Someone actually honked at me…

Picking up from where I left off, I was sitting home alone late one night while both of my old roommates were away for the week. Late one night, it must have been a week day night, I was sitting around the apartment still dressed (thong and bra with newly acquired breastforms, short jean shorts, form-fitting color block spandex tank, and a pair of my newly acquired high heels!), and got the urge to do something crazy.

I know it had to be absolutely incredibly late (like 400am late) because I never would have done this otherwise, but I opened my apartment door and peeked out into the hallway. No one there. I looked to my right, saw the door to the exit stair and took a few steps out of my apartment. I slowly turned the handle and pushed the door open. Before I stepped into the stairwell, I listened for footsteps, but heard none.

I pressed onward… slowly stepping down the stairs to the basement level. The large chunky high heels made their trademark clank on the metal stairs as I continued, but I still didn’t hear anything or anyone else. I got down to the basement level and turned down the long hallway towards the side exit, my heels again clicking as my stride sped up and developed rhythm. I approached the door to the outside world and hesitated. My heart was racing, part nervous from what I was about to do and part excited from the look and feel of my clothes and the sound of my high heels so far.

This side exit door would sometimes get stuck on the door jamb and stay party open enough so you could re-enter. That was my plan, but if it failed I would have to submit and enter the building through the main or rear entrance. The chance of being caught was exponentially higher at those two entrances, so I was scared if something went wrong. But still, I continued…

I pushed the door open, peeked outside and saw no cars moving and no people anywhere. I took a step outside and slowly guided the door to its resting spot against the jamb, still partially open. I did a quick scan of the surroundings and didn’t see any lights on inside any apartments in my building or the others in the complex, and I started to walk. That’s all that I really wanted to do, anyway. Just walk.

I followed the concrete sidewalk around to the back of the building, continued around two wings and up the hill on the other side. Approaching the front of the building now, I was coming up to the main drive around the whole complex as well as a driveway that led to a small spur of parking between a few of the buildings. I turned down the drive to head towards the front of my building, planning on walking past and back down the hill towards the door I had used to step outside. That’s when I saw my shadow creep out in front of me and slowly grow longer and darker. A car was coming behind me…

The feeling I had was unreal… for the whole time up until then, I was excited, turned on, and totally aroused. But when I realized what was happening, I freaked out. I picked up my pace down the hill, past the main entrance to my building. Behind me, I can hear the car coming but just before I feel it’s going to pass me, it turns off the main drive down the spur between buildings. A wave of relief comes over me as I feel I went unnoticed, and then I heard it. beep beeeep. There were two short honks on the horn from the car before it disappeared around the building and I knew that they were directed at me.

Who were they honking at? Were they honking at me? Oh dear god… they saw me. Wait, they saw me. And honked!

The feelings of fear quickly subsided and I became excited again almost instantly. That someone had seen me, albeit from behind, but still felt that a honk was appropriate was such a turn-on, I felt accomplished, but even more so, sexy. The last few hundred yards to the door, I slowed my pace again and began to walk with a bit more confidence. I reached the door and moved quickly through the hallway and up the stairs to my apartment, still a bit nervous of being caught face to face by a complete stranger.

When I got into my apartment though, I ran to my room, kicked off my shoes, and went straight to bed with a smile on my face.

Welcome advice and a somewhat recent scare

Thanks to Janie for her advice-filled post about broaching the subject of crossdressing with a (more specifically, my) significant other. As her post mentions, it’s a response to one of my posts from a while back about how I’m looking forward to when my now fiancee starts school again this fall so I may have a few more opportunities to dress. She also links to a post from Gabrielle over at myCDlife about how to tell your wife that you’re a crossdresser. Between both of these posts, there’s plenty of advice which I will certainly retain for when I do eventually build up the confidence to tell.

