The New Susan

by: Sean McBride

 

Debbie and I had been dating for several months before she first indicated that she was dissatisfied with our sex life. It came as a complete shock to me when one evening, after I thought that I had performed magnificently in the sack, Debby held me in her arms and softly asked if I had ever been interested in doing some sexual experimenting.

In my post-orgasmic haze, I murmured something about being completely satisfied with our sexual relationship. "You’re perfect in bed, baby," I said, and then went back to sleep.

Wrong answer. Debbie stiffened and pulled away from me. Even as a sleepy, insensitive male, I immediately knew that something was very wrong. That woke me up, and I spent the rest of the evening trying to find out what I had done which so upset her.

Finally, after several hours of pleading, my girlfriend finally admitted that she didn’t get much pleasure out of our lovemaking. Of course this put my male ego in jeopardy, so I adopted my best macho attitude and forcefully pushed her down on the bed; promising that I would give her everything she wanted and more than she could ever hope to handle.

Now I’m smart enough to know that I’m not the most endowed man in the world, so I set about burying my face in between Debbie’s thighs. For almost an hour, I licked and sucked and caressed and did everything that I thought she would like. At times it seemed that I was winning this little battle or ours, but other times Debbie just seemed to be contented, and not actually in the throes of passion, as I had arrogantly promised.

I redoubled my efforts and serviced her until my tongue was worn out and my jaw threatened to lock up--but it was no use. Even though my ego was on the line, I ultimately had to admit that I had failed in my desire to give my girlfriend "more than she could handle." Debbie had enjoyed some pleasure, but not the spectacular fireworks that I had hoped for. Finally, I realized that I had lost. The last few minutes consisted of me just rubbing my face against her sex and absentmindedly wondering how I could have been so naïve to Debbie’s boredom with me in bed.

Debbie finally pushed me aside, and I’ll give her credit, she was as tender as she could be expected when she explained that she had faked her orgasms with me for the last few months. But the bottom line, she said, was that she needed real pleasure in order to continue in our relationship. She was almost apologetic as she explained that she cared deeply for me, but needed to find somebody who would provide her with more sexual satisfaction. And then the final blow. She had been invited to go to New Orleans for the weekend with one of her co-workers, and she wanted to see if he could give her what was missing in our relationship.

In other words, she wanted some big he-man to fuck her silly.

I was crushed, and as I realized that Debbie was breaking up with me, desperation set in. I threw myself at her feet and begged Debbie to give me a second chance. I started to panic, and swore that I would do anything to please her. "I’ll do better. Teach me what I need to know," I begged. "I’ll do anything, just don’t leave me!"

Debbie smiled softly and bent over to kiss me on the forehead. "Sweetie," she cooed, "I could teach you to please any woman orally, but that would just be a mechanical thing. You’re never going to be the real macho guy who sweeps a girl off her feet. You’re a sweet and sensitive guy, and I’m sure that somewhere out there, there’s a girl who will love you for the great guy you are—I still love you for the great guy you are, but I just need someone a little stronger in my life."

The soothing tone in her voice made it seem like everything was going to be all right. But somewhere deep inside me, I feared that I would never be able to get over Debbie if she left me. Tears started to escape my eyes as I thought of how I had been such a disappointment to her. I knew that I would probably be a disappointment to every other woman from now on; which sent me into a full-blown crying fit.

It’s hard to convince your girlfriend that you’ll be manlier from now on when you’re bawling your eyes out on the floor at her feet. Debbie was right. I was a complete wuss.

Debbie plopped down on the floor beside me and held me as I got it all out of my system. I felt so safe and secure in her arms, and I dreaded having to go on without her. I dried my eyes and begged one last time. "Please…"

She cut me off. "Brian, I love you, but with you, it’s more like what I feel for my girlfriends. We can still be friends, but I need something different."

We were silent for a few minutes, and I had a moment of clarity pass before me. Of course Debbie was right. I was, and would always be the nice sweet guy that girls loved to hang with because I wasn’t any sort of a sexual threat. I was nothing but a girl with a penis for all they cared. The problem was that despite my wimpy nature, I still loved Debbie. So I pushed my ego down and decided that I had to figure out some way to stay in Debbie’s life. Previous experience told me that "we can still be friends" actually meant "I never want to see you again!"

In desperation, I blurted out "Then let me be your girlfriend. I know that I’m not much of a man, but I don’t want to loose you. Even if that means never sleeping with you again, just don’t cut me out of your life completely! I don’t know what I’d do without you!"

