A Sissy in Need Is a Sissy Indeed

The Erotic Adventures of a Sissy Named Jamie

Part I: A Sissy in Need Is a Sissy Indeed

Jamie Michelle

February 19, 2008

"Hello, ma'am. I do yard work and I noticed that you might need some help with yours," the man said in a deeply sonorous voice when I opened my front door upon hearing someone knock.

He stood there before me in the light of the mid-morning Sun, and I had to catch myself from showing amazement, as I was stricken by the fact that here was one of the most breathtaking examples of the masculine sex that I've had the fortune to lay eyes on. His stature was around 6'2'', with him appearing to be in his early-30s, and I could tell through the T-shirt and shorts he was wearing that he had a body that would make the Greek gods envious. He was Caucasian, but his skin was beautifully bronzed. He had dark eyes and hair--of which his hair was mid-length and lied down nicely with just the slightest waviness to it, with bangs hanging just off to the sides of his eyes. His face was warm and inviting, with youthful, angular good-looks, while being smooth-shaven.

"Oh--hmm--I've kind of let it go a bit, haven't I?," I replied to him in a feminine voice after discreetly clearing the lump in my throat.

"Well that's quite alright, ma'am, or else I wouldn't have any work. My name's Brutus, by the way."

"My name is Jamie. Good to meet you, Brutus," I said, while offering my hand for him to shake.

He took my hand; gently, but with a firmness to it that evinced a powerful grip, he shook it.

"It's good to meet you, too, Jamie."

It was in that moment that I first became especially aware of my fragility and smallness compared to him. I weighed only 145 lbs. and stood a mere 5'8'' next to his imposing stature. The largeness of his hand enveloped my dainty palm and fingers. The skin of his hand was thick, and rougher than mine. It wasn't unappealingly course, but it gave me the impression that he could handle thorn bushes with little worry.

So then also, awareness came to me of my long, natural fingernails that were painted deep pink with metallic sparkles; and the feminine gold ring with diamonds and a pink tourmaline center-stone that adorned the ring finger of my right hand, given to me by my mother for my 29th birthday less than a year ago.

The contrast with his hand made an impression within my psyche.

* * * * *

Looking out my front living room window, I could see Brutus hard at work in the hot afternoon Sun. He had long since shed his T-shirt, in an apparent attempt to beat the heat. Sweat poured off of him, and his dark skin glistened in the rays of the overhead Sun. His muscles were well-defined. He was built, but without being freakishly large. I could even see a six-pack on him.

A nice love trail extended up from the waistband of his shorts, going past his navel. Mmm, I mused, wouldn't I like to take a journey down that cute love trail of his to find out what treasure lies at the end.

Sitting there on my couch as I stroked the long, elbow-length tresses of my naturally curly and flowing brunette hair while smoking a Misty Light Menthol 120 that I had retrieved from my pink suede cigarette pouch, I observed him through the window. While doing so, my mind drifted back to when he was standing in my doorway, holding my hand to shake it. I thought about how little and delicate he made me feel in that instant; the femininity of my hand being grasped by his massive paw.

* * * * *

After the oddly pleasant formality of the handshake had passed, Brutus quoted me a price for doing the yard work, to be paid upon completion. It sounded like a fair deal, so I readily accepted his offer. Once our business had been agreed to, he set upon beginning his task, and I closed my door behind him.

Thence alone in my living room, a slight shiver went down my spine. Oh, my, I thought--isn't he something. I noticed that I had a partial erection, which thankfully my panties had kept down, saving me from embarrassing myself in front of him. Standing there barefoot wearing a pink camisole top with lace trim, a short denim skirt, and pink bikini-cut satin and lace silk panties, I reflected upon our contrasting differences. It was all more confirmation that I had been right in my decision to come out of the closet and live my life as an open sissy-faggot. I could never be a real man--not like Brutus.

I reached under my skirt to feel my semi-erect pansy stem through my panties, whereupon I noticed that my panty-gusset was considerably wet. During my time talking with Brutus I had been leaking precum quite profusely.

Still in my living room, I pulled my panties down from under my skirt and stepped out of them, taking them with me to my bathroom to tidy myself up a bit. I soaked up some of the moisture from my panties with a dry washcloth, and from under my sink I retrieved an Always Regular Dri-Weave Pantiliner. Had I known that today I would be in the presence of such a hunky man like Brutus then I would have worn a pantiliner to begin with, in case I were to cream my panties as I just did.