But first, a quick story… living with my girlfriend has posed a challenge that by now you know is self-imposed: how to dress without her knowing or finding out. Some nights, we’d go out for a few drinks but stay out later and drink more than anticipated. She would often hurry into bed immediately upon arriving at home, a cross between being a bit drunk and definitely exhausted from a long day and late night, while I would stay up for a bit to watch SportsCenter and head to bed well after she has fallen asleep. Over time, I began to notice that I had an hour or two to myself and I started to take those opportunities to slip into some of the less cumbersome pieces of my wardrobe, with breastforms, high heels and all, and just lounge around dressed comfortably (t-shirt and boyshorts usually). I’d even step out onto our balcony to smoke a quick cigarette, unafraid that someone in an adjacent building might be awake and notice me.

I don’t remember exactly when this happened – I think about 7 or 8 months ago (and for the record, I was going to tell this story as part of the “Old Stories” category sometime soon actually) – but one night while dressed in my typical comfy clothes, I fell asleep on the couch. My girlfriend, having been in bed for almost two hours now, felt that I wasn’t there beside her and woke up. (This happens occasionally, where subconsciously she knows I’m not there, wakes up, finds me passed out in the living room, and wakes me up to come to bed.) But this time…

She came out to the living room and saw me there on the couch… Boyshorts. Tight t-shirt. Breasts. High heels. Ohmygod.

Sensing her, I woke. Of course, she freaked out. Started to cry. Stood there hesitantly, wondering what to do or say. All the questions you would expect were thrown at me in one quick instant. “How long have you been doing this?” “When?” “Why?” “What does this mean?” In the meantime, I scrambled. Shoes off. Breastforms out. Standing there in the living room, I as well freaked out quite a bit.

Oddly enough, she ran back into bed… I quickly changed into my boxers and climbed into bed with her. With some reassuring words that I’ve been dressing since long before I met her and that she has nothing to worry about (ie. I’m not cheating on her), she calmed down and fell asleep again. The next day was normal… no further discussion at all, and it hasn’t come up again since.

So I’ve rambled on a bit further than expected. More, especially about the recent advice, later…

Heating up a bit more

I was not exactly a model student in college so instead of graduating after four years, I had to go for an extra year. To boot, during that fifth year, I didn’t finish my final project and was given an “incomplete” for my final project. I would have time to finish it on my own, but that’s neither here nor there. The point of this story is that my last year of college, I moved off campus to a large apartment complex a few miles from school. I moved in with two of my good friends, one guy and former roommate, and a female friend of ours.

Don’t be misled… nothing would ever happen with either of them. But having a girl as a roommate only kept the desire to dress going. They both traveled regularly on the weekends, and I was still dating long-distance. That meant I had the apartment to myself on the weekend quite frequently. I’m sure it’s pretty easy to figure out what I would be doing on those weekends…

I had the time and opportunity to dress more often, so that’s when the one glaring hole in my wardrobe showed itself: I didn’t have any shoes. Somehow, I decided it would be smart for me to walk right into the local Payless store, browse the women’s shoes, and buy two pairs for myself. Good lord, I even tried them on in the store! I figured that if anyone asked me why I was buying women’s shoes, I would tell them that it was because I had lost a bet with friends and had to dress as a woman to serve drinks one night. Almost as if I were their waitress…

But thankfully, no one said anything. I left Payless and walked home with a big bag holding a pair of chunky-heeled pumps and high-heeled, above-the-ankle zip-up boots. Whoa… So that morning when I got home, I tried them on immediately. The first time in my. own. high. heels! It was awesome… and that’s when I really began to dress with fervor.

I’ve read about other crossdressers doing this, so while I know I’m not the only one that has ever done this, I still feel kind of weird about it. But anyway, I’d keep my eyes open in my apartment building’s laundry room and if I saw some unclaimed clothes in there for a few days in a row, I’d sift through them and take what I liked. I’m not talking about opening a dryer while it’s running, and I’m not talking about underwear or intimates… I can thank Victoria’s Secret for those. I’m talking about clothes that would be thrown onto a chair in the corner of the room, left unclaimed for sometimes days! So I think I had found a few shirts that I liked and I definitely remember taking a pair of short jean shorts.

Now with a full wardrobe, including shoes… I quickly became more adventurous.

