Share your first experiences with CD!

Crossdressing as a part of or type of selfbondage.
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TheWingmen
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Location: North America

Share your first experiences with CD!

Post by TheWingmen »

Thought it might be fun to share stories about how you got into it!

Very first thong was one with a black lace waist band, black and grey snakeskin pattern for the fabric, and a tiny pink bow on the front that my girlfriend at the time bought and sprung on me out of nowhere one night before a typical dinner and a movie date after reading that "forcing" your man to wear women's underwear would get them all hot and bothered. Little did she know that I had been sneaking around at home when family was out of the house trying stuff on and it had turned me on for ages. So you can imagine I was pretty excited when she got on board and we could share it.
Over the 2 years I dated her it became a regular occurrence for us to be out on a date, we would walk past a VS and she would tell me to wait outside while she went in. She would come out with something for her, and then would discretely put something for me in my pocket. I would then have to go to the nearest restroom and put said item on and hand off my male underwear to her. We would then continue on our date (often dinner and a movie as mentioned above). She would always find moments when I wasn't expecting it to grab a handful of it and give it a tug to remind me what I was wearing which would just turn me on more.
When this little "game" of buying things while we were out started she would buy items in my appropriate size, but as time progressed she got a little more sadistic with it and would buy items that were much smaller than they should be (for example at VS my size should be between M and L and she would buy things in XS to make them very tight and hard to forget I was wearing).
I remember the most sadistic she got with it was while browsing an American Apparel store downtown she came across the thong leotards they sell. She knew I had a thing for seeing her wear them and when she started looking I thought I was going to get a show that night :wink: . But then she grabbed an extra small size (which she wasn't) and I instantly knew what was about to happen. As soon as we were out of the store I was given the usual instructions. But this time to put it on I had to completely strip :oops: . Not only was it tight around my waist, but the fact that it went over my shoulders combined with the torso length on an extra small being much shorter than my torso made it pull up quite tight too. And every time I bent over or moved I could feel it rubbing and making turning me on more. I swear that was the longest walk I had ever taken, lets just say when we got home I couldn't wait to get out of it and get to business, but she was having none of that. Off came all my clothes except for the leotard, on went the handcuffs, and I was told I had to take care of her before I could take it off and have my way.
There was also a period of time after we moved off to college where she would lock away my male clothing and each morning I would receive a message from her letting me know which thong I was supposed to wear for the day, then sometime during the day she might randomly show up and check, it was quite fun.

Anyways thats how I collected most of the female clothing I own (although I purchase my own items now). Let me know how you got into it!

PS- I apologize if there is already a thread in here with this theme, I used the search bar for a bit and could turn up nothing
nullbound
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Re: Share your first experiences with CD!

Post by nullbound »

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Last edited by nullbound on 03 Oct 2017, 00:48, edited 1 time in total.
8ruce
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Re: Share your first experiences with CD!

Post by 8ruce »

I'm not sure where to put this. It was my first time out in public dressing enfemme and it was my first playtime in front of someone other than a partner. Either way, here is my first time. I'm sorry for the length, but I hope you enjoy the read.

My now wife got me to dress up in stockings and a thong for her one night shortly after we moved in together. Up until the night in question, it had always been individual pieces. So here goes the story....

My wife was out of town on business (about half way through a three week trip), and told me to get home and get showered. She had informed me that there was some conspiring going on behind the scenes, and I was going for a special time with one of our friends. I was instructed to answer her texts, and and do what I was told. My wife informed me that I was to bring her pictures of the night's events as well as there being a conversation between the three of us via phone during the festivities...

Anyway, I rushed home, stripped out of my work clothes and I'm not even sure the water got hot in the shower before I was in, scrubbing, and shaving like my life depended on it.

After the shower, I towel dried off and applied baby oil to soothe the quick shaving job. Luckily, I had only nicked myself once, and it wasn't in an important spot. There was a text waiting for me when I walked into the bedroom. I was told to dress in black stockings, a florescent pink thong and bra, black tennis skirt, and a fairly tight fitting red top. I was to change my nipple rings out for the stirrups before stuffing my bra. My first order of business was to paint my toenails my favorite shade of purple.

I figured makeup was coming next, so I slid the fresh stockings up my freshly shaven legs (and I have to say there is nothing like that feeling!). After both were up and where I liked them (why does that seam at the top drive me freaking crazy?), I went to tucking and hiding everything under the pink Candy's thong that felt smaller than it looked laying on the bed. I got the bra clasped, spun, and up easily enough and realized that I had forgotten to change my nipple piercings. So, I reached into the cups one at a time and pulled the barbells out and replaced them with the stirrups like instructed. My stirrups are our signal for playtime. If I'm wearing them, I'm in the mood. If I'm told to put them in, look out... Last thing I did was to stuff my bra with the homemade forms made from stockings and rice before pulling on the top and skirt.

