My First Crossdressing Ad

Growing up, I had always been a weird, lanky nerdy with long hair and a quiet demeanor. Even when I signed up to play sports in middle school, I was never what anyone would consider to be masculine and preferred hanging out and talking with my female friends than getting rough and dirty with the other boys. That's not to say I was particular effeminate either - Although I did not having much muscle, I still had broad shoulders and a relatively square jaw line. As I got older and went through high school and college, I stopped trying to traditional guy things, and instead opted for things like theatre and the arts instead.

Being a sensitive, artistic guy who preferred to listen to women than compete for their attention, I didn't have any trouble finding female companions for my bed. I've had many great experiences with woman and love everything about a woman's body. My willingness to listen to their needs and given them the pleasure they wanted led me to explore a number of kinky things that some people wait till their 30s or later to experiences - but those are different stories.

The first time I can remember dressing up in women's clothes was when I was 18. The girl I was seeing and another female friend of ours had learned a tattoo parlor did a "Thigh High Thursdays" special, and were interested in getting some tattoos. $20 off the ink if you wore thigh high stocking and let them take a picture for their wall. I keenly noticed that the ad made no reference to gender, and suggested I should dress up too. The girls lit up, and excitedly ran to pick out some of my girlfriends clothing I could wear. I wore a leopard print top, with a black knee length skirt and fishnet stockings. I was not at all passable, and had a bright blue mohawk at the time, but felt sexier then ever before getting to shimmy about in stockings.

The tattoo parlor, with some hesitation, honored the special and snapped a picture of me. They later updated the promotion to specify women only, but kept my picture on the wall anyway.

Though nothing else eventful happened that evening, it planted a seed in my head.

I was 21 when I first posted an ad on Craigslist looking to explore that part of me further.

"Feminize me -m4m - m4w - m4t

21 year old slim submissive guy wants to be dressed to the nines, but I don't have any clothes, no makeup, and I live with my parents so you would need to be accommodating. I'm not smooth, but I can shave at your place if you'd like. I'm 5'10" and 135 lbs, been told I'd make an excellent girl, and I'll be pretty passable with the right makeup and a wig. I'm not looking for anything sexual unless we both click (sorry guys,I'm more into girls and trans) but you of course get to see me all dressed up in whatever you like. Looking for tonight or anytime this week, but mostly tonight."

I didn't have much hope for a quality response, even though I immediately got several from lonely men who couldn't string together more of a sentence than "Hi" or "Still Looking?" and more dick pics than I care to look at. After an hour of that I had resigned myself to playing alone that night, but then I got a response which caught my eye.

"Good evening, I saw you ad and I wanted to express my interest, though I'm not exactly sure I'm what you're looking for. Older daddy type who's helped girls like you dress up in the past. I love the look of tight clothes on a pretty body and like to make it a reality. I have some clothes here which you can model for me and keep. No touching unless you're comfortable with it, and I'm disease free should we get that far. If you'd like to get together and dress up I'm happy to give you a safe place for it"

He also included a clothed picture of himself, and two little outfits that he wanted me to wear. He was an older man, seemingly in his mid 40s, with some extra weight. His hair was starting to grey and he wasn't terrible attractive, but he did look kind and his response was very intriguing to me - I'd never really been attracted to men in the past, but the idea of modeling for one was very appealing! The clothes in the picture looked a little slutty - a white sequin two-piece outfit with a miniskirt and sleeveless crop top, and a blue shimmery lycra micro dress and matching thong. I was more turned on then ever by the prospect, so I replied to him that I'd be interested with a picture of myself. We exchanged numbers and a location, and I told him I'd be on my way.

I of course had reservations as I drove to his place about half an hour away from me - Would he still want to do this once I got there? Is he going to be rude and demeaning once I was dressed up? Was the nice guy response just a facade so he could lure me into darker things? Before any of those thought could get the better of me, I was walking up the stairs to his apartment and at his door. I swallowed my insecurities and knocked.

He opened it and looked exactly like his picture - a good first sign for meeting someone over the internet. He smiled and invited me in. "I'm glad you made it. You mentioned you would have to shave so I left some razors and shave gel in the bathroom for you. There's also a joint if you want to smoke. I already drew you a warm bath."

I thanked him, and told him this was my first time so it may take a bit of time to shave. He laughed and said "I can help if you want."

I didn't want him to help with that, but I did feel like I may take up more time in his bathroom than he'd appreciate, so I offered "No, but you can watch if you want. We can talk and get to know each other while I make myself smooth."

And that's how I ended up naked in his tub, carefully trying to shave my legs for the first time, while I sat, clothed, admiring while sharing the joint he had rolled for us. I nervously chatted away with him, telling him that I'd never done anything like this, and that I wasn't gay, but wanted to explore this aspect of my personality. He chatted back about his experiences, as well as about his life in general. I was in a very vulnerable position, but he was calm, patient, and every bit the nice guy his response made him out to be. He would flirt with me and compliment me, but kept his distance and respected my boundaries. Any apprehension I had previously melted away as he made me feel comfortable and relaxed.

When I was finishing up the last of the hair on my legs, he went back to the bedroom and came back with the sequined set of cloths. "Can you try these on first?" I blushed and said "Yes" and started to put it on. He left so I could dress up.

