Is this what a woman feels the first time she's fucked?

In no way do I advocate the taking of any medicine not prescribed by a doctor.  The statute of limitations has run out on anything mentioned here.


I woke up the next day and realized that just a few hours earlier a dick was shooting a load of cum in my ass. I had been fucked by a man last night!  Yes, I had co-operated and, in fact, I was riding cowgirl when he shot that big load in me.  But in the light of day it was different.  OK, yes I love dressing in women's clothing and yes, I had sucked a cock when I was still in middle school but this was something else.  Last night I was not only dressed like a woman but I was used like one.  I had been fucked!  At that moment I hated him for fucking me. I hated myself for letting him seduce me. I hated him for the dried cum I felt in my panties. I hated myself for enjoying the feel of his dick sliding in and out of my ass.  Most of all, I was ashamed because I wanted the feeling of his cock in me again.  Is this what a girl feels when she loses her virginity?  Does she hate him for making her a woman and herself because she' gave up her innocence?  Is she ashamed because she wants to fuck again?  Is this what my wife felt when her high school boyfriend fucked her the first time?  Or maybe what she felt after an ex-boyfriend fucked her making me a cuckold when we had been married a couple of years.  What did all this mean?  I couldn't be a faggot, could I?  Yes I had loved sucking my neighbors cock for three years but we had been kids then and kids experiment with same sex relationships.  Now, years later, I wasn't a kid, I was an adult and I had let a thirty-seven year old bi-sexual man fuck me like a sissy faggot.  He had used me as a pussy just like he would have used his ex-wife.  Yes, I was really fucking stoned but is that an excuse?  Or did it just loosen me up and let me do something I wanted to do anyway? 

First a little background on him.  He was thirty-seven and divorced as I said.  About six foot three making him nine inches taller than me but fairly slim.  He lived by himself down the road from us in a house that belonged to his mother who was in a nursing home.  The two of us shared an interest in photography and we were always showing up at each others house to show off our latest photos.  While he never said or did anything overt, I always had the feeling when we were mounting our cameras on tripods, he would like to mount me on his mano-pod.  Little did I know.