I knew another text was coming, but just not when. I headed back to the bathroom to start the foundation process, and *ding.* I was told to send a pic of the progress. Doing what I was told, I received the next text that informed me that my makeup was to be perfect. *gulp* I gave it the best effort I could muster, and about 30 minutes later, I sent another picture of my progress. I was told to go check the top drawer of my wife's dresser and I'd find a wig and another small box. "Put the wig on and what's in the box too." I was so excited by the wig. I just stopped and stared in the mirror. Where did I go? Who was this person staring back at me? In the box was a pair of clip on hoop earrings and a matching necklace. I couldn't believe my eyes. There was a woman staring back at me. I worried about the feelings I was getting. I didn't want to ruin the work I did tucking, but I could feel the pressure building.

After another picture sent, the reply told me to put on a pair of slutty heels, and stuff a medium sized plug in my rear. Doing as I was told yet again, I slid the pumps onto my feet before kneeling on the end of the bed with the lube, plug, and a damp rag. I was nervous. Could I get the plug in without needing to tuck again? Would I ruin any of the work that I did? Well, the answers were no and yes, respectively. The plug was not cooperating, and I had to fix a bunch of things before I ventured on. In the mirror was a total slut wearing 4" heels, black sheer stockings, a skirt that barely covered the tops of the stockings, a tight red shirt hiding fake cleavage, and a perfectly framed face. There goes that pressure again...

The last text was a set of instructions. First, a pic. Second, get a bag. Put a posture collar, ball gag, wrist/ankle cuffs, locks, keys, and flats in the bag. Third, put makeup essentials, my driver's license, a $20 bill, and a condom in a clutch. Fourth, get the car keys and bring the two bags.

Wait. What? But I've never gone outside like this before.

Well, after a stern text, I was told to bring my sissy ass to (place redacted), which was an hour away. WTF? My neighbors are on their back porch (which is all of 6 feet from my car). So, I ventured onto my back stoop which was hidden from most views in the daylight. Thankfully, in the "winter time", I was concealed in darkness about two hours ago...

So, I sat down on my stoop, lit a smoke, and waited out the neighbors. Not thinking about it, I flicked the butt down the sidewalk. About 5 more minutes of sitting on that plug was all I needed to make a break (and hopefully not my ankle) for the car.

First thing I thanked the stars for was the refuel I had done that morning. I started the car and made my way out of my small town, on to the highway, and toward uncertainty.

Every single car. Every. Single. Car. Were they looking at me? Is my wig crooked? Am I sitting lady-like enough? OH GOD OH GOD OH GOD. Let me tell you the cruise control was set for 2 mph UNDER the speed limit, but the cruise control on my brain was BROKEN.

I finally made it to our friend's house. Street parking was usually pretty easy to find. But do you think it was on that night? Nope. I had to park a block down the quiet street. I could hear the foot falls on the concrete. That noise. I have always connected that noise with utter sexiness. And that pressure down below was starting to connect to it as well. As I rounded the corner, I saw the door open leaving the storm door fogged up. I knocked. There were more people in there.

Terrified, I knocked a little louder. Our friend came to greet me at the door. "Awww, what a cute little thing we have at our door." She turned to the unseen living room, and asked if anyone called for a good time. That feeling. It wasn't my Adam's apple. It was my stomach and my heart having a party in my throat.

I was ordered in. My bag and clutch were taken from me, and I was relieved to see that there was only one other person there. He looked me up and down, wolf whistled, and turned the stereo on. My friend told me that I had done a good job with my dressing and makeup, and that she wanted to see everything.

She told me to turn around slowly, and feel free to start dancing. The wiser part of me figured that wasn't a request, so I tried my best attempt at dancing like a girl. I had no idea what the hell I was doing, and apparently it showed. I was so terrified, that my brain wasn't even registering what was playing. He got up off his chair and offered to dance with me. She got up and joined us. I had no idea what was going to happen, but she started to manually move my parts around like a marionette. I was so humiliated when the music changed. She told me to turn around away from him. Mockingly, I was shown how to grind. I felt dirty. I felt his cock through his jeans and my skirt.

As she left the room, I was taking my instructions from him now. Shakily rubbing my ass in his crotch, I heard it. The click of a shutter. If I didn't have that makeup on, I would have been as white as a sheet of paper.

