. One pair in particular, a pair of pink satin panties. I picked them up and they felt, well amazing is the only word I can think of to describe the feeling. They were silky and smooth, just the feel of them in my hand began to make my cock hard.

I had seen panties before and had washed my wife's panties many times, but I had never gotten excited about them the way these excited me. As I held them, my dick demanded attention, so I unzipped my pants and released it. I began stroking my cock while I held the panties, then without thinking, I wrapped the panties around my cock. The feel of them was electric and precum oozed from my dick. After several minutes, again almost without thinking, I stripped out of my clothes, then slipped the panties on. I rubbed at my hard dick now encased in satin, but it wasn't until I looked up and saw myself in the mirror that excitement peaked.

I looked at the reflection in the mirror and what I saw was the men from the magazine, men who advertised that they enjoyed dressing in women's underwear and wanted to have sex with other men. As soon as the thought materialized, my dick began to pulse. I looked down surprised to see a large wet spot in the panties. Experimentally, I ran my finger over the spot and saw that the tip of my finger was now wet with my precum. I raised my finger to my mouth and my tongue flicked out to taste the slippery fluid. It tasted salty, but I found the taste appealing, and I could feel my cock responding. I pulled out my cock and found even more precum dribbling from the tip. I quickly caught it with my finger and slid my finger into my mouth. The taste was even more potent and I sucked greedily at my finger.

I was incredibly horny by this time and laid down on the bed to masturbate. It didn't take long and I was shooting a very large load of cum. As the waves of pleasure subsided, I considered the globs of cum spread across my stomach. Again, I dipped my finger in the warm fluid then brought my finger up to my mouth. This time the taste was different. The saltiness was there but there was something else, something new and wonderful. I began scooping the remaining cum off my body and putting it in my mouth. It took several minutes but I got every drop. I had my first taste of cum and I found that it excited me as I had never been excited before.

I had many such sessions in the following days and weeks and found myself masturbating at every opportunity. Whenever I thought about my hidden stash of panties I became erect and was soon seeking a quite place to relieve my tension. After one such session, I simply didn't take my panties off and my journey of exploration began.

I found I liked wearing panties. It was exciting both the fell of them and the idea that no one around me had any idea I was wearing them. My stash had numerous pairs but only a few of them were large enough for me to wear comfortably, so the next leg of my exploration was to find or buy panties that were the right size. I finally worked up the courage to visit a local clothing store. Still hesitant to expose my fetish, I mixed in several pairs of the appropriate size panties with clothes I couldn't properly wear as a ruse so the cashier wouldn't think I was buying them for me.

I wore panties every day under my regular clothes but just as with the porno, the excitement began to fade over time. I continued to masturbate and to lick up my own cum, but the thrill began to lessen. I knew it was time to change things up, but what could I change. Then one day while doing laundry, I happened upon one of my wife's bras. Though I had seen then, indeed, held then before, I suddenly felt that twinge of excitement as I thought about wearing one. I knew the one I had stumbled one was one she wore often, so I rummaged through her drawers until I found one I hadn't seen her wear.

Now dawning my new treasure along with my own panties, the old excitement was back. I would pose in front of the mirror, watch as my cock grew stiff, then masturbate to a rousing orgasm. Over time began to realize, that my fantasies were shifting. I began fantasizing about other men, about how they would respond to seeing me dressed in women's underwear, imagining them getting turned on, their cocks stiffening at the sight of me. Eventually, my fantasies turned to my interactions with them. I visualized holding their cocks in my hands. How they feel, if it would be similar to holding my own cock.

The first time I imagined jerking them off, I came almost immediately. The thought of jerking another man's cock was incredibly exciting. Each session I would push my fantasies further until I was sucking their cocks, tasting their cum, and with each new image, my excitement grew. My climaxes came more quickly and were more intense. I looked at the cum covering my fingers afterword, wondering what it tasted like. Final one day, I licked the cum of my hand, holding it in my mouth, savoring the taste of it. It was salty but had an appealing flavor and wondered if other men's cum tasted the same. I began to realize what I wanted next, to experience sex with another man. The thought was both thrilling and frightening at the same time, but I knew I was going to try it.

