Expanding Horizons & Wardrobe Ch. 03

My name is Joe and I was a straight married man, married to my wife, Bonnie, who I met 18 years ago. Having stumbled into sissy hypnosis videos along with wearing women's underwear, I began to feel my manhood slipping away. My crossdressing clothing now consisted of two pairs of panties, pantyhose, two skirts and two tops. My job had progressed nicely and I now had my own office in the tech company -- the nice thing about an office is that you have a door which you can close. To my benefit (or detriment, depending on how you look at it), the office afforded me the opportunity to dive deeper into crossdressing. I no longer needed to go to the men's room to change into my panties when I got to work and I found that I could also wear my pantyhose at work, if I wore jeans and medium length socks. It is hard to describe the feeling of wearing pantyhose for the first time, but needless to say, it was exhilarating and also sexually stimulating as I found myself often leaking precum in my panties.

Meanwhile, at the end of every work day I would head home to my "straight life" with my "straight wife" Bonnie. Bonnie and I rarely had sex -- my sex drive really seemed to fall off a cliff and sex with Bonnie became like a chore. Our frequency for sex was once about every four to sex weeks -- we would mention sex about once a month then eventually we would have a five minute quickie and we were done for another month or so. To be honest, I found myself less and less interested in traditional sex as I was beginning to feel like less and less of a man -- I often found myself daydreaming of getting pegged while wearing panties. These thoughts led to personal exploration of self anal play when Bonnie wasn't around.

Being a secret sissy and having to hide my girly clothes, I tried to keep them as clean as possible because washing and drying them had to be done discreetly, either at work or at home when no one was around. Drying my girly underwear was also a challenge as I only had two-pair of panties and I would typically leave them hanging over the edge of the wastebasket under my desk to dry while I worked. To remedy the constant cleaning of precum in my panties, I decided that panty liners would be very helpful and after a successful test run of a panty liner that I found in my wife, Bonnie's supplies, I decided that I needed my own supply as wearing panties was now a daily routine which meant it would be the same for panty liners and, while one or two would go unnoticed, a daily use would get noticed by Bonnie. This led to another trip to the local Walmart, with self-checkout, to buy panty liners. As you can probably guess, my trip to the Walmart had to be done while wearing panties and panty hose which kept me in a girly mindset -- this was also very encouraged by the many hypnotic sissy videos that I found myself watching, now on a daily basis.

Of course, when going to the store outwardly dressed as a man, I did not feel comfortable buying panty liners. I wandered the toiletries aisle getting some shampoo, deodorant, shaving cream and toothpaste. Then I did a couple of walk-bys through the feminine products aisle glancing at the panty liners to decide which ones to buy and then when I felt like no one was staring at me, I grabbed a box of nicely sized liners and stuffed them in my shopping basket. However, walking by the feminine products aisles, my interest was piqued by lipstick and false nails -- somehow I just couldn't help myself and, after doing many more not-so discreet walk-bys, I picked out a bright red lipstick and a set of press-on nails. As I now reflect back on the red lipstick purchase, it was clearly related to seeing all the cock sucking videos over-and-over again as I had begun to wonder what it would be like to suck on a cock.

In total, I must have spent a good hour or two shopping for my new girly products: panty liners, another pair of pantyhose, red lipstick and red press-on nails. I was so sexually excited that I must have leaked a ton of precum -- that's when the second embarrassing incident happened. Just when I thought no one was around and I had just picked the press-on nails off the top shelf I heard a child's voice say "mommy that man peed in his pants" and I looked down to see a young girl staring at the good-sized wet spot, from my precum, on the front of my jeans. I looked up to see her mother looking at me as I was holding the red press-on nails in-hand. Just my luck -- children just seem to have no filter and say things just as they see them. This little girl's mother was less polite that the mother that I bumped into on my first shopping experience; she glanced in my basket and said, point-blank, to my face, "It looks like you need to use those pantyliners and I suggest you buy some foundation before putting on that lipstick!". Immediately, I felt warm blood rushing to my ears as I'm sure I turned redder than red -- I wanted to die right there, on the spot.

