First Time En Femme with a Lady Top

Lucy's dick was hefty. I first admired the weight of it in my hands as I held it up, exposing her balls fully. I leaned in to get my first taste. Starting at her balls I went to town. Getting Lucy to 100% hard was my first order and starting at the balls was a good way to do that. Once I felt the shaft was rock hard I began to lick slowly up her veiny shaft until I reached the head. I didn't put it in my mouth yet but I did lick all around the rim of her dick head and lash the very top of head with my tongue as I built up saliva with the excitement of tasting dick.

Then I went at it. I allowed Lucy's spongy head to push itself into my mouth and deeper towards my throat before lifting away from it, lashing the head with my tongue and going back down. I settled into this head bobbing. Lucy was really getting into it. She had her head back and was moaning and encouraging me. "Oh yeah, suck that dick, girl." That sort of thing. She would stroke my hair and lightly hold the base of my pony tail as I went down on her over and over again.

While I settled into the blowjob and appreciated the texture and flavor of Lucy's dick and eventually her precum as it began to stream out, I also allowed myself time to appreciate myself being on my knees in a super sexy outfit in full makeup. At first glance anyone would have surely thought that I was simply a sexy, lithe young woman pleasuring an older transgendered woman.

Surprising to me was that barely any of the lipstick had come off on Lucy's dick. It must have been quality stuff. I liked that it stayed on my lips as the texture of it coupled with the visual of it on my face helped me feel that much more immersed in what I was doing.

Eventually, Lucy began to really huff and puff and I felt like she might cum. I wasn't sure what the plan was so I just kept at it, thinking I'd be happy to swallow a load now and let her fuck me later but Lucy had other plans. She applied gentle but firm pressure pushing me away, which was a sign I was very familiar with to back off the cock I was currently consuming.

I let Lucy's big dick drop in front of me and wiped the extra saliva from my face and mouth with my hand. Holding Lucy's thighs while on my knees I looked at her expectedly.

Lucy helped me get up and said, "Let's go into the bedroom now."

I nodded and silently let her guide me back down the hall by the hand. We went further down the hall than we had before, all the way to the end where I could see a bed waiting for us. We went into the room and a king sized bed dominated the space. Lucy turned around when we were both in the room and grabbed my face, laying a deep kiss on me.

She then looked me in the eye and told me, "Take off my dress." I help Lucy remove her dress by undoing her zipper and pulling it up over her head, revealing her full figure. God, she was amazing. Strong but womanly, I was now able to really feast my eyes on a feature I had never really found sexually attractive until now. Lucy's boobs were perfectly sized in my mind. Each one was just large enough to hold in one hand and perfectly perky. I helped her take off her bra and Lucy let me play with them for a second. I must have looked like a child with a new toy because Lucy laughed and said, "First time, huh?"

I nodded and laughed. Lucy leaned in and kissed me before telling me to take off my underwear. While I did that, Lucy crawled onto the bed. My tent was back on my skirt but we were well beyond caring about that as I also started towards the bed.

"I want you to get in a 69 with your ass towards me," she directed.

I did just that. I took the initiative and began to go back down on Lucy. She was back to full mast in no time.

I was happy to realize that Lucy was making preparations behind me with a bottle of lube. Lucy pushed my skirt up around my waist, exposing my hole to the air. Lucy had quite the nails on her, so I was assuming she wouldn't be using those on me and I was right. As I was in doggy style, sucking on Lucy's fat dick, I felt something cool touch my asshole and recognize the plastic of a lubed up dildo. Lucy began to apply pressure and being that the dildo wasn't all that big, I pushed out a little and it slid right in.

Lucy moaned in appreciation when that happened and began the task of loosening me up. I began to really enjoy the anal stimulation back there to the point that I was letting Lucy's cock drop every now and then to give a little moan. When this began happening Lucy got the message that I was ready to get fucked because she slightly patted my ass and began to move me off her.

"Ok Daisy, are you ready to take me?" She knew I was but I appreciated her asking anyway.

"Yes, please," I responded sincerely.

"Ok, take off your shirt and skirt, you won't be needing those," She said with a smile.

I stripped down to just the garter belt and stocking.

Lucy had me grab the top of the headboard and arch my back with my skinny stockinged legs spread out quite wide and my ass presented to her. Lucy ran her hands all around my ass cheeks, hips, and waist as she appreciated my body. Lucy methodically unrolled a condom over her penis and began to apply copious amounts of lube to her shaft and then put a dollop on the head to lead the way.

The dildo Lucy had used to warm me up was quite a bit smaller than her cock so I knew I was in for a real stretching as I felt the battering ram of her girthy dick rest at the opening at my ass.

Lucy held me by my hips as she began to apply pressure. I braced myself and clenched the headboard and pushed back lightly but consistently, opening myself as much as I could. Lucy's head was slowly beginning to impose its will on my body. Her dickhead was plugging up my hole and had gotten purchase but I could tell that it would be intense when my body actually yielded and let it push its way in.

And it certainly WAS intense. Suddenly my sphincter let up and Lucy's head and shaft sank a couple inches into me. I yelped and felt the sudden but not problematic pain that comes from a really good initial stretch. One of my legs began to shake a little and I began to breath a little more intensely to diffuse the intense and amazing feeling of being stretched out so suddenly.

