Like a Deer in Headlights

"Alright man. I'm headed out," Bruce said to me as I wrestled with the controller for a bit.

"Friday night date?" I said as I paid attention to the screen without giving away my expression which was one of rising glee.

"Yup. This blonde I met at the gym. You'll like her, she's a little nerdy and nice to talk to," Bruce said as he got up, his hulking frame leaving a shadow on his chair.

Bruce was my roommate for many many years. We met when we were in college, and have been together as roommates ever since. Me and Bruce were diametrically opposite people. He was the stereotypical jock and player, going from girl to girl, bringing girls home, and according to one other mutual friend "drowning in pussy", while according to another mutual (female) friend "can get it anytime."

Bruce was to some people the epitome of tall, dark, and handsome. With his broad chest, muscular shoulders, brunette hair that he kept combed pretty neatly, he was not bad to look at. He grew up in the Midwest, played football in highschool and college and was now a "Finance bro".

Whereas I was a scrawny kid when I met Bruce, and now a scrawny man. I never had too much luck with the ladies, and while that bothered me at some point, it didn't now (and I'll get to that in a bit).

I was the stereotypical nerd and introvert, staying home on Fridays, and according to one mutual friend "being a loner loser" and according to another mutual (female) friend "could get it if he wants but isn't my first choice mainly because he's not my type but I'm sure he's someone's type?"

I was short, thin and even at the age of 22 (I'm 29 now), thought I wasn't done with puberty. My slender body caught up a bit in my mid twenties and age helped but I was definitely not the same species of man Bruce was. A fact I knew and embraced actually.

"What about you? You got plans?" Bruce said to me as I put the controller down.

"Nah man. You know me. SkyRim's Gate 4: MistBorn's abdication just got out, so I'm all set! I will probably take a shower before that though" I said. That was a bald faced lie. Well, not the shower, that I was going to do.

You see, at some point in my adolescent and young adult life, I let curiosity get the better of me, and I put on a pair of women's underwear, also known as panties. Just like how Batman's life changed when he put on the mask, so did mine when I wore those panties. It awakened something in me, something that to this date I could not get rid of.

As I grew, so too did this desire. What started out as a liking for panties grew into a liking for bras, a liking for stockings, a liking for high heels, a liking for imagining myself as the woman in porn, and a liking for spending my Friday nights in my bedroom wearing lingerie and fucking myself silly with my 8 inch dildo.

Yup, I had become a full fledged sissy.

Which brings me to my earlier point, at some time in the recent past I just gave up on pursuing women, and decided I had more fun being one. I had never been out as a woman however, and the only person who had ever seen me as a woman was my mirror.

It wasn't that I was gay or preferred cock. I still loved women. It's just, the more I looked at them, the more I wanted to be them and not be with them.

Fridays have become my Feminization days. Bruce would inevitably be out and I would have the house to myself. I would take the time to shower, shave and put on makeup, drink a glass of wine, relax and unwind before fucking myself silly with my 8 inch dildo.

Bruce had obviously no idea.

I did a very good job of cleaning up after myself and hiding things. I had a chest under my bed, with most of my femme accessories: bras, panties, garters, wigs, makeup and sex toys. Bruce was usually out the whole night, so at some point when I was femme-ed out, I would slowly put everything back in the chest under my bed, and pretend like all I did was play video games.

"Alright bud. I'm out. Have a good one!" Bruce said as he gathered his coat. I exchanged farewells and immediately ran upstairs. I waited till I could see him get in his Uber from the window in my bedroom, and ran to the bathroom to start my everything shower.

For the uninitiated, an everything shower is a concept that has existed for a while but made popular by "Tik Tok girlies". It basically involved a shower, a full body shave, followed by a moisturizing regime and other care activities. For me, it involved converting myself into a woman.

Like most things that one enjoys, I had no idea how the simple act of wearing panties escalated into something like this. It started off small, as I liked wearing panties under my clothes. I would feel a secret rush when I talked to other women while wearing them, almost like it was a little secret of mine. I would imagine them having no idea that there was a chance we were wearing the same underwear. From there, it went into bra wearing and stockings and garters.