How it all came about is really a cliche right out of sissy fiction.  Believe it or not, he actually caught me dressed.  This was before my wife found out that it was to her benefit sexually to have a sissy cuckold for a husband and back then basically just put up with my crossdressing but only if she was not there.  At the time this happened, she was to be gone for about six weeks helping take care of a seriously ill parent.  We had weird schedules at work and I was due for four days off, work seven days, then off two days.  I had taken those seven days of vacation time so I was going to be off for 13 days and I planned to spend a lot of that time in pantyhose and makeup.  It was late fall, going into winter so I was going to be wearing long sleeves and long pants for quite a while.  That allowed me to shave and Nair from neck to toe, from armpit to fingernails, something I had always wanted to do.  I started out in the morning planning on taking a very long time that day to get completely dressed.  I began with coats of red nail polish on my toe and fingernails, three coats each and letting them dry fully in between.  Oh, I forgot to mention that I also started the morning with a type of prescription mild amphetamine so that I would have "speed dick."  If you don't know what that is, amphetamines cause blood to be pulled into the body core which means that there is no excess blood flow to the penis.  No excess blood flow, no hard on.  Oh, you can get turned on but most men couldn't get an erection if the Playmate of the Year and Penthouse Pet of the Year were arguing over who was going to suck their dick.  Anyway, back to dressing.  By lunch time, I was wearing a pair of black panties with a strip of red and black lace across the front and suntan sheer to waist Sheer Energy pantyhose.  I was also wearing a panty girdle, my wife's long line bra and the half slip she wore with her really short skirts.  With my balls tucked up inside me and a shriveled dick, that girdle made me flatter than most women would be.  About that time I took a second amphetimine so if I was speeding before, I was flying that afternoon.  By around four in the afternoon, I was finished with my makeup (red lipstick of course) and was wearing a short red skirt (mine) with a white semi-sheer blouse of my wife's and a pair of black pumps (mine) with a three inch heel.  I had one wig and my wife had two but mine seemed to work best with what I was wearing.  It was a medium length dark blond with bangs.  I didn't really need the bangs to hide my eyebrows as mine have always been fairly thin and light but I liked the look with what I was wearing.  Oh, I forgot to mention that I have a very deep crease in each ear lobe which allowed me to pierce my ears but the holes not show.  I had done that several months earlier so I was wearing pierced dangle type earrings, a matching necklace and bracelet and a couple of rings that fit my little fingers along with my wedding band (ours matched).  By the time I finished everything, it was almost five and I walked outside for a cigarette (Eve menthol).  Because of the carport wall, the curve in our driveway, the curve in the road and a large shrub on one side, you had to be almost halfway up our driveway to see in the carport.  So I had no problem worrying about nosy neighbors.  I could enjoy the click of my heels, the red lipstick stain on my cigarette plus the feel of cool air and the slip swishing across my legs.  I had gone back inside, got something to drink and watched the news for a few minutes.  But that's another thing about speed, you can't stay with any one thing for a long time and another reason it took so long to get dressed.  You will start one thing, then start something else, then go back to the first thing. And I forgot to mention that I had taken a third capsule about four so I was back to flying again.  By that time it was dark and I had loaded up a bowl in my pipe and went back out on the carport.  I took a few hits off the pipe, took it back inside, got my cigarettes.  I standing at the back of my car, breeze blowing on and tickling my exposed legs and with that short a skirt, a lot of leg was exposed.  I had probably taken the third or fourth puff on my cigarette when a set of headlights were coming down the road.  Again, nothing to worry about except that instead of going around the curve, they came up my driveway.  Suddenly I'm standing there, cigarette up to my red lips lit by the headlights of his car.  I remember thinking, "Al can't be here right now, he's going to have to leave."  But of course he didn't.  He got out and came up, looking me over as much as he could in the dim light.  Of course he had all the questions of how long had I been dressing like this, etc.  We ended up sitting on the sofa with his arm on the back of the sofa behind me.  I have to admit he was sneaky plus between the speed and pot, my brain was running about five minutes behind my body.  He started by just barely touching my neck with his fingers but soon he was running them up by my ear and every stroke of his fingers was sending shivers through my body because the speed had me very sensitive.  Next it was a question of had I ever kissed a man.  I said no, that I had kissed a boy when I was younger but never a man.  He started kissing me but said I tasted like cigarettes and asked me to brush my teeth which I did. Al followed me into the bathroom and stood behind me rubbing my shoulders.  I freshened my lipstick and we walked back to the sofa.  As we sat kissing again, I felt his hand at my knee sliding up and down a few inches.  I really can't describe the feeling of his hand sliding over the nylon wrapped around my legs other than it was just overwhelming, like nothing I had ever felt before.  I don't know if I moaned but I know I was probably shaking like a leaf.  I'm pretty sure he knew I was his for the taking but he still worked slow.  He had me stand up and he moved the coffee table before removing the cushions and pulling out the sofa bed telling me if I would lay down, he would massage my legs.  Of course I wanted more of the feeling so I was back on the sofa in a hurry.  Al took his time and rubbed my legs from feet to the bottom of the girdle several times before he began pulling the girdle and hose off.  I hadn't noticed it but when he was in the bathroom with me, he had picked up a bottle of hand cream.  After he got my hose off, he started rubbing my legs with the cream and then asked me to take my panties off so he could massage my ass cheeks.  Yeah, I know but remember like I said, my brain was about five minutes behind.  Before long, he had  me laying on my side rubbing my neck and snuggling up behind me with my head on his arm.  I don't know when he took them off but I remember thinking Al didn't have his pants on.  Of course he was positioning his cock and pushing it into my ass.  I do remember when the head popped into me he stopped and asked if I was ok and I said I was fine.  It's kind of funny that he waited to ask me then but Al wanted to know if I had ever had sex with a man before.  I told him no, but the same boy I had kissed, I sucked his cock for three years.  After a minute or so Al started moving his hips pushing his cock deeper and deeper in me and I was really enjoying the feel of something in my ass.  I turned my head back over my shoulder and Al leaned in and kissed me more.  I do remember thinking I could really get into this kissing men thing.  I asked Al if we could try a different position and that's how I ended up cowgirl on him.  I would loosen up as much as possible to slide down on his dick and then tighten up as much as I could on the upstroke.  Of course I had learned that from my wife who had tremendous control of vaginal muscles. I think Al really liked that because he would moan every time I did it.  I don't think it took too long doing that before he grabbed me, yelled I'm cumming and tried to shove all of his dick and maybe his balls in me.  What amazed me was how hot his cum felt in my ass and how much of it he pumped in me.  I never realized you could feel the heat of cum like that. The next surprise I got was after I got a warm washcloth to clean his cock with.  By the time I got back, he had gone soft but in looking at it I thought how did that huge thing fit in my ass.  Even soft, Al's cock was bigger than my little one when I was hard.  I didn't realize then that Al was one of those who was almost as big soft as they were hard.  He was fairly thick and about seven and a half inches hard but when you consider that the last cock I saw up close belonged to the boy next door when I was 15, Al's seemed like a monster.

