#1105 - Sissy Story 34 - First time out

our sissy appointment.. with erotic tales..
i'm not sure.. you really like this collection..
anyway we arrived at numebr 34.. a lot..
for today i choosen another first time fantasy..
i'm really addicted by first time stories.. they are my favorite..
maybe because i'm a virgin sissy.. i don't know..
anywyay for today there is a strange casual encounter..
in which a virgin crossdresser receives her first taste and loves it.
enjoy the sissy story number 34! ;)


Anna Malice




First time out


On the surface I appear to be just a normal average clean cut guy. But internally I am a very conflicted person not really knowing who I am. I'm small in stature standing only 5'6" and weighing 130 pounds and while this led to much ridicule growing up it has been a blessing of sorts in my adult life. You see one of the conflicts in me is my desire to be a woman. I have been dealing with it off and on since I was 10. And as many other young people I was also taught that these feelings were not normal and that there was something wrong with me for feeling this way. Because of that I went for months and years denying everything and trying to shut it out of my mind. After I graduated high school, I left home and joined the United States Air Force (USAF) and have been in for 5 years. I have managed to make some rank and with that rank and my time in one of the perks I have is that I now have a room to myself. I reside in what is known as an Unaccompanied Non-commissioned Officer dormitory or NCOQ.

Having a room to myself I have been able to spend time wearing women's clothing and I enjoy it tremendously. I had done some crossdressing when I was younger but I was always so afraid I would get caught and was almost never able to spend more than a few minutes in various states of being dressed but never completely done up.

As my time rooming alone became a reality I began to acquire some articles of women's clothing. At first it was just a couple pairs of panties and pantyhose that I bought at Target. Then I ordered a dress and a couple of skirts and blouses online, which I had to send back three times trying to get things that fit me right. I would change into the panties and pantyhose when I got home from work and wear them around my room and sleep in them. Then I ordered a floor length nightgown and was loving sleeping in all that smooth material. I decided one night to shave everything from my neck down, not that there was much anyway but a little patch on my chest, one on my lower back, some on my forearms and underarms and a sparse growth on my legs.

Once shaved, my whole body felt electric and so silky smooth I couldn't believe I hadn't done this before. But then I slid on the panties and pantyhose and an incredible feeling cursed through my body and I was hooked. Every night when I got off work I would rush home and change into my girl clothes and sit around watching TV relishing the feeling of all those silky things against my smooth skin. But I needed to complete my outfit so I set out to get a pair of shoes and a wig and some lipstick.

That was two years ago, I have progressed quite a bit since then. I have about twenty complete outfits, but actually some of the things double up, and five wigs of different colors and lengths. I now have like thirty pairs of high heels and can't believe I still want more but I love them. I threw out all my male underwear and now only wear girl's panties, of which I own around a hundred pairs. Every time I see another pair of sexy silky panties I have to buy them. Some but not all have matching bras that go with them. I also have two pairs of silicone breast form and two v-strings, which are prosthetic vaginas.

I get all dressed up and go out at least once a week but I change almost every night and don't change back until morning when it's time to go to work but even then I wear my silky underthings under my uniform. It is so erotic working all day long in my male world but being totally encased in my silky sexy lingerie.

One night I went home after work and changed into a black leather skirt that came down to about mid-thigh and has a slit on the left side about half way up. I was already wearing my v-string and a pair of bright blue silk and lace panties and black pantyhose so I picked out the matching bright blue silk and lace bra and after gluing on my c-cup breast forms I slipped the bra up my arms and fastened it in back. I then picked out a black silk blouse with a cowl neck and pulled it over my head and tucked it into my skirt. I slipped my toes into a pair of 4.5 inch red stilettos and decided on a long blonde wig to complete my outfit. I walked around my room admiring myself in all the mirrors and thinking how hot I looked and how if I didn't know who it was there was no way I would ever be able to tell she wasn't a real girl.

After a couple of hours of sitting around dressed, I decided I needed to venture out and feel the breeze blowing up my skirt and hear the clicking of my heels as I walked. So I did my makeup and grabbed my room key and headed out to walk to the post office, which was only a couple blocks away. As I left the building a couple guys saw me going down the staircase on one end of the building and stood and stared, one even whistled as I stepped out of their view. That made me feel so good to be attractive to a guy, it caused an unfamiliar stir in my crotch. I had often thought about guys seeing me and thinking I was attractive and maybe even hitting on me but I have never had the opportunity to do anything with anyone, so to have a guy whistle at me sent shivers through me but it excited me so much. I almost wished he had pursued me but alas he did not.

As I walked, hearing the clicking of my high heels on the sidewalk and feeling my thighs slipping back and forth in my hose was pure excitement. I made it to the post office, retrieved my mail and back to my dorm without anything out of the ordinary occurring. I was standing at the door to my room with my key in to door when a voice behind me asked if I was Davis' latest flavor of the week. I turned slightly and saw my neighbor standing there checking out my legs and moving his gaze up the rest of my body taking in the sight as he did. I shook my head yes and at the same time said yes I guess I am, remembering to raise my voice a couple octaves and speak from my throat and not my chest.

He then said well you are definitely the hottest I've seen with him. This startled me a little and I turned to face him and smiled saying thank you that is very kind of you. He simply looked into my eyes and said just telling it like it is, you are very hot, way too sexy to be with Davis. I smiled again and as I was becoming very aware of his presence, I moved my hand to touch his arm as I once again said thank you. I stood looking up into his eyes, even in my high heels he was a head taller than me and these big beautiful brown eyes that seemed to look right through me.