There was a long silence, and then an odd look came into Debbie’s eyes, and she took my face in her hands and looked me over from head to toe. I was too scared to speak, and only found some relief when a sly smile crossed Debbie’s face. "Even if I go away with Jack for the weekend? You’re willing to wait at home for me like my girlfriend, knowing that I’m out with another man?" she asked. "Even if I stop by your apartment at 3:00am, reeking of sex from an all-night orgy with fifteen guys, you’d still be just happy to be in my life?"

I hated the idea of her being with Jack (I’d hated her boss the moment I’d first met him. He was a typical company president who threw his wealth around like honey to attract pretty secretaries). Still, I figured that it was better to wait for Debbie at home than to never see her again. Even if I had to wait for her after a she had had her way with a roomful of men. I tearfully admitted that I would do whatever and put up with whatever it took to stay with her.

Debbie’s breathing got a little erratic as she pressed on. "What if I didn’t break up with you?" she asked. "What if I kept you as my little sex slave? Kept you tied up during the day, or dressed up in some cute little maid’s outfit? Made you clean my house. Made you wait for me while I was out on my dates. What if I made you suck all the slime out of me when I finally got back home? Could you do that? Clean me out after a bunch of guys had filled me up?" A shiver went down her spine as she thought about this, and I realized that she was very turned on by this thought. I also realized that I had finally found a way to get Debbie sexually aroused, even if it meant that I would be turned into nothing more than her little sexual plaything.

"Yes," I whispered. "I’ll do anything. Just tell me what you want. Teach me to please you," I begged. I turned to kiss her breasts, but it wasn’t necessary. Debbie erupted in orgasm without me having even touched her.

When she caught her breath, she asked one more time if I was serious. I eagerly said yes, and then she told me to start proving myself as she pushed me down between her legs.

Her juices were everywhere, and I licked it all up, even those juices that had seeped down between her ass checks. I licked her from navel to ass, and this time my tongue stayed as ready-to-go as my cock was. Debbie had several smaller orgasms while she told me that she could show me how to please her, but said that it would be on her own terms. If I was serious in staying with her, she explained that there would be a major change in our relationship.

I’ll be your mistress, and you’ll be my little sissy slave," she said as she stroked my hair and had yet another orgasm. "I’ll dress you up and make you live like a silly little French maid, or maybe a cheap whore. I’ll make you go on a strict diet, make you shave your legs and wear makeup at all times. I may even put you on female hormones and make you get breast implants. Do you think you could do that for me?" she asked.

I popped my head up and pleaded "Yes, mistress."

Looking up at her from between her legs, my face smeared with her essence, I admitted that female domination had long been one of my deepest fantasies anyway. I began to elaborate, revealing those deepest fantasies of mine that I thought she would like to hear. Debbie smiled at my disclosures, but cautioned me, saying that what she had in mind went far beyond simple female domination. "It won’t be a game, it will be for real," she said. "You’ll learn to please me as a woman would, and I’ll treat you as the little sissy that I think you are deep down inside."

At this pronouncement, my world went black and I suddenly had an orgasm of my own. Debbie smiled and scooped up some of my cum from the floor. There was a lot of it, by my standards anyway, and she rolled her fingers around in the sticky mess for a minute and then brought it to my lips. Never wavering, I started to lick up my own semen.

I voraciously sucked it all down as Debbie told me in detail about her college roommate, and how much she had enjoyed it when they became more than just roommates. "For a few months we were quite the lesbian couple on campus," Debbie admitted. "And even though we both finally decided that we were mainly interested in men, I still miss those long weekends in bed with Susan. If we stay together, I think I will turn you into my new Susan."

Licking the last of my cum from her fingers, I bent over and kissed her feet, and quietly asked Debbie to be my mistress and turn me into her new Susan. I was rock hard again, as I envisioned myself as a beautiful woman and Debbie all dressed up as my S & M mistress. Admittedly, I’d never crossdressed before, let alone what Debbie had in mind for me, but that doesn’t mean that I hadn’t thought about it before. Besides, I couldn’t deny that I was completely aroused by the idea--especially since it was such a turn on for my new mistress as well.

As I was thinking about this, Debbie suddenly stood up—of course, I stayed on the floor. "Be sure that this is what you want. If we start this new relationship, I may never let you go. I’ll make you do things that you will hate, but I will love. I’ll work you hard and transform you completely, body and spirit. So be positive about this before you agree."

Still lost in a sexual haze, I murmured out a "yes mistress." Once again, she smiled, and then went to the door. "I’m going away with Jack for the weekend, if you’re serious about this, then I’ll expect to see Susan waiting for me when I get back on Monday. If not, I’ll understand, but it will be over between us."

