First Time En Femme with a Lady Top

I always knew I was a bottom. A submissive. I would fantasize about being the more feminine person in a sexual dalliance. Submitting my body, most specifically my mouth and my ass, to a bigger, stronger man. I liked to stay fit but never wanted to gain too much muscle mass so I could be the thinner, smaller person in bed. It didn't hurt that my natural predisposition was towards being quite skinny.

I hadn't really thought too much about dressing up as a woman, even though the fact that I was a bit feminine in my features was something that I was clearly aware of and even proud of. At 21 years old, I was about 6 feet tall but I was very toned and thin without even trying. I had long slim legs like a model and always have and likely always will have a thigh gap. I have a pretty thin waist naturally leading to a small hip and then down to the aforementioned legs. And I have very little hair naturally. I am a man, so I do have to shave the blonde, thin hair on my face and I get hair on my legs like anyone does, but my chest, back, belly and behind are almost completely hair free naturally. To top things off I wore my hair shoulder length and had certainly noticed while playing with it that it could be worn in a typically womanly style which worked well with my elfin features.

I still thought of myself sexually as a gay man who had sex with other gay men, not necessarily in a vanilla way, but certainly without any extra accessories or clothing or anything like that.

This all changed one evening while I was logged onto a hookup site looking to set something up in the near future to get some dick. My regular fuck buddy, a hot older guy in his 40's, had recently moved away and I was in the midst of a bit of a dry spell. So I was on the prowl but not really finding much of anything when I received a message that sent my world spinning a little.

"Hey, I couldn't help but notice from your pictures that you have a body that would look amazing dressed up in crossdressing accoutrement! Feel free to ignore this if you're not interested but I would be happy to help you explore getting in touch with the girl inside you :-) Our "positions" in the bedroom clearly line up as well. Hit me up if you want to talk about hanging out! - Lucy"

I was caught off guard but immediately intrigued. Of course, the first thing I needed to do was see who I was dealing with here. I clicked on her profile and was instantly even more intrigued. Lucy looked like a strong, powerful woman. She had all the womanly parts we often notice on first glance; Nice perky boobs, a full head of black wavy hair, smooth and soft and lightly tanned skin, very tastefully done makeup, and a classy black dress that went down to about mid thigh, which showed off her well toned legs that looked much more robust than mine. She listed her height as 6'2" and her weight suggested quite a bit more muscle than mine did. Lucy's face had a perfect mixture of strength and femininity. She had a somewhat square jaw but a fine nose and high cheek bones. She was 38 and she was somehow both a bombshell and a stud.

Her profile description read: Strong woman with topping equipment seeks young twinks, femmes, and more to help them explore their sexuality. Obviously, beginners and first-timers welcome!

I thought about it for like 5 seconds before I began to draft my reply letting Lucy know I was extremely interested. I did want to find out a little bit more about what I would be getting into. I also like to feel out my sexual partners at least a little before I get involved in anything. I wrote that I would love to talk more and was wondering what she had in mind. I let her know I didn't have any clothes or makeup or anything and I didn't have a ton of money at the time for extraneous purchases. I made sure she knew I wasn't trying to get anything from her financially, I just wanted to be honest.

Lucy responded right away and letting me know my lack of supplies was no problem. She asked me what my measurements were; waist, hips, chest, thighs, and legs. She felt like she might have some clothes that might fit from when she was younger and a bit less muscled. Lucy said all she asks is that I was completely shaved except my head and to make sure I was very clean inside and out. She made this last point with a ;-) emoji. She stated we could begin with playing around with clothes and see where things went. If I wanted to come and dress up but didn't feel like hooking up if I wasn't feeling it, that would be fine. She liked sex with someone who wanted her, not someone who felt obligated for any reason.

I was really turned on and excited by this point. Just talking about the idea of crossdressing was waking desires in me that had been hiding under the surface for quite a while. I got out my measuring tape and quickly got to work on getting my numbers to Lucy. I got completely naked to make it easier. I must have looked quite funny, as I was sporting a rock hard boner while taking the numbers down. I began thinking about the implications of what I was doing. I was measuring my body so I could dress up as a hot young woman and let's face it, unless things felt really off, I would then be (wo)man-handled by another hot woman with a dick.