"Don't stop. Your wife wants to see these pictures. Show her how much of a whore you are."

Next thing I knew, there was a chair in the middle of the living room, and I was giving the first lap dance of my life while being photographed. After what seemed an eternity, I was told to get up off of him. I had no idea what was going to happen next. "Go to the bathroom. And make sure you sit down to pee like the sissy girl you are. And don't make me come up there to watch and make sure." I tottered upstairs in the heels, used the bathroom, washed my hands, and slowly made my way down the steps.

The chair in the living room had disappeared. These foam blocks were brought out, and I was confused.

"Strip. Slowly." Off came my top. Apparently, I took it off like a man, and that was the wrong way. She threw it back. "Put it on and take it off again." Confused, the top went right back on. This time I had help. "You have to look dainty while you're giving a strip tease." Again, I got a mockingly abrupt lesson on how to take my clothes off.

I wasn't going to be ridiculed for the skirt. I spun around, bent over at my waist and shimmied the waist of the skirt in my thumbs. Once it was passed my thighs, it fell freely around my heels. Stepping out of the skirt, still bent at the waist, I almost went face-first into the couch picking it up off the floor. "Well, that didn't go as I had planned," I remember thinking to myself...

Silence is what I got. Silence and an unimpressed glare. It didn't strike me right away, but there I was: heels, stockings, bright pink thong, stuffed bra, and plug. I guess my face changed accordingly when I figured it out, and she laughed one of those obnoxious laughs all the while shooting pictures. "Your wife is going to LOVE these."

"Come here," was said from behind the camera. "Crawl." So, I got down on my hands and knees and made my way across the floor among the noises of the camera. "Turn around and take your plug out." The feeling was the strangest yet. I now am holding a butt plug in front of a stranger. One that I had smuggled into the house, and I was holding it like I was being questioned about contraband at the airport.

"Put this one in." What the hell? "That's not going to fit" I thought to myself. But, silently, I found the condom in my clutch. Realizing that I was still holding the first one, I pulled the condom off of it, balled it up, and threw it into a side pocket of my bag. The still warm plug followed its way into the small side pocket. The fresh condom made it over the new, larger plug, and with the help of a little lube, up my ass.

Wow. I couldn't move without being reminded that it was there.

I was told to stand in the middle of the room and take off my bra. Flippantly, I pulled the homemade breastforms out and juggled them into my open bag. I can now say in hindsight, that was the wrong thing to do. She got up off her chair, pulled one out of bag, and stared at me. I knew I was in trouble.

"Are you ready for the next part? This is what your wife asked me to do while you were up here. She told me that you had tried it once before and liked it so much." I had no idea what she was talking about, but I figured that I didn't really have much choice. My new friend reappeared to grab the foam blocks from their resting places on the couch and brought them over.

"Spread your legs" was the only instruction I got, and both went to work quickly wrapping my stocking clad legs with pallet wrap. Once my legs were done, my arms were next.

(Now I have to say that my wife and I had experimented with saran wrap once before. Once. I liked it, but we had to cut our session short so I had asked her to try it again at some point.)

I didn't realize that this was that point. This was fucking serious. The mystery foam was finally brought into the picture. I had to close my legs around the long piece before they wrapped my legs together. Similarly, my arms trapped a piece of foam each before my trunk was wrapped. Gauze pads were stuck to my chest over my nipples and the wrapping commenced. It felt like they used a whole industrial roll on me before they tore the ends off.

A few more pictures, and my posture collar went around my neck, followed by a few more pictures.

The two of them laid me down on a blanket on the hardwood floor before she straddled me. I had no idea why she was holding safety shears in her hand, and at that point, I didn't care. I was in heaven. I was trapped. If I could get my hand to my crotch, it would have been all over.

What she did was cut the plastic away from my nipples, exposing my stirrups. A few tweaks and twists later, and hooks had been attached to them. Followed by a few fishing sinkers. Alright. I'm not moving anymore. Between the plug in my ass, the weights on my chest, and my posture collar, I wouldn't have moved even if there was no saran wrap...

So the next four hours were spent on the floor alternately being ignored (she was in the room) and ridiculed. Every time I would find bliss and start to nod off into subspace, a well placed squirt of water would bring me back to the reality of my situation. At some point, my lipstick found its way out of my clutch and my body became a canvas for bright, red, humiliating artwork. That and the nipple torture sent me over the edge. I started to struggle more only tiring myself out more.

