Caught Relaxing Pt. 01

This is going to be a short series of stories. This one really starts the journey out, they won't all be in exact order or have a proper linear flow to them. Just depends on what's has caught my interest that day, and needs to flow out of me.

It's Friday night, no plans or anything to do a perfect night to dress up. Hangout have a drink and relax being Stephanie. Stephanie is my female name. I enjoy crossdressing, and exploring my feminine side. Starting my transformation off with a fresh shower, shaving all the right areas making sure my legs and ass are silky smooth some vanilla body soap for a fresh clean scent. Afterwards a little baby powder to enhance my fresh feminine scent. Next tuck my oversized clit away taping it in place, dawn a cute pink thong to smooth everything out. Next a pair of suntan pantyhose, some thin white sissy socks, then over that a cute pair of daisy Dukes; with a white tight angora sweater finishing my look of with a slut anklet and 6in black high heels. I pour myself a glass of wine, turn the TV on time to just relax and enjoy the sensations of feeling feminine.

Just as I'm getting into the movie on TV, I hear a knock, along with the door opening. One of my friends calls out hey man are you home? In a flash I try scrambling to the bedroom. Something not easily done in high heels. I tell him to grab a beer, will be out in a bit. This gives me a couple of minutes to take the sweater, shorts and socks off replacing them with normal men's sweats. I carefully try to hide the anklet under a pair of men's short socks it's too delicate for fast removal.

It's not long before he's asking where I'm at, and up to. Just about this time I wander out, telling Sir I was just hanging out in my boxers watching TV and had to put something on (little does he know at this time I still have a thong and pantyhose on, but I can feel them even under my manly clothes). With fresh beers in hand we head off to the game room to play darts. During the course of playing, I had not noticed the back of my shirt sliding up or my sweats sliding down slightly, exposing my pantyhose and thong. Sir certainly noticed, as eventually he reached out and grabbed my pantyhose, demanding to know what I was wearing.

Here I was caught dead to rights three's no explaining away my way out of this. He has a hand full of the waist of my pantyhose pulled tightly up. If I had balls like a normal guy, they would be hurting from the wedgie. I'm forced to admit, I like to wear pantyhose and sometimes cross-dress. This is the first time I've ever been caught like this. It feels like time has stopped, what seems like hours he relinquishes some of the tension on my pantyhose, asking so do you cross-dress a lot? There is no denying it; I weakly admit yes, I play dress up as much as I can. His only reply was, huh, show me. With that his big hand lets me free. I try to protest, that's just a personal thing, and no one needs to see me dressed that way. Sir crosses his big arms and just glares at me. I feel the need to please him, and show him my gurl side.

I head back to my room, where I put on a bra, add in my big fake silicon breasts. Over that, my white angora sweater, a simple plaid red school girl skirt. A long brown wig to give me a more feminine appearance. Slip on some white ruffly sissy socks, and high heel Mary Janes. Finishing my hurried look with slut red lipstick and a fresh spritz of vanilla body spray. As I apply the lipstick, the sensation on my lips is interesting. It's different than just chap stick, much thicker yet slicker than normal chap stick. Grabbing a glass of wine, I head back to the game room. I stop as I enter the room, terrified as to what he will say or how he will respond. He is sitting on a bar stool, watching me, as I saunter in. Sir commands me, come all the way in, and "turn around slowly so I can get a good look at you". I am at his command, I slide my legs forward, slowly moving my hips as I walk to center stage. Once in the middle of the room I cross my legs, and use them to spin myself around. So smoothly, and gracefully. Standing facing away from him, I instinctively know he doesn't want to see me from the front side, but the back side. I feel really gurly as if I am a girl presenting myself to a suiter. Making sure to present my backside as that is where all the fun parts he might be interested in are. Again time feels as if it stands still, as I wait for Sir's approval.

Eventually he bellows, well you are not the prettiest girl, but hell if I care. Do whatever you want...

We go back to general chatting about random topics and playing darts. The whole time, I can't help but want to move more feminine and act slightly more feminine. Including now getting him drinks whenever he asks. That true gurl nature is coming out, wanting to be submissive and servile to someone more dominate. As the night progresses, and the alcohol flows, I lose more and more games to Sir...