She closed the door with a wicked smile and I lay naked on the floor for several hours. I thought about what Debbie had said. I cried a little, thought a little, and drank a little to ease my pain at being unworthy to be Debbie’s boyfriend. Hours passed, and ultimately I realized that I was truly in love with Debbie, and would do just about anything to be with her. Even if I was just to be a sex slave. But better yet, I hoped that even if I couldn’t be her boyfriend ever again, perhaps I would please her enough to become her girlfriend. Her new Susan!

This once again turned me on, and I started to masturbate. But just as I approached the point of no return, I suddenly realized that a good little sissy-slave wouldn’t cum without his mistress’ permission.

I intuitively knew what I had to do. I quickly cleaned myself up, grabbed my credit cards and headed out the door. I went to the all-night Wall-Mart, and headed immediately for the makeup section. I didn’t know what to buy, so I boldly filled my basket with lipsticks and eye shadows, fingernail polishes and mascara. Basically, I bought a bit of everything and then headed to the shoe department.

I had no idea what my size was, so I once again pushed aside my pride and tried on a pair of pumps right there in the middle of the store. Size ten pumps fit me, so I bought four pair of shoes and then crossed the aisle and grabbed a nice supply of silk panties and some pantyhose.

My shopping spree was turning me on, and I was so intent on buying everything that I needed that I didn’t notice that I was being watched by one of the late-night store employees. She made her presence known when I found myself looking at bras, but unsure what the sizing meant.

"Can I help you?" she asked, startling me from behind. That was the only time that night when my resolve faltered, but Jessica the store clerk immediately put me at ease and laughed when she said that a lot of guys showed up at Wal-Mart looking for their Halloween costumes late at night. "Although you’re starting a bit early," she joked. "It’s still September."

Jessica told me not to be embarrassed, and pulled out a tape measure and proceeded to take my measurements. Within minutes, I had several bras to match my panty selections, and Jessica had helped me select a few sexy skirts, blouses and dresses. To save me from embarrassment, Jessica rang up my order at her register in the women’s section.

Even though my bill came to $760, Jessica told me that if I really wanted to be a hit at the Halloween party, I should invest in a corset and some breast forms. "We don’t sell the stuff you really want here," she said, "but I get off in an hour. I could take you to a little place I know and help you pick out the rest of your outfit." By this point in the evening I was so horny that I immediately agreed to wait for her outside by the loading dock.

So I stood there with my shopping cart full of female finery, waiting for Jessica to finish her shift. At one point a tall Black man came out for a cigarette break and smiled when he saw the lingerie and makeup that filled my shopping bags. "You must be waiting for Jessica," he laughed as he snuffed out his cigarette.

"It seems like every month or so she ends up with some little boy waiting for her with a bag full of sissy clothes." I blushed and tried to deny it, but the guy just ignored my protestations and came closer to where I was waiting. Looking around to make sure that we were alone, he introduced himself as Tyrone and offered me a joint. Truth be told, a joint seemed like exactly what I needed at the moment, so I gratefully accepted.

Within minutes I was more at ease with Tyrone, and told him about my "Halloween party," and how Jessica was going to help me with my costume. Tyrone looked me up and down, and told me that I would be very convincing as a woman. "Especially with Jessica’s help" he smirked.

Tyrone then asked me if I could walk in heels. I told him that I had never tried them before, and soon Tyrone had me practicing in a pair of pumps and walking across the loading dock while he gave me suggestions on how to make my walk more feminine.

By the time we finished the joint, Tyrone had talked me into putting on my full outfit. For modesty, I stripped behind the dumpster and pulled on the pantyhose, skirt and blouse. I felt so sexy as I stepped out from the shadows for the first time in full drag. But Tyrone laughed when he saw me, and said something about the bulge in my panties spoiling the illusion. Fortunately Tyrone had the solution for my problem. He went back into the store and returned with a roll of duct tape. Without saying a word, Tyrone lifted my skirt and pulled gown my panties. Using the tape he pushed my testicles up into my body cavity as he started to stroke my cock.

I came after just a few strokes and Tyrone scooped a bit of it up and slid his fingers into my mouth. I licked my semen from his hand while Tyrone continued to tape me up. When he was finished with me, there was no longer a bulge down there. Everything had been pushed up inside me and taped securely into place.

But Tyrone wasn’t finished with me. He pushed me to my knees and told me to unzip him. Behind the Dumpster, I fished out my first cock and eagerly wrapped my lips around it. I did my best to deep throat him, but Tyrone was huge and I gagged each time he thrust forward. Finally he flipped me around, lifted my skirt and aimed his cockhead at my virgin anus.