So that brings us back to the next day.  I felt  like a log had been shoved up my ass, I hated him and I hated me.  I hated me because I wanted to get dressed, go to his house as soon as he got home from work and ask him to fuck me again.  I wanted to call him and tell him to get up to my house and fuck me.  I was ashamed because I wanted to suck a man's dick instead of a boy's dick like I had when I was fifteen.  I was ashamed because I wanted him to make me his cocksucking sissy faggot slut, to use my ass as pussy for his pleasure.  I was ashamed because I wanted to spend all those days off making myself look as pretty possible so Al would want me.  I hated myself because I wanted Al to think I was the best fuck he had ever had and if he had a choice between fucking a hot woman and fucking me, he would choose me.  I hated myself and Al every day when I woke up but I loved it every night when Al was fucking me.  I did get to suck a man's cock for the first time and apparently I hadn't lost my touch in my seven year layoff.  I also found out that Al was good for more than one time a night.  That first night he didn't try for a second time because he didn't want to scare me.  What he didn't know was, as stoned as I was, when I was washing his cock after we had fucked, I wanted to suck it so bad but I didn't. Isn't it funny.  I spent three years sucking my neighbors dick from age thirteen to almost 16 and it never bothered me.  But the first time someone fucked my ass, I was so upset.  In the time since then, I think I know why.  As a child, and I'm talking about around age seven or eight long before I was sexually aware, I enjoyed having things in my ass.  I would put things like a golf ball, the handle end of my baseball bat, a broom handle or anything that would penetrate my ass.  I would use shampoo bottles in the shower and as a teen, I would run my arm between my legs, rest my hand on the side of the tub, group my finger and thumb together and see how much I could get in my ass,  I didn't know it was called fisting but that's what I was trying to do.  Once I got most of my hand in.  Basically, every chance I got, I was putting something in my ass and the larger the better.  So that's what I think subconsciously scared me when I enjoyed Al fucking me for the first time.  Sure I enjoyed giving what in essence was my middle and high school boyfriend blowjobs.  But I didn't wake up in the morning wanting to run next door and jump in his bed to suck his cock.  If I got a chance to suck his cock, I would and I would try to make his eyes cross when he shot cum down my throat but if we didn't get a chance, no big deal.  But when I woke up that next day after Al fucked me, I was scared.because the feeling of his dick in my ass brought back those thoughts of broom handles, bats, balls or whatever.  I wanted Al's dick in my ass again. I wanted him to pull up my skirt, pull down my panties and fuck me like a sissy faggot.  Today, that would be no big deal to me emotionally.   But then, it scared the hell out of me that I could possibly be a cock loving sissy.

Oh, two things for those who ask. One, although this reads like some sissy fiction you find online, it's not.  Al really did catch me dressed and fucked me that night.  Since he was a social worker specializing in drug abuse/addiction, I'm pretty sure he was quite aware of how stoned (and vulnerable) I was that night and knew I was easy prey.   Second, this was just before everyone had a cell phone and even if you did, the cell companies along with landlines charged for long distance.  My wife and I only talked once a week to avoid a huge phone bill so I didn't have to worry about her calling every night.

Do You Remember Your First Orgasm?