Hiking up my skirt in order to wipe off my sissy-clit, I saw a long strand of clear precum hanging quite a distance as it drained from the meatus of my fairy wand. I gathered up the precum on my right index finger, bringing it to my mouth in order to taste myself. Sweet, as always--but then, the precum from all the cocks that I've ever tasted has been pleasantly sweet.

* * * * *

Again a knock sounded at my door.

"Well, how do you like your yard now, miss?," Brutus inquired upon my opening of the door.

"Wow, it's very nice. Thank you, Brutus," I answered as I handed him his money.

"You're welcome, miss. I'm glad you're pleased with the work," Brutus responded as he took hold of the money, gliding his hand over mine as he did so.

"Yes, I am. It's beautiful."

"Well, thank you, Jamie.

"Ma'am, if it's too much of a bother then don't even consider it, but would it be too imposing for me to ask to use your shower to get cleaned up? You see, I had an appointment to keep and I got caught up trying to finish your yard in one day, so I'm running a bit late."

"Well, um ...," I was caught in befuddlement as I ran his words across my mind just to make sure I really heard him say what I thought he just did. This gorgeous stud of a man is offering to be naked inside my house, even if it is while just bathing?! And he thinks that might be imposing upon me?!

* * * * *

I remembered that today is my laundry day, and I realized that Brutus didn't have any towels in which to dry himself off. Thankfully, in the dryer were some towels that had just gotten done.

I knocked on the bathroom door and informed Brutus that I was coming in to put some towels on the bathroom shelf. As I walked from the shelf upon which I had placed some towels next to where Brutus was showering, he reached out from the shower and firmly but gently grabbed my arm.

"You don't have to go if you don't want to, you know," he said to me while holding my arm. At the same time he turned off the water. I froze and my legs buckled slightly without my control. His action sent an electric chill up my vertebrae, and I strained to keep myself from tipping over and possibly fainting.

Is he offering what I think he is?, I thought to myself. Brutus saw the look of bewilderment in my eyes. Just then he reached out with his other hand and placed it on the top of my head.

He was pushing my head down with his hand. He was therein answering the question he saw in my eyes. He was telling me that it's okay: that I am accepted, that it's alright to desire cock, that I'm not wrong for wanting to please and be pleased by hard, throbbing dick.

Down to his crotch he pushed my head, and I let him. I looked at his impressive manhood, my eyes just inches away. His cock was very much how I fantasized it would be: dark, uncut and large. He was partially hard, and his member looked like it would push ten inches when fully erect.

As he stood there in the bathtub with the curtain pulled open enough for me to view him in all his manly glory, I looked up at him from my lowered stance, seeing him covered in wetness. I looked into his eyes with another unspoken question I had.

"Go ahead," he said.

And so I did. I took Brutus's masculine member in my hands while looking at it intently. Pulling back the foreskin from the head of his cock while rubbing the length of his shaft, his penis pulsed and began to grow hard. I brought my lips toward the tip of his cock and playfully planted a pink lipstick kiss on it.

I felt Brutus's cock pulse again as I planted my kiss.

That's it, baby, get hard for me.

I kissed Brutus's dick again, this time not letting my lips off. I worked my lips from the tip of his cock to around the mushroom-shaped head of his shaft, while at the same time stroking his cock back and forth with my right hand and caressing his ample balls with my left. As I did so, I felt him grow harder in my mouth.

Mmm, no matter how thoroughly a man washes, some remnant of the salaciously scrumptious flavor and fragrance of dick still remains. With impassioned ebullience I continued to use my mouth to stimulate Brutus's penis while cherishing the taste of his big cock as it blended with the waxy flavor of my pink lipstick.

Back and forth I bobbed my head, working his cock inside my mouth while Brutus grew ever harder.

My, he really is a full ten inches!

I joyously played with his enormous dick, slapping it across my face and rubbing my lips all over it, taking in the wonderful scents, flavors and textures of his manhood.

* * * * *

Having been sensually undressed by him in my bathroom and then tenderly carried naked in his arms to my bed, Brutus positioned me on my back while spreading my legs. He moved himself between my thighs while lying on top of me as he brought his lips to mine.