I had become quite adept at buying these things. When I first ventured into this world I was very discreet, using fake names and a PO box to collect the things. As time grew on, I became more confident, almost careless, and I would have things shipped directly home. I had even gained enough confidence to shop in person at a Victoria's secret, and while I never outright stated the panties and lingerie were mine, it was obvious to anyone who rang me out. They wouldn't say anything because a sale is a sale after all, plus I'm sure they didn't care who did what to their product.

As I finished shaving my body smooth from the neck down, including my genitals and my taint, I thought some more about how I got to where I was. Like I said, it was an escalation, but at some point it kept getting racier. The first time I bought a dildo was about a year ago. I hesitated, and went back and forth on it, but I eventually did after much consultation with the sissy side of reddit.

If you aren't a sissy or into sissies then you probably aren't familiar with the rabbit hole that the sissy side of reddit was. This was entire subreddits and pages full of advice, guidance and rules that sissies gave to other sissies. While the panties may have awakened something, I'm sure reddit helped evolve it.

I stepped out of the shower, now completely shaved and moisturized, and wrapped a towel around myself girly-style (that meant I wrapped it around my chest instead of my waist). I liked even the littlest touches while I got feminized as they helped with the mindset.

I took out my chest and laid out a matching pink lace thong, garter set, pink thigh highs, and a bralette, while putting on my playlist. Yes, I had a playlist for Feminization Fridays, I was nothing if not thorough!

As Shania Twain crooned about how good it was to feel like a woman, a sentiment I wholeheartedly agreed with, I started to put my stockings own, enjoying the smooth feeling of the nylon thigh highs on my freshly shaved legs. I then put on the garter first and then the panties as I learnt the hard way once that if I needed to take the panties off, I had to take the garters off too. By putting the garters on first, I could remove the panties whenever I wanted, and keeping the garters on made me look hotter in my professional opinion.

I then moved on to the bra, completing my clothing for the night. I took a look at myself in the mirror before I could fix my wig and make up.

Makeup was the trickiest thing to master as a sissy. When I first started, I would just use some lip gloss or lipstick and call it a day. But, the more I learnt, the more I wanted the whole package. I learnt about facial structure, the best foundations, the best primers to cover a five o'clock shadow, and the best lipstick color for your face (which apparently should match your nipples, who knew?).

Somewhere down the line, I decided that I wanted the full experience and that a wig would complete it. I had thought about growing my hair out, but decided against it as I didn't want the hassle of maintaining it. Keep in mind that I still wanted to maintain the outward appearance of a dude.

I fixed my wig on and took a look at myself in the mirror. I wasn't exactly a woman, but I was definitely not a man. I was somewhere in between, but it didn't matter to me, I liked it and I think I looked hot.

The very last step in my process was wearing high heels. High heels was something I initially thought was excessive, plus being born as a man, I found it hard to find any in my size, but as I learnt on Reddit, there were high heels made especially for people like me. I loved the feeling wearing them gave me, I felt empowered in a way, and while initially I felt like a baby deer taking it's first steps, as time wore on I grew more comfortable in them. Besides, as a self described "Short king" who was barely five feet and eight inches, I liked the extra height.

My usual routine was to close the room door and turn on some sissy porn, but today I felt like relaxing for a bit. I decided to head downstairs and grab a glass of wine. A step that I would shortly realize was a mistake.

I pattered downstairs in my heels, enjoying the feeling of my lingerie on my body and the sound of my heels on the hardwood floor.

I walked over to the wine fridge and grabbed a bottle. I took a quick look around to see if Bruce had left any wine glasses out, but he was as organized as a slob could be and had taken his glass upstairs. I opened the bottle and poured a little bit in an empty cup and swirled it. My mom was a big fan of wine and taught me a lot, so I was a little wine snob.

After checking the bouquet, I decided the wine was good enough, and I filled up the glass and turned to head back upstairs. As I turned, I heard a noise behind me.

"What the fuck?" the voice said as I felt like a deer in headlights.