I'm sure most of us remember it in some shape, form or fashion but I remember almost every single detail of mine.  The one thing I can't remember about it was my age.  I know I was older than 10 so I was either 11 or 12, but I'm not sure which.  I know it was a dry orgasm, it was during the summer, it was between one and two in the morning and I was standing in front of the dresser, looking in the  mirror in my parents room.  I know that sounds like a strange place to have your first orgasm but there is a good explanation for that.   You see, my mother was taking her turn working midnight shift at the hospital on base and, since she was doing midnights, my father traded duty with other people so that he was the base Assistant Duty Officer some of the nights she worked.  That way, he got his overnight duty out of the way while she was doing the overnights.  Since I was always a responsible child, even at that young age, I was allowed to babysit my brothers.   Now can you think of anything more perfect for a sissy like me who would dress up in his mother's clothes anytime he had the chance?  I would usually give them about 15 minutes after they left to make sure they weren't coming back for anything, then I would be out of my bed like a shot and into her lingerie drawers and her closet.  Many times I would wear a grayish black skirt with little flecks of blue in it, a blue sweater, stockings, her heels which fit me at that time and of course underwear.  Bra stuffed with panties, wearing a pair of panties and long leg girdle.  I would ad a scarf and lipstick before going out on the back porch to feel the breeze across my nylon covered legs.  This particular night my outfit varied a little.  I had managed to avoid a haircut for a while and my hair was slightly long and combed back over my ears.  If I let it hang down it looked faintly feminine (at least in my mind it did).  This particular night I was wearing the usual white panties with a long leg panty girdle and, at that age, I knew nothing about tucking.  But I could let my penis lay flat against my stomach and allow the firm center panel of the girdle to mash it flat (and it did).  I knew that rubbing myself through the girdle always felt really good.  Anyway, I had raided the closet for the nurses uniform she wore the night before.  This was back when nurses uniforms were very heavily starched, had buttons up the front and on each sleeve that were placed in similar to cufflinks.  She would hang her worn uniforms back up until she could take the buttons out before sending them to the laundry.  The nurses hats were also starched heavily, then folded and buttoned, then held to the hair with hairpins. So there I was, white nylon stockings (about as thick as tights) attached to the garter tabs of the panty girdle with a soft nylon panty underneath.  I seem to remember that I was wearing  her longline bra with panties stuffing the cups and of course back then a lady always wore a slip.  Most of hers were just very plain nylon to wear under her uniforms.  And on top of that, her uniform and with my hair barely long enough, I was able to pin one of her nurses caps on.  Shoes were my mother's spare pair of white nursing oxfords.  Normally the only makeup my mother wore was face powder and lipstick but for some reason she had started wearing a little mascara and some eye shadow not long before that (I think I know why but that's another story).  So I was able to use more than just lipstick and powder that night.  I'm sure with no practice using shadow and mascara I probably looked terrible but I thought I looked beautiful.  Oh and I topped it off with clip-on button style pearl colored earrings.  This particular night all along as I was dressing I kept rubbing myself and it felt different somehow, I guess better than normal.  After I was finished dressing, I walked around the house, peeked in their room to make sure my brothers were still asleep, went into the kitchen to get something to drink more to see my lipstick marks on the glass than anything else.  This was also during the short time that my mother smoked but she only did it in the house, never in public.  And yes, I was sneaking her cigarettes when I could but again that night, it seemed more erotic(?) to light up a cigarette and see red lip marks on the filter.  Can you imagine how intense a feeling it would be for an 11-12 year old sissy boy to be standing on his back porch, looking like his mother in all her clothes and smoking one of her cigarettes.  I went back inside, put the cigarette out in an ashtray that she used and went back into the bedroom.  I was standing there in front of the mirror and, as I said, rubbing seemed more pleasurable that night that previously so I rubbed a little more.  That was when it happened and I didn't have any idea what was going on.  The MOST intense pleasure started through me but I honestly thought something was wrong.  I remember being really scared that I was sick or something but couldn't stop rubbing my dick, my vision blurring and my legs collapsing as I went to the floor and everything just exploded.  I really think I passed out for a short while because the next thing I was aware of, I was laying on the floor next to my parents bed on my side with the most incredible feeling throughout my body.  I could really feel the stockings on my legs, the pressure of the girdle encasing me from my waist almost to my knees, the bra tight around my chest and the taste of lipstick.  It was so amazing that I was really sad that I had to put everything away, shower to clean up my face and go to bed.  Of course I have cum many times since then while dressed in women's clothing.  Being a sissy faggot, I've sucked dicks and/or taken them up my ass while crossdressed and cum while doing it.  Nothing, including my first time with a girl, has ever come close to that night and my first time cumming.

Oh, the other story about my mother and the makeup?  I honestly think she was having an affair with someone in the neighborhood.

Humiliation

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