Dressed in a garter belt and stockings with full makeup and a smoothly shaved body, I realized just how feminine my sex noises had always been.

In a high pitch voice I let out, "Oh fuck, oh fuck, oh fuck." as I adjusted to the feeling of this huge dick in my ass. It was something I often did when first accepting a cock into me.

Lucy was rubbing my sides and massaging my ass and giving some pretty intense moans of her own.

She asked, "Are you ok, does it feel alright?"

"It feels so good, holy shit, just go slow," I replied while breathing heavily.

Lucy was very patient and let me get used to her without moving. It really didn't take too long however before I began to glide back and forth to get her dick to slide a little bit deeper inside me. Lucy picked up on this and began to work with me. Slowly but surely more and more of Lucy's cock had found its way into me and the pace began to pick up.

My hole had given up any sort of resistance to the fucking that was beginning to happen and I began to sink into the pure bliss of getting reamed out. The length of each stroke got longer and the power stronger until I felt Lucy's thighs smack my ass on a particular stroke. This cause me to emit a particularly high pitched moan but truth be told I was already moaning like a woman with every invasion of Lucy's cock head deep into my body and each punch that my prostate took.

Lucy had also reached the next level of bliss as she settled into long dicking me, grunting and moaning the whole time. Smack, smack, smack...the sound of flesh crashing into flesh.

Lucy pulled my upper torso towards her and I felt her tits on my back as she thrust all the way into me and held me fully impaled on her dick.

Somehow, without pulling out of me, Lucy maneuvered us onto our sides, with her behind me. My one leg was flat on the bed and she held my other leg spread and high up, opening me to her fucking. I'd always felt I looked sexy as hell being fucked on my side and this was no exception at all. My belly was taught and prominent and covered in sweat while framed by the garter belt as Lucy began to piston back in and out of me. This was all done in front of a full length mirror on Lucy's wall. I really got to appreciate the hot scene I was taking part in as Lucy went to town using my body.

I rested back on Lucy and turned my head allowing her to kiss me as she was fucking me so incredibly hard, my prostate getting battered and my whimpering and whining was at a fever pitch.

Lucy finally slowed in this position and pulled out for the first time. She turned me on my back and lifted my legs up, tucking a pillow under my ass. It was at this moment I noticed yet another mirror above the bed. It was in that mirror that I watched as I felt Lucy put her dick up to my hole with my legs high and spread wide, each ankle held in Lucy's strong hand. Lucy then leaned in and sank her cock all the way into me with one smooth fuck forward. As Lucy did that, I felt a huge drop of precum leak out of me and down my shaft. I then watched in the overhead mirror as Lucy began to long dick me over and over again, crashing past my prostate and hitting me deep inside at the end of the stroke. I began to lose it as Lucy picked up steam and really fucked me hard. I was practically yelling over and over again, covered in sweat and other fluids.

Lucy leaned down a bit and let go of my legs, putting her hands to either side of my head like she was planking. Her tits were hanging in my face and I began to lick and suck them which cause Lucy to moan loudly and somehow pick up steam. She then fully laid down onto me as we yelped and moaned and groaned as we fucked. Lucy's head was next to mine, my chin was on her shoulder and I was able to wrap my long legs around her waist.

I watched in the mirror this unbelievable scene of this now disheveled, sticky, sweaty blonde girl in her early twenties, her skinny black-stockinged legs wrapped around a woman with the woman's hips crashing down over and over driving a fat dick into the girl's body again and again.

Suddenly I heard Lucy exclaim, "I'm gonna cum!"

Lucy gave three full strokes, cock head all the way down to balls, each one making me yelp loudly before she growled and gave one last stroke that was so intense and strong I felt like she was trying to fuck a hole through me! With that I could feel Lucy tense up and her hips giving short, quick jabs as her balls and shaft contracted and she filled the condom up deep inside me.

Ever the generous lover, Lucy quickly regained her composure and lifted herself up enough to free my rock hard cock from between us. My legs spread as wide as can be and with a dick still firmly buried in me, Lucy began to jerk me off with abandon. I resisted the desire to cum right away just to let a little more pressure build up down there but as Lucy's slick hand rode its way up and down my shaft, it was too much for me to take and I felt a massive orgasm approach.

When it finally came I saw stars. I moaned and spouted gibberish and my legs shook as my loins tensed up. I drew my hips back as much as I could and then thrusted forward as my balls contracted and sent my cum flying over my body, covering my stomach and chest with the first rope and then shooting again and again, all the way up to my neck and chin. Lucy encouraged me while continuing to stroke my dick and even slightly stroke in and out of my ass with her semi hard dick.

As the orgasm finally subsided Lucy flopped down next to me. I began to process what I could see in the mirror above me. A blonde girl covered with cum, sweat, and smeared makeup with her skinny legs spread wide and still raised a bit to let a battered asshole get some cool air on it. Garter belt and stockings askew. Next to her lay a more mature woman, not old, but certainly no longer young, panting and recovering after a massive orgasm. The whole scene was incredibly hot and satisfying.

I leaned over and cuddled up to Lucy, She held me in one of her arms as I rested on her bosom.

"That was amazing," I whispered.

She replied, "It sure as hell was. And that was only the first time..."