We reveled in each other as our mouths frolicked. Lips to lips, tongue to tongue, we embraced in amorous desire while fervently caressing each other's nude bodies.

I could feel the pleasant sensation from the course stubble of his evening shadow against my smooth, nymphly made-up face as our mouths were locked together. Experiencing the roughness of his stubble upon the softness of my face made me feel even more feminine. It made me all the more cognizant of how far I am from being a real man, as I couldn't grow a beard like that even if I had wanted to.

After a long session of passionate and deep French kissing, Brutus looked about my room and spotted a bottle of Pjur Original Eros Bodyglide silicone sexual lubricant on my nightstand. He used its contents as he began fingering me.

He entered me first with the middle finger of his right hand. In and out he worked his finger, making sure to pay attention to that special button of pleasure inside me. Then another finger was worked in. I was adoring his treatment, as he was working my pussy wonderfully. I let him know with my girlish moans of pleasure.

A third finger entered me. Mmm, how nice it is to have a hunky man here to give me such attention, I thought.

Just as I was really getting into the motions of his three fingers inside me, Brutus pulled his hand away from my quivering opening and lifted my legs up onto his shoulders as he kneeled with his knees at the sides of my thighs. I then saw him squeeze out some lube which he proceeded to stroke across his hard and very massive dick, getting it slick all over. I awaited in excited, trembling anticipation, for I knew what that meant and therefore what was coming next.

Brutus moved forward and I could feel the warm tip of his throbbing shaft pressing against the entrance of my awaiting passage. I pushed out with the muscles of my love-canal in order to open myself wider so as to better receive him.

Oh, yes, there it goes--that's the feeling I so very much crave.

The engorged head of his prodigious cock slipped past my anus into my rectum. He held it there for a moment before pushing further. As he moved his pelvis closer to me I felt more and more of his lengthy and thick rod of pulsing flesh slowly slide into me. Up into me he expertly worked his impressive member, sliding his cock-head past the bend connecting my rectum and sigmoid colon, until the full length of his veiny, stiff phallus was inside me all the way to the base of his balls.

Brutus then started his thrusting motions as he worked his stiff and massive dick in and out of me. His bare cock felt so absolutely wonderful inside me, stretching me wide as he plowed me relentlessly. With each thrust by him my femininely soft legs and dainty feet swayed in the air while being held high on his shoulders.

The copulatory sounds we were creating were an aural sexual symphony, with each of us hitting our notes perfectly. The sonance of bare skin smacking upon skin--that of the flesh of his front pelvis hitting my tushy with every forward thrust by him, making my erect clitty sway with the rhythms of his motioning--mixed with the moist and squishy sounds that my well-lubricated boy-pussy was producing as his stiff cock slid back and forth inside me, with the occasional queef of air compressed by my lover's cock escaping from my boygina and chiming in along with it.

I could even hear his large, low-hanging balls slapping against my derrière each time he thrust into me. It was a quieter flesh-smacking sound that came right after the sound of his pelvis hitting my heinie: the time it took his swinging testicles to catch up with his forward motions.

As he leaned toward me, our tongues and lips danced together as I continued to feel his unyielding manhood pushing me to ever-greater heights of womanly ecstasy. At the same time that our mouths rollicked, my petite hands and long, painted fingernails adoringly stroked Brutus's powerfully-built and gorgeously hairy chest as I fully gave myself over to him, thereby letting myself go and completely taking in the utterly and marvelously mind-blowing sensations of his colossally virile hardness far within me, thrusting unrelentingly, methodically working me over into a heated rhapsody. Nothing felt so wonderful as being deeply impaled upon Brutus's big, hard cock as I ecstatically luxuriated in the sublime sensuousness of his studly body.

We were a tangle of nakedness, embraced in erotic desire and passion, with his dark, sun-kissed flesh intertwined with my alabaster lightness. He enveloped me in the warm comfort of his nude masculinity, surrounding me with his body's largeness and muscularity, making me feel protected and looked-after.

The air was thick with the smell of our engorged, horny cocks--and yes, even the smell of a sweet, concupiscent vagina dripping with its own wetness: as it was the beautiful smell of sex; the smell of aroused genitals in lovemaking action. It mattered not that I had to substitute my eager anus and rectum in place of a real vagina--the heavy, raunchy odor of coition was still the same. What's more, I could taste the coital fragrance wafting through the air as I inhaled it into my mouth.