Shit. It was Bruce, standing there, his coat dropped to the floor with his jaw not far behind.

"B-bruce. I c-can explain," I said offering no explanation whatsoever. I tried to imagine what he thought, his roommate dressed up like a girl, in the most feminine lingerie imaginable.

Bruce said nothing, making the already tense air, more tense. I suppose the ball was still in my court and I did owe him an explanation.

"Okay. So I crossdress from time to time. It's not- I mean it is- like it's just a hobby. I'm not trans or gay or anything. I just like wearing women's clothes and relaxing," I said offering what I thought was the simplest and most succinct explanation I could offer.

"O-oh. I see. Th-thats not- I mean that's not a problem. I can see why you thought you should hide it, but I don't - I mean- you don't." He said before taking a sharp breath, "I mean- wow. Sorry," he said clearly struggling to say anything.

"Can I offer you a drink?" I said hoping that would calm him and me down. He nodded. I got a glass and poured some scotch before walking towards him to give it to him. It was then that it dawned on me how exposed I was.

I was in our kitchen wearing pretty transparent lace lingerie. I could have sworn that if you stared at my crotch for a bit, you could see my whole penis, to say nothing of my ass cheeks which were held together by a lacy string in between them.

He took the drink and downed it before sighing.

"Sorry. It's just shock. I didn't expect you to be here like this."

"The same could be said about you! What happened to your date?" I asked as I downed my own wine.

"She had to ditch. Last minute," he said.

"Oh I'm sorry. Look, this is awkward, who are we kidding? I can go back and get changed and we can try to forget about all of this. Or I could go upstairs, get changed and never come back down or run into you again. Or I could go upstairs, get changed and move out," I said while he chuckled.

Humor was always a coping mechanism of sorts for me.

"No. No. I mean. Look, it's okay. I promise I'm cool. You don't have to move out or anything. Tell you what, why don't you sit with me. Let's get some more drinks, and you tell me more about all of this? That is- if you want. I mean-" he said, reverting back to the awkwardness that I thought had disappeared. Looks like the shot of whiskey was wearing off.

"Um okay. Yeah. I can do that," I said as he sat down on the sofa. I refilled my glass and was about to sit down when I realized that it may not be the best idea to lounge on the sofa in a skimpy g-string.

"Actually, it's getting a little chilly here. I'll just grab a robe," I said as I walked away, once again fully aware that I was exposing my whole ass to him as I climbed the stairs, a thought that weirdly excited me.

I grabbed a satin robe I had gotten free from Victoria's (Buy 17 panties, get a robe free or something or the other), and headed downstairs. I didn't remove any of my makeup or wig or heels. A part of me really wanted to, but another part of me wanted to keep it on, if for nothing else, but all of the effort that it took to get ready.

I climbed downstairs and found Bruce sitting on our three seater couch with a full glass of whiskey, and a glass of wine topped up for me on the other end of the couch. I sat down and clocked my glass with him, while we both took big sips.

"So.." Bruce began.

I took a deep breath. Should I explain everything? Right from the panties to the dildos? Was I going to do this? Instead I decided to take a passive approach.

"Well, what do you want to know?" I replied.

"Um. Well, how did this start? What is this?" Bruce asked as he looked at me. I felt his eyes dart from the wig on my head to my lips.

"Well, I don't know. I mean I do. It started one night when I was dared to wear a pair of panties and I guess I really really liked them. And well, from there it just kinda grew. I'm not trans and I'm not gay, I still like women but I like feeling like one more I guess. Until now, it's just been me and no one else who has seen this side of me," I said.

Bruce nodded. I hadn't been this open with anyone yet.

"I'm curious. Tell me more about this dare," he said as he sipped on his drink gingerly.