After the last game, he drops his pen on the floor, and fains trying to pick it up from his barstool. At this point I am in total gurl mode and jump to get it. Except, I am in heels and picking it up plus being drunk means just dropping to my knees. I carefully kneel down and on both knees to pick up the fallen pen. As I look up, he is rubbing his cock through his loose gym shorts. I can see the outline of his cock through the thin material. Something about his half hard cock through those shorts has me mesmerized. I just can't take my eyes off watching him pleasure himself. He spreads his legs a little more and messages his balls. My entire world has succumb to just watching what Sir is doing now. As he slides up and down, I can see more and more of the outline of his cock. It's as if he is hypnotizing me, I have never seen anything so large.

It's not long as his large hand slides up and under his shorts. For a second I feel cheated as he is pleasuring himself without me to watch. However, it's only a second or two, before he uses his hand to pull that big cock out and display it to me. Its then that I get a good look at a real cock, a cock that pleases pussy...I instinctively move forward a little bit to get a better view of his veiny monster.

He starts stroking his long hard dominate cock in front of me, as I kneel in front of him. Long forgotten why I am here. He strokes his cock up and down, my mouth opens in awe. About then, he points his cock down towards my awaiting mouth. I lick the precum, slipping my hand under his balls, to gently hold them while licking up and down getting the whole shaft wet with my tongue. He opens his legs more allowing me further access to provide him pleasure. No words have been spoken, no words need to be spoken, his cock needs worshiping and I am here to worship it.

With it all nice and wet, I take him into my mouth, sliding my tongue along the bottom of his shaft, slowly bobbing my head up and down off of him. He moans in pleasure, as I continue my onslaught of his cock. Attempting to swallow as much of it as I can handle without gagging. Occasionally, turning my head slightly to vary the sensation he receives. Then wrapping my fingers around his shaft following just in front of my mouth to further enhance his pleasure. I in a whirl of pleasure myself, lost completely in the act I am performing, enjoying the sensation of a hard cock in my mouth, my tongue all over it.

It's not long, maybe ten minutes before I feel his balls start to tighten up. I know what's coming, but I can't stop the rhythm or the flow. That's the most critical time to keep it consistent. I know this from the times I have received head. Just thinking about that, it's no longer me receiving head but giving head. With my mind wandering of, I am thrust back into reality at the first gush of his cum entering my mouth. It's so much, and each spasm of his cock leaves more and more cum. I have been so lost in what I was doing, never considered what would happen when he cums. There is only one real option here, and that is to swallow every drop I can. It seems he has not cum in months, there so much of it, I find it difficult to keep my pace up and down plus try to swallow it, doing so I lose some of his nourishment out of the seal my mouth has formed around his cock. I slow to allow me a second to swallow some of his nut. In the meantime, I can hear him growling loudly with orgasm. Just hearing him cumming, I feel a wash of accomplishment run over me. It's almost as if I had just cum, such a simple act of pleasure and enjoyable for me as well.

Once he has finished cumming, I stay there gently nuzzling his cock for leftover cum. For the first time I look up, and see his head fully back, and then looking down on me. I take his cock out of my mouth licking the last stream of sperm connecting us, and clean up his cock with my tongue. Getting up, I notice that Sir's drink is low, licking my lips, and thanking him; I grab it scurrying off to refresh it. I am sure he will want a fresh drink after that.

We sit idle and quite for a few minutes after. While I am still enjoying the satisfaction of what I had just done for him, it does feel a little bit awkward, neither of use have ever done something of this nature.

Eventually Sir speaks up, and says, that was a onetime thing, he just really needed to cum and my ass looked good tonight. I thank him, for letting me take care of his needs. Don't worry about it, just two animals needing some fun. Lastly I apply a little more lipstick, I know that by now that it is all gone from the act I just performed.

We continue our night of playing darts having more and more drinks, it's not long before he starts playfully swatting me on the ass. I don't know why, but it just feels so good. It feels like I am his little slut...

After Sir kicks my ass in darts for the umpteenth time, he sits back on the stool. Legs spread wide, and starts rubbing his cock again. Just like last time, I am completely mesmerized, hypnotized by his dominance. So flagrantly pleasuring himself through his gym shorts. No words are spoken when he pulls his cock out, I drop down to my knees and start pleasuring him all over again. Sucking his cock as if it contained a magic elixir of happiness to life. Well maybe it does...I have never felt like floating on cloud nine until now...This happens a few more times tonight, each and every time no words need to be spoken about what I am to do. I am here to provide him pleasure.

The next day, Sir texts me. Thanks me for my help and reliving his stress but he's not like that and will not be happening again. I tell him, it's no worries, I enjoyed taking care of the relief, as it was very oddly relaxing and stress reliving for me as well. Tonight turned into a real relaxing night. Who knows what the future will hold, stress can only build up so long before it needs release.