I sent Lucy my measurements and waited for her response.

It came: "Very nice. The speed at which you replied tells me you're pretty excited, huh? Can you come to my place after you eat a small lunch on Friday? I'll message you my address on Friday morning. Also let me know what your girl name will be, I'll be calling you by that name going forward."

I was actually free on Friday so I thought for a minute about what I wanted to be called and responded. I decided on Daisy. I don't know why, it just popped into my head. Maybe because it reminded me of exuberant, bright dispositions, things I hoped to embody as a young woman. I also confirmed my availability and pressed send. There it was. I felt there was almost no way this wasn't gonna happen now.

Lucy responded, "Great, I'll be in touch on Friday. I'm excited, Daisy! XOXO"

My stomach fluttered with anticipation and my loins stirred. I was going to get a whole new perspective on things this week. It was just what my sex life needed!

Friday was days away but I was pretty busy so I actually had less time to dwell on things than I usually do when I'm looking forward to a hookup. When I did have a moment to think on it, I would look at myself in the mirror and imagine my smooth-shaved pale white skin with lipstick, makeup, and hair done to accentuate my feminine features. I did a first round of shaving on Tuesday night. I spent a long time making sure my legs, armpits, and other parts were perfectly smooth. This would make it easier on Friday morning. After shaving myself I lay in bed and imagined myself all dressed up and the scenario that was going to play out in just a couple days. I masturbated and then resolved to hold off orgasming until Friday at Lucy's house.

Friday finally arrived and after a busy week I was able to get a real good rest the night before. I woke with a nervous energy and stirring inside me that I get when I'm feeling a fuck is imminent. I was in the middle of re-shaving my body to complete smoothness when I heard a new message on the hookup site arrive. I practically jumped at it when it went off.

"Good morning, Daisy! I hope you are excited to come over today. You can get here around 1 or so. I can't wait! I've got a couple cute outfits that should be perfect for your skinny figure." Lucy also included her address.

I replied that I was super excited and I would see her at 1 o'clock.

I finished preparing myself. I finished shaving, got all cleaned out, and got dressed. I wore a simple pair of tight exercise pants and a shirt with no underwear. I figured, what was the point of underwear today?

The drive over to Lucy's house was a blur but next thing I knew I found myself outside a fairly normal one story house on the outskirts of the city. It was a cute little house with a very well manicured front yard and a nice wagon in the driveway. The normality of it put me at ease. You never know when you're going to show up somewhere and it'll be a complete mess, which often doesn't bode well for the inside.

With a little bit of nerves, I walked up and knocked on the door. In no time, the door opened and there she was. Lucy was everything her photos promised and more. She was a babe as a woman and had the magnetism of an alpha all at the same time. I had to look up a couple inches to meet her gaze as she looked me up and down, nodding approvingly. Lucy was wearing a simple tight dark purple dress along with sheer stockings and the perfect amount of makeup, as she had on in her profile pictures.

"Hi, Daisy! So happy to have you visit me," she said with her slightly smoky voice, opening the screen and allowing me to walk in, guiding me subtly by the lower back as I floated past her.

"Thanks for having me," I squeeked. I didn't mean for it to come out so meekly but it had the effect of setting the tone for our relationship well somehow. It was in stark contrast to Lucy's relaxed and confident delivery of her greeting.

Lucy laughed and said, "The pleasure is mine."

Lucy had me come into the living room and sit down as she fetched us a couple waters. We sat for a minute catching up. What we did with our time, how our weeks were, etc. It felt nice and put me at ease. Lucy was really good at that. She was really controlling the mood of the visit from the very start. She wanted me to be relaxed while she was feeling me out personality wise.

I actually brought up dressing up first. I asked how long she had been doing it and she told me she had started dressing up as a 19 year old in college before becoming serious about it in her 20's. Eventually she went "full time". She had had a mentor who had helped her figure things out in her early twenties. It was one of the reasons she liked to do what we were doing.

This was a very obvious segue into us shifting gears into the ultimate purpose of my visit. She asked if I was ready to give it a go.