"Relax, or this is going to hurt," he said and then spat on my ass. He waited as the saliva dribbled down to my hole, and then he began to firmly press into me. Fortunately the marijuana had loosened me up. There was a pop and suddenly Tyrone was inside me, thrusting away for all he was worth. I would have screamed out in pain, but Tyrone covered my mouth with his hand until the pain numbed into pleasure.

I was leaning against the dumpster, being fucked by a man I had just met a few minutes ago when I saw Jessica come out of the building. She smiled at the sight of me being taken from behind and simply came over, bent down and started to stroke me while licking Tyrone’s balls. All the while he continued to fuck me until I felt like I was going to split in two.

Within moments, I felt a red-hot liquid pulse into me, and I sent another load dribbling down the side of the dumpster. Wow, that was amazing, I thought. Who needs to be a man when you can enjoy sex like that?

After we caught our breath, Tyrone pulled out of me and told Jessica that he got off at 5am. Jessica gave him a long kiss and said that we would be ready. She grabbed me by my testicles and dragged me to her car, where she gave me a kiss on the cheek and then ordered me into her trunk.

Tyron pushed me down inside, and then threw as many of my shopping bags that would fit in after me and slammed close the trunk. So I lay there, without any space to move, completely wasted, dressed in a skirt and heels with semen leaking out of my ass and the taste of my own cum in my mouth. I wondered if this was what Debbie had in mind for me? Was Susan really such an easy skank? Or was that just me? Truthfully, I didn’t care. I was as aroused as I had ever been in my entire life and determined to see this adventure out to its conclusion.

The car started to move, and I was driven around for quite some time. Every once and a while we would pull over and Jessica would knock on the trunk and ask if I was all right. When she was satisfied that everything was okay, she would drive some more. At one point we must have driven for an hour along a bumpy back road. For the life of me, I had no idea where we were. My high was rapidly disappearing, and I began to get a little scared.

But I was still horny, and that seemed to get me through the panicked claustrophobia that continually welled up inside of me.

We finally stopped. I heard a garage door closing behind us and then, when the trunk was opened, I was blinded by a camera flash and quickly hauled to me feet by two very strong women. I was dragged like a rag doll inside a house and then thrown roughly down and bound tightly to a chair with a roll of duct tape.

I was gagged and blindfolded, and left to wait while Jessica and two strange women went through my shopping bags and my wallet. Derisive laughter filled the air as this trio of harpies appropriated those of my purchases that they could use. They made constant jokes at my expense, about the "silly little sissy tied up in a chair, just waiting for Tyrone and his friends to come make him into a woman." They laughed that Tyrone would probably make me into a blonde, because only a blonde bimbo would get into a stranger’s car without knowing what was waiting for me.

The laughed and called me "Silly, Slutty Sally," and by this point I was terrified that they might be right in all of the dire predictions that they were making about me.

It was all too much. I started to softly cry beneath my blindfold. The laughter died down as I decided to just let the tears flow freely. Finally, the room got completely quiet and Jessica removed my blindfold. She looked as sad and scared as I felt and she untied me and gently held me until I calmed down a bit. "Easy sweetie," she whispered, "we were just teasing."

After twenty minutes of a good cry, I finally collected myself enough to stop shaking. Jessica and her two friends, Paula and Carmen apologized for scaring me so. Somehow they got the idea that I was looking for some big bondage/forced feminization/rape scenario. Usually when Tyrone found a little sissy boy, that’s what they had wanted to happen.

But I shook my head "no." Paula brought me a nice cup of tea, and Jessica held me as I explained what had happened to me during the last few hours, and how I was determined to make Debbie proud of me when she came back on Monday.

Once again, I broke into tears as I told them of how Debbie was going to leave me. There was a long, awkward moment and finally Carmen spoke up. She said that she had three questions for me, and that I should think hard before answering each one.

First, she asked if I really loved Debbie so much that I was willing to become her little sissy sex slave for real? I already knew the answer to this one, and I quickly answered yes. Carmen just clicked her tongue and said that it wasn’t enough. She asked about what I wanted for me? Could I be happy if I went through with this?

I thought about this question a bit longer, but once again, it only took me a few moments to answer in the affirmative. There was no denying how much I was sexually excited by the thought of being transformed into Debbie’s new female sex slave. But I also knew that there was something much deeper going on here. "I’ve never been all that good as a man," I finally offered up to the group. "Something tells me that I’m more cut out to be a girl. Something is making me want to give it a try. Hopefully, it’s enough to keep Debbie happy, but more importantly, maybe it’s the thing that will finally make me happy."

Jessica, Carmen and Paula took this in, and then Carmen once again broke the silence with her final question-- the most important question of all. "Do you want to be a blonde, brunette or redhead?"

"Susan is a redhead" I answered.