He was a pretty big black guy, muscular chest and arms and no facial hair and of course being in the military he had short hair. He stuck out his hand and said hey I'm Mark, I reciprocated and smiling said I'm Amy; it's very nice to meet you. Looking down at me, he smiled and said the pleasure is all mine. Smiling up at him I said oh you're a smooth one aren't you? He feigned ignorance and said who me, as we both laughed.

He says Amy can I ask you a personal question, sure I answer back to him as I turn to unlock the door. Just then he puts his hand on my arm and says I don't think Davis is home. No I know he's not but he gave me his key so I can wait for him inside. Oh was all he managed. So what was your personal question Mark? I continued.

Oh he mumbles then looks up at me and asks, so how long have you been seeing Davis. Oh I don't know three or four weeks I think. Oh so it's serious he continues. I don't know if it's really serious after only a month but you never know and I don't think he is looking for something really serious anyway. But that doesn't mean we don't really like each other. Oh he mumbles. Why do you ask? I was going to see if you wanted to go out with me since he's not here. Oh that's sweet I respond but since I am seeing him that wouldn't be right. Ok he says. He must be talented in bed to keep a hot girl like you with him. Startled I shook my head and say excuse me that's not something you should be asking. Well as fine as you are and as normal as he is that seems to be the only possible explanation.

Well tell me this then, have you ever been with a black guy, he asks as I turn to go into the room. I laugh a little and shake my head in disbelief again. That's even worse Mark; you shouldn't ask a girl questions like that, I say still with my back to him. I guess that's a no then he says and then he says you know it's true what they say about black guys. I turn my head to the side looking back over my shoulder at him and ask what's true. Just then I see him pulling out the biggest cock I have ever seen and he was rock hard. It must have been nine inches long and really thick. As I turned to face him, I can't stop staring, he begins to run his fist from the base up to the head of his hard on and says that we're bigger. Staring at his huge cock with my mouth gaped open, I moan that's for sure. He smiles and asks if I want to touch it.

I move my head affirmatively before realizing I was doing it and then shake my head no saying I shouldn't. He just smiles and says it's ok, go ahead. He's a little farther away, as he has now moved back into his room out of the hall and out of sight of anybody venturing out into the hallway. Still slowly moving his grip up and down on his penis, he smiles at me and reaches for my hand and pulls me into his doorway and says it really is ok; go ahead as he puts my hand on the head.

I moan as I move my hand on his cock, feeling how hard it is and the heat emanating from that beautiful tool. Oh my god Mark, I moan again it's so big and so hard, I've never seen or felt anything like it. No I imagine you haven't but you know it would feel so good sliding between those bright red lips of yours. Having wrapped my slender fingers around his cock and seeing that my bright red painted nails didn't touch I realized how big around he was as I began to stroke him. Brought back to reality by him saying that to me I stare up at him and tell him I can't do that I'm with Davis, all the while slowly stroking his engorged member. Feeling the pre cum ooze from his cock I realize I'm playing with him the whole time I'm telling him no.

Amy you'll love it he says to me as he pushes down on my shoulders pushing me down to my knees in front of him as he rubs the head of his cock slick with pre cum back and forth across my lips. Involuntarily my mouth opens and he pushes his cock between my bright red lips and into my warm wet mouth. It feels so good to have his big cock in my mouth that I lose track of what is going on and I go to work servicing his cock. Sliding him in to the back of my throat and then back out until just the head remains over and over again and rolling my tongue around his hard on. All the while moving my closed fist up and down on what remained outside my mouth. He moans yes Amy yes suck that black cock baby and as I moan around his cock, I do.

As I continued to suck he's getting closer and put his hands on either side of my head and started fucking my mouth. Then he pushes it in and holds it there and as I'm looking up at him he just smiles and says swallow baby. Huh I moan as the first blast hits the back of my throat, then another and another as he grunts out his thick hot seed filling my mouth to overflowing. Swallowing as much as I can but some still trickles out of the corner of my mouth and drips onto my chest and blouse. After he stops shooting he groans and manipulates all he can out of his cock into my mouth and on my face and then he pushes his cock into my mouth all the way in past my gag reflex and into my throat and holds it there as he softens.

I can't believe what I have just done as I sit there on my knees with my lips wrapped around this huge black cock with his cum stains on my blouse and all I can think about is milking this beautiful cock with my mouth. Looking up at him as I lick him clean I smile and say thank you, I loved that so very much. He shakes his head and says once again it's all my pleasure. That was hot but I want some of that hot little pussy Amy. You think it was good in your mouth wait until I get all this dick stuffed in your hot little box, you will be begging me to never take it out and then you will be begging for me to pump your womb full of my hot seed.

No, I shout in horror, knowing that he would find me out and fearing the outcome if he did as I scramble to my feet and retreat to my room across the hall. As I close the door and stand there leaning against it still not believing what just happened and truly wishing I had a pussy to let him stuff full of that magnificent cock and still not able to catch my breath I listen as he says he'll see me later and then the outside door banging closed.

I clean up and dress for bed and think to myself what wonderful dreams I will have tonight. I bring his cum from my chest to my mouth and lick it off my fingers and remember the taste he left in my mind and how wonderful I felt as he exploded into my body. I wonder if we will ever hook up again and I hope that we will and I hope to taste his cock again. I write a note and slip it under his door telling him that what I did was wrong but that I loved sucking his cock so much and that I would be willing to do it again if he so desired. Actually Mark, I'll suck your cock anywhere, anytime you desire. Smiles, Amy