"I am very ready," I said with a coy smile.

Lucy laughed and said, "Ok then!"

"Why don't you start by stripping down?"

When I had been a bit less experienced I was very conscious about getting naked in front of others but now that I had had a couple regular relationships of various sorts, I had no problem with it.

I quickly tore my clothes off and found myself completely naked in Lucy's living room with her appraising eyes looking me over. She gave me a smoldering look as she hummed her approval and said, "Very, very nice."

The fact that I had Lucy's approval was already a turn on for me and my dick responded in kind. It began to swell slightly and get hard. Lucy noticed and cocked her eyebrow while walking over to me. She reached out and put her hands on my hips and stroked my waist, hips, and butt cheeks up and down several times before lifting her hands up to push my hair back behind my ears and holding my face delicately in her hands. I was beginning to really get into it now as my breath became a bit faster and heavier.

Lucy leaned in and kissed me full on the lips, slowly pushing her tongue into my mouth in an intense French kiss that lasted maybe 10 seconds. She pulled away and looked down at my now hard cock with a rye smile, which I returned.

"Clearly, you liked that. Let's go into the other room, shall we?"

It wasn't really a question and Lucy grabbed my hand and led me down a hallway from the living room into what would have normally been a guest room for most people, I assume. For Lucy, it was a dressing room, filled with clothes and accessories of all sorts. There was also a vanity with all the lighting and mirrors for doing makeup.

I took it all in, a bit overwhelmed. I wasn't sure where I was supposed to start in a place like this but luckily, Lucy had already gotten a lot of things all figured out.

"Wow, this is something else," I exclaimed.

Lucy laughed and said, "Well, it's about 20 years of collecting stuff. I should probably get rid of some of it but you just never know when you're gonna need something. Case in point.."

With that she grabbed a red garter belt that had been laid out on a bench along with some other select pieces.

"Why don't we start with this."

With that we began to get me dressed for the first time so I could really transform into Daisy.

Lucy had me put on the garter belt first. She then gave me two black stockings to pull on. Once those were up, the black material stark against the white of my upper thighs, Lucy fastened the three clips on each side of the garter belt to each stocking, allowing her hands to linger on my body as she did so.

Once that was done, Lucy stepped back and allowed me to admire myself in the mirror. The long black stockings on my skinny legs made me feel incredibly sexy with the straps from the garter and then the garter itself snug around my waist. I was only wearing two pieces of clothing and I was already feeling my feminine side rising strong to the surface. Without even thinking about it, I walked a couple of steps with a sashay to my movements.

Lucy laughed and smiled with appreciation towards me. "I think this is gonna work out pretty well!"

I beamed at her and put my hands on my hips, my confidence rising.

"What's next?" I asked.

Lucy considered the collection of clothes that were laid out on the bench. She seemed to make a decision and grabbed a pleated checkered red and black skirt and handed it to me.

"Go ahead and start with that."

I slipped the skirt on and pulled it up to my waist. I drew the zipper up and fastened the waistband. The skirt fit perfectly. It hugged my waist a little below my belly button and went down to my upper-middle thigh, just below where the stockings ended. I gave a little shake of my hips and laughed, enjoying how the skirt would flow up and reveal the white of my thighs and the hint of my bare ass when I did so.

Lucy had a big smile on her face as she watched me enjoy the clothes.

"We'll keep it simple for now," she said.

With that, Lucy handed me a tight, black woman's t-shirt that ended about two inches above my belly button. The effect was that I had a bared midriff and a skirt that just barely covered the bottom of my ass and the top of my stockings. My long slim legs were certainly a highlight as well. It was a casual but super hot look.

Lucy walked behind me as I looked at myself in the mirror and grabbed my shoulders.

"Sexy, huh?"

I hummed an affirmative and admired us in the mirror.

Me, almost completely feminine, being held by the strong hands of an amazon goddess.

Lucy grabbed my chin with one of her hands and gently turned my head. She leaned in and gave me another deep French kiss which made my body tingle with lust.

As Lucy released her grip on me, we both realized my skirt was tenting a bit as her kiss had re-awakened a massive erection from me.