There was a collective squeal and all three women grabbed me and drove me into the bathroom. Within moments I was naked and the transformation had begun. I was immediately smeared with a depilatory from head to toe. Paula began plucking my eyebrows into a high feminine arch while Carmen brought out a vibrant red hair coloring kit. It took about an hour to get everything done to me. When I left that bathroom, the room was a complete mess, but I looked like heaven.

My body was completely smooth except for a small patch of pubic hair that had also been dyed red to match my new do. Jessica had taken a file to my feet and painted my toenails a deep red. Carmen had bonded false nails onto my fingers and varnished them in a matching color.

I was powdered and puffed and pampered by three girls playing with a real-life Barbie doll. And then Carmen came over carrying a tattered old box. "These were my first pair," she said as she handed me the box. "I give them to you."

I opened the box to find a pair of plastic breasts and some medical adhesive. Suddenly it hit me. Carmen was a man, or at least she used to be. I threw myself into her arms and we both threatened to start crying again until Jessica finally broke us up. There was something of a mock ceremony that followed as Carmen kissed my nipples goodbye and then attached my new false breasts with the glue. It would be eight days before these tits came off and I saw my nipples again.

From there I was tightly laced into a corset and dressed in some of the clothing that I had purchased earlier. Looking in the mirror, I was amazed at the woman looking back at me—and I hadn’t even started on my makeup yet. I still looked almost believable. I looked like I could be a Susan!

Of course there was still one prominent problem. Try as hard as I might, there was no way that my cock would go down enough so that it could be tucked into a more ladylike position.

Jessica had the perfect solution, and she dropped to her knees and crawled under my skirt. No sooner had she swallowed me than I erupted with a mind-blowing orgasm. Jessica drained me dry while Carmen and Paula held me on my feet. Jessica then stood up so that I could lick what was left of me from off of her lips. As we stood there making out, Carmen and Paula got a little jealous. Their insistent mouths quickly joined ours, and within moments the four of us had fallen in a writhing heap of sex upon the floor.

To my pleasured surprise, Carmen still had her penis, and while it was small, it still worked and Jessica was content to ride it. Paula pushed me down and climbed on top of me. I was barely able to see my cock past my new stick-on breasts, but I could sure feel it as Paula bobbed up and down on top of me. It was an amazing sight, but one that quickly disappeared from view when Carmen suddenly sat on my chest and fed her "little clittie" into my open mouth.

That’s how we were positioned when Tyrone and two of his friends walked in on us. They didn’t say a word, they just stripped naked and then the real fucking began. For the next two hours it was a non-stop sexfest and I’m happy to say that I was usually the center of attention. My every orifice was stretched open wide and filled with cum-coated genitalia. I must have swallowed a gallon of cum and spurted back a gallon of my own. My only disappointment was that the guys were using condoms whenever they fucked me. Oh how I wanted to feel their juice dribbling out of my newly drilled pussy.

We eventually fell asleep in a tangled heap right there on the floor. Tyrone had finally run out of steam and he just dropped off after shooting one last load into my happily-numb behind. He was big enough that even when he softened, he still stayed implanted firmly inside me. It felt great, being filled with Tyrone while he slept. For my part, I slept soundly in Carmen’s arms, with my mouth sucking on her breasts like a newborn baby.

I slumbered away peacefully, filled with erotic dreams of me as a talented and horny woman who spent all her time pleasuring Mistress Debbie and her new friends Carmen, Jessica, Paula and Tyrone.

It was after 1pm when I was awakened out of my sex dreams by the sounds of real sex. I opened my eyes and saw that Jessica was riding Tyrone like a cowgirl on a bucking bronco. Her delighted squeals woke everybody, and the orgy started up anew (although for only one round this time).

And then, just as soon as it had started, our wonderful sexfest ended. The guys kissed us all goodbye as they gingerly headed out the door. Tyrone whispered in my ear as he left that he thought that I was going to make a "damn sexy little bitch." It was a bit vulgar for my tastes, but nevertheless, his comment made my day—and left me wanting a bit more time to show him just what a damn sexy little bitch I could be when I put my mind to it.

But that would have to wait because after the guys left, we four "girls" had some very important things to do. First on the agenda was more beauty sleep, so we all climbed into one big bed and slept for a few more hours. Then it was time for a quick bite to eat, followed by a shave and complete makeover for me. Thanks to Carmen, Jessica and Paula, I left the house that afternoon looking like nothing more than a totally natural woman—and a damn sexy little bitch to boot.

First stop was the mall. To my surprise, it was only a few minutes away (Jessica had been driving around in circles last night). We parked and went straight to a booth where I had my ears pierced three times on each side. I think the girl read me as a man, but with Carmen fiercely standing guard over me, she wisely kept her mouth shut.