Almost caught up

I’ve almost taken you through all of the hows and whens (I’m still trying to figure out the “whys” myself) of my crossdressing, from the start as a young teenager through college, but I’m not quite up to today just yet. From the previous story, you may have noticed that crossdressing had taken a decidedly different turn for me: it was no longer about just dressing as a woman for my own gratification, but I was starting to have some serious sexual desires and fantasies where I play the role of the woman, dressed my best of course.

Through college, I had dated steadily, going very short periods of time without a girlfriend. Over the past ten years ranging up to this day, I’ve had three very long-term relationships with very little single time in between. Shortly after my sophomore year began, I had sex with my then-girlfriend for the first time, and I was off and running in that respect. So needless to say, being in the dorms in college and having a girlfriend almost constantly, I did not get to dress that often (pretty much never I guess); and looking back now, I almost feel as though I had kicked the habit for quite some time.

Summers at home, starting the summer after my sophomore year, were often rather busy; I was working two jobs, an office job during the day and waiting tables at night, seeing my girlfriend (the second of the three long-term relationships at that time) whenever I could, and after that, seeing my old high school crew in the remainder. Being at home did, however, take me back to when I was a teenager peering through my sister’s closet trying to find a dress or a pair of panties and a bra that I could wear.

Ironically, and with no sort of premeditation about it, before I left for college I had stowed one of my sister’s bras and a pair panties deep in the closet in my bedroom where no one, not even my mom, would find them; it was just where I always hid them back in high school so I didn’t have to go into her room every day. This was especially convenient at that time because my sister had moved out of the house. So in the little free time that I had those summers, I at least had something I could slip on late at night while I watched television in bed or to wear while sleeping. There were a few items left in the closet in her old bedroom which I had tried on, I think a few old dresses or blouses, but I had grown considerably since high school and nothing fit.

So for a while, I was left with just the two basics that I needed to rekindle my desire to dress every summer. Good enough for the time being, but that would change.

Back in the day…

Posting earlier today has me thinking of two things:

1. I had a pair of shoes a few years ago, when I was living alone, that was hands down my absolute favorite pair of shoes ever. I’ve probably gone through about a dozen pairs of heels over the last 6 years, and the Tustin 6″ Platform remains above and beyond all others.
   
   

   tustin 6 inch platform shoe, the one's i miss the most

   
   I had to throw them out after probably half a year of being able to wear them around the apartment whenever I wanted. Oh, I miss them… =/

2. This is my second post today… whoa! As I’m realizing that there are more things I’d like to share, I’m finding that I want to post more and more often. So, enjoy!
   

Oh, that first college summer

College, of course, was a lot of fun. For the first time in my life, after four years at an all-boys high school, I was starting to attract a bit of attention from girls. Though through the end of my freshman year (I still had not had sex, nor even received or given oral sex in any fashion) my sex life was starting to gain traction, it didn’t provide the sort of sexual release that I was truly hoping for. However, with non-stop high speed internet access in my dorm room, I was able to spend a fair amount of time searching for porn.

With respect to school, I failed miserably in my first semester (I think I failed 3 of the 5 classes I took), was forced to take a reduced class load in the spring semester, and after numerous discussions with my parents about how to get back on track, we decided that I would spend the summer living on campus and taking summer classes. Somehow, with luck on my side, I was given a “double” room in one of the dorms, but only I would be living there. So for the summer, I had the room to myself…

Ironically, despite all of my curiosity and exploration while in high school, I don’t remember dressing at all that summer. Looking back, I kind of wish I did because now, I wish I had that kind of alone time to do whatever I wanted. But I do remember masturbating a bunch and watching a lot of porn. It has to have been around that time when I first say videos from ideepthroat.com.

This woman, Heather, has the skills that fascinated me… to deep throat a long cock, to literally fuck it with her mouth, to take it anally, and to swallow huge loads of cum without even batting an eye. I was absolutely fascinated. Still wondering what it would feel like to have my own dick sucked and to see a woman swallow my load, my curiosity leaped a bit further.

And so it was that summer, in the privacy of my dorm room, when I first jerked off and… ate my own cum…! I know some of you are probably thinking that it’s gross, that I’m a freak, or something else like that. But I don’t really care… Watching Heather in those videos was just so awe-inspiring and such an incredible turn on that after a while, I would watch more intently exactly what she was doing, studying her moves and mannerisms.