Lucy said, "Oops, I almost forgot."

She grabbed a pair of black underwear and gave them to me.

"They're a little tight by design, especially if you're hard, but these are good and comfortable. I have a feeling we won't be needing them for long but for now they'll help you keep your bits secured."

I slid the the panties on and they did secure my hard cock to my body, very tightly of course, as they were not really meant to be worn over an engorged dick. But at least the tent in my cute skirt had disappeared.

Lucy admired me and said, "Ok, final touches."

I was sat down at the vanity where Lucy began by simply pulling my hair back in a ponytail and securing it. She then went to work with the makeup. To be honest, I'm not sure exactly what she did but by the end my creamy skin looked faultless and my lips had a sexy red lipstick on them. The final detail was perfectly applied eyeliner to give my eyes a little bit of extra sexiness.

Lucy leaned back a little, admiring her work and said, "Well Daisy, I think you were made for this honey. You barely needed anything compared to a lot of other women to make yourself look fine as hell."

I felt incredibly sexy. Lucy grabbed my hand and pulled me up and we admired the finished product in the mirror. I took a minute to appreciate the feeling of the stockings on my legs and how long and lithe they look. I loved the feeling of the cool air on my skinny, toned belly. I loved how the outfit accentuated my thin, delicate feminine features and how my bone structure really suited the getup I was wearing. Besides the fact that I had no boobs, I looked like a model in their early twenties.

"Do you want shoes or do you just want to go barefoot for now?" Lucy asked.

"I like wearing no shoes actually. Maybe next time?" I said hinting at doing this again already. I also didn't feel like trying to figure out walking in anything tricky with how sexy I already felt.

Lucy laughed. "Yes, maybe next time. What do you say we go have a drink in the living room and relax," Lucy said.

Of course I agreed. I was happy to just be myself at that moment. It felt a lot more right than I had even expected it to.

We went into the living room and I realized there were quite a few mirrors here as well. As Lucy went into the kitchen to get some wine, I admired myself in the mirrors, checking out the curves of my ass and everything else I generally didn't get to appreciate much when wearing my normal clothes.

We stood around a little nursing our wine and talking about what an amazing feeling it was that I was having. Lucy was getting really touchy and feely as she talked about different things I could do and different types of clothes I could wear and how they would work on me, including lingerie and things like that.

Lucy then guided me to the couch and we sat down next to each other. I crossed my legs and let myself look very ladylike, perched on the edge of the couch while Lucy crossed her legs and leaned back comfortably. We both knew what was about to happen.

We both put our wine glasses to the side and began to get a little flirty with each other while we talked. I was mostly allowing my hand to rest on Lucy's knee and strong thigh, lightly stroking her stockings as the conversation became less and less important. Before too long, Lucy put her arm around my waist and pulled my body towards her. Our lips met and we began making out hard. Lucy's hand was exploring my body and lingering more and more on the curves of my ass. My hands were appreciating her body as well but were more specifically beginning to ride up her thighs towards her crotch.

Lucy broke the kiss and asked, "Have you ever given a blowjob with lipstick on?" I shook my head no. "Well if you want to try it, now's your chance," she said with a laugh.

Not wasting a moment, I immediately began pushing Lucy's dress up until her entire pantied crotch was exposed. I grabbed both sides of Lucy's underwear and began to pull as she lifted her hips slightly. As I dragged her underwear down her legs, I was excited by what I found under them.

Lucy had described her dick as being 8"x5" online but I had been so caught up in the thought of dressing that I hadn't ever considered that her cock was theoretically so big. Well. It was.

Barely even hard at all somehow, Lucy's uncut cock was already impressive. We continued to make out as I began to play with her balls and go to work at waking the beast up. It didn't take long before Lucy's dick was just about fully hard and my mouth was salivating at the upcoming taste of it I was about to get. It was time to go to work.

I got on my knees. Lucy grabbed me a couple pillows to kneel on and I settled in between her legs on the ground. I looked over to my left and since the mirror went to the ground I was able to admire myself, made up as girl, on my knees, about to suck a fat dick.