Written by Missy Sissy

25 Sep 2005

In my last story I told you how I sucked-off a complete stranger in a pub toilet. (pub-lunch-with-creamy-dessert.) I finished that tale by saying I knew it wouldn't be long before I sucked cock again. Well, I got much more than I bargained for. Here's what happened. It also explains why I've decided to changed my name slightly now.

As usual, I went out last Saturday night for a drink with pals. As usual, I was dressed as a male, except, as usual, for the sheer mesh pink panties I was wearing beneath my trousers.

It was a fun night, made even better by some lovely eye-candy we enjoyed in one particular pub. There was a gaggle of eighteen year old, blonde girls, dressed in sexy, revealing clothes. They all appeared to have boyfriends with them so I and my forty-something mates simply enjoyed the stunning views from afar. However, for me, I couldn't help but wonder if their underwear was as sexy as my own. (I'm sure it was!)

The thing is, the visual delights of such adorable young women doesn't necessarily create lust for them in me. However it always allows me to imagine I'm one of them. That makes me very horny indeed.

Later that night the guys drifted away and I found myself drinking with a chap I know, called Peter. I was so turned-on by then I really wanted to suck a cock. When closing time came I told Peter I was not ready to call it a night and asked if he had any booze at home. He said he did but only vodka and he didn't have any mixers. So we walked the short distance to my house and grabbed my two litre carton of orange juice. While there, I popped upstairs and selected one of my vintage nighties. It was a pretty, salmon pink, chiffon over nylon, mid-thigh, lace-hemmed, frothy affair. I quickly folded it and put it away in the inside pocket of my jacket.

We then took a taxi to his flat and got stuck into the vodka while listening to some music. A while later I needed to use the toilet so excused myself. When I came out from the loo I saw the living room was empty and realised Peter had crashed. Well, that was no good to me. I knew what I wanted.

(I'd better say, it was a few weeks ago, I was round at Peter's place with my then current girlfriend. During the course of that evening I recall drunkenly saying something about my preference for wearing ladies' underwear.)

So, in the living room, I undressed completely, except for my pink panties and put on my lovely nightie. I then entered Peter's bedroom and slipped into bed beside him.

He was still awake, naked and said,

"What's on your mind?"

I snuggled up close to him, laid my head on his chest, put my hand on his tummy and whispered,

"Please, I'd like to suck your cock, please, if that's ok?"

As I spoke, I slid my hand down to his cock and gently stroked it. It was soft and small but started to grow as I touched him.

"Please." I repeated.

He put his arm around me, sending lovely shivers through me as he caressed my nightie. He told me,

"I don't normally do this sort of thing."

I kissed his chest, stroked his cock again and said,

"Please. I want to taste your cum."

He groaned and said,

"Ok, but don't tell anyone."

I whispered,

"Thank you."

I pulled back the covers and started kissing down from his tummy, teasing my way past his cock, until my tongue found his hairy balls. I licked and kissed his sack while continuing to stroke his growing cock. Before long he was fully erect, about five inches and slim with it. That was perfect for me, I can't cope with big cocks. I kissed and licked my way up to the tip of his hard-on then flicked my tongue all around the bulbous head. I was rewarded with the sight of a little pre-cum which I hungrily licked from his pee-hole. I gave his shaft a firm squeeze with my fingers, slid my wet lips over the tip and sucked all the way down, until I had his entire cock in my mouth. Then I started sucking, slowly at first, increasing the tempo until I was bobbing up and down on his lovely pole.

Now, the truth is, I must have been down on Peter for a good half hour, licking, fondling, kissing, wanking his cock and trying to suck the cum out of him. I even made my best attempt to deep throat him, which did make me gag but that didn't stop me trying several times. Anyway, no matter what I did he just wouldn't cum. Apparently he had taken a little speed earlier, which delays orgasm. I didn't know anything about that, all I wanted was his cum in my mouth, which was getting tired by then. So I asked him to wank himself off into my mouth. That didn't work either. He remained hard as a rock but was nowhere near cumming.

Then I got the surprise of my life. Peter said,

"I know what you want."

With that he roughly turned me over onto my front and positioned himself behind me. He reached under my nightie, pulled my flimsy panties down my legs and threw them onto the floor. It all happened so fast but was so exciting, to be exposed to his lust like that. He reached over to the bedside table, unwrapped a condom and put it on. While he was doing that I grabbed a couple of pillows and thrust them under my hips. (I may have been a virgin up to that point but I'd read enough stories to know the pillows would help present my sissy pussy at a better angle for penetration.) Peter lifted the hem of my nightie, grabbed a tube of hand cream, spread my legs wide and lubed me up with his finger. He grabbed my hips and pulled me towards him. I felt his cock slide between my cheeks until it was pressing at my hole. He said,

"You want this, don't you?"

I was in a frenzy by then and begged him,

"Yes, yes please. Fuck me, please."

Peter pushed steadily forward and I felt his rock hard cock slip inside me. Perhaps I was relaxed from the booze or it may have been the lube or the fact he had a slim cock but he entered me very easily. My biggest fear about being fucked was that it would hurt but there was no pain at all, just the wonderful sensation of having my pussy filled by a warm, living cock. Once he was fully inside he began slowly, rhythmically fucking me. It was incredible. I may like to think of myself as a sissy boy but as he drove in and out of me I allowed myself to believe I really was a girl, getting fucked for the very first time. Peter's rough hands grasping and rubbing me through my pretty nightie made the illusion seem even more plausible.