I haven’t had my own cum that many times since that first night, and most of the times that I have intended to, I end up chickening out. I don’t know why… =/ But I do know this, and this is a thought that I still have to this day, I would absolutely love to suck a big, long cock and take as much cum as I could. It’s an experience that will probably never happen, but I like to think that just from watching Heather, I’d be pretty damn good at it.

A late night drive, finally

(continued from my last post…)

It was nice and warm out, so I ran to my room and threw on a pair of sneakers, grabbed my car keys, and headed for the door. You can’t imagine my nervousness!!! I hesitated and waited at the door, worried sick that my nosy neighbor across the street or the state police trooper that lived next door would see me and either approach me or tell my parents. We lived on a quiet side street, only a dozen houses or so, where cars very rarely passed, so I thought that someone would surely notice my hatchback lighting up and pulling away well after midnight!

But after a few minutes, I dismissed my jitters, surveyed the street to see if any lights were on in the houses or if any cars were coming, and ran out the door to my car. Butterflies took me over as I started the car and as quickly as I could, shifted into first and sped up the street. After a few turns, I was finally out of my neighborhood and started to calm down. I drove back into a few neighborhoods were I knew there wouldn’t be much traffic until I had almost forgotten about the two bumps I had in my t-shirt.

After about half an hour, I decided that I would head back home, but instead of taking neighborhood streets, I would take the main drag, Route 1. Looking back, I must have been crazy! There are cars and trucks on that road all night, and being a few miles from home, I had a ton of traffic lights to stop through. But I did it anyway…

I did have to stop at a few red lights, but not once did another car pull up next to me. I got really nervous when I saw a big 18 wheeler come up next to me, thinking that the driver would be able to see down from his cab into my car, right at my crossdressed chest! But as he pulled up on my left, I realized he wouldn’t be able to see me. A few minutes later, I had arrived back into my neighborhood and took a lap around the block just to make sure no one was out and about. I pulled up to my house, in neutral so I was as quiet as possible, shut off the car, and sprinted back inside.

With comfort comes confidence

This must have been the summer after my senior year of high school, I think. I was home alone for a night, maybe a weekend or so. My parents would occasionally travel for a few days to see old college friends and at this point, my sister that had been living at home had now moved out. Of course, I was slick enough to hold on to some key garments of my sister’s that would stick with me for a few years: bra and panties and a pair of bike shorts.

As time had past from my early experiences with dressing, porn, and masturbation, I had grown to be more comfortable wearing a bra and panties around the house while home alone. A big bonus was that my senior year of high school, I was able to leave school as early as something like 115pm because I had study halls scheduled at the end of the day. So back in those days, I was able to dress with panties and a “stuffed” bra for at least a few hours before my parents would arrive home from work.

As was the case with most high-schoolers in the mid 1990s, most of my clothes were probably too big for me. I did however have some t-shirts that I didn’t wear too often because they were smaller than I would want them to be. So this one summer night while I was home alone and dressed for most of the day, I had been lounging around in a pair of Champion basketball shorts and a small t-shirt that helped show off my bust more than my normal t-shirts. With the shorts, I had rolled them up over the waistband a few times to make them seem a bit shorter, like girls used to do with those types of boys’ shorts.

As night fell, I continued to watch TV and surf some of the adult-oriented chat rooms on America Online (I tell you more about this some other time). The next thing I knew, it had gotten past midnight and I was getting bored, but not quite ready for bed. Despite how comfortable I felt now wearing a bra and panties, the chat rooms helped me develop more confidence as my feminine self, and it was that confidence and comfort that had me thinking that I was ready to go out for a drive…

Teenage influences

So now I had begun to dress more often and more realistically (perhaps?) with the breasts and hips I had created and access to my sister’s wardrobe. Keep in mind, I was still rather young and nervous, but curious. At that point, there was no way that I was going to go shopping for myself, dress to pass in public, or anything else that might expose my secret hobby. I wasn’t even sure if dressing was something I wanted to continue to do or if it was just a phase. However, I knew that when I was dressed, at home, alone, my mind would race with different thoughts and fantasies.