"Well, I was just out of high school and I had a girlfriend and we hadn't gone all the way-" I said, reverting back to older parlances of that era " -and a bunch of us were playing truth or dare. So one of the girls dared me to swap underwear with someone of the opposite gender. So it just made sense to swap with my girlfriend. That was also the day I saw a girl's bottom naked for the first time. I was incredibly turned on the whole time, and I initially thought it was because I saw a girl naked from the waist down but the more I thought about it, the more I realized it was the panties. The fabric, the way it felt on my cock, the way I kept thinking of how the other girls were wearing similar things, and how they felt. Me and my girlfriend had sex later that night of course, but she let me keep the panties. And I guess from there things just grew," I said.

"Wow. That's wow. And this girl?" He asked.

"We broke up somewhere down the line. Unrelated reasons. " I said.

"I see. Well, that's- wow. Again, I mean it, you don't have to hide this part of yourself from me. I don't judge and you shouldn't have to feel like you're hiding this." He said as earnestly as I could.

I appreciated his honesty there. I looked at him and he looked back at me sincerely.

"Thanks Bruce." I said as I nodded, tipping my glass to him.

"You're welcome Kev- er you still go by Kevin when you're dressed like this?" He asked with an eyebrow raised.

"Kendra." I said as I blushed. It was true. I had a name for my femme self.

"Okay Kendra. I like that! I room with Kevin, but sometimes Kendra comes out to play! I could live with that." Bruce said as he nodded.

"So what do you want to do now? Should we play something?" I asked as I got more comfortable in my seat. I had nearly forgotten that I was wearing next to nothing under this robe. I was almost done with my wine.

Bruce looked at me, his brow slightly furrowed.

"Hm. Tell you what. I'd like to get to know this Kendra a bit more. Why don't we play truth or drink. I'll top you-" he said before adding awkwardly" -your wine glass. Top your wine glass I mean, and we ask each other questions. No limits. If there's a question we would rather not answer, then we take a sip of our drink. It's a fun game and a great ice breaker!" He said trying to forget the awkward flub he had just made.

It felt like he was really trying to get to know me. Not just me Kevin, but the part of me that I had hidden from the world. Kendra.

"Um okay. That sounds fun." I said as I lowered my voice to my more feminine octave.

He went to grab more wine and topped my glass.

"So who goes first?" I said as I took my glass.

"You. You can ask me anything." He said as he looked at me. He had gotten more comfortable in the couch, leaning back on one end of the arm rest with his other arm over the span of the couch.

What do I ask Bruce? I knew most of the things about him. There wasn't much that I didn't know. But Kendra was a whole new ball game to him. I decided to poke him in that sphere.

"What were you thinking when you saw me in the kitchen?"

An excellent question, I had thought to myself, even though I knew the answer. It was a reaction of shock. I could still hear his voice scream "What the fuck", but I wanted more. It almost felt like I was seeking his validation.

"Well, I opened the door and I was faced with a woman in a pink thong grabbing wine from the shelf. I thought you had someone over, and well, I thought that was a nice ass, and then I saw your side profile when you grabbed your glass, and I thought to myself that the side profile looked familiar and then you turned to face me, you hadn't looked or spotted me yet and that's when it hit me. It was you! And I guess I couldn't believe what I was seeing because I was so sure it was a hot chick- I mean not to say you're not hot-" he said fumbling at the end. What would we be without this awkwardness?

I could feel myself blushing. I took a sip of wine to cool myself down, as my mind fixated on his compliments about my butt. Was I turned on by that? I felt myself shiver internally as I tried not to think about it too much.

The game. I could focus on the game. I rattled my mind trying to think of a good question.

"What's your biggest turn on?" I asked.

What was I doing? What were we doing? Why were we playing these childish game? I couldn't help but ask myself these questions on one hand, but on the other I wanted to know more about Bruce from another angle. It was almost as if Kendra wanted to know Bruce.

"Well, a lot of things. I think my biggest turn on is knowing that the girl is having a good time. That turns me on because I like the fact that she's having a good time because of me. I know that sounds a little narcissistic but you know," he said as I nodded.

I did know. I've been his roommate for so long that I knew exactly what girls felt about him. Our wall were only so thick and sometimes he didn't even bother closing the door of his room completely. But this is a fact I never disclosed to him.