There wasn’t that much time to shop as we had slept too late into the day, but we did manage to get me some trendy club clothes and matching shoes. We also barged into a lingerie store and bought some see-through teddies and some very revealing bra and panty sets.

I was constantly frightened that somebody would see me as a man in drag, but thanks to the constant coaching from my girlfriends, I passed by almost everybody unnoticed. Those few who did suspect that something was amiss soon found themselves face to face with the wrath of Carmen. "Never piss of a queen, honey" she would tell me with a wink in her eye.

We didn’t get all our shopping done, but the most notable event of the day was that I got the poor shoe clerk all hot and bothered while he was waiting on me. The poor kid had no idea what was going on. He stammered and fumbled about, completely overrun by the four sexy women who kept him hopping that afternoon. He was completely lost in his lust, and I was sure that it was me that he wanted most of all. He spent most of his time helping me out, and he kept touching my thighs suggestively as he put me into a mountain of pumps and sandals. He even gave me a nice discount on the shoes (of course I did buy four pairs before we left).

He was a really sweet kid, just a little unsure of himself around four high-energy women. I found his soft-spoken manner to be quite endearing. Carmen could see that I was interested, and that the clerk was interested, but neither of us was going to make the first move.

So she took matters into her own hands. As we were ready to leave and the poor kid was watching me go, still unable to summon enough courage to speak, Carmen suddenly giggled and said, "let’s have some fun."

She sauntered back into the store just as the kid’s manager was pulling down the security gate. She walked directly past her and over to the kid (his name was Jonathan). From out in the corridor, we watched the master at work. Jonathan started to squeak out that they were closed, but Carmen put her finger to his lips and told him to be quiet. "You like my friend, don’t you?" she asked and Jonathan answered by blushing bright red.

"Good, she likes you too," Carmen said. "You should meet us tonight at The Beat Factory. I’m sure that Susan would love to show you her new shoes." Jonathan lit up for a moment, and then suddenly frowned. It turns out that he wasn’t 21 yet, but Carmen told him not to worry. She took his hand and wrote something on it that made Jonathan blush again. "Just show this to Sergio at the door."

Then she wheeled about and sauntered out. Jonathan was torn between watching Carmen’s ass as she left and looking at me waiting on the other side of the gate. I was afraid that Carmen might take the boy away from me if I didn’t put up a fight, so I reached over and unexpectedly kissed Jessica full on the mouth right in the middle of the mall. I also fondled her breasts for good measure, all the while never taking my eyes off of Jonathan.

The kid forgot all about Carmen’s ass and almost came in his pants.

"Damn girl," Carmen kidded, "that isn’t fair." We laughed like a pack of schoolgirls and left to go home and get ready for a night of dancing.

Okay, so we had some time to kill before the club got going that night. There were three horny girls waiting around (Jessica had to work again) so it wasn’t long before we were all naked and rolling around on the floor. And once again Tyrone walked in to the sight of me with Carmen’s cock stuffed inside my mouth while Paula had a double ended dildo shoved inside the two of us.

Tyrone just laughed, "Damn, you girls never quit."

We were up to the challenge, so the three of us attacked him. And no, we never quit until we had sucked every last ounce of pleasure out of him. Tyrone was exhausted, but we girls were just getting warmed up. I dressed in my sexy new outfit, and we all headed out to dance the night away at The Beat Factory.

Sergio met us at the door. He was a big bald bouncer who seemed to be on an intimate basis with Paula and Carmen--and he looked like he would be interested in letting me get to know him as well. He told me that some kid was waiting inside, and even though he wasn’t old enough to get in and even though Sergio could loose his job, he had let the kid in because he was a friend of Carmen’s. And because of the promise that was written on the kid’s hand. We all promised pay Sergio for his kindness later on that night, and then we kissed and rubbed up against him as we passed into the club.

Jonathan was easy to spot. He was the anxious kid who stuck out like a sore thumb, sitting painfully alone in a booth sipping gingerly on a Pepsi. He was a meek little mouse in a room full of hungry cats. That changed immediately when we three drop-dead gorgeous club hotties suddenly piled into his booth and started ordering drinks. I thought it was cute, how this shy young man slowly warmed up to the three vivacious females who were hanging all over him.

It turns out that the kid could dance. He could do all the Latin dances with Carmen, and all the disco stuff that Paula liked. He saved all the slow dances for me, which was a good thing because I can’t dance at all.

Yet here I was, dancing backwards in my new heels with Jonathan.