Something else which delighted me and made me feel even more girlish was the fact that all the while Peter was fucking me, my cock remained limp and flaccid. Maybe he was too small to effectively hit my g-spot but I didn't want to be reminded of my maleness anyway. I just wanted him to use me like a slut, which he continued to do with relish. I felt so weak and helpless as he kept me pinned to the bed but I did my best to buck my hips to meet his tempo. I was rewarded with the sound and feeling of his balls slapping against my bum cheeks with every stroke.

Peter asked,

"Oh, you've done this before haven't you?"

I honestly, breathlessly replied,

"No. Not until tonight. This is my first time."

He said,

"Well I'd better give you something to remember then eh?

"Oh yes, yes, please fuck me hard." I heard myself say.

True to his word, he carried on fucking me enthusiastically. He must have been going at it for well over an hour and I loved every minute of it. All the while I whimpered and gasped my encouragement, desperately wanting to inspire him to the ultimate pleasure.

Eventually his thrusts became harder and even more urgent. He gripped my hip bones through my nightie and plunged into me, forcefully holding me to him for a moment. I felt his cock swell and twitch inside my pussy as the first wave of orgasm racked his body. He moaned and slowly, powerfully resumed fucking me. I could feel every glorious pulse as his cock repeatedly pumped inside me. When he finally finished unloading he withdrew and collapsed beside me. That was my cue to get what I came for. I rolled him onto his back and peeled the condom off his softening cock, making sure it turned inside out, spilling all his cum onto his tummy. I hungrily lapped up his warm sticky juice and descended onto his cock, taking it all into my mouth and sucking up the last drops of his tasty cum.

Once I had cleaned him up I looked Peter in the eye and licked the final traces of his cum from my lips.

"Thank you." I said.

He smiled and called me a,

"Dirty slut."

I giggled and said,


He did offer to give me a hand job but I politely declined. I wanted to remain all girl while in his bed. After a few minutes I realised it was getting light outside and decided it was time to go home. (We must have been fucking for much longer than I imagined.) I found my panties, put them on and removed my nightie, dropping it on the bed. Then I returned to the living room and put my male clothes back on. I looked round the bedroom door and said goodbye to Peter. Being an outwardly straight guy and possibly a bit ashamed of the fact he had just fucked another guy, he asked that we never speak of it again. Knowing I'll see him around town sooner or later I agreed that it was our little secret. I thanked him one more time then let myself out.

I couldn't be bothered to call a taxi so began the two mile walk home. All the way I kept thinking about my fabulous experience and how, at the age of forty five, I'd finally lost my virginity, albeit so unexpectedly. I had gone from being a cock-sucking sissy to a fully-fucked sexy seductress in one wonderful step. In my girlish glee I felt like skipping home but thought better of it. When I was half-way home I had another realisation. I'd left my pretty nightie on Peter's bed! I have many, many more beautiful nighties so that's not a problem. However, whereas we agreed to never repeat the performance, maybe I subconsciously left it there, just in case? Peter did tell me he wasn't particularly turned-on by silky clothes but I wonder if he's worn it since? I'll let you know if we ever get it on again. I must say, I would love for him to fuck me all night, just like he did that first and only time.

By the way, once I returned home I needed to catch up on my sleep. So I got undressed and slipped into a full length, sheer over nylon, baby pink vintage nightie. I kept my panties on though and despite the large swelling therein I continued to deny myself an orgasm. I just drifted off to sleep, no longer a sissy or even a girl but believing I was now the woman I should have been born.

Thank you so much Peter.

Hope you enjoyed hearing about my long overdue deflowering. I must go now. I've met a chap online who has kindly agreed to call round early tomorrow morning and fuck my face until he cums in my mouth, for nothing in return. (Isn't that nice of him!?) I've already decided on my outfit and want to try it on, just to be sure it's sexy enough. What is it, I hear you ask?

Well, although I have loved being a pink sissy boy in the past my latest experience has changed all that. Tomorrow my look will be sophisticated yet slightly slutty woman.

I shall be wearing black nylon fully fashioned stockings, a red and black six-drop retro-style suspender belt, totally sheer red high-waist panties, (Secrets In Lace.) a red vintage lace and satin full soft cup bra, B cup silicone boobs, a red nylon vintage mid-thigh lacy full slip, (Vanity Fair.) three inch black spike heels, a blonde wig and bright red cock-ready lipstick. Oh and I just remebered, I have two identical, silky, flowing, ankle-length, long-sleeved, semi-sheer, fine nylon robes. (Shadowline.) One bright red, the other jet black. They have gorgeous lavish deep lace around the neckline and cuffs. I must top-off my look with one of those! Red or black though? I had better go choose. Decisions decisions. I'm such a lucky lady.

The chap says he's never been with a tranny before so I thought I'd better make the effort for him. It's only polite don't you think? :-)

In that outfit, I wonder if I can seduce him into fucking me too?

I'll tell you the full tale as soon as I can. Think I shall call it "Cum for breakfast." ;-)

Missy Sissy