"Makes sense. But like what else?" I asked as I wondered to myself what I was trying to do. Was I trying to get him to admit that I turned him on? That seemed like a foolish pursuit. For one, why would he be turned on by me? Secondly, why would I want him to be turned on by me? I was more confused with that second internal question.

"Uh huh. That's another question madame, I let you ask me two in a row, but lets just call that pretty privilege shall we? My turn: What's your biggest fantasy? And I mean Kendra's," He said as he downed his drink.

I thought for a minute. What did Kendra like?

Big cock. Big thick veiny cock. said the voice inside me but that wasn't something I could say. No, while Kendra did like that, that wasn't so much of a fantasy. I closed my eyes and let Kendra speak.

"I think my biggest fantasy is having sex with someone as me. Kendra. And they treat me like one of their girls. Like a lady. Fuck me like one. I know that sounds oxymoronic and counter intuitive but I guess that's what I want," I said as I got up to get the bottle of wine and the bottle of scotch.

It was true. I did want that. I wanted to feel like a girl inside and out. I wanted to be fucked but I also wanted to be made love to.

"Wow. That's pretty hot and honest," he said as I topped his tumbler with scotch. As I did so, I noticed he shifted his seat slightly, not only moving a little closer but as if he was hiding his crotch. Was he getting a boner?

I sat back down on the sofa and felt myself sitting closer to him than I was originally.

"Okay. Your turn." I said looking at him.

"You mean it's your turn to ask. Jeez Kendra, how drunk are you?" he said with a wink.

"Oh right. Well, okay. Uh. What's your biggest fantasies." I said as I realized I slurred at the end there. The alcohol was getting to me. Either that or Kendra was acting drunk. I couldn't tell.

"Fantasies? Well a couple. A threesome has always been on my mind. I'd love to be handcuffed. In terms of outfits, schoolgirl. Sexiest outfit hands down," he said very matter of factly.

"I have a schoolgirl outfit" I almost said and thankfully didn't. What was happening to me?

"Oh. That's impressive. I mean yes they're all super hot but I'm surprised you haven't done any of those yet?" I asked with genuine surprise.

His lady friends and their loud exclamations weren't new to me. I could count on both hands the times someone has said "It's so big".

Honestly it was pretty depressing back then, but as Kendra, it was more impressive than depressing.

"Well, no. In the sense, I'm not complaining and this may sound really douchey but I haven't found anyone who really wants to do anything other than vanilla sex. I mean don't get me wrong, I love - what was the word Mark used - drowning in pussy? - but sometimes I wish it wasn't just vanilla." He said.

Kevin would have thought that was pretty braggadocious and standoffish of Bruce. Kendra felt pity and lust. I felt like I was in the middle of both Kendra and Kevin who seemed to be playing a tug of war in my brain, and the alcohol was clearly favoring Kendra.

"Oh? Well, I never heard any lady complain from your room so I thought you were happy too." I said and regretted it instantly.

"Wait. You can hear me? Hear us? Have you been listening to me from time to time?" He asked as my eyes grew wide.

Fuck.

One month earlier

"Fuck. It's so big" said the girl's voice. She had breathy quality to it. It was a Friday and instead of being out, Bruce decided to bring his conquest back home, much to my chagrin.

Fridays were usually my time alone. My time alone to be me. To be Kendra.

I tried to go to sleep but the noises had just gotten louder. And this girl seemed to be a screamer.

"Fuck me. Please. Please please fuck me. Fuck me like the dirty little whore I am." She screamed while I heard the bed creak.

Fuck. That was hot. That sounded hot. Did he forget to close the door again?

I shouldn't. I really shouldn't. But I couldn't help myself and I tiptoed to Bruce's bedroom.

The door was slightly ajar.

I took a peek. I already could feel my boner in my pants. I saw a naked brunette girl bouncing up and down, her tits bouncing freely while she moaned. Her back was to me while Bruce was on the bottom. I stood there transfixed. Unable to move.

Suddenly Bruce moved her around, she exclaimed and was on the bottom now and I could only see Bruce's back, his muscular back, arching as he thrust into the nameless brunette, each thrust punctuated with a moan from her.