I knew there were video shops in town, I had visited some of them during my search for porn. I also knew they had booths and though I hadn't seen glory holes in the ones I had been to, I had read about them, so I had a new quest, to search for glory holes. I prepared myself by dressing in my sexiest panties and bra. I even dawned a pair of fishnet stockings, once dressed I headed out. My second stop yielded me success. There were quite a few booths, though small, all seemed to have glory holes some even had two, one in either side.

It was a bit early, being only late afternoon, so I left to grab a bite and waste some time until the sun went down. When I arrived back at the store, I was pleased to see several cars in the lot. I quickly went inside, headed back to the viewing booths and found an open booth. The smell was the first thing I noticed. There was a heady odor about the booth, the smell of man sex and it was exciting. I took a deep breath, savoring the odor as my cock began to rise. I dropped money into the machine and sat down to wait.

My wait wasn't long before I heard the door on the booth next door open and close. I heard the machine start up and I leaned forward to glance through the holes. I was rewarded by the sight of the man unzipping his pants and pulling out his semi erect cock. I was riveted on the sight as he began stroking himself watching his cock grow harder with each stroke. He was soon fully hard, a fully 7" or more and uncut. The foreskin partially covered the head of his cock even while fully erect. Suddenly the cock turned toward the hole surprising me as I had been so focused on the cock.

I backed away from the hole, but just as I did, that beautiful cock slid through the opening. This was it, my dreams and fantasies made real. Here was a man's hard cock and it was expecting me to suck it. I slowly lifted my hand up, wrapping my fingers around the shaft. I felt it pulse in my hand as I began moving my hand up and down the shaft. I watched mesmerized by the sight of the head disappearing into the fore skin on the up stroke then the down stroke revealing the swollen purple head. I heard a soft whisper from the other booth, "Suck it."

I leaned forward and on the next down stroke as the purple head peaked out, my tongue flicked out and I ran it around the head. I heard the man moan and as my passed over the tip, I tasted an amazing salty flavor. When I pulled back the tip was oozing a clear liquid. As it began to drip, I quickly caught it on my tongue. The taste was different than my own, more potent, more sexually arousing. I wanted more, so I opened my mouth wide and wrapped my lips around the head. With the head of his cock in my mouth, I was rewarded with more of that salty sweet fluid. I gently sucked trying to elicit more of that intoxicating nectar.

I heard another soft whisper, moans mixed with pleas to suck it deeper. I began working my lips further down the shaft, taking almost all of his cock. As I pulled back, I increased the strength of my sucking, pulling at the skin, until just the head remained. Then my tongue slurped around the head, then I felt the cock jerk. It began thrusting, working its way deeper into my mouth. I knew what was happening, he was about to cum and I wanted him to cum. My lips clamped down harder and I matched his movements until with one hard thrust, I felt my mouth filled with hot cum. He thrust several more times and with each thrust came another hot spurt of cum. I sucked even harder, coaxing as much cum out of his cock as I could.

After a few moments, his cock began to soften and he pulled it out of my mouth and back through the hole. My mouth was filled with cum, some of it dribbling down my chin. I savored the flavor, rolling it around in my mouth with my tongue, then I took my first swallow of another man's cum. As I did, I felt my own cock release, my own cum spilling out onto the floor beneath me. The orgasm took me by surprise, but it had rocked me. I had fulfilled my fantasy of sucking another man's cock. I had reached orgasm, not from masturbation but from experiencing the taste of another man's cum. The orgasm had been intense but I knew there was more, that it could be better.

I was wearing women's underwear but the man didn't know that. I had played the female role and pleasured a man and as that thought arose, so did my own cock. This was what I wanted, this was what excited me more than anything, playing the feminine role in a sexual encounter. I wasn't sure how, but I knew I had to find a way to have an encounter with a man dressed as a woman. As my mind played over the possibilities, my cock began to throb again.