I admired myself in the mirror. Even though I didn't have any makeup on, my long blonde hair and hairless body evoked a certain feminine appearance. I was definitely a guy in women's clothing, but a smooth, submissive one who loved how the clothing fell on my body. I modeled for myself before walking to the bedroom, trying my best to swing my hips in a sexy fashion.

This was my first time seeing his bedroom, and it was certainly impressive. He had a huge TV, a king size bed with silken sheets, and large cushy chairs on the other side of the room. He sat in the chair, with a camera on his lap, grinning from ear to ear as he scanned my body. "Would it be OK if I took pictures of you as you model? Just for us."

I couldn't help of thinking of my picture on the wall of the tattoo parlor. "Yes, please, but only if you send me copies." He smiled and started taking pictures.

"How about you go over to the bed... Good like that... Climb up there now... Good... Look back at me?... Excellent..."

For the next 20 minutes, I took his direction and posed in all the ways he wanted me to. Sometimes he would have me look seductively at the camera, other times he would ask me to get on all fours with my ass up in the air. I relished in the attention. Hearing the camera click and knowing his eyes were lustfully tracing my body was making me giddy.

"OK" he said "Lets try this one on next." He handed me the blue micro dress with matching thong. I began to undress and lay out the next dress.

"Do you mind if I get more comfortable?" He asked. "That's fine" I said, focused on getting into the tight blue dress. It clung to my skin and barely covered my ass. I slid the thong up my legs but it wasn't anywhere large enough to cover my cock. I started to feel a little silly.

"I can't fit in this thong," I said dismayed. "That's fine, I like your cute cock," he replied. I blushed and turned to see he had gotten completely undressed. I began to feel vulnerable again, wearing a tight slutty dress and matching thong that couldn't contain my manhood, as this older man stood nude before me. His cock was hard. He was not as long as me, but was thicker, and unshaven. He looked at me with a hungry look in his eyes.

I returned to my position on the bed, modeling the new dress. He picked up his camera and began to give direction again.

"Mm, that's good... Get that sissy ass up in the air... Spread your legs and show off your cock... Good... Get on your knees like you're going to suck cock... Excellent... Just like that baby... Good now back into bed with you... Great, what a perfect view..."

"I think that's enough pictures." He said, and set the camera down. "Would it be OK it I laid down with you a bit before you go?"

"OK" I said "But don't try to kiss me on the lips and we're not having sex."

He didn't respond to that but crawled into bed with me anyway. I turned by back to him and rested my backside against his body. He wrapped me in his arms and held me close, while kissing my neck and running his hand up and down my body. I could feel his cock against my ass, the thin fabric of the thong the only thing between it and my flesh. In that moment it all became so clear to me, that not only did I seek out this experience with another man, but that I gleefully took his directions in stride, and that this man's lust for me was turning me on immensely. I wanted him to want me, to long for me, and I wanted to see him cum.

At that time, he also made his lust for me abundantly clear, and came close to violating my boundaries. I felt his strong hand move the thong to the side, and press the head of his thick cock to my tight virgin asshole. I quickly moved away, off the bed, knowing I couldn't take that thick cock inside of me.

"I'm sorry" he said, "Your ass was just so delicious I couldn't resist."

I considered getting dressed and leaving immediately, but the thoughts I had previously were infesting my brain - Of course he wanted to fuck me! I had dressed up like a perfect slut for him and modeled these beautiful clothes for him, which he was gifting to me as well. It's only natural that he was horny, and that he should want something in return. And in truth, I wanted to give him something in return.

Without saying a word, I crawled back into bed, but this time between his legs. He looked at me, a bit confused at first, but then recognized the hungry look in my eyes. I had never sucked a cock before, but this man had been so kind and generous I couldn't help but want to take him into my mouth. I started slowly, licking the shaft all the way down to his hairy balls. He tasted sweaty and musky, which never sounded like a turn on before but only served to increase my desire in that moment. He groaned with pleasure.

"Fuck baby that's nice, keep doing that."

I did. I licked him thoroughly, his cock dripping with my saliva before I was brave enough to wrap my lips around the tip and start the slow decent to the base. I bobbed my head up and down his cock, like many women had done to me, and caressed his balls as the head of the cock reached my throat. His hands found their way into my hair, and a felt him taking control of my head as my mouth worked on his cock. He firmly, but gently, started guiding my head to the rhythm he wanted, and his hips began to buck as well as he fucked my face.

It wasn't long before I felt him close to finishing. I did not want to swallow his cum on our first meeting, so I slipped my mouth off of him and turned myself around. I got on my knees and left my check fall to the bed, my legs spread and ass high in the air for his viewing pleasure.

"Cum on my asshole daddy" I said, pulling the thong to the side and exposing my virgin hole to him. I didn't look back to get a confirmed from him, and was scared he may try to take liberties with me in this position. I was delighted when I felt his warm sticky cum land on my ass and drop between my cheeks, and to feel his fingers rubbing the cum onto my asshole.

After a few minutes to cool down, I got dressed, kissed him on the cheek, and thanked him for the clothes and experience.

The next day he e-mailed me a ZIP folder with all the pictures from the night before - My favorite being the one with my hair disheveled, dressed in a tight blue dress and pulling a thong to side while sticky white cum dries on my ass.