Such an erotically potent and thrilling scent, I thought to myself as I was having my mind totally screwed out by Brutus: for his large and stiff manhood continued to skillfully work back and forth inside me, with its beautifully massive, bulbous head sliding across that very special spot within my fag-pussy, hitting it just right. What the head of his cock was hitting was my sissy G-spot--my prostate--and, oh, did it feel so utterly wonderful!

Being totally naked and having my smooth-shaven legs spread apart as Brutus's huge cock worked rhythmically inside me made me feel so exposed. So vulnerable. So used. But oddly, I relished that feeling. It felt so emasculating. So feminine. So womanly.

I needed it. I needed to feel like that. I needed to feel him deep inside of me. Now more than ever.

"Oh, yes, Brutus! Deeper! Your huge cock feels so good in me! Fuck me! Fuck me hard!" The words leaped from my mouth without me even considering them. At another time I might have been embarrassed by having said such remarks, but in this moment of burning passion I didn't care.

What came next I couldn't help: I started to spurt my sissy-cream uncontrollably. Intense waves of orgasmic pleasure coursed from my pussy's G-spot, with the waves spreading throughout every part of me as my entire body shook in climactic bliss. As my pink-painted toes curled and my smooth-shaven legs stiffened, jet after jet of thick, white semen streamed from my erect, pulsating clit in magnificent arcs through the air onto my face, chest and stomach as I involuntarily let out a squeal of pleasure. I could taste the creamy spurts that landed in my mouth, and with each pulse of cum shooting from my clit the muscles in my pussy clenched around Brutus's thick shaft, holding him inside me even snugger.

"Oh, Jamie, darling, I'm going to cum in you!," Brutus yelled out while tightening his grip on my legs.

"Fill me with your cum, baby! Give it to me!," I moaned loudly in response. I wanted him so much, and in the most intimate of ways.

I could feel his stiff cock throb heavily inside me as Brutus resounded with deep grunts of erotic pleasure. And I noticed the extra lubrication that was produced as he unloaded torrents of his semen within me, making the thrusts of his dick glide even smoother across the insides of my ass-pussy.

Brutus continued to pound my pansy-cunt like there was no tomorrow, with his manly tool of pleasure just as hard as ever, and I couldn't hold back from squirting my love-juices in yet another round of orgasms on my part. I noticed this time that my discharges were clearer and didn't gush as far, mostly draining from the head of my undulating clit onto my smooth stomach.

Just then Brutus moved my left leg from off his shoulder onto his opposite side while maneuvering himself behind me in the spoon position. I desirously pushed my ass back towards him, covetous to feel his hard cock in my ass as he continued to hump me. He held my naked body close to his as he kissed my neck and nibbled on my left earlobe, all the while I continued to feel the supremely enjoyable deep-penetrating rhythms of his rigidly potent manhood working my pussy over for all its worth.

* * * * *

Altogether Brutus must have cummed in my ass at least four times last night, with his beautiful dick not leaving my lower pleasure-hole even once the entire time. After cumming in me for the concluding time last night, we fell asleep in the spoon position with Brutus still keeping his cock fully inside me. Even after his lengthy cock became soft, it never once slipped out of my pussy as I slept enwrapped in his strong arms, feeling the warmth of his body pressed against mine and smelling the delicious and comforting fragrance of his natural masculine scent.

He gave me the best dicking I've ever experienced in my entire life--by far. I lost count of how many times I came, as after awhile it felt like one non-stop orgasm. But I do know there was quite a wet-spot on my bed in front of me where my clitty had spurt several times. He fucked me for hours and hours last night, draining his big balls deep inside me, and I adored every intensely delightful moment of it.

And here I was, awaking to feel the huge stiffness of his morning wood inside me. What an utterly exquisite way to start the day!

Just then I could feel Brutus begin to stir as he started to wake up. That reminded me of something I had wanted to ask him.

"By the way, whatever happened to your appointment, Brutus?"

"Oh, that was just a card game. I definitely don't mind missing it in order to spend some quality time with you, precious Jamie."

With that he leaned over and started to nibble on my left earlobe while motioning his hips, once again working his very stiff and large cock back and forth inside me.

Mmm, I could tell that this was going to be a wonderful--and extremely pleasurable--morning!

Finis.