I remember thinking for the first time, right after that woman confronted me "you are a sissy, no real man would do this" -- I had been told many times over-and-over again in sissy videos that I was a sissy but I had never thought it directly, until now. Regardless of my embarrassment, I was now committed to my purchases. Being very embarrassed and self-aware of my wet spot, I held the shopping basket in front of my crotch until I got to the self-checkout and once again paid in cash so as to avoid any credit card record of my purchase so that my wife, Bonnie, would not see or question my purchases. Holding my bag in front of my crotch as I exited the store, I thought I was home free until the employee at the door, in charge of checking purchases, asked to see my receipt and proceeded to check each of my items against the receipt. Of course the older gentleman who checked my receipt didn't seem concerned about anything, as he was just doing his job; however, he raised an eyebrow at me when he noticed the wet spot on my crotch which I couldn't hide when he asked me to show him my purchases and my receipt. I threw the receipt away as soon as I left the store -- there was no way I would return these purchases and I wanted no record of my purchase!

With a growing inventory of crossdressing clothing, the art of keeping my girl clothes available and hidden became a bit more work. As I searched around my office at work, I found that if I stood on my desk I could lift up the ceiling tiles and put my crossdressing clothing on top of the ceiling tiles with no one the wiser. My office at work now became my crossdressing world. First thing in the morning I would strip off my jeans and boxers, replacing them with panties, pantyliners and pantyhose. Some days I would sit at my desk the entire day in a skirt and pantyhose, only bothering to put jeans over my clothes when I had to walk to the bathroom or go talk to someone. Even when I went out of my office I would not bother to put socks over pantyhose -- I would just slip on my shoes and I figured you would have to look hard to see the tiny bit of black pantyhose between my shoes and jeans -- no one seemed to catch on.

As I continued to expand my world of sissy hypnosis videos, I began to notice that a lot of the women in the videos had panty bulges and were actually transgender or crossdressers. I was, and still am, amazed at how some of the girls with cocks have such beautiful boobs and were drop-dead gorgeous. I found myself aroused and constantly excited by the thought of clean-shaven cocks combined with beautiful boobs and full girl clothes. As a result, I found myself watching more-and-more videos of cocksucking and cum shots as I was constantly being encouraged by sissy videos to swallow cum -- however, everytime I would masturbate into my hand and stare at my cum I could not get myself to the point where I could actually put my cum in my mouth.

My fascination with sucking cocks continued to grow and when I saw a video of a girly boi sucking on his own cock I was intrigued. Could I suck my own cock?

It was probably about a month after I had bought the lipstick and fake nails, that Bonnie told me she was going out of town for a "girls" weekend with some of her friends. I always encourage her to see her girl friends as they are all married and Bonnie always comes home telling me how terrible their husbands are and how she is glad that I help around the house and that I am always nice to her. Bonnie and her friends all left on Friday afternoon before I was off work so I grabbed every piece of crossdressing clothing I had stashed at work and headed for home. As I started driving home and was incredibly excited about the prospect of dressing up, I kept thinking about trying to look even more girly -- so I decided to make a stop at the dreaded Walmart, one more time, for a sports bra, foundation (as suggested by the not so nice mother), eye shadow and a pair of heeled sandals that were women's size 12. I was still very embarrassed while shopping for girly stuff so I used my standard walk-by routine through the feminine products aisles glancing at what I wanted to buy and then when I felt like no one was staring at me I quickly put the products in my shopping basket.

Once I got home, I decided that the best way to start was to have a few drinks of hard alcohol, which is very uncommon for me, and it doesn't take much for me to get a nice buzz. Normally, my alcohol consumption is one beer every week or so -- a 12 pack of beer usually lasts a couple of months in the fridge. We do keep some hard liquor on-hand for the few times that we decide to make mixed drinks -- so I grabbed a bottle of vodka and mixed several very strong drinks with a little bit of orange juice as I was intentionally trying to get a good buzz on. Next I watched a few sissy cock sucking videos which got me incredibly turned on so I headed off to the master bath to take a shower and start getting dressed. I always shave after showering, which includes shaving my chest; this time however, I decided to shave my entire upper body, except for my arm hair. It was then that I decided that I wanted to shave my pubic hair so I took the hair clippers and first took my bush down to almost nothing with a number 2 on the hair clipper and then I made a thin vertical landing strip and shaved my cock and balls completely bare. Seeing my bare cock with the girly landing strip made my cock look just like all the sissy cocks I watched in the sissy hypnosis videos and I began leaking precum just from shaving. With the intoxication in full effect as I think I was on my third vodka, I began shaving the upper part of my legs around my cock and somewhere along the way I decided that pantyhose would be much better on hairless legs to I shaved from my neck down to my toes with only arm hair remaining.