I could feel my penis leaking pre-cum. I needed to take care of this.

I slowly slipped back to my room and undressed. I left the door slightly ajar, both to continue to heat them and on the off chance he could see me.

That was the moment I realized I wasn't myself. I was becoming more like Kendra.

Because see, I didn't want to fuck that unnamed brunette. I wanted to be that unnamed brunette. I wanted to bounce on his cock, and have his large hands on my hips.

My hands trembled as I wore my sexiest pair of panties. The panties were essential.

They made me feel like Kendra. I then took my dildo out and lubed it good. I moved my panties to the side, knelt on the floor and penetrated myself. Just like the brunette.

With each thrust I wished I was her.

I wished I was bouncing on his cock and he was fucking me. I wished I was the one he was making love to. I wished I was on his bed and his thick member was filling my insides up. I imagined him on the bottom with me riding.

Each moan she made only turned me on. At some point I lost count of how long I was bouncing. I felt a orgasm coming on. My mind was tuned out of everything else and only focused on riding that dildo. I came ropes all over the floor.

As I was cumming I realized the door was ajar. Once I came to, I peeked outside and saw that both Bruce and the brunette were asleep. Or so it seemed. I got back to my room and made sure my door was locked before never thinking of this night ever again.

Until now.

Present day.

Fuck.

"Er. I elect to not answer that. I can drink." I said grabbing the bottle before realizing that it was empty.

"Tell you what. You don't want to answer that, that's fine. How about you do a dare instead. I dare you to take off your robe." He said with a tongue in cheek tone.

"Oh. So truth or drink has become truth or dare huh?" I said as I got up to oblige him and took off my robe.

That nakedness and awkwardness I felt merely an hour ago, had just like my inhibitions, vanished.

I observed him carefully. His eyes darted around my body, starting at my chest and moving to my crotch. The lace was pretty see through, which both helped and hurt me. Helped me, because it was obvious I was being turned on. I was leaking pre-cum and it had formed a wet spot in my panties. Hurting me, because it was obvious I was being turned on.

My own eyes darted to his crotch. He was wearing jeans, which made it hard to spot whether it was an accurate boner or just incorrectly fitted jeans. But I hoped he was as turned on as I was.

"Well, unless you have better ideas." He said as he chuckled.

"Well, no. None that I can say out loud just yet," I said with a wink. Fuck. Kevin was gone and Kendra was here to stay. At least tonight. Whatever impulses of Kevin I had, had come off with the robe. I found myself sitting closer to Bruce.

"Since I still have my drink, I can continue to play drink or dare. Well, unless you have any objections?" He said with a sly smile.

"Works for me." I said. There was something about this situation that I liked. I liked that he now had the power. It wasn't just "Answer this question else get sloshed." It was now, " Answer this question or else do as I say." And I loved that.

"Okay. Your turn to ask me," he said and I decided to go for the big one.

"Do I - like this-" I said gesturing to my body "-turn you on?" I asked as I braced for the worst.

A few outcomes popped to my head. The first being that he would drink his glass. The second being that he would laugh and say "Of course not." What he did was something I was not expecting but wanted to hear from the moment he caught me.

"Yes. Incredibly so. You're so fucking hot. I can't believe you're my roommate." He said while I turned the color of my thong.

"Well, Kevin is. I'm just Kendra. A girl who finds herself in her underwear on your couch," I said with a smile. I was so close to him, I could feel his breath on me.

I wanted to kiss him. I wanted to straddle him. I wanted him to rip my panties off and fuck me right there on that couch. What was stopping me? Before I could act on any of my impulses he cleared his throat.

"Okay. I'm almost done with this bottle too so I'd be open to dares pretty soon but here's one. Do I turn you on?" He asked me.

Yes. Yes. Yes. Every inch of my body was screaming it. But Kendra was a little more manipulative.

"And what's the dare?" I asked with a sly smile on my face.

He froze for a bit. I guess he wasn't expecting that.

"A lap dance. Not just any lap dance but a strip tease too." He said with a smile.