He was the perfect partner, and he never pushed me beyond what I could handle. I wouldn’t have believed it a few hours ago, but I felt perfectly capable and oh so very feminine wrapped up in Jonathan’s big strong arms. Boy! Was I getting hooked on this becoming a girl thing!

We were in the middle of a slow song; I had my head resting on Jonathan’s chest and was enjoying his hand softly rubbing my ass when Jonathan suddenly stopped and looked me straight in the eye. "So what’s your real name?" he asked.

The magic suddenly came crashing down around me. He had been too nice of a guy to lie to, or to sic Carmen on, so I swallowed deeply and told him the truth, expecting to be punched or at least deserted on the dance floor when Jonathan found out that I was really a man in drag. But Jonathan just shrugged and said, "cool." Then he pulled me in tight again and we resumed our dance.

I knew right then that I was going to give this kid the best night of his life.

I whispered into Jonathan’s ear that I wanted him to take me home. He didn’t get it at first, but when I started running my tongue inside of his ear and kneading his crotch, he finally got the idea. Carmen saw what was going on, and she asked if she could come too. Paula, on the other hand, was determined to thank Sergio for a night of fun with a night full of one-on-one fun, so we left her behind.

For a shoe store clerk, Jonathan had a great car and a spectacular house in a really upscale neighborhood. When Carmen and I questioned him, Jonathan explained that his dad was out of town on business, and that’s why he had the use of the Jag, the house and the hottub.

He was so cute, this nervous little boy driving daddy’s car for a night of naughty fun. I couldn’t help myself. I leaned over and decided to give Jonathan a taste of what was to come.

Jonathan may have been a little boy about some things, but he was all man when I peeled back his underwear. He jutted straight up, and I swear that he was the mirror image of the gearshift in size and solidity. Undaunted, I gave him my most enthusiastic blowjob ever, and was wiping cum from my lips before we were halfway to his house.

Did I say house? It was more like a mansion. Daddy was obviously a very important man, and we wasted no time before we began to sample his largess. Expensive wines were opened as Carmen, Jonathan and I jumped into the hottub. We all stripped down to nothing, or just nothing plus the breast forms in my case. If I was a little worried about Jonathan’s reaction to my real body, I shouldn’t have been. No sooner did my little clittie pop out than a feral look came into Jonathan’s eyes. In no time I was bent over the side of the pool while Jonathan plowed into me from behind while Paula sucked roughly on his nipples.

There was a loud groan and I got my wish as Jonathan shot a copious load deep into my ass. It would be dribbling out for days to come. But Jonathan wasn’t done. He kissed me hard on the lips and then surprised me by leaning over the edge of the tub himself. "Do me now," he commanded.

Who was I to disappoint my gracious host? Which is why I was fucking Jonathan while Carmen licked his balls when the lights to the pool suddenly came on. We scrambled to cover ourselves, but it was too late. Jonathan’s dad had caught us.

It was rather embarrassing, tits and cocks hanging out like that. But to make matters worse, it turned out that Jonathan’s dad was Jack, the guy who was supposed to be away fucking my girlfriend in New Orleans that very weekend.

Sure enough, Debbie was there too, although she didn’t recognize me at first. Talk about an awkward moment. Jonathan had been caught red handed, but it was also clear that daddy had been caught with his plaything as well. Debbie was dressed in a leather outfit that was mostly a collection of straps and buckles and padlocks. It was actually a bit funny, father and son learning about each other’s kinky side all at once, but no one was laughing. The two men needed some time to talk, so we three "girls" waited for them in the dark by the pool.

Debbie hadn’t been expecting company, and she was too angry at being interrupted to see straight, which is the only reason that I can think of that she took so long to recognize me. But eventually she did see past my smeared makeup, and then, boy did the shit hit ever the fan.

She let loose with a string of expletives that never seemed to end. I tried to explain what had happened, but Debbie wasn’t listening. She started to get violent, and I curled into a ball and began to cry in fear as she punched and kicked me.

I just wanted to die. I thought that I had done what my girlfriend wanted me to do. I was becoming Susan for her. What more could I have done? I had come to the point where I was willing to do anything to make her happy. Even if that meant becoming a complete sissy sex slave. What more could I have done to prove my sincerity?

Debbie wasn’t impressed. She continued her assault on me until finally Carmen could stand it no longer. With one mighty heave, Carmen pushed Debbie into the hottub and told her to stay in until she had calmed down. Debbie kept trying to get out, but Carmen kept pushing her back in.

So Debbie changed tactics. She said that as soon as she got home she was going to call all my family and friends and tell them that I had become a little sissy. Actually, over the past few hours I had been so enamored with the new me that I thinking about doing the same thing myself, but hearing the threat fall so venomously from the lips of the woman I loved made it almost unbearable to think about.