The first piece of clothing I put on my black lace panties which felt heavenly on my now hairless cock which I tucked down and back as far as I could so that my crotch was somewhat smooth then as I was about to put on the pantyhose, I thought to myself, I have press-on nails for my fingers but nothing for my toes. So I looked through Bonnie's makeup supplies and found a large number of toenail polish bottles. Once I found a nice red one, I began painting my toenails which took an enormous amount of time but when I was done they were a very sexy bright red. As I put on the pantyhose, I could see my red toenails nicely through the pantyhose. Next was the sports bra which I stuffed with rolled up socks which gave me about a C-cup. My burgundy colored leather mini-skirt and gold sequin top were perfect with my black pantyhose. As I stared in the mirror, I was beginning to see a girl looking back at me but I was missing girly hair so I rummaged through the closet drawers and found a long blonde wig which Bonnie had used for a Halloween party. Now with the wig on all that was left was my makeup and nails. Putting on foundation was actually pretty fun and easy to do and bar far the easiest part of the process which yielded a nice clean look for my face without any trace of facial hair. Lipstick was also quick and easy to do and I loved sexy red lips looking back at me in the mirror. Finally was the eye-shadow and press-on nails. The press-on nails were quite easy to put on once I found the right sizes but applying eyeshadow was a little more work given my inebriated state so I went completely overboard making my eyes completely dark. All in all when I was down, I was very happy with the slutty girl looking back at me in the mirror.

Once I put the newly purchased heels on, I was a complete sissy -- the only thing out of the norm was my arm hair which I could not convince myself to shave as I could always put clothing over everything else. This meant that I would have to start shopping for long sleeve tops in the near future. I was so happy with the look that I started taking pictures with my phone. Seeing my sissy self in the mirror was absolutely mind blowing -- I remember looking at myself in the mirror thinking my ass and legs are really sexy. I had never thought anything like that before but I workout regularly at the gym, mainly on the stairmaster, and I bike a lot so I have well built, lean legs. I started taking pictures with my and I even stripped back down to my panties and painted toes in the heels and took pictures of myself from the waist down in panties and heels. At this point I was definitely drunk and sexually aroused so I decided to put to the test my ability to suck my own cock. Not having yet bought, or ever used, an anal dildo, I went on a short hunt through the house and found that the handle of a lint roller might work nicely for my boi pussy, which the sissy hypnosis videos successfully renamed my ass to and I had now begun to mentally accept.

Laying on my bed in my black lace panties, sequin top, wig, full makeup and false nails on. I proceeded to lift my legs up to the point that they were over my head with my paint toes touching the headboard, putting my sissy clitty, also known as a cock by my straight alter-ego, directly above my head. I proceeded to apply a generous amount of lube and slowly inserted the handle of the lint brush into my sissy pussy. By the time I had the lint brush fully inserted in my sissy pussy, I had my first experience of precum dripping onto my face -- it actually was a turn on for me and I began trying to bend my back and stomach more and more to see how close I could get to sucking my on cock. It wasn't easy but I think being somewhat intoxicated helped as my cock got closer and closer to my face. Finally after what seemed like a couple hours -- who knows, it might have been only 30 minutes but it seemed like forever -- the soft head of my cock brushed the tip of my nose. My cock was literally less than 2 inches from my mouth so I adjusted my head a bit and by using my feet on the headboard behind my head, I was able to press down and for the first time ever I had a cock enter my mouth. It was my own but it was still a cock and it was in my mouth.

At this point there was no going back, I kept working at it probably for another 30 minutes or so not even thinking about the precum that I was obviously now tasting. Using my feet and legs, I actually was able to develop a slight bit of motion with my cock, managing to get about halfway in my mouth with each thrust. This was all that I needed, with the lint brush still lodged in my sissy pussy I couldn't have stopped my orgasm if I had wanted to. Almost without control, my cock started to pulse and I could feel the large vein pumping cum into my mouth as my lipstick cover cock exploded with the largest load that I had experienced in a couple of years. I swallowed at least twice but the load was big enough that it spilled out of my mouth and actually out of my nose as well. Wanting to see my cum covered face in the mirror I got up, finding it a bit difficult given the position I had been in for what seemed like hours. Standing in front of the full-length mirror, I couldn't help myself as I took a picture with my phone of the slut who had craved cock and now had cum literally dripping off her chin and out her nose. I even gathered up the cum and placed the good-sized remaining load on my tongue for a final photo op. It was like a switch had just been completely flipped in my head, never again would I even hesitate about tasting cum.