Looking back to that time of my life, it’s a bit easier for me to identify a few factors which definitely influenced, increased, and encouraged my desire to crossdress and explore further. As a young teenager my friends and I had discovered porn, I was still a virgin and would remain so until I was 19 years old, and I was going to an all-boys high school. Having an older sister living at home facilitated crossdressing rather nicely as well, providing a wardrobe through which I would search for outfits and inspiration.

As my libido grew through high school, I struggled a bit with the fact that I never really had much interaction with girls. There was a “sister school” that we would have mixers with and they provided cheerleaders for our sports teams, but I was often more concerned with doing well in school and working in my spare time rather than chasing girls. Masturbation is just a part of life for teenage boys, but watching porn on occasion allowed me to calm my desires and sort of refocus until the urge came again.

I had gotten my hands on a porn video that I kept at home and that’s when things started to turn in a different direction for me, I think. I had a TV/VCR combination in my room and was able to watch it whenever I wanted after my family went to bed (my parents and sister’s bedrooms were well away from my own). Now, I was able to dress and watch porn at the same time, so that after I’d get my fill of the video I would slip into the bathroom to masturbate. It’s sounds so crude, I know.

As time went by, I became fascinated with the different roles that the man and woman had in the videos. One of the things you observe early on in run-of-the-mill porn is how the strapping guy would pound away at his woman, leaving her wasted but satisfied, sometimes hungry for more. Or, conversely, the woman diligently works on her man, sucking his cock, riding on top of him, or offering herself from behind. Her overall goal, often, is to bring her man to cum, either inside of her, somewhere on her body, or in her mouth. Remember, this is a basic assessment at best; certainly not applicable to all types of porn, merely what I was exposed to early on.

I could have masturbated all I wanted, but at that point in my life, I was never going to know what it would be like to be that man, to fuck a girl. While most teenage boys would watch and masturbate to the fantasy of indeed being that man, I would often fantasize about what it was like to be the woman. The women often derived so much pleasure that I became intensely curious about what it would be like and feel like to have a cock deep inside of me, to have my lips and my tongue all over his cock, or to accept his cum as a gift, a reward to me for my work.

Though I have never been attracted to a man in any way, a lack of exposure to and interaction with girls and crossdressing during all of these fantasies surely heightened my curiosity and desire to know what it felt like to be that woman.

Getting creative

When I started crossdressing, as I’ve mentioned in the past, it was always with something I pulled out of my sister’s room. As time went by and I continued to dress while home alone, I became much more comfortable wearing women’s panties and bras. This is kind of funny and a little bit embarassing, but I remember trying to think of how to create, as realistic as possible, a respectable chest and hips.

Both of my sisters have very small chests; actually, they are both probably the most petite women that I have ever met, both about five feet tall and weighing in around 100 pounds… tiny. If I remember correctly, my sister that was living at home for a short time when I was in high school was a 32B. Nothing special there. It did work out well for me though because as a 14 year old, I still hadn’t grown as much as I would by the time I was in college.

So, back to the embarassing part, I used to go to the kitchen and take some plastic sandwich bags, fill them with water and tie them off with some twine. After some trial and error, I was able to fill them both to the same size and keep them from leaking for quite a while. Into the bra they would go, and all of a sudden I had breasts that for all I knew, moved and looked like real ones!

As for a pair of hips, I had found some bike shorts in my sister’s room; you know, the short, tight, spandex shorts that girls wear jogging or riding a bike. She had a pair that fit me perfectly, and when I pulled them up to my waist, they extended down just below my butt. I tried a bunch of different “fillers,” and eventually settled on using two washcloths from the bathroom. Again, after some trial and error, I had found just the right way to fold them and push them into the shorts, and the spandex material would smooth over the wrinkles and folds and give a nice contoured look.

So there you have it… I had created my own breasts and hips! My mind would immediately turn to the dresses and skirts in my sister’s room, and since I now had some girly curves, I spent plenty of time trying to find one that fit me right.