"When I’m done with you," she spat, "you won’t have a job. No friends, no family, no money, nothing."

Carmen started to take up my defense, but Jonathan—my knight in shining armor, cut her off. He reached into the hottub and pulled Debbie out by her hair. "You might want to think about that," he glowered. "As much pain as you can inflict on Susan, I’ll make sure it’s double for you."

Debbie started to protest, but Jack cut her off. "And I’ll help him. Those pictures I took of you this weekend, they’ll be all over the company by Monday if you even decide to fuck with my son or his girlfriend."

"You’ll go down too," Debbie yelled. But Jack just smiled. "No I won’t. I’m not in any of the pictures. And trust me, I was in New Orleans all weekend. I can get an alibi in no time. Your career will be over and you’ll be the laughingstock of the industry."

Debbie was dumbfounded. This was supposed to be her weekend of sexual triumph, and it had all gone so very wrong. "This little tantrum is most unbecoming, even on a little office slut like you," Jack cautioned. "You came to me, asking me to make you feel like a woman. Judging by this display of yours, you obviously need a lot of work. So here’s what I’ll do. I’ll give you what you need, and you’ll love me for it. You will be my personal sex slave. Of course I’ll share you with the rest of the managers and some of our select clients. And don’t shake your head because you don’t have a choice, my pet. You’ll be a whore for my needs, but I’ll also turn you into a perfect lady. Maybe one day you’ll be as feminine as my son’s girlfriend here."

With that Debbie sunk back into the hottub; she would threaten me no more.

Jonathan and Carmen helped me to my feet and started to lead me away. But not before Jack stopped me. "I’m always glad to meet Jonathan’s lady friends. If there’s anything I can ever do to help you, please don’t hesitate to ask." I smiled and kissed him on the cheek. I knew that I had liked Debbie’s boss from the moment that I first met him. And I knew deep down that his son was just as great a guy as his father was.

I moved in with Jessica, Carmen and Paula the very next day. It wasn’t a long stay. Two months later I moved in with Jonathan. Thanks to daddy’s deep pockets, I was now living full time as a woman. For Jonathan’s sake (and for mine) I underwent a full hormone treatment. I legally changed my name and gender, as well as endured countless hours of electrolysis, various facial reconstruction surgeries and liposuction proceedures. I even had some ribs removed. By the time I got my breast implants a year later, I was a more realistic-looking woman than Carmen was—something I never let her forget.

Of course, she still had her penis, and mine was scheduled to come off in less than a month.

Our wedding was scheduled just four months after that final surgery. It was a storybook occasion in a big Catholic church (we didn’t tell the priest of my past). Carmen, Jessica and Paula were my bridesmaids, and while I know that all brides look beautiful, I never thought that I would feel so radiant as I did walking down the aisle in that backless, beaded dress. It oozed as much sex appeal as was allowed in a church. Every eye in the sanctuary smiled upon me. I think that most of women were jealous and the knockout woman that Jonathan had landed at the altar smote the men with desire. Even the priest wanted a crack at me, if the erection he sported under his robe during the ceremony is any indication of his state of mind.

We spent three weeks in Hawaii for our Honeymoon. It was the first time that we had dared to enjoy sex with my brand new vagina. We went slowly at first, and then when we were certain that I wasn’t going to be torn apart, things got a little more arduous. By this time we were finished with our Honeymoon, we were fucking like newlyweds every single time that we were alone.

We returned home very much in love. Within the year Jonathan had finished his school and was ready to take a position in his father’s company. He was now going to be a big businessman just like daddy, although sometimes we still play "shoe salesman and the horny customer" late at night in our bedroom.

I am still great friends with Carmen, Jessica and Paula. Jonathan has even softened somewhat towards Tyrone and allowed him to rejoin our circle of friends. Occasionally the six of us will get together for one of our orgies, but mostly I am quite content to spend my time and energies seeing to Jonathan’s needs.

I finally got the full storybook ending when we adopted a baby girl. Of course Carmen was the godmother to the girl we named Susan. Jack was so happy to finally be a grandfather that he set about spoiling the girl from day one.

And on day two the new nanny arrived. Her name was Deborah, and she looked remarkably like a well used version of the girl I used to date oh so long ago. But this nanny was now a completely meek and subservient little helper, so it couldn’t have been Debbie.

 

 

 

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© 2001 by Sean McBride. All Rights Reserved. These documents (including, without limitation, all articles, text, images, logos, compilation design) may printed for personal use only. No portion of these documents may be stored electronically, distributed electronically, or otherwise made available without express written consent of the copyright holder.