By the time she started cutting me loose, I was a mess. I was hot and sweaty. My makeup was smeared. My ass ass was sore. My nipples were raw. My body was stiff. I really had no idea how long I was wrapped up, but all I wanted was to curl up in a ball and drift into the best sleep I've ever had.

After a little bit, I was told to go upstairs, leave the plug in the sink, and get a shower. The hot water was amazing. It felt like putty melting in the falling water, but it brought me back to the world. After I was out and dried off, I looked in the mirror and I was back. I felt like I didn't want to go back. And I got my wish for a few more hours because in all the prep at home, I left my masculine clothes on my floor in my bedroom. I walked downstairs in a towel, trying to figure out what I was going to do.

Not thinking, I had the towel wrapped around my waist. She looked cross at me and asked me what I was doing. Confused, I didn't know what to say. I was told that I had my towel in the wrong place. I had to rewrap the towel around my chest, like "the good sissy I was." I was asked again what I was doing. "I'm trying to figure out what to wear to head home." "Well, where are the clothes you brought?"

I pointed at the neatly folded skirt and top laying next to my bra on a chair. "Well, put those on. What's wrong? What clothes do you want?" I guess I wanted my jeans and a tshirt, and she could see that. "I didn't bring anything else."

"Why not?"

"Because I wasn't told to bring anything else."

"Well, at least you can follow some directions. Gather up and put on what you wore when you walked in the door."

So, that's what I did. I put on my stockings, bright pink underwear, stuffed my bra, and put my skirt, top, and flats back on before heading downstairs. When I got downstairs, I had some makeup put back on my face, my wig fitted, and my earrings clipped back on. I had a condom slid to me. "I told you to leave as you came. The only thing that you can have is your flats. You've been in your heels for a long time." Sheepishly, I took the condom, found my plug in my bag, and reinserted it. It's one thing to put a plug in. It's another to have someone put it in for you. But it's a completely different story having to do it in front of another person.

The last thing that got handed to me was the memory stick from the camera. "Make sure you don't look at those before your wife sees them."

By the time I made it back to my car, I had enough time to drive home and shower (for a third time) and go to work for a LONG day...

Best night of my kinky life.... Thank you honey.

PS - We still have those pics too.
New Bound
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Re: Share your first experiences with CD!

Post by New Bound »

During High school About 30 something years my girlfriend and I along some of her friends where celebrating Halloween at a friends house. As the liquor flowed the girls started getting silly and we started a game of truth or dare.
Eventually the truth was getting boring and I took a dare to put on a dress. Being young dumb and full of cum I accepted the dare. My girlfriend got a blue gown from the closet. I thought no big deal and pulled it on over my Tshirt and jeans
spun around a few times and figured it was over. WRONG!!! I was told that I was going to be completely made over and to strip down. A High school boy in a bedroom full of drunk girls what do you think I did.
The girls treated me like a prom queen they put me in panties stockings with a garter belt bra stuffed with pantyhose a long blonde wig and full make up. They commented on how beautiful I looked. They tried heels on me but I was to drunk to wear them and they settled on flats. We all went back Downstairs and continued to party. After the party the girls took some pictures with a instant camera. and gave them to me to remember the night. They then removed all traces of makeup and clothes from me and thanked me for being such a good sport. When I got home that night I was turned on by the evening as there was no sex with any of the girls that night, they told me they where not lesbians
I jerked off several times that night. I lost the pictures in a flood but will always have the memories of that night.
CDTammy
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Re: Share your first experiences with CD!

Post by CDTammy »

When I was five years old, my step monster used the closet in my room for her overflow. One day she was doing a quick change and left a pair of suntan Leggs pantyhose on the floor. Curious, I put them on. My life changed, at least secretly from that point on. I slept in those hose, I wore them under my clothing. Keep in mind, I knew nothing about sex. I just knew these felt good. Later, I slipped into her bedroom and discovered that she had a three drawer dresser that was full of pantyhose. She never noticed losing a pair here and there over the years.
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bound_jenny
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Re: Share your first experiences with CD!

Post by bound_jenny »

CDTammy wrote:When I was five years old, my step monster
You're using autocorrect, aren't you? That devilish little device is responsible for more hilarious typos than any spelling error could. :rofl:

When I was five, I also had a step monster - it was hiding under the stairs in the basement. No relation to the monster hiding under the bed. :mrgreen:

Jenny.
Helplessness is a doorway to the innermost reaches of the soul.
If my corset isn't tight, it just isn't right!
Kink is the spice of life!
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CDTammy
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Re: Share your first experiences with CD!

Post by CDTammy »

Yes. Typo, we'll go with that.
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