I didn't know if he expected me to be honest because I was more turned on by him than I have with anyone else in a long time. But I needed this. This feeling of playing with his emotions. I wanted that power back.

"Sure. Pick a song," I said and I got up.

He had an impressed look on his face as the music started playing. I closed my eyes and let the music guide me. I swayed my hips to either side and moved my ass around to the music, giving myself a little spank.

I turned around and unhooked my bra, not removing just yet, but continuing to dance, with a sly smile on my face. I moved closer to him before I took my bra off and flung it towards him. I was inches away from his body, and it was hard to mistake it now. He was incredibly turned on. He was tenting through his jeans.

I moved forward to him and spread his legs.

"Mind if I take a seat?" I said coyly as I sat on his groin, facing him. I could feel his boner poke me, poke at the fabric of my thong. I was also unmistakably turned on.

I moved my " tits" close to his face, pretending like I could motorboat him. He took it as a challenge and stuck his tongue out, flicking my nipple with it, making me moan involuntarily.

Fuck. This was getting very hot.

I got off his groin and turned around and continued to grind on him, this time my ass facing him. I did this for some time, until I felt like I couldn't take it anymore.

I then moved away from him and turned around to face him. My own boner was very much visible, almost tenting through the lace of my panties. But he didn't seem to mind. He paid no attention to it. I put one thumb on one side of the waistband and one thumb on the other.

"Should I take those off?" I said with the same coy tune I used before.

He didn't say anything but nod. He was rubbing his crotch through his jeans almost involuntarily.

I turned around and peeled my panties, giving him a good look at my entire ass. Other than garters and stockings I was completely naked.

I then repeated the routine with my garters. This time he responded " No. Keep them on."

I then found myself on my knees, crawling towards him. There was no stopping Kendra. This was happening.

Bruce seemed to know this too, as the minute I got on my knees he unzipped his jeans and threw them aside. He was now in his boxers. I could clearly see the outline of his penis.

I was very close to his penis. My hands wandered to his waistband.

"Can I see it?" I said. He nodded.

I removed his boxers and was faced with his thick veiny cock. It was as big as I imagined.

"It's so big!" I said, exactly like all of the girls had said before. He didn't say anything. My hands had already started to stroke him.

"Can I please suck your cock?" I asked. He nodded.

I had never sucked a cock before. There was one time I had gotten very close to doing it. I had gathered up some courage to go to a an adult bookstore with a gloryhole, in complete boy mode though, while wearing lingerie underneath it of course, and saw a thick cock poke out and chickened out at the last minute. But the way I was going, I dared you to tell me this was my first time.

I started with the tip, slowly swirling my tongue around the circumference of his bulbous head before taking more of the shaft. He was huge, meaty and I couldn't get enough of him. There was something empowering about being on my knees in front of a man like him. It felt both oddly satisfying as well as oddly powerful. But I wasn't thinking about power. I was just thinking of his cock and the way it felt in my mouth.

I continued to suck on him, taking him deeper and deeper, while I paused to gasp for air, a thread of drool mixed with pre-cum leaving my painted lips as I stroked his cock. I would then pay attention to his gargantuan balls, sucking on them or licking on them like a depraved cock whore (which I totally was by the way.)

His moans and groans meant I was doing something right. Meanwhile my own cock, was completely erect and had been since I took the panties off. I would stroke my own cock from time to time but held off on doing it as I didn't want post but clarity to hit, and I didn't think stroking ones cock was very lady like and I intended to play the part of the lady tonight with perfection.

After a while, I could feel his cock twitch in my mouth. Was he close?

"Kendra. Stop," he said breathing heavily as I caught my breath. I looked at him, straight in his eyes as he said "I want to fuck you."

I almost jumped up in joy. He took my hand and helped me up and were both standing. He always towered over me at six feet, but it felt that way even now with my heels on. I gazed into his eyes before kissing him, passionately and furiously while one of my hands found his cock and gave it gentle strokes. His hands meanwhile found my bare ass, and covered them almost entirely as he gave it a healthy squeeze.

This was my first time kissing a man, but it didn't feel too different. At some point we broke the kids but before I could realize anything, he had scooped me up in his arms, and was carrying me up the stairs. I held on to his neck as he carried me effortlessly back to his bedroom before dropping me on his bed.

I giggled as he started to take the rest of his clothes off. I got on all fours, with my butthole exposed towards him and once again emulating every girl who was in this very spot before me said "Please. Please fuck me. Please."

I saw him approach me from behind. I felt his cock right near my entrance. I thought I felt him enter me but it was just the meat of his shaft, resting near my hole as he leaned in to my ear to whisper something.

"Do you have lube?"

"Bedside drawer. My room" I said as I felt him run to get lube, leaving me as vulnerable as ever on all fours wearing garters, thigh highs and my heels.

My mind wandered as I waited for him. A part of me wondered if he was going to back out. A part of me thought back to all the other girls who were on all fours just like me. A part of me wanted to be better than them, treated not just like his private cock gobbling whore but with love. A part of me was very happy when he came back with the tube of lube. I heard the snap of the bottle and felt the cold lube drip through my hole while he messaged it with his fingers.

I then felt him enter me.

I've fucked myself silly with my dildo countless times, in countless positions, I even once fucked myself upside down (lay on the floor with my legs up and dildoed myself, not the best angle). But nothing felt like the real thing.

I could feel his head make it's way through me, as I moaned softly. He then pushed more of himself through me as I continued to moan. His hands then moved to my hips for comfort. He was now completely in me, as I could feel my insides stretch to accommodate him. He felt slightly bigger than my dildo but in a good way.

He started to thrust and I could feel it, in more ways than one. I felt him move inside me, whereas outside I felt his balls touch mine. My mind briefly wandered to how he must have felt, fucking me, was I tight like the other girls? Did I give him the same pleasures?

My negative wandering thoughts were slowly moved by a simmering feeling inside me. He was hitting a spot inside me. Repeatedly. And it felt fucking good.

"Oh fuck. Just like that." I felt myself moan while he remained silent, scarily so. He also paid almost no attention to what remained of my masculinity, dangling between my legs, flopping about, while still erect. If anything, it actually helped me feel more feminine.

"Oh fuck. Please. Please fuck me with your big cock. Fuck me like the whore I am. Please. Fill me up with your cum." I moaned.

Just when I thought I was going to cum, he stopped and pulled out. I groaned moaning his absence in me, and in one fell swoop, he turned me over. Exactly like he did the nameless brunette that night I watched them.

I was on my back, my legs spread as he entered me again and thrusted. With each thrust I felt my legs rise, as if with the inertia. I wrapped my legs around his naked torso, every thrust of his making my heels click.

At some point he looked at me, right in the eyes, and slowed his thrusts down. He kissed me, while he kept thrusting, slower but more rhythmic, more passionate, while my lips remained locked with his.

The dirty talk and begging was replaced with moans that spoke a thousand words.

My arms wrapped around the name of his neck, as my legs wrapped around his waist. I was submitting to him in a way I hadn't ever before, which was saying something because I hadn't done this at all before, but in a way this position felt more vulnerable, and more passionate than the doggy. While I was also completely at his mercy then, it felt lustful, and salacious while this felt more close.

My cock (or should I start calling it a clit?) rubbed against both my garters and his torso with every thrust. I could feel my own orgasm rising once again, and I didn't think I could hold it in any longer.

"Fuck. I'm close." I said as he nodded in agreement. While it seemed like we were making love in silence, I was moaning the whole time, at one point I was sure I had lost my voice in the ecstasy.

What began as a simple accident with me caught like a deer in headlights, then turned into a cat and mouse game, and then a dirty talking fiesta and finally into whatever this was.

With every thrust, it felt like he was making me his girl, his woman, his whore. And I loved it.

I finally came, in a messy fashion, squirting all over my garter belt and his belly while he finished inside me. We lay there intertwined, in our own juices for what felt like hours before he pulled out, and held me close.

Right before I could fall asleep in his arms he whispered "Now you owe me my fantasies Kendra."

****